# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2011
#data_New_Global_Publ_Block
data_global
_journal_name_full CrystEngComm
_journal_coden_cambridge 1350
#TrackingRef '- Form_II.cif'
_audit_creation_method
;
manual editing of the CIF file
created by SHELXTL Ver. 6.10
and processed with modiCIfer-03272007.
;
# 1. SUBMISSION DETAILS
_publ_contact_author_name 'Guzei, Ilia A.'
_publ_contact_author_address
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI 53706
USA
;
_publ_contact_author_phone 608-263-4694
_publ_contact_author_fax 608-262-0381
_publ_contact_author_email iguzei@chem.wisc.edu
_publ_contact_letter
;
Please consider this CIF submission
for publication in
;
_publ_requested_category FA
# FA 'Full article'
# FI 'Full submission - inorganic (Acta C)'
# FO 'Full submission - organic (Acta C)'
# FM 'Full submission - metal-organic (Acta C)'
# CI 'CIF-access paper - inorganic (Acta C)'
# CO 'CIF-access paper - organic (Acta C)'
# CM 'CIF-access paper - metal-organic (Acta C)'
# 2. TITLE AND AUTHOR LIST
_publ_section_title
;
;
loop_
_publ_author_name
_publ_author_address
I.A.Guzei
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI 53706
USA
;
'Erica Gunn'
;
Department of Chemistry
University of Wisconsin-Madison
1101 University Ave
Madison, WI 53706
USA
;
'Lara Spencer' ''
'Jennifer Schomaker' ''
'Jared Rigoli' ''
_publ_section_synopsis
;
;
_publ_section_abstract
;
;
_publ_section_comment
;
;
_publ_section_references
;
Allen, F.H. (2002). Acta Cryst. B58, 380-388.
Bruker-AXS. (2007-2009). APEX2 (Ver. 2.1-4), SADABS,
SAINTPLUS,
SHELXTL. Bruker-AXS Inc., Madison, WI, USA.
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M.,
Macrae, C. F., McCabe, P., Pearson, J,
& Taylor, R. (2002). Acta Cryst. B58, 389-397.
Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc.
97, 1358-1367.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Pushmann,
H. (2009). J. Appl. Cryst. 42, 339--341.
Frisch, M. J., Trucks, G. W.,
Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman,
J. R., Montgomery, Jr., J. A., Vreven, T., Kudin, K. N., Burant,
J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V.,
Mennucci, B. et al. (2004).
Gaussian 03, Revision C.02,
Gaussian, Inc., Wallingford, CT, USA.
Guzei I.A. (2007). In-house Crystallographic Programs: FCF_filter,INSerter,
modiCIFer.
Molecular Structure Laboratory, University of Wisconsin-Madison,
Madison, WI, USA.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2009). publCIF. In preparation.
;
_publ_section_acknowledgements
;
The manuscript was prepared with the beta test version 1.0.2.
of program publCIF (Westrip, 2009) and Ilia A. Guzei's
program modiCIFer.
;
_publ_section_figure_captions
;
Figure 1. Molecular structure of (I). The thermal ellipsoids are
shown at 50% probability level.
;
_publ_section_exptl_prep
;
;
_publ_section_exptl_refinement
;
All H-atoms were placed in idealized locations and
refined as riding with appropriate thermal displacement
coefficients U~iso~(H) = 1.2 or 1.5 times U~eq~(bearing atom).
;
_iucr_refine_instruction_details ?
#3. data
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\ms'
data_guzei08
_database_code_depnum_ccdc_archive 'CCDC 809204'
#TrackingRef '- Form_II.cif'
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H13 N3 O S'
_chemical_formula_sum 'C16 H13 N3 O S'
_chemical_formula_weight 295.35
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'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 1 21/n 1 '
_symmetry_space_group_name_Hall '-P 2yn '
_symmetry_int_tables_number 14
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'
_cell_length_a 10.1716(2)
_cell_length_b 12.1281(3)
_cell_length_c 12.4038(3)
_cell_angle_alpha 90.00
_cell_angle_beta 111.8165(10)
_cell_angle_gamma 90.00
_cell_volume 1420.57(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 999
_cell_measurement_theta_min 2.44
_cell_measurement_theta_max 33.35
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.41
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.21
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.381
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 616
_exptl_absorpt_coefficient_mu 0.230
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
SADABS (Bruker-AXS, 2007)
;
_exptl_absorpt_correction_T_min 0.9117
_exptl_absorpt_correction_T_max 0.9534
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_source .
_diffrn_radiation_monochromator 'mirror optics'
_diffrn_measurement_device_type 'Bruker SMART APEX2 area detector'
_diffrn_measurement_method '0.60\% \w and 0.6\% \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 45510
_diffrn_reflns_av_R_equivalents 0.0215
_diffrn_reflns_av_sigmaI/netI 0.0118
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.44
_diffrn_reflns_theta_max 33.35
_reflns_number_total 5485
_reflns_number_gt 4961
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX2 Ver. 2.1-4 (Bruker-AXS, 2009)'
_computing_cell_refinement 'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_reduction 'SAINT Ver. 7.24A'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL, OLEX2 (Dolomanov et al., 2009)'
_computing_molecular_graphics SHELXTL
_computing_publication_material SHELXTL
_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^)+(0.0584P)^2^+0.6808P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 5485
_refine_ls_number_parameters 191
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0434
_refine_ls_R_factor_gt 0.0395
_refine_ls_wR_factor_ref 0.1146
_refine_ls_wR_factor_gt 0.1111
_refine_ls_goodness_of_fit_ref 1.066
_refine_ls_restrained_S_all 1.066
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
S1 S 0.55098(3) 0.57581(2) 0.13810(2) 0.02037(7) Uani 1 1 d . . .
O1 O 0.52548(9) 0.35655(8) 0.46838(8) 0.02756(18) Uani 1 1 d . . .
N1 N 0.50923(8) 0.46888(7) 0.31191(7) 0.01618(14) Uani 1 1 d . . .
N2 N 0.73641(8) 0.46311(7) 0.31997(7) 0.01493(14) Uani 1 1 d . . .
N3 N 1.05416(9) 0.26951(7) 0.60648(8) 0.01865(15) Uani 1 1 d . . .
C1 C 0.60812(9) 0.49810(8) 0.26349(8) 0.01470(15) Uani 1 1 d . . .
C2 C 0.72839(10) 0.40307(8) 0.41360(8) 0.01557(15) Uani 1 1 d . . .
C3 C 0.57953(10) 0.40310(8) 0.40839(9) 0.01849(17) Uani 1 1 d . . .
C4 C 0.83206(10) 0.34805(8) 0.49747(8) 0.01747(16) Uani 1 1 d . . .
H4 H 0.8044 0.3148 0.5551 0.021 Uiso 1 1 calc R . .
C5 C 0.97984(10) 0.33201(8) 0.51287(8) 0.01519(15) Uani 1 1 d . . .
C6 C 1.03991(10) 0.37376(8) 0.43642(8) 0.01677(16) Uani 1 1 d . . .
H6 H 0.9854 0.4178 0.3719 0.020 Uiso 1 1 calc R . .
C7 C 1.18033(10) 0.34985(9) 0.45637(9) 0.01889(17) Uani 1 1 d . . .
H7 H 1.2234 0.3769 0.4055 0.023 Uiso 1 1 calc R . .
C8 C 1.25700(10) 0.28581(9) 0.55183(9) 0.02004(18) Uani 1 1 d . . .
H8 H 1.3533 0.2680 0.5675 0.024 Uiso 1 1 calc R . .
C9 C 1.18970(10) 0.24845(9) 0.62386(9) 0.02027(18) Uani 1 1 d . . .
H9 H 1.2431 0.2053 0.6895 0.024 Uiso 1 1 calc R . .
C10 C 0.35888(9) 0.47401(8) 0.25488(8) 0.01632(16) Uani 1 1 d . . .
C11 C 0.28431(14) 0.56672(12) 0.26171(15) 0.0415(4) Uani 1 1 d . . .
H11 H 0.3321 0.6297 0.3035 0.050 Uiso 1 1 calc R . .
C12 C 0.13720(15) 0.56653(15) 0.20613(18) 0.0541(5) Uani 1 1 d . . .
H12 H 0.0843 0.6296 0.2110 0.065 Uiso 1 1 calc R . .
C13 C 0.06808(12) 0.47583(13) 0.14436(11) 0.0329(3) Uani 1 1 d . . .
H13 H -0.0320 0.4770 0.1058 0.039 Uiso 1 1 calc R . .
C14 C 0.14340(12) 0.38335(11) 0.13818(10) 0.0268(2) Uani 1 1 d . . .
H14 H 0.0955 0.3207 0.0957 0.032 Uiso 1 1 calc R . .
C15 C 0.28955(11) 0.38202(9) 0.19426(10) 0.02243(19) Uani 1 1 d . . .
H15 H 0.3419 0.3181 0.1910 0.027 Uiso 1 1 calc R . .
C16 C 0.71173(12) 0.57549(10) 0.10928(10) 0.0248(2) Uani 1 1 d . . .
H16B H 0.6968 0.6165 0.0376 0.037 Uiso 1 1 calc R . .
H16A H 0.7383 0.4993 0.1005 0.037 Uiso 1 1 calc R . .
H16C H 0.7876 0.6105 0.1741 0.037 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 0.01742(12) 0.02609(13) 0.01764(11) 0.00690(8) 0.00657(8) 0.00485(8)
O1 0.0179(3) 0.0363(4) 0.0312(4) 0.0158(3) 0.0124(3) 0.0027(3)
N1 0.0115(3) 0.0195(3) 0.0175(3) 0.0028(3) 0.0054(3) 0.0005(3)
N2 0.0133(3) 0.0167(3) 0.0149(3) 0.0014(2) 0.0055(3) 0.0003(2)
N3 0.0150(3) 0.0202(4) 0.0203(4) 0.0058(3) 0.0060(3) 0.0022(3)
C1 0.0138(3) 0.0157(4) 0.0148(3) 0.0003(3) 0.0056(3) 0.0002(3)
C2 0.0130(3) 0.0170(4) 0.0174(4) 0.0020(3) 0.0064(3) 0.0000(3)
C3 0.0141(4) 0.0207(4) 0.0210(4) 0.0052(3) 0.0070(3) 0.0014(3)
C4 0.0140(4) 0.0205(4) 0.0186(4) 0.0049(3) 0.0069(3) 0.0014(3)
C5 0.0136(3) 0.0160(4) 0.0160(3) 0.0020(3) 0.0056(3) 0.0002(3)
C6 0.0151(4) 0.0193(4) 0.0166(4) 0.0019(3) 0.0066(3) -0.0003(3)
C7 0.0164(4) 0.0215(4) 0.0208(4) 0.0005(3) 0.0093(3) -0.0006(3)
C8 0.0144(4) 0.0206(4) 0.0251(4) 0.0012(3) 0.0074(3) 0.0013(3)
C9 0.0152(4) 0.0208(4) 0.0235(4) 0.0060(3) 0.0057(3) 0.0027(3)
C10 0.0120(3) 0.0194(4) 0.0174(4) -0.0004(3) 0.0054(3) 0.0012(3)
C11 0.0209(5) 0.0311(6) 0.0562(9) -0.0206(6) -0.0045(5) 0.0093(4)
C12 0.0213(6) 0.0515(9) 0.0702(11) -0.0319(8) -0.0054(6) 0.0175(6)
C13 0.0137(4) 0.0504(8) 0.0310(6) -0.0096(5) 0.0042(4) 0.0043(4)
C14 0.0176(4) 0.0322(5) 0.0263(5) -0.0012(4) 0.0031(4) -0.0049(4)
C15 0.0170(4) 0.0210(4) 0.0255(5) -0.0023(3) 0.0035(3) -0.0004(3)
C16 0.0226(5) 0.0306(5) 0.0250(5) 0.0087(4) 0.0132(4) 0.0033(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7242(9) . yes
S1 C16 1.7989(11) . yes
O1 C3 1.2159(12) . ?
N1 C3 1.3943(12) . ?
N1 C1 1.3954(12) . ?
N1 C10 1.4279(12) . ?
N2 C1 1.3017(11) . ?
N2 C2 1.3986(12) . ?
N3 C9 1.3385(13) . ?
N3 C5 1.3572(12) . ?
C2 C4 1.3506(13) . ?
C2 C3 1.4914(13) . ?
C4 C5 1.4561(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.3999(13) . ?
C6 C7 1.3866(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.3881(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.3882(15) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.3766(15) . ?
C10 C15 1.3832(14) . ?
C11 C12 1.3955(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3764(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3876(15) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16B 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16C 0.9800 . ?
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_3
_geom_angle_publ_flag
C1 S1 C16 98.71(5) . . yes
C3 N1 C1 107.04(8) . . ?
C3 N1 C10 124.29(8) . . ?
C1 N1 C10 125.89(8) . . ?
C1 N2 C2 105.10(8) . . ?
C9 N3 C5 117.21(9) . . ?
N2 C1 N1 115.11(8) . . ?
N2 C1 S1 126.74(7) . . ?
N1 C1 S1 118.15(7) . . ?
C4 C2 N2 128.83(9) . . ?
C4 C2 C3 121.53(8) . . ?
N2 C2 C3 109.61(8) . . ?
O1 C3 N1 125.92(9) . . ?
O1 C3 C2 131.00(9) . . ?
N1 C3 C2 103.05(8) . . ?
C2 C4 C5 129.75(9) . . ?
C2 C4 H4 115.1 . . ?
C5 C4 H4 115.1 . . ?
N3 C5 C6 122.48(8) . . ?
N3 C5 C4 113.98(8) . . ?
C6 C5 C4 123.51(8) . . ?
C7 C6 C5 118.91(9) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 118.96(9) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 118.46(9) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
N3 C9 C8 123.98(9) . . ?
N3 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
C11 C10 C15 120.73(10) . . ?
C11 C10 N1 121.22(9) . . ?
C15 C10 N1 118.04(9) . . ?
C10 C11 C12 118.84(12) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.60(12) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.19(11) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 119.76(11) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 119.86(10) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
S1 C16 H16B 109.5 . . ?
S1 C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
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
C2 N2 C1 N1 1.24(11) . . . . ?
C2 N2 C1 S1 -179.14(7) . . . . ?
C3 N1 C1 N2 -2.88(12) . . . . ?
C10 N1 C1 N2 -164.53(9) . . . . ?
C3 N1 C1 S1 177.46(7) . . . . ?
C10 N1 C1 S1 15.81(13) . . . . ?
C16 S1 C1 N2 5.97(10) . . . . ?
C16 S1 C1 N1 -174.41(8) . . . . ?
C1 N2 C2 C4 178.76(10) . . . . ?
C1 N2 C2 C3 0.80(10) . . . . ?
C1 N1 C3 O1 -175.16(11) . . . . ?
C10 N1 C3 O1 -13.14(17) . . . . ?
C1 N1 C3 C2 2.97(10) . . . . ?
C10 N1 C3 C2 164.99(9) . . . . ?
C4 C2 C3 O1 -2.55(18) . . . . ?
N2 C2 C3 O1 175.58(12) . . . . ?
C4 C2 C3 N1 179.45(9) . . . . ?
N2 C2 C3 N1 -2.41(11) . . . . ?
N2 C2 C4 C5 -2.30(18) . . . . ?
C3 C2 C4 C5 175.45(10) . . . . ?
C9 N3 C5 C6 -0.04(15) . . . . ?
C9 N3 C5 C4 177.94(9) . . . . ?
C2 C4 C5 N3 -178.60(10) . . . . ?
C2 C4 C5 C6 -0.64(17) . . . . ?
N3 C5 C6 C7 0.48(15) . . . . ?
C4 C5 C6 C7 -177.31(9) . . . . ?
C5 C6 C7 C8 -0.35(15) . . . . ?
C6 C7 C8 C9 -0.17(15) . . . . ?
C5 N3 C9 C8 -0.53(16) . . . . ?
C7 C8 C9 N3 0.64(17) . . . . ?
C3 N1 C10 C11 109.96(15) . . . . ?
C1 N1 C10 C11 -91.41(15) . . . . ?
C3 N1 C10 C15 -68.73(13) . . . . ?
C1 N1 C10 C15 89.90(12) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
N1 C10 C11 C12 -178.79(16) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C11 C10 C15 C14 0.92(19) . . . . ?
N1 C10 C15 C14 179.62(10) . . . . ?
C13 C14 C15 C10 -0.76(19) . . . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.579
_refine_diff_density_min -0.716
_refine_diff_density_rms 0.063
# File processed with modiCIFer (v.3-27-2007). I.A.Guzei, UW-Madison.
# Attachment '- Form_III.cif'
data_schomaker03a
_database_code_depnum_ccdc_archive 'CCDC 809205'
#TrackingRef '- Form_III.cif'
_chemical_name_systematic ?
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H13 N3 O S'
_chemical_formula_sum 'C16 H13 N3 O S'
_chemical_formula_weight 295.35
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P b c a '
_symmetry_space_group_name_Hall '-P 2ac 2ab '
_symmetry_int_tables_number 61
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'
_cell_length_a 17.0269(4)
_cell_length_b 23.4679(6)
_cell_length_c 6.9207(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2765.41(12)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 9892
_cell_measurement_theta_min 3.7670
_cell_measurement_theta_max 71.3085
_exptl_crystal_description needle
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.49
_exptl_crystal_size_mid 0.29
_exptl_crystal_size_min 0.09
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.419
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1232
_exptl_absorpt_coefficient_mu 2.094
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
SADABS (Bruker-AXS, 2007)
;
_exptl_absorpt_correction_T_min 0.4268
_exptl_absorpt_correction_T_max 0.8339
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 1.54178
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker SMART APEX2 area detector'
_diffrn_measurement_method '0.50\% \w and 0.5 \% \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 38391
_diffrn_reflns_av_R_equivalents 0.0250
_diffrn_reflns_av_sigmaI/netI 0.0098
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_k_min -28
_diffrn_reflns_limit_k_max 27
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_theta_min 3.77
_diffrn_reflns_theta_max 71.85
_reflns_number_total 2682
_reflns_number_gt 2571
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX2 Ver. 2.1-4 (Bruker-AXS, 2007)'
_computing_cell_refinement 'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_reduction 'SAINT Ver. 7.24A'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material SHELXTL
_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^)+(0.0611P)^2^+0.9749P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2682
_refine_ls_number_parameters 191
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0318
_refine_ls_R_factor_gt 0.0308
_refine_ls_wR_factor_ref 0.0892
_refine_ls_wR_factor_gt 0.0880
_refine_ls_goodness_of_fit_ref 1.022
_refine_ls_restrained_S_all 1.022
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
S1 S 0.239510(18) 0.420757(12) 0.19908(4) 0.01707(12) Uani 1 1 d . . .
O1 O 0.49575(5) 0.52343(4) 0.23689(13) 0.0210(2) Uani 1 1 d . . .
N1 N 0.38557(6) 0.46473(4) 0.21477(14) 0.0159(2) Uani 1 1 d . . .
N2 N 0.28766(6) 0.53073(4) 0.20329(13) 0.0151(2) Uani 1 1 d . . .
N3 N 0.35388(6) 0.71501(4) 0.23093(15) 0.0182(2) Uani 1 1 d . . .
C1 C 0.30525(7) 0.47667(5) 0.20454(15) 0.0146(2) Uani 1 1 d . . .
C2 C 0.35996(7) 0.55928(5) 0.21319(15) 0.0152(2) Uani 1 1 d . . .
C3 C 0.42533(7) 0.51684(5) 0.22331(16) 0.0165(3) Uani 1 1 d . . .
C4 C 0.37441(7) 0.61574(5) 0.21480(16) 0.0165(3) Uani 1 1 d . . .
H4 H 0.4283 0.6260 0.2230 0.020 Uiso 1 1 calc R . .
C5 C 0.31959(7) 0.66341(5) 0.20586(15) 0.0160(3) Uani 1 1 d . . .
C6 C 0.23911(7) 0.65726(5) 0.17088(18) 0.0181(3) Uani 1 1 d . . .
H6 H 0.2166 0.6206 0.1541 0.022 Uiso 1 1 calc R . .
C7 C 0.19299(7) 0.70579(5) 0.16117(18) 0.0198(3) Uani 1 1 d . . .
H7 H 0.1383 0.7028 0.1360 0.024 Uiso 1 1 calc R . .
C8 C 0.22740(8) 0.75868(6) 0.18850(17) 0.0204(3) Uani 1 1 d . . .
H8 H 0.1969 0.7925 0.1836 0.024 Uiso 1 1 calc R . .
C9 C 0.30759(8) 0.76092(5) 0.22326(17) 0.0203(3) Uani 1 1 d . . .
H9 H 0.3310 0.7972 0.2428 0.024 Uiso 1 1 calc R . .
C10 C 0.42188(7) 0.40967(5) 0.21308(17) 0.0158(3) Uani 1 1 d . . .
C11 C 0.42067(7) 0.37787(5) 0.04392(17) 0.0198(3) Uani 1 1 d . . .
H11 H 0.3950 0.3920 -0.0681 0.024 Uiso 1 1 calc R . .
C12 C 0.45758(7) 0.32502(5) 0.04094(19) 0.0226(3) Uani 1 1 d . . .
H12 H 0.4564 0.3026 -0.0732 0.027 Uiso 1 1 calc R . .
C13 C 0.49600(7) 0.30499(5) 0.20360(19) 0.0221(3) Uani 1 1 d . . .
H13 H 0.5219 0.2692 0.2000 0.026 Uiso 1 1 calc R . .
C14 C 0.49679(7) 0.33711(5) 0.37164(19) 0.0233(3) Uani 1 1 d . . .
H14 H 0.5231 0.3231 0.4830 0.028 Uiso 1 1 calc R . .
C15 C 0.45914(7) 0.38988(5) 0.37811(18) 0.0194(3) Uani 1 1 d . . .
H15 H 0.4590 0.4118 0.4934 0.023 Uiso 1 1 calc R . .
C16 C 0.14957(7) 0.46102(5) 0.20986(17) 0.0200(3) Uani 1 1 d . . .
H16A H 0.1496 0.4848 0.3262 0.030 Uiso 1 1 calc R . .
H16B H 0.1048 0.4348 0.2141 0.030 Uiso 1 1 calc R . .
H16C H 0.1454 0.4853 0.0952 0.030 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 0.01405(18) 0.01220(18) 0.02498(19) -0.00006(10) -0.00094(10) -0.00141(10)
O1 0.0140(4) 0.0171(5) 0.0318(5) -0.0004(3) -0.0012(3) -0.0003(3)
N1 0.0136(5) 0.0120(5) 0.0221(5) -0.0007(3) -0.0005(4) 0.0004(4)
N2 0.0150(5) 0.0127(5) 0.0177(5) 0.0001(3) -0.0004(3) -0.0003(4)
N3 0.0187(5) 0.0134(5) 0.0225(5) -0.0006(4) -0.0004(4) -0.0005(4)
C1 0.0134(6) 0.0141(6) 0.0162(6) 0.0000(4) -0.0003(4) -0.0005(4)
C2 0.0146(6) 0.0150(6) 0.0161(5) -0.0005(4) 0.0002(4) 0.0009(5)
C3 0.0174(6) 0.0137(6) 0.0184(5) -0.0003(4) 0.0001(4) -0.0001(4)
C4 0.0147(6) 0.0160(6) 0.0189(6) -0.0006(4) -0.0001(4) -0.0008(5)
C5 0.0185(6) 0.0141(6) 0.0153(6) -0.0003(4) 0.0015(4) -0.0006(5)
C6 0.0180(6) 0.0162(6) 0.0200(6) -0.0010(5) 0.0004(4) -0.0013(4)
C7 0.0179(6) 0.0204(6) 0.0212(6) -0.0006(5) -0.0007(5) 0.0020(5)
C8 0.0236(7) 0.0158(6) 0.0217(6) 0.0002(4) -0.0003(5) 0.0047(5)
C9 0.0241(6) 0.0128(6) 0.0239(6) -0.0010(4) -0.0001(5) 0.0005(5)
C10 0.0116(6) 0.0114(6) 0.0244(6) 0.0012(4) 0.0021(4) -0.0007(4)
C11 0.0198(6) 0.0174(6) 0.0221(6) 0.0009(5) 0.0009(5) 0.0011(4)
C12 0.0223(6) 0.0170(6) 0.0286(6) -0.0037(5) 0.0046(5) 0.0002(4)
C13 0.0150(6) 0.0115(6) 0.0397(7) 0.0026(5) 0.0033(5) 0.0010(5)
C14 0.0187(6) 0.0193(6) 0.0318(7) 0.0074(5) -0.0054(5) -0.0006(5)
C15 0.0190(6) 0.0162(6) 0.0230(6) 0.0008(5) -0.0014(5) -0.0021(4)
C16 0.0136(6) 0.0207(6) 0.0258(6) -0.0019(4) -0.0008(4) 0.0010(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7252(12) . yes
S1 C16 1.8009(13) . yes
O1 C3 1.2126(15) . ?
N1 C1 1.3978(15) . ?
N1 C3 1.3991(15) . ?
N1 C10 1.4324(15) . ?
N2 C1 1.3035(15) . ?
N2 C2 1.4033(15) . ?
N3 C9 1.3359(16) . ?
N3 C5 1.3555(15) . ?
C2 C4 1.3478(17) . ?
C2 C3 1.4953(16) . ?
C4 C5 1.4582(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3991(17) . ?
C6 C7 1.3851(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3855(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3875(19) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.3885(16) . ?
C10 C15 1.3866(17) . ?
C11 C12 1.3906(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3843(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3858(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3953(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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_3
_geom_angle_publ_flag
C1 S1 C16 98.73(6) . . yes
C1 N1 C3 107.48(9) . . ?
C1 N1 C10 127.07(10) . . ?
C3 N1 C10 125.44(10) . . ?
C1 N2 C2 105.23(10) . . ?
C9 N3 C5 117.47(11) . . ?
N2 C1 N1 114.86(10) . . ?
N2 C1 S1 126.23(10) . . ?
N1 C1 S1 118.91(9) . . ?
C4 C2 N2 129.05(11) . . ?
C4 C2 C3 121.24(11) . . ?
N2 C2 C3 109.71(10) . . ?
O1 C3 N1 126.39(11) . . ?
O1 C3 C2 130.90(11) . . ?
N1 C3 C2 102.71(9) . . ?
C2 C4 C5 129.57(11) . . ?
C2 C4 H4 115.2 . . ?
C5 C4 H4 115.2 . . ?
N3 C5 C6 122.42(11) . . ?
N3 C5 C4 113.84(11) . . ?
C6 C5 C4 123.72(11) . . ?
C7 C6 C5 118.61(12) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C6 119.37(11) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 118.27(11) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
N3 C9 C8 123.85(11) . . ?
N3 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C11 C10 C15 121.42(11) . . ?
C11 C10 N1 119.03(10) . . ?
C15 C10 N1 119.53(10) . . ?
C10 C11 C12 119.02(11) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 120.29(11) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.16(11) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.34(11) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 118.76(11) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
C2 N2 C1 N1 0.02(12) . . . . ?
C2 N2 C1 S1 178.83(8) . . . . ?
C3 N1 C1 N2 0.70(13) . . . . ?
C10 N1 C1 N2 -178.14(10) . . . . ?
C3 N1 C1 S1 -178.20(8) . . . . ?
C10 N1 C1 S1 2.95(15) . . . . ?
C16 S1 C1 N2 -3.99(11) . . . . ?
C16 S1 C1 N1 174.78(9) . . . . ?
C1 N2 C2 C4 179.49(11) . . . . ?
C1 N2 C2 C3 -0.70(11) . . . . ?
C1 N1 C3 O1 178.55(11) . . . . ?
C10 N1 C3 O1 -2.59(18) . . . . ?
C1 N1 C3 C2 -1.02(11) . . . . ?
C10 N1 C3 C2 177.85(10) . . . . ?
C4 C2 C3 O1 1.37(19) . . . . ?
N2 C2 C3 O1 -178.46(12) . . . . ?
C4 C2 C3 N1 -179.09(10) . . . . ?
N2 C2 C3 N1 1.08(11) . . . . ?
N2 C2 C4 C5 -0.33(19) . . . . ?
C3 C2 C4 C5 179.88(10) . . . . ?
C9 N3 C5 C6 0.72(17) . . . . ?
C9 N3 C5 C4 179.51(10) . . . . ?
C2 C4 C5 N3 173.49(11) . . . . ?
C2 C4 C5 C6 -7.74(19) . . . . ?
N3 C5 C6 C7 0.15(18) . . . . ?
C4 C5 C6 C7 -178.52(11) . . . . ?
C5 C6 C7 C8 -0.77(18) . . . . ?
C6 C7 C8 C9 0.52(18) . . . . ?
C5 N3 C9 C8 -1.01(18) . . . . ?
C7 C8 C9 N3 0.40(19) . . . . ?
C1 N1 C10 C11 69.70(15) . . . . ?
C3 N1 C10 C11 -108.94(13) . . . . ?
C1 N1 C10 C15 -111.94(13) . . . . ?
C3 N1 C10 C15 69.42(15) . . . . ?
C15 C10 C11 C12 0.13(17) . . . . ?
N1 C10 C11 C12 178.46(10) . . . . ?
C10 C11 C12 C13 -1.06(18) . . . . ?
C11 C12 C13 C14 1.09(18) . . . . ?
C12 C13 C14 C15 -0.20(18) . . . . ?
C11 C10 C15 C14 0.75(17) . . . . ?
N1 C10 C15 C14 -177.57(10) . . . . ?
C13 C14 C15 C10 -0.71(17) . . . . ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 67.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.279
_refine_diff_density_min -0.410
_refine_diff_density_rms 0.086
# File processed with modiCIFer (v.3-27-2007). I.A.Guzei, UW-Madison.