# Electronic Supplementary Material (ESI) for ChemComm.
# 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_racmebuam
_database_code_depnum_ccdc_archive 'CCDC 950602'
_audit_update_record             
;
2013-07-16 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H17 O7, C4 H12 N'
_chemical_formula_sum            'C16 H29 N O7'
_chemical_melting_point          ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         347.40

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration rm

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                   6.1806(13)
_cell_length_b                   14.641(3)
_cell_length_c                   20.360(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1842.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4552
_cell_measurement_theta_min      1.71
_cell_measurement_theta_max      28.40
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9142
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         28.40
_reflns_number_total             4552
_reflns_number_gt                3677
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.0502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         4552
_refine_ls_number_parameters     274
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.030

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 0.35973(18) 0.04356(7) 0.62684(5) 0.0289(2) Uani 1 1 d . . .
C2 C 0.4777(2) 0.02662(9) 0.56805(7) 0.0231(3) Uani 1 1 d . . .
O3 O 0.33780(17) 0.03359(7) 0.51392(5) 0.0279(2) Uani 1 1 d . . .
C4 C 0.2394(2) -0.05467(11) 0.50542(9) 0.0330(4) Uani 1 1 d . . .
H4 H 0.1221 -0.0634 0.5386 0.040 Uiso 1 1 calc R . .
C5 C 0.1475(3) -0.06238(13) 0.43740(11) 0.0475(5) Uani 1 1 d . . .
H5A H 0.0488 -0.1156 0.4354 0.057 Uiso 1 1 calc R . .
H5B H 0.0619 -0.0069 0.4274 0.057 Uiso 1 1 calc R . .
O6 O 0.3139(2) -0.07288(8) 0.38883(6) 0.0432(3) Uani 1 1 d . . .
C7 C 0.4631(3) -0.14355(11) 0.40267(8) 0.0354(4) Uani 1 1 d . . .
O8 O 0.56790(17) -0.12701(7) 0.46433(5) 0.0289(2) Uani 1 1 d . . .
C9 C 0.4242(2) -0.12093(10) 0.51897(8) 0.0281(3) Uani 1 1 d . . .
H9 H 0.3698 -0.1824 0.5327 0.034 Uiso 1 1 calc R . .
C10 C 0.5472(2) -0.07386(9) 0.57379(8) 0.0253(3) Uani 1 1 d . . .
H10 H 0.7074 -0.0822 0.5702 0.030 Uiso 1 1 calc R . .
O11 O 0.4631(2) -0.10395(7) 0.63522(6) 0.0350(3) Uani 1 1 d . . .
C12 C 0.4148(3) -0.02540(11) 0.67397(8) 0.0332(4) Uani 1 1 d . . .
C13 C 0.6546(2) 0.09947(9) 0.55859(7) 0.0244(3) Uani 1 1 d . . .
O14 O 0.84561(17) 0.07378(7) 0.55594(7) 0.0389(3) Uani 1 1 d . . .
O15 O 0.58687(17) 0.18038(7) 0.55466(6) 0.0295(2) Uani 1 1 d . . .
C16 C 0.6383(4) -0.13648(14) 0.35129(8) 0.0445(4) Uani 1 1 d . . .
H16A H 0.7069 -0.0763 0.3540 0.067 Uiso 1 1 calc R . .
H16B H 0.5747 -0.1446 0.3076 0.067 Uiso 1 1 calc R . .
H16C H 0.7470 -0.1840 0.3589 0.067 Uiso 1 1 calc R . .
C17 C 0.3565(4) -0.23776(12) 0.40228(10) 0.0468(5) Uani 1 1 d . . .
H17A H 0.4676 -0.2849 0.4076 0.070 Uiso 1 1 calc R . .
H17B H 0.2810 -0.2469 0.3605 0.070 Uiso 1 1 calc R . .
H17C H 0.2526 -0.2418 0.4385 0.070 Uiso 1 1 calc R . .
C18 C 0.2201(3) -0.04632(14) 0.71513(10) 0.0496(5) Uani 1 1 d . . .
H18A H 0.0990 -0.0633 0.6866 0.074 Uiso 1 1 calc R . .
H18B H 0.1808 0.0077 0.7409 0.074 Uiso 1 1 calc R . .
H18C H 0.2532 -0.0971 0.7449 0.074 Uiso 1 1 calc R . .
C19 C 0.6119(3) 0.00411(14) 0.71296(10) 0.0474(5) Uani 1 1 d . . .
H19A H 0.6561 -0.0454 0.7424 0.071 Uiso 1 1 calc R . .
H19B H 0.5764 0.0585 0.7389 0.071 Uiso 1 1 calc R . .
H19C H 0.7306 0.0184 0.6827 0.071 Uiso 1 1 calc R . .
C20 C 0.158(2) 0.3681(6) 0.6196(4) 0.0398(17) Uani 0.560(6) 1 d P A 1
H20B H 0.3157 0.3599 0.6183 0.060 Uiso 0.560(6) 1 calc PR A 1
H20C H 0.1181 0.3993 0.6604 0.060 Uiso 0.560(6) 1 calc PR A 1
H20A H 0.1123 0.4048 0.5819 0.060 Uiso 0.560(6) 1 calc PR A 1
C21 C 0.0506(9) 0.2770(5) 0.6171(5) 0.030(3) Uani 0.560(6) 1 d P A 1
H21 H -0.1066 0.2876 0.6083 0.036 Uiso 0.560(6) 1 calc PR A 1
C22 C 0.069(3) 0.2250(9) 0.6822(5) 0.057(3) Uani 0.560(6) 1 d P A 1
H22A H 0.0284 0.1604 0.6751 0.068 Uiso 0.560(6) 1 calc PR A 1
H22B H -0.0340 0.2514 0.7143 0.068 Uiso 0.560(6) 1 calc PR A 1
C23 C 0.3068(7) 0.2296(2) 0.71172(17) 0.0544(13) Uani 0.560(6) 1 d P A 1
H23A H 0.4106 0.2086 0.6786 0.082 Uiso 0.560(6) 1 calc PR A 1
H23B H 0.3158 0.1903 0.7506 0.082 Uiso 0.560(6) 1 calc PR A 1
H23C H 0.3405 0.2927 0.7241 0.082 Uiso 0.560(6) 1 calc PR A 1
N24 N 0.144(4) 0.2192(15) 0.5581(10) 0.023(2) Uani 0.560(6) 1 d PD A 1
H24A H 0.1422 0.2535 0.5208 0.035 Uiso 0.560(6) 1 calc PRD A 1
H24B H 0.0619 0.1683 0.5522 0.035 Uiso 0.560(6) 1 calc PRD A 1
H24C H 0.2828 0.2024 0.5673 0.035 Uiso 0.560(6) 1 calc PRD A 1
C25 C 0.031(4) 0.2306(13) 0.6779(8) 0.076(6) Uani 0.440(6) 1 d P A 2
H25B H 0.1712 0.2050 0.6905 0.114 Uiso 0.440(6) 1 calc PR A 2
H25A H -0.0738 0.1809 0.6719 0.114 Uiso 0.440(6) 1 calc PR A 2
H25C H -0.0204 0.2719 0.7124 0.114 Uiso 0.440(6) 1 calc PR A 2
C26 C 0.0538(18) 0.2815(8) 0.6159(6) 0.046(5) Uani 0.440(6) 1 d P A 2
H26 H -0.0945 0.3015 0.6024 0.055 Uiso 0.440(6) 1 calc PR A 2
C27 C 0.197(3) 0.3675(11) 0.6177(8) 0.068(5) Uani 0.440(6) 1 d P A 2
H27A H 0.2176 0.3910 0.5726 0.082 Uiso 0.440(6) 1 calc PR A 2
H27B H 0.1245 0.4155 0.6440 0.082 Uiso 0.440(6) 1 calc PR A 2
C28 C 0.4137(9) 0.3445(4) 0.6479(3) 0.072(2) Uani 0.440(6) 1 d P A 2
H28B H 0.3917 0.3077 0.6875 0.108 Uiso 0.440(6) 1 calc PR A 2
H28A H 0.4894 0.4010 0.6595 0.108 Uiso 0.440(6) 1 calc PR A 2
H28C H 0.5004 0.3099 0.6162 0.108 Uiso 0.440(6) 1 calc PR A 2
N29 N 0.129(5) 0.2213(19) 0.5674(12) 0.020(3) Uani 0.440(6) 1 d PD A 2
H29C H 0.2705 0.2082 0.5749 0.030 Uiso 0.440(6) 1 calc PRD A 2
H29A H 0.1146 0.2478 0.5272 0.030 Uiso 0.440(6) 1 calc PRD A 2
H29B H 0.0498 0.1689 0.5687 0.030 Uiso 0.440(6) 1 calc PRD A 2


_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 1.4234(18) . ?
O1 C12 1.4339(19) . ?
C2 O3 1.4046(18) . ?
C2 C10 1.5369(19) . ?
C2 C13 1.5394(19) . ?
O3 C4 1.4384(19) . ?
C4 C5 1.501(3) . ?
C4 C9 1.524(2) . ?
C5 O6 1.435(2) . ?
O6 C7 1.415(2) . ?
C7 O8 1.433(2) . ?
C7 C16 1.509(3) . ?
C7 C17 1.529(2) . ?
O8 C9 1.4263(19) . ?
C9 C10 1.516(2) . ?
C10 O11 1.4241(19) . ?
O11 C12 1.426(2) . ?
C12 C18 1.498(2) . ?
C12 C19 1.517(3) . ?
C13 O14 1.2401(18) . ?
C13 O15 1.2590(17) . ?
C20 C21 1.491(13) . ?
C21 C22 1.534(16) . ?
C21 N24 1.58(2) . ?
C22 C23 1.589(18) . ?
C25 C26 1.47(2) . ?
C26 N29 1.40(3) . ?
C26 C27 1.54(2) . ?
C27 C28 1.513(19) . ?

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 C12 108.56(11) . . ?
O3 C2 O1 109.36(11) . . ?
O3 C2 C10 107.53(12) . . ?
O1 C2 C10 104.24(11) . . ?
O3 C2 C13 106.78(11) . . ?
O1 C2 C13 110.39(12) . . ?
C10 C2 C13 118.32(11) . . ?
C2 O3 C4 106.82(11) . . ?
O3 C4 C5 109.79(14) . . ?
O3 C4 C9 103.49(12) . . ?
C5 C4 C9 113.75(14) . . ?
O6 C5 C4 111.88(14) . . ?
C7 O6 C5 114.10(14) . . ?
O6 C7 O8 110.22(13) . . ?
O6 C7 C16 106.24(14) . . ?
O8 C7 C16 105.75(14) . . ?
O6 C7 C17 112.20(15) . . ?
O8 C7 C17 110.60(14) . . ?
C16 C7 C17 111.56(15) . . ?
C9 O8 C7 114.36(12) . . ?
O8 C9 C10 106.89(11) . . ?
O8 C9 C4 111.42(13) . . ?
C10 C9 C4 102.69(12) . . ?
O11 C10 C9 108.85(12) . . ?
O11 C10 C2 105.13(12) . . ?
C9 C10 C2 103.83(12) . . ?
C10 O11 C12 108.22(11) . . ?
O11 C12 O1 104.32(13) . . ?
O11 C12 C18 108.22(14) . . ?
O1 C12 C18 109.12(14) . . ?
O11 C12 C19 110.55(14) . . ?
O1 C12 C19 109.90(14) . . ?
C18 C12 C19 114.25(16) . . ?
O14 C13 O15 126.81(14) . . ?
O14 C13 C2 118.12(12) . . ?
O15 C13 C2 115.07(12) . . ?
C20 C21 C22 112.3(8) . . ?
C20 C21 N24 110.0(10) . . ?
C22 C21 N24 111.4(10) . . ?
C21 C22 C23 112.0(8) . . ?
N29 C26 C25 108.5(15) . . ?
N29 C26 C27 110.0(15) . . ?
C25 C26 C27 116.6(13) . . ?
C28 C27 C26 109.7(10) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        28.40
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_rmebuam
_database_code_depnum_ccdc_archive 'CCDC 950603'
_audit_update_record             
;
2013-07-16 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H17 O7, C5 H14 N'
_chemical_formula_sum            'C17 H31 N O7'
_chemical_melting_point          ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         361.43

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration rm

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                   6.3376(5)
_cell_length_b                   15.4586(12)
_cell_length_c                   20.0153(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1960.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4035
_cell_measurement_theta_min      1.66
_cell_measurement_theta_max      26.49
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11503
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.49
_reflns_number_total             4035
_reflns_number_gt                3545
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0428P)²+0.4299P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_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   ?
_refine_ls_number_reflns         4035
_refine_ls_number_parameters     236
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.921
_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
O15 O 0.56438(17) 0.16469(7) 0.03018(5) 0.0267(2) Uani 1 1 d . . .
O3 O 0.32609(18) 0.02128(6) 0.00896(5) 0.0276(2) Uani 1 1 d . . .
O8 O 0.55689(17) -0.13235(7) -0.03301(5) 0.0282(2) Uani 1 1 d . . .
N25 N 0.13491(17) 0.20069(7) 0.05866(5) 0.0224(3) Uani 1 1 d D . .
O1 O 0.36716(18) 0.04767(6) 0.12197(5) 0.0286(2) Uani 1 1 d . . .
O14 O 0.82811(17) 0.07052(7) 0.04653(6) 0.0318(3) Uani 1 1 d . . .
O6 O 0.2961(2) -0.09228(8) -0.11025(6) 0.0407(3) Uani 1 1 d . . .
O11 O 0.46643(19) -0.09115(7) 0.13976(5) 0.0305(3) Uani 1 1 d . . .
C2 C 0.4713(2) 0.02294(9) 0.06167(7) 0.0224(3) Uani 1 1 d . . .
C4 C 0.2338(3) -0.06412(10) 0.00754(8) 0.0297(4) Uani 1 1 d . . .
H4 H 0.1237 -0.0695 0.0431 0.036 Uiso 1 1 calc R . .
C13 C 0.6397(2) 0.09137(9) 0.04415(7) 0.0221(3) Uani 1 1 d . . .
C9 C 0.4210(2) -0.12294(9) 0.02342(7) 0.0245(3) Uani 1 1 d . . .
H9 H 0.3745 -0.1802 0.0415 0.029 Uiso 1 1 calc R . .
C10 C 0.5428(2) -0.07105(9) 0.07477(7) 0.0231(3) Uani 1 1 d . . .
H10 H 0.6989 -0.0786 0.0707 0.028 Uiso 1 1 calc R . .
C24 C 0.3483(3) 0.35821(11) 0.12556(9) 0.0377(4) Uani 1 1 d . . .
H24A H 0.4835 0.3808 0.1417 0.057 Uiso 1 1 calc R . .
H24B H 0.2346 0.3977 0.1385 0.057 Uiso 1 1 calc R . .
H24C H 0.3524 0.3531 0.0768 0.057 Uiso 1 1 calc R . .
C12 C 0.4250(3) -0.01164(10) 0.17378(8) 0.0308(4) Uani 1 1 d . . .
C21 C 0.1071(2) 0.22523(10) 0.13055(7) 0.0256(3) Uani 1 1 d . . .
H21 H 0.0883 0.1705 0.1566 0.031 Uiso 1 1 calc R . .
C17 C 0.3576(3) -0.24606(11) -0.08847(8) 0.0379(4) Uani 1 1 d . . .
H17A H 0.2745 -0.2587 -0.1286 0.057 Uiso 1 1 calc R . .
H17B H 0.2664 -0.2493 -0.0490 0.057 Uiso 1 1 calc R . .
H17C H 0.4719 -0.2885 -0.0844 0.057 Uiso 1 1 calc R . .
C19 C 0.6200(3) 0.02082(12) 0.20942(9) 0.0429(5) Uani 1 1 d . . .
H19A H 0.5910 0.0776 0.2291 0.064 Uiso 1 1 calc R . .
H19B H 0.7365 0.0258 0.1774 0.064 Uiso 1 1 calc R . .
H19C H 0.6590 -0.0200 0.2448 0.064 Uiso 1 1 calc R . .
C7 C 0.4513(3) -0.15520(11) -0.09387(8) 0.0332(4) Uani 1 1 d . . .
C23 C 0.3060(3) 0.27369(12) 0.23235(8) 0.0417(4) Uani 1 1 d . . .
H23C H 0.1894 0.3107 0.2470 0.063 Uiso 1 1 calc R . .
H23B H 0.4399 0.2978 0.2483 0.063 Uiso 1 1 calc R . .
H23A H 0.2871 0.2154 0.2506 0.063 Uiso 1 1 calc R . .
C5 C 0.1382(3) -0.08046(11) -0.05990(9) 0.0390(4) Uani 1 1 d . . .
H5B H 0.0482 -0.1327 -0.0577 0.047 Uiso 1 1 calc R . .
H5A H 0.0472 -0.0309 -0.0723 0.047 Uiso 1 1 calc R . .
C16 C 0.6181(3) -0.14932(14) -0.14745(9) 0.0474(5) Uani 1 1 d . . .
H16A H 0.6771 -0.0907 -0.1481 0.071 Uiso 1 1 calc R . .
H16B H 0.5548 -0.1623 -0.1910 0.071 Uiso 1 1 calc R . .
H16C H 0.7306 -0.1911 -0.1380 0.071 Uiso 1 1 calc R . .
C20 C -0.0946(3) 0.27736(13) 0.13755(10) 0.0421(4) Uani 1 1 d . . .
H20A H -0.2129 0.2444 0.1189 0.063 Uiso 1 1 calc R . .
H20B H -0.0800 0.3321 0.1133 0.063 Uiso 1 1 calc R . .
H20C H -0.1212 0.2892 0.1849 0.063 Uiso 1 1 calc R . .
C22 C 0.3086(3) 0.26936(11) 0.15627(7) 0.0279(3) Uani 1 1 d . . .
H22 H 0.4300 0.2316 0.1433 0.033 Uiso 1 1 calc R . .
C18 C 0.2350(2) -0.02481(11) 0.21939(9) 0.0492(5) Uani 1 1 d . . .
H18A H 0.1131 -0.0427 0.1926 0.074 Uiso 1 1 calc R . .
H18B H 0.2026 0.0295 0.2425 0.074 Uiso 1 1 calc R . .
H18C H 0.2673 -0.0697 0.2524 0.074 Uiso 1 1 calc R . .
H25A H 0.2682 0.1817 0.0493 0.034(5) Uiso 1 1 d RD . .
H25B H 0.0345 0.1632 0.0439 0.040(5) Uiso 1 1 d RD . .
H25C H 0.1072 0.2425 0.0277 0.041(5) Uiso 1 1 d RD . .


_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
O15 C13 1.2612(17) . ?
O3 C2 1.4000(17) . ?
O3 C4 1.4442(18) . ?
O8 C9 1.4279(18) . ?
O8 C7 1.4340(18) . ?
N25 C21 1.4983(19) . ?
O1 C2 1.4277(18) . ?
O1 C12 1.4318(19) . ?
O14 C13 1.2379(19) . ?
O6 C7 1.421(2) . ?
O6 C5 1.432(2) . ?
O11 C10 1.4223(18) . ?
O11 C12 1.4295(19) . ?
C2 C13 1.543(2) . ?
C2 C10 1.5444(19) . ?
C4 C5 1.501(2) . ?
C4 C9 1.528(2) . ?
C9 C10 1.515(2) . ?
C24 C22 1.526(2) . ?
C12 C19 1.513(3) . ?
C12 C18 1.525(2) . ?
C21 C20 1.518(2) . ?
C21 C22 1.536(2) . ?
C17 C7 1.529(2) . ?
C7 C16 1.508(3) . ?
C23 C22 1.524(2) . ?

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 O3 C4 107.32(11) . . ?
C9 O8 C7 114.55(12) . . ?
C2 O1 C12 108.82(11) . . ?
C7 O6 C5 114.12(12) . . ?
C10 O11 C12 108.07(11) . . ?
O3 C2 O1 109.78(12) . . ?
O3 C2 C13 107.21(11) . . ?
O1 C2 C13 109.16(11) . . ?
O3 C2 C10 107.67(11) . . ?
O1 C2 C10 104.12(11) . . ?
C13 C2 C10 118.72(12) . . ?
O3 C4 C5 109.57(13) . . ?
O3 C4 C9 103.04(12) . . ?
C5 C4 C9 113.60(14) . . ?
O14 C13 O15 127.41(13) . . ?
O14 C13 C2 118.69(13) . . ?
O15 C13 C2 113.88(12) . . ?
O8 C9 C10 106.45(12) . . ?
O8 C9 C4 111.36(12) . . ?
C10 C9 C4 102.79(12) . . ?
O11 C10 C9 109.36(12) . . ?
O11 C10 C2 105.13(12) . . ?
C9 C10 C2 103.50(11) . . ?
O11 C12 O1 104.64(12) . . ?
O11 C12 C19 111.08(14) . . ?
O1 C12 C19 109.78(14) . . ?
O11 C12 C18 108.39(14) . . ?
O1 C12 C18 108.48(13) . . ?
C19 C12 C18 114.02(15) . . ?
N25 C21 C20 108.80(13) . . ?
N25 C21 C22 109.66(12) . . ?
C20 C21 C22 115.67(13) . . ?
O6 C7 O8 110.50(13) . . ?
O6 C7 C16 106.23(14) . . ?
O8 C7 C16 105.20(14) . . ?
O6 C7 C17 112.10(14) . . ?
O8 C7 C17 110.34(13) . . ?
C16 C7 C17 112.19(16) . . ?
O6 C5 C4 111.83(14) . . ?
C23 C22 C24 111.39(14) . . ?
C23 C22 C21 110.21(13) . . ?
C24 C22 C21 113.70(13) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_rnea
_database_code_depnum_ccdc_archive 'CCDC 950604'
_audit_update_record             
;
2013-07-16 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H31 N O7'
_chemical_formula_weight         445.50

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           orthorhombic
_symmetry_space_group_name_H-M   P212121
_chemical_absolute_configuration rm

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                   7.6206(4)
_cell_length_b                   11.4755(9)
_cell_length_c                   26.5274(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2319.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4679
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.31

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8259
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         26.31
_reflns_number_total             4679
_reflns_number_gt                4396
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.4082P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         4679
_refine_ls_number_parameters     298
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.080
_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 0.50472(16) 0.25747(12) 0.37893(4) 0.0312(3) Uani 1 1 d . . .
C2 C 0.3850(2) 0.24860(15) 0.33809(5) 0.0229(3) Uani 1 1 d . . .
O3 O 0.37859(15) 0.35434(10) 0.31135(4) 0.0235(2) Uani 1 1 d . . .
C4 C 0.2353(2) 0.42283(14) 0.33091(6) 0.0249(3) Uani 1 1 d . . .
H4 H 0.2718 0.4632 0.3626 0.030 Uiso 1 1 calc R . .
C5 C 0.1801(2) 0.51069(14) 0.29205(7) 0.0267(4) Uani 1 1 d . . .
H5B H 0.1009 0.5686 0.3078 0.032 Uiso 1 1 calc R . .
H5A H 0.2848 0.5525 0.2794 0.032 Uiso 1 1 calc R . .
O6 O 0.09196(15) 0.45608(10) 0.25069(4) 0.0264(3) Uani 1 1 d . . .
C7 C -0.0510(2) 0.38223(15) 0.26580(6) 0.0256(3) Uani 1 1 d . . .
O8 O 0.01565(14) 0.29148(10) 0.29719(4) 0.0256(3) Uani 1 1 d . . .
C9 C 0.0952(2) 0.33153(15) 0.34236(6) 0.0252(3) Uani 1 1 d . . .
H9 H 0.0067 0.3603 0.3673 0.030 Uiso 1 1 calc R . .
C10 C 0.2038(2) 0.23228(16) 0.36314(6) 0.0262(4) Uani 1 1 d . . .
H10 H 0.1511 0.1540 0.3564 0.031 Uiso 1 1 calc R . .
O11 O 0.23334(18) 0.25362(14) 0.41531(4) 0.0391(3) Uani 1 1 d . . .
C12 C 0.4157(3) 0.24079(19) 0.42593(6) 0.0362(4) Uani 1 1 d . . .
C13 C 0.4448(2) 0.14802(14) 0.30324(6) 0.0227(3) Uani 1 1 d . . .
O14 O 0.43385(18) 0.04935(11) 0.32303(5) 0.0332(3) Uani 1 1 d . . .
O15 O 0.49624(17) 0.17193(11) 0.25992(4) 0.0296(3) Uani 1 1 d . . .
C16 C -0.1151(3) 0.32426(17) 0.21845(7) 0.0343(4) Uani 1 1 d . . .
H16C H -0.2130 0.2722 0.2266 0.051 Uiso 1 1 calc R . .
H16A H -0.0194 0.2790 0.2034 0.051 Uiso 1 1 calc R . .
H16B H -0.1545 0.3838 0.1945 0.051 Uiso 1 1 calc R . .
C17 C -0.1960(2) 0.45075(18) 0.29139(8) 0.0348(4) Uani 1 1 d . . .
H17C H -0.1499 0.4877 0.3220 0.052 Uiso 1 1 calc R . .
H17B H -0.2921 0.3980 0.3004 0.052 Uiso 1 1 calc R . .
H17A H -0.2397 0.5109 0.2684 0.052 Uiso 1 1 calc R . .
C18 C 0.4679(4) 0.33458(15) 0.46040(6) 0.0634(7) Uani 1 1 d . . .
H18A H 0.4365 0.4101 0.4457 0.095 Uiso 1 1 calc R . .
H18C H 0.5950 0.3314 0.4659 0.095 Uiso 1 1 calc R . .
H18B H 0.4072 0.3249 0.4927 0.095 Uiso 1 1 calc R . .
H32B H 0.4540 0.4158 0.1926 0.038(6) Uiso 1 1 d RD . .
H32C H 0.2786 0.3768 0.2114 0.028(5) Uiso 1 1 d RD . .
H32A H 0.4352 0.2979 0.2228 0.043(6) Uiso 1 1 d RD . .
C19 C 0.4532(3) 0.1200(2) 0.44601(8) 0.0463(5) Uani 1 1 d . . .
H19B H 0.5792 0.1119 0.4524 0.069 Uiso 1 1 calc R . .
H19C H 0.4163 0.0618 0.4211 0.069 Uiso 1 1 calc R . .
H19A H 0.3883 0.1080 0.4775 0.069 Uiso 1 1 calc R . .
C20 C 0.2193(2) 0.33510(15) 0.11979(6) 0.0244(3) Uani 1 1 d . . .
C21 C 0.2017(2) 0.45375(17) 0.11765(6) 0.0302(4) Uani 1 1 d . . .
H21 H 0.2754 0.5013 0.1379 0.036 Uiso 1 1 calc R . .
C22 C 0.0763(3) 0.50676(18) 0.08589(7) 0.0368(4) Uani 1 1 d . . .
H22 H 0.0679 0.5893 0.0846 0.044 Uiso 1 1 calc R . .
C23 C -0.0322(3) 0.4406(2) 0.05727(7) 0.0395(5) Uani 1 1 d . . .
H23 H -0.1180 0.4772 0.0367 0.047 Uiso 1 1 calc R . .
C24 C -0.0189(2) 0.31806(19) 0.05773(6) 0.0346(4) Uani 1 1 d . . .
C25 C -0.1299(3) 0.2474(2) 0.02746(7) 0.0473(6) Uani 1 1 d . . .
H25 H -0.2161 0.2835 0.0068 0.057 Uiso 1 1 calc R . .
C26 C -0.1160(3) 0.1303(3) 0.02734(8) 0.0529(6) Uani 1 1 d . . .
H26 H -0.1924 0.0849 0.0070 0.063 Uiso 1 1 calc R . .
C27 C 0.0119(3) 0.0751(2) 0.05736(7) 0.0468(5) Uani 1 1 d . . .
H27 H 0.0224 -0.0074 0.0569 0.056 Uiso 1 1 calc R . .
C28 C 0.1216(3) 0.14039(18) 0.08731(6) 0.0356(4) Uani 1 1 d . . .
H28 H 0.2074 0.1021 0.1073 0.043 Uiso 1 1 calc R . .
C29 C 0.1095(2) 0.26325(16) 0.08905(6) 0.0273(4) Uani 1 1 d . . .
C30 C 0.3548(2) 0.27903(15) 0.15408(6) 0.0261(4) Uani 1 1 d . . .
H30 H 0.3077 0.2018 0.1651 0.031 Uiso 1 1 calc R . .
C31 C 0.5280(3) 0.2576(2) 0.12716(7) 0.0388(4) Uani 1 1 d . . .
H31A H 0.6082 0.2160 0.1497 0.058 Uiso 1 1 calc R . .
H31B H 0.5802 0.3324 0.1175 0.058 Uiso 1 1 calc R . .
H31C H 0.5072 0.2107 0.0969 0.058 Uiso 1 1 calc R . .
N32 N 0.38717(18) 0.35134(12) 0.20066(4) 0.0245(3) Uani 1 1 d D . .


_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 1.4197(19) . ?
O1 C12 1.433(2) . ?
C2 O3 1.406(2) . ?
C2 C10 1.544(2) . ?
C2 C13 1.547(2) . ?
O3 C4 1.4418(19) . ?
C4 C5 1.502(2) . ?
C4 C9 1.527(2) . ?
C5 O6 1.431(2) . ?
O6 C7 1.437(2) . ?
C7 O8 1.427(2) . ?
C7 C16 1.503(2) . ?
C7 C17 1.517(2) . ?
O8 C9 1.419(2) . ?
C9 C10 1.512(2) . ?
C10 O11 1.423(2) . ?
O11 C12 1.425(2) . ?
C12 C18 1.467(3) . ?
C12 C19 1.512(3) . ?
C13 O15 1.245(2) . ?
C13 O14 1.251(2) . ?
C20 C21 1.369(3) . ?
C20 C29 1.430(2) . ?
C20 C30 1.519(2) . ?
C21 C22 1.412(3) . ?
C22 C23 1.355(3) . ?
C23 C24 1.410(3) . ?
C24 C25 1.421(3) . ?
C24 C29 1.429(2) . ?
C25 C26 1.348(4) . ?
C26 C27 1.409(4) . ?
C27 C28 1.375(3) . ?
C28 C29 1.414(3) . ?
C30 N32 1.509(2) . ?
C30 C31 1.521(3) . ?

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 C12 110.50(13) . . ?
O3 C2 O1 110.21(13) . . ?
O3 C2 C10 106.89(13) . . ?
O1 C2 C10 104.78(12) . . ?
O3 C2 C13 110.63(12) . . ?
O1 C2 C13 108.69(13) . . ?
C10 C2 C13 115.45(13) . . ?
C2 O3 C4 108.37(12) . . ?
O3 C4 C5 109.34(13) . . ?
O3 C4 C9 103.14(12) . . ?
C5 C4 C9 113.64(14) . . ?
O6 C5 C4 111.34(13) . . ?
C5 O6 C7 113.58(12) . . ?
O8 C7 O6 108.87(12) . . ?
O8 C7 C16 106.28(14) . . ?
O6 C7 C16 105.91(13) . . ?
O8 C7 C17 112.12(14) . . ?
O6 C7 C17 111.80(14) . . ?
C16 C7 C17 111.52(14) . . ?
C9 O8 C7 114.10(12) . . ?
O8 C9 C10 107.31(13) . . ?
O8 C9 C4 110.67(13) . . ?
C10 C9 C4 101.91(13) . . ?
O11 C10 C9 108.13(14) . . ?
O11 C10 C2 104.85(13) . . ?
C9 C10 C2 103.98(13) . . ?
C10 O11 C12 109.17(13) . . ?
O11 C12 O1 106.02(13) . . ?
O11 C12 C18 108.18(19) . . ?
O1 C12 C18 108.41(17) . . ?
O11 C12 C19 110.39(18) . . ?
O1 C12 C19 109.85(16) . . ?
C18 C12 C19 113.68(16) . . ?
O15 C13 O14 127.43(15) . . ?
O15 C13 C2 118.68(15) . . ?
O14 C13 C2 113.88(13) . . ?
C21 C20 C29 119.50(16) . . ?
C21 C20 C30 120.82(16) . . ?
C29 C20 C30 119.68(15) . . ?
C20 C21 C22 121.28(18) . . ?
C23 C22 C21 120.41(19) . . ?
C22 C23 C24 120.66(18) . . ?
C23 C24 C25 121.45(19) . . ?
C23 C24 C29 119.54(18) . . ?
C25 C24 C29 119.0(2) . . ?
C26 C25 C24 121.6(2) . . ?
C25 C26 C27 120.1(2) . . ?
C28 C27 C26 120.1(2) . . ?
C27 C28 C29 121.5(2) . . ?
C28 C29 C20 123.74(16) . . ?
C28 C29 C24 117.68(17) . . ?
C20 C29 C24 118.58(17) . . ?
N32 C30 C20 111.62(13) . . ?
N32 C30 C31 109.37(14) . . ?
C20 C30 C31 112.17(14) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.31
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_rpea
_database_code_depnum_ccdc_archive 'CCDC 950605'
_audit_update_record             
;
2013-07-16 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C12 H17 O7, C8 H12 N '
_chemical_formula_sum            'C20 H29 N O7'
_chemical_formula_weight         395.44

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   P21
_chemical_absolute_configuration rm

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

_cell_length_a                   14.4045(11)
_cell_length_b                   6.2322(5)
_cell_length_c                   23.4872(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.762(2)
_cell_angle_gamma                90.00
_cell_volume                     2048.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7077
_cell_measurement_theta_min      1.46
_cell_measurement_theta_max      25.84

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10530
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         25.84
_reflns_number_total             7077
_reflns_number_gt                5714
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         7077
_refine_ls_number_parameters     516
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.415
_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 0.25840(12) 0.3425(3) 0.13720(9) 0.0272(5) Uani 1 1 d . . .
C2 C 0.26325(19) 0.4763(5) 0.18689(13) 0.0222(7) Uani 1 1 d . . .
O3 O 0.29613(12) 0.3559(3) 0.23870(9) 0.0253(5) Uani 1 1 d . . .
C4 C 0.2139(2) 0.2521(5) 0.25172(14) 0.0287(7) Uani 1 1 d . . .
H4 H 0.1955 0.1246 0.2256 0.034 Uiso 1 1 calc R . .
C5 C 0.2359(2) 0.1827(6) 0.31460(15) 0.0392(9) Uani 1 1 d . . .
H5B H 0.1888 0.0728 0.3195 0.047 Uiso 1 1 calc R . .
H5A H 0.3000 0.1155 0.3247 0.047 Uiso 1 1 calc R . .
O6 O 0.23396(14) 0.3561(4) 0.35430(9) 0.0351(5) Uani 1 1 d . . .
C7 C 0.1495(2) 0.4818(5) 0.33904(14) 0.0286(7) Uani 1 1 d . . .
O8 O 0.14269(13) 0.5758(3) 0.28241(9) 0.0254(5) Uani 1 1 d . . .
C9 C 0.13554(19) 0.4233(5) 0.23659(13) 0.0254(7) Uani 1 1 d . . .
H9 H 0.0706 0.3561 0.2262 0.031 Uiso 1 1 calc R . .
C10 C 0.15790(18) 0.5345(5) 0.18387(13) 0.0231(7) Uani 1 1 d . . .
H10 H 0.1470 0.6929 0.1839 0.028 Uiso 1 1 calc R . .
O11 O 0.10414(13) 0.4333(4) 0.13221(9) 0.0332(6) Uani 1 1 d . . .
C12 C 0.1678(2) 0.3686(6) 0.09677(13) 0.0292(7) Uani 1 1 d . . .
C13 C 0.33639(19) 0.6564(5) 0.18775(12) 0.0214(6) Uani 1 1 d . . .
O14 O 0.30846(13) 0.8451(4) 0.18556(9) 0.0305(5) Uani 1 1 d . . .
O15 O 0.42127(12) 0.5941(3) 0.19087(9) 0.0253(5) Uani 1 1 d . . .
C16 C 0.1626(2) 0.6631(6) 0.38196(14) 0.0372(8) Uani 1 1 d . . .
H16B H 0.1700 0.6058 0.4216 0.056 Uiso 1 1 calc R . .
H16C H 0.1065 0.7573 0.3724 0.056 Uiso 1 1 calc R . .
H16A H 0.2198 0.7449 0.3799 0.056 Uiso 1 1 calc R . .
C17 C 0.0606(2) 0.3516(6) 0.34015(16) 0.0422(9) Uani 1 1 d . . .
H17C H 0.0539 0.2343 0.3117 0.063 Uiso 1 1 calc R . .
H17B H 0.0042 0.4445 0.3300 0.063 Uiso 1 1 calc R . .
H17A H 0.0665 0.2921 0.3795 0.063 Uiso 1 1 calc R . .
C18 C 0.1359(2) 0.1537(6) 0.07004(16) 0.0442(10) Uani 1 1 d . . .
H18C H 0.1783 0.1083 0.0453 0.066 Uiso 1 1 calc R . .
H18B H 0.0702 0.1648 0.0462 0.066 Uiso 1 1 calc R . .
H18A H 0.1383 0.0480 0.1013 0.066 Uiso 1 1 calc R . .
C19 C 0.1736(2) 0.5408(6) 0.05269(16) 0.0439(10) Uani 1 1 d . . .
H19C H 0.1981 0.6734 0.0733 0.066 Uiso 1 1 calc R . .
H19A H 0.1099 0.5668 0.0276 0.066 Uiso 1 1 calc R . .
H19B H 0.2168 0.4941 0.0285 0.066 Uiso 1 1 calc R . .
C20 C 0.4468(2) 0.0969(5) 0.08305(14) 0.0281(7) Uani 1 1 d . . .
C21 C 0.4391(2) 0.2802(6) 0.04898(15) 0.0381(9) Uani 1 1 d . . .
H21 H 0.4737 0.4055 0.0643 0.046 Uiso 1 1 calc R . .
C22 C 0.3804(2) 0.2820(7) -0.00783(16) 0.0458(10) Uani 1 1 d . . .
H22 H 0.3756 0.4083 -0.0310 0.055 Uiso 1 1 calc R . .
C23 C 0.3296(2) 0.1016(7) -0.03026(15) 0.0453(10) Uani 1 1 d . . .
H23 H 0.2894 0.1029 -0.0687 0.054 Uiso 1 1 calc R . .
C24 C 0.3377(3) -0.0803(7) 0.00355(15) 0.0448(10) Uani 1 1 d . . .
H24 H 0.3030 -0.2056 -0.0117 0.054 Uiso 1 1 calc R . .
C25 C 0.3955(2) -0.0827(6) 0.05935(15) 0.0362(8) Uani 1 1 d . . .
H25 H 0.4002 -0.2101 0.0821 0.043 Uiso 1 1 calc R . .
C26 C 0.51132(19) 0.0858(5) 0.14421(13) 0.0290(7) Uani 1 1 d . . .
H26 H 0.5337 -0.0657 0.1517 0.035 Uiso 1 1 calc R . .
C27 C 0.5989(2) 0.2295(7) 0.15328(15) 0.0494(11) Uani 1 1 d . . .
H27A H 0.6309 0.2068 0.1213 0.074 Uiso 1 1 calc R . .
H27B H 0.6430 0.1943 0.1908 0.074 Uiso 1 1 calc R . .
H27C H 0.5793 0.3800 0.1536 0.074 Uiso 1 1 calc R . .
N28 N 0.45652(15) 0.1445(4) 0.18878(10) 0.0231(6) Uani 1 1 d D . .
H28C H 0.4889 0.1355 0.2256 0.028 Uiso 1 1 d RD . .
H28A H 0.4047 0.0527 0.1885 0.028 Uiso 1 1 d RD . .
H28B H 0.4311 0.2826 0.1886 0.028 Uiso 1 1 d RD . .
O29 O 0.75777(13) 0.8810(4) 0.36884(9) 0.0296(5) Uani 1 1 d . . .
C30 C 0.75256(19) 0.9962(5) 0.31587(13) 0.0225(7) Uani 1 1 d . . .
O31 O 0.72719(12) 0.8568(3) 0.26783(9) 0.0265(5) Uani 1 1 d . . .
C32 C 0.8139(2) 0.7578(5) 0.26055(15) 0.0305(8) Uani 1 1 d . . .
H32 H 0.8340 0.6414 0.2902 0.037 Uiso 1 1 calc R . .
C33 C 0.7979(2) 0.6667(6) 0.19951(16) 0.0431(10) Uani 1 1 d . . .
H33B H 0.8503 0.5659 0.1980 0.052 Uiso 1 1 calc R . .
H33A H 0.7372 0.5848 0.1904 0.052 Uiso 1 1 calc R . .
O34 O 0.79383(14) 0.8295(4) 0.15649(10) 0.0405(6) Uani 1 1 d . . .
C35 C 0.8731(2) 0.9720(6) 0.16847(14) 0.0312(8) Uani 1 1 d . . .
O36 O 0.87657(13) 1.0801(3) 0.22300(9) 0.0257(5) Uani 1 1 d . . .
C37 C 0.88649(19) 0.9410(5) 0.27245(13) 0.0253(7) Uani 1 1 d . . .
H37 H 0.9533 0.8858 0.2858 0.030 Uiso 1 1 calc R . .
C38 C 0.85676(18) 1.0670(5) 0.32026(13) 0.0231(7) Uani 1 1 d . . .
H38 H 0.8627 1.2255 0.3155 0.028 Uiso 1 1 calc R . .
O39 O 0.90950(13) 0.9930(4) 0.37581(9) 0.0375(6) Uani 1 1 d . . .
C40 C 0.8431(2) 0.9417(6) 0.41063(15) 0.0371(9) Uani 1 1 d . . .
C41 C 0.67401(19) 1.1698(5) 0.30767(12) 0.0219(7) Uani 1 1 d . . .
O42 O 0.69899(13) 1.3596(4) 0.30721(10) 0.0320(5) Uani 1 1 d . . .
O43 O 0.58969(12) 1.0996(3) 0.30155(9) 0.0256(5) Uani 1 1 d . . .
C44 C 0.8534(2) 1.1425(7) 0.12202(14) 0.0441(9) Uani 1 1 d . . .
H44C H 0.8462 1.0760 0.0834 0.066 Uiso 1 1 calc R . .
H44B H 0.9067 1.2444 0.1289 0.066 Uiso 1 1 calc R . .
H44A H 0.7944 1.2185 0.1234 0.066 Uiso 1 1 calc R . .
C45 C 0.9670(2) 0.8561(6) 0.17023(15) 0.0404(9) Uani 1 1 d . . .
H45C H 0.9804 0.7549 0.2031 0.061 Uiso 1 1 calc R . .
H45B H 1.0189 0.9612 0.1752 0.061 Uiso 1 1 calc R . .
H45A H 0.9619 0.7777 0.1335 0.061 Uiso 1 1 calc R . .
C46 C 0.8806(3) 0.7503(8) 0.44787(18) 0.0634(13) Uani 1 1 d . . .
H46A H 0.8919 0.6323 0.4228 0.095 Uiso 1 1 calc R . .
H46C H 0.8337 0.7053 0.4696 0.095 Uiso 1 1 calc R . .
H46B H 0.9407 0.7882 0.4756 0.095 Uiso 1 1 calc R . .
C47 C 0.8245(2) 1.1372(7) 0.44456(15) 0.0496(10) Uani 1 1 d . . .
H47A H 0.8840 1.1813 0.4719 0.074 Uiso 1 1 calc R . .
H47B H 0.7766 1.1022 0.4666 0.074 Uiso 1 1 calc R . .
H47C H 0.8009 1.2547 0.4172 0.074 Uiso 1 1 calc R . .
C48 C 0.55084(19) 0.5560(5) 0.40478(13) 0.0254(7) Uani 1 1 d . . .
C49 C 0.5470(2) 0.3636(6) 0.43367(14) 0.0365(8) Uani 1 1 d . . .
H49 H 0.5130 0.2455 0.4131 0.044 Uiso 1 1 calc R . .
C50 C 0.5922(3) 0.3425(6) 0.49241(16) 0.0445(9) Uani 1 1 d . . .
H50 H 0.5887 0.2105 0.5120 0.053 Uiso 1 1 calc R . .
C51 C 0.6421(2) 0.5116(7) 0.52243(15) 0.0407(9) Uani 1 1 d . . .
H51 H 0.6733 0.4963 0.5627 0.049 Uiso 1 1 calc R . .
C52 C 0.6470(2) 0.7036(6) 0.49413(14) 0.0359(8) Uani 1 1 d . . .
H52 H 0.6815 0.8207 0.5150 0.043 Uiso 1 1 calc R . .
C53 C 0.6015(2) 0.7265(6) 0.43527(14) 0.0307(8) Uani 1 1 d . . .
H53 H 0.6052 0.8589 0.4159 0.037 Uiso 1 1 calc R . .
C54 C 0.49267(18) 0.5842(5) 0.34207(13) 0.0241(7) Uani 1 1 d . . .
H54 H 0.4628 0.4430 0.3282 0.029 Uiso 1 1 calc R . .
C55 C 0.4132(2) 0.7469(6) 0.33863(14) 0.0342(8) Uani 1 1 d . . .
H55A H 0.4408 0.8862 0.3528 0.051 Uiso 1 1 calc R . .
H55C H 0.3706 0.6986 0.3630 0.051 Uiso 1 1 calc R . .
H55B H 0.3768 0.7609 0.2979 0.051 Uiso 1 1 calc R . .
N56 N 0.55390(15) 0.6504(4) 0.30189(10) 0.0217(6) Uani 1 1 d D . .
H56A H 0.5134 0.6420 0.2640 0.026 Uiso 1 1 d RD . .
H56C H 0.5781 0.7751 0.3089 0.026 Uiso 1 1 d RD . .
H56B H 0.6021 0.5510 0.3048 0.026 Uiso 1 1 d RD . .


_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 1.422(3) . ?
O1 C12 1.429(3) . ?
C2 O3 1.412(3) . ?
C2 C13 1.536(4) . ?
C2 C10 1.545(4) . ?
O3 C4 1.445(3) . ?
C4 C5 1.499(5) . ?
C4 C9 1.532(4) . ?
C4 H4 1.0000 . ?
C5 O6 1.432(4) . ?
C5 H5B 0.9900 . ?
C5 H5A 0.9900 . ?
O6 C7 1.420(4) . ?
C7 O8 1.435(4) . ?
C7 C16 1.496(5) . ?
C7 C17 1.521(4) . ?
O8 C9 1.421(4) . ?
C9 C10 1.519(4) . ?
C9 H9 1.0000 . ?
C10 O11 1.422(3) . ?
C10 H10 1.0000 . ?
O11 C12 1.435(3) . ?
C12 C18 1.504(5) . ?
C12 C19 1.507(5) . ?
C13 O14 1.240(4) . ?
C13 O15 1.268(3) . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16A 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17A 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18A 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 C25 1.383(4) . ?
C20 C21 1.384(5) . ?
C20 C26 1.515(4) . ?
C21 C22 1.399(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.373(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 N28 1.499(3) . ?
C26 C27 1.521(4) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N28 H28C 0.8811 . ?
N28 H28A 0.9394 . ?
N28 H28B 0.9350 . ?
O29 C30 1.423(3) . ?
O29 C40 1.430(4) . ?
C30 O31 1.402(3) . ?
C30 C38 1.544(4) . ?
C30 C41 1.544(4) . ?
O31 C32 1.439(3) . ?
C32 C33 1.508(5) . ?
C32 C37 1.528(4) . ?
C32 H32 1.0000 . ?
C33 O34 1.423(4) . ?
C33 H33B 0.9900 . ?
C33 H33A 0.9900 . ?
O34 C35 1.420(4) . ?
C35 O36 1.437(4) . ?
C35 C44 1.501(5) . ?
C35 C45 1.525(4) . ?
O36 C37 1.429(4) . ?
C37 C38 1.513(4) . ?
C37 H37 1.0000 . ?
C38 O39 1.421(3) . ?
C38 H38 1.0000 . ?
O39 C40 1.434(3) . ?
C40 C46 1.502(5) . ?
C40 C47 1.514(5) . ?
C41 O42 1.237(3) . ?
C41 O43 1.266(3) . ?
C44 H44C 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44A 0.9800 . ?
C45 H45C 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45A 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46C 0.9800 . ?
C46 H46B 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 C49 1.385(4) . ?
C48 C53 1.388(4) . ?
C48 C54 1.521(4) . ?
C49 C50 1.385(5) . ?
C49 H49 0.9500 . ?
C50 C51 1.372(5) . ?
C50 H50 0.9500 . ?
C51 C52 1.379(5) . ?
C51 H51 0.9500 . ?
C52 C53 1.389(4) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C54 N56 1.495(3) . ?
C54 C55 1.517(4) . ?
C54 H54 1.0000 . ?
C55 H55A 0.9800 . ?
C55 H55C 0.9800 . ?
C55 H55B 0.9800 . ?
N56 H56A 0.9428 . ?
N56 H56C 0.8516 . ?
N56 H56B 0.9204 . ?

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 C12 109.7(2) . . ?
O3 C2 O1 109.7(2) . . ?
O3 C2 C13 106.8(2) . . ?
O1 C2 C13 109.8(2) . . ?
O3 C2 C10 106.8(2) . . ?
O1 C2 C10 104.1(2) . . ?
C13 C2 C10 119.5(2) . . ?
C2 O3 C4 107.3(2) . . ?
O3 C4 C5 110.2(3) . . ?
O3 C4 C9 103.6(2) . . ?
C5 C4 C9 113.7(3) . . ?
O3 C4 H4 109.7 . . ?
C5 C4 H4 109.7 . . ?
C9 C4 H4 109.7 . . ?
O6 C5 C4 113.0(3) . . ?
O6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
O6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
H5B C5 H5A 107.8 . . ?
C7 O6 C5 113.6(2) . . ?
O6 C7 O8 108.9(2) . . ?
O6 C7 C16 106.5(3) . . ?
O8 C7 C16 106.6(3) . . ?
O6 C7 C17 112.0(3) . . ?
O8 C7 C17 111.2(3) . . ?
C16 C7 C17 111.3(3) . . ?
C9 O8 C7 113.9(2) . . ?
O8 C9 C10 108.7(2) . . ?
O8 C9 C4 111.9(2) . . ?
C10 C9 C4 102.7(2) . . ?
O8 C9 H9 111.1 . . ?
C10 C9 H9 111.1 . . ?
C4 C9 H9 111.1 . . ?
O11 C10 C9 108.4(2) . . ?
O11 C10 C2 105.3(2) . . ?
C9 C10 C2 104.6(2) . . ?
O11 C10 H10 112.7 . . ?
C9 C10 H10 112.7 . . ?
C2 C10 H10 112.7 . . ?
C10 O11 C12 109.0(2) . . ?
O1 C12 O11 104.8(2) . . ?
O1 C12 C18 108.4(3) . . ?
O11 C12 C18 108.6(3) . . ?
O1 C12 C19 110.2(2) . . ?
O11 C12 C19 110.3(3) . . ?
C18 C12 C19 114.1(3) . . ?
O14 C13 O15 126.3(3) . . ?
O14 C13 C2 118.5(2) . . ?
O15 C13 C2 115.2(3) . . ?
C7 C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
C7 C17 H17C 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
C7 C17 H17A 109.5 . . ?
H17C C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?
C12 C18 H18C 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
C12 C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
C12 C19 H19C 109.5 . . ?
C12 C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19C C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C25 C20 C21 118.2(3) . . ?
C25 C20 C26 119.5(3) . . ?
C21 C20 C26 122.2(3) . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 119.3(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 121.3(3) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?
N28 C26 C20 110.2(2) . . ?
N28 C26 C27 108.4(3) . . ?
C20 C26 C27 114.0(3) . . ?
N28 C26 H26 108.0 . . ?
C20 C26 H26 108.0 . . ?
C27 C26 H26 108.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 N28 H28C 115.2 . . ?
C26 N28 H28A 113.4 . . ?
H28C N28 H28A 101.7 . . ?
C26 N28 H28B 119.5 . . ?
H28C N28 H28B 100.3 . . ?
H28A N28 H28B 104.5 . . ?
C30 O29 C40 108.9(2) . . ?
O31 C30 O29 109.9(2) . . ?
O31 C30 C38 107.1(2) . . ?
O29 C30 C38 103.7(2) . . ?
O31 C30 C41 106.9(2) . . ?
O29 C30 C41 110.3(2) . . ?
C38 C30 C41 118.7(3) . . ?
C30 O31 C32 107.1(2) . . ?
O31 C32 C33 109.5(3) . . ?
O31 C32 C37 103.5(2) . . ?
C33 C32 C37 113.5(3) . . ?
O31 C32 H32 110.1 . . ?
C33 C32 H32 110.1 . . ?
C37 C32 H32 110.1 . . ?
O34 C33 C32 112.2(3) . . ?
O34 C33 H33B 109.2 . . ?
C32 C33 H33B 109.2 . . ?
O34 C33 H33A 109.2 . . ?
C32 C33 H33A 109.2 . . ?
H33B C33 H33A 107.9 . . ?
C35 O34 C33 114.2(3) . . ?
O34 C35 O36 109.0(2) . . ?
O34 C35 C44 107.1(3) . . ?
O36 C35 C44 106.0(3) . . ?
O34 C35 C45 112.0(3) . . ?
O36 C35 C45 110.8(2) . . ?
C44 C35 C45 111.6(3) . . ?
C37 O36 C35 114.5(2) . . ?
O36 C37 C38 107.3(2) . . ?
O36 C37 C32 111.9(2) . . ?
C38 C37 C32 102.8(2) . . ?
O36 C37 H37 111.5 . . ?
C38 C37 H37 111.5 . . ?
C32 C37 H37 111.5 . . ?
O39 C38 C37 109.2(2) . . ?
O39 C38 C30 105.5(2) . . ?
C37 C38 C30 104.1(2) . . ?
O39 C38 H38 112.5 . . ?
C37 C38 H38 112.5 . . ?
C30 C38 H38 112.5 . . ?
C38 O39 C40 108.2(2) . . ?
O29 C40 O39 104.4(2) . . ?
O29 C40 C46 108.7(3) . . ?
O39 C40 C46 108.2(3) . . ?
O29 C40 C47 110.1(3) . . ?
O39 C40 C47 110.3(3) . . ?
C46 C40 C47 114.6(3) . . ?
O42 C41 O43 127.0(3) . . ?
O42 C41 C30 117.7(2) . . ?
O43 C41 C30 115.3(3) . . ?
C35 C44 H44C 109.5 . . ?
C35 C44 H44B 109.5 . . ?
H44C C44 H44B 109.5 . . ?
C35 C44 H44A 109.5 . . ?
H44C C44 H44A 109.5 . . ?
H44B C44 H44A 109.5 . . ?
C35 C45 H45C 109.5 . . ?
C35 C45 H45B 109.5 . . ?
H45C C45 H45B 109.5 . . ?
C35 C45 H45A 109.5 . . ?
H45C C45 H45A 109.5 . . ?
H45B C45 H45A 109.5 . . ?
C40 C46 H46A 109.5 . . ?
C40 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
C40 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46C C46 H46B 109.5 . . ?
C40 C47 H47A 109.5 . . ?
C40 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C40 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C49 C48 C53 119.2(3) . . ?
C49 C48 C54 119.8(3) . . ?
C53 C48 C54 120.8(3) . . ?
C50 C49 C48 120.4(3) . . ?
C50 C49 H49 119.8 . . ?
C48 C49 H49 119.8 . . ?
C51 C50 C49 120.3(3) . . ?
C51 C50 H50 119.9 . . ?
C49 C50 H50 119.9 . . ?
C50 C51 C52 120.0(3) . . ?
C50 C51 H51 120.0 . . ?
C52 C51 H51 120.0 . . ?
C51 C52 C53 120.2(3) . . ?
C51 C52 H52 119.9 . . ?
C53 C52 H52 119.9 . . ?
C48 C53 C52 120.0(3) . . ?
C48 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
N56 C54 C55 109.4(2) . . ?
N56 C54 C48 111.8(2) . . ?
C55 C54 C48 111.3(2) . . ?
N56 C54 H54 108.0 . . ?
C55 C54 H54 108.0 . . ?
C48 C54 H54 108.0 . . ?
C54 C55 H55A 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
C54 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55C C55 H55B 109.5 . . ?
C54 N56 H56A 104.9 . . ?
C54 N56 H56C 114.0 . . ?
H56A N56 H56C 111.4 . . ?
C54 N56 H56B 108.3 . . ?
H56A N56 H56B 108.6 . . ?
H56C N56 H56B 109.4 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.84
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_snea
_database_code_depnum_ccdc_archive 'CCDC 950606'
_audit_update_record             
;
2013-07-16 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 O7, C12 H14 N '
_chemical_formula_sum            'C24 H31 N O7'
_chemical_formula_weight         445.50

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   P21
_chemical_absolute_configuration rm


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

_cell_length_a                   13.740(5)
_cell_length_b                   6.188(3)
_cell_length_c                   15.056(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.998(8)
_cell_angle_gamma                90.00
_cell_volume                     1169.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4368
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.51

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6011
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         26.51
_reflns_number_total             4368
_reflns_number_gt                3950
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0588P)²+0.3240P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         4368
_refine_ls_number_parameters     298
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.055
_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 0.82843(13) 0.8525(3) 0.12634(13) 0.0280(4) Uani 1 1 d . . .
C2 C 0.78997(16) 0.7717(4) 0.19436(16) 0.0206(5) Uani 1 1 d . . .
O3 O 0.75132(12) 0.9436(3) 0.23276(12) 0.0227(3) Uani 1 1 d . . .
C4 C 0.83756(17) 1.0187(4) 0.31949(17) 0.0227(5) Uani 1 1 d . . .
H4 H 0.8852 1.1167 0.3023 0.027 Uiso 1 1 calc R . .
C5 C 0.79331(18) 1.1359(4) 0.38280(18) 0.0260(5) Uani 1 1 d . . .
H5B H 0.8521 1.2087 0.4367 0.031 Uiso 1 1 calc R . .
H5A H 0.7425 1.2481 0.3439 0.031 Uiso 1 1 calc R . .
O6 O 0.74065(13) 0.9903(3) 0.42167(13) 0.0279(4) Uani 1 1 d . . .
C7 C 0.80439(19) 0.8121(4) 0.47235(18) 0.0280(5) Uani 1 1 d . . .
O8 O 0.83923(12) 0.6916(3) 0.40972(12) 0.0242(4) Uani 1 1 d . . .
C9 C 0.89654(17) 0.8134(4) 0.36631(16) 0.0216(5) Uani 1 1 d . . .
H9 H 0.9717 0.8422 0.4127 0.026 Uiso 1 1 calc R . .
C10 C 0.89026(16) 0.6837(4) 0.27851(16) 0.0215(5) Uani 1 1 d . . .
H10 H 0.8872 0.5242 0.2879 0.026 Uiso 1 1 calc R . .
O11 O 0.97651(12) 0.7458(3) 0.25490(12) 0.0277(4) Uani 1 1 d . . .
C12 C 0.93535(18) 0.7785(4) 0.15225(18) 0.0284(5) Uani 1 1 d . . .
C13 C 0.69538(16) 0.6163(4) 0.14258(16) 0.0208(5) Uani 1 1 d . . .
O14 O 0.71188(13) 0.4212(3) 0.16173(13) 0.0282(4) Uani 1 1 d . . .
O15 O 0.61053(12) 0.7028(3) 0.08402(12) 0.0271(4) Uani 1 1 d . . .
C16 C 0.7307(2) 0.6630(5) 0.4951(2) 0.0386(7) Uani 1 1 d . . .
H16A H 0.6701 0.6244 0.4347 0.058 Uiso 1 1 calc R . .
H16B H 0.7047 0.7361 0.5390 0.058 Uiso 1 1 calc R . .
H16C H 0.7693 0.5317 0.5264 0.058 Uiso 1 1 calc R . .
C17 C 0.8994(2) 0.8827(5) 0.56447(19) 0.0349(6) Uani 1 1 d . . .
H17B H 0.9326 0.7553 0.6038 0.052 Uiso 1 1 calc R . .
H17A H 0.8747 0.9806 0.6022 0.052 Uiso 1 1 calc R . .
H17C H 0.9515 0.9575 0.5464 0.052 Uiso 1 1 calc R . .
C18 C 0.9981(2) 0.9568(5) 0.1317(2) 0.0446(7) Uani 1 1 d . . .
H18A H 0.9918 1.0893 0.1646 0.067 Uiso 1 1 calc R . .
H18C H 0.9701 0.9825 0.0615 0.067 Uiso 1 1 calc R . .
H18B H 1.0732 0.9145 0.1557 0.067 Uiso 1 1 calc R . .
C19 C 0.93280(14) 0.5743(3) 0.1007(2) 0.0443(7) Uani 1 1 d . . .
H19A H 1.0057 0.5215 0.1191 0.066 Uiso 1 1 calc R . .
H19B H 0.8994 0.5993 0.0304 0.066 Uiso 1 1 calc R . .
H19C H 0.8916 0.4663 0.1184 0.066 Uiso 1 1 calc R . .
H32A H 0.5724 0.9755 0.1024 0.034(8) Uiso 1 1 d RD . .
H32C H 0.6018 1.2052 0.1274 0.032(7) Uiso 1 1 d RD . .
H32B H 0.4900 1.1465 0.0537 0.029(7) Uiso 1 1 d RD . .
C20 C 0.42249(17) 0.9349(4) 0.17108(18) 0.0222(5) Uani 1 1 d . . .
C21 C 0.36150(19) 0.8629(4) 0.07826(18) 0.0268(5) Uani 1 1 d . . .
H21 H 0.3769 0.9131 0.0258 0.032 Uiso 1 1 calc R . .
C22 C 0.27673(19) 0.7166(5) 0.05948(19) 0.0323(6) Uani 1 1 d . . .
H22 H 0.2378 0.6644 -0.0046 0.039 Uiso 1 1 calc R . .
C23 C 0.25083(19) 0.6503(4) 0.1329(2) 0.0321(6) Uani 1 1 d . . .
H23 H 0.1915 0.5572 0.1192 0.039 Uiso 1 1 calc R . .
C24 C 0.31116(18) 0.7181(4) 0.23018(18) 0.0276(5) Uani 1 1 d . . .
C25 C 0.2868(2) 0.6449(5) 0.3077(2) 0.0361(6) Uani 1 1 d . . .
H25 H 0.2271 0.5528 0.2942 0.043 Uiso 1 1 calc R . .
C26 C 0.3474(2) 0.7038(5) 0.4023(2) 0.0383(6) Uani 1 1 d . . .
H26 H 0.3303 0.6513 0.4535 0.046 Uiso 1 1 calc R . .
C27 C 0.4345(2) 0.8422(5) 0.4224(2) 0.0358(6) Uani 1 1 d . . .
H27 H 0.4764 0.8833 0.4877 0.043 Uiso 1 1 calc R . .
C28 C 0.4604(2) 0.9189(5) 0.34977(19) 0.0302(5) Uani 1 1 d . . .
H28 H 0.5200 1.0122 0.3653 0.036 Uiso 1 1 calc R . .
C29 C 0.39887(18) 0.8609(4) 0.25041(18) 0.0245(5) Uani 1 1 d . . .
C30 C 0.51203(18) 1.0978(4) 0.19128(17) 0.0234(5) Uani 1 1 d . . .
H30 H 0.5743 1.0487 0.2506 0.028 Uiso 1 1 calc R . .
C31 C 0.4823(2) 1.3239(5) 0.2110(2) 0.0380(6) Uani 1 1 d . . .
H31C H 0.5436 1.4204 0.2262 0.057 Uiso 1 1 calc R . .
H31B H 0.4619 1.3197 0.2661 0.057 Uiso 1 1 calc R . .
H31A H 0.4224 1.3773 0.1532 0.057 Uiso 1 1 calc R . .
N32 N 0.54706(13) 1.1086(2) 0.10891(13) 0.0219(4) Uani 1 1 d D . .


_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 1.421(3) . ?
O1 C12 1.433(3) . ?
C2 O3 1.413(3) . ?
C2 C10 1.543(3) . ?
C2 C13 1.548(3) . ?
O3 C4 1.438(3) . ?
C4 C5 1.508(3) . ?
C4 C9 1.518(3) . ?
C5 O6 1.422(3) . ?
O6 C7 1.422(3) . ?
C7 O8 1.429(3) . ?
C7 C16 1.509(4) . ?
C7 C17 1.532(3) . ?
O8 C9 1.426(3) . ?
C9 C10 1.519(3) . ?
C10 O11 1.422(3) . ?
O11 C12 1.428(3) . ?
C12 C19 1.476(3) . ?
C12 C18 1.508(4) . ?
C13 O14 1.240(3) . ?
C13 O15 1.260(3) . ?
C20 C21 1.379(3) . ?
C20 C29 1.434(3) . ?
C20 C30 1.522(3) . ?
C21 C22 1.410(4) . ?
C22 C23 1.355(4) . ?
C23 C24 1.421(4) . ?
C24 C25 1.414(4) . ?
C24 C29 1.424(3) . ?
C25 C26 1.374(4) . ?
C26 C27 1.401(4) . ?
C27 C28 1.364(4) . ?
C28 C29 1.433(4) . ?
C30 N32 1.503(3) . ?
C30 C31 1.520(4) . ?

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 C12 109.38(17) . . ?
O3 C2 O1 109.99(19) . . ?
O3 C2 C10 106.76(18) . . ?
O1 C2 C10 104.27(17) . . ?
O3 C2 C13 107.16(16) . . ?
O1 C2 C13 109.75(19) . . ?
C10 C2 C13 118.73(19) . . ?
C2 O3 C4 107.88(16) . . ?
O3 C4 C5 109.54(18) . . ?
O3 C4 C9 103.78(18) . . ?
C5 C4 C9 112.7(2) . . ?
O6 C5 C4 111.03(19) . . ?
C7 O6 C5 114.01(17) . . ?
O6 C7 O8 110.43(19) . . ?
O6 C7 C16 105.8(2) . . ?
O8 C7 C16 105.5(2) . . ?
O6 C7 C17 112.1(2) . . ?
O8 C7 C17 110.8(2) . . ?
C16 C7 C17 111.9(2) . . ?
C9 O8 C7 114.97(18) . . ?
O8 C9 C4 111.42(17) . . ?
O8 C9 C10 105.85(18) . . ?
C4 C9 C10 101.98(18) . . ?
O11 C10 C9 108.47(18) . . ?
O11 C10 C2 104.83(18) . . ?
C9 C10 C2 104.12(18) . . ?
C10 O11 C12 107.79(17) . . ?
O11 C12 O1 104.53(18) . . ?
O11 C12 C19 111.2(2) . . ?
O1 C12 C19 109.15(19) . . ?
O11 C12 C18 108.5(2) . . ?
O1 C12 C18 108.6(2) . . ?
C19 C12 C18 114.3(2) . . ?
O14 C13 O15 127.3(2) . . ?
O14 C13 C2 116.79(19) . . ?
O15 C13 C2 115.9(2) . . ?
C21 C20 C29 119.4(2) . . ?
C21 C20 C30 121.7(2) . . ?
C29 C20 C30 118.9(2) . . ?
C20 C21 C22 121.5(2) . . ?
C23 C22 C21 120.0(2) . . ?
C22 C23 C24 121.0(2) . . ?
C25 C24 C23 121.4(2) . . ?
C25 C24 C29 119.1(2) . . ?
C23 C24 C29 119.5(2) . . ?
C26 C25 C24 121.5(2) . . ?
C25 C26 C27 119.4(3) . . ?
C28 C27 C26 121.1(3) . . ?
C27 C28 C29 121.0(3) . . ?
C24 C29 C28 117.9(2) . . ?
C24 C29 C20 118.6(2) . . ?
C28 C29 C20 123.5(2) . . ?
N32 C30 C31 108.8(2) . . ?
N32 C30 C20 111.62(19) . . ?
C31 C30 C20 112.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        26.51
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_spea
_database_code_depnum_ccdc_archive 'CCDC 950607'
_audit_update_record             
;
2013-07-16 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 O7, C8 H12 N'
_chemical_formula_sum            'C20 H29 N O7'
_chemical_formula_weight         395.44

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   P21
_chemical_absolute_configuration rm


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

_cell_length_a                   14.634(3)
_cell_length_b                   6.2305(12)
_cell_length_c                   11.855(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.86(3)
_cell_angle_gamma                90.00
_cell_volume                     1053.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4682
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      28.37

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8188
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         28.37
_reflns_number_total             4682
_reflns_number_gt                4129
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0492P)²+0.1055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         4682
_refine_ls_number_parameters     262
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.018
_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 0.24133(8) 0.78174(17) -0.25009(9) 0.0303(2) Uani 1 1 d . . .
C2 C 0.24684(10) 0.8819(2) -0.14071(12) 0.0238(3) Uani 1 1 d . . .
O3 O 0.26785(7) 0.72706(16) -0.05221(9) 0.0269(2) Uani 1 1 d . . .
C4 C 0.18091(11) 0.6425(2) -0.03398(14) 0.0293(3) Uani 1 1 d . . .
H4 H 0.1553 0.5334 -0.0947 0.035 Uiso 1 1 calc R . .
C5 C 0.19605(12) 0.5427(3) 0.08393(16) 0.0374(4) Uani 1 1 d . . .
H5B H 0.1401 0.4573 0.0893 0.045 Uiso 1 1 calc R . .
H5A H 0.2503 0.4440 0.0951 0.045 Uiso 1 1 calc R . .
O6 O 0.21269(8) 0.70051(19) 0.17355(10) 0.0361(3) Uani 1 1 d . . .
C7 C 0.14419(12) 0.8657(3) 0.16002(14) 0.0336(3) Uani 1 1 d . . .
O8 O 0.13817(7) 0.97463(17) 0.05168(9) 0.0285(2) Uani 1 1 d . . .
C9 C 0.11676(11) 0.8397(2) -0.04820(13) 0.0267(3) Uani 1 1 d . . .
H9 H 0.0490 0.7991 -0.0689 0.032 Uiso 1 1 calc R . .
C10 C 0.14620(10) 0.9621(2) -0.14518(12) 0.0254(3) Uani 1 1 d . . .
H10 H 0.1427 1.1213 -0.1363 0.030 Uiso 1 1 calc R . .
O11 O 0.09216(7) 0.8871(2) -0.25287(9) 0.0352(3) Uani 1 1 d . . .
C12 C 0.15478(11) 0.8399(3) -0.32638(14) 0.0346(4) Uani 1 1 d . . .
C13 C 0.32752(10) 1.0470(2) -0.11815(12) 0.0240(3) Uani 1 1 d . . .
O14 O 0.30616(9) 1.23972(17) -0.12447(12) 0.0403(3) Uani 1 1 d . . .
O15 O 0.40914(7) 0.96937(16) -0.09682(9) 0.0274(2) Uani 1 1 d . . .
C16 C 0.18170(15) 1.0286(3) 0.25219(14) 0.0471(4) Uani 1 1 d . . .
H16B H 0.1868 0.9636 0.3286 0.071 Uiso 1 1 calc R . .
H16C H 0.1390 1.1517 0.2438 0.071 Uiso 1 1 calc R . .
H16A H 0.2437 1.0769 0.2442 0.071 Uiso 1 1 calc R . .
C17 C 0.04824(13) 0.7795(3) 0.16859(18) 0.0462(5) Uani 1 1 d . . .
H17C H 0.0231 0.6888 0.1014 0.069 Uiso 1 1 calc R . .
H17B H 0.0055 0.8999 0.1704 0.069 Uiso 1 1 calc R . .
H17A H 0.0546 0.6947 0.2395 0.069 Uiso 1 1 calc R . .
C18 C 0.11672(15) 0.6490(4) -0.4000(2) 0.0589(6) Uani 1 1 d . . .
H18A H 0.1121 0.5260 -0.3501 0.088 Uiso 1 1 calc R . .
H18C H 0.1589 0.6136 -0.4510 0.088 Uiso 1 1 calc R . .
H18B H 0.0544 0.6834 -0.4469 0.088 Uiso 1 1 calc R . .
C19 C 0.17005(15) 1.0359(4) -0.39593(17) 0.0506(5) Uani 1 1 d . . .
H19A H 0.1108 1.0763 -0.4482 0.076 Uiso 1 1 calc R . .
H19B H 0.2166 1.0027 -0.4413 0.076 Uiso 1 1 calc R . .
H19C H 0.1926 1.1552 -0.3432 0.076 Uiso 1 1 calc R . .
C20 C 0.44750(11) 0.5611(3) -0.31907(13) 0.0309(3) Uani 1 1 d . . .
C21 C 0.45652(15) 0.7495(3) -0.37780(15) 0.0423(4) Uani 1 1 d . . .
H21 H 0.4987 0.8575 -0.3413 0.051 Uiso 1 1 calc R . .
C22 C 0.40383(10) 0.78212(17) -0.49090(11) 0.0527(5) Uani 1 1 d . . .
H22 H 0.4090 0.9132 -0.5299 0.063 Uiso 1 1 calc R . .
H28A H 0.4242 0.6692 -0.1113 0.029(4) Uiso 1 1 d RD . .
H28C H 0.4026 0.4424 -0.1193 0.027(4) Uiso 1 1 d RD . .
H28B H 0.4868 0.5151 -0.0367 0.042(5) Uiso 1 1 d RD . .
C23 C 0.34485(14) 0.6234(4) -0.54463(15) 0.0501(5) Uani 1 1 d . . .
H23 H 0.3107 0.6427 -0.6221 0.060 Uiso 1 1 calc R . .
C24 C 0.33495(13) 0.4355(4) -0.48641(15) 0.0462(5) Uani 1 1 d . . .
H24 H 0.2933 0.3270 -0.5235 0.055 Uiso 1 1 calc R . .
C25 C 0.38599(12) 0.4048(3) -0.37334(14) 0.0384(4) Uani 1 1 d . . .
H25 H 0.3785 0.2760 -0.3334 0.046 Uiso 1 1 calc R . .
C26 C 0.50793(10) 0.5249(3) -0.19905(13) 0.0294(3) Uani 1 1 d . . .
H26 H 0.5560 0.6416 -0.1832 0.035 Uiso 1 1 calc R . .
C27 C 0.55952(13) 0.3105(3) -0.18760(14) 0.0387(4) Uani 1 1 d . . .
H27B H 0.6018 0.3010 -0.1111 0.058 Uiso 1 1 calc R . .
H27A H 0.5959 0.2998 -0.2475 0.058 Uiso 1 1 calc R . .
H27C H 0.5139 0.1929 -0.1969 0.058 Uiso 1 1 calc R . .
N28 N 0.45077(8) 0.53761(15) -0.10882(9) 0.0240(2) Uani 1 1 d D . .


_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 1.4252(18) . ?
O1 C12 1.430(2) . ?
C2 O3 1.4081(17) . ?
C2 C13 1.544(2) . ?
C2 C10 1.5448(19) . ?
O3 C4 1.4371(18) . ?
C4 C5 1.501(2) . ?
C4 C9 1.533(2) . ?
C5 O6 1.428(2) . ?
O6 C7 1.421(2) . ?
C7 O8 1.4380(18) . ?
C7 C16 1.503(3) . ?
C7 C17 1.528(2) . ?
O8 C9 1.4290(18) . ?
C9 C10 1.519(2) . ?
C10 O11 1.4226(18) . ?
O11 C12 1.429(2) . ?
C12 C18 1.507(3) . ?
C12 C19 1.518(3) . ?
C13 O14 1.2390(18) . ?
C13 O15 1.2610(17) . ?
C20 C25 1.384(3) . ?
C20 C21 1.386(2) . ?
C20 C26 1.516(2) . ?
C21 C22 1.405(2) . ?
C22 C23 1.373(3) . ?
C23 C24 1.383(3) . ?
C24 C25 1.395(2) . ?
C26 N28 1.4995(17) . ?
C26 C27 1.525(2) . ?

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 C12 109.12(11) . . ?
O3 C2 O1 109.67(11) . . ?
O3 C2 C13 107.20(11) . . ?
O1 C2 C13 109.61(11) . . ?
O3 C2 C10 107.19(11) . . ?
O1 C2 C10 104.47(11) . . ?
C13 C2 C10 118.51(12) . . ?
C2 O3 C4 108.03(11) . . ?
O3 C4 C5 109.86(13) . . ?
O3 C4 C9 103.32(11) . . ?
C5 C4 C9 113.23(13) . . ?
O6 C5 C4 111.92(13) . . ?
C7 O6 C5 114.55(13) . . ?
O6 C7 O8 110.14(12) . . ?
O6 C7 C16 105.83(14) . . ?
O8 C7 C16 105.68(13) . . ?
O6 C7 C17 111.97(15) . . ?
O8 C7 C17 110.53(14) . . ?
C16 C7 C17 112.42(15) . . ?
C9 O8 C7 114.89(11) . . ?
O8 C9 C10 106.56(11) . . ?
O8 C9 C4 111.38(12) . . ?
C10 C9 C4 102.45(12) . . ?
O11 C10 C9 108.65(12) . . ?
O11 C10 C2 105.08(11) . . ?
C9 C10 C2 103.91(12) . . ?
C10 O11 C12 108.12(11) . . ?
O11 C12 O1 105.34(13) . . ?
O11 C12 C18 108.15(15) . . ?
O1 C12 C18 109.15(15) . . ?
O11 C12 C19 110.95(14) . . ?
O1 C12 C19 109.32(14) . . ?
C18 C12 C19 113.59(17) . . ?
O14 C13 O15 126.78(14) . . ?
O14 C13 C2 117.54(13) . . ?
O15 C13 C2 115.67(12) . . ?
C25 C20 C21 119.17(16) . . ?
C25 C20 C26 120.99(14) . . ?
C21 C20 C26 119.78(16) . . ?
C20 C21 C22 120.56(17) . . ?
C23 C22 C21 119.58(14) . . ?
C22 C23 C24 120.21(16) . . ?
C23 C24 C25 120.17(19) . . ?
C20 C25 C24 120.27(16) . . ?
N28 C26 C20 111.11(12) . . ?
N28 C26 C27 109.06(12) . . ?
C20 C26 C27 112.82(13) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033
