# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

data_global
_publ_contact_author_email       D.W.YOUNG@SUSSEX.AC.UK
_publ_contact_author_name        'Dr Douglas W Young'
_journal_name_full               Org.Biomol.Chem.
_journal_coden_Cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_requested_category         FO
loop_
_publ_author_name
D.W.Young
P.B.Hitchcock
S.Rahman

data_apr396
_database_code_CSD               209172

_audit_creation_date             2003-06-06T11:07:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C18 H25 N1 O7'
_chemical_formula_sum            'C18 H25 N1 O7'
_chemical_formula_weight         367.39
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration syn

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

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   P6(1)
_symmetry_space_group_name_Hall  'P 61'
_symmetry_Int_Tables_number      169
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z-1/6'
'x-y, x, z+1/6'

_cell_length_a                   8.994(2)
_cell_length_b                   8.994(2)
_cell_length_c                   43.134(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3021.7(10)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7
_cell_measurement_theta_max      10
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_special_details           
;
?
;

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

_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_number            2787
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         21.98
_diffrn_reflns_theta_full        21.98
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             1259
_reflns_number_gt                1031
_reflns_threshold_expression     >2sigma(I)

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

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_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^)+(0.0742P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1259
_refine_ls_number_parameters     242
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_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   1(2)
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   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
O1 O 0.3618(6) 0.2716(5) 0.08974(14) 0.1038(15) Uani 1 1 d . . .
O2 O 0.2588(6) 0.1161(6) 0.13962(12) 0.1036(17) Uani 1 1 d . . .
H2 H 0.343(12) 0.210(14) 0.1290(16) 0.155 Uiso 1 1 d R . .
O3 O -0.1108(4) -0.0781(5) 0.05267(9) 0.0753(11) Uani 1 1 d . . .
O4 O -0.4327(5) -0.4064(5) 0.03104(9) 0.0730(10) Uani 1 1 d . . .
O5 O -0.2439(5) -0.4570(5) 0.05560(9) 0.0733(11) Uani 1 1 d . . .
O6 O -0.6712(6) -0.3954(10) 0.13091(13) 0.134(2) Uani 1 1 d . . .
O7 O -0.9010(5) -0.5409(6) 0.10119(10) 0.0902(13) Uani 1 1 d . . .
N N -0.1945(4) -0.2146(5) 0.09862(10) 0.0555(10) Uani 1 1 d . . .
C1 C 0.0892(6) 0.0329(6) 0.09374(13) 0.0586(13) Uani 1 1 d . . .
C2 C 0.1138(7) 0.0107(7) 0.12503(15) 0.0712(16) Uani 1 1 d . . .
C3 C -0.0128(7) -0.1229(8) 0.14183(15) 0.0747(16) Uani 1 1 d . . .
H3 H 0.008 -0.137 0.1624 0.09 Uiso 1 1 calc R . .
C4 C -0.1657(7) -0.2337(7) 0.12920(13) 0.0637(14) Uani 1 1 d . . .
C5 C -0.0739(6) -0.0833(6) 0.07948(14) 0.0588(13) Uani 1 1 d . . .
C6 C 0.2267(7) 0.1707(7) 0.07656(15) 0.0745(17) Uani 1 1 d . . .
C7 C 0.2120(9) 0.1946(9) 0.04264(19) 0.102(2) Uani 1 1 d . . .
H7A H 0.1118 0.204 0.0389 0.153 Uiso 1 1 calc R . .
H7B H 0.2027 0.0979 0.0315 0.153 Uiso 1 1 calc R . .
H7C H 0.3122 0.2975 0.0358 0.153 Uiso 1 1 calc R . .
C8 C -0.3021(8) -0.3804(9) 0.14739(16) 0.0901(18) Uani 1 1 d . . .
H8A H -0.3256 -0.4869 0.138 0.135 Uiso 1 1 calc R . .
H8B H -0.4048 -0.3728 0.1475 0.135 Uiso 1 1 calc R . .
H8C H -0.2633 -0.3757 0.1683 0.135 Uiso 1 1 calc R . .
C9 C -0.3642(6) -0.3203(6) 0.08386(12) 0.0579(13) Uani 1 1 d . . .
H9 H -0.433 -0.417 0.0978 0.069 Uiso 1 1 calc R . .
C10 C -0.4574(7) -0.2183(7) 0.08055(18) 0.0783(17) Uani 1 1 d . . .
H10A H -0.4107 -0.1431 0.0627 0.094 Uiso 1 1 calc R . .
H10B H -0.433 -0.1462 0.0987 0.094 Uiso 1 1 calc R . .
C11 C -0.6522(7) -0.3265(8) 0.07673(17) 0.0787(17) Uani 1 1 d . . .
H11 H -0.6781 -0.4091 0.0599 0.094 Uiso 1 1 calc R . .
C12 C -0.7366(8) -0.4211(9) 0.10541(17) 0.0826(18) Uani 1 1 d . . .
C13 C -0.7237(10) -0.2075(11) 0.0682(3) 0.144(4) Uani 1 1 d . . .
H13A H -0.6721 -0.1484 0.0492 0.216 Uiso 1 1 calc R . .
H13B H -0.6975 -0.1253 0.0845 0.216 Uiso 1 1 calc R . .
H13C H -0.8459 -0.2748 0.0656 0.216 Uiso 1 1 calc R . .
C14 C -0.9981(11) -0.6263(13) 0.12894(18) 0.118(3) Uani 1 1 d . . .
H14A H -0.9925 -0.5422 0.1437 0.142 Uiso 1 1 calc R . .
H14B H -0.9509 -0.6909 0.1387 0.142 Uiso 1 1 calc R . .
C15 C -1.1764(10) -0.7419(12) 0.1197(3) 0.135(3) Uani 1 1 d . . .
H15A H -1.2205 -0.6774 0.1094 0.203 Uiso 1 1 calc R . .
H15B H -1.2444 -0.7964 0.1378 0.203 Uiso 1 1 calc R . .
H15C H -1.1811 -0.8278 0.1059 0.203 Uiso 1 1 calc R . .
C16 C -0.3494(6) -0.3939(6) 0.05352(13) 0.0612(13) Uani 1 1 d . . .
C17 C -0.2315(12) -0.5395(12) 0.0276(2) 0.113(3) Uani 1 1 d . . .
H17A H -0.3462 -0.6187 0.0202 0.136 Uiso 1 1 calc R . .
H17B H -0.173 -0.453 0.0118 0.136 Uiso 1 1 calc R . .
C18 C -0.147(2) -0.625(3) 0.0322(3) 0.267(12) Uani 1 1 d . . .
H18A H -0.0397 -0.5514 0.0423 0.401 Uiso 1 1 calc R . .
H18B H -0.1257 -0.6612 0.0125 0.401 Uiso 1 1 calc R . .
H18C H -0.2149 -0.7238 0.0449 0.401 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 0.075(3) 0.076(2) 0.113(4) 0.002(3) -0.015(3) 0.002(2)
O2 0.080(3) 0.094(3) 0.096(4) -0.013(3) -0.039(3) 0.013(2)
O3 0.069(2) 0.074(2) 0.050(3) 0.0073(19) -0.005(2) 0.0113(18)
O4 0.071(2) 0.070(2) 0.065(3) -0.005(2) -0.011(2) 0.0255(18)
O5 0.073(2) 0.082(2) 0.073(3) -0.024(2) -0.012(2) 0.046(2)
O6 0.085(3) 0.234(7) 0.075(4) -0.041(4) -0.004(3) 0.073(4)
O7 0.065(2) 0.111(3) 0.081(3) -0.005(3) 0.001(2) 0.034(2)
N 0.052(2) 0.052(2) 0.055(3) -0.003(2) 0.003(2) 0.0198(19)
C1 0.057(3) 0.050(3) 0.056(4) -0.005(2) -0.002(3) 0.017(3)
C2 0.065(3) 0.065(3) 0.076(5) -0.009(3) -0.012(3) 0.027(3)
C3 0.071(4) 0.081(4) 0.058(4) 0.003(3) -0.002(3) 0.027(3)
C4 0.072(4) 0.064(3) 0.051(4) 0.007(3) 0.005(3) 0.032(3)
C5 0.058(3) 0.050(3) 0.060(4) -0.005(3) 0.002(3) 0.021(2)
C6 0.058(3) 0.054(3) 0.087(5) -0.004(3) -0.008(3) 0.010(3)
C7 0.080(4) 0.081(4) 0.093(5) 0.008(4) 0.001(4) 0.001(3)
C8 0.082(4) 0.110(5) 0.065(4) 0.020(4) 0.007(3) 0.039(4)
C9 0.051(3) 0.051(3) 0.058(3) -0.006(2) 0.000(2) 0.015(2)
C10 0.064(3) 0.067(3) 0.106(5) -0.015(3) -0.008(3) 0.035(3)
C11 0.068(3) 0.083(4) 0.094(5) -0.020(4) -0.010(3) 0.044(3)
C12 0.072(4) 0.118(5) 0.067(5) -0.030(4) -0.005(4) 0.054(4)
C13 0.085(4) 0.119(6) 0.245(13) -0.002(7) -0.029(7) 0.065(4)
C14 0.114(6) 0.165(7) 0.081(5) 0.012(6) 0.024(5) 0.074(6)
C15 0.083(5) 0.134(7) 0.150(9) -0.006(6) 0.025(5) 0.025(5)
C16 0.053(3) 0.055(3) 0.058(4) -0.002(2) -0.001(3) 0.014(2)
C17 0.125(6) 0.132(6) 0.113(7) -0.046(5) -0.005(5) 0.087(5)
C18 0.38(2) 0.41(3) 0.202(14) -0.209(17) -0.170(16) 0.34(2)

#----------------------------------------------------------------------------#
#                   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
O1 C6 1.233(7) . ?
O2 C2 1.327(7) . ?
O3 C5 1.211(6) . ?
O4 C16 1.196(6) . ?
O5 C16 1.330(6) . ?
O5 C17 1.449(8) . ?
O6 C12 1.213(8) . ?
O7 C12 1.337(8) . ?
O7 C14 1.455(9) . ?
N C4 1.371(7) . ?
N C5 1.404(6) . ?
N C9 1.479(6) . ?
C1 C2 1.398(8) . ?
C1 C6 1.442(8) . ?
C1 C5 1.445(7) . ?
C2 C3 1.377(9) . ?
C3 C4 1.346(8) . ?
C4 C8 1.498(8) . ?
C6 C7 1.494(10) . ?
C9 C16 1.502(7) . ?
C9 C10 1.528(8) . ?
C10 C11 1.529(8) . ?
C11 C12 1.478(10) . ?
C11 C13 1.544(10) . ?
C14 C15 1.464(12) . ?
C17 C18 1.339(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
C16 O5 C17 114.6(5) . . ?
C12 O7 C14 116.3(6) . . ?
C4 N C5 123.8(4) . . ?
C4 N C9 122.2(4) . . ?
C5 N C9 113.7(4) . . ?
C2 C1 C6 119.3(5) . . ?
C2 C1 C5 118.9(5) . . ?
C6 C1 C5 121.8(5) . . ?
O2 C2 C3 117.5(6) . . ?
O2 C2 C1 121.7(6) . . ?
C3 C2 C1 120.8(5) . . ?
C4 C3 C2 121.7(6) . . ?
C3 C4 N 118.9(5) . . ?
C3 C4 C8 121.6(5) . . ?
N C4 C8 119.4(5) . . ?
O3 C5 N 118.9(4) . . ?
O3 C5 C1 125.3(5) . . ?
N C5 C1 115.8(5) . . ?
O1 C6 C1 120.1(6) . . ?
O1 C6 C7 118.1(5) . . ?
C1 C6 C7 121.8(5) . . ?
N C9 C16 111.6(4) . . ?
N C9 C10 110.7(4) . . ?
C16 C9 C10 112.3(5) . . ?
C9 C10 C11 115.2(4) . . ?
C12 C11 C10 111.8(5) . . ?
C12 C11 C13 109.0(7) . . ?
C10 C11 C13 109.0(5) . . ?
O6 C12 O7 120.8(7) . . ?
O6 C12 C11 126.0(6) . . ?
O7 C12 C11 113.1(6) . . ?
O7 C14 C15 107.8(7) . . ?
O4 C16 O5 124.2(5) . . ?
O4 C16 C9 124.0(5) . . ?
O5 C16 C9 111.6(5) . . ?
C18 C17 O5 112.6(8) . . ?

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
C6 C1 C2 O2 1.9(8) . . . . ?
C5 C1 C2 O2 -178.1(5) . . . . ?
C6 C1 C2 C3 -177.8(6) . . . . ?
C5 C1 C2 C3 2.2(8) . . . . ?
O2 C2 C3 C4 178.3(6) . . . . ?
C1 C2 C3 C4 -2.0(9) . . . . ?
C2 C3 C4 N 1.3(9) . . . . ?
C2 C3 C4 C8 179.1(6) . . . . ?
C5 N C4 C3 -1.1(8) . . . . ?
C9 N C4 C3 -174.0(5) . . . . ?
C5 N C4 C8 -178.9(5) . . . . ?
C9 N C4 C8 8.2(7) . . . . ?
C4 N C5 O3 179.4(5) . . . . ?
C9 N C5 O3 -7.2(7) . . . . ?
C4 N C5 C1 1.4(7) . . . . ?
C9 N C5 C1 174.8(4) . . . . ?
C2 C1 C5 O3 -179.7(5) . . . . ?
C6 C1 C5 O3 0.3(8) . . . . ?
C2 C1 C5 N -1.9(7) . . . . ?
C6 C1 C5 N 178.2(5) . . . . ?
C2 C1 C6 O1 -2.8(9) . . . . ?
C5 C1 C6 O1 177.1(5) . . . . ?
C2 C1 C6 C7 176.3(6) . . . . ?
C5 C1 C6 C7 -3.7(9) . . . . ?
C4 N C9 C16 -131.6(5) . . . . ?
C5 N C9 C16 54.8(5) . . . . ?
C4 N C9 C10 102.5(6) . . . . ?
C5 N C9 C10 -71.1(6) . . . . ?
N C9 C10 C11 -159.1(5) . . . . ?
C16 C9 C10 C11 75.4(7) . . . . ?
C9 C10 C11 C12 68.8(7) . . . . ?
C9 C10 C11 C13 -170.6(8) . . . . ?
C14 O7 C12 O6 5.0(9) . . . . ?
C14 O7 C12 C11 -173.4(6) . . . . ?
C10 C11 C12 O6 13.8(9) . . . . ?
C13 C11 C12 O6 -106.9(8) . . . . ?
C10 C11 C12 O7 -168.0(5) . . . . ?
C13 C11 C12 O7 71.4(7) . . . . ?
C12 O7 C14 C15 175.7(7) . . . . ?
C17 O5 C16 O4 2.0(8) . . . . ?
C17 O5 C16 C9 176.5(6) . . . . ?
N C9 C16 O4 -141.1(5) . . . . ?
C10 C9 C16 O4 -16.1(7) . . . . ?
N C9 C16 O5 44.4(5) . . . . ?
C10 C9 C16 O5 169.4(4) . . . . ?
C16 O5 C17 C18 -169.8(12) . . . . ?

#===END