# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2014
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-(2-Ethyl-1,1-dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(3-nitro-benzylidene)-hydrazine
;
_chemical_name_common
;
N-(2-Ethyl-1,1-dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(3-nitro-benzylidene)-hydrazine
;
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H16 N4 O4 S'
_chemical_formula_sum 'C17 H16 N4 O4 S'
_chemical_formula_weight 372.40
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 monoclinic
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 10.6782(2)
_cell_length_b 8.32550(10)
_cell_length_c 20.3120(5)
_cell_angle_alpha 90.00
_cell_angle_beta 105.218(3)
_cell_angle_gamma 90.00
_cell_volume 1742.44(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 4869
_cell_measurement_theta_min 4.2873
_cell_measurement_theta_max 76.3791
_exptl_crystal_description prismatic
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.27
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.14
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.420
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 776
_exptl_absorpt_coefficient_mu 1.932
_exptl_absorpt_correction_T_min 0.70148
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 7916
_diffrn_reflns_av_R_equivalents 0.0152
_diffrn_reflns_av_sigmaI/netI 0.0161
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 4.29
_diffrn_reflns_theta_max 76.57
_reflns_number_total 3521
_reflns_number_gt 3196
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0616P)^2^+0.2957P] 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 3521
_refine_ls_number_parameters 236
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0397
_refine_ls_R_factor_gt 0.0366
_refine_ls_wR_factor_ref 0.1048
_refine_ls_wR_factor_gt 0.1008
_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
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 0.28445(3) 0.44636(4) 0.375726(19) 0.04468(13) Uani 1 1 d . . .
O1 O 0.21580(11) 0.56112(12) 0.32725(7) 0.0650(4) Uani 1 1 d . . .
O2 O 0.25975(13) 0.43880(14) 0.44158(7) 0.0651(3) Uani 1 1 d . . .
O3 O 1.12745(16) -0.3507(2) 0.61734(10) 0.1003(6) Uani 1 1 d . . .
O4 O 1.27780(11) -0.1926(2) 0.67017(7) 0.0786(4) Uani 1 1 d . . .
N1 N 0.43972(11) 0.47158(14) 0.38759(7) 0.0470(3) Uani 1 1 d . . .
N2 N 0.55773(11) 0.05790(14) 0.43318(6) 0.0448(3) Uani 1 1 d . . .
N3 N 0.67564(11) 0.10827(16) 0.47692(7) 0.0491(3) Uani 1 1 d . . .
N4 N 1.16849(13) -0.2173(2) 0.63480(7) 0.0610(4) Uani 1 1 d . . .
C1 C 0.25899(12) 0.25345(14) 0.33932(6) 0.0362(3) Uani 1 1 d . . .
C2 C 0.14339(13) 0.21907(16) 0.29173(7) 0.0423(3) Uani 1 1 d . . .
H2 H 0.0819 0.2993 0.2767 0.051 Uiso 1 1 calc R . .
C3 C 0.12010(14) 0.06456(17) 0.26674(7) 0.0461(3) Uani 1 1 d . . .
H3 H 0.0430 0.0404 0.2344 0.055 Uiso 1 1 calc R . .
C4 C 0.21135(15) -0.05350(16) 0.28979(7) 0.0474(3) Uani 1 1 d . . .
H4 H 0.1941 -0.1582 0.2741 0.057 Uiso 1 1 calc R . .
C5 C 0.32823(14) -0.01840(16) 0.33595(7) 0.0433(3) Uani 1 1 d . . .
H5 H 0.3895 -0.0993 0.3501 0.052 Uiso 1 1 calc R . .
C6 C 0.35573(12) 0.13728(15) 0.36167(6) 0.0351(3) Uani 1 1 d . . .
C7 C 0.48144(12) 0.17605(15) 0.41051(6) 0.0374(3) Uani 1 1 d . . .
C8 C 0.51496(15) 0.34816(17) 0.43333(8) 0.0524(4) Uani 1 1 d . . .
H8A H 0.5012 0.3621 0.4783 0.063 Uiso 1 1 calc R . .
H8B H 0.6065 0.3657 0.4373 0.063 Uiso 1 1 calc R . .
C9 C 0.74717(13) -0.00860(17) 0.50380(7) 0.0411(3) Uani 1 1 d . . .
H9 H 0.7173 -0.1133 0.4948 0.049 Uiso 1 1 calc R . .
C10 C 0.87664(13) 0.02076(17) 0.54894(6) 0.0399(3) Uani 1 1 d . . .
C11 C 0.95829(13) -0.10910(19) 0.57144(7) 0.0423(3) Uani 1 1 d . . .
H11 H 0.9305 -0.2135 0.5594 0.051 Uiso 1 1 calc R . .
C12 C 1.08174(14) -0.0796(2) 0.61214(7) 0.0459(3) Uani 1 1 d . . .
C13 C 1.12729(15) 0.0721(2) 0.63120(8) 0.0546(4) Uani 1 1 d . . .
H13 H 1.2110 0.0879 0.6586 0.065 Uiso 1 1 calc R . .
C14 C 1.04546(16) 0.2010(2) 0.60863(8) 0.0571(4) Uani 1 1 d . . .
H14 H 1.0743 0.3049 0.6210 0.068 Uiso 1 1 calc R . .
C15 C 0.92117(15) 0.17635(19) 0.56789(7) 0.0490(3) Uani 1 1 d . . .
H15 H 0.8669 0.2637 0.5530 0.059 Uiso 1 1 calc R . .
C16 C 0.48628(17) 0.5074(2) 0.32655(10) 0.0619(4) Uani 1 1 d . . .
H16A H 0.4164 0.5553 0.2916 0.074 Uiso 1 1 calc R . .
H16B H 0.5113 0.4081 0.3085 0.074 Uiso 1 1 calc R . .
C17 C 0.6007(2) 0.6205(3) 0.34358(14) 0.0853(7) Uani 1 1 d . . .
H17A H 0.5777 0.7163 0.3640 0.128 Uiso 1 1 calc R . .
H17B H 0.6246 0.6480 0.3026 0.128 Uiso 1 1 calc R . .
H17C H 0.6727 0.5693 0.3750 0.128 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 0.03719(19) 0.02854(18) 0.0638(2) -0.00555(13) 0.00527(15) 0.00317(11)
O1 0.0475(6) 0.0331(5) 0.1010(10) 0.0072(5) -0.0044(6) 0.0074(4)
O2 0.0704(8) 0.0561(7) 0.0737(8) -0.0226(6) 0.0277(6) -0.0048(5)
O3 0.0799(10) 0.0657(9) 0.1323(15) 0.0181(9) -0.0132(10) 0.0224(8)
O4 0.0425(6) 0.1141(12) 0.0707(8) 0.0236(8) -0.0003(6) 0.0208(7)
N1 0.0377(6) 0.0316(5) 0.0641(8) -0.0026(5) 0.0002(5) -0.0010(4)
N2 0.0357(6) 0.0411(6) 0.0505(6) 0.0020(5) -0.0014(5) 0.0038(4)
N3 0.0362(6) 0.0467(7) 0.0555(7) 0.0030(5) -0.0037(5) 0.0041(5)
N4 0.0455(7) 0.0794(11) 0.0544(7) 0.0196(7) 0.0064(6) 0.0179(7)
C1 0.0344(6) 0.0287(6) 0.0424(6) 0.0005(5) 0.0049(5) 0.0006(5)
C2 0.0341(6) 0.0376(6) 0.0496(7) 0.0048(5) 0.0012(5) 0.0012(5)
C3 0.0424(7) 0.0438(7) 0.0442(7) 0.0000(6) -0.0027(6) -0.0084(6)
C4 0.0548(8) 0.0345(7) 0.0472(7) -0.0051(5) 0.0032(6) -0.0052(6)
C5 0.0478(7) 0.0305(6) 0.0464(7) -0.0021(5) 0.0032(6) 0.0045(5)
C6 0.0344(6) 0.0302(6) 0.0381(6) -0.0007(5) 0.0051(5) 0.0020(5)
C7 0.0334(6) 0.0350(6) 0.0409(6) 0.0003(5) 0.0045(5) 0.0027(5)
C8 0.0433(7) 0.0382(7) 0.0627(9) -0.0061(6) -0.0092(6) 0.0024(6)
C9 0.0363(6) 0.0436(7) 0.0415(7) 0.0044(5) 0.0071(5) 0.0045(5)
C10 0.0348(6) 0.0486(7) 0.0357(6) 0.0037(5) 0.0080(5) 0.0056(5)
C11 0.0374(6) 0.0493(7) 0.0391(6) 0.0064(6) 0.0081(5) 0.0048(6)
C12 0.0355(7) 0.0627(9) 0.0384(6) 0.0100(6) 0.0076(5) 0.0107(6)
C13 0.0385(7) 0.0764(11) 0.0438(7) -0.0042(7) 0.0017(6) -0.0017(7)
C14 0.0529(9) 0.0577(9) 0.0561(9) -0.0132(7) 0.0065(7) -0.0039(7)
C15 0.0450(8) 0.0508(8) 0.0484(8) -0.0045(6) 0.0073(6) 0.0070(6)
C16 0.0546(9) 0.0478(8) 0.0828(12) 0.0017(8) 0.0168(8) -0.0031(7)
C17 0.0588(11) 0.0556(11) 0.149(2) -0.0015(12) 0.0410(13) -0.0080(9)
_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 O1 1.4286(11) . ?
S1 O2 1.4312(13) . ?
S1 N1 1.6252(12) . ?
S1 C1 1.7592(13) . ?
O3 N4 1.213(2) . ?
O4 N4 1.2168(19) . ?
N1 C8 1.4739(18) . ?
N1 C16 1.482(2) . ?
N2 C7 1.2831(17) . ?
N2 N3 1.4011(16) . ?
N3 C9 1.2687(18) . ?
N4 C12 1.470(2) . ?
C1 C2 1.3833(17) . ?
C1 C6 1.4009(17) . ?
C2 C3 1.3814(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3813(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3995(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4802(17) . ?
C7 C8 1.5196(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.4650(18) . ?
C9 H9 0.9300 . ?
C10 C11 1.3888(19) . ?
C10 C15 1.399(2) . ?
C11 C12 1.3817(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(2) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.510(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
O1 S1 O2 119.11(8) . . ?
O1 S1 N1 109.56(7) . . ?
O2 S1 N1 107.35(7) . . ?
O1 S1 C1 109.03(7) . . ?
O2 S1 C1 107.86(7) . . ?
N1 S1 C1 102.67(6) . . ?
C8 N1 C16 114.87(13) . . ?
C8 N1 S1 111.68(10) . . ?
C16 N1 S1 117.07(10) . . ?
C7 N2 N3 112.23(11) . . ?
C9 N3 N2 112.50(13) . . ?
O3 N4 O4 123.01(16) . . ?
O3 N4 C12 118.23(14) . . ?
O4 N4 C12 118.76(17) . . ?
C2 C1 C6 122.04(12) . . ?
C2 C1 S1 119.58(10) . . ?
C6 C1 S1 118.33(9) . . ?
C3 C2 C1 119.41(12) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 119.79(12) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.84(13) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.87(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 116.99(11) . . ?
C5 C6 C7 121.11(11) . . ?
C1 C6 C7 121.91(11) . . ?
N2 C7 C6 116.87(12) . . ?
N2 C7 C8 122.48(12) . . ?
C6 C7 C8 120.64(11) . . ?
N1 C8 C7 114.79(11) . . ?
N1 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
N1 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.5 . . ?
N3 C9 C10 120.27(14) . . ?
N3 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C15 119.46(13) . . ?
C11 C10 C9 118.94(13) . . ?
C15 C10 C9 121.57(13) . . ?
C12 C11 C10 118.46(14) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C13 C12 C11 122.97(14) . . ?
C13 C12 N4 118.80(14) . . ?
C11 C12 N4 118.22(15) . . ?
C12 C13 C14 118.30(14) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C15 C14 C13 120.45(15) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 120.37(14) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
N1 C16 C17 111.27(17) . . ?
N1 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N1 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 S1 N1 C8 -175.71(10) . . . . ?
O2 S1 N1 C8 53.60(12) . . . . ?
C1 S1 N1 C8 -59.95(12) . . . . ?
O1 S1 N1 C16 -40.37(13) . . . . ?
O2 S1 N1 C16 -171.06(11) . . . . ?
C1 S1 N1 C16 75.39(12) . . . . ?
C7 N2 N3 C9 174.67(13) . . . . ?
O1 S1 C1 C2 -30.74(14) . . . . ?
O2 S1 C1 C2 99.94(12) . . . . ?
N1 S1 C1 C2 -146.88(12) . . . . ?
O1 S1 C1 C6 151.57(11) . . . . ?
O2 S1 C1 C6 -77.75(12) . . . . ?
N1 S1 C1 C6 35.43(12) . . . . ?
C6 C1 C2 C3 2.0(2) . . . . ?
S1 C1 C2 C3 -175.59(12) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 -2.3(2) . . . . ?
C3 C4 C5 C6 1.5(2) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 -179.25(13) . . . . ?
C2 C1 C6 C5 -2.8(2) . . . . ?
S1 C1 C6 C5 174.88(10) . . . . ?
C2 C1 C6 C7 177.51(12) . . . . ?
S1 C1 C6 C7 -4.86(18) . . . . ?
N3 N2 C7 C6 177.77(11) . . . . ?
N3 N2 C7 C8 -3.7(2) . . . . ?
C5 C6 C7 N2 -6.8(2) . . . . ?
C1 C6 C7 N2 172.88(13) . . . . ?
C5 C6 C7 C8 174.64(14) . . . . ?
C1 C6 C7 C8 -5.6(2) . . . . ?
C16 N1 C8 C7 -80.35(17) . . . . ?
S1 N1 C8 C7 56.03(17) . . . . ?
N2 C7 C8 N1 161.23(14) . . . . ?
C6 C7 C8 N1 -20.3(2) . . . . ?
N2 N3 C9 C10 177.54(12) . . . . ?
N3 C9 C10 C11 -172.81(13) . . . . ?
N3 C9 C10 C15 5.0(2) . . . . ?
C15 C10 C11 C12 0.0(2) . . . . ?
C9 C10 C11 C12 177.87(12) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C10 C11 C12 N4 -178.94(12) . . . . ?
O3 N4 C12 C13 -179.59(17) . . . . ?
O4 N4 C12 C13 0.5(2) . . . . ?
O3 N4 C12 C11 -0.7(2) . . . . ?
O4 N4 C12 C11 179.38(14) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
N4 C12 C13 C14 178.96(14) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C10 0.0(2) . . . . ?
C11 C10 C15 C14 0.1(2) . . . . ?
C9 C10 C15 C14 -177.74(14) . . . . ?
C8 N1 C16 C17 -80.71(17) . . . . ?
S1 N1 C16 C17 145.33(13) . . . . ?
_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full 66.50
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max 0.198
_refine_diff_density_min -0.303
_refine_diff_density_rms 0.044
_database_code_depnum_ccdc_archive 'CCDC 968345'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(2-methyl-benzylidene)-hydrazine
;
_chemical_name_common
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(2-methyl-benzylidene)-hydrazine
;
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H15 N3 O2 S'
_chemical_formula_sum 'C16 H15 N3 O2 S'
_chemical_formula_weight 313.37
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 monoclinic
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 14.3069(3)
_cell_length_b 7.0786(2)
_cell_length_c 14.4568(6)
_cell_angle_alpha 90.00
_cell_angle_beta 91.803(2)
_cell_angle_gamma 90.00
_cell_volume 1463.36(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 7923
_cell_measurement_theta_min 3.0534
_cell_measurement_theta_max 76.2085
_exptl_crystal_description prismatic
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.33
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_min 0.16
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.422
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 656
_exptl_absorpt_coefficient_mu 2.062
_exptl_absorpt_correction_T_min 0.71728
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 12899
_diffrn_reflns_av_R_equivalents 0.0138
_diffrn_reflns_av_sigmaI/netI 0.0102
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 6.19
_diffrn_reflns_theta_max 76.52
_reflns_number_total 3053
_reflns_number_gt 2857
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0598P)^2^+0.2288P] 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 3053
_refine_ls_number_parameters 203
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0352
_refine_ls_R_factor_gt 0.0334
_refine_ls_wR_factor_ref 0.0995
_refine_ls_wR_factor_gt 0.0975
_refine_ls_goodness_of_fit_ref 1.070
_refine_ls_restrained_S_all 1.070
_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 0.67304(2) 0.01825(5) 0.89292(2) 0.04225(12) Uani 1 1 d . . .
O1 O 0.75209(7) 0.12918(18) 0.92234(7) 0.0615(3) Uani 1 1 d . . .
O2 O 0.66054(8) -0.16549(16) 0.93094(7) 0.0641(3) Uani 1 1 d . . .
N1 N 0.57909(7) 0.14015(16) 0.91153(6) 0.0388(2) Uani 1 1 d . . .
N2 N 0.42096(7) -0.02090(14) 0.72046(7) 0.0380(2) Uani 1 1 d . . .
N3 N 0.33937(7) -0.01126(15) 0.77207(8) 0.0424(3) Uani 1 1 d . . .
C1 C 0.67126(9) 0.00366(15) 0.77122(9) 0.0358(3) Uani 1 1 d . . .
C2 C 0.75564(10) -0.00600(19) 0.72647(11) 0.0469(3) Uani 1 1 d . . .
H2 H 0.8118 -0.0128 0.7604 0.056 Uiso 1 1 calc R . .
C3 C 0.75500(11) -0.0054(2) 0.63106(11) 0.0533(4) Uani 1 1 d . . .
H3 H 0.8110 -0.0150 0.6004 0.064 Uiso 1 1 calc R . .
C4 C 0.67148(11) 0.00948(19) 0.58083(10) 0.0493(3) Uani 1 1 d . . .
H4 H 0.6718 0.0123 0.5165 0.059 Uiso 1 1 calc R . .
C5 C 0.58729(9) 0.02020(18) 0.62552(9) 0.0413(3) Uani 1 1 d . . .
H5 H 0.5317 0.0324 0.5910 0.050 Uiso 1 1 calc R . .
C6 C 0.58532(8) 0.01275(15) 0.72192(8) 0.0329(2) Uani 1 1 d . . .
C7 C 0.49521(8) 0.01514(15) 0.76959(8) 0.0329(2) Uani 1 1 d . . .
C8 C 0.49319(8) 0.05336(18) 0.87275(8) 0.0385(3) Uani 1 1 d . . .
H8A H 0.4408 0.1360 0.8847 0.046 Uiso 1 1 calc R . .
H8B H 0.4826 -0.0649 0.9046 0.046 Uiso 1 1 calc R . .
C9 C 0.26602(9) 0.00357(16) 0.72119(9) 0.0389(3) Uani 1 1 d . . .
H9 H 0.2706 0.0000 0.6572 0.047 Uiso 1 1 calc R . .
C10 C 0.17417(8) 0.02623(17) 0.76161(9) 0.0383(3) Uani 1 1 d . . .
C11 C 0.09597(8) 0.07762(19) 0.70611(9) 0.0441(3) Uani 1 1 d . . .
C12 C 0.01229(9) 0.1140(2) 0.74933(11) 0.0543(3) Uani 1 1 d . . .
H12 H -0.0398 0.1505 0.7136 0.065 Uiso 1 1 calc R . .
C13 C 0.00486(10) 0.0971(2) 0.84369(11) 0.0589(4) Uani 1 1 d . . .
H13 H -0.0517 0.1230 0.8710 0.071 Uiso 1 1 calc R . .
C14 C 0.08147(11) 0.0417(2) 0.89801(11) 0.0567(4) Uani 1 1 d . . .
H14 H 0.0762 0.0276 0.9616 0.068 Uiso 1 1 calc R . .
C15 C 0.16591(10) 0.0075(2) 0.85718(10) 0.0470(3) Uani 1 1 d . . .
H15 H 0.2176 -0.0282 0.8936 0.056 Uiso 1 1 calc R . .
C16 C 0.10039(11) 0.0949(3) 0.60226(10) 0.0642(4) Uani 1 1 d . . .
H16A H 0.0404 0.1329 0.5772 0.096 Uiso 1 1 calc R . .
H16B H 0.1172 -0.0249 0.5765 0.096 Uiso 1 1 calc R . .
H16C H 0.1464 0.1877 0.5871 0.096 Uiso 1 1 calc R . .
H1 H 0.5850(13) 0.254(3) 0.8878(13) 0.077 Uiso 1 1 d . . .
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 0.04299(19) 0.0499(2) 0.03365(18) 0.00421(11) -0.00254(12) 0.00563(11)
O1 0.0446(5) 0.0888(8) 0.0504(5) -0.0066(5) -0.0111(4) -0.0026(5)
O2 0.0854(8) 0.0569(6) 0.0504(6) 0.0194(5) 0.0067(5) 0.0182(5)
N1 0.0419(5) 0.0438(5) 0.0308(5) -0.0024(4) 0.0017(4) -0.0008(4)
N2 0.0336(5) 0.0448(5) 0.0357(5) -0.0018(4) 0.0046(4) 0.0009(4)
N3 0.0334(5) 0.0540(6) 0.0401(6) -0.0015(4) 0.0062(4) -0.0004(4)
C1 0.0367(6) 0.0350(6) 0.0358(6) 0.0014(4) 0.0051(5) 0.0017(4)
C2 0.0364(6) 0.0522(8) 0.0526(8) 0.0021(5) 0.0079(6) 0.0032(5)
C3 0.0473(8) 0.0595(9) 0.0545(9) -0.0013(6) 0.0229(6) 0.0013(6)
C4 0.0599(8) 0.0528(8) 0.0362(6) -0.0013(5) 0.0168(6) -0.0034(6)
C5 0.0458(7) 0.0453(7) 0.0330(6) -0.0009(4) 0.0038(5) -0.0043(5)
C6 0.0364(6) 0.0309(5) 0.0316(6) -0.0008(4) 0.0053(4) -0.0008(4)
C7 0.0355(6) 0.0311(5) 0.0324(6) 0.0006(4) 0.0041(4) 0.0003(4)
C8 0.0391(6) 0.0450(6) 0.0316(6) -0.0018(5) 0.0061(4) -0.0034(5)
C9 0.0362(6) 0.0428(6) 0.0377(6) -0.0013(4) 0.0029(5) -0.0003(4)
C10 0.0334(6) 0.0394(6) 0.0420(6) -0.0013(5) 0.0030(5) -0.0028(4)
C11 0.0373(6) 0.0452(7) 0.0497(7) 0.0058(5) -0.0006(5) -0.0038(5)
C12 0.0340(6) 0.0574(8) 0.0716(9) 0.0077(7) 0.0012(6) 0.0020(5)
C13 0.0409(7) 0.0647(9) 0.0721(10) -0.0050(8) 0.0172(6) 0.0007(6)
C14 0.0491(8) 0.0737(10) 0.0482(8) -0.0076(7) 0.0141(6) -0.0067(7)
C15 0.0393(7) 0.0597(8) 0.0421(7) -0.0020(5) 0.0028(5) -0.0026(5)
C16 0.0502(8) 0.0909(13) 0.0509(8) 0.0173(8) -0.0077(6) -0.0031(8)
_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 O2 1.4254(11) . ?
S1 O1 1.4305(11) . ?
S1 N1 1.6268(10) . ?
S1 C1 1.7617(13) . ?
N1 C8 1.4693(15) . ?
N1 H1 0.88(2) . ?
N2 C7 1.2848(16) . ?
N2 N3 1.4066(14) . ?
N3 C9 1.2667(17) . ?
C1 C2 1.3893(17) . ?
C1 C6 1.4031(18) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3866(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3958(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.4809(15) . ?
C7 C8 1.5170(15) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.4637(16) . ?
C9 H9 0.9300 . ?
C10 C15 1.3967(19) . ?
C10 C11 1.4040(17) . ?
C11 C12 1.3918(18) . ?
C11 C16 1.5096(19) . ?
C12 C13 1.377(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.3825(19) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
O2 S1 O1 119.59(7) . . ?
O2 S1 N1 107.81(6) . . ?
O1 S1 N1 108.02(6) . . ?
O2 S1 C1 109.49(6) . . ?
O1 S1 C1 108.40(6) . . ?
N1 S1 C1 102.13(5) . . ?
C8 N1 S1 113.62(8) . . ?
C8 N1 H1 108.8(12) . . ?
S1 N1 H1 109.4(12) . . ?
C7 N2 N3 112.51(10) . . ?
C9 N3 N2 112.47(11) . . ?
C2 C1 C6 121.74(12) . . ?
C2 C1 S1 118.85(11) . . ?
C6 C1 S1 119.31(9) . . ?
C3 C2 C1 119.15(14) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.27(12) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.56(13) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.55(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 117.65(11) . . ?
C5 C6 C7 120.63(11) . . ?
C1 C6 C7 121.72(11) . . ?
N2 C7 C6 117.21(10) . . ?
N2 C7 C8 122.53(10) . . ?
C6 C7 C8 120.23(10) . . ?
N1 C8 C7 114.08(9) . . ?
N1 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N3 C9 C10 121.00(12) . . ?
N3 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C15 C10 C11 119.95(11) . . ?
C15 C10 C9 119.31(12) . . ?
C11 C10 C9 120.63(12) . . ?
C12 C11 C10 118.20(12) . . ?
C12 C11 C16 119.67(13) . . ?
C10 C11 C16 122.13(12) . . ?
C13 C12 C11 121.54(13) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 120.13(13) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.62(14) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C10 120.52(14) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 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
O2 S1 N1 C8 -57.36(10) . . . . ?
O1 S1 N1 C8 172.11(8) . . . . ?
C1 S1 N1 C8 57.94(9) . . . . ?
C7 N2 N3 C9 162.39(11) . . . . ?
O2 S1 C1 C2 -96.62(11) . . . . ?
O1 S1 C1 C2 35.43(12) . . . . ?
N1 S1 C1 C2 149.31(10) . . . . ?
O2 S1 C1 C6 86.92(10) . . . . ?
O1 S1 C1 C6 -141.03(9) . . . . ?
N1 S1 C1 C6 -27.15(10) . . . . ?
C6 C1 C2 C3 0.44(19) . . . . ?
S1 C1 C2 C3 -175.93(10) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 C5 C6 C1 3.09(17) . . . . ?
C4 C5 C6 C7 -177.12(11) . . . . ?
C2 C1 C6 C5 -2.76(16) . . . . ?
S1 C1 C6 C5 173.59(9) . . . . ?
C2 C1 C6 C7 177.45(11) . . . . ?
S1 C1 C6 C7 -6.19(14) . . . . ?
N3 N2 C7 C6 -178.83(9) . . . . ?
N3 N2 C7 C8 2.94(15) . . . . ?
C5 C6 C7 N2 16.15(16) . . . . ?
C1 C6 C7 N2 -164.06(10) . . . . ?
C5 C6 C7 C8 -165.57(10) . . . . ?
C1 C6 C7 C8 14.21(16) . . . . ?
S1 N1 C8 C7 -56.46(12) . . . . ?
N2 C7 C8 N1 -164.50(11) . . . . ?
C6 C7 C8 N1 17.32(15) . . . . ?
N2 N3 C9 C10 -176.56(10) . . . . ?
N3 C9 C10 C15 -8.09(18) . . . . ?
N3 C9 C10 C11 168.03(12) . . . . ?
C15 C10 C11 C12 1.85(19) . . . . ?
C9 C10 C11 C12 -174.24(12) . . . . ?
C15 C10 C11 C16 -178.39(14) . . . . ?
C9 C10 C11 C16 5.5(2) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C16 C11 C12 C13 179.01(15) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C15 1.4(2) . . . . ?
C13 C14 C15 C10 -0.8(2) . . . . ?
C11 C10 C15 C14 -0.9(2) . . . . ?
C9 C10 C15 C14 175.26(13) . . . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 76.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 0.191
_refine_diff_density_min -0.355
_refine_diff_density_rms 0.040
_database_code_depnum_ccdc_archive 'CCDC 968346'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(4-methyl-benzylidene)-hydrazine
;
_chemical_name_common
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(4-methyl-benzylidene)-hydrazine
;
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H15 N3 O2 S'
_chemical_formula_sum 'C16 H15 N3 O2 S'
_chemical_formula_weight 313.37
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 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a 7.31700(10)
_cell_length_b 13.0149(2)
_cell_length_c 16.1806(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1540.88(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 8893
_cell_measurement_theta_min 3.3930
_cell_measurement_theta_max 76.3192
_exptl_crystal_description rod
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.27
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.13
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.351
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 656
_exptl_absorpt_coefficient_mu 1.959
_exptl_absorpt_correction_T_min 0.89906
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 14336
_diffrn_reflns_av_R_equivalents 0.0225
_diffrn_reflns_av_sigmaI/netI 0.0161
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_theta_min 4.36
_diffrn_reflns_theta_max 76.52
_reflns_number_total 3189
_reflns_number_gt 3052
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0485P)^2^+0.0887P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.446(14)
_refine_ls_number_reflns 3188
_refine_ls_number_parameters 204
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0290
_refine_ls_R_factor_gt 0.0275
_refine_ls_wR_factor_ref 0.0772
_refine_ls_wR_factor_gt 0.0756
_refine_ls_goodness_of_fit_ref 1.065
_refine_ls_restrained_S_all 1.065
_refine_ls_shift/su_max 0.000
_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 0.09089(5) 0.91572(3) 0.12058(2) 0.04799(10) Uani 1 1 d . . .
O1 O 0.1882(2) 0.96169(9) 0.18744(8) 0.0627(3) Uani 1 1 d . . .
O2 O -0.08819(18) 0.95178(10) 0.10082(9) 0.0659(3) Uani 1 1 d . . .
N1 N 0.21599(18) 0.92594(9) 0.03790(8) 0.0455(3) Uani 1 1 d . . .
N2 N 0.05828(18) 0.69517(9) -0.07621(7) 0.0468(3) Uani 1 1 d . . .
N3 N 0.0605(2) 0.74126(10) -0.15489(8) 0.0507(3) Uani 1 1 d . . .
C1 C 0.0860(2) 0.78152(10) 0.13595(8) 0.0455(3) Uani 1 1 d . . .
C2 C 0.0779(3) 0.74344(14) 0.21552(10) 0.0614(4) Uani 1 1 d . . .
H2 H 0.0688 0.7880 0.2603 0.074 Uiso 1 1 calc R . .
C3 C 0.0833(3) 0.63855(15) 0.22790(10) 0.0697(5) Uani 1 1 d . . .
H3 H 0.0742 0.6119 0.2811 0.084 Uiso 1 1 calc R . .
C4 C 0.1024(3) 0.57315(12) 0.16119(11) 0.0622(4) Uani 1 1 d . . .
H4 H 0.1084 0.5026 0.1700 0.075 Uiso 1 1 calc R . .
C5 C 0.1126(2) 0.61109(11) 0.08143(10) 0.0506(3) Uani 1 1 d . . .
H5 H 0.1271 0.5662 0.0372 0.061 Uiso 1 1 calc R . .
C6 C 0.10110(19) 0.71695(10) 0.06743(8) 0.0412(3) Uani 1 1 d . . .
C7 C 0.10122(19) 0.75787(10) -0.01795(8) 0.0398(3) Uani 1 1 d . . .
C8 C 0.1425(2) 0.87019(11) -0.03375(9) 0.0461(3) Uani 1 1 d . . .
H8A H 0.2298 0.8749 -0.0787 0.055 Uiso 1 1 calc R . .
H8B H 0.0310 0.9039 -0.0516 0.055 Uiso 1 1 calc R . .
C9 C 0.0533(2) 0.67461(12) -0.21214(9) 0.0503(3) Uani 1 1 d . . .
H9 H 0.0498 0.6053 -0.1981 0.060 Uiso 1 1 calc R . .
C10 C 0.0504(2) 0.70360(12) -0.29937(9) 0.0488(3) Uani 1 1 d . . .
C11 C 0.0658(3) 0.80465(13) -0.32503(10) 0.0655(5) Uani 1 1 d . . .
H11 H 0.0796 0.8568 -0.2862 0.079 Uiso 1 1 calc R . .
C12 C 0.0606(3) 0.82820(15) -0.40825(12) 0.0711(5) Uani 1 1 d . . .
H12 H 0.0700 0.8965 -0.4245 0.085 Uiso 1 1 calc R . .
C13 C 0.0419(2) 0.75324(16) -0.46788(10) 0.0589(4) Uani 1 1 d . . .
C14 C 0.0277(3) 0.65308(16) -0.44200(11) 0.0657(5) Uani 1 1 d . . .
H14 H 0.0155 0.6011 -0.4811 0.079 Uiso 1 1 calc R . .
C15 C 0.0313(3) 0.62800(14) -0.35912(10) 0.0608(4) Uani 1 1 d . . .
H15 H 0.0207 0.5596 -0.3432 0.073 Uiso 1 1 calc R . .
C16 C 0.0397(3) 0.7800(2) -0.55857(12) 0.0840(7) Uani 1 1 d . . .
H16A H 0.1206 0.7349 -0.5879 0.126 Uiso 1 1 calc R . .
H16B H 0.0791 0.8498 -0.5658 0.126 Uiso 1 1 calc R . .
H16C H -0.0822 0.7724 -0.5797 0.126 Uiso 1 1 calc R . .
H1 H 0.330(4) 0.905(2) 0.0508(17) 0.101 Uiso 1 1 d . . .
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 0.05682(19) 0.03960(16) 0.04756(17) -0.00271(13) 0.00443(15) 0.00239(15)
O1 0.0861(8) 0.0501(6) 0.0520(6) -0.0129(5) 0.0011(6) -0.0035(6)
O2 0.0586(6) 0.0610(6) 0.0781(8) 0.0031(6) 0.0074(6) 0.0114(6)
N1 0.0531(6) 0.0372(5) 0.0461(6) 0.0017(5) 0.0004(5) -0.0031(5)
N2 0.0568(7) 0.0445(6) 0.0392(6) 0.0006(5) 0.0010(5) -0.0027(5)
N3 0.0648(8) 0.0505(6) 0.0369(5) 0.0012(5) -0.0002(5) -0.0026(6)
C1 0.0532(7) 0.0416(6) 0.0416(7) 0.0027(5) 0.0028(6) -0.0025(6)
C2 0.0817(11) 0.0611(9) 0.0413(7) 0.0025(6) 0.0076(8) -0.0079(9)
C3 0.0973(13) 0.0657(10) 0.0463(8) 0.0188(7) 0.0011(9) -0.0146(11)
C4 0.0797(10) 0.0450(7) 0.0620(9) 0.0161(7) -0.0051(9) -0.0080(8)
C5 0.0606(8) 0.0400(7) 0.0513(8) 0.0026(6) -0.0056(7) -0.0023(6)
C6 0.0442(6) 0.0392(6) 0.0404(6) 0.0045(5) 0.0002(5) -0.0017(5)
C7 0.0411(6) 0.0398(6) 0.0385(6) 0.0016(5) 0.0005(5) 0.0006(5)
C8 0.0549(8) 0.0420(7) 0.0414(6) 0.0060(6) -0.0023(6) -0.0035(6)
C9 0.0589(8) 0.0500(7) 0.0420(7) -0.0023(6) 0.0037(6) -0.0051(6)
C10 0.0555(8) 0.0511(7) 0.0398(7) -0.0044(6) 0.0025(6) -0.0051(6)
C11 0.0978(14) 0.0519(8) 0.0466(8) -0.0059(7) 0.0019(9) -0.0150(9)
C12 0.1006(15) 0.0598(9) 0.0529(9) 0.0076(8) -0.0002(10) -0.0200(10)
C13 0.0575(9) 0.0781(11) 0.0410(7) 0.0010(7) -0.0009(6) -0.0093(8)
C14 0.0845(12) 0.0676(11) 0.0450(8) -0.0126(8) -0.0043(8) -0.0044(9)
C15 0.0831(11) 0.0514(8) 0.0480(8) -0.0069(7) -0.0009(7) -0.0050(8)
C16 0.0859(14) 0.122(2) 0.0435(9) 0.0096(11) -0.0020(8) -0.0154(13)
_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 O1 1.4267(13) . ?
S1 O2 1.4281(13) . ?
S1 N1 1.6263(13) . ?
S1 C1 1.7646(14) . ?
N1 C8 1.4696(18) . ?
N1 H1 0.90(3) . ?
N2 C7 1.2856(18) . ?
N2 N3 1.4075(16) . ?
N3 C9 1.270(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.3955(19) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3988(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.4807(17) . ?
C7 C8 1.5145(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.461(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(2) . ?
C10 C15 1.386(2) . ?
C11 C12 1.382(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(3) . ?
C13 C16 1.508(2) . ?
C14 C15 1.381(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
O1 S1 O2 119.33(8) . . ?
O1 S1 N1 107.98(7) . . ?
O2 S1 N1 107.78(8) . . ?
O1 S1 C1 108.56(7) . . ?
O2 S1 C1 109.77(8) . . ?
N1 S1 C1 102.02(6) . . ?
C8 N1 S1 113.74(10) . . ?
C8 N1 H1 111.9(18) . . ?
S1 N1 H1 107.8(18) . . ?
C7 N2 N3 112.95(11) . . ?
C9 N3 N2 111.60(13) . . ?
C2 C1 C6 121.87(14) . . ?
C2 C1 S1 119.18(12) . . ?
C6 C1 S1 118.85(10) . . ?
C3 C2 C1 119.28(16) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.92(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.95(14) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.94(15) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 117.99(13) . . ?
C1 C6 C7 121.65(12) . . ?
C5 C6 C7 120.35(12) . . ?
N2 C7 C6 117.11(12) . . ?
N2 C7 C8 122.52(12) . . ?
C6 C7 C8 120.32(11) . . ?
N1 C8 C7 114.61(11) . . ?
N1 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
N1 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
N3 C9 C10 121.92(15) . . ?
N3 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C11 C10 C15 118.26(15) . . ?
C11 C10 C9 122.28(14) . . ?
C15 C10 C9 119.46(15) . . ?
C12 C11 C10 120.07(16) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 121.85(18) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C13 C12 117.76(16) . . ?
C14 C13 C16 121.01(18) . . ?
C12 C13 C16 121.22(19) . . ?
C13 C14 C15 121.29(17) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 120.76(17) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 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
O1 S1 N1 C8 172.71(10) . . . . ?
O2 S1 N1 C8 -57.14(12) . . . . ?
C1 S1 N1 C8 58.42(11) . . . . ?
C7 N2 N3 C9 167.14(14) . . . . ?
O1 S1 C1 C2 33.49(17) . . . . ?
O2 S1 C1 C2 -98.56(16) . . . . ?
N1 S1 C1 C2 147.34(15) . . . . ?
O1 S1 C1 C6 -142.86(13) . . . . ?
O2 S1 C1 C6 85.10(14) . . . . ?
N1 S1 C1 C6 -29.00(14) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
S1 C1 C2 C3 -176.76(17) . . . . ?
C1 C2 C3 C4 2.0(4) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C2 C1 C6 C5 -1.6(2) . . . . ?
S1 C1 C6 C5 174.66(12) . . . . ?
C2 C1 C6 C7 177.15(15) . . . . ?
S1 C1 C6 C7 -6.6(2) . . . . ?
C4 C5 C6 C1 2.3(2) . . . . ?
C4 C5 C6 C7 -176.49(15) . . . . ?
N3 N2 C7 C6 179.42(13) . . . . ?
N3 N2 C7 C8 2.1(2) . . . . ?
C1 C6 C7 N2 -158.73(14) . . . . ?
C5 C6 C7 N2 20.0(2) . . . . ?
C1 C6 C7 C8 18.7(2) . . . . ?
C5 C6 C7 C8 -162.65(14) . . . . ?
S1 N1 C8 C7 -53.27(15) . . . . ?
N2 C7 C8 N1 -171.05(14) . . . . ?
C6 C7 C8 N1 11.72(19) . . . . ?
N2 N3 C9 C10 178.84(14) . . . . ?
N3 C9 C10 C11 3.8(3) . . . . ?
N3 C9 C10 C15 -176.09(16) . . . . ?
C15 C10 C11 C12 0.4(3) . . . . ?
C9 C10 C11 C12 -179.4(2) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C11 C12 C13 C16 -179.0(2) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C16 C13 C14 C15 179.4(2) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C9 C10 C15 C14 179.88(18) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 76.52
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.136
_refine_diff_density_min -0.265
_refine_diff_density_rms 0.031
_database_code_depnum_ccdc_archive 'CCDC 968347'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(3-methyl-benzylidene)-hydrazine
;
_chemical_name_common
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(3-methyl-benzylidene)-hydrazine
;
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H15 N3 O2 S'
_chemical_formula_sum 'C16 H15 N3 O2 S'
_chemical_formula_weight 313.37
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 Triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.1464(3)
_cell_length_b 8.3969(3)
_cell_length_c 11.1659(4)
_cell_angle_alpha 86.728(3)
_cell_angle_beta 84.540(3)
_cell_angle_gamma 86.400(3)
_cell_volume 757.83(5)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 6969
_cell_measurement_theta_min 5.2808
_cell_measurement_theta_max 76.3913
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.373
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 328
_exptl_absorpt_coefficient_mu 1.991
_exptl_absorpt_correction_T_min 0.63160
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 13396
_diffrn_reflns_av_R_equivalents 0.0197
_diffrn_reflns_av_sigmaI/netI 0.0147
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 5.29
_diffrn_reflns_theta_max 76.58
_reflns_number_total 3149
_reflns_number_gt 2832
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0720P)^2^+0.1379P] 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 3149
_refine_ls_number_parameters 204
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0388
_refine_ls_R_factor_gt 0.0346
_refine_ls_wR_factor_ref 0.1081
_refine_ls_wR_factor_gt 0.1022
_refine_ls_goodness_of_fit_ref 0.972
_refine_ls_restrained_S_all 0.972
_refine_ls_shift/su_max 0.048
_refine_ls_shift/su_mean 0.001
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 -0.38050(4) 0.25220(4) 0.53551(3) 0.04721(14) Uani 1 1 d . . .
O1 O -0.50183(13) 0.22351(15) 0.45593(12) 0.0644(3) Uani 1 1 d . . .
O2 O -0.42053(14) 0.35883(14) 0.63055(11) 0.0632(3) Uani 1 1 d . . .
N1 N -0.32073(15) 0.08105(15) 0.59626(13) 0.0486(3) Uani 1 1 d . . .
N2 N 0.12127(15) 0.11583(15) 0.62159(11) 0.0476(3) Uani 1 1 d . . .
N3 N 0.12764(16) 0.01430(16) 0.72608(11) 0.0508(3) Uani 1 1 d . . .
C1 C -0.20049(16) 0.31556(15) 0.45066(12) 0.0407(3) Uani 1 1 d . . .
C2 C -0.21748(19) 0.41933(18) 0.35114(14) 0.0503(3) Uani 1 1 d . . .
H2 H -0.3217 0.4524 0.3286 0.060 Uiso 1 1 calc R . .
C3 C -0.0774(2) 0.47294(19) 0.28591(14) 0.0544(4) Uani 1 1 d . . .
H3 H -0.0869 0.5416 0.2182 0.065 Uiso 1 1 calc R . .
C4 C 0.07747(19) 0.42480(18) 0.32100(14) 0.0497(3) Uani 1 1 d . . .
H4 H 0.1712 0.4627 0.2773 0.060 Uiso 1 1 calc R . .
C5 C 0.09399(17) 0.32121(16) 0.42013(12) 0.0423(3) Uani 1 1 d . . .
H5 H 0.1988 0.2903 0.4426 0.051 Uiso 1 1 calc R . .
C6 C -0.04528(15) 0.26216(14) 0.48720(11) 0.0374(3) Uani 1 1 d . . .
C7 C -0.02647(16) 0.15108(15) 0.59364(12) 0.0392(3) Uani 1 1 d . . .
C8 C -0.17681(18) 0.08478(18) 0.66493(13) 0.0472(3) Uani 1 1 d . . .
H8A H -0.1479 -0.0230 0.6950 0.057 Uiso 1 1 calc R . .
H8B H -0.2067 0.1490 0.7340 0.057 Uiso 1 1 calc R . .
C9 C 0.27483(19) -0.01484(18) 0.75285(13) 0.0493(3) Uani 1 1 d . . .
H9 H 0.3604 0.0307 0.7042 0.059 Uiso 1 1 calc R . .
C10 C 0.31425(19) -0.11751(18) 0.85751(13) 0.0483(3) Uani 1 1 d . . .
C11 C 0.4785(2) -0.1471(2) 0.87909(15) 0.0558(4) Uani 1 1 d . . .
H11 H 0.5601 -0.1029 0.8258 0.067 Uiso 1 1 calc R . .
C12 C 0.5243(2) -0.2410(2) 0.97825(15) 0.0614(4) Uani 1 1 d . . .
C13 C 0.4007(3) -0.3067(2) 1.05491(16) 0.0745(5) Uani 1 1 d . . .
H13 H 0.4281 -0.3712 1.1214 0.089 Uiso 1 1 calc R . .
C14 C 0.2370(3) -0.2780(3) 1.03434(17) 0.0782(6) Uani 1 1 d . . .
H14 H 0.1557 -0.3229 1.0876 0.094 Uiso 1 1 calc R . .
C15 C 0.1917(2) -0.1841(2) 0.93629(15) 0.0614(4) Uani 1 1 d . . .
H15 H 0.0809 -0.1657 0.9231 0.074 Uiso 1 1 calc R . .
C20 C 0.7038(3) -0.2696(3) 1.0003(2) 0.0890(7) Uani 1 1 d . . .
H20A H 0.7120 -0.3125 1.0812 0.133 Uiso 1 1 calc R . .
H20B H 0.7572 -0.1704 0.9892 0.133 Uiso 1 1 calc R . .
H20C H 0.7563 -0.3440 0.9445 0.133 Uiso 1 1 calc R . .
H1 H -0.316(3) 0.013(3) 0.5464(18) 0.069(6) Uiso 1 1 d . . .
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 0.02695(19) 0.0509(2) 0.0629(2) -0.00325(15) -0.00104(14) 0.00026(13)
O1 0.0330(5) 0.0751(8) 0.0870(8) 0.0019(6) -0.0152(5) -0.0078(5)
O2 0.0484(6) 0.0634(7) 0.0742(7) -0.0117(6) 0.0089(5) 0.0094(5)
N1 0.0349(6) 0.0474(7) 0.0633(8) -0.0010(6) -0.0011(5) -0.0065(5)
N2 0.0381(6) 0.0537(7) 0.0503(6) 0.0094(5) -0.0067(5) -0.0025(5)
N3 0.0438(7) 0.0581(7) 0.0495(6) 0.0101(5) -0.0067(5) -0.0036(5)
C1 0.0324(6) 0.0398(6) 0.0502(7) -0.0052(5) -0.0052(5) -0.0003(5)
C2 0.0406(7) 0.0501(8) 0.0612(8) 0.0009(6) -0.0146(6) 0.0026(6)
C3 0.0531(9) 0.0555(8) 0.0544(8) 0.0109(7) -0.0113(7) -0.0042(7)
C4 0.0431(8) 0.0520(8) 0.0530(8) 0.0046(6) -0.0018(6) -0.0070(6)
C5 0.0311(6) 0.0439(7) 0.0519(7) -0.0001(5) -0.0047(5) -0.0028(5)
C6 0.0319(6) 0.0357(6) 0.0448(6) -0.0044(5) -0.0042(5) -0.0007(5)
C7 0.0344(6) 0.0385(6) 0.0446(7) -0.0040(5) -0.0023(5) -0.0013(5)
C8 0.0375(7) 0.0519(8) 0.0505(7) 0.0025(6) 0.0013(6) -0.0024(6)
C9 0.0425(8) 0.0562(8) 0.0486(7) 0.0070(6) -0.0067(6) -0.0038(6)
C10 0.0500(8) 0.0505(7) 0.0445(7) 0.0015(6) -0.0073(6) -0.0033(6)
C11 0.0522(9) 0.0590(9) 0.0565(8) 0.0036(7) -0.0125(7) -0.0003(7)
C12 0.0753(12) 0.0551(9) 0.0560(9) -0.0044(7) -0.0247(8) 0.0076(8)
C13 0.1042(16) 0.0688(11) 0.0498(9) 0.0095(8) -0.0188(9) 0.0077(10)
C14 0.0903(15) 0.0844(13) 0.0558(10) 0.0192(9) 0.0039(10) -0.0094(11)
C15 0.0568(10) 0.0701(10) 0.0553(9) 0.0088(7) -0.0017(7) -0.0054(8)
C20 0.0853(15) 0.0880(14) 0.0986(15) -0.0084(12) -0.0482(13) 0.0196(12)
_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 O1 1.4304(12) . ?
S1 O2 1.4283(12) . ?
S1 N1 1.6206(13) . ?
S1 C1 1.7627(14) . ?
N1 C8 1.4635(19) . ?
N1 H1 0.82(2) . ?
N2 C7 1.2844(17) . ?
N2 N3 1.4083(16) . ?
N3 C9 1.2688(19) . ?
C1 C2 1.384(2) . ?
C1 C6 1.4044(17) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3797(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.4001(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4819(18) . ?
C7 C8 1.5142(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.4607(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(2) . ?
C10 C15 1.390(2) . ?
C11 C12 1.389(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(3) . ?
C12 C20 1.508(3) . ?
C13 C14 1.379(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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
O1 S1 O2 119.93(7) . . ?
O1 S1 N1 107.51(7) . . ?
O2 S1 N1 107.42(8) . . ?
O1 S1 C1 109.45(7) . . ?
O2 S1 C1 107.91(7) . . ?
N1 S1 C1 103.37(6) . . ?
C8 N1 S1 114.69(10) . . ?
C8 N1 H1 116.2(15) . . ?
S1 N1 H1 109.5(15) . . ?
C7 N2 N3 113.24(11) . . ?
C9 N3 N2 111.62(12) . . ?
C2 C1 C6 122.21(13) . . ?
C2 C1 S1 118.53(10) . . ?
C6 C1 S1 119.25(10) . . ?
C3 C2 C1 119.00(13) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.17(14) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.68(14) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.72(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 117.19(12) . . ?
C5 C6 C7 120.38(11) . . ?
C1 C6 C7 122.40(12) . . ?
N2 C7 C6 116.93(11) . . ?
N2 C7 C8 122.63(12) . . ?
C6 C7 C8 120.44(11) . . ?
N1 C8 C7 114.24(11) . . ?
N1 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N3 C9 C10 122.17(14) . . ?
N3 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C11 C10 C15 119.46(14) . . ?
C11 C10 C9 118.80(14) . . ?
C15 C10 C9 121.73(14) . . ?
C10 C11 C12 121.74(16) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 117.84(17) . . ?
C13 C12 C20 121.57(17) . . ?
C11 C12 C20 120.60(19) . . ?
C12 C13 C14 120.91(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 121.19(18) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 118.87(18) . . ?
C14 C15 H15 120.6 . . ?
C10 C15 H15 120.6 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 S1 N1 C8 170.24(10) . . . . ?
O2 S1 N1 C8 -59.43(12) . . . . ?
C1 S1 N1 C8 54.52(12) . . . . ?
C7 N2 N3 C9 -178.34(13) . . . . ?
O1 S1 C1 C2 39.56(13) . . . . ?
O2 S1 C1 C2 -92.52(12) . . . . ?
N1 S1 C1 C2 153.89(12) . . . . ?
O1 S1 C1 C6 -141.69(11) . . . . ?
O2 S1 C1 C6 86.22(12) . . . . ?
N1 S1 C1 C6 -27.37(12) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
S1 C1 C2 C3 178.34(12) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 -1.33(19) . . . . ?
C4 C5 C6 C7 -179.93(12) . . . . ?
C2 C1 C6 C5 1.4(2) . . . . ?
S1 C1 C6 C5 -177.25(9) . . . . ?
C2 C1 C6 C7 -179.99(12) . . . . ?
S1 C1 C6 C7 1.32(17) . . . . ?
N3 N2 C7 C6 177.89(11) . . . . ?
N3 N2 C7 C8 -1.7(2) . . . . ?
C5 C6 C7 N2 1.46(19) . . . . ?
C1 C6 C7 N2 -177.07(12) . . . . ?
C5 C6 C7 C8 -178.89(12) . . . . ?
C1 C6 C7 C8 2.58(19) . . . . ?
S1 N1 C8 C7 -56.26(15) . . . . ?
N2 C7 C8 N1 -155.72(14) . . . . ?
C6 C7 C8 N1 24.66(17) . . . . ?
N2 N3 C9 C10 -179.92(13) . . . . ?
N3 C9 C10 C11 178.32(15) . . . . ?
N3 C9 C10 C15 -2.5(3) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 C12 178.70(15) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C10 C11 C12 C20 -179.27(16) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C20 C12 C13 C14 179.3(2) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C10 -0.2(3) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C9 C10 C15 C14 -179.04(17) . . . . ?
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full 76.58
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max 0.292
_refine_diff_density_min -0.362
_refine_diff_density_rms 0.036
_database_code_depnum_ccdc_archive 'CCDC 968348'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(3-methyl-benzylidene)-hydrazine
;
_chemical_name_common
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(4-methoxy-benzylidene)-hydrazine
;
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H15 N3 O3 S'
_chemical_formula_sum 'C16 H15 N3 O3 S'
_chemical_formula_weight 329.37
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 monoclinic
_symmetry_space_group_name_H-M 'P n'
_symmetry_space_group_name_Hall 'P -2yac'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'
_cell_length_a 26.6368(10)
_cell_length_b 7.1909(2)
_cell_length_c 8.6143(3)
_cell_angle_alpha 90.00
_cell_angle_beta 112.741(4)
_cell_angle_gamma 90.00
_cell_volume 1521.74(9)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 5605
_cell_measurement_theta_min 3.5954
_cell_measurement_theta_max 76.3324
_exptl_crystal_description needle
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.09
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.373
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 328
_exptl_absorpt_coefficient_mu 1.991
_exptl_absorpt_correction_T_min 0.95698
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 13329
_diffrn_reflns_av_R_equivalents 0.0259
_diffrn_reflns_av_sigmaI/netI 0.0265
_diffrn_reflns_limit_h_min -33
_diffrn_reflns_limit_h_max 33
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_theta_min 3.60
_diffrn_reflns_theta_max 76.52
_reflns_number_total 5846
_reflns_number_gt 4883
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0804P)^2^+0.2667P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.00
_refine_ls_number_reflns 5846
_refine_ls_number_parameters 423
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.0517
_refine_ls_R_factor_gt 0.0419
_refine_ls_wR_factor_ref 0.1377
_refine_ls_wR_factor_gt 0.1273
_refine_ls_goodness_of_fit_ref 1.043
_refine_ls_restrained_S_all 1.043
_refine_ls_shift/su_max 0.203
_refine_ls_shift/su_mean 0.035
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 0.83136(5) 0.05277(19) 0.98255(13) 0.0449(3) Uani 1 1 d . . .
S2 S 0.08987(5) 0.4477(2) 0.12001(13) 0.0457(4) Uani 1 1 d . . .
O1 O 0.8819(2) 0.1416(8) 1.0128(7) 0.0629(13) Uani 1 1 d . . .
O2 O 0.8312(3) -0.1288(7) 1.0462(6) 0.0647(14) Uani 1 1 d . . .
O3 O 0.4512(2) 0.0351(7) 1.2131(7) 0.0569(13) Uani 1 1 d . . .
O4 O 0.0902(3) 0.6320(7) 0.0557(6) 0.0628(14) Uani 1 1 d . . .
O5 O 0.0392(2) 0.3563(7) 0.0904(7) 0.0599(12) Uani 1 1 d . . .
O6 O 0.4704(2) 0.4725(8) -0.1020(6) 0.0578(12) Uani 1 1 d . . .
N1 N 0.7956(2) 0.1865(7) 1.0552(6) 0.0456(11) Uani 1 1 d . . .
N2 N 0.6572(2) 0.0310(7) 0.7793(7) 0.0441(12) Uani 1 1 d . . .
N3 N 0.6363(2) 0.0496(7) 0.9044(7) 0.0455(13) Uani 1 1 d . . .
N4 N 0.1244(2) 0.3159(6) 0.0451(7) 0.0461(12) Uani 1 1 d . . .
N5 N 0.2636(2) 0.4660(7) 0.3245(6) 0.0412(11) Uani 1 1 d . . .
N6 N 0.2864(3) 0.4600(7) 0.2004(7) 0.0464(13) Uani 1 1 d . . .
C1 C 0.7920(3) 0.0572(8) 0.7661(8) 0.0384(13) Uani 1 1 d . . .
C2 C 0.8165(3) 0.0494(9) 0.6497(9) 0.0513(17) Uani 1 1 d . . .
H2 H 0.8540 0.0353 0.6871 0.062 Uiso 1 1 calc R . .
C3 C 0.7857(3) 0.0622(10) 0.4800(9) 0.0546(18) Uani 1 1 d . . .
H3 H 0.8022 0.0552 0.4027 0.066 Uiso 1 1 calc R . .
C4 C 0.7300(3) 0.0857(11) 0.4253(7) 0.0561(16) Uani 1 1 d . . .
H4 H 0.7095 0.0989 0.3107 0.067 Uiso 1 1 calc R . .
C5 C 0.7035(3) 0.0899(9) 0.5377(7) 0.0432(12) Uani 1 1 d . . .
H5 H 0.6659 0.1028 0.4988 0.052 Uiso 1 1 calc R . .
C6 C 0.7360(3) 0.0740(7) 0.7148(7) 0.0363(12) Uani 1 1 d . . .
C7 C 0.7084(3) 0.0770(8) 0.8359(7) 0.0369(11) Uani 1 1 d . . .
C8 C 0.7412(3) 0.1169(8) 1.0203(7) 0.0399(12) Uani 1 1 d . . .
H8A H 0.7217 0.2074 1.0593 0.048 Uiso 1 1 calc R . .
H8B H 0.7440 0.0034 1.0840 0.048 Uiso 1 1 calc R . .
C9 C 0.5851(3) 0.0179(11) 0.8416(8) 0.0490(15) Uani 1 1 d . . .
H9 H 0.5685 -0.0074 0.7270 0.059 Uiso 1 1 calc R . .
C10 C 0.5505(3) 0.0195(10) 0.9429(7) 0.0438(13) Uani 1 1 d . . .
C11 C 0.5718(3) 0.0844(10) 1.1088(9) 0.0520(15) Uani 1 1 d . . .
H11 H 0.6076 0.1260 1.1557 0.062 Uiso 1 1 calc R . .
C12 C 0.5405(3) 0.0875(10) 1.2035(9) 0.0519(14) Uani 1 1 d . . .
H12 H 0.5553 0.1262 1.3152 0.062 Uiso 1 1 calc R . .
C13 C 0.4866(3) 0.0320(9) 1.1302(8) 0.0442(14) Uani 1 1 d . . .
C14 C 0.4649(3) -0.0288(11) 0.9667(9) 0.0587(19) Uani 1 1 d . . .
H14 H 0.4289 -0.0682 0.9191 0.070 Uiso 1 1 calc R . .
C15 C 0.4978(3) -0.0310(9) 0.8704(8) 0.0506(15) Uani 1 1 d . . .
H15 H 0.4831 -0.0670 0.7580 0.061 Uiso 1 1 calc R . .
C16 C 0.4727(3) 0.0661(14) 1.3819(10) 0.076(2) Uani 1 1 d . . .
H16A H 0.5024 -0.0183 1.4347 0.113 Uiso 1 1 calc R . .
H16B H 0.4453 0.0465 1.4266 0.113 Uiso 1 1 calc R . .
H16C H 0.4857 0.1917 1.4035 0.113 Uiso 1 1 calc R . .
C17 C 0.1302(3) 0.4471(8) 0.3400(8) 0.0408(14) Uani 1 1 d . . .
C18 C 0.1044(3) 0.4490(9) 0.4520(8) 0.0489(16) Uani 1 1 d . . .
H18 H 0.0668 0.4591 0.4149 0.059 Uiso 1 1 calc R . .
C19 C 0.1373(3) 0.4352(11) 0.6235(9) 0.061(2) Uani 1 1 d . . .
H19 H 0.1214 0.4371 0.7025 0.073 Uiso 1 1 calc R . .
C20 C 0.1927(3) 0.4188(10) 0.6761(8) 0.0535(15) Uani 1 1 d . . .
H20 H 0.2143 0.4131 0.7904 0.064 Uiso 1 1 calc R . .
C21 C 0.2161(3) 0.4111(9) 0.5601(9) 0.0468(13) Uani 1 1 d . . .
H21 H 0.2535 0.3924 0.5976 0.056 Uiso 1 1 calc R . .
C22 C 0.1870(2) 0.4295(8) 0.3929(8) 0.0381(12) Uani 1 1 d . . .
C23 C 0.2131(3) 0.4296(7) 0.2700(8) 0.0363(12) Uani 1 1 d . . .
C24 C 0.1811(3) 0.3836(10) 0.0873(8) 0.0472(14) Uani 1 1 d . . .
H24A H 0.1795 0.4939 0.0208 0.057 Uiso 1 1 calc R . .
H24B H 0.2008 0.2892 0.0533 0.057 Uiso 1 1 calc R . .
C25 C 0.3368(2) 0.4888(11) 0.2586(8) 0.0436(12) Uani 1 1 d . . .
H25 H 0.3541 0.5174 0.3723 0.052 Uiso 1 1 calc R . .
C26 C 0.3689(2) 0.4801(10) 0.1600(8) 0.0464(14) Uani 1 1 d . . .
C27 C 0.4247(3) 0.5391(9) 0.2298(10) 0.0532(16) Uani 1 1 d . . .
H27 H 0.4390 0.5841 0.3395 0.064 Uiso 1 1 calc R . .
C28 C 0.4565(3) 0.5316(9) 0.1438(8) 0.0509(16) Uani 1 1 d . . .
H28 H 0.4929 0.5654 0.1955 0.061 Uiso 1 1 calc R . .
C29 C 0.4357(3) 0.4733(9) -0.0246(9) 0.0457(14) Uani 1 1 d . . .
C30 C 0.3816(3) 0.4206(12) -0.0992(9) 0.0597(18) Uani 1 1 d . . .
H30 H 0.3674 0.3803 -0.2104 0.072 Uiso 1 1 calc R . .
C31 C 0.3487(3) 0.4278(11) -0.0076(8) 0.0592(18) Uani 1 1 d . . .
H31 H 0.3121 0.3965 -0.0603 0.071 Uiso 1 1 calc R . .
C32 C 0.4484(3) 0.4186(12) -0.2817(9) 0.0634(18) Uani 1 1 d . . .
H32A H 0.4305 0.3005 -0.2950 0.095 Uiso 1 1 calc R . .
H32B H 0.4777 0.4097 -0.3202 0.095 Uiso 1 1 calc R . .
H32C H 0.4228 0.5108 -0.3466 0.095 Uiso 1 1 calc R . .
H4N H 0.121(3) 0.250(7) 0.067(9) 0.076 Uiso 1 1 d . . .
H1N H 0.795(2) 0.321(6) 1.016(7) 0.076 Uiso 1 1 d . . .
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 0.0410(7) 0.0566(9) 0.0324(7) 0.0009(6) 0.0090(6) 0.0054(6)
S2 0.0413(7) 0.0570(9) 0.0359(7) 0.0032(6) 0.0118(6) 0.0033(6)
O1 0.041(3) 0.097(4) 0.044(3) -0.005(3) 0.009(2) 0.001(3)
O2 0.073(4) 0.059(3) 0.052(3) 0.010(2) 0.012(3) 0.014(3)
O3 0.039(2) 0.082(3) 0.057(3) -0.014(2) 0.026(2) -0.012(2)
O4 0.074(4) 0.062(3) 0.048(3) 0.018(2) 0.019(3) 0.013(3)
O5 0.039(2) 0.082(3) 0.056(3) -0.006(3) 0.014(2) -0.004(2)
O6 0.044(2) 0.093(3) 0.043(2) 0.005(2) 0.0239(19) -0.003(2)
N1 0.040(3) 0.068(3) 0.030(2) -0.005(2) 0.015(2) -0.006(2)
N2 0.036(3) 0.061(3) 0.040(3) 0.001(2) 0.020(2) 0.000(2)
N3 0.043(3) 0.058(3) 0.043(3) 0.0034(19) 0.024(2) -0.002(2)
N4 0.055(3) 0.044(2) 0.040(3) -0.003(2) 0.019(2) -0.003(2)
N5 0.049(3) 0.048(3) 0.033(2) 0.0007(18) 0.022(2) 0.004(2)
N6 0.046(3) 0.061(3) 0.042(3) -0.005(2) 0.027(2) 0.001(2)
C1 0.037(3) 0.046(3) 0.036(3) 0.0026(19) 0.018(2) 0.000(2)
C2 0.044(3) 0.070(5) 0.050(4) -0.002(3) 0.028(3) 0.005(3)
C3 0.044(3) 0.081(5) 0.050(4) 0.003(3) 0.030(3) 0.005(3)
C4 0.061(4) 0.085(4) 0.026(3) 0.013(3) 0.021(3) -0.004(3)
C5 0.039(3) 0.065(3) 0.023(2) 0.006(2) 0.009(2) 0.000(3)
C6 0.045(3) 0.038(2) 0.027(2) 0.0016(19) 0.016(2) 0.002(2)
C7 0.041(3) 0.043(2) 0.030(3) 0.000(2) 0.017(2) 0.003(2)
C8 0.051(3) 0.048(3) 0.022(2) -0.006(2) 0.016(2) -0.006(3)
C9 0.053(4) 0.061(3) 0.039(3) 0.001(3) 0.025(3) 0.008(3)
C10 0.050(3) 0.056(3) 0.033(3) -0.001(2) 0.025(2) 0.002(3)
C11 0.038(3) 0.063(3) 0.059(4) -0.015(3) 0.022(3) -0.010(2)
C12 0.037(3) 0.070(3) 0.051(4) -0.007(3) 0.019(3) -0.007(3)
C13 0.043(3) 0.056(4) 0.040(3) 0.000(2) 0.024(3) 0.001(3)
C14 0.039(3) 0.085(5) 0.062(4) -0.012(3) 0.030(3) -0.010(3)
C15 0.043(3) 0.078(4) 0.033(3) -0.001(2) 0.018(3) 0.001(3)
C16 0.048(3) 0.135(7) 0.057(4) -0.005(4) 0.034(3) -0.022(4)
C17 0.042(3) 0.050(3) 0.029(3) -0.0001(19) 0.012(2) 0.005(2)
C18 0.038(3) 0.068(4) 0.040(3) 0.000(2) 0.015(3) 0.003(3)
C19 0.065(5) 0.094(5) 0.032(3) -0.006(3) 0.027(3) -0.004(4)
C20 0.040(3) 0.083(4) 0.038(3) -0.006(3) 0.015(2) 0.005(3)
C21 0.042(3) 0.057(3) 0.045(3) 0.003(3) 0.022(3) 0.001(3)
C22 0.034(3) 0.047(3) 0.037(3) 0.000(2) 0.018(2) -0.001(2)
C23 0.040(3) 0.037(2) 0.035(3) 0.001(2) 0.018(2) 0.001(2)
C24 0.048(3) 0.060(3) 0.041(3) 0.006(3) 0.025(3) 0.000(3)
C25 0.034(3) 0.056(3) 0.041(3) -0.004(3) 0.015(2) -0.001(2)
C26 0.029(3) 0.053(3) 0.056(3) -0.003(3) 0.014(2) 0.001(2)
C27 0.039(3) 0.065(4) 0.052(3) -0.018(3) 0.015(3) -0.011(3)
C28 0.036(3) 0.066(4) 0.041(3) -0.003(2) 0.004(2) -0.008(3)
C29 0.032(3) 0.054(3) 0.051(3) 0.005(3) 0.016(3) 0.000(2)
C30 0.043(3) 0.104(5) 0.033(3) -0.013(3) 0.015(3) -0.005(4)
C31 0.030(3) 0.110(5) 0.036(3) -0.005(3) 0.011(2) -0.007(3)
C32 0.074(4) 0.082(4) 0.040(3) -0.002(3) 0.028(3) -0.002(3)
_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 O2 1.417(6) . ?
S1 O1 1.421(6) . ?
S1 N1 1.639(6) . ?
S1 C1 1.751(7) . ?
S2 O5 1.432(5) . ?
S2 O4 1.438(5) . ?
S2 N4 1.618(6) . ?
S2 C17 1.781(6) . ?
S2 H4N 1.79(6) . ?
O3 C16 1.360(9) . ?
O3 C13 1.386(7) . ?
O6 C29 1.332(8) . ?
O6 C32 1.480(8) . ?
N1 C8 1.450(8) . ?
N1 H1N 1.02(5) . ?
N2 C7 1.300(9) . ?
N2 N3 1.398(7) . ?
N3 C9 1.279(9) . ?
N4 C24 1.492(8) . ?
N4 H4N 0.53(5) . ?
N5 C23 1.268(9) . ?
N5 N6 1.420(7) . ?
N6 C25 1.257(9) . ?
C1 C6 1.386(8) . ?
C1 C2 1.393(9) . ?
C2 C3 1.376(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.439(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.491(8) . ?
C7 C8 1.515(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.493(8) . ?
C9 H9 0.9300 . ?
C10 C15 1.346(9) . ?
C10 C11 1.398(9) . ?
C11 C12 1.373(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(10) . ?
C14 C15 1.421(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.383(9) . ?
C17 C22 1.407(9) . ?
C18 C19 1.399(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(11) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.353(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.475(8) . ?
C23 C24 1.509(9) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.419(9) . ?
C25 H25 0.9300 . ?
C26 C31 1.383(10) . ?
C26 C27 1.435(8) . ?
C27 C28 1.326(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.402(10) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(9) . ?
C30 C31 1.389(10) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
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
O2 S1 O1 119.2(4) . . ?
O2 S1 N1 107.7(3) . . ?
O1 S1 N1 108.4(3) . . ?
O2 S1 C1 109.8(3) . . ?
O1 S1 C1 108.8(3) . . ?
N1 S1 C1 101.4(3) . . ?
O5 S2 O4 120.0(3) . . ?
O5 S2 N4 107.5(3) . . ?
O4 S2 N4 107.3(3) . . ?
O5 S2 C17 109.1(3) . . ?
O4 S2 C17 108.8(3) . . ?
N4 S2 C17 102.8(3) . . ?
O5 S2 H4N 95(2) . . ?
O4 S2 H4N 124(2) . . ?
N4 S2 H4N 17(2) . . ?
C17 S2 H4N 97(2) . . ?
C16 O3 C13 117.6(5) . . ?
C29 O6 C32 117.0(6) . . ?
C8 N1 S1 113.6(4) . . ?
C8 N1 H1N 112(3) . . ?
S1 N1 H1N 111(3) . . ?
C7 N2 N3 111.1(5) . . ?
C9 N3 N2 109.6(5) . . ?
C24 N4 S2 112.9(4) . . ?
C24 N4 H4N 120(8) . . ?
S2 N4 H4N 100(8) . . ?
C23 N5 N6 114.5(5) . . ?
C25 N6 N5 113.4(5) . . ?
C6 C1 C2 121.3(6) . . ?
C6 C1 S1 117.9(4) . . ?
C2 C1 S1 120.7(5) . . ?
C3 C2 C1 120.6(7) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.4(6) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.9(6) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 118.2(6) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 118.5(5) . . ?
C1 C6 C7 122.6(5) . . ?
C5 C6 C7 118.8(6) . . ?
N2 C7 C6 117.6(5) . . ?
N2 C7 C8 122.5(6) . . ?
C6 C7 C8 119.7(6) . . ?
N1 C8 C7 114.1(5) . . ?
N1 C8 H8A 108.7 . . ?
C7 C8 H8A 108.8 . . ?
N1 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N3 C9 C10 123.3(6) . . ?
N3 C9 H9 118.3 . . ?
C10 C9 H9 118.4 . . ?
C15 C10 C11 120.1(5) . . ?
C15 C10 C9 119.6(5) . . ?
C11 C10 C9 120.2(6) . . ?
C12 C11 C10 120.9(6) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.0(6) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.8(6) . . ?
C14 C13 O3 115.7(6) . . ?
C12 C13 O3 123.5(6) . . ?
C13 C14 C15 119.5(6) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C10 C15 C14 119.6(6) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 122.4(6) . . ?
C18 C17 S2 119.0(5) . . ?
C22 C17 S2 118.4(5) . . ?
C17 C18 C19 117.3(7) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.4 . . ?
C20 C19 C18 120.6(7) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 119.9(6) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 122.5(6) . . ?
C22 C21 H21 118.8 . . ?
C20 C21 H21 118.7 . . ?
C21 C22 C17 117.1(6) . . ?
C21 C22 C23 121.9(6) . . ?
C17 C22 C23 121.0(5) . . ?
N5 C23 C22 117.5(6) . . ?
N5 C23 C24 121.5(6) . . ?
C22 C23 C24 121.0(6) . . ?
N4 C24 C23 115.9(5) . . ?
N4 C24 H24A 108.3 . . ?
C23 C24 H24A 108.3 . . ?
N4 C24 H24B 108.3 . . ?
C23 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
N6 C25 C26 123.5(6) . . ?
N6 C25 H25 118.3 . . ?
C26 C25 H25 118.2 . . ?
C31 C26 C25 123.8(6) . . ?
C31 C26 C27 116.0(6) . . ?
C25 C26 C27 120.1(6) . . ?
C28 C27 C26 122.5(6) . . ?
C28 C27 H27 118.8 . . ?
C26 C27 H27 118.8 . . ?
C27 C28 C29 120.5(6) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
O6 C29 C30 124.4(6) . . ?
O6 C29 C28 116.4(6) . . ?
C30 C29 C28 119.1(6) . . ?
C29 C30 C31 119.9(6) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.1 . . ?
C26 C31 C30 121.8(6) . . ?
C26 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
O6 C32 H32A 109.5 . . ?
O6 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O6 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
O2 S1 N1 C8 -54.1(5) . . . . ?
O1 S1 N1 C8 175.6(4) . . . . ?
C1 S1 N1 C8 61.2(4) . . . . ?
C7 N2 N3 C9 174.8(6) . . . . ?
O5 S2 N4 C24 -172.6(4) . . . . ?
O4 S2 N4 C24 57.0(5) . . . . ?
C17 S2 N4 C24 -57.6(4) . . . . ?
C23 N5 N6 C25 -177.2(6) . . . . ?
O2 S1 C1 C6 81.8(6) . . . . ?
O1 S1 C1 C6 -146.1(5) . . . . ?
N1 S1 C1 C6 -32.0(5) . . . . ?
O2 S1 C1 C2 -100.0(6) . . . . ?
O1 S1 C1 C2 32.1(6) . . . . ?
N1 S1 C1 C2 146.3(5) . . . . ?
C6 C1 C2 C3 1.4(10) . . . . ?
S1 C1 C2 C3 -176.7(5) . . . . ?
C1 C2 C3 C4 0.9(11) . . . . ?
C2 C3 C4 C5 -2.4(12) . . . . ?
C3 C4 C5 C6 1.6(11) . . . . ?
C2 C1 C6 C5 -2.2(9) . . . . ?
S1 C1 C6 C5 176.0(4) . . . . ?
C2 C1 C6 C7 178.1(6) . . . . ?
S1 C1 C6 C7 -3.6(8) . . . . ?
C4 C5 C6 C1 0.7(9) . . . . ?
C4 C5 C6 C7 -179.6(6) . . . . ?
N3 N2 C7 C6 -177.0(5) . . . . ?
N3 N2 C7 C8 8.3(8) . . . . ?
C1 C6 C7 N2 -157.5(6) . . . . ?
C5 C6 C7 N2 22.9(8) . . . . ?
C1 C6 C7 C8 17.4(8) . . . . ?
C5 C6 C7 C8 -162.2(5) . . . . ?
S1 N1 C8 C7 -54.2(6) . . . . ?
N2 C7 C8 N1 -173.2(6) . . . . ?
C6 C7 C8 N1 12.1(8) . . . . ?
N2 N3 C9 C10 177.7(6) . . . . ?
N3 C9 C10 C15 -174.3(7) . . . . ?
N3 C9 C10 C11 9.8(12) . . . . ?
C15 C10 C11 C12 3.9(11) . . . . ?
C9 C10 C11 C12 179.7(7) . . . . ?
C10 C11 C12 C13 -2.5(11) . . . . ?
C11 C12 C13 C14 1.3(11) . . . . ?
C11 C12 C13 O3 -178.0(7) . . . . ?
C16 O3 C13 C14 169.9(8) . . . . ?
C16 O3 C13 C12 -10.7(10) . . . . ?
C12 C13 C14 C15 -1.4(11) . . . . ?
O3 C13 C14 C15 178.0(6) . . . . ?
C11 C10 C15 C14 -3.9(11) . . . . ?
C9 C10 C15 C14 -179.7(7) . . . . ?
C13 C14 C15 C10 2.7(11) . . . . ?
O5 S2 C17 C18 -29.8(6) . . . . ?
O4 S2 C17 C18 102.7(6) . . . . ?
N4 S2 C17 C18 -143.8(5) . . . . ?
O5 S2 C17 C22 145.1(5) . . . . ?
O4 S2 C17 C22 -82.4(6) . . . . ?
N4 S2 C17 C22 31.1(5) . . . . ?
C22 C17 C18 C19 0.9(10) . . . . ?
S2 C17 C18 C19 175.6(5) . . . . ?
C17 C18 C19 C20 -0.6(11) . . . . ?
C18 C19 C20 C21 -1.7(12) . . . . ?
C19 C20 C21 C22 3.9(11) . . . . ?
C20 C21 C22 C17 -3.4(10) . . . . ?
C20 C21 C22 C23 177.1(6) . . . . ?
C18 C17 C22 C21 1.0(9) . . . . ?
S2 C17 C22 C21 -173.7(5) . . . . ?
C18 C17 C22 C23 -179.5(6) . . . . ?
S2 C17 C22 C23 5.8(8) . . . . ?
N6 N5 C23 C22 178.7(5) . . . . ?
N6 N5 C23 C24 0.1(8) . . . . ?
C21 C22 C23 N5 -20.1(9) . . . . ?
C17 C22 C23 N5 160.5(5) . . . . ?
C21 C22 C23 C24 158.6(6) . . . . ?
C17 C22 C23 C24 -20.9(9) . . . . ?
S2 N4 C24 C23 49.8(6) . . . . ?
N5 C23 C24 N4 171.1(5) . . . . ?
C22 C23 C24 N4 -7.4(8) . . . . ?
N5 N6 C25 C26 176.7(6) . . . . ?
N6 C25 C26 C31 -4.2(13) . . . . ?
N6 C25 C26 C27 171.6(7) . . . . ?
C31 C26 C27 C28 -4.7(10) . . . . ?
C25 C26 C27 C28 179.2(7) . . . . ?
C26 C27 C28 C29 3.2(11) . . . . ?
C32 O6 C29 C30 2.7(11) . . . . ?
C32 O6 C29 C28 -177.6(6) . . . . ?
C27 C28 C29 O6 179.1(6) . . . . ?
C27 C28 C29 C30 -1.1(11) . . . . ?
O6 C29 C30 C31 -179.6(7) . . . . ?
C28 C29 C30 C31 0.7(12) . . . . ?
C25 C26 C31 C30 -179.7(8) . . . . ?
C27 C26 C31 C30 4.3(11) . . . . ?
C29 C30 C31 C26 -2.5(13) . . . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 76.52
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.189
_refine_diff_density_min -0.337
_refine_diff_density_rms 0.054
_database_code_depnum_ccdc_archive 'CCDC 968349'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
4-[(1,1-Dioxo-2,3-dihydro-1H-1l6-benzo[e][1,2]
thiazin-4-ylidene)-hydrazonomethyl]-2-ethoxy-phenol
;
_chemical_name_common
;
4-[(1,1-Dioxo-2,3-dihydro-1H-1l6-benzo[e][1,2]
thiazin-4-ylidene)-hydrazonomethyl]-2-ethoxy-phenol
;
_chemical_melting_point ?
_chemical_formula_moiety 'C18 H19 N3 O3 S'
_chemical_formula_sum 'C18 H19 N3 O3 S'
_chemical_formula_weight 357.42
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 monoclinic
_symmetry_space_group_name_H-M 'C 1 2/c 1'
_symmetry_space_group_name_Hall '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 14.1043(2)
_cell_length_b 8.49190(10)
_cell_length_c 28.3452(4)
_cell_angle_alpha 90.00
_cell_angle_beta 93.671(2)
_cell_angle_gamma 90.00
_cell_volume 3388.00(8)
_cell_formula_units_Z 8
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 10424
_cell_measurement_theta_min 4.6859
_cell_measurement_theta_max 76.2400
_exptl_crystal_description prismatic
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.14
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.401
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1504
_exptl_absorpt_coefficient_mu 1.896
_exptl_absorpt_correction_T_min 0.78694
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 17290
_diffrn_reflns_av_R_equivalents 0.0260
_diffrn_reflns_av_sigmaI/netI 0.0179
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -35
_diffrn_reflns_limit_l_max 35
_diffrn_reflns_theta_min 6.09
_diffrn_reflns_theta_max 76.43
_reflns_number_total 3539
_reflns_number_gt 3327
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.1285P)^2^+4.4618P] 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 3539
_refine_ls_number_parameters 232
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0620
_refine_ls_R_factor_gt 0.0600
_refine_ls_wR_factor_ref 0.1915
_refine_ls_wR_factor_gt 0.1888
_refine_ls_goodness_of_fit_ref 1.048
_refine_ls_restrained_S_all 1.048
_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 0.36554(4) 0.05728(6) 0.436771(19) 0.0357(2) Uani 1 1 d . . .
O1 O 0.46447(13) 0.0302(2) 0.43208(8) 0.0509(5) Uani 1 1 d . . .
O2 O 0.32591(14) 0.2057(2) 0.42210(7) 0.0480(5) Uani 1 1 d . . .
O3 O 0.02561(14) 0.1088(2) 0.69805(6) 0.0476(5) Uani 1 1 d . . .
N1 N 0.34350(15) 0.0311(3) 0.49180(7) 0.0375(4) Uani 1 1 d . . .
N2 N 0.11432(13) -0.1704(2) 0.48886(6) 0.0345(4) Uani 1 1 d . . .
N3 N 0.09065(14) -0.1140(2) 0.53321(6) 0.0357(4) Uani 1 1 d . . .
C1 C 0.29919(16) -0.0930(3) 0.40685(8) 0.0332(4) Uani 1 1 d . . .
C2 C 0.32953(18) -0.1467(3) 0.36430(8) 0.0413(5) Uani 1 1 d . . .
H2 H 0.3844 -0.1060 0.3524 0.050 Uiso 1 1 calc R . .
C3 C 0.2774(2) -0.2619(4) 0.33949(9) 0.0470(6) Uani 1 1 d . . .
H3 H 0.2966 -0.2982 0.3107 0.056 Uiso 1 1 calc R . .
C4 C 0.1961(2) -0.3226(3) 0.35809(9) 0.0458(6) Uani 1 1 d . . .
H4 H 0.1613 -0.4001 0.3415 0.055 Uiso 1 1 calc R . .
C5 C 0.16622(17) -0.2698(3) 0.40075(8) 0.0382(5) Uani 1 1 d . . .
H5 H 0.1114 -0.3114 0.4124 0.046 Uiso 1 1 calc R . .
C6 C 0.21794(15) -0.1538(2) 0.42672(7) 0.0307(4) Uani 1 1 d . . .
C7 C 0.18749(15) -0.1023(2) 0.47326(7) 0.0299(4) Uani 1 1 d . . .
C8 C 0.24209(18) 0.0266(3) 0.50011(9) 0.0381(5) Uani 1 1 d . . .
H8A H 0.2140 0.1274 0.4912 0.046 Uiso 1 1 calc R . .
H8B H 0.2352 0.0121 0.5337 0.046 Uiso 1 1 calc R . .
C9 C 0.01200(16) -0.1705(3) 0.54524(8) 0.0350(5) Uani 1 1 d . . .
H9 H -0.0234 -0.2349 0.5242 0.042 Uiso 1 1 calc R . .
C10 C -0.02349(15) -0.1363(3) 0.59136(8) 0.0341(5) Uani 1 1 d . . .
C11 C 0.01926(16) -0.0205(3) 0.62075(8) 0.0353(5) Uani 1 1 d . . .
H11 H 0.0680 0.0411 0.6101 0.042 Uiso 1 1 calc R . .
C12 C -0.01106(16) 0.0019(3) 0.66551(8) 0.0366(5) Uani 1 1 d . . .
C13 C -0.08590(18) -0.0900(3) 0.68110(9) 0.0429(6) Uani 1 1 d . . .
C14 C -0.12887(19) -0.2019(4) 0.65191(10) 0.0498(6) Uani 1 1 d . . .
H14 H -0.1786 -0.2620 0.6623 0.060 Uiso 1 1 calc R . .
C15 C -0.09787(17) -0.2251(3) 0.60680(9) 0.0432(6) Uani 1 1 d . . .
H15 H -0.1271 -0.3004 0.5870 0.052 Uiso 1 1 calc R . .
C16 C -0.11768(17) -0.0697(3) 0.72521(7) 0.0386(5) Uani 1 1 d . . .
H16A H -0.0974 -0.1567 0.7450 0.058 Uiso 1 1 calc R . .
H16B H -0.1858 -0.0644 0.7231 0.058 Uiso 1 1 calc R . .
H16C H -0.0922 0.0264 0.7386 0.058 Uiso 1 1 calc R . .
C17 C 0.0934(2) 0.2183(4) 0.68266(10) 0.0579(8) Uani 1 1 d . . .
H17A H 0.0649 0.2818 0.6571 0.070 Uiso 1 1 calc R . .
H17B H 0.1470 0.1622 0.6710 0.070 Uiso 1 1 calc R . .
C18 C 0.1266(3) 0.3222(5) 0.72286(12) 0.0799(12) Uani 1 1 d . . .
H18A H 0.0753 0.3886 0.7313 0.120 Uiso 1 1 calc R . .
H18B H 0.1784 0.3862 0.7136 0.120 Uiso 1 1 calc R . .
H18C H 0.1476 0.2585 0.7495 0.120 Uiso 1 1 calc R . .
H1 H 0.365(3) -0.050(5) 0.5021(15) 0.067(12) Uiso 1 1 d . . .
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 0.0363(3) 0.0325(3) 0.0393(3) 0.00010(19) 0.0089(2) -0.00674(19)
O1 0.0368(9) 0.0551(11) 0.0622(12) -0.0067(9) 0.0136(8) -0.0088(8)
O2 0.0591(11) 0.0330(9) 0.0531(10) 0.0068(7) 0.0118(8) -0.0023(8)
O3 0.0569(11) 0.0566(11) 0.0302(8) -0.0039(7) 0.0106(7) -0.0174(9)
N1 0.0400(10) 0.0364(10) 0.0362(10) -0.0025(8) 0.0030(8) -0.0092(8)
N2 0.0377(9) 0.0370(10) 0.0293(9) -0.0055(7) 0.0069(7) -0.0047(7)
N3 0.0387(10) 0.0401(10) 0.0291(9) -0.0051(7) 0.0078(7) -0.0041(8)
C1 0.0368(10) 0.0311(10) 0.0319(10) 0.0004(8) 0.0040(8) -0.0009(8)
C2 0.0428(12) 0.0471(13) 0.0350(11) 0.0021(10) 0.0104(9) 0.0027(10)
C3 0.0547(14) 0.0552(15) 0.0318(11) -0.0089(10) 0.0071(10) 0.0061(12)
C4 0.0539(14) 0.0480(14) 0.0352(11) -0.0120(10) 0.0007(10) -0.0029(11)
C5 0.0406(11) 0.0399(12) 0.0339(11) -0.0042(9) 0.0019(9) -0.0061(9)
C6 0.0345(10) 0.0310(10) 0.0269(9) -0.0001(8) 0.0030(8) -0.0007(8)
C7 0.0332(10) 0.0286(10) 0.0281(10) -0.0013(7) 0.0037(8) -0.0018(8)
C8 0.0439(12) 0.0360(11) 0.0354(11) -0.0088(9) 0.0105(9) -0.0099(9)
C9 0.0350(10) 0.0369(11) 0.0335(10) -0.0023(8) 0.0049(8) -0.0006(8)
C10 0.0314(10) 0.0390(11) 0.0324(10) -0.0003(9) 0.0053(8) 0.0023(8)
C11 0.0345(10) 0.0413(12) 0.0307(10) 0.0025(9) 0.0072(8) -0.0013(9)
C12 0.0386(11) 0.0411(12) 0.0307(11) 0.0003(9) 0.0059(8) -0.0012(9)
C13 0.0415(12) 0.0550(14) 0.0337(12) -0.0010(10) 0.0142(9) -0.0037(11)
C14 0.0431(13) 0.0610(16) 0.0474(14) -0.0051(12) 0.0189(11) -0.0153(12)
C15 0.0377(11) 0.0500(14) 0.0428(12) -0.0079(10) 0.0096(9) -0.0072(10)
C16 0.0399(11) 0.0559(14) 0.0224(10) -0.0071(9) 0.0204(8) -0.0163(10)
C17 0.0684(18) 0.0651(18) 0.0412(13) -0.0037(13) 0.0110(12) -0.0290(15)
C18 0.100(3) 0.093(3) 0.0480(16) -0.0159(17) 0.0116(17) -0.049(2)
_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 O1 1.4286(19) . ?
S1 O2 1.4298(19) . ?
S1 N1 1.625(2) . ?
S1 C1 1.767(2) . ?
O3 C12 1.372(3) . ?
O3 C17 1.422(3) . ?
N1 C8 1.465(3) . ?
N1 H1 0.80(4) . ?
N2 C7 1.286(3) . ?
N2 N3 1.406(2) . ?
N3 C9 1.275(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.479(3) . ?
C7 C8 1.515(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.459(3) . ?
C9 H9 0.9300 . ?
C10 C15 1.386(3) . ?
C10 C11 1.400(3) . ?
C11 C12 1.378(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.406(3) . ?
C13 C16 1.366(3) . ?
C13 C14 1.375(4) . ?
C14 C15 1.392(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.492(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
O1 S1 O2 118.73(12) . . ?
O1 S1 N1 108.38(12) . . ?
O2 S1 N1 107.71(12) . . ?
O1 S1 C1 109.25(11) . . ?
O2 S1 C1 108.17(11) . . ?
N1 S1 C1 103.54(10) . . ?
C12 O3 C17 117.30(19) . . ?
C8 N1 S1 113.99(17) . . ?
C8 N1 H1 105(3) . . ?
S1 N1 H1 112(3) . . ?
C7 N2 N3 113.33(18) . . ?
C9 N3 N2 111.79(19) . . ?
C2 C1 C6 122.2(2) . . ?
C2 C1 S1 118.23(18) . . ?
C6 C1 S1 119.53(17) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.14(19) . . ?
C1 C6 C7 122.60(19) . . ?
C5 C6 C7 120.25(19) . . ?
N2 C7 C6 117.30(19) . . ?
N2 C7 C8 123.07(19) . . ?
C6 C7 C8 119.63(18) . . ?
N1 C8 C7 114.11(19) . . ?
N1 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N3 C9 C10 121.2(2) . . ?
N3 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C15 C10 C11 120.0(2) . . ?
C15 C10 C9 119.0(2) . . ?
C11 C10 C9 120.9(2) . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O3 C12 C11 125.8(2) . . ?
O3 C12 C13 114.5(2) . . ?
C11 C12 C13 119.7(2) . . ?
C16 C13 C14 118.7(2) . . ?
C16 C13 C12 121.0(2) . . ?
C14 C13 C12 120.3(2) . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 120.1(2) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C18 109.7(2) . . ?
O3 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
O3 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O1 S1 N1 C8 -169.33(17) . . . . ?
O2 S1 N1 C8 61.04(19) . . . . ?
C1 S1 N1 C8 -53.39(19) . . . . ?
C7 N2 N3 C9 172.6(2) . . . . ?
O1 S1 C1 C2 -38.7(2) . . . . ?
O2 S1 C1 C2 91.8(2) . . . . ?
N1 S1 C1 C2 -154.1(2) . . . . ?
O1 S1 C1 C6 141.30(19) . . . . ?
O2 S1 C1 C6 -88.1(2) . . . . ?
N1 S1 C1 C6 26.0(2) . . . . ?
C6 C1 C2 C3 1.6(4) . . . . ?
S1 C1 C2 C3 -178.41(19) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
S1 C1 C6 C5 178.16(17) . . . . ?
C2 C1 C6 C7 177.1(2) . . . . ?
S1 C1 C6 C7 -2.9(3) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 C7 -177.7(2) . . . . ?
N3 N2 C7 C6 -179.99(18) . . . . ?
N3 N2 C7 C8 -0.3(3) . . . . ?
C1 C6 C7 N2 -177.2(2) . . . . ?
C5 C6 C7 N2 1.6(3) . . . . ?
C1 C6 C7 C8 3.1(3) . . . . ?
C5 C6 C7 C8 -178.0(2) . . . . ?
S1 N1 C8 C7 59.2(3) . . . . ?
N2 C7 C8 N1 149.3(2) . . . . ?
C6 C7 C8 N1 -31.1(3) . . . . ?
N2 N3 C9 C10 175.93(19) . . . . ?
N3 C9 C10 C15 -166.6(2) . . . . ?
N3 C9 C10 C11 10.6(4) . . . . ?
C15 C10 C11 C12 1.8(4) . . . . ?
C9 C10 C11 C12 -175.3(2) . . . . ?
C17 O3 C12 C11 7.6(4) . . . . ?
C17 O3 C12 C13 -172.5(3) . . . . ?
C10 C11 C12 O3 178.8(2) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
O3 C12 C13 C16 0.4(4) . . . . ?
C11 C12 C13 C16 -179.7(2) . . . . ?
O3 C12 C13 C14 -179.9(3) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C16 C13 C14 C15 -180.0(3) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C11 C10 C15 C14 -1.4(4) . . . . ?
C9 C10 C15 C14 175.7(2) . . . . ?
C13 C14 C15 C10 0.4(4) . . . . ?
C12 O3 C17 C18 -178.8(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full 76.43
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max 1.148
_refine_diff_density_min -0.590
_refine_diff_density_rms 0.079
_database_code_depnum_ccdc_archive 'CCDC 968350'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(2-methoxy-benzylidene)-hydrazine
;
_chemical_name_common
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(2-methoxy-benzylidene)-hydrazine
;
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H15 N3 O3 S'
_chemical_formula_sum 'C16 H15 N3 O3 S'
_chemical_formula_weight 329.37
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 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a 6.64540(10)
_cell_length_b 10.9886(2)
_cell_length_c 21.2138(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1549.11(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 7711
_cell_measurement_theta_min 4.0196
_cell_measurement_theta_max 76.3178
_exptl_crystal_description needle
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.47
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.412
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 688
_exptl_absorpt_coefficient_mu 2.027
_exptl_absorpt_correction_T_min 0.70929
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 11602
_diffrn_reflns_av_R_equivalents 0.0185
_diffrn_reflns_av_sigmaI/netI 0.0147
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_theta_min 4.17
_diffrn_reflns_theta_max 76.51
_reflns_number_total 3222
_reflns_number_gt 3112
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0508P)^2^+0.2628P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.003(16)
_refine_ls_number_reflns 3222
_refine_ls_number_parameters 212
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0308
_refine_ls_R_factor_gt 0.0297
_refine_ls_wR_factor_ref 0.0818
_refine_ls_wR_factor_gt 0.0806
_refine_ls_goodness_of_fit_ref 0.922
_refine_ls_restrained_S_all 0.922
_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 -0.26592(7) 0.19585(3) 0.87260(2) 0.05791(13) Uani 1 1 d . . .
O1 O -0.4654(3) 0.16274(17) 0.88921(9) 0.0987(6) Uani 1 1 d . . .
O2 O -0.1285(3) 0.10397(12) 0.85406(8) 0.0883(5) Uani 1 1 d . . .
O3 O 0.77580(17) 0.70996(10) 0.86611(5) 0.0552(3) Uani 1 1 d . . .
N1 N -0.1661(2) 0.26621(13) 0.93196(7) 0.0563(4) Uani 1 1 d . . .
N2 N 0.1782(2) 0.48000(13) 0.85167(6) 0.0516(3) Uani 1 1 d . . .
N3 N 0.3213(2) 0.48162(14) 0.90006(7) 0.0575(4) Uani 1 1 d . . .
C1 C -0.2739(2) 0.30838(14) 0.81380(7) 0.0473(3) Uani 1 1 d . . .
C2 C -0.4252(3) 0.3051(2) 0.76877(10) 0.0660(5) Uani 1 1 d . . .
H2 H -0.5216 0.2438 0.7695 0.079 Uiso 1 1 calc R . .
C3 C -0.4307(3) 0.3943(2) 0.72287(10) 0.0690(5) Uani 1 1 d . . .
H3 H -0.5318 0.3934 0.6925 0.083 Uiso 1 1 calc R . .
C4 C -0.2875(3) 0.48416(17) 0.72194(8) 0.0584(4) Uani 1 1 d . . .
H4 H -0.2923 0.5436 0.6908 0.070 Uiso 1 1 calc R . .
C5 C -0.1369(2) 0.48760(15) 0.76644(7) 0.0490(3) Uani 1 1 d . . .
H5 H -0.0415 0.5494 0.7651 0.059 Uiso 1 1 calc R . .
C6 C -0.1262(2) 0.39897(13) 0.81360(7) 0.0410(3) Uani 1 1 d . . .
C7 C 0.0356(2) 0.40401(13) 0.86174(7) 0.0430(3) Uani 1 1 d . . .
C8 C 0.0285(3) 0.32268(17) 0.91951(8) 0.0579(4) Uani 1 1 d . . .
H8A H 0.1281 0.2589 0.9146 0.070 Uiso 1 1 calc R . .
H8B H 0.0665 0.3706 0.9560 0.070 Uiso 1 1 calc R . .
C9 C 0.4591(2) 0.55803(14) 0.89024(7) 0.0447(3) Uani 1 1 d . . .
H9 H 0.4589 0.6033 0.8532 0.054 Uiso 1 1 calc R . .
C10 C 0.6190(2) 0.57608(13) 0.93652(7) 0.0419(3) Uani 1 1 d . . .
C11 C 0.7818(2) 0.65338(13) 0.92332(7) 0.0448(3) Uani 1 1 d . . .
C12 C 0.9346(3) 0.66890(16) 0.96737(9) 0.0566(4) Uani 1 1 d . . .
H12 H 1.0418 0.7207 0.9588 0.068 Uiso 1 1 calc R . .
C13 C 0.9261(3) 0.60701(17) 1.02381(9) 0.0643(5) Uani 1 1 d . . .
H13 H 1.0301 0.6161 1.0528 0.077 Uiso 1 1 calc R . .
C14 C 0.7657(3) 0.53168(16) 1.03822(8) 0.0601(4) Uani 1 1 d . . .
H14 H 0.7610 0.4914 1.0767 0.072 Uiso 1 1 calc R . .
C15 C 0.6129(3) 0.51696(15) 0.99486(8) 0.0504(4) Uani 1 1 d . . .
H15 H 0.5043 0.4670 1.0046 0.060 Uiso 1 1 calc R . .
C16 C 0.9397(3) 0.7850(2) 0.84852(11) 0.0701(5) Uani 1 1 d . . .
H16A H 1.0625 0.7392 0.8510 0.105 Uiso 1 1 calc R . .
H16B H 0.9471 0.8535 0.8765 0.105 Uiso 1 1 calc R . .
H16C H 0.9207 0.8132 0.8061 0.105 Uiso 1 1 calc R . .
H1 H -0.261(4) 0.318(2) 0.9491(10) 0.084 Uiso 1 1 d . . .
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 0.0676(3) 0.04196(19) 0.0642(2) 0.00102(16) 0.0010(2) -0.01525(18)
O1 0.0832(10) 0.1092(13) 0.1038(13) 0.0310(10) -0.0016(9) -0.0509(10)
O2 0.1339(14) 0.0459(7) 0.0850(10) -0.0115(7) -0.0037(10) 0.0176(8)
O3 0.0520(6) 0.0574(6) 0.0564(6) 0.0091(5) -0.0020(5) -0.0129(5)
N1 0.0727(10) 0.0463(7) 0.0499(7) 0.0028(6) 0.0091(7) -0.0126(7)
N2 0.0464(7) 0.0587(8) 0.0497(7) 0.0082(6) -0.0045(5) -0.0099(6)
N3 0.0548(8) 0.0640(8) 0.0536(8) 0.0105(6) -0.0105(6) -0.0158(7)
C1 0.0470(7) 0.0445(7) 0.0505(7) -0.0044(6) 0.0024(6) -0.0039(7)
C2 0.0569(10) 0.0720(12) 0.0690(11) -0.0034(10) -0.0095(8) -0.0159(9)
C3 0.0588(10) 0.0878(14) 0.0604(11) -0.0038(10) -0.0160(9) -0.0016(10)
C4 0.0656(10) 0.0629(9) 0.0466(8) 0.0010(7) -0.0048(8) 0.0084(9)
C5 0.0551(8) 0.0479(8) 0.0440(8) -0.0018(6) 0.0021(6) -0.0013(7)
C6 0.0427(7) 0.0413(7) 0.0390(7) -0.0052(5) 0.0036(6) -0.0005(6)
C7 0.0460(7) 0.0404(7) 0.0425(7) -0.0005(6) 0.0022(6) -0.0029(6)
C8 0.0667(10) 0.0552(9) 0.0519(9) 0.0103(8) -0.0077(7) -0.0166(8)
C9 0.0407(7) 0.0464(7) 0.0469(8) 0.0045(6) 0.0012(6) -0.0001(6)
C10 0.0399(7) 0.0382(7) 0.0475(7) -0.0024(6) 0.0021(6) 0.0029(6)
C11 0.0455(7) 0.0393(6) 0.0497(7) -0.0037(6) -0.0004(6) 0.0013(6)
C12 0.0501(8) 0.0511(9) 0.0686(10) -0.0076(8) -0.0082(7) -0.0047(8)
C13 0.0654(11) 0.0647(11) 0.0627(11) -0.0049(9) -0.0222(9) 0.0030(9)
C14 0.0712(10) 0.0590(9) 0.0500(8) 0.0038(7) -0.0078(8) 0.0112(9)
C15 0.0531(8) 0.0451(8) 0.0529(8) 0.0033(7) 0.0018(7) 0.0040(7)
C16 0.0632(11) 0.0668(11) 0.0805(13) 0.0117(10) 0.0033(9) -0.0198(9)
_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 O2 1.4169(16) . ?
S1 O1 1.4191(16) . ?
S1 N1 1.6199(15) . ?
S1 C1 1.7571(16) . ?
O3 C11 1.3643(18) . ?
O3 C16 1.416(2) . ?
N1 C8 1.458(2) . ?
N1 H1 0.93(2) . ?
N2 C7 1.2813(19) . ?
N2 N3 1.3990(18) . ?
N3 C9 1.260(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.398(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.484(2) . ?
C7 C8 1.518(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.461(2) . ?
C9 H9 0.9300 . ?
C10 C15 1.398(2) . ?
C10 C11 1.403(2) . ?
C11 C12 1.390(2) . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
O2 S1 O1 119.22(12) . . ?
O2 S1 N1 106.98(10) . . ?
O1 S1 N1 108.17(10) . . ?
O2 S1 C1 108.90(9) . . ?
O1 S1 C1 109.18(9) . . ?
N1 S1 C1 103.20(7) . . ?
C11 O3 C16 118.51(14) . . ?
C8 N1 S1 115.17(12) . . ?
C8 N1 H1 114.2(15) . . ?
S1 N1 H1 108.8(15) . . ?
C7 N2 N3 112.86(13) . . ?
C9 N3 N2 112.40(13) . . ?
C2 C1 C6 121.67(16) . . ?
C2 C1 S1 119.49(13) . . ?
C6 C1 S1 118.84(12) . . ?
C3 C2 C1 119.07(17) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 120.17(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.95(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.59(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 117.56(14) . . ?
C5 C6 C7 120.23(13) . . ?
C1 C6 C7 122.21(13) . . ?
N2 C7 C6 116.47(13) . . ?
N2 C7 C8 122.79(14) . . ?
C6 C7 C8 120.75(13) . . ?
N1 C8 C7 115.12(14) . . ?
N1 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
N1 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
N3 C9 C10 120.57(14) . . ?
N3 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C15 C10 C11 118.69(14) . . ?
C15 C10 C9 120.70(14) . . ?
C11 C10 C9 120.60(13) . . ?
O3 C11 C12 124.29(15) . . ?
O3 C11 C10 115.51(13) . . ?
C12 C11 C10 120.19(15) . . ?
C13 C12 C11 119.57(16) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 121.25(16) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 119.32(16) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 120.95(16) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 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
O2 S1 N1 C8 59.25(15) . . . . ?
O1 S1 N1 C8 -171.15(14) . . . . ?
C1 S1 N1 C8 -55.55(14) . . . . ?
C7 N2 N3 C9 -178.89(15) . . . . ?
O2 S1 C1 C2 96.85(17) . . . . ?
O1 S1 C1 C2 -34.86(18) . . . . ?
N1 S1 C1 C2 -149.74(15) . . . . ?
O2 S1 C1 C6 -82.93(14) . . . . ?
O1 S1 C1 C6 145.35(14) . . . . ?
N1 S1 C1 C6 30.47(14) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
S1 C1 C2 C3 179.73(16) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 -179.45(14) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
S1 C1 C6 C5 -179.70(11) . . . . ?
C2 C1 C6 C7 179.55(16) . . . . ?
S1 C1 C6 C7 -0.67(19) . . . . ?
N3 N2 C7 C6 178.24(13) . . . . ?
N3 N2 C7 C8 -1.6(2) . . . . ?
C5 C6 C7 N2 -10.7(2) . . . . ?
C1 C6 C7 N2 170.27(14) . . . . ?
C5 C6 C7 C8 169.11(15) . . . . ?
C1 C6 C7 C8 -9.9(2) . . . . ?
S1 N1 C8 C7 51.1(2) . . . . ?
N2 C7 C8 N1 164.54(16) . . . . ?
C6 C7 C8 N1 -15.3(2) . . . . ?
N2 N3 C9 C10 177.96(14) . . . . ?
N3 C9 C10 C15 -5.6(2) . . . . ?
N3 C9 C10 C11 174.50(15) . . . . ?
C16 O3 C11 C12 3.2(2) . . . . ?
C16 O3 C11 C10 -177.21(15) . . . . ?
C15 C10 C11 O3 -178.68(13) . . . . ?
C9 C10 C11 O3 1.2(2) . . . . ?
C15 C10 C11 C12 0.9(2) . . . . ?
C9 C10 C11 C12 -179.25(14) . . . . ?
O3 C11 C12 C13 -179.86(16) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C11 C12 C13 C14 -1.5(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C10 0.6(3) . . . . ?
C11 C10 C15 C14 -1.5(2) . . . . ?
C9 C10 C15 C14 178.63(15) . . . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 76.51
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.119
_refine_diff_density_min -0.319
_refine_diff_density_rms 0.031
_database_code_depnum_ccdc_archive 'CCDC 968351'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(3-methoxy-benzylidene)-hydrazine
;
_chemical_name_common
;
N-(1,1-Dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(3-methoxy-benzylidene)-hydrazine
;
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H15 N3 O3 S'
_chemical_formula_sum 'C16 H15 N3 O3 S'
_chemical_formula_weight 329.37
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 triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.2437(4)
_cell_length_b 9.5959(5)
_cell_length_c 11.1377(6)
_cell_angle_alpha 95.383(4)
_cell_angle_beta 107.003(4)
_cell_angle_gamma 112.475(5)
_cell_volume 757.18(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 4254
_cell_measurement_theta_min 4.2646
_cell_measurement_theta_max 76.3547
_exptl_crystal_description rod
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.37
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.11
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.445
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 344
_exptl_absorpt_coefficient_mu 2.073
_exptl_absorpt_correction_T_min 0.67314
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 6708
_diffrn_reflns_av_R_equivalents 0.0178
_diffrn_reflns_av_sigmaI/netI 0.0186
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 4.27
_diffrn_reflns_theta_max 76.55
_reflns_number_total 3154
_reflns_number_gt 2900
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0681P)^2^+0.1363P] 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 3154
_refine_ls_number_parameters 212
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0373
_refine_ls_R_factor_gt 0.0348
_refine_ls_wR_factor_ref 0.1024
_refine_ls_wR_factor_gt 0.0991
_refine_ls_goodness_of_fit_ref 0.962
_refine_ls_restrained_S_all 0.962
_refine_ls_shift/su_max 0.000
_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 0.32265(4) 0.61228(4) 0.32907(3) 0.04143(12) Uani 1 1 d . . .
O1 O 0.41080(15) 0.77725(13) 0.34890(12) 0.0572(3) Uani 1 1 d . . .
O2 O 0.38704(16) 0.52146(15) 0.26361(12) 0.0573(3) Uani 1 1 d . . .
O3 O 0.27840(17) -0.00570(17) 0.89606(12) 0.0670(4) Uani 1 1 d . . .
N3 N -0.03916(16) 0.20651(13) 0.53402(11) 0.0405(3) Uani 1 1 d . . .
N2 N -0.11288(15) 0.26522(13) 0.43131(11) 0.0388(2) Uani 1 1 d . . .
N1 N 0.33797(15) 0.57374(14) 0.46953(11) 0.0421(3) Uani 1 1 d . . .
C9 C 0.22286(18) 0.41132(16) 0.46516(14) 0.0411(3) Uani 1 1 d . . .
H9A H 0.2459 0.3969 0.5526 0.049 Uiso 1 1 calc R . .
H9B H 0.2607 0.3448 0.4201 0.049 Uiso 1 1 calc R . .
C2 C 0.07797(18) 0.54415(15) 0.24882(12) 0.0376(3) Uani 1 1 d . . .
C7 C -0.04813(17) 0.43145(15) 0.29000(12) 0.0358(3) Uani 1 1 d . . .
C8 C 0.01455(17) 0.36298(14) 0.39834(12) 0.0343(3) Uani 1 1 d . . .
C11 C -0.12128(19) 0.02337(15) 0.66161(13) 0.0393(3) Uani 1 1 d . . .
C10 C -0.16667(19) 0.09682(15) 0.55564(13) 0.0401(3) Uani 1 1 d . . .
H10 H -0.2915 0.0628 0.5027 0.048 Uiso 1 1 calc R . .
C3 C 0.0170(2) 0.60771(19) 0.14801(15) 0.0495(3) Uani 1 1 d . . .
H3 H 0.1037 0.6823 0.1229 0.059 Uiso 1 1 calc R . .
C16 C -0.2646(2) -0.06979(17) 0.69976(15) 0.0481(3) Uani 1 1 d . . .
H16 H -0.3879 -0.0861 0.6571 0.058 Uiso 1 1 calc R . .
C12 C 0.0645(2) 0.04859(16) 0.72625(13) 0.0422(3) Uani 1 1 d . . .
H12 H 0.1608 0.1119 0.7016 0.051 Uiso 1 1 calc R . .
C6 C -0.2402(2) 0.38456(19) 0.22332(15) 0.0494(3) Uani 1 1 d . . .
H6 H -0.3282 0.3089 0.2467 0.059 Uiso 1 1 calc R . .
C13 C 0.1033(2) -0.02136(18) 0.82681(14) 0.0462(3) Uani 1 1 d . . .
C14 C -0.0406(2) -0.11543(19) 0.86457(16) 0.0540(4) Uani 1 1 d . . .
H14 H -0.0139 -0.1628 0.9321 0.065 Uiso 1 1 calc R . .
C5 C -0.3007(2) 0.4487(2) 0.12364(17) 0.0600(4) Uani 1 1 d . . .
H5 H -0.4288 0.4169 0.0818 0.072 Uiso 1 1 calc R . .
C15 C -0.2229(2) -0.13804(19) 0.80140(17) 0.0556(4) Uani 1 1 d . . .
H15 H -0.3185 -0.1997 0.8274 0.067 Uiso 1 1 calc R . .
C4 C -0.1737(2) 0.5597(2) 0.08480(16) 0.0589(4) Uani 1 1 d . . .
H4 H -0.2160 0.6017 0.0170 0.071 Uiso 1 1 calc R . .
C17 C 0.4265(3) 0.0772(3) 0.8535(2) 0.0706(5) Uani 1 1 d . . .
H17A H 0.3974 0.0281 0.7659 0.106 Uiso 1 1 calc R . .
H17B H 0.5413 0.0776 0.9077 0.106 Uiso 1 1 calc R . .
H17C H 0.4411 0.1819 0.8582 0.106 Uiso 1 1 calc R . .
H1 H 0.309(3) 0.636(3) 0.513(2) 0.085 Uiso 1 1 d . . .
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 0.03287(18) 0.0474(2) 0.0480(2) 0.01874(14) 0.01817(14) 0.01672(14)
O1 0.0460(6) 0.0491(6) 0.0718(7) 0.0241(5) 0.0225(5) 0.0123(5)
O2 0.0519(6) 0.0738(7) 0.0640(7) 0.0223(6) 0.0325(5) 0.0349(6)
O3 0.0558(7) 0.0998(10) 0.0590(7) 0.0480(7) 0.0217(5) 0.0395(7)
N3 0.0384(6) 0.0434(6) 0.0409(6) 0.0178(5) 0.0122(5) 0.0186(5)
N2 0.0349(5) 0.0414(6) 0.0393(6) 0.0160(4) 0.0105(4) 0.0161(4)
N1 0.0301(5) 0.0486(6) 0.0439(6) 0.0148(5) 0.0106(4) 0.0141(5)
C9 0.0309(6) 0.0495(7) 0.0465(7) 0.0212(6) 0.0122(5) 0.0199(5)
C2 0.0368(6) 0.0424(6) 0.0375(6) 0.0134(5) 0.0140(5) 0.0194(5)
C7 0.0335(6) 0.0403(6) 0.0350(6) 0.0117(5) 0.0106(5) 0.0178(5)
C8 0.0316(6) 0.0367(6) 0.0355(6) 0.0101(5) 0.0108(5) 0.0161(5)
C11 0.0442(7) 0.0350(6) 0.0403(7) 0.0118(5) 0.0161(5) 0.0173(5)
C10 0.0380(6) 0.0392(6) 0.0422(7) 0.0129(5) 0.0129(5) 0.0161(5)
C3 0.0506(8) 0.0572(8) 0.0472(8) 0.0264(7) 0.0197(6) 0.0250(7)
C16 0.0438(7) 0.0426(7) 0.0556(8) 0.0166(6) 0.0183(6) 0.0147(6)
C12 0.0453(7) 0.0442(7) 0.0423(7) 0.0180(6) 0.0191(6) 0.0202(6)
C6 0.0342(7) 0.0595(9) 0.0494(8) 0.0225(7) 0.0093(6) 0.0170(6)
C13 0.0502(8) 0.0530(8) 0.0416(7) 0.0193(6) 0.0173(6) 0.0260(6)
C14 0.0626(9) 0.0571(9) 0.0505(8) 0.0293(7) 0.0255(7) 0.0264(7)
C5 0.0405(7) 0.0804(11) 0.0553(9) 0.0293(8) 0.0058(7) 0.0274(8)
C15 0.0545(9) 0.0536(9) 0.0614(9) 0.0284(7) 0.0282(7) 0.0170(7)
C4 0.0569(9) 0.0763(11) 0.0499(8) 0.0339(8) 0.0126(7) 0.0356(8)
C17 0.0475(9) 0.0992(15) 0.0683(11) 0.0412(10) 0.0187(8) 0.0313(9)
_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 O2 1.4260(11) . ?
S1 O1 1.4297(11) . ?
S1 N1 1.6213(12) . ?
S1 C2 1.7671(13) . ?
O3 C13 1.3644(18) . ?
O3 C17 1.419(2) . ?
N3 C10 1.2730(17) . ?
N3 N2 1.4041(14) . ?
N2 C8 1.2865(17) . ?
N1 C9 1.4697(18) . ?
N1 H1 0.87(2) . ?
C9 C8 1.5155(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 C3 1.3850(18) . ?
C2 C7 1.4046(18) . ?
C7 C6 1.4019(18) . ?
C7 C8 1.4827(16) . ?
C11 C16 1.390(2) . ?
C11 C12 1.4002(19) . ?
C11 C10 1.4592(18) . ?
C10 H10 0.9300 . ?
C3 C4 1.385(2) . ?
C3 H3 0.9300 . ?
C16 C15 1.383(2) . ?
C16 H16 0.9300 . ?
C12 C13 1.3797(19) . ?
C12 H12 0.9300 . ?
C6 C5 1.378(2) . ?
C6 H6 0.9300 . ?
C13 C14 1.394(2) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C5 C4 1.384(2) . ?
C5 H5 0.9300 . ?
C15 H15 0.9300 . ?
C4 H4 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
O2 S1 O1 118.95(7) . . ?
O2 S1 N1 108.86(7) . . ?
O1 S1 N1 107.24(7) . . ?
O2 S1 C2 108.46(7) . . ?
O1 S1 C2 109.16(7) . . ?
N1 S1 C2 102.99(6) . . ?
C13 O3 C17 117.07(12) . . ?
C10 N3 N2 112.44(11) . . ?
C8 N2 N3 113.08(10) . . ?
C9 N1 S1 114.40(9) . . ?
C9 N1 H1 110.6(16) . . ?
S1 N1 H1 108.9(16) . . ?
N1 C9 C8 112.58(10) . . ?
N1 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C3 C2 C7 122.02(12) . . ?
C3 C2 S1 118.09(11) . . ?
C7 C2 S1 119.87(10) . . ?
C6 C7 C2 116.84(12) . . ?
C6 C7 C8 120.38(12) . . ?
C2 C7 C8 122.78(11) . . ?
N2 C8 C7 117.54(11) . . ?
N2 C8 C9 123.28(11) . . ?
C7 C8 C9 119.17(11) . . ?
C16 C11 C12 120.14(13) . . ?
C16 C11 C10 119.13(13) . . ?
C12 C11 C10 120.71(12) . . ?
N3 C10 C11 121.44(12) . . ?
N3 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C2 C3 C4 119.70(14) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C15 C16 C11 119.67(14) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C13 C12 C11 119.42(13) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C5 C6 C7 121.08(14) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
O3 C13 C12 124.47(14) . . ?
O3 C13 C14 115.14(13) . . ?
C12 C13 C14 120.39(14) . . ?
C15 C14 C13 119.79(14) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C6 C5 C4 121.04(14) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C14 C15 C16 120.58(14) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C3 C4 C5 119.31(14) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C10 N3 N2 C8 -172.19(12) . . . . ?
O2 S1 N1 C9 -61.39(11) . . . . ?
O1 S1 N1 C9 168.69(9) . . . . ?
C2 S1 N1 C9 53.58(10) . . . . ?
S1 N1 C9 C8 -62.17(14) . . . . ?
O2 S1 C2 C3 -88.60(13) . . . . ?
O1 S1 C2 C3 42.41(13) . . . . ?
N1 S1 C2 C3 156.14(12) . . . . ?
O2 S1 C2 C7 92.92(12) . . . . ?
O1 S1 C2 C7 -136.06(11) . . . . ?
N1 S1 C2 C7 -22.34(12) . . . . ?
C3 C2 C7 C6 0.6(2) . . . . ?
S1 C2 C7 C6 178.99(11) . . . . ?
C3 C2 C7 C8 -179.52(12) . . . . ?
S1 C2 C7 C8 -1.11(18) . . . . ?
N3 N2 C8 C7 179.59(10) . . . . ?
N3 N2 C8 C9 -0.89(18) . . . . ?
C6 C7 C8 N2 -2.84(19) . . . . ?
C2 C7 C8 N2 177.26(12) . . . . ?
C6 C7 C8 C9 177.62(13) . . . . ?
C2 C7 C8 C9 -2.29(19) . . . . ?
N1 C9 C8 N2 -146.20(13) . . . . ?
N1 C9 C8 C7 33.32(17) . . . . ?
N2 N3 C10 C11 -177.52(11) . . . . ?
C16 C11 C10 N3 165.53(14) . . . . ?
C12 C11 C10 N3 -13.1(2) . . . . ?
C7 C2 C3 C4 -0.1(2) . . . . ?
S1 C2 C3 C4 -178.53(13) . . . . ?
C12 C11 C16 C15 -0.3(2) . . . . ?
C10 C11 C16 C15 -178.98(14) . . . . ?
C16 C11 C12 C13 0.8(2) . . . . ?
C10 C11 C12 C13 179.45(13) . . . . ?
C2 C7 C6 C5 -1.0(2) . . . . ?
C8 C7 C6 C5 179.04(15) . . . . ?
C17 O3 C13 C12 -5.8(3) . . . . ?
C17 O3 C13 C14 174.35(17) . . . . ?
C11 C12 C13 O3 179.66(14) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
O3 C13 C14 C15 179.53(15) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C7 C6 C5 C4 1.1(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C11 C16 C15 C14 -0.5(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full 76.55
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max 0.185
_refine_diff_density_min -0.378
_refine_diff_density_rms 0.042
_database_code_depnum_ccdc_archive 'CCDC 968352'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-(2-Ethyl-1,1-dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(4-methyl-benzylidene)-hydrazine
;
_chemical_name_common
;
N-(2-Ethyl-1,1-dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(4-methyl-benzylidene)-hydrazine
;
_chemical_melting_point ?
_chemical_formula_moiety 'C18 H19 N3 O2 S'
_chemical_formula_sum 'C18 H19 N3 O2 S'
_chemical_formula_weight 341.42
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 monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
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 8.4612(3)
_cell_length_b 8.3500(3)
_cell_length_c 24.9103(9)
_cell_angle_alpha 90.00
_cell_angle_beta 94.490(3)
_cell_angle_gamma 90.00
_cell_volume 1754.54(11)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 6006
_cell_measurement_theta_min 3.5566
_cell_measurement_theta_max 76.4475
_exptl_crystal_description prismatic
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.26
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.17
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.293
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 720
_exptl_absorpt_coefficient_mu 1.762
_exptl_absorpt_correction_T_min 0.57807
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16129
_diffrn_reflns_av_R_equivalents 0.0423
_diffrn_reflns_av_sigmaI/netI 0.0252
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -31
_diffrn_reflns_limit_l_max 29
_diffrn_reflns_theta_min 3.56
_diffrn_reflns_theta_max 76.65
_reflns_number_total 3674
_reflns_number_gt 3109
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0986P)^2^+0.2888P] 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 3674
_refine_ls_number_parameters 219
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0608
_refine_ls_R_factor_gt 0.0533
_refine_ls_wR_factor_ref 0.1637
_refine_ls_wR_factor_gt 0.1526
_refine_ls_goodness_of_fit_ref 1.041
_refine_ls_restrained_S_all 1.041
_refine_ls_shift/su_max 0.031
_refine_ls_shift/su_mean 0.001
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 0.60721(6) 0.92794(6) 0.11390(2) 0.0615(2) Uani 1 1 d . . .
O1 O 0.6001(3) 1.04017(18) 0.15702(7) 0.0852(6) Uani 1 1 d . . .
O2 O 0.7415(2) 0.9317(2) 0.08258(8) 0.0841(5) Uani 1 1 d . . .
N1 N 0.4492(2) 0.94700(18) 0.07254(6) 0.0553(4) Uani 1 1 d . . .
N2 N 0.3298(2) 0.5427(2) 0.03441(7) 0.0597(4) Uani 1 1 d . . .
N3 N 0.2542(2) 0.5923(2) -0.01519(7) 0.0668(5) Uani 1 1 d . . .
C1 C 0.5882(2) 0.7329(2) 0.13993(7) 0.0514(4) Uani 1 1 d . . .
C2 C 0.6641(3) 0.6994(3) 0.18997(8) 0.0637(5) Uani 1 1 d . . .
H2 H 0.7218 0.7786 0.2090 0.076 Uiso 1 1 calc R . .
C3 C 0.6537(3) 0.5475(3) 0.21138(8) 0.0681(6) Uani 1 1 d . . .
H3 H 0.7039 0.5239 0.2450 0.082 Uiso 1 1 calc R . .
C4 C 0.5682(3) 0.4312(2) 0.18256(9) 0.0670(6) Uani 1 1 d . . .
H4 H 0.5623 0.3285 0.1968 0.080 Uiso 1 1 calc R . .
C5 C 0.4913(3) 0.4648(2) 0.13299(8) 0.0595(5) Uani 1 1 d . . .
H5 H 0.4335 0.3848 0.1144 0.071 Uiso 1 1 calc R . .
C6 C 0.4992(2) 0.6177(2) 0.11037(7) 0.0479(4) Uani 1 1 d . . .
C7 C 0.4167(2) 0.6544(2) 0.05709(7) 0.0488(4) Uani 1 1 d . . .
C8 C 0.4404(3) 0.8174(2) 0.03244(7) 0.0570(4) Uani 1 1 d . . .
H8A H 0.5375 0.8164 0.0142 0.068 Uiso 1 1 calc R . .
H8B H 0.3533 0.8388 0.0057 0.068 Uiso 1 1 calc R . .
C9 C 0.1739(2) 0.4821(3) -0.03854(8) 0.0567(4) Uani 1 1 d . . .
H9 H 0.1709 0.3819 -0.0224 0.068 Uiso 1 1 calc R . .
C10 C 0.0851(2) 0.5083(2) -0.09067(7) 0.0549(4) Uani 1 1 d . . .
C11 C 0.0868(3) 0.6543(3) -0.11707(9) 0.0693(6) Uani 1 1 d . . .
H11 H 0.1452 0.7392 -0.1016 0.083 Uiso 1 1 calc R . .
C12 C 0.0018(3) 0.6742(3) -0.16636(9) 0.0770(6) Uani 1 1 d . . .
H12 H 0.0033 0.7728 -0.1837 0.092 Uiso 1 1 calc R . .
C13 C -0.0856(3) 0.5488(3) -0.19038(9) 0.0714(6) Uani 1 1 d . . .
C14 C -0.0853(3) 0.4048(4) -0.16418(10) 0.0801(7) Uani 1 1 d . . .
H14 H -0.1426 0.3196 -0.1799 0.096 Uiso 1 1 calc R . .
C15 C -0.0014(3) 0.3833(3) -0.11460(9) 0.0714(6) Uani 1 1 d . . .
H15 H -0.0033 0.2845 -0.0974 0.086 Uiso 1 1 calc R . .
C16 C -0.1760(4) 0.5702(5) -0.24474(11) 0.1039(11) Uani 1 1 d . . .
H16A H -0.2243 0.6743 -0.2466 0.156 Uiso 1 1 calc R . .
H16B H -0.2567 0.4895 -0.2495 0.156 Uiso 1 1 calc R . .
H16C H -0.1044 0.5604 -0.2726 0.156 Uiso 1 1 calc R . .
C17 C 0.2987(3) 0.9782(3) 0.09720(9) 0.0690(5) Uani 1 1 d . . .
H17A H 0.3178 1.0532 0.1267 0.083 Uiso 1 1 calc R . .
H17B H 0.2601 0.8791 0.1117 0.083 Uiso 1 1 calc R . .
C18 C 0.1759(4) 1.0451(6) 0.05731(15) 0.1217(14) Uani 1 1 d . . .
H18A H 0.2111 1.1465 0.0445 0.183 Uiso 1 1 calc R . .
H18B H 0.0785 1.0594 0.0741 0.183 Uiso 1 1 calc R . .
H18C H 0.1588 0.9724 0.0275 0.183 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 0.0745(3) 0.0483(3) 0.0591(3) 0.00542(18) -0.0107(2) -0.0127(2)
O1 0.1307(15) 0.0497(8) 0.0700(10) -0.0064(7) -0.0251(10) -0.0097(9)
O2 0.0690(10) 0.0875(12) 0.0949(12) 0.0254(9) 0.0014(9) -0.0196(8)
N1 0.0704(10) 0.0456(8) 0.0489(8) 0.0051(6) -0.0029(7) -0.0029(7)
N2 0.0694(10) 0.0567(9) 0.0504(8) -0.0003(7) -0.0118(7) -0.0038(7)
N3 0.0810(11) 0.0634(10) 0.0527(9) -0.0003(7) -0.0166(8) -0.0055(8)
C1 0.0594(10) 0.0452(9) 0.0482(9) 0.0003(7) -0.0034(7) -0.0013(7)
C2 0.0770(13) 0.0563(11) 0.0545(10) -0.0018(8) -0.0164(9) -0.0020(9)
C3 0.0907(15) 0.0599(12) 0.0507(10) 0.0046(9) -0.0135(10) 0.0098(10)
C4 0.0909(15) 0.0471(10) 0.0609(12) 0.0082(8) -0.0071(10) 0.0037(9)
C5 0.0753(12) 0.0449(9) 0.0567(10) 0.0008(8) -0.0042(9) -0.0015(8)
C6 0.0531(9) 0.0461(8) 0.0438(8) -0.0014(7) 0.0003(7) 0.0002(7)
C7 0.0557(9) 0.0481(9) 0.0419(8) -0.0020(6) 0.0006(7) -0.0005(7)
C8 0.0710(11) 0.0559(10) 0.0431(8) 0.0047(7) -0.0018(8) -0.0053(8)
C9 0.0575(10) 0.0585(11) 0.0525(10) -0.0012(8) -0.0054(8) -0.0022(8)
C10 0.0508(9) 0.0625(11) 0.0503(10) -0.0035(8) -0.0035(7) -0.0001(8)
C11 0.0765(13) 0.0658(13) 0.0634(12) 0.0002(10) -0.0086(10) -0.0039(10)
C12 0.0857(15) 0.0769(15) 0.0662(13) 0.0145(11) -0.0074(11) 0.0044(12)
C13 0.0569(11) 0.1048(18) 0.0511(11) 0.0067(11) -0.0059(8) 0.0016(11)
C14 0.0760(14) 0.0976(18) 0.0629(13) -0.0014(12) -0.0178(11) -0.0236(13)
C15 0.0775(13) 0.0705(13) 0.0629(12) 0.0053(10) -0.0158(10) -0.0178(11)
C16 0.0889(18) 0.156(3) 0.0632(14) 0.0208(17) -0.0204(13) -0.0060(18)
C17 0.0794(14) 0.0652(13) 0.0628(12) 0.0049(10) 0.0070(10) 0.0061(10)
C18 0.096(2) 0.171(4) 0.098(2) 0.040(2) 0.0083(17) 0.052(2)
_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 O2 1.4283(19) . ?
S1 O1 1.4301(17) . ?
S1 N1 1.6309(17) . ?
S1 C1 1.7645(18) . ?
N1 C8 1.470(2) . ?
N1 C17 1.479(3) . ?
N2 C7 1.290(2) . ?
N2 N3 1.408(2) . ?
N3 C9 1.259(3) . ?
C1 C2 1.386(2) . ?
C1 C6 1.396(2) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.482(2) . ?
C7 C8 1.513(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.465(2) . ?
C9 H9 0.9300 . ?
C10 C15 1.383(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(4) . ?
C13 C16 1.513(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.489(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
O2 S1 O1 118.56(12) . . ?
O2 S1 N1 107.50(10) . . ?
O1 S1 N1 109.26(10) . . ?
O2 S1 C1 108.67(10) . . ?
O1 S1 C1 108.56(9) . . ?
N1 S1 C1 103.20(8) . . ?
C8 N1 C17 114.36(17) . . ?
C8 N1 S1 110.65(13) . . ?
C17 N1 S1 116.39(13) . . ?
C7 N2 N3 112.07(17) . . ?
C9 N3 N2 112.46(18) . . ?
C2 C1 C6 121.87(17) . . ?
C2 C1 S1 117.91(14) . . ?
C6 C1 S1 120.21(13) . . ?
C3 C2 C1 119.61(18) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.52(18) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.95(19) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.81(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.23(16) . . ?
C1 C6 C7 121.77(16) . . ?
C5 C6 C7 121.00(16) . . ?
N2 C7 C6 117.06(16) . . ?
N2 C7 C8 124.16(16) . . ?
C6 C7 C8 118.77(15) . . ?
N1 C8 C7 112.80(14) . . ?
N1 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N3 C9 C10 121.42(19) . . ?
N3 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C15 C10 C11 118.97(19) . . ?
C15 C10 C9 119.13(19) . . ?
C11 C10 C9 121.90(18) . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.41(19) . . ?
C14 C13 C16 120.8(2) . . ?
C12 C13 C16 120.8(3) . . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 120.2(2) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 111.5(2) . . ?
N1 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N1 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O2 S1 N1 C8 58.89(15) . . . . ?
O1 S1 N1 C8 -171.24(13) . . . . ?
C1 S1 N1 C8 -55.87(14) . . . . ?
O2 S1 N1 C17 -168.34(15) . . . . ?
O1 S1 N1 C17 -38.46(18) . . . . ?
C1 S1 N1 C17 76.90(16) . . . . ?
C7 N2 N3 C9 177.48(19) . . . . ?
O2 S1 C1 C2 90.94(19) . . . . ?
O1 S1 C1 C2 -39.3(2) . . . . ?
N1 S1 C1 C2 -155.15(17) . . . . ?
O2 S1 C1 C6 -88.96(18) . . . . ?
O1 S1 C1 C6 140.81(17) . . . . ?
N1 S1 C1 C6 24.95(18) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
S1 C1 C2 C3 -179.20(18) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
S1 C1 C6 C5 178.96(15) . . . . ?
C2 C1 C6 C7 179.34(18) . . . . ?
S1 C1 C6 C7 -0.8(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -180.0(2) . . . . ?
N3 N2 C7 C6 178.44(16) . . . . ?
N3 N2 C7 C8 -2.3(3) . . . . ?
C1 C6 C7 N2 -175.96(18) . . . . ?
C5 C6 C7 N2 4.3(3) . . . . ?
C1 C6 C7 C8 4.8(3) . . . . ?
C5 C6 C7 C8 -174.96(18) . . . . ?
C17 N1 C8 C7 -67.9(2) . . . . ?
S1 N1 C8 C7 65.85(18) . . . . ?
N2 C7 C8 N1 142.89(19) . . . . ?
C6 C7 C8 N1 -37.9(2) . . . . ?
N2 N3 C9 C10 179.77(18) . . . . ?
N3 C9 C10 C15 -179.9(2) . . . . ?
N3 C9 C10 C11 0.9(3) . . . . ?
C15 C10 C11 C12 0.6(4) . . . . ?
C9 C10 C11 C12 179.7(2) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C11 C12 C13 C16 -178.9(2) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C16 C13 C14 C15 179.3(3) . . . . ?
C11 C10 C15 C14 -0.2(4) . . . . ?
C9 C10 C15 C14 -179.4(2) . . . . ?
C13 C14 C15 C10 -0.3(4) . . . . ?
C8 N1 C17 C18 -67.5(3) . . . . ?
S1 N1 C17 C18 161.5(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 76.65
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 0.443
_refine_diff_density_min -0.285
_refine_diff_density_rms 0.057
_database_code_depnum_ccdc_archive 'CCDC 968353'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-(2-Ethyl-1,1-dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(4-methyl-benzylidene)-hydrazine
;
_chemical_name_common
;
N-(2-Ethyl-1,1-dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(4-methyl-benzylidene)-hydrazine
;
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H13 N3 O2 S'
_chemical_formula_sum 'C15 H13 N3 O2 S'
_chemical_formula_weight 299.34
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 triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.5087(5)
_cell_length_b 9.0853(6)
_cell_length_c 19.3952(8)
_cell_angle_alpha 89.564(4)
_cell_angle_beta 79.817(4)
_cell_angle_gamma 73.739(6)
_cell_volume 1415.28(14)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 5132
_cell_measurement_theta_min 4.6335
_cell_measurement_theta_max 76.4550
_exptl_crystal_description needle
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.405
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 624
_exptl_absorpt_coefficient_mu 2.107
_exptl_absorpt_correction_T_min 0.69003
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 27929
_diffrn_reflns_av_R_equivalents 0.0605
_diffrn_reflns_av_sigmaI/netI 0.0444
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 4.64
_diffrn_reflns_theta_max 76.66
_reflns_number_total 5889
_reflns_number_gt 3807
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.1559P)^2^+0.3380P] 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 5889
_refine_ls_number_parameters 385
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1163
_refine_ls_R_factor_gt 0.0851
_refine_ls_wR_factor_ref 0.2664
_refine_ls_wR_factor_gt 0.2201
_refine_ls_goodness_of_fit_ref 1.050
_refine_ls_restrained_S_all 1.050
_refine_ls_shift/su_max 0.000
_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 0.44655(11) 0.94167(11) 0.20759(5) 0.0596(3) Uani 1 1 d . . .
S2 S 0.41550(13) 1.59420(12) -0.28695(5) 0.0650(3) Uani 1 1 d . . .
O1 O 0.3777(4) 0.9520(4) 0.28134(14) 0.0750(8) Uani 1 1 d . . .
O2 O 0.5575(4) 0.7981(4) 0.17901(17) 0.0805(9) Uani 1 1 d . . .
O3 O 0.3477(4) 1.6160(4) -0.21341(15) 0.0817(9) Uani 1 1 d . . .
O4 O 0.5229(4) 1.6835(4) -0.31546(17) 0.0838(9) Uani 1 1 d . . .
N1 N 0.5428(4) 1.0701(4) 0.19196(18) 0.0651(9) Uani 1 1 d . . .
N2 N 0.4508(4) 1.2155(4) 0.02139(17) 0.0610(8) Uani 1 1 d . . .
N3 N 0.5988(4) 1.2600(4) 0.00166(17) 0.0645(8) Uani 1 1 d . . .
N4 N 0.5147(5) 1.4174(4) -0.30290(19) 0.0694(9) Uani 1 1 d . . .
N5 N 0.4261(4) 1.3264(4) -0.47444(18) 0.0653(8) Uani 1 1 d . . .
N6 N 0.5762(4) 1.2078(4) -0.49448(17) 0.0664(8) Uani 1 1 d . . .
C1 C 0.2846(4) 0.9978(4) 0.15893(17) 0.0517(8) Uani 1 1 d . . .
C2 C 0.1438(4) 0.9494(5) 0.1811(2) 0.0590(9) Uani 1 1 d . . .
H2 H 0.1369 0.8903 0.2203 0.071 Uiso 1 1 calc R . .
C3 C 0.0148(5) 0.9894(5) 0.1447(2) 0.0669(10) Uani 1 1 d . . .
H3 H -0.0793 0.9561 0.1588 0.080 Uiso 1 1 calc R . .
C4 C 0.0245(5) 1.0790(5) 0.0874(2) 0.0711(11) Uani 1 1 d . . .
H4 H -0.0637 1.1064 0.0631 0.085 Uiso 1 1 calc R . .
C5 C 0.1641(5) 1.1284(5) 0.0655(2) 0.0639(10) Uani 1 1 d . . .
H5 H 0.1692 1.1885 0.0266 0.077 Uiso 1 1 calc R . .
C6 C 0.2977(4) 1.0886(4) 0.10143(19) 0.0533(8) Uani 1 1 d . . .
C7 C 0.4472(4) 1.1416(4) 0.07758(19) 0.0552(8) Uani 1 1 d . . .
C8 C 0.5889(5) 1.1015(6) 0.1186(2) 0.0693(11) Uani 1 1 d . . .
H8A H 0.6734 1.0119 0.0957 0.083 Uiso 1 1 calc R . .
H8B H 0.6386 1.1857 0.1164 0.083 Uiso 1 1 calc R . .
C9 C 0.5930(5) 1.3391(5) -0.0524(2) 0.0612(9) Uani 1 1 d . . .
H9 H 0.4967 1.3618 -0.0717 0.073 Uiso 1 1 calc R . .
C10 C 0.7308(5) 1.3962(4) -0.0859(2) 0.0601(9) Uani 1 1 d . . .
C11 C 0.8726(6) 1.3779(6) -0.0573(2) 0.0783(12) Uani 1 1 d . . .
H11 H 0.8784 1.3341 -0.0139 0.094 Uiso 1 1 calc R . .
C12 C 1.0061(6) 1.4240(7) -0.0924(3) 0.0949(16) Uani 1 1 d . . .
H12 H 1.1026 1.4077 -0.0736 0.114 Uiso 1 1 calc R . .
C13 C 0.9950(7) 1.4937(7) -0.1547(3) 0.0962(16) Uani 1 1 d . . .
H13 H 1.0833 1.5273 -0.1777 0.115 Uiso 1 1 calc R . .
C14 C 0.8555(8) 1.5144(6) -0.1837(3) 0.0926(16) Uani 1 1 d . . .
H14 H 0.8500 1.5606 -0.2265 0.111 Uiso 1 1 calc R . .
C15 C 0.7221(6) 1.4665(5) -0.1494(2) 0.0745(11) Uani 1 1 d . . .
H15 H 0.6268 1.4816 -0.1689 0.089 Uiso 1 1 calc R . .
C16 C 0.2529(5) 1.6226(4) -0.33479(19) 0.0588(9) Uani 1 1 d . . .
C17 C 0.1083(5) 1.7410(5) -0.3121(2) 0.0729(11) Uani 1 1 d . . .
H17 H 0.1005 1.8043 -0.2734 0.087 Uiso 1 1 calc R . .
C18 C -0.0222(6) 1.7638(6) -0.3471(3) 0.0817(13) Uani 1 1 d . . .
H18 H -0.1187 1.8431 -0.3322 0.098 Uiso 1 1 calc R . .
C19 C -0.0118(5) 1.6707(6) -0.4039(3) 0.0802(13) Uani 1 1 d . . .
H19 H -0.1014 1.6872 -0.4271 0.096 Uiso 1 1 calc R . .
C20 C 0.1306(5) 1.5523(5) -0.4270(2) 0.0702(10) Uani 1 1 d . . .
H20 H 0.1356 1.4894 -0.4654 0.084 Uiso 1 1 calc R . .
C21 C 0.2681(5) 1.5262(4) -0.3928(2) 0.0595(9) Uani 1 1 d . . .
C22 C 0.4209(5) 1.3991(4) -0.4183(2) 0.0587(9) Uani 1 1 d . . .
C23 C 0.5625(5) 1.3657(5) -0.3770(2) 0.0721(11) Uani 1 1 d . . .
H23A H 0.6146 1.2558 -0.3798 0.087 Uiso 1 1 calc R . .
H23B H 0.6453 1.4140 -0.3995 0.087 Uiso 1 1 calc R . .
C24 C 0.5735(5) 1.1314(5) -0.5480(2) 0.0610(9) Uani 1 1 d . . .
H24 H 0.4781 1.1573 -0.5678 0.073 Uiso 1 1 calc R . .
C25 C 0.7152(5) 1.0026(4) -0.58036(18) 0.0566(8) Uani 1 1 d . . .
C26 C 0.8510(5) 0.9460(6) -0.5477(2) 0.0736(11) Uani 1 1 d . . .
H26 H 0.8519 0.9870 -0.5040 0.088 Uiso 1 1 calc R . .
C27 C 0.9854(6) 0.8281(6) -0.5803(3) 0.0835(13) Uani 1 1 d . . .
H27 H 1.0769 0.7906 -0.5586 0.100 Uiso 1 1 calc R . .
C28 C 0.9839(6) 0.7664(6) -0.6446(2) 0.0800(12) Uani 1 1 d . . .
H28 H 1.0749 0.6883 -0.6666 0.096 Uiso 1 1 calc R . .
C29 C 0.8483(6) 0.8203(6) -0.6763(2) 0.0773(12) Uani 1 1 d . . .
H29 H 0.8467 0.7779 -0.7196 0.093 Uiso 1 1 calc R . .
C30 C 0.7141(5) 0.9374(5) -0.6439(2) 0.0688(10) Uani 1 1 d . . .
H30 H 0.6218 0.9725 -0.6654 0.083 Uiso 1 1 calc R . .
H1 H 0.495(6) 1.152(6) 0.216(3) 0.083 Uiso 1 1 d . . .
H4N H 0.473(6) 1.352(6) -0.284(3) 0.083 Uiso 1 1 d . . .
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 0.0566(5) 0.0636(6) 0.0627(6) 0.0051(4) -0.0192(4) -0.0187(4)
S2 0.0728(6) 0.0633(6) 0.0625(6) 0.0014(4) -0.0168(4) -0.0224(5)
O1 0.0735(17) 0.099(2) 0.0596(16) 0.0137(14) -0.0199(13) -0.0313(16)
O2 0.0693(17) 0.0704(19) 0.098(2) -0.0051(16) -0.0289(15) -0.0047(14)
O3 0.092(2) 0.091(2) 0.0602(16) -0.0062(15) -0.0145(14) -0.0224(18)
O4 0.083(2) 0.083(2) 0.096(2) 0.0111(17) -0.0227(17) -0.0368(17)
N1 0.0626(19) 0.082(2) 0.0617(19) 0.0084(16) -0.0208(15) -0.0325(18)
N2 0.0527(16) 0.070(2) 0.0646(18) 0.0017(15) -0.0076(13) -0.0260(15)
N3 0.0594(18) 0.071(2) 0.069(2) 0.0055(16) -0.0107(15) -0.0290(16)
N4 0.080(2) 0.066(2) 0.064(2) 0.0056(16) -0.0228(17) -0.0183(18)
N5 0.0570(17) 0.066(2) 0.071(2) 0.0014(16) -0.0116(14) -0.0136(15)
N6 0.0586(18) 0.072(2) 0.0659(19) -0.0051(16) -0.0101(14) -0.0145(16)
C1 0.0493(17) 0.056(2) 0.0524(18) -0.0053(15) -0.0125(14) -0.0176(15)
C2 0.0558(19) 0.062(2) 0.062(2) 0.0016(17) -0.0078(16) -0.0243(17)
C3 0.052(2) 0.083(3) 0.072(2) 0.003(2) -0.0114(17) -0.029(2)
C4 0.053(2) 0.090(3) 0.077(3) 0.010(2) -0.0223(18) -0.024(2)
C5 0.0544(19) 0.076(3) 0.065(2) 0.0108(19) -0.0187(16) -0.0204(18)
C6 0.0447(16) 0.055(2) 0.0610(19) -0.0035(15) -0.0102(14) -0.0156(15)
C7 0.0512(18) 0.059(2) 0.0570(19) -0.0032(16) -0.0067(15) -0.0194(16)
C8 0.060(2) 0.093(3) 0.067(2) 0.012(2) -0.0183(17) -0.037(2)
C9 0.064(2) 0.062(2) 0.063(2) -0.0030(17) -0.0151(17) -0.0226(18)
C10 0.064(2) 0.058(2) 0.061(2) -0.0040(16) -0.0078(16) -0.0230(17)
C11 0.078(3) 0.091(3) 0.079(3) 0.015(2) -0.018(2) -0.042(3)
C12 0.078(3) 0.111(4) 0.107(4) 0.017(3) -0.019(3) -0.045(3)
C13 0.101(4) 0.102(4) 0.090(4) -0.003(3) 0.011(3) -0.055(3)
C14 0.127(4) 0.084(3) 0.064(3) 0.002(2) 0.008(3) -0.042(3)
C15 0.087(3) 0.077(3) 0.063(2) 0.007(2) -0.016(2) -0.027(2)
C16 0.068(2) 0.057(2) 0.0556(19) 0.0078(16) -0.0128(16) -0.0244(18)
C17 0.075(3) 0.067(3) 0.071(2) 0.001(2) -0.009(2) -0.014(2)
C18 0.067(3) 0.078(3) 0.084(3) 0.001(2) -0.003(2) -0.002(2)
C19 0.063(2) 0.086(3) 0.083(3) 0.003(2) -0.021(2) -0.003(2)
C20 0.069(2) 0.071(3) 0.071(2) -0.0034(19) -0.0193(19) -0.016(2)
C21 0.059(2) 0.055(2) 0.066(2) 0.0078(16) -0.0124(16) -0.0176(17)
C22 0.065(2) 0.055(2) 0.058(2) 0.0030(16) -0.0112(16) -0.0204(17)
C23 0.070(2) 0.071(3) 0.068(2) -0.0070(19) -0.0198(19) -0.003(2)
C24 0.056(2) 0.066(2) 0.063(2) 0.0090(18) -0.0123(16) -0.0195(18)
C25 0.060(2) 0.061(2) 0.0512(18) 0.0040(15) -0.0088(15) -0.0214(17)
C26 0.067(2) 0.088(3) 0.064(2) -0.009(2) -0.0137(18) -0.017(2)
C27 0.064(2) 0.094(3) 0.083(3) -0.010(2) -0.018(2) -0.004(2)
C28 0.080(3) 0.077(3) 0.073(3) -0.005(2) 0.001(2) -0.014(2)
C29 0.093(3) 0.084(3) 0.055(2) -0.007(2) -0.004(2) -0.031(3)
C30 0.070(2) 0.083(3) 0.058(2) 0.0038(19) -0.0155(18) -0.028(2)
_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 O2 1.427(3) . ?
S1 O1 1.440(3) . ?
S1 N1 1.602(3) . ?
S1 C1 1.763(3) . ?
S2 O4 1.424(3) . ?
S2 O3 1.434(3) . ?
S2 N4 1.595(4) . ?
S2 C16 1.758(4) . ?
N1 C8 1.455(5) . ?
N1 H1 0.84(5) . ?
N2 C7 1.276(5) . ?
N2 N3 1.417(4) . ?
N3 C9 1.267(5) . ?
N4 C23 1.466(5) . ?
N4 H4N 0.83(5) . ?
N5 C22 1.266(5) . ?
N5 N6 1.416(4) . ?
N6 C24 1.260(5) . ?
C1 C2 1.387(5) . ?
C1 C6 1.390(5) . ?
C2 C3 1.371(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.481(5) . ?
C7 C8 1.520(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.460(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(6) . ?
C10 C15 1.387(6) . ?
C11 C12 1.385(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.393(6) . ?
C16 C21 1.396(5) . ?
C17 C18 1.368(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.408(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.486(5) . ?
C22 C23 1.522(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.473(5) . ?
C24 H24 0.9300 . ?
C25 C30 1.375(5) . ?
C25 C26 1.387(5) . ?
C26 C27 1.387(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.375(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.370(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.381(6) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
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
O2 S1 O1 117.5(2) . . ?
O2 S1 N1 107.9(2) . . ?
O1 S1 N1 108.25(19) . . ?
O2 S1 C1 109.03(17) . . ?
O1 S1 C1 109.83(16) . . ?
N1 S1 C1 103.38(17) . . ?
O4 S2 O3 117.4(2) . . ?
O4 S2 N4 108.1(2) . . ?
O3 S2 N4 108.2(2) . . ?
O4 S2 C16 108.93(19) . . ?
O3 S2 C16 109.61(19) . . ?
N4 S2 C16 103.69(19) . . ?
C8 N1 S1 116.4(3) . . ?
C8 N1 H1 111(3) . . ?
S1 N1 H1 113(3) . . ?
C7 N2 N3 113.4(3) . . ?
C9 N3 N2 110.9(3) . . ?
C23 N4 S2 116.1(3) . . ?
C23 N4 H4N 104(3) . . ?
S2 N4 H4N 119(4) . . ?
C22 N5 N6 113.1(3) . . ?
C24 N6 N5 111.7(3) . . ?
C2 C1 C6 121.8(3) . . ?
C2 C1 S1 117.2(3) . . ?
C6 C1 S1 120.9(3) . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.6(3) . . ?
C1 C6 C7 122.2(3) . . ?
C5 C6 C7 120.2(3) . . ?
N2 C7 C6 116.9(3) . . ?
N2 C7 C8 123.6(3) . . ?
C6 C7 C8 119.4(3) . . ?
N1 C8 C7 115.4(3) . . ?
N1 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
N1 C8 H8B 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
N3 C9 C10 122.9(4) . . ?
N3 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C11 C10 C15 118.8(4) . . ?
C11 C10 C9 122.0(4) . . ?
C15 C10 C9 119.2(4) . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.7(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 120.1(5) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.0(5) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C21 121.4(4) . . ?
C17 C16 S2 118.1(3) . . ?
C21 C16 S2 120.5(3) . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.5(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 120.7(4) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C21 120.5(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 117.3(4) . . ?
C16 C21 C22 122.6(3) . . ?
C20 C21 C22 120.0(4) . . ?
N5 C22 C21 117.3(4) . . ?
N5 C22 C23 123.8(4) . . ?
C21 C22 C23 118.9(3) . . ?
N4 C23 C22 115.5(3) . . ?
N4 C23 H23A 108.4 . . ?
C22 C23 H23A 108.4 . . ?
N4 C23 H23B 108.4 . . ?
C22 C23 H23B 108.4 . . ?
H23A C23 H23B 107.5 . . ?
N6 C24 C25 122.7(3) . . ?
N6 C24 H24 118.6 . . ?
C25 C24 H24 118.6 . . ?
C30 C25 C26 119.2(4) . . ?
C30 C25 C24 120.0(4) . . ?
C26 C25 C24 120.9(4) . . ?
C27 C26 C25 119.8(4) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C28 C27 C26 120.3(4) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 119.9(4) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.0(4) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C25 C30 C29 120.8(4) . . ?
C25 C30 H30 119.6 . . ?
C29 C30 H30 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
O2 S1 N1 C8 65.2(3) . . . . ?
O1 S1 N1 C8 -166.6(3) . . . . ?
C1 S1 N1 C8 -50.2(3) . . . . ?
C7 N2 N3 C9 -176.9(3) . . . . ?
O4 S2 N4 C23 -64.6(4) . . . . ?
O3 S2 N4 C23 167.3(3) . . . . ?
C16 S2 N4 C23 50.9(3) . . . . ?
C22 N5 N6 C24 175.8(4) . . . . ?
O2 S1 C1 C2 89.8(3) . . . . ?
O1 S1 C1 C2 -40.3(3) . . . . ?
N1 S1 C1 C2 -155.6(3) . . . . ?
O2 S1 C1 C6 -91.2(3) . . . . ?
O1 S1 C1 C6 138.8(3) . . . . ?
N1 S1 C1 C6 23.5(3) . . . . ?
C6 C1 C2 C3 1.3(6) . . . . ?
S1 C1 C2 C3 -179.7(3) . . . . ?
C1 C2 C3 C4 -1.0(6) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C2 C1 C6 C5 -1.0(5) . . . . ?
S1 C1 C6 C5 -180.0(3) . . . . ?
C2 C1 C6 C7 179.6(3) . . . . ?
S1 C1 C6 C7 0.6(5) . . . . ?
C4 C5 C6 C1 0.4(6) . . . . ?
C4 C5 C6 C7 179.8(4) . . . . ?
N3 N2 C7 C6 -179.1(3) . . . . ?
N3 N2 C7 C8 -1.4(5) . . . . ?
C1 C6 C7 N2 175.3(3) . . . . ?
C5 C6 C7 N2 -4.1(5) . . . . ?
C1 C6 C7 C8 -2.5(5) . . . . ?
C5 C6 C7 C8 178.1(4) . . . . ?
S1 N1 C8 C7 54.1(5) . . . . ?
N2 C7 C8 N1 158.1(4) . . . . ?
C6 C7 C8 N1 -24.3(5) . . . . ?
N2 N3 C9 C10 -177.9(3) . . . . ?
N3 C9 C10 C11 -5.3(6) . . . . ?
N3 C9 C10 C15 172.6(4) . . . . ?
C15 C10 C11 C12 -2.2(7) . . . . ?
C9 C10 C11 C12 175.7(5) . . . . ?
C10 C11 C12 C13 2.5(8) . . . . ?
C11 C12 C13 C14 -1.8(9) . . . . ?
C12 C13 C14 C15 0.9(9) . . . . ?
C11 C10 C15 C14 1.3(7) . . . . ?
C9 C10 C15 C14 -176.7(4) . . . . ?
C13 C14 C15 C10 -0.7(8) . . . . ?
O4 S2 C16 C17 -90.2(3) . . . . ?
O3 S2 C16 C17 39.5(4) . . . . ?
N4 S2 C16 C17 154.8(3) . . . . ?
O4 S2 C16 C21 91.2(3) . . . . ?
O3 S2 C16 C21 -139.0(3) . . . . ?
N4 S2 C16 C21 -23.7(4) . . . . ?
C21 C16 C17 C18 0.2(6) . . . . ?
S2 C16 C17 C18 -178.4(4) . . . . ?
C16 C17 C18 C19 0.3(7) . . . . ?
C17 C18 C19 C20 -0.1(8) . . . . ?
C18 C19 C20 C21 -0.5(7) . . . . ?
C17 C16 C21 C20 -0.8(6) . . . . ?
S2 C16 C21 C20 177.7(3) . . . . ?
C17 C16 C21 C22 179.9(4) . . . . ?
S2 C16 C21 C22 -1.7(5) . . . . ?
C19 C20 C21 C16 0.9(6) . . . . ?
C19 C20 C21 C22 -179.7(4) . . . . ?
N6 N5 C22 C21 180.0(3) . . . . ?
N6 N5 C22 C23 1.3(6) . . . . ?
C16 C21 C22 N5 -174.7(4) . . . . ?
C20 C21 C22 N5 5.9(6) . . . . ?
C16 C21 C22 C23 4.1(6) . . . . ?
C20 C21 C22 C23 -175.3(4) . . . . ?
S2 N4 C23 C22 -54.3(5) . . . . ?
N5 C22 C23 N4 -158.0(4) . . . . ?
C21 C22 C23 N4 23.3(6) . . . . ?
N5 N6 C24 C25 179.1(3) . . . . ?
N6 C24 C25 C30 -171.0(4) . . . . ?
N6 C24 C25 C26 8.8(6) . . . . ?
C30 C25 C26 C27 1.9(7) . . . . ?
C24 C25 C26 C27 -177.8(4) . . . . ?
C25 C26 C27 C28 -0.5(8) . . . . ?
C26 C27 C28 C29 -0.8(8) . . . . ?
C27 C28 C29 C30 0.7(7) . . . . ?
C26 C25 C30 C29 -2.1(6) . . . . ?
C24 C25 C30 C29 177.7(4) . . . . ?
C28 C29 C30 C25 0.8(7) . . . . ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 76.66
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max 1.274
_refine_diff_density_min -0.616
_refine_diff_density_rms 0.089
_database_code_depnum_ccdc_archive 'CCDC 968354'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_c:\nadeem
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
N-(2-Ethyl-1,1-dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(4-methyl-benzylidene)-hydrazine
;
_chemical_name_common
;
N-(2-Ethyl-1,1-dioxo-2,3-dihydro-1H-1\l^6^-benzo[e][1,2]
thiazin-4-ylidene)-N'-(4-methyl-benzylidene)-hydrazine
;
_chemical_melting_point ?
_chemical_formula_moiety 'C15 H12 Br N3 O2 S'
_chemical_formula_sum 'C15 H12 Br N3 O2 S'
_chemical_formula_weight 378.25
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 n a 21'
_symmetry_space_group_name_Hall 'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
_cell_length_a 6.34070(10)
_cell_length_b 16.6106(4)
_cell_length_c 14.4754(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1524.59(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 8900
_cell_measurement_theta_min 3.0487
_cell_measurement_theta_max 76.3170
_exptl_crystal_description rod
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.34
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.648
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 760
_exptl_absorpt_coefficient_mu 5.051
_exptl_absorpt_correction_T_min 0.49783
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details ?
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_type CuK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 13287
_diffrn_reflns_av_R_equivalents 0.0243
_diffrn_reflns_av_sigmaI/netI 0.0181
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 4.05
_diffrn_reflns_theta_max 76.63
_reflns_number_total 3054
_reflns_number_gt 2988
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.1309P)^2^+0.3266P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.05(3)
_refine_ls_number_reflns 3054
_refine_ls_number_parameters 199
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0570
_refine_ls_R_factor_gt 0.0565
_refine_ls_wR_factor_ref 0.1520
_refine_ls_wR_factor_gt 0.1507
_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
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
Br1 Br 0.93070(8) -0.16876(3) 0.00019(4) 0.0611(2) Uani 1 1 d . . .
S1 S -0.29270(14) 0.13932(5) 0.03543(7) 0.0388(2) Uani 1 1 d . . .
O2 O -0.4042(5) 0.0720(2) -0.0021(3) 0.0553(7) Uani 1 1 d . . .
O1 O -0.3374(6) 0.2184(2) 0.0005(3) 0.0603(9) Uani 1 1 d . . .
C1 C -0.3307(5) 0.13771(19) 0.1557(3) 0.0339(7) Uani 1 1 d . . .
N3 N 0.2934(5) -0.0206(2) 0.1936(3) 0.0414(7) Uani 1 1 d . . .
N2 N 0.1198(5) 0.0191(2) 0.2331(3) 0.0410(7) Uani 1 1 d . . .
C2 C -0.5058(7) 0.1768(2) 0.1920(4) 0.0441(9) Uani 1 1 d . . .
H2 H -0.5988 0.2037 0.1532 0.053 Uiso 1 1 calc R . .
C11 C 0.6589(6) -0.1098(2) 0.1413(3) 0.0372(7) Uani 1 1 d . . .
H11 H 0.5811 -0.0876 0.0931 0.045 Uiso 1 1 calc R . .
C3 C -0.5408(7) 0.1754(3) 0.2857(4) 0.0492(11) Uani 1 1 d . . .
H3 H -0.6572 0.2017 0.3106 0.059 Uiso 1 1 calc R . .
C7 C 0.0018(6) 0.05529(19) 0.1740(3) 0.0324(7) Uani 1 1 d . . .
C5 C -0.2273(6) 0.0955(3) 0.3065(3) 0.0423(8) Uani 1 1 d . . .
H5 H -0.1362 0.0679 0.3457 0.051 Uiso 1 1 calc R . .
C6 C -0.1861(5) 0.0968(2) 0.2117(3) 0.0327(7) Uani 1 1 d . . .
C9 C 0.4038(6) -0.0548(2) 0.2555(3) 0.0382(8) Uani 1 1 d . . .
H9 H 0.3625 -0.0509 0.3170 0.046 Uiso 1 1 calc R . .
C10 C 0.5946(5) -0.1003(2) 0.2322(3) 0.0358(8) Uani 1 1 d . . .
N1 N -0.0448(5) 0.1247(2) 0.0226(2) 0.0386(7) Uani 1 1 d . . .
C12 C 0.8419(6) -0.1531(2) 0.1237(3) 0.0382(8) Uani 1 1 d . . .
C15 C 0.7133(7) -0.1335(3) 0.3037(3) 0.0435(9) Uani 1 1 d . . .
H15 H 0.6700 -0.1268 0.3646 0.052 Uiso 1 1 calc R . .
C8 C 0.0437(6) 0.0549(3) 0.0707(3) 0.0392(8) Uani 1 1 d . . .
H8A H 0.1949 0.0536 0.0605 0.047 Uiso 1 1 calc R . .
H8B H -0.0156 0.0062 0.0443 0.047 Uiso 1 1 calc R . .
C14 C 0.8952(8) -0.1766(3) 0.2846(4) 0.0499(10) Uani 1 1 d . . .
H14 H 0.9730 -0.1990 0.3326 0.060 Uiso 1 1 calc R . .
C4 C -0.4011(8) 0.1345(3) 0.3432(4) 0.0489(10) Uani 1 1 d . . .
H4 H -0.4247 0.1334 0.4066 0.059 Uiso 1 1 calc R . .
C13 C 0.9615(7) -0.1863(3) 0.1943(4) 0.0446(9) Uani 1 1 d . . .
H13 H 1.0844 -0.2146 0.1812 0.053 Uiso 1 1 calc R . .
H1 H 0.0310 0.1645 0.0189 0.053 Uiso 1 1 d 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
Br1 0.0721(4) 0.0669(3) 0.0442(3) -0.0080(2) 0.0200(2) 0.0041(2)
S1 0.0384(4) 0.0434(4) 0.0348(5) 0.0045(4) -0.0029(3) 0.0038(3)
O2 0.0520(15) 0.0707(19) 0.0433(17) -0.008(2) -0.0094(15) -0.0127(13)
O1 0.0681(18) 0.0563(17) 0.057(2) 0.0216(19) 0.0056(18) 0.0223(14)
C1 0.0314(16) 0.0337(15) 0.037(2) -0.0016(13) 0.0000(14) 0.0008(11)
N3 0.0385(15) 0.0489(17) 0.0368(17) 0.0024(14) 0.0031(13) 0.0120(13)
N2 0.0332(13) 0.0491(17) 0.0407(19) 0.0029(14) 0.0039(15) 0.0081(12)
C2 0.0351(19) 0.0412(18) 0.056(3) -0.0036(17) -0.0008(19) 0.0064(14)
C11 0.0399(17) 0.0379(16) 0.0338(19) 0.0046(14) 0.0010(15) 0.0011(12)
C3 0.039(2) 0.052(2) 0.057(3) -0.009(2) 0.009(2) 0.0081(14)
C7 0.0309(15) 0.0324(14) 0.0339(18) 0.0007(13) -0.0005(13) -0.0017(12)
C5 0.0419(19) 0.052(2) 0.033(2) -0.0042(16) -0.0047(16) 0.0038(15)
C6 0.0321(14) 0.0341(14) 0.0320(19) -0.0035(13) 0.0000(13) 0.0002(11)
C9 0.0361(17) 0.0422(18) 0.0362(19) 0.0027(15) 0.0025(14) 0.0054(13)
C10 0.0355(16) 0.0337(15) 0.038(2) 0.0020(14) -0.0005(14) 0.0031(12)
N1 0.0399(15) 0.0412(14) 0.035(2) 0.0061(12) 0.0023(12) -0.0006(11)
C12 0.0427(18) 0.0334(14) 0.038(2) -0.0048(14) 0.0059(17) -0.0012(13)
C15 0.045(2) 0.051(2) 0.035(2) 0.0037(16) 0.0020(17) 0.0088(15)
C8 0.0410(18) 0.0411(17) 0.036(2) 0.0019(15) 0.0050(14) 0.0093(14)
C14 0.050(2) 0.053(2) 0.047(3) 0.0027(18) -0.005(2) 0.0139(16)
C4 0.051(2) 0.061(3) 0.034(2) -0.0086(18) 0.0046(18) 0.0031(17)
C13 0.0396(19) 0.0431(17) 0.051(3) -0.0028(19) 0.0014(17) 0.0083(15)
_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
Br1 C12 1.892(4) . ?
S1 O2 1.430(3) . ?
S1 O1 1.436(3) . ?
S1 N1 1.602(3) . ?
S1 C1 1.758(4) . ?
C1 C2 1.389(6) . ?
C1 C6 1.400(5) . ?
N3 C9 1.272(6) . ?
N3 N2 1.404(4) . ?
N2 C7 1.286(5) . ?
C2 C3 1.374(8) . ?
C2 H2 0.9300 . ?
C11 C10 1.386(6) . ?
C11 C12 1.389(5) . ?
C11 H11 0.9300 . ?
C3 C4 1.392(8) . ?
C3 H3 0.9300 . ?
C7 C6 1.480(5) . ?
C7 C8 1.518(6) . ?
C5 C4 1.385(6) . ?
C5 C6 1.397(6) . ?
C5 H5 0.9300 . ?
C9 C10 1.466(5) . ?
C9 H9 0.9300 . ?
C10 C15 1.394(6) . ?
N1 C8 1.464(5) . ?
N1 H1 0.8185 . ?
C12 C13 1.387(7) . ?
C15 C14 1.385(6) . ?
C15 H15 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C14 C13 1.382(8) . ?
C14 H14 0.9300 . ?
C4 H4 0.9300 . ?
C13 H13 0.9300 . ?
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
O2 S1 O1 118.9(3) . . ?
O2 S1 N1 108.8(2) . . ?
O1 S1 N1 106.94(19) . . ?
O2 S1 C1 107.2(2) . . ?
O1 S1 C1 109.6(2) . . ?
N1 S1 C1 104.33(18) . . ?
C2 C1 C6 122.1(4) . . ?
C2 C1 S1 118.5(3) . . ?
C6 C1 S1 119.4(3) . . ?
C9 N3 N2 110.7(4) . . ?
C7 N2 N3 113.9(3) . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C10 C11 C12 118.6(4) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
N2 C7 C6 116.1(3) . . ?
N2 C7 C8 123.4(3) . . ?
C6 C7 C8 120.4(3) . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 117.0(3) . . ?
C5 C6 C7 120.4(3) . . ?
C1 C6 C7 122.7(4) . . ?
N3 C9 C10 121.5(4) . . ?
N3 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C15 120.1(4) . . ?
C11 C10 C9 121.3(4) . . ?
C15 C10 C9 118.6(4) . . ?
C8 N1 S1 116.2(3) . . ?
C8 N1 H1 116.4 . . ?
S1 N1 H1 117.5 . . ?
C13 C12 C11 121.8(4) . . ?
C13 C12 Br1 118.7(3) . . ?
C11 C12 Br1 119.5(3) . . ?
C14 C15 C10 120.3(4) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
N1 C8 C7 113.4(3) . . ?
N1 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C13 C14 C15 120.2(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C14 C13 C12 119.0(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
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
O2 S1 C1 C2 -88.1(3) . . . . ?
O1 S1 C1 C2 42.3(4) . . . . ?
N1 S1 C1 C2 156.5(3) . . . . ?
O2 S1 C1 C6 91.3(3) . . . . ?
O1 S1 C1 C6 -138.3(3) . . . . ?
N1 S1 C1 C6 -24.1(3) . . . . ?
C9 N3 N2 C7 179.7(4) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
S1 C1 C2 C3 179.0(3) . . . . ?
C1 C2 C3 C4 -0.3(7) . . . . ?
N3 N2 C7 C6 178.8(3) . . . . ?
N3 N2 C7 C8 0.6(5) . . . . ?
C4 C5 C6 C1 -1.3(6) . . . . ?
C4 C5 C6 C7 179.4(4) . . . . ?
C2 C1 C6 C5 1.2(5) . . . . ?
S1 C1 C6 C5 -178.2(3) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
S1 C1 C6 C7 1.0(5) . . . . ?
N2 C7 C6 C5 0.2(5) . . . . ?
C8 C7 C6 C5 178.5(4) . . . . ?
N2 C7 C6 C1 -179.0(3) . . . . ?
C8 C7 C6 C1 -0.7(5) . . . . ?
N2 N3 C9 C10 -179.8(3) . . . . ?
C12 C11 C10 C15 0.3(5) . . . . ?
C12 C11 C10 C9 179.6(3) . . . . ?
N3 C9 C10 C11 -1.9(6) . . . . ?
N3 C9 C10 C15 177.4(4) . . . . ?
O2 S1 N1 C8 -62.6(4) . . . . ?
O1 S1 N1 C8 167.8(3) . . . . ?
C1 S1 N1 C8 51.6(3) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
C10 C11 C12 Br1 178.9(3) . . . . ?
C11 C10 C15 C14 -0.3(6) . . . . ?
C9 C10 C15 C14 -179.7(4) . . . . ?
S1 N1 C8 C7 -55.8(4) . . . . ?
N2 C7 C8 N1 -154.4(3) . . . . ?
C6 C7 C8 N1 27.4(5) . . . . ?
C10 C15 C14 C13 0.5(7) . . . . ?
C6 C5 C4 C3 0.7(7) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
C15 C14 C13 C12 -0.7(7) . . . . ?
C11 C12 C13 C14 0.7(6) . . . . ?
Br1 C12 C13 C14 -178.6(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 76.63
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max 1.001
_refine_diff_density_min -0.583
_refine_diff_density_rms 0.068
_database_code_depnum_ccdc_archive 'CCDC 968355'