# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_2mb14fea
_database_code_depnum_ccdc_archive 'CCDC 1444118'
_audit_update_record             
;
2015-12-24 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;
_audit_creation_date             2015-12-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014-3
_chemical_name_common            'imidazole derivative'
_chemical_name_systematic        'imidozolyl thiozole'
_chemical_formula_moiety         'C16 H9 F N2 O S'
_chemical_formula_sum            'C16 H9 F N2 O S'
_chemical_formula_weight         296.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   6.3722(18)
_cell_length_b                   11.278(3)
_cell_length_c                   17.837(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1281.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4906
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      26.541
_cell_measurement_theta_min      2.912
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.864
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1429 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.8906.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.46
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14858
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.563
_diffrn_reflns_theta_min         2.136
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2731
_reflns_number_total             2957
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1063 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.4672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0770
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.91531(11) 0.85052(6) 0.37223(4) 0.01827(16) Uani 1 1 d . . . . .
F1 F -0.1811(3) 0.86904(16) 0.13840(10) 0.0333(4) Uani 1 1 d . . . . .
O1 O 0.6502(3) 1.02454(16) 0.29740(11) 0.0218(4) Uani 1 1 d . . . . .
N1 N 1.0345(3) 0.6568(2) 0.46027(12) 0.0190(5) Uani 1 1 d . . . . .
N2 N 0.7037(3) 0.66875(19) 0.41409(12) 0.0151(5) Uani 1 1 d . . . . .
C1 C 0.9141(5) 0.5591(2) 0.48346(14) 0.0179(5) Uani 1 1 d . . . . .
C2 C 0.9722(5) 0.4640(2) 0.52855(15) 0.0212(6) Uani 1 1 d . . . . .
H2 H 1.1103 0.4580 0.5483 0.025 Uiso 1 1 calc R . . . .
C3 C 0.8226(5) 0.3786(2) 0.54375(15) 0.0239(7) Uani 1 1 d . . . . .
H3 H 0.8587 0.3136 0.5751 0.029 Uiso 1 1 calc R . . . .
C4 C 0.6195(5) 0.3852(2) 0.51434(15) 0.0234(7) Uani 1 1 d . . . . .
H4 H 0.5217 0.3242 0.5257 0.028 Uiso 1 1 calc R . . . .
C5 C 0.5580(5) 0.4785(2) 0.46908(14) 0.0200(6) Uani 1 1 d . . . . .
H5 H 0.4207 0.4834 0.4485 0.024 Uiso 1 1 calc R . . . .
C6 C 0.7085(4) 0.5644(2) 0.45557(14) 0.0160(5) Uani 1 1 d . . . . .
C7 C 0.9017(4) 0.7175(2) 0.42047(14) 0.0168(5) Uani 1 1 d . . . . .
C8 C 0.5655(4) 0.7320(2) 0.37085(14) 0.0167(5) Uani 1 1 d . . . . .
H8 H 0.4242 0.7091 0.3621 0.020 Uiso 1 1 calc R . . . .
C9 C 0.6545(4) 0.8310(2) 0.34213(14) 0.0170(6) Uani 1 1 d . . . . .
C10 C 0.5631(4) 0.9281(2) 0.29840(14) 0.0166(5) Uani 1 1 d . . . . .
C11 C 0.3649(4) 0.9085(2) 0.25601(14) 0.0166(6) Uani 1 1 d . . . . .
C12 C 0.3148(5) 0.7993(2) 0.22414(15) 0.0201(6) Uani 1 1 d . . . . .
H12 H 0.4067 0.7338 0.2305 0.024 Uiso 1 1 calc R . . . .
C13 C 0.1319(5) 0.7860(2) 0.18338(15) 0.0226(6) Uani 1 1 d . . . . .
H13 H 0.0969 0.7121 0.1611 0.027 Uiso 1 1 calc R . . . .
C14 C 0.0026(5) 0.8821(3) 0.17599(15) 0.0229(6) Uani 1 1 d . . . . .
C15 C 0.0472(4) 0.9921(2) 0.20566(15) 0.0208(6) Uani 1 1 d . . . . .
H15 H -0.0457 1.0571 0.1988 0.025 Uiso 1 1 calc R . . . .
C16 C 0.2308(5) 1.0047(2) 0.24557(14) 0.0185(6) Uani 1 1 d . . . . .
H16 H 0.2665 1.0797 0.2662 0.022 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.731(3) . ?
S1 C9 1.760(3) . ?
F1 C14 1.357(3) . ?
O1 C10 1.221(3) . ?
N1 C1 1.405(3) . ?
N1 C7 1.300(3) . ?
N2 C6 1.391(3) . ?
N2 C7 1.382(3) . ?
N2 C8 1.371(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.402(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.352(4) . ?
C9 C10 1.466(4) . ?
C10 C11 1.488(4) . ?
C11 C12 1.393(4) . ?
C11 C16 1.394(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(4) . ?
C14 C15 1.378(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(4) . ?
C16 H16 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 S1 C9 89.76(13) . . ?
C7 N1 C1 102.6(2) . . ?
C7 N2 C6 105.8(2) . . ?
C8 N2 C6 139.0(2) . . ?
C8 N2 C7 115.2(2) . . ?
C2 C1 N1 129.0(3) . . ?
C2 C1 C6 119.1(3) . . ?
C6 C1 N1 111.9(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 122.0 . . ?
C4 C5 C6 116.0(3) . . ?
C6 C5 H5 122.0 . . ?
N2 C6 C1 104.2(2) . . ?
C5 C6 N2 132.0(3) . . ?
C5 C6 C1 123.8(3) . . ?
N1 C7 S1 134.1(2) . . ?
N1 C7 N2 115.4(2) . . ?
N2 C7 S1 110.48(19) . . ?
N2 C8 H8 124.0 . . ?
C9 C8 N2 111.9(2) . . ?
C9 C8 H8 124.0 . . ?
C8 C9 S1 112.6(2) . . ?
C8 C9 C10 130.7(3) . . ?
C10 C9 S1 116.3(2) . . ?
O1 C10 C9 119.5(3) . . ?
O1 C10 C11 120.7(2) . . ?
C9 C10 C11 119.8(2) . . ?
C12 C11 C10 122.2(2) . . ?
C12 C11 C16 119.5(3) . . ?
C16 C11 C10 118.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.2(3) . . ?
C14 C13 H13 120.9 . . ?
F1 C14 C13 118.8(3) . . ?
F1 C14 C15 117.7(3) . . ?
C13 C14 C15 123.5(3) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 C14 117.8(3) . . ?
C16 C15 H15 121.1 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.6(3) . . ?
C15 C16 H16 119.7 . . ?

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
S1 C9 C10 O1 -14.4(3) . . . . ?
S1 C9 C10 C11 165.83(18) . . . . ?
F1 C14 C15 C16 178.3(2) . . . . ?
O1 C10 C11 C12 147.4(3) . . . . ?
O1 C10 C11 C16 -29.8(4) . . . . ?
N1 C1 C2 C3 179.6(3) . . . . ?
N1 C1 C6 N2 -0.1(3) . . . . ?
N1 C1 C6 C5 179.1(2) . . . . ?
N2 C8 C9 S1 -2.4(3) . . . . ?
N2 C8 C9 C10 -174.6(3) . . . . ?
C1 N1 C7 S1 178.8(2) . . . . ?
C1 N1 C7 N2 -0.8(3) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C1 C6 N2 179.6(2) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 N2 -179.6(2) . . . . ?
C4 C5 C6 C1 1.5(4) . . . . ?
C6 N2 C7 S1 -178.94(16) . . . . ?
C6 N2 C7 N1 0.8(3) . . . . ?
C6 N2 C8 C9 -178.7(3) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
C7 S1 C9 C8 2.8(2) . . . . ?
C7 S1 C9 C10 176.2(2) . . . . ?
C7 N1 C1 C2 -179.2(3) . . . . ?
C7 N1 C1 C6 0.5(3) . . . . ?
C7 N2 C6 C1 -0.4(3) . . . . ?
C7 N2 C6 C5 -179.4(3) . . . . ?
C7 N2 C8 C9 0.6(3) . . . . ?
C8 N2 C6 C1 179.0(3) . . . . ?
C8 N2 C6 C5 0.0(5) . . . . ?
C8 N2 C7 S1 1.5(3) . . . . ?
C8 N2 C7 N1 -178.8(2) . . . . ?
C8 C9 C10 O1 157.5(3) . . . . ?
C8 C9 C10 C11 -22.3(4) . . . . ?
C9 S1 C7 N1 178.0(3) . . . . ?
C9 S1 C7 N2 -2.36(19) . . . . ?
C9 C10 C11 C12 -32.8(4) . . . . ?
C9 C10 C11 C16 150.0(2) . . . . ?
C10 C11 C12 C13 -178.1(2) . . . . ?
C10 C11 C16 C15 178.9(2) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C11 C16 C15 1.6(4) . . . . ?
C12 C13 C14 F1 -177.7(2) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C16 C11 C12 C13 -0.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# End of CIF  ============================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_mb1plus
_database_code_depnum_ccdc_archive 'CCDC 1444119'
_audit_update_record             
;
2015-12-24 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;
_audit_creation_date             2015-12-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014-3
_chemical_name_common            'imidazole derivative'
_chemical_name_systematic        'imidazolyl thiozole'
_chemical_formula_moiety         'C17 H12 N2 O S'
_chemical_formula_sum            'C17 H12 N2 O S'
_chemical_formula_weight         292.35
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.940(3)
_cell_length_b                   12.584(4)
_cell_length_c                   11.973(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.959(3)
_cell_angle_gamma                90
_cell_volume                     1379.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5298
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.401
_cell_measurement_theta_min      2.271
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1326 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.8010.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.51
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15518
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_min         2.271
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2604
_reflns_number_total             3174
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0276(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²+0.8514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0905
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.62908(4) 0.37223(3) 0.84370(4) 0.02155(13) Uani 1 1 d . . . . .
O1 O 0.30010(13) 0.39849(11) 0.75355(11) 0.0305(3) Uani 1 1 d . . . . .
N1 N 0.89229(15) 0.28333(11) 0.85167(12) 0.0206(3) Uani 1 1 d . . . . .
N2 N 0.68718(14) 0.27473(11) 0.67986(11) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.91942(17) 0.22882(13) 0.76028(14) 0.0187(3) Uani 1 1 d . . . . .
C2 C 1.04811(18) 0.18157(14) 0.76440(15) 0.0235(4) Uani 1 1 d . . . . .
H2 H 1.1347 0.1833 0.8362 0.028 Uiso 1 1 calc R . . . .
C3 C 1.04558(18) 0.13201(14) 0.66050(16) 0.0249(4) Uani 1 1 d . . . . .
H3 H 1.1325 0.0999 0.6614 0.030 Uiso 1 1 calc R . . . .
C4 C 0.91914(18) 0.12766(13) 0.55420(15) 0.0225(4) Uani 1 1 d . . . . .
H4 H 0.9224 0.0932 0.4847 0.027 Uiso 1 1 calc R . . . .
C5 C 0.78948(18) 0.17238(13) 0.54819(14) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.7026 0.1688 0.4768 0.024 Uiso 1 1 calc R . . . .
C6 C 0.79394(17) 0.22280(12) 0.65263(14) 0.0174(3) Uani 1 1 d . . . . .
C7 C 0.75341(17) 0.30711(13) 0.79925(14) 0.0182(3) Uani 1 1 d . . . . .
C8 C 0.54259(17) 0.30196(13) 0.62213(14) 0.0185(3) Uani 1 1 d . . . . .
H8 H 0.4845 0.2855 0.5399 0.022 Uiso 1 1 calc R . . . .
C9 C 0.49291(17) 0.35509(13) 0.69649(14) 0.0201(3) Uani 1 1 d . . . . .
C10 C 0.34097(18) 0.38650(13) 0.67012(15) 0.0216(4) Uani 1 1 d . . . . .
C11 C 0.24032(17) 0.40122(13) 0.54115(15) 0.0201(3) Uani 1 1 d . . . . .
C12 C 0.28767(18) 0.44175(14) 0.45468(16) 0.0250(4) Uani 1 1 d . . . . .
H12 H 0.3879 0.4588 0.4772 0.030 Uiso 1 1 calc R . . . .
C13 C 0.19083(19) 0.45752(14) 0.33640(16) 0.0264(4) Uani 1 1 d . . . . .
H13 H 0.2254 0.4861 0.2791 0.032 Uiso 1 1 calc R . . . .
C14 C 0.04371(18) 0.43228(14) 0.29977(16) 0.0244(4) Uani 1 1 d . . . . .
C15 C -0.00331(18) 0.39139(14) 0.38671(16) 0.0250(4) Uani 1 1 d . . . . .
H15 H -0.1033 0.3730 0.3636 0.030 Uiso 1 1 calc R . . . .
C16 C 0.09228(17) 0.37702(13) 0.50556(16) 0.0222(4) Uani 1 1 d . . . . .
H16 H 0.0572 0.3505 0.5635 0.027 Uiso 1 1 calc R . . . .
C17 C -0.0614(2) 0.45066(17) 0.17071(17) 0.0328(4) Uani 1 1 d . . . . .
H17A H -0.1218 0.3872 0.1405 0.049 Uiso 1 1 calc GR . . . .
H17B H -0.0064 0.4653 0.1200 0.049 Uiso 1 1 calc GR . . . .
H17C H -0.1243 0.5115 0.1678 0.049 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.7306(17) . ?
S1 C9 1.7675(17) . ?
O1 C10 1.226(2) . ?
N1 C1 1.404(2) . ?
N1 C7 1.309(2) . ?
N2 C6 1.389(2) . ?
N2 C7 1.381(2) . ?
N2 C8 1.373(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.403(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.351(2) . ?
C9 C10 1.471(2) . ?
C10 C11 1.488(2) . ?
C11 C12 1.391(2) . ?
C11 C16 1.397(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(2) . ?
C14 C15 1.395(2) . ?
C14 C17 1.508(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C7 S1 C9 89.80(8) . . ?
C7 N1 C1 103.02(13) . . ?
C7 N2 C6 106.40(13) . . ?
C8 N2 C6 138.13(14) . . ?
C8 N2 C7 115.47(13) . . ?
C2 C1 N1 129.30(15) . . ?
C2 C1 C6 118.96(15) . . ?
C6 C1 N1 111.73(14) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.78(15) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.07(16) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.36(15) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 122.0 . . ?
C4 C5 C6 115.97(15) . . ?
C6 C5 H5 122.0 . . ?
N2 C6 C1 104.23(13) . . ?
C5 C6 N2 131.91(15) . . ?
C5 C6 C1 123.85(15) . . ?
N1 C7 S1 134.98(13) . . ?
N1 C7 N2 114.62(14) . . ?
N2 C7 S1 110.40(11) . . ?
N2 C8 H8 124.1 . . ?
C9 C8 N2 111.81(14) . . ?
C9 C8 H8 124.1 . . ?
C8 C9 S1 112.51(12) . . ?
C8 C9 C10 126.86(15) . . ?
C10 C9 S1 120.26(12) . . ?
O1 C10 C9 119.80(15) . . ?
O1 C10 C11 121.87(15) . . ?
C9 C10 C11 118.32(14) . . ?
C12 C11 C10 122.17(15) . . ?
C12 C11 C16 118.37(16) . . ?
C16 C11 C10 119.43(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.88(16) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.15(16) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 117.80(16) . . ?
C13 C14 C17 120.76(16) . . ?
C15 C14 C17 121.42(16) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.41(16) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.37(16) . . ?
C15 C16 H16 119.8 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
S1 C9 C10 O1 -18.7(2) . . . . ?
S1 C9 C10 C11 162.18(12) . . . . ?
O1 C10 C11 C12 146.09(17) . . . . ?
O1 C10 C11 C16 -31.8(2) . . . . ?
N1 C1 C2 C3 179.82(16) . . . . ?
N1 C1 C6 N2 -0.36(18) . . . . ?
N1 C1 C6 C5 -179.33(15) . . . . ?
N2 C8 C9 S1 -0.14(18) . . . . ?
N2 C8 C9 C10 -173.01(15) . . . . ?
C1 N1 C7 S1 179.50(15) . . . . ?
C1 N1 C7 N2 -1.29(18) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C1 C6 N2 178.77(14) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C4 C5 C6 N2 -179.44(16) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C6 N2 C7 S1 -179.47(11) . . . . ?
C6 N2 C7 N1 1.12(19) . . . . ?
C6 N2 C8 C9 -179.57(17) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C7 S1 C9 C8 0.78(13) . . . . ?
C7 S1 C9 C10 174.18(14) . . . . ?
C7 N1 C1 C2 -178.03(17) . . . . ?
C7 N1 C1 C6 0.99(18) . . . . ?
C7 N2 C6 C1 -0.40(17) . . . . ?
C7 N2 C6 C5 178.45(17) . . . . ?
C7 N2 C8 C9 -0.8(2) . . . . ?
C8 N2 C6 C1 178.42(18) . . . . ?
C8 N2 C6 C5 -2.7(3) . . . . ?
C8 N2 C7 S1 1.41(17) . . . . ?
C8 N2 C7 N1 -178.00(14) . . . . ?
C8 C9 C10 O1 153.64(17) . . . . ?
C8 C9 C10 C11 -25.4(3) . . . . ?
C9 S1 C7 N1 178.05(18) . . . . ?
C9 S1 C7 N2 -1.19(12) . . . . ?
C9 C10 C11 C12 -34.9(2) . . . . ?
C9 C10 C11 C16 147.27(16) . . . . ?
C10 C11 C12 C13 -178.03(16) . . . . ?
C10 C11 C16 C15 179.16(15) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C11 C16 C15 1.2(2) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C12 C13 C14 C17 179.47(17) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C11 -1.4(3) . . . . ?
C16 C11 C12 C13 -0.1(3) . . . . ?
C17 C14 C15 C16 -178.39(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# End of CIF  ============================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
