
data_global


data_p-Cl
#TrackingRef '2011nb0020-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 Cl N2 S'
_chemical_formula_sum            'C13 H19 Cl N2 S'
_chemical_formula_weight         270.81

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.987(7)
_cell_length_b                   8.170(4)
_cell_length_c                   24.959(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2852(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7860
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      33.9

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7692
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13636
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2526
_reflns_number_gt                2278
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0000P)²+5.3737P] 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         2526
_refine_ls_number_parameters     176
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0914
_refine_ls_wR_factor_ref         0.1342
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.324
_refine_ls_restrained_S_all      1.323
_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
S1 S 0.10725(9) 0.19900(13) 0.00544(4) 0.0326(3) Uani 1 1 d . . .
C1 C 0.2158(3) 0.1836(5) 0.12300(16) 0.0318(11) Uani 1 1 d . . .
H1A H 0.1501 0.2048 0.1162 0.038 Uiso 1 1 calc R . .
C2 C 0.2426(3) 0.0887(5) 0.16674(16) 0.0312(10) Uani 1 1 d . . .
H2A H 0.1951 0.0426 0.1894 0.037 Uiso 1 1 calc R . .
C3 C 0.3384(3) 0.0617(5) 0.17719(16) 0.0298(10) Uani 1 1 d . . .
C4 C 0.4085(3) 0.1268(5) 0.14449(17) 0.0356(11) Uani 1 1 d . . .
H4 H 0.4741 0.1085 0.1522 0.043 Uiso 1 1 calc R . .
C5 C 0.3817(3) 0.2194(5) 0.10030(17) 0.0346(11) Uani 1 1 d . . .
H5 H 0.4294 0.2639 0.0774 0.042 Uiso 1 1 calc R . .
C6 C 0.2855(3) 0.2473(5) 0.08930(16) 0.0266(10) Uani 1 1 d . . .
C7 C 0.1882(3) 0.3529(5) 0.01158(16) 0.0303(10) Uani 1 1 d . A .
C8A C 0.1161(3) 0.5201(5) -0.06190(17) 0.0341(11) Uani 0.607(6) 1 d PD A 1
H8A1 H 0.0504 0.5028 -0.0484 0.041 Uiso 0.607(6) 1 calc PR A 1
H8A2 H 0.1273 0.4412 -0.0914 0.041 Uiso 0.607(6) 1 calc PR A 1
C9A C 0.125(2) 0.695(2) -0.0838(11) 0.035(3) Uani 0.607(6) 1 d PD A 1
H9A1 H 0.1092 0.7736 -0.0550 0.042 Uiso 0.607(6) 1 calc PR A 1
H9A2 H 0.1917 0.7147 -0.0951 0.042 Uiso 0.607(6) 1 calc PR A 1
C10A C 0.0590(9) 0.7236(16) -0.1309(7) 0.037(3) Uani 0.607(6) 1 d PD A 1
H10A H -0.0065 0.6889 -0.1211 0.045 Uiso 0.607(6) 1 calc PR A 1
H10B H 0.0803 0.6552 -0.1614 0.045 Uiso 0.607(6) 1 calc PR A 1
C11A C 0.0568(6) 0.9038(9) -0.1486(3) 0.0379(18) Uani 0.607(6) 1 d PD A 1
H11A H 0.0062 0.9173 -0.1760 0.045 Uiso 0.607(6) 1 calc PR A 1
H11B H 0.0391 0.9721 -0.1174 0.045 Uiso 0.607(6) 1 calc PR A 1
C12A C 0.1495(6) 0.9664(10) -0.1713(4) 0.0437(19) Uani 0.607(6) 1 d PD A 1
H12A H 0.1688 0.8967 -0.2018 0.052 Uiso 0.607(6) 1 calc PR A 1
H12B H 0.1999 0.9586 -0.1435 0.052 Uiso 0.607(6) 1 calc PR A 1
C13A C 0.1411(8) 1.1447(11) -0.1902(4) 0.050(3) Uani 0.607(6) 1 d PD A 1
H13A H 0.2027 1.1811 -0.2046 0.075 Uiso 0.607(6) 1 calc PR A 1
H13B H 0.1231 1.2144 -0.1598 0.075 Uiso 0.607(6) 1 calc PR A 1
H13C H 0.0922 1.1525 -0.2181 0.075 Uiso 0.607(6) 1 calc PR A 1
C8B C 0.1161(3) 0.5201(5) -0.06190(17) 0.0341(11) Uani 0.393(6) 1 d PD A 2
H8B1 H 0.0496 0.5189 -0.0484 0.041 Uiso 0.393(6) 1 calc PR A 2
H8B2 H 0.1225 0.4383 -0.0909 0.041 Uiso 0.393(6) 1 calc PR A 2
C9B C 0.145(3) 0.692(3) -0.0815(17) 0.035(3) Uani 0.393(6) 1 d PD A 2
H9B1 H 0.1348 0.7700 -0.0517 0.042 Uiso 0.393(6) 1 calc PR A 2
H9B2 H 0.2136 0.6909 -0.0901 0.042 Uiso 0.393(6) 1 calc PR A 2
C10B C 0.0906(16) 0.753(3) -0.1298(12) 0.037(3) Uani 0.393(6) 1 d PD A 2
H10C H 0.0216 0.7567 -0.1210 0.045 Uiso 0.393(6) 1 calc PR A 2
H10D H 0.0989 0.6731 -0.1594 0.045 Uiso 0.393(6) 1 calc PR A 2
C11B C 0.1226(11) 0.9235(16) -0.1494(5) 0.0379(18) Uani 0.393(6) 1 d PD A 2
H11C H 0.1167 1.0016 -0.1192 0.045 Uiso 0.393(6) 1 calc PR A 2
H11D H 0.1911 0.9179 -0.1593 0.045 Uiso 0.393(6) 1 calc PR A 2
C12B C 0.0672(9) 0.9898(14) -0.1965(4) 0.0437(19) Uani 0.393(6) 1 d PD A 2
H12C H -0.0010 1.0004 -0.1863 0.052 Uiso 0.393(6) 1 calc PR A 2
H12D H 0.0713 0.9110 -0.2265 0.052 Uiso 0.393(6) 1 calc PR A 2
C13B C 0.1042(12) 1.1556(16) -0.2151(6) 0.044(4) Uani 0.393(6) 1 d PD A 2
H13D H 0.0652 1.1944 -0.2452 0.066 Uiso 0.393(6) 1 calc PR A 2
H13E H 0.1709 1.1448 -0.2266 0.066 Uiso 0.393(6) 1 calc PR A 2
H13F H 0.1002 1.2341 -0.1855 0.066 Uiso 0.393(6) 1 calc PR A 2
N1 N 0.2643(3) 0.3526(4) 0.04569(13) 0.0303(9) Uani 1 1 d . . .
H1 H 0.3069 0.4297 0.0397 0.036 Uiso 1 1 calc R . .
N2 N 0.1841(3) 0.4880(4) -0.01877(13) 0.0330(9) Uani 1 1 d . . .
H2 H 0.2266 0.5649 -0.0121 0.040 Uiso 1 1 calc R A 1
Cl2 Cl 0.37183(9) -0.05714(15) 0.23245(5) 0.0435(3) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 1.699(5) . ?
C1 C6 1.389(6) . ?
C1 C2 1.390(6) . ?
C1 H1A 0.9500 . ?
C2 C3 1.383(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.382(6) . ?
C3 Cl2 1.750(4) . ?
C4 C5 1.389(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9500 . ?
C6 N1 1.419(5) . ?
C7 N2 1.340(5) . ?
C7 N1 1.363(5) . ?
C8A N2 1.460(5) . ?
C8A C9A 1.533(9) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A C10A 1.512(10) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A C11A 1.537(11) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.504(10) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A C13A 1.536(10) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C9B C10B 1.508(14) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B C11B 1.547(14) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.509(13) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B C13B 1.523(13) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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 119.7(4) . . ?
C6 C1 H1A 120.1 . . ?
C2 C1 H1A 120.1 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 Cl2 119.3(4) . . ?
C2 C3 Cl2 119.8(3) . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.8(4) . . ?
C1 C6 N1 123.0(4) . . ?
C5 C6 N1 117.0(4) . . ?
N2 C7 N1 112.8(4) . . ?
N2 C7 S1 122.1(3) . . ?
N1 C7 S1 125.1(3) . . ?
N2 C8A C9A 112.2(6) . . ?
N2 C8A H8A1 109.2 . . ?
C9A C8A H8A1 109.2 . . ?
N2 C8A H8A2 109.2 . . ?
C9A C8A H8A2 109.2 . . ?
H8A1 C8A H8A2 107.9 . . ?
C10A C9A C8A 112.0(9) . . ?
C10A C9A H9A1 109.2 . . ?
C8A C9A H9A1 109.2 . . ?
C10A C9A H9A2 109.2 . . ?
C8A C9A H9A2 109.2 . . ?
H9A1 C9A H9A2 107.9 . . ?
C9A C10A C11A 112.7(10) . . ?
C9A C10A H10A 109.1 . . ?
C11A C10A H10A 109.1 . . ?
C9A C10A H10B 109.1 . . ?
C11A C10A H10B 109.1 . . ?
H10A C10A H10B 107.8 . . ?
C12A C11A C10A 114.6(8) . . ?
C12A C11A H11A 108.6 . . ?
C10A C11A H11A 108.6 . . ?
C12A C11A H11B 108.6 . . ?
C10A C11A H11B 108.6 . . ?
H11A C11A H11B 107.6 . . ?
C11A C12A C13A 111.9(7) . . ?
C11A C12A H12A 109.2 . . ?
C13A C12A H12A 109.2 . . ?
C11A C12A H12B 109.2 . . ?
C13A C12A H12B 109.2 . . ?
H12A C12A H12B 107.9 . . ?
C12A C13A H13A 109.5 . . ?
C12A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C12A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C10B C9B H9B1 108.5 . . ?
C10B C9B H9B2 108.5 . . ?
H9B1 C9B H9B2 107.5 . . ?
C9B C10B C11B 113.9(12) . . ?
C9B C10B H10C 108.8 . . ?
C11B C10B H10C 108.8 . . ?
C9B C10B H10D 108.8 . . ?
C11B C10B H10D 108.8 . . ?
H10C C10B H10D 107.7 . . ?
C12B C11B C10B 114.9(12) . . ?
C12B C11B H11C 108.5 . . ?
C10B C11B H11C 108.5 . . ?
C12B C11B H11D 108.5 . . ?
C10B C11B H11D 108.5 . . ?
H11C C11B H11D 107.5 . . ?
C11B C12B C13B 112.5(11) . . ?
C11B C12B H12C 109.1 . . ?
C13B C12B H12C 109.1 . . ?
C11B C12B H12D 109.1 . . ?
C13B C12B H12D 109.1 . . ?
H12C C12B H12D 107.8 . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C7 N1 C6 130.1(4) . . ?
C7 N1 H1 115.0 . . ?
C6 N1 H1 115.0 . . ?
C7 N2 C8A 126.3(4) . . ?
C7 N2 H2 116.9 . . ?
C8A N2 H2 116.9 . . ?

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
N1 H1 S1 0.88 2.65 3.500(4) 163.1 8_665
N2 H2 S1 0.88 2.61 3.442(4) 158.9 8_665

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.058

data_global

# Attachment '2011nb0034a-final.cif'


data_p-NO2
#TrackingRef '2011nb0034a-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
Marco Wenzel
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 N3 O2 S'
_chemical_formula_sum            'C13 H19 N3 O2 S'
_chemical_formula_weight         281.37

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2833(5)
_cell_length_b                   14.9019(15)
_cell_length_c                   18.0119(18)
_cell_angle_alpha                91.957(7)
_cell_angle_beta                 95.987(7)
_cell_angle_gamma                92.116(7)
_cell_volume                     1408.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8919
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9551
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11029
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4960
_reflns_number_gt                4467
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0422P)²+0.6313P] 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         4960
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.7700(3) 0.04702(12) 0.43195(9) 0.0290(4) Uani 1 1 d . . .
H1A H 1.7193 0.0306 0.4807 0.043 Uiso 1 1 calc R . .
H1B H 1.9478 0.0696 0.4379 0.043 Uiso 1 1 calc R . .
H1C H 1.7523 -0.0060 0.3978 0.043 Uiso 1 1 calc R . .
C2 C 1.6007(3) 0.11944(12) 0.40015(9) 0.0254(4) Uani 1 1 d . . .
H2A H 1.6162 0.1722 0.4355 0.030 Uiso 1 1 calc R . .
H2B H 1.4212 0.0966 0.3953 0.030 Uiso 1 1 calc R . .
C3 C 1.6668(3) 0.14911(10) 0.32435(8) 0.0195(3) Uani 1 1 d . . .
H3A H 1.8427 0.1755 0.3300 0.023 Uiso 1 1 calc R . .
H3B H 1.6627 0.0956 0.2901 0.023 Uiso 1 1 calc R . .
C4 C 1.4886(3) 0.21724(10) 0.28931(8) 0.0193(3) Uani 1 1 d . . .
H4A H 1.5009 0.2722 0.3221 0.023 Uiso 1 1 calc R . .
H4B H 1.3115 0.1923 0.2867 0.023 Uiso 1 1 calc R . .
C5 C 1.5438(3) 0.24296(10) 0.21119(8) 0.0185(3) Uani 1 1 d . . .
H5A H 1.7140 0.2737 0.2139 0.022 Uiso 1 1 calc R . .
H5B H 1.5453 0.1880 0.1788 0.022 Uiso 1 1 calc R . .
C6 C 1.3439(3) 0.30441(11) 0.17769(8) 0.0190(3) Uani 1 1 d . . .
H6A H 1.1731 0.2749 0.1779 0.023 Uiso 1 1 calc R . .
H6B H 1.3490 0.3607 0.2088 0.023 Uiso 1 1 calc R . .
C7 C 1.2252(3) 0.37580(10) 0.05952(8) 0.0149(3) Uani 1 1 d . . .
C8 C 1.4484(3) 0.36260(10) -0.05787(8) 0.0147(3) Uani 1 1 d . . .
C9 C 1.4845(3) 0.41251(10) -0.12069(8) 0.0169(3) Uani 1 1 d . . .
H9 H 1.3912 0.4651 -0.1294 0.020 Uiso 1 1 calc R . .
C10 C 1.6529(3) 0.38659(10) -0.17005(8) 0.0172(3) Uani 1 1 d . . .
H10 H 1.6752 0.4203 -0.2129 0.021 Uiso 1 1 calc R . .
C11 C 1.7892(3) 0.31014(10) -0.15570(8) 0.0155(3) Uani 1 1 d . . .
C12 C 1.7541(3) 0.25833(10) -0.09487(8) 0.0163(3) Uani 1 1 d . . .
H12 H 1.8490 0.2061 -0.0863 0.020 Uiso 1 1 calc R . .
C13 C 1.5796(3) 0.28349(10) -0.04678(8) 0.0168(3) Uani 1 1 d . . .
H13 H 1.5487 0.2470 -0.0062 0.020 Uiso 1 1 calc R . .
N1 N 1.3849(2) 0.32603(8) 0.10117(7) 0.0166(3) Uani 1 1 d . . .
H1 H 1.5191 0.3056 0.0820 0.020 Uiso 1 1 calc R . .
N2 N 1.2737(2) 0.39551(8) -0.01123(7) 0.0165(3) Uani 1 1 d . . .
H2 H 1.1766 0.4368 -0.0314 0.020 Uiso 1 1 calc R . .
N3 N 1.9764(2) 0.28432(8) -0.20525(7) 0.0172(3) Uani 1 1 d . . .
O1 O 2.1030(2) 0.21816(7) -0.18961(6) 0.0231(2) Uani 1 1 d . . .
O2 O 2.0033(2) 0.32876(7) -0.26043(6) 0.0235(3) Uani 1 1 d . . .
S1 S 0.96466(7) 0.41808(2) 0.09283(2) 0.01693(10) Uani 1 1 d . . .
C14 C 1.2031(4) 0.52855(13) 0.68299(10) 0.0354(4) Uani 1 1 d . . .
H14A H 1.1703 0.4857 0.7213 0.053 Uiso 1 1 calc R . .
H14B H 1.2715 0.5856 0.7071 0.053 Uiso 1 1 calc R . .
H14C H 1.3268 0.5042 0.6515 0.053 Uiso 1 1 calc R . .
C15 C 0.9572(3) 0.54428(12) 0.63522(10) 0.0309(4) Uani 1 1 d . . .
H15A H 0.8871 0.4859 0.6126 0.037 Uiso 1 1 calc R . .
H15B H 0.8328 0.5676 0.6678 0.037 Uiso 1 1 calc R . .
C16 C 0.9840(3) 0.60907(12) 0.57359(9) 0.0275(4) Uani 1 1 d . . .
H16A H 1.1103 0.5860 0.5415 0.033 Uiso 1 1 calc R . .
H16B H 1.0529 0.6675 0.5964 0.033 Uiso 1 1 calc R . .
C17 C 0.7404(3) 0.62496(11) 0.52467(9) 0.0243(4) Uani 1 1 d . . .
H17A H 0.6144 0.6489 0.5564 0.029 Uiso 1 1 calc R . .
H17B H 0.6702 0.5667 0.5020 0.029 Uiso 1 1 calc R . .
C18 C 0.7745(3) 0.68968(11) 0.46276(9) 0.0253(4) Uani 1 1 d . . .
H18A H 0.8460 0.7479 0.4852 0.030 Uiso 1 1 calc R . .
H18B H 0.8984 0.6655 0.4305 0.030 Uiso 1 1 calc R . .
C19 C 0.5299(3) 0.70521(13) 0.41552(10) 0.0298(4) Uani 1 1 d . . .
H19A H 0.4523 0.6467 0.3955 0.036 Uiso 1 1 calc R . .
H19B H 0.4095 0.7333 0.4470 0.036 Uiso 1 1 calc R . .
C20 C 0.4210(3) 0.82950(10) 0.33129(8) 0.0173(3) Uani 1 1 d . . .
C21 C 0.3881(3) 0.93262(10) 0.22220(8) 0.0162(3) Uani 1 1 d . . .
C22 C 0.4956(3) 0.94216(10) 0.15468(8) 0.0194(3) Uani 1 1 d . . .
H22 H 0.6395 0.9087 0.1455 0.023 Uiso 1 1 calc R . .
C23 C 0.3968(3) 0.99885(11) 0.10189(9) 0.0208(3) Uani 1 1 d . . .
H23 H 0.4710 1.0046 0.0564 0.025 Uiso 1 1 calc R . .
C24 C 0.1873(3) 1.04772(10) 0.11559(8) 0.0183(3) Uani 1 1 d . . .
C25 C 0.0836(3) 1.04213(10) 0.18283(9) 0.0199(3) Uani 1 1 d . . .
H25 H -0.0565 1.0775 0.1922 0.024 Uiso 1 1 calc R . .
C26 C 0.1831(3) 0.98539(10) 0.23631(9) 0.0200(3) Uani 1 1 d . . .
H26 H 0.1128 0.9821 0.2826 0.024 Uiso 1 1 calc R . .
N4 N 0.5695(2) 0.76279(10) 0.35375(8) 0.0248(3) Uani 1 1 d . . .
H4 H 0.7020 0.7529 0.3292 0.030 Uiso 1 1 calc R . .
N5 N 0.5011(2) 0.87021(9) 0.26960(7) 0.0186(3) Uani 1 1 d . . .
H5 H 0.6509 0.8537 0.2582 0.022 Uiso 1 1 calc R . .
N6 N 0.0734(2) 1.10438(9) 0.05815(7) 0.0219(3) Uani 1 1 d . . .
O3 O 0.1646(2) 1.10578(8) -0.00222(6) 0.0311(3) Uani 1 1 d . . .
O4 O -0.1107(2) 1.14819(8) 0.07160(7) 0.0319(3) Uani 1 1 d . . .
S2 S 0.16881(7) 0.85807(3) 0.37390(2) 0.02368(11) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.516(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.520(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.518(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.525(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.515(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.4620(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.3329(19) . ?
C7 N2 1.3652(19) . ?
C7 S1 1.6919(14) . ?
C8 C13 1.399(2) . ?
C8 C9 1.400(2) . ?
C8 N2 1.4020(18) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 N3 1.4533(18) . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?
N3 O2 1.2304(17) . ?
N3 O1 1.2357(17) . ?
C14 C15 1.512(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.510(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.513(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.519(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.501(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N4 1.456(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 N4 1.337(2) . ?
C20 N5 1.3809(19) . ?
C20 S2 1.6668(15) . ?
C21 N5 1.393(2) . ?
C21 C26 1.401(2) . ?
C21 C22 1.404(2) . ?
C22 C23 1.369(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(2) . ?
C24 N6 1.453(2) . ?
C25 C26 1.379(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N4 H4 0.8800 . ?
N5 H5 0.8800 . ?
N6 O4 1.2315(17) . ?
N6 O3 1.2349(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 112.98(13) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 113.76(13) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 114.03(12) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 110.58(12) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C5 111.58(12) . . ?
N1 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 N2 119.92(13) . . ?
N1 C7 S1 121.60(11) . . ?
N2 C7 S1 118.46(11) . . ?
C13 C8 C9 119.15(13) . . ?
C13 C8 N2 124.60(13) . . ?
C9 C8 N2 116.22(13) . . ?
C10 C9 C8 121.09(14) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 118.43(14) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 121.84(13) . . ?
C12 C11 N3 119.06(13) . . ?
C10 C11 N3 119.10(13) . . ?
C13 C12 C11 119.31(14) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C8 120.06(14) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C7 N1 C6 122.02(12) . . ?
C7 N1 H1 119.0 . . ?
C6 N1 H1 119.0 . . ?
C7 N2 C8 132.37(13) . . ?
C7 N2 H2 113.8 . . ?
C8 N2 H2 113.8 . . ?
O2 N3 O1 122.81(12) . . ?
O2 N3 C11 119.23(12) . . ?
O1 N3 C11 117.96(12) . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C14 114.38(14) . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 115.16(14) . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 C18 113.84(13) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 112.88(13) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
N4 C19 C18 111.93(13) . . ?
N4 C19 H19A 109.2 . . ?
C18 C19 H19A 109.2 . . ?
N4 C19 H19B 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
N4 C20 N5 112.13(13) . . ?
N4 C20 S2 122.77(12) . . ?
N5 C20 S2 125.10(12) . . ?
N5 C21 C26 126.11(13) . . ?
N5 C21 C22 115.19(13) . . ?
C26 C21 C22 118.70(14) . . ?
C23 C22 C21 121.16(14) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 119.26(14) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 120.73(14) . . ?
C25 C24 N6 119.80(14) . . ?
C23 C24 N6 119.47(13) . . ?
C26 C25 C24 120.19(14) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 119.87(14) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
C20 N4 C19 125.26(13) . . ?
C20 N4 H4 117.4 . . ?
C19 N4 H4 117.4 . . ?
C20 N5 C21 131.75(13) . . ?
C20 N5 H5 114.1 . . ?
C21 N5 H5 114.1 . . ?
O4 N6 O3 122.97(13) . . ?
O4 N6 C24 118.61(13) . . ?
O3 N6 C24 118.42(13) . . ?

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
N1 H1 S1 0.88 2.83 3.3296(13) 117.9 1_655
N2 H2 S1 0.88 2.56 3.4079(13) 161.4 2_765
N4 H4 O2 0.88 2.42 3.2625(17) 159.2 2_865
N4 H4 S2 0.88 2.90 3.4009(14) 117.9 1_655
N5 H5 O1 0.88 2.17 2.9811(16) 153.0 2_865

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.044

data_global

# Attachment '2011nb0036-final.cif'


data_p-CN
#TrackingRef '2011nb0036-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
Marco Wenzel
;

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N3 S'
_chemical_formula_sum            'C14 H19 N3 S'
_chemical_formula_weight         261.38

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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.466(3)
_cell_length_b                   8.049(3)
_cell_length_c                   13.472(5)
_cell_angle_alpha                82.276(9)
_cell_angle_beta                 82.154(10)
_cell_angle_gamma                63.734(8)
_cell_volume                     716.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3323
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.7

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9626
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6649
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_sigmaI/netI    0.1232
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3271
_reflns_number_gt                2464
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.1923P)²+0.0000P] 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         3271
_refine_ls_number_parameters     179
_refine_ls_number_restraints     195
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.1018
_refine_ls_wR_factor_ref         0.2781
_refine_ls_wR_factor_gt          0.2625
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.049
_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
S1 S 0.97250(10) 0.00943(9) 0.66121(6) 0.0359(3) Uani 1 1 d . . .
N1 N 0.5759(3) 0.1883(3) 0.70112(19) 0.0290(6) Uani 1 1 d . . .
H1 H 0.4550 0.2499 0.6803 0.035 Uiso 1 1 calc R A 1
N2 N 0.6965(3) 0.1689(3) 0.53224(19) 0.0289(6) Uani 1 1 d . . .
H2 H 0.8049 0.1424 0.4904 0.035 Uiso 1 1 calc R B .
N3 N -0.1410(4) 0.5288(4) 0.2807(2) 0.0384(6) Uani 1 1 d . . .
C6A C 0.5936(4) 0.1577(4) 0.8096(2) 0.0339(7) Uani 0.369(4) 1 d PDU B 1
H6A1 H 0.5971 0.2673 0.8334 0.041 Uiso 0.369(4) 1 calc PR B 1
H6A2 H 0.7213 0.0485 0.8236 0.041 Uiso 0.369(4) 1 calc PR B 1
C5A C 0.4087(11) 0.1233(9) 0.8710(6) 0.0321(9) Uani 0.369(4) 1 d PDU B 1
H5A1 H 0.4089 0.1297 0.9438 0.039 Uiso 0.369(4) 1 calc PR B 1
H5A2 H 0.2797 0.2204 0.8484 0.039 Uiso 0.369(4) 1 calc PR B 1
C4A C 0.433(3) -0.069(3) 0.851(2) 0.0370(19) Uani 0.369(4) 1 d PDU B 1
H4A1 H 0.4303 -0.0734 0.7785 0.044 Uiso 0.369(4) 1 calc PR B 1
H4A2 H 0.5645 -0.1646 0.8716 0.044 Uiso 0.369(4) 1 calc PR B 1
C3A C 0.2684(14) -0.1159(11) 0.9084(7) 0.0383(10) Uani 0.369(4) 1 d PDU B 1
H3A1 H 0.2695 -0.1081 0.9811 0.046 Uiso 0.369(4) 1 calc PR B 1
H3A2 H 0.1374 -0.0205 0.8873 0.046 Uiso 0.369(4) 1 calc PR B 1
C2A C 0.285(2) -0.3039(17) 0.8940(12) 0.078(2) Uani 0.369(4) 1 d PDU B 1
H2A1 H 0.4167 -0.4001 0.9136 0.094 Uiso 0.369(4) 1 calc PR B 1
H2A2 H 0.2785 -0.3112 0.8219 0.094 Uiso 0.369(4) 1 calc PR B 1
C1A C 0.117(4) -0.346(4) 0.956(2) 0.060(3) Uani 0.369(4) 1 d PDU B 1
H1A1 H 0.1259 -0.4635 0.9382 0.091 Uiso 0.369(4) 1 calc PR B 1
H1A2 H -0.0136 -0.2454 0.9419 0.091 Uiso 0.369(4) 1 calc PR B 1
H1A3 H 0.1342 -0.3565 1.0280 0.091 Uiso 0.369(4) 1 calc PR B 1
C6B C 0.5936(4) 0.1577(4) 0.8096(2) 0.0339(7) Uani 0.631(4) 1 d PDU B 2
H6B1 H 0.4779 0.2573 0.8439 0.041 Uiso 0.631(4) 1 calc PR B 2
H6B2 H 0.7173 0.1633 0.8238 0.041 Uiso 0.631(4) 1 calc PR B 2
C5B C 0.6000(7) -0.0315(5) 0.8505(4) 0.0321(9) Uani 0.631(4) 1 d PDU B 2
H5B1 H 0.6362 -0.0588 0.9208 0.039 Uiso 0.631(4) 1 calc PR B 2
H5B2 H 0.7049 -0.1293 0.8103 0.039 Uiso 0.631(4) 1 calc PR B 2
C4B C 0.3978(16) -0.0363(13) 0.8472(10) 0.0370(19) Uani 0.631(4) 1 d PDU B 2
H4B1 H 0.2894 0.0778 0.8740 0.044 Uiso 0.631(4) 1 calc PR B 2
H4B2 H 0.3761 -0.0363 0.7763 0.044 Uiso 0.631(4) 1 calc PR B 2
C3B C 0.3842(8) -0.2056(7) 0.9074(4) 0.0383(10) Uani 0.631(4) 1 d PDU B 2
H3B1 H 0.4926 -0.3197 0.8806 0.046 Uiso 0.631(4) 1 calc PR B 2
H3B2 H 0.4062 -0.2057 0.9783 0.046 Uiso 0.631(4) 1 calc PR B 2
C2B C 0.1887(13) -0.2104(12) 0.9043(7) 0.078(2) Uani 0.631(4) 1 d PDU B 2
H2B1 H 0.1755 -0.2272 0.8347 0.094 Uiso 0.631(4) 1 calc PR B 2
H2B2 H 0.0799 -0.0888 0.9220 0.094 Uiso 0.631(4) 1 calc PR B 2
C1B C 0.159(2) -0.366(2) 0.9760(11) 0.060(3) Uani 0.631(4) 1 d PDU B 2
H1B1 H 0.0261 -0.3587 0.9706 0.091 Uiso 0.631(4) 1 calc PR B 2
H1B2 H 0.1706 -0.3506 1.0454 0.091 Uiso 0.631(4) 1 calc PR B 2
H1B3 H 0.2622 -0.4879 0.9573 0.091 Uiso 0.631(4) 1 calc PR B 2
C7 C 0.7310(4) 0.1290(3) 0.6317(2) 0.0284(6) Uani 1 1 d . B .
C8 C 0.5145(4) 0.2459(3) 0.4857(2) 0.0285(6) Uani 1 1 d . B .
C9 C 0.5130(4) 0.3473(3) 0.3926(2) 0.0297(6) Uani 1 1 d . . .
H9 H 0.6272 0.3677 0.3667 0.036 Uiso 1 1 calc R B .
C10 C 0.3466(4) 0.4184(4) 0.3378(2) 0.0319(7) Uani 1 1 d . B .
H10 H 0.3463 0.4869 0.2746 0.038 Uiso 1 1 calc R . .
C11 C 0.1790(4) 0.3878(3) 0.3770(2) 0.0301(6) Uani 1 1 d . . .
C12 C 0.1801(4) 0.2871(3) 0.4692(2) 0.0302(6) Uani 1 1 d . B .
H12 H 0.0655 0.2674 0.4952 0.036 Uiso 1 1 calc R . .
C13 C 0.3472(4) 0.2148(3) 0.5238(2) 0.0286(6) Uani 1 1 d . . .
H13 H 0.3478 0.1448 0.5865 0.034 Uiso 1 1 calc R B .
C14 C 0.0012(4) 0.4654(4) 0.3218(2) 0.0330(7) Uani 1 1 d . B .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 1.700(3) . ?
N1 C7 1.334(4) . ?
N1 C6A 1.463(4) . ?
N1 H1 0.8800 . ?
N2 C7 1.368(4) . ?
N2 C8 1.416(3) . ?
N2 H2 0.8800 . ?
N3 C14 1.139(4) . ?
C6A C5A 1.622(8) . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C5A C4A 1.535(16) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C4A C3A 1.519(15) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C3A C2A 1.501(12) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C2A C1A 1.546(16) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?
C5B C4B 1.534(10) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C4B C3B 1.526(9) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C3B C2B 1.484(8) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C2B C1B 1.554(9) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C1B H1B1 0.9800 . ?
C1B H1B2 0.9800 . ?
C1B H1B3 0.9800 . ?
C8 C13 1.397(4) . ?
C8 C9 1.400(4) . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(4) . ?
C11 C14 1.455(4) . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 H13 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
C7 N1 C6A 124.3(2) . . ?
C7 N1 H1 117.9 . . ?
C6A N1 H1 117.9 . . ?
C7 N2 C8 130.5(2) . . ?
C7 N2 H2 114.7 . . ?
C8 N2 H2 114.7 . . ?
N1 C6A C5A 111.9(3) . . ?
N1 C6A H6A1 109.2 . . ?
C5A C6A H6A1 109.2 . . ?
N1 C6A H6A2 109.2 . . ?
C5A C6A H6A2 109.2 . . ?
H6A1 C6A H6A2 107.9 . . ?
C4A C5A C6A 108.7(8) . . ?
C4A C5A H5A1 110.0 . . ?
C6A C5A H5A1 110.0 . . ?
C4A C5A H5A2 110.0 . . ?
C6A C5A H5A2 110.0 . . ?
H5A1 C5A H5A2 108.3 . . ?
C3A C4A C5A 112.4(15) . . ?
C3A C4A H4A1 109.1 . . ?
C5A C4A H4A1 109.1 . . ?
C3A C4A H4A2 109.1 . . ?
C5A C4A H4A2 109.1 . . ?
H4A1 C4A H4A2 107.9 . . ?
C2A C3A C4A 115.1(11) . . ?
C2A C3A H3A1 108.5 . . ?
C4A C3A H3A1 108.5 . . ?
C2A C3A H3A2 108.5 . . ?
C4A C3A H3A2 108.5 . . ?
H3A1 C3A H3A2 107.5 . . ?
C3A C2A C1A 112.9(17) . . ?
C3A C2A H2A1 109.0 . . ?
C1A C2A H2A1 109.0 . . ?
C3A C2A H2A2 109.0 . . ?
C1A C2A H2A2 109.0 . . ?
H2A1 C2A H2A2 107.8 . . ?
C2A C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
C2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
C4B C5B H5B1 109.3 . . ?
C4B C5B H5B2 109.3 . . ?
H5B1 C5B H5B2 107.9 . . ?
C3B C4B C5B 113.1(8) . . ?
C3B C4B H4B1 109.0 . . ?
C5B C4B H4B1 109.0 . . ?
C3B C4B H4B2 109.0 . . ?
C5B C4B H4B2 109.0 . . ?
H4B1 C4B H4B2 107.8 . . ?
C2B C3B C4B 113.2(6) . . ?
C2B C3B H3B1 108.9 . . ?
C4B C3B H3B1 108.9 . . ?
C2B C3B H3B2 108.9 . . ?
C4B C3B H3B2 108.9 . . ?
H3B1 C3B H3B2 107.8 . . ?
C3B C2B C1B 114.5(6) . . ?
C3B C2B H2B1 108.6 . . ?
C1B C2B H2B1 108.6 . . ?
C3B C2B H2B2 108.6 . . ?
C1B C2B H2B2 108.6 . . ?
H2B1 C2B H2B2 107.6 . . ?
C2B C1B H1B1 109.5 . . ?
C2B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
C2B C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?
N1 C7 N2 119.1(2) . . ?
N1 C7 S1 122.8(2) . . ?
N2 C7 S1 118.1(2) . . ?
C13 C8 C9 119.8(2) . . ?
C13 C8 N2 123.9(3) . . ?
C9 C8 N2 116.2(2) . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 C14 119.8(2) . . ?
C10 C11 C14 119.8(3) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 119.5(3) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
N3 C14 C11 178.1(3) . . ?

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
C7 N1 C6A C5A -144.3(3) . . . . ?
N1 C6A C5A C4A 71.6(12) . . . . ?
C6A C5A C4A C3A 178.4(13) . . . . ?
C5A C4A C3A C2A -179.0(13) . . . . ?
C4A C3A C2A C1A 178.3(16) . . . . ?
C5B C4B C3B C2B 179.9(8) . . . . ?
C4B C3B C2B C1B -172.3(11) . . . . ?
C6A N1 C7 N2 -178.8(2) . . . . ?
C6A N1 C7 S1 -0.3(3) . . . . ?
C8 N2 C7 N1 -9.5(4) . . . . ?
C8 N2 C7 S1 171.9(2) . . . . ?
C7 N2 C8 C13 -33.3(4) . . . . ?
C7 N2 C8 C9 151.4(3) . . . . ?
C13 C8 C9 C10 0.3(4) . . . . ?
N2 C8 C9 C10 175.9(2) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C9 C10 C11 C14 178.4(2) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C14 C11 C12 C13 -178.8(2) . . . . ?
C11 C12 C13 C8 0.7(4) . . . . ?
C9 C8 C13 C12 -0.8(4) . . . . ?
N2 C8 C13 C12 -175.9(2) . . . . ?

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
N1 H1 N3 0.88 2.27 3.029(3) 144.0 2_566
N2 H2 S1 0.88 2.52 3.327(3) 152.0 2_756

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.929
_refine_diff_density_min         -1.303
_refine_diff_density_rms         0.134

data_global

# Attachment '2011nb0052-final.cif'


data_p-Methyl
#TrackingRef '2011nb0052-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N2 S'
_chemical_formula_sum            'C14 H22 N2 S'
_chemical_formula_weight         250.40

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'
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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   10.731(3)
_cell_length_b                   8.475(2)
_cell_length_c                   16.092(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.010(7)
_cell_angle_gamma                90.00
_cell_volume                     1431.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3122
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9363
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5504
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2520
_reflns_number_gt                2051
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0851P)²+16.4959P] 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         2520
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0980
_refine_ls_wR_factor_ref         0.3108
_refine_ls_wR_factor_gt          0.3033
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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 0.1423(7) 0.5725(9) 0.0772(5) 0.0312(17) Uani 1 1 d . . .
H1A H 0.0883 0.6028 0.1168 0.047 Uiso 1 1 calc R . .
H1B H 0.1424 0.4574 0.0715 0.047 Uiso 1 1 calc R . .
H1C H 0.1092 0.6204 0.0216 0.047 Uiso 1 1 calc R . .
C2 C 0.2770(6) 0.6298(8) 0.1110(4) 0.0234(15) Uani 1 1 d . . .
C3 C 0.3722(6) 0.6021(8) 0.0659(4) 0.0231(15) Uani 1 1 d . . .
H3 H 0.3519 0.5461 0.0137 0.028 Uiso 1 1 calc R . .
C4 C 0.4963(6) 0.6542(8) 0.0953(4) 0.0218(14) Uani 1 1 d . . .
H4 H 0.5593 0.6367 0.0627 0.026 Uiso 1 1 calc R . .
C5 C 0.5274(6) 0.7326(8) 0.1730(4) 0.0196(14) Uani 1 1 d . . .
C6 C 0.4331(7) 0.7613(8) 0.2181(4) 0.0249(15) Uani 1 1 d . . .
H6 H 0.4539 0.8150 0.2710 0.030 Uiso 1 1 calc R . .
C7 C 0.3097(7) 0.7129(9) 0.1874(4) 0.0274(16) Uani 1 1 d . . .
H7 H 0.2459 0.7364 0.2185 0.033 Uiso 1 1 calc R . .
C8 C 0.7688(6) 0.7394(7) 0.2086(4) 0.0188(14) Uani 1 1 d . . .
C9 C 0.9951(6) 0.7762(8) 0.2822(4) 0.0230(15) Uani 1 1 d . . .
H9A H 1.0483 0.8726 0.2871 0.028 Uiso 1 1 calc R . .
H9B H 1.0163 0.7097 0.2366 0.028 Uiso 1 1 calc R . .
C10 C 1.0241(6) 0.6856(8) 0.3665(4) 0.0226(15) Uani 1 1 d . . .
H10A H 0.9959 0.7495 0.4107 0.027 Uiso 1 1 calc R . .
H10B H 0.9745 0.5862 0.3599 0.027 Uiso 1 1 calc R . .
C11 C 1.1652(6) 0.6463(8) 0.3965(4) 0.0248(15) Uani 1 1 d . . .
H11A H 1.2145 0.7456 0.4070 0.030 Uiso 1 1 calc R . .
H11B H 1.1951 0.5882 0.3509 0.030 Uiso 1 1 calc R . .
C12 C 1.1911(7) 0.5467(9) 0.4774(4) 0.0265(16) Uani 1 1 d . . .
H12A H 1.1610 0.6050 0.5228 0.032 Uiso 1 1 calc R . .
H12B H 1.1415 0.4477 0.4667 0.032 Uiso 1 1 calc R . .
C13 C 1.3306(7) 0.5063(9) 0.5081(5) 0.0343(18) Uani 1 1 d . . .
H13A H 1.3794 0.6051 0.5228 0.041 Uiso 1 1 calc R . .
H13B H 1.3623 0.4551 0.4612 0.041 Uiso 1 1 calc R . .
C14 C 1.3558(9) 0.3972(11) 0.5851(5) 0.043(2) Uani 1 1 d . . .
H14A H 1.4473 0.3755 0.6018 0.064 Uiso 1 1 calc R . .
H14B H 1.3094 0.2979 0.5708 0.064 Uiso 1 1 calc R . .
H14C H 1.3267 0.4480 0.6324 0.064 Uiso 1 1 calc R . .
N1 N 0.6507(5) 0.7937(7) 0.2089(4) 0.0215(12) Uani 1 1 d . . .
H1 H 0.6495 0.8834 0.2363 0.026 Uiso 1 1 calc R . .
N2 N 0.8610(5) 0.8197(7) 0.2606(4) 0.0224(13) Uani 1 1 d . . .
H2 H 0.8385 0.9064 0.2837 0.027 Uiso 1 1 calc R . .
S1 S 0.80203(15) 0.58515(19) 0.14796(10) 0.0204(5) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.514(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.390(10) . ?
C2 C7 1.397(10) . ?
C3 C4 1.389(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(10) . ?
C5 N1 1.426(8) . ?
C6 C7 1.376(10) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N2 1.341(8) . ?
C8 N1 1.349(8) . ?
C8 S1 1.713(7) . ?
C9 N2 1.455(8) . ?
C9 C10 1.533(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.527(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.528(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.515(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.525(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.8(6) . . ?
C3 C2 C1 120.6(6) . . ?
C7 C2 C1 121.6(6) . . ?
C4 C3 C2 121.7(6) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.4(6) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.3(6) . . ?
C6 C5 N1 116.2(6) . . ?
C4 C5 N1 124.4(6) . . ?
C7 C6 C5 120.9(6) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 120.9(7) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
N2 C8 N1 113.4(6) . . ?
N2 C8 S1 121.9(5) . . ?
N1 C8 S1 124.7(5) . . ?
N2 C9 C10 110.3(5) . . ?
N2 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 113.2(5) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 112.4(6) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 113.3(6) . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 113.5(7) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 N1 C5 131.9(6) . . ?
C8 N1 H1 114.1 . . ?
C5 N1 H1 114.1 . . ?
C8 N2 C9 125.9(6) . . ?
C8 N2 H2 117.1 . . ?
C9 N2 H2 117.1 . . ?

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
N1 H1 S1 0.88 2.50 3.344(6) 160.2 2_655
N2 H2 S1 0.88 2.54 3.371(6) 156.9 2_655

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.125

data_global

# Attachment '2011nb0054-final.cif'


data_p-COOMe
#TrackingRef '2011nb0054-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 N2 O2 S'
_chemical_formula_sum            'C15 H22 N2 O2 S'
_chemical_formula_weight         294.41

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


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                   11.0875(8)
_cell_length_b                   7.4703(6)
_cell_length_c                   37.579(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.356(7)
_cell_angle_gamma                90.00
_cell_volume                     3061.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7813
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5


_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9915
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10229
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_sigmaI/netI    0.1302
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5045
_reflns_number_gt                2789
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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.

Data completeness only 93.5%, but this is sufficient for proof of structure and hydrogen bonding network
;

_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)+(0.1156P)²+3.3397P] 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         5045
_refine_ls_number_parameters     365
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.0864
_refine_ls_wR_factor_ref         0.2537
_refine_ls_wR_factor_gt          0.2149
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.043
_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
S1 S 0.69171(13) 0.37202(18) 0.25588(4) 0.0215(4) Uani 1 1 d . . .
O1 O 0.6407(3) 0.2784(6) 0.06658(11) 0.0270(10) Uani 1 1 d . . .
O2 O 0.4370(4) 0.2997(6) 0.05060(13) 0.0393(12) Uani 1 1 d . . .
N1 N 0.4967(4) 0.1795(6) 0.22122(14) 0.0227(12) Uani 1 1 d . . .
H1 H 0.4324 0.1147 0.2236 0.027 Uiso 1 1 calc R . .
N2 N 0.5271(4) 0.1753(6) 0.28238(14) 0.0218(11) Uani 1 1 d . . .
H2 H 0.4680 0.0951 0.2785 0.026 Uiso 1 1 calc R . .
C1 C 0.6488(6) 0.2933(9) 0.02799(18) 0.0313(16) Uani 1 1 d . . .
H1A H 0.6041 0.1940 0.0146 0.047 Uiso 1 1 calc R . .
H1B H 0.7350 0.2888 0.0253 0.047 Uiso 1 1 calc R . .
H1C H 0.6127 0.4072 0.0184 0.047 Uiso 1 1 calc R . .
C2 C 0.5276(5) 0.2810(8) 0.07404(18) 0.0240(14) Uani 1 1 d . . .
C3 C 0.5248(5) 0.2562(7) 0.11253(17) 0.0201(14) Uani 1 1 d . . .
C4 C 0.4110(5) 0.2623(7) 0.12384(17) 0.0225(14) Uani 1 1 d . . .
H4 H 0.3381 0.2822 0.1067 0.027 Uiso 1 1 calc R . .
C5 C 0.4055(5) 0.2391(7) 0.16022(17) 0.0233(14) Uani 1 1 d . . .
H5 H 0.3283 0.2426 0.1678 0.028 Uiso 1 1 calc R . .
C6 C 0.5118(5) 0.2109(7) 0.18563(16) 0.0192(13) Uani 1 1 d . . .
C7 C 0.6252(5) 0.2022(7) 0.17438(17) 0.0210(13) Uani 1 1 d . . .
H7 H 0.6981 0.1808 0.1914 0.025 Uiso 1 1 calc R . .
C8 C 0.6296(5) 0.2252(7) 0.13813(17) 0.0210(14) Uani 1 1 d . . .
H8 H 0.7067 0.2195 0.1305 0.025 Uiso 1 1 calc R . .
C9 C 0.5677(5) 0.2352(7) 0.25276(17) 0.0206(14) Uani 1 1 d . . .
C10 C 0.5685(5) 0.2261(8) 0.31977(17) 0.0241(14) Uani 1 1 d . . .
H10A H 0.6025 0.3489 0.3209 0.029 Uiso 1 1 calc R . .
H10B H 0.6341 0.1437 0.3312 0.029 Uiso 1 1 calc R . .
C11 C 0.4616(5) 0.2186(8) 0.34006(16) 0.0206(13) Uani 1 1 d . . .
H11A H 0.3989 0.3067 0.3293 0.025 Uiso 1 1 calc R . .
H11B H 0.4240 0.0982 0.3369 0.025 Uiso 1 1 calc R . .
C12 C 0.4982(5) 0.2572(8) 0.38020(17) 0.0246(15) Uani 1 1 d . . .
H12A H 0.5570 0.1648 0.3914 0.029 Uiso 1 1 calc R . .
H12B H 0.5401 0.3747 0.3835 0.029 Uiso 1 1 calc R . .
C13 C 0.3893(5) 0.2596(8) 0.39932(17) 0.0249(14) Uani 1 1 d . . .
H13A H 0.3450 0.1445 0.3947 0.030 Uiso 1 1 calc R . .
H13B H 0.3327 0.3559 0.3887 0.030 Uiso 1 1 calc R . .
C14 C 0.4210(6) 0.2884(8) 0.43994(18) 0.0284(15) Uani 1 1 d . . .
H14A H 0.4693 0.3999 0.4448 0.034 Uiso 1 1 calc R . .
H14B H 0.4730 0.1880 0.4510 0.034 Uiso 1 1 calc R . .
C15 C 0.3068(6) 0.3013(10) 0.4579(2) 0.0376(17) Uani 1 1 d . . .
H15A H 0.2554 0.4013 0.4473 0.056 Uiso 1 1 calc R . .
H15B H 0.3325 0.3211 0.4840 0.056 Uiso 1 1 calc R . .
H15C H 0.2600 0.1896 0.4539 0.056 Uiso 1 1 calc R . .
S2 S -0.19216(13) 0.84466(18) 0.24338(4) 0.0221(4) Uani 1 1 d . . .
O3 O -0.1430(3) 0.9400(6) 0.43269(11) 0.0265(10) Uani 1 1 d . . .
O4 O 0.0608(4) 0.9124(6) 0.44847(12) 0.0331(11) Uani 1 1 d . . .
N3 N 0.0025(4) 1.0317(6) 0.27768(13) 0.0209(12) Uani 1 1 d . . .
H3 H 0.0685 1.0925 0.2753 0.025 Uiso 1 1 calc R . .
N4 N -0.0257(4) 1.0381(6) 0.21720(14) 0.0227(12) Uani 1 1 d . . .
H4A H 0.0345 1.1164 0.2212 0.027 Uiso 1 1 calc R . .
C16 C -0.1509(5) 0.9267(9) 0.47041(16) 0.0307(16) Uani 1 1 d U . .
H16A H -0.1130 0.8144 0.4803 0.046 Uiso 1 1 calc R . .
H16B H -0.2372 0.9285 0.4731 0.046 Uiso 1 1 calc R . .
H16C H -0.1078 1.0280 0.4836 0.046 Uiso 1 1 calc R . .
C17 C -0.0297(5) 0.9355(8) 0.42527(17) 0.0237(14) Uani 1 1 d . . .
C18 C -0.0255(5) 0.9574(7) 0.38626(17) 0.0213(14) Uani 1 1 d . . .
C19 C 0.0869(5) 0.9524(7) 0.37528(17) 0.0230(14) Uani 1 1 d . . .
H19 H 0.1597 0.9342 0.3925 0.028 Uiso 1 1 calc R . .
C20 C 0.0933(5) 0.9740(7) 0.33918(17) 0.0223(14) Uani 1 1 d . . .
H20 H 0.1708 0.9684 0.3318 0.027 Uiso 1 1 calc R . .
C21 C -0.0123(5) 1.0039(7) 0.31332(16) 0.0193(13) Uani 1 1 d . . .
C22 C -0.1260(5) 1.0123(7) 0.32452(17) 0.0241(14) Uani 1 1 d . . .
H22 H -0.1990 1.0321 0.3074 0.029 Uiso 1 1 calc R . .
C23 C -0.1307(5) 0.9914(7) 0.36095(16) 0.0210(13) Uani 1 1 d . . .
H23 H -0.2074 1.0006 0.3687 0.025 Uiso 1 1 calc R . .
C24 C -0.0685(5) 0.9800(7) 0.24603(16) 0.0196(13) Uani 1 1 d . . .
C25 C -0.0681(5) 0.9855(8) 0.17935(16) 0.0239(14) Uani 1 1 d . . .
H25A H -0.1352 1.0659 0.1681 0.029 Uiso 1 1 calc R . .
H25B H -0.1005 0.8617 0.1784 0.029 Uiso 1 1 calc R . .
C26 C 0.0373(5) 0.9961(8) 0.15862(16) 0.0236(14) Uani 1 1 d . . .
H26A H 0.1012 0.9088 0.1690 0.028 Uiso 1 1 calc R . .
H26B H 0.0739 1.1172 0.1617 0.028 Uiso 1 1 calc R . .
C27 C -0.0023(5) 0.9580(8) 0.11849(17) 0.0252(14) Uani 1 1 d . . .
H27A H -0.0626 1.0493 0.1077 0.030 Uiso 1 1 calc R . .
H27B H -0.0427 0.8395 0.1153 0.030 Uiso 1 1 calc R . .
C28 C 0.1068(5) 0.9599(8) 0.09874(17) 0.0266(15) Uani 1 1 d . . .
H28A H 0.1488 1.0770 0.1029 0.032 Uiso 1 1 calc R . .
H28B H 0.1658 0.8663 0.1093 0.032 Uiso 1 1 calc R . .
C29 C 0.0729(6) 0.9286(9) 0.05847(17) 0.0319(16) Uani 1 1 d . . .
H29A H 0.0187 1.0269 0.0476 0.038 Uiso 1 1 calc R . .
H29B H 0.0261 0.8155 0.0542 0.038 Uiso 1 1 calc R . .
C30 C 0.1825(6) 0.9184(9) 0.03976(19) 0.0364(17) Uani 1 1 d . . .
H30A H 0.2349 1.0233 0.0463 0.055 Uiso 1 1 calc R . .
H30B H 0.1545 0.9159 0.0135 0.055 Uiso 1 1 calc R . .
H30C H 0.2292 0.8094 0.0474 0.055 Uiso 1 1 calc R . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 1.700(6) . ?
O1 C2 1.333(7) . ?
O1 C1 1.473(7) . ?
O2 C2 1.219(7) . ?
N1 C9 1.365(7) . ?
N1 C6 1.397(7) . ?
N1 H1 0.8800 . ?
N2 C9 1.350(7) . ?
N2 C10 1.448(8) . ?
N2 H2 0.8800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.464(9) . ?
C3 C8 1.389(8) . ?
C3 C4 1.402(8) . ?
C4 C5 1.390(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(8) . ?
C7 C8 1.383(8) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.521(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.518(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.512(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.519(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.542(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
S2 C24 1.692(6) . ?
O3 C17 1.335(7) . ?
O3 C16 1.439(7) . ?
O4 C17 1.218(7) . ?
N3 C24 1.359(7) . ?
N3 C21 1.394(7) . ?
N3 H3 0.8800 . ?
N4 C24 1.331(7) . ?
N4 C25 1.469(7) . ?
N4 H4A 0.8800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.484(8) . ?
C18 C19 1.382(8) . ?
C18 C23 1.390(8) . ?
C19 C20 1.381(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.399(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.401(8) . ?
C22 C23 1.388(8) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C25 C26 1.519(8) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.519(8) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.529(8) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.511(8) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.511(8) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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
C2 O1 C1 115.6(5) . . ?
C9 N1 C6 129.1(5) . . ?
C9 N1 H1 115.5 . . ?
C6 N1 H1 115.5 . . ?
C9 N2 C10 128.2(5) . . ?
C9 N2 H2 115.9 . . ?
C10 N2 H2 115.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 122.2(6) . . ?
O2 C2 C3 124.6(5) . . ?
O1 C2 C3 113.2(5) . . ?
C8 C3 C4 118.8(6) . . ?
C8 C3 C2 122.8(5) . . ?
C4 C3 C2 118.4(5) . . ?
C5 C4 C3 119.7(6) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 N1 116.7(5) . . ?
C5 C6 C7 119.8(6) . . ?
N1 C6 C7 123.4(5) . . ?
C8 C7 C6 119.0(5) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C3 122.0(5) . . ?
C7 C8 H8 119.0 . . ?
C3 C8 H8 119.0 . . ?
N2 C9 N1 112.9(5) . . ?
N2 C9 S1 121.9(5) . . ?
N1 C9 S1 125.2(5) . . ?
N2 C10 C11 109.7(5) . . ?
N2 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C10 113.5(5) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 112.4(5) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 114.7(5) . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 112.9(5) . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 O3 C16 115.5(5) . . ?
C24 N3 C21 130.5(5) . . ?
C24 N3 H3 114.8 . . ?
C21 N3 H3 114.8 . . ?
C24 N4 C25 127.0(5) . . ?
C24 N4 H4A 116.5 . . ?
C25 N4 H4A 116.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 O3 122.6(6) . . ?
O4 C17 C18 123.7(5) . . ?
O3 C17 C18 113.7(5) . . ?
C19 C18 C23 119.4(6) . . ?
C19 C18 C17 118.9(5) . . ?
C23 C18 C17 121.6(5) . . ?
C20 C19 C18 119.9(6) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 121.1(5) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
N3 C21 C20 117.6(5) . . ?
N3 C21 C22 123.4(5) . . ?
C20 C21 C22 119.0(6) . . ?
C23 C22 C21 119.1(6) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C18 121.3(5) . . ?
C22 C23 H23 119.3 . . ?
C18 C23 H23 119.3 . . ?
N4 C24 N3 112.6(5) . . ?
N4 C24 S2 123.4(5) . . ?
N3 C24 S2 123.8(4) . . ?
N4 C25 C26 109.9(5) . . ?
N4 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
N4 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C25 C26 C27 112.8(5) . . ?
C25 C26 H26A 109.0 . . ?
C27 C26 H26A 109.0 . . ?
C25 C26 H26B 109.0 . . ?
C27 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C26 C27 C28 111.6(5) . . ?
C26 C27 H27A 109.3 . . ?
C28 C27 H27A 109.3 . . ?
C26 C27 H27B 109.3 . . ?
C28 C27 H27B 109.3 . . ?
H27A C27 H27B 108.0 . . ?
C29 C28 C27 114.1(5) . . ?
C29 C28 H28A 108.7 . . ?
C27 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
C27 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C28 C29 C30 113.4(5) . . ?
C28 C29 H29A 108.9 . . ?
C30 C29 H29A 108.9 . . ?
C28 C29 H29B 108.9 . . ?
C30 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
C1 O1 C2 O2 -2.1(8) . . . . ?
C1 O1 C2 C3 177.0(5) . . . . ?
O2 C2 C3 C8 176.2(6) . . . . ?
O1 C2 C3 C8 -2.8(8) . . . . ?
O2 C2 C3 C4 -3.1(9) . . . . ?
O1 C2 C3 C4 177.9(5) . . . . ?
C8 C3 C4 C5 0.6(8) . . . . ?
C2 C3 C4 C5 180.0(5) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C4 C5 C6 N1 -176.7(5) . . . . ?
C4 C5 C6 C7 -1.3(8) . . . . ?
C9 N1 C6 C5 -142.6(6) . . . . ?
C9 N1 C6 C7 42.2(9) . . . . ?
C5 C6 C7 C8 1.2(8) . . . . ?
N1 C6 C7 C8 176.2(5) . . . . ?
C6 C7 C8 C3 -0.1(8) . . . . ?
C4 C3 C8 C7 -0.8(8) . . . . ?
C2 C3 C8 C7 179.9(5) . . . . ?
C10 N2 C9 N1 -170.9(5) . . . . ?
C10 N2 C9 S1 7.0(8) . . . . ?
C6 N1 C9 N2 -178.3(5) . . . . ?
C6 N1 C9 S1 4.0(8) . . . . ?
C9 N2 C10 C11 147.3(5) . . . . ?
N2 C10 C11 C12 175.9(5) . . . . ?
C10 C11 C12 C13 176.6(5) . . . . ?
C11 C12 C13 C14 177.1(5) . . . . ?
C12 C13 C14 C15 176.5(5) . . . . ?
C16 O3 C17 O4 3.7(8) . . . . ?
C16 O3 C17 C18 -177.5(5) . . . . ?
O4 C17 C18 C19 -0.3(9) . . . . ?
O3 C17 C18 C19 -179.1(5) . . . . ?
O4 C17 C18 C23 -177.1(6) . . . . ?
O3 C17 C18 C23 4.2(8) . . . . ?
C23 C18 C19 C20 -2.6(8) . . . . ?
C17 C18 C19 C20 -179.4(5) . . . . ?
C18 C19 C20 C21 1.1(9) . . . . ?
C24 N3 C21 C20 143.6(6) . . . . ?
C24 N3 C21 C22 -39.2(9) . . . . ?
C19 C20 C21 N3 177.4(5) . . . . ?
C19 C20 C21 C22 0.1(8) . . . . ?
N3 C21 C22 C23 -176.9(5) . . . . ?
C20 C21 C22 C23 0.2(8) . . . . ?
C21 C22 C23 C18 -1.9(9) . . . . ?
C19 C18 C23 C22 3.1(9) . . . . ?
C17 C18 C23 C22 179.8(5) . . . . ?
C25 N4 C24 N3 170.1(5) . . . . ?
C25 N4 C24 S2 -5.9(8) . . . . ?
C21 N3 C24 N4 177.7(5) . . . . ?
C21 N3 C24 S2 -6.3(8) . . . . ?
C24 N4 C25 C26 -149.9(5) . . . . ?
N4 C25 C26 C27 -175.3(5) . . . . ?
C25 C26 C27 C28 -177.0(5) . . . . ?
C26 C27 C28 C29 -178.2(5) . . . . ?
C27 C28 C29 C30 -176.1(5) . . . . ?

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
N1 H1 S1 0.88 2.48 3.321(5) 159.9 2_645
N2 H2 S1 0.88 2.60 3.440(5) 159.9 2_645
N3 H3 S2 0.88 2.50 3.334(5) 157.7 2
N4 H4A S2 0.88 2.63 3.462(5) 159.1 2

_diffrn_measured_fraction_theta_max 0.935
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.935
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.110

data_global

# Attachment '2012nb005-final.cif'


data_p-CF3
#TrackingRef '2012nb005-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
Stephen Moore
;

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 F3 N2 S'
_chemical_formula_sum            'C14 H19 F3 N2 S'
_chemical_formula_weight         304.37

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'
F F 0.0171 0.0103 '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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


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                   13.298(8)
_cell_length_b                   13.278(6)
_cell_length_c                   8.673(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.912(18)
_cell_angle_gamma                90.00
_cell_volume                     1530.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1707
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.4

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9140
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8095
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_sigmaI/netI    0.1028
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3436
_reflns_number_gt                2288
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0438P)²+0.0000P] 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         3436
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1325
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 -0.2932(2) 0.0921(2) -0.8674(3) 0.0388(8) Uani 1 1 d . . .
H1A H -0.3036 0.1165 -0.9733 0.058 Uiso 1 1 calc R . .
H1B H -0.3514 0.1101 -0.8067 0.058 Uiso 1 1 calc R . .
H1C H -0.2855 0.0187 -0.8683 0.058 Uiso 1 1 calc R . .
C2 C -0.1983(2) 0.1402(2) -0.7953(3) 0.0284(6) Uani 1 1 d . . .
H2A H -0.1399 0.1228 -0.8581 0.034 Uiso 1 1 calc R . .
H2B H -0.2059 0.2144 -0.7964 0.034 Uiso 1 1 calc R . .
C3 C -0.17815(18) 0.10495(19) -0.6301(3) 0.0220(6) Uani 1 1 d . . .
H3A H -0.1716 0.0307 -0.6296 0.026 Uiso 1 1 calc R . .
H3B H -0.2367 0.1226 -0.5679 0.026 Uiso 1 1 calc R . .
C4 C -0.08349(18) 0.15063(19) -0.5540(3) 0.0202(6) Uani 1 1 d . . .
H4A H -0.0913 0.2246 -0.5477 0.024 Uiso 1 1 calc R . .
H4B H -0.0251 0.1363 -0.6183 0.024 Uiso 1 1 calc R . .
C5 C -0.06354(18) 0.10799(19) -0.3916(3) 0.0194(5) Uani 1 1 d . . .
H5A H -0.1222 0.1218 -0.3275 0.023 Uiso 1 1 calc R . .
H5B H -0.0549 0.0341 -0.3979 0.023 Uiso 1 1 calc R . .
C6 C 0.03044(18) 0.15466(19) -0.3157(3) 0.0196(6) Uani 1 1 d . . .
H6A H 0.0897 0.1397 -0.3780 0.024 Uiso 1 1 calc R . .
H6B H 0.0226 0.2287 -0.3101 0.024 Uiso 1 1 calc R . .
C7 C 0.11906(17) 0.13852(17) -0.0583(3) 0.0178(5) Uani 1 1 d . . .
C8 C 0.27215(17) 0.24700(19) -0.0192(3) 0.0184(5) Uani 1 1 d . . .
C9 C 0.33771(17) 0.1802(2) 0.0581(3) 0.0218(6) Uani 1 1 d . . .
H9 H 0.3249 0.1099 0.0563 0.026 Uiso 1 1 calc R . .
C10 C 0.42191(17) 0.21824(19) 0.1376(3) 0.0234(6) Uani 1 1 d . . .
H10 H 0.4665 0.1736 0.1914 0.028 Uiso 1 1 calc R . .
C11 C 0.44152(18) 0.3215(2) 0.1390(3) 0.0226(6) Uani 1 1 d . . .
C12 C 0.37770(19) 0.3882(2) 0.0584(3) 0.0243(6) Uani 1 1 d . . .
H12 H 0.3922 0.4583 0.0571 0.029 Uiso 1 1 calc R . .
C13 C 0.29251(18) 0.35080(19) -0.0199(3) 0.0216(6) Uani 1 1 d . . .
H13 H 0.2481 0.3955 -0.0739 0.026 Uiso 1 1 calc R . .
C14 C 0.53431(19) 0.3618(2) 0.2208(3) 0.0294(7) Uani 1 1 d . . .
N1 N 0.04591(14) 0.11325(15) -0.1595(2) 0.0188(5) Uani 1 1 d . . .
H1 H 0.0027 0.0674 -0.1301 0.023 Uiso 1 1 calc R . .
N2 N 0.18481(14) 0.21176(15) -0.1031(2) 0.0199(5) Uani 1 1 d . . .
H2 H 0.1717 0.2401 -0.1933 0.024 Uiso 1 1 calc R . .
F1 F 0.57094(12) 0.29787(13) 0.3287(2) 0.0446(5) Uani 1 1 d . . .
F2 F 0.61049(12) 0.37713(15) 0.1242(2) 0.0529(6) Uani 1 1 d . . .
F3 F 0.51906(13) 0.45066(14) 0.2909(3) 0.0634(7) Uani 1 1 d . . .
S1 S 0.12384(5) 0.08229(5) 0.11945(7) 0.01920(18) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.530(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.522(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.527(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.533(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.525(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.470(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.331(3) . ?
C7 N2 1.373(3) . ?
C7 S1 1.712(3) . ?
C8 C9 1.399(3) . ?
C8 C13 1.405(3) . ?
C8 N2 1.429(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(3) . ?
C11 C14 1.501(3) . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 F1 1.343(3) . ?
C14 F3 1.346(3) . ?
C14 F2 1.351(3) . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 111.9(2) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 113.6(2) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 111.4(2) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 111.2(2) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 C5 109.5(2) . . ?
N1 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N1 C7 N2 116.8(2) . . ?
N1 C7 S1 119.21(19) . . ?
N2 C7 S1 123.99(16) . . ?
C9 C8 C13 120.5(2) . . ?
C9 C8 N2 121.3(2) . . ?
C13 C8 N2 118.2(2) . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 C14 120.3(2) . . ?
C12 C11 C14 119.1(2) . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
F1 C14 F3 107.2(2) . . ?
F1 C14 F2 105.4(2) . . ?
F3 C14 F2 106.0(2) . . ?
F1 C14 C11 112.2(2) . . ?
F3 C14 C11 113.1(2) . . ?
F2 C14 C11 112.5(2) . . ?
C7 N1 C6 126.2(2) . . ?
C7 N1 H1 116.9 . . ?
C6 N1 H1 116.9 . . ?
C7 N2 C8 127.1(2) . . ?
C7 N2 H2 116.5 . . ?
C8 N2 H2 116.5 . . ?

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
N1 H1 S1 0.88 2.61 3.465(2) 164.8 3
N2 H2 S1 0.88 2.92 3.714(2) 150.7 4_565

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.079

data_global

# Attachment '2012nb025 - final.cif'


data_p-Br
#TrackingRef '2012nb025 - final.cif'


_chemical_compound_source        'Nathalie Busschaert'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 Br N2 S'
_chemical_formula_sum            'C13 H19 Br N2 S'
_chemical_formula_weight         315.27

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   17.3563(8)
_cell_length_b                   7.8428(3)
_cell_length_c                   21.0265(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.599(7)
_cell_angle_gamma                90.00
_cell_volume                     2837.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    20191
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    3.026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5067
_exptl_absorpt_correction_T_max  0.9704
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26506
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6491
_reflns_number_gt                4955
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0253P)²+0.3437P] 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         6491
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0739
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 -0.44792(16) 0.7550(3) 0.47632(11) 0.0335(6) Uani 1 1 d . . .
H1A H -0.5019 0.7879 0.4620 0.050 Uiso 1 1 calc R . .
H1B H -0.4249 0.8349 0.5093 0.050 Uiso 1 1 calc R . .
H1C H -0.4467 0.6395 0.4942 0.050 Uiso 1 1 calc R . .
C2 C -0.40162(13) 0.7591(3) 0.41939(10) 0.0225(5) Uani 1 1 d . . .
H2A H -0.4255 0.6790 0.3861 0.027 Uiso 1 1 calc R . .
H2B H -0.4046 0.8751 0.4006 0.027 Uiso 1 1 calc R . .
C3 C -0.31692(13) 0.7113(3) 0.43798(10) 0.0181(5) Uani 1 1 d . . .
H3A H -0.3144 0.5944 0.4559 0.022 Uiso 1 1 calc R . .
H3B H -0.2938 0.7894 0.4723 0.022 Uiso 1 1 calc R . .
C4 C -0.26785(13) 0.7181(3) 0.38281(10) 0.0169(5) Uani 1 1 d . . .
H4A H -0.2927 0.6471 0.3469 0.020 Uiso 1 1 calc R . .
H4B H -0.2660 0.8370 0.3673 0.020 Uiso 1 1 calc R . .
C5 C -0.18576(13) 0.6552(3) 0.40296(9) 0.0154(5) Uani 1 1 d . . .
H5A H -0.1878 0.5343 0.4162 0.019 Uiso 1 1 calc R . .
H5B H -0.1624 0.7215 0.4407 0.019 Uiso 1 1 calc R . .
C6 C -0.13370(13) 0.6699(3) 0.35048(9) 0.0169(5) Uani 1 1 d . . .
H6A H -0.1589 0.6137 0.3110 0.020 Uiso 1 1 calc R . .
H6B H -0.1258 0.7916 0.3406 0.020 Uiso 1 1 calc R . .
C7 C 0.00668(13) 0.6130(3) 0.34602(9) 0.0143(5) Uani 1 1 d . . .
C8 C 0.14757(13) 0.5365(3) 0.36480(9) 0.0153(5) Uani 1 1 d . . .
C9 C 0.20539(13) 0.5823(3) 0.41382(10) 0.0184(5) Uani 1 1 d . . .
H9 H 0.1915 0.6168 0.4541 0.022 Uiso 1 1 calc R . .
C10 C 0.28308(14) 0.5786(3) 0.40495(11) 0.0222(5) Uani 1 1 d . . .
H10 H 0.3225 0.6097 0.4387 0.027 Uiso 1 1 calc R . .
C11 C 0.30214(13) 0.5285(3) 0.34554(11) 0.0199(5) Uani 1 1 d . . .
C12 C 0.24482(14) 0.4803(3) 0.29639(10) 0.0191(5) Uani 1 1 d . . .
H12 H 0.2587 0.4460 0.2561 0.023 Uiso 1 1 calc R . .
C13 C 0.16760(14) 0.4823(3) 0.30601(9) 0.0167(5) Uani 1 1 d . . .
H13 H 0.1284 0.4469 0.2728 0.020 Uiso 1 1 calc R . .
C14 C 0.54360(15) 0.5091(3) 0.21589(11) 0.0307(6) Uani 1 1 d . . .
H14A H 0.4880 0.5175 0.2001 0.046 Uiso 1 1 calc R . .
H14B H 0.5581 0.5997 0.2473 0.046 Uiso 1 1 calc R . .
H14C H 0.5546 0.3978 0.2363 0.046 Uiso 1 1 calc R . .
C15 C 0.59068(13) 0.5284(3) 0.15974(10) 0.0217(5) Uani 1 1 d . . .
H15A H 0.5751 0.4377 0.1279 0.026 Uiso 1 1 calc R . .
H15B H 0.5781 0.6397 0.1386 0.026 Uiso 1 1 calc R . .
C16 C 0.67829(14) 0.5179(3) 0.18019(10) 0.0194(5) Uani 1 1 d . . .
H16A H 0.6911 0.4027 0.1977 0.023 Uiso 1 1 calc R . .
H16B H 0.6928 0.6011 0.2151 0.023 Uiso 1 1 calc R . .
C17 C 0.72726(14) 0.5528(3) 0.12627(9) 0.0174(5) Uani 1 1 d . . .
H17A H 0.7128 0.4707 0.0910 0.021 Uiso 1 1 calc R . .
H17B H 0.7158 0.6690 0.1092 0.021 Uiso 1 1 calc R . .
C18 C 0.81345(13) 0.5380(3) 0.14891(9) 0.0167(5) Uani 1 1 d . . .
H18A H 0.8249 0.4207 0.1649 0.020 Uiso 1 1 calc R . .
H18B H 0.8273 0.6173 0.1853 0.020 Uiso 1 1 calc R . .
C19 C 0.86373(13) 0.5774(3) 0.09686(9) 0.0189(5) Uani 1 1 d . . .
H19A H 0.8541 0.4919 0.0621 0.023 Uiso 1 1 calc R . .
H19B H 0.8501 0.6912 0.0783 0.023 Uiso 1 1 calc R . .
C20 C 1.00439(13) 0.6471(3) 0.09938(9) 0.0140(5) Uani 1 1 d . . .
C21 C 1.14848(13) 0.6731(3) 0.12631(9) 0.0132(4) Uani 1 1 d . . .
C22 C 1.20228(14) 0.7470(3) 0.17278(9) 0.0165(5) Uani 1 1 d . . .
H22 H 1.1868 0.7807 0.2126 0.020 Uiso 1 1 calc R . .
C23 C 1.27859(14) 0.7724(3) 0.16176(10) 0.0187(5) Uani 1 1 d . . .
H23 H 1.3154 0.8214 0.1941 0.022 Uiso 1 1 calc R . .
C24 C 1.30065(13) 0.7257(3) 0.10301(10) 0.0181(5) Uani 1 1 d . . .
C25 C 1.24765(14) 0.6508(3) 0.05657(9) 0.0179(5) Uani 1 1 d . . .
H25 H 1.2632 0.6188 0.0166 0.021 Uiso 1 1 calc R . .
C26 C 1.17213(13) 0.6222(3) 0.06804(9) 0.0164(5) Uani 1 1 d . . .
H26 H 1.1362 0.5679 0.0364 0.020 Uiso 1 1 calc R . .
N1 N -0.05894(11) 0.5897(2) 0.37123(8) 0.0165(4) Uani 1 1 d . . .
H1 H -0.0569 0.5185 0.4038 0.020 Uiso 1 1 calc R . .
N2 N 0.06957(11) 0.5341(2) 0.37826(8) 0.0172(4) Uani 1 1 d . . .
H2 H 0.0609 0.4736 0.4118 0.021 Uiso 1 1 calc R . .
N3 N 0.94540(11) 0.5746(2) 0.12361(8) 0.0169(4) Uani 1 1 d . . .
H3 H 0.9571 0.5186 0.1599 0.020 Uiso 1 1 calc R . .
N4 N 1.07260(11) 0.6428(2) 0.14013(7) 0.0143(4) Uani 1 1 d . . .
H4 H 1.0685 0.6176 0.1803 0.017 Uiso 1 1 calc R . .
S1 S 0.01011(3) 0.73606(7) 0.27974(2) 0.01545(12) Uani 1 1 d . . .
S2 S 0.99385(3) 0.74430(7) 0.02648(2) 0.01585(12) Uani 1 1 d . . .
Br1 Br 0.407632(15) 0.52571(3) 0.331258(13) 0.03549(8) Uani 1 1 d . . .
Br2 Br 1.404166(14) 0.76440(3) 0.086548(11) 0.02553(7) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.528(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.517(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.528(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.514(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.520(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.456(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.331(3) . ?
C7 N2 1.356(3) . ?
C7 S1 1.703(2) . ?
C8 C9 1.387(3) . ?
C8 C13 1.394(3) . ?
C8 N2 1.419(3) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C11 Br1 1.894(2) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.529(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.527(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.529(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.513(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.519(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N3 1.454(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 N3 1.330(3) . ?
C20 N4 1.367(3) . ?
C20 S2 1.700(2) . ?
C21 C22 1.386(3) . ?
C21 C26 1.401(3) . ?
C21 N4 1.406(3) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C24 Br2 1.899(2) . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?
N3 H3 0.8800 . ?
N4 H4 0.8800 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 112.65(19) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 114.47(18) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 112.00(17) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 113.57(17) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 C5 109.96(16) . . ?
N1 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N1 C7 N2 114.38(17) . . ?
N1 C7 S1 121.90(17) . . ?
N2 C7 S1 123.71(17) . . ?
C9 C8 C13 119.8(2) . . ?
C9 C8 N2 118.07(18) . . ?
C13 C8 N2 121.9(2) . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 118.6(2) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 Br1 119.42(16) . . ?
C10 C11 Br1 119.70(18) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 119.6(2) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C14 113.03(18) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 114.35(18) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 112.11(17) . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C16 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C19 113.33(17) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
N3 C19 C18 109.98(17) . . ?
N3 C19 H19A 109.7 . . ?
C18 C19 H19A 109.7 . . ?
N3 C19 H19B 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
N3 C20 N4 113.32(17) . . ?
N3 C20 S2 122.73(17) . . ?
N4 C20 S2 123.88(16) . . ?
C22 C21 C26 119.2(2) . . ?
C22 C21 N4 119.16(18) . . ?
C26 C21 N4 121.55(19) . . ?
C21 C22 C23 120.72(19) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C24 119.4(2) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 Br2 119.81(16) . . ?
C23 C24 Br2 119.89(17) . . ?
C24 C25 C26 120.27(19) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.0(2) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
C7 N1 C6 126.64(17) . . ?
C7 N1 H1 116.7 . . ?
C6 N1 H1 116.7 . . ?
C7 N2 C8 128.34(17) . . ?
C7 N2 H2 115.8 . . ?
C8 N2 H2 115.8 . . ?
C20 N3 C19 127.26(18) . . ?
C20 N3 H3 116.4 . . ?
C19 N3 H3 116.4 . . ?
C20 N4 C21 128.57(17) . . ?
C20 N4 H4 115.7 . . ?
C21 N4 H4 115.7 . . ?

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
N2 H2 S2 0.88 2.48 3.3124(17) 158.3 2_645
N3 H3 S1 0.88 2.58 3.3703(18) 150.0 2_645
N4 H4 S1 0.88 2.61 3.3423(16) 141.1 1_655
N1 H1 S2 0.88 2.75 3.5491(18) 152.0 2_645

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.091

data_global

# Attachment '2012nb032-final.cif'


data_p-F
#TrackingRef '2012nb032-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
Samuel J. Bradberry
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 F N2 S'
_chemical_formula_sum            'C13 H19 F N2 S'
_chemical_formula_weight         254.36

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   17.405(12)
_cell_length_b                   8.732(6)
_cell_length_c                   17.612(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2677(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6838
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      31.4

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8819
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19097
_diffrn_reflns_av_R_equivalents  0.1075
_diffrn_reflns_av_sigmaI/netI    0.1049
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4720
_reflns_number_gt                4121
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0430P)²+0.4468P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.24(12)
_refine_ls_number_reflns         4720
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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 1.0974(3) 0.3992(6) 1.0273(3) 0.0278(13) Uani 1 1 d . . .
C2 C 1.0374(3) 0.4877(6) 1.0539(3) 0.0232(12) Uani 1 1 d . . .
H2A H 1.0349 0.5179 1.1057 0.028 Uiso 1 1 calc R . .
C3 C 0.9809(3) 0.5311(5) 1.0027(3) 0.0212(11) Uani 1 1 d . . .
H3A H 0.9381 0.5892 1.0197 0.025 Uiso 1 1 calc R . .
C4 C 0.9866(3) 0.4897(5) 0.9256(3) 0.0178(10) Uani 1 1 d . . .
C5 C 1.0504(3) 0.4076(5) 0.9000(3) 0.0224(12) Uani 1 1 d . . .
H5 H 1.0559 0.3844 0.8476 0.027 Uiso 1 1 calc R . .
C6 C 1.1060(3) 0.3598(5) 0.9521(3) 0.0237(12) Uani 1 1 d . . .
H6 H 1.1490 0.3012 0.9359 0.028 Uiso 1 1 calc R . .
C7 C 0.8944(3) 0.4828(5) 0.8147(3) 0.0162(10) Uani 1 1 d . . .
C8 C 0.7791(3) 0.5122(5) 0.7310(3) 0.0190(11) Uani 1 1 d . . .
H8A H 0.8068 0.4464 0.6943 0.023 Uiso 1 1 calc R . .
H8B H 0.7600 0.6032 0.7033 0.023 Uiso 1 1 calc R . .
C9 C 0.7111(3) 0.4241(5) 0.7635(3) 0.0215(11) Uani 1 1 d . . .
H9A H 0.7305 0.3362 0.7934 0.026 Uiso 1 1 calc R . .
H9B H 0.6822 0.4918 0.7983 0.026 Uiso 1 1 calc R . .
C10 C 0.6576(3) 0.3660(6) 0.7025(3) 0.0285(13) Uani 1 1 d . . .
H10A H 0.6862 0.2947 0.6691 0.034 Uiso 1 1 calc R . .
H10B H 0.6405 0.4536 0.6711 0.034 Uiso 1 1 calc R . .
C11 C 0.5860(3) 0.2826(6) 0.7346(3) 0.0318(13) Uani 1 1 d . . .
H11A H 0.6025 0.2117 0.7753 0.038 Uiso 1 1 calc R . .
H11B H 0.5510 0.3591 0.7574 0.038 Uiso 1 1 calc R . .
C12 C 0.5435(3) 0.1941(6) 0.6752(3) 0.0312(13) Uani 1 1 d . . .
H12A H 0.5781 0.1159 0.6532 0.037 Uiso 1 1 calc R . .
H12B H 0.5279 0.2645 0.6339 0.037 Uiso 1 1 calc R . .
C13 C 0.4708(3) 0.1137(7) 0.7077(4) 0.0428(16) Uani 1 1 d . . .
H13A H 0.4446 0.0579 0.6670 0.064 Uiso 1 1 calc R . .
H13B H 0.4360 0.1908 0.7290 0.064 Uiso 1 1 calc R . .
H13C H 0.4861 0.0417 0.7477 0.064 Uiso 1 1 calc R . .
C14 C 0.6466(3) 0.8395(5) 0.6748(3) 0.0224(11) Uani 1 1 d . . .
C15 C 0.7127(3) 0.8961(6) 0.6439(3) 0.0261(12) Uani 1 1 d . . .
H15 H 0.7218 0.8920 0.5908 0.031 Uiso 1 1 calc R . .
C16 C 0.7658(3) 0.9597(6) 0.6930(3) 0.0243(12) Uani 1 1 d . . .
H16 H 0.8119 1.0016 0.6729 0.029 Uiso 1 1 calc R . .
C17 C 0.7538(3) 0.9641(5) 0.7710(3) 0.0177(10) Uani 1 1 d . . .
C18 C 0.6852(3) 0.9069(5) 0.8001(3) 0.0182(11) Uani 1 1 d . . .
H18 H 0.6753 0.9118 0.8530 0.022 Uiso 1 1 calc R . .
C19 C 0.6311(3) 0.8422(5) 0.7511(3) 0.0238(12) Uani 1 1 d . . .
H19 H 0.5845 0.8009 0.7703 0.029 Uiso 1 1 calc R . .
C20 C 0.8429(3) 0.9826(5) 0.8836(2) 0.0145(10) Uani 1 1 d . . .
C21 C 0.9555(3) 1.0237(5) 0.9680(3) 0.0190(11) Uani 1 1 d . . .
H21A H 0.9282 0.9607 1.0062 0.023 Uiso 1 1 calc R . .
H21B H 0.9741 1.1176 0.9936 0.023 Uiso 1 1 calc R . .
C22 C 1.0236(3) 0.9345(5) 0.9374(3) 0.0187(10) Uani 1 1 d . . .
H22A H 1.0468 0.9934 0.8952 0.022 Uiso 1 1 calc R . .
H22B H 1.0048 0.8364 0.9163 0.022 Uiso 1 1 calc R . .
C23 C 1.0866(3) 0.8997(5) 0.9964(3) 0.0226(11) Uani 1 1 d . . .
H23A H 1.1103 0.9969 1.0134 0.027 Uiso 1 1 calc R . .
H23B H 1.0631 0.8497 1.0412 0.027 Uiso 1 1 calc R . .
C24 C 1.1481(3) 0.7964(5) 0.9637(3) 0.0227(11) Uani 1 1 d . . .
H24A H 1.1712 0.8477 0.9191 0.027 Uiso 1 1 calc R . .
H24B H 1.1236 0.7007 0.9457 0.027 Uiso 1 1 calc R . .
C25 C 1.2127(3) 0.7547(6) 1.0202(3) 0.0292(13) Uani 1 1 d . . .
H25A H 1.2386 0.8499 1.0369 0.035 Uiso 1 1 calc R . .
H25B H 1.1897 0.7059 1.0655 0.035 Uiso 1 1 calc R . .
C26 C 1.2722(3) 0.6471(6) 0.9864(3) 0.0299(13) Uani 1 1 d . . .
H26A H 1.3115 0.6242 1.0245 0.045 Uiso 1 1 calc R . .
H26B H 1.2963 0.6959 0.9423 0.045 Uiso 1 1 calc R . .
H26C H 1.2471 0.5519 0.9705 0.045 Uiso 1 1 calc R . .
F1 F 1.15257(18) 0.3519(3) 1.07763(16) 0.0389(8) Uani 1 1 d . . .
F2 F 0.59216(16) 0.7751(3) 0.62796(15) 0.0320(7) Uani 1 1 d . . .
N1 N 0.9268(2) 0.5452(5) 0.8779(2) 0.0205(10) Uani 1 1 d . . .
H2 H 0.9066 0.6302 0.8924 0.025 Uiso 1 1 d R . .
N2 N 0.8324(2) 0.5615(4) 0.7906(2) 0.0202(9) Uani 1 1 d . . .
H3 H 0.8226 0.6461 0.8136 0.024 Uiso 1 1 d R . .
N3 N 0.8102(2) 1.0348(5) 0.8175(2) 0.0191(9) Uani 1 1 d . . .
H3B H 0.8265 1.1247 0.8018 0.023 Uiso 1 1 calc R . .
N4 N 0.9020(2) 1.0661(4) 0.9070(2) 0.0196(9) Uani 1 1 d . . .
H4 H 0.9099 1.1542 0.8841 0.023 Uiso 1 1 calc R . .
S1 S 0.92774(7) 0.32669(13) 0.76799(7) 0.0194(3) Uani 1 1 d . . .
S2 S 0.80980(7) 0.82662(13) 0.93026(7) 0.0188(3) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 F1 1.371(5) . ?
C1 C6 1.376(7) . ?
C1 C2 1.381(7) . ?
C2 C3 1.387(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.407(7) . ?
C3 H3A 0.9500 . ?
C4 C5 1.396(6) . ?
C4 N1 1.423(6) . ?
C5 C6 1.398(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.348(6) . ?
C7 N1 1.361(6) . ?
C7 S1 1.695(5) . ?
C8 N2 1.466(6) . ?
C8 C9 1.523(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.510(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.550(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.496(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.555(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.365(7) . ?
C14 C19 1.371(7) . ?
C14 F2 1.377(5) . ?
C15 C16 1.383(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(6) . ?
C17 N3 1.420(5) . ?
C18 C19 1.396(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 N4 1.327(6) . ?
C20 N3 1.373(6) . ?
C20 S2 1.692(4) . ?
C21 N4 1.469(5) . ?
C21 C22 1.517(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.539(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.513(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.546(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.520(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 H2 0.8595 . ?
N2 H3 0.8596 . ?
N3 H3B 0.8800 . ?
N4 H4 0.8800 . ?

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
F1 C1 C6 118.1(5) . . ?
F1 C1 C2 118.6(4) . . ?
C6 C1 C2 123.3(5) . . ?
C1 C2 C3 117.9(4) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 H2A 121.1 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 N1 124.5(5) . . ?
C3 C4 N1 115.5(4) . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 118.8(5) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N2 C7 N1 112.6(4) . . ?
N2 C7 S1 122.1(4) . . ?
N1 C7 S1 125.3(4) . . ?
N2 C8 C9 111.8(4) . . ?
N2 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 112.4(4) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 113.2(4) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 112.7(5) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 112.3(5) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 123.4(5) . . ?
C15 C14 F2 119.2(5) . . ?
C19 C14 F2 117.4(5) . . ?
C14 C15 C16 117.3(5) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
C15 C16 C17 121.9(5) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C18 118.9(4) . . ?
C16 C17 N3 118.6(4) . . ?
C18 C17 N3 122.4(4) . . ?
C17 C18 C19 119.8(5) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C14 C19 C18 118.7(5) . . ?
C14 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
N4 C20 N3 113.8(4) . . ?
N4 C20 S2 123.7(3) . . ?
N3 C20 S2 122.5(3) . . ?
N4 C21 C22 111.4(4) . . ?
N4 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
N4 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C23 114.7(4) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 111.4(4) . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C23 C24 C25 114.2(4) . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
C25 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C26 C25 C24 112.9(4) . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C7 N1 C4 130.5(4) . . ?
C7 N1 H2 114.8 . . ?
C4 N1 H2 114.7 . . ?
C7 N2 C8 125.6(4) . . ?
C7 N2 H3 116.7 . . ?
C8 N2 H3 117.6 . . ?
C20 N3 C17 129.1(4) . . ?
C20 N3 H3B 115.4 . . ?
C17 N3 H3B 115.4 . . ?
C20 N4 C21 125.5(4) . . ?
C20 N4 H4 117.3 . . ?
C21 N4 H4 117.2 . . ?

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
F1 C1 C2 C3 -178.3(4) . . . . ?
C6 C1 C2 C3 3.8(8) . . . . ?
C1 C2 C3 C4 -2.0(7) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
C2 C3 C4 N1 -177.9(4) . . . . ?
C3 C4 C5 C6 3.6(7) . . . . ?
N1 C4 C5 C6 179.5(4) . . . . ?
F1 C1 C6 C5 -179.8(4) . . . . ?
C2 C1 C6 C5 -1.9(8) . . . . ?
C4 C5 C6 C1 -1.9(7) . . . . ?
N2 C8 C9 C10 -177.3(4) . . . . ?
C8 C9 C10 C11 -177.3(4) . . . . ?
C9 C10 C11 C12 -166.4(4) . . . . ?
C10 C11 C12 C13 -178.8(4) . . . . ?
C19 C14 C15 C16 -0.4(7) . . . . ?
F2 C14 C15 C16 -180.0(4) . . . . ?
C14 C15 C16 C17 1.1(7) . . . . ?
C15 C16 C17 C18 -2.0(7) . . . . ?
C15 C16 C17 N3 -178.4(4) . . . . ?
C16 C17 C18 C19 2.0(7) . . . . ?
N3 C17 C18 C19 178.3(4) . . . . ?
C15 C14 C19 C18 0.4(7) . . . . ?
F2 C14 C19 C18 -180.0(4) . . . . ?
C17 C18 C19 C14 -1.3(7) . . . . ?
N4 C21 C22 C23 174.1(4) . . . . ?
C21 C22 C23 C24 173.9(4) . . . . ?
C22 C23 C24 C25 -179.2(4) . . . . ?
C23 C24 C25 C26 178.3(4) . . . . ?
N2 C7 N1 C4 172.2(4) . . . . ?
S1 C7 N1 C4 -9.4(7) . . . . ?
C5 C4 N1 C7 35.8(7) . . . . ?
C3 C4 N1 C7 -148.1(5) . . . . ?
N1 C7 N2 C8 -171.0(4) . . . . ?
S1 C7 N2 C8 10.6(6) . . . . ?
C9 C8 N2 C7 92.3(5) . . . . ?
N4 C20 N3 C17 170.6(4) . . . . ?
S2 C20 N3 C17 -9.8(7) . . . . ?
C16 C17 N3 C20 -132.9(5) . . . . ?
C18 C17 N3 C20 50.7(7) . . . . ?
N3 C20 N4 C21 -169.3(4) . . . . ?
S2 C20 N4 C21 11.0(7) . . . . ?
C22 C21 N4 C20 90.1(5) . . . . ?

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
N1 H2 S2 0.86 2.49 3.321(4) 161.5 .
N1 H2 S2 0.86 2.49 3.321(4) 161.5 .
N3 H3B S1 0.88 2.56 3.383(4) 155.4 1_565
N4 H4 S1 0.88 2.56 3.373(4) 154.3 1_565

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.065

data_global

# Attachment '2012nb035c-final.cif'


data_p-OCOMe
#TrackingRef '2012nb035c-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
Jennifer R. Hiscock
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 N2 O2 S'
_chemical_formula_sum            'C15 H22 N2 O2 S'
_chemical_formula_weight         294.41

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   5.553(4)
_cell_length_b                   9.157(8)
_cell_length_c                   30.91(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.215(8)
_cell_angle_gamma                90.00
_cell_volume                     1569(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3306
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      30.7

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9773
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24561
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3586
_reflns_number_gt                3121
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0722P)²+0.9038P] 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         3586
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.1805
_refine_ls_wR_factor_gt          0.1729
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_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 -0.5198(5) 0.6290(3) 0.35550(9) 0.0395(7) Uani 1 1 d . . .
H1A H -0.6175 0.7126 0.3454 0.059 Uiso 1 1 calc R . .
H1B H -0.4586 0.6460 0.3854 0.059 Uiso 1 1 calc R . .
H1C H -0.6192 0.5405 0.3542 0.059 Uiso 1 1 calc R . .
O2 O -0.1590(4) 0.5161(2) 0.33099(6) 0.0425(5) Uani 1 1 d . . .
C2 C -0.3120(5) 0.6103(3) 0.32714(8) 0.0310(6) Uani 1 1 d . . .
C3 C -0.1371(4) 0.7098(3) 0.26480(8) 0.0296(5) Uani 1 1 d . . .
C4 C -0.1759(5) 0.6270(3) 0.22772(8) 0.0331(6) Uani 1 1 d . . .
H4 H -0.3113 0.5637 0.2247 0.040 Uiso 1 1 calc R . .
C5 C -0.0154(5) 0.6368(3) 0.19462(8) 0.0330(6) Uani 1 1 d . . .
H5 H -0.0401 0.5793 0.1692 0.040 Uiso 1 1 calc R . .
C6 C 0.1809(5) 0.7311(3) 0.19913(8) 0.0296(5) Uani 1 1 d . . .
C7 C 0.2176(5) 0.8128(3) 0.23727(8) 0.0306(6) Uani 1 1 d . . .
H7 H 0.3529 0.8761 0.2406 0.037 Uiso 1 1 calc R . .
C8 C 0.0590(5) 0.8027(3) 0.27036(8) 0.0307(6) Uani 1 1 d . . .
H8 H 0.0845 0.8581 0.2962 0.037 Uiso 1 1 calc R . .
C9 C 0.4261(5) 0.6717(3) 0.13442(8) 0.0320(6) Uani 1 1 d . . .
C10 C 0.7211(5) 0.6656(3) 0.07692(8) 0.0359(6) Uani 1 1 d . . .
H10A H 0.6033 0.6304 0.0540 0.043 Uiso 1 1 calc R . .
H10B H 0.8095 0.5800 0.0893 0.043 Uiso 1 1 calc R . .
C11 C 0.8981(5) 0.7702(3) 0.05725(9) 0.0361(6) Uani 1 1 d . . .
H11A H 1.0169 0.8041 0.0802 0.043 Uiso 1 1 calc R . .
H11B H 0.8095 0.8567 0.0455 0.043 Uiso 1 1 calc R . .
C12 C 1.0312(5) 0.6974(3) 0.02092(8) 0.0355(6) Uani 1 1 d . . .
H12A H 0.9114 0.6611 -0.0015 0.043 Uiso 1 1 calc R . .
H12B H 1.1220 0.6121 0.0329 0.043 Uiso 1 1 calc R . .
C13 C 1.2067(5) 0.8007(3) -0.00040(9) 0.0354(6) Uani 1 1 d . . .
H13A H 1.1160 0.8863 -0.0122 0.043 Uiso 1 1 calc R . .
H13B H 1.3270 0.8365 0.0220 0.043 Uiso 1 1 calc R . .
C14 C 1.3393(5) 0.7290(3) -0.03692(9) 0.0384(7) Uani 1 1 d . . .
H14A H 1.2191 0.6928 -0.0593 0.046 Uiso 1 1 calc R . .
H14B H 1.4309 0.6438 -0.0251 0.046 Uiso 1 1 calc R . .
C15 C 1.5133(6) 0.8331(3) -0.05823(9) 0.0438(7) Uani 1 1 d . . .
H15A H 1.5943 0.7811 -0.0810 0.066 Uiso 1 1 calc R . .
H15B H 1.6339 0.8686 -0.0364 0.066 Uiso 1 1 calc R . .
H15C H 1.4230 0.9160 -0.0709 0.066 Uiso 1 1 calc R . .
N1 N 0.3453(4) 0.7589(2) 0.16672(7) 0.0338(5) Uani 1 1 d . . .
H1 H 0.4063 0.8476 0.1674 0.041 Uiso 1 1 calc R . .
N2 N 0.5931(4) 0.7386(3) 0.11099(7) 0.0361(5) Uani 1 1 d . . .
H2 H 0.6265 0.8309 0.1165 0.043 Uiso 1 1 calc R . .
O1 O -0.3153(3) 0.7128(2) 0.29603(6) 0.0348(5) Uani 1 1 d . . .
S1 S 0.33601(14) 0.49998(7) 0.12358(2) 0.0383(2) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.497(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O2 C2 1.212(3) . ?
C2 O1 1.343(3) . ?
C3 C4 1.381(4) . ?
C3 C8 1.385(4) . ?
C3 O1 1.421(3) . ?
C4 C5 1.397(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(4) . ?
C6 N1 1.416(3) . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N2 1.355(3) . ?
C9 N1 1.373(3) . ?
C9 S1 1.678(3) . ?
C10 N2 1.465(3) . ?
C10 C11 1.523(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.532(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.533(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.530(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.532(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.3(2) . . ?
O2 C2 C1 125.7(2) . . ?
O1 C2 C1 111.1(2) . . ?
C4 C3 C8 121.7(2) . . ?
C4 C3 O1 119.5(2) . . ?
C8 C3 O1 118.5(2) . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 119.5(2) . . ?
C5 C6 N1 125.0(2) . . ?
C7 C6 N1 115.5(2) . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C3 C8 C7 118.4(2) . . ?
C3 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
N2 C9 N1 112.8(2) . . ?
N2 C9 S1 121.50(19) . . ?
N1 C9 S1 125.74(18) . . ?
N2 C10 C11 110.5(2) . . ?
N2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 111.6(2) . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 113.0(2) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 113.3(2) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 113.1(2) . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 N1 C6 131.3(2) . . ?
C9 N1 H1 114.4 . . ?
C6 N1 H1 114.4 . . ?
C9 N2 C10 123.5(2) . . ?
C9 N2 H2 118.3 . . ?
C10 N2 H2 118.3 . . ?
C2 O1 C3 119.42(19) . . ?

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
N1 H1 O2 0.88 2.08 2.928(3) 160.4 2
N2 H2 O2 0.88 2.35 3.120(4) 146.7 2

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.058

data_global

# Attachment '2012nb036d-final.cif'


data_p-OEt
#TrackingRef '2012nb036d-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
Jennifer R. Hiscock
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 N2 O S'
_chemical_formula_sum            'C15 H24 N2 O S'
_chemical_formula_weight         280.42

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.390(10)
_cell_length_b                   9.689(11)
_cell_length_c                   19.62(2)
_cell_angle_alpha                93.19(2)
_cell_angle_beta                 101.167(18)
_cell_angle_gamma                90.09(3)
_cell_volume                     1562(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3738
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      31.2


_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9473
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12058
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_sigmaI/netI    0.1410
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5451
_reflns_number_gt                3650
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0413P)²+2.2437P] 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         5451
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.0970
_refine_ls_wR_factor_ref         0.2111
_refine_ls_wR_factor_gt          0.1868
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_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 -0.1923(8) 0.3324(6) -0.2096(3) 0.0388(15) Uani 1 1 d . . .
H1A H -0.2157 0.3770 -0.2540 0.058 Uiso 1 1 calc R . .
H1B H -0.2840 0.3452 -0.1857 0.058 Uiso 1 1 calc R . .
H1C H -0.1756 0.2333 -0.2183 0.058 Uiso 1 1 calc R . .
C3 C 0.0074(7) 0.3324(6) -0.0941(3) 0.0296(13) Uani 1 1 d . . .
H3A H 0.0295 0.2332 -0.1025 0.035 Uiso 1 1 calc R . .
H3B H -0.0868 0.3384 -0.0705 0.035 Uiso 1 1 calc R . .
C4 C 0.1544(7) 0.3988(6) -0.0456(3) 0.0300(13) Uani 1 1 d . . .
H4A H 0.1341 0.4984 -0.0374 0.036 Uiso 1 1 calc R . .
H4B H 0.2502 0.3905 -0.0681 0.036 Uiso 1 1 calc R . .
C5 C 0.1913(7) 0.3312(6) 0.0243(3) 0.0296(13) Uani 1 1 d . . .
H5A H 0.2117 0.2316 0.0159 0.035 Uiso 1 1 calc R . .
H5B H 0.0948 0.3388 0.0463 0.035 Uiso 1 1 calc R . .
C6 C 0.3388(7) 0.3964(6) 0.0748(2) 0.0283(13) Uani 1 1 d . . .
H6A H 0.4376 0.3856 0.0545 0.034 Uiso 1 1 calc R . .
H6B H 0.3210 0.4964 0.0833 0.034 Uiso 1 1 calc R . .
C7 C 0.4791(6) 0.3512(5) 0.1958(3) 0.0243(12) Uani 1 1 d . . .
C8 C 0.5739(7) 0.2659(6) 0.3167(3) 0.0268(13) Uani 1 1 d . . .
C9 C 0.6743(7) 0.3727(6) 0.3515(3) 0.0296(13) Uani 1 1 d . . .
H9 H 0.6757 0.4593 0.3311 0.036 Uiso 1 1 calc R . .
C10 C 0.7730(7) 0.3529(5) 0.4162(3) 0.0278(13) Uani 1 1 d . . .
H10 H 0.8437 0.4252 0.4388 0.033 Uiso 1 1 calc R . .
C11 C 0.7685(7) 0.2293(5) 0.4473(3) 0.0265(13) Uani 1 1 d . . .
C12 C 0.6649(7) 0.1221(6) 0.4134(3) 0.0296(13) Uani 1 1 d . . .
H12 H 0.6606 0.0370 0.4349 0.035 Uiso 1 1 calc R . .
C13 C 0.5691(7) 0.1401(5) 0.3487(3) 0.0267(12) Uani 1 1 d . . .
H13 H 0.4998 0.0671 0.3258 0.032 Uiso 1 1 calc R . .
C14 C 0.9607(7) 0.3065(5) 0.5495(3) 0.0293(13) Uani 1 1 d . . .
H14A H 0.8958 0.3883 0.5587 0.035 Uiso 1 1 calc R . .
H14B H 1.0421 0.3345 0.5224 0.035 Uiso 1 1 calc R . .
C15 C 1.0444(7) 0.2492(6) 0.6175(3) 0.0369(15) Uani 1 1 d . . .
H15A H 1.1160 0.3204 0.6451 0.055 Uiso 1 1 calc R . .
H15B H 1.1089 0.1688 0.6078 0.055 Uiso 1 1 calc R . .
H15C H 0.9625 0.2212 0.6437 0.055 Uiso 1 1 calc R . .
C16 C 0.2981(7) 0.1169(6) -0.2167(3) 0.0349(14) Uani 1 1 d . . .
H16A H 0.2798 0.0627 -0.2613 0.052 Uiso 1 1 calc R . .
H16B H 0.3121 0.2147 -0.2248 0.052 Uiso 1 1 calc R . .
H16C H 0.2043 0.1059 -0.1944 0.052 Uiso 1 1 calc R . .
C17 C 0.4488(7) 0.0667(6) -0.1701(3) 0.0300(13) Uani 1 1 d . . .
H17A H 0.5412 0.0726 -0.1945 0.036 Uiso 1 1 calc R . .
H17B H 0.4327 -0.0318 -0.1619 0.036 Uiso 1 1 calc R . .
C18 C 0.4927(7) 0.1482(6) -0.0997(3) 0.0287(13) Uani 1 1 d . . .
H18A H 0.5095 0.2465 -0.1080 0.034 Uiso 1 1 calc R . .
H18B H 0.3994 0.1432 -0.0757 0.034 Uiso 1 1 calc R . .
C19 C 0.6432(7) 0.0981(6) -0.0517(3) 0.0289(13) Uani 1 1 d . . .
H19A H 0.7376 0.1058 -0.0748 0.035 Uiso 1 1 calc R . .
H19B H 0.6280 -0.0008 -0.0440 0.035 Uiso 1 1 calc R . .
C20 C 0.6806(6) 0.1789(6) 0.0187(2) 0.0266(13) Uani 1 1 d . . .
H20A H 0.6964 0.2778 0.0111 0.032 Uiso 1 1 calc R . .
H20B H 0.5864 0.1714 0.0418 0.032 Uiso 1 1 calc R . .
C21 C 0.8308(7) 0.1278(5) 0.0662(3) 0.0276(13) Uani 1 1 d . . .
H21A H 0.8172 0.0286 0.0736 0.033 Uiso 1 1 calc R . .
H21B H 0.9268 0.1384 0.0444 0.033 Uiso 1 1 calc R . .
C22 C 0.9751(6) 0.1879(5) 0.1886(2) 0.0242(12) Uani 1 1 d . . .
C23 C 1.0707(7) 0.2494(5) 0.3135(3) 0.0258(12) Uani 1 1 d . . .
C24 C 1.0662(7) 0.1277(6) 0.3480(3) 0.0297(13) Uani 1 1 d . . .
H24 H 0.9971 0.0535 0.3263 0.036 Uiso 1 1 calc R . .
C25 C 1.1595(7) 0.1137(5) 0.4122(3) 0.0301(13) Uani 1 1 d . . .
H25 H 1.1557 0.0299 0.4348 0.036 Uiso 1 1 calc R . .
C26 C 1.2611(7) 0.2225(6) 0.4451(3) 0.0276(13) Uani 1 1 d . . .
C27 C 1.2669(7) 0.3460(5) 0.4119(3) 0.0272(13) Uani 1 1 d . . .
H27 H 1.3351 0.4204 0.4338 0.033 Uiso 1 1 calc R . .
C28 C 1.1703(7) 0.3580(5) 0.3457(3) 0.0294(13) Uani 1 1 d . . .
H28 H 1.1732 0.4415 0.3227 0.035 Uiso 1 1 calc R . .
C29 C 1.4533(7) 0.3057(6) 0.5455(3) 0.0354(14) Uani 1 1 d . . .
H29A H 1.3887 0.3879 0.5544 0.042 Uiso 1 1 calc R . .
H29B H 1.5331 0.3325 0.5173 0.042 Uiso 1 1 calc R . .
C30 C 1.5398(8) 0.2505(7) 0.6136(3) 0.0478(18) Uani 1 1 d . . .
H30A H 1.6112 0.3227 0.6404 0.072 Uiso 1 1 calc R . .
H30B H 1.6046 0.1703 0.6040 0.072 Uiso 1 1 calc R . .
H30C H 1.4593 0.2228 0.6406 0.072 Uiso 1 1 calc R . .
C47 C -0.0379(7) 0.3975(6) -0.1638(3) 0.0292(13) Uani 1 1 d . . .
H47A H 0.0534 0.3868 -0.1889 0.035 Uiso 1 1 calc R . .
H47B H -0.0551 0.4976 -0.1557 0.035 Uiso 1 1 calc R . .
N1 N 0.3595(5) 0.3264(5) 0.1404(2) 0.0281(11) Uani 1 1 d . . .
H1 H 0.2874 0.2633 0.1439 0.034 Uiso 1 1 d R . .
N2 N 0.4675(5) 0.2780(4) 0.2517(2) 0.0242(10) Uani 1 1 d . . .
H2 H 0.3777 0.2286 0.2470 0.029 Uiso 1 1 d R . .
N3 N 0.8558(6) 0.2088(4) 0.1337(2) 0.0283(11) Uani 1 1 d . . .
H3 H 0.7871 0.2756 0.1379 0.034 Uiso 1 1 d R . .
N4 N 0.9672(5) 0.2650(4) 0.24666(19) 0.0265(11) Uani 1 1 d . . .
H4 H 0.8936 0.3301 0.2439 0.032 Uiso 1 1 d R . .
O1 O 0.8578(5) 0.1995(4) 0.51200(17) 0.0313(9) Uani 1 1 d . . .
O2 O 1.3499(5) 0.1973(4) 0.50991(18) 0.0329(10) Uani 1 1 d . . .
S1 S 0.63145(17) 0.46497(14) 0.19180(7) 0.0272(4) Uani 1 1 d . . .
S2 S 1.12539(17) 0.07127(14) 0.18254(7) 0.0277(4) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C47 1.538(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C47 1.519(7) . ?
C3 C4 1.522(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.530(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.538(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.470(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.339(6) . ?
C7 N2 1.357(6) . ?
C7 S1 1.703(5) . ?
C8 C9 1.393(7) . ?
C8 C13 1.405(7) . ?
C8 N2 1.419(6) . ?
C9 C10 1.398(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(7) . ?
C10 H10 0.9500 . ?
C11 O1 1.389(6) . ?
C11 C12 1.404(7) . ?
C12 C13 1.385(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O1 1.424(6) . ?
C14 C15 1.518(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.508(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.533(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.520(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.525(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.516(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 N3 1.480(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 N4 1.340(6) . ?
C22 N3 1.346(6) . ?
C22 S2 1.711(6) . ?
C23 C28 1.387(7) . ?
C23 C24 1.396(7) . ?
C23 N4 1.442(6) . ?
C24 C25 1.363(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.401(7) . ?
C25 H25 0.9500 . ?
C26 O2 1.378(6) . ?
C26 C27 1.399(7) . ?
C27 C28 1.402(7) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 O2 1.423(6) . ?
C29 C30 1.518(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
N1 H1 0.8740 . ?
N2 H2 0.8788 . ?
N3 H3 0.8783 . ?
N4 H4 0.8795 . ?

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
C47 C1 H1A 109.5 . . ?
C47 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C47 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C47 C3 C4 114.4(4) . . ?
C47 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C47 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 111.8(4) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 113.2(4) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 C5 108.4(4) . . ?
N1 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
N1 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
N1 C7 N2 114.7(5) . . ?
N1 C7 S1 120.0(4) . . ?
N2 C7 S1 125.3(4) . . ?
C9 C8 C13 119.1(5) . . ?
C9 C8 N2 123.9(5) . . ?
C13 C8 N2 116.8(5) . . ?
C8 C9 C10 120.2(5) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 O1 125.4(5) . . ?
C10 C11 C12 119.6(5) . . ?
O1 C11 C12 114.9(5) . . ?
C13 C12 C11 120.1(5) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.3(5) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
O1 C14 C15 107.1(4) . . ?
O1 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O1 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C16 C17 C18 114.0(5) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 114.7(5) . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 113.3(5) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 112.8(4) . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
N3 C21 C20 109.4(4) . . ?
N3 C21 H21A 109.8 . . ?
C20 C21 H21A 109.8 . . ?
N3 C21 H21B 109.8 . . ?
C20 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?
N4 C22 N3 115.3(5) . . ?
N4 C22 S2 123.5(4) . . ?
N3 C22 S2 121.2(4) . . ?
C28 C23 C24 119.3(5) . . ?
C28 C23 N4 120.2(5) . . ?
C24 C23 N4 120.5(5) . . ?
C25 C24 C23 120.9(5) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 120.3(5) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
O2 C26 C27 124.7(5) . . ?
O2 C26 C25 115.4(5) . . ?
C27 C26 C25 119.9(5) . . ?
C26 C27 C28 119.0(5) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C23 C28 C27 120.7(5) . . ?
C23 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
O2 C29 C30 106.7(5) . . ?
O2 C29 H29A 110.4 . . ?
C30 C29 H29A 110.4 . . ?
O2 C29 H29B 110.4 . . ?
C30 C29 H29B 110.4 . . ?
H29A C29 H29B 108.6 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C3 C47 C1 112.6(4) . . ?
C3 C47 H47A 109.1 . . ?
C1 C47 H47A 109.1 . . ?
C3 C47 H47B 109.1 . . ?
C1 C47 H47B 109.1 . . ?
H47A C47 H47B 107.8 . . ?
C7 N1 C6 125.7(4) . . ?
C7 N1 H1 116.8 . . ?
C6 N1 H1 117.4 . . ?
C7 N2 C8 131.9(5) . . ?
C7 N2 H2 114.4 . . ?
C8 N2 H2 113.6 . . ?
C22 N3 C21 125.1(5) . . ?
C22 N3 H3 118.0 . . ?
C21 N3 H3 117.0 . . ?
C22 N4 C23 124.8(5) . . ?
C22 N4 H4 117.8 . . ?
C23 N4 H4 117.4 . . ?
C11 O1 C14 117.1(4) . . ?
C26 O2 C29 117.2(4) . . ?

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
C47 C3 C4 C5 178.6(5) . . . . ?
C3 C4 C5 C6 -179.7(5) . . . . ?
C4 C5 C6 N1 178.3(5) . . . . ?
C13 C8 C9 C10 2.2(8) . . . . ?
N2 C8 C9 C10 178.6(5) . . . . ?
C8 C9 C10 C11 -2.0(9) . . . . ?
C9 C10 C11 O1 -178.3(5) . . . . ?
C9 C10 C11 C12 0.6(8) . . . . ?
C10 C11 C12 C13 0.7(8) . . . . ?
O1 C11 C12 C13 179.7(5) . . . . ?
C11 C12 C13 C8 -0.5(8) . . . . ?
C9 C8 C13 C12 -1.0(8) . . . . ?
N2 C8 C13 C12 -177.6(5) . . . . ?
C16 C17 C18 C19 179.4(5) . . . . ?
C17 C18 C19 C20 -178.4(5) . . . . ?
C18 C19 C20 C21 179.9(4) . . . . ?
C19 C20 C21 N3 -178.4(4) . . . . ?
C28 C23 C24 C25 -0.8(8) . . . . ?
N4 C23 C24 C25 -177.8(5) . . . . ?
C23 C24 C25 C26 0.5(9) . . . . ?
C24 C25 C26 O2 180.0(5) . . . . ?
C24 C25 C26 C27 0.0(8) . . . . ?
O2 C26 C27 C28 179.8(5) . . . . ?
C25 C26 C27 C28 -0.2(8) . . . . ?
C24 C23 C28 C27 0.6(8) . . . . ?
N4 C23 C28 C27 177.5(5) . . . . ?
C26 C27 C28 C23 -0.1(8) . . . . ?
C4 C3 C47 C1 -177.0(5) . . . . ?
N2 C7 N1 C6 176.9(5) . . . . ?
S1 C7 N1 C6 -4.2(8) . . . . ?
C5 C6 N1 C7 177.1(5) . . . . ?
N1 C7 N2 C8 174.0(5) . . . . ?
S1 C7 N2 C8 -4.9(8) . . . . ?
C9 C8 N2 C7 33.2(9) . . . . ?
C13 C8 N2 C7 -150.3(5) . . . . ?
N4 C22 N3 C21 -174.5(5) . . . . ?
S2 C22 N3 C21 6.1(7) . . . . ?
C20 C21 N3 C22 177.9(5) . . . . ?
N3 C22 N4 C23 172.8(5) . . . . ?
S2 C22 N4 C23 -7.7(8) . . . . ?
C28 C23 N4 C22 119.4(6) . . . . ?
C24 C23 N4 C22 -63.7(8) . . . . ?
C10 C11 O1 C14 1.0(8) . . . . ?
C12 C11 O1 C14 -178.0(5) . . . . ?
C15 C14 O1 C11 -179.8(5) . . . . ?
C27 C26 O2 C29 0.7(8) . . . . ?
C25 C26 O2 C29 -179.3(5) . . . . ?
C30 C29 O2 C26 -178.4(5) . . . . ?

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
N1 H1 S2 0.87 2.54 3.390(5) 165.7 1_455
N2 H2 S2 0.88 2.67 3.502(5) 157.9 1_455
N3 H3 S1 0.88 2.55 3.397(5) 161.2 .
N4 H4 S1 0.88 2.62 3.453(5) 157.7 .

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.073

data_global

# Attachment '2012nb104-final.cif'


data_p-I
#TrackingRef '2012nb104-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
Jennifer R. Hiscock
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 I N2 S'
_chemical_formula_sum            'C13 H19 I N2 S'
_chemical_formula_weight         362.26

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   11.4798(8)
_cell_length_b                   8.4051(6)
_cell_length_c                   15.6294(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.550(7)
_cell_angle_gamma                90.00
_cell_volume                     1472.03(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11974
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.6

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    2.300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8026
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13677
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3362
_reflns_number_gt                2859
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0233P)²+0.0000P] 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         3362
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0562
_refine_ls_wR_factor_gt          0.0541
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C10 C 1.1498(2) 0.1464(3) 0.38682(16) 0.0211(5) Uani 1 1 d . . .
H10A H 1.1946 0.2480 0.3940 0.025 Uiso 1 1 calc R . .
H10B H 1.1725 0.0870 0.3382 0.025 Uiso 1 1 calc R . .
C11 C 1.1862(2) 0.0498(3) 0.47074(17) 0.0255(6) Uani 1 1 d . . .
H11A H 1.1628 0.1088 0.5192 0.031 Uiso 1 1 calc R . .
H11B H 1.1420 -0.0521 0.4634 0.031 Uiso 1 1 calc R . .
C12 C 1.3189(3) 0.0148(3) 0.49595(19) 0.0336(7) Uani 1 1 d . . .
H12A H 1.3633 0.1165 0.5066 0.040 Uiso 1 1 calc R . .
H12B H 1.3435 -0.0396 0.4465 0.040 Uiso 1 1 calc R . .
C13 C 1.3519(3) -0.0886(4) 0.5774(2) 0.0472(9) Uani 1 1 d . . .
H13A H 1.4382 -0.1076 0.5911 0.071 Uiso 1 1 calc R . .
H13B H 1.3098 -0.1905 0.5667 0.071 Uiso 1 1 calc R . .
H13C H 1.3291 -0.0345 0.6268 0.071 Uiso 1 1 calc R . .
S1 S 0.78913(5) 0.08362(7) 0.14125(4) 0.01672(12) Uani 1 1 d . . .
C1 C 0.3043(2) 0.1358(3) 0.12685(15) 0.0165(5) Uani 1 1 d . . .
C2 C 0.3406(2) 0.2202(3) 0.20452(15) 0.0199(5) Uani 1 1 d . . .
H2A H 0.2854 0.2447 0.2400 0.024 Uiso 1 1 calc R . .
C3 C 0.4575(2) 0.2675(3) 0.22915(15) 0.0192(5) Uani 1 1 d . . .
H3 H 0.4825 0.3255 0.2821 0.023 Uiso 1 1 calc R . .
C4 C 0.5402(2) 0.2330(3) 0.17907(15) 0.0161(5) Uani 1 1 d . . .
C5 C 0.5027(2) 0.1517(3) 0.10036(15) 0.0173(5) Uani 1 1 d . . .
H5 H 0.5576 0.1297 0.0643 0.021 Uiso 1 1 calc R . .
C6 C 0.3848(2) 0.1027(3) 0.07477(16) 0.0183(5) Uani 1 1 d . . .
H6 H 0.3592 0.0463 0.0213 0.022 Uiso 1 1 calc R . .
C7 C 0.7658(2) 0.2349(3) 0.20692(14) 0.0159(5) Uani 1 1 d . . .
C8 C 0.9805(2) 0.2721(3) 0.27635(15) 0.0189(5) Uani 1 1 d . . .
H8A H 1.0286 0.3704 0.2789 0.023 Uiso 1 1 calc R . .
H8B H 0.9962 0.2053 0.2279 0.023 Uiso 1 1 calc R . .
C9 C 1.0173(2) 0.1823(3) 0.36246(16) 0.0212(5) Uani 1 1 d . . .
H9A H 0.9953 0.2462 0.4098 0.025 Uiso 1 1 calc R . .
H9B H 0.9724 0.0809 0.3581 0.025 Uiso 1 1 calc R . .
N1 N 0.65624(16) 0.2928(2) 0.21098(12) 0.0171(4) Uani 1 1 d . . .
H1 H 0.6583 0.3844 0.2386 0.021 Uiso 1 1 calc R . .
N2 N 0.85459(16) 0.3129(2) 0.25939(12) 0.0184(4) Uani 1 1 d . . .
H2 H 0.8350 0.3975 0.2864 0.022 Uiso 1 1 calc R . .
I1 I 0.126313(14) 0.063211(19) 0.088060(10) 0.02108(6) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C10 C9 1.517(3) . ?
C10 C11 1.522(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.516(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.520(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
S1 C7 1.692(2) . ?
C1 C6 1.386(3) . ?
C1 C2 1.389(3) . ?
C1 I1 2.092(2) . ?
C2 C3 1.372(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 N1 1.410(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.334(3) . ?
C7 N1 1.362(3) . ?
C8 N2 1.453(3) . ?
C8 C9 1.521(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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 C10 C11 113.3(2) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 113.6(2) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 112.5(3) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C1 C2 120.3(2) . . ?
C6 C1 I1 120.34(17) . . ?
C2 C1 I1 119.39(17) . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 122.0(2) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 N1 115.9(2) . . ?
C5 C4 N1 125.1(2) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N2 C7 N1 112.7(2) . . ?
N2 C7 S1 122.80(18) . . ?
N1 C7 S1 124.48(17) . . ?
N2 C8 C9 110.68(19) . . ?
N2 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 113.1(2) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C7 N1 C4 131.8(2) . . ?
C7 N1 H1 114.1 . . ?
C4 N1 H1 114.1 . . ?
C7 N2 C8 126.4(2) . . ?
C7 N2 H2 116.8 . . ?
C8 N2 H2 116.8 . . ?

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
C9 C10 C11 C12 -179.5(2) . . . . ?
C10 C11 C12 C13 -177.1(2) . . . . ?
C6 C1 C2 C3 -1.1(4) . . . . ?
I1 C1 C2 C3 -179.87(18) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C2 C3 C4 N1 178.2(2) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
N1 C4 C5 C6 -178.0(2) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
I1 C1 C6 C5 179.68(17) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C11 C10 C9 C8 -177.3(2) . . . . ?
N2 C8 C9 C10 -176.0(2) . . . . ?
N2 C7 N1 C4 -168.2(2) . . . . ?
S1 C7 N1 C4 13.2(4) . . . . ?
C3 C4 N1 C7 147.0(2) . . . . ?
C5 C4 N1 C7 -36.7(4) . . . . ?
N1 C7 N2 C8 174.0(2) . . . . ?
S1 C7 N2 C8 -7.4(3) . . . . ?
C9 C8 N2 C7 -99.1(3) . . . . ?

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
N1 H1 S1 0.88 2.49 3.328(2) 159.1 2_655
N2 H2 S1 0.88 2.54 3.380(2) 159.5 2_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.093

data_global

# Attachment '2012nb105-final.cif'


data_p-COCF3
#TrackingRef '2012nb105-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
Jennifer R. Hiscock
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 F3 N2 O S'
_chemical_formula_sum            'C15 H19 F3 N2 O S'
_chemical_formula_weight         332.38

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'
F F 0.0171 0.0103 '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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2392(4)
_cell_length_b                   11.0200(9)
_cell_length_c                   14.5788(11)
_cell_angle_alpha                75.946(5)
_cell_angle_beta                 79.884(6)
_cell_angle_gamma                79.501(6)
_cell_volume                     795.20(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7183
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9388
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7651
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3632
_reflns_number_gt                3230
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0430P)²+0.3403P] 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         3632
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
S1 S 0.03970(6) 0.05271(3) 0.13070(2) 0.01717(10) Uani 1 1 d . . .
C1 C -1.1141(3) 0.45002(14) -0.29474(10) 0.0203(3) Uani 1 1 d . . .
C2 C -1.0393(3) 0.48475(13) -0.20741(9) 0.0177(3) Uani 1 1 d . . .
C3 C -0.8567(3) 0.39218(12) -0.15046(9) 0.0155(3) Uani 1 1 d . . .
C4 C -0.7812(3) 0.26669(12) -0.15929(9) 0.0161(3) Uani 1 1 d . . .
H4 H -0.8506 0.2365 -0.2041 0.019 Uiso 1 1 calc R . .
C5 C -0.6066(3) 0.18646(12) -0.10329(9) 0.0158(3) Uani 1 1 d . . .
H5 H -0.5593 0.1009 -0.1089 0.019 Uiso 1 1 calc R . .
C6 C -0.4985(2) 0.22987(12) -0.03828(9) 0.0144(3) Uani 1 1 d . . .
C7 C -0.5706(3) 0.35575(13) -0.02995(9) 0.0180(3) Uani 1 1 d . . .
H7 H -0.4968 0.3866 0.0134 0.022 Uiso 1 1 calc R . .
C8 C -0.7491(3) 0.43505(13) -0.08488(10) 0.0185(3) Uani 1 1 d . . .
H8 H -0.7998 0.5200 -0.0781 0.022 Uiso 1 1 calc R . .
C9 C -0.2431(3) 0.14221(12) 0.09921(9) 0.0153(3) Uani 1 1 d . . .
C10 C -0.3712(3) 0.21616(14) 0.25149(10) 0.0218(3) Uani 1 1 d . . .
H10A H -0.4012 0.3059 0.2563 0.026 Uiso 1 1 calc R . .
H10B H -0.1885 0.1807 0.2623 0.026 Uiso 1 1 calc R . .
C11 C -0.5594(3) 0.14359(14) 0.32795(10) 0.0232(3) Uani 1 1 d . . .
H11A H -0.5558 0.1651 0.3898 0.028 Uiso 1 1 calc R . .
H11B H -0.7396 0.1713 0.3115 0.028 Uiso 1 1 calc R . .
C12 C -0.4953(3) 0.00121(14) 0.33937(10) 0.0223(3) Uani 1 1 d . . .
H12A H -0.3163 -0.0268 0.3569 0.027 Uiso 1 1 calc R . .
H12B H -0.4962 -0.0202 0.2773 0.027 Uiso 1 1 calc R . .
C13 C -0.6865(3) -0.07076(15) 0.41475(10) 0.0251(3) Uani 1 1 d . . .
H13A H -0.7003 -0.0426 0.4752 0.030 Uiso 1 1 calc R . .
H13B H -0.8621 -0.0502 0.3938 0.030 Uiso 1 1 calc R . .
C14 C -0.6032(3) -0.21257(16) 0.43270(11) 0.0299(3) Uani 1 1 d . . .
H14A H -0.4297 -0.2328 0.4553 0.036 Uiso 1 1 calc R . .
H14B H -0.5833 -0.2398 0.3716 0.036 Uiso 1 1 calc R . .
C15 C -0.7945(4) -0.28763(19) 0.50555(14) 0.0404(4) Uani 1 1 d . . .
H15A H -0.7292 -0.3782 0.5134 0.061 Uiso 1 1 calc R . .
H15B H -0.9662 -0.2696 0.4832 0.061 Uiso 1 1 calc R . .
H15C H -0.8113 -0.2634 0.5669 0.061 Uiso 1 1 calc R . .
N1 N -0.3092(2) 0.14563(10) 0.01188(8) 0.0153(2) Uani 1 1 d . . .
H1 H -0.2203 0.0864 -0.0171 0.018 Uiso 1 1 calc R . .
N2 N -0.4078(2) 0.20854(11) 0.15570(8) 0.0198(3) Uani 1 1 d . . .
H2 H -0.5513 0.2516 0.1337 0.024 Uiso 1 1 calc R . .
O1 O -1.1326(2) 0.58772(10) -0.19152(8) 0.0257(2) Uani 1 1 d . . .
F1 F -1.2616(2) 0.54608(9) -0.34398(7) 0.0338(2) Uani 1 1 d . . .
F2 F -0.90236(17) 0.41751(9) -0.35379(6) 0.0273(2) Uani 1 1 d . . .
F3 F -1.24867(18) 0.35233(9) -0.26731(7) 0.0303(2) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 1.6928(13) . ?
C1 F1 1.3269(16) . ?
C1 F2 1.3302(16) . ?
C1 F3 1.3358(17) . ?
C1 C2 1.5452(19) . ?
C2 O1 1.2108(17) . ?
C2 C3 1.4688(18) . ?
C3 C4 1.3982(18) . ?
C3 C8 1.4001(19) . ?
C4 C5 1.3793(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3985(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3987(18) . ?
C6 N1 1.4032(16) . ?
C7 C8 1.3802(19) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N2 1.3305(17) . ?
C9 N1 1.3672(17) . ?
C10 N2 1.4666(17) . ?
C10 C11 1.524(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.518(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.515(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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
F1 C1 F2 107.68(11) . . ?
F1 C1 F3 107.77(12) . . ?
F2 C1 F3 107.61(12) . . ?
F1 C1 C2 111.50(12) . . ?
F2 C1 C2 111.36(11) . . ?
F3 C1 C2 110.75(11) . . ?
O1 C2 C3 124.42(13) . . ?
O1 C2 C1 117.49(12) . . ?
C3 C2 C1 118.08(11) . . ?
C4 C3 C8 118.83(12) . . ?
C4 C3 C2 124.27(12) . . ?
C8 C3 C2 116.89(12) . . ?
C5 C4 C3 120.35(12) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.62(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 119.30(12) . . ?
C5 C6 N1 117.63(11) . . ?
C7 C6 N1 122.95(12) . . ?
C8 C7 C6 119.86(12) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C3 121.02(12) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
N2 C9 N1 117.85(12) . . ?
N2 C9 S1 123.41(10) . . ?
N1 C9 S1 118.73(10) . . ?
N2 C10 C11 111.09(12) . . ?
N2 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
N2 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 113.49(11) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 113.28(12) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 112.51(12) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 113.85(14) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 N1 C6 129.35(11) . . ?
C9 N1 H1 115.3 . . ?
C6 N1 H1 115.3 . . ?
C9 N2 C10 125.72(12) . . ?
C9 N2 H2 117.1 . . ?
C10 N2 H2 117.1 . . ?

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
F1 C1 C2 O1 4.25(18) . . . . ?
F2 C1 C2 O1 124.55(13) . . . . ?
F3 C1 C2 O1 -115.75(14) . . . . ?
F1 C1 C2 C3 -174.62(11) . . . . ?
F2 C1 C2 C3 -54.32(16) . . . . ?
F3 C1 C2 C3 65.38(15) . . . . ?
O1 C2 C3 C4 169.51(13) . . . . ?
C1 C2 C3 C4 -11.70(19) . . . . ?
O1 C2 C3 C8 -11.9(2) . . . . ?
C1 C2 C3 C8 166.89(12) . . . . ?
C8 C3 C4 C5 0.87(19) . . . . ?
C2 C3 C4 C5 179.44(12) . . . . ?
C3 C4 C5 C6 -1.26(19) . . . . ?
C4 C5 C6 C7 0.44(19) . . . . ?
C4 C5 C6 N1 -175.91(11) . . . . ?
C5 C6 C7 C8 0.76(19) . . . . ?
N1 C6 C7 C8 176.90(12) . . . . ?
C6 C7 C8 C3 -1.2(2) . . . . ?
C4 C3 C8 C7 0.3(2) . . . . ?
C2 C3 C8 C7 -178.34(12) . . . . ?
N2 C10 C11 C12 70.22(15) . . . . ?
C10 C11 C12 C13 -179.08(12) . . . . ?
C11 C12 C13 C14 -173.82(13) . . . . ?
C12 C13 C14 C15 -178.23(14) . . . . ?
N2 C9 N1 C6 15.5(2) . . . . ?
S1 C9 N1 C6 -165.47(10) . . . . ?
C5 C6 N1 C9 -153.53(13) . . . . ?
C7 C6 N1 C9 30.3(2) . . . . ?
N1 C9 N2 C10 179.79(12) . . . . ?
S1 C9 N2 C10 0.8(2) . . . . ?
C11 C10 N2 C9 -108.18(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
N1 H1 S1 0.88 2.48 3.3380(11) 165.4 2
N2 H2 O1 0.88 2.40 3.0444(15) 130.4 2_365

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.056

data_global

# Attachment '2012ncs0199-final.cif'


data_p-OMe
#TrackingRef '2012ncs0199-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N2 O S'
_chemical_formula_sum            'C14 H22 N2 O S'
_chemical_formula_weight         266.40

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   36.040(5)
_cell_length_b                   4.347(5)
_cell_length_c                   9.590(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 95.300(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1496.0(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2378
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      26.6

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_type              'DLS beamline I19'
_diffrn_source                   synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_radiation_collimation    'Confocal mirrors'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8777
_diffrn_reflns_av_R_equivalents  0.1318
_diffrn_reflns_av_sigmaI/netI    0.1148
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         24.21
_reflns_number_total             2402
_reflns_number_gt                1218
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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.

Data completeness only 90.8%, but this is sufficient for proof of structure and hydrogen bonding network
;

_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)+(0.1863P)²+0.0000P] 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         2402
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.0993
_refine_ls_wR_factor_ref         0.2973
_refine_ls_wR_factor_gt          0.2443
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_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 0.46481(15) 0.7234(17) 1.1180(7) 0.0593(17) Uani 1 1 d . . .
H1A H 0.4871 0.7653 1.0696 0.089 Uiso 1 1 calc R . .
H1B H 0.4704 0.5630 1.1886 0.089 Uiso 1 1 calc R . .
H1C H 0.4571 0.9116 1.1638 0.089 Uiso 1 1 calc R . .
C2 C 0.43352(13) 0.6154(15) 1.0128(7) 0.0551(17) Uani 1 1 d . . .
H2A H 0.4416 0.4269 0.9661 0.066 Uiso 1 1 calc R . .
H2B H 0.4286 0.7757 0.9401 0.066 Uiso 1 1 calc R . .
C3 C 0.39687(13) 0.5463(15) 1.0805(6) 0.0491(15) Uani 1 1 d . . .
H3A H 0.4021 0.3911 1.1553 0.059 Uiso 1 1 calc R . .
H3B H 0.3886 0.7366 1.1250 0.059 Uiso 1 1 calc R . .
C4 C 0.36491(12) 0.4272(15) 0.9767(6) 0.0491(16) Uani 1 1 d . . .
H4A H 0.3730 0.2344 0.9335 0.059 Uiso 1 1 calc R . .
H4B H 0.3599 0.5805 0.9010 0.059 Uiso 1 1 calc R . .
C5 C 0.32838(13) 0.3649(14) 1.0453(6) 0.0462(15) Uani 1 1 d . . .
H5A H 0.3332 0.2134 1.1219 0.055 Uiso 1 1 calc R . .
H5B H 0.3197 0.5580 1.0864 0.055 Uiso 1 1 calc R . .
C6 C 0.29788(12) 0.2411(14) 0.9375(6) 0.0460(15) Uani 1 1 d . . .
H6A H 0.2939 0.3860 0.8579 0.055 Uiso 1 1 calc R . .
H6B H 0.3056 0.0403 0.9010 0.055 Uiso 1 1 calc R . .
C7 C 0.23104(12) 0.0853(12) 0.9406(6) 0.0364(13) Uani 1 1 d . . .
C8 C 0.16203(11) 0.0539(13) 0.9601(5) 0.0371(13) Uani 1 1 d . . .
C9 C 0.14116(12) -0.1500(12) 1.0347(6) 0.0374(13) Uani 1 1 d . . .
H9 H 0.1526 -0.2560 1.1140 0.045 Uiso 1 1 calc R . .
C10 C 0.10321(12) -0.1971(13) 0.9919(6) 0.0404(13) Uani 1 1 d . . .
H10 H 0.0888 -0.3304 1.0442 0.048 Uiso 1 1 calc R . .
C11 C 0.08667(11) -0.0504(13) 0.8739(6) 0.0371(13) Uani 1 1 d . . .
C12 C 0.10794(13) 0.1526(12) 0.7990(6) 0.0414(13) Uani 1 1 d . . .
H12 H 0.0968 0.2543 0.7180 0.050 Uiso 1 1 calc R . .
C13 C 0.14548(12) 0.2043(13) 0.8443(6) 0.0393(13) Uani 1 1 d . . .
H13 H 0.1596 0.3443 0.7946 0.047 Uiso 1 1 calc R . .
C14 C 0.02692(13) -0.2947(14) 0.8944(6) 0.0467(14) Uani 1 1 d . . .
H14A H 0.0016 -0.3022 0.8479 0.070 Uiso 1 1 calc R . .
H14B H 0.0261 -0.2225 0.9909 0.070 Uiso 1 1 calc R . .
H14C H 0.0379 -0.5008 0.8952 0.070 Uiso 1 1 calc R . .
N1 N 0.26293(10) 0.2043(11) 1.0052(5) 0.0421(12) Uani 1 1 d . . .
H1 H 0.2628 0.2632 1.0930 0.051 Uiso 1 1 calc R . .
N2 N 0.20046(10) 0.1167(10) 1.0137(5) 0.0408(12) Uani 1 1 d . . .
H2 H 0.2043 0.1806 1.1009 0.049 Uiso 1 1 calc R . .
O1 O 0.04925(8) -0.0860(8) 0.8197(4) 0.0434(10) Uani 1 1 d . . .
S1 S 0.22995(3) -0.1058(3) 0.78263(15) 0.0425(5) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.516(8) . ?
C2 C3 1.554(7) . ?
C3 C4 1.541(7) . ?
C4 C5 1.549(6) . ?
C5 C6 1.535(7) . ?
C6 N1 1.478(6) . ?
C7 N1 1.357(6) . ?
C7 N2 1.366(6) . ?
C7 S1 1.725(6) . ?
C8 C13 1.376(7) . ?
C8 C9 1.401(7) . ?
C8 N2 1.458(6) . ?
C9 C10 1.406(6) . ?
C10 C11 1.385(8) . ?
C11 C12 1.408(8) . ?
C11 O1 1.408(5) . ?
C12 C13 1.401(6) . ?
C14 O1 1.446(6) . ?

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
C1 C2 C3 113.0(5) . . ?
C4 C3 C2 114.1(5) . . ?
C3 C4 C5 113.5(5) . . ?
C6 C5 C4 111.0(5) . . ?
N1 C6 C5 109.2(5) . . ?
N1 C7 N2 114.7(5) . . ?
N1 C7 S1 122.3(4) . . ?
N2 C7 S1 123.0(4) . . ?
C13 C8 C9 120.0(4) . . ?
C13 C8 N2 121.5(5) . . ?
C9 C8 N2 118.4(5) . . ?
C8 C9 C10 119.8(5) . . ?
C11 C10 C9 120.3(5) . . ?
C10 C11 C12 119.5(4) . . ?
C10 C11 O1 125.2(5) . . ?
C12 C11 O1 115.4(4) . . ?
C13 C12 C11 119.9(5) . . ?
C8 C13 C12 120.5(5) . . ?
C7 N1 C6 124.1(5) . . ?
C7 N2 C8 125.8(5) . . ?
C11 O1 C14 116.4(4) . . ?

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
N1 H1 S1 0.88 2.71 3.482(5) 147.6 4_566
N2 H2 S1 0.88 2.65 3.434(5) 149.4 4_566

_diffrn_measured_fraction_theta_max 0.908
_diffrn_reflns_theta_full        24.21
_diffrn_measured_fraction_theta_full 0.908
_refine_diff_density_max         1.085
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.100

data_global

# Attachment '2012ncs0603-final.cif'


data_p-Ethyl
#TrackingRef '2012ncs0603-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 N2 S'
_chemical_formula_sum            'C15 H24 N2 S'
_chemical_formula_weight         264.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1181 0.1169 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   13.07(2)
_cell_length_b                   13.28(3)
_cell_length_c                   8.885(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.56(2)
_cell_angle_gamma                90.00
_cell_volume                     1539(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2681
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      26.6

_exptl_crystal_description       blade
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9941
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_type              'DLS beamline I19'
_diffrn_source                   synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_radiation_collimation    'Confocal mirrors'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10433
_diffrn_reflns_av_R_equivalents  0.2114
_diffrn_reflns_av_sigmaI/netI    0.1373
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         24.20
_reflns_number_total             2637
_reflns_number_gt                1418
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.1728P)²+0.2975P] 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     SHELXL
_refine_ls_extinction_coef       0.016(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2637
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1794
_refine_ls_R_factor_gt           0.1039
_refine_ls_wR_factor_ref         0.3229
_refine_ls_wR_factor_gt          0.2559
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.6158(6) 0.6004(7) 0.2027(8) 0.090(3) Uani 1 1 d . . .
H1A H 0.6694 0.5708 0.2710 0.135 Uiso 1 1 calc R . .
H1B H 0.6410 0.6632 0.1607 0.135 Uiso 1 1 calc R . .
H1C H 0.5978 0.5531 0.1206 0.135 Uiso 1 1 calc R . .
C2 C 0.5253(5) 0.6212(7) 0.2858(8) 0.081(2) Uani 1 1 d . . .
H2A H 0.5447 0.6676 0.3701 0.097 Uiso 1 1 calc R . .
H2B H 0.5015 0.5576 0.3299 0.097 Uiso 1 1 calc R . .
C3 C 0.4364(5) 0.6681(6) 0.1884(7) 0.0638(19) Uani 1 1 d . . .
C4 C 0.3696(4) 0.6065(5) 0.1009(7) 0.0610(18) Uani 1 1 d . . .
H4 H 0.3783 0.5355 0.1037 0.073 Uiso 1 1 calc R . .
C5 C 0.2899(4) 0.6487(5) 0.0090(7) 0.0572(17) Uani 1 1 d . . .
H5 H 0.2459 0.6063 -0.0520 0.069 Uiso 1 1 calc R . .
C6 C 0.2748(4) 0.7521(5) 0.0065(6) 0.0509(16) Uani 1 1 d . . .
C7 C 0.3432(4) 0.8143(5) 0.0916(6) 0.0546(16) Uani 1 1 d . . .
H7 H 0.3358 0.8854 0.0871 0.066 Uiso 1 1 calc R . .
C8 C 0.4218(5) 0.7710(6) 0.1826(7) 0.0654(19) Uani 1 1 d . . .
H8 H 0.4666 0.8134 0.2422 0.078 Uiso 1 1 calc R . .
C9 C 0.1231(4) 0.8649(5) -0.0461(6) 0.0498(15) Uani 1 1 d . . .
C10 C 0.0361(4) 0.8463(4) -0.3055(6) 0.0492(15) Uani 1 1 d . . .
H10A H 0.0269 0.7726 -0.2971 0.059 Uiso 1 1 calc R . .
H10B H 0.0977 0.8590 -0.3622 0.059 Uiso 1 1 calc R . .
C11 C -0.0581(5) 0.8925(5) -0.3902(6) 0.0514(16) Uani 1 1 d . . .
H11A H -0.1189 0.8814 -0.3312 0.062 Uiso 1 1 calc R . .
H11B H -0.0479 0.9660 -0.3995 0.062 Uiso 1 1 calc R . .
C12 C -0.0779(4) 0.8476(4) -0.5461(6) 0.0492(15) Uani 1 1 d . . .
H12A H -0.0876 0.7740 -0.5366 0.059 Uiso 1 1 calc R . .
H12B H -0.0170 0.8589 -0.6049 0.059 Uiso 1 1 calc R . .
C13 C -0.1727(5) 0.8927(5) -0.6330(6) 0.0518(16) Uani 1 1 d . . .
H13A H -0.2341 0.8778 -0.5771 0.062 Uiso 1 1 calc R . .
H13B H -0.1649 0.9668 -0.6368 0.062 Uiso 1 1 calc R . .
C14 C -0.1898(5) 0.8531(6) -0.7924(7) 0.0654(19) Uani 1 1 d . . .
H14A H -0.1956 0.7788 -0.7893 0.079 Uiso 1 1 calc R . .
H14B H -0.1296 0.8701 -0.8499 0.079 Uiso 1 1 calc R . .
C15 C -0.2871(5) 0.8969(6) -0.8749(7) 0.075(2) Uani 1 1 d . . .
H15A H -0.2948 0.8692 -0.9772 0.113 Uiso 1 1 calc R . .
H15B H -0.2812 0.9704 -0.8802 0.113 Uiso 1 1 calc R . .
H15C H -0.3471 0.8790 -0.8198 0.113 Uiso 1 1 calc R . .
N1 N 0.1910(3) 0.7924(4) -0.0865(5) 0.0510(13) Uani 1 1 d . . .
H1 H 0.1822 0.7682 -0.1786 0.061 Uiso 1 1 calc R . .
N2 N 0.0505(4) 0.8909(4) -0.1536(5) 0.0494(13) Uani 1 1 d . . .
H2 H 0.0077 0.9389 -0.1310 0.059 Uiso 1 1 calc R . .
S001 S 0.12585(11) 0.91904(11) 0.12579(16) 0.0521(6) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.460(10) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.537(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.381(10) . ?
C3 C4 1.397(9) . ?
C4 C5 1.400(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.403(8) . ?
C6 N1 1.435(7) . ?
C7 C8 1.391(8) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N2 1.349(7) . ?
C9 N1 1.372(8) . ?
C9 S001 1.686(7) . ?
C10 N2 1.475(7) . ?
C10 C11 1.530(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.515(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.539(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.515(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.542(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 113.6(6) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C8 C3 C4 118.6(6) . . ?
C8 C3 C2 121.3(6) . . ?
C4 C3 C2 120.1(7) . . ?
C3 C4 C5 120.5(7) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.3(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.3(5) . . ?
C5 C6 N1 118.8(5) . . ?
C7 C6 N1 121.9(6) . . ?
C8 C7 C6 119.5(6) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C3 C8 C7 121.8(6) . . ?
C3 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
N2 C9 N1 115.6(5) . . ?
N2 C9 S001 120.4(5) . . ?
N1 C9 S001 123.9(4) . . ?
N2 C10 C11 110.0(5) . . ?
N2 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C10 112.3(5) . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 113.1(5) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 113.6(5) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 112.5(6) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 N1 C6 126.5(5) . . ?
C9 N1 H1 116.8 . . ?
C6 N1 H1 116.8 . . ?
C9 N2 C10 126.1(5) . . ?
C9 N2 H2 116.9 . . ?
C10 N2 H2 116.9 . . ?

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
N2 H2 S001 0.88 2.57 3.437(7) 167.8 3_575

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        24.20
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.087

data_global

# Attachment 'jenny102-final.cif'


data_p-Propyl
#TrackingRef 'jenny102-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
Jennifer R. Hiscock
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H26 N2 S'
_chemical_formula_sum            'C16 H26 N2 S'
_chemical_formula_weight         278.45

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'
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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   22.536(5)
_cell_length_b                   7.7393(16)
_cell_length_c                   9.223(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.488(7)
_cell_angle_gamma                90.00
_cell_volume                     1591.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6425
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.8

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9405
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11058
_diffrn_reflns_av_R_equivalents  0.1524
_diffrn_reflns_av_sigmaI/netI    0.1956
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2808
_reflns_number_gt                1216
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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)+(0.0544P)²+0.0000P] 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         2808
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1934
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_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 0.0378(2) 0.9442(6) 0.8369(5) 0.0424(13) Uani 1 1 d . . .
H1A H 0.0122 0.8558 0.8720 0.064 Uiso 1 1 calc R . .
H1B H 0.0160 1.0540 0.8247 0.064 Uiso 1 1 calc R . .
H1C H 0.0742 0.9588 0.9084 0.064 Uiso 1 1 calc R . .
C2 C 0.0548(2) 0.8888(5) 0.6916(5) 0.0360(13) Uani 1 1 d . . .
H2A H 0.0177 0.8636 0.6230 0.043 Uiso 1 1 calc R . .
H2B H 0.0783 0.7805 0.7060 0.043 Uiso 1 1 calc R . .
C3 C 0.0910(2) 1.0221(5) 0.6227(5) 0.0359(13) Uani 1 1 d . . .
H3A H 0.1283 1.0460 0.6909 0.043 Uiso 1 1 calc R . .
H3B H 0.0677 1.1309 0.6098 0.043 Uiso 1 1 calc R . .
C4 C 0.1077(2) 0.9687(6) 0.4754(5) 0.0369(12) Uani 1 1 d . . .
H4A H 0.1338 0.8653 0.4893 0.044 Uiso 1 1 calc R . .
H4B H 0.0707 0.9361 0.4092 0.044 Uiso 1 1 calc R . .
C5 C 0.1398(2) 1.1094(5) 0.4030(5) 0.0403(13) Uani 1 1 d . . .
H5A H 0.1133 1.2120 0.3889 0.048 Uiso 1 1 calc R . .
H5B H 0.1762 1.1429 0.4706 0.048 Uiso 1 1 calc R . .
C6 C 0.1579(2) 1.0623(6) 0.2579(5) 0.0428(13) Uani 1 1 d . . .
H6A H 0.1218 1.0300 0.1884 0.051 Uiso 1 1 calc R . .
H6B H 0.1766 1.1635 0.2172 0.051 Uiso 1 1 calc R . .
C7 C 0.2305(2) 0.8656(6) 0.1715(5) 0.0359(13) Uani 1 1 d . . .
C8 C 0.3021(2) 0.6399(6) 0.1188(5) 0.0324(12) Uani 1 1 d . . .
C9 C 0.2936(2) 0.4631(6) 0.0990(5) 0.0370(12) Uani 1 1 d . . .
H9 H 0.2645 0.4043 0.1453 0.044 Uiso 1 1 calc R . .
C10 C 0.3276(2) 0.3739(6) 0.0122(5) 0.0427(14) Uani 1 1 d . . .
H10 H 0.3209 0.2535 -0.0018 0.051 Uiso 1 1 calc R . .
C11 C 0.3703(2) 0.4516(7) -0.0543(5) 0.0417(13) Uani 1 1 d . . .
C12 C 0.3797(2) 0.6291(6) -0.0306(5) 0.0429(14) Uani 1 1 d . . .
H12 H 0.4096 0.6871 -0.0744 0.051 Uiso 1 1 calc R . .
C13 C 0.3455(2) 0.7202(6) 0.0560(5) 0.0381(13) Uani 1 1 d . . .
H13 H 0.3525 0.8403 0.0719 0.046 Uiso 1 1 calc R . .
C14 C 0.4080(3) 0.3551(6) -0.1496(6) 0.0635(17) Uani 1 1 d . . .
H14A H 0.3837 0.3374 -0.2470 0.076 Uiso 1 1 calc R . .
H14B H 0.4426 0.4289 -0.1639 0.076 Uiso 1 1 calc R . .
C15 C 0.4306(3) 0.1901(9) -0.0952(7) 0.101(3) Uani 1 1 d . . .
H15A H 0.3961 0.1133 -0.0880 0.121 Uiso 1 1 calc R . .
H15B H 0.4524 0.2064 0.0053 0.121 Uiso 1 1 calc R . .
C16 C 0.4718(2) 0.1004(7) -0.1851(5) 0.0658(18) Uani 1 1 d . . .
H16A H 0.4853 -0.0092 -0.1381 0.099 Uiso 1 1 calc R . .
H16B H 0.5066 0.1741 -0.1922 0.099 Uiso 1 1 calc R . .
H16C H 0.4503 0.0776 -0.2835 0.099 Uiso 1 1 calc R . .
N1 N 0.19978(17) 0.9195(4) 0.2734(4) 0.0354(10) Uani 1 1 d . . .
H1 H 0.2053 0.8648 0.3579 0.042 Uiso 1 1 d R . .
N2 N 0.26612(17) 0.7278(5) 0.2088(4) 0.0374(11) Uani 1 1 d . . .
H2 H 0.2673 0.6885 0.2987 0.045 Uiso 1 1 d R . .
S1 S 0.22188(6) 0.95749(14) 0.00275(13) 0.0401(4) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.509(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.513(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.519(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.516(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.500(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.447(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.314(5) . ?
C7 N2 1.349(5) . ?
C7 S1 1.696(5) . ?
C8 C13 1.359(6) . ?
C8 C9 1.390(6) . ?
C8 N2 1.418(6) . ?
C9 C10 1.372(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.357(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.402(6) . ?
C11 C14 1.507(7) . ?
C12 C13 1.381(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.438(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.502(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 H1 0.8799 . ?
N2 H2 0.8799 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 113.8(4) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 114.2(4) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 113.3(4) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 115.4(4) . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C4 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
N1 C6 C5 110.9(4) . . ?
N1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 N2 115.1(4) . . ?
N1 C7 S1 121.5(4) . . ?
N2 C7 S1 123.3(4) . . ?
C13 C8 C9 119.2(5) . . ?
C13 C8 N2 122.7(4) . . ?
C9 C8 N2 118.0(5) . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 122.4(5) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 117.6(5) . . ?
C10 C11 C14 122.9(5) . . ?
C12 C11 C14 119.5(5) . . ?
C13 C12 C11 120.5(5) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C8 C13 C12 120.7(4) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C11 115.9(5) . . ?
C15 C14 H14A 108.3 . . ?
C11 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C11 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 C16 115.7(6) . . ?
C14 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 N1 C6 125.2(4) . . ?
C7 N1 H1 117.4 . . ?
C6 N1 H1 117.4 . . ?
C7 N2 C8 126.9(4) . . ?
C7 N2 H2 116.6 . . ?
C8 N2 H2 116.5 . . ?

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
C1 C2 C3 C4 -179.2(4) . . . . ?
C2 C3 C4 C5 175.6(4) . . . . ?
C3 C4 C5 C6 179.3(4) . . . . ?
C4 C5 C6 N1 -61.9(5) . . . . ?
C13 C8 C9 C10 -2.4(6) . . . . ?
N2 C8 C9 C10 179.8(4) . . . . ?
C8 C9 C10 C11 1.0(7) . . . . ?
C9 C10 C11 C12 0.6(7) . . . . ?
C9 C10 C11 C14 179.9(4) . . . . ?
C10 C11 C12 C13 -0.9(7) . . . . ?
C14 C11 C12 C13 179.8(4) . . . . ?
C9 C8 C13 C12 2.2(7) . . . . ?
N2 C8 C13 C12 179.8(4) . . . . ?
C11 C12 C13 C8 -0.5(7) . . . . ?
C10 C11 C14 C15 -43.2(8) . . . . ?
C12 C11 C14 C15 136.0(6) . . . . ?
C11 C14 C15 C16 -175.8(5) . . . . ?
N2 C7 N1 C6 -178.7(4) . . . . ?
S1 C7 N1 C6 -2.2(6) . . . . ?
C5 C6 N1 C7 -169.3(4) . . . . ?
N1 C7 N2 C8 177.5(4) . . . . ?
S1 C7 N2 C8 1.0(6) . . . . ?
C13 C8 N2 C7 58.1(6) . . . . ?
C9 C8 N2 C7 -124.3(5) . . . . ?

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
N1 H1 S1 0.88 2.83 3.595(4) 146.6 4_576
N2 H2 S1 0.88 2.54 3.346(4) 153.4 4_576

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.059

data_global

# Attachment 'jenny104-final.cif'


data_p-COMe
#TrackingRef 'jenny104-final.cif'


_audit_creation_method           SHELXL-97
_chemical_compound_source        
;
Nathalie Busschaert
Jennifer R. Hiscock
;
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 N2 O S'
_chemical_formula_sum            'C15 H22 N2 O S'
_chemical_formula_weight         278.41

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.756(6)
_cell_length_b                   10.120(7)
_cell_length_c                   37.38(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2934(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5101
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      31.1

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9664
_exptl_absorpt_correction_T_max  0.9914

_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Left)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12353
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_sigmaI/netI    0.1033
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.68
_reflns_number_total             2507
_reflns_number_gt                2098
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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 > 2σ(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.

Data completeness only 89.8%, but this is sufficient for proof of structure and hydrogen bonding network
;

_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)+(0.1002P)²+6.6631P] 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         2507
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0970
_refine_ls_wR_factor_ref         0.2504
_refine_ls_wR_factor_gt          0.2373
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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 0.7688(8) -0.0203(6) -0.05283(12) 0.0435(14) Uani 1 1 d . . .
H1A H 0.7708 0.0112 -0.0776 0.065 Uiso 1 1 calc R . .
H1B H 0.6724 -0.0818 -0.0496 0.065 Uiso 1 1 calc R . .
H1C H 0.8774 -0.0657 -0.0474 0.065 Uiso 1 1 calc R . .
C2 C 0.7470(7) 0.0963(5) -0.02772(11) 0.0382(12) Uani 1 1 d . . .
H2A H 0.6388 0.1431 -0.0338 0.046 Uiso 1 1 calc R . .
H2B H 0.8437 0.1587 -0.0314 0.046 Uiso 1 1 calc R . .
C3 C 0.7418(7) 0.0553(5) 0.01192(10) 0.0318(11) Uani 1 1 d . . .
H3A H 0.6436 -0.0056 0.0157 0.038 Uiso 1 1 calc R . .
H3B H 0.8489 0.0067 0.0178 0.038 Uiso 1 1 calc R . .
C4 C 0.7240(7) 0.1720(5) 0.03737(11) 0.0367(12) Uani 1 1 d . . .
H4A H 0.6195 0.2228 0.0309 0.044 Uiso 1 1 calc R . .
H4B H 0.8248 0.2309 0.0344 0.044 Uiso 1 1 calc R . .
C5 C 0.7112(6) 0.1300(5) 0.07685(11) 0.0322(11) Uani 1 1 d . . .
H5A H 0.6176 0.0642 0.0795 0.039 Uiso 1 1 calc R . .
H5B H 0.8206 0.0872 0.0841 0.039 Uiso 1 1 calc R . .
C6 C 0.6758(6) 0.2463(5) 0.10156(10) 0.0328(11) Uani 1 1 d . . .
H6A H 0.7689 0.3126 0.0994 0.039 Uiso 1 1 calc R . .
H6B H 0.5653 0.2889 0.0950 0.039 Uiso 1 1 calc R . .
C7 C 0.6416(6) 0.2714(5) 0.16748(10) 0.0271(11) Uani 1 1 d . . .
C8 C 0.6389(6) 0.2394(5) 0.23489(10) 0.0251(10) Uani 1 1 d . . .
C9 C 0.7128(6) 0.1515(5) 0.26007(10) 0.0267(10) Uani 1 1 d . . .
H9 H 0.7712 0.0744 0.2521 0.032 Uiso 1 1 calc R . .
C10 C 0.7000(6) 0.1779(5) 0.29648(11) 0.0306(11) Uani 1 1 d . . .
H10 H 0.7500 0.1185 0.3132 0.037 Uiso 1 1 calc R . .
C11 C 0.6150(6) 0.2902(5) 0.30869(11) 0.0271(10) Uani 1 1 d . . .
C12 C 0.5376(6) 0.3738(5) 0.28334(11) 0.0290(10) Uani 1 1 d . . .
H12 H 0.4782 0.4504 0.2914 0.035 Uiso 1 1 calc R . .
C13 C 0.5456(6) 0.3478(5) 0.24683(11) 0.0274(10) Uani 1 1 d . . .
H13 H 0.4878 0.4035 0.2303 0.033 Uiso 1 1 calc R . .
C14 C 0.6048(6) 0.3286(5) 0.34745(12) 0.0315(11) Uani 1 1 d . . .
C15 C 0.6691(6) 0.2293(5) 0.37476(11) 0.0331(11) Uani 1 1 d . . .
H15A H 0.6553 0.2658 0.3989 0.050 Uiso 1 1 calc R . .
H15B H 0.7912 0.2105 0.3704 0.050 Uiso 1 1 calc R . .
H15C H 0.6023 0.1474 0.3727 0.050 Uiso 1 1 calc R . .
N1 N 0.6671(5) 0.1969(4) 0.13849(9) 0.0330(10) Uani 1 1 d . . .
H1 H 0.6796 0.1113 0.1418 0.040 Uiso 1 1 calc R . .
N2 N 0.6626(5) 0.2027(4) 0.19874(8) 0.0268(9) Uani 1 1 d . . .
H2 H 0.6972 0.1206 0.1958 0.032 Uiso 1 1 calc R . .
S1 S 0.58922(15) 0.43388(13) 0.16402(3) 0.0303(4) Uani 1 1 d . . .
O1 O 0.5448(5) 0.4348(4) 0.35694(8) 0.0381(9) Uani 1 1 d . . .


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.518(7) . ?
C2 C3 1.540(6) . ?
C3 C4 1.522(6) . ?
C4 C5 1.539(6) . ?
C5 C6 1.521(6) . ?
C6 N1 1.470(5) . ?
C7 N1 1.335(5) . ?
C7 N2 1.370(5) . ?
C7 S1 1.698(5) . ?
C8 C13 1.388(6) . ?
C8 N2 1.413(5) . ?
C8 C9 1.417(6) . ?
C9 C10 1.390(6) . ?
C10 C11 1.391(7) . ?
C11 C12 1.405(6) . ?
C11 C14 1.502(6) . ?
C12 C13 1.391(6) . ?
C14 O1 1.223(6) . ?
C14 C15 1.517(6) . ?

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
C1 C2 C3 112.9(4) . . ?
C4 C3 C2 113.3(4) . . ?
C3 C4 C5 113.0(4) . . ?
C6 C5 C4 112.4(4) . . ?
N1 C6 C5 108.4(4) . . ?
N1 C7 N2 112.8(4) . . ?
N1 C7 S1 121.4(3) . . ?
N2 C7 S1 125.8(3) . . ?
C13 C8 N2 125.7(4) . . ?
C13 C8 C9 119.6(4) . . ?
N2 C8 C9 114.7(4) . . ?
C10 C9 C8 120.1(4) . . ?
C9 C10 C11 120.8(4) . . ?
C10 C11 C12 118.3(4) . . ?
C10 C11 C14 123.6(4) . . ?
C12 C11 C14 118.2(4) . . ?
C13 C12 C11 121.9(4) . . ?
C8 C13 C12 119.3(4) . . ?
O1 C14 C11 121.8(4) . . ?
O1 C14 C15 120.8(4) . . ?
C11 C14 C15 117.4(4) . . ?
C7 N1 C6 125.3(4) . . ?
C7 N2 C8 131.8(4) . . ?

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
C1 C2 C3 C4 178.7(4) . . . . ?
C2 C3 C4 C5 177.6(4) . . . . ?
C3 C4 C5 C6 -174.3(4) . . . . ?
C4 C5 C6 N1 -179.6(4) . . . . ?
C13 C8 C9 C10 -3.6(7) . . . . ?
N2 C8 C9 C10 179.2(4) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C9 C10 C11 C12 2.0(7) . . . . ?
C9 C10 C11 C14 -176.5(4) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
C14 C11 C12 C13 178.0(4) . . . . ?
N2 C8 C13 C12 -178.1(4) . . . . ?
C9 C8 C13 C12 5.0(7) . . . . ?
C11 C12 C13 C8 -3.0(7) . . . . ?
C10 C11 C14 O1 172.2(5) . . . . ?
C12 C11 C14 O1 -6.3(7) . . . . ?
C10 C11 C14 C15 -8.9(7) . . . . ?
C12 C11 C14 C15 172.6(4) . . . . ?
N2 C7 N1 C6 -171.6(4) . . . . ?
S1 C7 N1 C6 8.3(7) . . . . ?
C5 C6 N1 C7 178.4(4) . . . . ?
N1 C7 N2 C8 -175.8(4) . . . . ?
S1 C7 N2 C8 4.3(7) . . . . ?
C13 C8 N2 C7 17.5(8) . . . . ?
C9 C8 N2 C7 -165.5(5) . . . . ?

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
N1 H1 O1 0.88 2.50 3.125(6) 129.1 3_645
N1 H1 S1 0.88 2.67 3.401(4) 141.2 8_755
N2 H2 S1 0.88 2.78 3.576(4) 151.3 8_755

_diffrn_measured_fraction_theta_max 0.897
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.897
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.080


