# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

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#                                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
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data_gar6954

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.31
_chemical_absolute_configuration .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.2054(1)
_cell_length_b                   10.5740(1)
_cell_length_c                   8.6556(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.960(1)
_cell_angle_gamma                90.00
_cell_volume                     746.934(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    1080
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8021
_exptl_absorpt_correction_T_max  0.9298
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3697
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         7.86
_diffrn_reflns_theta_max         67.01
_reflns_number_total             2081
_reflns_number_gt                2077
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0410P)^2^+0.1097P] 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    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(17)
_refine_ls_number_reflns         2081
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.24500(14) 0.82356(12) 0.90648(13) 0.0417(3) Uani 1 1 d . . .
N1 N 0.17917(19) 0.64511(18) 0.48014(18) 0.0499(4) Uani 1 1 d . . .
O2 O 0.02702(17) 0.69881(17) 0.41787(17) 0.0656(5) Uani 1 1 d . . .
O3 O 0.72916(15) 0.68069(14) 0.79604(17) 0.0528(4) Uani 1 1 d . . .
O4 O 0.75683(14) 0.48790(11) 0.70025(14) 0.0430(3) Uani 1 1 d . . .
O5 O 0.5489(2) 0.78351(13) 0.43721(16) 0.0558(4) Uani 1 1 d . . .
O6 O 0.61313(15) 0.59070(12) 0.35915(13) 0.0425(3) Uani 1 1 d . . .
C1 C 0.35602(18) 0.62261(16) 0.83992(17) 0.0337(4) Uani 1 1 d . . .
C2 C 0.27957(18) 0.69748(17) 0.94324(19) 0.0364(4) Uani 1 1 d . . .
C3 C 0.2401(2) 0.6499(2) 1.0833(2) 0.0455(4) Uani 1 1 d . . .
H3 H 0.1911 0.7023 1.1530 0.055 Uiso 1 1 calc R . .
C4 C 0.2732(2) 0.5247(2) 1.1200(2) 0.0468(5) Uani 1 1 d . . .
H4 H 0.2473 0.4920 1.2155 0.056 Uiso 1 1 calc R . .
C5 C 0.3437(2) 0.44789(19) 1.0179(2) 0.0446(4) Uani 1 1 d . . .
H5 H 0.3638 0.3623 1.0425 0.053 Uiso 1 1 calc R . .
C6 C 0.3853(2) 0.49647(17) 0.87849(19) 0.0391(4) Uani 1 1 d . . .
H6 H 0.4340 0.4434 0.8092 0.047 Uiso 1 1 calc R . .
C7 C 0.39703(18) 0.68200(16) 0.68926(17) 0.0328(3) Uani 1 1 d . . .
H7 H 0.4503 0.7641 0.7168 0.039 Uiso 1 1 calc R . .
C8 C 0.23780(19) 0.71132(16) 0.59397(18) 0.0352(4) Uani 1 1 d . . .
C9 C 0.13754(19) 0.82413(18) 0.6288(2) 0.0404(4) Uani 1 1 d . . .
H9 H 0.1916 0.9019 0.5959 0.049 Uiso 1 1 calc R . .
C10 C -0.0159(2) 0.7991(2) 0.5193(2) 0.0554(6) Uani 1 1 d . . .
H10A H -0.1065 0.7730 0.5775 0.066 Uiso 1 1 calc R . .
H10B H -0.0488 0.8752 0.4593 0.066 Uiso 1 1 calc R . .
C11 C 0.1018(2) 0.83792(19) 0.7980(2) 0.0432(4) Uani 1 1 d . . .
H11A H 0.0539 0.9215 0.8123 0.052 Uiso 1 1 calc R . .
H11B H 0.0207 0.7742 0.8204 0.052 Uiso 1 1 calc R . .
C12 C 0.51903(19) 0.60483(15) 0.60488(18) 0.0335(4) Uani 1 1 d . . .
H12 H 0.4752 0.5192 0.5798 0.040 Uiso 1 1 calc R . .
C13 C 0.67859(19) 0.59660(17) 0.71217(18) 0.0351(4) Uani 1 1 d . . .
C14 C 0.9102(2) 0.4777(2) 0.7994(2) 0.0506(5) Uani 1 1 d . . .
H14A H 0.9883 0.5380 0.7658 0.076 Uiso 1 1 calc R . .
H14B H 0.9534 0.3927 0.7926 0.076 Uiso 1 1 calc R . .
H14C H 0.8913 0.4955 0.9060 0.076 Uiso 1 1 calc R . .
C15 C 0.55916(18) 0.67214(16) 0.45813(19) 0.0345(4) Uani 1 1 d . . .
C16 C 0.6632(2) 0.6433(2) 0.2167(2) 0.0474(4) Uani 1 1 d . . .
H16A H 0.5775 0.6982 0.1691 0.071 Uiso 1 1 calc R . .
H16B H 0.6824 0.5752 0.1457 0.071 Uiso 1 1 calc R . .
H16C H 0.7632 0.6917 0.2400 0.071 Uiso 1 1 calc R . .

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
O1 0.0392(6) 0.0409(7) 0.0446(6) -0.0063(5) 0.0028(5) 0.0020(5)
N1 0.0470(8) 0.0573(10) 0.0429(8) -0.0019(7) -0.0066(6) -0.0010(7)
O2 0.0510(8) 0.0829(12) 0.0575(9) -0.0050(8) -0.0189(6) 0.0023(8)
O3 0.0395(6) 0.0498(8) 0.0667(8) -0.0218(7) -0.0051(6) 0.0016(6)
O4 0.0434(6) 0.0377(7) 0.0467(6) -0.0011(5) -0.0010(5) 0.0063(6)
O5 0.0775(9) 0.0387(8) 0.0550(8) 0.0055(6) 0.0257(7) 0.0046(7)
O6 0.0537(7) 0.0417(6) 0.0332(6) 0.0018(5) 0.0099(5) 0.0085(6)
C1 0.0280(7) 0.0399(10) 0.0328(8) -0.0020(7) 0.0007(6) -0.0039(6)
C2 0.0314(7) 0.0404(9) 0.0370(8) -0.0034(7) 0.0017(6) -0.0021(7)
C3 0.0410(9) 0.0591(12) 0.0369(9) -0.0041(8) 0.0063(7) -0.0016(9)
C4 0.0431(9) 0.0628(13) 0.0350(8) 0.0057(8) 0.0056(7) -0.0070(9)
C5 0.0454(9) 0.0463(10) 0.0417(9) 0.0072(8) 0.0032(7) -0.0052(8)
C6 0.0408(8) 0.0393(9) 0.0375(8) 0.0007(7) 0.0053(6) -0.0017(8)
C7 0.0329(7) 0.0321(8) 0.0335(8) -0.0016(6) 0.0039(6) -0.0011(7)
C8 0.0342(8) 0.0378(9) 0.0340(8) 0.0039(7) 0.0057(6) -0.0049(7)
C9 0.0329(8) 0.0422(10) 0.0461(9) 0.0071(8) 0.0039(7) 0.0005(8)
C10 0.0376(9) 0.0809(16) 0.0465(11) 0.0110(10) -0.0006(8) 0.0062(10)
C11 0.0349(8) 0.0447(10) 0.0500(10) -0.0012(8) 0.0051(7) 0.0047(8)
C12 0.0346(7) 0.0319(8) 0.0343(8) -0.0015(7) 0.0040(6) -0.0023(7)
C13 0.0352(8) 0.0363(8) 0.0349(8) 0.0004(7) 0.0090(6) -0.0023(7)
C14 0.0431(9) 0.0502(11) 0.0572(11) 0.0092(9) -0.0012(8) 0.0064(9)
C15 0.0319(7) 0.0353(9) 0.0363(8) 0.0003(7) 0.0034(6) 0.0011(7)
C16 0.0502(10) 0.0591(11) 0.0339(9) 0.0048(8) 0.0095(7) 0.0043(9)

_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 1.393(2) . ?
O1 C11 1.434(2) . ?
N1 C8 1.263(2) . ?
N1 O2 1.425(2) . ?
O2 C10 1.443(3) . ?
O3 C13 1.195(2) . ?
O4 C13 1.326(2) . ?
O4 C14 1.452(2) . ?
O5 C15 1.193(2) . ?
O6 C15 1.323(2) . ?
O6 C16 1.450(2) . ?
C1 C6 1.390(2) . ?
C1 C2 1.392(2) . ?
C1 C7 1.516(2) . ?
C2 C3 1.382(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.503(2) . ?
C7 C12 1.534(2) . ?
C7 H7 0.9900 . ?
C8 C9 1.497(2) . ?
C9 C10 1.519(2) . ?
C9 C11 1.531(3) . ?
C9 H9 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C15 1.522(2) . ?
C12 C13 1.527(2) . ?
C12 H12 0.9900 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?

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 C11 112.61(13) . . ?
C8 N1 O2 108.78(17) . . ?
N1 O2 C10 108.80(13) . . ?
C13 O4 C14 114.57(14) . . ?
C15 O6 C16 116.39(15) . . ?
C6 C1 C2 118.03(15) . . ?
C6 C1 C7 123.76(15) . . ?
C2 C1 C7 118.17(15) . . ?
C3 C2 C1 121.25(17) . . ?
C3 C2 O1 119.23(15) . . ?
C1 C2 O1 119.50(15) . . ?
C4 C3 C2 119.51(18) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.34(18) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.98(19) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.83(17) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C8 C7 C1 107.43(12) . . ?
C8 C7 C12 114.93(13) . . ?
C1 C7 C12 113.78(14) . . ?
C8 C7 H7 106.7 . . ?
C1 C7 H7 106.7 . . ?
C12 C7 H7 106.7 . . ?
N1 C8 C9 115.21(15) . . ?
N1 C8 C7 123.56(16) . . ?
C9 C8 C7 121.22(14) . . ?
C8 C9 C10 99.97(15) . . ?
C8 C9 C11 115.61(14) . . ?
C10 C9 C11 112.64(14) . . ?
C8 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
C11 C9 H9 109.4 . . ?
O2 C10 C9 105.58(15) . . ?
O2 C10 H10A 110.6 . . ?
C9 C10 H10A 110.6 . . ?
O2 C10 H10B 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
O1 C11 C9 113.00(13) . . ?
O1 C11 H11A 109.0 . . ?
C9 C11 H11A 109.0 . . ?
O1 C11 H11B 109.0 . . ?
C9 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C15 C12 C13 106.75(12) . . ?
C15 C12 C7 110.92(13) . . ?
C13 C12 C7 107.55(12) . . ?
C15 C12 H12 110.5 . . ?
C13 C12 H12 110.5 . . ?
C7 C12 H12 110.5 . . ?
O3 C13 O4 123.51(15) . . ?
O3 C13 C12 123.29(15) . . ?
O4 C13 C12 113.18(14) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 O6 124.55(16) . . ?
O5 C15 C12 124.78(16) . . ?
O6 C15 C12 110.62(14) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 O2 C10 -7.6(2) . . . . ?
C6 C1 C2 C3 2.8(2) . . . . ?
C7 C1 C2 C3 -179.38(14) . . . . ?
C6 C1 C2 O1 -178.54(14) . . . . ?
C7 C1 C2 O1 -0.7(2) . . . . ?
C11 O1 C2 C3 -102.49(16) . . . . ?
C11 O1 C2 C1 78.80(17) . . . . ?
C1 C2 C3 C4 -1.7(2) . . . . ?
O1 C2 C3 C4 179.64(15) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C2 C1 C6 C5 -1.8(2) . . . . ?
C7 C1 C6 C5 -179.53(15) . . . . ?
C6 C1 C7 C8 110.84(17) . . . . ?
C2 C1 C7 C8 -66.88(18) . . . . ?
C6 C1 C7 C12 -17.5(2) . . . . ?
C2 C1 C7 C12 164.73(13) . . . . ?
O2 N1 C8 C9 -1.0(2) . . . . ?
O2 N1 C8 C7 179.38(14) . . . . ?
C1 C7 C8 N1 -102.74(19) . . . . ?
C12 C7 C8 N1 25.0(2) . . . . ?
C1 C7 C8 C9 77.70(18) . . . . ?
C12 C7 C8 C9 -154.58(14) . . . . ?
N1 C8 C9 C10 8.4(2) . . . . ?
C7 C8 C9 C10 -171.96(15) . . . . ?
N1 C8 C9 C11 129.62(17) . . . . ?
C7 C8 C9 C11 -50.8(2) . . . . ?
N1 O2 C10 C9 12.6(2) . . . . ?
C8 C9 C10 O2 -12.00(18) . . . . ?
C11 C9 C10 O2 -135.28(16) . . . . ?
C2 O1 C11 C9 -84.77(18) . . . . ?
C8 C9 C11 O1 48.3(2) . . . . ?
C10 C9 C11 O1 162.40(16) . . . . ?
C8 C7 C12 C15 57.60(17) . . . . ?
C1 C7 C12 C15 -177.96(13) . . . . ?
C8 C7 C12 C13 173.98(14) . . . . ?
C1 C7 C12 C13 -61.57(16) . . . . ?
C14 O4 C13 O3 0.6(2) . . . . ?
C14 O4 C13 C12 179.26(14) . . . . ?
C15 C12 C13 O3 83.5(2) . . . . ?
C7 C12 C13 O3 -35.6(2) . . . . ?
C15 C12 C13 O4 -95.13(15) . . . . ?
C7 C12 C13 O4 145.78(13) . . . . ?
C16 O6 C15 O5 0.3(2) . . . . ?
C16 O6 C15 C12 -177.26(13) . . . . ?
C13 C12 C15 O5 -91.9(2) . . . . ?
C7 C12 C15 O5 24.9(2) . . . . ?
C13 C12 C15 O6 85.64(15) . . . . ?
C7 C12 C15 O6 -157.49(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.890
_diffrn_reflns_theta_full        67.01
_diffrn_measured_fraction_theta_full 0.890
_refine_diff_density_max         0.096
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.023
#=============================================================================
#  end of cif data for "gar6954" (compound 5a)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
_database_code_depnum_ccdc_archive 'CCDC 961434'