# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_42
_database_code_depnum_ccdc_archive 'CCDC 1547069'
_audit_update_record             
;
2017-04-30 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;



# start Validation Reply Form ================================================

_vrf_PLAT029_42                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.882 Note  
RESPONSE: The crystal selected for data collection was a very thin colourless 
needle which diffracted very weakly at high angles and, consequently, a number 
of reflections are missing, in particular in the 0.90-0.84 A resolution range.
However it was without doubt the best crystal selected after a rigorous 
analysis of the crystals obtained. 
;

# end Validation Reply Form ==================================================



_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H30 N2 O6'
_chemical_formula_sum            'C25 H30 N2 O6'
_chemical_formula_weight         454.51

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   14.6880(15)
_cell_length_b                   5.0342(5)
_cell_length_c                   16.7218(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.151(4)
_cell_angle_gamma                90
_cell_volume                     1224.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3412
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      24.71

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9572
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   
;
program SADABS, Bruker (2001).
;

_diffrn_ambient_temperature      193(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  
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_reflns_number            12797
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.216
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.882
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.882
_diffrn_reflns_point_group_measured_fraction_max 0.712
_diffrn_reflns_point_group_measured_fraction_full 0.713
_reflns_number_total             3145
_reflns_number_gt                2575
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.437
_reflns_Friedel_fraction_max     0.494
_reflns_Friedel_fraction_full    0.495

_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       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'
_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)+(0.1031P)²+0.0690P] 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       .
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3145
_refine_ls_number_parameters     307
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.014
_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
O1 O 0.4469(3) 0.0364(8) 0.5307(2) 0.0776(12) Uani 1 1 d . . . . .
O2 O 0.4750(2) 0.3097(8) 0.63611(18) 0.0629(10) Uani 1 1 d . . . . .
O3 O 0.2295(2) 0.6916(5) 0.45214(14) 0.0419(7) Uani 1 1 d . . . . .
O4 O 0.2495(3) 0.1442(5) 0.33073(16) 0.0556(9) Uani 1 1 d . . . . .
O5 O 0.2936(2) 0.0206(5) 0.16161(19) 0.0526(8) Uani 1 1 d . . . . .
O6 O 0.4032(2) 0.3309(6) 0.15418(19) 0.0474(7) Uani 1 1 d . . . . .
N1 N 0.2830(2) 0.2756(6) 0.48364(18) 0.0382(8) Uani 1 1 d D . . . .
H1N H 0.281(3) 0.114(5) 0.464(2) 0.046 Uiso 1 1 d D U . . .
N2 N 0.2663(2) 0.4591(6) 0.17962(19) 0.0338(7) Uani 1 1 d D . . . .
H2N H 0.289(3) 0.624(5) 0.179(2) 0.041 Uiso 1 1 d D U . . .
C1 C 0.4243(3) 0.2022(10) 0.5740(2) 0.0485(11) Uani 1 1 d . . . . .
C2 C 0.3260(3) 0.3212(9) 0.5648(2) 0.0434(10) Uani 1 1 d . . . . .
H2 H 0.329765 0.516572 0.575543 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2744(3) 0.1845(10) 0.6281(2) 0.0516(11) Uani 1 1 d . . . . .
H3A H 0.271271 -0.008518 0.616762 0.062 Uiso 1 1 calc R U . . .
H3B H 0.310467 0.209199 0.682230 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1778(3) 0.2867(9) 0.6300(3) 0.0489(11) Uani 1 1 d . U . . .
C5 C 0.1621(5) 0.4949(12) 0.6790(3) 0.0746(16) Uani 1 1 d . U . . .
H5 H 0.210673 0.580892 0.712802 0.090 Uiso 1 1 calc R U . . .
C6 C 0.0649(6) 0.5787(12) 0.6762(4) 0.090(2) Uani 1 1 d . U . . .
H6 H 0.049365 0.720852 0.709168 0.108 Uiso 1 1 calc R U . . .
C7 C -0.0020(5) 0.4497(14) 0.6260(5) 0.0856(18) Uani 1 1 d . U . . .
H7 H -0.064039 0.506356 0.623785 0.103 Uiso 1 1 calc R U . . .
C8 C 0.0162(4) 0.2530(13) 0.5813(4) 0.0806(17) Uani 1 1 d . U . . .
H8 H -0.032505 0.165831 0.547886 0.097 Uiso 1 1 calc R U . . .
C9 C 0.1048(4) 0.1688(11) 0.5815(3) 0.0605(13) Uani 1 1 d . U . . .
H9 H 0.116459 0.025455 0.547465 0.073 Uiso 1 1 calc R U . . .
C10 C 0.5683(3) 0.1996(16) 0.6499(3) 0.0785(18) Uani 1 1 d . . . . .
H10A H 0.598642 0.231171 0.602284 0.118 Uiso 1 1 calc R U . . .
H10B H 0.565117 0.008125 0.659757 0.118 Uiso 1 1 calc R U . . .
H10C H 0.603408 0.285876 0.697063 0.118 Uiso 1 1 calc R U . . .
C1' C 0.2443(3) 0.4636(7) 0.4341(2) 0.0315(8) Uani 1 1 d . . . . .
C2' C 0.2225(3) 0.3635(7) 0.3462(2) 0.0340(9) Uani 1 1 d . . . . .
C3' C 0.1703(3) 0.5393(8) 0.2844(2) 0.0362(9) Uani 1 1 d . . . . .
H3'1 H 0.197166 0.719925 0.289443 0.043 Uiso 1 1 calc R U . . .
H3'2 H 0.105757 0.551742 0.294767 0.043 Uiso 1 1 calc R U . . .
C4' C 0.1718(3) 0.4383(7) 0.1985(2) 0.0325(9) Uani 1 1 d . . . . .
H4' H 0.154688 0.245878 0.197148 0.039 Uiso 1 1 calc R U . . .
C5' C 0.1041(3) 0.5827(9) 0.1339(2) 0.0427(10) Uani 1 1 d . . . . .
H5' H 0.120974 0.775146 0.134071 0.051 Uiso 1 1 calc R U . . .
C6' C 0.0049(3) 0.5584(14) 0.1509(3) 0.0668(15) Uani 1 1 d . . . . .
H6'1 H -0.010832 0.370364 0.155366 0.100 Uiso 1 1 calc R U . . .
H6'2 H -0.036572 0.639814 0.106577 0.100 Uiso 1 1 calc R U . . .
H6'3 H -0.001404 0.649497 0.201597 0.100 Uiso 1 1 calc R U . . .
C7' C 0.1117(4) 0.4682(14) 0.0511(3) 0.0681(15) Uani 1 1 d . . . . .
H7'1 H 0.090317 0.283573 0.048642 0.102 Uiso 1 1 calc R U . . .
H7'2 H 0.175991 0.474255 0.041581 0.102 Uiso 1 1 calc R U . . .
H7'3 H 0.073718 0.572831 0.009596 0.102 Uiso 1 1 calc R U . . .
C1" C 0.3171(3) 0.2507(7) 0.1656(2) 0.0384(10) Uani 1 1 d . . . . .
C2" C 0.4682(4) 0.1164(11) 0.1472(4) 0.0750(16) Uani 1 1 d . . . . .
H2"1 H 0.441511 -0.011834 0.105400 0.090 Uiso 1 1 calc R U . . .
H2"2 H 0.481831 0.020996 0.199251 0.090 Uiso 1 1 calc R U . . .
C3" C 0.5548(4) 0.2333(11) 0.1243(3) 0.0596(13) Uani 1 1 d . . . . .
C4" C 0.5851(5) 0.1593(17) 0.0523(4) 0.096(2) Uani 1 1 d . . . . .
H4" H 0.549626 0.039612 0.016571 0.116 Uiso 1 1 calc R U . . .
C5" C 0.6674(5) 0.260(2) 0.0324(4) 0.104(3) Uani 1 1 d . . . . .
H5" H 0.687954 0.209906 -0.016788 0.125 Uiso 1 1 calc R U . . .
C6" C 0.7165(5) 0.4263(18) 0.0820(4) 0.097(2) Uani 1 1 d . . . . .
H6" H 0.775706 0.480329 0.071805 0.116 Uiso 1 1 calc R U . . .
C7" C 0.6824(6) 0.519(3) 0.1473(5) 0.135(4) Uani 1 1 d . . . . .
H7" H 0.714616 0.654185 0.179341 0.163 Uiso 1 1 calc R U . . .
C8" C 0.6018(5) 0.421(2) 0.1683(4) 0.112(3) Uani 1 1 d . . . . .
H8" H 0.579386 0.488101 0.214860 0.135 Uiso 1 1 calc R 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
O1 C1 1.183(6) . ?
O2 C1 1.306(5) . ?
O2 C10 1.465(6) . ?
O3 C1' 1.214(4) . ?
O4 C2' 1.213(5) . ?
O5 C1" 1.208(5) . ?
O6 C1" 1.366(5) . ?
O6 C2" 1.457(6) . ?
N1 C1' 1.331(5) . ?
N1 C2 1.431(5) . ?
N1 H1N 0.88(2) . ?
N2 C1" 1.327(5) . ?
N2 C4' 1.470(5) . ?
N2 H2N 0.89(2) . ?
C1 C2 1.551(6) . ?
C2 C3 1.548(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.513(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.370(7) . ?
C4 C9 1.383(7) . ?
C5 C6 1.483(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.364(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.291(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.368(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C1' C2' 1.544(5) . ?
C2' C3' 1.488(5) . ?
C3' C4' 1.527(5) . ?
C3' H3'1 0.9900 . ?
C3' H3'2 0.9900 . ?
C4' C5' 1.542(5) . ?
C4' H4' 1.0000 . ?
C5' C7' 1.519(7) . ?
C5' C6' 1.528(7) . ?
C5' H5' 1.0000 . ?
C6' H6'1 0.9800 . ?
C6' H6'2 0.9800 . ?
C6' H6'3 0.9800 . ?
C7' H7'1 0.9800 . ?
C7' H7'2 0.9800 . ?
C7' H7'3 0.9800 . ?
C2" C3" 1.499(8) . ?
C2" H2"1 0.9900 . ?
C2" H2"2 0.9900 . ?
C3" C8" 1.329(9) . ?
C3" C4" 1.393(8) . ?
C4" C5" 1.394(11) . ?
C4" H4" 0.9500 . ?
C5" C6" 1.318(10) . ?
C5" H5" 0.9500 . ?
C6" C7" 1.347(10) . ?
C6" H6" 0.9500 . ?
C7" C8" 1.373(10) . ?
C7" H7" 0.9500 . ?
C8" H8" 0.9500 . ?

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
C1 O2 C10 112.6(4) . . ?
C1" O6 C2" 115.0(3) . . ?
C1' N1 C2 124.6(3) . . ?
C1' N1 H1N 116(3) . . ?
C2 N1 H1N 119(3) . . ?
C1" N2 C4' 123.6(3) . . ?
C1" N2 H2N 121(3) . . ?
C4' N2 H2N 116(3) . . ?
O1 C1 O2 127.0(5) . . ?
O1 C1 C2 123.3(4) . . ?
O2 C1 C2 109.7(4) . . ?
N1 C2 C3 112.6(3) . . ?
N1 C2 C1 108.2(3) . . ?
C3 C2 C1 107.4(3) . . ?
N1 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
C4 C3 C2 114.5(3) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C9 119.7(5) . . ?
C5 C4 C3 120.7(5) . . ?
C9 C4 C3 119.5(4) . . ?
C4 C5 C6 116.3(6) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 H5 121.9 . . ?
C7 C6 C5 119.3(5) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C6 122.1(7) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 120.7(7) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 121.8(5) . . ?
C8 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C1' N1 126.4(3) . . ?
O3 C1' C2' 121.7(3) . . ?
N1 C1' C2' 111.9(3) . . ?
O4 C2' C3' 123.1(3) . . ?
O4 C2' C1' 118.0(3) . . ?
C3' C2' C1' 118.9(3) . . ?
C2' C3' C4' 112.4(3) . . ?
C2' C3' H3'1 109.1 . . ?
C4' C3' H3'1 109.1 . . ?
C2' C3' H3'2 109.1 . . ?
C4' C3' H3'2 109.1 . . ?
H3'1 C3' H3'2 107.9 . . ?
N2 C4' C3' 108.5(3) . . ?
N2 C4' C5' 110.6(3) . . ?
C3' C4' C5' 114.1(3) . . ?
N2 C4' H4' 107.8 . . ?
C3' C4' H4' 107.8 . . ?
C5' C4' H4' 107.8 . . ?
C7' C5' C6' 109.5(4) . . ?
C7' C5' C4' 109.6(4) . . ?
C6' C5' C4' 111.7(3) . . ?
C7' C5' H5' 108.6 . . ?
C6' C5' H5' 108.6 . . ?
C4' C5' H5' 108.6 . . ?
C5' C6' H6'1 109.5 . . ?
C5' C6' H6'2 109.5 . . ?
H6'1 C6' H6'2 109.5 . . ?
C5' C6' H6'3 109.5 . . ?
H6'1 C6' H6'3 109.5 . . ?
H6'2 C6' H6'3 109.5 . . ?
C5' C7' H7'1 109.5 . . ?
C5' C7' H7'2 109.5 . . ?
H7'1 C7' H7'2 109.5 . . ?
C5' C7' H7'3 109.5 . . ?
H7'1 C7' H7'3 109.5 . . ?
H7'2 C7' H7'3 109.5 . . ?
O5 C1" N2 127.2(4) . . ?
O5 C1" O6 122.5(4) . . ?
N2 C1" O6 110.2(3) . . ?
O6 C2" C3" 108.6(4) . . ?
O6 C2" H2"1 110.0 . . ?
C3" C2" H2"1 110.0 . . ?
O6 C2" H2"2 110.0 . . ?
C3" C2" H2"2 110.0 . . ?
H2"1 C2" H2"2 108.4 . . ?
C8" C3" C4" 117.6(6) . . ?
C8" C3" C2" 122.1(5) . . ?
C4" C3" C2" 120.1(6) . . ?
C3" C4" C5" 120.2(7) . . ?
C3" C4" H4" 119.9 . . ?
C5" C4" H4" 119.9 . . ?
C6" C5" C4" 119.8(6) . . ?
C6" C5" H5" 120.1 . . ?
C4" C5" H5" 120.1 . . ?
C5" C6" C7" 119.8(7) . . ?
C5" C6" H6" 120.1 . . ?
C7" C6" H6" 120.1 . . ?
C6" C7" C8" 121.0(8) . . ?
C6" C7" H7" 119.5 . . ?
C8" C7" H7" 119.5 . . ?
C3" C8" C7" 120.9(6) . . ?
C3" C8" H8" 119.5 . . ?
C7" C8" H8" 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O2 C1 O1 -0.9(7) . . . . ?
C10 O2 C1 C2 178.1(4) . . . . ?
C1' N1 C2 C3 114.6(4) . . . . ?
C1' N1 C2 C1 -126.9(4) . . . . ?
O1 C1 C2 N1 -21.1(6) . . . . ?
O2 C1 C2 N1 159.8(4) . . . . ?
O1 C1 C2 C3 100.7(5) . . . . ?
O2 C1 C2 C3 -78.4(5) . . . . ?
N1 C2 C3 C4 -63.6(5) . . . . ?
C1 C2 C3 C4 177.4(4) . . . . ?
C2 C3 C4 C5 -89.8(5) . . . . ?
C2 C3 C4 C9 90.0(5) . . . . ?
C9 C4 C5 C6 0.3(7) . . . . ?
C3 C4 C5 C6 -179.9(4) . . . . ?
C4 C5 C6 C7 -0.6(8) . . . . ?
C5 C6 C7 C8 1.1(9) . . . . ?
C6 C7 C8 C9 -1.3(10) . . . . ?
C7 C8 C9 C4 1.0(9) . . . . ?
C5 C4 C9 C8 -0.5(8) . . . . ?
C3 C4 C9 C8 179.7(4) . . . . ?
C2 N1 C1' O3 -9.5(6) . . . . ?
C2 N1 C1' C2' 168.0(4) . . . . ?
O3 C1' C2' O4 171.0(4) . . . . ?
N1 C1' C2' O4 -6.7(5) . . . . ?
O3 C1' C2' C3' -8.6(6) . . . . ?
N1 C1' C2' C3' 173.8(3) . . . . ?
O4 C2' C3' C4' -11.5(6) . . . . ?
C1' C2' C3' C4' 168.0(3) . . . . ?
C1" N2 C4' C3' 115.3(4) . . . . ?
C1" N2 C4' C5' -118.9(4) . . . . ?
C2' C3' C4' N2 -67.3(4) . . . . ?
C2' C3' C4' C5' 169.0(3) . . . . ?
N2 C4' C5' C7' 57.0(4) . . . . ?
C3' C4' C5' C7' 179.6(4) . . . . ?
N2 C4' C5' C6' 178.6(4) . . . . ?
C3' C4' C5' C6' -58.8(5) . . . . ?
C4' N2 C1" O5 4.3(6) . . . . ?
C4' N2 C1" O6 -176.7(3) . . . . ?
C2" O6 C1" O5 -7.5(6) . . . . ?
C2" O6 C1" N2 173.5(4) . . . . ?
C1" O6 C2" C3" 172.7(4) . . . . ?
O6 C2" C3" C8" 56.3(8) . . . . ?
O6 C2" C3" C4" -119.3(6) . . . . ?
C8" C3" C4" C5" 6.6(12) . . . . ?
C2" C3" C4" C5" -177.6(7) . . . . ?
C3" C4" C5" C6" 0.0(13) . . . . ?
C4" C5" C6" C7" -7.0(15) . . . . ?
C5" C6" C7" C8" 7.5(17) . . . . ?
C4" C3" C8" C7" -6.2(13) . . . . ?
C2" C3" C8" C7" 178.0(8) . . . . ?
C6" C7" C8" C3" -0.6(17) . . . . ?

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
N1 H1N O3 0.88(2) 2.26(3) 3.070(4) 154(4) 1_545
N2 H2N O5 0.89(2) 2.02(3) 2.877(4) 160(4) 1_565

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_36
_database_code_depnum_ccdc_archive 'CCDC 1547068'
_audit_update_record             
;
2017-04-30 deposited with the CCDC.
2017-08-22 downloaded from the CCDC.
;


# start Validation Reply Form ================================================

_vrf_PLAT340_36                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0101 Ang. 
RESPONSE: This might be caused by The low quality of the used crystal.
However it was without doubt the best crystal selected after a rigorous
analysis of the crystals obtained.
;

_vrf_PLAT029_36                  
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.970 Note   
RESPONSE: The crystal selected for data collection was a very thin colourless 
plate which diffracted very weakly at high angles and, consequently, a number 
of reflections are missing, in particular in the 0.90-0.84 A resolution range. 
;

# end Validation Reply Form ==================================================



_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N2 O5, C H2 Cl2'
_chemical_formula_sum            'C23 H26 Cl2 N2 O5'
_chemical_formula_weight         481.36

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'
Cl Cl 0.1484 0.1585 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.9737(8)
_cell_length_b                   4.9511(4)
_cell_length_c                   22.0555(19)
_cell_angle_alpha                90
_cell_angle_beta                 102.768(3)
_cell_angle_gamma                90
_cell_volume                     1168.69(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3322
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      21.50

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.315
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9398
_exptl_absorpt_correction_T_max  0.9692
_exptl_absorpt_process_details   
;
   program SADABS, Bruker (2001).
;
_diffrn_ambient_temperature      193(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  
;
 Bruker-Nonius X8kappa APEX II CCD area detector
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_diffrn_detector_area_resol_mean 8.26
_diffrn_reflns_number            15430
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.893
_diffrn_reflns_theta_max         25.229
_diffrn_reflns_theta_full        25.229
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_point_group_measured_fraction_full 0.812
_reflns_number_total             3422
_reflns_number_gt                2692
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.487
_reflns_Friedel_fraction_max     0.609
_reflns_Friedel_fraction_full    0.609

_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       'APEX2 Software Suite (Bruker, 2007)'
_computing_cell_refinement       'APEX2 Software Suite (Bruker, 2007)'
_computing_data_reduction        'APEX2 Software Suite (Bruker, 2007)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL and publCIF (Westrip, 2010)'
_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)+(0.2000P)²] 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       .

_chemical_absolute_configuration rm
_refine_ls_number_reflns         3422
_refine_ls_number_parameters     297
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0842
_refine_ls_wR_factor_ref         0.2513
_refine_ls_wR_factor_gt          0.2366
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.051
_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
O1 O 0.9568(7) 0.284(2) 0.4529(3) 0.122(3) Uani 1 1 d . . . . .
O2 O 0.8579(5) 0.5949(18) 0.3882(3) 0.098(2) Uani 1 1 d . . . . .
O3 O 0.7238(5) 0.7146(13) 0.4691(2) 0.0766(16) Uani 1 1 d . . . . .
O4 O 0.7828(5) 0.7928(8) 0.6779(2) 0.0618(13) Uani 1 1 d . . . . .
O5 O 0.9927(4) 0.0535(8) 0.8084(2) 0.0563(12) Uani 1 1 d . . . . .
N1 N 0.7563(5) 0.3635(9) 0.6444(2) 0.0428(12) Uani 1 1 d D . . . .
H1N H 0.747(6) 0.189(6) 0.652(3) 0.051 Uiso 1 1 d D U . . .
N2 N 0.9533(4) 0.4864(9) 0.7806(2) 0.0372(10) Uani 1 1 d D . . . .
H2N H 0.983(5) 0.656(7) 0.777(3) 0.045 Uiso 1 1 d D U . . .
C1 C 0.8802(7) 0.455(2) 0.4387(4) 0.073(2) Uani 1 1 d . . . . .
C2 C 0.7985(6) 0.5351(17) 0.4835(3) 0.0601(17) Uani 1 1 d . . . . .
C3 C 0.8175(6) 0.3857(16) 0.5439(3) 0.0579(17) Uani 1 1 d . . . . .
H3A H 0.898228 0.441547 0.570761 0.069 Uiso 1 1 calc R U . . .
H3B H 0.822378 0.189817 0.535771 0.069 Uiso 1 1 calc R U . . .
C4 C 0.7144(5) 0.4348(13) 0.5783(3) 0.0488(14) Uani 1 1 d . . . . .
H4 H 0.692096 0.630951 0.575203 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5988(6) 0.2711(17) 0.5488(4) 0.0674(19) Uani 1 1 d . . . . .
H5A H 0.532683 0.304050 0.571336 0.101 Uiso 1 1 calc R U . . .
H5B H 0.619802 0.078443 0.550702 0.101 Uiso 1 1 calc R U . . .
H5C H 0.569612 0.325550 0.505251 0.101 Uiso 1 1 calc R U . . .
C6 C 0.9252(9) 0.515(4) 0.3409(4) 0.127(5) Uani 1 1 d . . . . .
H6A H 0.900123 0.331509 0.326469 0.191 Uiso 1 1 calc R U . . .
H6B H 1.015298 0.518337 0.358689 0.191 Uiso 1 1 calc R U . . .
H6C H 0.905344 0.640301 0.305750 0.191 Uiso 1 1 calc R U . . .
C1' C 0.7853(5) 0.5490(12) 0.6883(3) 0.0410(13) Uani 1 1 d . . . . .
C2' C 0.8211(4) 0.4415(10) 0.7551(2) 0.0372(12) Uani 1 1 d . . . . .
H2' H 0.804067 0.243038 0.754608 0.045 Uiso 1 1 calc R U . . .
C3' C 0.7416(5) 0.5817(12) 0.7950(3) 0.0467(14) Uani 1 1 d . . . . .
H3'1 H 0.762941 0.776216 0.798450 0.056 Uiso 1 1 calc R U . . .
H3'2 H 0.652188 0.565684 0.774225 0.056 Uiso 1 1 calc R U . . .
C4' C 0.7615(5) 0.4628(12) 0.8588(3) 0.0450(14) Uani 1 1 d . . . . .
C5' C 0.6877(6) 0.2503(13) 0.8718(3) 0.0502(14) Uani 1 1 d . . . . .
H5' H 0.622883 0.180765 0.839732 0.060 Uiso 1 1 calc R U . . .
C6' C 0.7079(6) 0.1371(14) 0.9319(3) 0.0551(16) Uani 1 1 d . . . . .
H6' H 0.656964 -0.007565 0.940148 0.066 Uiso 1 1 calc R U . . .
C7' C 0.8000(7) 0.2354(16) 0.9778(3) 0.0608(17) Uani 1 1 d . . . . .
H7' H 0.813788 0.159293 1.018267 0.073 Uiso 1 1 calc R U . . .
C8' C 0.8738(6) 0.4450(14) 0.9661(3) 0.0587(16) Uani 1 1 d . . . . .
H8' H 0.938761 0.512393 0.998385 0.070 Uiso 1 1 calc R U . . .
C9' C 0.8534(6) 0.5583(13) 0.9071(3) 0.0496(14) Uani 1 1 d . . . . .
H9' H 0.903966 0.705294 0.899893 0.059 Uiso 1 1 calc R U . . .
C1" C 1.0279(5) 0.2853(11) 0.8085(2) 0.0384(12) Uani 1 1 d . . . . .
C2" C 1.1586(5) 0.3630(12) 0.8401(3) 0.0453(14) Uani 1 1 d . . . . .
C3" C 1.2164(7) 0.2058(16) 0.8918(3) 0.0643(18) Uani 1 1 d . . . . .
H3" H 1.172414 0.060520 0.905214 0.077 Uiso 1 1 calc R U . . .
C4" C 1.3364(10) 0.263(2) 0.9225(4) 0.087(3) Uani 1 1 d . . . . .
H4" H 1.374255 0.157900 0.957639 0.105 Uiso 1 1 calc R U . . .
C5" C 1.4009(8) 0.463(2) 0.9043(5) 0.085(3) Uani 1 1 d . . . . .
H5" H 1.484798 0.494690 0.925684 0.102 Uiso 1 1 calc R U . . .
C6" C 1.3479(7) 0.621(2) 0.8555(5) 0.090(3) Uani 1 1 d . . . . .
H6" H 1.394077 0.766436 0.843665 0.108 Uiso 1 1 calc R U . . .
C7" C 1.2224(6) 0.5710(17) 0.8214(4) 0.066(2) Uani 1 1 d . . . . .
H7" H 1.185164 0.679838 0.786753 0.079 Uiso 1 1 calc R U . . .
Cl1 Cl 0.4037(5) 0.1002(16) 0.73898(19) 0.223(3) Uani 1 1 d D U . . .
Cl2 Cl 0.4003(7) -0.3100(13) 0.6483(4) 0.245(3) Uani 1 1 d D U . . .
C7 C 0.4531(13) 0.005(2) 0.6740(5) 0.155(5) Uani 1 1 d D U . . .
H7A H 0.545561 0.005934 0.683201 0.186 Uiso 1 1 calc R U . . .
H7B H 0.423161 0.138334 0.640520 0.186 Uiso 1 1 calc R 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
O1 C1 1.185(11) . ?
O2 C1 1.289(11) . ?
O2 C6 1.461(10) . ?
O3 C2 1.203(9) . ?
O4 C1' 1.227(7) . ?
O5 C1" 1.211(7) . ?
N1 C1' 1.321(8) . ?
N1 C4 1.471(7) . ?
N1 H1N 0.89(3) . ?
N2 C1" 1.348(7) . ?
N2 C2' 1.452(7) . ?
N2 H2N 0.91(3) . ?
C1 C2 1.526(10) . ?
C2 C3 1.498(10) . ?
C3 C4 1.515(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.525(10) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C1' C2' 1.535(8) . ?
C2' C3' 1.535(8) . ?
C2' H2' 1.0000 . ?
C3' C4' 1.495(8) . ?
C3' H3'1 0.9900 . ?
C3' H3'2 0.9900 . ?
C4' C9' 1.379(9) . ?
C4' C5' 1.396(9) . ?
C5' C6' 1.411(9) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.353(10) . ?
C6' H6' 0.9500 . ?
C7' C8' 1.375(10) . ?
C7' H7' 0.9500 . ?
C8' C9' 1.388(9) . ?
C8' H8' 0.9500 . ?
C9' H9' 0.9500 . ?
C1" C2" 1.500(9) . ?
C2" C7" 1.360(10) . ?
C2" C3" 1.409(9) . ?
C3" C4" 1.371(13) . ?
C3" H3" 0.9500 . ?
C4" C5" 1.328(15) . ?
C4" H4" 0.9500 . ?
C5" C6" 1.355(14) . ?
C5" H5" 0.9500 . ?
C6" C7" 1.437(12) . ?
C6" H6" 0.9500 . ?
C7" H7" 0.9500 . ?
Cl1 C7 1.708(6) . ?
Cl2 C7 1.716(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
C1 O2 C6 116.2(10) . . ?
C1' N1 C4 122.0(5) . . ?
C1' N1 H1N 124(4) . . ?
C4 N1 H1N 114(4) . . ?
C1" N2 C2' 121.2(4) . . ?
C1" N2 H2N 122(4) . . ?
C2' N2 H2N 117(4) . . ?
O1 C1 O2 126.9(8) . . ?
O1 C1 C2 120.0(8) . . ?
O2 C1 C2 113.1(7) . . ?
O3 C2 C3 123.5(6) . . ?
O3 C2 C1 119.0(7) . . ?
C3 C2 C1 117.4(7) . . ?
C2 C3 C4 113.2(6) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 C3 110.7(5) . . ?
N1 C4 C5 110.2(5) . . ?
C3 C4 C5 110.1(6) . . ?
N1 C4 H4 108.6 . . ?
C3 C4 H4 108.6 . . ?
C5 C4 H4 108.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
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 . . ?
O4 C1' N1 123.8(6) . . ?
O4 C1' C2' 120.7(5) . . ?
N1 C1' C2' 115.6(5) . . ?
N2 C2' C3' 110.7(4) . . ?
N2 C2' C1' 109.9(4) . . ?
C3' C2' C1' 109.7(4) . . ?
N2 C2' H2' 108.8 . . ?
C3' C2' H2' 108.8 . . ?
C1' C2' H2' 108.8 . . ?
C4' C3' C2' 112.2(4) . . ?
C4' C3' H3'1 109.2 . . ?
C2' C3' H3'1 109.2 . . ?
C4' C3' H3'2 109.2 . . ?
C2' C3' H3'2 109.2 . . ?
H3'1 C3' H3'2 107.9 . . ?
C9' C4' C5' 117.2(6) . . ?
C9' C4' C3' 121.5(5) . . ?
C5' C4' C3' 121.3(6) . . ?
C4' C5' C6' 121.0(6) . . ?
C4' C5' H5' 119.5 . . ?
C6' C5' H5' 119.5 . . ?
C7' C6' C5' 119.7(6) . . ?
C7' C6' H6' 120.1 . . ?
C5' C6' H6' 120.1 . . ?
C6' C7' C8' 120.3(6) . . ?
C6' C7' H7' 119.8 . . ?
C8' C7' H7' 119.8 . . ?
C7' C8' C9' 120.0(7) . . ?
C7' C8' H8' 120.0 . . ?
C9' C8' H8' 120.0 . . ?
C4' C9' C8' 121.7(6) . . ?
C4' C9' H9' 119.2 . . ?
C8' C9' H9' 119.2 . . ?
O5 C1" N2 122.5(5) . . ?
O5 C1" C2" 121.0(5) . . ?
N2 C1" C2" 116.4(5) . . ?
C7" C2" C3" 119.6(6) . . ?
C7" C2" C1" 123.8(6) . . ?
C3" C2" C1" 116.6(6) . . ?
C4" C3" C2" 119.8(8) . . ?
C4" C3" H3" 120.1 . . ?
C2" C3" H3" 120.1 . . ?
C5" C4" C3" 121.5(8) . . ?
C5" C4" H4" 119.2 . . ?
C3" C4" H4" 119.2 . . ?
C4" C5" C6" 120.4(8) . . ?
C4" C5" H5" 119.8 . . ?
C6" C5" H5" 119.8 . . ?
C5" C6" C7" 120.7(9) . . ?
C5" C6" H6" 119.7 . . ?
C7" C6" H6" 119.7 . . ?
C2" C7" C6" 118.0(8) . . ?
C2" C7" H7" 121.0 . . ?
C6" C7" H7" 121.0 . . ?
Cl1 C7 Cl2 112.4(5) . . ?
Cl1 C7 H7A 109.1 . . ?
Cl2 C7 H7A 109.1 . . ?
Cl1 C7 H7B 109.1 . . ?
Cl2 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O2 C1 O1 6.8(15) . . . . ?
C6 O2 C1 C2 -175.1(8) . . . . ?
O1 C1 C2 O3 177.9(9) . . . . ?
O2 C1 C2 O3 -0.4(11) . . . . ?
O1 C1 C2 C3 -1.4(12) . . . . ?
O2 C1 C2 C3 -179.6(7) . . . . ?
O3 C2 C3 C4 13.7(11) . . . . ?
C1 C2 C3 C4 -167.2(6) . . . . ?
C1' N1 C4 C3 105.0(6) . . . . ?
C1' N1 C4 C5 -133.1(6) . . . . ?
C2 C3 C4 N1 -160.9(6) . . . . ?
C2 C3 C4 C5 77.1(8) . . . . ?
C4 N1 C1' O4 -1.8(9) . . . . ?
C4 N1 C1' C2' 177.0(5) . . . . ?
C1" N2 C2' C3' 108.5(5) . . . . ?
C1" N2 C2' C1' -130.1(5) . . . . ?
O4 C1' C2' N2 -70.3(7) . . . . ?
N1 C1' C2' N2 110.8(5) . . . . ?
O4 C1' C2' C3' 51.7(7) . . . . ?
N1 C1' C2' C3' -127.2(5) . . . . ?
N2 C2' C3' C4' -65.1(6) . . . . ?
C1' C2' C3' C4' 173.4(5) . . . . ?
C2' C3' C4' C9' 89.3(7) . . . . ?
C2' C3' C4' C5' -90.7(6) . . . . ?
C9' C4' C5' C6' -0.7(8) . . . . ?
C3' C4' C5' C6' 179.3(5) . . . . ?
C4' C5' C6' C7' 0.0(9) . . . . ?
C5' C6' C7' C8' 0.1(10) . . . . ?
C6' C7' C8' C9' 0.5(10) . . . . ?
C5' C4' C9' C8' 1.3(8) . . . . ?
C3' C4' C9' C8' -178.7(6) . . . . ?
C7' C8' C9' C4' -1.2(10) . . . . ?
C2' N2 C1" O5 7.5(8) . . . . ?
C2' N2 C1" C2" -172.6(4) . . . . ?
O5 C1" C2" C7" 149.8(6) . . . . ?
N2 C1" C2" C7" -30.1(8) . . . . ?
O5 C1" C2" C3" -29.6(8) . . . . ?
N2 C1" C2" C3" 150.5(5) . . . . ?
C7" C2" C3" C4" -0.1(10) . . . . ?
C1" C2" C3" C4" 179.3(6) . . . . ?
C2" C3" C4" C5" -0.9(12) . . . . ?
C3" C4" C5" C6" 1.9(13) . . . . ?
C4" C5" C6" C7" -1.9(13) . . . . ?
C3" C2" C7" C6" 0.2(10) . . . . ?
C1" C2" C7" C6" -179.2(6) . . . . ?
C5" C6" C7" C2" 0.8(12) . . . . ?

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
N1 H1N O4 0.89(3) 2.05(3) 2.919(6) 163(6) 1_545
N2 H2N O5 0.91(3) 2.09(4) 2.886(6) 146(5) 1_565

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.092

