 
data_elaf011
 
_audit_creation_method            SHELXL-2014
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C18 H21 N5 O S'
_chemical_formula_sum
 'C18 H21 N5 O S' 
_chemical_formula_weight          355.46

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/n'
_space_group_name_Hall            '-P 2yn'
 
_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+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    7.1287(2)
_cell_length_b                    15.0536(6)
_cell_length_c                    16.4704(6)
_cell_angle_alpha                 90
_cell_angle_beta                  97.810(2)
_cell_angle_gamma                 90
_cell_volume                      1751.09(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     5701 
_cell_measurement_theta_min       2.50 
_cell_measurement_theta_max       28.26 
 
_exptl_crystal_description        yellow 
_exptl_crystal_colour             block 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.348          
_exptl_crystal_F_000              752
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.060
_exptl_crystal_size_min           0.060
_exptl_absorpt_coefficient_mu     0.202
_shelx_estimated_absorpt_T_min    0.961
_shelx_estimated_absorpt_T_max    0.988
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.9608 
_exptl_absorpt_correction_T_max   0.9880 
_exptl_absorpt_process_details    SADABS 
 
_exptl_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  ? 
_diffrn_reflns_number             24802
_diffrn_reflns_av_unetI/netI      0.0443
_diffrn_reflns_av_R_equivalents   0.0503
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          2.706
_diffrn_reflns_theta_max          30.081
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.969
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.969
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.969
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4975
_reflns_number_gt                 3839
_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        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014 (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)+(0.0716P)²+0.4404P] 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          4975
_refine_ls_number_parameters      226
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0633
_refine_ls_R_factor_gt            0.0454
_refine_ls_wR_factor_ref          0.1330
_refine_ls_wR_factor_gt           0.1203
_refine_ls_goodness_of_fit_ref    1.033
_refine_ls_restrained_S_all       1.033
_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 0.77866(5) 0.78044(3) 0.23039(2) 0.02304(12) Uani 1 1 d . . . . .
O1 O 0.75438(16) 0.84787(8) -0.40901(7) 0.0288(3) Uani 1 1 d . . . . .
N1 N 0.71452(17) 0.95352(9) -0.00366(8) 0.0186(3) Uani 1 1 d . . . . .
N2 N 0.93624(17) 1.00867(9) 0.15438(8) 0.0197(3) Uani 1 1 d . . . . .
N3 N 0.86086(17) 0.92564(8) 0.15511(8) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.7833 0.9063 0.1127 0.022 Uiso 1 1 calc R U . . .
N4 N 1.05370(17) 0.89985(9) 0.27593(8) 0.0197(3) Uani 1 1 d . . . . .
H4 H 1.1074 0.9505 0.2655 0.024 Uiso 1 1 calc R U . . .
N5 N 0.62982(16) 0.95603(8) -0.28317(7) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.6222(2) 0.93578(11) -0.07823(9) 0.0200(3) Uani 1 1 d . . . . .
H1 H 0.5752 0.8772 -0.0886 0.024 Uiso 1 1 calc R U . . .
C2 C 0.59058(19) 0.99758(10) -0.14153(9) 0.0186(3) Uani 1 1 d . . . . .
C3 C 0.6543(2) 1.08368(10) -0.12457(9) 0.0194(3) Uani 1 1 d . . . . .
H3A H 0.6311 1.1287 -0.1651 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7517(2) 1.10355(10) -0.04824(9) 0.0200(3) Uani 1 1 d . . . . .
H4A H 0.7975 1.1620 -0.0361 0.024 Uiso 1 1 calc R U . . .
C5 C 0.7816(2) 1.03664(10) 0.01066(9) 0.0193(3) Uani 1 1 d . . . . .
C6 C 0.8936(2) 1.05686(11) 0.08997(9) 0.0197(3) Uani 1 1 d . . . . .
H6 H 0.9432 1.1155 0.0945 0.024 Uiso 1 1 calc R U . . .
C7 C 0.9066(2) 0.87257(10) 0.22225(9) 0.0191(3) Uani 1 1 d . . . . .
C8 C 0.4932(2) 0.97286(11) -0.22532(9) 0.0202(3) Uani 1 1 d . . . . .
H8A H 0.4157 0.9189 -0.2210 0.024 Uiso 1 1 calc R U . . .
H8B H 0.4071 1.0216 -0.2467 0.024 Uiso 1 1 calc R U . . .
C9 C 0.5257(2) 0.95108(11) -0.36667(9) 0.0209(3) Uani 1 1 d . . . . .
H9A H 0.4616 1.0084 -0.3810 0.025 Uiso 1 1 calc R U . . .
H9B H 0.4276 0.9042 -0.3690 0.025 Uiso 1 1 calc R U . . .
C10 C 0.6606(2) 0.93032(11) -0.42768(10) 0.0253(3) Uani 1 1 d . . . . .
H10A H 0.5892 0.9277 -0.4836 0.030 Uiso 1 1 calc R U . . .
H10B H 0.7557 0.9784 -0.4266 0.030 Uiso 1 1 calc R U . . .
C11 C 0.8576(2) 0.85196(12) -0.32832(11) 0.0272(4) Uani 1 1 d . . . . .
H11A H 0.9542 0.8994 -0.3261 0.033 Uiso 1 1 calc R U . . .
H11B H 0.9239 0.7949 -0.3154 0.033 Uiso 1 1 calc R U . . .
C12 C 0.7272(2) 0.87040(10) -0.26516(10) 0.0206(3) Uani 1 1 d . . . . .
H12A H 0.6326 0.8222 -0.2660 0.025 Uiso 1 1 calc R U . . .
H12B H 0.8015 0.8724 -0.2098 0.025 Uiso 1 1 calc R U . . .
C13 C 1.1303(2) 0.85381(10) 0.34844(9) 0.0193(3) Uani 1 1 d . . . . .
C14 C 1.3195(2) 0.82855(10) 0.35683(9) 0.0210(3) Uani 1 1 d . . . . .
H14 H 1.3909 0.8374 0.3128 0.025 Uiso 1 1 calc R U . . .
C15 C 1.4042(2) 0.79045(10) 0.42923(10) 0.0240(3) Uani 1 1 d . . . . .
H15 H 1.5342 0.7744 0.4350 0.029 Uiso 1 1 calc R U . . .
C16 C 1.3004(3) 0.77560(11) 0.49318(10) 0.0268(4) Uani 1 1 d . . . . .
H16 H 1.3585 0.7489 0.5426 0.032 Uiso 1 1 calc R U . . .
C17 C 1.1114(2) 0.79989(11) 0.48461(10) 0.0273(4) Uani 1 1 d . . . . .
H17 H 1.0396 0.7894 0.5282 0.033 Uiso 1 1 calc R U . . .
C18 C 1.0258(2) 0.83952(11) 0.41279(10) 0.0239(3) Uani 1 1 d . . . . .
H18 H 0.8965 0.8568 0.4076 0.029 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 C7 1.6752(16) . ?
O1 C10 1.424(2) . ?
O1 C11 1.430(2) . ?
N1 C1 1.3391(19) . ?
N1 C5 1.349(2) . ?
N2 C6 1.2870(19) . ?
N2 N3 1.3612(18) . ?
N3 C7 1.3673(19) . ?
N3 H3 0.8800 . ?
N4 C7 1.3410(19) . ?
N4 C13 1.4239(19) . ?
N4 H4 0.8800 . ?
N5 C9 1.4731(18) . ?
N5 C8 1.4738(18) . ?
N5 C12 1.4750(19) . ?
C1 C2 1.393(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(2) . ?
C2 C8 1.505(2) . ?
C3 C4 1.384(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.395(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.467(2) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.515(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.512(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.390(2) . ?
C13 C18 1.393(2) . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(2) . ?
C17 H17 0.9500 . ?
C18 H18 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
C10 O1 C11 109.29(12) . . ?
C1 N1 C5 117.63(13) . . ?
C6 N2 N3 118.40(13) . . ?
N2 N3 C7 119.51(13) . . ?
N2 N3 H3 120.2 . . ?
C7 N3 H3 120.2 . . ?
C7 N4 C13 125.48(13) . . ?
C7 N4 H4 117.3 . . ?
C13 N4 H4 117.3 . . ?
C9 N5 C8 108.60(11) . . ?
C9 N5 C12 107.90(12) . . ?
C8 N5 C12 110.76(12) . . ?
N1 C1 C2 124.25(14) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 117.23(14) . . ?
C3 C2 C8 120.84(14) . . ?
C1 C2 C8 121.94(14) . . ?
C4 C3 C2 119.62(14) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 119.10(14) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
N1 C5 C4 122.09(14) . . ?
N1 C5 C6 119.03(13) . . ?
C4 C5 C6 118.87(14) . . ?
N2 C6 C5 130.98(15) . . ?
N2 C6 H6 114.5 . . ?
C5 C6 H6 114.5 . . ?
N4 C7 N3 115.69(13) . . ?
N4 C7 S1 125.89(12) . . ?
N3 C7 S1 118.41(11) . . ?
N5 C8 C2 111.88(11) . . ?
N5 C8 H8A 109.2 . . ?
C2 C8 H8A 109.2 . . ?
N5 C8 H8B 109.2 . . ?
C2 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N5 C9 C10 110.18(12) . . ?
N5 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N5 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
O1 C10 C9 111.00(13) . . ?
O1 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
O1 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O1 C11 C12 111.13(12) . . ?
O1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
O1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N5 C12 C11 109.80(13) . . ?
N5 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
N5 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C18 119.64(14) . . ?
C14 C13 N4 118.23(13) . . ?
C18 C13 N4 121.96(14) . . ?
C15 C14 C13 120.16(14) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.39(15) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.52(15) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.59(15) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 119.69(15) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C6 N2 N3 C7 178.86(13) . . . . ?
C5 N1 C1 C2 -0.3(2) . . . . ?
N1 C1 C2 C3 -2.2(2) . . . . ?
N1 C1 C2 C8 177.28(13) . . . . ?
C1 C2 C3 C4 2.7(2) . . . . ?
C8 C2 C3 C4 -176.79(13) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C1 N1 C5 C4 2.2(2) . . . . ?
C1 N1 C5 C6 -176.21(12) . . . . ?
C3 C4 C5 N1 -1.7(2) . . . . ?
C3 C4 C5 C6 176.78(13) . . . . ?
N3 N2 C6 C5 -4.2(2) . . . . ?
N1 C5 C6 N2 -3.9(2) . . . . ?
C4 C5 C6 N2 177.62(15) . . . . ?
C13 N4 C7 N3 -177.70(13) . . . . ?
C13 N4 C7 S1 1.8(2) . . . . ?
N2 N3 C7 N4 -13.29(19) . . . . ?
N2 N3 C7 S1 167.19(10) . . . . ?
C9 N5 C8 C2 -168.17(13) . . . . ?
C12 N5 C8 C2 73.51(16) . . . . ?
C3 C2 C8 N5 80.82(17) . . . . ?
C1 C2 C8 N5 -98.63(16) . . . . ?
C8 N5 C9 C10 -177.85(13) . . . . ?
C12 N5 C9 C10 -57.74(16) . . . . ?
C11 O1 C10 C9 -59.22(16) . . . . ?
N5 C9 C10 O1 59.59(17) . . . . ?
C10 O1 C11 C12 59.62(17) . . . . ?
C9 N5 C12 C11 57.82(15) . . . . ?
C8 N5 C12 C11 176.56(12) . . . . ?
O1 C11 C12 N5 -59.90(17) . . . . ?
C7 N4 C13 C14 120.90(16) . . . . ?
C7 N4 C13 C18 -63.9(2) . . . . ?
C18 C13 C14 C15 -0.9(2) . . . . ?
N4 C13 C14 C15 174.48(14) . . . . ?
C13 C14 C15 C16 1.3(2) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C16 C17 C18 C13 0.9(2) . . . . ?
C14 C13 C18 C17 -0.2(2) . . . . ?
N4 C13 C18 C17 -175.38(15) . . . . ?
 
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 H3 N1  0.88 2.04 2.7131(18) 132.5 .
N4 H4 N5  0.88 2.33 3.1205(17) 149.6 3_775
C11 H11B S1  0.99 2.78 3.6233(16) 143.4 4_675
C12 H12A S1  0.99 2.95 3.9145(16) 164.3 4_575
C12 H12B N2  0.99 2.66 3.3479(19) 126.8 3_775
 
_refine_diff_density_max    0.638
_refine_diff_density_min   -0.278
_refine_diff_density_rms    0.063

_shelxl_version_number 2014-3



