data_2008src0864
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C27 H28 N4 O3 S'
_chemical_formula_weight          488.59
 
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    P2(1)/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                    8.9260(8)
_cell_length_b                    15.4665(7)
_cell_length_c                    17.7890(15)
_cell_angle_alpha                 90.00
_cell_angle_beta                  99.900(3)
_cell_angle_gamma                 90.00
_cell_volume                      2419.3(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     27399
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.1
 
_exptl_crystal_description        lath
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.34
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.341
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1032
_exptl_absorpt_coefficient_mu     0.171
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9441
_exptl_absorpt_correction_T_max   0.9915
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 ?
;
 
_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   graphite
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             31632
_diffrn_reflns_av_R_equivalents   0.1765
_diffrn_reflns_av_sigmaI/netI     0.1476
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -19
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          2.99
_diffrn_reflns_theta_max          27.21
_reflns_number_total              5360
_reflns_number_gt                 2847
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'Sheldrick, G.M. (2008). Acta Cryst. A64, 112-1'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material   ?
 
_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)+(0.0664P)²+1.3409P] 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          5360
_refine_ls_number_parameters      316
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1647
_refine_ls_R_factor_gt            0.0749
_refine_ls_wR_factor_ref          0.1743
_refine_ls_wR_factor_gt           0.1418
_refine_ls_goodness_of_fit_ref    1.010
_refine_ls_restrained_S_all       1.010
_refine_ls_shift/su_max           0.002
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.0850(4) 0.3804(2) 0.16157(19) 0.0211(8) Uani 1 1 d . . .
C2 C -0.0850(4) 0.3693(2) 0.16333(19) 0.0200(8) Uani 1 1 d . . .
C3 C -0.1617(4) 0.4533(2) 0.1291(2) 0.0232(8) Uani 1 1 d . . .
H3 H -0.2196 0.4449 0.0763 0.028 Uiso 1 1 calc R . .
C4 C 0.3457(4) 0.3369(2) 0.1723(2) 0.0282(9) Uani 1 1 d . . .
H4A H 0.4106 0.2893 0.1966 0.034 Uiso 1 1 calc R . .
H4B H 0.3748 0.3902 0.2021 0.034 Uiso 1 1 calc R . .
C5 C 0.3755(5) 0.3496(3) 0.0914(2) 0.0374(10) Uani 1 1 d . . .
H5A H 0.4833 0.3631 0.0928 0.056 Uiso 1 1 calc R . .
H5B H 0.3130 0.3974 0.0672 0.056 Uiso 1 1 calc R . .
H5C H 0.3496 0.2965 0.0620 0.056 Uiso 1 1 calc R . .
C6 C 0.1543(4) 0.2281(2) 0.19998(19) 0.0223(8) Uani 1 1 d . . .
H6A H 0.0459 0.2238 0.2051 0.027 Uiso 1 1 calc R . .
H6B H 0.2163 0.2173 0.2508 0.027 Uiso 1 1 calc R . .
C7 C 0.1896(5) 0.1588(2) 0.1448(2) 0.0277(9) Uani 1 1 d . . .
H7A H 0.1673 0.1016 0.1640 0.042 Uiso 1 1 calc R . .
H7B H 0.2973 0.1618 0.1403 0.042 Uiso 1 1 calc R . .
H7C H 0.1268 0.1682 0.0946 0.042 Uiso 1 1 calc R . .
C8 C -0.1595(4) 0.2910(2) 0.11923(19) 0.0195(8) Uani 1 1 d . . .
C9 C -0.1246(4) 0.2704(2) 0.0483(2) 0.0238(8) Uani 1 1 d . . .
H9 H -0.0507 0.3034 0.0283 0.029 Uiso 1 1 calc R . .
C10 C -0.1964(4) 0.2020(2) 0.0061(2) 0.0237(8) Uani 1 1 d . . .
H10 H -0.1694 0.1874 -0.0417 0.028 Uiso 1 1 calc R . .
C11 C -0.3071(4) 0.1552(2) 0.03357(19) 0.0211(8) Uani 1 1 d . . .
C12 C -0.3430(4) 0.1751(2) 0.10399(19) 0.0236(8) Uani 1 1 d . . .
H12 H -0.4187 0.1428 0.1232 0.028 Uiso 1 1 calc R . .
C13 C -0.2683(4) 0.2422(2) 0.1468(2) 0.0226(8) Uani 1 1 d . . .
H13 H -0.2921 0.2548 0.1956 0.027 Uiso 1 1 calc R . .
C14 C -0.3490(6) 0.0619(3) -0.0759(2) 0.0447(12) Uani 1 1 d . . .
H14A H -0.4148 0.0139 -0.0969 0.067 Uiso 1 1 calc R . .
H14B H -0.2426 0.0432 -0.0679 0.067 Uiso 1 1 calc R . .
H14C H -0.3631 0.1106 -0.1116 0.067 Uiso 1 1 calc R . .
C15 C -0.0024(4) 0.3657(2) 0.30926(19) 0.0211(8) Uani 1 1 d . . .
C16 C 0.0223(4) 0.2869(2) 0.34660(19) 0.0222(8) Uani 1 1 d . . .
H16 H -0.0397 0.2385 0.3296 0.027 Uiso 1 1 calc R . .
C17 C 0.1389(4) 0.2795(2) 0.4093(2) 0.0256(9) Uani 1 1 d . . .
H17 H 0.1565 0.2256 0.4349 0.031 Uiso 1 1 calc R . .
C18 C 0.2284(5) 0.3493(2) 0.4344(2) 0.0328(10) Uani 1 1 d . . .
H18 H 0.3089 0.3433 0.4766 0.039 Uiso 1 1 calc R . .
C19 C 0.2017(5) 0.4288(2) 0.3983(2) 0.0332(10) Uani 1 1 d . . .
H19 H 0.2625 0.4774 0.4162 0.040 Uiso 1 1 calc R . .
C20 C 0.0862(5) 0.4369(2) 0.3360(2) 0.0286(9) Uani 1 1 d . . .
H20 H 0.0672 0.4913 0.3114 0.034 Uiso 1 1 calc R . .
C21 C -0.2629(4) 0.4770(2) 0.1852(2) 0.0234(8) Uani 1 1 d . . .
C22 C -0.3850(4) 0.5414(2) 0.1710(2) 0.0257(9) Uani 1 1 d . . .
C23 C -0.4869(5) 0.5510(2) 0.2215(2) 0.0271(9) Uani 1 1 d . . .
H23 H -0.4747 0.5169 0.2666 0.033 Uiso 1 1 calc R . .
C24 C -0.6060(5) 0.6096(2) 0.2070(2) 0.0308(9) Uani 1 1 d . . .
H24 H -0.6768 0.6144 0.2410 0.037 Uiso 1 1 calc R . .
C25 C -0.6208(5) 0.6609(3) 0.1428(3) 0.0419(11) Uani 1 1 d . . .
H25 H -0.7007 0.7021 0.1331 0.050 Uiso 1 1 calc R . .
C26 C -0.5198(5) 0.6525(3) 0.0923(3) 0.0480(13) Uani 1 1 d . . .
H26 H -0.5309 0.6878 0.0480 0.058 Uiso 1 1 calc R . .
C27 C -0.4029(5) 0.5932(3) 0.1061(3) 0.0394(11) Uani 1 1 d . . .
H27 H -0.3342 0.5876 0.0711 0.047 Uiso 1 1 calc R . .
N1 N 0.1321(4) 0.45860(17) 0.14508(18) 0.0278(8) Uani 1 1 d . . .
N2 N 0.1855(4) 0.31673(17) 0.17491(16) 0.0235(7) Uani 1 1 d . . .
N3 N -0.1213(3) 0.37147(17) 0.24293(16) 0.0212(7) Uani 1 1 d . . .
N4 N -0.2276(3) 0.43666(17) 0.24896(17) 0.0228(7) Uani 1 1 d . . .
O1 O -0.0120(3) 0.57231(15) 0.06027(14) 0.0331(7) Uani 1 1 d . . .
O2 O 0.0038(3) 0.58342(14) 0.19833(14) 0.0292(6) Uani 1 1 d . . .
O3 O -0.3881(3) 0.08832(14) -0.00425(14) 0.0276(6) Uani 1 1 d . . .
S1 S -0.00396(12) 0.52870(5) 0.13213(5) 0.0260(3) 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 N2 1.325(4) . ?
C1 N1 1.330(4) . ?
C1 C2 1.532(5) . ?
C2 N3 1.506(4) . ?
C2 C8 1.531(5) . ?
C2 C3 1.545(5) . ?
C3 C21 1.501(5) . ?
C3 S1 1.822(4) . ?
C3 H3 1.0000 . ?
C4 N2 1.473(5) . ?
C4 C5 1.520(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N2 1.483(4) . ?
C6 C7 1.523(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.384(5) . ?
C8 C9 1.389(5) . ?
C9 C10 1.388(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(5) . ?
C10 H10 0.9500 . ?
C11 O3 1.370(4) . ?
C11 C12 1.380(5) . ?
C12 C13 1.388(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O3 1.437(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.386(5) . ?
C15 C20 1.391(5) . ?
C15 N3 1.448(4) . ?
C16 C17 1.393(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 N4 1.285(4) . ?
C21 C22 1.466(5) . ?
C22 C27 1.390(5) . ?
C22 C23 1.393(5) . ?
C23 C24 1.388(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
N1 S1 1.615(3) . ?
N3 N4 1.402(4) . ?
O1 S1 1.436(3) . ?
O2 S1 1.442(3) . ?
 
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
N2 C1 N1 119.0(3) . . ?
N2 C1 C2 123.7(3) . . ?
N1 C1 C2 117.3(3) . . ?
N3 C2 C8 110.8(3) . . ?
N3 C2 C1 113.0(3) . . ?
C8 C2 C1 115.0(3) . . ?
N3 C2 C3 101.5(3) . . ?
C8 C2 C3 109.9(3) . . ?
C1 C2 C3 105.7(3) . . ?
C21 C3 C2 102.7(3) . . ?
C21 C3 S1 112.0(2) . . ?
C2 C3 S1 103.8(2) . . ?
C21 C3 H3 112.5 . . ?
C2 C3 H3 112.5 . . ?
S1 C3 H3 112.5 . . ?
N2 C4 C5 112.7(3) . . ?
N2 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
N2 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 112.8(3) . . ?
N2 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.5(3) . . ?
C13 C8 C2 121.3(3) . . ?
C9 C8 C2 120.1(3) . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
O3 C11 C12 115.4(3) . . ?
O3 C11 C10 124.8(3) . . ?
C12 C11 C10 119.8(3) . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 120.9(3) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 119.8(3) . . ?
C16 C15 N3 118.6(3) . . ?
C20 C15 N3 121.6(3) . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.1(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C15 120.3(3) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
N4 C21 C22 123.0(3) . . ?
N4 C21 C3 112.6(3) . . ?
C22 C21 C3 124.4(3) . . ?
C27 C22 C23 118.7(4) . . ?
C27 C22 C21 120.7(4) . . ?
C23 C22 C21 120.6(3) . . ?
C24 C23 C22 120.9(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 119.5(4) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.3(4) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 120.2(4) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C22 120.4(4) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?
C1 N1 S1 112.6(3) . . ?
C1 N2 C4 117.9(3) . . ?
C1 N2 C6 125.8(3) . . ?
C4 N2 C6 116.0(3) . . ?
N4 N3 C15 113.2(3) . . ?
N4 N3 C2 110.3(2) . . ?
C15 N3 C2 121.2(3) . . ?
C21 N4 N3 110.4(3) . . ?
C11 O3 C14 117.5(3) . . ?
O1 S1 O2 116.06(15) . . ?
O1 S1 N1 111.32(17) . . ?
O2 S1 N1 110.37(16) . . ?
O1 S1 C3 110.76(17) . . ?
O2 S1 C3 109.14(16) . . ?
N1 S1 C3 97.63(15) . . ?
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              27.21
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.481
_refine_diff_density_min   -0.481
_refine_diff_density_rms    0.077
 
