# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_dbr2vr_a
_database_code_depnum_ccdc_archive 'CCDC 1479963'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.38 H3.23 N0.15 O0.77 S0.15'
_chemical_formula_weight         63.30

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           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7273(11)
_cell_length_b                   13.2654(14)
_cell_length_c                   15.7765(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.263(4)
_cell_angle_gamma                90.00
_cell_volume                     2019.4(4)
_cell_formula_units_Z            26
_cell_measurement_temperature    298
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      27.35

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            46124
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3549
_reflns_number_gt                2956
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2σ(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)+(0.0706P)²+1.7369P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3549
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1538
_refine_ls_wR_factor_gt          0.1463
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_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
C1 C 0.6480(3) 0.15478(19) 0.35751(15) 0.0418(6) Uani 1 1 d . . .
C2 C 0.6373(3) 0.1077(2) 0.43471(17) 0.0525(7) Uani 1 1 d . . .
H2 H 0.6296 0.1455 0.4850 0.063 Uiso 1 1 calc R . .
C3 C 0.6381(3) 0.0044(2) 0.43569(19) 0.0614(8) Uani 1 1 d . . .
H3 H 0.6341 -0.0306 0.4879 0.074 Uiso 1 1 calc R . .
C4 C 0.6449(3) -0.0494(2) 0.3612(2) 0.0642(8) Uani 1 1 d . . .
H4 H 0.6427 -0.1210 0.3628 0.077 Uiso 1 1 calc R . .
C5 C 0.6547(3) -0.0016(2) 0.28478(18) 0.0578(8) Uani 1 1 d . . .
H5 H 0.6586 -0.0395 0.2341 0.069 Uiso 1 1 calc R . .
C6 C 0.6589(3) 0.1028(2) 0.28309(15) 0.0448(6) Uani 1 1 d . . .
C7 C 0.6776(3) 0.1690(2) 0.20776(15) 0.0476(6) Uani 1 1 d . . .
C8 C 0.8217(3) 0.1647(2) 0.17787(17) 0.0547(7) Uani 1 1 d . . .
H8 H 0.8894 0.1502 0.2296 0.066 Uiso 1 1 calc R . .
C9 C 0.8455(4) 0.2735(2) 0.1526(2) 0.0640(8) Uani 1 1 d . . .
C10 C 0.7551(3) 0.3403(2) 0.19670(16) 0.0471(6) Uani 1 1 d . . .
C11 C 0.7362(3) 0.4400(2) 0.19891(16) 0.0484(6) Uani 1 1 d . . .
H11 H 0.6617 0.4594 0.2289 0.058 Uiso 1 1 calc R . .
C12 C 0.8067(3) 0.5251(2) 0.16478(16) 0.0479(6) Uani 1 1 d . . .
C13 C 0.9247(3) 0.5207(3) 0.1231(2) 0.0624(8) Uani 1 1 d . . .
H13 H 0.9672 0.4574 0.1156 0.075 Uiso 1 1 calc R . .
C14 C 0.9801(4) 0.6064(3) 0.0929(2) 0.0740(10) Uani 1 1 d . . .
H14 H 1.0602 0.6016 0.0644 0.089 Uiso 1 1 calc R . .
C15 C 0.9231(4) 0.6970(3) 0.1029(3) 0.0896(12) Uani 1 1 d . . .
H15 H 0.9632 0.7559 0.0821 0.108 Uiso 1 1 calc R . .
C16 C 0.8068(5) 0.7043(3) 0.1431(3) 0.0982(14) Uani 1 1 d . . .
H16 H 0.7660 0.7683 0.1501 0.118 Uiso 1 1 calc R . .
C17 C 0.7489(4) 0.6189(2) 0.1736(2) 0.0706(9) Uani 1 1 d . . .
H17 H 0.6678 0.6247 0.2011 0.085 Uiso 1 1 calc R . .
C18 C 0.5659(3) 0.1602(2) 0.13018(17) 0.0590(8) Uani 1 1 d . . .
C19 C 0.3660(7) 0.0768(4) 0.0638(3) 0.137(3) Uani 1 1 d . . .
H19A H 0.4037 0.0896 0.0094 0.164 Uiso 1 1 calc R . .
H19B H 0.3302 0.0069 0.0628 0.164 Uiso 1 1 calc R . .
C20 C 0.2576(7) 0.1452(9) 0.0727(5) 0.210(4) Uani 1 1 d . . .
H20A H 0.1845 0.1375 0.0244 0.315 Uiso 1 1 calc R . .
H20B H 0.2936 0.2143 0.0737 0.315 Uiso 1 1 calc R . .
H20C H 0.2195 0.1314 0.1261 0.315 Uiso 1 1 calc R . .
C21 C 0.8489(5) 0.0876(3) 0.1097(2) 0.0848(11) Uani 1 1 d . . .
H21A H 0.7580 0.0636 0.0816 0.102 Uiso 1 1 calc R . .
H21B H 0.8948 0.1231 0.0658 0.102 Uiso 1 1 calc R . .
C22 C 0.9297(8) 0.0019(5) 0.1362(4) 0.158(3) Uani 1 1 d . . .
H22A H 0.9385 -0.0411 0.0867 0.237 Uiso 1 1 calc R . .
H22B H 0.8847 -0.0360 0.1783 0.237 Uiso 1 1 calc R . .
H22C H 1.0220 0.0235 0.1619 0.237 Uiso 1 1 calc R . .
N1 N 0.6678(2) 0.27401(16) 0.23805(13) 0.0460(5) Uani 1 1 d . . .
O1 O 0.4773(3) 0.0896(2) 0.13681(16) 0.1038(11) Uani 1 1 d . . .
O2 O 0.5644(3) 0.2144(2) 0.07067(16) 0.1095(11) Uani 1 1 d . . .
O3 O 0.9240(4) 0.2978(2) 0.1034(2) 0.1152(12) Uani 1 1 d . . .
O4 O 0.7647(2) 0.33469(15) 0.38602(12) 0.0651(6) Uani 1 1 d . . .
O5 O 0.5159(2) 0.32699(17) 0.34877(14) 0.0714(6) Uani 1 1 d . . .
S001 S 0.64804(7) 0.28525(5) 0.34105(4) 0.0453(2) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.378(3) . ?
C1 C2 1.385(3) . ?
C1 S001 1.750(3) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.507(3) . ?
C7 N1 1.480(3) . ?
C7 C18 1.535(4) . ?
C7 C8 1.535(4) . ?
C8 C9 1.523(4) . ?
C8 C21 1.532(4) . ?
C8 H8 1.0000 . ?
C9 O3 1.200(4) . ?
C9 C10 1.482(4) . ?
C10 C11 1.336(4) . ?
C10 N1 1.435(3) . ?
C11 C12 1.459(4) . ?
C11 H11 0.9500 . ?
C12 C17 1.379(4) . ?
C12 C13 1.394(4) . ?
C13 C14 1.369(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.342(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 O2 1.181(3) . ?
C18 O1 1.287(4) . ?
C19 C20 1.411(9) . ?
C19 O1 1.487(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.414(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 S001 1.667(2) . ?
O4 S001 1.420(2) . ?
O5 S001 1.419(2) . ?

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
C6 C1 C2 123.1(3) . . ?
C6 C1 S001 111.56(18) . . ?
C2 C1 S001 125.3(2) . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 C7 114.2(2) . . ?
C5 C6 C7 127.2(2) . . ?
N1 C7 C6 105.96(19) . . ?
N1 C7 C18 105.1(2) . . ?
C6 C7 C18 116.1(2) . . ?
N1 C7 C8 103.4(2) . . ?
C6 C7 C8 115.2(2) . . ?
C18 C7 C8 109.5(2) . . ?
C9 C8 C21 113.8(3) . . ?
C9 C8 C7 102.7(2) . . ?
C21 C8 C7 119.0(3) . . ?
C9 C8 H8 106.8 . . ?
C21 C8 H8 106.8 . . ?
C7 C8 H8 106.8 . . ?
O3 C9 C10 127.4(3) . . ?
O3 C9 C8 123.7(3) . . ?
C10 C9 C8 108.9(2) . . ?
C11 C10 N1 120.2(2) . . ?
C11 C10 C9 134.0(2) . . ?
N1 C10 C9 105.5(2) . . ?
C10 C11 C12 133.2(3) . . ?
C10 C11 H11 113.4 . . ?
C12 C11 H11 113.4 . . ?
C17 C12 C13 117.1(3) . . ?
C17 C12 C11 116.4(3) . . ?
C13 C12 C11 126.5(3) . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
O2 C18 O1 124.5(3) . . ?
O2 C18 C7 121.6(3) . . ?
O1 C18 C7 113.9(2) . . ?
C20 C19 O1 109.3(5) . . ?
C20 C19 H19A 109.8 . . ?
O1 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
O1 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C8 117.9(4) . . ?
C22 C21 H21A 107.8 . . ?
C8 C21 H21A 107.8 . . ?
C22 C21 H21B 107.8 . . ?
C8 C21 H21B 107.8 . . ?
H21A C21 H21B 107.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 N1 C7 111.3(2) . . ?
C10 N1 S001 122.42(17) . . ?
C7 N1 S001 114.78(16) . . ?
C18 O1 C19 116.7(3) . . ?
O5 S001 O4 116.88(15) . . ?
O5 S001 N1 109.63(13) . . ?
O4 S001 N1 110.18(12) . . ?
O5 S001 C1 110.85(13) . . ?
O4 S001 C1 113.44(12) . . ?
N1 S001 C1 93.35(11) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.046
