# 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_mo_tbquin1
_database_code_depnum_ccdc_archive 'CCDC 1484089'
_audit_update_record             
;
2016-06-08 deposited with the CCDC.
2016-09-22 downloaded from the CCDC.
;
_audit_creation_date             2016-04-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N2 O2 S'
_chemical_formula_sum            'C16 H18 N2 O2 S'
_chemical_formula_weight         302.38
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.4138(6)
_cell_length_b                   7.6858(7)
_cell_length_c                   15.2182(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.722(3)
_cell_angle_gamma                90
_cell_volume                     739.41(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8629
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      29.81
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0662 before and 0.0353 after correction.
The Ratio of minimum to maximum transmission is 0.9571.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.480
_diffrn_reflns_theta_min         1.358
_diffrn_ambient_temperature      299.43
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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_standards_number         0
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3981
_reflns_number_total             4469
_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  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1634 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4469
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.020
_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)+(0.0459P)²+0.0980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0903
_refine_special_details          
;
H atoms were positioned geometrically and allowed to ride on their parent atoms 
except for H atoms bonded to N atoms ; those H atoms were located from a 
difference Fourier map and refined freely.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C5(H5), C11(H11), C2(H2A), C14(H14), C3(H3), C4(H4), C12(H12)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.64841(8) 0.37546(7) 0.70986(3) 0.04180(14) Uani 1 1 d . . . . .
O2 O 0.8270(3) 0.4703(3) 0.69166(13) 0.0647(6) Uani 1 1 d . . . . .
O1 O 0.6736(4) 0.1966(3) 0.73716(13) 0.0667(6) Uani 1 1 d . . . . .
N1 N 0.3765(3) 0.6245(3) 0.92402(15) 0.0461(5) Uani 1 1 d . . . . .
N2 N 0.5541(3) 0.4723(2) 0.78784(12) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.5691(3) 0.6767(3) 0.97111(13) 0.0341(4) Uani 1 1 d . . . . .
C8 C 0.4963(4) 0.6568(3) 0.78375(14) 0.0402(5) Uani 1 1 d . . . . .
H8 H 0.4532 0.6914 0.7214 0.048 Uiso 1 1 calc R . . . .
C6 C 0.7213(3) 0.7512(2) 0.92706(14) 0.0344(4) Uani 1 1 d . . . . .
C10 C 0.4539(3) 0.3860(3) 0.61262(12) 0.0365(4) Uani 1 1 d . . . . .
C15 C 0.2558(4) 0.3193(4) 0.61524(16) 0.0506(6) Uani 1 1 d . . . . .
H15 H 0.2220 0.2773 0.6684 0.061 Uiso 1 1 calc R . . . .
C7 C 0.6792(4) 0.7715(3) 0.82712(15) 0.0427(5) Uani 1 1 d . . . . .
H7A H 0.8057 0.7409 0.8035 0.051 Uiso 1 1 calc R . . . .
H7B H 0.6462 0.8922 0.8122 0.051 Uiso 1 1 calc R . . . .
C5 C 0.9136(4) 0.8024(3) 0.97706(19) 0.0491(6) Uani 1 1 d . . . . .
H5 H 1.0138 0.8554 0.9483 0.059 Uiso 1 1 calc R . . . .
C11 C 0.5024(4) 0.4516(3) 0.53392(16) 0.0477(5) Uani 1 1 d . . . . .
H11 H 0.6354 0.4987 0.5325 0.057 Uiso 1 1 calc R . . . .
C2 C 0.6175(5) 0.6507(3) 1.06375(15) 0.0479(6) Uani 1 1 d . . . . .
H2A H 0.5182 0.6004 1.0940 0.057 Uiso 1 1 calc R . . . .
C13 C 0.1538(4) 0.3764(4) 0.45813(13) 0.0485(5) Uani 1 1 d . . . . .
C9 C 0.3110(3) 0.6787(3) 0.83306(16) 0.0484(5) Uani 1 1 d . . . . .
H9A H 0.2667 0.7995 0.8312 0.058 Uiso 1 1 calc R . . . .
H9B H 0.1925 0.6086 0.8050 0.058 Uiso 1 1 calc R . . . .
C14 C 0.1072(4) 0.3155(4) 0.53754(18) 0.0556(6) Uani 1 1 d . . . . .
H14 H -0.0268 0.2709 0.5392 0.067 Uiso 1 1 calc R . . . .
C3 C 0.8139(5) 0.7001(4) 1.11000(17) 0.0612(8) Uani 1 1 d . . . . .
H3 H 0.8459 0.6803 1.1711 0.073 Uiso 1 1 calc R . . . .
C4 C 0.9599(5) 0.7767(4) 1.0679(2) 0.0610(7) Uani 1 1 d . . . . .
H4 H 1.0897 0.8116 1.0999 0.073 Uiso 1 1 calc R . . . .
C12 C 0.3518(5) 0.4467(4) 0.45730(16) 0.0534(6) Uani 1 1 d . . . . .
H12 H 0.3843 0.4913 0.4044 0.064 Uiso 1 1 calc R . . . .
C16 C -0.0091(5) 0.3685(5) 0.37377(18) 0.0727(9) Uani 1 1 d . . . . .
H16A H -0.0027 0.2569 0.3461 0.109 Uiso 1 1 calc GR . . . .
H16B H 0.0198 0.4580 0.3335 0.109 Uiso 1 1 calc GR . . . .
H16C H -0.1476 0.3858 0.3882 0.109 Uiso 1 1 calc GR . . . .
H2 H 0.506(5) 0.414(4) 0.822(2) 0.055(9) Uiso 1 1 d . . . . .
H1 H 0.299(5) 0.576(5) 0.952(2) 0.065(10) Uiso 1 1 d . . . . .


_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 O2 1.424(2) . ?
S1 O1 1.437(2) . ?
S1 N2 1.6034(19) . ?
S1 C10 1.7692(19) . ?
N1 C1 1.379(3) . ?
N1 C9 1.439(3) . ?
N1 H1 0.80(4) . ?
N2 C8 1.464(3) . ?
N2 H2 0.78(3) . ?
C1 C6 1.397(3) . ?
C1 C2 1.406(3) . ?
C8 H8 0.9800 . ?
C8 C7 1.525(3) . ?
C8 C9 1.518(3) . ?
C6 C7 1.507(3) . ?
C6 C5 1.392(3) . ?
C10 C15 1.377(3) . ?
C10 C11 1.382(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.388(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.378(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.389(4) . ?
C13 C14 1.375(4) . ?
C13 C12 1.382(4) . ?
C13 C16 1.513(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C14 H14 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.355(5) . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
O2 S1 O1 119.40(14) . . ?
O2 S1 N2 108.83(12) . . ?
O2 S1 C10 106.90(11) . . ?
O1 S1 N2 105.55(12) . . ?
O1 S1 C10 108.35(12) . . ?
N2 S1 C10 107.27(10) . . ?
C1 N1 C9 120.4(2) . . ?
C1 N1 H1 116(3) . . ?
C9 N1 H1 123(3) . . ?
S1 N2 H2 117(2) . . ?
C8 N2 S1 122.85(16) . . ?
C8 N2 H2 117(2) . . ?
N1 C1 C6 120.47(19) . . ?
N1 C1 C2 120.4(2) . . ?
C6 C1 C2 119.1(2) . . ?
N2 C8 H8 109.4 . . ?
N2 C8 C7 111.76(18) . . ?
N2 C8 C9 107.5(2) . . ?
C7 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
C9 C8 C7 109.31(18) . . ?
C1 C6 C7 120.40(18) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 120.9(2) . . ?
C15 C10 S1 118.85(17) . . ?
C15 C10 C11 120.3(2) . . ?
C11 C10 S1 120.74(17) . . ?
C10 C15 H15 120.4 . . ?
C10 C15 C14 119.2(2) . . ?
C14 C15 H15 120.4 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 C8 111.75(18) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 121.9(3) . . ?
C4 C5 H5 119.0 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(2) . . ?
C12 C11 H11 120.2 . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2A 120.1 . . ?
C14 C13 C12 118.5(2) . . ?
C14 C13 C16 120.7(3) . . ?
C12 C13 C16 120.8(2) . . ?
N1 C9 C8 108.53(18) . . ?
N1 C9 H9A 110.0 . . ?
N1 C9 H9B 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C15 C14 H14 119.3 . . ?
C13 C14 C15 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.3 . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 N2 C8 C7 -92.1(2) . . . . ?
S1 N2 C8 C9 147.95(16) . . . . ?
S1 C10 C15 C14 -175.3(2) . . . . ?
S1 C10 C11 C12 175.3(2) . . . . ?
O2 S1 N2 C8 53.5(2) . . . . ?
O2 S1 C10 C15 -173.5(2) . . . . ?
O2 S1 C10 C11 9.9(2) . . . . ?
O1 S1 N2 C8 -177.21(19) . . . . ?
O1 S1 C10 C15 56.6(2) . . . . ?
O1 S1 C10 C11 -120.0(2) . . . . ?
N1 C1 C6 C7 -1.5(3) . . . . ?
N1 C1 C6 C5 179.9(2) . . . . ?
N1 C1 C2 C3 178.5(2) . . . . ?
N2 S1 C10 C15 -56.9(2) . . . . ?
N2 S1 C10 C11 126.5(2) . . . . ?
N2 C8 C7 C6 -71.0(2) . . . . ?
N2 C8 C9 N1 60.4(2) . . . . ?
C1 N1 C9 C8 44.9(3) . . . . ?
C1 C6 C7 C8 -17.2(3) . . . . ?
C1 C6 C5 C4 2.0(3) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C10 S1 N2 C8 -61.8(2) . . . . ?
C10 C15 C14 C13 0.2(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C15 C10 C11 C12 -1.3(4) . . . . ?
C7 C8 C9 N1 -61.1(2) . . . . ?
C7 C6 C5 C4 -176.5(2) . . . . ?
C5 C6 C7 C8 161.3(2) . . . . ?
C11 C10 C15 C14 1.3(4) . . . . ?
C2 C1 C6 C7 176.5(2) . . . . ?
C2 C1 C6 C5 -2.1(3) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C9 N1 C1 C6 -13.4(3) . . . . ?
C9 N1 C1 C2 168.6(2) . . . . ?
C9 C8 C7 C6 47.9(2) . . . . ?
C14 C13 C12 C11 1.8(4) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C16 C13 C14 C15 179.0(3) . . . . ?
C16 C13 C12 C11 -178.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method hexane/dichloromethane
