# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 906384'
#TrackingRef 'p21n_final.txt'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N2 O6'
_chemical_formula_sum            'C18 H20 N2 O6'
_chemical_formula_weight         360.36

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   'P 21/n'

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

_cell_length_a                   6.7348(18)
_cell_length_b                   28.345(7)
_cell_length_c                   9.559(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.640(7)
_cell_angle_gamma                90.00
_cell_volume                     1808.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(1)
_cell_measurement_reflns_used    728
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      23.65

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8163
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(1)
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14806
_diffrn_reflns_av_R_equivalents  0.1187
_diffrn_reflns_av_sigmaI/netI    0.1116
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3163
_reflns_number_gt                1241
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker SMART V5.625'
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-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^)+(0.0815P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3163
_refine_ls_number_parameters     241
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2010
_refine_ls_R_factor_gt           0.0807
_refine_ls_wR_factor_ref         0.2188
_refine_ls_wR_factor_gt          0.1768
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.106
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5393(7) 0.05780(17) 0.4305(5) 0.0737(14) Uani 1 1 d . . .
H1 H 0.624(7) 0.0859(18) 0.430(5) 0.088 Uiso 1 1 d . . .
C1 C 0.5762(8) 0.0700(2) 0.0869(6) 0.0670(15) Uani 1 1 d . . .
O1 O 0.6897(7) 0.05085(13) 0.0171(5) 0.1048(16) Uani 1 1 d . . .
C2 C 0.4376(7) 0.04704(17) 0.1778(5) 0.0619(14) Uani 1 1 d . . .
H2 H 0.3480 0.0244 0.1238 0.074 Uiso 1 1 calc R . .
C3 C 0.5491(7) 0.02430(19) 0.3156(6) 0.0701(15) Uani 1 1 d . . .
H3 H 0.4777 -0.0045 0.3361 0.084 Uiso 1 1 calc R . .
C4 C 0.7650(10) 0.0119(2) 0.3066(7) 0.090(2) Uani 1 1 d . . .
O2 O 0.8990(7) 0.03809(17) 0.3329(6) 0.1250(18) Uani 1 1 d . . .
O3 O 0.7762(6) -0.03114(16) 0.2543(5) 0.1132(17) Uani 1 1 d . . .
C5 C 0.9824(11) -0.0421(3) 0.2293(11) 0.172(4) Uani 1 1 d D . .
H5A H 1.0097 -0.0278 0.1417 0.206 Uiso 1 1 calc R . .
H5B H 1.0773 -0.0296 0.3056 0.206 Uiso 1 1 calc R . .
C6 C 1.0029(14) -0.0925(3) 0.2218(11) 0.239(6) Uani 1 1 d D . .
H6A H 0.9666 -0.1065 0.3062 0.359 Uiso 1 1 calc R . .
H6B H 1.1393 -0.1003 0.2128 0.359 Uiso 1 1 calc R . .
H6C H 0.9165 -0.1042 0.1414 0.359 Uiso 1 1 calc R . .
C7 C 0.3479(8) 0.08202(19) 0.3945(5) 0.0661(15) Uani 1 1 d . . .
H7 H 0.2418 0.0611 0.4190 0.079 Uiso 1 1 calc R . .
C8 C 0.3398(11) 0.1267(2) 0.4762(6) 0.0723(16) Uani 1 1 d . . .
O4 O 0.4801(7) 0.14543(15) 0.5417(5) 0.1050(16) Uani 1 1 d . . .
O5 O 0.1542(6) 0.14332(13) 0.4645(4) 0.0794(12) Uani 1 1 d . . .
C9 C 0.1282(11) 0.1887(2) 0.5324(7) 0.093(2) Uani 1 1 d . . .
H9A H 0.2287 0.2108 0.5095 0.111 Uiso 1 1 calc R . .
H9B H 0.1438 0.1847 0.6341 0.111 Uiso 1 1 calc R . .
C10 C -0.0738(12) 0.2068(2) 0.4818(7) 0.118(3) Uani 1 1 d . . .
H10A H -0.0829 0.2141 0.3831 0.177 Uiso 1 1 calc R . .
H10B H -0.0981 0.2348 0.5334 0.177 Uiso 1 1 calc R . .
H10C H -0.1719 0.1833 0.4960 0.177 Uiso 1 1 calc R . .
C11 C 0.3197(7) 0.08803(17) 0.2331(5) 0.0585(14) Uani 1 1 d . . .
H11 H 0.1776 0.0866 0.1943 0.070 Uiso 1 1 calc R . .
C12 C 0.4163(8) 0.1314(2) 0.1840(5) 0.0589(14) Uani 1 1 d . . .
O6 O 0.3835(5) 0.17215(13) 0.2121(4) 0.0764(12) Uani 1 1 d . . .
N2 N 0.5580(6) 0.11850(14) 0.0973(4) 0.0575(11) Uani 1 1 d . . .
C13 C 0.6720(8) 0.15110(17) 0.0251(6) 0.0583(14) Uani 1 1 d . . .
C14 C 0.8527(9) 0.16684(19) 0.0892(6) 0.0732(16) Uani 1 1 d . . .
H14 H 0.9037 0.1565 0.1791 0.088 Uiso 1 1 calc R . .
C15 C 0.9600(9) 0.1989(2) 0.0168(7) 0.0808(17) Uani 1 1 d . . .
H15 H 1.0838 0.2099 0.0589 0.097 Uiso 1 1 calc R . .
C16 C 0.8847(11) 0.21423(19) -0.1147(7) 0.0801(18) Uani 1 1 d . . .
H16 H 0.9558 0.2358 -0.1619 0.096 Uiso 1 1 calc R . .
C17 C 0.7055(11) 0.1978(2) -0.1758(6) 0.0868(19) Uani 1 1 d . . .
H17 H 0.6547 0.2079 -0.2661 0.104 Uiso 1 1 calc R . .
C18 C 0.5970(9) 0.16639(19) -0.1067(6) 0.0727(16) Uani 1 1 d . . .
H18 H 0.4732 0.1556 -0.1496 0.087 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
N1 0.064(3) 0.074(3) 0.082(3) 0.012(3) 0.007(3) -0.007(3)
C1 0.062(4) 0.069(4) 0.075(4) -0.003(3) 0.029(3) -0.001(3)
O1 0.118(4) 0.077(3) 0.138(4) -0.015(2) 0.085(3) 0.002(2)
C2 0.051(3) 0.061(3) 0.075(4) -0.010(3) 0.018(3) -0.003(3)
C3 0.044(3) 0.063(4) 0.105(5) 0.010(3) 0.020(3) -0.002(3)
C4 0.060(5) 0.063(4) 0.147(6) 0.022(4) 0.023(4) -0.005(4)
O2 0.055(3) 0.116(4) 0.206(5) 0.000(3) 0.024(3) -0.015(3)
O3 0.062(3) 0.083(3) 0.205(5) 0.016(3) 0.052(3) 0.010(2)
C5 0.089(6) 0.125(7) 0.325(14) 0.010(7) 0.115(7) 0.022(5)
C6 0.243(12) 0.176(10) 0.349(16) 0.076(10) 0.227(12) 0.095(9)
C7 0.058(4) 0.072(4) 0.072(4) 0.001(3) 0.020(3) -0.008(3)
C8 0.076(5) 0.085(4) 0.059(4) -0.006(3) 0.020(4) -0.016(4)
O4 0.098(4) 0.124(4) 0.090(3) -0.033(3) 0.001(3) -0.025(3)
O5 0.079(3) 0.075(3) 0.092(3) -0.022(2) 0.041(2) -0.014(2)
C9 0.116(6) 0.078(4) 0.091(5) -0.019(4) 0.042(4) -0.012(4)
C10 0.129(7) 0.108(6) 0.126(6) -0.026(4) 0.053(5) 0.005(5)
C11 0.045(3) 0.063(3) 0.069(4) -0.009(3) 0.013(3) -0.003(3)
C12 0.058(3) 0.060(4) 0.059(3) 0.002(3) 0.008(3) 0.007(3)
O6 0.090(3) 0.063(2) 0.083(3) -0.001(2) 0.036(2) 0.009(2)
N2 0.062(3) 0.057(3) 0.057(3) 0.001(2) 0.021(2) 0.002(2)
C13 0.061(4) 0.054(3) 0.061(4) -0.001(3) 0.013(3) 0.002(3)
C14 0.078(5) 0.073(4) 0.070(4) 0.001(3) 0.014(4) 0.005(3)
C15 0.064(4) 0.082(4) 0.096(5) -0.003(4) 0.012(4) -0.008(3)
C16 0.095(5) 0.072(4) 0.081(5) 0.000(3) 0.039(4) 0.000(4)
C17 0.102(5) 0.099(5) 0.060(4) 0.001(3) 0.012(4) -0.007(4)
C18 0.073(4) 0.083(4) 0.060(4) -0.001(3) 0.001(3) -0.015(3)

_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
N1 C3 1.460(6) . ?
N1 C7 1.461(6) . ?
N1 H1 0.98(5) . ?
C1 O1 1.208(5) . ?
C1 N2 1.386(6) . ?
C1 C2 1.504(7) . ?
C2 C11 1.541(6) . ?
C2 C3 1.566(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.510(7) . ?
C3 H3 0.9800 . ?
C4 O2 1.170(6) . ?
C4 O3 1.323(7) . ?
O3 C5 1.473(7) . ?
C5 C6 1.437(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.493(7) . ?
C7 C11 1.538(6) . ?
C7 H7 0.9800 . ?
C8 O4 1.187(6) . ?
C8 O5 1.327(6) . ?
O5 C9 1.461(6) . ?
C9 C10 1.475(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.497(6) . ?
C11 H11 0.9800 . ?
C12 O6 1.212(5) . ?
C12 N2 1.393(6) . ?
N2 C13 1.435(6) . ?
C13 C14 1.363(7) . ?
C13 C18 1.364(7) . ?
C14 C15 1.400(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.352(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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
C3 N1 C7 104.8(4) . . ?
C3 N1 H1 116(3) . . ?
C7 N1 H1 97(3) . . ?
O1 C1 N2 123.6(5) . . ?
O1 C1 C2 127.7(5) . . ?
N2 C1 C2 108.6(4) . . ?
C1 C2 C11 105.1(4) . . ?
C1 C2 C3 113.5(4) . . ?
C11 C2 C3 103.5(4) . . ?
C1 C2 H2 111.4 . . ?
C11 C2 H2 111.4 . . ?
C3 C2 H2 111.4 . . ?
N1 C3 C4 109.5(5) . . ?
N1 C3 C2 107.5(4) . . ?
C4 C3 C2 114.0(5) . . ?
N1 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
O2 C4 O3 125.8(6) . . ?
O2 C4 C3 124.1(6) . . ?
O3 C4 C3 109.9(6) . . ?
C4 O3 C5 110.9(5) . . ?
C6 C5 O3 108.4(6) . . ?
C6 C5 H5A 110.0 . . ?
O3 C5 H5A 110.0 . . ?
C6 C5 H5B 110.0 . . ?
O3 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 111.6(5) . . ?
N1 C7 C11 106.0(4) . . ?
C8 C7 C11 115.0(4) . . ?
N1 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C11 C7 H7 108.0 . . ?
O4 C8 O5 124.1(6) . . ?
O4 C8 C7 125.0(6) . . ?
O5 C8 C7 110.9(5) . . ?
C8 O5 C9 116.3(5) . . ?
O5 C9 C10 108.7(5) . . ?
O5 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
O5 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C7 113.9(4) . . ?
C12 C11 C2 104.3(4) . . ?
C7 C11 C2 105.1(4) . . ?
C12 C11 H11 111.1 . . ?
C7 C11 H11 111.1 . . ?
C2 C11 H11 111.1 . . ?
O6 C12 N2 122.8(5) . . ?
O6 C12 C11 127.8(5) . . ?
N2 C12 C11 109.3(4) . . ?
C1 N2 C12 112.2(4) . . ?
C1 N2 C13 123.1(4) . . ?
C12 N2 C13 124.7(4) . . ?
C14 C13 C18 120.6(5) . . ?
C14 C13 N2 119.8(5) . . ?
C18 C13 N2 119.5(5) . . ?
C13 C14 C15 118.6(6) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C16 C15 C14 120.6(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.4(6) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.1(6) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C13 C18 C17 119.6(5) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.058