 
data_mo_180849lt_0m
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C27 H24 N4 O S' 
_chemical_formula_weight          452.56

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    15.9136(5)
_cell_length_b                    8.7495(3)
_cell_length_c                    17.2835(6)
_cell_angle_alpha                 90
_cell_angle_beta                  112.4710(10)
_cell_angle_gamma                 90
_cell_volume                      2223.77(13)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9862
_cell_measurement_theta_min       2.6544
_cell_measurement_theta_max       26.4027
 
_exptl_crystal_description        Tabullar
_exptl_crystal_colour             Colorless
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.352          
_exptl_crystal_F_000              952
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.24
_exptl_crystal_size_min           0.12
_exptl_absorpt_coefficient_mu     0.174
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8962  
_exptl_absorpt_correction_T_max   0.9485
_exptl_absorpt_process_details    'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  8.3333
_diffrn_reflns_number             38317
_diffrn_reflns_av_unetI/netI      0.0176
_diffrn_reflns_av_R_equivalents   0.0297
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          1.385
_diffrn_reflns_theta_max          26.416
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4554
_reflns_number_gt                 4044
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction         'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0577P)²+0.8623P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4554
_refine_ls_number_parameters      300
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0411
_refine_ls_R_factor_gt            0.0320
_refine_ls_wR_factor_ref          0.1091
_refine_ls_wR_factor_gt           0.0910
_refine_ls_goodness_of_fit_ref    1.188
_refine_ls_restrained_S_all       1.188
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.40474(3) 0.03615(4) 0.36826(2) 0.01648(12) Uani 1 1 d . . . . .
O1 O -0.06516(7) 0.38106(12) 0.39230(7) 0.0189(2) Uani 1 1 d . . . . .
N1 N 0.20891(8) -0.20136(14) 0.44911(8) 0.0150(3) Uani 1 1 d . . . . .
N2 N 0.41752(8) 0.22702(14) 0.48524(8) 0.0151(3) Uani 1 1 d . . . . .
N3 N 0.31557(8) -0.21889(14) 0.39376(8) 0.0162(3) Uani 1 1 d . . . . .
N4 N 0.34339(9) 0.02618(16) 0.64015(9) 0.0224(3) Uani 1 1 d . . . . .
C1 C -0.14030(11) 0.38213(19) 0.31322(10) 0.0230(3) Uani 1 1 d . . . . .
H24 H -0.1175 0.3786 0.2680 0.034 Uiso 1 1 calc R U . . .
H3 H -0.1759 0.4756 0.3082 0.034 Uiso 1 1 calc R U . . .
H1 H -0.1789 0.2929 0.3093 0.034 Uiso 1 1 calc R U . . .
C2 C -0.01148(10) 0.25260(17) 0.41171(9) 0.0155(3) Uani 1 1 d . . . . .
C3 C 0.05763(10) 0.25047(18) 0.49134(9) 0.0177(3) Uani 1 1 d . . . . .
H4 H 0.0665 0.3356 0.5277 0.021 Uiso 1 1 calc R U . . .
C4 C 0.11324(10) 0.12327(18) 0.51699(9) 0.0179(3) Uani 1 1 d . . . . .
H5 H 0.1599 0.1218 0.5714 0.022 Uiso 1 1 calc R U . . .
C5 C 0.10217(10) -0.00259(18) 0.46452(9) 0.0155(3) Uani 1 1 d . . . . .
C6 C 0.15608(10) -0.14725(18) 0.49724(9) 0.0169(3) Uani 1 1 d . . . . .
H23 H 0.1983 -0.1295 0.5558 0.020 Uiso 1 1 calc R U . . .
H22 H 0.1135 -0.2292 0.4980 0.020 Uiso 1 1 calc R U . . .
C7 C 0.28599(10) -0.13934(17) 0.44347(9) 0.0144(3) Uani 1 1 d . . . . .
C8 C 0.33115(10) -0.00210(17) 0.48798(9) 0.0151(3) Uani 1 1 d . . . . .
C9 C 0.38067(9) 0.09056(17) 0.45521(9) 0.0140(3) Uani 1 1 d . . . . .
C10 C 0.39986(10) 0.31554(17) 0.54733(9) 0.0152(3) Uani 1 1 d . . . . .
C11 C 0.47163(10) 0.35318(18) 0.62132(9) 0.0181(3) Uani 1 1 d . . . . .
H9 H 0.5306 0.3124 0.6333 0.022 Uiso 1 1 calc R U . . .
C12 C 0.45585(11) 0.45153(18) 0.67759(10) 0.0215(3) Uani 1 1 d . . . . .
H10 H 0.5043 0.4786 0.7283 0.026 Uiso 1 1 calc R U . . .
C13 C 0.36925(12) 0.51021(19) 0.65953(10) 0.0239(4) Uani 1 1 d . . . . .
H2 H 0.3588 0.5787 0.6976 0.029 Uiso 1 1 calc R U . . .
C14 C 0.03461(10) 0.00407(18) 0.38459(10) 0.0172(3) Uani 1 1 d . . . . .
H6 H 0.0271 -0.0795 0.3475 0.021 Uiso 1 1 calc R U . . .
C15 C -0.02227(10) 0.13021(17) 0.35769(9) 0.0169(3) Uani 1 1 d . . . . .
H7 H -0.0681 0.1326 0.3028 0.020 Uiso 1 1 calc R U . . .
C16 C 0.18875(10) -0.33161(17) 0.39955(9) 0.0148(3) Uani 1 1 d . . . . .
C17 C 0.25602(10) -0.34050(17) 0.36588(9) 0.0151(3) Uani 1 1 d . . . . .
C18 C 0.45033(11) 0.22394(18) 0.36134(10) 0.0195(3) Uani 1 1 d . . . . .
H15 H 0.5031 0.2151 0.3446 0.023 Uiso 1 1 calc R U . . .
H14 H 0.4034 0.2884 0.3199 0.023 Uiso 1 1 calc R U . . .
C19 C 0.47904(10) 0.29167(18) 0.44831(10) 0.0189(3) Uani 1 1 d . . . . .
H12 H 0.5429 0.2643 0.4825 0.023 Uiso 1 1 calc R U . . .
H13 H 0.4737 0.4044 0.4452 0.023 Uiso 1 1 calc R U . . .
C20 C 0.31303(11) 0.37236(18) 0.52912(9) 0.0196(3) Uani 1 1 d . . . . .
H8 H 0.2645 0.3455 0.4784 0.024 Uiso 1 1 calc R U . . .
C21 C 0.29814(12) 0.46921(19) 0.58628(10) 0.0238(4) Uani 1 1 d . . . . .
H11 H 0.2388 0.5076 0.5750 0.029 Uiso 1 1 calc R U . . .
C22 C 0.33763(10) 0.01919(17) 0.57173(10) 0.0166(3) Uani 1 1 d . . . . .
C23 C 0.25796(10) -0.46344(17) 0.31475(9) 0.0166(3) Uani 1 1 d . . . . .
H16 H 0.3030 -0.4693 0.2913 0.020 Uiso 1 1 calc R U . . .
C24 C 0.19238(10) -0.57654(18) 0.29927(9) 0.0173(3) Uani 1 1 d . . . . .
C25 C 0.19321(11) -0.71587(18) 0.24812(10) 0.0226(3) Uani 1 1 d . . . . .
H19 H 0.2364 -0.7002 0.2208 0.034 Uiso 1 1 calc R U . . .
H18 H 0.1322 -0.7326 0.2054 0.034 Uiso 1 1 calc R U . . .
H17 H 0.2116 -0.8054 0.2849 0.034 Uiso 1 1 calc R U . . .
C26 C 0.12484(10) -0.56344(18) 0.33287(9) 0.0184(3) Uani 1 1 d . . . . .
H21 H 0.0799 -0.6411 0.3207 0.022 Uiso 1 1 calc R U . . .
C27 C 0.12120(10) -0.44202(18) 0.38282(9) 0.0174(3) Uani 1 1 d . . . . .
H20 H 0.0748 -0.4345 0.4046 0.021 Uiso 1 1 calc R U . . .
 
 
_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 C9 1.7527(15) . ?
S1 C18 1.8185(16) . ?
O1 C2 1.3735(18) . ?
O1 C1 1.4313(19) . ?
N1 C7 1.3783(18) . ?
N1 C16 1.3876(19) . ?
N1 C6 1.4688(18) . ?
N2 C9 1.3439(19) . ?
N2 C10 1.4357(18) . ?
N2 C19 1.4707(18) . ?
N3 C7 1.3242(19) . ?
N3 C17 1.3832(19) . ?
N4 C22 1.152(2) . ?
C1 H24 0.9800 . ?
C1 H3 0.9800 . ?
C1 H1 0.9800 . ?
C2 C15 1.388(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.385(2) . ?
C3 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C4 H5 0.9500 . ?
C5 C14 1.390(2) . ?
C5 C6 1.512(2) . ?
C6 H23 0.9900 . ?
C6 H22 0.9900 . ?
C7 C8 1.459(2) . ?
C8 C9 1.393(2) . ?
C8 C22 1.424(2) . ?
C10 C20 1.387(2) . ?
C10 C11 1.390(2) . ?
C11 C12 1.391(2) . ?
C11 H9 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H10 0.9500 . ?
C13 C21 1.385(2) . ?
C13 H2 0.9500 . ?
C14 C15 1.390(2) . ?
C14 H6 0.9500 . ?
C15 H7 0.9500 . ?
C16 C27 1.391(2) . ?
C16 C17 1.402(2) . ?
C17 C23 1.400(2) . ?
C18 C19 1.515(2) . ?
C18 H15 0.9900 . ?
C18 H14 0.9900 . ?
C19 H12 0.9900 . ?
C19 H13 0.9900 . ?
C20 C21 1.389(2) . ?
C20 H8 0.9500 . ?
C21 H11 0.9500 . ?
C23 C24 1.388(2) . ?
C23 H16 0.9500 . ?
C24 C26 1.408(2) . ?
C24 C25 1.509(2) . ?
C25 H19 0.9800 . ?
C25 H18 0.9800 . ?
C25 H17 0.9800 . ?
C26 C27 1.384(2) . ?
C26 H21 0.9500 . ?
C27 H20 0.9500 . ?
 
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
C9 S1 C18 91.97(7) . . ?
C2 O1 C1 116.94(12) . . ?
C7 N1 C16 106.37(12) . . ?
C7 N1 C6 129.09(13) . . ?
C16 N1 C6 124.54(12) . . ?
C9 N2 C10 125.92(12) . . ?
C9 N2 C19 116.03(12) . . ?
C10 N2 C19 118.02(12) . . ?
C7 N3 C17 105.32(12) . . ?
O1 C1 H24 109.5 . . ?
O1 C1 H3 109.5 . . ?
H24 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H24 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C2 C15 124.18(13) . . ?
O1 C2 C3 115.72(13) . . ?
C15 C2 C3 120.10(14) . . ?
C4 C3 C2 119.52(14) . . ?
C4 C3 H4 120.2 . . ?
C2 C3 H4 120.2 . . ?
C3 C4 C5 121.33(14) . . ?
C3 C4 H5 119.3 . . ?
C5 C4 H5 119.3 . . ?
C14 C5 C4 118.08(14) . . ?
C14 C5 C6 121.30(14) . . ?
C4 C5 C6 120.35(13) . . ?
N1 C6 C5 115.07(12) . . ?
N1 C6 H23 108.5 . . ?
C5 C6 H23 108.5 . . ?
N1 C6 H22 108.5 . . ?
C5 C6 H22 108.5 . . ?
H23 C6 H22 107.5 . . ?
N3 C7 N1 112.68(13) . . ?
N3 C7 C8 123.32(13) . . ?
N1 C7 C8 124.00(13) . . ?
C9 C8 C22 120.33(14) . . ?
C9 C8 C7 120.39(13) . . ?
C22 C8 C7 118.27(13) . . ?
N2 C9 C8 126.25(14) . . ?
N2 C9 S1 111.48(11) . . ?
C8 C9 S1 122.25(11) . . ?
C20 C10 C11 121.40(14) . . ?
C20 C10 N2 119.11(13) . . ?
C11 C10 N2 119.26(13) . . ?
C10 C11 C12 119.02(14) . . ?
C10 C11 H9 120.5 . . ?
C12 C11 H9 120.5 . . ?
C13 C12 C11 120.00(15) . . ?
C13 C12 H10 120.0 . . ?
C11 C12 H10 120.0 . . ?
C21 C13 C12 120.22(15) . . ?
C21 C13 H2 119.9 . . ?
C12 C13 H2 119.9 . . ?
C15 C14 C5 121.55(14) . . ?
C15 C14 H6 119.2 . . ?
C5 C14 H6 119.2 . . ?
C2 C15 C14 119.37(14) . . ?
C2 C15 H7 120.3 . . ?
C14 C15 H7 120.3 . . ?
N1 C16 C27 132.60(14) . . ?
N1 C16 C17 105.58(12) . . ?
C27 C16 C17 121.80(14) . . ?
N3 C17 C23 129.30(13) . . ?
N3 C17 C16 110.05(13) . . ?
C23 C17 C16 120.60(14) . . ?
C19 C18 S1 105.35(10) . . ?
C19 C18 H15 110.7 . . ?
S1 C18 H15 110.7 . . ?
C19 C18 H14 110.7 . . ?
S1 C18 H14 110.7 . . ?
H15 C18 H14 108.8 . . ?
N2 C19 C18 106.37(12) . . ?
N2 C19 H12 110.5 . . ?
C18 C19 H12 110.5 . . ?
N2 C19 H13 110.5 . . ?
C18 C19 H13 110.5 . . ?
H12 C19 H13 108.6 . . ?
C10 C20 C21 118.90(15) . . ?
C10 C20 H8 120.5 . . ?
C21 C20 H8 120.5 . . ?
C13 C21 C20 120.44(15) . . ?
C13 C21 H11 119.8 . . ?
C20 C21 H11 119.8 . . ?
N4 C22 C8 175.51(16) . . ?
C24 C23 C17 118.23(14) . . ?
C24 C23 H16 120.9 . . ?
C17 C23 H16 120.9 . . ?
C23 C24 C26 119.92(14) . . ?
C23 C24 C25 120.97(14) . . ?
C26 C24 C25 119.10(14) . . ?
C24 C25 H19 109.5 . . ?
C24 C25 H18 109.5 . . ?
H19 C25 H18 109.5 . . ?
C24 C25 H17 109.5 . . ?
H19 C25 H17 109.5 . . ?
H18 C25 H17 109.5 . . ?
C27 C26 C24 122.70(14) . . ?
C27 C26 H21 118.6 . . ?
C24 C26 H21 118.6 . . ?
C26 C27 C16 116.71(14) . . ?
C26 C27 H20 121.6 . . ?
C16 C27 H20 121.6 . . ?
 
_refine_diff_density_max    0.541
_refine_diff_density_min   -0.489
_refine_diff_density_rms    0.150

_shelxl_version_number 2014/6



