# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_vaninm
_database_code_depnum_ccdc_archive 'CCDC 1573859'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.27

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                   7.8201(16)
_cell_length_b                   8.3180(17)
_cell_length_c                   11.360(2)
_cell_angle_alpha                91.58(3)
_cell_angle_beta                 92.89(3)
_cell_angle_gamma                116.34(3)
_cell_volume                     660.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9448
_cell_measurement_theta_min      1.798
_cell_measurement_theta_max      28.201

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   0.940
_exptl_transmission_factor_max   0.982
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   
'Absorption corrections were made using the program SADABS (Sheldrick, 1996)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9448
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.798
_diffrn_reflns_theta_max         28.201
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3173
_reflns_number_gt                2594
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXS-2017 (Sheldrick, 2017)'
_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)+(0.0633P)²+0.1072P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3173
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
O2 O 0.61799(13) 0.43897(11) 0.38328(8) 0.0327(2) Uani 1 1 d . . . . .
O3 O 0.82352(13) 0.75409(13) 0.50804(8) 0.0362(2) Uani 1 1 d . . . . .
O5 O 0.85310(15) 0.00452(13) 0.87227(9) 0.0473(3) Uani 1 1 d . . . . .
N2 N 1.08743(16) 0.24589(16) 0.97422(10) 0.0326(3) Uani 1 1 d . . . . .
N1 N 0.86327(15) 0.49458(15) 0.62452(10) 0.0328(3) Uani 1 1 d . . . . .
C3 C 0.53933(16) 0.59413(15) 0.22609(10) 0.0250(2) Uani 1 1 d . . . . .
H3 H 0.466346 0.487794 0.181285 0.032(4) Uiso 1 1 calc R . . . .
C4 C 0.62532(15) 0.59015(15) 0.33413(10) 0.0245(2) Uani 1 1 d . . . . .
C5 C 0.73562(17) 0.75206(16) 0.40282(11) 0.0280(3) Uani 1 1 d . . . . .
C2 C 0.56209(16) 0.75931(16) 0.18362(11) 0.0278(3) Uani 1 1 d . . . . .
C10 C 0.93370(16) 0.28916(16) 0.79379(10) 0.0271(3) Uani 1 1 d . . . . .
C9 C 0.95713(17) 0.16805(17) 0.88357(11) 0.0304(3) Uani 1 1 d . . . . .
C11 C 0.98808(17) 0.47056(16) 0.81738(11) 0.0296(3) Uani 1 1 d . . . . .
H11 H 1.050056 0.526755 0.889641 0.035(4) Uiso 1 1 calc R . . . .
C12 C 0.94830(18) 0.56668(17) 0.73117(12) 0.0320(3) Uani 1 1 d . . . . .
H12 H 0.982510 0.687489 0.748384 0.039(4) Uiso 1 1 calc R . . . .
C14 C 0.84643(19) 0.21330(18) 0.68307(12) 0.0338(3) Uani 1 1 d . . . . .
H14 H 0.809136 0.092440 0.663784 0.043(4) Uiso 1 1 calc R . . . .
C13 C 0.81598(19) 0.32113(18) 0.60187(12) 0.0359(3) Uani 1 1 d . . . . .
H13 H 0.759523 0.269706 0.527580 0.047(4) Uiso 1 1 calc R . . . .
C6 C 0.75823(19) 0.91507(17) 0.36004(13) 0.0353(3) Uani 1 1 d . . . . .
H6 H 0.830790 1.021729 0.404609 0.055(5) Uiso 1 1 calc R . . . .
C1 C 0.47707(19) 0.76744(18) 0.06817(12) 0.0353(3) Uani 1 1 d . . . . .
C7 C 0.67215(19) 0.91813(17) 0.25056(13) 0.0353(3) Uani 1 1 d . . . . .
H7 H 0.688308 1.027257 0.221870 0.058(5) Uiso 1 1 calc R . . . .
C8 C 0.5102(2) 0.27373(16) 0.31512(12) 0.0361(3) Uani 1 1 d . . . . .
H8A H 0.379790 0.253700 0.302788 0.044(4) Uiso 1 1 calc R . . . .
H8B H 0.514768 0.176542 0.356605 0.048(4) Uiso 1 1 calc R . . . .
H8C H 0.563875 0.280040 0.240214 0.043(4) Uiso 1 1 calc R . . . .
O1 O 0.37463(14) 0.64089(13) 0.00074(8) 0.0390(2) Uani 1 1 d . . . . .
H5 H 0.819(3) 0.646(3) 0.5305(19) 0.072(6) Uiso 1 1 d . . . . .
H1 H 0.510(3) 0.895(3) 0.0479(17) 0.059(5) Uiso 1 1 d . . . . .
H2A H 1.106(2) 0.173(2) 1.0233(15) 0.041(4) Uiso 1 1 d . . . . .
H2B H 1.174(2) 0.365(2) 0.9773(15) 0.045(4) Uiso 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
O2 C4 1.3691(14) . ?
O2 C8 1.4305(16) . ?
O3 C5 1.3443(15) . ?
O3 H5 0.93(2) . ?
O5 C9 1.2354(16) . ?
N2 C9 1.3378(17) . ?
N2 H2A 0.890(17) . ?
N2 H2B 0.914(18) . ?
N1 C13 1.3346(18) . ?
N1 C12 1.3396(18) . ?
C3 C4 1.3778(16) . ?
C3 C2 1.4073(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.4177(17) . ?
C5 C6 1.3922(18) . ?
C2 C7 1.3906(19) . ?
C2 C1 1.4572(18) . ?
C10 C11 1.3879(18) . ?
C10 C14 1.3904(18) . ?
C10 C9 1.5134(17) . ?
C11 C12 1.3886(17) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C13 1.3875(19) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C6 C7 1.3903(19) . ?
C6 H6 0.9300 . ?
C1 O1 1.2173(17) . ?
C1 H1 1.011(19) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C8 115.89(10) . . ?
C5 O3 H5 116.9(14) . . ?
C9 N2 H2A 116.7(11) . . ?
C9 N2 H2B 122.5(11) . . ?
H2A N2 H2B 119.2(15) . . ?
C13 N1 C12 117.12(11) . . ?
C4 C3 C2 119.91(11) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
O2 C4 C3 125.32(11) . . ?
O2 C4 C5 114.58(10) . . ?
C3 C4 C5 120.09(11) . . ?
O3 C5 C6 118.39(12) . . ?
O3 C5 C4 121.91(11) . . ?
C6 C5 C4 119.69(11) . . ?
C7 C2 C3 119.89(12) . . ?
C7 C2 C1 119.16(12) . . ?
C3 C2 C1 120.92(12) . . ?
C11 C10 C14 118.13(11) . . ?
C11 C10 C9 123.55(11) . . ?
C14 C10 C9 118.27(11) . . ?
O5 C9 N2 123.13(12) . . ?
O5 C9 C10 119.30(11) . . ?
N2 C9 C10 117.53(11) . . ?
C10 C11 C12 118.83(12) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N1 C12 C11 123.46(12) . . ?
N1 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
C13 C14 C10 118.82(12) . . ?
C13 C14 H14 120.6 . . ?
C10 C14 H14 120.6 . . ?
N1 C13 C14 123.60(12) . . ?
N1 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C7 C6 C5 119.89(12) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
O1 C1 C2 126.86(12) . . ?
O1 C1 H1 120.9(11) . . ?
C2 C1 H1 112.2(11) . . ?
C6 C7 C2 120.52(12) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
C8 O2 C4 C3 -0.41(17) . . . . ?
C8 O2 C4 C5 -179.03(11) . . . . ?
C2 C3 C4 O2 -178.15(11) . . . . ?
C2 C3 C4 C5 0.40(17) . . . . ?
O2 C4 C5 O3 -0.55(17) . . . . ?
C3 C4 C5 O3 -179.25(11) . . . . ?
O2 C4 C5 C6 178.02(11) . . . . ?
C3 C4 C5 C6 -0.68(18) . . . . ?
C4 C3 C2 C7 0.34(18) . . . . ?
C4 C3 C2 C1 178.24(11) . . . . ?
C11 C10 C9 O5 156.01(13) . . . . ?
C14 C10 C9 O5 -21.47(18) . . . . ?
C11 C10 C9 N2 -21.94(18) . . . . ?
C14 C10 C9 N2 160.57(12) . . . . ?
C14 C10 C11 C12 1.82(18) . . . . ?
C9 C10 C11 C12 -175.67(11) . . . . ?
C13 N1 C12 C11 -0.15(19) . . . . ?
C10 C11 C12 N1 -1.5(2) . . . . ?
C11 C10 C14 C13 -0.62(18) . . . . ?
C9 C10 C14 C13 177.00(12) . . . . ?
C12 N1 C13 C14 1.5(2) . . . . ?
C10 C14 C13 N1 -1.1(2) . . . . ?
O3 C5 C6 C7 178.84(12) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C7 C2 C1 O1 -178.34(14) . . . . ?
C3 C2 C1 O1 3.7(2) . . . . ?
C5 C6 C7 C2 0.5(2) . . . . ?
C3 C2 C7 C6 -0.8(2) . . . . ?
C1 C2 C7 C6 -178.75(13) . . . . ?

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
_geom_hbond_publ_flag
C11 H11 O1 0.93 2.53 3.299(2) 140.1 1_656 yes
C6 H6 O3 0.93 2.63 3.436(2) 145.2 2_776 yes
O3 H5 N1 0.93(2) 1.81(2) 2.6867(16) 157(2) . yes
N2 H2A O5 0.890(17) 2.039(18) 2.9283(17) 176.7(15) 2_757 yes
N2 H2B O1 0.914(18) 2.131(18) 3.043(2) 175.1(15) 1_656 yes

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vahexa
_database_code_depnum_ccdc_archive 'CCDC 1573863'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 N4 O4'
_chemical_formula_weight         308.34

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   17.887(2)
_cell_length_b                   7.0953(9)
_cell_length_c                   23.419(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2972.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    38485
_cell_measurement_theta_min      1.739
_cell_measurement_theta_max      28.317

_exptl_crystal_description       needles
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   0.940
_exptl_transmission_factor_max   0.992
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   
'Absorption corrections were made using the program SADABS (Sheldrick, 1996)'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38485
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.739
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3711
_reflns_number_gt                3036
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXS-2017 (Sheldrick, 2017)'
_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)+(0.0524P)²+0.8141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3711
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O4 O 0.16076(5) 0.86687(12) 0.03796(3) 0.0236(2) Uani 1 1 d . . . . .
N3 N 0.12674(5) 0.30017(14) 0.37261(4) 0.0196(2) Uani 1 1 d . . . . .
N2 N 0.18207(5) 0.07052(14) 0.43785(4) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.11272(5) 0.34028(14) 0.47586(4) 0.0188(2) Uani 1 1 d . . . . .
C9 C 0.12223(6) 0.43558(16) 0.42051(5) 0.0202(2) Uani 1 1 d . . . . .
H9A H 0.168459 0.512254 0.421473 0.024 Uiso 1 1 calc R U . . .
H9B H 0.079570 0.521908 0.414089 0.024 Uiso 1 1 calc R U . . .
N4 N 0.04602(5) 0.08695(14) 0.42697(4) 0.0230(2) Uani 1 1 d . . . . .
O1 O 0.12281(5) 0.74073(14) 0.30647(4) 0.0337(2) Uani 1 1 d . . . . .
C4 C 0.12343(6) 0.93465(16) 0.13487(5) 0.0180(2) Uani 1 1 d . . . . .
O2 O 0.16164(6) 0.46131(14) 0.27412(4) 0.0382(3) Uani 1 1 d . . . . .
C2 C 0.15421(6) 0.70753(16) 0.20783(5) 0.0192(2) Uani 1 1 d . . . . .
C5 C 0.15936(6) 0.82062(16) 0.09397(5) 0.0174(2) Uani 1 1 d . . . . .
C1 C 0.14509(7) 0.64164(18) 0.26760(5) 0.0230(2) Uani 1 1 d . . . . .
C3 C 0.12144(6) 0.87830(16) 0.19143(5) 0.0197(2) Uani 1 1 d . . . . .
H3 H 0.097795 0.955672 0.219174 0.024 Uiso 1 1 calc R U . . .
C6 C 0.19490(6) 0.65666(16) 0.11113(5) 0.0208(2) Uani 1 1 d . . . . .
H6 H 0.221598 0.583373 0.083986 0.025 Uiso 1 1 calc R U . . .
C12 C 0.05709(7) 0.18572(18) 0.37267(5) 0.0242(3) Uani 1 1 d . . . . .
H12A H 0.013765 0.269199 0.365429 0.029 Uiso 1 1 calc R U . . .
H12B H 0.059472 0.092282 0.341328 0.029 Uiso 1 1 calc R U . . .
C11 C 0.19039(6) 0.17057(17) 0.38364(5) 0.0231(2) Uani 1 1 d . . . . .
H11A H 0.193790 0.077746 0.352186 0.028 Uiso 1 1 calc R U . . .
H11B H 0.237485 0.243846 0.384236 0.028 Uiso 1 1 calc R U . . .
C7 C 0.19177(6) 0.59866(16) 0.16769(5) 0.0215(2) Uani 1 1 d . . . . .
H7 H 0.215306 0.484544 0.178964 0.026 Uiso 1 1 calc R U . . .
C10 C 0.17693(7) 0.21079(17) 0.48372(5) 0.0235(2) Uani 1 1 d . . . . .
H10A H 0.223740 0.285159 0.484857 0.028 Uiso 1 1 calc R U . . .
H10B H 0.171735 0.145038 0.520793 0.028 Uiso 1 1 calc R U . . .
C13 C 0.04365(6) 0.22644(17) 0.47324(5) 0.0233(2) Uani 1 1 d . . . . .
H13B H 0.036576 0.160546 0.510105 0.028 Uiso 1 1 calc R U . . .
H13A H 0.000322 0.311060 0.467368 0.028 Uiso 1 1 calc R U . . .
O3 O 0.09184(5) 1.09488(12) 0.11289(4) 0.0259(2) Uani 1 1 d . . . . .
C14 C 0.11135(7) -0.03599(17) 0.43624(6) 0.0248(3) Uani 1 1 d . . . . .
H14A H 0.105050 -0.104572 0.472738 0.030 Uiso 1 1 calc R U . . .
H14B H 0.113818 -0.130437 0.405182 0.030 Uiso 1 1 calc R U . . .
C8 C 0.05961(8) 1.22402(19) 0.15263(6) 0.0321(3) Uani 1 1 d . . . . .
H8A H 0.016718 1.164624 0.171450 0.048 Uiso 1 1 calc R U . . .
H8B H 0.042992 1.337354 0.132356 0.048 Uiso 1 1 calc R U . . .
H8C H 0.096985 1.258729 0.181362 0.048 Uiso 1 1 calc R U . . .
H2 H 0.1476(11) 0.410(3) 0.3121(9) 0.068(6) Uiso 1 1 d . . . . .
H5 H 0.1355(10) 0.966(3) 0.0295(8) 0.052(5) Uiso 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
O4 C5 1.3523(13) . ?
N3 C9 1.4791(15) . ?
N3 C11 1.4861(15) . ?
N3 C12 1.4871(15) . ?
N2 C11 1.4621(15) . ?
N2 C10 1.4673(16) . ?
N2 C14 1.4740(15) . ?
N1 C9 1.4719(14) . ?
N1 C13 1.4773(14) . ?
N1 C10 1.4823(15) . ?
N4 C12 1.4655(16) . ?
N4 C13 1.4681(15) . ?
N4 C14 1.4744(16) . ?
O1 C1 1.2173(15) . ?
C4 O3 1.3700(13) . ?
C4 C3 1.3840(16) . ?
C4 C5 1.4089(15) . ?
O2 C1 1.3221(16) . ?
C2 C7 1.3898(16) . ?
C2 C3 1.3997(16) . ?
C2 C1 1.4847(15) . ?
C5 C6 1.3852(16) . ?
C6 C7 1.3883(16) . ?
O3 C8 1.4276(15) . ?

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 N3 C11 108.17(9) . . ?
C9 N3 C12 107.96(9) . . ?
C11 N3 C12 107.68(9) . . ?
C11 N2 C10 108.22(9) . . ?
C11 N2 C14 108.30(9) . . ?
C10 N2 C14 108.22(9) . . ?
C9 N1 C13 108.13(9) . . ?
C9 N1 C10 107.73(9) . . ?
C13 N1 C10 108.31(9) . . ?
N1 C9 N3 112.07(9) . . ?
C12 N4 C13 108.78(9) . . ?
C12 N4 C14 107.67(9) . . ?
C13 N4 C14 108.24(9) . . ?
O3 C4 C3 126.07(10) . . ?
O3 C4 C5 114.16(10) . . ?
C3 C4 C5 119.76(10) . . ?
C7 C2 C3 119.87(10) . . ?
C7 C2 C1 121.05(10) . . ?
C3 C2 C1 119.02(10) . . ?
O4 C5 C6 118.46(10) . . ?
O4 C5 C4 121.90(10) . . ?
C6 C5 C4 119.63(10) . . ?
O1 C1 O2 123.09(11) . . ?
O1 C1 C2 124.00(11) . . ?
O2 C1 C2 112.89(10) . . ?
C4 C3 C2 120.12(10) . . ?
C5 C6 C7 120.48(10) . . ?
N4 C12 N3 112.03(9) . . ?
N2 C11 N3 111.93(9) . . ?
C6 C7 C2 120.00(11) . . ?
N2 C10 N1 112.22(9) . . ?
N4 C13 N1 112.04(9) . . ?
C4 O3 C8 117.02(9) . . ?
N2 C14 N4 112.38(9) . . ?

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
_geom_hbond_publ_flag
C10 H10A O4 0.99 2.64 3.2165(14) 117.2 2_565 yes
C14 H14A O4 0.99 2.61 3.4595(15) 144.5 8_566 yes
C14 H14B O1 0.99 2.49 3.4333(16) 158.9 1_545 yes
C8 H8A O1 0.98 2.61 3.4027(17) 138.6 4 yes
O2 H2 N3 0.99(2) 1.66(2) 2.6490(13) 173.3(19) . yes
O4 H5 N1 0.860(19) 1.91(2) 2.6779(13) 148.7(18) 8_575 yes

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_vappzh2o
_database_code_depnum_ccdc_archive 'CCDC 1573866'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H19 N2 O4.50'
_chemical_formula_weight         263.29

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                   30.274(3)
_cell_length_b                   6.7982(7)
_cell_length_c                   14.2368(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.727(2)
_cell_angle_gamma                90
_cell_volume                     2639.6(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    18650
_cell_measurement_theta_min      3.177
_cell_measurement_theta_max      28.345

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   0.942
_exptl_transmission_factor_max   0.968
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   
'Absorption corrections were made using the program SADABS (Sheldrick, 1996)'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18650
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.177
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3291
_reflns_number_gt                2851
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXS-2017 (Sheldrick, 2017)'
_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)+(0.0639P)²+2.0855P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3291
_refine_ls_number_parameters     189
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_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
O2 O 0.03902(3) 0.14442(15) 0.42218(8) 0.0332(2) Uani 1 1 d D . . . .
N1 N 0.04632(4) 0.33510(16) 0.12570(8) 0.0234(2) Uani 1 1 d . . . . .
C2 C 0.12562(4) 0.18037(18) 0.49879(9) 0.0201(2) Uani 1 1 d . . . . .
O1 O 0.07057(4) 0.42886(16) 0.49818(8) 0.0372(3) Uani 1 1 d . . . . .
C1 C 0.07491(4) 0.2571(2) 0.47180(9) 0.0233(3) Uani 1 1 d . . . . .
N2 N 0.14429(4) 0.35348(17) 0.29544(8) 0.0252(2) Uani 1 1 d . . . . .
C9 C 0.13299(4) 0.2337(2) 0.20233(10) 0.0268(3) Uani 1 1 d . . . . .
H9A H 0.154860 0.117456 0.221949 0.032 Uiso 1 1 calc R U . . .
H9B H 0.139956 0.311550 0.151540 0.032 Uiso 1 1 calc R U . . .
C11 C 0.05616(5) 0.4545(2) 0.22020(11) 0.0315(3) Uani 1 1 d . . . . .
H11A H 0.048558 0.376079 0.269938 0.038 Uiso 1 1 calc R U . . .
H11B H 0.034817 0.572253 0.200545 0.038 Uiso 1 1 calc R U . . .
C12 C 0.10973(5) 0.5176(2) 0.27183(12) 0.0327(3) Uani 1 1 d . . . . .
H12A H 0.115684 0.611102 0.225234 0.039 Uiso 1 1 calc R U . . .
H12B H 0.116140 0.587901 0.337403 0.039 Uiso 1 1 calc R U . . .
C10 C 0.08004(5) 0.16403(19) 0.15017(11) 0.0276(3) Uani 1 1 d . . . . .
H10A H 0.074030 0.092525 0.085152 0.033 Uiso 1 1 calc R U . . .
H10B H 0.073767 0.072548 0.197136 0.033 Uiso 1 1 calc R U . . .
C4 C 0.21330(4) 0.23348(17) 0.58560(8) 0.0185(2) Uani 1 1 d . . . . .
C5 C 0.22134(4) 0.04732(17) 0.55295(9) 0.0191(2) Uani 1 1 d . . . . .
C3 C 0.16593(4) 0.29835(18) 0.55826(9) 0.0204(2) Uani 1 1 d . . . . .
H3 H 0.160770 0.424704 0.580240 0.024 Uiso 1 1 calc R U . . .
C6 C 0.18118(4) -0.06751(18) 0.49082(9) 0.0222(2) Uani 1 1 d . . . . .
H6 H 0.186228 -0.190961 0.465752 0.027 Uiso 1 1 calc R U . . .
C7 C 0.13353(4) -0.00285(18) 0.46502(9) 0.0220(2) Uani 1 1 d . . . . .
H7 H 0.106404 -0.084125 0.424286 0.026 Uiso 1 1 calc R U . . .
O3 O 0.25486(3) 0.33597(12) 0.64543(7) 0.0231(2) Uani 1 1 d . . . . .
O4 O 0.26699(3) -0.02356(13) 0.58046(7) 0.0248(2) Uani 1 1 d . . . . .
C8 C 0.24810(5) 0.53069(19) 0.67394(11) 0.0309(3) Uani 1 1 d . . . . .
H8A H 0.229533 0.608001 0.610867 0.046 Uiso 1 1 calc R U . . .
H8B H 0.280141 0.592157 0.713966 0.046 Uiso 1 1 calc R U . . .
H8C H 0.229974 0.525795 0.716603 0.046 Uiso 1 1 calc R U . . .
O5 O 0.000000 -0.1242(3) 0.250000 0.0839(9) Uani 1 2 d DS TU P . .
H5 H 0.2902(7) 0.056(3) 0.6224(15) 0.044(5) Uiso 1 1 d . . . . .
H2A H 0.1414(7) 0.274(3) 0.3425(15) 0.044(5) Uiso 1 1 d . . . . .
H1A H 0.0145(7) 0.284(3) 0.0989(14) 0.045(5) Uiso 1 1 d . . . . .
H1B H 0.0509(7) 0.412(3) 0.0782(14) 0.038(4) Uiso 1 1 d . . . . .
H5A H 0.0178(9) -0.037(2) 0.3199(10) 0.136(13) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2650(16) . ?
N1 C10 1.4856(16) . ?
N1 C11 1.4863(17) . ?
C2 C7 1.3928(17) . ?
C2 C3 1.3973(16) . ?
C2 C1 1.5049(15) . ?
O1 C1 1.2505(17) . ?
N2 C9 1.4642(17) . ?
N2 C12 1.4655(18) . ?
C9 C10 1.5204(16) . ?
C11 C12 1.5231(18) . ?
C4 O3 1.3653(13) . ?
C4 C3 1.3850(15) . ?
C4 C5 1.4054(16) . ?
C5 O4 1.3512(13) . ?
C5 C6 1.3915(16) . ?
C6 C7 1.3961(16) . ?
O3 C8 1.4251(15) . ?

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
C10 N1 C11 111.58(10) . . ?
C7 C2 C3 119.12(10) . . ?
C7 C2 C1 122.09(11) . . ?
C3 C2 C1 118.78(11) . . ?
O1 C1 O2 123.81(11) . . ?
O1 C1 C2 118.40(11) . . ?
O2 C1 C2 117.78(11) . . ?
C9 N2 C12 110.66(10) . . ?
N2 C9 C10 113.45(10) . . ?
N1 C11 C12 110.11(10) . . ?
N2 C12 C11 113.62(11) . . ?
N1 C10 C9 110.01(10) . . ?
O3 C4 C3 125.05(10) . . ?
O3 C4 C5 114.89(10) . . ?
C3 C4 C5 120.04(10) . . ?
O4 C5 C6 119.06(10) . . ?
O4 C5 C4 121.83(10) . . ?
C6 C5 C4 119.10(10) . . ?
C4 C3 C2 120.86(11) . . ?
C5 C6 C7 120.57(11) . . ?
C2 C7 C6 120.24(11) . . ?
C4 O3 C8 116.38(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
C7 C2 C1 O1 -174.66(12) . . . . ?
C3 C2 C1 O1 4.34(17) . . . . ?
C7 C2 C1 O2 4.31(17) . . . . ?
C3 C2 C1 O2 -176.70(11) . . . . ?
C12 N2 C9 C10 -53.41(15) . . . . ?
C10 N1 C11 C12 55.21(15) . . . . ?
C9 N2 C12 C11 52.94(16) . . . . ?
N1 C11 C12 N2 -54.20(16) . . . . ?
C11 N1 C10 C9 -55.69(14) . . . . ?
N2 C9 C10 N1 55.16(15) . . . . ?
O3 C4 C5 O4 0.76(16) . . . . ?
C3 C4 C5 O4 -178.09(11) . . . . ?
O3 C4 C5 C6 -179.43(10) . . . . ?
C3 C4 C5 C6 1.71(17) . . . . ?
O3 C4 C3 C2 -178.32(10) . . . . ?
C5 C4 C3 C2 0.40(18) . . . . ?
C7 C2 C3 C4 -1.40(18) . . . . ?
C1 C2 C3 C4 179.58(10) . . . . ?
O4 C5 C6 C7 176.96(11) . . . . ?
C4 C5 C6 C7 -2.85(18) . . . . ?
C3 C2 C7 C6 0.27(18) . . . . ?
C1 C2 C7 C6 179.26(11) . . . . ?
C5 C6 C7 C2 1.87(18) . . . . ?
C3 C4 O3 C8 -5.38(17) . . . . ?
C5 C4 O3 C8 175.84(11) . . . . ?

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
_geom_hbond_publ_flag
C9 H9A O3 0.99 2.58 3.1719(15) 118.4 7_556 yes
C11 H11B O5 0.99 2.55 3.450(2) 150.9 1_565 yes
C10 H10A O2 0.99 2.64 3.6021(17) 164.2 6 yes
C6 H6 O4 0.95 2.65 3.5501(15) 158.6 7_546 yes
N1 H1B O1 0.911(19) 1.85(2) 2.7508(15) 170.6(17) 6_565 yes
N1 H1A O2 0.935(19) 1.79(2) 2.7003(14) 164.3(18) 2 yes
N1 H1A O1 0.935(19) 2.532(19) 3.2590(15) 134.7(16) 2 yes
O4 H5 O3 0.88(2) 2.278(19) 2.6943(12) 108.9(15) . yes
O5 H5A O2 1.0815(10) 1.7989(10) 2.8681(16) 169.0(9) . yes
O4 H5 N2 0.88(2) 1.92(2) 2.7482(14) 157.1(18) 7_556 yes

_refine_diff_density_max         0.533
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_vacafnam
_database_code_depnum_ccdc_archive 'CCDC 1573861'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 N6 O7'
_chemical_formula_weight         484.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.8016(14)
_cell_length_b                   10.7859(15)
_cell_length_c                   11.3248(16)
_cell_angle_alpha                70.022(3)
_cell_angle_beta                 78.358(3)
_cell_angle_gamma                86.692(3)
_cell_volume                     1102.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    12503
_cell_measurement_theta_min      1.950
_cell_measurement_theta_max      27.279

_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   0.966
_exptl_transmission_factor_max   0.970
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   
'Absorption corrections were made using the program SADABS (Sheldrick, 1996)'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12503
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.950
_diffrn_reflns_theta_max         27.279
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4823
_reflns_number_gt                3560
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXS-2017 (Sheldrick, 2017)'
_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)+(0.0776P)²+0.3315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4823
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
O3 O 0.46140(15) 0.30151(14) 0.41921(14) 0.0339(4) Uani 1 1 d . . . . .
O4 O 0.50652(17) 0.56389(15) 0.30254(16) 0.0374(4) Uani 1 1 d . . . . .
O1 O 0.88926(15) 0.09645(14) 0.20605(15) 0.0364(4) Uani 1 1 d . . . . .
O2 O 1.00635(17) 0.27738(16) 0.06785(16) 0.0394(4) Uani 1 1 d . . . . .
C7 C 0.8114(2) 0.4439(2) 0.13619(19) 0.0274(4) Uani 1 1 d . . . . .
H7 H 0.890147 0.479492 0.070572 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6783(2) 0.2564(2) 0.29038(19) 0.0268(4) Uani 1 1 d . . . . .
H3 H 0.666347 0.163621 0.330114 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7130(2) 0.5278(2) 0.17280(19) 0.0290(5) Uani 1 1 d . . . . .
H6 H 0.724581 0.620559 0.132311 0.035 Uiso 1 1 calc R U . . .
C2 C 0.7961(2) 0.30829(19) 0.19453(19) 0.0260(4) Uani 1 1 d . . . . .
C1 C 0.8998(2) 0.2165(2) 0.1581(2) 0.0286(5) Uani 1 1 d . . . . .
C4 C 0.5800(2) 0.33997(19) 0.32688(19) 0.0264(4) Uani 1 1 d . . . . .
C8 C 0.4363(2) 0.1631(2) 0.4802(2) 0.0375(5) Uani 1 1 d . . . . .
H8A H 0.433957 0.122465 0.415323 0.056 Uiso 1 1 calc R U . . .
H8B H 0.346724 0.148011 0.540300 0.056 Uiso 1 1 calc R U . . .
H8C H 0.510934 0.123890 0.526762 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5980(2) 0.4772(2) 0.26807(19) 0.0273(4) Uani 1 1 d . . . . .
O5 O 0.19372(15) 0.14063(14) 0.97227(15) 0.0354(4) Uani 1 1 d . . . . .
O6 O -0.11624(16) 0.78673(14) 0.63729(16) 0.0388(4) Uani 1 1 d . . . . .
O7 O -0.09288(16) 0.33724(14) 0.79159(15) 0.0390(4) Uani 1 1 d . . . . .
N6 N 0.16294(18) 0.77792(16) 0.45826(16) 0.0277(4) Uani 1 1 d . . . . .
N4 N 0.08635(18) 0.44427(16) 0.63546(16) 0.0282(4) Uani 1 1 d . . . . .
N3 N -0.10192(17) 0.56104(16) 0.71328(16) 0.0274(4) Uani 1 1 d . . . . .
C9 C 0.2060(2) 0.01885(19) 1.01360(19) 0.0266(4) Uani 1 1 d . . . . .
N5 N 0.26288(19) 0.58409(18) 0.46472(17) 0.0324(4) Uani 1 1 d . . . . .
C17 C -0.0387(2) 0.44117(19) 0.7177(2) 0.0282(4) Uani 1 1 d . . . . .
C19 C 0.1423(2) 0.5647(2) 0.55215(19) 0.0281(4) Uani 1 1 d . . . . .
N2 N 0.10999(19) -0.05803(19) 1.10619(18) 0.0334(4) Uani 1 1 d . . . . .
C15 C -0.0508(2) 0.6879(2) 0.63269(19) 0.0280(4) Uani 1 1 d . . . . .
N1 N 0.5355(2) -0.00825(19) 0.79216(18) 0.0383(5) Uani 1 1 d . . . . .
C16 C -0.2344(2) 0.5568(2) 0.8015(2) 0.0393(5) Uani 1 1 d . . . . .
H16A H -0.221437 0.594142 0.866195 0.059 Uiso 1 1 calc R U . . .
H16B H -0.266980 0.465105 0.843701 0.059 Uiso 1 1 calc R U . . .
H16C H -0.303574 0.608311 0.753705 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3313(2) -0.04405(19) 0.95900(19) 0.0254(4) Uani 1 1 d . . . . .
C14 C 0.4189(2) 0.0343(2) 0.8490(2) 0.0331(5) Uani 1 1 d . . . . .
H14 H 0.394010 0.123744 0.812198 0.040 Uiso 1 1 calc R U . . .
C18 C 0.1614(2) 0.3216(2) 0.6436(2) 0.0377(5) Uani 1 1 d . . . . .
H18A H 0.107957 0.264458 0.617798 0.057 Uiso 1 1 calc R U . . .
H18B H 0.173637 0.276506 0.731896 0.057 Uiso 1 1 calc R U . . .
H18C H 0.252794 0.341354 0.586550 0.057 Uiso 1 1 calc R U . . .
C13 C 0.5689(2) -0.1345(2) 0.8472(2) 0.0345(5) Uani 1 1 d . . . . .
H13 H 0.652309 -0.166743 0.809113 0.041 Uiso 1 1 calc R U . . .
C22 C 0.0777(2) 0.67997(19) 0.55116(19) 0.0271(4) Uani 1 1 d . . . . .
C12 C 0.4894(2) -0.2194(2) 0.9554(2) 0.0355(5) Uani 1 1 d . . . . .
H12 H 0.516875 -0.308279 0.990519 0.043 Uiso 1 1 calc R U . . .
C11 C 0.3686(2) -0.1735(2) 1.0124(2) 0.0321(5) Uani 1 1 d . . . . .
H11 H 0.311820 -0.230496 1.087526 0.038 Uiso 1 1 calc R U . . .
C20 C 0.2711(2) 0.7159(2) 0.4097(2) 0.0331(5) Uani 1 1 d . . . . .
H20 H 0.345675 0.760700 0.343423 0.040 Uiso 1 1 calc R U . . .
C21 C 0.1449(3) 0.9206(2) 0.4240(2) 0.0401(6) Uani 1 1 d . . . . .
H21A H 0.223264 0.966001 0.356971 0.060 Uiso 1 1 calc R U . . .
H21B H 0.141524 0.946166 0.499697 0.060 Uiso 1 1 calc R U . . .
H21C H 0.057729 0.945339 0.392435 0.060 Uiso 1 1 calc R U . . .
H2B H 0.040(3) -0.014(3) 1.143(3) 0.068(9) Uiso 1 1 d . . . . .
H2A H 0.116(3) -0.148(3) 1.129(3) 0.057(8) Uiso 1 1 d . . . . .
H2 H 1.067(4) 0.216(3) 0.042(3) 0.080(10) Uiso 1 1 d . . . . .
H5 H 0.441(3) 0.525(3) 0.366(3) 0.071(10) Uiso 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
O3 C4 1.373(2) . ?
O3 C8 1.426(2) . ?
O4 C5 1.357(2) . ?
O1 C1 1.222(2) . ?
O2 C1 1.325(3) . ?
C7 C6 1.384(3) . ?
C7 C2 1.387(3) . ?
C3 C4 1.380(3) . ?
C3 C2 1.406(3) . ?
C6 C5 1.383(3) . ?
C2 C1 1.476(3) . ?
C4 C5 1.405(3) . ?
O5 C9 1.242(2) . ?
O6 C15 1.223(3) . ?
O7 C17 1.219(2) . ?
N6 C20 1.345(3) . ?
N6 C22 1.382(3) . ?
N6 C21 1.463(3) . ?
N4 C17 1.376(3) . ?
N4 C19 1.383(3) . ?
N4 C18 1.460(3) . ?
N3 C17 1.391(3) . ?
N3 C15 1.413(2) . ?
N3 C16 1.462(3) . ?
C9 N2 1.331(3) . ?
C9 C10 1.495(3) . ?
N5 C20 1.343(3) . ?
N5 C19 1.355(3) . ?
C19 C22 1.360(3) . ?
C15 C22 1.421(3) . ?
N1 C14 1.333(3) . ?
N1 C13 1.342(3) . ?
C10 C11 1.380(3) . ?
C10 C14 1.391(3) . ?
C13 C12 1.370(3) . ?
C12 C11 1.380(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 C8 116.98(16) . . ?
C6 C7 C2 120.53(19) . . ?
C4 C3 C2 120.18(18) . . ?
C5 C6 C7 120.26(19) . . ?
C7 C2 C3 119.35(18) . . ?
C7 C2 C1 121.72(18) . . ?
C3 C2 C1 118.93(18) . . ?
O1 C1 O2 123.12(19) . . ?
O1 C1 C2 123.74(19) . . ?
O2 C1 C2 113.14(18) . . ?
O3 C4 C3 125.63(18) . . ?
O3 C4 C5 114.59(17) . . ?
C3 C4 C5 119.78(18) . . ?
O4 C5 C6 117.84(18) . . ?
O4 C5 C4 122.25(18) . . ?
C6 C5 C4 119.90(18) . . ?
C20 N6 C22 106.08(17) . . ?
C20 N6 C21 126.39(18) . . ?
C22 N6 C21 127.44(18) . . ?
C17 N4 C19 119.12(18) . . ?
C17 N4 C18 119.37(17) . . ?
C19 N4 C18 121.39(19) . . ?
C17 N3 C15 126.75(17) . . ?
C17 N3 C16 117.23(17) . . ?
C15 N3 C16 116.02(17) . . ?
O5 C9 N2 121.56(19) . . ?
O5 C9 C10 119.77(18) . . ?
N2 C9 C10 118.66(18) . . ?
C20 N5 C19 103.27(18) . . ?
O7 C17 N4 121.43(19) . . ?
O7 C17 N3 120.95(19) . . ?
N4 C17 N3 117.62(17) . . ?
N5 C19 C22 112.24(18) . . ?
N5 C19 N4 126.2(2) . . ?
C22 C19 N4 121.54(19) . . ?
O6 C15 N3 120.83(19) . . ?
O6 C15 C22 128.08(19) . . ?
N3 C15 C22 111.08(18) . . ?
C14 N1 C13 116.66(19) . . ?
C11 C10 C14 117.60(19) . . ?
C11 C10 C9 124.53(18) . . ?
C14 C10 C9 117.84(18) . . ?
N1 C14 C10 124.1(2) . . ?
N1 C13 C12 123.6(2) . . ?
C19 C22 N6 105.41(18) . . ?
C19 C22 C15 123.88(18) . . ?
N6 C22 C15 130.71(19) . . ?
C13 C12 C11 118.8(2) . . ?
C10 C11 C12 119.3(2) . . ?
N5 C20 N6 113.01(18) . . ?

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
C2 C7 C6 C5 -0.1(3) . . . . ?
C6 C7 C2 C3 0.8(3) . . . . ?
C6 C7 C2 C1 -179.59(19) . . . . ?
C4 C3 C2 C7 -0.8(3) . . . . ?
C4 C3 C2 C1 179.66(18) . . . . ?
C7 C2 C1 O1 -179.11(19) . . . . ?
C3 C2 C1 O1 0.5(3) . . . . ?
C7 C2 C1 O2 1.1(3) . . . . ?
C3 C2 C1 O2 -179.37(18) . . . . ?
C8 O3 C4 C3 -1.7(3) . . . . ?
C8 O3 C4 C5 178.68(18) . . . . ?
C2 C3 C4 O3 -179.71(18) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C7 C6 C5 O4 178.35(19) . . . . ?
C7 C6 C5 C4 -0.8(3) . . . . ?
O3 C4 C5 O4 1.4(3) . . . . ?
C3 C4 C5 O4 -178.23(19) . . . . ?
O3 C4 C5 C6 -179.47(18) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C19 N4 C17 O7 178.97(18) . . . . ?
C18 N4 C17 O7 -4.9(3) . . . . ?
C19 N4 C17 N3 -0.6(3) . . . . ?
C18 N4 C17 N3 175.45(18) . . . . ?
C15 N3 C17 O7 -179.95(19) . . . . ?
C16 N3 C17 O7 0.7(3) . . . . ?
C15 N3 C17 N4 -0.3(3) . . . . ?
C16 N3 C17 N4 -179.70(18) . . . . ?
C20 N5 C19 C22 0.3(2) . . . . ?
C20 N5 C19 N4 -179.52(19) . . . . ?
C17 N4 C19 N5 -179.15(19) . . . . ?
C18 N4 C19 N5 4.8(3) . . . . ?
C17 N4 C19 C22 1.1(3) . . . . ?
C18 N4 C19 C22 -174.94(19) . . . . ?
C17 N3 C15 O6 179.9(2) . . . . ?
C16 N3 C15 O6 -0.8(3) . . . . ?
C17 N3 C15 C22 0.8(3) . . . . ?
C16 N3 C15 C22 -179.81(18) . . . . ?
O5 C9 C10 C11 167.5(2) . . . . ?
N2 C9 C10 C11 -12.5(3) . . . . ?
O5 C9 C10 C14 -10.4(3) . . . . ?
N2 C9 C10 C14 169.7(2) . . . . ?
C13 N1 C14 C10 -0.8(3) . . . . ?
C11 C10 C14 N1 0.4(3) . . . . ?
C9 C10 C14 N1 178.4(2) . . . . ?
C14 N1 C13 C12 0.9(3) . . . . ?
N5 C19 C22 N6 -0.4(2) . . . . ?
N4 C19 C22 N6 179.41(17) . . . . ?
N5 C19 C22 C15 179.66(19) . . . . ?
N4 C19 C22 C15 -0.5(3) . . . . ?
C20 N6 C22 C19 0.4(2) . . . . ?
C21 N6 C22 C19 -176.3(2) . . . . ?
C20 N6 C22 C15 -179.7(2) . . . . ?
C21 N6 C22 C15 3.6(4) . . . . ?
O6 C15 C22 C19 -179.3(2) . . . . ?
N3 C15 C22 C19 -0.4(3) . . . . ?
O6 C15 C22 N6 0.8(4) . . . . ?
N3 C15 C22 N6 179.70(19) . . . . ?
N1 C13 C12 C11 -0.6(4) . . . . ?
C14 C10 C11 C12 0.0(3) . . . . ?
C9 C10 C11 C12 -177.9(2) . . . . ?
C13 C12 C11 C10 0.1(3) . . . . ?
C19 N5 C20 N6 0.0(2) . . . . ?
C22 N6 C20 N5 -0.2(2) . . . . ?
C21 N6 C20 N5 176.5(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
_geom_hbond_publ_flag
C6 H6 O5 0.95 2.54 3.476(3) 168.5 2_666 yes
C16 H16C O3 0.98 2.63 3.574(3) 161.6 2_566 yes
C18 H18B O5 0.98 2.66 3.634(3) 175.7 . yes
C18 H18C O3 0.98 2.62 3.527(3) 154.5 . yes
C21 H21A N1 0.98 2.58 3.517(3) 160.8 2_666 yes
N2 H2B O1 0.93(3) 2.01(3) 2.936(2) 174(3) 1_456 yes
N2 H2A O7 0.92(3) 1.93(3) 2.835(2) 167(3) 2_557 yes
O2 H2 O5 0.94(4) 1.66(4) 2.588(2) 167(3) 1_654 yes
O4 H5 N5 0.86(3) 2.06(3) 2.751(2) 136(3) . yes

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_vanthbh2o
_database_code_depnum_ccdc_archive 'CCDC 1573860'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 N4 O7'
_chemical_formula_weight         368.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.3765(10)
_cell_length_b                   8.4985(10)
_cell_length_c                   12.2641(14)
_cell_angle_alpha                79.403(2)
_cell_angle_beta                 76.928(2)
_cell_angle_gamma                80.829(2)
_cell_volume                     829.58(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15774
_cell_measurement_theta_min      1.725
_cell_measurement_theta_max      28.325

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   0.932
_exptl_transmission_factor_max   0.943
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.50
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   
'Absorption corrections were made using the program SADABS (Sheldrick, 1996)'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15774
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.725
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4122
_reflns_number_gt                3649
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXS-2017 (Sheldrick, 2017)'
_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)+(0.0613P)²+0.2407P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4122
_refine_ls_number_parameters     281
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.062
_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
O1 O 0.4634(2) -0.18557(19) 0.04181(15) 0.0433(5) Uani 0.690(4) 1 d D U P A 1
O2 O 0.06924(11) 0.30727(10) 0.20847(7) 0.0297(2) Uani 1 1 d . . . . .
H2 H 0.916(2) 0.9018(19) 0.0720(14) 0.036(4) Uiso 1 1 d . . . . .
O3 O -0.12075(11) 0.15554(11) 0.38993(7) 0.0293(2) Uani 1 1 d . . . . .
O4 O 0.78774(10) 0.68803(9) 0.20975(7) 0.02609(19) Uani 1 1 d . . . . .
O5 O 0.89208(9) 1.18919(9) 0.02713(6) 0.02258(17) Uani 1 1 d . . . . .
H5 H -0.113(3) 0.259(3) 0.3729(17) 0.062(6) Uiso 1 1 d . . . . .
O6 O 0.21963(12) 0.39845(12) 0.41173(9) 0.0376(2) Uani 1 1 d D . . . .
H6A H 0.1307(13) 0.407(2) 0.3875(16) 0.058(6) Uiso 1 1 d D . . . .
H6B H 0.2882(19) 0.3241(17) 0.3837(16) 0.063(6) Uiso 1 1 d D . . . .
O7 O 0.88131(12) 0.47211(11) 0.39071(8) 0.0320(2) Uani 1 1 d D . . . .
H7A H 0.840(2) 0.5176(19) 0.4487(9) 0.048(5) Uiso 1 1 d D . . . .
H7B H 0.853(3) 0.540(2) 0.3366(12) 0.069(6) Uiso 1 1 d D . . . .
N1 N 0.67864(11) 1.17979(10) 0.17957(7) 0.01977(19) Uani 1 1 d . . . . .
N2 N 0.83103(11) 0.94176(11) 0.12087(7) 0.01908(19) Uani 1 1 d . . . . .
N3 N 0.49616(11) 0.86407(11) 0.36822(8) 0.02098(19) Uani 1 1 d . . . . .
N4 N 0.45236(11) 1.13409(11) 0.34123(8) 0.0219(2) Uani 1 1 d . . . . .
C1 C 0.3599(5) -0.2332(4) 0.1287(3) 0.0288(7) Uani 0.690(4) 1 d . U P A 1
H1 H 0.360043 -0.345547 0.155169 0.035 Uiso 0.690(4) 1 calc DR U P A 1
C2 C 0.23894(14) -0.11797(15) 0.18955(10) 0.0272(2) Uani 1 1 d . . . . .
C3 C 0.22149(14) 0.05058(15) 0.16059(9) 0.0247(2) Uani 1 1 d . . . . .
H3 H 0.291988 0.100614 0.095930 0.030 Uiso 1 1 calc R U . . .
C4 C 0.10130(14) 0.14305(13) 0.22667(9) 0.0220(2) Uani 1 1 d . . . . .
C5 C -0.00159(13) 0.06796(14) 0.32352(9) 0.0218(2) Uani 1 1 d . . . . .
C6 C 0.01664(15) -0.09851(14) 0.35108(10) 0.0264(2) Uani 1 1 d . . . . .
H6 H -0.052840 -0.149020 0.416092 0.032 Uiso 1 1 calc R U . . .
C7 C 0.13627(15) -0.19149(14) 0.28380(11) 0.0287(2) Uani 1 1 d . . . . .
H7 H 0.147897 -0.305735 0.302324 0.034 Uiso 1 1 calc R U . . .
C8 C 0.15654(18) 0.39117(16) 0.10583(11) 0.0361(3) Uani 1 1 d . . . . .
H8A H 0.275112 0.373130 0.105589 0.054 Uiso 1 1 calc R U . . .
H8B H 0.118011 0.506881 0.100738 0.054 Uiso 1 1 calc R U . . .
H8C H 0.136267 0.350970 0.040848 0.054 Uiso 1 1 calc R U . . .
C9 C 0.74699(13) 0.83452(12) 0.20479(8) 0.0187(2) Uani 1 1 d . . . . .
C10 C 0.80537(12) 1.10857(12) 0.10485(8) 0.0182(2) Uani 1 1 d . . . . .
C11 C 0.58475(12) 1.08300(12) 0.26342(8) 0.0182(2) Uani 1 1 d . . . . .
C12 C 0.40331(13) 0.99656(14) 0.40191(9) 0.0234(2) Uani 1 1 d . . . . .
H12 H 0.310969 0.993123 0.463354 0.028 Uiso 1 1 calc R U . . .
C13 C 0.61619(12) 0.91711(12) 0.27736(8) 0.0188(2) Uani 1 1 d . . . . .
C14 C 0.47279(14) 0.69760(14) 0.41788(10) 0.0287(3) Uani 1 1 d . . . . .
H14A H 0.562478 0.649826 0.457480 0.043 Uiso 1 1 calc R U . . .
H14B H 0.473430 0.635632 0.357792 0.043 Uiso 1 1 calc R U . . .
H14C H 0.366777 0.695508 0.471715 0.043 Uiso 1 1 calc R U . . .
C15 C 0.64776(15) 1.35621(13) 0.16725(11) 0.0290(3) Uani 1 1 d . . . . .
H15A H 0.567502 1.388210 0.233402 0.043 Uiso 1 1 calc R U . . .
H15B H 0.603805 1.398544 0.098600 0.043 Uiso 1 1 calc R U . . .
H15C H 0.751345 1.399824 0.161494 0.043 Uiso 1 1 calc R U . . .
O1A O 0.4203(5) -0.3363(4) 0.1231(3) 0.0508(13) Uani 0.310(4) 1 d D U P A 2
C1A C 0.3806(9) -0.1870(6) 0.1042(5) 0.0186(13) Uani 0.310(4) 1 d . U P A 2
H1A H 0.435941 -0.120970 0.040148 0.022 Uiso 0.310(4) 1 calc DR U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.260(2) . ?
O2 C4 1.3648(13) . ?
O2 C8 1.4309(14) . ?
O3 C5 1.3536(13) . ?
O4 C9 1.2313(13) . ?
O5 C10 1.2291(13) . ?
N1 C11 1.3718(13) . ?
N1 C10 1.3756(13) . ?
N1 C15 1.4657(14) . ?
N2 C10 1.3835(13) . ?
N2 C9 1.3846(13) . ?
N3 C12 1.3379(14) . ?
N3 C13 1.3815(13) . ?
N3 C14 1.4589(14) . ?
N4 C12 1.3355(14) . ?
N4 C11 1.3598(13) . ?
C1 C2 1.468(4) . ?
C2 C7 1.3864(18) . ?
C2 C3 1.4033(17) . ?
C2 C1A 1.513(7) . ?
C3 C4 1.3787(16) . ?
C4 C5 1.4122(14) . ?
C5 C6 1.3848(16) . ?
C6 C7 1.3866(17) . ?
C9 C13 1.4244(14) . ?
C11 C13 1.3782(14) . ?
O1A C1A 1.252(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C8 117.41(9) . . ?
C11 N1 C10 118.78(9) . . ?
C11 N1 C15 122.02(9) . . ?
C10 N1 C15 119.20(9) . . ?
C10 N2 C9 128.34(9) . . ?
C12 N3 C13 106.24(9) . . ?
C12 N3 C14 126.31(9) . . ?
C13 N3 C14 127.46(9) . . ?
C12 N4 C11 103.22(9) . . ?
O1 C1 C2 121.0(2) . . ?
C7 C2 C3 120.43(11) . . ?
C7 C2 C1 113.19(13) . . ?
C3 C2 C1 126.37(13) . . ?
C7 C2 C1A 131.59(17) . . ?
C3 C2 C1A 107.97(16) . . ?
C4 C3 C2 119.51(10) . . ?
O2 C4 C3 126.00(10) . . ?
O2 C4 C5 114.08(10) . . ?
C3 C4 C5 119.92(10) . . ?
O3 C5 C6 118.72(10) . . ?
O3 C5 C4 121.27(10) . . ?
C6 C5 C4 120.01(10) . . ?
C5 C6 C7 120.01(11) . . ?
C2 C7 C6 120.10(11) . . ?
O4 C9 N2 120.72(9) . . ?
O4 C9 C13 128.02(10) . . ?
N2 C9 C13 111.25(9) . . ?
O5 C10 N1 121.63(9) . . ?
O5 C10 N2 121.32(9) . . ?
N1 C10 N2 117.05(9) . . ?
N4 C11 N1 126.03(9) . . ?
N4 C11 C13 111.72(9) . . ?
N1 C11 C13 122.25(9) . . ?
N4 C12 N3 113.83(9) . . ?
C11 C13 N3 104.99(9) . . ?
C11 C13 C9 122.28(9) . . ?
N3 C13 C9 132.71(10) . . ?
O1A C1A C2 115.9(4) . . ?

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
O1 C1 C2 C7 -179.2(3) . . . . ?
O1 C1 C2 C3 0.8(4) . . . . ?
C7 C2 C3 C4 0.04(17) . . . . ?
C1 C2 C3 C4 -180.0(2) . . . . ?
C1A C2 C3 C4 -179.1(3) . . . . ?
C8 O2 C4 C3 6.56(17) . . . . ?
C8 O2 C4 C5 -173.72(10) . . . . ?
C2 C3 C4 O2 -179.45(10) . . . . ?
C2 C3 C4 C5 0.84(16) . . . . ?
O2 C4 C5 O3 0.34(15) . . . . ?
C3 C4 C5 O3 -179.92(10) . . . . ?
O2 C4 C5 C6 179.29(9) . . . . ?
C3 C4 C5 C6 -0.98(16) . . . . ?
O3 C5 C6 C7 179.19(10) . . . . ?
C4 C5 C6 C7 0.21(17) . . . . ?
C3 C2 C7 C6 -0.80(17) . . . . ?
C1 C2 C7 C6 179.20(19) . . . . ?
C1A C2 C7 C6 178.1(4) . . . . ?
C5 C6 C7 C2 0.67(17) . . . . ?
C10 N2 C9 O4 -177.87(10) . . . . ?
C10 N2 C9 C13 2.38(15) . . . . ?
C11 N1 C10 O5 178.98(9) . . . . ?
C15 N1 C10 O5 -0.93(15) . . . . ?
C11 N1 C10 N2 -0.93(14) . . . . ?
C15 N1 C10 N2 179.16(9) . . . . ?
C9 N2 C10 O5 178.69(10) . . . . ?
C9 N2 C10 N1 -1.40(16) . . . . ?
C12 N4 C11 N1 179.20(10) . . . . ?
C12 N4 C11 C13 -0.48(12) . . . . ?
C10 N1 C11 N4 -177.67(9) . . . . ?
C15 N1 C11 N4 2.23(16) . . . . ?
C10 N1 C11 C13 1.98(15) . . . . ?
C15 N1 C11 C13 -178.11(10) . . . . ?
C11 N4 C12 N3 0.54(12) . . . . ?
C13 N3 C12 N4 -0.40(12) . . . . ?
C14 N3 C12 N4 -179.95(10) . . . . ?
N4 C11 C13 N3 0.27(12) . . . . ?
N1 C11 C13 N3 -179.43(9) . . . . ?
N4 C11 C13 C9 178.85(9) . . . . ?
N1 C11 C13 C9 -0.85(16) . . . . ?
C12 N3 C13 C11 0.07(11) . . . . ?
C14 N3 C13 C11 179.61(10) . . . . ?
C12 N3 C13 C9 -178.30(11) . . . . ?
C14 N3 C13 C9 1.24(19) . . . . ?
O4 C9 C13 C11 179.08(10) . . . . ?
N2 C9 C13 C11 -1.20(14) . . . . ?
O4 C9 C13 N3 -2.8(2) . . . . ?
N2 C9 C13 N3 176.95(10) . . . . ?
C7 C2 C1A O1A -4.2(8) . . . . ?
C3 C2 C1A O1A 174.9(5) . . . . ?

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
_geom_hbond_publ_flag
N2 H2 O5 0.888(18) 1.929(18) 2.8158(12) 176.7(15) 2_775 yes
O3 H5 O7 0.87(2) 1.86(2) 2.6950(13) 160(2) 1_455 yes
O6 H6A O7 0.850(2) 2.067(8) 2.8627(14) 155.6(18) 1_455 yes
O6 H6B N4 0.850(2) 2.012(4) 2.8551(13) 171(2) 1_545 yes
O7 H7A O6 0.850(2) 1.907(4) 2.7482(13) 170.2(17) 2_666 yes
O7 H7B O4 0.850(2) 1.932(3) 2.7816(12) 177(2) . yes
C12 H12 O3 0.95 2.43 3.2892(14) 151.1 2_566 yes
C14 H14A O6 0.98 2.63 3.5789(16) 163.1 2_666 yes

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.044

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vadabcoh2o
_database_code_depnum_ccdc_archive 'CCDC 1573867'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H42 N4 O9'
_chemical_formula_weight         578.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   25.812(2)
_cell_length_b                   10.0083(9)
_cell_length_c                   11.1713(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.700(2)
_cell_angle_gamma                90
_cell_volume                     2844.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    33471
_cell_measurement_theta_min      1.601
_cell_measurement_theta_max      28.388

_exptl_crystal_description       needles
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   0.958
_exptl_transmission_factor_max   0.990
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   
'Absorption corrections were made using the program SADABS (Sheldrick, 1996)'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33471
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.601
_diffrn_reflns_theta_max         28.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7090
_reflns_number_gt                5794
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXS-2017 (Sheldrick, 2017)'
_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)+(0.0537P)²+2.1316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7090
_refine_ls_number_parameters     396
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1290
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
O2A O 0.03057(5) 0.28052(15) 0.53879(13) 0.0334(3) Uani 1 1 d . . . . .
N2B N 0.03590(5) 0.61404(14) 0.25676(13) 0.0204(3) Uani 1 1 d D . . . .
O1A O 0.05681(5) 0.40991(14) 0.70064(13) 0.0320(3) Uani 1 1 d . . . . .
O3A O 0.25438(5) 0.43485(15) 0.74242(12) 0.0335(3) Uani 1 1 d . . . . .
O4A O 0.27799(5) 0.30423(13) 0.54966(12) 0.0259(3) Uani 1 1 d . . . . .
N2A N 0.46376(5) 0.39838(14) 0.79966(13) 0.0212(3) Uani 1 1 d . . . . .
C3A C 0.16070(6) 0.39272(16) 0.67603(15) 0.0203(3) Uani 1 1 d . . . . .
H3A H 0.151317 0.440059 0.742926 0.024 Uiso 1 1 calc R U . . .
N1A N 0.36719(5) 0.36595(14) 0.71305(12) 0.0210(3) Uani 1 1 d . . . . .
C2A C 0.12161(6) 0.33204(16) 0.59144(15) 0.0191(3) Uani 1 1 d . . . . .
C5A C 0.22693(6) 0.31512(16) 0.56394(14) 0.0198(3) Uani 1 1 d . . . . .
N1B N 0.12555(5) 0.64471(15) 0.19505(14) 0.0246(3) Uani 1 1 d . . . . .
C1A C 0.06513(6) 0.33987(17) 0.60887(15) 0.0213(3) Uani 1 1 d . . . . .
C6A C 0.18808(7) 0.25650(17) 0.47971(15) 0.0220(3) Uani 1 1 d . . . . .
H6A H 0.197391 0.210437 0.412064 0.026 Uiso 1 1 calc R U . . .
C4A C 0.21281(6) 0.38414(16) 0.66279(15) 0.0201(3) Uani 1 1 d . . . . .
C7A C 0.13555(7) 0.26436(17) 0.49313(15) 0.0219(3) Uani 1 1 d . . . . .
H7A H 0.109216 0.223410 0.435034 0.026 Uiso 1 1 calc R U . . .
C9B C 0.03577(7) 0.55235(18) 0.13604(16) 0.0259(4) Uani 1 1 d . . . . .
H9AA H 0.006137 0.587855 0.076682 0.031 Uiso 1 1 calc R U . . .
H9AB H 0.031592 0.454305 0.141249 0.031 Uiso 1 1 calc R U . . .
C13A C 0.43942(7) 0.53024(18) 0.76259(19) 0.0311(4) Uani 1 1 d . . . . .
H13A H 0.454274 0.566930 0.693346 0.037 Uiso 1 1 calc R U . . .
H13B H 0.446494 0.594304 0.830923 0.037 Uiso 1 1 calc R U . . .
C8A C 0.24401(7) 0.53770(19) 0.82281(17) 0.0299(4) Uani 1 1 d . . . . .
H8A H 0.224976 0.610607 0.776038 0.045 Uiso 1 1 calc R U . . .
H8B H 0.277285 0.571600 0.867869 0.045 Uiso 1 1 calc R U . . .
H8C H 0.222621 0.501827 0.879981 0.045 Uiso 1 1 calc R U . . .
C13B C 0.07663(7) 0.5490(2) 0.34707(17) 0.0301(4) Uani 1 1 d . . . . .
H26B H 0.066862 0.454866 0.358743 0.036 Uiso 1 1 calc R U . . .
H27B H 0.079633 0.595638 0.426115 0.036 Uiso 1 1 calc R U . . .
C11A C 0.37952(7) 0.3045(2) 0.83302(16) 0.0294(4) Uani 1 1 d . . . . .
H11A H 0.374949 0.206476 0.825265 0.035 Uiso 1 1 calc R U . . .
H11B H 0.354872 0.338151 0.885001 0.035 Uiso 1 1 calc R U . . .
C10B C 0.08830(8) 0.5857(2) 0.09503(17) 0.0323(4) Uani 1 1 d . . . . .
H21B H 0.103606 0.503226 0.066702 0.039 Uiso 1 1 calc R U . . .
H20B H 0.082012 0.649292 0.026212 0.039 Uiso 1 1 calc R U . . .
C9A C 0.45857(7) 0.3077(2) 0.69210(18) 0.0333(4) Uani 1 1 d . . . . .
H9A H 0.470866 0.216820 0.717782 0.040 Uiso 1 1 calc R U . . .
H9B H 0.480135 0.341356 0.633163 0.040 Uiso 1 1 calc R U . . .
C12A C 0.43650(7) 0.33623(19) 0.89337(16) 0.0268(4) Uani 1 1 d . . . . .
H12B H 0.436511 0.398517 0.962220 0.032 Uiso 1 1 calc R U . . .
H12A H 0.454809 0.253218 0.924663 0.032 Uiso 1 1 calc R U . . .
C14B C 0.12950(7) 0.5550(2) 0.3008(2) 0.0384(5) Uani 1 1 d . . . . .
H29B H 0.157229 0.587729 0.366383 0.046 Uiso 1 1 calc R U . . .
H28B H 0.139410 0.464221 0.277576 0.046 Uiso 1 1 calc R U . . .
C14A C 0.37983(8) 0.5082(2) 0.7257(2) 0.0416(5) Uani 1 1 d . . . . .
H14A H 0.361372 0.547822 0.788029 0.050 Uiso 1 1 calc R U . . .
H14B H 0.367318 0.554100 0.647698 0.050 Uiso 1 1 calc R U . . .
C10A C 0.40026(7) 0.3040(2) 0.63340(18) 0.0361(5) Uani 1 1 d . . . . .
H10A H 0.395481 0.352121 0.554881 0.043 Uiso 1 1 calc R U . . .
H10B H 0.389191 0.210115 0.617084 0.043 Uiso 1 1 calc R U . . .
C4B C 0.27422(6) 0.87995(16) 0.64094(14) 0.0195(3) Uani 1 1 d . . . . .
C12B C 0.04733(7) 0.75903(17) 0.24824(17) 0.0261(4) Uani 1 1 d . . . . .
H24B H 0.042566 0.804936 0.324130 0.031 Uiso 1 1 calc R U . . .
H25B H 0.023043 0.799652 0.179892 0.031 Uiso 1 1 calc R U . . .
C6B C 0.27421(7) 0.70103(17) 0.49736(16) 0.0240(3) Uani 1 1 d . . . . .
H6B H 0.256298 0.631797 0.448913 0.029 Uiso 1 1 calc R U . . .
C11B C 0.10467(7) 0.77409(19) 0.2276(2) 0.0323(4) Uani 1 1 d . . . . .
H22B H 0.106171 0.839307 0.161640 0.039 Uiso 1 1 calc R U . . .
H23B H 0.126616 0.808574 0.302483 0.039 Uiso 1 1 calc R U . . .
C5B C 0.24722(6) 0.77827(17) 0.56931(15) 0.0207(3) Uani 1 1 d . . . . .
O3B O 0.24399(5) 0.95162(12) 0.70743(12) 0.0262(3) Uani 1 1 d . . . . .
C3B C 0.32722(6) 0.90102(16) 0.64038(15) 0.0202(3) Uani 1 1 d . . . . .
H3B H 0.345362 0.969135 0.689879 0.024 Uiso 1 1 calc R U . . .
C2B C 0.35424(6) 0.82248(16) 0.56725(14) 0.0193(3) Uani 1 1 d . . . . .
C7B C 0.32719(6) 0.72350(17) 0.49512(15) 0.0223(3) Uani 1 1 d . . . . .
H7B H 0.344977 0.670884 0.444002 0.027 Uiso 1 1 calc R U . . .
C8B C 0.26839(7) 1.06261(17) 0.77446(17) 0.0264(4) Uani 1 1 d . . . . .
H8AA H 0.281072 1.125619 0.718786 0.040 Uiso 1 1 calc R U . . .
H8AB H 0.298065 1.031150 0.834310 0.040 Uiso 1 1 calc R U . . .
H8AC H 0.242791 1.107361 0.816369 0.040 Uiso 1 1 calc R U . . .
O1B O 0.43430(5) 0.93623(13) 0.63960(12) 0.0272(3) Uani 1 1 d . . . . .
O2B O 0.43717(5) 0.76444(15) 0.51476(13) 0.0344(3) Uani 1 1 d . . . . .
O4B O 0.19545(5) 0.75573(14) 0.56634(13) 0.0300(3) Uani 1 1 d . . . . .
O6 O 0.43074(7) -0.01402(16) 0.89276(16) 0.0422(4) Uani 1 1 d . . . . .
C1B C 0.41247(6) 0.84133(17) 0.57266(15) 0.0220(3) Uani 1 1 d . . . . .
H5B H 0.1831(10) 0.805(3) 0.617(2) 0.043(7) Uiso 1 1 d . . . . .
H5A H 0.2978(10) 0.334(3) 0.617(2) 0.048(7) Uiso 1 1 d . . . . .
H6AB H 0.4347(13) -0.093(4) 0.936(3) 0.085(11) Uiso 1 1 d . . . . .
H6AA H 0.4274(11) -0.034(3) 0.812(3) 0.061(8) Uiso 1 1 d . . . . .
H2A H 0.5011(10) 0.412(2) 0.829(2) 0.041(6) Uiso 1 1 d . . . . .
H2B H 0.0022(5) 0.603(3) 0.274(3) 0.074(9) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2A C1A 1.235(2) . ?
N2B C13B 1.480(2) . ?
N2B C9B 1.483(2) . ?
N2B C12B 1.487(2) . ?
O1A C1A 1.289(2) . ?
O3A C4A 1.371(2) . ?
O3A C8A 1.421(2) . ?
O4A C5A 1.3584(19) . ?
N2A C13A 1.490(2) . ?
N2A C12A 1.492(2) . ?
N2A C9A 1.494(2) . ?
C3A C4A 1.381(2) . ?
C3A C2A 1.399(2) . ?
N1A C11A 1.460(2) . ?
N1A C14A 1.462(2) . ?
N1A C10A 1.470(2) . ?
C2A C7A 1.388(2) . ?
C2A C1A 1.505(2) . ?
C5A C6A 1.385(2) . ?
C5A C4A 1.402(2) . ?
N1B C10B 1.469(2) . ?
N1B C11B 1.471(2) . ?
N1B C14B 1.474(2) . ?
C6A C7A 1.391(2) . ?
C9B C10B 1.539(2) . ?
C13A C14A 1.540(3) . ?
C13B C14B 1.540(3) . ?
C11A C12A 1.544(2) . ?
C9A C10A 1.538(3) . ?
C4B O3B 1.3676(19) . ?
C4B C3B 1.385(2) . ?
C4B C5B 1.405(2) . ?
C12B C11B 1.543(2) . ?
C6B C5B 1.385(2) . ?
C6B C7B 1.390(2) . ?
C5B O4B 1.3501(19) . ?
O3B C8B 1.426(2) . ?
C3B C2B 1.401(2) . ?
C2B C7B 1.389(2) . ?
C2B C1B 1.506(2) . ?
O1B C1B 1.279(2) . ?
O2B C1B 1.247(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13B N2B C9B 109.24(14) . . ?
C13B N2B C12B 110.29(14) . . ?
C9B N2B C12B 108.55(14) . . ?
C4A O3A C8A 117.92(13) . . ?
C13A N2A C12A 109.74(14) . . ?
C13A N2A C9A 109.76(15) . . ?
C12A N2A C9A 108.80(14) . . ?
C4A C3A C2A 120.35(15) . . ?
C11A N1A C14A 108.11(16) . . ?
C11A N1A C10A 108.60(15) . . ?
C14A N1A C10A 109.06(16) . . ?
C7A C2A C3A 119.51(15) . . ?
C7A C2A C1A 120.90(14) . . ?
C3A C2A C1A 119.59(15) . . ?
O4A C5A C6A 119.47(15) . . ?
O4A C5A C4A 121.21(15) . . ?
C6A C5A C4A 119.32(15) . . ?
C10B N1B C11B 108.76(15) . . ?
C10B N1B C14B 108.22(15) . . ?
C11B N1B C14B 108.48(16) . . ?
O2A C1A O1A 124.47(15) . . ?
O2A C1A C2A 120.31(15) . . ?
O1A C1A C2A 115.21(14) . . ?
C5A C6A C7A 120.67(15) . . ?
O3A C4A C3A 125.30(15) . . ?
O3A C4A C5A 114.51(14) . . ?
C3A C4A C5A 120.16(15) . . ?
C2A C7A C6A 120.00(15) . . ?
N2B C9B C10B 108.26(14) . . ?
N2A C13A C14A 107.63(14) . . ?
N2B C13B C14B 108.80(14) . . ?
N1A C11A C12A 110.99(14) . . ?
N1B C10B C9B 110.92(14) . . ?
N2A C9A C10A 107.85(14) . . ?
N2A C12A C11A 107.84(14) . . ?
N1B C14B C13B 110.31(15) . . ?
N1A C14A C13A 111.20(15) . . ?
N1A C10A C9A 110.98(15) . . ?
O3B C4B C3B 125.23(15) . . ?
O3B C4B C5B 114.56(14) . . ?
C3B C4B C5B 120.21(15) . . ?
N2B C12B C11B 108.10(13) . . ?
C5B C6B C7B 120.84(16) . . ?
N1B C11B C12B 110.57(14) . . ?
O4B C5B C6B 119.02(15) . . ?
O4B C5B C4B 121.93(15) . . ?
C6B C5B C4B 119.03(15) . . ?
C4B O3B C8B 116.87(13) . . ?
C4B C3B C2B 120.41(15) . . ?
C7B C2B C3B 119.17(15) . . ?
C7B C2B C1B 120.90(15) . . ?
C3B C2B C1B 119.85(15) . . ?
C2B C7B C6B 120.32(15) . . ?
O2B C1B O1B 123.21(16) . . ?
O2B C1B C2B 119.72(16) . . ?
O1B C1B C2B 117.05(15) . . ?

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
C4A C3A C2A C7A -0.8(2) . . . . ?
C4A C3A C2A C1A 178.65(15) . . . . ?
C7A C2A C1A O2A 3.5(2) . . . . ?
C3A C2A C1A O2A -175.93(16) . . . . ?
C7A C2A C1A O1A -177.31(15) . . . . ?
C3A C2A C1A O1A 3.3(2) . . . . ?
O4A C5A C6A C7A 179.01(15) . . . . ?
C4A C5A C6A C7A -0.7(2) . . . . ?
C8A O3A C4A C3A -20.8(3) . . . . ?
C8A O3A C4A C5A 161.48(16) . . . . ?
C2A C3A C4A O3A -177.21(16) . . . . ?
C2A C3A C4A C5A 0.4(2) . . . . ?
O4A C5A C4A O3A -1.5(2) . . . . ?
C6A C5A C4A O3A 178.18(15) . . . . ?
O4A C5A C4A C3A -179.35(15) . . . . ?
C6A C5A C4A C3A 0.3(2) . . . . ?
C3A C2A C7A C6A 0.4(2) . . . . ?
C1A C2A C7A C6A -178.98(15) . . . . ?
C5A C6A C7A C2A 0.3(3) . . . . ?
C13B N2B C9B C10B -65.95(18) . . . . ?
C12B N2B C9B C10B 54.35(18) . . . . ?
C12A N2A C13A C14A -52.8(2) . . . . ?
C9A N2A C13A C14A 66.7(2) . . . . ?
C9B N2B C13B C14B 53.7(2) . . . . ?
C12B N2B C13B C14B -65.5(2) . . . . ?
C14A N1A C11A C12A -53.0(2) . . . . ?
C10A N1A C11A C12A 65.2(2) . . . . ?
C11B N1B C10B C9B -64.91(19) . . . . ?
C14B N1B C10B C9B 52.8(2) . . . . ?
N2B C9B C10B N1B 10.7(2) . . . . ?
C13A N2A C9A C10A -53.2(2) . . . . ?
C12A N2A C9A C10A 66.9(2) . . . . ?
C13A N2A C12A C11A 65.72(19) . . . . ?
C9A N2A C12A C11A -54.39(19) . . . . ?
N1A C11A C12A N2A -10.5(2) . . . . ?
C10B N1B C14B C13B -65.3(2) . . . . ?
C11B N1B C14B C13B 52.5(2) . . . . ?
N2B C13B C14B N1B 10.9(2) . . . . ?
C11A N1A C14A C13A 66.7(2) . . . . ?
C10A N1A C14A C13A -51.2(2) . . . . ?
N2A C13A C14A N1A -12.2(3) . . . . ?
C11A N1A C10A C9A -52.3(2) . . . . ?
C14A N1A C10A C9A 65.3(2) . . . . ?
N2A C9A C10A N1A -11.6(2) . . . . ?
C13B N2B C12B C11B 51.73(19) . . . . ?
C9B N2B C12B C11B -67.91(18) . . . . ?
C10B N1B C11B C12B 50.9(2) . . . . ?
C14B N1B C11B C12B -66.6(2) . . . . ?
N2B C12B C11B N1B 13.0(2) . . . . ?
C7B C6B C5B O4B 178.16(16) . . . . ?
C7B C6B C5B C4B -0.3(3) . . . . ?
O3B C4B C5B O4B 0.8(2) . . . . ?
C3B C4B C5B O4B -179.20(15) . . . . ?
O3B C4B C5B C6B 179.19(15) . . . . ?
C3B C4B C5B C6B -0.8(2) . . . . ?
C3B C4B O3B C8B 4.7(2) . . . . ?
C5B C4B O3B C8B -175.29(15) . . . . ?
O3B C4B C3B C2B -179.13(15) . . . . ?
C5B C4B C3B C2B 0.9(2) . . . . ?
C4B C3B C2B C7B 0.2(2) . . . . ?
C4B C3B C2B C1B -176.64(15) . . . . ?
C3B C2B C7B C6B -1.2(2) . . . . ?
C1B C2B C7B C6B 175.52(15) . . . . ?
C5B C6B C7B C2B 1.3(3) . . . . ?
C7B C2B C1B O2B -2.3(2) . . . . ?
C3B C2B C1B O2B 174.41(16) . . . . ?
C7B C2B C1B O1B 178.80(15) . . . . ?
C3B C2B C1B O1B -4.5(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
_geom_hbond_publ_flag
C9B H9AA O2A 0.99 2.42 3.292(2) 146.2 2 yes
C9B H9AB O2A 0.99 2.61 3.500(2) 149.2 4_565 yes
C13A H13B O2B 0.99 2.54 3.495(3) 162.6 4_576 yes
C12A H12B O1B 0.99 2.59 3.579(2) 178.6 4_576 yes
C12B H25B O2A 0.99 2.60 3.493(2) 149.4 2 yes
C8B H8AA O4A 0.98 2.59 3.525(2) 159.0 1_565 yes
O4B H5B N1B 0.86(3) 1.91(3) 2.6816(19) 149(2) 4_576 yes
O4B H5B O3B 0.86(3) 2.26(2) 2.6893(18) 111(2) . yes
O4A H5A O3A 0.89(3) 2.18(3) 2.6757(18) 115(2) . yes
O4A H5A N1A 0.89(3) 1.95(3) 2.7566(19) 150(2) . yes
O6 H6AB O2B 0.92(4) 1.92(4) 2.844(2) 175(3) 4_566 yes
O6 H6AA O1B 0.91(3) 1.99(3) 2.888(2) 169(3) 1_545 yes
N2A H2A O1B 0.97(2) 1.66(2) 2.6316(18) 173(2) 2_646 yes
N2A H2A O2B 0.97(2) 2.61(2) 3.294(2) 127.0(17) 2_646 yes
N2B H2B O2A 0.931(2) 2.65(3) 3.2548(19) 123(2) 3_566 yes
N2B H2B O1A 0.931(2) 1.599(3) 2.5286(18) 177(3) 3_566 yes

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_vapzo
_database_code_depnum_ccdc_archive 'CCDC 1573865'
_audit_update_record             
;
2017-12-07 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 N2 O5'
_chemical_formula_weight         264.24

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                   7.3089(6)
_cell_length_b                   7.3878(6)
_cell_length_c                   10.8979(9)
_cell_angle_alpha                94.1980(10)
_cell_angle_beta                 90.084(2)
_cell_angle_gamma                98.0510(10)
_cell_volume                     581.05(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    14056
_cell_measurement_theta_min      1.874
_cell_measurement_theta_max      28.324

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   0.940
_exptl_transmission_factor_max   0.953
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.42
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   
'Absorption corrections were made using the program SADABS (Sheldrick, 1996)'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14056
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.874
_diffrn_reflns_theta_max         28.324
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2873
_reflns_number_gt                2626
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXS-2017 (Sheldrick, 2017)'
_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)+(0.0596P)²+0.1403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2873
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
O1 O 0.24945(10) 0.21843(10) 0.96105(7) 0.02429(18) Uani 1 1 d . . . . .
O2 O 0.46200(11) 0.09934(12) 0.84449(8) 0.0317(2) Uani 1 1 d . . . . .
C2 C 0.15055(13) 0.01649(12) 0.78500(8) 0.0179(2) Uani 1 1 d . . . . .
C1 C 0.28859(14) 0.12124(13) 0.87254(9) 0.0196(2) Uani 1 1 d . . . . .
C5 C -0.11277(13) -0.18349(13) 0.62374(9) 0.0186(2) Uani 1 1 d . . . . .
C3 C 0.20594(13) -0.06453(13) 0.67328(9) 0.0181(2) Uani 1 1 d . . . . .
H3 H 0.333259 -0.052458 0.653087 0.022 Uiso 1 1 calc R U . . .
O4 O -0.24595(10) -0.28225(11) 0.54996(7) 0.02682(19) Uani 1 1 d . . . . .
C4 C 0.07544(13) -0.16217(13) 0.59224(9) 0.01742(19) Uani 1 1 d . . . . .
C7 C -0.03577(14) -0.00063(13) 0.81467(9) 0.0200(2) Uani 1 1 d . . . . .
H7 H -0.073793 0.056540 0.889423 0.024 Uiso 1 1 calc R U . . .
C6 C -0.16611(13) -0.10175(14) 0.73448(9) 0.0202(2) Uani 1 1 d . . . . .
H6 H -0.293113 -0.115180 0.755577 0.024 Uiso 1 1 calc R U . . .
O3 O 0.11457(10) -0.24520(10) 0.48078(6) 0.02249(17) Uani 1 1 d . . . . .
C8 C 0.30266(14) -0.21488(15) 0.44307(10) 0.0246(2) Uani 1 1 d . . . . .
H8A H 0.347090 -0.083042 0.449473 0.037 Uiso 1 1 calc R U . . .
H8B H 0.311687 -0.263895 0.357603 0.037 Uiso 1 1 calc R U . . .
H8C H 0.378336 -0.276900 0.496229 0.037 Uiso 1 1 calc R U . . .
O5 O 0.73303(11) 0.29621(12) -0.03132(7) 0.0317(2) Uani 1 1 d . . . . .
N1 N 0.77378(13) 0.53996(12) 0.31662(8) 0.0242(2) Uani 1 1 d . . . . .
N2 N 0.74364(12) 0.36899(11) 0.08115(8) 0.02009(19) Uani 1 1 d . . . . .
C12 C 0.58972(14) 0.39359(14) 0.14598(9) 0.0225(2) Uani 1 1 d . . . . .
H12 H 0.470306 0.353925 0.111180 0.027 Uiso 1 1 calc R U . . .
C9 C 0.91192(14) 0.42240(14) 0.13390(9) 0.0210(2) Uani 1 1 d . . . . .
H9 H 1.021103 0.400090 0.091675 0.025 Uiso 1 1 calc R U . . .
C10 C 0.92153(15) 0.51005(14) 0.25047(10) 0.0237(2) Uani 1 1 d . . . . .
H10 H 1.040338 0.551548 0.285683 0.028 Uiso 1 1 calc R U . . .
C11 C 0.61004(15) 0.47731(14) 0.26338(10) 0.0237(2) Uani 1 1 d . . . . .
H11 H 0.501613 0.491269 0.309011 0.028 Uiso 1 1 calc R U . . .
H2 H 0.542(3) 0.163(3) 0.8973(18) 0.064(6) Uiso 1 1 d . . . . .
H5 H -0.208(3) -0.325(2) 0.4848(19) 0.054(5) Uiso 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
O1 C1 1.2185(12) . ?
O2 C1 1.3332(12) . ?
C2 C7 1.3907(13) . ?
C2 C3 1.4026(13) . ?
C2 C1 1.4823(13) . ?
C5 O4 1.3562(12) . ?
C5 C6 1.3906(13) . ?
C5 C4 1.4084(13) . ?
C3 C4 1.3863(13) . ?
C4 O3 1.3691(11) . ?
C7 C6 1.3899(14) . ?
O3 C8 1.4276(12) . ?
O5 N2 1.2997(11) . ?
N1 C10 1.3344(14) . ?
N1 C11 1.3367(14) . ?
N2 C9 1.3519(13) . ?
N2 C12 1.3559(13) . ?
C12 C11 1.3782(14) . ?
C9 C10 1.3801(14) . ?

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
C7 C2 C3 120.02(9) . . ?
C7 C2 C1 119.21(8) . . ?
C3 C2 C1 120.77(9) . . ?
O1 C1 O2 122.88(9) . . ?
O1 C1 C2 124.04(9) . . ?
O2 C1 C2 113.08(8) . . ?
O4 C5 C6 118.08(9) . . ?
O4 C5 C4 122.41(9) . . ?
C6 C5 C4 119.51(9) . . ?
C4 C3 C2 120.19(9) . . ?
O3 C4 C3 124.84(9) . . ?
O3 C4 C5 115.39(8) . . ?
C3 C4 C5 119.76(9) . . ?
C6 C7 C2 119.72(9) . . ?
C7 C6 C5 120.77(9) . . ?
C4 O3 C8 116.37(8) . . ?
C10 N1 C11 115.69(9) . . ?
O5 N2 C9 119.11(8) . . ?
O5 N2 C12 121.36(8) . . ?
C9 N2 C12 119.53(9) . . ?
N2 C12 C11 118.64(9) . . ?
N2 C9 C10 118.51(9) . . ?
N1 C10 C9 123.86(9) . . ?
N1 C11 C12 123.66(10) . . ?

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
C7 C2 C1 O1 -11.91(15) . . . . ?
C3 C2 C1 O1 167.97(9) . . . . ?
C7 C2 C1 O2 168.39(9) . . . . ?
C3 C2 C1 O2 -11.73(14) . . . . ?
C7 C2 C3 C4 -0.14(15) . . . . ?
C1 C2 C3 C4 179.98(9) . . . . ?
C2 C3 C4 O3 179.50(8) . . . . ?
C2 C3 C4 C5 -1.50(15) . . . . ?
O4 C5 C4 O3 1.18(14) . . . . ?
C6 C5 C4 O3 -179.09(8) . . . . ?
O4 C5 C4 C3 -177.91(9) . . . . ?
C6 C5 C4 C3 1.82(14) . . . . ?
C3 C2 C7 C6 1.46(15) . . . . ?
C1 C2 C7 C6 -178.66(9) . . . . ?
C2 C7 C6 C5 -1.14(15) . . . . ?
O4 C5 C6 C7 179.24(9) . . . . ?
C4 C5 C6 C7 -0.50(15) . . . . ?
C3 C4 O3 C8 -5.16(14) . . . . ?
C5 C4 O3 C8 175.80(8) . . . . ?
O5 N2 C12 C11 -177.78(9) . . . . ?
C9 N2 C12 C11 1.69(15) . . . . ?
O5 N2 C9 C10 175.92(9) . . . . ?
C12 N2 C9 C10 -3.55(15) . . . . ?
C11 N1 C10 C9 0.64(15) . . . . ?
N2 C9 C10 N1 2.45(16) . . . . ?
C10 N1 C11 C12 -2.67(15) . . . . ?
N2 C12 C11 N1 1.57(16) . . . . ?

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
_geom_hbond_publ_flag
C12 H12 O1 0.95 2.36 3.2593(13) 157.1 1_554 yes
C9 H9 O1 0.95 2.64 3.5418(13) 158.7 1_654 yes
C10 H10 O3 0.95 2.52 3.1891(13) 127.2 1_665 yes
O2 H2 O5 0.88(2) 1.74(2) 2.6016(11) 165.5(19) 1_556 yes
O4 H5 N1 0.82(2) 2.02(2) 2.7889(12) 156.8(18) 1_445 yes

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_vainm2
_database_code_depnum_ccdc_archive 'CCDC 1573862'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N4 O6'
_chemical_formula_weight         412.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   19.046(2)
_cell_length_b                   7.1278(8)
_cell_length_c                   15.6486(18)
_cell_angle_alpha                90
_cell_angle_beta                 113.193(2)
_cell_angle_gamma                90
_cell_volume                     1952.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    23004
_cell_measurement_theta_min      2.327
_cell_measurement_theta_max      28.350

_exptl_crystal_description       rectangular
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   0.977
_exptl_transmission_factor_max   0.985
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   
'Absorption corrections were made using the program SADABS (Sheldrick, 1996)'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23004
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         28.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4885
_reflns_number_gt                3424
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXS-2017 (Sheldrick, 2017)'
_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)+(0.0521P)²+0.2421P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4885
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O3 O 0.48980(6) 0.24999(15) 0.47349(7) 0.0303(3) Uani 1 1 d . . . . .
O5A O 0.10352(6) 0.65601(16) 0.09861(8) 0.0366(3) Uani 1 1 d . . . . .
C10B C 0.07021(8) 0.1699(2) 0.23846(10) 0.0266(3) Uani 1 1 d . . . . .
N1A N 0.32936(8) 0.72762(19) 0.39915(9) 0.0336(3) Uani 1 1 d . . . . .
C3 C 0.39442(8) 0.3035(2) 0.31624(10) 0.0223(3) Uani 1 1 d . . . . .
H3 H 0.356207 0.234749 0.327523 0.027 Uiso 1 1 calc R U . . .
N1B N 0.17416(8) 0.1432(2) 0.42202(9) 0.0351(3) Uani 1 1 d . . . . .
N2A N 0.15993(8) 0.9144(2) 0.07095(10) 0.0354(3) Uani 1 1 d . . . . .
C4 C 0.46656(8) 0.3213(2) 0.38547(9) 0.0223(3) Uani 1 1 d . . . . .
C10A C 0.21670(9) 0.7650(2) 0.22087(10) 0.0271(3) Uani 1 1 d . . . . .
C14A C 0.29245(9) 0.8003(2) 0.23773(11) 0.0284(3) Uani 1 1 d . . . . .
H14A H 0.307042 0.839534 0.189048 0.034 Uiso 1 1 calc R U . . .
C9A C 0.15499(9) 0.7753(2) 0.12422(11) 0.0287(3) Uani 1 1 d . . . . .
C13A C 0.34656(9) 0.7770(2) 0.32764(11) 0.0311(4) Uani 1 1 d . . . . .
H13A H 0.398724 0.797321 0.338744 0.037 Uiso 1 1 calc R U . . .
C8 C 0.43218(10) 0.1742(2) 0.50001(11) 0.0336(4) Uani 1 1 d . . . . .
H8A H 0.390837 0.265797 0.486787 0.050 Uiso 1 1 calc R U . . .
H8B H 0.454168 0.145837 0.566672 0.050 Uiso 1 1 calc R U . . .
H8C H 0.411871 0.058928 0.464836 0.050 Uiso 1 1 calc R U . . .
C9B C 0.01216(9) 0.1745(2) 0.13960(11) 0.0307(4) Uani 1 1 d . . . . .
C11A C 0.19797(9) 0.7118(2) 0.29434(11) 0.0352(4) Uani 1 1 d . . . . .
H11A H 0.146540 0.685349 0.284826 0.042 Uiso 1 1 calc R U . . .
C14B C 0.14486(9) 0.2277(3) 0.26417(12) 0.0359(4) Uani 1 1 d . . . . .
H14B H 0.161984 0.277768 0.219475 0.043 Uiso 1 1 calc R U . . .
C11B C 0.04860(9) 0.1009(3) 0.30677(11) 0.0394(4) Uani 1 1 d . . . . .
H11B H -0.002460 0.060886 0.291803 0.047 Uiso 1 1 calc R U . . .
C13B C 0.19405(9) 0.2112(3) 0.35602(12) 0.0399(4) Uani 1 1 d . . . . .
H13B H 0.245389 0.251104 0.373072 0.048 Uiso 1 1 calc R U . . .
C12B C 0.10181(10) 0.0905(3) 0.39693(11) 0.0413(4) Uani 1 1 d . . . . .
H12B H 0.086071 0.043465 0.443396 0.050 Uiso 1 1 calc R U . . .
C12A C 0.25572(10) 0.6983(3) 0.38174(12) 0.0380(4) Uani 1 1 d . . . . .
H12A H 0.242358 0.666225 0.432339 0.046 Uiso 1 1 calc R U . . .
O1 O 0.25579(6) 0.24127(17) 0.15951(8) 0.0350(3) Uani 1 1 d . . . . .
O4 O 0.59744(6) 0.41969(17) 0.42952(8) 0.0317(3) Uani 1 1 d . . . . .
N2B N 0.02796(9) 0.2808(2) 0.07967(10) 0.0337(3) Uani 1 1 d . . . . .
O5B O -0.04692(7) 0.0815(2) 0.11816(8) 0.0526(4) Uani 1 1 d . . . . .
C1 C 0.30238(8) 0.3518(2) 0.15321(10) 0.0244(3) Uani 1 1 d . . . . .
C7 C 0.43280(8) 0.4914(2) 0.21410(10) 0.0229(3) Uani 1 1 d . . . . .
H7 H 0.420558 0.555161 0.156717 0.028 Uiso 1 1 calc R U . . .
C2 C 0.37757(8) 0.38681(19) 0.22946(10) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.50616(9) 0.5028(2) 0.28281(10) 0.0252(3) Uani 1 1 d . . . . .
H6 H 0.544184 0.572414 0.271556 0.030 Uiso 1 1 calc R U . . .
C5 C 0.52436(8) 0.4140(2) 0.36721(10) 0.0230(3) Uani 1 1 d . . . . .
O2 O 0.29106(7) 0.44738(18) 0.07692(7) 0.0366(3) Uani 1 1 d . . . . .
H2A H 0.1920(11) 1.005(3) 0.0956(13) 0.047(6) Uiso 1 1 d . . . . .
H2B H 0.1224(12) 0.920(3) 0.0102(15) 0.057(6) Uiso 1 1 d . . . . .
H5 H 0.6058(13) 0.355(3) 0.4876(16) 0.073(7) Uiso 1 1 d . . . . .
H2BA H -0.0086(12) 0.289(3) 0.0192(15) 0.050(6) Uiso 1 1 d . . . . .
H2AB H 0.0678(11) 0.362(3) 0.1000(13) 0.045(5) Uiso 1 1 d . . . . .
H2 H 0.2444(13) 0.405(3) 0.0257(16) 0.074(7) Uiso 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
O3 C4 1.3678(17) . ?
O3 C8 1.4237(19) . ?
O5A C9A 1.2392(18) . ?
C10B C11B 1.379(2) . ?
C10B C14B 1.379(2) . ?
C10B C9B 1.506(2) . ?
N1A C13A 1.331(2) . ?
N1A C12A 1.336(2) . ?
C3 C4 1.380(2) . ?
C3 C2 1.399(2) . ?
N1B C13B 1.324(2) . ?
N1B C12B 1.330(2) . ?
N2A C9A 1.322(2) . ?
C4 C5 1.406(2) . ?
C10A C14A 1.384(2) . ?
C10A C11A 1.384(2) . ?
C10A C9A 1.508(2) . ?
C14A C13A 1.388(2) . ?
C9B O5B 1.2330(19) . ?
C9B N2B 1.329(2) . ?
C11A C12A 1.380(2) . ?
C14B C13B 1.377(2) . ?
C11B C12B 1.377(2) . ?
O1 C1 1.2192(18) . ?
O4 C5 1.3495(17) . ?
C1 O2 1.3165(18) . ?
C1 C2 1.480(2) . ?
C7 C2 1.385(2) . ?
C7 C6 1.390(2) . ?
C6 C5 1.380(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 C8 116.97(12) . . ?
C11B C10B C14B 117.94(14) . . ?
C11B C10B C9B 118.78(14) . . ?
C14B C10B C9B 123.26(14) . . ?
C13A N1A C12A 117.14(14) . . ?
C4 C3 C2 120.01(13) . . ?
C13B N1B C12B 117.05(14) . . ?
O3 C4 C3 125.71(13) . . ?
O3 C4 C5 114.23(12) . . ?
C3 C4 C5 120.02(13) . . ?
C14A C10A C11A 118.81(14) . . ?
C14A C10A C9A 121.64(14) . . ?
C11A C10A C9A 119.50(14) . . ?
C10A C14A C13A 118.26(15) . . ?
O5A C9A N2A 123.67(14) . . ?
O5A C9A C10A 119.71(14) . . ?
N2A C9A C10A 116.62(14) . . ?
N1A C13A C14A 123.61(15) . . ?
O5B C9B N2B 123.38(15) . . ?
O5B C9B C10B 119.34(14) . . ?
N2B C9B C10B 117.28(14) . . ?
C12A C11A C10A 118.48(16) . . ?
C13B C14B C10B 118.58(16) . . ?
C12B C11B C10B 119.32(15) . . ?
N1B C13B C14B 124.00(15) . . ?
N1B C12B C11B 123.11(16) . . ?
N1A C12A C11A 123.64(16) . . ?
O1 C1 O2 122.90(13) . . ?
O1 C1 C2 123.21(13) . . ?
O2 C1 C2 113.87(13) . . ?
C2 C7 C6 119.86(13) . . ?
C7 C2 C3 119.83(13) . . ?
C7 C2 C1 120.70(13) . . ?
C3 C2 C1 119.36(13) . . ?
C5 C6 C7 120.71(14) . . ?
O4 C5 C6 118.46(13) . . ?
O4 C5 C4 122.31(13) . . ?
C6 C5 C4 119.23(13) . . ?

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
_geom_hbond_publ_flag
C8 H8A O4 0.98 2.56 3.225(2) 125.0 3_666 yes
C14B H14B O1 0.95 2.34 3.143(2) 142.4 . yes
N2A H2A O1 0.87(2) 2.09(2) 2.9475(19) 171.4(18) 1_565 yes
N2A H2B O5B 0.94(2) 1.96(2) 2.8938(18) 176.4(19) 3_565 yes
O4 H5 N1A 0.98(2) 1.81(2) 2.7000(17) 150(2) 3_666 yes
N2B H2BA O5A 0.93(2) 2.05(2) 2.9588(18) 165.9(17) 3_565 yes
N2B H2AB O5A 0.90(2) 2.21(2) 2.9960(19) 145.1(16) . yes
O2 H2 N1B 0.98(2) 1.68(2) 2.6454(17) 166(2) 4_565 yes

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_vaphz
_database_code_depnum_ccdc_archive 'CCDC 1573864'
_audit_update_record             
;
2017-09-11 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 N3 O4'
_chemical_formula_weight         438.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.1376(4)
_cell_length_b                   9.5383(5)
_cell_length_c                   16.6511(9)
_cell_angle_alpha                98.3390(10)
_cell_angle_beta                 101.0090(10)
_cell_angle_gamma                108.2880(10)
_cell_volume                     1030.69(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13988
_cell_measurement_theta_min      1.277
_cell_measurement_theta_max      28.345

_exptl_crystal_description       block
_exptl_crystal_colour            'yellow orange'
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             458
_exptl_transmission_factor_min   0.943
_exptl_transmission_factor_max   0.957
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.45
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   
'Absorption corrections were made using the program SADABS (Sheldrick, 1996)'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13988
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.277
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5128
_reflns_number_gt                4180
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_structure_solution    'SHELXS-2017 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXS-2017 (Sheldrick, 2017)'
_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)+(0.0524P)²+0.2137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5128
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O3 O 0.16500(12) 0.58909(9) 0.29552(5) 0.02533(19) Uani 1 1 d . . . . .
C5 C 0.32322(16) 0.45163(12) 0.22300(7) 0.0206(2) Uani 1 1 d . . . . .
C4 C 0.14013(17) 0.46975(12) 0.23281(7) 0.0195(2) Uani 1 1 d . . . . .
C6 C 0.31748(17) 0.33529(13) 0.16103(7) 0.0240(2) Uani 1 1 d . . . . .
H6 H 0.440977 0.323095 0.154176 0.029 Uiso 1 1 calc R U . . .
C3 C -0.04402(17) 0.37049(12) 0.18200(7) 0.0203(2) Uani 1 1 d . . . . .
H3 H -0.167815 0.381402 0.189416 0.024 Uiso 1 1 calc R U . . .
C2 C -0.04808(17) 0.25352(12) 0.11943(7) 0.0205(2) Uani 1 1 d . . . . .
C7 C 0.13279(18) 0.23650(13) 0.10894(7) 0.0231(2) Uani 1 1 d . . . . .
H7 H 0.129924 0.157517 0.066261 0.028 Uiso 1 1 calc R U . . .
O4 O 0.50629(12) 0.54357(10) 0.27333(6) 0.0288(2) Uani 1 1 d . . . . .
C23 C 0.6999(2) 0.57140(15) 0.03825(8) 0.0309(3) Uani 1 1 d . . . . .
N3 N 0.65024(18) 0.43658(13) -0.01385(7) 0.0335(3) Uani 1 1 d . . . . .
C24 C 0.4521(2) 0.36565(14) -0.05199(8) 0.0310(3) Uani 1 1 d . . . . .
C1 C -0.24690(17) 0.14770(12) 0.06641(7) 0.0214(2) Uani 1 1 d . . . . .
C26 C 0.1907(3) 0.14705(17) -0.14676(9) 0.0489(4) Uani 1 1 d . . . . .
H26 H 0.151351 0.052016 -0.184469 0.059 Uiso 1 1 calc R U . . .
C25 C 0.3896(3) 0.22202(16) -0.10766(9) 0.0421(4) Uani 1 1 d . . . . .
H25 H 0.488370 0.178586 -0.117392 0.050 Uiso 1 1 calc R U . . .
C22 C 0.9085(2) 0.65498(18) 0.07966(9) 0.0409(3) Uani 1 1 d . . . . .
H22 H 1.011344 0.615468 0.070607 0.049 Uiso 1 1 calc R U . . .
O1 O -0.40880(12) 0.14237(9) 0.08498(5) 0.0271(2) Uani 1 1 d . . . . .
O2 O -0.24013(13) 0.05953(10) 0.00015(5) 0.0288(2) Uani 1 1 d . . . . .
N2 N 0.61113(14) 0.80538(10) 0.39799(6) 0.0223(2) Uani 1 1 d . . . . .
C8 C -0.01677(18) 0.60533(14) 0.31298(8) 0.0279(3) Uani 1 1 d . . . . .
H8A H -0.098040 0.621912 0.263206 0.042 Uiso 1 1 calc R U . . .
H8B H 0.019694 0.692013 0.359837 0.042 Uiso 1 1 calc R U . . .
H8C H -0.096421 0.513171 0.327848 0.042 Uiso 1 1 calc R U . . .
C21 C 0.9594(3) 0.79189(18) 0.13230(10) 0.0498(4) Uani 1 1 d . . . . .
H21 H 1.098506 0.847409 0.159824 0.060 Uiso 1 1 calc R U . . .
C9 C 0.71109(18) 0.66914(13) 0.49811(8) 0.0270(3) Uani 1 1 d . . . . .
H9 H 0.653753 0.577332 0.456666 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5130(2) 0.94387(14) 0.29918(8) 0.0296(3) Uani 1 1 d . . . . .
H18 H 0.453337 0.853896 0.256415 0.036 Uiso 1 1 calc R U . . .
C20 C 0.70288(16) 0.80648(12) 0.47672(7) 0.0211(2) Uani 1 1 d . . . . .
C19 C 0.60580(17) 0.93805(13) 0.38162(7) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.78541(15) 1.07665(11) 0.52381(6) 0.0235(2) Uani 1 1 d . . . . .
C13 C 0.79100(16) 0.94395(13) 0.54009(7) 0.0216(2) Uani 1 1 d . . . . .
C11 C 0.8901(2) 0.80554(15) 0.64062(8) 0.0306(3) Uani 1 1 d . . . . .
H11 H 0.953147 0.803274 0.695857 0.037 Uiso 1 1 calc R U . . .
C12 C 0.88621(18) 0.93882(14) 0.62247(7) 0.0275(3) Uani 1 1 d . . . . .
H12 H 0.947244 1.029229 0.664892 0.033 Uiso 1 1 calc R U . . .
C15 C 0.68404(18) 1.21277(13) 0.42421(8) 0.0276(3) Uani 1 1 d . . . . .
H15 H 0.740307 1.304184 0.465953 0.033 Uiso 1 1 calc R U . . .
C17 C 0.5095(2) 1.07784(16) 0.28147(8) 0.0337(3) Uani 1 1 d . . . . .
H17 H 0.449345 1.080880 0.226006 0.040 Uiso 1 1 calc R U . . .
C10 C 0.8009(2) 0.66909(15) 0.57782(8) 0.0309(3) Uani 1 1 d . . . . .
H10 H 0.804163 0.576637 0.591786 0.037 Uiso 1 1 calc R U . . .
C14 C 0.69392(17) 1.07509(12) 0.44542(7) 0.0219(2) Uani 1 1 d . . . . .
C16 C 0.5950(2) 1.21389(15) 0.34496(9) 0.0316(3) Uani 1 1 d . . . . .
H16 H 0.589331 1.306194 0.331542 0.038 Uiso 1 1 calc R U . . .
H5 H 0.495(3) 0.618(2) 0.3092(12) 0.058(5) Uiso 1 1 d . . . . .
H2 H -0.377(4) -0.020(3) -0.0307(14) 0.087(7) Uiso 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
O3 C4 1.3695(12) . ?
O3 C8 1.4314(14) . ?
C5 O4 1.3521(13) . ?
C5 C6 1.3860(15) . ?
C5 C4 1.4069(15) . ?
C4 C3 1.3791(15) . ?
C6 C7 1.3873(16) . ?
C3 C2 1.4007(14) . ?
C2 C7 1.3903(16) . ?
C2 C1 1.4752(15) . ?
C23 N3 1.3435(16) . ?
C23 C22 1.4256(19) . ?
C23 C24 1.4326(19) 2_665 ?
N3 C24 1.3393(18) . ?
C24 C25 1.4232(18) . ?
C1 O1 1.2401(14) . ?
C1 O2 1.3051(13) . ?
C26 C25 1.351(2) . ?
C26 C21 1.412(3) 2_665 ?
C22 C21 1.362(2) . ?
N2 C19 1.3430(15) . ?
N2 C20 1.3459(15) . ?
C9 C10 1.3594(18) . ?
C9 C20 1.4220(16) . ?
C18 C17 1.3590(19) . ?
C18 C19 1.4226(17) . ?
C20 C13 1.4338(15) . ?
C19 C14 1.4348(15) . ?
N1 C14 1.3392(15) . ?
N1 C13 1.3432(15) . ?
C13 C12 1.4248(17) . ?
C11 C12 1.3560(18) . ?
C11 C10 1.4225(18) . ?
C15 C16 1.3541(18) . ?
C15 C14 1.4274(17) . ?
C17 C16 1.4257(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 C8 116.73(8) . . ?
O4 C5 C6 118.53(10) . . ?
O4 C5 C4 121.85(10) . . ?
C6 C5 C4 119.62(10) . . ?
O3 C4 C3 125.57(10) . . ?
O3 C4 C5 114.35(9) . . ?
C3 C4 C5 120.08(9) . . ?
C5 C6 C7 120.52(10) . . ?
C4 C3 C2 119.83(10) . . ?
C7 C2 C3 120.19(10) . . ?
C7 C2 C1 120.91(10) . . ?
C3 C2 C1 118.89(10) . . ?
C6 C7 C2 119.75(10) . . ?
N3 C23 C22 119.36(13) . . ?
N3 C23 C24 121.42(12) . 2_665 ?
C22 C23 C24 119.21(12) . 2_665 ?
C24 N3 C23 116.23(12) . . ?
N3 C24 C25 118.93(13) . . ?
N3 C24 C23 122.36(11) . 2_665 ?
C25 C24 C23 118.72(13) . 2_665 ?
O1 C1 O2 122.73(10) . . ?
O1 C1 C2 121.55(9) . . ?
O2 C1 C2 115.71(10) . . ?
C25 C26 C21 120.86(14) . 2_665 ?
C26 C25 C24 120.43(15) . . ?
C21 C22 C23 119.49(15) . . ?
C19 N2 C20 117.18(9) . . ?
C22 C21 C26 121.29(15) . 2_665 ?
C10 C9 C20 120.06(11) . . ?
C17 C18 C19 120.15(11) . . ?
N2 C20 C9 119.76(10) . . ?
N2 C20 C13 121.11(10) . . ?
C9 C20 C13 119.13(11) . . ?
N2 C19 C18 119.57(10) . . ?
N2 C19 C14 121.39(10) . . ?
C18 C19 C14 119.04(11) . . ?
C14 N1 C13 116.96(9) . . ?
N1 C13 C12 119.40(10) . . ?
N1 C13 C20 121.76(10) . . ?
C12 C13 C20 118.84(11) . . ?
C12 C11 C10 120.69(12) . . ?
C11 C12 C13 120.34(11) . . ?
C16 C15 C14 120.41(11) . . ?
C18 C17 C16 120.93(12) . . ?
C9 C10 C11 120.93(12) . . ?
N1 C14 C15 119.54(10) . . ?
N1 C14 C19 121.61(10) . . ?
C15 C14 C19 118.85(11) . . ?
C15 C16 C17 120.62(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
_geom_hbond_publ_flag
C6 H6 O1 0.95 2.55 3.3663(14) 144.1 1_655 yes
C8 H8B N1 0.98 2.52 3.4735(15) 163.6 2_676 yes
O4 H5 N2 0.892(19) 1.976(19) 2.7992(12) 152.7(17) . yes
O2 H2 O1 1.01(2) 1.60(2) 2.6115(11) 176(2) 2_455 yes

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041

