# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_MAI2II
_database_code_depnum_ccdc_archive 'CCDC 1014288'
_audit_update_record             
;
2014-07-16 deposited with the CCDC.
2014-12-03 downloaded from the CCDC.
;

_audit_creation_date             2013-07-19T16:21:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H21 N O2 S'
_chemical_formula_sum            'C19 H21 N O2 S'
_chemical_formula_weight         327.43
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   9.952(2)
_cell_length_b                   15.043(4)
_cell_length_c                   11.100(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.067(9)
_cell_angle_gamma                90
_cell_volume                     1661.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2708
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      22.62
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.972


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_number            15969
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             3783
_reflns_number_gt                2916
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 2012),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2sigma(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)+(0.0663P)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_number_reflns         3783
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.063

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'


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 0.71177(9) 0.28445(4) 0.48785(6) 0.02931(19) Uani 1 1 d . . .
O1 O 0.8388(2) 0.32909(11) 0.48843(18) 0.0393(5) Uani 1 1 d . . .
O2 O 0.5899(2) 0.33398(12) 0.47258(18) 0.0392(6) Uani 1 1 d . . .
C1 C 0.7140(3) -0.02107(15) 0.4912(2) 0.0285(6) Uani 1 1 d . . .
H1 H 0.6761 0.034 0.5156 0.034 Uiso 1 1 calc R . .
C2 C 0.7428(3) -0.08468(18) 0.5760(2) 0.0340(7) Uani 1 1 d . . .
H2 H 0.7264 -0.0724 0.6586 0.041 Uiso 1 1 calc R . .
C3 C 0.7952(3) -0.16622(17) 0.5434(3) 0.0344(7) Uani 1 1 d . . .
H3 H 0.8132 -0.2102 0.6028 0.041 Uiso 1 1 calc R . .
C4 C 0.8209(3) -0.18281(17) 0.4240(3) 0.0340(7) Uani 1 1 d . . .
H4 H 0.8577 -0.2384 0.4003 0.041 Uiso 1 1 calc R . .
C5 C 0.7934(3) -0.11866(15) 0.3380(2) 0.0281(6) Uani 1 1 d . . .
H5 H 0.8115 -0.131 0.2557 0.034 Uiso 1 1 calc R . .
C6 C 0.7399(3) -0.03675(16) 0.3696(2) 0.0241(6) Uani 1 1 d . . .
C7 C 0.7128(3) 0.03352(16) 0.2733(2) 0.0281(6) Uani 1 1 d . . .
H7 H 0.6983 0.0019 0.1952 0.034 Uiso 1 1 calc R . .
C8 C 0.5899(3) 0.08725(18) 0.2984(2) 0.0333(7) Uani 1 1 d . . .
H8 H 0.5047 0.0629 0.2782 0.04 Uiso 1 1 calc R . .
C9 C 0.5946(3) 0.16757(18) 0.3475(3) 0.0283(7) Uani 1 1 d . . .
H9 H 0.5123 0.1971 0.3638 0.034 Uiso 1 1 calc R . .
N10 N 0.7161(3) 0.21147(12) 0.37694(18) 0.0263(5) Uani 1 1 d . . .
C11 C 0.8426(3) 0.16201(18) 0.3631(2) 0.0269(6) Uani 1 1 d . . .
H11A H 0.8616 0.1278 0.4374 0.032 Uiso 1 1 calc R . .
H11B H 0.9177 0.2041 0.3499 0.032 Uiso 1 1 calc R . .
C12 C 0.8309(3) 0.09876(17) 0.2558(2) 0.0282(7) Uani 1 1 d . . .
H12 H 0.8103 0.1356 0.1832 0.034 Uiso 1 1 calc R . .
C13 C 0.9643(3) 0.05344(18) 0.2337(2) 0.0350(7) Uani 1 1 d . . .
H13A H 1.0327 0.0983 0.2151 0.053 Uiso 1 1 calc R . .
H13B H 0.9557 0.0123 0.1657 0.053 Uiso 1 1 calc R . .
H13C H 0.9911 0.0204 0.306 0.053 Uiso 1 1 calc R . .
C14 C 0.7006(3) 0.22128(15) 0.6205(2) 0.0229(6) Uani 1 1 d . . .
C15 C 0.5759(3) 0.19227(17) 0.6587(2) 0.0249(6) Uani 1 1 d . . .
H15 H 0.4964 0.2096 0.6175 0.03 Uiso 1 1 calc R . .
C16 C 0.5697(3) 0.13730(17) 0.7585(2) 0.0276(6) Uani 1 1 d . . .
H16 H 0.4847 0.1167 0.7854 0.033 Uiso 1 1 calc R . .
C17 C 0.6857(3) 0.11132(15) 0.8207(2) 0.0278(6) Uani 1 1 d . . .
C18 C 0.8092(3) 0.14101(16) 0.7805(2) 0.0296(7) Uani 1 1 d . . .
H18 H 0.8888 0.1238 0.8216 0.036 Uiso 1 1 calc R . .
C19 C 0.8174(3) 0.19578(17) 0.6804(2) 0.0273(7) Uani 1 1 d . . .
H19 H 0.9025 0.2159 0.6528 0.033 Uiso 1 1 calc R . .
C20 C 0.6765(4) 0.05340(18) 0.9305(3) 0.0468(9) Uani 1 1 d . . .
H20A H 0.6553 -0.0076 0.9062 0.07 Uiso 1 1 calc R . .
H20B H 0.6056 0.0758 0.9836 0.07 Uiso 1 1 calc R . .
H20C H 0.7627 0.0542 0.9734 0.07 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O1 1.431(2) . ?
S1 O2 1.433(2) . ?
S1 N10 1.650(2) . ?
S1 C14 1.756(2) . ?
C1 C2 1.372(4) . ?
C1 C6 1.395(3) . ?
C1 H1 0.95 . ?
C2 C3 1.381(4) . ?
C2 H2 0.95 . ?
C3 C4 1.374(4) . ?
C3 H3 0.95 . ?
C4 C5 1.384(4) . ?
C4 H4 0.95 . ?
C5 C6 1.388(3) . ?
C5 H5 0.95 . ?
C6 C7 1.527(3) . ?
C7 C8 1.492(4) . ?
C7 C12 1.544(4) . ?
C7 H7 1 . ?
C8 C9 1.327(4) . ?
C8 H8 0.95 . ?
C9 N10 1.416(4) . ?
C9 H9 0.95 . ?
N10 C11 1.471(4) . ?
C11 C12 1.529(4) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.513(4) . ?
C12 H12 1 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 C15 1.382(4) . ?
C14 C19 1.393(4) . ?
C15 C16 1.384(4) . ?
C15 H15 0.95 . ?
C16 C17 1.400(4) . ?
C16 H16 0.95 . ?
C17 C18 1.382(4) . ?
C17 C20 1.501(3) . ?
C18 C19 1.385(4) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?


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
O1 S1 O2 120.26(11) . . ?
O1 S1 N10 106.95(13) . . ?
O2 S1 N10 106.30(13) . . ?
O1 S1 C14 107.88(14) . . ?
O2 S1 C14 109.02(14) . . ?
N10 S1 C14 105.49(10) . . ?
C2 C1 C6 120.5(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 121.3(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 117.8(2) . . ?
C5 C6 C7 120.4(2) . . ?
C1 C6 C7 121.9(2) . . ?
C8 C7 C6 112.9(2) . . ?
C8 C7 C12 107.7(2) . . ?
C6 C7 C12 113.2(2) . . ?
C8 C7 H7 107.6 . . ?
C6 C7 H7 107.6 . . ?
C12 C7 H7 107.6 . . ?
C9 C8 C7 122.8(3) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C8 C9 N10 123.3(3) . . ?
C8 C9 H9 118.3 . . ?
N10 C9 H9 118.3 . . ?
C9 N10 C11 118.10(19) . . ?
C9 N10 S1 117.34(19) . . ?
C11 N10 S1 116.0(2) . . ?
N10 C11 C12 109.4(2) . . ?
N10 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
N10 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 109.9(2) . . ?
C13 C12 C7 113.7(2) . . ?
C11 C12 C7 110.8(2) . . ?
C13 C12 H12 107.4 . . ?
C11 C12 H12 107.4 . . ?
C7 C12 H12 107.4 . . ?
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 121.0(2) . . ?
C15 C14 S1 119.1(2) . . ?
C19 C14 S1 119.7(2) . . ?
C14 C15 C16 118.3(3) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C17 121.6(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 118.9(2) . . ?
C18 C17 C20 120.3(3) . . ?
C16 C17 C20 120.8(3) . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C6 C1 C2 C3 -1.4(4) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C5 C6 C7 178.9(3) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C2 C1 C6 C7 -178.2(3) . . . . ?
C5 C6 C7 C8 144.4(3) . . . . ?
C1 C6 C7 C8 -36.5(4) . . . . ?
C5 C6 C7 C12 -93.0(3) . . . . ?
C1 C6 C7 C12 86.2(3) . . . . ?
C6 C7 C8 C9 99.4(3) . . . . ?
C12 C7 C8 C9 -26.3(3) . . . . ?
C7 C8 C9 N10 2.4(4) . . . . ?
C8 C9 N10 C11 -6.1(4) . . . . ?
C8 C9 N10 S1 -152.7(2) . . . . ?
O1 S1 N10 C9 -171.37(19) . . . . ?
O2 S1 N10 C9 -41.7(2) . . . . ?
C14 S1 N10 C9 73.9(2) . . . . ?
O1 S1 N10 C11 41.32(19) . . . . ?
O2 S1 N10 C11 170.95(17) . . . . ?
C14 S1 N10 C11 -73.4(2) . . . . ?
C9 N10 C11 C12 33.9(3) . . . . ?
S1 N10 C11 C12 -179.06(17) . . . . ?
N10 C11 C12 C13 175.0(2) . . . . ?
N10 C11 C12 C7 -58.4(3) . . . . ?
C8 C7 C12 C13 178.1(2) . . . . ?
C6 C7 C12 C13 52.6(3) . . . . ?
C8 C7 C12 C11 53.6(3) . . . . ?
C6 C7 C12 C11 -71.9(3) . . . . ?
O1 S1 C14 C15 161.86(19) . . . . ?
O2 S1 C14 C15 29.7(2) . . . . ?
N10 S1 C14 C15 -84.1(2) . . . . ?
O1 S1 C14 C19 -22.8(2) . . . . ?
O2 S1 C14 C19 -155.0(2) . . . . ?
N10 S1 C14 C19 91.2(2) . . . . ?
C19 C14 C15 C16 0.2(4) . . . . ?
S1 C14 C15 C16 175.46(19) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C15 C16 C17 C20 178.5(2) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C20 C17 C18 C19 -178.8(2) . . . . ?
C17 C18 C19 C14 0.2(4) . . . . ?
C15 C14 C19 C18 -0.4(4) . . . . ?
S1 C14 C19 C18 -175.69(18) . . . . ?


#----------------------------------------------------------------------------#
# END OF CIF FILE FOR MAI2II                                                 #
#----------------------------------------------------------------------------#
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
