# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1a
_audit_block_doi                 10.5517/cc1kk3mv
_database_code_depnum_ccdc_archive 'CCDC 1446417'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N2 O6'
_chemical_formula_sum            'C14 H18 N2 O6'
_chemical_formula_weight         310.30

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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.7507(8)
_cell_length_b                   13.2608(11)
_cell_length_c                   12.6760(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.655(4)
_cell_angle_gamma                90.00
_cell_volume                     1467.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4424
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      27.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12194
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3358
_reflns_number_gt                2390
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0738P)²+0.5913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3358
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C1 C 1.0992(2) 0.09463(18) 0.29180(19) 0.0532(5) Uani 1 1 d . . .
H1A H 1.1154 0.0467 0.3493 0.064 Uiso 1 1 calc R . .
H1B H 1.0906 0.1619 0.3209 0.064 Uiso 1 1 calc R . .
C2 C 1.2259(3) 0.0891(4) 0.2171(3) 0.1125(14) Uani 1 1 d . . .
H2A H 1.3037 0.1391 0.2361 0.135 Uiso 1 1 calc R . .
H2B H 1.2732 0.0229 0.2207 0.135 Uiso 1 1 calc R . .
C3 C 1.1581(3) 0.1084(2) 0.1081(2) 0.0746(8) Uani 1 1 d . . .
H3A H 1.1835 0.0543 0.0607 0.090 Uiso 1 1 calc R . .
H3B H 1.1959 0.1715 0.0809 0.090 Uiso 1 1 calc R . .
C4 C 0.9864(2) 0.11362(15) 0.11831(16) 0.0464(5) Uani 1 1 d . . .
H4 H 0.9353 0.0716 0.0631 0.056 Uiso 1 1 calc R . .
C5 C 0.81446(19) 0.10871(12) 0.25419(13) 0.0320(4) Uani 1 1 d . . .
C6 C 0.6907(2) 0.05038(14) 0.18621(16) 0.0411(4) Uani 1 1 d . . .
C7 C 0.5782(3) -0.1082(2) 0.1517(2) 0.0793(9) Uani 1 1 d . . .
H7A H 0.4743 -0.0930 0.1662 0.119 Uiso 1 1 calc R . .
H7B H 0.5992 -0.1779 0.1676 0.119 Uiso 1 1 calc R . .
H7C H 0.5927 -0.0957 0.0784 0.119 Uiso 1 1 calc R . .
C8 C 0.7954(2) 0.09288(13) 0.37168(14) 0.0373(4) Uani 1 1 d . . .
H8A H 0.8095 0.0220 0.3883 0.045 Uiso 1 1 calc R . .
H8B H 0.8743 0.1304 0.4120 0.045 Uiso 1 1 calc R . .
C9 C 0.6416(2) 0.12578(14) 0.40469(16) 0.0426(5) Uani 1 1 d . . .
C10 C 0.4861(3) 0.1449(3) 0.5479(2) 0.0867(10) Uani 1 1 d . . .
H10A H 0.4785 0.2171 0.5504 0.130 Uiso 1 1 calc R . .
H10B H 0.4788 0.1179 0.6177 0.130 Uiso 1 1 calc R . .
H10C H 0.4044 0.1185 0.5019 0.130 Uiso 1 1 calc R . .
C11 C 0.8746(2) 0.30056(13) 0.28467(14) 0.0407(4) Uani 1 1 d . . .
C12 C 0.8081(2) 0.21881(13) 0.21287(14) 0.0357(4) Uani 1 1 d . . .
H12 H 0.7023 0.2361 0.1897 0.043 Uiso 1 1 calc R . .
C13 C 0.9070(2) 0.21906(14) 0.11770(14) 0.0418(5) Uani 1 1 d . . .
H13 H 0.8415 0.2269 0.0526 0.050 Uiso 1 1 calc R . .
C14 C 1.0078(3) 0.31042(15) 0.13380(16) 0.0491(5) Uani 1 1 d . . .
N1 N 0.96181(16) 0.06821(11) 0.22296(12) 0.0361(4) Uani 1 1 d . . .
N2 N 0.9853(2) 0.35015(12) 0.23206(13) 0.0489(5) Uani 1 1 d . . .
H2 H 1.0356 0.4010 0.2581 0.059 Uiso 1 1 calc R . .
O1 O 0.6169(2) 0.08473(14) 0.11273(14) 0.0717(5) Uani 1 1 d . . .
O2 O 0.68206(18) -0.04461(11) 0.21709(13) 0.0570(4) Uani 1 1 d . . .
O3 O 0.53987(19) 0.15605(15) 0.34699(14) 0.0705(5) Uani 1 1 d . . .
O4 O 0.6322(2) 0.11654(14) 0.50836(12) 0.0651(5) Uani 1 1 d . . .
O5 O 0.8359(2) 0.32348(11) 0.37096(11) 0.0586(5) Uani 1 1 d . . .
O6 O 1.0925(2) 0.34653(13) 0.07200(14) 0.0734(6) Uani 1 1 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
C1 N1 1.482(3) . ?
C1 C2 1.505(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.491(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.518(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.485(2) . ?
C4 C13 1.561(3) . ?
C4 H4 0.9800 . ?
C5 N1 1.474(2) . ?
C5 C8 1.524(2) . ?
C5 C6 1.547(3) . ?
C5 C12 1.551(2) . ?
C6 O1 1.190(2) . ?
C6 O2 1.323(2) . ?
C7 O2 1.459(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.499(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O3 1.185(3) . ?
C9 O4 1.327(3) . ?
C10 O4 1.453(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O5 1.204(2) . ?
C11 N2 1.378(3) . ?
C11 C12 1.508(3) . ?
C12 C13 1.529(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.505(3) . ?
C13 H13 0.9800 . ?
C14 O6 1.211(2) . ?
C14 N2 1.378(3) . ?
N2 H2 0.8600 . ?

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
N1 C1 C2 102.7(2) . . ?
N1 C1 H1A 111.2 . . ?
C2 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
C3 C2 C1 108.0(2) . . ?
C3 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C3 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
C2 C3 C4 105.4(2) . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
N1 C4 C3 105.00(19) . . ?
N1 C4 C13 106.12(14) . . ?
C3 C4 C13 118.88(18) . . ?
N1 C4 H4 108.8 . . ?
C3 C4 H4 108.8 . . ?
C13 C4 H4 108.8 . . ?
N1 C5 C8 111.39(14) . . ?
N1 C5 C6 105.15(13) . . ?
C8 C5 C6 111.04(14) . . ?
N1 C5 C12 105.40(13) . . ?
C8 C5 C12 117.12(14) . . ?
C6 C5 C12 105.88(14) . . ?
O1 C6 O2 123.89(19) . . ?
O1 C6 C5 124.78(18) . . ?
O2 C6 C5 111.26(17) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C5 112.89(16) . . ?
C9 C8 H8A 109.0 . . ?
C5 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C5 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O3 C9 O4 123.4(2) . . ?
O3 C9 C8 125.33(19) . . ?
O4 C9 C8 111.27(19) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 N2 124.49(18) . . ?
O5 C11 C12 127.54(18) . . ?
N2 C11 C12 107.89(16) . . ?
C11 C12 C13 104.98(15) . . ?
C11 C12 C5 117.95(15) . . ?
C13 C12 C5 104.98(14) . . ?
C11 C12 H12 109.5 . . ?
C13 C12 H12 109.5 . . ?
C5 C12 H12 109.5 . . ?
C14 C13 C12 104.55(15) . . ?
C14 C13 C4 117.60(18) . . ?
C12 C13 C4 105.57(14) . . ?
C14 C13 H13 109.6 . . ?
C12 C13 H13 109.6 . . ?
C4 C13 H13 109.6 . . ?
O6 C14 N2 124.20(19) . . ?
O6 C14 C13 127.47(19) . . ?
N2 C14 C13 108.31(16) . . ?
C5 N1 C1 116.51(14) . . ?
C5 N1 C4 105.75(14) . . ?
C1 N1 C4 105.77(16) . . ?
C14 N2 C11 113.59(16) . . ?
C14 N2 H2 123.2 . . ?
C11 N2 H2 123.2 . . ?
C6 O2 C7 115.35(19) . . ?
C9 O4 C10 115.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.86 2.23 2.978(2) 145.4 2_755
N2 H2 O2 0.86 2.57 3.255(2) 136.9 2_755

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_1c
_audit_block_doi                 10.5517/cc1kk3nw
_database_code_depnum_ccdc_archive 'CCDC 1446418'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N2 O6'
_chemical_formula_sum            'C20 H22 N2 O6'
_chemical_formula_weight         386.40

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'



loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7337(10)
_cell_length_b                   10.5429(13)
_cell_length_c                   11.3995(14)
_cell_angle_alpha                64.657(4)
_cell_angle_beta                 80.000(4)
_cell_angle_gamma                74.626(4)
_cell_volume                     912.50(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6498
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      27.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13728
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4152
_reflns_number_gt                3120
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0708P)²+0.1423P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4152
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_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
C1 C 0.58114(19) 0.63166(18) 0.27118(17) 0.0385(4) Uani 1 1 d . . .
H1 H 0.5207 0.5581 0.3263 0.046 Uiso 1 1 calc R . .
C2 C 0.4846(2) 0.7396(2) 0.1571(2) 0.0588(5) Uani 1 1 d . . .
H2A H 0.5242 0.8275 0.1143 0.071 Uiso 1 1 calc R . .
H2B H 0.3730 0.7625 0.1845 0.071 Uiso 1 1 calc R . .
C3 C 0.5101(3) 0.6593(3) 0.0678(2) 0.0783(7) Uani 1 1 d . . .
H3A H 0.4163 0.6236 0.0737 0.094 Uiso 1 1 calc R . .
H3B H 0.5305 0.7231 -0.0219 0.094 Uiso 1 1 calc R . .
C4 C 0.6534(2) 0.5344(2) 0.11367(18) 0.0487(4) Uani 1 1 d . . .
H4A H 0.6212 0.4429 0.1563 0.058 Uiso 1 1 calc R . .
H4B H 0.7307 0.5326 0.0418 0.058 Uiso 1 1 calc R . .
C5 C 0.83289(18) 0.47118(16) 0.29956(14) 0.0307(3) Uani 1 1 d . . .
C6 C 0.77277(18) 0.33708(16) 0.39890(15) 0.0340(3) Uani 1 1 d . . .
C7 C 0.7634(3) 0.09765(19) 0.4463(2) 0.0532(5) Uani 1 1 d . . .
H7A H 0.8494 0.0364 0.5001 0.080 Uiso 1 1 calc R . .
H7B H 0.7404 0.0508 0.3974 0.080 Uiso 1 1 calc R . .
H7C H 0.6706 0.1171 0.5002 0.080 Uiso 1 1 calc R . .
C8 C 0.98894(18) 0.42932(16) 0.22847(15) 0.0341(4) Uani 1 1 d . . .
H8A H 0.9718 0.3762 0.1821 0.041 Uiso 1 1 calc R . .
H8B H 1.0212 0.5160 0.1646 0.041 Uiso 1 1 calc R . .
C9 C 1.12099(19) 0.33995(16) 0.31651(16) 0.0354(4) Uani 1 1 d . . .
C10 C 1.3943(2) 0.2344(2) 0.3204(2) 0.0602(5) Uani 1 1 d . . .
H10A H 1.4209 0.2835 0.3656 0.090 Uiso 1 1 calc R . .
H10B H 1.4828 0.2168 0.2623 0.090 Uiso 1 1 calc R . .
H10C H 1.3700 0.1445 0.3822 0.090 Uiso 1 1 calc R . .
C11 C 0.94228(18) 0.67013(16) 0.30632(14) 0.0315(3) Uani 1 1 d . . .
C12 C 0.83071(18) 0.56830(16) 0.37171(14) 0.0312(3) Uani 1 1 d . . .
H12 H 0.8525 0.5101 0.4632 0.037 Uiso 1 1 calc R . .
C13 C 0.66345(19) 0.66669(17) 0.35947(16) 0.0360(4) Uani 1 1 d . . .
H13 H 0.6052 0.6460 0.4449 0.043 Uiso 1 1 calc R . .
C14 C 0.6921(2) 0.81690(18) 0.30129(17) 0.0401(4) Uani 1 1 d . . .
C15 C 0.92443(19) 0.93513(16) 0.20617(15) 0.0343(4) Uani 1 1 d . . .
C16 C 0.8511(2) 1.05515(18) 0.10404(16) 0.0421(4) Uani 1 1 d . . .
H16 H 0.7553 1.0569 0.0778 0.050 Uiso 1 1 calc R . .
C17 C 0.9224(2) 1.17162(19) 0.04222(18) 0.0506(5) Uani 1 1 d . . .
H17 H 0.8730 1.2532 -0.0248 0.061 Uiso 1 1 calc R . .
C18 C 1.0659(3) 1.16812(19) 0.07890(19) 0.0515(5) Uani 1 1 d . . .
H18 H 1.1151 1.2457 0.0345 0.062 Uiso 1 1 calc R . .
C19 C 1.1371(2) 1.0498(2) 0.18144(19) 0.0507(5) Uani 1 1 d . . .
H19 H 1.2333 1.0484 0.2069 0.061 Uiso 1 1 calc R . .
C20 C 1.0659(2) 0.93261(18) 0.24683(17) 0.0424(4) Uani 1 1 d . . .
H20 H 1.1127 0.8535 0.3171 0.051 Uiso 1 1 calc R . .
N1 N 0.71651(16) 0.56771(14) 0.20519(12) 0.0358(3) Uani 1 1 d . . .
N2 N 0.85425(15) 0.81160(13) 0.26752(12) 0.0331(3) Uani 1 1 d . . .
O1 O 0.69666(15) 0.33030(13) 0.49869(12) 0.0493(3) Uani 1 1 d . . .
O2 O 0.80795(16) 0.23095(12) 0.35799(12) 0.0483(3) Uani 1 1 d . . .
O3 O 1.10807(15) 0.28835(14) 0.43308(12) 0.0505(3) Uani 1 1 d . . .
O4 O 1.25806(14) 0.32164(14) 0.24705(12) 0.0490(3) Uani 1 1 d . . .
O5 O 1.08504(13) 0.63723(12) 0.29003(12) 0.0420(3) Uani 1 1 d . . .
O6 O 0.59385(16) 0.92626(14) 0.28709(16) 0.0628(4) Uani 1 1 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
C1 N1 1.456(2) . ?
C1 C2 1.517(3) . ?
C1 C13 1.541(2) . ?
C1 H1 0.9800 . ?
C2 C3 1.536(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.460(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.456(2) . ?
C5 C8 1.521(2) . ?
C5 C6 1.541(2) . ?
C5 C12 1.559(2) . ?
C6 O1 1.1976(19) . ?
C6 O2 1.3336(19) . ?
C7 O2 1.443(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.497(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O3 1.1984(19) . ?
C9 O4 1.3328(19) . ?
C10 O4 1.438(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O5 1.2062(19) . ?
C11 N2 1.3988(19) . ?
C11 C12 1.508(2) . ?
C12 C13 1.540(2) . ?
C12 H12 0.9800 . ?
C13 C14 1.504(2) . ?
C13 H13 0.9800 . ?
C14 O6 1.206(2) . ?
C14 N2 1.395(2) . ?
C15 C20 1.383(3) . ?
C15 C16 1.391(2) . ?
C15 N2 1.4337(19) . ?
C16 C17 1.380(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(2) . ?
C19 H19 0.9300 . ?
C20 H20 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
N1 C1 C2 101.11(14) . . ?
N1 C1 C13 101.97(12) . . ?
C2 C1 C13 126.34(15) . . ?
N1 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
C13 C1 H1 108.6 . . ?
C1 C2 C3 102.48(15) . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C4 C3 C2 107.00(16) . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3A 110.3 . . ?
C4 C3 H3B 110.3 . . ?
C2 C3 H3B 110.3 . . ?
H3A C3 H3B 108.6 . . ?
N1 C4 C3 101.96(15) . . ?
N1 C4 H4A 111.4 . . ?
C3 C4 H4A 111.4 . . ?
N1 C4 H4B 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.2 . . ?
N1 C5 C8 109.45(12) . . ?
N1 C5 C6 112.03(12) . . ?
C8 C5 C6 111.02(12) . . ?
N1 C5 C12 99.10(11) . . ?
C8 C5 C12 117.24(12) . . ?
C6 C5 C12 107.49(11) . . ?
O1 C6 O2 123.41(14) . . ?
O1 C6 C5 124.31(13) . . ?
O2 C6 C5 112.19(13) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C5 113.60(12) . . ?
C9 C8 H8A 108.8 . . ?
C5 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C5 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O3 C9 O4 123.55(16) . . ?
O3 C9 C8 126.01(14) . . ?
O4 C9 C8 110.42(13) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 N2 124.42(14) . . ?
O5 C11 C12 126.37(14) . . ?
N2 C11 C12 109.20(13) . . ?
C11 C12 C13 104.53(12) . . ?
C11 C12 C5 113.02(11) . . ?
C13 C12 C5 106.18(12) . . ?
C11 C12 H12 110.9 . . ?
C13 C12 H12 110.9 . . ?
C5 C12 H12 110.9 . . ?
C14 C13 C12 104.97(12) . . ?
C14 C13 C1 114.50(14) . . ?
C12 C13 C1 104.65(12) . . ?
C14 C13 H13 110.8 . . ?
C12 C13 H13 110.8 . . ?
C1 C13 H13 110.8 . . ?
O6 C14 N2 123.97(16) . . ?
O6 C14 C13 126.90(15) . . ?
N2 C14 C13 109.11(13) . . ?
C20 C15 C16 120.71(15) . . ?
C20 C15 N2 119.83(14) . . ?
C16 C15 N2 119.44(15) . . ?
C17 C16 C15 119.14(17) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C16 120.57(17) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.09(17) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.31(18) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 119.12(17) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C5 N1 C1 108.80(12) . . ?
C5 N1 C4 126.51(13) . . ?
C1 N1 C4 107.26(13) . . ?
C14 N2 C11 111.76(13) . . ?
C14 N2 C15 124.55(13) . . ?
C11 N2 C15 123.63(13) . . ?
C6 O2 C7 116.80(13) . . ?
C9 O4 C10 116.00(15) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_1g
_audit_block_doi                 10.5517/cc1kk3px
_database_code_depnum_ccdc_archive 'CCDC 1446419'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 N2 O6'
_chemical_formula_sum            'C22 H26 N2 O6'
_chemical_formula_weight         414.45

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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.0950(13)
_cell_length_b                   10.2803(13)
_cell_length_c                   19.4298(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.348(6)
_cell_angle_gamma                90.00
_cell_volume                     2091.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7604
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      23.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31020
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.62
_reflns_number_total             4835
_reflns_number_gt                2820
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0667P)²+0.6053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4835
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C1 C 0.2258(2) 1.0180(2) 0.73797(11) 0.0477(5) Uani 1 1 d . . .
H1 H 0.1740 1.0222 0.7702 0.057 Uiso 1 1 calc R . .
C2 C 0.3614(3) 1.0596(3) 0.78114(14) 0.0756(8) Uani 1 1 d . . .
H2A H 0.3979 1.1113 0.7512 0.091 Uiso 1 1 calc R . .
H2B H 0.3631 1.1099 0.8237 0.091 Uiso 1 1 calc R . .
C3 C 0.4326(3) 0.9346(3) 0.80311(16) 0.0855(9) Uani 1 1 d . . .
H3A H 0.4232 0.9006 0.8476 0.103 Uiso 1 1 calc R . .
H3B H 0.5227 0.9457 0.8101 0.103 Uiso 1 1 calc R . .
C4 C 0.3690(3) 0.8466(3) 0.73889(17) 0.0942(10) Uani 1 1 d . . .
H4A H 0.4015 0.8628 0.6991 0.113 Uiso 1 1 calc R . .
H4B H 0.3821 0.7557 0.7528 0.113 Uiso 1 1 calc R . .
C5 C 0.14393(19) 0.85150(19) 0.64693(10) 0.0400(5) Uani 1 1 d . . .
C6 C 0.0233(2) 0.8059(2) 0.66258(11) 0.0486(5) Uani 1 1 d . . .
C7 C -0.1662(3) 0.8716(3) 0.68327(17) 0.0791(9) Uani 1 1 d . . .
H7A H -0.2197 0.8161 0.6449 0.095 Uiso 1 1 calc R . .
H7B H -0.1450 0.8246 0.7291 0.095 Uiso 1 1 calc R . .
C8 C -0.2329(3) 0.9872(4) 0.6873(2) 0.1220(15) Uani 1 1 d . . .
H8A H -0.1789 1.0426 0.7247 0.183 Uiso 1 1 calc R . .
H8B H -0.3083 0.9659 0.6988 0.183 Uiso 1 1 calc R . .
H8C H -0.2567 1.0315 0.6413 0.183 Uiso 1 1 calc R . .
C9 C 0.1874(2) 0.7404(2) 0.60909(12) 0.0473(5) Uani 1 1 d . . .
H9A H 0.2696 0.7626 0.6047 0.057 Uiso 1 1 calc R . .
H9B H 0.1991 0.6631 0.6392 0.057 Uiso 1 1 calc R . .
C10 C 0.0956(2) 0.7101(2) 0.53475(12) 0.0435(5) Uani 1 1 d . . .
C11 C 0.0729(3) 0.5873(3) 0.42748(13) 0.0665(7) Uani 1 1 d . . .
H11A H -0.0171 0.6056 0.4172 0.080 Uiso 1 1 calc R . .
H11B H 0.0820 0.4956 0.4184 0.080 Uiso 1 1 calc R . .
C12 C 0.1233(3) 0.6671(3) 0.37973(15) 0.0839(9) Uani 1 1 d . . .
H12A H 0.1131 0.7577 0.3886 0.126 Uiso 1 1 calc R . .
H12B H 0.0773 0.6472 0.3296 0.126 Uiso 1 1 calc R . .
H12C H 0.2123 0.6483 0.3900 0.126 Uiso 1 1 calc R . .
C13 C 0.20561(17) 1.01419(19) 0.56227(10) 0.0361(4) Uani 1 1 d . . .
C14 C 0.11953(17) 0.98461(18) 0.60653(10) 0.0349(4) Uani 1 1 d . . .
H14 H 0.0297 0.9919 0.5759 0.042 Uiso 1 1 calc R . .
C15 C 0.15282(19) 1.08998(19) 0.66543(10) 0.0390(5) Uani 1 1 d . . .
H15 H 0.0751 1.1310 0.6686 0.047 Uiso 1 1 calc R . .
C16 C 0.2326(2) 1.1868(2) 0.64240(11) 0.0441(5) Uani 1 1 d . . .
C17 C 0.34761(18) 1.1938(2) 0.55162(11) 0.0408(5) Uani 1 1 d . . .
C18 C 0.3102(2) 1.3103(2) 0.51654(13) 0.0544(6) Uani 1 1 d . . .
H18 H 0.2350 1.3502 0.5166 0.065 Uiso 1 1 calc R . .
C19 C 0.3856(2) 1.3674(3) 0.48119(14) 0.0680(7) Uani 1 1 d . . .
H19 H 0.3609 1.4461 0.4571 0.082 Uiso 1 1 calc R . .
C20 C 0.4958(3) 1.3097(3) 0.48113(14) 0.0660(7) Uani 1 1 d . . .
H20 H 0.5454 1.3487 0.4566 0.079 Uiso 1 1 calc R . .
C21 C 0.5338(2) 1.1954(3) 0.51675(15) 0.0665(7) Uani 1 1 d . . .
H21 H 0.6099 1.1570 0.5171 0.080 Uiso 1 1 calc R . .
C22 C 0.4595(2) 1.1356(2) 0.55268(13) 0.0559(6) Uani 1 1 d . . .
H22 H 0.4852 1.0572 0.5771 0.067 Uiso 1 1 calc R . .
N1 N 0.23708(17) 0.88112(18) 0.71903(9) 0.0523(5) Uani 1 1 d . . .
N2 N 0.26860(14) 1.13066(16) 0.58704(8) 0.0377(4) Uani 1 1 d . . .
O1 O 0.00056(19) 0.69450(17) 0.67162(11) 0.0803(6) Uani 1 1 d . . .
O2 O -0.04959(14) 0.90420(15) 0.66812(9) 0.0558(4) Uani 1 1 d . . .
O3 O -0.00612(14) 0.76107(15) 0.50692(9) 0.0540(4) Uani 1 1 d . . .
O4 O 0.14363(15) 0.61781(15) 0.50321(8) 0.0589(4) Uani 1 1 d . . .
O5 O 0.21724(14) 0.95219(15) 0.51228(8) 0.0524(4) Uani 1 1 d . . .
O6 O 0.26364(17) 1.29462(16) 0.66651(9) 0.0653(5) Uani 1 1 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
C1 N1 1.471(3) . ?
C1 C2 1.521(3) . ?
C1 C15 1.560(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.494(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.513(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.430(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.471(3) . ?
C5 C9 1.521(3) . ?
C5 C6 1.541(3) . ?
C5 C14 1.556(3) . ?
C6 O1 1.198(3) . ?
C6 O2 1.321(3) . ?
C7 C8 1.417(4) . ?
C7 O2 1.457(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.499(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O3 1.198(2) . ?
C10 O4 1.333(2) . ?
C11 O4 1.454(3) . ?
C11 C12 1.480(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O5 1.204(2) . ?
C13 N2 1.389(2) . ?
C13 C14 1.513(3) . ?
C14 C15 1.530(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.495(3) . ?
C15 H15 0.9800 . ?
C16 O6 1.209(2) . ?
C16 N2 1.391(2) . ?
C17 C22 1.372(3) . ?
C17 C18 1.373(3) . ?
C17 N2 1.436(2) . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.358(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.358(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 H22 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
N1 C1 C2 104.83(19) . . ?
N1 C1 C15 106.82(16) . . ?
C2 C1 C15 119.2(2) . . ?
N1 C1 H1 108.5 . . ?
C2 C1 H1 108.5 . . ?
C15 C1 H1 108.5 . . ?
C3 C2 C1 104.4(2) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C4 102.7(2) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C3 103.3(2) . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 C9 112.36(16) . . ?
N1 C5 C6 104.91(15) . . ?
C9 C5 C6 107.62(17) . . ?
N1 C5 C14 104.38(16) . . ?
C9 C5 C14 116.51(16) . . ?
C6 C5 C14 110.48(16) . . ?
O1 C6 O2 123.7(2) . . ?
O1 C6 C5 124.0(2) . . ?
O2 C6 C5 112.25(18) . . ?
C8 C7 O2 109.4(2) . . ?
C8 C7 H7A 109.8 . . ?
O2 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
O2 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C5 113.48(17) . . ?
C10 C9 H9A 108.9 . . ?
C5 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C5 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
O3 C10 O4 124.3(2) . . ?
O3 C10 C9 125.60(19) . . ?
O4 C10 C9 110.06(18) . . ?
O4 C11 C12 109.0(2) . . ?
O4 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
O4 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 N2 124.03(17) . . ?
O5 C13 C14 127.50(18) . . ?
N2 C13 C14 108.43(16) . . ?
C13 C14 C15 103.97(15) . . ?
C13 C14 C5 115.25(16) . . ?
C15 C14 C5 106.67(15) . . ?
C13 C14 H14 110.2 . . ?
C15 C14 H14 110.2 . . ?
C5 C14 H14 110.2 . . ?
C16 C15 C14 105.52(15) . . ?
C16 C15 C1 113.86(17) . . ?
C14 C15 C1 105.35(16) . . ?
C16 C15 H15 110.6 . . ?
C14 C15 H15 110.6 . . ?
C1 C15 H15 110.6 . . ?
O6 C16 N2 124.21(19) . . ?
O6 C16 C15 127.99(19) . . ?
N2 C16 C15 107.80(17) . . ?
C22 C17 C18 120.7(2) . . ?
C22 C17 N2 119.24(19) . . ?
C18 C17 N2 120.02(18) . . ?
C17 C18 C19 119.1(2) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 119.0(2) . . ?
C17 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C4 N1 C1 109.5(2) . . ?
C4 N1 C5 122.63(19) . . ?
C1 N1 C5 110.19(16) . . ?
C13 N2 C16 112.64(16) . . ?
C13 N2 C17 122.69(15) . . ?
C16 N2 C17 124.09(17) . . ?
C6 O2 C7 116.65(19) . . ?
C10 O4 C11 117.05(18) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_2b
_audit_block_doi                 10.5517/cc1kk3qy
_database_code_depnum_ccdc_archive 'CCDC 1446420'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N2 O6 S'
_chemical_formula_sum            'C14 H18 N2 O6 S'
_chemical_formula_weight         342.36

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'
S S 0.1246 0.1234 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   7.952(2)
_cell_length_b                   12.865(3)
_cell_length_c                   16.507(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.409(12)
_cell_angle_gamma                90.00
_cell_volume                     1611.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7108
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  '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            15735
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3698
_reflns_number_gt                2813
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0750P)²+0.5919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3698
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_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
C1 C 0.3485(3) 0.97890(16) 0.86170(12) 0.0412(5) Uani 1 1 d . . .
H1A H 0.4238 0.9186 0.8656 0.049 Uiso 1 1 calc R . .
H1B H 0.2501 0.9604 0.8821 0.049 Uiso 1 1 calc R . .
C2 C 0.3884(3) 1.18094(15) 0.83543(13) 0.0430(5) Uani 1 1 d . . .
H2A H 0.3533 1.2453 0.8564 0.052 Uiso 1 1 calc R . .
H2B H 0.4766 1.1961 0.8073 0.052 Uiso 1 1 calc R . .
C3 C 0.2309(2) 1.12611(13) 0.77583(11) 0.0306(4) Uani 1 1 d . . .
H3 H 0.1317 1.1293 0.7995 0.037 Uiso 1 1 calc R . .
C4 C 0.3065(3) 1.19500(14) 0.64606(12) 0.0345(4) Uani 1 1 d . . .
C5 C 0.1648(2) 1.15184(13) 0.68097(11) 0.0300(4) Uani 1 1 d . . .
H5 H 0.0625 1.1982 0.6683 0.036 Uiso 1 1 calc R . .
C6 C 0.1151(2) 1.04543(13) 0.63655(11) 0.0302(4) Uani 1 1 d . . .
H6 H -0.0087 1.0444 0.6017 0.036 Uiso 1 1 calc R . .
C7 C 0.2372(3) 1.03488(15) 0.58194(12) 0.0358(4) Uani 1 1 d . . .
C8 C 0.4629(4) 1.1423(2) 0.54256(16) 0.0599(7) Uani 1 1 d . . .
H8A H 0.5738 1.1102 0.5710 0.090 Uiso 1 1 calc R . .
H8B H 0.4796 1.2158 0.5383 0.090 Uiso 1 1 calc R . .
H8C H 0.4169 1.1134 0.4867 0.090 Uiso 1 1 calc R . .
C9 C 0.1504(2) 0.96335(13) 0.70869(12) 0.0305(4) Uani 1 1 d . . .
C10 C -0.0122(3) 0.94414(15) 0.73917(14) 0.0406(5) Uani 1 1 d . . .
C11 C -0.2852(3) 1.0067(2) 0.74816(19) 0.0656(7) Uani 1 1 d . . .
H11A H -0.3511 0.9460 0.7234 0.098 Uiso 1 1 calc R . .
H11B H -0.3590 1.0670 0.7332 0.098 Uiso 1 1 calc R . .
H11C H -0.2452 0.9994 0.8088 0.098 Uiso 1 1 calc R . .
C12 C 0.2182(3) 0.85755(14) 0.69040(13) 0.0376(4) Uani 1 1 d . . .
H12A H 0.3267 0.8672 0.6758 0.045 Uiso 1 1 calc R . .
H12B H 0.2448 0.8152 0.7413 0.045 Uiso 1 1 calc R . .
C13 C 0.0870(3) 0.80155(15) 0.61918(15) 0.0444(5) Uani 1 1 d . . .
C14 C 0.0422(5) 0.6554(2) 0.5288(2) 0.0897(11) Uani 1 1 d . . .
H14A H -0.0730 0.6505 0.5359 0.135 Uiso 1 1 calc R . .
H14B H 0.0903 0.5870 0.5290 0.135 Uiso 1 1 calc R . .
H14C H 0.0338 0.6889 0.4758 0.135 Uiso 1 1 calc R . .
N1 N 0.28754(19) 1.01784(11) 0.77515(9) 0.0288(3) Uani 1 1 d . . .
N2 N 0.3391(2) 1.12357(13) 0.59070(10) 0.0375(4) Uani 1 1 d . . .
O1 O 0.3816(2) 1.27736(12) 0.66274(11) 0.0557(4) Uani 1 1 d . . .
O2 O 0.2464(2) 0.96271(13) 0.53682(10) 0.0543(4) Uani 1 1 d . . .
O3 O -0.0188(2) 0.87331(14) 0.78567(15) 0.0769(6) Uani 1 1 d . . .
O4 O -0.13416(18) 1.01803(11) 0.71649(10) 0.0451(4) Uani 1 1 d . . .
O5 O -0.0624(2) 0.82864(13) 0.58633(13) 0.0701(6) Uani 1 1 d . . .
O6 O 0.1563(2) 0.71585(13) 0.59799(12) 0.0653(5) Uani 1 1 d . . .
S1 S 0.47155(10) 1.08812(5) 0.92138(4) 0.0619(2) Uani 1 1 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
C1 N1 1.453(2) . ?
C1 S1 1.823(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.516(3) . ?
C2 S1 1.821(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.465(2) . ?
C3 C5 1.531(3) . ?
C3 H3 0.9800 . ?
C4 O1 1.207(2) . ?
C4 N2 1.374(3) . ?
C4 C5 1.516(3) . ?
C5 C6 1.548(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.516(3) . ?
C6 C9 1.553(2) . ?
C6 H6 0.9800 . ?
C7 O2 1.206(2) . ?
C7 N2 1.382(3) . ?
C8 N2 1.459(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N1 1.473(2) . ?
C9 C12 1.527(2) . ?
C9 C10 1.541(3) . ?
C10 O3 1.203(3) . ?
C10 O4 1.329(2) . ?
C11 O4 1.453(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.502(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O5 1.201(3) . ?
C13 O6 1.325(3) . ?
C14 O6 1.453(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
N1 C1 S1 103.47(13) . . ?
N1 C1 H1A 111.1 . . ?
S1 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
S1 C1 H1B 111.1 . . ?
H1A C1 H1B 109.0 . . ?
C3 C2 S1 103.74(13) . . ?
C3 C2 H2A 111.0 . . ?
S1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
S1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
N1 C3 C2 104.54(15) . . ?
N1 C3 C5 102.11(14) . . ?
C2 C3 C5 121.80(16) . . ?
N1 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C5 C3 H3 109.2 . . ?
O1 C4 N2 124.04(18) . . ?
O1 C4 C5 127.45(18) . . ?
N2 C4 C5 108.51(15) . . ?
C4 C5 C3 113.68(15) . . ?
C4 C5 C6 104.93(14) . . ?
C3 C5 C6 104.72(14) . . ?
C4 C5 H5 111.1 . . ?
C3 C5 H5 111.1 . . ?
C6 C5 H5 111.1 . . ?
C7 C6 C5 104.03(14) . . ?
C7 C6 C9 113.22(14) . . ?
C5 C6 C9 106.04(14) . . ?
C7 C6 H6 111.1 . . ?
C5 C6 H6 111.1 . . ?
C9 C6 H6 111.1 . . ?
O2 C7 N2 123.93(19) . . ?
O2 C7 C6 127.16(19) . . ?
N2 C7 C6 108.90(15) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C12 110.17(14) . . ?
N1 C9 C10 109.87(15) . . ?
C12 C9 C10 107.59(15) . . ?
N1 C9 C6 99.86(13) . . ?
C12 C9 C6 116.61(16) . . ?
C10 C9 C6 112.49(15) . . ?
O3 C10 O4 123.67(19) . . ?
O3 C10 C9 122.05(18) . . ?
O4 C10 C9 113.95(16) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 112.24(16) . . ?
C13 C12 H12A 109.2 . . ?
C9 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C9 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
O5 C13 O6 123.7(2) . . ?
O5 C13 C12 125.17(19) . . ?
O6 C13 C12 111.07(18) . . ?
O6 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C3 109.46(14) . . ?
C1 N1 C9 121.55(15) . . ?
C3 N1 C9 107.30(14) . . ?
C4 N2 C7 113.59(16) . . ?
C4 N2 C8 122.96(18) . . ?
C7 N2 C8 123.38(18) . . ?
C10 O4 C11 116.00(18) . . ?
C13 O6 C14 116.2(2) . . ?
C2 S1 C1 94.20(9) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.090
####################################################################### 
# 
# 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_2f
_audit_block_doi                 10.5517/cc1kk3rz
_database_code_depnum_ccdc_archive 'CCDC 1446421'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 Br N2 O6 S'
_chemical_formula_sum            'C19 H19 Br N2 O6 S'
_chemical_formula_weight         483.33

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8046(14)
_cell_length_b                   10.5597(17)
_cell_length_c                   11.8943(19)
_cell_angle_alpha                69.617(4)
_cell_angle_beta                 83.083(4)
_cell_angle_gamma                73.659(4)
_cell_volume                     994.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9135
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    2.212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.538
_exptl_absorpt_correction_T_max  0.642
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14775
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.57
_reflns_number_total             4523
_reflns_number_gt                3870
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0415P)²+0.5572P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4523
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.35948(4) 0.24141(3) 0.99732(2) 0.05916(12) Uani 1 1 d . . .
C1 C 0.8509(3) 1.0261(3) 0.8461(2) 0.0442(5) Uani 1 1 d . . .
H1A H 0.7727 1.0389 0.9087 0.053 Uiso 1 1 calc R . .
H1B H 0.8742 1.1149 0.8010 0.053 Uiso 1 1 calc R . .
C2 C 1.0372(3) 0.7966(3) 0.8078(3) 0.0571(7) Uani 1 1 d . . .
H2A H 1.1443 0.7686 0.7777 0.068 Uiso 1 1 calc R . .
H2B H 0.9989 0.7139 0.8478 0.068 Uiso 1 1 calc R . .
C3 C 0.9294(2) 0.8991(2) 0.7071(2) 0.0374(5) Uani 1 1 d . . .
H3 H 0.9846 0.9678 0.6549 0.045 Uiso 1 1 calc R . .
C4 C 0.6722(2) 1.0538(2) 0.67972(17) 0.0278(4) Uani 1 1 d . . .
C5 C 0.7245(2) 1.1786(2) 0.58601(18) 0.0310(4) Uani 1 1 d . . .
C6 C 0.7321(3) 1.4137(2) 0.5397(2) 0.0497(6) Uani 1 1 d . . .
H6A H 0.8295 1.3860 0.4981 0.074 Uiso 1 1 calc R . .
H6B H 0.7459 1.4697 0.5843 0.074 Uiso 1 1 calc R . .
H6C H 0.6502 1.4670 0.4826 0.074 Uiso 1 1 calc R . .
C7 C 0.5186(2) 1.1032(2) 0.74454(18) 0.0314(4) Uani 1 1 d . . .
H7A H 0.4918 1.0224 0.8046 0.038 Uiso 1 1 calc R . .
H7B H 0.5356 1.1623 0.7860 0.038 Uiso 1 1 calc R . .
C8 C 0.3813(2) 1.1827(2) 0.6627(2) 0.0335(4) Uani 1 1 d . . .
C9 C 0.1072(3) 1.2879(3) 0.6617(3) 0.0645(8) Uani 1 1 d . . .
H9A H 0.1249 1.3688 0.5982 0.097 Uiso 1 1 calc R . .
H9B H 0.0246 1.3167 0.7150 0.097 Uiso 1 1 calc R . .
H9C H 0.0764 1.2284 0.6283 0.097 Uiso 1 1 calc R . .
C10 C 0.5709(2) 0.8488(2) 0.67922(17) 0.0304(4) Uani 1 1 d . . .
C11 C 0.6749(2) 0.9468(2) 0.61655(17) 0.0291(4) Uani 1 1 d . . .
H11 H 0.6475 0.9946 0.5320 0.035 Uiso 1 1 calc R . .
C12 C 0.8448(2) 0.8511(2) 0.62828(19) 0.0342(4) Uani 1 1 d . . .
H12 H 0.8974 0.8634 0.5492 0.041 Uiso 1 1 calc R . .
C13 C 0.8252(3) 0.7046(2) 0.6839(2) 0.0374(5) Uani 1 1 d . . .
C14 C 0.6020(3) 0.5929(2) 0.77459(18) 0.0326(4) Uani 1 1 d . . .
C15 C 0.6794(3) 0.4843(2) 0.8708(2) 0.0419(5) Uani 1 1 d . . .
H15 H 0.7773 0.4839 0.8930 0.050 Uiso 1 1 calc R . .
C16 C 0.6103(3) 0.3766(2) 0.9335(2) 0.0462(5) Uani 1 1 d . . .
H16 H 0.6620 0.3029 0.9976 0.055 Uiso 1 1 calc R . .
C17 C 0.4639(3) 0.3788(2) 0.90064(19) 0.0410(5) Uani 1 1 d . . .
C18 C 0.3884(3) 0.4833(2) 0.8026(2) 0.0415(5) Uani 1 1 d . . .
H18 H 0.2918 0.4819 0.7795 0.050 Uiso 1 1 calc R . .
C19 C 0.4582(3) 0.5905(2) 0.73897(19) 0.0373(4) Uani 1 1 d . . .
H19 H 0.4090 0.6612 0.6721 0.045 Uiso 1 1 calc R . .
N1 N 0.79551(19) 0.96954(18) 0.76773(15) 0.0320(4) Uani 1 1 d . . .
N2 N 0.6651(2) 0.71112(17) 0.71480(15) 0.0308(3) Uani 1 1 d . . .
O1 O 0.7969(2) 1.17322(17) 0.49493(15) 0.0449(4) Uani 1 1 d . . .
O2 O 0.6882(2) 1.29042(16) 0.62116(15) 0.0442(4) Uani 1 1 d . . .
O3 O 0.38711(19) 1.21716(18) 0.55567(15) 0.0474(4) Uani 1 1 d . . .
O4 O 0.25083(18) 1.2126(2) 0.72713(17) 0.0517(4) Uani 1 1 d . . .
O5 O 0.42931(17) 0.88078(16) 0.69507(16) 0.0427(4) Uani 1 1 d . . .
O6 O 0.9276(2) 0.59721(18) 0.6988(2) 0.0600(5) Uani 1 1 d . . .
S1 S 1.02986(10) 0.89365(10) 0.90906(9) 0.0811(3) Uani 1 1 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
Br1 C17 1.899(2) . ?
C1 N1 1.457(3) . ?
C1 S1 1.820(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.517(3) . ?
C2 S1 1.819(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.463(3) . ?
C3 C12 1.550(3) . ?
C3 H3 0.9800 . ?
C4 N1 1.465(2) . ?
C4 C7 1.526(3) . ?
C4 C5 1.545(3) . ?
C4 C11 1.554(3) . ?
C5 O1 1.200(3) . ?
C5 O2 1.331(2) . ?
C6 O2 1.448(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.502(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O3 1.195(3) . ?
C8 O4 1.326(3) . ?
C9 O4 1.442(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O5 1.206(2) . ?
C10 N2 1.399(2) . ?
C10 C11 1.515(3) . ?
C11 C12 1.542(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.507(3) . ?
C12 H12 0.9800 . ?
C13 O6 1.205(3) . ?
C13 N2 1.402(3) . ?
C14 C15 1.387(3) . ?
C14 C19 1.392(3) . ?
C14 N2 1.431(3) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(3) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 H19 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
N1 C1 S1 103.68(15) . . ?
N1 C1 H1A 111.0 . . ?
S1 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
S1 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C3 C2 S1 104.02(17) . . ?
C3 C2 H2A 111.0 . . ?
S1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
S1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
N1 C3 C2 104.37(19) . . ?
N1 C3 C12 101.82(16) . . ?
C2 C3 C12 122.5(2) . . ?
N1 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C12 C3 H3 109.1 . . ?
N1 C4 C7 109.49(15) . . ?
N1 C4 C5 111.07(15) . . ?
C7 C4 C5 111.23(16) . . ?
N1 C4 C11 99.63(14) . . ?
C7 C4 C11 117.16(16) . . ?
C5 C4 C11 107.71(15) . . ?
O1 C5 O2 123.77(19) . . ?
O1 C5 C4 123.92(18) . . ?
O2 C5 C4 112.21(16) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C4 113.68(16) . . ?
C8 C7 H7A 108.8 . . ?
C4 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C4 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
O3 C8 O4 124.4(2) . . ?
O3 C8 C7 125.99(19) . . ?
O4 C8 C7 109.61(18) . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 C10 N2 124.12(19) . . ?
O5 C10 C11 126.83(18) . . ?
N2 C10 C11 109.03(16) . . ?
C10 C11 C12 104.60(16) . . ?
C10 C11 C4 113.37(15) . . ?
C12 C11 C4 106.10(15) . . ?
C10 C11 H11 110.8 . . ?
C12 C11 H11 110.8 . . ?
C4 C11 H11 110.8 . . ?
C13 C12 C11 105.08(16) . . ?
C13 C12 C3 115.07(19) . . ?
C11 C12 C3 104.81(15) . . ?
C13 C12 H12 110.5 . . ?
C11 C12 H12 110.5 . . ?
C3 C12 H12 110.5 . . ?
O6 C13 N2 124.1(2) . . ?
O6 C13 C12 126.9(2) . . ?
N2 C13 C12 108.98(17) . . ?
C15 C14 C19 120.0(2) . . ?
C15 C14 N2 120.49(19) . . ?
C19 C14 N2 119.48(18) . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 Br1 119.20(19) . . ?
C16 C17 Br1 119.51(17) . . ?
C17 C18 C19 119.0(2) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C14 120.3(2) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C1 N1 C3 110.51(17) . . ?
C1 N1 C4 122.48(16) . . ?
C3 N1 C4 108.23(15) . . ?
C10 N2 C13 111.91(17) . . ?
C10 N2 C14 122.96(17) . . ?
C13 N2 C14 125.13(17) . . ?
C5 O2 C6 116.74(18) . . ?
C8 O4 C9 116.6(2) . . ?
C2 S1 C1 94.32(11) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_2g
_audit_block_doi                 10.5517/cc1kk3s0
_database_code_depnum_ccdc_archive 'CCDC 1446422'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 N2 O6 S'
_chemical_formula_sum            'C21 H24 N2 O6 S'
_chemical_formula_weight         432.48

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'
S S 0.1246 0.1234 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.954(7)
_cell_length_b                   16.203(10)
_cell_length_c                   13.457(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.401(19)
_cell_angle_gamma                90.00
_cell_volume                     2157(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7495
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      23.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22017
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.41
_reflns_number_total             4809
_reflns_number_gt                3091
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.1767P)²+1.6003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.070(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4809
_refine_ls_number_parameters     274
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0927
_refine_ls_wR_factor_ref         0.3022
_refine_ls_wR_factor_gt          0.2615
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.062
_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
C1 C 0.4235(4) 0.0259(2) 0.2411(3) 0.0508(9) Uani 1 1 d . . .
H1 H 0.3296 0.0260 0.2567 0.061 Uiso 1 1 calc R . .
C2 C 0.4272(5) 0.0021(3) 0.1323(3) 0.0707(12) Uani 1 1 d . . .
H2A H 0.3665 -0.0436 0.1139 0.085 Uiso 1 1 calc R . .
H2B H 0.5180 -0.0132 0.1196 0.085 Uiso 1 1 calc R . .
C3 C 0.3924(4) 0.1625(3) 0.1756(3) 0.0586(10) Uani 1 1 d . . .
H3A H 0.4377 0.2137 0.1626 0.070 Uiso 1 1 calc R . .
H3B H 0.3061 0.1747 0.1994 0.070 Uiso 1 1 calc R . .
C4 C 0.5064(4) 0.1327(2) 0.3536(2) 0.0425(8) Uani 1 1 d . . .
C5 C 0.3755(4) 0.1382(2) 0.4058(3) 0.0502(9) Uani 1 1 d . . .
C6 C 0.1933(5) 0.2267(4) 0.4369(5) 0.101(2) Uani 1 1 d D . .
H6A H 0.1822 0.2848 0.4514 0.121 Uiso 1 1 calc R . .
H6B H 0.1921 0.1953 0.4982 0.121 Uiso 1 1 calc R . .
C7 C 0.0836(7) 0.1970(5) 0.3567(6) 0.136(3) Uani 1 1 d D . .
H7A H 0.0814 0.2322 0.2992 0.204 Uiso 1 1 calc R . .
H7B H -0.0025 0.1986 0.3825 0.204 Uiso 1 1 calc R . .
H7C H 0.1029 0.1414 0.3381 0.204 Uiso 1 1 calc R . .
C8 C 0.5870(4) 0.2134(2) 0.3648(2) 0.0463(8) Uani 1 1 d . . .
H8A H 0.6667 0.2085 0.3298 0.056 Uiso 1 1 calc R . .
H8B H 0.5320 0.2580 0.3342 0.056 Uiso 1 1 calc R . .
C9 C 0.6298(4) 0.2340(2) 0.4738(3) 0.0532(9) Uani 1 1 d . . .
C10 C 0.7485(5) 0.3271(4) 0.5849(4) 0.1042(11) Uani 1 1 d DU . .
H10A H 0.7258 0.2851 0.6316 0.125 Uiso 1 1 calc R . .
H10B H 0.6966 0.3763 0.5956 0.125 Uiso 1 1 calc R . .
C11 C 0.8990(5) 0.3463(5) 0.6023(5) 0.1191(14) Uani 1 1 d DU . .
H11A H 0.9488 0.3037 0.5731 0.179 Uiso 1 1 calc R . .
H11B H 0.9270 0.3491 0.6729 0.179 Uiso 1 1 calc R . .
H11C H 0.9162 0.3983 0.5721 0.179 Uiso 1 1 calc R . .
C12 C 0.6284(4) -0.0665(2) 0.2904(3) 0.0487(9) Uani 1 1 d . . .
C13 C 0.5142(4) -0.0190(2) 0.3259(3) 0.0451(8) Uani 1 1 d . . .
H13 H 0.4598 -0.0542 0.3652 0.054 Uiso 1 1 calc R . .
C14 C 0.5806(3) 0.05205(19) 0.3904(2) 0.0406(8) Uani 1 1 d . . .
H14 H 0.5713 0.0426 0.4613 0.049 Uiso 1 1 calc R . .
C15 C 0.7279(4) 0.0478(2) 0.3723(2) 0.0452(8) Uani 1 1 d . . .
C16 C 0.8785(4) -0.0509(2) 0.2933(3) 0.0510(9) Uani 1 1 d . . .
C17 C 0.9807(4) -0.0647(3) 0.3708(3) 0.0628(11) Uani 1 1 d . . .
H17 H 0.9652 -0.0556 0.4369 0.075 Uiso 1 1 calc R . .
C18 C 1.1067(5) -0.0924(3) 0.3484(4) 0.0790(14) Uani 1 1 d . . .
H18 H 1.1755 -0.1012 0.4000 0.095 Uiso 1 1 calc R . .
C19 C 1.1306(5) -0.1066(3) 0.2525(5) 0.0860(17) Uani 1 1 d . . .
H19 H 1.2151 -0.1250 0.2388 0.103 Uiso 1 1 calc R . .
C20 C 1.0299(7) -0.0937(4) 0.1758(5) 0.0927(18) Uani 1 1 d . . .
H20 H 1.0460 -0.1041 0.1102 0.111 Uiso 1 1 calc R . .
C21 C 0.9029(5) -0.0650(3) 0.1959(3) 0.0741(13) Uani 1 1 d . . .
H21 H 0.8353 -0.0554 0.1436 0.089 Uiso 1 1 calc R . .
N1 N 0.4764(3) 0.11073(17) 0.2466(2) 0.0445(7) Uani 1 1 d . . .
N2 N 0.7485(3) -0.02301(17) 0.3159(2) 0.0463(7) Uani 1 1 d . . .
O1 O 0.3292(3) 0.08176(17) 0.4502(2) 0.0624(8) Uani 1 1 d . . .
O2 O 0.3182(3) 0.21224(18) 0.3921(3) 0.0785(10) Uani 1 1 d . . .
O3 O 0.5916(3) 0.19906(18) 0.5447(2) 0.0672(8) Uani 1 1 d . . .
O4 O 0.7157(4) 0.2976(3) 0.4816(3) 0.0985(11) Uani 1 1 d U . .
O5 O 0.6232(3) -0.13224(18) 0.2465(2) 0.0718(9) Uani 1 1 d . . .
O6 O 0.8174(3) 0.09534(16) 0.4022(2) 0.0644(8) Uani 1 1 d . . .
S1 S 0.37129(17) 0.09604(9) 0.06346(9) 0.0887(6) Uani 1 1 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
C1 N1 1.471(5) . ?
C1 C2 1.519(6) . ?
C1 C13 1.555(5) . ?
C1 H1 0.9800 . ?
C2 S1 1.836(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.462(5) . ?
C3 S1 1.846(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.480(4) . ?
C4 C8 1.531(5) . ?
C4 C5 1.551(5) . ?
C4 C14 1.555(4) . ?
C5 O1 1.212(4) . ?
C5 O2 1.331(4) . ?
C6 O2 1.461(6) . ?
C6 C7 1.525(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.518(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O3 1.207(5) . ?
C9 O4 1.335(5) . ?
C10 O4 1.472(6) . ?
C10 C11 1.523(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O5 1.217(4) . ?
C12 N2 1.397(5) . ?
C12 C13 1.495(5) . ?
C13 C14 1.545(5) . ?
C13 H13 0.9800 . ?
C14 C15 1.514(5) . ?
C14 H14 0.9800 . ?
C15 O6 1.212(4) . ?
C15 N2 1.404(4) . ?
C16 C21 1.379(6) . ?
C16 C17 1.391(6) . ?
C16 N2 1.435(5) . ?
C17 C18 1.397(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.357(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.401(7) . ?
C20 H20 0.9300 . ?
C21 H21 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
N1 C1 C2 103.8(3) . . ?
N1 C1 C13 103.0(3) . . ?
C2 C1 C13 120.9(3) . . ?
N1 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
C13 C1 H1 109.4 . . ?
C1 C2 S1 103.7(3) . . ?
C1 C2 H2A 111.0 . . ?
S1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
S1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
N1 C3 S1 101.8(3) . . ?
N1 C3 H3A 111.4 . . ?
S1 C3 H3A 111.4 . . ?
N1 C3 H3B 111.4 . . ?
S1 C3 H3B 111.4 . . ?
H3A C3 H3B 109.3 . . ?
N1 C4 C8 110.4(3) . . ?
N1 C4 C5 111.5(3) . . ?
C8 C4 C5 111.3(3) . . ?
N1 C4 C14 98.3(2) . . ?
C8 C4 C14 117.4(3) . . ?
C5 C4 C14 107.3(3) . . ?
O1 C5 O2 124.6(3) . . ?
O1 C5 C4 124.4(3) . . ?
O2 C5 C4 110.9(3) . . ?
O2 C6 C7 103.4(5) . . ?
O2 C6 H6A 111.1 . . ?
C7 C6 H6A 111.1 . . ?
O2 C6 H6B 111.1 . . ?
C7 C6 H6B 111.1 . . ?
H6A C6 H6B 109.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C4 111.8(3) . . ?
C9 C8 H8A 109.3 . . ?
C4 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C4 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
O3 C9 O4 123.7(4) . . ?
O3 C9 C8 125.5(4) . . ?
O4 C9 C8 110.8(3) . . ?
O4 C10 C11 108.8(4) . . ?
O4 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
O4 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 N2 123.4(3) . . ?
O5 C12 C13 127.8(3) . . ?
N2 C12 C13 108.8(3) . . ?
C12 C13 C14 105.6(3) . . ?
C12 C13 C1 114.0(3) . . ?
C14 C13 C1 103.9(3) . . ?
C12 C13 H13 111.0 . . ?
C14 C13 H13 111.0 . . ?
C1 C13 H13 111.0 . . ?
C15 C14 C13 103.7(3) . . ?
C15 C14 C4 114.9(3) . . ?
C13 C14 C4 106.8(3) . . ?
C15 C14 H14 110.4 . . ?
C13 C14 H14 110.4 . . ?
C4 C14 H14 110.4 . . ?
O6 C15 N2 123.5(3) . . ?
O6 C15 C14 127.4(3) . . ?
N2 C15 C14 109.1(3) . . ?
C21 C16 C17 119.7(4) . . ?
C21 C16 N2 120.8(4) . . ?
C17 C16 N2 119.5(3) . . ?
C16 C17 C18 119.2(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 121.1(5) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 119.9(5) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.3(5) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 119.8(5) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C3 N1 C1 109.1(3) . . ?
C3 N1 C4 122.4(3) . . ?
C1 N1 C4 107.8(3) . . ?
C12 N2 C15 111.8(3) . . ?
C12 N2 C16 123.8(3) . . ?
C15 N2 C16 124.2(3) . . ?
C5 O2 C6 117.2(3) . . ?
C9 O4 C10 113.5(4) . . ?
C2 S1 C3 94.04(18) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.41
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.950
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.150
####################################################################### 
# 
# 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_3a
_audit_block_doi                 10.5517/cc1kk3t1
_database_code_depnum_ccdc_archive 'CCDC 1446423'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 N2 O6'
_chemical_formula_sum            'C21 H24 N2 O6'
_chemical_formula_weight         400.42

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3547(17)
_cell_length_b                   10.5618(19)
_cell_length_c                   11.822(2)
_cell_angle_alpha                63.544(5)
_cell_angle_beta                 75.007(5)
_cell_angle_gamma                71.573(5)
_cell_volume                     982.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4081
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11140
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3371
_reflns_number_gt                2259
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0758P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3371
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
C1 C 0.1098(2) 0.6385(2) 0.29833(19) 0.0330(5) Uani 1 1 d . . .
H1 H 0.0466 0.5689 0.3530 0.040 Uiso 1 1 calc R . .
C2 C 0.0137(2) 0.7687(3) 0.2078(2) 0.0493(6) Uani 1 1 d . . .
H2A H 0.0743 0.8385 0.1513 0.059 Uiso 1 1 calc R . .
H2B H -0.0698 0.8151 0.2553 0.059 Uiso 1 1 calc R . .
C3 C -0.0487(3) 0.7207(3) 0.1300(3) 0.0644(8) Uani 1 1 d . . .
H3A H -0.1183 0.6595 0.1857 0.077 Uiso 1 1 calc R . .
H3B H -0.1044 0.8053 0.0668 0.077 Uiso 1 1 calc R . .
C4 C 0.0808(3) 0.6369(3) 0.0637(2) 0.0626(8) Uani 1 1 d . . .
H4A H 0.1415 0.7026 -0.0011 0.075 Uiso 1 1 calc R . .
H4B H 0.0389 0.5989 0.0216 0.075 Uiso 1 1 calc R . .
C5 C 0.1820(3) 0.5120(3) 0.1570(2) 0.0491(6) Uani 1 1 d . . .
H5A H 0.1249 0.4402 0.2163 0.059 Uiso 1 1 calc R . .
H5B H 0.2676 0.4656 0.1111 0.059 Uiso 1 1 calc R . .
C6 C 0.3492(2) 0.4674(2) 0.31433(18) 0.0276(5) Uani 1 1 d . . .
C7 C 0.2889(2) 0.3346(2) 0.4151(2) 0.0333(5) Uani 1 1 d . . .
C8 C 0.2675(3) 0.0993(3) 0.4612(3) 0.0641(8) Uani 1 1 d . . .
H8A H 0.3295 0.0403 0.5282 0.096 Uiso 1 1 calc R . .
H8B H 0.2697 0.0444 0.4141 0.096 Uiso 1 1 calc R . .
H8C H 0.1647 0.1287 0.4975 0.096 Uiso 1 1 calc R . .
C9 C 0.5004(2) 0.4208(2) 0.23932(19) 0.0331(5) Uani 1 1 d . . .
H9A H 0.4861 0.3636 0.1996 0.040 Uiso 1 1 calc R . .
H9B H 0.5300 0.5071 0.1717 0.040 Uiso 1 1 calc R . .
C10 C 0.6269(2) 0.3341(2) 0.3181(2) 0.0336(5) Uani 1 1 d . . .
C11 C 0.8921(3) 0.2300(3) 0.3061(3) 0.0656(8) Uani 1 1 d . . .
H11A H 0.9099 0.2786 0.3514 0.098 Uiso 1 1 calc R . .
H11B H 0.9786 0.2197 0.2434 0.098 Uiso 1 1 calc R . .
H11C H 0.8764 0.1356 0.3651 0.098 Uiso 1 1 calc R . .
C12 C 0.2148(2) 0.8120(2) 0.33209(19) 0.0343(5) Uani 1 1 d . . .
C13 C 0.1896(2) 0.6613(2) 0.38457(19) 0.0309(5) Uani 1 1 d . . .
H13 H 0.1348 0.6349 0.4716 0.037 Uiso 1 1 calc R . .
C14 C 0.3498(2) 0.5624(2) 0.38239(18) 0.0256(5) Uani 1 1 d . . .
H14 H 0.3744 0.5019 0.4692 0.031 Uiso 1 1 calc R . .
C15 C 0.4540(2) 0.6659(2) 0.30923(18) 0.0284(5) Uani 1 1 d . . .
C16 C 0.4281(2) 0.9352(2) 0.21150(18) 0.0298(5) Uani 1 1 d . . .
C17 C 0.5632(2) 0.9379(2) 0.2365(2) 0.0406(6) Uani 1 1 d . . .
H17 H 0.6136 0.8594 0.3008 0.049 Uiso 1 1 calc R . .
C18 C 0.6221(3) 1.0595(3) 0.1641(2) 0.0505(6) Uani 1 1 d . . .
H18 H 0.7129 1.0626 0.1800 0.061 Uiso 1 1 calc R . .
C19 C 0.5484(3) 1.1759(2) 0.0690(2) 0.0487(6) Uani 1 1 d . . .
H19 H 0.5903 1.2563 0.0199 0.058 Uiso 1 1 calc R . .
C20 C 0.4125(3) 1.1733(2) 0.0465(2) 0.0465(6) Uani 1 1 d . . .
H20 H 0.3610 1.2531 -0.0163 0.056 Uiso 1 1 calc R . .
C21 C 0.3524(2) 1.0525(2) 0.1172(2) 0.0398(6) Uani 1 1 d . . .
H21 H 0.2612 1.0501 0.1013 0.048 Uiso 1 1 calc R . .
N1 N 0.23711(17) 0.56791(18) 0.22709(15) 0.0318(4) Uani 1 1 d . . .
N2 N 0.36709(17) 0.80847(17) 0.28005(15) 0.0290(4) Uani 1 1 d . . .
O1 O 0.21065(17) 0.33103(16) 0.51392(14) 0.0489(4) Uani 1 1 d . . .
O2 O 0.32531(18) 0.22598(16) 0.37697(15) 0.0518(5) Uani 1 1 d . . .
O3 O 0.61409(17) 0.28520(16) 0.43239(15) 0.0487(4) Uani 1 1 d . . .
O4 O 0.75894(15) 0.31435(17) 0.24369(14) 0.0494(4) Uani 1 1 d . . .
O5 O 0.12042(17) 0.92043(16) 0.33380(17) 0.0552(5) Uani 1 1 d . . .
O6 O 0.59006(15) 0.63385(14) 0.28112(14) 0.0414(4) Uani 1 1 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
C1 N1 1.470(2) . ?
C1 C2 1.500(3) . ?
C1 C13 1.543(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.524(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.521(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.519(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.466(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.473(3) . ?
C6 C9 1.526(3) . ?
C6 C7 1.539(3) . ?
C6 C14 1.543(3) . ?
C7 O1 1.199(2) . ?
C7 O2 1.330(3) . ?
C8 O2 1.437(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.494(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O3 1.200(2) . ?
C10 O4 1.335(2) . ?
C11 O4 1.442(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O5 1.210(2) . ?
C12 N2 1.394(2) . ?
C12 C13 1.502(3) . ?
C13 C14 1.533(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.512(3) . ?
C14 H14 0.9800 . ?
C15 O6 1.206(2) . ?
C15 N2 1.399(2) . ?
C16 C21 1.379(3) . ?
C16 C17 1.382(3) . ?
C16 N2 1.432(2) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
N1 C1 C2 110.15(17) . . ?
N1 C1 C13 103.05(15) . . ?
C2 C1 C13 118.63(18) . . ?
N1 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
C13 C1 H1 108.2 . . ?
C1 C2 C3 109.3(2) . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C2 110.24(19) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C3 C4 C5 111.8(2) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C4 109.36(19) . . ?
N1 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N1 C6 C9 110.40(15) . . ?
N1 C6 C7 111.09(15) . . ?
C9 C6 C7 111.09(16) . . ?
N1 C6 C14 100.18(14) . . ?
C9 C6 C14 115.95(16) . . ?
C7 C6 C14 107.65(15) . . ?
O1 C7 O2 123.15(19) . . ?
O1 C7 C6 124.41(19) . . ?
O2 C7 C6 112.31(17) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C6 114.14(16) . . ?
C10 C9 H9A 108.7 . . ?
C6 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C6 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
O3 C10 O4 123.6(2) . . ?
O3 C10 C9 125.86(19) . . ?
O4 C10 C9 110.49(17) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 N2 124.41(19) . . ?
O5 C12 C13 126.64(18) . . ?
N2 C12 C13 108.94(16) . . ?
C12 C13 C14 104.79(15) . . ?
C12 C13 C1 113.36(16) . . ?
C14 C13 C1 105.24(15) . . ?
C12 C13 H13 111.0 . . ?
C14 C13 H13 111.0 . . ?
C1 C13 H13 111.0 . . ?
C15 C14 C13 104.65(15) . . ?
C15 C14 C6 113.33(15) . . ?
C13 C14 C6 106.19(15) . . ?
C15 C14 H14 110.8 . . ?
C13 C14 H14 110.8 . . ?
C6 C14 H14 110.8 . . ?
O6 C15 N2 124.33(17) . . ?
O6 C15 C14 126.86(18) . . ?
N2 C15 C14 108.80(16) . . ?
C21 C16 C17 120.59(19) . . ?
C21 C16 N2 118.85(18) . . ?
C17 C16 N2 120.53(18) . . ?
C16 C17 C18 118.7(2) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.8(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 119.8(2) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C5 N1 C1 111.11(16) . . ?
C5 N1 C6 118.56(17) . . ?
C1 N1 C6 108.00(14) . . ?
C12 N2 C15 111.65(16) . . ?
C12 N2 C16 123.95(16) . . ?
C15 N2 C16 124.31(16) . . ?
C7 O2 C8 116.88(17) . . ?
C10 O4 C11 117.14(18) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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_4a
_audit_block_doi                 10.5517/cc1kk3v2
_database_code_depnum_ccdc_archive 'CCDC 1446424'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O10'
_chemical_formula_sum            'C18 H22 N2 O10'
_chemical_formula_weight         426.38

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5073(18)
_cell_length_b                   10.502(2)
_cell_length_c                   11.966(3)
_cell_angle_alpha                101.061(7)
_cell_angle_beta                 101.512(7)
_cell_angle_gamma                93.112(7)
_cell_volume                     1023.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4613
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.74

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15619
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_sigmaI/netI    0.0827
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.62
_reflns_number_total             4690
_reflns_number_gt                2699
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0750P)²+0.0494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4690
_refine_ls_number_parameters     276
_refine_ls_number_restraints     372
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1606
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.071
_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
C1 C 0.2562(2) 0.2677(2) 0.73487(17) 0.0320(5) Uani 1 1 d U . .
C2 C 0.1477(3) 0.3567(2) 0.67937(19) 0.0396(6) Uani 1 1 d U . .
C3 C 0.1236(4) 0.5755(3) 0.6644(3) 0.0751(9) Uani 1 1 d U . .
H3A H 0.1172 0.5559 0.5818 0.113 Uiso 1 1 calc R . .
H3B H 0.1793 0.6605 0.6972 0.113 Uiso 1 1 calc R . .
H3C H 0.0168 0.5738 0.6793 0.113 Uiso 1 1 calc R . .
C4 C 0.3816(3) 0.2272(2) 0.68825(19) 0.0411(6) Uani 1 1 d U . .
H4 H 0.4447 0.1692 0.7219 0.049 Uiso 1 1 calc R . .
C5 C 0.4228(3) 0.2695(3) 0.5887(2) 0.0450(6) Uani 1 1 d U . .
C6 C 0.6159(4) 0.2531(4) 0.4696(3) 0.1025(13) Uani 1 1 d U . .
H6A H 0.5444 0.2118 0.3975 0.154 Uiso 1 1 calc R . .
H6B H 0.7216 0.2251 0.4703 0.154 Uiso 1 1 calc R . .
H6C H 0.6210 0.3460 0.4771 0.154 Uiso 1 1 calc R . .
C7 C 0.3050(2) 0.1454(2) 0.89528(17) 0.0294(5) Uani 1 1 d U . .
C8 C 0.4864(2) 0.1914(2) 0.92836(17) 0.0325(5) Uani 1 1 d U . .
C9 C 0.6760(3) 0.3745(3) 1.0028(2) 0.0614(8) Uani 1 1 d U . .
H9A H 0.7272 0.3361 1.0656 0.092 Uiso 1 1 calc R . .
H9B H 0.6797 0.4671 1.0297 0.092 Uiso 1 1 calc R . .
H9C H 0.7313 0.3567 0.9398 0.092 Uiso 1 1 calc R . .
C10 C 0.2797(3) 0.0041(2) 0.82472(19) 0.0376(5) Uani 1 1 d U . .
H10A H 0.3326 -0.0012 0.7595 0.045 Uiso 1 1 calc R . .
H10B H 0.3295 -0.0526 0.8738 0.045 Uiso 1 1 calc R . .
C11 C 0.1054(3) -0.0426(2) 0.7798(2) 0.0410(6) Uani 1 1 d U . .
C12 C -0.1116(4) -0.0726(5) 0.6163(3) 0.1204(15) Uani 1 1 d U . .
H12A H -0.1342 -0.1649 0.6077 0.181 Uiso 1 1 calc R . .
H12B H -0.1361 -0.0499 0.5412 0.181 Uiso 1 1 calc R . .
H12C H -0.1766 -0.0277 0.6652 0.181 Uiso 1 1 calc R . .
C13 C 0.0655(2) 0.2641(2) 0.86763(18) 0.0347(5) Uani 1 1 d U . .
H13A H -0.0253 0.2117 0.8130 0.042 Uiso 1 1 calc R . .
H13B H 0.0492 0.3555 0.8722 0.042 Uiso 1 1 calc R . .
C14 C 0.3420(3) 0.2356(2) 1.11745(18) 0.0346(5) Uani 1 1 d U . .
C15 C 0.2345(2) 0.1562(2) 1.00694(17) 0.0306(5) Uani 1 1 d U . .
H15 H 0.2048 0.0689 1.0184 0.037 Uiso 1 1 calc R . .
C16 C 0.0843(2) 0.2298(2) 0.98710(17) 0.0305(5) Uani 1 1 d U . .
H16 H -0.0111 0.1753 0.9907 0.037 Uiso 1 1 calc R . .
C17 C 0.1180(2) 0.3466(2) 1.08636(18) 0.0323(5) Uani 1 1 d U . .
C18 C 0.3382(3) 0.4403(3) 1.2604(2) 0.0535(7) Uani 1 1 d U . .
H18A H 0.3337 0.4053 1.3283 0.080 Uiso 1 1 calc R . .
H18B H 0.2798 0.5161 1.2621 0.080 Uiso 1 1 calc R . .
H18C H 0.4485 0.4640 1.2596 0.080 Uiso 1 1 calc R . .
N1 N 0.21714(18) 0.23540(16) 0.83166(14) 0.0291(4) Uani 1 1 d . . .
N2 N 0.2664(2) 0.34272(17) 1.15621(14) 0.0344(4) Uani 1 1 d . . .
O1 O 0.0212(2) 0.32005(19) 0.61399(16) 0.0660(6) Uani 1 1 d . . .
O2 O 0.2101(2) 0.47963(16) 0.71687(14) 0.0481(4) Uani 1 1 d . . .
O3 O 0.3521(2) 0.33904(19) 0.53113(15) 0.0578(5) Uani 1 1 d . . .
O4 O 0.5567(2) 0.2177(2) 0.56614(16) 0.0767(6) Uani 1 1 d . . .
O5 O 0.59103(17) 0.12019(16) 0.92567(14) 0.0497(5) Uani 1 1 d . . .
O6 O 0.50940(16) 0.31975(15) 0.96259(13) 0.0398(4) Uani 1 1 d . . .
O7 O 0.0162(2) -0.0791(2) 0.83369(18) 0.0808(7) Uani 1 1 d . . .
O8 O 0.0585(2) -0.0348(2) 0.66947(16) 0.0821(7) Uani 1 1 d . . .
O9 O 0.4712(2) 0.21175(17) 1.16733(13) 0.0549(5) Uani 1 1 d . . .
O10 O 0.03179(19) 0.43214(16) 1.10497(14) 0.0491(5) Uani 1 1 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
C1 C4 1.351(3) . ?
C1 N1 1.363(3) . ?
C1 C2 1.502(3) . ?
C2 O1 1.192(3) . ?
C2 O2 1.326(3) . ?
C3 O2 1.445(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.446(3) . ?
C4 H4 0.9300 . ?
C5 O3 1.202(3) . ?
C5 O4 1.342(3) . ?
C6 O4 1.451(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N1 1.469(2) . ?
C7 C8 1.541(3) . ?
C7 C10 1.541(3) . ?
C7 C15 1.558(3) . ?
C8 O5 1.195(2) . ?
C8 O6 1.323(3) . ?
C9 O6 1.450(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.493(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O7 1.183(3) . ?
C11 O8 1.320(3) . ?
C12 O8 1.460(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N1 1.468(2) . ?
C13 C16 1.520(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O9 1.205(2) . ?
C14 N2 1.375(3) . ?
C14 C15 1.514(3) . ?
C15 C16 1.531(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.504(3) . ?
C16 H16 0.9800 . ?
C17 O10 1.206(2) . ?
C17 N2 1.375(3) . ?
C18 N2 1.455(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C4 C1 N1 125.53(19) . . ?
C4 C1 C2 119.59(19) . . ?
N1 C1 C2 114.87(17) . . ?
O1 C2 O2 125.9(2) . . ?
O1 C2 C1 123.7(2) . . ?
O2 C2 C1 110.41(19) . . ?
O2 C3 H3A 109.5 . . ?
O2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 C5 123.4(2) . . ?
C1 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
O3 C5 O4 122.6(2) . . ?
O3 C5 C4 127.8(2) . . ?
O4 C5 C4 109.5(2) . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 109.79(17) . . ?
N1 C7 C10 112.61(16) . . ?
C8 C7 C10 109.34(16) . . ?
N1 C7 C15 103.74(14) . . ?
C8 C7 C15 110.28(16) . . ?
C10 C7 C15 110.98(17) . . ?
O5 C8 O6 125.1(2) . . ?
O5 C8 C7 124.3(2) . . ?
O6 C8 C7 110.53(17) . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 112.25(17) . . ?
C11 C10 H10A 109.2 . . ?
C7 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C7 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O7 C11 O8 122.6(2) . . ?
O7 C11 C10 126.3(2) . . ?
O8 C11 C10 111.0(2) . . ?
O8 C12 H12A 109.5 . . ?
O8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C16 104.91(15) . . ?
N1 C13 H13A 110.8 . . ?
C16 C13 H13A 110.8 . . ?
N1 C13 H13B 110.8 . . ?
C16 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
O9 C14 N2 123.7(2) . . ?
O9 C14 C15 127.76(19) . . ?
N2 C14 C15 108.53(17) . . ?
C14 C15 C16 104.92(16) . . ?
C14 C15 C7 115.27(17) . . ?
C16 C15 C7 106.81(15) . . ?
C14 C15 H15 109.9 . . ?
C16 C15 H15 109.9 . . ?
C7 C15 H15 109.9 . . ?
C17 C16 C13 113.80(17) . . ?
C17 C16 C15 104.27(16) . . ?
C13 C16 C15 107.75(16) . . ?
C17 C16 H16 110.3 . . ?
C13 C16 H16 110.3 . . ?
C15 C16 H16 110.3 . . ?
O10 C17 N2 123.5(2) . . ?
O10 C17 C16 127.09(19) . . ?
N2 C17 C16 109.42(16) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C13 123.16(16) . . ?
C1 N1 C7 122.88(16) . . ?
C13 N1 C7 112.78(16) . . ?
C14 N2 C17 112.85(17) . . ?
C14 N2 C18 122.69(18) . . ?
C17 N2 C18 124.46(18) . . ?
C2 O2 C3 116.4(2) . . ?
C5 O4 C6 116.3(2) . . ?
C8 O6 C9 115.80(17) . . ?
C11 O8 C12 116.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.124
####################################################################### 
# 
# 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_4d
_audit_block_doi                 10.5517/cc1kk3w3
_database_code_depnum_ccdc_archive 'CCDC 1446425'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 N2 O10'
_chemical_formula_sum            'C19 H24 N2 O10'
_chemical_formula_weight         440.40

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6218(14)
_cell_length_b                   15.664(2)
_cell_length_c                   16.949(3)
_cell_angle_alpha                77.049(5)
_cell_angle_beta                 78.276(4)
_cell_angle_gamma                89.931(5)
_cell_volume                     2181.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6597
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      24.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18054
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0797
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7366
_reflns_number_gt                4545
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1178P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7366
_refine_ls_number_parameters     571
_refine_ls_number_restraints     828
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1974
_refine_ls_wR_factor_gt          0.1796
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.026
_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
C1 C 0.8301(5) -0.2142(3) 0.5741(2) 0.0581(10) Uani 1 1 d U . .
H1A H 0.9260 -0.2455 0.5684 0.087 Uiso 1 1 calc R . .
H1B H 0.7414 -0.2550 0.5993 0.087 Uiso 1 1 calc R . .
H1C H 0.8360 -0.1735 0.6082 0.087 Uiso 1 1 calc R . .
C2 C 0.6796(4) -0.1174(2) 0.4796(2) 0.0347(7) Uani 1 1 d U . .
C3 C 0.7009(3) -0.07755(19) 0.38828(18) 0.0304(7) Uani 1 1 d U . .
H3 H 0.6046 -0.0873 0.3685 0.037 Uiso 1 1 calc R . .
C4 C 0.8383(4) -0.12532(19) 0.34854(17) 0.0310(7) Uani 1 1 d U . .
H4 H 0.7950 -0.1715 0.3275 0.037 Uiso 1 1 calc R . .
C5 C 0.9157(4) -0.16837(19) 0.41973(19) 0.0350(7) Uani 1 1 d U . .
C6 C 0.7547(4) 0.02013(19) 0.36283(17) 0.0310(7) Uani 1 1 d U . .
H6 H 0.6644 0.0547 0.3501 0.037 Uiso 1 1 calc R . .
C7 C 0.8206(4) 0.0548(2) 0.42683(19) 0.0418(8) Uani 1 1 d U . .
H7A H 0.9041 0.0188 0.4430 0.063 Uiso 1 1 calc R . .
H7B H 0.7376 0.0535 0.4744 0.063 Uiso 1 1 calc R . .
H7C H 0.8618 0.1140 0.4035 0.063 Uiso 1 1 calc R . .
C8 C 0.9408(3) -0.05857(19) 0.27409(17) 0.0280(7) Uani 1 1 d U . .
C9 C 1.1183(4) -0.06126(19) 0.27738(19) 0.0322(7) Uani 1 1 d U . .
C10 C 1.3182(4) -0.0178(3) 0.3376(3) 0.0639(11) Uani 1 1 d U . .
H10A H 1.3435 -0.0759 0.3628 0.096 Uiso 1 1 calc R . .
H10B H 1.3362 0.0219 0.3709 0.096 Uiso 1 1 calc R . .
H10C H 1.3843 0.0005 0.2833 0.096 Uiso 1 1 calc R . .
C11 C 0.9249(4) -0.0782(2) 0.19122(18) 0.0371(7) Uani 1 1 d U . .
H11A H 1.0040 -0.0421 0.1476 0.045 Uiso 1 1 calc R . .
H11B H 0.9489 -0.1390 0.1926 0.045 Uiso 1 1 calc R . .
C12 C 0.7663(4) -0.0630(2) 0.1693(2) 0.0433(8) Uani 1 1 d U . .
C13 C 0.6407(7) -0.0341(5) 0.0564(3) 0.141(3) Uani 1 1 d U . .
H13A H 0.5652 -0.0821 0.0831 0.211 Uiso 1 1 calc R . .
H13B H 0.6648 -0.0302 -0.0022 0.211 Uiso 1 1 calc R . .
H13C H 0.5968 0.0195 0.0671 0.211 Uiso 1 1 calc R . .
C14 C 0.9228(4) 0.10328(19) 0.23066(17) 0.0290(7) Uani 1 1 d U . .
C15 C 0.8091(4) 0.1764(2) 0.23963(19) 0.0381(8) Uani 1 1 d U . .
C16 C 0.5683(6) 0.2323(4) 0.2116(4) 0.1070(19) Uani 1 1 d U . .
H16A H 0.5181 0.2260 0.2687 0.161 Uiso 1 1 calc R . .
H16B H 0.4903 0.2237 0.1806 0.161 Uiso 1 1 calc R . .
H16C H 0.6174 0.2901 0.1900 0.161 Uiso 1 1 calc R . .
C17 C 1.0579(4) 0.1179(2) 0.17265(19) 0.0391(8) Uani 1 1 d U . .
H17 H 1.1275 0.0727 0.1698 0.047 Uiso 1 1 calc R . .
C18 C 1.0986(5) 0.2018(2) 0.1144(2) 0.0424(8) Uani 1 1 d U . .
C19 C 1.3054(6) 0.2886(3) 0.0175(3) 0.0918(16) Uani 1 1 d U . .
H19A H 1.2559 0.2948 -0.0292 0.138 Uiso 1 1 calc R . .
H19B H 1.4184 0.2892 -0.0008 0.138 Uiso 1 1 calc R . .
H19C H 1.2783 0.3364 0.0440 0.138 Uiso 1 1 calc R . .
C20 C 0.3341(4) 0.6802(3) 0.5739(2) 0.0537(10) Uani 1 1 d U . .
H20A H 0.4333 0.7114 0.5675 0.081 Uiso 1 1 calc R . .
H20B H 0.3342 0.6233 0.6098 0.081 Uiso 1 1 calc R . .
H20C H 0.2491 0.7124 0.5975 0.081 Uiso 1 1 calc R . .
C21 C 0.1812(4) 0.6281(2) 0.48190(19) 0.0344(7) Uani 1 1 d U . .
C22 C 0.1998(3) 0.63164(19) 0.38990(17) 0.0299(7) Uani 1 1 d U . .
H22 H 0.1030 0.6514 0.3709 0.036 Uiso 1 1 calc R . .
C23 C 0.3370(3) 0.69843(19) 0.34938(17) 0.0304(7) Uani 1 1 d U . .
H23 H 0.2932 0.7548 0.3285 0.036 Uiso 1 1 calc R . .
C24 C 0.4158(4) 0.7075(2) 0.41976(19) 0.0342(7) Uani 1 1 d U . .
C25 C 0.2519(3) 0.54617(19) 0.36397(17) 0.0299(7) Uani 1 1 d U . .
H25 H 0.1606 0.5175 0.3526 0.036 Uiso 1 1 calc R . .
C26 C 0.3214(4) 0.4815(2) 0.42691(19) 0.0429(8) Uani 1 1 d U . .
H26A H 0.3618 0.4334 0.4035 0.064 Uiso 1 1 calc R . .
H26B H 0.2405 0.4598 0.4755 0.064 Uiso 1 1 calc R . .
H26C H 0.4060 0.5103 0.4416 0.064 Uiso 1 1 calc R . .
C27 C 0.4357(3) 0.66711(18) 0.27446(17) 0.0280(7) Uani 1 1 d U . .
C28 C 0.6138(4) 0.6679(2) 0.27654(18) 0.0310(7) Uani 1 1 d U . .
C29 C 0.8151(4) 0.5953(3) 0.3357(3) 0.0658(12) Uani 1 1 d U . .
H29A H 0.8813 0.6072 0.2812 0.099 Uiso 1 1 calc R . .
H29B H 0.8345 0.5380 0.3657 0.099 Uiso 1 1 calc R . .
H29C H 0.8388 0.6384 0.3643 0.099 Uiso 1 1 calc R . .
C30 C 0.4195(4) 0.7277(2) 0.19200(18) 0.0361(7) Uani 1 1 d U . .
H30A H 0.4492 0.7872 0.1927 0.043 Uiso 1 1 calc R . .
H30B H 0.4946 0.7109 0.1477 0.043 Uiso 1 1 calc R . .
C31 C 0.2577(4) 0.7273(2) 0.1722(2) 0.0420(8) Uani 1 1 d U . .
C32 C 0.1259(6) 0.7653(4) 0.0588(3) 0.1040(19) Uani 1 1 d U . .
H32A H 0.0594 0.7134 0.0848 0.156 Uiso 1 1 calc R . .
H32B H 0.1517 0.7706 0.0001 0.156 Uiso 1 1 calc R . .
H32C H 0.0709 0.8158 0.0706 0.156 Uiso 1 1 calc R . .
C33 C 0.4150(4) 0.52667(19) 0.23067(17) 0.0299(7) Uani 1 1 d U . .
C34 C 0.3021(4) 0.4488(2) 0.24179(19) 0.0393(8) Uani 1 1 d U . .
C35 C 0.0545(6) 0.4041(3) 0.2211(3) 0.0933(17) Uani 1 1 d U . .
H35A H 0.1019 0.3563 0.1997 0.140 Uiso 1 1 calc R . .
H35B H -0.0262 0.4271 0.1917 0.140 Uiso 1 1 calc R . .
H35C H 0.0080 0.3837 0.2789 0.140 Uiso 1 1 calc R . .
C36 C 0.5482(4) 0.5387(2) 0.17079(18) 0.0369(8) Uani 1 1 d U . .
H36 H 0.6202 0.5843 0.1671 0.044 Uiso 1 1 calc R . .
C37 C 0.5827(4) 0.4831(2) 0.1121(2) 0.0416(8) Uani 1 1 d U . .
C38 C 0.7815(6) 0.4436(3) 0.0099(2) 0.0816(14) Uani 1 1 d U . .
H38A H 0.7748 0.3829 0.0379 0.122 Uiso 1 1 calc R . .
H38B H 0.8887 0.4601 -0.0192 0.122 Uiso 1 1 calc R . .
H38C H 0.7126 0.4528 -0.0289 0.122 Uiso 1 1 calc R . .
N1 N 0.8100(3) -0.16613(16) 0.49184(15) 0.0365(7) Uani 1 1 d . . .
N2 N 0.8725(3) 0.02547(15) 0.28526(14) 0.0272(6) Uani 1 1 d . . .
N3 N 0.3123(3) 0.67039(17) 0.49260(15) 0.0350(6) Uani 1 1 d . . .
N4 N 0.3680(3) 0.57830(15) 0.28513(14) 0.0275(6) Uani 1 1 d . . .
O1 O 0.5702(3) -0.10960(15) 0.53469(14) 0.0508(7) Uani 1 1 d . . .
O2 O 1.0413(3) -0.20231(16) 0.41667(15) 0.0582(7) Uani 1 1 d . . .
O3 O 1.2127(3) -0.09770(15) 0.23567(14) 0.0485(6) Uani 1 1 d . . .
O4 O 1.1525(2) -0.01764(14) 0.33104(13) 0.0396(6) Uani 1 1 d . . .
O5 O 0.6417(3) -0.0661(2) 0.21493(17) 0.0667(8) Uani 1 1 d . . .
O6 O 0.7830(4) -0.0485(3) 0.08813(17) 0.1091(14) Uani 1 1 d . . .
O7 O 0.8264(3) 0.23073(16) 0.27672(15) 0.0607(7) Uani 1 1 d . . .
O8 O 0.6878(3) 0.16767(17) 0.20454(16) 0.0598(7) Uani 1 1 d . . .
O9 O 1.0102(3) 0.26087(17) 0.10128(15) 0.0592(7) Uani 1 1 d . . .
O10 O 1.2508(3) 0.20666(17) 0.07561(15) 0.0678(8) Uani 1 1 d . . .
O11 O 0.0731(3) 0.59353(16) 0.53755(14) 0.0507(7) Uani 1 1 d . . .
O12 O 0.5411(3) 0.74325(17) 0.41550(14) 0.0565(7) Uani 1 1 d . . .
O13 O 0.7084(3) 0.72339(15) 0.23364(14) 0.0496(6) Uani 1 1 d . . .
O14 O 0.6501(2) 0.59880(14) 0.32931(13) 0.0398(6) Uani 1 1 d . . .
O15 O 0.1346(3) 0.70498(19) 0.21863(16) 0.0652(8) Uani 1 1 d . . .
O16 O 0.2708(4) 0.7596(2) 0.09059(15) 0.0780(9) Uani 1 1 d . . .
O17 O 0.3238(3) 0.37622(16) 0.27836(15) 0.0651(8) Uani 1 1 d . . .
O18 O 0.1756(3) 0.47289(16) 0.21063(15) 0.0542(7) Uani 1 1 d . . .
O19 O 0.4917(3) 0.43118(17) 0.10105(15) 0.0612(7) Uani 1 1 d . . .
O20 O 0.7340(3) 0.49668(17) 0.06985(15) 0.0615(7) Uani 1 1 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
C1 N1 1.472(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.211(4) . ?
C2 N1 1.383(4) . ?
C2 C3 1.507(4) . ?
C3 C4 1.522(4) . ?
C3 C6 1.539(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.522(4) . ?
C4 C8 1.557(4) . ?
C4 H4 0.9800 . ?
C5 O2 1.202(4) . ?
C5 N1 1.375(4) . ?
C6 N2 1.475(3) . ?
C6 C7 1.520(4) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N2 1.476(4) . ?
C8 C11 1.536(4) . ?
C8 C9 1.543(4) . ?
C9 O3 1.197(3) . ?
C9 O4 1.330(4) . ?
C10 O4 1.455(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.493(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O5 1.183(4) . ?
C12 O6 1.320(4) . ?
C13 O6 1.435(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C17 1.346(4) . ?
C14 N2 1.365(4) . ?
C14 C15 1.520(4) . ?
C15 O7 1.192(4) . ?
C15 O8 1.325(4) . ?
C16 O8 1.451(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.450(5) . ?
C17 H17 0.9300 . ?
C18 O9 1.209(4) . ?
C18 O10 1.337(4) . ?
C19 O10 1.444(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N3 1.469(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O11 1.212(3) . ?
C21 N3 1.373(4) . ?
C21 C22 1.523(4) . ?
C22 C23 1.522(4) . ?
C22 C25 1.539(4) . ?
C22 H22 0.9800 . ?
C23 C24 1.520(4) . ?
C23 C27 1.554(4) . ?
C23 H23 0.9800 . ?
C24 O12 1.199(4) . ?
C24 N3 1.375(4) . ?
C25 N4 1.482(3) . ?
C25 C26 1.516(4) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 N4 1.468(4) . ?
C27 C30 1.535(4) . ?
C27 C28 1.544(4) . ?
C28 O13 1.194(3) . ?
C28 O14 1.322(4) . ?
C29 O14 1.448(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.500(5) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 O15 1.186(4) . ?
C31 O16 1.343(4) . ?
C32 O16 1.452(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C36 1.351(4) . ?
C33 N4 1.361(4) . ?
C33 C34 1.515(4) . ?
C34 O17 1.201(4) . ?
C34 O18 1.325(4) . ?
C35 O18 1.457(5) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.452(5) . ?
C36 H36 0.9300 . ?
C37 O19 1.200(4) . ?
C37 O20 1.346(4) . ?
C38 O20 1.449(4) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 124.1(3) . . ?
O1 C2 C3 128.0(3) . . ?
N1 C2 C3 107.9(3) . . ?
C2 C3 C4 104.2(2) . . ?
C2 C3 C6 114.3(2) . . ?
C4 C3 C6 105.6(2) . . ?
C2 C3 H3 110.8 . . ?
C4 C3 H3 110.8 . . ?
C6 C3 H3 110.8 . . ?
C5 C4 C3 104.5(2) . . ?
C5 C4 C8 118.2(3) . . ?
C3 C4 C8 108.3(2) . . ?
C5 C4 H4 108.5 . . ?
C3 C4 H4 108.5 . . ?
C8 C4 H4 108.5 . . ?
O2 C5 N1 124.4(3) . . ?
O2 C5 C4 128.5(3) . . ?
N1 C5 C4 107.0(3) . . ?
N2 C6 C7 112.8(2) . . ?
N2 C6 C3 102.6(2) . . ?
C7 C6 C3 115.3(3) . . ?
N2 C6 H6 108.6 . . ?
C7 C6 H6 108.6 . . ?
C3 C6 H6 108.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C11 112.1(2) . . ?
N2 C8 C9 112.6(2) . . ?
C11 C8 C9 107.3(2) . . ?
N2 C8 C4 101.9(2) . . ?
C11 C8 C4 111.3(2) . . ?
C9 C8 C4 111.5(2) . . ?
O3 C9 O4 124.8(3) . . ?
O3 C9 C8 123.4(3) . . ?
O4 C9 C8 111.8(3) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 115.5(3) . . ?
C12 C11 H11A 108.4 . . ?
C8 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C8 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
O5 C12 O6 123.1(3) . . ?
O5 C12 C11 127.7(3) . . ?
O6 C12 C11 109.2(3) . . ?
O6 C13 H13A 109.5 . . ?
O6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C14 N2 125.8(3) . . ?
C17 C14 C15 120.6(3) . . ?
N2 C14 C15 113.6(2) . . ?
O7 C15 O8 126.1(3) . . ?
O7 C15 C14 123.2(3) . . ?
O8 C15 C14 110.5(3) . . ?
O8 C16 H16A 109.5 . . ?
O8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 C18 122.2(3) . . ?
C14 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
O9 C18 O10 123.0(3) . . ?
O9 C18 C17 126.1(3) . . ?
O10 C18 C17 110.9(3) . . ?
O10 C19 H19A 109.5 . . ?
O10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O11 C21 N3 124.5(3) . . ?
O11 C21 C22 127.5(3) . . ?
N3 C21 C22 108.0(2) . . ?
C23 C22 C21 103.6(2) . . ?
C23 C22 C25 105.7(2) . . ?
C21 C22 C25 115.0(2) . . ?
C23 C22 H22 110.7 . . ?
C21 C22 H22 110.7 . . ?
C25 C22 H22 110.7 . . ?
C24 C23 C22 104.6(2) . . ?
C24 C23 C27 119.1(3) . . ?
C22 C23 C27 107.7(2) . . ?
C24 C23 H23 108.3 . . ?
C22 C23 H23 108.3 . . ?
C27 C23 H23 108.3 . . ?
O12 C24 N3 124.4(3) . . ?
O12 C24 C23 128.2(3) . . ?
N3 C24 C23 107.3(3) . . ?
N4 C25 C26 112.5(2) . . ?
N4 C25 C22 102.7(2) . . ?
C26 C25 C22 114.8(2) . . ?
N4 C25 H25 108.9 . . ?
C26 C25 H25 108.9 . . ?
C22 C25 H25 108.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N4 C27 C30 112.3(2) . . ?
N4 C27 C28 112.5(2) . . ?
C30 C27 C28 106.8(2) . . ?
N4 C27 C23 103.0(2) . . ?
C30 C27 C23 111.4(2) . . ?
C28 C27 C23 110.9(2) . . ?
O13 C28 O14 124.1(3) . . ?
O13 C28 C27 123.7(3) . . ?
O14 C28 C27 112.2(2) . . ?
O14 C29 H29A 109.5 . . ?
O14 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O14 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C27 115.5(3) . . ?
C31 C30 H30A 108.4 . . ?
C27 C30 H30A 108.4 . . ?
C31 C30 H30B 108.4 . . ?
C27 C30 H30B 108.4 . . ?
H30A C30 H30B 107.5 . . ?
O15 C31 O16 123.2(3) . . ?
O15 C31 C30 127.9(3) . . ?
O16 C31 C30 108.9(3) . . ?
O16 C32 H32A 109.5 . . ?
O16 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O16 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C36 C33 N4 126.5(3) . . ?
C36 C33 C34 119.6(3) . . ?
N4 C33 C34 113.9(2) . . ?
O17 C34 O18 125.7(3) . . ?
O17 C34 C33 123.0(3) . . ?
O18 C34 C33 111.2(3) . . ?
O18 C35 H35A 109.5 . . ?
O18 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O18 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 C37 122.3(3) . . ?
C33 C36 H36 118.8 . . ?
C37 C36 H36 118.8 . . ?
O19 C37 O20 122.9(3) . . ?
O19 C37 C36 126.1(3) . . ?
O20 C37 C36 111.0(3) . . ?
O20 C38 H38A 109.5 . . ?
O20 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O20 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C5 N1 C2 113.7(3) . . ?
C5 N1 C1 123.2(3) . . ?
C2 N1 C1 123.0(3) . . ?
C14 N2 C6 122.4(2) . . ?
C14 N2 C8 122.4(2) . . ?
C6 N2 C8 115.1(2) . . ?
C21 N3 C24 113.8(2) . . ?
C21 N3 C20 123.0(3) . . ?
C24 N3 C20 123.1(3) . . ?
C33 N4 C27 123.4(2) . . ?
C33 N4 C25 122.1(2) . . ?
C27 N4 C25 114.3(2) . . ?
C9 O4 C10 114.7(3) . . ?
C12 O6 C13 116.4(4) . . ?
C15 O8 C16 115.5(4) . . ?
C18 O10 C19 115.6(3) . . ?
C28 O14 C29 115.6(3) . . ?
C31 O16 C32 117.4(4) . . ?
C34 O18 C35 116.3(3) . . ?
C37 O20 C38 115.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.079
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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_4e
_audit_block_doi                 10.5517/cc1kk3x4
_database_code_depnum_ccdc_archive 'CCDC 1446426'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 N2 O10'
_chemical_formula_sum            'C24 H26 N2 O10'
_chemical_formula_weight         502.47

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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   13.2804(18)
_cell_length_b                   12.6107(15)
_cell_length_c                   17.7624(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.573(7)
_cell_angle_gamma                90.00
_cell_volume                     2419.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7495
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      23.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24729
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.58
_reflns_number_total             5556
_reflns_number_gt                3549
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0777P)²+0.0844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5556
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
C1 C 0.23472(18) 0.43163(15) -0.05146(14) 0.0400(5) Uani 1 1 d . . .
H1 H 0.3056 0.4610 -0.0419 0.048 Uiso 1 1 calc R . .
C2 C 0.2177(2) 0.32311(16) -0.06123(15) 0.0483(6) Uani 1 1 d . . .
H2A H 0.2763 0.2803 -0.0591 0.058 Uiso 1 1 calc R . .
C3 C 0.1142(2) 0.27815(16) -0.07412(14) 0.0492(6) Uani 1 1 d . . .
H3 H 0.1041 0.2049 -0.0786 0.059 Uiso 1 1 calc R . .
C4 C 0.0261(2) 0.34252(16) -0.08032(15) 0.0461(5) Uani 1 1 d . . .
H4 H -0.0448 0.3129 -0.0903 0.055 Uiso 1 1 calc R . .
C5 C 0.04274(17) 0.45140(15) -0.07175(13) 0.0352(4) Uani 1 1 d . . .
H5 H -0.0180 0.4942 -0.0769 0.042 Uiso 1 1 calc R . .
C6 C 0.14783(16) 0.49753(14) -0.05570(12) 0.0293(4) Uani 1 1 d . . .
C7 C 0.17114(16) 0.61547(13) -0.03592(13) 0.0300(4) Uani 1 1 d . . .
H7A H 0.2355 0.6249 0.0296 0.036 Uiso 1 1 calc R . .
H7B H 0.0963 0.6480 -0.0490 0.036 Uiso 1 1 calc R . .
C8 C 0.20966(15) 0.67479(13) -0.09088(12) 0.0257(4) Uani 1 1 d . . .
H8 H 0.2596 0.6270 -0.1003 0.031 Uiso 1 1 calc R . .
C9 C 0.39645(15) 0.76410(13) 0.04207(12) 0.0269(4) Uani 1 1 d . . .
C10 C 0.46446(15) 0.66037(14) 0.06111(13) 0.0302(4) Uani 1 1 d . . .
C11 C 0.5591(2) 0.51738(17) 0.16504(17) 0.0594(7) Uani 1 1 d . . .
H11A H 0.6411 0.5406 0.1880 0.089 Uiso 1 1 calc R . .
H11B H 0.5307 0.4674 0.1158 0.089 Uiso 1 1 calc R . .
H11C H 0.5602 0.4842 0.2142 0.089 Uiso 1 1 calc R . .
C12 C 0.45373(17) 0.84340(14) 0.10430(13) 0.0337(4) Uani 1 1 d . . .
H12 H 0.4103 0.9060 0.0936 0.040 Uiso 1 1 calc R . .
C13 C 0.57890(17) 0.83599(15) 0.18649(13) 0.0345(5) Uani 1 1 d . . .
C14 C 0.7261(2) 0.9211(2) 0.32811(15) 0.0669(7) Uani 1 1 d . . .
H14A H 0.7852 0.9235 0.3135 0.100 Uiso 1 1 calc R . .
H14B H 0.7411 0.8595 0.3650 0.100 Uiso 1 1 calc R . .
H14C H 0.7343 0.9836 0.3621 0.100 Uiso 1 1 calc R . .
C15 C 0.22186(15) 0.87248(13) -0.08223(12) 0.0273(4) Uani 1 1 d . . .
C16 C 0.19727(16) 0.93239(14) -0.01894(13) 0.0322(4) Uani 1 1 d . . .
C17 C 0.1405(3) 0.9098(2) 0.0837(2) 0.0728(8) Uani 1 1 d . . .
H17A H 0.0530 0.9148 0.0547 0.109 Uiso 1 1 calc R . .
H17B H 0.1766 0.9793 0.1020 0.109 Uiso 1 1 calc R . .
H17C H 0.1775 0.8652 0.1374 0.109 Uiso 1 1 calc R . .
C18 C 0.30116(17) 0.94228(14) -0.10010(13) 0.0354(5) Uani 1 1 d . . .
H18A H 0.2527 1.0028 -0.1376 0.042 Uiso 1 1 calc R . .
H18B H 0.3722 0.9687 -0.0416 0.042 Uiso 1 1 calc R . .
C19 C 0.34486(18) 0.88141(16) -0.14876(15) 0.0406(5) Uani 1 1 d . . .
C20 C 0.5172(2) 0.8314(2) -0.1461(2) 0.0724(8) Uani 1 1 d . . .
H20A H 0.4807 0.8586 -0.2073 0.109 Uiso 1 1 calc R . .
H20B H 0.4992 0.7572 -0.1495 0.109 Uiso 1 1 calc R . .
H20C H 0.6053 0.8416 -0.1095 0.109 Uiso 1 1 calc R . .
C21 C -0.02489(17) 0.68061(15) -0.21921(12) 0.0348(5) Uani 1 1 d . . .
C22 C 0.10315(15) 0.71950(13) -0.18584(12) 0.0282(4) Uani 1 1 d . . .
H22 H 0.1186 0.7053 -0.2326 0.034 Uiso 1 1 calc R . .
C23 C 0.09847(15) 0.83909(13) -0.17344(12) 0.0277(4) Uani 1 1 d . . .
H23 H 0.0919 0.8754 -0.2249 0.033 Uiso 1 1 calc R . .
C24 C -0.02120(17) 0.85714(16) -0.18199(13) 0.0364(5) Uani 1 1 d . . .
N1 N 0.28409(12) 0.77032(10) -0.04137(10) 0.0265(3) Uani 1 1 d . . .
N2 N -0.08529(14) 0.76327(13) -0.21107(11) 0.0398(4) Uani 1 1 d . . .
H2 H -0.1579 0.7567 -0.2233 0.048 Uiso 1 1 d R . .
O1 O 0.50180(13) 0.63121(11) 0.01747(10) 0.0458(4) Uani 1 1 d . . .
O2 O 0.47647(12) 0.60777(10) 0.13066(9) 0.0406(4) Uani 1 1 d . . .
O3 O 0.65501(12) 0.76961(12) 0.20342(10) 0.0536(4) Uani 1 1 d . . .
O4 O 0.60308(12) 0.91622(12) 0.24393(9) 0.0507(4) Uani 1 1 d . . .
O5 O 0.21118(13) 1.02554(10) -0.00488(10) 0.0486(4) Uani 1 1 d . . .
O6 O 0.16192(13) 0.86500(10) 0.01924(10) 0.0418(4) Uani 1 1 d . . .
O7 O 0.28000(15) 0.83344(16) -0.21922(12) 0.0751(6) Uani 1 1 d . . .
O8 O 0.46679(13) 0.88708(11) -0.10394(11) 0.0515(4) Uani 1 1 d . . .
O9 O -0.06790(13) 0.59358(11) -0.24774(10) 0.0515(4) Uani 1 1 d . . .
O10 O -0.05755(13) 0.93856(12) -0.17035(11) 0.0561(4) Uani 1 1 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
C1 C2 1.382(3) . ?
C1 C6 1.388(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.518(2) . ?
C7 C8 1.535(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.480(2) . ?
C8 C22 1.545(2) . ?
C8 H8 0.9800 . ?
C9 C12 1.350(2) . ?
C9 N1 1.362(2) . ?
C9 C10 1.512(2) . ?
C10 O1 1.195(2) . ?
C10 O2 1.328(2) . ?
C11 O2 1.448(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.442(3) . ?
C12 H12 0.9300 . ?
C13 O3 1.208(2) . ?
C13 O4 1.337(2) . ?
C14 O4 1.438(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N1 1.474(2) . ?
C15 C16 1.539(3) . ?
C15 C18 1.541(2) . ?
C15 C23 1.549(2) . ?
C16 O5 1.193(2) . ?
C16 O6 1.331(2) . ?
C17 O6 1.447(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.502(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O7 1.192(2) . ?
C19 O8 1.327(2) . ?
C20 O8 1.444(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O9 1.205(2) . ?
C21 N2 1.373(2) . ?
C21 C22 1.520(3) . ?
C22 C23 1.531(2) . ?
C22 H22 0.9800 . ?
C23 C24 1.523(3) . ?
C23 H23 0.9800 . ?
C24 O10 1.203(2) . ?
C24 N2 1.372(2) . ?
N2 H2 0.8600 . ?

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 C1 C6 121.06(19) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C4 C3 C2 119.37(18) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 121.18(18) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 117.89(17) . . ?
C5 C6 C7 120.42(16) . . ?
C1 C6 C7 121.52(16) . . ?
C6 C7 C8 115.40(15) . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
N1 C8 C7 111.93(14) . . ?
N1 C8 C22 102.85(12) . . ?
C7 C8 C22 116.11(14) . . ?
N1 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C22 C8 H8 108.5 . . ?
C12 C9 N1 125.94(15) . . ?
C12 C9 C10 118.62(15) . . ?
N1 C9 C10 115.27(14) . . ?
O1 C10 O2 125.39(17) . . ?
O1 C10 C9 122.70(17) . . ?
O2 C10 C9 111.91(15) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 C13 123.33(16) . . ?
C9 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
O3 C13 O4 122.67(17) . . ?
O3 C13 C12 126.99(17) . . ?
O4 C13 C12 110.32(16) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 111.47(14) . . ?
N1 C15 C18 110.25(14) . . ?
C16 C15 C18 109.33(14) . . ?
N1 C15 C23 103.09(13) . . ?
C16 C15 C23 110.65(14) . . ?
C18 C15 C23 111.96(14) . . ?
O5 C16 O6 125.42(18) . . ?
O5 C16 C15 124.30(18) . . ?
O6 C16 C15 110.25(14) . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C15 111.45(14) . . ?
C19 C18 H18A 109.3 . . ?
C15 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C15 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
O7 C19 O8 122.8(2) . . ?
O7 C19 C18 125.35(18) . . ?
O8 C19 C18 111.86(18) . . ?
O8 C20 H20A 109.5 . . ?
O8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O9 C21 N2 124.95(18) . . ?
O9 C21 C22 127.38(18) . . ?
N2 C21 C22 107.67(15) . . ?
C21 C22 C23 104.13(14) . . ?
C21 C22 C8 114.45(14) . . ?
C23 C22 C8 106.88(13) . . ?
C21 C22 H22 110.4 . . ?
C23 C22 H22 110.4 . . ?
C8 C22 H22 110.4 . . ?
C24 C23 C22 105.09(14) . . ?
C24 C23 C15 118.12(15) . . ?
C22 C23 C15 108.16(13) . . ?
C24 C23 H23 108.4 . . ?
C22 C23 H23 108.4 . . ?
C15 C23 H23 108.4 . . ?
O10 C24 N2 125.34(18) . . ?
O10 C24 C23 127.62(18) . . ?
N2 C24 C23 106.94(16) . . ?
C9 N1 C15 122.11(13) . . ?
C9 N1 C8 121.99(13) . . ?
C15 N1 C8 115.45(13) . . ?
C24 N2 C21 114.98(16) . . ?
C24 N2 H2 122.5 . . ?
C21 N2 H2 122.5 . . ?
C10 O2 C11 115.92(16) . . ?
C13 O4 C14 116.70(16) . . ?
C16 O6 C17 116.36(16) . . ?
C19 O8 C20 115.79(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O3 0.86 2.05 2.877(2) 160.2 4_475

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.58
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.129
####################################################################### 
# 
# 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_4f
_audit_block_doi                 10.5517/cc1kk3y5
_database_code_depnum_ccdc_archive 'CCDC 1446427'
_audit_update_record             
;
2016-01-11 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 N2 O10'
_chemical_formula_sum            'C30 H30 N2 O10'
_chemical_formula_weight         578.56

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.685(2)
_cell_length_b                   11.358(2)
_cell_length_c                   13.190(2)
_cell_angle_alpha                74.859(6)
_cell_angle_beta                 68.301(5)
_cell_angle_gamma                76.133(6)
_cell_volume                     1417.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8008
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.26

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21308
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         27.51
_reflns_number_total             6464
_reflns_number_gt                4284
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0556P)²+0.2244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6464
_refine_ls_number_parameters     430
_refine_ls_number_restraints     928
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.53489(18) 0.95545(19) 0.73449(15) 0.0540(5) Uani 1 1 d U . .
H1 H 0.5444 1.0368 0.6993 0.065 Uiso 1 1 calc R . .
C2 C 0.4525(2) 0.9285(2) 0.84410(16) 0.0683(6) Uani 1 1 d U . .
H2 H 0.4074 0.9921 0.8832 0.082 Uiso 1 1 calc R . .
C3 C 0.4371(2) 0.8090(3) 0.89530(17) 0.0711(6) Uani 1 1 d U . .
H3 H 0.3803 0.7918 0.9686 0.085 Uiso 1 1 calc R . .
C4 C 0.5052(2) 0.7148(2) 0.83889(18) 0.0717(6) Uani 1 1 d U . .
H4 H 0.4949 0.6336 0.8742 0.086 Uiso 1 1 calc R . .
C5 C 0.58935(19) 0.73964(19) 0.72929(16) 0.0570(5) Uani 1 1 d U . .
H5 H 0.6362 0.6757 0.6909 0.068 Uiso 1 1 calc R . .
C6 C 0.60238(15) 0.86003(16) 0.67859(13) 0.0399(4) Uani 1 1 d U . .
C7 C 0.67036(15) 0.88080(14) 0.47230(13) 0.0360(4) Uani 1 1 d U . .
C8 C 0.79372(15) 0.91634(15) 0.37241(12) 0.0347(3) Uani 1 1 d U A .
H8 H 0.7682 0.9995 0.3331 0.042 Uiso 1 1 calc R . .
C9 C 0.90065(15) 0.92070(15) 0.42207(12) 0.0359(4) Uani 1 1 d U . .
H9 H 0.9416 0.9960 0.3870 0.043 Uiso 1 1 calc R . .
C10 C 0.82172(16) 0.92050(15) 0.54364(13) 0.0380(4) Uani 1 1 d U . .
C11 C 1.02235(19) 0.67126(19) 0.69108(15) 0.0529(5) Uani 1 1 d U . .
H11 H 0.9391 0.6426 0.7206 0.063 Uiso 1 1 calc R . .
C12 C 1.0894(2) 0.6751(2) 0.76174(17) 0.0658(6) Uani 1 1 d U . .
H12 H 1.0511 0.6488 0.8379 0.079 Uiso 1 1 calc R . .
C13 C 1.2118(2) 0.7173(2) 0.72047(18) 0.0617(5) Uani 1 1 d U . .
H13 H 1.2562 0.7202 0.7684 0.074 Uiso 1 1 calc R . .
C14 C 1.26855(19) 0.75536(18) 0.60805(17) 0.0539(5) Uani 1 1 d U . .
H14 H 1.3517 0.7841 0.5795 0.065 Uiso 1 1 calc R . .
C15 C 1.20199(16) 0.75100(16) 0.53675(15) 0.0446(4) Uani 1 1 d U . .
H15 H 1.2417 0.7764 0.4606 0.054 Uiso 1 1 calc R . .
C16 C 1.07719(16) 0.70935(15) 0.57708(13) 0.0387(4) Uani 1 1 d U . .
C17 C 1.00508(16) 0.69781(15) 0.50118(13) 0.0387(4) Uani 1 1 d U . .
H17A H 0.9103 0.6922 0.5447 0.046 Uiso 1 1 calc R . .
H17B H 1.0457 0.6212 0.4741 0.046 Uiso 1 1 calc R . .
C18 C 1.00982(15) 0.80439(15) 0.40063(12) 0.0351(3) Uani 1 1 d U . .
H18 H 1.1003 0.8292 0.3719 0.042 Uiso 1 1 calc R . .
C19 C 1.08333(15) 0.68877(15) 0.24566(13) 0.0385(4) Uani 1 1 d U . .
C20 C 1.22207(18) 0.65754(19) 0.26145(15) 0.0466(4) Uani 1 1 d U . .
C21 C 1.4359(2) 0.7195(3) 0.2054(2) 0.0932(9) Uani 1 1 d U . .
H21A H 1.4345 0.7113 0.2801 0.140 Uiso 1 1 calc R . .
H21B H 1.4837 0.7858 0.1581 0.140 Uiso 1 1 calc R . .
H21C H 1.4812 0.6438 0.1794 0.140 Uiso 1 1 calc R . .
C22 C 1.06446(17) 0.63799(17) 0.17146(14) 0.0465(4) Uani 1 1 d U . .
H22 H 0.9774 0.6495 0.1670 0.056 Uiso 1 1 calc R . .
C23 C 1.17554(18) 0.56638(17) 0.09874(15) 0.0481(4) Uani 1 1 d U . .
C24 C 1.2287(3) 0.4374(2) -0.0317(2) 0.0819(7) Uani 1 1 d U . .
H24A H 1.2921 0.4856 -0.0898 0.123 Uiso 1 1 calc R . .
H24B H 1.1839 0.4006 -0.0638 0.123 Uiso 1 1 calc R . .
H24C H 1.2767 0.3737 0.0106 0.123 Uiso 1 1 calc R . .
C25 C 0.86108(15) 0.82926(15) 0.28667(12) 0.0354(3) Uani 1 1 d U . .
C26 C 0.76649(15) 0.73651(16) 0.30520(14) 0.0395(4) Uani 1 1 d U A .
C27 C 0.6653(2) 0.56909(19) 0.4309(2) 0.0678(6) Uani 1 1 d U A .
H27A H 0.5758 0.6167 0.4408 0.102 Uiso 1 1 calc R . .
H27B H 0.6679 0.5154 0.4999 0.102 Uiso 1 1 calc R . .
H27C H 0.6866 0.5205 0.3753 0.102 Uiso 1 1 calc R . .
O9 O 0.9343(2) 1.11338(18) 0.08477(15) 0.0707(6) Uani 0.775(3) 1 d PU A 1
C29 C 0.9655(3) 1.0134(3) 0.13492(18) 0.0459(6) Uani 0.775(3) 1 d PDU A 1
C28 C 0.8874(8) 0.9103(5) 0.1685(6) 0.0426(10) Uani 0.775(3) 1 d PU A 1
H28A H 0.9341 0.8555 0.1157 0.051 Uiso 0.775(3) 1 calc PR A 1
H28B H 0.7991 0.9448 0.1592 0.051 Uiso 0.775(3) 1 calc PR A 1
O10 O 1.0800(3) 0.9794(3) 0.1628(4) 0.0634(10) Uani 0.775(3) 1 d PDU A 1
C30 C 1.1730(7) 1.0675(7) 0.1236(7) 0.0735(18) Uani 0.775(3) 1 d PDU A 1
H30A H 1.1950 1.0941 0.0445 0.110 Uiso 0.775(3) 1 calc PR A 1
H30B H 1.2549 1.0296 0.1410 0.110 Uiso 0.775(3) 1 calc PR A 1
H30C H 1.1309 1.1376 0.1590 0.110 Uiso 0.775(3) 1 calc PR A 1
O9' O 1.1198(5) 0.9106(6) 0.0348(4) 0.0561(18) Uani 0.225(3) 1 d PU A 2
C29' C 1.0335(9) 0.9337(8) 0.1177(6) 0.0438(15) Uani 0.225(3) 1 d PDU A 2
C28' C 0.893(3) 0.8861(18) 0.163(2) 0.0374(19) Uani 0.225(3) 1 d PU A 2
H28C H 0.8218 0.9542 0.1524 0.045 Uiso 0.225(3) 1 calc PR A 2
H28D H 0.8972 0.8247 0.1224 0.045 Uiso 0.225(3) 1 calc PR A 2
O10' O 1.0410(11) 1.0124(12) 0.1753(11) 0.052(2) Uani 0.225(3) 1 d PDU A 2
C30' C 1.163(2) 1.068(2) 0.139(2) 0.070(5) Uani 0.225(3) 1 d PDU A 2
H30D H 1.1514 1.1465 0.0909 0.106 Uiso 0.225(3) 1 calc PR A 2
H30E H 1.2396 1.0147 0.0986 0.106 Uiso 0.225(3) 1 calc PR A 2
H30F H 1.1797 1.0790 0.2021 0.106 Uiso 0.225(3) 1 calc PR A 2
N1 N 0.69481(13) 0.88651(13) 0.56675(10) 0.0379(3) Uani 1 1 d . . .
N2 N 0.98703(12) 0.76591(13) 0.31080(10) 0.0359(3) Uani 1 1 d . A .
O1 O 0.56649(11) 0.85819(12) 0.47073(10) 0.0486(3) Uani 1 1 d U . .
O2 O 0.85653(12) 0.94407(12) 0.61203(10) 0.0527(3) Uani 1 1 d . . .
O3 O 1.25574(15) 0.56624(15) 0.32149(12) 0.0712(4) Uani 1 1 d U . .
O4 O 1.29716(12) 0.74579(13) 0.20328(11) 0.0583(4) Uani 1 1 d U . .
O5 O 1.29476(13) 0.55128(14) 0.08888(12) 0.0664(4) Uani 1 1 d U . .
O6 O 1.12845(14) 0.51615(13) 0.04028(11) 0.0648(4) Uani 1 1 d U . .
O7 O 0.70199(12) 0.74253(13) 0.24560(11) 0.0570(4) Uani 1 1 d U . .
O8 O 0.76477(11) 0.65167(11) 0.39569(10) 0.0487(3) Uani 1 1 d U . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.374(2) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.4405(19) . ?
C7 O1 1.2061(18) . ?
C7 N1 1.384(2) . ?
C7 C8 1.526(2) . ?
C8 C9 1.528(2) . ?
C8 C25 1.554(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.511(2) . ?
C9 C18 1.549(2) . ?
C9 H9 0.9800 . ?
C10 O2 1.2023(19) . ?
C10 N1 1.402(2) . ?
C11 C12 1.384(3) . ?
C11 C16 1.386(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.517(2) . ?
C17 C18 1.539(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N2 1.4794(19) . ?
C18 H18 0.9800 . ?
C19 C22 1.352(2) . ?
C19 N2 1.368(2) . ?
C19 C20 1.518(2) . ?
C20 O3 1.198(2) . ?
C20 O4 1.329(2) . ?
C21 O4 1.449(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.447(2) . ?
C22 H22 0.9300 . ?
C23 O5 1.206(2) . ?
C23 O6 1.352(2) . ?
C24 O6 1.442(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 N2 1.471(2) . ?
C25 C28' 1.53(3) . ?
C25 C26 1.544(2) . ?
C25 C28 1.551(7) . ?
C26 O7 1.2031(19) . ?
C26 O8 1.321(2) . ?
C27 O8 1.453(2) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O9 C29 1.194(3) . ?
C29 O10 1.346(3) . ?
C29 C28 1.481(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
O10 C30 1.444(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
O9' C29' 1.185(9) . ?
C29' O10' 1.348(5) . ?
C29' C28' 1.57(3) . ?
C28' H28C 0.9700 . ?
C28' H28D 0.9700 . ?
O10' C30' 1.450(5) . ?
C30' H30D 0.9600 . ?
C30' H30E 0.9600 . ?
C30' H30F 0.9600 . ?

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
C6 C1 C2 118.88(19) . . ?
C6 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.09(19) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.91(19) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.28(16) . . ?
C5 C6 N1 119.39(15) . . ?
C1 C6 N1 119.23(15) . . ?
O1 C7 N1 125.23(14) . . ?
O1 C7 C8 127.13(15) . . ?
N1 C7 C8 107.53(12) . . ?
C7 C8 C9 105.01(12) . . ?
C7 C8 C25 118.06(12) . . ?
C9 C8 C25 107.56(12) . . ?
C7 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C25 C8 H8 108.6 . . ?
C10 C9 C8 104.28(12) . . ?
C10 C9 C18 113.73(13) . . ?
C8 C9 C18 106.39(12) . . ?
C10 C9 H9 110.7 . . ?
C8 C9 H9 110.7 . . ?
C18 C9 H9 110.7 . . ?
O2 C10 N1 123.67(14) . . ?
O2 C10 C9 128.42(14) . . ?
N1 C10 C9 107.91(13) . . ?
C12 C11 C16 121.08(18) . . ?
C12 C11 H11 119.5 . . ?
C16 C11 H11 119.5 . . ?
C13 C12 C11 120.59(18) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.57(17) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.06(17) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 121.24(16) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 117.45(15) . . ?
C11 C16 C17 119.91(14) . . ?
C15 C16 C17 122.54(14) . . ?
C16 C17 C18 115.18(13) . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
N2 C18 C17 111.33(12) . . ?
N2 C18 C9 103.60(12) . . ?
C17 C18 C9 116.19(12) . . ?
N2 C18 H18 108.5 . . ?
C17 C18 H18 108.5 . . ?
C9 C18 H18 108.5 . . ?
C22 C19 N2 125.87(15) . . ?
C22 C19 C20 118.48(15) . . ?
N2 C19 C20 115.64(14) . . ?
O3 C20 O4 125.46(17) . . ?
O3 C20 C19 123.33(18) . . ?
O4 C20 C19 111.18(16) . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 C23 122.06(16) . . ?
C19 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
O5 C23 O6 122.74(16) . . ?
O5 C23 C22 126.63(17) . . ?
O6 C23 C22 110.63(15) . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C25 C28' 110.4(10) . . ?
N2 C25 C26 111.19(13) . . ?
C28' C25 C26 103.2(10) . . ?
N2 C25 C28 113.4(3) . . ?
C28' C25 C28 10.7(9) . . ?
C26 C25 C28 110.3(3) . . ?
N2 C25 C8 103.39(12) . . ?
C28' C25 C8 118.6(7) . . ?
C26 C25 C8 110.27(12) . . ?
C28 C25 C8 108.0(2) . . ?
O7 C26 O8 125.03(15) . . ?
O7 C26 C25 124.12(16) . . ?
O8 C26 C25 110.84(13) . . ?
O8 C27 H27A 109.5 . . ?
O8 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O8 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O9 C29 O10 123.8(3) . . ?
O9 C29 C28 124.2(4) . . ?
O10 C29 C28 111.9(4) . . ?
C29 C28 C25 120.2(6) . . ?
C29 C28 H28A 107.3 . . ?
C25 C28 H28A 107.3 . . ?
C29 C28 H28B 107.3 . . ?
C25 C28 H28B 107.3 . . ?
H28A C28 H28B 106.9 . . ?
C29 O10 C30 117.2(4) . . ?
O9' C29' O10' 123.4(9) . . ?
O9' C29' C28' 122.4(11) . . ?
O10' C29' C28' 113.8(11) . . ?
C25 C28' C29' 109.7(19) . . ?
C25 C28' H28C 109.7 . . ?
C29' C28' H28C 109.7 . . ?
C25 C28' H28D 109.7 . . ?
C29' C28' H28D 109.7 . . ?
H28C C28' H28D 108.2 . . ?
C29' O10' C30' 119.3(15) . . ?
O10' C30' H30D 109.5 . . ?
O10' C30' H30E 109.5 . . ?
H30D C30' H30E 109.5 . . ?
O10' C30' H30F 109.5 . . ?
H30D C30' H30F 109.5 . . ?
H30E C30' H30F 109.5 . . ?
C7 N1 C10 113.08(12) . . ?
C7 N1 C6 124.90(13) . . ?
C10 N1 C6 122.02(13) . . ?
C19 N2 C25 121.92(13) . . ?
C19 N2 C18 122.56(12) . . ?
C25 N2 C18 115.05(12) . . ?
C20 O4 C21 115.25(18) . . ?
C23 O6 C24 116.10(16) . . ?
C26 O8 C27 116.16(14) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.047
#===============================================================
####################################################################### 
# 
# 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_4m
_database_code_depnum_ccdc_archive 'CCDC 1477027'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H30 N2 O10'
_chemical_formula_sum            'C22 H30 N2 O10'
_chemical_formula_weight         482.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   13.234(3)
_cell_length_b                   9.2233(16)
_cell_length_c                   20.475(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.781(6)
_cell_angle_gamma                90
_cell_volume                     2437.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6148
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      21.58

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32511
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.578
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4783
_reflns_number_gt                2692
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0944P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4783
_refine_ls_number_parameters     314
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1769
_refine_ls_wR_factor_gt          0.1525
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.162
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36357(19) 0.6620(3) 0.27533(12) 0.0365(6) Uani 1 1 d . . . . .
H1 H 0.4027 0.5855 0.3031 0.044 Uiso 1 1 calc R U . . .
C2 C 0.3531(2) 0.6297(3) 0.20160(14) 0.0425(7) Uani 1 1 d . . . . .
C3 C 0.3573(3) 0.7727(4) 0.09811(14) 0.0654(10) Uani 1 1 d . . . . .
H3A H 0.3687 0.8719 0.0876 0.098 Uiso 1 1 calc R U . . .
H3B H 0.2883 0.7445 0.0762 0.098 Uiso 1 1 calc R U . . .
H3C H 0.4064 0.7119 0.0830 0.098 Uiso 1 1 calc R U . . .
C4 C 0.4069(2) 0.8672(3) 0.21512(14) 0.0452(7) Uani 1 1 d . . . . .
C5 C 0.4222(2) 0.8047(3) 0.28533(12) 0.0375(7) Uani 1 1 d . . . . .
H5 H 0.4960 0.7841 0.3021 0.045 Uiso 1 1 calc R U . . .
C6 C 0.26008(19) 0.6937(3) 0.29664(12) 0.0358(6) Uani 1 1 d . . . . .
H6 H 0.2405 0.6080 0.3193 0.043 Uiso 1 1 calc R U . . .
C7 C 0.16791(19) 0.7395(3) 0.24111(13) 0.0415(7) Uani 1 1 d . . . . .
H7A H 0.1208 0.7954 0.2613 0.050 Uiso 1 1 calc R U . . .
H7B H 0.1933 0.8035 0.2107 0.050 Uiso 1 1 calc R U . . .
C8 C 0.1066(2) 0.6182(4) 0.20006(16) 0.0659(10) Uani 1 1 d . . . . .
H8 H 0.1552 0.5579 0.1822 0.079 Uiso 1 1 calc R U . . .
C9 C 0.0522(3) 0.5222(4) 0.2415(2) 0.1004(14) Uani 1 1 d . . . . .
H9A H 0.0014 0.5780 0.2575 0.151 Uiso 1 1 calc R U . . .
H9B H 0.1020 0.4841 0.2789 0.151 Uiso 1 1 calc R U . . .
H9C H 0.0187 0.4436 0.2144 0.151 Uiso 1 1 calc R U . . .
C10 C 0.0292(3) 0.6845(5) 0.14079(19) 0.1124(17) Uani 1 1 d . . . . .
H10A H -0.0089 0.6084 0.1142 0.169 Uiso 1 1 calc R U . . .
H10B H 0.0659 0.7401 0.1139 0.169 Uiso 1 1 calc R U . . .
H10C H -0.0180 0.7464 0.1572 0.169 Uiso 1 1 calc R U . . .
C11 C 0.38292(19) 0.8941(3) 0.33869(12) 0.0344(6) Uani 1 1 d . . . . .
C12 C 0.3559(2) 1.0496(3) 0.31397(13) 0.0412(7) Uani 1 1 d . . . . .
C13 C 0.2374(3) 1.1940(4) 0.2401(2) 0.0881(13) Uani 1 1 d . . . . .
H13A H 0.2429 1.2673 0.2740 0.132 Uiso 1 1 calc R U . . .
H13B H 0.1676 1.1911 0.2139 0.132 Uiso 1 1 calc R U . . .
H13C H 0.2840 1.2162 0.2116 0.132 Uiso 1 1 calc R U . . .
C14 C 0.46707(19) 0.9046(3) 0.40443(13) 0.0382(7) Uani 1 1 d . . . . .
H14A H 0.5271 0.9530 0.3947 0.046 Uiso 1 1 calc R U . . .
H14B H 0.4408 0.9652 0.4357 0.046 Uiso 1 1 calc R U . . .
C15 C 0.5013(2) 0.7640(3) 0.43790(14) 0.0500(7) Uani 1 1 d . U . . .
C16 C 0.6114(3) 0.6587(3) 0.53241(17) 0.0754(11) Uani 1 1 d . . . . .
H16A H 0.5622 0.6118 0.5535 0.113 Uiso 1 1 calc R U . . .
H16B H 0.6709 0.6874 0.5659 0.113 Uiso 1 1 calc R U . . .
H16C H 0.6325 0.5927 0.5016 0.113 Uiso 1 1 calc R U . . .
C17 C 0.23445(19) 0.8464(3) 0.39247(12) 0.0327(6) Uani 1 1 d . . . . .
C18 C 0.1553(3) 0.7351(3) 0.40231(13) 0.0408(7) Uani 1 1 d . . . . .
C19 C 0.1281(3) 0.5289(4) 0.4610(2) 0.1000(14) Uani 1 1 d . . . . .
H19A H 0.0857 0.5776 0.4866 0.150 Uiso 1 1 calc R U . . .
H19B H 0.1654 0.4517 0.4872 0.150 Uiso 1 1 calc R U . . .
H19C H 0.0849 0.4897 0.4209 0.150 Uiso 1 1 calc R U . . .
C20 C 0.2409(2) 0.9711(3) 0.42769(12) 0.0401(7) Uani 1 1 d . . . . .
H20 H 0.2831 1.0452 0.4181 0.048 Uiso 1 1 calc R U . . .
C21 C 0.1844(2) 0.9932(3) 0.47994(13) 0.0390(7) Uani 1 1 d . . . . .
C22 C 0.1369(3) 1.1640(4) 0.55309(15) 0.0677(10) Uani 1 1 d . . . . .
H22A H 0.0642 1.1456 0.5372 0.102 Uiso 1 1 calc R U . . .
H22B H 0.1473 1.2642 0.5653 0.102 Uiso 1 1 calc R U . . .
H22C H 0.1634 1.1043 0.5915 0.102 Uiso 1 1 calc R U . . .
N1 N 0.37023(17) 0.7570(3) 0.17041(11) 0.0456(6) Uani 1 1 d . . . . .
N2 N 0.29152(15) 0.8112(2) 0.34686(10) 0.0338(5) Uani 1 1 d . . . . .
O1 O 0.33454(16) 0.5151(2) 0.17337(10) 0.0578(6) Uani 1 1 d . . . . .
O2 O 0.42583(17) 0.9880(3) 0.19933(10) 0.0654(6) Uani 1 1 d . . . . .
O3 O 0.41089(16) 1.1519(2) 0.33110(10) 0.0600(6) Uani 1 1 d . . . . .
O4 O 0.26395(15) 1.0551(2) 0.27137(10) 0.0531(6) Uani 1 1 d . . . . .
O5 O 0.4748(2) 0.6451(2) 0.41795(10) 0.0808(7) Uani 1 1 d . U . . .
O6 O 0.56441(16) 0.7850(2) 0.49661(10) 0.0653(7) Uani 1 1 d . . . . .
O7 O 0.06601(16) 0.7394(2) 0.37574(10) 0.0572(6) Uani 1 1 d . . . . .
O8 O 0.20055(16) 0.6307(2) 0.44322(10) 0.0579(6) Uani 1 1 d . . . . .
O9 O 0.13605(16) 0.9020(2) 0.50241(9) 0.0551(6) Uani 1 1 d . . . . .
O10 O 0.19032(16) 1.1307(2) 0.50123(9) 0.0536(6) Uani 1 1 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
C1 C2 1.515(4) . ?
C1 C5 1.518(3) . ?
C1 C6 1.554(3) . ?
C1 H1 0.9800 . ?
C2 O1 1.204(3) . ?
C2 N1 1.378(4) . ?
C3 N1 1.459(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 O2 1.202(3) . ?
C4 N1 1.382(3) . ?
C4 C5 1.520(4) . ?
C5 C11 1.547(4) . ?
C5 H5 0.9800 . ?
C6 N2 1.488(3) . ?
C6 C7 1.531(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.522(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.515(5) . ?
C8 C10 1.532(5) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.472(3) . ?
C11 C12 1.537(4) . ?
C11 C14 1.549(3) . ?
C12 O3 1.196(3) . ?
C12 O4 1.332(3) . ?
C13 O4 1.440(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.490(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O5 1.196(3) . ?
C15 O6 1.317(3) . ?
C16 O6 1.442(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C20 1.350(3) . ?
C17 N2 1.364(3) . ?
C17 C18 1.511(4) . ?
C18 O7 1.187(3) . ?
C18 O8 1.329(3) . ?
C19 O8 1.445(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.449(4) . ?
C20 H20 0.9300 . ?
C21 O9 1.207(3) . ?
C21 O10 1.338(3) . ?
C22 O10 1.433(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 C1 C5 103.7(2) . . ?
C2 C1 C6 115.1(2) . . ?
C5 C1 C6 104.8(2) . . ?
C2 C1 H1 110.9 . . ?
C5 C1 H1 110.9 . . ?
C6 C1 H1 110.9 . . ?
O1 C2 N1 124.2(3) . . ?
O1 C2 C1 128.0(3) . . ?
N1 C2 C1 107.8(2) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 N1 124.6(3) . . ?
O2 C4 C5 127.9(3) . . ?
N1 C4 C5 107.5(2) . . ?
C1 C5 C4 104.1(2) . . ?
C1 C5 C11 108.4(2) . . ?
C4 C5 C11 118.0(2) . . ?
C1 C5 H5 108.6 . . ?
C4 C5 H5 108.6 . . ?
C11 C5 H5 108.6 . . ?
N2 C6 C7 111.5(2) . . ?
N2 C6 C1 101.64(19) . . ?
C7 C6 C1 116.7(2) . . ?
N2 C6 H6 108.9 . . ?
C7 C6 H6 108.9 . . ?
C1 C6 H6 108.9 . . ?
C8 C7 C6 116.5(2) . . ?
C8 C7 H7A 108.2 . . ?
C6 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
C6 C7 H7B 108.2 . . ?
H7A C7 H7B 107.3 . . ?
C9 C8 C7 112.5(3) . . ?
C9 C8 C10 111.1(3) . . ?
C7 C8 C10 109.0(3) . . ?
C9 C8 H8 108.0 . . ?
C7 C8 H8 108.0 . . ?
C10 C8 H8 108.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 112.6(2) . . ?
N2 C11 C5 102.50(19) . . ?
C12 C11 C5 110.8(2) . . ?
N2 C11 C14 112.6(2) . . ?
C12 C11 C14 107.4(2) . . ?
C5 C11 C14 110.9(2) . . ?
O3 C12 O4 124.8(3) . . ?
O3 C12 C11 123.9(3) . . ?
O4 C12 C11 111.3(2) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C11 115.6(2) . . ?
C15 C14 H14A 108.4 . . ?
C11 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
C11 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
O5 C15 O6 121.7(3) . . ?
O5 C15 C14 127.2(3) . . ?
O6 C15 C14 111.1(2) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C20 C17 N2 126.1(2) . . ?
C20 C17 C18 118.1(2) . . ?
N2 C17 C18 115.8(2) . . ?
O7 C18 O8 125.2(3) . . ?
O7 C18 C17 124.4(3) . . ?
O8 C18 C17 110.3(3) . . ?
O8 C19 H19A 109.5 . . ?
O8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 C21 122.2(2) . . ?
C17 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
O9 C21 O10 122.3(2) . . ?
O9 C21 C20 125.9(2) . . ?
O10 C21 C20 111.8(2) . . ?
O10 C22 H22A 109.5 . . ?
O10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 N1 C4 112.9(2) . . ?
C2 N1 C3 124.1(2) . . ?
C4 N1 C3 123.0(3) . . ?
C17 N2 C11 123.2(2) . . ?
C17 N2 C6 122.3(2) . . ?
C11 N2 C6 114.26(19) . . ?
C12 O4 C13 115.0(2) . . ?
C15 O6 C16 117.4(2) . . ?
C18 O8 C19 113.4(3) . . ?
C21 O10 C22 116.2(2) . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 1477028'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N2 O6, H2 O'
_chemical_formula_sum            'C18 H22 N2 O7'
_chemical_formula_weight         378.37

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6267(14)
_cell_length_b                   10.6646(15)
_cell_length_c                   11.1642(17)
_cell_angle_alpha                113.847(4)
_cell_angle_beta                 92.046(5)
_cell_angle_gamma                97.197(5)
_cell_volume                     927.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4886
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14275
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.003
_diffrn_reflns_theta_max         27.614
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4258
_reflns_number_gt                2816
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+0.1459P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4258
_refine_ls_number_parameters     255
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2475(2) 0.75490(19) 0.27006(19) 0.0429(5) Uani 1 1 d . . . . .
H1 H 1.1645 0.7995 0.3084 0.051 Uiso 1 1 calc R U . . .
C2 C 1.3836(2) 0.8301(2) 0.2582(2) 0.0492(5) Uani 1 1 d . . . . .
H2 H 1.3915 0.9259 0.2880 0.059 Uiso 1 1 calc R U . . .
C3 C 1.5075(2) 0.7655(2) 0.20298(19) 0.0467(5) Uani 1 1 d . . . . .
H3 H 1.5989 0.8172 0.1956 0.056 Uiso 1 1 calc R U . . .
C4 C 1.4953(2) 0.6243(2) 0.15874(19) 0.0463(5) Uani 1 1 d . . . . .
H4 H 1.5794 0.5804 0.1218 0.056 Uiso 1 1 calc R U . . .
C5 C 1.3590(2) 0.5460(2) 0.16840(18) 0.0398(4) Uani 1 1 d . . . . .
H5 H 1.3509 0.4501 0.1376 0.048 Uiso 1 1 calc R U . . .
C6 C 1.2359(2) 0.61255(18) 0.22432(17) 0.0328(4) Uani 1 1 d . . . . .
C7 C 0.9456(2) 0.54491(18) 0.19496(18) 0.0352(4) Uani 1 1 d . . . . .
C8 C 0.8269(2) 0.45768(17) 0.23481(17) 0.0334(4) Uani 1 1 d . . . . .
H8 H 0.7508 0.5130 0.2864 0.040 Uiso 1 1 calc R U . . .
C9 C 0.92118(19) 0.40366(16) 0.31735(17) 0.0300(4) Uani 1 1 d . . . . .
H9 H 0.8974 0.4453 0.4092 0.036 Uiso 1 1 calc R U . . .
C10 C 1.0906(2) 0.45133(17) 0.30693(17) 0.0316(4) Uani 1 1 d . . . . .
C11 C 0.7432(2) 0.32889(19) 0.1180(2) 0.0457(5) Uani 1 1 d . . . . .
H11A H 0.6327 0.3116 0.1291 0.055 Uiso 1 1 calc R U . . .
H11B H 0.7532 0.3396 0.0363 0.055 Uiso 1 1 calc R U . . .
C12 C 0.7329(3) 0.0791(2) 0.0373(2) 0.0681(7) Uani 1 1 d . . . . .
H12A H 0.6308 0.0724 0.0677 0.102 Uiso 1 1 calc R U . . .
H12B H 0.7866 0.0080 0.0434 0.102 Uiso 1 1 calc R U . . .
H12C H 0.7221 0.0676 -0.0526 0.102 Uiso 1 1 calc R U . . .
C13 C 0.8675(2) 0.24493(17) 0.25830(17) 0.0315(4) Uani 1 1 d . . . . .
C14 C 0.7240(2) 0.20915(19) 0.3229(2) 0.0410(5) Uani 1 1 d . . . . .
C15 C 0.5017(3) 0.2887(3) 0.4301(3) 0.0809(9) Uani 1 1 d . . . . .
H15A H 0.4276 0.2146 0.3669 0.121 Uiso 1 1 calc R U . . .
H15B H 0.4550 0.3718 0.4642 0.121 Uiso 1 1 calc R U . . .
H15C H 0.5309 0.2644 0.5009 0.121 Uiso 1 1 calc R U . . .
C16 C 0.9911(2) 0.15726(18) 0.26647(17) 0.0350(4) Uani 1 1 d . . . . .
H16A H 0.9485 0.0599 0.2187 0.042 Uiso 1 1 calc R U . . .
H16B H 1.0816 0.1771 0.2243 0.042 Uiso 1 1 calc R U . . .
C17 C 1.04283(19) 0.18395(18) 0.40539(18) 0.0313(4) Uani 1 1 d . . . . .
C18 C 1.1987(3) 0.1147(2) 0.5382(2) 0.0517(5) Uani 1 1 d . . . . .
H18A H 1.2554 0.2066 0.5854 0.078 Uiso 1 1 calc R U . . .
H18B H 1.2672 0.0479 0.5302 0.078 Uiso 1 1 calc R U . . .
H18C H 1.1118 0.1007 0.5852 0.078 Uiso 1 1 calc R U . . .
N1 N 1.09467(16) 0.53415(14) 0.23681(14) 0.0313(3) Uani 1 1 d . . . . .
N2 N 0.82353(19) 0.21590(15) 0.11894(15) 0.0410(4) Uani 1 1 d . . . . .
O1 O 0.91844(17) 0.61313(16) 0.13539(16) 0.0591(4) Uani 1 1 d . . . . .
O2 O 1.20569(15) 0.42936(14) 0.35463(14) 0.0475(4) Uani 1 1 d . . . . .
O3 O 0.68793(18) 0.09901(15) 0.32649(18) 0.0663(5) Uani 1 1 d . . . . .
O4 O 0.63969(15) 0.31151(14) 0.36755(16) 0.0550(4) Uani 1 1 d . . . . .
O5 O 1.00301(16) 0.26983(14) 0.50272(13) 0.0468(4) Uani 1 1 d . . . . .
O6 O 1.14078(15) 0.09791(13) 0.40857(12) 0.0425(3) Uani 1 1 d . . . . .
O7 O 0.1088(3) 0.2000(2) 0.9804(2) 0.0919(6) Uani 1 1 d D . . . .
H7A H 0.106(3) 0.250(2) 0.926(2) 0.158(16) Uiso 1 1 d D . . . .
H7B H 0.0093(18) 0.204(4) 1.016(3) 0.19(2) Uiso 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
C1 C2 1.378(3) . ?
C1 C6 1.381(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.433(2) . ?
C7 O1 1.204(2) . ?
C7 N1 1.387(2) . ?
C7 C8 1.497(2) . ?
C8 C9 1.528(2) . ?
C8 C11 1.531(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.511(2) . ?
C9 C13 1.547(2) . ?
C9 H9 0.9800 . ?
C10 O2 1.202(2) . ?
C10 N1 1.395(2) . ?
C11 N2 1.467(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.469(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N2 1.483(2) . ?
C13 C16 1.527(2) . ?
C13 C14 1.538(3) . ?
C14 O3 1.194(2) . ?
C14 O4 1.324(2) . ?
C15 O4 1.445(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.499(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O5 1.199(2) . ?
C17 O6 1.333(2) . ?
C18 O6 1.447(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O7 H7A 0.9570(10) . ?
O7 H7B 0.9571(10) . ?

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 C1 C6 119.23(18) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C3 C2 C1 120.89(19) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 119.48(18) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.75(18) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.99(17) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 120.66(16) . . ?
C5 C6 N1 120.02(15) . . ?
C1 C6 N1 119.32(16) . . ?
O1 C7 N1 124.70(17) . . ?
O1 C7 C8 126.35(16) . . ?
N1 C7 C8 108.95(14) . . ?
C7 C8 C9 105.34(13) . . ?
C7 C8 C11 113.04(16) . . ?
C9 C8 C11 105.87(13) . . ?
C7 C8 H8 110.8 . . ?
C9 C8 H8 110.8 . . ?
C11 C8 H8 110.8 . . ?
C10 C9 C8 104.57(13) . . ?
C10 C9 C13 116.21(14) . . ?
C8 C9 C13 105.76(13) . . ?
C10 C9 H9 110.0 . . ?
C8 C9 H9 110.0 . . ?
C13 C9 H9 110.0 . . ?
O2 C10 N1 123.86(16) . . ?
O2 C10 C9 127.50(16) . . ?
N1 C10 C9 108.56(14) . . ?
N2 C11 C8 104.30(14) . . ?
N2 C11 H11A 110.9 . . ?
C8 C11 H11A 110.9 . . ?
N2 C11 H11B 110.9 . . ?
C8 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C16 110.06(15) . . ?
N2 C13 C14 110.77(14) . . ?
C16 C13 C14 108.06(14) . . ?
N2 C13 C9 101.18(13) . . ?
C16 C13 C9 116.15(14) . . ?
C14 C13 C9 110.49(15) . . ?
O3 C14 O4 123.58(18) . . ?
O3 C14 C13 123.88(18) . . ?
O4 C14 C13 112.43(15) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C13 112.62(15) . . ?
C17 C16 H16A 109.1 . . ?
C13 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C13 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
O5 C17 O6 123.02(16) . . ?
O5 C17 C16 125.98(16) . . ?
O6 C17 C16 111.00(16) . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 N1 C10 112.21(14) . . ?
C7 N1 C6 123.96(14) . . ?
C10 N1 C6 123.39(14) . . ?
C11 N2 C12 111.80(15) . . ?
C11 N2 C13 107.52(14) . . ?
C12 N2 C13 116.72(15) . . ?
C14 O4 C15 117.00(16) . . ?
C17 O6 C18 115.75(15) . . ?
H7A O7 H7B 104.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O1 0.9570(10) 1.876(8) 2.806(2) 164(2) 2_666
O7 H7B N2 0.9571(10) 1.993(6) 2.940(3) 170(3) 1_456

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_5cc
_database_code_depnum_ccdc_archive 'CCDC 1477029'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 Br N2 O6'
_chemical_formula_sum            'C18 H19 Br N2 O6'
_chemical_formula_weight         439.26

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1148(17)
_cell_length_b                   11.372(3)
_cell_length_c                   12.653(3)
_cell_angle_alpha                110.960(7)
_cell_angle_beta                 91.815(8)
_cell_angle_gamma                93.310(8)
_cell_volume                     952.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7485
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    2.194
_shelx_estimated_absorpt_T_min   0.579
_shelx_estimated_absorpt_T_max   0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_T_max  0.617
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13870
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.923
_diffrn_reflns_theta_max         27.650
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4378
_reflns_number_gt                3375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0665P)²+0.3894P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.055(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4378
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.24199(5) 0.95562(3) 0.91204(3) 0.0592(2) Uani 1 1 d . . . . .
C1 C 1.1557(5) 0.5826(3) 0.6976(3) 0.0467(7) Uani 1 1 d . . . . .
H1 H 1.1929 0.5328 0.6267 0.056 Uiso 1 1 calc R U . . .
C2 C 1.2143(5) 0.7094(3) 0.7436(3) 0.0485(8) Uani 1 1 d . . . . .
H2 H 1.2915 0.7457 0.7038 0.058 Uiso 1 1 calc R U . . .
C3 C 1.1577(4) 0.7817(3) 0.8485(3) 0.0410(7) Uani 1 1 d . . . . .
C4 C 1.0455(5) 0.7297(3) 0.9097(3) 0.0445(7) Uani 1 1 d . . . . .
H4 H 1.0095 0.7794 0.9810 0.053 Uiso 1 1 calc R U . . .
C5 C 0.9869(4) 0.6027(3) 0.8635(3) 0.0412(7) Uani 1 1 d . . . . .
H5 H 0.9110 0.5661 0.9037 0.049 Uiso 1 1 calc R U . . .
C6 C 1.0416(4) 0.5305(3) 0.7579(2) 0.0360(6) Uani 1 1 d . . . . .
C7 C 0.8510(4) 0.3564(3) 0.6100(2) 0.0402(7) Uani 1 1 d . . . . .
C8 C 0.7928(4) 0.2194(3) 0.5854(2) 0.0361(6) Uani 1 1 d . . . . .
H8 H 0.8443 0.1658 0.5148 0.043 Uiso 1 1 calc R U . . .
C9 C 0.8750(4) 0.1920(2) 0.6863(2) 0.0317(6) Uani 1 1 d . . . . .
H9 H 0.9611 0.1244 0.6598 0.038 Uiso 1 1 calc R U . . .
C10 C 0.9839(4) 0.3124(3) 0.7608(2) 0.0355(6) Uani 1 1 d . . . . .
C11 C 0.5809(4) 0.1908(3) 0.5831(3) 0.0418(7) Uani 1 1 d . . . . .
H11A H 0.5181 0.2669 0.6212 0.050 Uiso 1 1 calc R U . . .
H11B H 0.5278 0.1518 0.5058 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3698(4) 0.0793(3) 0.6697(3) 0.0511(8) Uani 1 1 d . . . . .
H12A H 0.3250 0.1562 0.7204 0.077 Uiso 1 1 calc R U . . .
H12B H 0.3660 0.0172 0.7049 0.077 Uiso 1 1 calc R U . . .
H12C H 0.2912 0.0488 0.6009 0.077 Uiso 1 1 calc R U . . .
C13 C 0.7050(4) 0.1467(2) 0.7399(2) 0.0301(6) Uani 1 1 d . . . . .
C14 C 0.6343(4) 0.2602(3) 0.8363(2) 0.0345(6) Uani 1 1 d . . . . .
C15 C 0.4850(6) 0.3309(4) 1.0081(3) 0.0636(11) Uani 1 1 d . . . . .
H15A H 0.5792 0.3994 1.0416 0.095 Uiso 1 1 calc R U . . .
H15B H 0.4411 0.3003 1.0652 0.095 Uiso 1 1 calc R U . . .
H15C H 0.3813 0.3598 0.9762 0.095 Uiso 1 1 calc R U . . .
C16 C 0.7461(4) 0.0387(3) 0.7802(2) 0.0391(6) Uani 1 1 d . . . . .
H16A H 0.8525 0.0659 0.8354 0.047 Uiso 1 1 calc R U . . .
H16B H 0.6378 0.0205 0.8181 0.047 Uiso 1 1 calc R U . . .
C17 C 0.7894(4) -0.0807(3) 0.6863(3) 0.0419(7) Uani 1 1 d . . . . .
C18 C 0.7101(7) -0.3006(4) 0.6048(5) 0.0830(14) Uani 1 1 d . . . . .
H18A H 0.7225 -0.2970 0.5307 0.124 Uiso 1 1 calc R U . . .
H18B H 0.6074 -0.3603 0.6024 0.124 Uiso 1 1 calc R U . . .
H18C H 0.8247 -0.3266 0.6290 0.124 Uiso 1 1 calc R U . . .
N1 N 0.9725(3) 0.4005(2) 0.70705(19) 0.0357(5) Uani 1 1 d . . . . .
N2 N 0.5642(3) 0.1035(2) 0.64366(19) 0.0346(5) Uani 1 1 d . . . . .
O1 O 0.8025(4) 0.4198(2) 0.5576(2) 0.0635(7) Uani 1 1 d . . . . .
O2 O 1.0691(3) 0.3315(2) 0.84919(19) 0.0488(5) Uani 1 1 d . . . . .
O3 O 0.6316(3) 0.36361(19) 0.83057(19) 0.0496(6) Uani 1 1 d . . . . .
O4 O 0.5660(3) 0.2297(2) 0.91964(17) 0.0462(5) Uani 1 1 d . . . . .
O5 O 0.9131(4) -0.0913(2) 0.6230(3) 0.0745(8) Uani 1 1 d . . . . .
O6 O 0.6734(4) -0.1766(2) 0.6841(2) 0.0603(7) Uani 1 1 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
Br1 C3 1.900(3) . ?
C1 C6 1.378(4) . ?
C1 C2 1.382(4) . ?
C2 C3 1.376(5) . ?
C3 C4 1.378(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.377(4) . ?
C6 N1 1.434(4) . ?
C7 O1 1.198(4) . ?
C7 N1 1.396(4) . ?
C7 C8 1.505(4) . ?
C8 C11 1.521(4) . ?
C8 C9 1.527(4) . ?
C9 C10 1.507(4) . ?
C9 C13 1.555(4) . ?
C10 O2 1.197(3) . ?
C10 N1 1.402(4) . ?
C11 N2 1.457(4) . ?
C12 N2 1.465(4) . ?
C13 N2 1.472(3) . ?
C13 C16 1.528(4) . ?
C13 C14 1.547(4) . ?
C14 O3 1.205(3) . ?
C14 O4 1.320(4) . ?
C15 O4 1.450(4) . ?
C16 C17 1.506(4) . ?
C17 O5 1.191(4) . ?
C17 O6 1.320(4) . ?
C18 O6 1.453(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
C6 C1 C2 119.3(3) . . ?
C3 C2 C1 119.6(3) . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 Br1 119.3(2) . . ?
C4 C3 Br1 119.4(2) . . ?
C3 C4 C5 119.1(3) . . ?
C6 C5 C4 119.7(3) . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 N1 119.9(2) . . ?
C1 C6 N1 119.0(3) . . ?
O1 C7 N1 124.3(3) . . ?
O1 C7 C8 127.2(3) . . ?
N1 C7 C8 108.5(2) . . ?
C7 C8 C11 114.0(2) . . ?
C7 C8 C9 104.9(2) . . ?
C11 C8 C9 105.7(2) . . ?
C10 C9 C8 105.8(2) . . ?
C10 C9 C13 115.9(2) . . ?
C8 C9 C13 106.2(2) . . ?
O2 C10 N1 124.8(3) . . ?
O2 C10 C9 127.4(3) . . ?
N1 C10 C9 107.8(2) . . ?
N2 C11 C8 103.2(2) . . ?
N2 C13 C16 110.7(2) . . ?
N2 C13 C14 109.4(2) . . ?
C16 C13 C14 111.6(2) . . ?
N2 C13 C9 101.2(2) . . ?
C16 C13 C9 113.6(2) . . ?
C14 C13 C9 109.8(2) . . ?
O3 C14 O4 124.2(2) . . ?
O3 C14 C13 122.3(2) . . ?
O4 C14 C13 113.3(2) . . ?
C17 C16 C13 113.8(2) . . ?
O5 C17 O6 123.0(3) . . ?
O5 C17 C16 126.2(3) . . ?
O6 C17 C16 110.8(3) . . ?
C7 N1 C10 112.4(2) . . ?
C7 N1 C6 122.2(2) . . ?
C10 N1 C6 124.0(2) . . ?
C11 N2 C12 113.0(2) . . ?
C11 N2 C13 108.1(2) . . ?
C12 N2 C13 116.4(2) . . ?
C14 O4 C15 115.5(3) . . ?
C17 O6 C18 116.9(3) . . ?

_refine_diff_density_max         0.559
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.090

