# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2768_GuillotICMMO
_database_code_depnum_ccdc_archive 'CCDC 2074275'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2021-03-30 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 N2 O2 S'
_chemical_formula_sum            'C17 H22 N2 O2 S'
_chemical_formula_weight         318.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 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 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1239 '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                   10.3118(3)
_cell_length_b                   9.8749(3)
_cell_length_c                   16.4567(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.3960(10)
_cell_angle_gamma                90
_cell_volume                     1615.62(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9722
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      33.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8858
_exptl_absorpt_correction_T_max  0.9465
_exptl_absorpt_process_details   'Bruker APEX2'
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57631
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.109
_diffrn_reflns_theta_max         33.226
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6152
_reflns_number_gt                5567
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0414P)²+0.4923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         6152
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
C1 C 0.05448(8) 0.47666(8) 0.24018(5) 0.01805(13) Uani 1 1 d . . . . .
H1 H 0.013583 0.524430 0.276967 0.022 Uiso 1 1 calc R U . . .
C2 C 0.11585(7) 0.53832(7) 0.18657(4) 0.01489(12) Uani 1 1 d . . . . .
H2 H 0.122789 0.633790 0.181969 0.018 Uiso 1 1 calc R U . . .
C3 C 0.16901(6) 0.44364(7) 0.13771(4) 0.01184(11) Uani 1 1 d . . . . .
C4 C 0.14685(7) 0.30881(7) 0.15809(4) 0.01343(12) Uani 1 1 d . . . . .
C5 C 0.19690(8) 0.19848(7) 0.12226(5) 0.01719(13) Uani 1 1 d . . . . .
H5 H 0.180439 0.107980 0.136384 0.021 Uiso 1 1 calc R U . . .
C6 C 0.27103(8) 0.22623(8) 0.06568(5) 0.01888(13) Uani 1 1 d . . . . .
H6 H 0.307990 0.153489 0.041353 0.023 Uiso 1 1 calc R U . . .
C7 C 0.29293(7) 0.36023(8) 0.04329(5) 0.01632(12) Uani 1 1 d . . . . .
H7 H 0.343750 0.375899 0.003766 0.020 Uiso 1 1 calc R U . . .
C8 C 0.24205(6) 0.46998(7) 0.07759(4) 0.01193(11) Uani 1 1 d . . . . .
C9 C 0.13830(7) 0.67259(8) 0.00738(4) 0.01519(12) Uani 1 1 d . . . . .
H9A H 0.063761 0.655262 0.033499 0.018 Uiso 1 1 calc R U . . .
H9B H 0.113116 0.633740 -0.050136 0.018 Uiso 1 1 calc R U . . .
C10 C 0.15994(7) 0.82399(8) 0.00246(5) 0.01793(13) Uani 1 1 d . . . . .
H10A H 0.078046 0.866572 -0.033938 0.022 Uiso 1 1 calc R U . . .
H10B H 0.177153 0.864240 0.059426 0.022 Uiso 1 1 calc R U . . .
C11 C 0.37194(7) 0.63110(8) 0.01888(4) 0.01498(12) Uani 1 1 d . . . . .
H11A H 0.348991 0.591420 -0.038410 0.018 Uiso 1 1 calc R U . . .
H11B H 0.454671 0.586402 0.052681 0.018 Uiso 1 1 calc R U . . .
C12 C 0.39709(7) 0.78237(8) 0.01359(5) 0.01736(13) Uani 1 1 d . . . . .
H12A H 0.428426 0.820581 0.071097 0.021 Uiso 1 1 calc R U . . .
H12B H 0.468166 0.797619 -0.015719 0.021 Uiso 1 1 calc R U . . .
C13 C 0.27260(7) 0.93051(7) -0.09896(4) 0.01385(12) Uani 1 1 d . . . . .
C14 C 0.12317(7) 1.08055(7) -0.20105(4) 0.01306(11) Uani 1 1 d . . . . .
C15 C 0.15404(9) 1.02121(10) -0.27895(5) 0.02358(16) Uani 1 1 d . . . . .
H15A H 0.251683 1.014069 -0.269671 0.035 Uiso 1 1 calc R U . . .
H15B H 0.116861 1.080219 -0.327416 0.035 Uiso 1 1 calc R U . . .
H15C H 0.113513 0.931037 -0.290037 0.035 Uiso 1 1 calc R U . . .
C16 C 0.20018(9) 1.21022(8) -0.17292(6) 0.02564(17) Uani 1 1 d . . . . .
H16A H 0.175863 1.246397 -0.123492 0.038 Uiso 1 1 calc R U . . .
H16B H 0.177585 1.276710 -0.218729 0.038 Uiso 1 1 calc R U . . .
H16C H 0.296959 1.191549 -0.158317 0.038 Uiso 1 1 calc R U . . .
C17 C -0.02714(7) 1.10354(8) -0.21820(5) 0.01874(13) Uani 1 1 d . . . . .
H17A H -0.074865 1.018604 -0.236986 0.028 Uiso 1 1 calc R U . . .
H17B H -0.055731 1.172390 -0.262217 0.028 Uiso 1 1 calc R U . . .
H17C H -0.047933 1.134472 -0.166491 0.028 Uiso 1 1 calc R U . . .
N1 N 0.26191(6) 0.60707(6) 0.05772(4) 0.01200(10) Uani 1 1 d . . . . .
N2 N 0.27405(6) 0.85001(7) -0.03197(4) 0.01743(12) Uani 1 1 d . . . . .
O1 O 0.37066(6) 0.95224(7) -0.12522(4) 0.02178(12) Uani 1 1 d . . . . .
O2 O 0.14891(5) 0.98234(6) -0.13166(3) 0.01579(10) Uani 1 1 d . . . . .
S1 S 0.05874(2) 0.30209(2) 0.23429(2) 0.01794(5) Uani 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
C1 C2 1.3587(10) . ?
C1 S1 1.7278(8) . ?
C2 C3 1.4336(9) . ?
C3 C4 1.4064(9) . ?
C3 C8 1.4176(9) . ?
C4 C5 1.4010(10) . ?
C4 S1 1.7341(7) . ?
C5 C6 1.3800(11) . ?
C6 C7 1.4078(11) . ?
C7 C8 1.3877(10) . ?
C8 N1 1.4203(9) . ?
C9 N1 1.4727(9) . ?
C9 C10 1.5170(11) . ?
C10 N2 1.4579(9) . ?
C11 N1 1.4619(9) . ?
C11 C12 1.5225(11) . ?
C12 N2 1.4536(9) . ?
C13 O1 1.2196(9) . ?
C13 O2 1.3468(8) . ?
C13 N2 1.3560(9) . ?
C14 O2 1.4678(8) . ?
C14 C16 1.5130(11) . ?
C14 C17 1.5171(10) . ?
C14 C15 1.5181(10) . ?

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 S1 112.80(6) . . ?
C1 C2 C3 112.66(7) . . ?
C4 C3 C8 119.35(6) . . ?
C4 C3 C2 111.91(6) . . ?
C8 C3 C2 128.68(6) . . ?
C5 C4 C3 122.31(6) . . ?
C5 C4 S1 126.65(6) . . ?
C3 C4 S1 110.98(5) . . ?
C6 C5 C4 117.49(7) . . ?
C5 C6 C7 121.29(7) . . ?
C8 C7 C6 121.55(7) . . ?
C7 C8 C3 117.97(6) . . ?
C7 C8 N1 123.88(6) . . ?
C3 C8 N1 118.12(6) . . ?
N1 C9 C10 110.20(6) . . ?
N2 C10 C9 109.87(6) . . ?
N1 C11 C12 110.37(6) . . ?
N2 C12 C11 109.98(6) . . ?
O1 C13 O2 125.30(6) . . ?
O1 C13 N2 124.06(6) . . ?
O2 C13 N2 110.64(6) . . ?
O2 C14 C16 110.45(6) . . ?
O2 C14 C17 102.03(5) . . ?
C16 C14 C17 110.95(6) . . ?
O2 C14 C15 111.52(6) . . ?
C16 C14 C15 111.99(7) . . ?
C17 C14 C15 109.49(6) . . ?
C8 N1 C11 115.56(6) . . ?
C8 N1 C9 113.08(5) . . ?
C11 N1 C9 109.82(5) . . ?
C13 N2 C12 120.56(6) . . ?
C13 N2 C10 125.69(6) . . ?
C12 N2 C10 113.74(6) . . ?
C13 O2 C14 121.22(5) . . ?
C1 S1 C4 91.63(3) . . ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.048

