# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_zgf79
_database_code_depnum_ccdc_archive 'CCDC 1518169'
_audit_update_record             
;
2016-11-21 deposited with the CCDC.
2017-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'3,5-dimethoxy-2-((R)-2-nitro-1-phenylethyl)phenyl ((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate'
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H31 N O8 S'
_chemical_formula_sum            'C26 H31 N O8 S'
_chemical_formula_weight         517.58

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)

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

_cell_length_a                   11.7760(9)
_cell_length_b                   8.4171(6)
_cell_length_c                   13.9685(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.786(3)
_cell_angle_gamma                90.00
_cell_volume                     1257.01(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    7191
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      30.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9381
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_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_reflns_number            16348
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         31.10
_reflns_number_total             7584
_reflns_number_gt                7288
_reflns_threshold_expression     >2sigma(I)

_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-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 > 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)+(0.0612P)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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(8)
_refine_ls_number_reflns         7584
_refine_ls_number_parameters     330
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_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 0.6402(2) 0.6362(3) 0.86534(19) 0.0123(4) Uani 1 1 d . . .
C2 C 0.5134(2) 0.6686(3) 0.8171(2) 0.0132(4) Uani 1 1 d . . .
H2 H 0.4830 0.7683 0.7845 0.016 Uiso 1 1 calc R . .
C3 C 0.4320(2) 0.5489(3) 0.81839(19) 0.0128(4) Uani 1 1 d . . .
C4 C 0.2587(2) 0.7261(3) 0.7469(2) 0.0208(5) Uani 1 1 d . . .
H4A H 0.2963 0.7980 0.8073 0.031 Uiso 1 1 calc R . .
H4B H 0.1676 0.7262 0.7224 0.031 Uiso 1 1 calc R . .
H4C H 0.2802 0.7620 0.6898 0.031 Uiso 1 1 calc R . .
C5 C 0.4771(2) 0.4000(3) 0.86186(19) 0.0138(4) Uani 1 1 d . . .
H5 H 0.4205 0.3171 0.8578 0.017 Uiso 1 1 calc R . .
C6 C 0.6046(2) 0.3742(3) 0.91077(18) 0.0128(4) Uani 1 1 d . . .
C7 C 0.5727(3) 0.1016(3) 0.9409(2) 0.0187(5) Uani 1 1 d . . .
H7A H 0.5160 0.1236 0.9743 0.028 Uiso 1 1 calc R . .
H7B H 0.6216 0.0059 0.9721 0.028 Uiso 1 1 calc R . .
H7C H 0.5238 0.0851 0.8651 0.028 Uiso 1 1 calc R . .
C8 C 0.6907(2) 0.4940(3) 0.91600(19) 0.0134(4) Uani 1 1 d . . .
C9 C 0.8297(2) 0.4674(3) 0.97743(18) 0.0132(4) Uani 1 1 d . . .
H9 H 0.8393 0.3606 1.0113 0.016 Uiso 1 1 calc R . .
C10 C 0.8913(2) 0.5871(3) 1.0676(2) 0.0154(4) Uani 1 1 d . . .
H10A H 0.9827 0.5681 1.1017 0.018 Uiso 1 1 calc R . .
H10B H 0.8771 0.6963 1.0386 0.018 Uiso 1 1 calc R . .
C11 C 0.8993(2) 0.4591(3) 0.90593(19) 0.0139(4) Uani 1 1 d . . .
C12 C 0.8532(2) 0.3572(3) 0.8189(2) 0.0175(4) Uani 1 1 d . . .
H12 H 0.7781 0.2998 0.8035 0.021 Uiso 1 1 calc R . .
C13 C 0.9161(3) 0.3387(3) 0.7543(2) 0.0206(5) Uani 1 1 d . . .
H13 H 0.8837 0.2686 0.6957 0.025 Uiso 1 1 calc R . .
C14 C 1.0259(3) 0.4224(3) 0.7751(2) 0.0204(5) Uani 1 1 d . . .
H14 H 1.0688 0.4100 0.7312 0.025 Uiso 1 1 calc R . .
C15 C 1.0715(3) 0.5238(3) 0.8610(2) 0.0213(5) Uani 1 1 d . . .
H15 H 1.1465 0.5812 0.8758 0.026 Uiso 1 1 calc R . .
C16 C 1.0094(2) 0.5433(3) 0.9263(2) 0.0169(5) Uani 1 1 d . . .
H16 H 1.0420 0.6139 0.9846 0.020 Uiso 1 1 calc R . .
C17 C 0.7353(2) 0.7223(3) 0.68603(19) 0.0156(4) Uani 1 1 d . . .
H17A H 0.8223 0.6821 0.7158 0.019 Uiso 1 1 calc R . .
H17B H 0.6792 0.6310 0.6785 0.019 Uiso 1 1 calc R . .
C18 C 0.7041(2) 0.7935(3) 0.5772(2) 0.0156(5) Uani 1 1 d . . .
C19 C 0.7427(3) 0.9706(3) 0.5732(2) 0.0178(5) Uani 1 1 d . . .
H19A H 0.6830 1.0443 0.5831 0.021 Uiso 1 1 calc R . .
H19B H 0.8277 0.9918 0.6282 0.021 Uiso 1 1 calc R . .
C20 C 0.7387(3) 0.9879(4) 0.4608(2) 0.0227(5) Uani 1 1 d . . .
H20A H 0.6790 1.0717 0.4201 0.027 Uiso 1 1 calc R . .
H20B H 0.8225 1.0134 0.4644 0.027 Uiso 1 1 calc R . .
C21 C 0.6949(3) 0.8238(3) 0.4119(2) 0.0215(6) Uani 1 1 d . . .
H21 H 0.7115 0.8007 0.3487 0.026 Uiso 1 1 calc R . .
C22 C 0.7612(3) 0.7094(3) 0.5064(2) 0.0198(5) Uani 1 1 d . . .
C23 C 0.7209(3) 0.5352(4) 0.4817(3) 0.0289(6) Uani 1 1 d . . .
H23A H 0.7462 0.4955 0.4276 0.043 Uiso 1 1 calc R . .
H23B H 0.6298 0.5275 0.4559 0.043 Uiso 1 1 calc R . .
H23C H 0.7610 0.4713 0.5459 0.043 Uiso 1 1 calc R . .
C24 C 0.9038(3) 0.7175(4) 0.5501(2) 0.0257(6) Uani 1 1 d . . .
H24A H 0.9408 0.6498 0.6128 0.039 Uiso 1 1 calc R . .
H24B H 0.9314 0.8275 0.5693 0.039 Uiso 1 1 calc R . .
H24C H 0.9308 0.6805 0.4964 0.039 Uiso 1 1 calc R . .
C25 C 0.5564(3) 0.8104(4) 0.3925(2) 0.0254(6) Uani 1 1 d . . .
H25A H 0.5103 0.9097 0.3621 0.031 Uiso 1 1 calc R . .
H25B H 0.5148 0.7206 0.3450 0.031 Uiso 1 1 calc R . .
C26 C 0.5656(3) 0.7814(3) 0.5035(2) 0.0208(5) Uani 1 1 d . . .
N1 N 0.8385(2) 0.5718(3) 1.14796(19) 0.0210(5) Uani 1 1 d . . .
O1 O 0.30588(16) 0.5675(2) 0.77812(15) 0.0171(3) Uani 1 1 d . . .
O2 O 0.65568(18) 0.2340(2) 0.95713(15) 0.0179(4) Uani 1 1 d . . .
O3 O 0.7372(2) 0.6314(3) 1.1286(2) 0.0373(6) Uani 1 1 d . . .
O4 O 0.8993(2) 0.5004(3) 1.22909(18) 0.0331(5) Uani 1 1 d . . .
O5 O 0.72861(16) 0.7536(2) 0.87273(13) 0.0137(3) Uani 1 1 d . . .
O6 O 0.60018(19) 0.9388(2) 0.72933(16) 0.0198(4) Uani 1 1 d . . .
O7 O 0.82902(18) 0.9591(2) 0.82037(15) 0.0206(4) Uani 1 1 d . . .
O8 O 0.48297(19) 0.7438(3) 0.52778(17) 0.0269(5) Uani 1 1 d . . .
S1 S 0.71926(5) 0.86271(7) 0.77490(5) 0.01341(11) 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 1.383(3) . ?
C1 C8 1.391(3) . ?
C1 O5 1.408(3) . ?
C2 C3 1.396(3) . ?
C2 H2 0.9500 . ?
C3 O1 1.359(3) . ?
C3 C5 1.397(3) . ?
C4 O1 1.441(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 O2 1.359(3) . ?
C6 C8 1.411(3) . ?
C7 O2 1.436(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.513(3) . ?
C9 C11 1.536(3) . ?
C9 C10 1.536(3) . ?
C9 H9 1.0000 . ?
C10 N1 1.500(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.398(3) . ?
C11 C12 1.399(4) . ?
C12 C13 1.394(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.528(4) . ?
C17 S1 1.780(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C26 1.524(4) . ?
C18 C19 1.566(4) . ?
C18 C22 1.578(4) . ?
C19 C20 1.557(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.531(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C25 1.541(4) . ?
C21 C22 1.553(4) . ?
C21 H21 1.0000 . ?
C22 C24 1.529(4) . ?
C22 C23 1.536(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.527(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 O8 1.199(4) . ?
N1 O3 1.215(3) . ?
N1 O4 1.215(3) . ?
O5 S1 1.6113(18) . ?
O6 S1 1.426(2) . ?
O7 S1 1.430(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
C2 C1 C8 124.2(2) . . ?
C2 C1 O5 120.8(2) . . ?
C8 C1 O5 114.9(2) . . ?
C1 C2 C3 117.3(2) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
O1 C3 C2 123.3(2) . . ?
O1 C3 C5 115.7(2) . . ?
C2 C3 C5 121.0(2) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C3 C5 H5 120.2 . . ?
O2 C6 C5 123.0(2) . . ?
O2 C6 C8 115.5(2) . . ?
C5 C6 C8 121.4(2) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C8 C6 116.4(2) . . ?
C1 C8 C9 123.1(2) . . ?
C6 C8 C9 120.5(2) . . ?
C8 C9 C11 112.54(19) . . ?
C8 C9 C10 113.2(2) . . ?
C11 C9 C10 111.4(2) . . ?
C8 C9 H9 106.3 . . ?
C11 C9 H9 106.3 . . ?
C10 C9 H9 106.3 . . ?
N1 C10 C9 110.9(2) . . ?
N1 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C16 C11 C12 118.5(2) . . ?
C16 C11 C9 123.1(2) . . ?
C12 C11 C9 118.4(2) . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 118.9(3) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 120.2(2) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 S1 112.44(18) . . ?
C18 C17 H17A 109.1 . . ?
S1 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
S1 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C26 C18 C17 112.9(2) . . ?
C26 C18 C19 106.5(2) . . ?
C17 C18 C19 117.1(2) . . ?
C26 C18 C22 99.4(2) . . ?
C17 C18 C22 117.4(2) . . ?
C19 C18 C22 101.4(2) . . ?
C20 C19 C18 103.8(2) . . ?
C20 C19 H19A 111.0 . . ?
C18 C19 H19A 111.0 . . ?
C20 C19 H19B 111.0 . . ?
C18 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
C21 C20 C19 103.1(2) . . ?
C21 C20 H20A 111.1 . . ?
C19 C20 H20A 111.1 . . ?
C21 C20 H20B 111.1 . . ?
C19 C20 H20B 111.1 . . ?
H20A C20 H20B 109.1 . . ?
C20 C21 C25 106.1(2) . . ?
C20 C21 C22 103.0(2) . . ?
C25 C21 C22 102.9(2) . . ?
C20 C21 H21 114.5 . . ?
C25 C21 H21 114.5 . . ?
C22 C21 H21 114.5 . . ?
C24 C22 C23 108.5(3) . . ?
C24 C22 C21 112.9(2) . . ?
C23 C22 C21 113.8(2) . . ?
C24 C22 C18 114.5(2) . . ?
C23 C22 C18 113.3(2) . . ?
C21 C22 C18 93.4(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C21 102.3(2) . . ?
C26 C25 H25A 111.3 . . ?
C21 C25 H25A 111.3 . . ?
C26 C25 H25B 111.3 . . ?
C21 C25 H25B 111.3 . . ?
H25A C25 H25B 109.2 . . ?
O8 C26 C18 126.3(3) . . ?
O8 C26 C25 127.5(3) . . ?
C18 C26 C25 106.0(2) . . ?
O3 N1 O4 123.4(3) . . ?
O3 N1 C10 118.3(2) . . ?
O4 N1 C10 118.3(2) . . ?
C3 O1 C4 116.6(2) . . ?
C6 O2 C7 117.52(19) . . ?
C1 O5 S1 123.53(15) . . ?
O6 S1 O7 118.67(12) . . ?
O6 S1 O5 109.85(11) . . ?
O7 S1 O5 102.65(10) . . ?
O6 S1 C17 111.04(12) . . ?
O7 S1 C17 110.23(12) . . ?
O5 S1 C17 102.92(11) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        31.10
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.115
