data_02esp402
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Pedro Cintas
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H19 N O2 S'
_chemical_formula_weight          337.42
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   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                    6.16440(10)
_cell_length_b                    10.8967(3)
_cell_length_c                    24.7631(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  93.3830(10)
_cell_angle_gamma                 90.00
_cell_volume                      1660.48(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4585
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.350
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              712
_exptl_absorpt_coefficient_mu     0.207
_exptl_absorpt_correction_type    Multi-scans
_exptl_absorpt_correction_T_min   0.9406
_exptl_absorpt_correction_T_max   0.9796
_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             5309
_diffrn_reflns_av_R_equivalents   0.0243
_diffrn_reflns_av_sigmaI/netI     0.0422
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -29
_diffrn_reflns_limit_l_max        29
_diffrn_reflns_theta_min          3.10
_diffrn_reflns_theta_max          25.02
_reflns_number_total              2901
_reflns_number_gt                 2320
_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)+(0.0372P)²+0.5760P] 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          2901
_refine_ls_number_parameters      219
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0506
_refine_ls_R_factor_gt            0.0352
_refine_ls_wR_factor_ref          0.0867
_refine_ls_wR_factor_gt           0.0810
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_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 0.7289(3) 0.89371(17) 0.66411(7) 0.0221(4) Uani 1 1 d . . .
H1 H 0.5921 0.9253 0.6732 0.027 Uiso 1 1 calc R . .
C2 C 0.7977(3) 0.90799(18) 0.61196(7) 0.0266(5) Uani 1 1 d . . .
H2 H 0.7092 0.9508 0.5855 0.032 Uiso 1 1 calc R . .
C3 C 0.9953(3) 0.85970(17) 0.59867(7) 0.0246(4) Uani 1 1 d . . .
H3 H 1.0403 0.8672 0.5628 0.029 Uiso 1 1 calc R . .
C4 C 1.1274(3) 0.80045(17) 0.63760(7) 0.0238(4) Uani 1 1 d . . .
H4 H 1.2637 0.7683 0.6285 0.029 Uiso 1 1 calc R . .
C5 C 1.0608(3) 0.78786(17) 0.68994(7) 0.0207(4) Uani 1 1 d . . .
H5 H 1.1522 0.7483 0.7168 0.025 Uiso 1 1 calc R . .
C6 C 0.8609(3) 0.83320(16) 0.70269(6) 0.0161(4) Uani 1 1 d . . .
C7 C 0.7982(3) 0.90159(17) 0.79566(6) 0.0157(4) Uani 1 1 d . . .
C8 C 0.7194(3) 0.84159(16) 0.84800(6) 0.0157(4) Uani 1 1 d . . .
C9 C 0.6649(3) 0.93587(16) 0.88962(6) 0.0164(4) Uani 1 1 d . . .
C10 C 0.4569(3) 0.98465(16) 0.89119(7) 0.0198(4) Uani 1 1 d . . .
H10 H 0.3423 0.9521 0.8682 0.024 Uiso 1 1 calc R . .
C11 C 0.4148(3) 1.08064(17) 0.92616(7) 0.0237(4) Uani 1 1 d . . .
H11 H 0.2725 1.1139 0.9266 0.028 Uiso 1 1 calc R . .
C12 C 0.5801(3) 1.12771(17) 0.96035(7) 0.0241(4) Uani 1 1 d . . .
H12 H 0.5514 1.1930 0.9843 0.029 Uiso 1 1 calc R . .
C13 C 0.7873(3) 1.07926(17) 0.95943(7) 0.0223(4) Uani 1 1 d . . .
H13 H 0.9007 1.1111 0.9830 0.027 Uiso 1 1 calc R . .
C14 C 0.8304(3) 0.98439(16) 0.92423(7) 0.0200(4) Uani 1 1 d . . .
H14 H 0.9735 0.9522 0.9237 0.024 Uiso 1 1 calc R . .
C15 C 0.9064(3) 0.74728(16) 0.86345(6) 0.0175(4) Uani 1 1 d . . .
H15 H 1.0482 0.7904 0.8602 0.021 Uiso 1 1 calc R . .
C16 C 0.9063(3) 0.69299(16) 0.92038(7) 0.0232(4) Uani 1 1 d . . .
C17 C 0.7036(3) 0.6347(2) 0.93945(7) 0.0327(5) Uani 1 1 d . . .
H17A H 0.7308 0.6055 0.9767 0.049 Uiso 1 1 calc R . .
H17B H 0.6619 0.5653 0.9159 0.049 Uiso 1 1 calc R . .
H17C H 0.5859 0.6952 0.9382 0.049 Uiso 1 1 calc R . .
C18 C 0.8855(3) 0.64789(16) 0.81818(7) 0.0188(4) Uani 1 1 d . . .
H18A H 1.0256 0.6372 0.8012 0.023 Uiso 1 1 calc R . .
H18B H 0.8418 0.5681 0.8333 0.023 Uiso 1 1 calc R . .
C19 C 0.7103(3) 0.69526(16) 0.77666(6) 0.0172(4) Uani 1 1 d . . .
C20 C 0.6388(3) 0.60622(17) 0.73259(7) 0.0211(4) Uani 1 1 d . . .
H20A H 0.7633 0.5847 0.7116 0.032 Uiso 1 1 calc R . .
H20B H 0.5255 0.6442 0.7087 0.032 Uiso 1 1 calc R . .
H20C H 0.5812 0.5319 0.7488 0.032 Uiso 1 1 calc R . .
N1 N 0.7857(2) 0.81491(13) 0.75615(5) 0.0165(3) Uani 1 1 d . . .
O1 O 0.8677(2) 1.00544(11) 0.79211(5) 0.0215(3) Uani 1 1 d . . .
O2 O 1.0740(2) 0.69481(13) 0.94892(5) 0.0353(4) Uani 1 1 d . . .
S1 S 0.49400(7) 0.74510(4) 0.820174(17) 0.01885(14) 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 C6 1.385(2) . ?
C1 C2 1.392(2) . ?
C2 C3 1.384(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.389(2) . ?
C5 C6 1.381(2) . ?
C6 N1 1.442(2) . ?
C7 O1 1.215(2) . ?
C7 N1 1.359(2) . ?
C7 C8 1.555(2) . ?
C8 C9 1.507(2) . ?
C8 C15 1.575(2) . ?
C8 S1 1.8432(17) . ?
C9 C10 1.391(2) . ?
C9 C14 1.397(2) . ?
C10 C11 1.392(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.388(3) . ?
C15 C16 1.529(2) . ?
C15 C18 1.559(2) . ?
C16 O2 1.217(2) . ?
C16 C17 1.503(3) . ?
C18 C19 1.536(2) . ?
C19 N1 1.484(2) . ?
C19 C20 1.506(2) . ?
C19 S1 1.8448(17) . ?
 
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
C6 C1 C2 119.63(17) . . ?
C3 C2 C1 119.92(17) . . ?
C2 C3 C4 120.10(16) . . ?
C3 C4 C5 120.11(17) . . ?
C6 C5 C4 119.64(17) . . ?
C5 C6 C1 120.57(15) . . ?
C5 C6 N1 119.99(15) . . ?
C1 C6 N1 119.42(15) . . ?
O1 C7 N1 126.91(15) . . ?
O1 C7 C8 125.52(15) . . ?
N1 C7 C8 107.49(14) . . ?
C9 C8 C7 112.13(14) . . ?
C9 C8 C15 117.91(13) . . ?
C7 C8 C15 102.50(13) . . ?
C9 C8 S1 116.81(12) . . ?
C7 C8 S1 101.20(10) . . ?
C15 C8 S1 104.09(11) . . ?
C10 C9 C14 118.64(16) . . ?
C10 C9 C8 121.51(15) . . ?
C14 C9 C8 119.56(15) . . ?
C9 C10 C11 120.69(17) . . ?
C12 C11 C10 120.11(17) . . ?
C13 C12 C11 119.70(17) . . ?
C12 C13 C14 120.38(17) . . ?
C13 C14 C9 120.47(17) . . ?
C16 C15 C18 112.95(14) . . ?
C16 C15 C8 115.88(14) . . ?
C18 C15 C8 104.50(13) . . ?
O2 C16 C17 121.17(17) . . ?
O2 C16 C15 118.86(17) . . ?
C17 C16 C15 119.93(16) . . ?
C19 C18 C15 105.84(14) . . ?
N1 C19 C20 113.71(13) . . ?
N1 C19 C18 107.58(14) . . ?
C20 C19 C18 115.63(15) . . ?
N1 C19 S1 101.13(11) . . ?
C20 C19 S1 114.98(12) . . ?
C18 C19 S1 102.23(11) . . ?
C7 N1 C6 123.86(14) . . ?
C7 N1 C19 111.72(13) . . ?
C6 N1 C19 124.04(13) . . ?
C8 S1 C19 80.30(8) . . ?
 
_diffrn_measured_fraction_theta_max    0.990
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.990
_refine_diff_density_max    0.273
_refine_diff_density_min   -0.252
_refine_diff_density_rms    0.046
