# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_chav137b
_database_code_depnum_ccdc_archive 'CCDC 1822383'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2019-01-28 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         'C8 H4 N16 O6, 2(C3 H7 N O)'
_chemical_formula_sum            'C14 H18 N18 O8'
_chemical_formula_weight         566.46

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.8361(4)
_cell_length_b                   11.0288(4)
_cell_length_c                   17.3634(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.3283(10)
_cell_angle_gamma                90
_cell_volume                     2264.71(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5789
_cell_measurement_theta_min      2.348
_cell_measurement_theta_max      29.965

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6987
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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 SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13128
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.525
_diffrn_reflns_theta_max         30.001
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3186
_reflns_number_gt                2682
_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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0495P)²+1.5726P] 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         3186
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
N1 N 0.51583(8) 0.67870(9) 0.44340(6) 0.0221(2) Uani 1 1 d . . . . .
N2 N 0.56331(8) 0.56863(8) 0.43829(5) 0.0206(2) Uani 1 1 d . . . . .
O3 O 0.52144(8) 0.49347(8) 0.38978(5) 0.0287(2) Uani 1 1 d . . . . .
C4 C 0.65350(10) 0.53300(10) 0.48411(6) 0.0203(2) Uani 1 1 d . . . . .
N5 N 0.70199(9) 0.42577(9) 0.47714(6) 0.0236(2) Uani 1 1 d . . . . .
H5A H 0.6761 0.3744 0.4419 0.028 Uiso 1 1 calc R U . . .
H5B H 0.7601 0.4058 0.5078 0.028 Uiso 1 1 calc R U . . .
N6 N 0.69272(8) 0.61366(8) 0.53891(5) 0.0202(2) Uani 1 1 d . . . . .
O7 O 0.77408(8) 0.58139(8) 0.58307(5) 0.0282(2) Uani 1 1 d . . . . .
N8 N 0.65054(8) 0.72501(9) 0.54562(6) 0.0213(2) Uani 1 1 d . . . . .
C9 C 0.56477(9) 0.74960(10) 0.49650(6) 0.0200(2) Uani 1 1 d . . . . .
N10 N 0.52117(8) 0.86791(9) 0.50086(5) 0.0212(2) Uani 1 1 d . . . . .
C11 C 0.54141(9) 0.94241(10) 0.56521(6) 0.0210(2) Uani 1 1 d . . . . .
N12 N 0.57752(10) 0.90938(10) 0.63354(6) 0.0300(2) Uani 1 1 d . . . . .
O13 O 0.58086(9) 1.01594(9) 0.67621(5) 0.0340(2) Uani 1 1 d . . . . .
N14 N 0.54568(10) 1.11529(10) 0.63211(6) 0.0290(2) Uani 1 1 d . . . . .
C15 C 0.52100(9) 1.07022(10) 0.56433(6) 0.0207(2) Uani 1 1 d . . . . .
C16 C 0.67155(11) 0.29692(13) 0.77890(7) 0.0303(3) Uani 1 1 d . . . . .
H16A H 0.6230 0.3634 0.7599 0.046 Uiso 1 1 calc R U . . .
H16B H 0.7107 0.3213 0.8273 0.046 Uiso 1 1 calc R U . . .
H16C H 0.6251 0.2251 0.7879 0.046 Uiso 1 1 calc R U . . .
N17 N 0.75453(8) 0.26862(9) 0.72185(5) 0.0227(2) Uani 1 1 d . . . . .
C18 C 0.83526(13) 0.17308(13) 0.74082(8) 0.0367(3) Uani 1 1 d . . . . .
H18A H 0.7957 0.0952 0.7429 0.055 Uiso 1 1 calc R U . . .
H18B H 0.8726 0.1900 0.7911 0.055 Uiso 1 1 calc R U . . .
H18C H 0.8920 0.1696 0.7013 0.055 Uiso 1 1 calc R U . . .
C19 C 0.75003(10) 0.32179(10) 0.65363(7) 0.0230(2) Uani 1 1 d . . . . .
H19 H 0.6943 0.3829 0.6452 0.028 Uiso 1 1 calc R U . . .
O20 O 0.81227(8) 0.29899(8) 0.59931(5) 0.0273(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
N1 C9 1.3243(15) . ?
N1 N2 1.3422(13) . ?
N2 O3 1.2682(13) . ?
N2 C4 1.3631(15) . ?
C4 N5 1.3222(14) . ?
C4 N6 1.3697(15) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N6 O7 1.2577(13) . ?
N6 N8 1.3326(13) . ?
N8 C9 1.3271(15) . ?
C9 N10 1.4063(14) . ?
N10 C15 1.3965(14) 5_676 ?
N10 C11 1.3997(14) . ?
C11 N12 1.2969(15) . ?
C11 C15 1.4301(15) . ?
N12 O13 1.3891(13) . ?
O13 N14 1.3908(14) . ?
N14 C15 1.2998(15) . ?
C15 N10 1.3965(14) 5_676 ?
C16 N17 1.4569(15) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N17 C19 1.3207(15) . ?
N17 C18 1.4513(16) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O20 1.2458(14) . ?
C19 H19 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
C9 N1 N2 114.05(10) . . ?
O3 N2 N1 118.80(10) . . ?
O3 N2 C4 118.35(9) . . ?
N1 N2 C4 122.84(9) . . ?
N5 C4 N2 122.48(10) . . ?
N5 C4 N6 120.55(11) . . ?
N2 C4 N6 116.97(10) . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O7 N6 N8 119.19(9) . . ?
O7 N6 C4 117.99(9) . . ?
N8 N6 C4 122.79(10) . . ?
C9 N8 N6 114.31(9) . . ?
N1 C9 N8 128.93(10) . . ?
N1 C9 N10 115.73(10) . . ?
N8 C9 N10 115.33(10) . . ?
C15 N10 C11 113.84(9) 5_676 . ?
C15 N10 C9 121.98(9) 5_676 . ?
C11 N10 C9 122.44(9) . . ?
N12 C11 N10 127.21(11) . . ?
N12 C11 C15 109.63(10) . . ?
N10 C11 C15 123.14(10) . . ?
C11 N12 O13 104.56(10) . . ?
N12 O13 N14 111.81(9) . . ?
C15 N14 O13 104.39(9) . . ?
N14 C15 N10 127.36(10) . 5_676 ?
N14 C15 C11 109.61(10) . . ?
N10 C15 C11 123.02(10) 5_676 . ?
N17 C16 H16A 109.5 . . ?
N17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 N17 C18 121.88(10) . . ?
C19 N17 C16 120.73(10) . . ?
C18 N17 C16 117.19(10) . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O20 C19 N17 125.86(11) . . ?
O20 C19 H19 117.1 . . ?
N17 C19 H19 117.1 . . ?

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
C9 N1 N2 O3 179.05(9) . . . . ?
C9 N1 N2 C4 0.38(14) . . . . ?
O3 N2 C4 N5 3.44(15) . . . . ?
N1 N2 C4 N5 -177.88(10) . . . . ?
O3 N2 C4 N6 -176.35(9) . . . . ?
N1 N2 C4 N6 2.33(15) . . . . ?
N5 C4 N6 O7 -1.54(15) . . . . ?
N2 C4 N6 O7 178.25(9) . . . . ?
N5 C4 N6 N8 176.46(10) . . . . ?
N2 C4 N6 N8 -3.75(15) . . . . ?
O7 N6 N8 C9 -179.78(10) . . . . ?
C4 N6 N8 C9 2.24(15) . . . . ?
N2 N1 C9 N8 -2.16(17) . . . . ?
N2 N1 C9 N10 176.79(9) . . . . ?
N6 N8 C9 N1 0.89(17) . . . . ?
N6 N8 C9 N10 -178.07(9) . . . . ?
N1 C9 N10 C15 -33.44(15) . . . 5_676 ?
N8 C9 N10 C15 145.67(11) . . . 5_676 ?
N1 C9 N10 C11 162.56(10) . . . . ?
N8 C9 N10 C11 -18.34(15) . . . . ?
C15 N10 C11 N12 178.09(12) 5_676 . . . ?
C9 N10 C11 N12 -16.71(18) . . . . ?
C15 N10 C11 C15 -0.10(17) 5_676 . . . ?
C9 N10 C11 C15 165.09(10) . . . . ?
N10 C11 N12 O13 -178.74(11) . . . . ?
C15 C11 N12 O13 -0.34(13) . . . . ?
C11 N12 O13 N14 0.04(14) . . . . ?
N12 O13 N14 C15 0.29(14) . . . . ?
O13 N14 C15 N10 178.37(11) . . . 5_676 ?
O13 N14 C15 C11 -0.49(13) . . . . ?
N12 C11 C15 N14 0.55(14) . . . . ?
N10 C11 C15 N14 179.03(11) . . . . ?
N12 C11 C15 N10 -178.36(11) . . . 5_676 ?
N10 C11 C15 N10 0.11(18) . . . 5_676 ?
C18 N17 C19 O20 -0.74(19) . . . . ?
C16 N17 C19 O20 -175.44(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
N5 H5A O20 0.88 2.05 2.8138(13) 144.9 7_656
N5 H5B O20 0.88 2.05 2.8167(14) 144.5 .
C19 H19 O7 0.95 2.63 3.1317(15) 113.2 .
C18 H18C O3 0.98 2.63 3.4214(16) 138.0 7_656

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.291
_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_chav174
_database_code_depnum_ccdc_archive 'CCDC 1822384'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2019-01-28 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         ?
_chemical_formula_sum            'C10 H9 N11 O6'
_chemical_formula_weight         379.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.5158(3)
_cell_length_b                   9.6613(5)
_cell_length_c                   27.7811(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.635(2)
_cell_angle_gamma                90
_cell_volume                     1477.47(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3961
_cell_measurement_theta_min      3.188
_cell_measurement_theta_max      74.743

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    1.254
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_process_details   'TWINABS v2012/1 (Bruker, 2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   '1uS microfocus'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3431
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.188
_diffrn_reflns_theta_max         74.829
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             3431
_reflns_number_gt                3101
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
The crystal was a two component non-merohedral twin (BASF 0.3720).  
Initial refinement was performed on the main component and final 
refinement was done on both components with HKLF 5 file.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0955P)²+0.7183P] 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       0.0101(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3431
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1714
_refine_ls_wR_factor_gt          0.1610
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
N1 N 0.6754(5) 0.2406(3) 0.61305(10) 0.0403(6) Uani 1 1 d . . . . .
N2 N 0.8158(5) 0.2767(3) 0.57815(10) 0.0386(6) Uani 1 1 d . . . . .
O3 O 0.7746(6) 0.2262(3) 0.53665(9) 0.0592(8) Uani 1 1 d . . . . .
C4 C 1.0090(6) 0.3653(3) 0.58475(12) 0.0354(7) Uani 1 1 d . . . . .
N5 N 1.1485(6) 0.3943(3) 0.54997(10) 0.0440(7) Uani 1 1 d . . . . .
H5A H 1.2696 0.4495 0.5551 0.053 Uiso 1 1 calc R U . . .
H5B H 1.1195 0.3581 0.5219 0.053 Uiso 1 1 calc R U . . .
N6 N 1.0481(5) 0.4197(3) 0.62917(10) 0.0354(6) Uani 1 1 d . . . . .
O7 O 1.2285(5) 0.5003(3) 0.63741(9) 0.0512(7) Uani 1 1 d . . . . .
N8 N 0.9091(5) 0.3903(3) 0.66561(10) 0.0392(6) Uani 1 1 d . . . . .
C9 C 0.7354(5) 0.3005(3) 0.65535(11) 0.0332(6) Uani 1 1 d . . . . .
N10 N 0.6021(5) 0.2596(3) 0.69432(9) 0.0358(6) Uani 1 1 d . . . . .
C11 C 0.6882(6) 0.2840(3) 0.74268(12) 0.0367(7) Uani 1 1 d . . . . .
N12 N 0.8740(6) 0.3542(4) 0.75814(11) 0.0578(9) Uani 1 1 d . . . . .
O13 O 0.8796(6) 0.3392(4) 0.80828(10) 0.0677(9) Uani 1 1 d . . . . .
N14 N 0.6892(6) 0.2574(4) 0.82216(11) 0.0554(9) Uani 1 1 d . . . . .
C15 C 0.5719(6) 0.2233(3) 0.78217(12) 0.0383(7) Uani 1 1 d . . . . .
N16 N 0.3669(6) 0.1457(3) 0.77712(11) 0.0458(7) Uani 1 1 d . . . . .
H16 H 0.2938 0.1155 0.8015 0.055 Uiso 1 1 calc R U . . .
C17 C 0.2851(6) 0.1192(3) 0.73073(12) 0.0396(7) Uani 1 1 d . . . . .
N18 N 0.0972(6) 0.0463(4) 0.71675(12) 0.0519(8) Uani 1 1 d . . . . .
O19 O 0.0894(5) 0.0542(3) 0.66608(10) 0.0517(7) Uani 1 1 d . . . . .
N20 N 0.2755(5) 0.1359(3) 0.65063(11) 0.0432(7) Uani 1 1 d . . . . .
C21 C 0.3964(5) 0.1748(3) 0.68962(11) 0.0335(6) Uani 1 1 d . . . . .
O23 O 0.5984(5) 0.5472(3) 0.55662(12) 0.0584(8) Uani 1 1 d . . . . .
C24 C 0.6051(6) 0.6719(4) 0.56067(12) 0.0385(7) Uani 1 1 d . . . . .
O25 O 0.8007(4) 0.7408(3) 0.54871(10) 0.0479(6) Uani 1 1 d . . . . .
C26 C 0.7709(8) 0.8877(4) 0.55822(18) 0.0609(11) Uani 1 1 d . . . . .
H26A H 0.8194 0.9424 0.5312 0.073 Uiso 1 1 calc R U . . .
H26B H 0.8687 0.9150 0.5869 0.073 Uiso 1 1 calc R U . . .
C27 C 0.5053(10) 0.9078(5) 0.56543(19) 0.0666(12) Uani 1 1 d . . . . .
H27A H 0.4826 0.9718 0.5917 0.080 Uiso 1 1 calc R U . . .
H27B H 0.4207 0.9432 0.5363 0.080 Uiso 1 1 calc R U . . .
C28 C 0.4162(6) 0.7676(4) 0.57716(13) 0.0448(8) Uani 1 1 d . . . . .
H28A H 0.2601 0.7494 0.5603 0.054 Uiso 1 1 calc R U . . .
H28B H 0.3998 0.7581 0.6116 0.054 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
N1 N2 1.325(4) . ?
N1 C9 1.332(4) . ?
N2 O3 1.260(4) . ?
N2 C4 1.370(4) . ?
C4 N5 1.303(4) . ?
C4 N6 1.346(4) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 O7 1.273(4) . ?
N6 N8 1.338(4) . ?
N8 C9 1.310(4) . ?
C9 N10 1.403(4) . ?
N10 C21 1.399(4) . ?
N10 C11 1.416(4) . ?
C11 N12 1.280(5) . ?
C11 C15 1.431(5) . ?
N12 O13 1.399(4) . ?
O13 N14 1.388(5) . ?
N14 C15 1.292(5) . ?
C15 N16 1.356(5) . ?
N16 C17 1.363(5) . ?
N16 H16 0.8600 . ?
C17 N18 1.293(5) . ?
C17 C21 1.435(4) . ?
N18 O19 1.408(4) . ?
O19 N20 1.385(4) . ?
N20 C21 1.292(4) . ?
O23 C24 1.210(5) . ?
C24 O25 1.328(4) . ?
C24 C28 1.487(5) . ?
O25 C26 1.454(5) . ?
C26 C27 1.504(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.484(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?

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
N2 N1 C9 114.0(3) . . ?
O3 N2 N1 119.2(3) . . ?
O3 N2 C4 117.3(3) . . ?
N1 N2 C4 123.5(3) . . ?
N5 C4 N6 121.9(3) . . ?
N5 C4 N2 121.7(3) . . ?
N6 C4 N2 116.4(3) . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O7 N6 N8 118.2(3) . . ?
O7 N6 C4 118.8(3) . . ?
N8 N6 C4 123.0(3) . . ?
C9 N8 N6 114.9(3) . . ?
N8 C9 N1 128.1(3) . . ?
N8 C9 N10 115.5(3) . . ?
N1 C9 N10 116.4(3) . . ?
C21 N10 C9 123.7(3) . . ?
C21 N10 C11 114.0(3) . . ?
C9 N10 C11 121.6(3) . . ?
N12 C11 N10 128.3(3) . . ?
N12 C11 C15 110.4(3) . . ?
N10 C11 C15 121.3(3) . . ?
C11 N12 O13 104.2(3) . . ?
N14 O13 N12 111.5(3) . . ?
C15 N14 O13 104.6(3) . . ?
N14 C15 N16 126.8(3) . . ?
N14 C15 C11 109.3(3) . . ?
N16 C15 C11 123.9(3) . . ?
C15 N16 C17 115.2(3) . . ?
C15 N16 H16 122.4 . . ?
C17 N16 H16 122.4 . . ?
N18 C17 N16 126.7(3) . . ?
N18 C17 C21 109.9(3) . . ?
N16 C17 C21 123.3(3) . . ?
C17 N18 O19 104.1(3) . . ?
N20 O19 N18 111.4(3) . . ?
C21 N20 O19 105.0(3) . . ?
N20 C21 N10 128.4(3) . . ?
N20 C21 C17 109.5(3) . . ?
N10 C21 C17 122.0(3) . . ?
O23 C24 O25 119.8(3) . . ?
O23 C24 C28 129.0(3) . . ?
O25 C24 C28 111.2(3) . . ?
C24 O25 C26 109.9(3) . . ?
O25 C26 C27 105.8(3) . . ?
O25 C26 H26A 110.6 . . ?
C27 C26 H26A 110.6 . . ?
O25 C26 H26B 110.6 . . ?
C27 C26 H26B 110.6 . . ?
H26A C26 H26B 108.7 . . ?
C28 C27 C26 104.5(4) . . ?
C28 C27 H27A 110.9 . . ?
C26 C27 H27A 110.9 . . ?
C28 C27 H27B 110.9 . . ?
C26 C27 H27B 110.9 . . ?
H27A C27 H27B 108.9 . . ?
C27 C28 C24 104.6(3) . . ?
C27 C28 H28A 110.8 . . ?
C24 C28 H28A 110.8 . . ?
C27 C28 H28B 110.8 . . ?
C24 C28 H28B 110.8 . . ?
H28A C28 H28B 108.9 . . ?

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
C9 N1 N2 O3 -179.9(3) . . . . ?
C9 N1 N2 C4 1.3(5) . . . . ?
O3 N2 C4 N5 -1.4(5) . . . . ?
N1 N2 C4 N5 177.4(3) . . . . ?
O3 N2 C4 N6 179.1(3) . . . . ?
N1 N2 C4 N6 -2.1(5) . . . . ?
N5 C4 N6 O7 -0.9(5) . . . . ?
N2 C4 N6 O7 178.6(3) . . . . ?
N5 C4 N6 N8 -179.2(3) . . . . ?
N2 C4 N6 N8 0.2(5) . . . . ?
O7 N6 N8 C9 -176.2(3) . . . . ?
C4 N6 N8 C9 2.2(5) . . . . ?
N6 N8 C9 N1 -3.2(5) . . . . ?
N6 N8 C9 N10 174.6(3) . . . . ?
N2 N1 C9 N8 1.5(5) . . . . ?
N2 N1 C9 N10 -176.3(3) . . . . ?
N8 C9 N10 C21 173.9(3) . . . . ?
N1 C9 N10 C21 -8.1(4) . . . . ?
N8 C9 N10 C11 -16.0(4) . . . . ?
N1 C9 N10 C11 162.0(3) . . . . ?
C21 N10 C11 N12 178.4(4) . . . . ?
C9 N10 C11 N12 7.4(6) . . . . ?
C21 N10 C11 C15 1.0(4) . . . . ?
C9 N10 C11 C15 -170.0(3) . . . . ?
N10 C11 N12 O13 -177.6(3) . . . . ?
C15 C11 N12 O13 0.0(4) . . . . ?
C11 N12 O13 N14 -0.1(5) . . . . ?
N12 O13 N14 C15 0.1(5) . . . . ?
O13 N14 C15 N16 -178.4(3) . . . . ?
O13 N14 C15 C11 -0.1(4) . . . . ?
N12 C11 C15 N14 0.0(4) . . . . ?
N10 C11 C15 N14 177.8(3) . . . . ?
N12 C11 C15 N16 178.4(3) . . . . ?
N10 C11 C15 N16 -3.8(5) . . . . ?
N14 C15 N16 C17 -177.1(4) . . . . ?
C11 C15 N16 C17 4.9(5) . . . . ?
C15 N16 C17 N18 178.8(3) . . . . ?
C15 N16 C17 C21 -3.5(5) . . . . ?
N16 C17 N18 O19 178.5(3) . . . . ?
C21 C17 N18 O19 0.6(4) . . . . ?
C17 N18 O19 N20 -1.1(4) . . . . ?
N18 O19 N20 C21 1.2(4) . . . . ?
O19 N20 C21 N10 -179.7(3) . . . . ?
O19 N20 C21 C17 -0.8(4) . . . . ?
C9 N10 C21 N20 -10.2(5) . . . . ?
C11 N10 C21 N20 179.0(3) . . . . ?
C9 N10 C21 C17 171.0(3) . . . . ?
C11 N10 C21 C17 0.2(4) . . . . ?
N18 C17 C21 N20 0.1(4) . . . . ?
N16 C17 C21 N20 -177.9(3) . . . . ?
N18 C17 C21 N10 179.1(3) . . . . ?
N16 C17 C21 N10 1.1(5) . . . . ?
O23 C24 O25 C26 -177.9(4) . . . . ?
C28 C24 O25 C26 3.1(4) . . . . ?
C24 O25 C26 C27 -14.6(5) . . . . ?
O25 C26 C27 C28 19.9(5) . . . . ?
C26 C27 C28 C24 -17.8(5) . . . . ?
O23 C24 C28 C27 -169.1(4) . . . . ?
O25 C24 C28 C27 9.8(4) . . . . ?

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
N5 H5A O23 0.86 2.04 2.884(4) 165.9 1_655
N5 H5B O25 0.86 2.25 3.065(4) 158.0 3_766
N16 H16 O7 0.86 2.04 2.837(4) 153.6 2_646
C27 H27A N20 0.97 2.60 3.528(6) 161.2 1_565
C28 H28A O25 0.97 2.54 3.446(4) 156.4 1_455
C28 H28B O13 0.97 2.59 3.379(5) 138.6 2_656

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.107


# start Validation Reply Form
_vrf_PLAT021_chav174             
;
PROBLEM: Ratio Unique / Expected Reflections too High ...      1.136       
RESPONSE: Unique reflections is greater than one due to SHELXL HLKF 5
refinement.
;
_vrf_PLAT029_chav174             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.945 Note  
RESPONSE: Low data completeness is often encountered in low symmetry unit 
cells when utilizing Cu radiation.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_chav177
_database_code_depnum_ccdc_archive 'CCDC 1822385'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2019-01-28 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         'C14 H4 N26 O8, 4(C3 H7 N O)'
_chemical_formula_sum            'C26 H32 N30 O12'
_chemical_formula_weight         956.81

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                   9.5919(4)
_cell_length_b                   12.8830(6)
_cell_length_c                   17.5266(8)
_cell_angle_alpha                100.2430(10)
_cell_angle_beta                 96.5340(10)
_cell_angle_gamma                101.589(2)
_cell_volume                     2062.57(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2409
_cell_measurement_theta_min      2.984
_cell_measurement_theta_max      21.593

_exptl_crystal_description       block
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6849
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   '1uS microfocus'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18483
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             7482
_reflns_number_gt                3845
_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 APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
Three of the four DMF molecules displayed two-component disorder.  THe 
ratios of major:minor components were refined using free variables. Bond 
lenghts for all DMF molecules were restrained to literature values and 
anisotropic displacment parameters were restrained using enhanced rigid-
bond restraints (esds = 0.004).  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1169P)²+0.9094P] 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         7482
_refine_ls_number_parameters     723
_refine_ls_number_restraints     348
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2405
_refine_ls_wR_factor_gt          0.1930
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.054
_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
N1 N 0.9019(4) 0.5392(3) 0.5548(2) 0.0564(10) Uani 1 1 d . . . . .
N2 N 0.9533(4) 0.4872(3) 0.6072(2) 0.0548(9) Uani 1 1 d . . . . .
C4 C 0.8783(4) 0.3929(3) 0.6212(2) 0.0458(10) Uani 1 1 d . . . . .
O5 O 1.0778(4) 0.5265(3) 0.64545(19) 0.0756(10) Uani 1 1 d . . . . .
N5 N 0.9313(4) 0.3455(3) 0.6752(2) 0.0602(10) Uani 1 1 d . . . . .
H5A H 0.8824 0.2856 0.6829 0.072 Uiso 1 1 calc R U . . .
H5B H 1.0147 0.3747 0.7027 0.072 Uiso 1 1 calc R U . . .
N6 N 0.7478(4) 0.3499(3) 0.57675(19) 0.0502(9) Uani 1 1 d . . . . .
O7 O 0.6753(4) 0.2611(3) 0.58738(19) 0.0702(10) Uani 1 1 d . . . . .
N8 N 0.6905(4) 0.3972(3) 0.5228(2) 0.0521(9) Uani 1 1 d . . . . .
C9 C 0.7728(5) 0.4895(3) 0.5169(2) 0.0475(10) Uani 1 1 d . . . . .
N10 N 0.7133(4) 0.5418(3) 0.4611(2) 0.0505(9) Uani 1 1 d . . . . .
C11 C 0.7807(5) 0.6423(3) 0.4487(2) 0.0476(10) Uani 1 1 d . . . . .
N12 N 0.9058(4) 0.7019(3) 0.4825(2) 0.0656(11) Uani 1 1 d . . . . .
O13 O 0.9217(4) 0.7924(2) 0.4489(2) 0.0733(10) Uani 1 1 d . . . . .
N14 N 0.8050(4) 0.7867(3) 0.3932(2) 0.0654(11) Uani 1 1 d . . . . .
C15 C 0.7183(5) 0.6954(3) 0.3931(2) 0.0467(10) Uani 1 1 d . . . . .
N16 N 0.5855(4) 0.6517(3) 0.34652(19) 0.0475(9) Uani 1 1 d . . . . .
C17 C 0.5213(5) 0.5488(3) 0.3553(2) 0.0458(10) Uani 1 1 d . . . . .
N18 N 0.3998(4) 0.4889(3) 0.3189(2) 0.0596(10) Uani 1 1 d . . . . .
O19 O 0.3825(4) 0.3969(2) 0.35091(19) 0.0734(10) Uani 1 1 d . . . . .
N20 N 0.4973(4) 0.4028(3) 0.4084(2) 0.0657(11) Uani 1 1 d . . . . .
C21 C 0.5825(5) 0.4951(3) 0.4112(2) 0.0461(10) Uani 1 1 d . . . . .
C22 C 0.5197(4) 0.7076(3) 0.2966(2) 0.0450(10) Uani 1 1 d . . . . .
N23 N 0.5568(4) 0.8150(3) 0.31569(19) 0.0567(10) Uani 1 1 d . . . . .
N24 N 0.4998(4) 0.8673(3) 0.2663(2) 0.0550(10) Uani 1 1 d . . . . .
C25 C 0.4089(4) 0.8072(3) 0.2041(2) 0.0439(10) Uani 1 1 d . . . . .
N26 N 0.3571(4) 0.7008(3) 0.1904(2) 0.0594(10) Uani 1 1 d . . . . .
N27 N 0.4185(4) 0.6483(3) 0.2385(2) 0.0620(11) Uani 1 1 d . . . . .
N28 N 0.3603(3) 0.8606(2) 0.14731(18) 0.0427(8) Uani 1 1 d . . . . .
C29 C 0.3952(4) 0.9736(3) 0.1568(2) 0.0483(11) Uani 1 1 d . . . . .
N30 N 0.4477(5) 1.0453(3) 0.2211(2) 0.0697(12) Uani 1 1 d . . . . .
O31 O 0.4594(5) 1.1436(2) 0.1983(2) 0.0892(13) Uani 1 1 d . . . . .
N32 N 0.4115(5) 1.1302(3) 0.1175(2) 0.0754(13) Uani 1 1 d . . . . .
C33 C 0.3730(5) 1.0273(3) 0.0939(2) 0.0482(11) Uani 1 1 d . . . . .
N34 N 0.3121(4) 0.9732(3) 0.01768(19) 0.0474(9) Uani 1 1 d . . . . .
C35 C 0.2718(4) 0.8624(3) 0.0098(2) 0.0470(10) Uani 1 1 d . . . . .
N36 N 0.2130(5) 0.7937(3) -0.0543(2) 0.0684(12) Uani 1 1 d . . . . .
O37 O 0.1961(4) 0.6938(3) -0.03318(19) 0.0827(12) Uani 1 1 d . . . . .
N38 N 0.2472(5) 0.7038(3) 0.0459(2) 0.0694(12) Uani 1 1 d . . . . .
C39 C 0.2944(4) 0.8075(3) 0.0721(2) 0.0468(10) Uani 1 1 d . . . . .
C40 C 0.2525(5) 1.0283(3) -0.0370(2) 0.0451(10) Uani 1 1 d . . . . .
N41 N 0.3472(4) 1.1029(3) -0.05838(19) 0.0486(9) Uani 1 1 d . . . . .
N42 N 0.2869(4) 1.1567(3) -0.10635(19) 0.0468(9) Uani 1 1 d . . . . .
O43 O 0.3671(3) 1.2321(3) -0.12953(19) 0.0662(9) Uani 1 1 d . . . . .
C44 C 0.1438(5) 1.1343(3) -0.1328(2) 0.0471(10) Uani 1 1 d . . . . .
N45 N 0.0882(4) 1.1856(3) -0.1818(2) 0.0688(12) Uani 1 1 d . . . . .
H45A H 0.1430 1.2355 -0.1985 0.083 Uiso 1 1 calc R U . . .
H45B H -0.0032 1.1696 -0.1976 0.083 Uiso 1 1 calc R U . . .
N46 N 0.0592(4) 1.0539(3) -0.1065(2) 0.0521(9) Uani 1 1 d . . . . .
O47 O -0.0754(3) 1.0309(3) -0.1308(2) 0.0730(10) Uani 1 1 d . . . . .
N48 N 0.1116(4) 0.9989(3) -0.05672(19) 0.0500(9) Uani 1 1 d . . . . .
C49 C 0.3417(8) 0.6125(4) 0.7945(3) 0.109(2) Uani 1 1 d D U . . .
H49A H 0.2753 0.5707 0.7492 0.163 Uiso 1 1 calc R U . . .
H49B H 0.4314 0.6422 0.7788 0.163 Uiso 1 1 calc R U . . .
H49C H 0.3023 0.6704 0.8193 0.163 Uiso 1 1 calc R U . . .
C50 C 0.4791(8) 0.5955(5) 0.9133(4) 0.156(4) Uani 1 1 d D U . . .
H50A H 0.4759 0.5523 0.9527 0.234 Uiso 1 1 calc R U . . .
H50B H 0.4666 0.6661 0.9353 0.234 Uiso 1 1 calc R U . . .
H50C H 0.5706 0.6019 0.8951 0.234 Uiso 1 1 calc R U . . .
N51 N 0.3657(4) 0.5446(3) 0.8486(2) 0.0771(12) Uani 1 1 d D U . . .
C52 C 0.2957(6) 0.4450(3) 0.8391(3) 0.0940(18) Uani 1 1 d D U . . .
H52 H 0.3143 0.4072 0.8782 0.113 Uiso 1 1 calc R U . . .
O53 O 0.2042(4) 0.3969(2) 0.78013(19) 0.0787(10) Uani 1 1 d D U . . .
C54A C 0.8253(13) 0.9027(6) 0.6693(6) 0.138(5) Uani 0.624(9) 1 d D U P A 1
H54A H 0.7726 0.8733 0.7070 0.207 Uiso 0.624(9) 1 calc R U P A 1
H54B H 0.9114 0.9539 0.6962 0.207 Uiso 0.624(9) 1 calc R U P A 1
H54C H 0.8504 0.8452 0.6346 0.207 Uiso 0.624(9) 1 calc R U P A 1
C55A C 0.6299(10) 0.8828(6) 0.5651(5) 0.112(4) Uani 0.624(9) 1 d D U P A 1
H55A H 0.5509 0.9161 0.5544 0.169 Uiso 0.624(9) 1 calc R U P A 1
H55B H 0.5960 0.8172 0.5828 0.169 Uiso 0.624(9) 1 calc R U P A 1
H55C H 0.6707 0.8662 0.5181 0.169 Uiso 0.624(9) 1 calc R U P A 1
N56A N 0.7379(7) 0.9557(4) 0.6250(3) 0.059(3) Uani 0.624(9) 1 d D U P A 1
C57A C 0.7449(8) 1.0589(4) 0.6419(4) 0.064(2) Uani 0.624(9) 1 d D U P A 1
H57A H 0.6815 1.0870 0.6117 0.077 Uiso 0.624(9) 1 calc R U P A 1
O58A O 0.833(2) 1.1226(5) 0.6969(9) 0.079(5) Uani 0.624(9) 1 d D U P A 1
C54B C 0.722(3) 0.8522(7) 0.6219(10) 0.153(10) Uani 0.376(9) 1 d D U P A 2
H54D H 0.7126 0.8182 0.5677 0.229 Uiso 0.376(9) 1 calc R U P A 2
H54E H 0.6333 0.8288 0.6411 0.229 Uiso 0.376(9) 1 calc R U P A 2
H54F H 0.7988 0.8325 0.6518 0.229 Uiso 0.376(9) 1 calc R U P A 2
C55B C 0.684(3) 1.0023(11) 0.5645(9) 0.225(19) Uani 0.376(9) 1 d D U P A 2
H55D H 0.5987 1.0250 0.5780 0.338 Uiso 0.376(9) 1 calc R U P A 2
H55E H 0.6575 0.9434 0.5196 0.338 Uiso 0.376(9) 1 calc R U P A 2
H55F H 0.7491 1.0617 0.5523 0.338 Uiso 0.376(9) 1 calc R U P A 2
N56B N 0.7520(17) 0.9673(6) 0.6296(6) 0.105(10) Uani 0.376(9) 1 d D U P A 2
C57B C 0.8206(14) 1.0345(7) 0.6930(5) 0.072(4) Uani 0.376(9) 1 d D U P A 2
H57B H 0.8630 1.0069 0.7330 0.086 Uiso 0.376(9) 1 calc R U P A 2
O58B O 0.832(3) 1.1349(8) 0.7029(12) 0.065(7) Uani 0.376(9) 1 d D U P A 2
C59A C 0.2441(15) 0.9157(9) 0.5754(5) 0.119(4) Uani 0.579(7) 1 d D U P B 1
H59A H 0.1707 0.9472 0.5532 0.179 Uiso 0.579(7) 1 calc R U P B 1
H59B H 0.2507 0.8523 0.5390 0.179 Uiso 0.579(7) 1 calc R U P B 1
H59C H 0.3350 0.9672 0.5860 0.179 Uiso 0.579(7) 1 calc R U P B 1
C60A C 0.2056(16) 0.7747(6) 0.6491(6) 0.123(5) Uani 0.579(7) 1 d D U P B 1
H60A H 0.3007 0.7678 0.6678 0.185 Uiso 0.579(7) 1 calc R U P B 1
H60B H 0.1733 0.7310 0.5973 0.185 Uiso 0.579(7) 1 calc R U P B 1
H60C H 0.1410 0.7510 0.6838 0.185 Uiso 0.579(7) 1 calc R U P B 1
N61A N 0.2084(12) 0.8862(6) 0.6468(4) 0.1189(12) Uani 0.579(7) 1 d D U P B 1
C62A C 0.1975(13) 0.9557(6) 0.7078(4) 0.110(4) Uani 0.579(7) 1 d D U P B 1
H62A H 0.1811 1.0224 0.7009 0.133 Uiso 0.579(7) 1 calc R U P B 1
O63A O 0.2081(10) 0.9369(7) 0.7758(3) 0.1189(12) Uani 0.579(7) 1 d D U P B 1
C59B C 0.1845(19) 0.9433(10) 0.6198(6) 0.138(6) Uani 0.421(7) 1 d D U P B 2
H59D H 0.1120 0.9764 0.6407 0.208 Uiso 0.421(7) 1 calc R U P B 2
H59E H 0.1499 0.9070 0.5662 0.208 Uiso 0.421(7) 1 calc R U P B 2
H59F H 0.2701 0.9981 0.6222 0.208 Uiso 0.421(7) 1 calc R U P B 2
C60B C 0.2660(19) 0.7791(10) 0.6214(8) 0.130(7) Uani 0.421(7) 1 d D U P B 2
H60D H 0.3275 0.7521 0.6564 0.195 Uiso 0.421(7) 1 calc R U P B 2
H60E H 0.3187 0.8046 0.5824 0.195 Uiso 0.421(7) 1 calc R U P B 2
H60F H 0.1846 0.7220 0.5961 0.195 Uiso 0.421(7) 1 calc R U P B 2
N61B N 0.2169(13) 0.8666(8) 0.6650(5) 0.1189(12) Uani 0.421(7) 1 d D U P B 2
C62B C 0.1837(15) 0.8662(8) 0.7347(5) 0.098(4) Uani 0.421(7) 1 d D U P B 2
H62B H 0.2017 0.8109 0.7593 0.117 Uiso 0.421(7) 1 calc R U P B 2
O63B O 0.1284(13) 0.9371(9) 0.7702(5) 0.1189(12) Uani 0.421(7) 1 d D U P B 2
C64A C 0.0705(13) 0.3312(10) 0.2022(4) 0.169(5) Uani 0.673(8) 1 d D U P C 1
H64A H 0.0496 0.2563 0.2056 0.253 Uiso 0.673(8) 1 calc R U P C 1
H64B H -0.0148 0.3589 0.2057 0.253 Uiso 0.673(8) 1 calc R U P C 1
H64C H 0.1449 0.3715 0.2445 0.253 Uiso 0.673(8) 1 calc R U P C 1
C65A C 0.1298(14) 0.4482(6) 0.1124(7) 0.160(5) Uani 0.673(8) 1 d D U P C 1
H65A H 0.2138 0.4964 0.1444 0.240 Uiso 0.673(8) 1 calc R U P C 1
H65B H 0.0457 0.4740 0.1238 0.240 Uiso 0.673(8) 1 calc R U P C 1
H65C H 0.1380 0.4455 0.0580 0.240 Uiso 0.673(8) 1 calc R U P C 1
N66A N 0.1179(11) 0.3416(6) 0.1289(4) 0.1189(12) Uani 0.673(8) 1 d D U P C 1
C67A C 0.1294(8) 0.2597(5) 0.0771(4) 0.089(3) Uani 0.673(8) 1 d D U P C 1
H67A H 0.1026 0.1906 0.0873 0.107 Uiso 0.673(8) 1 calc R U P C 1
O68A O 0.1749(8) 0.2692(6) 0.0138(4) 0.1189(12) Uani 0.673(8) 1 d D U P C 1
C64B C 0.142(2) 0.2786(11) 0.1558(7) 0.139(7) Uani 0.327(8) 1 d D U P C 2
H64D H 0.0547 0.2524 0.1755 0.208 Uiso 0.327(8) 1 calc R U P C 2
H64E H 0.2201 0.3041 0.1986 0.208 Uiso 0.327(8) 1 calc R U P C 2
H64F H 0.1618 0.2211 0.1189 0.208 Uiso 0.327(8) 1 calc R U P C 2
C65B C 0.084(2) 0.4534(12) 0.1667(8) 0.112(7) Uani 0.327(8) 1 d D U P C 2
H65D H 0.1577 0.4834 0.2116 0.169 Uiso 0.327(8) 1 calc R U P C 2
H65E H -0.0055 0.4271 0.1839 0.169 Uiso 0.327(8) 1 calc R U P C 2
H65F H 0.0735 0.5084 0.1374 0.169 Uiso 0.327(8) 1 calc R U P C 2
N66B N 0.124(2) 0.3655(10) 0.1177(5) 0.1189(12) Uani 0.327(8) 1 d D U P C 2
C67B C 0.138(2) 0.3645(9) 0.0450(6) 0.142(7) Uani 0.327(8) 1 d D U P C 2
H67B H 0.1586 0.4302 0.0290 0.170 Uiso 0.327(8) 1 calc R U P C 2
O68B O 0.1251(18) 0.2789(12) -0.0049(6) 0.1189(12) Uani 0.327(8) 1 d D U P C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.315(5) . ?
N1 N2 1.336(4) . ?
N2 O5 1.259(4) . ?
N2 C4 1.359(5) . ?
C4 N5 1.322(5) . ?
C4 N6 1.351(5) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 O7 1.270(4) . ?
N6 N8 1.338(4) . ?
N8 C9 1.316(5) . ?
C9 N10 1.414(5) . ?
N10 C11 1.391(5) . ?
N10 C21 1.400(5) . ?
C11 N12 1.299(5) . ?
C11 C15 1.432(5) . ?
N12 O13 1.386(4) . ?
O13 N14 1.380(4) . ?
N14 C15 1.296(5) . ?
C15 N16 1.385(5) . ?
N16 C17 1.388(5) . ?
N16 C22 1.401(5) . ?
C17 N18 1.286(5) . ?
C17 C21 1.435(5) . ?
N18 O19 1.387(4) . ?
O19 N20 1.386(4) . ?
N20 C21 1.289(5) . ?
C22 N27 1.328(5) . ?
C22 N23 1.328(5) . ?
N23 N24 1.323(4) . ?
N24 C25 1.327(5) . ?
C25 N26 1.329(5) . ?
C25 N28 1.396(4) . ?
N26 N27 1.328(4) . ?
N28 C39 1.385(5) . ?
N28 C29 1.402(5) . ?
C29 N30 1.300(5) . ?
C29 C33 1.421(5) . ?
N30 O31 1.382(4) . ?
O31 N32 1.407(5) . ?
N32 C33 1.280(5) . ?
C33 N34 1.393(5) . ?
N34 C35 1.379(5) . ?
N34 C40 1.424(5) . ?
C35 N36 1.291(5) . ?
C35 C39 1.422(5) . ?
N36 O37 1.385(5) . ?
O37 N38 1.392(4) . ?
N38 C39 1.301(5) . ?
C40 N48 1.316(5) . ?
C40 N41 1.321(5) . ?
N41 N42 1.333(4) . ?
N42 O43 1.269(4) . ?
N42 C44 1.353(5) . ?
C44 N45 1.304(5) . ?
C44 N46 1.364(5) . ?
N45 H45A 0.8600 . ?
N45 H45B 0.8600 . ?
N46 O47 1.270(4) . ?
N46 N48 1.334(4) . ?
C49 N51 1.430(4) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 N51 1.438(4) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
N51 C52 1.294(4) . ?
C52 O53 1.254(4) . ?
C52 H52 0.9300 . ?
C54A N56A 1.430(4) . ?
C54A H54A 0.9600 . ?
C54A H54B 0.9600 . ?
C54A H54C 0.9600 . ?
C55A N56A 1.438(4) . ?
C55A H55A 0.9600 . ?
C55A H55B 0.9600 . ?
C55A H55C 0.9600 . ?
N56A C57A 1.295(4) . ?
C57A O58A 1.254(4) . ?
C57A H57A 0.9300 . ?
C54B N56B 1.430(4) . ?
C54B H54D 0.9600 . ?
C54B H54E 0.9600 . ?
C54B H54F 0.9600 . ?
C55B N56B 1.438(4) . ?
C55B H55D 0.9600 . ?
C55B H55E 0.9600 . ?
C55B H55F 0.9600 . ?
N56B C57B 1.296(4) . ?
C57B O58B 1.254(4) . ?
C57B H57B 0.9300 . ?
C59A N61A 1.430(4) . ?
C59A H59A 0.9600 . ?
C59A H59B 0.9600 . ?
C59A H59C 0.9600 . ?
C60A N61A 1.438(4) . ?
C60A H60A 0.9600 . ?
C60A H60B 0.9600 . ?
C60A H60C 0.9600 . ?
N61A C62A 1.296(4) . ?
C62A O63A 1.254(4) . ?
C62A H62A 0.9300 . ?
C59B N61B 1.430(4) . ?
C59B H59D 0.9600 . ?
C59B H59E 0.9600 . ?
C59B H59F 0.9600 . ?
C60B N61B 1.438(4) . ?
C60B H60D 0.9600 . ?
C60B H60E 0.9600 . ?
C60B H60F 0.9600 . ?
N61B C62B 1.297(4) . ?
C62B O63B 1.254(4) . ?
C62B H62B 0.9300 . ?
C64A N66A 1.430(4) . ?
C64A H64A 0.9600 . ?
C64A H64B 0.9600 . ?
C64A H64C 0.9600 . ?
C65A N66A 1.438(4) . ?
C65A H65A 0.9600 . ?
C65A H65B 0.9600 . ?
C65A H65C 0.9600 . ?
N66A C67A 1.296(4) . ?
C67A O68A 1.254(4) . ?
C67A H67A 0.9300 . ?
C64B N66B 1.430(4) . ?
C64B H64D 0.9600 . ?
C64B H64E 0.9600 . ?
C64B H64F 0.9600 . ?
C65B N66B 1.438(4) . ?
C65B H65D 0.9600 . ?
C65B H65E 0.9600 . ?
C65B H65F 0.9600 . ?
N66B C67B 1.295(4) . ?
C67B O68B 1.254(4) . ?
C67B H67B 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
C9 N1 N2 113.6(3) . . ?
O5 N2 N1 118.8(3) . . ?
O5 N2 C4 117.9(3) . . ?
N1 N2 C4 123.3(4) . . ?
N5 C4 N6 121.9(4) . . ?
N5 C4 N2 121.4(4) . . ?
N6 C4 N2 116.7(3) . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O7 N6 N8 118.4(3) . . ?
O7 N6 C4 118.5(3) . . ?
N8 N6 C4 123.1(3) . . ?
C9 N8 N6 113.9(3) . . ?
N1 C9 N8 129.4(3) . . ?
N1 C9 N10 115.7(4) . . ?
N8 C9 N10 114.8(4) . . ?
C11 N10 C21 113.8(3) . . ?
C11 N10 C9 123.5(3) . . ?
C21 N10 C9 122.7(3) . . ?
N12 C11 N10 127.9(3) . . ?
N12 C11 C15 109.1(4) . . ?
N10 C11 C15 123.0(4) . . ?
C11 N12 O13 104.6(3) . . ?
N14 O13 N12 112.1(3) . . ?
C15 N14 O13 104.4(3) . . ?
N14 C15 N16 127.0(3) . . ?
N14 C15 C11 109.8(4) . . ?
N16 C15 C11 123.2(4) . . ?
C15 N16 C17 114.2(3) . . ?
C15 N16 C22 123.0(3) . . ?
C17 N16 C22 122.9(3) . . ?
N18 C17 N16 127.4(3) . . ?
N18 C17 C21 109.6(3) . . ?
N16 C17 C21 123.0(4) . . ?
C17 N18 O19 104.6(3) . . ?
N20 O19 N18 111.7(3) . . ?
C21 N20 O19 104.6(3) . . ?
N20 C21 N10 127.9(3) . . ?
N20 C21 C17 109.5(4) . . ?
N10 C21 C17 122.7(3) . . ?
N27 C22 N23 126.3(3) . . ?
N27 C22 N16 116.8(3) . . ?
N23 C22 N16 116.7(3) . . ?
N24 N23 C22 116.4(3) . . ?
N23 N24 C25 116.7(3) . . ?
N24 C25 N26 126.8(3) . . ?
N24 C25 N28 117.2(3) . . ?
N26 C25 N28 116.1(3) . . ?
N27 N26 C25 115.7(3) . . ?
C22 N27 N26 117.1(3) . . ?
C39 N28 C25 123.1(3) . . ?
C39 N28 C29 113.4(3) . . ?
C25 N28 C29 122.6(3) . . ?
N30 C29 N28 127.9(4) . . ?
N30 C29 C33 109.2(4) . . ?
N28 C29 C33 122.8(4) . . ?
C29 N30 O31 104.4(3) . . ?
N30 O31 N32 111.8(3) . . ?
C33 N32 O31 103.5(3) . . ?
N32 C33 N34 125.5(3) . . ?
N32 C33 C29 111.1(4) . . ?
N34 C33 C29 123.4(4) . . ?
C35 N34 C33 113.3(3) . . ?
C35 N34 C40 122.2(3) . . ?
C33 N34 C40 120.9(3) . . ?
N36 C35 N34 125.8(4) . . ?
N36 C35 C39 110.3(4) . . ?
N34 C35 C39 123.9(4) . . ?
C35 N36 O37 104.4(3) . . ?
N36 O37 N38 111.7(3) . . ?
C39 N38 O37 104.4(3) . . ?
N38 C39 N28 127.7(3) . . ?
N38 C39 C35 109.2(4) . . ?
N28 C39 C35 123.1(4) . . ?
N48 C40 N41 130.1(3) . . ?
N48 C40 N34 115.1(3) . . ?
N41 C40 N34 114.8(4) . . ?
C40 N41 N42 113.2(3) . . ?
O43 N42 N41 118.9(3) . . ?
O43 N42 C44 117.7(3) . . ?
N41 N42 C44 123.4(3) . . ?
N45 C44 N42 122.1(4) . . ?
N45 C44 N46 121.0(4) . . ?
N42 C44 N46 116.9(3) . . ?
C44 N45 H45A 120.0 . . ?
C44 N45 H45B 120.0 . . ?
H45A N45 H45B 120.0 . . ?
O47 N46 N48 118.9(3) . . ?
O47 N46 C44 118.1(3) . . ?
N48 N46 C44 123.0(3) . . ?
C40 N48 N46 113.4(3) . . ?
N51 C49 H49A 109.5 . . ?
N51 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
N51 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
N51 C50 H50A 109.5 . . ?
N51 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
N51 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C52 N51 C49 123.4(3) . . ?
C52 N51 C50 122.7(3) . . ?
C49 N51 C50 113.8(4) . . ?
O53 C52 N51 123.5(3) . . ?
O53 C52 H52 118.2 . . ?
N51 C52 H52 118.2 . . ?
N56A C54A H54A 109.5 . . ?
N56A C54A H54B 109.5 . . ?
H54A C54A H54B 109.5 . . ?
N56A C54A H54C 109.5 . . ?
H54A C54A H54C 109.5 . . ?
H54B C54A H54C 109.5 . . ?
N56A C55A H55A 109.5 . . ?
N56A C55A H55B 109.5 . . ?
H55A C55A H55B 109.5 . . ?
N56A C55A H55C 109.5 . . ?
H55A C55A H55C 109.5 . . ?
H55B C55A H55C 109.5 . . ?
C57A N56A C54A 123.4(3) . . ?
C57A N56A C55A 122.5(3) . . ?
C54A N56A C55A 113.8(4) . . ?
O58A C57A N56A 123.2(3) . . ?
O58A C57A H57A 118.4 . . ?
N56A C57A H57A 118.4 . . ?
N56B C54B H54D 109.5 . . ?
N56B C54B H54E 109.5 . . ?
H54D C54B H54E 109.5 . . ?
N56B C54B H54F 109.5 . . ?
H54D C54B H54F 109.5 . . ?
H54E C54B H54F 109.5 . . ?
N56B C55B H55D 109.5 . . ?
N56B C55B H55E 109.5 . . ?
H55D C55B H55E 109.5 . . ?
N56B C55B H55F 109.5 . . ?
H55D C55B H55F 109.5 . . ?
H55E C55B H55F 109.5 . . ?
C57B N56B C54B 123.3(3) . . ?
C57B N56B C55B 122.4(3) . . ?
C54B N56B C55B 113.8(4) . . ?
O58B C57B N56B 123.1(3) . . ?
O58B C57B H57B 118.5 . . ?
N56B C57B H57B 118.5 . . ?
N61A C59A H59A 109.5 . . ?
N61A C59A H59B 109.5 . . ?
H59A C59A H59B 109.5 . . ?
N61A C59A H59C 109.5 . . ?
H59A C59A H59C 109.5 . . ?
H59B C59A H59C 109.5 . . ?
N61A C60A H60A 109.5 . . ?
N61A C60A H60B 109.5 . . ?
H60A C60A H60B 109.5 . . ?
N61A C60A H60C 109.5 . . ?
H60A C60A H60C 109.5 . . ?
H60B C60A H60C 109.5 . . ?
C62A N61A C59A 123.3(3) . . ?
C62A N61A C60A 122.3(3) . . ?
C59A N61A C60A 113.8(4) . . ?
O63A C62A N61A 122.8(3) . . ?
O63A C62A H62A 118.6 . . ?
N61A C62A H62A 118.6 . . ?
N61B C59B H59D 109.5 . . ?
N61B C59B H59E 109.5 . . ?
H59D C59B H59E 109.5 . . ?
N61B C59B H59F 109.5 . . ?
H59D C59B H59F 109.5 . . ?
H59E C59B H59F 109.5 . . ?
N61B C60B H60D 109.5 . . ?
N61B C60B H60E 109.5 . . ?
H60D C60B H60E 109.5 . . ?
N61B C60B H60F 109.5 . . ?
H60D C60B H60F 109.5 . . ?
H60E C60B H60F 109.5 . . ?
C62B N61B C59B 123.1(3) . . ?
C62B N61B C60B 122.3(3) . . ?
C59B N61B C60B 113.7(4) . . ?
O63B C62B N61B 122.7(3) . . ?
O63B C62B H62B 118.6 . . ?
N61B C62B H62B 118.6 . . ?
N66A C64A H64A 109.5 . . ?
N66A C64A H64B 109.5 . . ?
H64A C64A H64B 109.5 . . ?
N66A C64A H64C 109.5 . . ?
H64A C64A H64C 109.5 . . ?
H64B C64A H64C 109.5 . . ?
N66A C65A H65A 109.5 . . ?
N66A C65A H65B 109.5 . . ?
H65A C65A H65B 109.5 . . ?
N66A C65A H65C 109.5 . . ?
H65A C65A H65C 109.5 . . ?
H65B C65A H65C 109.5 . . ?
C67A N66A C64A 123.1(3) . . ?
C67A N66A C65A 122.4(3) . . ?
C64A N66A C65A 113.8(4) . . ?
O68A C67A N66A 123.0(3) . . ?
O68A C67A H67A 118.5 . . ?
N66A C67A H67A 118.5 . . ?
N66B C64B H64D 109.5 . . ?
N66B C64B H64E 109.5 . . ?
H64D C64B H64E 109.5 . . ?
N66B C64B H64F 109.5 . . ?
H64D C64B H64F 109.5 . . ?
H64E C64B H64F 109.5 . . ?
N66B C65B H65D 109.5 . . ?
N66B C65B H65E 109.5 . . ?
H65D C65B H65E 109.5 . . ?
N66B C65B H65F 109.5 . . ?
H65D C65B H65F 109.5 . . ?
H65E C65B H65F 109.5 . . ?
C67B N66B C64B 123.4(3) . . ?
C67B N66B C65B 122.6(3) . . ?
C64B N66B C65B 113.9(4) . . ?
O68B C67B N66B 123.0(3) . . ?
O68B C67B H67B 118.5 . . ?
N66B C67B H67B 118.5 . . ?

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
C9 N1 N2 O5 178.2(4) . . . . ?
C9 N1 N2 C4 -1.2(6) . . . . ?
O5 N2 C4 N5 2.6(6) . . . . ?
N1 N2 C4 N5 -178.0(4) . . . . ?
O5 N2 C4 N6 -177.0(4) . . . . ?
N1 N2 C4 N6 2.5(6) . . . . ?
N5 C4 N6 O7 -0.4(6) . . . . ?
N2 C4 N6 O7 179.1(4) . . . . ?
N5 C4 N6 N8 178.6(4) . . . . ?
N2 C4 N6 N8 -1.8(6) . . . . ?
O7 N6 N8 C9 179.0(4) . . . . ?
C4 N6 N8 C9 0.0(6) . . . . ?
N2 N1 C9 N8 -1.0(7) . . . . ?
N2 N1 C9 N10 179.6(4) . . . . ?
N6 N8 C9 N1 1.6(7) . . . . ?
N6 N8 C9 N10 -179.0(3) . . . . ?
N1 C9 N10 C11 -3.4(6) . . . . ?
N8 C9 N10 C11 177.1(4) . . . . ?
N1 C9 N10 C21 174.4(4) . . . . ?
N8 C9 N10 C21 -5.1(6) . . . . ?
C21 N10 C11 N12 -175.8(5) . . . . ?
C9 N10 C11 N12 2.2(7) . . . . ?
C21 N10 C11 C15 3.2(6) . . . . ?
C9 N10 C11 C15 -178.8(4) . . . . ?
N10 C11 N12 O13 179.5(4) . . . . ?
C15 C11 N12 O13 0.4(5) . . . . ?
C11 N12 O13 N14 -0.6(5) . . . . ?
N12 O13 N14 C15 0.6(5) . . . . ?
O13 N14 C15 N16 -179.5(4) . . . . ?
O13 N14 C15 C11 -0.3(5) . . . . ?
N12 C11 C15 N14 -0.1(6) . . . . ?
N10 C11 C15 N14 -179.2(4) . . . . ?
N12 C11 C15 N16 179.1(4) . . . . ?
N10 C11 C15 N16 -0.1(7) . . . . ?
N14 C15 N16 C17 175.6(5) . . . . ?
C11 C15 N16 C17 -3.4(6) . . . . ?
N14 C15 N16 C22 -6.2(7) . . . . ?
C11 C15 N16 C22 174.8(4) . . . . ?
C15 N16 C17 N18 -179.0(4) . . . . ?
C22 N16 C17 N18 2.7(7) . . . . ?
C15 N16 C17 C21 3.8(6) . . . . ?
C22 N16 C17 C21 -174.4(4) . . . . ?
N16 C17 N18 O19 -177.6(4) . . . . ?
C21 C17 N18 O19 -0.1(5) . . . . ?
C17 N18 O19 N20 0.3(5) . . . . ?
N18 O19 N20 C21 -0.4(5) . . . . ?
O19 N20 C21 N10 178.4(4) . . . . ?
O19 N20 C21 C17 0.3(5) . . . . ?
C11 N10 C21 N20 179.3(5) . . . . ?
C9 N10 C21 N20 1.3(7) . . . . ?
C11 N10 C21 C17 -2.8(6) . . . . ?
C9 N10 C21 C17 179.2(4) . . . . ?
N18 C17 C21 N20 -0.1(6) . . . . ?
N16 C17 C21 N20 177.5(4) . . . . ?
N18 C17 C21 N10 -178.4(4) . . . . ?
N16 C17 C21 N10 -0.8(7) . . . . ?
C15 N16 C22 N27 159.6(4) . . . . ?
C17 N16 C22 N27 -22.3(6) . . . . ?
C15 N16 C22 N23 -25.4(6) . . . . ?
C17 N16 C22 N23 152.7(4) . . . . ?
N27 C22 N23 N24 -8.7(7) . . . . ?
N16 C22 N23 N24 176.8(4) . . . . ?
C22 N23 N24 C25 1.6(6) . . . . ?
N23 N24 C25 N26 7.9(7) . . . . ?
N23 N24 C25 N28 -173.2(4) . . . . ?
N24 C25 N26 N27 -10.2(7) . . . . ?
N28 C25 N26 N27 170.9(4) . . . . ?
N23 C22 N27 N26 6.4(7) . . . . ?
N16 C22 N27 N26 -179.1(4) . . . . ?
C25 N26 N27 C22 2.9(6) . . . . ?
N24 C25 N28 C39 164.1(4) . . . . ?
N26 C25 N28 C39 -16.9(6) . . . . ?
N24 C25 N28 C29 -4.8(6) . . . . ?
N26 C25 N28 C29 174.2(4) . . . . ?
C39 N28 C29 N30 174.6(5) . . . . ?
C25 N28 C29 N30 -15.5(7) . . . . ?
C39 N28 C29 C33 -3.7(6) . . . . ?
C25 N28 C29 C33 166.2(4) . . . . ?
N28 C29 N30 O31 -179.0(4) . . . . ?
C33 C29 N30 O31 -0.5(5) . . . . ?
C29 N30 O31 N32 0.3(6) . . . . ?
N30 O31 N32 C33 0.1(6) . . . . ?
O31 N32 C33 N34 177.4(4) . . . . ?
O31 N32 C33 C29 -0.4(5) . . . . ?
N30 C29 C33 N32 0.6(6) . . . . ?
N28 C29 C33 N32 179.1(4) . . . . ?
N30 C29 C33 N34 -177.3(4) . . . . ?
N28 C29 C33 N34 1.3(7) . . . . ?
N32 C33 N34 C35 -175.8(5) . . . . ?
C29 C33 N34 C35 1.8(6) . . . . ?
N32 C33 N34 C40 -16.6(7) . . . . ?
C29 C33 N34 C40 160.9(4) . . . . ?
C33 N34 C35 N36 180.0(4) . . . . ?
C40 N34 C35 N36 21.1(7) . . . . ?
C33 N34 C35 C39 -2.3(6) . . . . ?
C40 N34 C35 C39 -161.1(4) . . . . ?
N34 C35 N36 O37 178.6(4) . . . . ?
C39 C35 N36 O37 0.6(5) . . . . ?
C35 N36 O37 N38 -0.3(5) . . . . ?
N36 O37 N38 C39 -0.1(5) . . . . ?
O37 N38 C39 N28 -178.0(4) . . . . ?
O37 N38 C39 C35 0.5(5) . . . . ?
C25 N28 C39 N38 11.7(7) . . . . ?
C29 N28 C39 N38 -178.5(4) . . . . ?
C25 N28 C39 C35 -166.6(4) . . . . ?
C29 N28 C39 C35 3.2(6) . . . . ?
N36 C35 C39 N38 -0.8(5) . . . . ?
N34 C35 C39 N38 -178.8(4) . . . . ?
N36 C35 C39 N28 177.8(4) . . . . ?
N34 C35 C39 N28 -0.3(7) . . . . ?
C35 N34 C40 N48 45.8(6) . . . . ?
C33 N34 C40 N48 -111.5(5) . . . . ?
C35 N34 C40 N41 -135.8(4) . . . . ?
C33 N34 C40 N41 66.9(5) . . . . ?
N48 C40 N41 N42 1.4(7) . . . . ?
N34 C40 N41 N42 -176.7(3) . . . . ?
C40 N41 N42 O43 178.5(4) . . . . ?
C40 N41 N42 C44 -2.3(6) . . . . ?
O43 N42 C44 N45 1.6(6) . . . . ?
N41 N42 C44 N45 -177.5(4) . . . . ?
O43 N42 C44 N46 -179.3(4) . . . . ?
N41 N42 C44 N46 1.6(6) . . . . ?
N45 C44 N46 O47 -0.4(6) . . . . ?
N42 C44 N46 O47 -179.5(4) . . . . ?
N45 C44 N46 N48 179.6(4) . . . . ?
N42 C44 N46 N48 0.4(6) . . . . ?
N41 C40 N48 N46 0.4(7) . . . . ?
N34 C40 N48 N46 178.5(3) . . . . ?
O47 N46 N48 C40 178.6(4) . . . . ?
C44 N46 N48 C40 -1.3(6) . . . . ?
C49 N51 C52 O53 3.0(10) . . . . ?
C50 N51 C52 O53 -174.5(7) . . . . ?
C54A N56A C57A O58A 2.9(19) . . . . ?
C55A N56A C57A O58A 175.6(16) . . . . ?
C54B N56B C57B O58B -171(3) . . . . ?
C55B N56B C57B O58B 0(3) . . . . ?
C59A N61A C62A O63A -158.6(12) . . . . ?
C60A N61A C62A O63A 12.4(17) . . . . ?
C59B N61B C62B O63B -4.5(19) . . . . ?
C60B N61B C62B O63B -173.2(15) . . . . ?
C64A N66A C67A O68A -177.9(10) . . . . ?
C65A N66A C67A O68A 12.2(14) . . . . ?
C64B N66B C67B O68B 22(3) . . . . ?
C65B N66B C67B O68B -156(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
N5 H5A O58A 0.86 2.12 2.944(12) 159.5 1_545
N5 H5A O58B 0.86 2.01 2.835(18) 161.2 1_545
N5 H5B O53 0.86 2.08 2.906(5) 161.3 1_655
N45 H45A O53 0.86 2.16 2.947(5) 153.0 1_564
N45 H45B O58A 0.86 2.19 2.928(10) 143.2 1_454
N45 H45B O58B 0.86 2.13 2.878(15) 145.0 1_454
C49 H49A O5 0.96 2.37 3.287(6) 158.6 1_455
C52 H52 O43 0.93 2.39 3.083(5) 130.8 1_546
C54A H54B O47 0.96 3.00 3.529(10) 116.3 1_656
C57A H57A O7 0.93 2.37 3.096(6) 135.1 1_565
C57B H57B O47 0.93 2.34 3.146(9) 144.7 1_656
C59B H59F N23 0.96 2.61 3.483(16) 152.0 2_676
C64A H64C N18 0.96 2.66 3.572(12) 159.8 .
C65A H65A N26 0.96 2.65 3.478(11) 145.1 .
C65A H65A N27 0.96 2.64 3.593(13) 171.4 .

_refine_diff_density_max         0.522
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.055

