# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_FM104
_database_code_depnum_ccdc_archive 'CCDC 1060015'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-05-14 downloaded from the CCDC.
;

_audit_creation_date             2015-04-16
_audit_creation_method           SHELXL-2014/4
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_name_systematic        
'(3aR,6aS)-5-((S)-4-amino-4-carboxybutanoyl)-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole-3-carboxylic acid'
_chemical_melting_point          '> 353 (decomposition)'
_chemical_formula_moiety         "(C11 H14 N3 O6)','H2O"
_chemical_formula_sum            'C11 H16 N3 O7'
_chemical_formula_weight         302.27

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.4380(7)
_cell_length_b                   10.4231(15)
_cell_length_c                   22.933(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1299.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    341
_cell_measurement_theta_min      3.851
_cell_measurement_theta_max      13.333

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8953
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'Sadabs (Bruker, 2008/1)'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart Apex II'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            19388
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.776
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2982
_reflns_number_gt                1573
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_cell_refinement       'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_data_reduction        'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_structure_solution    'SHELXS-2013   (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/4 (Sheldrick, 2014)'
_computing_molecular_graphics    
'DIAMOND v3.2i (Brandenburg, Bonn (Germany) 1997-2012)'
_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     
'w=1/[σ²(Fo²)+(0.0346P)²+0.0178P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 483 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2982
_refine_ls_number_parameters     259
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.005
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6203(8) 0.6066(5) 0.77530(18) 0.0364(11) Uani 1 1 d . . . . .
C2 C 0.3915(8) 0.5987(4) 0.73691(18) 0.0310(10) Uani 1 1 d . . . . .
C3 C 0.4501(9) 0.5355(5) 0.67916(19) 0.0368(12) Uani 1 1 d . . . . .
C4 C 0.2261(9) 0.5183(5) 0.6408(2) 0.0405(12) Uani 1 1 d . . . . .
C5 C 0.2809(9) 0.4495(4) 0.58414(19) 0.0371(12) Uani 1 1 d . . . . .
C6 C -0.0812(9) 0.5614(5) 0.5409(2) 0.0437(14) Uani 1 1 d . . . . .
C7 C -0.1778(9) 0.5638(5) 0.47825(19) 0.0395(12) Uani 1 1 d . . . . .
C8 C 0.0041(8) 0.4897(5) 0.44055(17) 0.0335(11) Uani 1 1 d . . . . .
C9 C 0.1601(10) 0.4098(4) 0.48246(17) 0.0347(11) Uani 1 1 d . . . . .
C10 C 0.1267(8) 0.6009(4) 0.40986(17) 0.0324(10) Uani 1 1 d . . . . .
C11 C 0.3391(8) 0.5998(5) 0.36870(17) 0.0355(11) Uani 1 1 d . . . . .
N1 N 0.2981(11) 0.7330(4) 0.7303(2) 0.0506(13) Uani 1 1 d . . . . .
N2 N 0.1402(6) 0.4792(3) 0.53832(13) 0.0326(9) Uani 1 1 d . . . . .
N3 N 0.0233(7) 0.7099(4) 0.41868(15) 0.0483(11) Uani 1 1 d . . . . .
O1 O 0.6832(6) 0.4961(3) 0.79729(12) 0.0464(9) Uani 1 1 d . . . . .
O2 O 0.7309(7) 0.7057(3) 0.78255(15) 0.0649(11) Uani 1 1 d . . . . .
O3 O 0.4486(7) 0.3697(3) 0.57889(13) 0.0539(10) Uani 1 1 d . . . . .
O4 O -0.1766(6) 0.6939(3) 0.45664(14) 0.0626(11) Uani 1 1 d . . . . .
O5 O 0.3942(7) 0.6980(3) 0.34252(15) 0.0681(12) Uani 1 1 d . . . . .
O6 O 0.4499(5) 0.4920(3) 0.36368(11) 0.0408(8) Uani 1 1 d . . . . .
H1OX H 0.861(11) 0.505(6) 0.827(2) 0.106(18) Uiso 1 1 d . . . . .
H9B H 0.343(8) 0.401(4) 0.4724(15) 0.039(12) Uiso 1 1 d . . . . .
H1NA H 0.151(11) 0.746(5) 0.701(2) 0.085(17) Uiso 1 1 d . U . . .
H1NB H 0.423(9) 0.770(5) 0.717(2) 0.057(18) Uiso 1 1 d . U . . .
H1NC H 0.233(12) 0.765(6) 0.772(3) 0.13(2) Uiso 1 1 d . U . . .
H2 H 0.267(7) 0.548(4) 0.7590(17) 0.039(13) Uiso 1 1 d . . . . .
H3A H 0.573(8) 0.586(4) 0.6585(18) 0.055(15) Uiso 1 1 d . . . . .
H3B H 0.551(9) 0.445(5) 0.6857(19) 0.079(17) Uiso 1 1 d . . . . .
H4A H 0.148(9) 0.612(5) 0.6333(19) 0.073(16) Uiso 1 1 d . . . . .
H4B H 0.090(9) 0.475(4) 0.6596(18) 0.062(16) Uiso 1 1 d . . . . .
H6A H -0.213(9) 0.511(5) 0.5662(19) 0.075(17) Uiso 1 1 d . . . . .
H6B H -0.034(9) 0.656(5) 0.552(2) 0.072(16) Uiso 1 1 d . . . . .
H7 H -0.357(9) 0.535(4) 0.4782(16) 0.052(13) Uiso 1 1 d . . . . .
H8 H -0.071(8) 0.432(4) 0.4143(16) 0.046(13) Uiso 1 1 d . . . . .
H9A H 0.078(9) 0.318(4) 0.4869(18) 0.065(15) Uiso 1 1 d . . . . .
O7 O 0.8021(8) 0.2759(4) 0.65210(17) 0.0612(11) Uani 1 1 d . . . . .
H7OA H 0.690(12) 0.307(5) 0.627(2) 0.09(2) Uiso 1 1 d . U . . .
H7OB H 0.868(15) 0.197(7) 0.648(3) 0.13(3) Uiso 1 1 d . U . . .


_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 O2 1.207(5) . ?
C1 O1 1.303(5) . ?
C1 C2 1.526(6) . ?
C2 N1 1.496(6) . ?
C2 C3 1.513(6) . ?
C2 H2 0.99(4) . ?
C3 C4 1.513(6) . ?
C3 H3A 0.97(5) . ?
C3 H3B 1.10(5) . ?
C4 C5 1.514(6) . ?
C4 H4A 1.08(5) . ?
C4 H4B 0.97(5) . ?
C5 O3 1.240(5) . ?
C5 N2 1.336(5) . ?
C6 N2 1.479(5) . ?
C6 C7 1.529(6) . ?
C6 H6A 1.06(5) . ?
C6 H6B 1.05(5) . ?
C7 O4 1.444(5) . ?
C7 C8 1.524(6) . ?
C7 H7 1.02(5) . ?
C8 C10 1.511(6) . ?
C8 C9 1.529(6) . ?
C8 H8 0.95(4) . ?
C9 N2 1.475(5) . ?
C9 H9B 1.02(4) . ?
C9 H9A 1.07(5) . ?
C10 N3 1.284(5) . ?
C10 C11 1.492(6) . ?
C11 O5 1.224(5) . ?
C11 O6 1.280(5) . ?
N1 H1NA 1.06(6) . ?
N1 H1NB 0.84(5) . ?
N1 H1NC 1.07(7) . ?
N3 O4 1.402(5) . ?
O1 H1OX 1.19(6) . ?
O7 H7OA 0.90(6) . ?
O7 H7OB 0.90(7) . ?

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
O2 C1 O1 124.9(4) . . ?
O2 C1 C2 122.1(4) . . ?
O1 C1 C2 113.0(4) . . ?
N1 C2 C3 113.0(4) . . ?
N1 C2 C1 106.6(4) . . ?
C3 C2 C1 110.9(4) . . ?
N1 C2 H2 108(2) . . ?
C3 C2 H2 111(2) . . ?
C1 C2 H2 107(2) . . ?
C2 C3 C4 113.0(4) . . ?
C2 C3 H3A 110(3) . . ?
C4 C3 H3A 109(3) . . ?
C2 C3 H3B 111(2) . . ?
C4 C3 H3B 112(2) . . ?
H3A C3 H3B 101(3) . . ?
C5 C4 C3 113.4(4) . . ?
C5 C4 H4A 112(2) . . ?
C3 C4 H4A 108(3) . . ?
C5 C4 H4B 108(3) . . ?
C3 C4 H4B 114(3) . . ?
H4A C4 H4B 101(4) . . ?
O3 C5 N2 120.0(4) . . ?
O3 C5 C4 123.1(4) . . ?
N2 C5 C4 116.9(4) . . ?
N2 C6 C7 104.6(4) . . ?
N2 C6 H6A 107(3) . . ?
C7 C6 H6A 107(2) . . ?
N2 C6 H6B 111(3) . . ?
C7 C6 H6B 108(3) . . ?
H6A C6 H6B 119(4) . . ?
O4 C7 C8 106.1(4) . . ?
O4 C7 C6 109.6(4) . . ?
C8 C7 C6 107.5(4) . . ?
O4 C7 H7 106(2) . . ?
C8 C7 H7 118(2) . . ?
C6 C7 H7 109(2) . . ?
C10 C8 C7 99.3(4) . . ?
C10 C8 C9 117.8(4) . . ?
C7 C8 C9 106.2(3) . . ?
C10 C8 H8 113(2) . . ?
C7 C8 H8 114(3) . . ?
C9 C8 H8 107(2) . . ?
N2 C9 C8 103.8(3) . . ?
N2 C9 H9B 108(2) . . ?
C8 C9 H9B 116(2) . . ?
N2 C9 H9A 109(2) . . ?
C8 C9 H9A 109(3) . . ?
H9B C9 H9A 110(4) . . ?
N3 C10 C11 116.5(4) . . ?
N3 C10 C8 114.3(4) . . ?
C11 C10 C8 129.1(4) . . ?
O5 C11 O6 125.1(4) . . ?
O5 C11 C10 119.5(4) . . ?
O6 C11 C10 115.4(4) . . ?
C2 N1 H1NA 116(3) . . ?
C2 N1 H1NB 101(4) . . ?
H1NA N1 H1NB 108(4) . . ?
C2 N1 H1NC 109(4) . . ?
H1NA N1 H1NC 106(5) . . ?
H1NB N1 H1NC 117(5) . . ?
C5 N2 C9 121.8(3) . . ?
C5 N2 C6 124.7(4) . . ?
C9 N2 C6 112.2(3) . . ?
C10 N3 O4 109.4(3) . . ?
C1 O1 H1OX 111(3) . . ?
N3 O4 C7 109.2(3) . . ?
H7OA O7 H7OB 121(6) . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.046

#--------------------------------------------------------------------
_vrf_PLAT417_FM104               
;
PROBLEM: Short Inter D-H..H-D       H1NC   ..  H7OB    ..       2.04 Ang.  
RESPONSE: Atom H1NC is bonded to the amine N1 Nitrogen and is an acidic 
proton involved in a strong hydrogen bond with the water molecule 
(dH1NC...O7 = 1.76 \%A, \aN1-H1NC-O7 = 159 deg, dN1-H1NC = 1.07 \%A). 
;


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
