data_anass3m
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
#------------------------------------------------------------------------------
_publ_requested_journal ' ENTER JOURNAL NAME HERE'
_publ_contact_author
;
Madeleine Helliwell
;
_publ_contact_letter
;
ENTER TEXT OF LETTER
;
_publ_requested_coeditor_name ?
_publ_contact_author_phone ' ENTER PHONE NUMBER '
_publ_contact_author_fax ' ENTER FAX NUMBER '
_publ_contact_author_email ' ENTER EMAIL ADDRESS '
loop_
_publ_author_name
_publ_author_address
' FIRST AUTHORS NAME '
;
FIRST AUTHORS ADDRESS
;
_publ_section_title
;
ENTER SECTION TITLE
;
_publ_section_abstract
;
ENTER ABSTRACT
;
_publ_section_exptl_prep
;
ENTER EXPERIMENTAL SECTION
;
_publ_section_exptl_refinement
;
The structure was solved by the direct methods.
All non-H atoms were refined anisotropically.
H atoms bonded to C were included in calculated positions;
those bonded to N were found by difference Fourier methods
and refined isotropically.
;
_publ_section_comment
;
ENTER TEXT
;
_publ_section_references
;
Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and
SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison,
Wisconsin, USA.
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini,
G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori
and R. Spagna
SIR2004: an improved tool for crystal structure determination
and refinement
J. Appl. Cryst. (2005). 38, 381-388
Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97.
University of G\"ottingen, Germany.
Sheldrick, G, M. (2005). CELL_NOW. University
of G\"ottingen, Germany.
Sheldrick, G, M. (2007). TWINABS. University
of G\"ottingen, Germany.
Spek, A.L. (2003) J.Appl.Cryst. 36, 2003, 7-13.
;
_publ_section_acknowledgements
;
ENTER ACKNOWLEDGEMENTS
;
_publ_section_table_legends
;
ENTER TABLE LEGENDS
;
_publ_section_figure_captions
;
ENTER FIGURE CAPTIONS
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H13 N S2'
_chemical_formula_sum
'C16 H13 N S2'
_chemical_formula_weight 283.39
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'
'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 P2(1)/n
_symmetry_space_group_name_Hall -P2yn
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 9.5616(17)
_cell_length_b 9.1731(16)
_cell_length_c 15.889(3)
_cell_angle_alpha 90.00
_cell_angle_beta 92.058(3)
_cell_angle_gamma 90.00
_cell_volume 1392.7(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 915
_cell_measurement_theta_min 2.45
_cell_measurement_theta_max 26.36
_exptl_crystal_description prismatic
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.35
_exptl_crystal_size_min 0.30
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.352
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 592
_exptl_absorpt_coefficient_mu 0.366
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 10816
_diffrn_reflns_av_R_equivalents 0.0378
_diffrn_reflns_av_sigmaI/netI 0.0289
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.45
_diffrn_reflns_theta_max 26.44
_reflns_number_total 2859
_reflns_number_gt 2616
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker 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^)+(0.0441P)^2^+0.3687P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2859
_refine_ls_number_parameters 176
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0351
_refine_ls_R_factor_gt 0.0313
_refine_ls_wR_factor_ref 0.0805
_refine_ls_wR_factor_gt 0.0786
_refine_ls_goodness_of_fit_ref 1.044
_refine_ls_restrained_S_all 1.044
_refine_ls_shift/su_max 0.002
_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 0.69515(4) 0.68521(4) 1.14748(2) 0.01774(11) Uani 1 1 d . . .
S2 S 0.96911(4) 0.55263(4) 1.12932(2) 0.01869(11) Uani 1 1 d . . .
N1 N 0.78932(12) 0.59997(13) 1.00010(7) 0.0160(3) Uani 1 1 d . . .
H1N H 0.853(2) 0.5610(18) 0.9693(11) 0.024(5) Uiso 1 1 d . . .
C1 C 0.81952(14) 0.61174(15) 1.08305(9) 0.0159(3) Uani 1 1 d . . .
C2 C 0.59810(14) 0.80371(15) 1.07228(9) 0.0176(3) Uani 1 1 d . . .
H2 H 0.5070 0.8288 1.0976 0.021 Uiso 1 1 calc R . .
C3 C 0.56599(15) 0.71901(16) 0.99371(9) 0.0173(3) Uani 1 1 d . . .
H3 H 0.4757 0.7286 0.9673 0.021 Uiso 1 1 calc R . .
C4 C 0.65844(14) 0.63022(15) 0.95882(9) 0.0162(3) Uani 1 1 d . . .
C5 C 0.67803(14) 0.94509(15) 1.06082(9) 0.0167(3) Uani 1 1 d . . .
C6 C 0.74668(16) 0.97603(16) 0.98698(9) 0.0213(3) Uani 1 1 d . . .
H6 H 0.7398 0.9100 0.9410 0.026 Uiso 1 1 calc R . .
C7 C 0.82495(17) 1.10251(17) 0.98021(10) 0.0244(3) Uani 1 1 d . . .
H7 H 0.8723 1.1220 0.9299 0.029 Uiso 1 1 calc R . .
C8 C 0.83443(15) 1.20059(16) 1.04652(9) 0.0209(3) Uani 1 1 d . . .
H8 H 0.8886 1.2869 1.0419 0.025 Uiso 1 1 calc R . .
C9 C 0.76444(16) 1.17206(16) 1.11971(9) 0.0206(3) Uani 1 1 d . . .
H9 H 0.7693 1.2398 1.1650 0.025 Uiso 1 1 calc R . .
C10 C 0.68749(15) 1.04519(16) 1.12699(9) 0.0192(3) Uani 1 1 d . . .
H10 H 0.6406 1.0260 1.1775 0.023 Uiso 1 1 calc R . .
C11 C 0.63404(14) 0.55695(15) 0.87658(9) 0.0166(3) Uani 1 1 d . . .
C12 C 0.55876(15) 0.62852(16) 0.81139(9) 0.0192(3) Uani 1 1 d . . .
H12 H 0.5263 0.7252 0.8196 0.023 Uiso 1 1 calc R . .
C13 C 0.53136(15) 0.55930(17) 0.73513(9) 0.0227(3) Uani 1 1 d . . .
H13 H 0.4784 0.6077 0.6918 0.027 Uiso 1 1 calc R . .
C14 C 0.58121(15) 0.41925(18) 0.72184(9) 0.0230(3) Uani 1 1 d . . .
H14 H 0.5628 0.3722 0.6693 0.028 Uiso 1 1 calc R . .
C15 C 0.65784(15) 0.34805(17) 0.78524(9) 0.0210(3) Uani 1 1 d . . .
H15 H 0.6933 0.2529 0.7759 0.025 Uiso 1 1 calc R . .
C16 C 0.68264(14) 0.41601(16) 0.86235(9) 0.0177(3) Uani 1 1 d . . .
H16 H 0.7333 0.3659 0.9060 0.021 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 0.0178(2) 0.0194(2) 0.01627(19) 0.00174(13) 0.00341(14) 0.00180(13)
S2 0.01534(19) 0.0232(2) 0.01726(19) -0.00267(14) -0.00263(14) 0.00208(13)
N1 0.0116(6) 0.0197(6) 0.0165(6) -0.0024(5) 0.0007(5) 0.0003(5)
C1 0.0145(7) 0.0137(7) 0.0194(7) 0.0001(5) 0.0016(5) -0.0029(5)
C2 0.0133(7) 0.0193(7) 0.0202(7) 0.0021(6) 0.0024(6) 0.0032(5)
C3 0.0131(7) 0.0187(7) 0.0201(7) 0.0020(6) -0.0006(5) -0.0010(5)
C4 0.0137(7) 0.0163(7) 0.0185(7) 0.0034(5) -0.0015(5) -0.0029(5)
C5 0.0134(7) 0.0178(7) 0.0189(7) 0.0017(5) -0.0006(5) 0.0036(5)
C6 0.0263(8) 0.0185(7) 0.0194(7) -0.0026(6) 0.0045(6) -0.0002(6)
C7 0.0285(9) 0.0221(8) 0.0230(8) 0.0022(6) 0.0071(6) -0.0002(6)
C8 0.0190(7) 0.0177(7) 0.0258(8) 0.0023(6) -0.0038(6) -0.0007(6)
C9 0.0223(8) 0.0202(7) 0.0188(7) -0.0019(6) -0.0061(6) 0.0037(6)
C10 0.0187(7) 0.0229(8) 0.0158(7) 0.0015(6) 0.0002(6) 0.0049(6)
C11 0.0114(7) 0.0211(7) 0.0174(7) 0.0016(6) 0.0009(5) -0.0040(5)
C12 0.0144(7) 0.0222(8) 0.0211(7) 0.0046(6) 0.0015(6) -0.0015(6)
C13 0.0155(7) 0.0354(9) 0.0172(7) 0.0071(6) -0.0005(6) -0.0020(6)
C14 0.0160(7) 0.0367(9) 0.0164(7) -0.0043(6) 0.0018(6) -0.0056(6)
C15 0.0141(7) 0.0253(8) 0.0237(8) -0.0045(6) 0.0032(6) -0.0029(6)
C16 0.0130(7) 0.0209(7) 0.0190(7) 0.0001(6) -0.0003(5) -0.0016(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 1.7332(14) . ?
S1 C2 1.8414(14) . ?
S2 C1 1.6748(14) . ?
N1 C1 1.3434(18) . ?
N1 C4 1.4193(18) . ?
N1 H1N 0.875(19) . ?
C2 C3 1.493(2) . ?
C2 C5 1.520(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.337(2) . ?
C3 H3 0.9500 . ?
C4 C11 1.480(2) . ?
C5 C6 1.394(2) . ?
C5 C10 1.396(2) . ?
C6 C7 1.387(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.395(2) . ?
C11 C12 1.403(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
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 C2 100.76(7) . . ?
C1 N1 C4 126.34(12) . . ?
C1 N1 H1N 116.9(12) . . ?
C4 N1 H1N 116.4(12) . . ?
N1 C1 S2 123.69(11) . . ?
N1 C1 S1 118.87(11) . . ?
S2 C1 S1 117.38(8) . . ?
C3 C2 C5 115.68(12) . . ?
C3 C2 S1 108.61(10) . . ?
C5 C2 S1 109.73(9) . . ?
C3 C2 H2 107.5 . . ?
C5 C2 H2 107.5 . . ?
S1 C2 H2 107.5 . . ?
C4 C3 C2 123.00(13) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C3 C4 N1 120.84(13) . . ?
C3 C4 C11 123.85(13) . . ?
N1 C4 C11 115.31(12) . . ?
C6 C5 C10 118.69(14) . . ?
C6 C5 C2 121.91(13) . . ?
C10 C5 C2 119.36(13) . . ?
C7 C6 C5 120.48(14) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.32(14) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.63(14) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 120.17(14) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C5 120.69(14) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C16 C11 C12 118.63(13) . . ?
C16 C11 C4 121.39(13) . . ?
C12 C11 C4 119.97(13) . . ?
C13 C12 C11 120.49(14) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.13(14) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.01(14) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.91(15) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.80(14) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
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
C4 N1 C1 S2 171.26(11) . . . . ?
C4 N1 C1 S1 -6.0(2) . . . . ?
C2 S1 C1 N1 -27.24(12) . . . . ?
C2 S1 C1 S2 155.32(8) . . . . ?
C1 S1 C2 C3 47.34(11) . . . . ?
C1 S1 C2 C5 -79.99(10) . . . . ?
C5 C2 C3 C4 81.74(17) . . . . ?
S1 C2 C3 C4 -42.12(17) . . . . ?
C2 C3 C4 N1 6.6(2) . . . . ?
C2 C3 C4 C11 -173.55(13) . . . . ?
C1 N1 C4 C3 22.8(2) . . . . ?
C1 N1 C4 C11 -157.05(13) . . . . ?
C3 C2 C5 C6 -15.31(19) . . . . ?
S1 C2 C5 C6 107.96(14) . . . . ?
C3 C2 C5 C10 166.94(13) . . . . ?
S1 C2 C5 C10 -69.79(15) . . . . ?
C10 C5 C6 C7 1.2(2) . . . . ?
C2 C5 C6 C7 -176.53(14) . . . . ?
C5 C6 C7 C8 -0.8(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C10 1.1(2) . . . . ?
C8 C9 C10 C5 -0.6(2) . . . . ?
C6 C5 C10 C9 -0.5(2) . . . . ?
C2 C5 C10 C9 177.29(13) . . . . ?
C3 C4 C11 C16 -143.61(15) . . . . ?
N1 C4 C11 C16 36.24(18) . . . . ?
C3 C4 C11 C12 35.4(2) . . . . ?
N1 C4 C11 C12 -144.76(13) . . . . ?
C16 C11 C12 C13 1.1(2) . . . . ?
C4 C11 C12 C13 -177.89(13) . . . . ?
C11 C12 C13 C14 -1.5(2) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C14 C15 C16 C11 -1.4(2) . . . . ?
C12 C11 C16 C15 0.3(2) . . . . ?
C4 C11 C16 C15 179.35(13) . . . . ?
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
N1 H1N S2 0.875(19) 2.571(19) 3.4444(13) 176.4(15) 3_767
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 26.44
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 0.353
_refine_diff_density_min -0.176
_refine_diff_density_rms 0.052