data_02esp301
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Pedro Cintas - 02ESP301
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H15 N O2 S'
_chemical_formula_weight          309.37
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P21/c
 
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                    5.4079(9)
_cell_length_b                    16.685(3)
_cell_length_c                    16.587(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  89.04
_cell_angle_gamma                 90.00
_cell_volume                      1496.5(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     11522
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.373
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              648
_exptl_absorpt_coefficient_mu     0.223
_exptl_absorpt_correction_type    Multi-scans
_exptl_absorpt_correction_T_min   0.9568
_exptl_absorpt_correction_T_max   0.9781
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method        'φ and ω scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean  '9.091 pixels mm^1^'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             3635
_diffrn_reflns_av_R_equivalents   0.0624
_diffrn_reflns_av_sigmaI/netI     0.1064
_diffrn_reflns_limit_h_min        -3
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -19
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          3.46
_diffrn_reflns_theta_max          25.02
_reflns_number_total              2272
_reflns_number_gt                 1672
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO (Otwinowski and MInor, 1997)'
_computing_data_reduction         'DENZO, COLLECT, MAXUS (Mackay et al., 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'
 
_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)+(0.1454P)²+2.1246P] where P=(Fo²+2Fc²)/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        none
_refine_ls_number_reflns          2272
_refine_ls_number_parameters      201
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1122
_refine_ls_R_factor_gt            0.0824
_refine_ls_wR_factor_ref          0.2481
_refine_ls_wR_factor_gt           0.2176
_refine_ls_goodness_of_fit_ref    1.031
_refine_ls_restrained_S_all       1.031
_refine_ls_shift/su_max           0.006
_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 0.0131(4) 0.11543(8) 0.14330(9) 0.0303(5) Uani 1 1 d . . .
N1 N 0.0782(11) 0.1001(3) 0.2996(3) 0.0287(14) Uani 1 1 d . . .
O1 O -0.3668(9) 0.2195(2) 0.1317(2) 0.0353(12) Uani 1 1 d . . .
O2 O 0.3858(10) 0.0051(3) 0.3088(3) 0.0407(13) Uani 1 1 d . . .
C1 C -0.5547(14) 0.3032(3) 0.2323(4) 0.0320(16) Uani 1 1 d . . .
H1A H -0.5278 0.3512 0.1994 0.048 Uiso 1 1 calc R . .
H1B H -0.5231 0.3157 0.2890 0.048 Uiso 1 1 calc R . .
H1C H -0.7260 0.2850 0.2270 0.048 Uiso 1 1 calc R . .
C2 C -0.3796(13) 0.2373(3) 0.2040(4) 0.0271(15) Uani 1 1 d . . .
C3 C -0.2386(13) 0.1955(3) 0.2648(4) 0.0285(15) Uani 1 1 d . . .
H3 H -0.2694 0.2066 0.3202 0.034 Uiso 1 1 calc R . .
C4 C -0.0649(13) 0.1414(3) 0.2436(4) 0.0282(16) Uani 1 1 d . . .
C5 C 0.0471(14) 0.1099(3) 0.3864(4) 0.0280(16) Uani 1 1 d . . .
C6 C 0.2207(14) 0.1530(4) 0.4287(4) 0.0332(17) Uani 1 1 d . . .
H6 H 0.3585 0.1764 0.4013 0.040 Uiso 1 1 calc R . .
C7 C 0.1916(15) 0.1620(4) 0.5127(4) 0.0370(18) Uani 1 1 d . . .
H7 H 0.3109 0.1910 0.5423 0.044 Uiso 1 1 calc R . .
C8 C -0.0130(15) 0.1282(3) 0.5525(4) 0.0351(17) Uani 1 1 d . . .
H8 H -0.0342 0.1348 0.6091 0.042 Uiso 1 1 calc R . .
C9 C -0.1851(14) 0.0850(4) 0.5092(4) 0.0368(17) Uani 1 1 d . . .
H9 H -0.3230 0.0615 0.5364 0.044 Uiso 1 1 calc R . .
C10 C -0.1567(14) 0.0759(4) 0.4252(4) 0.0356(17) Uani 1 1 d . . .
H10 H -0.2756 0.0469 0.3954 0.043 Uiso 1 1 calc R . .
C11 C 0.2578(13) 0.0481(3) 0.2668(4) 0.0289(15) Uani 1 1 d . . .
C12 C 0.2697(14) 0.0516(3) 0.1758(4) 0.0293(15) Uani 1 1 d . . .
H12 H 0.4280 0.0787 0.1596 0.035 Uiso 1 1 calc R . .
C13 C 0.2642(13) -0.0296(3) 0.1348(4) 0.0289(16) Uani 1 1 d . . .
C14 C 0.4563(13) -0.0527(3) 0.0827(3) 0.0278(15) Uani 1 1 d . . .
H14 H 0.5964 -0.0190 0.0753 0.033 Uiso 1 1 calc R . .
C15 C 0.4427(15) -0.1259(3) 0.0412(4) 0.0346(18) Uani 1 1 d . . .
H15 H 0.5719 -0.1416 0.0050 0.042 Uiso 1 1 calc R . .
C16 C 0.2379(14) -0.1751(4) 0.0537(4) 0.0332(18) Uani 1 1 d . . .
H16 H 0.2262 -0.2244 0.0253 0.040 Uiso 1 1 calc R . .
C17 C 0.0510(14) -0.1528(4) 0.1072(4) 0.0341(17) Uani 1 1 d . . .
H17 H -0.0863 -0.1874 0.1159 0.041 Uiso 1 1 calc R . .
C18 C 0.0620(13) -0.0801(3) 0.1483(4) 0.0328(16) Uani 1 1 d . . .
H18 H -0.0664 -0.0651 0.1851 0.039 Uiso 1 1 calc R . .
 
 
_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 C4 1.764(6) . ?
S1 C12 1.837(7) . ?
N1 C4 1.399(8) . ?
N1 C11 1.405(8) . ?
N1 C5 1.456(8) . ?
O1 C2 1.237(7) . ?
O2 C11 1.223(7) . ?
C1 C2 1.520(9) . ?
C2 C3 1.452(9) . ?
C3 C4 1.346(9) . ?
C5 C6 1.384(9) . ?
C5 C10 1.388(10) . ?
C6 C7 1.407(9) . ?
C7 C8 1.398(10) . ?
C8 C9 1.387(10) . ?
C9 C10 1.407(10) . ?
C11 C12 1.511(9) . ?
C12 C13 1.516(8) . ?
C13 C14 1.395(10) . ?
C13 C18 1.396(9) . ?
C14 C15 1.404(8) . ?
C15 C16 1.392(10) . ?
C16 C17 1.385(10) . ?
C17 C18 1.394(9) . ?
 
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
C4 S1 C12 92.0(3) . . ?
C4 N1 C11 115.7(5) . . ?
C4 N1 C5 123.0(5) . . ?
C11 N1 C5 121.3(5) . . ?
O1 C2 C3 122.4(6) . . ?
O1 C2 C1 119.9(6) . . ?
C3 C2 C1 117.6(5) . . ?
C4 C3 C2 120.9(6) . . ?
C3 C4 N1 123.3(6) . . ?
C3 C4 S1 124.4(5) . . ?
N1 C4 S1 112.3(5) . . ?
C6 C5 C10 121.2(6) . . ?
C6 C5 N1 119.4(6) . . ?
C10 C5 N1 119.4(6) . . ?
C5 C6 C7 119.5(7) . . ?
C8 C7 C6 120.0(6) . . ?
C9 C8 C7 119.8(6) . . ?
C8 C9 C10 120.4(7) . . ?
C5 C10 C9 119.2(6) . . ?
O2 C11 N1 122.4(6) . . ?
O2 C11 C12 125.2(6) . . ?
N1 C11 C12 112.3(5) . . ?
C11 C12 C13 114.3(5) . . ?
C11 C12 S1 107.2(5) . . ?
C13 C12 S1 111.5(4) . . ?
C14 C13 C18 120.4(5) . . ?
C14 C13 C12 120.3(6) . . ?
C18 C13 C12 119.3(6) . . ?
C13 C14 C15 120.0(6) . . ?
C16 C15 C14 119.2(7) . . ?
C17 C16 C15 120.5(6) . . ?
C16 C17 C18 120.7(7) . . ?
C17 C18 C13 119.2(7) . . ?
 
_diffrn_measured_fraction_theta_max    0.857
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.857
_refine_diff_density_max    0.601
_refine_diff_density_min   -0.436
_refine_diff_density_rms    0.086
