Electronic Supplementary Information for Chemical Communications
This journal is © the Royal Society of Chemistry 2010

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  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 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
#
####################################################################### 

data_gl59f1
_database_code_depnum_ccdc_archive 'CCDC 764561'
#TrackingRef 'Compound 6a, D. BONNE.cif'


_audit_creation_date             2009-04-14T17:23:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C16 H19 N1 O6'
_chemical_formula_sum            'C16 H19 N O6'
_chemical_formula_weight         321.32
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
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                   6.92840(10)
_cell_length_b                   7.6008(2)
_cell_length_c                   31.6931(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1669.00(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7998
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      28.69
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_number            7998
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_full        28.69
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_reflns_number_total             2331
_reflns_number_gt                1498
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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^)+(0.1183P)^2^+0.0000P] 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_number_reflns         2331
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.105
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1961
_refine_ls_wR_factor_gt          0.1554
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.125

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.1491(5) 0.9395(4) 0.14451(11) 0.0443(8) Uani 1 1 d . . .
H1 H 0.0244 0.9909 0.1523 0.053 Uiso 1 1 calc R . .
C2 C 0.1199(5) 0.7448(4) 0.13138(10) 0.0392(7) Uani 1 1 d . . .
C3 C 0.3070(5) 0.6522(5) 0.14575(12) 0.0431(8) Uani 1 1 d . . .
H3A H 0.285 0.5274 0.1499 0.052 Uiso 1 1 calc R . .
H3B H 0.4084 0.6674 0.125 0.052 Uiso 1 1 calc R . .
C4 C 0.3619(5) 0.7420(4) 0.18766(11) 0.0413(8) Uani 1 1 d . . .
H4 H 0.5026 0.7524 0.1893 0.05 Uiso 1 1 calc R . .
C5 C 0.2746(5) 0.9240(4) 0.18333(12) 0.0442(8) Uani 1 1 d . . .
C6 C 0.2435(7) 1.0525(5) 0.11075(13) 0.0541(10) Uani 1 1 d . . .
C7 C 0.4387(8) 1.0529(7) 0.10248(19) 0.0844(16) Uani 1 1 d . . .
H7 H 0.5203 0.9819 0.1184 0.101 Uiso 1 1 calc R . .
C8 C 0.5145(11) 1.1563(10) 0.0712(3) 0.112(2) Uani 1 1 d . . .
H8 H 0.6464 1.1526 0.0658 0.134 Uiso 1 1 calc R . .
C9 C 0.4006(17) 1.2639(9) 0.0479(2) 0.118(3) Uani 1 1 d . . .
H9 H 0.4542 1.3356 0.0273 0.142 Uiso 1 1 calc R . .
C10 C 0.2081(16) 1.2660(7) 0.05506(19) 0.103(2) Uani 1 1 d . . .
H10 H 0.129 1.3374 0.0387 0.123 Uiso 1 1 calc R . .
C11 C 0.1282(10) 1.1639(6) 0.08632(16) 0.0752(14) Uani 1 1 d . . .
H11 H -0.004 1.169 0.0913 0.09 Uiso 1 1 calc R . .
C12 C -0.0530(5) 0.6668(5) 0.15445(12) 0.0457(9) Uani 1 1 d . . .
C13 C -0.2211(8) 0.4009(6) 0.1672(2) 0.0850(16) Uani 1 1 d . . .
H13A H -0.216 0.4248 0.197 0.128 Uiso 1 1 calc R . .
H13B H -0.2041 0.2771 0.1625 0.128 Uiso 1 1 calc R . .
H13C H -0.3441 0.437 0.1563 0.128 Uiso 1 1 calc R . .
C14 C 0.0830(6) 0.7273(5) 0.08421(12) 0.0495(9) Uani 1 1 d . . .
C15 C -0.1586(10) 0.7588(10) 0.03192(17) 0.107(2) Uani 1 1 d . . .
H15A H -0.0951 0.8511 0.0166 0.161 Uiso 1 1 calc R . .
H15B H -0.2959 0.7734 0.0297 0.161 Uiso 1 1 calc R . .
H15C H -0.1225 0.6469 0.0203 0.161 Uiso 1 1 calc R . .
C16 C 0.2883(6) 0.6478(5) 0.22695(12) 0.0482(9) Uani 1 1 d . . .
H16A H 0.3083 0.7222 0.2514 0.058 Uiso 1 1 calc R . .
H16B H 0.1508 0.6267 0.2242 0.058 Uiso 1 1 calc R . .
N1 N 0.3108(5) 1.0430(4) 0.20977(12) 0.0552(9) Uani 1 1 d . . .
O1 O -0.1567(4) 0.7450(4) 0.17810(11) 0.0765(10) Uani 1 1 d . . .
O2 O -0.0692(4) 0.4970(3) 0.14605(9) 0.0597(8) Uani 1 1 d . . .
O3 O 0.1998(5) 0.6909(4) 0.05804(9) 0.0693(9) Uani 1 1 d . . .
O4 O -0.1016(4) 0.7665(5) 0.07620(8) 0.0697(9) Uani 1 1 d . . .
O5 O 0.3853(4) 0.4846(3) 0.23304(9) 0.0568(7) Uani 1 1 d . . .
H5 H 0.4658 0.4953 0.2518 0.085 Uiso 1 1 calc R . .
O6 O 0.2107(5) 1.1999(3) 0.20030(11) 0.0758(10) Uani 1 1 d . . .
H6 H 0.265 1.2832 0.2117 0.114 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
C1 0.0426(19) 0.0485(19) 0.0417(18) -0.0057(17) -0.0120(15) 0.0067(16)
C2 0.0385(16) 0.0446(18) 0.0344(16) -0.0037(15) -0.0039(13) 0.0032(15)
C3 0.0345(16) 0.0512(19) 0.0437(19) -0.0045(16) 0.0001(15) 0.0046(15)
C4 0.0346(15) 0.0436(18) 0.0458(19) -0.0045(16) -0.0055(14) 0.0031(15)
C5 0.0445(18) 0.0431(18) 0.045(2) -0.0017(16) -0.0086(15) 0.0014(15)
C6 0.073(3) 0.0420(19) 0.047(2) 0.0019(18) -0.0114(19) -0.0002(18)
C7 0.068(3) 0.088(3) 0.097(4) 0.026(3) 0.004(3) -0.010(3)
C8 0.106(5) 0.112(5) 0.118(5) 0.018(4) 0.027(5) -0.031(4)
C9 0.182(9) 0.081(4) 0.091(5) 0.026(4) 0.009(5) -0.022(5)
C10 0.180(8) 0.058(3) 0.070(4) 0.015(3) -0.017(4) 0.007(4)
C11 0.110(4) 0.055(2) 0.061(3) 0.005(2) -0.018(3) 0.014(3)
C12 0.0383(17) 0.057(2) 0.0419(19) -0.0035(17) -0.0050(15) 0.0058(16)
C13 0.070(3) 0.073(3) 0.113(5) 0.015(3) 0.029(3) -0.009(3)
C14 0.060(2) 0.046(2) 0.042(2) -0.0027(16) -0.0061(17) -0.0023(18)
C15 0.121(5) 0.146(5) 0.056(3) -0.008(4) -0.047(3) 0.016(5)
C16 0.054(2) 0.0461(18) 0.045(2) -0.0006(16) -0.0089(17) 0.0038(17)
N1 0.066(2) 0.0364(15) 0.063(2) -0.0039(15) -0.0264(17) 0.0072(15)
O1 0.0494(15) 0.083(2) 0.098(2) -0.030(2) 0.0256(16) -0.0043(17)
O2 0.0585(16) 0.0495(15) 0.0710(19) -0.0003(14) 0.0181(14) -0.0066(13)
O3 0.086(2) 0.082(2) 0.0392(15) -0.0062(14) 0.0058(15) 0.0082(18)
O4 0.0669(18) 0.098(2) 0.0441(16) -0.0010(16) -0.0226(13) 0.0080(18)
O5 0.0687(18) 0.0428(13) 0.0589(18) 0.0005(12) -0.0254(14) 0.0009(13)
O6 0.091(2) 0.0466(15) 0.090(2) -0.0158(15) -0.0461(19) 0.0177(15)


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 C5 1.511(5) . ?
C1 C6 1.520(5) . ?
C1 C2 1.551(5) . ?
C1 H1 0.98 . ?
C2 C14 1.522(5) . ?
C2 C12 1.523(5) . ?
C2 C3 1.544(5) . ?
C3 C4 1.541(5) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 C5 1.516(5) . ?
C4 C16 1.524(5) . ?
C4 H4 0.98 . ?
C5 N1 1.258(5) . ?
C6 C7 1.378(7) . ?
C6 C11 1.398(6) . ?
C7 C8 1.371(8) . ?
C7 H7 0.93 . ?
C8 C9 1.354(10) . ?
C8 H8 0.93 . ?
C9 C10 1.353(12) . ?
C9 H9 0.93 . ?
C10 C11 1.375(9) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 O1 1.196(4) . ?
C12 O2 1.323(5) . ?
C13 O2 1.447(5) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 O3 1.191(5) . ?
C14 O4 1.338(5) . ?
C15 O4 1.459(5) . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C16 O5 1.424(4) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
N1 O6 1.412(4) . ?
O5 H5 0.82 . ?
O6 H6 0.82 . ?

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
C5 C1 C6 111.7(3) . . ?
C5 C1 C2 102.7(3) . . ?
C6 C1 C2 114.0(3) . . ?
C5 C1 H1 109.4 . . ?
C6 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
C14 C2 C12 107.8(3) . . ?
C14 C2 C3 113.0(3) . . ?
C12 C2 C3 110.0(3) . . ?
C14 C2 C1 111.6(3) . . ?
C12 C2 C1 110.2(3) . . ?
C3 C2 C1 104.2(3) . . ?
C4 C3 C2 105.1(3) . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C5 C4 C16 111.7(3) . . ?
C5 C4 C3 103.2(3) . . ?
C16 C4 C3 114.5(3) . . ?
C5 C4 H4 109.1 . . ?
C16 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
N1 C5 C1 126.9(3) . . ?
N1 C5 C4 121.1(3) . . ?
C1 C5 C4 112.0(3) . . ?
C7 C6 C11 117.0(5) . . ?
C7 C6 C1 123.9(4) . . ?
C11 C6 C1 119.1(5) . . ?
C8 C7 C6 121.0(6) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 121.1(7) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 119.4(7) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.7(7) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 120.7(7) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
O1 C12 O2 124.0(4) . . ?
O1 C12 C2 125.4(3) . . ?
O2 C12 C2 110.5(3) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 O4 124.7(4) . . ?
O3 C14 C2 126.2(4) . . ?
O4 C14 C2 109.1(3) . . ?
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 . . ?
O5 C16 C4 111.2(3) . . ?
O5 C16 H16A 109.4 . . ?
C4 C16 H16A 109.4 . . ?
O5 C16 H16B 109.4 . . ?
C4 C16 H16B 109.4 . . ?
H16A C16 H16B 108 . . ?
C5 N1 O6 111.6(3) . . ?
C12 O2 C13 117.5(3) . . ?
C14 O4 C15 115.6(4) . . ?
C16 O5 H5 109.5 . . ?
N1 O6 H6 109.5 . . ?