# Electronic Supplementary Material (ESI) for ChemComm.
# 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_scan_0m_p21_n
_database_code_depnum_ccdc_archive 'CCDC 1474384'
_audit_update_record             
;
2016-04-15 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'methyl 1,2-diallyl-3-((methoxymethoxy)methyl)-3-(2-nitrophenyl)pyrrolidine-2-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          340
_chemical_formula_moiety         'C21 H27 N2 O6'
_chemical_formula_sum            'C21 H27 N2 O6'
_chemical_formula_weight         403.45

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P12(1)/n1
_symmetry_space_group_name_Hall  '-P 2yn'

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                   12.5404(19)
_cell_length_b                   9.1067(11)
_cell_length_c                   19.609(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.204(5)
_cell_angle_gamma                90.00
_cell_volume                     2161.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4400
_cell_measurement_theta_min      2.2197
_cell_measurement_theta_max      23.7994

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             860
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7459
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_process_details   
'Sheldrick, G. M. (2008) SADABS. University of Göttingen, Germany.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'XOS X-beam microfocus source'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_measurement_device_type  'Bruker SMART X2S benchtop diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23318
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3823
_reflns_number_gt                2627
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'GIS (Bruker)'
_computing_cell_refinement       'APEX2 (Bruker, 2011); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009); XPREP (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Jmol (Jmol.org, 2008)'
_computing_publication_material  'APEX2 (Bruker, 2011)'


_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)+(0.0986P)²+0.0483P] 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_number_reflns         3823
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1833
_refine_ls_wR_factor_gt          0.1521
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.053
_refine_ls_shift/su_mean         0.006

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 0.62427(19) 0.0339(2) 0.24745(11) 0.0752(6) Uani 1 1 d . . .
O2 O 0.45546(15) 0.01700(17) 0.16268(8) 0.0472(5) Uani 1 1 d . . .
O3 O 0.22050(16) 0.38780(19) 0.00065(9) 0.0544(5) Uani 1 1 d . . .
O4 O 0.15913(18) 0.1769(2) -0.05183(9) 0.0629(6) Uani 1 1 d . . .
O5 O 0.5313(2) 0.6009(2) 0.16376(12) 0.0870(8) Uani 1 1 d . . .
O6 O 0.54434(18) 0.4088(2) 0.22661(10) 0.0658(6) Uani 1 1 d . . .
N1 N 0.15282(16) 0.2126(2) 0.11181(10) 0.0423(5) Uani 1 1 d . . .
N2 N 0.53032(18) 0.4686(2) 0.16987(11) 0.0478(5) Uani 1 1 d . . .
C1 C 0.6919(3) 0.0583(5) 0.2008(3) 0.1162(16) Uani 1 1 d . . .
H1A H 0.7166 -0.0363 0.1865 0.174 Uiso 1 1 calc R . .
H1B H 0.7564 0.1168 0.2248 0.174 Uiso 1 1 calc R . .
H1C H 0.6496 0.1110 0.1589 0.174 Uiso 1 1 calc R . .
C2 C 0.5323(3) -0.0518(3) 0.21861(15) 0.0618(8) Uani 1 1 d . . .
H2A H 0.4956 -0.0765 0.2561 0.074 Uiso 1 1 calc R . .
H2B H 0.5566 -0.1448 0.2013 0.074 Uiso 1 1 calc R . .
C3 C 0.3964(2) 0.1322(2) 0.18540(12) 0.0413(6) Uani 1 1 d . . .
H3A H 0.4470 0.1876 0.2241 0.050 Uiso 1 1 calc R . .
H3B H 0.3369 0.0900 0.2040 0.050 Uiso 1 1 calc R . .
C4 C 0.34582(19) 0.2369(2) 0.12402(11) 0.0341(5) Uani 1 1 d . . .
C5 C 0.23590(19) 0.1709(2) 0.07422(11) 0.0362(5) Uani 1 1 d . . .
C6 C 0.0370(2) 0.1930(3) 0.07302(14) 0.0543(7) Uani 1 1 d . . .
H6A H 0.0281 0.0968 0.0487 0.065 Uiso 1 1 calc R . .
H6B H 0.0159 0.2705 0.0365 0.065 Uiso 1 1 calc R . .
C7 C -0.0384(2) 0.1999(3) 0.12057(16) 0.0599(8) Uani 1 1 d . . .
H7 H -0.0243 0.1356 0.1601 0.072 Uiso 1 1 calc R . .
C8 C -0.1215(3) 0.2882(4) 0.11117(18) 0.0785(10) Uani 1 1 d . . .
H8A H -0.1376 0.3539 0.0721 0.094 Uiso 1 1 calc R . .
H8B H -0.1666 0.2876 0.1433 0.094 Uiso 1 1 calc R . .
C9 C 0.3019(2) 0.3754(2) 0.15532(13) 0.0427(6) Uani 1 1 d . . .
H9A H 0.3355 0.3813 0.2069 0.051 Uiso 1 1 calc R . .
H9B H 0.3212 0.4657 0.1331 0.051 Uiso 1 1 calc R . .
C10 C 0.1776(2) 0.3605(3) 0.14020(15) 0.0501(7) Uani 1 1 d . . .
H10A H 0.1535 0.3730 0.1840 0.060 Uiso 1 1 calc R . .
H10B H 0.1401 0.4350 0.1053 0.060 Uiso 1 1 calc R . .
C11 C 0.2322(2) 0.0013(2) 0.06292(12) 0.0424(6) Uani 1 1 d . . .
H11A H 0.1775 -0.0201 0.0176 0.051 Uiso 1 1 calc R . .
H11B H 0.3053 -0.0306 0.0581 0.051 Uiso 1 1 calc R . .
C12 C 0.2038(3) -0.0911(3) 0.11975(16) 0.0604(8) Uani 1 1 d . . .
H12 H 0.1479 -0.0542 0.1397 0.072 Uiso 1 1 calc R . .
C13 C 0.2469(4) -0.2125(3) 0.1433(2) 0.0996(14) Uani 1 1 d . . .
H13 H 0.2793 -0.3037 0.1611 0.119 Uiso 1 1 calc R . .
C14 C 0.2076(2) 0.2574(3) 0.00393(12) 0.0408(6) Uani 1 1 d . . .
C15 C 0.1214(4) 0.2568(4) -0.11798(15) 0.0991(14) Uani 1 1 d . . .
H15A H 0.0690 0.3332 -0.1128 0.149 Uiso 1 1 calc R . .
H15B H 0.0850 0.1887 -0.1556 0.149 Uiso 1 1 calc R . .
H15C H 0.1849 0.3023 -0.1301 0.149 Uiso 1 1 calc R . .
C16 C 0.43525(18) 0.2715(2) 0.08552(11) 0.0339(5) Uani 1 1 d . . .
C17 C 0.4411(2) 0.1926(2) 0.02542(12) 0.0392(6) Uani 1 1 d . . .
H17 H 0.3881 0.1175 0.0088 0.047 Uiso 1 1 calc R . .
C18 C 0.5197(2) 0.2183(3) -0.01105(13) 0.0472(6) Uani 1 1 d . . .
H18 H 0.5203 0.1604 -0.0512 0.057 Uiso 1 1 calc R . .
C19 C 0.5974(2) 0.3276(3) 0.01061(14) 0.0522(7) Uani 1 1 d . . .
H19 H 0.6509 0.3465 -0.0147 0.063 Uiso 1 1 calc R . .
C20 C 0.5960(2) 0.4085(3) 0.06941(14) 0.0491(6) Uani 1 1 d . . .
H20 H 0.6486 0.4845 0.0851 0.059 Uiso 1 1 calc R . .
C21 C 0.5173(2) 0.3789(2) 0.10586(12) 0.0386(6) 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
O1 C2 1.384(4) . ?
O1 C1 1.419(5) . ?
O2 C2 1.403(3) . ?
O2 C3 1.422(3) . ?
O3 C14 1.202(3) . ?
O4 C14 1.324(3) . ?
O4 C15 1.454(3) . ?
O5 N2 1.212(3) . ?
O6 N2 1.209(3) . ?
N1 C10 1.459(3) . ?
N1 C6 1.463(3) . ?
N1 C5 1.475(3) . ?
N2 C21 1.470(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.536(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C16 1.540(3) . ?
C4 C9 1.565(3) . ?
C4 C5 1.584(3) . ?
C5 C14 1.546(3) . ?
C5 C11 1.559(3) . ?
C6 C7 1.493(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.291(4) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C9 C10 1.514(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.512(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.264(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.398(3) . ?
C16 C21 1.400(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.372(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?

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 O1 C1 113.6(3) . . ?
C2 O2 C3 113.1(2) . . ?
C14 O4 C15 115.5(2) . . ?
C10 N1 C6 113.22(19) . . ?
C10 N1 C5 108.69(18) . . ?
C6 N1 C5 116.34(18) . . ?
O5 N2 O6 122.4(2) . . ?
O5 N2 C21 118.0(2) . . ?
O6 N2 C21 119.5(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 113.3(2) . . ?
O1 C2 H2A 108.9 . . ?
O2 C2 H2A 108.9 . . ?
O1 C2 H2B 108.9 . . ?
O2 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O2 C3 C4 110.75(17) . . ?
O2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
O2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C16 C4 C3 107.88(18) . . ?
C16 C4 C9 113.83(18) . . ?
C3 C4 C9 107.96(17) . . ?
C16 C4 C5 113.78(17) . . ?
C3 C4 C5 111.18(17) . . ?
C9 C4 C5 102.05(18) . . ?
N1 C5 C14 106.69(18) . . ?
N1 C5 C11 109.13(18) . . ?
C14 C5 C11 112.77(18) . . ?
N1 C5 C4 102.03(16) . . ?
C14 C5 C4 108.37(17) . . ?
C11 C5 C4 116.88(19) . . ?
N1 C6 C7 112.0(2) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 123.8(3) . . ?
C8 C7 H7 118.1 . . ?
C6 C7 H7 118.1 . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C10 C9 C4 107.54(18) . . ?
C10 C9 H9A 110.2 . . ?
C4 C9 H9A 110.2 . . ?
C10 C9 H9B 110.2 . . ?
C4 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N1 C10 C9 105.24(19) . . ?
N1 C10 H10A 110.7 . . ?
C9 C10 H10A 110.7 . . ?
N1 C10 H10B 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C12 C11 C5 116.79(19) . . ?
C12 C11 H11A 108.1 . . ?
C5 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C5 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?
C13 C12 C11 126.6(3) . . ?
C13 C12 H12 116.7 . . ?
C11 C12 H12 116.7 . . ?
C12 C13 H13 180.0 . . ?
O3 C14 O4 122.8(2) . . ?
O3 C14 C5 123.3(2) . . ?
O4 C14 C5 113.7(2) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 113.7(2) . . ?
C17 C16 C4 120.93(19) . . ?
C21 C16 C4 125.37(19) . . ?
C18 C17 C16 123.5(2) . . ?
C18 C17 H17 118.3 . . ?
C16 C17 H17 118.3 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 118.8(2) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C19 C20 C21 119.7(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 123.9(2) . . ?
C20 C21 N2 113.4(2) . . ?
C16 C21 N2 122.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.107
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.033
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'diethyl ether/pentane'
