# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_glo8988
_database_code_depnum_ccdc_archive 'CCDC 1584965'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N O5 S'
_chemical_formula_weight         361.40
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_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                   19.1685(5)
_cell_length_b                   5.7871(3)
_cell_length_c                   14.8903(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1651.78(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3051
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9647
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8858
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2765
_reflns_number_gt                2582
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP-SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0000P)²+1.8710P] 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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_number_reflns         2765
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.60158(12) 0.5405(5) 0.74489(16) 0.0314(6) Uani 1 1 d . . .
C1 C 0.57057(15) 0.3397(6) 0.7652(2) 0.0341(7) Uani 1 1 d . . .
O1 O 0.55762(12) 0.1788(4) 0.71567(16) 0.0460(6) Uani 1 1 d . . .
O2 O 0.55715(11) 0.3299(4) 0.85468(15) 0.0400(6) Uani 1 1 d . . .
C2 C 0.56951(15) 0.5538(6) 0.8941(2) 0.0355(7) Uani 1 1 d . . .
H2A H 0.5986 0.5394 0.9488 0.043 Uiso 1 1 calc R . .
H2B H 0.5248 0.6287 0.9105 0.043 Uiso 1 1 calc R . .
C3 C 0.60787(15) 0.6957(5) 0.82172(19) 0.0303(7) Uani 1 1 d . . .
H3 H 0.5817 0.8419 0.8096 0.036 Uiso 1 1 calc R . .
C4 C 0.68369(15) 0.7515(5) 0.84287(19) 0.0275(6) Uani 1 1 d . . .
C5 C 0.72729(15) 0.5973(5) 0.88736(19) 0.0318(7) Uani 1 1 d . . .
H5 H 0.7090 0.4546 0.9084 0.038 Uiso 1 1 calc R . .
C6 C 0.79648(16) 0.6486(6) 0.9014(2) 0.0329(7) Uani 1 1 d . . .
H6 H 0.8259 0.5427 0.9321 0.039 Uiso 1 1 calc R . .
C7 C 0.82283(14) 0.8570(6) 0.87004(19) 0.0307(7) Uani 1 1 d . . .
C8 C 0.78061(16) 1.0128(6) 0.8254(2) 0.0336(7) Uani 1 1 d . . .
H8 H 0.7990 1.1543 0.8035 0.040 Uiso 1 1 calc R . .
C9 C 0.71148(16) 0.9589(6) 0.8135(2) 0.0322(7) Uani 1 1 d . . .
H9 H 0.6819 1.0671 0.7843 0.039 Uiso 1 1 calc R . .
C10 C 0.95435(18) 0.7505(7) 0.8046(2) 0.0447(9) Uani 1 1 d . . .
H10A H 1.0043 0.7863 0.8044 0.067 Uiso 1 1 calc R . .
H10B H 0.9348 0.7811 0.7450 0.067 Uiso 1 1 calc R . .
H10C H 0.9476 0.5873 0.8198 0.067 Uiso 1 1 calc R . .
S1 S 0.91206(4) 0.92347(15) 0.88427(5) 0.0371(2) Uani 1 1 d . . .
O3 O 0.92199(12) 1.1608(4) 0.85984(19) 0.0550(7) Uani 1 1 d . . .
O4 O 0.93308(11) 0.8481(5) 0.97201(15) 0.0495(7) Uani 1 1 d . . .
C11 C 0.61173(15) 0.6147(6) 0.6519(2) 0.0371(8) Uani 1 1 d . . .
H11A H 0.5853 0.7593 0.6415 0.045 Uiso 1 1 calc R . .
H11B H 0.5927 0.4952 0.6111 0.045 Uiso 1 1 calc R . .
C12 C 0.68771(16) 0.6552(6) 0.62934(19) 0.0324(7) Uani 1 1 d . . .
C13 C 0.73818(16) 0.4936(6) 0.6530(2) 0.0363(8) Uani 1 1 d . . .
H13 H 0.7243 0.3531 0.6807 0.044 Uiso 1 1 calc R . .
C14 C 0.80751(17) 0.5335(6) 0.6369(2) 0.0379(8) Uani 1 1 d . . .
H14 H 0.8411 0.4217 0.6545 0.045 Uiso 1 1 calc R . .
C15 C 0.82904(16) 0.7355(6) 0.5952(2) 0.0341(7) Uani 1 1 d . . .
C16 C 0.77933(16) 0.8966(6) 0.5689(2) 0.0352(7) Uani 1 1 d . . .
H16 H 0.7930 1.0345 0.5391 0.042 Uiso 1 1 calc R . .
C17 C 0.70949(16) 0.8536(6) 0.58692(19) 0.0345(7) Uani 1 1 d . . .
H17 H 0.6757 0.9647 0.5694 0.041 Uiso 1 1 calc R . .
O5 O 0.89929(12) 0.7591(4) 0.58429(15) 0.0452(6) Uani 1 1 d . . .
C18 C 0.92445(19) 0.9592(7) 0.5380(2) 0.0494(9) Uani 1 1 d . . .
H18A H 0.9114 1.0983 0.5715 0.074 Uiso 1 1 calc R . .
H18B H 0.9038 0.9653 0.4778 0.074 Uiso 1 1 calc R . .
H18C H 0.9754 0.9509 0.5329 0.074 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
N1 C1 1.340(4) . ?
N1 C3 1.460(4) . ?
N1 C11 1.463(4) . ?
C1 O1 1.213(4) . ?
C1 O2 1.358(4) . ?
O2 C2 1.442(4) . ?
C2 C3 1.541(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.522(4) . ?
C3 H3 1.0000 . ?
C4 C9 1.384(4) . ?
C4 C5 1.391(4) . ?
C5 C6 1.375(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(4) . ?
C7 S1 1.766(3) . ?
C8 C9 1.373(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 S1 1.751(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
S1 O3 1.434(3) . ?
S1 O4 1.435(2) . ?
C11 C12 1.513(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.375(5) . ?
C12 C13 1.391(4) . ?
C13 C14 1.370(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(5) . ?
C14 H14 0.9500 . ?
C15 O5 1.363(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.388(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O5 C18 1.431(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C1 N1 C3 113.2(2) . . ?
C1 N1 C11 121.8(3) . . ?
C3 N1 C11 123.4(3) . . ?
O1 C1 N1 128.3(3) . . ?
O1 C1 O2 121.7(3) . . ?
N1 C1 O2 110.0(3) . . ?
C1 O2 C2 109.3(2) . . ?
O2 C2 C3 105.8(2) . . ?
O2 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
O2 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
N1 C3 C4 111.8(2) . . ?
N1 C3 C2 100.4(2) . . ?
C4 C3 C2 115.1(2) . . ?
N1 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C9 C4 C5 118.4(3) . . ?
C9 C4 C3 119.1(3) . . ?
C5 C4 C3 122.4(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 S1 118.9(2) . . ?
C6 C7 S1 120.1(2) . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C4 121.8(3) . . ?
C8 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 S1 O4 119.00(17) . . ?
O3 S1 C10 108.32(18) . . ?
O4 S1 C10 108.24(16) . . ?
O3 S1 C7 107.87(15) . . ?
O4 S1 C7 108.36(15) . . ?
C10 S1 C7 104.04(16) . . ?
N1 C11 C12 112.5(2) . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C17 C12 C13 117.8(3) . . ?
C17 C12 C11 121.6(3) . . ?
C13 C12 C11 120.6(3) . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
O5 C15 C14 115.6(3) . . ?
O5 C15 C16 125.2(3) . . ?
C14 C15 C16 119.2(3) . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C12 C17 C16 122.1(3) . . ?
C12 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C15 O5 C18 118.1(3) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C3 N1 C1 O1 179.3(3) . . . . ?
C11 N1 C1 O1 13.3(5) . . . . ?
C3 N1 C1 O2 -3.8(3) . . . . ?
C11 N1 C1 O2 -169.8(3) . . . . ?
O1 C1 O2 C2 -172.8(3) . . . . ?
N1 C1 O2 C2 10.1(3) . . . . ?
C1 O2 C2 C3 -11.9(3) . . . . ?
C1 N1 C3 C4 119.1(3) . . . . ?
C11 N1 C3 C4 -75.2(3) . . . . ?
C1 N1 C3 C2 -3.5(3) . . . . ?
C11 N1 C3 C2 162.3(3) . . . . ?
O2 C2 C3 N1 8.9(3) . . . . ?
O2 C2 C3 C4 -111.3(3) . . . . ?
N1 C3 C4 C9 99.7(3) . . . . ?
C2 C3 C4 C9 -146.5(3) . . . . ?
N1 C3 C4 C5 -77.4(3) . . . . ?
C2 C3 C4 C5 36.3(4) . . . . ?
C9 C4 C5 C6 -0.5(4) . . . . ?
C3 C4 C5 C6 176.7(3) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
C5 C6 C7 S1 -178.2(2) . . . . ?
C6 C7 C8 C9 0.8(5) . . . . ?
S1 C7 C8 C9 179.2(2) . . . . ?
C7 C8 C9 C4 -1.6(5) . . . . ?
C5 C4 C9 C8 1.5(4) . . . . ?
C3 C4 C9 C8 -175.8(3) . . . . ?
C8 C7 S1 O3 11.2(3) . . . . ?
C6 C7 S1 O3 -170.5(2) . . . . ?
C8 C7 S1 O4 141.3(2) . . . . ?
C6 C7 S1 O4 -40.4(3) . . . . ?
C8 C7 S1 C10 -103.7(3) . . . . ?
C6 C7 S1 C10 74.6(3) . . . . ?
C1 N1 C11 C12 -121.4(3) . . . . ?
C3 N1 C11 C12 74.0(4) . . . . ?
N1 C11 C12 C17 -131.3(3) . . . . ?
N1 C11 C12 C13 47.3(4) . . . . ?
C17 C12 C13 C14 1.9(5) . . . . ?
C11 C12 C13 C14 -176.8(3) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C13 C14 C15 O5 178.7(3) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
O5 C15 C16 C17 -177.9(3) . . . . ?
C14 C15 C16 C17 1.5(4) . . . . ?
C13 C12 C17 C16 -1.1(5) . . . . ?
C11 C12 C17 C16 177.5(3) . . . . ?
C15 C16 C17 C12 -0.6(5) . . . . ?
C14 C15 O5 C18 177.2(3) . . . . ?
C16 C15 O5 C18 -3.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040
#=============================================================================
#  end of cif data for "glo8988" (compound 2r) 
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

