# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  from this site to visualise CIF-encoded structures and 
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data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
(S)-5-{(S)-[(S)-2,2-Diethyl-1,3-dioxolan-4-yl][(2-meth
oxyphenyl)amino]methyl}pyrrolidin-2-one
;
_chemical_name_common            ?
_chemical_melting_point          390.6
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H28 N2 O4'
_chemical_formula_weight         348.43
_chemical_absolute_configuration syn

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   P21

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

_cell_length_a                   8.9990(10)
_cell_length_b                   8.0570(10)
_cell_length_c                   14.015(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.34(4)
_cell_angle_gamma                90.00
_cell_volume                     980.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2047
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         25.61
_reflns_number_total             1979
_reflns_number_gt                1797
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.1404P)^2^+0.0717P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.039(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_number_reflns         1979
_refine_ls_number_parameters     255
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1875
_refine_ls_wR_factor_gt          0.1802
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001

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
O2 O 0.3692(4) -0.0766(4) 0.1844(3) 0.0901(11) Uani 1 1 d . . .
N2 N 0.6632(3) 0.1883(4) 0.3441(2) 0.0588(7) Uani 1 1 d . . .
O4 O 0.7899(3) 0.3859(5) 0.4904(2) 0.0826(9) Uani 1 1 d . . .
N1 N 0.5920(4) -0.1590(4) 0.4205(2) 0.0633(8) Uani 1 1 d . . .
O1 O 0.4477(4) -0.3627(4) 0.4681(3) 0.0847(9) Uani 1 1 d . . .
C5 C 0.6055(4) 0.0416(4) 0.2861(3) 0.0549(7) Uani 1 1 d . . .
C13 C 0.8673(4) 0.3771(5) 0.4198(3) 0.0601(8) Uani 1 1 d . . .
C6 C 0.4293(4) 0.0557(6) 0.2500(3) 0.0639(8) Uani 1 1 d . . .
O3 O 0.2409(5) 0.1547(6) 0.1150(3) 0.1082(14) Uani 1 1 d . . .
C12 C 0.9993(4) 0.4671(6) 0.4182(4) 0.0743(11) Uani 1 1 d . . .
H25 H 1.0422 0.5393 0.4699 0.089 Uiso 1 1 calc R . .
C8 C 0.7984(3) 0.2683(4) 0.3409(2) 0.0535(7) Uani 1 1 d . . .
C4 C 0.6656(4) -0.1209(5) 0.3427(3) 0.0570(8) Uani 1 1 d . . .
C1 C 0.5143(4) -0.3047(5) 0.4106(3) 0.0613(8) Uani 1 1 d . . .
C9 C 0.8693(4) 0.2545(6) 0.2640(3) 0.0696(10) Uani 1 1 d . . .
H22 H 0.8274 0.1847 0.2108 0.083 Uiso 1 1 calc R . .
C2 C 0.5230(5) -0.3834(5) 0.3141(3) 0.0677(9) Uani 1 1 d . . .
H2 H 0.4235 -0.3790 0.2657 0.081 Uiso 1 1 calc R . .
H1 H 0.5552 -0.4984 0.3243 0.081 Uiso 1 1 calc R . .
C7 C 0.3722(6) 0.2092(6) 0.1895(4) 0.0828(13) Uani 1 1 d . . .
C10 C 1.0025(5) 0.3445(9) 0.2659(3) 0.0867(14) Uani 1 1 d . . .
H23 H 1.0492 0.3322 0.2146 0.104 Uiso 1 1 calc R . .
C3 C 0.6414(5) -0.2819(5) 0.2797(3) 0.0679(10) Uani 1 1 d . . .
H3 H 0.6039 -0.2557 0.2099 0.081 Uiso 1 1 calc R . .
H4 H 0.7374 -0.3427 0.2902 0.081 Uiso 1 1 calc R . .
C11 C 1.0660(5) 0.4510(7) 0.3426(4) 0.0869(14) Uani 1 1 d . . .
H24 H 1.1539 0.5116 0.3425 0.104 Uiso 1 1 calc R . .
C14 C 0.8509(6) 0.4821(11) 0.5755(4) 0.112(2) Uani 1 1 d . . .
H28 H 0.7832 0.4767 0.6181 0.168 Uiso 1 1 calc R . .
H26 H 0.8606 0.5953 0.5566 0.168 Uiso 1 1 calc R . .
H27 H 0.9505 0.4400 0.6099 0.168 Uiso 1 1 calc R . .
C15 C 0.2386(7) -0.0216(8) 0.1095(4) 0.0931(15) Uani 1 1 d DU . .
C16 C 0.2474(10) -0.0794(14) 0.0111(6) 0.140(3) Uani 1 1 d U . .
H16A H 0.1517 -0.0502 -0.0367 0.168 Uiso 1 1 calc R . .
H16B H 0.2542 -0.1996 0.0127 0.168 Uiso 1 1 calc R . .
C17 C 0.3789(16) -0.0128(18) -0.0253(8) 0.186(5) Uani 1 1 d U . .
H17A H 0.3742 -0.0590 -0.0892 0.278 Uiso 1 1 calc R . .
H17B H 0.4749 -0.0430 0.0203 0.278 Uiso 1 1 calc R . .
H17C H 0.3715 0.1059 -0.0302 0.278 Uiso 1 1 calc R . .
C18 C 0.0894(8) -0.089(2) 0.1333(6) 0.167(5) Uani 1 1 d DU . .
H18A H 0.1006 -0.2083 0.1383 0.201 Uiso 1 1 calc R . .
H18B H 0.0922 -0.0489 0.1991 0.201 Uiso 1 1 calc R . .
C19 C -0.0558(16) -0.059(4) 0.0764(11) 0.314(14) Uani 1 1 d DU . .
H19A H -0.1290 -0.1059 0.1078 0.471 Uiso 1 1 calc R . .
H19B H -0.0687 -0.1098 0.0126 0.471 Uiso 1 1 calc R . .
H19C H -0.0723 0.0581 0.0685 0.471 Uiso 1 1 calc R . .
H9 H 0.381(5) 0.066(6) 0.302(3) 0.060(10) Uiso 1 1 d . . .
H8 H 0.635(4) 0.045(6) 0.230(3) 0.049(8) Uiso 1 1 d . . .
H7 H 0.643(4) 0.188(6) 0.405(3) 0.049(9) Uiso 1 1 d . . .
H11 H 0.452(7) 0.258(10) 0.164(4) 0.11(2) Uiso 1 1 d . . .
H10 H 0.330(8) 0.289(12) 0.242(5) 0.12(2) Uiso 1 1 d . . .
H5 H 0.761(6) -0.085(8) 0.376(3) 0.077(13) Uiso 1 1 d . . .
H6 H 0.608(6) -0.100(9) 0.465(4) 0.091(18) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0869(18) 0.0505(16) 0.105(2) -0.0005(16) -0.0247(17) -0.0082(14)
N2 0.0616(15) 0.0458(15) 0.0732(17) -0.0084(14) 0.0256(13) -0.0098(13)
O4 0.0725(15) 0.083(2) 0.0950(19) -0.0348(18) 0.0273(14) -0.0228(15)
N1 0.091(2) 0.0405(15) 0.0594(16) -0.0016(13) 0.0208(14) -0.0036(14)
O1 0.101(2) 0.0576(17) 0.110(2) 0.0245(16) 0.0526(18) 0.0094(15)
C5 0.0602(17) 0.0462(17) 0.0605(16) -0.0008(15) 0.0197(13) -0.0074(15)
C13 0.0540(15) 0.0434(16) 0.0777(19) 0.0013(15) 0.0086(14) -0.0007(14)
C6 0.0642(19) 0.058(2) 0.0669(18) 0.0012(18) 0.0124(15) -0.0074(18)
O3 0.115(3) 0.079(2) 0.101(3) -0.0046(19) -0.026(2) 0.021(2)
C12 0.0591(19) 0.057(2) 0.095(3) 0.004(2) -0.0003(18) -0.0127(17)
C8 0.0483(14) 0.0395(15) 0.0692(17) 0.0085(14) 0.0091(13) 0.0005(12)
C4 0.0575(16) 0.0450(17) 0.0675(18) -0.0023(15) 0.0148(14) -0.0046(14)
C1 0.0690(18) 0.0399(15) 0.075(2) 0.0093(15) 0.0199(16) 0.0068(15)
C9 0.0628(18) 0.074(2) 0.072(2) 0.0064(19) 0.0178(16) -0.0083(18)
C2 0.073(2) 0.0390(16) 0.086(2) -0.0047(16) 0.0122(18) -0.0003(15)
C7 0.079(2) 0.056(2) 0.104(3) 0.003(2) 0.007(2) 0.006(2)
C10 0.069(2) 0.110(4) 0.081(2) 0.016(3) 0.0211(19) -0.019(2)
C3 0.081(2) 0.047(2) 0.080(2) -0.0045(17) 0.0291(19) 0.0067(17)
C11 0.061(2) 0.090(3) 0.105(3) 0.023(3) 0.014(2) -0.020(2)
C14 0.075(3) 0.147(6) 0.108(4) -0.066(4) 0.012(2) -0.014(3)
C15 0.097(3) 0.085(3) 0.077(3) -0.007(2) -0.012(2) 0.000(3)
C16 0.142(6) 0.146(8) 0.113(5) -0.040(5) 0.001(4) 0.009(6)
C17 0.244(13) 0.181(12) 0.159(8) -0.022(8) 0.102(9) 0.006(10)
C18 0.106(4) 0.248(14) 0.126(5) -0.005(8) -0.007(4) -0.007(7)
C19 0.192(12) 0.44(4) 0.272(18) -0.09(2) -0.008(12) -0.04(2)

_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
O2 C6 1.418(5) . ?
O2 C15 1.423(6) . ?
N2 C8 1.388(4) . ?
N2 C5 1.450(5) . ?
O4 C13 1.354(5) . ?
O4 C14 1.407(6) . ?
N1 C1 1.354(5) . ?
N1 C4 1.451(5) . ?
O1 C1 1.219(5) . ?
C5 C6 1.536(5) . ?
C5 C4 1.552(5) . ?
C13 C12 1.397(5) . ?
C13 C8 1.419(5) . ?
C6 C7 1.510(6) . ?
O3 C7 1.423(6) . ?
O3 C15 1.423(7) . ?
C12 C11 1.355(7) . ?
C8 C9 1.396(5) . ?
C4 C3 1.552(5) . ?
C1 C2 1.514(6) . ?
C9 C10 1.394(6) . ?
C2 C3 1.520(6) . ?
C10 C11 1.376(8) . ?
C15 C16 1.477(9) . ?
C15 C18 1.563(11) . ?
C16 C17 1.506(15) . ?
C18 C19 1.359(14) . ?

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 O2 C15 110.1(4) . . ?
C8 N2 C5 123.2(3) . . ?
C13 O4 C14 119.2(4) . . ?
C1 N1 C4 115.6(3) . . ?
N2 C5 C6 108.0(3) . . ?
N2 C5 C4 112.1(3) . . ?
C6 C5 C4 114.9(3) . . ?
O4 C13 C12 126.1(4) . . ?
O4 C13 C8 113.5(3) . . ?
C12 C13 C8 120.4(4) . . ?
O2 C6 C7 103.7(3) . . ?
O2 C6 C5 110.0(3) . . ?
C7 C6 C5 114.4(3) . . ?
C7 O3 C15 110.2(4) . . ?
C11 C12 C13 121.2(4) . . ?
N2 C8 C9 124.9(3) . . ?
N2 C8 C13 117.9(3) . . ?
C9 C8 C13 117.1(3) . . ?
N1 C4 C3 103.2(3) . . ?
N1 C4 C5 113.3(3) . . ?
C3 C4 C5 115.9(3) . . ?
O1 C1 N1 126.5(4) . . ?
O1 C1 C2 125.5(4) . . ?
N1 C1 C2 107.9(3) . . ?
C10 C9 C8 120.7(4) . . ?
C1 C2 C3 105.3(3) . . ?
O3 C7 C6 104.6(4) . . ?
C11 C10 C9 121.1(4) . . ?
C2 C3 C4 105.9(3) . . ?
C12 C11 C10 119.5(4) . . ?
O3 C15 O2 105.8(4) . . ?
O3 C15 C16 111.2(7) . . ?
O2 C15 C16 110.6(6) . . ?
O3 C15 C18 109.5(8) . . ?
O2 C15 C18 108.9(6) . . ?
C16 C15 C18 110.6(7) . . ?
C15 C16 C17 116.4(8) . . ?
C19 C18 C15 124.2(13) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.61
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 948365'