data_2007src1290

#Dr. I. Collins
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H14 N4 O3 S'
_chemical_formula_weight          318.35
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    6.6318(3)
_cell_length_b                    9.4254(4)
_cell_length_c                    12.0872(4)
_cell_angle_alpha                 112.574(2)
_cell_angle_beta                  90.804(2)
_cell_angle_gamma                 96.144(2)
_cell_volume                      692.39(5)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2950
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             'Light Brown'
_exptl_crystal_size_max           0.09
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.527
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              332
_exptl_absorpt_coefficient_mu     0.254
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9775
_exptl_absorpt_correction_T_max   0.9899
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details
;
SADABS was used to perform the Absorption correction
Parameter refinement on 10418 reflections reduced R(int) from 0.0988 to 0.0487
Ratio of minimum to maximum apparent transmission: 0.827304
The given Tmin and Tmax were generated using the SHELX SIZE command
;


_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type   
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             11744
_diffrn_reflns_av_R_equivalents   0.0494
_diffrn_reflns_av_sigmaI/netI     0.0507
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.10
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3162
_reflns_number_gt                 2534
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX (Farrugia, 1999)'
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0100P)²+1.4129P] where P=(Fo²+2Fc²)/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          3162
_refine_ls_number_parameters      201
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0785
_refine_ls_R_factor_gt            0.0572
_refine_ls_wR_factor_ref          0.1203
_refine_ls_wR_factor_gt           0.1083
_refine_ls_goodness_of_fit_ref    1.076
_refine_ls_restrained_S_all       1.075
_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
C1 C 0.5588(4) 0.8454(3) 0.3216(2) 0.0186(5) Uani 1 1 d . . .
C2 C 0.4481(4) 0.7907(3) 0.3951(2) 0.0184(5) Uani 1 1 d . . .
C3 C 0.2684(4) 0.8640(3) 0.4161(2) 0.0187(5) Uani 1 1 d . . .
C4 C 0.1258(4) 0.8315(3) 0.4934(2) 0.0192(5) Uani 1 1 d . . .
H4 H 0.0044 0.8791 0.5099 0.023 Uiso 1 1 calc R . .
C5 C 0.1703(4) 0.7299(3) 0.5423(2) 0.0209(5) Uani 1 1 d . . .
C6 C 0.4893(4) 0.6776(3) 0.4425(2) 0.0207(5) Uani 1 1 d . . .
C7 C 0.0408(4) 0.6919(3) 0.6296(2) 0.0259(6) Uani 1 1 d . . .
H7A H -0.0833 0.7420 0.6376 0.039 Uiso 1 1 calc R . .
H7B H 0.1159 0.7292 0.7078 0.039 Uiso 1 1 calc R . .
H7C H 0.0049 0.5795 0.6005 0.039 Uiso 1 1 calc R . .
C8 C 0.2986(4) 0.8585(3) 0.0753(2) 0.0205(5) Uani 1 1 d . . .
C9 C 0.3740(4) 0.7211(3) 0.0077(3) 0.0286(6) Uani 1 1 d . . .
H9 H 0.5117 0.7084 0.0197 0.034 Uiso 1 1 calc R . .
C10 C 0.2451(5) 0.6031(3) -0.0772(3) 0.0341(7) Uani 1 1 d . . .
H10 H 0.2954 0.5090 -0.1241 0.041 Uiso 1 1 calc R . .
C11 C 0.0434(5) 0.6205(3) -0.0947(2) 0.0294(6) Uani 1 1 d . . .
C12 C -0.0271(4) 0.7595(3) -0.0266(3) 0.0290(6) Uani 1 1 d . . .
H12 H -0.1641 0.7732 -0.0394 0.035 Uiso 1 1 calc R . .
C13 C 0.0989(4) 0.8793(3) 0.0601(2) 0.0238(6) Uani 1 1 d . . .
H13 H 0.0486 0.9731 0.1077 0.029 Uiso 1 1 calc R . .
C14 C -0.0977(5) 0.4904(4) -0.1862(3) 0.0418(8) Uani 1 1 d . . .
H14A H -0.1258 0.4060 -0.1582 0.063 Uiso 1 1 calc R . .
H14B H -0.0336 0.4523 -0.2630 0.063 Uiso 1 1 calc R . .
H14C H -0.2254 0.5288 -0.1967 0.063 Uiso 1 1 calc R . .
N1 N 0.4467(3) 0.9512(2) 0.30370(19) 0.0191(5) Uani 1 1 d . . .
N2 N 0.2591(3) 0.9591(2) 0.35879(19) 0.0205(5) Uani 1 1 d . . .
N3 N 0.7392(3) 0.8082(3) 0.2752(2) 0.0236(5) Uani 1 1 d D . .
H3A H 0.8025 0.7576 0.3109 0.035 Uiso 1 1 d D . .
H3B H 0.8137 0.8715 0.2485 0.035 Uiso 1 1 d D . .
N4 N 0.3437(3) 0.6551(2) 0.5156(2) 0.0226(5) Uani 1 1 d . . .
H4A H 0.3614 0.5880 0.5482 0.027 Uiso 1 1 calc R . .
O1 O 0.6388(3) 0.6040(2) 0.41884(18) 0.0266(4) Uani 1 1 d . . .
O2 O 0.6648(3) 0.9974(2) 0.15408(17) 0.0252(4) Uani 1 1 d . . .
O3 O 0.3721(3) 1.1473(2) 0.22096(17) 0.0262(4) Uani 1 1 d . . .
S1 S 0.45816(10) 1.00628(7) 0.18650(6) 0.02028(17) Uani 1 1 d . . .
 
 
_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
C1 N3 1.352(3) . ?
C1 C2 1.372(4) . ?
C1 N1 1.384(3) . ?
C2 C3 1.419(4) . ?
C2 C6 1.437(3) . ?
C3 N2 1.332(3) . ?
C3 C4 1.430(4) . ?
C4 C5 1.357(4) . ?
C4 H4 0.9500 . ?
C5 N4 1.390(3) . ?
C5 C7 1.493(4) . ?
C6 O1 1.245(3) . ?
C6 N4 1.372(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.379(4) . ?
C8 C9 1.390(4) . ?
C8 S1 1.754(3) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 C14 1.512(4) . ?
C12 C13 1.391(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 N2 1.415(3) . ?
N1 S1 1.685(2) . ?
N3 H3A 0.8859 . ?
N3 H3B 0.8907 . ?
N4 H4A 0.8800 . ?
O2 S1 1.4326(19) . ?
O3 S1 1.4177(19) . ?
 
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
N3 C1 C2 129.1(2) . . ?
N3 C1 N1 125.6(2) . . ?
C2 C1 N1 105.3(2) . . ?
C1 C2 C3 106.9(2) . . ?
C1 C2 C6 130.1(2) . . ?
C3 C2 C6 123.1(2) . . ?
N2 C3 C2 112.4(2) . . ?
N2 C3 C4 128.5(2) . . ?
C2 C3 C4 119.0(2) . . ?
C5 C4 C3 117.5(2) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C4 C5 N4 121.9(2) . . ?
C4 C5 C7 123.2(2) . . ?
N4 C5 C7 114.9(2) . . ?
O1 C6 N4 122.4(2) . . ?
O1 C6 C2 124.3(2) . . ?
N4 C6 C2 113.2(2) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 121.6(3) . . ?
C13 C8 S1 119.1(2) . . ?
C9 C8 S1 119.3(2) . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 118.9(3) . . ?
C10 C11 C14 120.7(3) . . ?
C12 C11 C14 120.4(3) . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C12 118.4(3) . . ?
C8 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 N2 112.4(2) . . ?
C1 N1 S1 126.03(18) . . ?
N2 N1 S1 116.11(16) . . ?
C3 N2 N1 102.9(2) . . ?
C1 N3 H3A 112.4 . . ?
C1 N3 H3B 119.9 . . ?
H3A N3 H3B 118.5 . . ?
C6 N4 C5 125.1(2) . . ?
C6 N4 H4A 117.4 . . ?
C5 N4 H4A 117.4 . . ?
O3 S1 O2 121.25(12) . . ?
O3 S1 N1 107.16(11) . . ?
O2 S1 N1 104.42(11) . . ?
O3 S1 C8 109.70(12) . . ?
O2 S1 C8 109.65(12) . . ?
N1 S1 C8 102.95(11) . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N3 H3A O1  0.89 2.48 3.080(3) 125.8 .
N3 H3B O2  0.89 2.22 2.783(3) 120.3 .
N4 H4A O1  0.88 2.00 2.854(3) 164.5 2_666
 
_diffrn_measured_fraction_theta_max    0.995
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.995
_refine_diff_density_max    0.337
_refine_diff_density_min   -0.419
_refine_diff_density_rms    0.075
