# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_Marek99
_database_code_depnum_ccdc_archive 'CCDC 1488151'
_audit_update_record             
;
2016-06-28 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Benzyl (S)-4-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-methyl-2-methyleneoctanoate '
_chemical_name_common            'Marek99 (Zack)'
_chemical_melting_point          329.15
_chemical_formula_moiety         'C28 H33 N O5'
_chemical_formula_sum            'C28 H33 N O5'
_chemical_formula_weight         463.55
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   6.003(6)
_cell_length_b                   14.84(3)
_cell_length_c                   28.93(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2577(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2168
_cell_measurement_theta_min      0.7
_cell_measurement_theta_max      24.14

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_T_max  0.9655
_exptl_absorpt_process_details   
;  
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'   
;
_exptl_special_details           
;   
 ?   
;

_diffrn_ambient_temperature      293(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  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_detector_area_resol_mean 95
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            2210
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         24.14
_reflns_number_total             2210
_reflns_number_gt                1814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius, 2006)'
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 3.5'
_computing_publication_material  ?

_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)+(0.1044P)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   0.0
_refine_ls_number_reflns         2210
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
O1 O -0.2690(4) 0.59071(17) 0.41437(7) 0.0472(7) Uani 1 1 d . . .
O2 O -0.1210(4) 0.46862(18) 0.37941(9) 0.0498(7) Uani 1 1 d . . .
O3 O 0.3850(4) 0.50244(18) 0.35107(8) 0.0488(7) Uani 1 1 d . . .
O4 O -0.0839(5) 0.3511(2) 0.27451(10) 0.0656(9) Uani 1 1 d . . .
O5 O 0.1619(6) 0.2428(2) 0.29229(10) 0.0714(9) Uani 1 1 d . . .
N1 N 0.2471(5) 0.3824(2) 0.31499(9) 0.0433(8) Uani 1 1 d . . .
C1 C -0.8088(8) 0.6678(3) 0.53858(15) 0.0623(12) Uani 1 1 d . . .
H1 H -0.9122 0.6964 0.5575 0.075 Uiso 1 1 calc R . .
C2 C -0.8446(7) 0.6626(3) 0.49175(16) 0.0628(12) Uani 1 1 d . . .
H2 H -0.9727 0.6876 0.4790 0.075 Uiso 1 1 calc R . .
C3 C -0.6905(7) 0.6205(3) 0.46352(14) 0.0560(11) Uani 1 1 d . . .
H3 H -0.7161 0.6172 0.4319 0.067 Uiso 1 1 calc R . .
C4 C -0.4993(6) 0.5831(2) 0.48184(12) 0.0454(9) Uani 1 1 d . . .
C5 C -0.4643(7) 0.5894(3) 0.52918(12) 0.0505(10) Uani 1 1 d . . .
H5 H -0.3352 0.5657 0.5422 0.061 Uiso 1 1 calc R . .
C6 C -0.6211(8) 0.6309(3) 0.55715(14) 0.0612(12) Uani 1 1 d . . .
H6 H -0.5981 0.6337 0.5889 0.073 Uiso 1 1 calc R . .
C7 C -0.3373(7) 0.5334(3) 0.45196(12) 0.0508(10) Uani 1 1 d . . .
H7A H -0.2083 0.5159 0.4701 0.061 Uiso 1 1 calc R . .
H7B H -0.4063 0.4793 0.4399 0.061 Uiso 1 1 calc R . .
C8 C -0.1709(6) 0.5479(3) 0.37895(12) 0.0424(9) Uani 1 1 d . . .
C9 C -0.1325(6) 0.6077(3) 0.33821(12) 0.0425(9) Uani 1 1 d . . .
C10 C -0.1545(8) 0.6964(3) 0.34179(15) 0.0640(12) Uani 1 1 d . . .
H10A H -0.1943 0.7220 0.3699 0.077 Uiso 1 1 calc R . .
H10B H -0.1301 0.7329 0.3162 0.077 Uiso 1 1 calc R . .
C11 C -0.0781(6) 0.5611(3) 0.29337(12) 0.0429(9) Uani 1 1 d . . .
H11A H -0.1362 0.5974 0.2682 0.051 Uiso 1 1 calc R . .
H11B H -0.1565 0.5039 0.2928 0.051 Uiso 1 1 calc R . .
C12 C 0.1741(6) 0.5424(3) 0.28370(12) 0.0414(9) Uani 1 1 d . . .
C13 C 0.3008(6) 0.6318(3) 0.28881(13) 0.0494(9) Uani 1 1 d . . .
H13A H 0.4550 0.6226 0.2814 0.074 Uiso 1 1 calc R . .
H13B H 0.2882 0.6529 0.3201 0.074 Uiso 1 1 calc R . .
H13C H 0.2384 0.6757 0.2682 0.074 Uiso 1 1 calc R . .
C14 C 0.1959(6) 0.5082(3) 0.23352(11) 0.0485(10) Uani 1 1 d . . .
H14A H 0.0965 0.4572 0.2297 0.058 Uiso 1 1 calc R . .
H14B H 0.1446 0.5554 0.2129 0.058 Uiso 1 1 calc R . .
C15 C 0.4296(7) 0.4795(3) 0.21808(12) 0.0532(10) Uani 1 1 d . . .
H15A H 0.5289 0.5309 0.2201 0.064 Uiso 1 1 calc R . .
H15B H 0.4847 0.4335 0.2390 0.064 Uiso 1 1 calc R . .
C16 C 0.4344(8) 0.4432(4) 0.16919(14) 0.0719(14) Uani 1 1 d . . .
H16A H 0.3803 0.4893 0.1483 0.086 Uiso 1 1 calc R . .
H16B H 0.3339 0.3921 0.1671 0.086 Uiso 1 1 calc R . .
C17 C 0.6664(9) 0.4136(4) 0.15360(17) 0.0922(18) Uani 1 1 d . . .
H17A H 0.6578 0.3887 0.1230 0.138 Uiso 1 1 calc R . .
H17B H 0.7225 0.3687 0.1745 0.138 Uiso 1 1 calc R . .
H17C H 0.7645 0.4646 0.1535 0.138 Uiso 1 1 calc R . .
C18 C 0.2695(6) 0.4765(2) 0.31949(12) 0.0406(8) Uani 1 1 d . . .
C19 C 0.0916(8) 0.3294(3) 0.29169(14) 0.0554(11) Uani 1 1 d . . .
C20 C 0.3870(8) 0.2402(3) 0.31131(15) 0.0693(13) Uani 1 1 d . . .
H20A H 0.4976 0.2431 0.2869 0.083 Uiso 1 1 calc R . .
H20B H 0.4106 0.1858 0.3292 0.083 Uiso 1 1 calc R . .
C21 C 0.3975(7) 0.3225(3) 0.34159(12) 0.0457(9) Uani 1 1 d . . .
H21 H 0.5490 0.3471 0.3423 0.055 Uiso 1 1 calc R . .
C22 C 0.3129(6) 0.3047(3) 0.39076(12) 0.0475(10) Uani 1 1 d . . .
H22A H 0.2979 0.3616 0.4069 0.057 Uiso 1 1 calc R . .
H22B H 0.1666 0.2772 0.3891 0.057 Uiso 1 1 calc R . .
C23 C 0.4662(6) 0.2441(3) 0.41779(11) 0.0446(9) Uani 1 1 d . . .
C24 C 0.4097(7) 0.1554(3) 0.42803(14) 0.0571(11) Uani 1 1 d . . .
H24 H 0.2734 0.1327 0.4182 0.069 Uiso 1 1 calc R . .
C25 C 0.5538(8) 0.1005(3) 0.45275(16) 0.0667(12) Uani 1 1 d . . .
H25 H 0.5144 0.0412 0.4590 0.080 Uiso 1 1 calc R . .
C26 C 0.7563(8) 0.1337(3) 0.46819(15) 0.0627(12) Uani 1 1 d . . .
H26 H 0.8524 0.0971 0.4850 0.075 Uiso 1 1 calc R . .
C27 C 0.8143(7) 0.2221(3) 0.45838(13) 0.0543(10) Uani 1 1 d . . .
H27 H 0.9489 0.2452 0.4689 0.065 Uiso 1 1 calc R . .
C28 C 0.6721(6) 0.2756(3) 0.43293(12) 0.0470(9) Uani 1 1 d . . .
H28 H 0.7147 0.3342 0.4257 0.056 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
O1 C8 1.342(4) . ?
O1 C7 1.440(5) . ?
O2 C8 1.214(5) . ?
O3 C18 1.210(4) . ?
O4 C19 1.208(5) . ?
O5 C19 1.354(6) . ?
O5 C20 1.459(6) . ?
N1 C19 1.394(5) . ?
N1 C18 1.409(6) . ?
N1 C21 1.482(5) . ?
C1 C6 1.363(6) . ?
C1 C2 1.373(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(5) . ?
C4 C7 1.495(5) . ?
C5 C6 1.386(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.494(5) . ?
C9 C10 1.327(6) . ?
C9 C11 1.506(5) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 C12 1.564(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C18 1.536(5) . ?
C12 C13 1.536(6) . ?
C12 C14 1.543(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.533(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.514(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.528(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C20 C21 1.505(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.533(5) . ?
C21 H21 0.9800 . ?
C22 C23 1.506(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.390(6) . ?
C23 C28 1.392(6) . ?
C24 C25 1.387(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.386(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.379(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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
C8 O1 C7 115.0(3) . . ?
C19 O5 C20 108.6(4) . . ?
C19 N1 C18 131.8(3) . . ?
C19 N1 C21 108.8(3) . . ?
C18 N1 C21 119.2(3) . . ?
C6 C1 C2 119.7(4) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 120.2(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.5(4) . . ?
C3 C4 C7 121.1(3) . . ?
C5 C4 C7 120.3(4) . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 120.7(4) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O1 C7 C4 109.3(3) . . ?
O1 C7 H7A 109.8 . . ?
C4 C7 H7A 109.8 . . ?
O1 C7 H7B 109.8 . . ?
C4 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
O2 C8 O1 124.0(3) . . ?
O2 C8 C9 123.2(3) . . ?
O1 C8 C9 112.9(3) . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 C11 123.0(3) . . ?
C8 C9 C11 116.1(3) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C9 C11 C12 116.4(3) . . ?
C9 C11 H11A 108.2 . . ?
C12 C11 H11A 108.2 . . ?
C9 C11 H11B 108.2 . . ?
C12 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C18 C12 C13 107.5(3) . . ?
C18 C12 C14 113.1(3) . . ?
C13 C12 C14 109.4(3) . . ?
C18 C12 C11 110.7(3) . . ?
C13 C12 C11 108.0(3) . . ?
C14 C12 C11 108.0(3) . . ?
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 C12 116.3(3) . . ?
C15 C14 H14A 108.2 . . ?
C12 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C12 C14 H14B 108.2 . . ?
H14A C14 H14B 107.4 . . ?
C16 C15 C14 112.9(3) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 113.3(4) . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 N1 116.1(3) . . ?
O3 C18 C12 121.3(3) . . ?
N1 C18 C12 122.3(3) . . ?
O4 C19 O5 122.0(4) . . ?
O4 C19 N1 129.3(4) . . ?
O5 C19 N1 108.7(4) . . ?
O5 C20 C21 103.7(3) . . ?
O5 C20 H20A 111.0 . . ?
C21 C20 H20A 111.0 . . ?
O5 C20 H20B 111.0 . . ?
C21 C20 H20B 111.0 . . ?
H20A C20 H20B 109.0 . . ?
N1 C21 C20 99.1(3) . . ?
N1 C21 C22 112.5(3) . . ?
C20 C21 C22 112.7(4) . . ?
N1 C21 H21 110.7 . . ?
C20 C21 H21 110.7 . . ?
C22 C21 H21 110.7 . . ?
C23 C22 C21 112.5(3) . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C28 117.9(4) . . ?
C24 C23 C22 121.8(4) . . ?
C28 C23 C22 120.3(4) . . ?
C25 C24 C23 120.9(4) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C27 C26 C25 119.4(4) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C28 C27 C26 119.9(4) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C23 121.6(4) . . ?
C27 C28 H28 119.2 . . ?
C23 C28 H28 119.2 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        24.14
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.053
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'Hexane and ethyl acetate'
