# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_70223a
_database_code_depnum_ccdc_archive 'CCDC 1555871'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H24 N4 O S'
_chemical_formula_weight         356.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.9414(11)
_cell_length_b                   15.879(3)
_cell_length_c                   19.207(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.096(3)
_cell_angle_gamma                90
_cell_volume                     1807.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2271
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      24.05

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13232
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.666
_diffrn_reflns_theta_max         27.613
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4176
_reflns_number_gt                2870
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.8497P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0098(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4176
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.30927(9) 0.82091(4) 0.16305(3) 0.03196(16) Uani 1 1 d . . . . .
N1 N 0.1069(3) 0.71929(10) 0.15574(8) 0.0283(4) Uani 1 1 d . . . . .
N2 N 0.1108(3) 0.58123(10) 0.19842(9) 0.0333(4) Uani 1 1 d . . . . .
N3 N -0.0098(3) 0.85657(11) 0.42151(9) 0.0318(4) Uani 1 1 d . . . . .
N4 N -0.1103(3) 0.92479(13) -0.07897(10) 0.0454(5) Uani 1 1 d . . . . .
O1 O 0.2906(3) 0.61292(10) 0.10231(9) 0.0525(5) Uani 1 1 d . . . . .
C1 C -0.1046(3) 0.80523(12) 0.23347(10) 0.0254(4) Uani 1 1 d . . . . .
C2 C 0.0848(3) 0.75705(12) 0.22244(10) 0.0254(4) Uani 1 1 d . . . . .
C3 C 0.2484(3) 0.74726(12) 0.27701(10) 0.0284(5) Uani 1 1 d . . . . .
H3 H 0.3822 0.7182 0.2693 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2181(3) 0.77942(12) 0.34235(10) 0.0281(4) Uani 1 1 d . . . . .
H4 H 0.3296 0.7704 0.3788 0.034 Uiso 1 1 calc R U . . .
C5 C 0.0231(3) 0.82555(12) 0.35552(10) 0.0252(4) Uani 1 1 d . . . . .
C6 C -0.1347(3) 0.83972(12) 0.29882(10) 0.0268(4) Uani 1 1 d . . . . .
H6 H -0.2627 0.8730 0.3051 0.032 Uiso 1 1 calc R U . . .
C7 C -0.1285(3) 0.82287(12) 0.09331(10) 0.0258(4) Uani 1 1 d . . . . .
C8 C 0.0635(3) 0.77198(12) 0.09596(10) 0.0263(4) Uani 1 1 d . . . . .
C9 C 0.1995(3) 0.77494(13) 0.04017(11) 0.0294(5) Uani 1 1 d . . . . .
H9 H 0.3326 0.7428 0.0417 0.035 Uiso 1 1 calc R U . . .
C10 C 0.1422(4) 0.82451(13) -0.01771(11) 0.0316(5) Uani 1 1 d . . . . .
H10 H 0.2353 0.8242 -0.0553 0.038 Uiso 1 1 calc R U . . .
C11 C -0.0516(4) 0.87521(13) -0.02156(11) 0.0305(5) Uani 1 1 d . . . . .
C12 C -0.1845(3) 0.87398(13) 0.03619(10) 0.0286(4) Uani 1 1 d . . . . .
H12 H -0.3133 0.9084 0.0360 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1759(4) 0.63585(13) 0.14898(11) 0.0314(5) Uani 1 1 d . . . . .
C14 C 0.2059(4) 0.49676(13) 0.19665(12) 0.0396(6) Uani 1 1 d . . . . .
H14A H 0.1320 0.4655 0.1581 0.059 Uiso 1 1 calc R U . . .
H14B H 0.1829 0.4681 0.2402 0.059 Uiso 1 1 calc R U . . .
H14C H 0.3663 0.5004 0.1905 0.059 Uiso 1 1 calc R U . . .
C15 C -0.1025(4) 0.58929(15) 0.23103(14) 0.0468(6) Uani 1 1 d . . . . .
H15A H -0.0755 0.6145 0.2769 0.070 Uiso 1 1 calc R U . . .
H15B H -0.1694 0.5340 0.2356 0.070 Uiso 1 1 calc R U . . .
H15C H -0.2045 0.6247 0.2023 0.070 Uiso 1 1 calc R U . . .
C16 C 0.1742(4) 0.85784(15) 0.47491(11) 0.0378(5) Uani 1 1 d . . . . .
H16A H 0.2423 0.8024 0.4789 0.057 Uiso 1 1 calc R U . . .
H16B H 0.1174 0.8735 0.5192 0.057 Uiso 1 1 calc R U . . .
H16C H 0.2865 0.8985 0.4625 0.057 Uiso 1 1 calc R U . . .
C17 C -0.1908(4) 0.91605(15) 0.42981(12) 0.0420(6) Uani 1 1 d . . . . .
H17A H -0.1622 0.9673 0.4044 0.063 Uiso 1 1 calc R U . . .
H17B H -0.1987 0.9290 0.4789 0.063 Uiso 1 1 calc R U . . .
H17C H -0.3328 0.8916 0.4117 0.063 Uiso 1 1 calc R U . . .
C18 C 0.0390(4) 0.93405(16) -0.13449(12) 0.0424(6) Uani 1 1 d . . . . .
H18A H 0.1711 0.9660 -0.1177 0.064 Uiso 1 1 calc R U . . .
H18B H -0.0389 0.9636 -0.1733 0.064 Uiso 1 1 calc R U . . .
H18C H 0.0851 0.8788 -0.1498 0.064 Uiso 1 1 calc R U . . .
C19 C -0.3065(4) 0.97765(16) -0.08098(13) 0.0464(6) Uani 1 1 d . . . . .
H19A H -0.4391 0.9434 -0.0753 0.070 Uiso 1 1 calc R U . . .
H19B H -0.3232 1.0067 -0.1255 0.070 Uiso 1 1 calc R U . . .
H19C H -0.2899 1.0186 -0.0435 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.771(2) . ?
S1 C7 1.7758(19) . ?
N1 C13 1.396(3) . ?
N1 C2 1.429(2) . ?
N1 C8 1.429(3) . ?
N2 C13 1.362(3) . ?
N2 C14 1.457(3) . ?
N2 C15 1.459(3) . ?
N3 C5 1.386(2) . ?
N3 C16 1.445(3) . ?
N3 C17 1.449(3) . ?
N4 C11 1.379(3) . ?
N4 C19 1.435(3) . ?
N4 C18 1.442(3) . ?
O1 C13 1.220(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.408(3) . ?
C5 C6 1.404(3) . ?
C7 C12 1.386(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.402(3) . ?
C11 C12 1.407(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C7 99.17(9) . . ?
C13 N1 C2 121.88(16) . . ?
C13 N1 C8 121.22(16) . . ?
C2 N1 C8 116.86(16) . . ?
C13 N2 C14 116.10(17) . . ?
C13 N2 C15 122.81(19) . . ?
C14 N2 C15 116.18(18) . . ?
C5 N3 C16 120.33(17) . . ?
C5 N3 C17 119.11(17) . . ?
C16 N3 C17 116.28(17) . . ?
C11 N4 C19 120.94(18) . . ?
C11 N4 C18 121.02(19) . . ?
C19 N4 C18 117.50(18) . . ?
C2 C1 C6 120.76(18) . . ?
C2 C1 S1 118.71(15) . . ?
C6 C1 S1 120.52(15) . . ?
C3 C2 C1 118.56(17) . . ?
C3 C2 N1 121.78(17) . . ?
C1 C2 N1 119.66(18) . . ?
C4 C3 C2 121.11(18) . . ?
C3 C4 C5 121.25(19) . . ?
N3 C5 C6 121.47(17) . . ?
N3 C5 C4 121.36(18) . . ?
C6 C5 C4 117.16(17) . . ?
C1 C6 C5 120.96(18) . . ?
C12 C7 C8 121.13(18) . . ?
C12 C7 S1 118.91(15) . . ?
C8 C7 S1 119.94(15) . . ?
C9 C8 C7 118.13(18) . . ?
C9 C8 N1 123.96(18) . . ?
C7 C8 N1 117.91(17) . . ?
C10 C9 C8 121.05(19) . . ?
C9 C10 C11 121.50(19) . . ?
N4 C11 C10 121.99(19) . . ?
N4 C11 C12 120.92(19) . . ?
C10 C11 C12 117.10(19) . . ?
C7 C12 C11 121.04(19) . . ?
O1 C13 N2 121.57(19) . . ?
O1 C13 N1 122.35(19) . . ?
N2 C13 N1 116.07(17) . . ?

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 S1 C1 C2 -33.49(17) . . . . ?
C7 S1 C1 C6 147.27(16) . . . . ?
C6 C1 C2 C3 -2.9(3) . . . . ?
S1 C1 C2 C3 177.85(15) . . . . ?
C6 C1 C2 N1 177.25(17) . . . . ?
S1 C1 C2 N1 -2.0(3) . . . . ?
C13 N1 C2 C3 45.2(3) . . . . ?
C8 N1 C2 C3 -132.4(2) . . . . ?
C13 N1 C2 C1 -135.0(2) . . . . ?
C8 N1 C2 C1 47.4(3) . . . . ?
C1 C2 C3 C4 4.5(3) . . . . ?
N1 C2 C3 C4 -175.72(18) . . . . ?
C2 C3 C4 C5 -1.9(3) . . . . ?
C16 N3 C5 C6 -166.14(19) . . . . ?
C17 N3 C5 C6 -10.2(3) . . . . ?
C16 N3 C5 C4 13.0(3) . . . . ?
C17 N3 C5 C4 168.92(19) . . . . ?
C3 C4 C5 N3 178.73(19) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
S1 C1 C6 C5 178.08(15) . . . . ?
N3 C5 C6 C1 -177.23(18) . . . . ?
C4 C5 C6 C1 3.6(3) . . . . ?
C1 S1 C7 C12 -146.78(16) . . . . ?
C1 S1 C7 C8 34.66(18) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
S1 C7 C8 C9 179.56(15) . . . . ?
C12 C7 C8 N1 -178.34(18) . . . . ?
S1 C7 C8 N1 0.2(3) . . . . ?
C13 N1 C8 C9 -42.8(3) . . . . ?
C2 N1 C8 C9 134.8(2) . . . . ?
C13 N1 C8 C7 136.5(2) . . . . ?
C2 N1 C8 C7 -45.9(3) . . . . ?
C7 C8 C9 C10 -2.4(3) . . . . ?
N1 C8 C9 C10 176.95(19) . . . . ?
C8 C9 C10 C11 1.7(3) . . . . ?
C19 N4 C11 C10 -178.5(2) . . . . ?
C18 N4 C11 C10 -7.1(3) . . . . ?
C19 N4 C11 C12 1.1(3) . . . . ?
C18 N4 C11 C12 172.5(2) . . . . ?
C9 C10 C11 N4 -179.9(2) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C8 C7 C12 C11 1.1(3) . . . . ?
S1 C7 C12 C11 -177.48(16) . . . . ?
N4 C11 C12 C7 178.6(2) . . . . ?
C10 C11 C12 C7 -1.8(3) . . . . ?
C14 N2 C13 O1 6.4(3) . . . . ?
C15 N2 C13 O1 -147.8(2) . . . . ?
C14 N2 C13 N1 -172.57(19) . . . . ?
C15 N2 C13 N1 33.2(3) . . . . ?
C2 N1 C13 O1 -145.8(2) . . . . ?
C8 N1 C13 O1 31.7(3) . . . . ?
C2 N1 C13 N2 33.1(3) . . . . ?
C8 N1 C13 N2 -149.37(19) . . . . ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.051

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_51231ba
_database_code_depnum_ccdc_archive 'CCDC 1555875'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 N3 O S'
_chemical_formula_weight         313.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   16.166(4)
_cell_length_b                   8.073(2)
_cell_length_c                   12.176(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.741(4)
_cell_angle_gamma                90
_cell_volume                     1566.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2093
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.53

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10950
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.557
_diffrn_reflns_theta_max         27.411
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3538
_reflns_number_gt                2280
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0510P)²+0.2566P] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3538
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29745(3) 0.19440(7) 0.46623(4) 0.04675(18) Uani 1 1 d . . . . .
N1 N 0.26600(10) 0.3627(2) 0.67353(14) 0.0426(4) Uani 1 1 d . . . . .
N2 N 0.60542(11) 0.3312(3) 0.62121(17) 0.0597(5) Uani 1 1 d . . . . .
N3 N 0.05883(12) -0.1850(2) 0.53648(17) 0.0573(5) Uani 1 1 d . . . . .
O1 O 0.16379(12) 0.5286(2) 0.72378(18) 0.0844(6) Uani 1 1 d . . . . .
C1 C 0.37544(12) 0.2767(2) 0.57068(16) 0.0382(5) Uani 1 1 d . . . . .
C2 C 0.35283(12) 0.3532(2) 0.66350(16) 0.0394(5) Uani 1 1 d . . . . .
C3 C 0.41574(14) 0.4203(3) 0.74170(18) 0.0477(5) Uani 1 1 d . . . . .
H3 H 0.4020 0.4684 0.8057 0.057 Uiso 1 1 calc R U . . .
C4 C 0.49793(14) 0.4176(3) 0.72707(18) 0.0510(6) Uani 1 1 d . . . . .
H4 H 0.5385 0.4680 0.7798 0.061 Uiso 1 1 calc R U . . .
C5 C 0.52233(13) 0.3408(3) 0.63442(18) 0.0452(5) Uani 1 1 d . . . . .
C6 C 0.45867(12) 0.2688(2) 0.55677(17) 0.0425(5) Uani 1 1 d . . . . .
H6 H 0.4725 0.2149 0.4949 0.051 Uiso 1 1 calc R U . . .
C7 C 0.62562(14) 0.2782(3) 0.5159(2) 0.0626(7) Uani 1 1 d . . . . .
H7A H 0.6126 0.1627 0.5051 0.094 Uiso 1 1 calc R U . . .
H7B H 0.6843 0.2954 0.5156 0.094 Uiso 1 1 calc R U . . .
H7C H 0.5933 0.3412 0.4568 0.094 Uiso 1 1 calc R U . . .
C8 C 0.66777(15) 0.4242(3) 0.6952(2) 0.0705(8) Uani 1 1 d . . . . .
H8A H 0.6544 0.5400 0.6890 0.106 Uiso 1 1 calc R U . . .
H8B H 0.7220 0.4058 0.6752 0.106 Uiso 1 1 calc R U . . .
H8C H 0.6684 0.3885 0.7705 0.106 Uiso 1 1 calc R U . . .
C9 C 0.22403(11) 0.1302(3) 0.54935(16) 0.0379(4) Uani 1 1 d . . . . .
C10 C 0.21411(12) 0.2199(3) 0.64346(16) 0.0395(5) Uani 1 1 d . . . . .
C11 C 0.15538(12) 0.1653(3) 0.70565(17) 0.0471(5) Uani 1 1 d . . . . .
H11 H 0.1497 0.2203 0.7711 0.056 Uiso 1 1 calc R U . . .
C12 C 0.10513(12) 0.0304(3) 0.67195(19) 0.0517(6) Uani 1 1 d . . . . .
H12 H 0.0657 -0.0029 0.7149 0.062 Uiso 1 1 calc R U . . .
C13 C 0.11188(12) -0.0580(3) 0.57471(18) 0.0447(5) Uani 1 1 d . . . . .
C14 C 0.17533(11) -0.0068(3) 0.51588(17) 0.0424(5) Uani 1 1 d . . . . .
H14 H 0.1845 -0.0662 0.4536 0.051 Uiso 1 1 calc R U . . .
C15 C -0.00184(15) -0.2454(3) 0.6019(2) 0.0678(7) Uani 1 1 d . . . . .
H15A H 0.0270 -0.2980 0.6681 0.102 Uiso 1 1 calc R U . . .
H15B H -0.0384 -0.3239 0.5588 0.102 Uiso 1 1 calc R U . . .
H15C H -0.0343 -0.1542 0.6220 0.102 Uiso 1 1 calc R U . . .
C16 C 0.07411(17) -0.2871(3) 0.4451(3) 0.0747(8) Uani 1 1 d . . . . .
H16A H 0.0834 -0.2178 0.3843 0.112 Uiso 1 1 calc R U . . .
H16B H 0.0263 -0.3569 0.4215 0.112 Uiso 1 1 calc R U . . .
H16C H 0.1228 -0.3546 0.4687 0.112 Uiso 1 1 calc R U . . .
C17 C 0.23453(17) 0.5076(3) 0.7067(2) 0.0620(7) Uani 1 1 d . . . . .
H17 H 0.2706 0.5981 0.7170 0.074 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.762(2) . ?
S1 C9 1.763(2) . ?
N1 C17 1.364(3) . ?
N1 C2 1.432(2) . ?
N1 C10 1.436(3) . ?
N2 C5 1.382(3) . ?
N2 C7 1.441(3) . ?
N2 C8 1.443(3) . ?
N3 C13 1.367(3) . ?
N3 C16 1.439(3) . ?
N3 C15 1.448(3) . ?
O1 C17 1.208(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.390(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.370(3) . ?
C4 C5 1.401(3) . ?
C5 C6 1.400(3) . ?
C9 C14 1.378(3) . ?
C9 C10 1.387(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.379(3) . ?
C12 C13 1.403(3) . ?
C13 C14 1.409(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C9 99.53(9) . . ?
C17 N1 C2 119.43(19) . . ?
C17 N1 C10 122.22(18) . . ?
C2 N1 C10 118.30(15) . . ?
C5 N2 C7 119.4(2) . . ?
C5 N2 C8 119.2(2) . . ?
C7 N2 C8 118.0(2) . . ?
C13 N3 C16 120.85(19) . . ?
C13 N3 C15 120.6(2) . . ?
C16 N3 C15 117.0(2) . . ?
C6 C1 C2 120.94(19) . . ?
C6 C1 S1 119.04(15) . . ?
C2 C1 S1 119.99(15) . . ?
C3 C2 C1 118.09(19) . . ?
C3 C2 N1 122.58(18) . . ?
C1 C2 N1 119.32(18) . . ?
C4 C3 C2 121.4(2) . . ?
C3 C4 C5 121.5(2) . . ?
N2 C5 C6 121.1(2) . . ?
N2 C5 C4 122.0(2) . . ?
C6 C5 C4 116.89(19) . . ?
C1 C6 C5 121.09(19) . . ?
C14 C9 C10 121.51(18) . . ?
C14 C9 S1 118.19(15) . . ?
C10 C9 S1 120.26(16) . . ?
C11 C10 C9 118.2(2) . . ?
C11 C10 N1 122.79(18) . . ?
C9 C10 N1 119.02(17) . . ?
C12 C11 C10 120.9(2) . . ?
C11 C12 C13 121.81(19) . . ?
N3 C13 C12 122.36(19) . . ?
N3 C13 C14 121.1(2) . . ?
C12 C13 C14 116.6(2) . . ?
C9 C14 C13 120.9(2) . . ?
O1 C17 N1 125.6(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
C9 S1 C1 C6 148.89(17) . . . . ?
C9 S1 C1 C2 -33.26(19) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
S1 C1 C2 C3 -178.11(16) . . . . ?
C6 C1 C2 N1 178.39(18) . . . . ?
S1 C1 C2 N1 0.6(3) . . . . ?
C17 N1 C2 C3 42.9(3) . . . . ?
C10 N1 C2 C3 -139.7(2) . . . . ?
C17 N1 C2 C1 -135.7(2) . . . . ?
C10 N1 C2 C1 41.7(3) . . . . ?
C1 C2 C3 C4 2.3(3) . . . . ?
N1 C2 C3 C4 -176.32(19) . . . . ?
C2 C3 C4 C5 -2.6(3) . . . . ?
C7 N2 C5 C6 13.2(3) . . . . ?
C8 N2 C5 C6 172.3(2) . . . . ?
C7 N2 C5 C4 -168.8(2) . . . . ?
C8 N2 C5 C4 -9.7(3) . . . . ?
C3 C4 C5 N2 -177.2(2) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
S1 C1 C6 C5 176.38(16) . . . . ?
N2 C5 C6 C1 179.2(2) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C1 S1 C9 C14 -148.45(16) . . . . ?
C1 S1 C9 C10 33.83(18) . . . . ?
C14 C9 C10 C11 2.0(3) . . . . ?
S1 C9 C10 C11 179.60(15) . . . . ?
C14 C9 C10 N1 -179.27(17) . . . . ?
S1 C9 C10 N1 -1.6(3) . . . . ?
C17 N1 C10 C11 -45.0(3) . . . . ?
C2 N1 C10 C11 137.6(2) . . . . ?
C17 N1 C10 C9 136.2(2) . . . . ?
C2 N1 C10 C9 -41.1(3) . . . . ?
C9 C10 C11 C12 -3.2(3) . . . . ?
N1 C10 C11 C12 178.08(19) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C16 N3 C13 C12 -171.8(2) . . . . ?
C15 N3 C13 C12 -6.5(3) . . . . ?
C16 N3 C13 C14 9.8(3) . . . . ?
C15 N3 C13 C14 175.1(2) . . . . ?
C11 C12 C13 N3 -175.6(2) . . . . ?
C11 C12 C13 C14 2.9(3) . . . . ?
C10 C9 C14 C13 1.8(3) . . . . ?
S1 C9 C14 C13 -175.93(15) . . . . ?
N3 C13 C14 C9 174.39(19) . . . . ?
C12 C13 C14 C9 -4.1(3) . . . . ?
C2 N1 C17 O1 -175.9(2) . . . . ?
C10 N1 C17 O1 6.8(4) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-2

