# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

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

data_L(phi)(H2O)
_database_code_depnum_ccdc_archive 'CCDC 1521933'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H30 N6 O8'
_chemical_formula_sum            'C32 H30 N6 O8'
_chemical_formula_weight         626.62

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                   9.4899(16)
_cell_length_b                   13.113(2)
_cell_length_c                   13.165(2)
_cell_angle_alpha                110.046(12)
_cell_angle_beta                 102.423(11)
_cell_angle_gamma                94.908(11)
_cell_volume                     1480.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1405
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      19.26

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_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  0.970
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14413
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.679
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             5142
_reflns_number_gt                2988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+0.7000P] 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         5142
_refine_ls_number_parameters     435
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C2 C 0.5640(3) 0.14018(19) -0.0064(2) 0.0419(6) Uani 1 1 d . . . . .
C7 C 0.6555(3) 0.12729(18) 0.0863(2) 0.0391(6) Uani 1 1 d . . . . .
C6 C 0.5966(2) 0.12313(19) 0.1750(2) 0.0386(6) Uani 1 1 d . . . . .
C1 C 0.6222(3) 0.1386(2) -0.1024(2) 0.0483(7) Uani 1 1 d . . . . .
C12 C 0.6845(3) 0.10321(19) 0.2643(2) 0.0409(6) Uani 1 1 d . . . . .
C5 C 0.4502(3) 0.13712(19) 0.1708(2) 0.0426(6) Uani 1 1 d . . . . .
C8 C 0.8027(3) 0.1173(2) 0.0915(2) 0.0428(6) Uani 1 1 d . . . . .
C14 C 0.3900(3) 0.1390(2) 0.2664(2) 0.0503(7) Uani 1 1 d . . . . .
C10 C 0.8875(3) 0.0995(2) 0.1810(2) 0.0502(7) Uani 1 1 d . . . . .
H10 H 0.9852 0.0933 0.1845 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3637(3) 0.1509(2) 0.0799(2) 0.0482(7) Uani 1 1 d . . . . .
H4 H 0.2671 0.1600 0.0777 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4210(3) 0.1513(2) -0.0094(2) 0.0475(7) Uani 1 1 d . . . . .
H3 H 0.3615 0.1592 -0.0714 0.057 Uiso 1 1 calc R U . . .
C28 C 0.8587(3) 0.3809(2) 0.3558(2) 0.0487(7) Uani 1 1 d . . . . .
H28 H 0.9530 0.3700 0.3824 0.058 Uiso 1 1 calc R U . . .
C11 C 0.8273(3) 0.0909(2) 0.2665(2) 0.0487(7) Uani 1 1 d . . . . .
H11 H 0.8845 0.0766 0.3254 0.058 Uiso 1 1 calc R U . . .
C9 C 0.8680(3) 0.1290(2) 0.0024(2) 0.0486(7) Uani 1 1 d . . . . .
C13 C 0.6225(3) 0.0975(2) 0.3567(2) 0.0485(7) Uani 1 1 d . . . . .
C30 C 0.6190(3) 0.4069(2) 0.3807(2) 0.0489(7) Uani 1 1 d . . . . .
H30 H 0.5528 0.4141 0.4245 0.059 Uiso 1 1 calc R U . . .
N6 N 0.0217(3) 0.2750(2) 0.55787(19) 0.0601(6) Uani 1 1 d . . . . .
C27 C 0.8168(3) 0.3905(2) 0.2528(2) 0.0489(7) Uani 1 1 d . . . . .
C32 C 0.6769(3) 0.4067(2) 0.2118(2) 0.0490(7) Uani 1 1 d . . . . .
H32 H 0.6493 0.4117 0.1418 0.059 Uiso 1 1 calc R U . . .
C21 C 0.8323(3) 0.1459(2) -0.1824(2) 0.0583(8) Uani 1 1 d . . . . .
H21A H 0.7767 0.0873 -0.2514 0.070 Uiso 1 1 calc R U . . .
H21B H 0.9329 0.1338 -0.1683 0.070 Uiso 1 1 calc R U . . .
C29 C 0.7582(3) 0.3878(2) 0.4187(2) 0.0476(7) Uani 1 1 d . . . . .
C31 C 0.5796(3) 0.4152(2) 0.2768(2) 0.0486(7) Uani 1 1 d . . . . .
C22 C 0.8285(3) 0.2559(2) -0.1974(2) 0.0620(8) Uani 1 1 d . . . . .
H22A H 0.8687 0.2533 -0.2598 0.074 Uiso 1 1 calc R U . . .
H22B H 0.7271 0.2648 -0.2171 0.074 Uiso 1 1 calc R U . . .
C20 C 0.1595(3) 0.3165(2) 0.5813(2) 0.0573(8) Uani 1 1 d . . . . .
H20 H 0.1929 0.3843 0.5791 0.069 Uiso 1 1 calc R U . . .
C15 C 0.4258(3) 0.1309(2) 0.4535(2) 0.0607(8) Uani 1 1 d . . . . .
H15A H 0.4692 0.0834 0.4892 0.073 Uiso 1 1 calc R U . . .
H15B H 0.3204 0.1074 0.4301 0.073 Uiso 1 1 calc R U . . .
C16 C 0.4646(3) 0.2517(3) 0.5374(2) 0.0651(9) Uani 1 1 d . . . . .
H16A H 0.5703 0.2737 0.5612 0.078 Uiso 1 1 calc R U . . .
H16B H 0.4245 0.2987 0.4996 0.078 Uiso 1 1 calc R U . . .
C17 C 0.4083(3) 0.2698(3) 0.6385(2) 0.0648(8) Uani 1 1 d . . . . .
H17A H 0.4441 0.2206 0.6749 0.078 Uiso 1 1 calc R U . . .
H17B H 0.4451 0.3449 0.6911 0.078 Uiso 1 1 calc R U . . .
C24 C 1.1588(3) 0.3665(2) 0.0251(3) 0.0619(8) Uani 1 1 d . . . . .
H24 H 1.1246 0.3566 0.0828 0.074 Uiso 1 1 calc R U . . .
C18 C 0.1590(3) 0.1590(2) 0.6017(2) 0.0598(8) Uani 1 1 d . . . . .
H18 H 0.1878 0.0979 0.6155 0.072 Uiso 1 1 calc R U . . .
C26 C 1.1610(4) 0.3814(3) -0.1325(3) 0.0736(10) Uani 1 1 d . . . . .
H26 H 1.1331 0.3841 -0.2036 0.088 Uiso 1 1 calc R U . . .
C25 C 1.2992(4) 0.3945(3) -0.0703(3) 0.0741(9) Uani 1 1 d . . . . .
H25 H 1.3834 0.4080 -0.0924 0.089 Uiso 1 1 calc R U . . .
O5 O 0.4405(2) 0.43341(18) 0.2426(2) 0.0647(6) Uani 1 1 d . . . . .
O2 O 0.5443(2) 0.13660(16) -0.19008(16) 0.0651(6) Uani 1 1 d . . . . .
O3 O 0.6894(2) 0.07408(17) 0.43297(17) 0.0647(6) Uani 1 1 d . . . . .
O4 O 0.2663(2) 0.15439(18) 0.26939(17) 0.0725(6) Uani 1 1 d . . . . .
O1 O 0.9965(2) 0.12959(17) 0.00670(17) 0.0670(6) Uani 1 1 d . . . . .
O6 O 0.7909(2) 0.37591(19) 0.51999(18) 0.0652(6) Uani 1 1 d . . . . .
O7 O 0.9118(3) 0.38351(19) 0.18666(19) 0.0682(6) Uani 1 1 d . . . . .
N1 N 0.7721(2) 0.13969(17) -0.08967(18) 0.0494(6) Uani 1 1 d . . . . .
N4 N 0.4817(2) 0.12171(17) 0.35437(19) 0.0489(6) Uani 1 1 d . . . . .
N2 N 1.0706(2) 0.36330(18) -0.07069(19) 0.0526(6) Uani 1 1 d . . . . .
N5 N 0.2484(2) 0.25018(18) 0.60909(18) 0.0518(6) Uani 1 1 d . . . . .
N3 N 1.2980(3) 0.3852(2) 0.0292(2) 0.0639(7) Uani 1 1 d . . . . .
C19 C 0.0213(3) 0.1754(3) 0.5705(2) 0.0616(8) Uani 1 1 d . . . . .
H19 H -0.0625 0.1263 0.5590 0.074 Uiso 1 1 calc R U . . .
O8 O 0.1859(4) 0.4124(5) 0.3140(3) 0.1647(18) Uani 1 1 d D . . . .
C23 C 0.9108(3) 0.3556(2) -0.0968(3) 0.0625(8) Uani 1 1 d . . . . .
H23A H 0.8863 0.4213 -0.1097 0.075 Uiso 1 1 calc R U . . .
H23B H 0.8781 0.3543 -0.0323 0.075 Uiso 1 1 calc R U . . .
H8A H 0.273(4) 0.424(6) 0.303(6) 0.30(4) Uiso 1 1 d D . . . .
H8B H 0.169(2) 0.3442(11) 0.2762(16) 0.002(5) Uiso 1 1 d D . . . .
H7 H 0.995(4) 0.383(3) 0.223(3) 0.106(15) Uiso 1 1 d . . . . .
H5 H 0.417(4) 0.424(3) 0.174(3) 0.094(14) Uiso 1 1 d . . . . .
H6 H 0.864(4) 0.347(3) 0.528(3) 0.116(15) 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
C2 C3 1.371(3) . ?
C2 C7 1.409(3) . ?
C2 C1 1.479(4) . ?
C7 C8 1.404(3) . ?
C7 C6 1.412(3) . ?
C6 C12 1.405(3) . ?
C6 C5 1.409(3) . ?
C1 O2 1.220(3) . ?
C1 N1 1.394(3) . ?
C12 C11 1.374(3) . ?
C12 C13 1.482(4) . ?
C5 C4 1.375(3) . ?
C5 C14 1.484(4) . ?
C8 C10 1.380(3) . ?
C8 C9 1.484(3) . ?
C14 O4 1.215(3) . ?
C14 N4 1.389(3) . ?
C10 C11 1.400(3) . ?
C4 C3 1.398(3) . ?
C28 C29 1.381(3) . ?
C28 C27 1.381(4) . ?
C9 O1 1.207(3) . ?
C9 N1 1.408(3) . ?
C13 O3 1.215(3) . ?
C13 N4 1.396(3) . ?
C30 C31 1.382(3) . ?
C30 C29 1.384(3) . ?
N6 C20 1.301(3) . ?
N6 C19 1.371(3) . ?
C27 O7 1.370(3) . ?
C27 C32 1.384(3) . ?
C32 C31 1.375(4) . ?
C21 N1 1.477(3) . ?
C21 C22 1.523(4) . ?
C29 O6 1.368(3) . ?
C31 O5 1.369(3) . ?
C22 C23 1.505(4) . ?
C20 N5 1.346(3) . ?
C15 N4 1.482(3) . ?
C15 C16 1.546(4) . ?
C16 C17 1.491(4) . ?
C17 N5 1.460(3) . ?
C24 N3 1.309(4) . ?
C24 N2 1.340(3) . ?
C18 C19 1.342(4) . ?
C18 N5 1.368(3) . ?
C26 C25 1.350(4) . ?
C26 N2 1.362(3) . ?
C25 N3 1.359(4) . ?
N2 C23 1.468(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
C3 C2 C7 120.5(2) . . ?
C3 C2 C1 120.0(2) . . ?
C7 C2 C1 119.4(2) . . ?
C8 C7 C2 121.3(2) . . ?
C8 C7 C6 119.7(2) . . ?
C2 C7 C6 119.0(2) . . ?
C12 C6 C5 121.5(2) . . ?
C12 C6 C7 119.3(2) . . ?
C5 C6 C7 119.3(2) . . ?
O2 C1 N1 120.2(3) . . ?
O2 C1 C2 122.4(2) . . ?
N1 C1 C2 117.4(2) . . ?
C11 C12 C6 120.2(2) . . ?
C11 C12 C13 120.5(2) . . ?
C6 C12 C13 119.4(2) . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 C14 119.9(2) . . ?
C6 C5 C14 119.6(2) . . ?
C10 C8 C7 119.8(2) . . ?
C10 C8 C9 120.1(2) . . ?
C7 C8 C9 120.1(2) . . ?
O4 C14 N4 120.3(3) . . ?
O4 C14 C5 122.6(3) . . ?
N4 C14 C5 117.1(2) . . ?
C8 C10 C11 120.3(2) . . ?
C5 C4 C3 120.0(2) . . ?
C2 C3 C4 120.7(2) . . ?
C29 C28 C27 118.8(2) . . ?
C12 C11 C10 120.6(2) . . ?
O1 C9 N1 120.5(2) . . ?
O1 C9 C8 123.0(3) . . ?
N1 C9 C8 116.6(2) . . ?
O3 C13 N4 120.0(3) . . ?
O3 C13 C12 122.8(2) . . ?
N4 C13 C12 117.2(2) . . ?
C31 C30 C29 119.2(3) . . ?
C20 N6 C19 104.8(2) . . ?
O7 C27 C28 121.2(2) . . ?
O7 C27 C32 117.4(3) . . ?
C28 C27 C32 121.4(2) . . ?
C31 C32 C27 118.7(3) . . ?
N1 C21 C22 113.3(2) . . ?
O6 C29 C28 122.0(2) . . ?
O6 C29 C30 117.4(2) . . ?
C28 C29 C30 120.7(3) . . ?
O5 C31 C32 121.8(3) . . ?
O5 C31 C30 117.0(3) . . ?
C32 C31 C30 121.1(2) . . ?
C23 C22 C21 115.4(2) . . ?
N6 C20 N5 112.4(3) . . ?
N4 C15 C16 109.8(2) . . ?
C17 C16 C15 113.6(2) . . ?
N5 C17 C16 111.3(2) . . ?
N3 C24 N2 113.0(3) . . ?
C19 C18 N5 106.1(3) . . ?
C25 C26 N2 106.4(3) . . ?
C26 C25 N3 110.4(3) . . ?
C1 N1 C9 124.5(2) . . ?
C1 N1 C21 117.6(2) . . ?
C9 N1 C21 117.9(2) . . ?
C14 N4 C13 124.9(2) . . ?
C14 N4 C15 117.3(2) . . ?
C13 N4 C15 117.8(2) . . ?
C24 N2 C26 105.8(3) . . ?
C24 N2 C23 126.6(3) . . ?
C26 N2 C23 127.3(2) . . ?
C20 N5 C18 106.3(2) . . ?
C20 N5 C17 127.1(2) . . ?
C18 N5 C17 126.6(2) . . ?
C24 N3 C25 104.3(3) . . ?
C18 C19 N6 110.4(3) . . ?
N2 C23 C22 114.2(2) . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_L(dnp)2
_database_code_depnum_ccdc_archive 'CCDC 1521934'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N6 O4, 2(C6 H3 N2 O5)'
_chemical_formula_sum            'C38 H30 N10 O14'
_chemical_formula_weight         850.72

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'
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'
H H 0.0000 0.0000 '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                   8.3794(12)
_cell_length_b                   10.8125(17)
_cell_length_c                   12.123(3)
_cell_angle_alpha                106.232(14)
_cell_angle_beta                 108.621(15)
_cell_angle_gamma                105.345(9)
_cell_volume                     920.7(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1083
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      18.38

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_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  0.970
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7823
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.933
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             3131
_reflns_number_gt                1731
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+0.8000P] 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         3131
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.9410(3) 0.2610(2) 0.3610(2) 0.0718(8) Uani 1 1 d . . . . .
O2 O 1.2857(3) 0.1543(2) 0.1566(2) 0.0655(7) Uani 1 1 d . . . . .
N2 N 1.1124(3) 0.2109(2) 0.2571(2) 0.0512(7) Uani 1 1 d . . . . .
N1 N 0.6504(4) -0.1278(3) 0.1755(3) 0.0655(9) Uani 1 1 d . . . . .
N3 N 0.3679(4) -0.2442(3) 0.0430(3) 0.0709(9) Uani 1 1 d . . . . .
C7 C 1.0894(4) 0.2911(3) 0.3578(3) 0.0528(9) Uani 1 1 d . . . . .
C8 C 1.2529(4) 0.4140(3) 0.4588(3) 0.0469(8) Uani 1 1 d . . . . .
C9 C 1.2402(4) 0.4999(3) 0.5601(3) 0.0531(9) Uani 1 1 d . . . . .
H9 H 1.1282 0.4813 0.5648 0.064 Uiso 1 1 calc R U . . .
C16 C 1.4222(4) 0.4414(3) 0.4513(3) 0.0434(8) Uani 1 1 d . . . . .
C18 C 1.2778(4) 0.2328(3) 0.2466(3) 0.0522(9) Uani 1 1 d . . . . .
C15 C 0.9535(4) 0.0880(3) 0.1533(3) 0.0615(10) Uani 1 1 d . . . . .
H15A H 0.9579 0.0824 0.0731 0.074 Uiso 1 1 calc R U . . .
H15B H 0.8423 0.1004 0.1512 0.074 Uiso 1 1 calc R U . . .
C14 C 0.9469(5) -0.0472(4) 0.1669(4) 0.0752(12) Uani 1 1 d . . . . .
H14A H 0.8882 -0.1213 0.0826 0.090 Uiso 1 1 calc R U . . .
H14B H 1.0715 -0.0402 0.2055 0.090 Uiso 1 1 calc R U . . .
C13 C 0.8520(5) -0.0891(4) 0.2416(4) 0.0785(12) Uani 1 1 d . . . . .
H13B H 0.9012 -0.0126 0.3236 0.094 Uiso 1 1 calc R U . . .
H13A H 0.8737 -0.1683 0.2559 0.094 Uiso 1 1 calc R U . . .
C12 C 0.5565(5) -0.0486(4) 0.2028(4) 0.0731(11) Uani 1 1 d . . . . .
H12 H 0.6052 0.0400 0.2672 0.088 Uiso 1 1 calc R U . . .
C11 C 0.3806(5) -0.1209(4) 0.1206(4) 0.0758(12) Uani 1 1 d . . . . .
H11 H 0.2848 -0.0918 0.1173 0.091 Uiso 1 1 calc R U . . .
C10 C 0.5347(5) -0.2451(4) 0.0790(4) 0.0729(11) Uani 1 1 d . . . . .
H10 H 0.5646 -0.3178 0.0415 0.087 Uiso 1 1 calc R U . . .
O4 O 0.0224(4) 0.3434(3) 0.0200(3) 0.0896(9) Uani 1 1 d . . . . .
O5 O 0.3105(4) 0.4387(3) 0.0748(3) 0.0951(10) Uani 1 1 d . . . . .
O6 O 0.7081(4) 0.8381(3) 0.4486(3) 0.1059(11) Uani 1 1 d . . . . .
O7 O 0.6047(4) 0.9273(3) 0.5810(3) 0.1072(11) Uani 1 1 d . . . . .
O3 O -0.1274(3) 0.4682(3) 0.1584(3) 0.0932(10) Uani 1 1 d . . . . .
N4 N 0.1733(4) 0.4362(3) 0.0930(3) 0.0710(9) Uani 1 1 d . . . . .
N5 N 0.5820(5) 0.8439(3) 0.4774(4) 0.0848(11) Uani 1 1 d . . . . .
C3 C 0.1919(5) 0.5462(3) 0.2017(3) 0.0586(9) Uani 1 1 d . . . . .
C2 C 0.3691(5) 0.6418(4) 0.2826(3) 0.0644(10) Uani 1 1 d . . . . .
H2 H 0.4671 0.6338 0.2651 0.077 Uiso 1 1 calc R U . . .
C1 C 0.3968(5) 0.7484(4) 0.3891(3) 0.0662(11) Uani 1 1 d . . . . .
C6 C 0.2502(6) 0.7642(4) 0.4139(4) 0.0747(12) Uani 1 1 d . . . . .
H6 H 0.2710 0.8385 0.4851 0.090 Uiso 1 1 calc R U . . .
C5 C 0.0790(5) 0.6718(4) 0.3345(4) 0.0747(11) Uani 1 1 d . . . . .
H5 H -0.0165 0.6856 0.3523 0.090 Uiso 1 1 calc R U . . .
C4 C 0.0358(5) 0.5536(4) 0.2243(4) 0.0661(10) Uani 1 1 d . . . . .
C17 C 1.4400(4) 0.3555(3) 0.3483(3) 0.0447(8) Uani 1 1 d . . . . .
C19 C 1.6060(4) 0.3849(3) 0.3435(3) 0.0544(9) Uani 1 1 d . . . . .
H19 H 1.6167 0.3275 0.2754 0.065 Uiso 1 1 calc R U . . .
H3 H 0.262(5) -0.313(4) -0.022(4) 0.096(14) 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 C7 1.216(3) . ?
O2 C18 1.214(3) . ?
N2 C7 1.388(4) . ?
N2 C18 1.396(4) . ?
N2 C15 1.477(3) . ?
N1 C10 1.308(4) . ?
N1 C12 1.352(4) . ?
N1 C13 1.498(4) . ?
N3 C10 1.328(4) . ?
N3 C11 1.354(4) . ?
N3 H3 0.92(4) . ?
C7 C8 1.482(4) . ?
C8 C9 1.371(4) . ?
C8 C16 1.409(4) . ?
C9 C19 1.398(4) 2_866 ?
C9 H9 0.9300 . ?
C16 C17 1.409(4) . ?
C16 C16 1.416(5) 2_866 ?
C18 C17 1.480(4) . ?
C15 C14 1.505(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 C13 1.468(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C12 C11 1.340(5) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
O4 N4 1.228(3) . ?
O5 N4 1.233(4) . ?
O6 N5 1.225(4) . ?
O7 N5 1.245(4) . ?
O3 C4 1.258(4) . ?
N4 C3 1.438(4) . ?
N5 C1 1.447(5) . ?
C3 C2 1.388(4) . ?
C3 C4 1.438(5) . ?
C2 C1 1.373(5) . ?
C2 H2 0.9300 . ?
C1 C6 1.395(5) . ?
C6 C5 1.343(5) . ?
C6 H6 0.9300 . ?
C5 C4 1.429(5) . ?
C5 H5 0.9300 . ?
C17 C19 1.366(4) . ?
C19 C9 1.398(4) 2_866 ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N2 C18 125.4(2) . . ?
C7 N2 C15 119.0(3) . . ?
C18 N2 C15 115.6(3) . . ?
C10 N1 C12 108.0(3) . . ?
C10 N1 C13 125.3(3) . . ?
C12 N1 C13 126.6(3) . . ?
C10 N3 C11 107.5(3) . . ?
C10 N3 H3 128(2) . . ?
C11 N3 H3 125(2) . . ?
O1 C7 N2 120.7(3) . . ?
O1 C7 C8 122.4(3) . . ?
N2 C7 C8 116.8(3) . . ?
C9 C8 C16 120.0(3) . . ?
C9 C8 C7 120.3(3) . . ?
C16 C8 C7 119.8(3) . . ?
C8 C9 C19 120.6(3) . 2_866 ?
C8 C9 H9 119.7 . . ?
C19 C9 H9 119.7 2_866 . ?
C8 C16 C17 121.5(2) . . ?
C8 C16 C16 119.3(3) . 2_866 ?
C17 C16 C16 119.2(3) . 2_866 ?
O2 C18 N2 120.7(3) . . ?
O2 C18 C17 122.2(3) . . ?
N2 C18 C17 117.2(3) . . ?
N2 C15 C14 113.0(3) . . ?
N2 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C13 C14 C15 116.6(3) . . ?
C13 C14 H14A 108.1 . . ?
C15 C14 H14A 108.1 . . ?
C13 C14 H14B 108.1 . . ?
C15 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?
C14 C13 N1 111.5(3) . . ?
C14 C13 H13B 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13A 109.3 . . ?
H13B C13 H13A 108.0 . . ?
C11 C12 N1 107.6(3) . . ?
C11 C12 H12 126.2 . . ?
N1 C12 H12 126.2 . . ?
C12 C11 N3 107.4(3) . . ?
C12 C11 H11 126.3 . . ?
N3 C11 H11 126.3 . . ?
N1 C10 N3 109.5(3) . . ?
N1 C10 H10 125.3 . . ?
N3 C10 H10 125.3 . . ?
O4 N4 O5 121.5(3) . . ?
O4 N4 C3 119.8(3) . . ?
O5 N4 C3 118.7(3) . . ?
O6 N5 O7 123.2(4) . . ?
O6 N5 C1 119.4(4) . . ?
O7 N5 C1 117.4(4) . . ?
C2 C3 C4 122.9(3) . . ?
C2 C3 N4 115.6(3) . . ?
C4 C3 N4 121.4(3) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C1 C6 121.1(3) . . ?
C2 C1 N5 118.9(4) . . ?
C6 C1 N5 120.0(4) . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C6 C5 C4 123.5(4) . . ?
C6 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
O3 C4 C5 119.5(4) . . ?
O3 C4 C3 126.6(3) . . ?
C5 C4 C3 113.8(3) . . ?
C19 C17 C16 120.2(3) . . ?
C19 C17 C18 120.5(3) . . ?
C16 C17 C18 119.3(3) . . ?
C17 C19 C9 120.7(3) . 2_866 ?
C17 C19 H19 119.6 . . ?
C9 C19 H19 119.6 2_866 . ?

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
C18 N2 C7 O1 -177.2(3) . . . . ?
C15 N2 C7 O1 0.1(5) . . . . ?
C18 N2 C7 C8 3.2(5) . . . . ?
C15 N2 C7 C8 -179.5(3) . . . . ?
O1 C7 C8 C9 -0.9(5) . . . . ?
N2 C7 C8 C9 178.7(3) . . . . ?
O1 C7 C8 C16 178.4(3) . . . . ?
N2 C7 C8 C16 -2.0(5) . . . . ?
C16 C8 C9 C19 0.1(5) . . . 2_866 ?
C7 C8 C9 C19 179.3(3) . . . 2_866 ?
C9 C8 C16 C17 -179.8(3) . . . . ?
C7 C8 C16 C17 0.9(5) . . . . ?
C9 C8 C16 C16 -0.3(6) . . . 2_866 ?
C7 C8 C16 C16 -179.6(4) . . . 2_866 ?
C7 N2 C18 O2 177.7(3) . . . . ?
C15 N2 C18 O2 0.2(5) . . . . ?
C7 N2 C18 C17 -3.0(5) . . . . ?
C15 N2 C18 C17 179.6(3) . . . . ?
C7 N2 C15 C14 -97.9(4) . . . . ?
C18 N2 C15 C14 79.7(4) . . . . ?
N2 C15 C14 C13 88.2(4) . . . . ?
C15 C14 C13 N1 68.4(4) . . . . ?
C10 N1 C13 C14 76.2(5) . . . . ?
C12 N1 C13 C14 -102.8(4) . . . . ?
C10 N1 C12 C11 0.1(5) . . . . ?
C13 N1 C12 C11 179.2(4) . . . . ?
N1 C12 C11 N3 -0.1(5) . . . . ?
C10 N3 C11 C12 0.0(5) . . . . ?
C12 N1 C10 N3 0.0(5) . . . . ?
C13 N1 C10 N3 -179.2(3) . . . . ?
C11 N3 C10 N1 0.0(5) . . . . ?
O4 N4 C3 C2 176.4(3) . . . . ?
O5 N4 C3 C2 -4.4(5) . . . . ?
O4 N4 C3 C4 -2.7(5) . . . . ?
O5 N4 C3 C4 176.5(4) . . . . ?
C4 C3 C2 C1 0.0(6) . . . . ?
N4 C3 C2 C1 -179.1(3) . . . . ?
C3 C2 C1 C6 -2.4(6) . . . . ?
C3 C2 C1 N5 176.7(3) . . . . ?
O6 N5 C1 C2 8.4(6) . . . . ?
O7 N5 C1 C2 -170.4(4) . . . . ?
O6 N5 C1 C6 -172.5(4) . . . . ?
O7 N5 C1 C6 8.7(5) . . . . ?
C2 C1 C6 C5 1.9(6) . . . . ?
N5 C1 C6 C5 -177.2(4) . . . . ?
C1 C6 C5 C4 1.1(6) . . . . ?
C6 C5 C4 O3 176.5(4) . . . . ?
C6 C5 C4 C3 -3.2(6) . . . . ?
C2 C3 C4 O3 -177.0(4) . . . . ?
N4 C3 C4 O3 2.0(6) . . . . ?
C2 C3 C4 C5 2.7(6) . . . . ?
N4 C3 C4 C5 -178.3(3) . . . . ?
C8 C16 C17 C19 179.9(3) . . . . ?
C16 C16 C17 C19 0.4(6) 2_866 . . . ?
C8 C16 C17 C18 -0.7(5) . . . . ?
C16 C16 C17 C18 179.8(4) 2_866 . . . ?
O2 C18 C17 C19 0.4(5) . . . . ?
N2 C18 C17 C19 -179.0(3) . . . . ?
O2 C18 C17 C16 -179.1(3) . . . . ?
N2 C18 C17 C16 1.6(5) . . . . ?
C16 C17 C19 C9 -0.2(5) . . . 2_866 ?
C18 C17 C19 C9 -179.6(3) . . . 2_866 ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.208
_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_L(dhpa)2
_database_code_depnum_ccdc_archive 'CCDC 1521930'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N6 O4, 2(C7 H7 N O3)'
_chemical_formula_sum            'C40 H36 N8 O10'
_chemical_formula_weight         788.77

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                   9.2173(10)
_cell_length_b                   10.4784(11)
_cell_length_c                   11.2283(9)
_cell_angle_alpha                101.512(8)
_cell_angle_beta                 98.485(8)
_cell_angle_gamma                108.836(10)
_cell_volume                     979.11(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1200
_cell_measurement_theta_min      3.74
_cell_measurement_theta_max      22.30

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5965
_diffrn_reflns_av_unetI/netI     0.0825
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.184
_diffrn_reflns_theta_max         25.249
_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             3537
_reflns_number_gt                1749
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+2.1000P] 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         3537
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1833
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.5703(4) 0.7942(4) 0.6655(3) 0.0666(10) Uani 1 1 d . . . . .
N2 N 0.7343(4) 0.8433(4) 0.8534(3) 0.0505(10) Uani 1 1 d . . . . .
O2 O 0.1560(5) 0.7326(4) 0.0313(4) 0.0701(11) Uani 1 1 d . . . . .
O5 O 0.8858(4) 0.8725(4) 1.0422(3) 0.0798(12) Uani 1 1 d . . . . .
O1 O 0.4183(5) 0.5653(5) -0.1501(3) 0.0847(12) Uani 1 1 d . . . . .
H1 H 0.3586 0.5374 -0.2193 0.127 Uiso 1 1 calc R U . . .
N1 N 0.8652(5) 0.5710(4) 0.5778(4) 0.0615(11) Uani 1 1 d . . . . .
C17 C 0.6023(6) 0.8451(5) 0.7776(4) 0.0502(12) Uani 1 1 d . . . . .
C19 C 0.5462(5) 0.9676(4) 0.9710(4) 0.0397(10) Uani 1 1 d . . . . .
O3 O 0.0931(5) 0.8672(5) 0.2386(3) 0.0844(12) Uani 1 1 d . . . . .
H3 H 0.0483 0.8466 0.1649 0.127 Uiso 1 1 calc R U . . .
N4 N 0.3469(5) 0.6208(4) -0.0620(4) 0.0638(12) Uani 1 1 d . . . . .
C20 C 0.6773(5) 0.9578(4) 1.0430(4) 0.0441(11) Uani 1 1 d . . . . .
C18 C 0.5041(5) 0.9130(4) 0.8399(4) 0.0432(11) Uani 1 1 d . . . . .
C9 C 0.3765(5) 0.9237(5) 0.7716(4) 0.0512(12) Uani 1 1 d . . . . .
H9 H 0.3498 0.8875 0.6853 0.061 Uiso 1 1 calc R U . . .
C8 C 0.2845(5) 0.9884(5) 0.8289(4) 0.0512(12) Uani 1 1 d . . . . .
H8 H 0.1975 0.9953 0.7809 0.061 Uiso 1 1 calc R U . . .
C16 C 0.7749(6) 0.8885(5) 0.9831(4) 0.0539(12) Uani 1 1 d . . . . .
C3 C 0.2535(6) 0.7547(5) 0.1430(4) 0.0586(14) Uani 1 1 d . . . . .
N3 N 0.7672(6) 0.5255(5) 0.3761(4) 0.0782(14) Uani 1 1 d . . . . .
C2 C 0.3830(6) 0.7151(5) 0.1565(4) 0.0577(13) Uani 1 1 d . . . . .
C15 C 0.8354(6) 0.7805(5) 0.7916(5) 0.0596(13) Uani 1 1 d . . . . .
H15A H 0.9428 0.8241 0.8409 0.071 Uiso 1 1 calc R U . . .
H15B H 0.8346 0.7990 0.7103 0.071 Uiso 1 1 calc R U . . .
C1 C 0.4279(6) 0.6489(5) 0.0490(5) 0.0633(14) Uani 1 1 d . . . . .
H1A H 0.5176 0.6262 0.0613 0.076 Uiso 1 1 calc R U . . .
C4 C 0.2184(7) 0.8246(5) 0.2484(5) 0.0632(14) Uani 1 1 d . . . . .
C10 C 0.7504(7) 0.4863(6) 0.4787(5) 0.0748(16) Uani 1 1 d . . . . .
H10 H 0.6680 0.4085 0.4823 0.090 Uiso 1 1 calc R U . . .
C11 C 0.8994(8) 0.6419(7) 0.4114(6) 0.0863(19) Uani 1 1 d . . . . .
H11 H 0.9413 0.6944 0.3586 0.104 Uiso 1 1 calc R U . . .
C14 C 0.7817(6) 0.6259(5) 0.7757(5) 0.0638(14) Uani 1 1 d . . . . .
H14A H 0.6725 0.5829 0.7302 0.077 Uiso 1 1 calc R U . . .
H14B H 0.7876 0.6076 0.8573 0.077 Uiso 1 1 calc R U . . .
C13 C 0.8802(7) 0.5594(6) 0.7061(5) 0.0701(15) Uani 1 1 d . . . . .
H13A H 0.9899 0.6046 0.7502 0.084 Uiso 1 1 calc R U . . .
H13B H 0.8474 0.4615 0.7054 0.084 Uiso 1 1 calc R U . . .
C6 C 0.4392(8) 0.8135(6) 0.3784(5) 0.0786(18) Uani 1 1 d . . . . .
H6 H 0.5025 0.8342 0.4575 0.094 Uiso 1 1 calc R U . . .
C7 C 0.4757(7) 0.7434(6) 0.2758(5) 0.0720(16) Uani 1 1 d . . . . .
H7 H 0.5616 0.7152 0.2862 0.086 Uiso 1 1 calc R U . . .
C5 C 0.3119(7) 0.8525(6) 0.3647(5) 0.0738(17) Uani 1 1 d . . . . .
H5 H 0.2880 0.8984 0.4346 0.089 Uiso 1 1 calc R U . . .
C12 C 0.9613(7) 0.6704(7) 0.5345(6) 0.0808(18) Uani 1 1 d . . . . .
H12 H 1.0525 0.7442 0.5808 0.097 Uiso 1 1 calc R U . . .
H2 H 0.186(7) 0.689(6) -0.020(5) 0.08(2) 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 C17 1.215(5) . ?
N2 C17 1.386(6) . ?
N2 C16 1.391(6) . ?
N2 C15 1.479(6) . ?
O2 C3 1.360(5) . ?
O5 C16 1.212(5) . ?
O1 N4 1.399(5) . ?
N1 C10 1.341(6) . ?
N1 C12 1.357(7) . ?
N1 C13 1.460(6) . ?
C17 C18 1.489(6) . ?
C19 C20 1.395(6) . ?
C19 C19 1.404(8) 2_677 ?
C19 C18 1.414(5) . ?
O3 C4 1.364(6) . ?
N4 C1 1.279(6) . ?
C20 C8 1.382(6) 2_677 ?
C20 C16 1.481(6) . ?
C18 C9 1.356(6) . ?
C9 C8 1.397(6) . ?
C8 C20 1.382(6) 2_677 ?
C3 C2 1.383(7) . ?
C3 C4 1.401(7) . ?
N3 C10 1.312(6) . ?
N3 C11 1.354(7) . ?
C2 C7 1.397(6) . ?
C2 C1 1.452(7) . ?
C15 C14 1.497(6) . ?
C4 C5 1.373(7) . ?
C11 C12 1.348(8) . ?
C14 C13 1.523(7) . ?
C6 C5 1.360(8) . ?
C6 C7 1.384(8) . ?

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
C17 N2 C16 125.5(4) . . ?
C17 N2 C15 117.2(4) . . ?
C16 N2 C15 117.3(4) . . ?
C10 N1 C12 105.8(5) . . ?
C10 N1 C13 126.7(5) . . ?
C12 N1 C13 127.5(5) . . ?
O4 C17 N2 120.9(4) . . ?
O4 C17 C18 122.2(4) . . ?
N2 C17 C18 116.9(4) . . ?
C20 C19 C19 119.9(5) . 2_677 ?
C20 C19 C18 121.1(4) . . ?
C19 C19 C18 119.0(5) 2_677 . ?
C1 N4 O1 111.1(4) . . ?
C8 C20 C19 119.9(4) 2_677 . ?
C8 C20 C16 119.6(4) 2_677 . ?
C19 C20 C16 120.4(4) . . ?
C9 C18 C19 120.2(4) . . ?
C9 C18 C17 120.5(4) . . ?
C19 C18 C17 119.3(4) . . ?
C18 C9 C8 120.9(4) . . ?
C20 C8 C9 120.0(4) 2_677 . ?
O5 C16 N2 120.8(5) . . ?
O5 C16 C20 122.8(4) . . ?
N2 C16 C20 116.5(4) . . ?
O2 C3 C2 124.1(5) . . ?
O2 C3 C4 116.2(5) . . ?
C2 C3 C4 119.8(4) . . ?
C10 N3 C11 104.9(5) . . ?
C3 C2 C7 119.4(5) . . ?
C3 C2 C1 121.4(4) . . ?
C7 C2 C1 119.2(5) . . ?
N2 C15 C14 112.2(4) . . ?
N4 C1 C2 121.5(5) . . ?
O3 C4 C5 118.6(5) . . ?
O3 C4 C3 121.4(5) . . ?
C5 C4 C3 119.9(5) . . ?
N3 C10 N1 112.4(5) . . ?
C12 C11 N3 110.0(6) . . ?
C15 C14 C13 112.5(4) . . ?
N1 C13 C14 112.3(4) . . ?
C5 C6 C7 120.7(5) . . ?
C6 C7 C2 119.7(5) . . ?
C6 C5 C4 120.5(6) . . ?
C11 C12 N1 106.9(5) . . ?

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_L(cat)
_database_code_depnum_ccdc_archive 'CCDC 1521931'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;
_audit_creation_date             2017-07-12
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2017.07.04 svn.r3433 for OlexSys, GUI svn.r5356)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 N6 O4, C6 H6 O2'
_chemical_formula_sum            'C32 H28 N6 O6'
_chemical_formula_weight         592.60
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4179(5)
_cell_length_b                   9.5207(5)
_cell_length_c                   16.3424(8)
_cell_angle_alpha                86.803(4)
_cell_angle_beta                 88.439(3)
_cell_angle_gamma                69.925(4)
_cell_volume                     1374.12(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1204
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.30
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.1091
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14271
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.248
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2872
_reflns_number_total             4740
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0621
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.3233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1959
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 N1A, C13B, H13E, H13F, C14B, H14E, H14F, C15B, H15E, H15F, N3B, C12B, H12B,
 C10B, H10B, C11B, H11B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N3A, C12A, H12A, C10A, H10A, C11A, H11A, C13A, H13C, H13D, C14A, H14C, H14D,
 C15A, H15C, H15D, N1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: N3A(0.6) C12A(0.6) H12A(0.6) C10A(0.6) H10A(0.6) N1A(0.4)
 C11A(0.6) H11A(0.6) C13A(0.6) H13C(0.6) H13D(0.6) C14A(0.6) H14C(0.6)
 H14D(0.6) C15A(0.6) H15C(0.6) H15D(0.6) C13B(0.4) H13E(0.4) H13F(0.4)
 C14B(0.4) H14E(0.4) H14F(0.4) C15B(0.4) H15E(0.4) H15F(0.4) N3B(0.4) C12B(0.4)
 H12B(0.4) C10B(0.4) H10B(0.4) N1B(0.6) C11B(0.4) H11B(0.4)
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C13(H13A,H13B), C13A(H13C,H13D), C14A(H14C,
 H14D), C15A(H15C,H15D), C13B(H13E,H13F), C14B(H14E,H14F), C15B(H15E,H15F)
4.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C18(H18), C23(H23), C19(H19), C12(H12), C10(H10), C12A(H12A),
 C10A(H10A), C11(H11), C11A(H11A), C2(H2), C5(H5), C4(H4), C3(H3), C12B(H12B),
 C10B(H10B), C11B(H11B)
4.c Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C8 C 0.3811(3) 0.1797(3) 0.42332(15) 0.0408(6) Uani 1 1 d . . . . .
C21 C 0.1942(3) 0.2257(3) 0.53353(15) 0.0407(7) Uani 1 1 d . . . . .
C16 C 0.2840(3) 0.4267(3) 0.48306(15) 0.0416(7) Uani 1 1 d . . . . .
C20 C 0.0989(3) 0.3243(3) 0.58968(15) 0.0431(7) Uani 1 1 d . . . . .
C9 C 0.2867(3) 0.2779(3) 0.47991(14) 0.0392(6) Uani 1 1 d . . . . .
C22 C 0.1969(3) 0.0779(3) 0.53006(15) 0.0417(7) Uani 1 1 d . . . . .
C7 C 0.4809(3) 0.2330(3) 0.36801(16) 0.0449(7) Uani 1 1 d . . . . .
C17 C 0.3805(3) 0.4825(3) 0.42638(16) 0.0450(7) Uani 1 1 d . . . . .
C24 C 0.3808(3) 0.0363(3) 0.42051(16) 0.0471(7) Uani 1 1 d . . . . .
H24 H 0.4419 -0.0271 0.3825 0.057 Uiso 1 1 calc R . . . .
C18 C 0.1910(3) 0.5205(3) 0.53895(16) 0.0468(7) Uani 1 1 d . . . . .
H18 H 0.1896 0.6183 0.5414 0.056 Uiso 1 1 calc R . . . .
C26 C -0.0016(3) 0.2713(4) 0.64412(16) 0.0515(8) Uani 1 1 d . . . . .
C23 C 0.2891(3) -0.0162(3) 0.47441(16) 0.0476(7) Uani 1 1 d . . . . .
H23 H 0.2906 -0.1141 0.4725 0.057 Uiso 1 1 calc R . . . .
C19 C 0.0991(3) 0.4683(4) 0.59179(16) 0.0497(7) Uani 1 1 d . . . . .
H19 H 0.0368 0.5322 0.6292 0.060 Uiso 1 1 calc R . . . .
C25 C 0.1009(3) 0.0213(4) 0.58644(16) 0.0504(8) Uani 1 1 d . . . . .
C15 C 0.5673(3) 0.4322(4) 0.31291(16) 0.0529(8) Uani 1 1 d . . . . .
H15A H 0.6673 0.3568 0.3107 0.064 Uiso 1 1 calc R . . . .
H15B H 0.5779 0.5236 0.3307 0.064 Uiso 1 1 calc R . . . .
C14 C 0.4980(4) 0.4606(4) 0.22827(17) 0.0592(8) Uani 1 1 d . . . . .
H14A H 0.4006 0.5403 0.2300 0.071 Uiso 1 1 calc R . . . .
H14B H 0.4815 0.3710 0.2121 0.071 Uiso 1 1 calc R . . . .
C13 C 0.5986(4) 0.5040(4) 0.16511(18) 0.0650(9) Uani 1 1 d . . . . .
H13A H 0.6932 0.4214 0.1603 0.078 Uiso 1 1 calc R . . . .
H13B H 0.5497 0.5233 0.1122 0.078 Uiso 1 1 calc R . . . .
C12 C 0.5271(4) 0.7724(4) 0.2025(2) 0.0717(10) Uani 1 1 d . . . . .
H12 H 0.4226 0.8020 0.1978 0.086 Uiso 1 1 calc R . . . .
N3 N 0.7559(4) 0.7802(4) 0.22478(19) 0.0849(9) Uani 1 1 d . . . . .
C10 C 0.7641(4) 0.6491(5) 0.2012(2) 0.0728(10) Uani 1 1 d . . . . .
H10 H 0.8552 0.5712 0.1946 0.087 Uiso 1 1 calc R . . . .
N3A N 0.1556(18) -0.253(2) 1.0004(11) 0.064(3) Uani 0.6 1 d . U P A 1
C12A C 0.263(3) -0.128(3) 0.9141(15) 0.086(7) Uani 0.6 1 d . U P A 1
H12A H 0.3213 -0.0701 0.8962 0.103 Uiso 0.6 1 calc R U P A 1
C10A C 0.0806(8) -0.2079(9) 0.9314(4) 0.063(2) Uani 0.6 1 d . U P A 1
H10A H -0.0117 -0.2202 0.9231 0.076 Uiso 0.6 1 calc R U P A 1
N2 N 0.4726(3) 0.3812(3) 0.37241(13) 0.0456(6) Uani 1 1 d . . . . .
N2A N 0.0077(3) 0.1228(3) 0.64043(13) 0.0519(6) Uani 1 1 d . . . . .
N1 N 0.6297(3) 0.6367(3) 0.18729(14) 0.0536(7) Uani 1 1 d . . . . .
N1A N 0.1138(9) -0.0755(9) 0.9056(5) 0.0583(19) Uani 0.4 1 d . U P B 2
C11 C 0.6077(5) 0.8561(4) 0.2261(2) 0.0752(10) Uani 1 1 d . . . . .
H11 H 0.5650 0.9545 0.2414 0.090 Uiso 1 1 calc R . . . .
C11A C 0.279(2) -0.2144(19) 0.9873(9) 0.081(5) Uani 0.6 1 d . U P A 1
H11A H 0.3625 -0.2412 1.0217 0.098 Uiso 0.6 1 calc R U P A 1
C1 C 0.7824(3) -0.3207(4) 0.82679(17) 0.0544(8) Uani 1 1 d . . . . .
C6 C 0.8090(3) -0.4258(4) 0.89265(18) 0.0550(8) Uani 1 1 d . . . . .
C2 C 0.7142(4) -0.1717(4) 0.8403(2) 0.0643(9) Uani 1 1 d . . . . .
H2 H 0.6960 -0.1019 0.7962 0.077 Uiso 1 1 calc R . . . .
C5 C 0.7704(4) -0.3766(4) 0.97055(19) 0.0678(9) Uani 1 1 d . . . . .
H5 H 0.7905 -0.4457 1.0150 0.081 Uiso 1 1 calc R . . . .
C4 C 0.7024(4) -0.2262(4) 0.9835(2) 0.0718(10) Uani 1 1 d . . . . .
H4 H 0.6773 -0.1947 1.0365 0.086 Uiso 1 1 calc R . . . .
C3 C 0.6718(4) -0.1234(4) 0.9187(2) 0.0732(10) Uani 1 1 d . . . . .
H3 H 0.6231 -0.0222 0.9272 0.088 Uiso 1 1 calc R . . . .
O4 O 0.5680(2) 0.1520(2) 0.32026(12) 0.0634(6) Uani 1 1 d . . . . .
O3 O 0.3806(2) 0.6104(2) 0.42640(12) 0.0613(6) Uani 1 1 d . . . . .
O5 O -0.0930(2) 0.3528(3) 0.69035(12) 0.0693(7) Uani 1 1 d . . . . .
O6 O 0.0997(3) -0.1053(3) 0.58626(13) 0.0650(6) Uani 1 1 d . . . . .
O2 O 0.8236(3) -0.3631(3) 0.74906(12) 0.0726(7) Uani 1 1 d . . . . .
H2A H 0.8520 -0.4546 0.7483 0.109 Uiso 1 1 calc GR . . . .
O1 O 0.8733(3) -0.5710(3) 0.87388(13) 0.0775(7) Uani 1 1 d . . . . .
H1 H 0.8636 -0.6252 0.9128 0.116 Uiso 1 1 calc GR . . . .
C13A C -0.102(2) 0.0871(19) 0.6968(10) 0.057(3) Uani 0.6 1 d . U P A 1
H13C H -0.1235 0.0015 0.6780 0.068 Uiso 0.6 1 calc R U P A 1
H13D H -0.1965 0.1715 0.6967 0.068 Uiso 0.6 1 calc R U P A 1
C14A C -0.0394(6) 0.0519(6) 0.7848(3) 0.0493(12) Uani 0.6 1 d . U P A 1
H14C H -0.0062 0.1321 0.8009 0.059 Uiso 0.6 1 calc R U P A 1
H14D H -0.1187 0.0459 0.8225 0.059 Uiso 0.6 1 calc R U P A 1
C15A C 0.0907(8) -0.0933(8) 0.7897(4) 0.0562(18) Uani 0.6 1 d . U P A 1
H15C H 0.0602 -0.1701 0.7665 0.067 Uiso 0.6 1 calc R U P A 1
H15D H 0.1737 -0.0824 0.7566 0.067 Uiso 0.6 1 calc R U P A 1
C13B C -0.070(3) 0.043(3) 0.6994(17) 0.059(5) Uani 0.4 1 d . U P B 2
H13E H -0.1147 -0.0139 0.6676 0.071 Uiso 0.4 1 calc R U P B 2
H13F H -0.1526 0.1188 0.7260 0.071 Uiso 0.4 1 calc R U P B 2
C14B C 0.0272(12) -0.0620(13) 0.7659(6) 0.051(2) Uani 0.4 1 d . U P B 2
H14E H -0.0110 -0.1431 0.7793 0.061 Uiso 0.4 1 calc R U P B 2
H14F H 0.1303 -0.1049 0.7459 0.061 Uiso 0.4 1 calc R U P B 2
C15B C 0.0248(10) 0.0224(9) 0.8413(5) 0.061(2) Uani 0.4 1 d . U P B 2
H15E H 0.0645 0.1024 0.8279 0.073 Uiso 0.4 1 calc R U P B 2
H15F H -0.0787 0.0672 0.8603 0.073 Uiso 0.4 1 calc R U P B 2
N3B N 0.183(3) -0.234(3) 1.0072(15) 0.058(4) Uani 0.4 1 d . U P B 2
C12B C 0.283(4) -0.134(4) 0.906(2) 0.064(5) Uani 0.4 1 d . U P B 2
H12B H 0.3514 -0.1224 0.8665 0.077 Uiso 0.4 1 calc R U P B 2
C10B C 0.0672(15) -0.1557(15) 0.9645(7) 0.070(3) Uani 0.4 1 d . U P B 2
H10B H -0.0312 -0.1549 0.9726 0.084 Uiso 0.4 1 calc R U P B 2
N1B N 0.1449(6) -0.1434(6) 0.8739(3) 0.0543(12) Uani 0.6 1 d . U P A 1
C11B C 0.305(3) -0.203(2) 0.9757(12) 0.050(3) Uani 0.4 1 d . U P B 2
H11B H 0.3967 -0.2310 1.0029 0.060 Uiso 0.4 1 calc R U P B 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
C8 C9 1.415(3) . ?
C8 C7 1.479(4) . ?
C8 C24 1.370(4) . ?
C21 C20 1.415(4) . ?
C21 C9 1.407(4) . ?
C21 C22 1.403(4) . ?
C16 C9 1.412(4) . ?
C16 C17 1.482(4) . ?
C16 C18 1.382(4) . ?
C20 C26 1.474(4) . ?
C20 C19 1.374(4) . ?
C22 C23 1.377(4) . ?
C22 C25 1.480(4) . ?
C7 N2 1.391(4) . ?
C7 O4 1.215(3) . ?
C17 N2 1.393(3) . ?
C17 O3 1.217(3) . ?
C24 C23 1.406(4) . ?
C18 C19 1.396(4) . ?
C26 N2A 1.392(4) . ?
C26 O5 1.218(3) . ?
C25 N2A 1.398(4) . ?
C25 O6 1.210(3) . ?
C15 C14 1.516(4) . ?
C15 N2 1.475(3) . ?
C14 C13 1.517(4) . ?
C13 N1 1.457(4) . ?
C12 N1 1.354(4) . ?
C12 C11 1.351(5) . ?
N3 C10 1.304(4) . ?
N3 C11 1.334(5) . ?
C10 N1 1.337(4) . ?
N3A C10A 1.318(15) . ?
N3A C11A 1.346(16) . ?
C12A C11A 1.40(3) . ?
C12A N1B 1.36(3) . ?
C10A N1B 1.336(8) . ?
N2A C13A 1.48(2) . ?
N2A C13B 1.52(3) . ?
N1A C15B 1.441(11) . ?
N1A C12B 1.49(4) . ?
N1A C10B 1.352(13) . ?
C1 C6 1.394(4) . ?
C1 C2 1.369(4) . ?
C1 O2 1.360(3) . ?
C6 C5 1.377(4) . ?
C6 O1 1.354(4) . ?
C2 C3 1.389(5) . ?
C5 C4 1.379(5) . ?
C4 C3 1.367(5) . ?
C13A C14A 1.546(15) . ?
C14A C15A 1.500(8) . ?
C15A N1B 1.477(8) . ?
C13B C14B 1.53(2) . ?
C14B C15B 1.504(13) . ?
N3B C10B 1.29(2) . ?
N3B C11B 1.36(2) . ?
C12B C11B 1.27(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
C9 C8 C7 119.4(3) . . ?
C24 C8 C9 120.1(2) . . ?
C24 C8 C7 120.5(2) . . ?
C9 C21 C20 119.1(3) . . ?
C22 C21 C20 121.1(3) . . ?
C22 C21 C9 119.7(2) . . ?
C9 C16 C17 120.1(2) . . ?
C18 C16 C9 119.9(3) . . ?
C18 C16 C17 120.0(3) . . ?
C21 C20 C26 119.3(3) . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 C26 121.0(3) . . ?
C21 C9 C8 119.1(3) . . ?
C21 C9 C16 119.9(2) . . ?
C16 C9 C8 121.0(2) . . ?
C21 C22 C25 120.3(2) . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 C25 119.3(3) . . ?
N2 C7 C8 117.6(2) . . ?
O4 C7 C8 122.1(3) . . ?
O4 C7 N2 120.3(3) . . ?
N2 C17 C16 116.7(2) . . ?
O3 C17 C16 122.3(3) . . ?
O3 C17 N2 121.0(2) . . ?
C8 C24 C23 120.7(3) . . ?
C16 C18 C19 120.0(3) . . ?
N2A C26 C20 117.8(2) . . ?
O5 C26 C20 122.7(3) . . ?
O5 C26 N2A 119.5(3) . . ?
C22 C23 C24 119.8(3) . . ?
C20 C19 C18 121.3(3) . . ?
N2A C25 C22 116.7(3) . . ?
O6 C25 C22 122.9(3) . . ?
O6 C25 N2A 120.5(3) . . ?
N2 C15 C14 110.9(2) . . ?
C15 C14 C13 111.7(3) . . ?
N1 C13 C14 111.6(2) . . ?
C11 C12 N1 105.8(3) . . ?
C10 N3 C11 103.4(3) . . ?
N3 C10 N1 114.0(3) . . ?
C10A N3A C11A 103.0(13) . . ?
N1B C12A C11A 106.5(17) . . ?
N3A C10A N1B 116.2(8) . . ?
C7 N2 C17 125.2(2) . . ?
C7 N2 C15 115.8(2) . . ?
C17 N2 C15 119.0(2) . . ?
C26 N2A C25 124.8(2) . . ?
C26 N2A C13A 111.6(7) . . ?
C26 N2A C13B 125.0(11) . . ?
C25 N2A C13A 123.4(8) . . ?
C25 N2A C13B 109.9(11) . . ?
C12 N1 C13 127.0(3) . . ?
C10 N1 C13 127.8(3) . . ?
C10 N1 C12 105.1(3) . . ?
C15B N1A C12B 123.9(15) . . ?
C10B N1A C15B 127.7(9) . . ?
C10B N1A C12B 107.0(16) . . ?
N3 C11 C12 111.8(3) . . ?
N3A C11A C12A 109.3(16) . . ?
C2 C1 C6 119.7(3) . . ?
O2 C1 C6 121.3(3) . . ?
O2 C1 C2 119.1(3) . . ?
C5 C6 C1 119.0(3) . . ?
O1 C6 C1 116.0(3) . . ?
O1 C6 C5 125.0(3) . . ?
C1 C2 C3 121.0(3) . . ?
C6 C5 C4 120.8(3) . . ?
C3 C4 C5 120.3(3) . . ?
C4 C3 C2 119.2(3) . . ?
N2A C13A C14A 110.5(12) . . ?
C15A C14A C13A 110.7(8) . . ?
N1B C15A C14A 113.7(5) . . ?
N2A C13B C14B 116.9(18) . . ?
C15B C14B C13B 110.0(15) . . ?
N1A C15B C14B 111.0(8) . . ?
C10B N3B C11B 107.8(18) . . ?
C11B C12B N1A 100(2) . . ?
N3B C10B N1A 107.9(14) . . ?
C12A N1B C15A 129.8(12) . . ?
C10A N1B C12A 103.1(11) . . ?
C10A N1B C15A 127.0(6) . . ?
C12B C11B N3B 114(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L(res)2
_database_code_depnum_ccdc_archive 'CCDC 1521932'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N6 O4, 2(C6 H6 O2)'
_chemical_formula_sum            'C38 H34 N6 O8'
_chemical_formula_weight         702.71

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                   9.7353(4)
_cell_length_b                   14.6502(6)
_cell_length_c                   11.7908(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.654(3)
_cell_angle_gamma                90
_cell_volume                     1666.67(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2100
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      20.47

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12812
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         25.038
_diffrn_reflns_theta_full        25.038
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             2842
_reflns_number_gt                1848
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.1000P] 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         2842
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C16 C 0.5839(2) 0.06461(12) 0.62642(18) 0.0403(5) Uani 1 1 d . . . . .
C9 C 0.56330(19) 0.02245(12) 0.51823(17) 0.0379(5) Uani 1 1 d . . . . .
C17 C 0.7169(2) 0.11091(14) 0.6652(2) 0.0445(5) Uani 1 1 d . . . . .
C19 C 0.6436(2) -0.01867(14) 0.33998(19) 0.0474(6) Uani 1 1 d . . . . .
H19 H 0.7122 -0.0175 0.2921 0.057 Uiso 1 1 calc R U . . .
C8 C 0.6668(2) 0.02375(13) 0.44485(18) 0.0409(5) Uani 1 1 d . . . . .
C1 C 0.3776(2) 0.15100(14) 0.24408(19) 0.0457(5) Uani 1 1 d . . . . .
C18 C 0.4810(2) 0.06338(13) 0.69567(19) 0.0466(5) Uani 1 1 d . . . . .
H18 H 0.4946 0.0924 0.7664 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4342(2) 0.22915(13) 0.42160(19) 0.0456(5) Uani 1 1 d . . . . .
C2 C 0.4711(2) 0.19995(13) 0.31868(19) 0.0465(6) Uani 1 1 d . . . . .
H2 H 0.5586 0.2132 0.2996 0.056 Uiso 1 1 calc R U . . .
C7 C 0.7977(2) 0.07281(13) 0.4808(2) 0.0466(6) Uani 1 1 d . . . . .
C13 C 0.8496(2) 0.32095(14) 0.6449(2) 0.0524(6) Uani 1 1 d . . . . .
H13A H 0.7574 0.2947 0.6384 0.063 Uiso 1 1 calc R U . . .
H13B H 0.8872 0.3216 0.7254 0.063 Uiso 1 1 calc R U . . .
C15 C 0.9454(2) 0.16292(14) 0.6231(2) 0.0524(6) Uani 1 1 d . . . . .
H15A H 1.0204 0.1315 0.5929 0.063 Uiso 1 1 calc R U . . .
H15B H 0.9656 0.1626 0.7059 0.063 Uiso 1 1 calc R U . . .
C12 C 0.9103(2) 0.48980(15) 0.6476(2) 0.0527(6) Uani 1 1 d . . . . .
H12 H 0.9781 0.4910 0.7111 0.063 Uiso 1 1 calc R U . . .
C14 C 0.9398(2) 0.26134(14) 0.5810(2) 0.0515(6) Uani 1 1 d . . . . .
H14B H 1.0329 0.2862 0.5899 0.062 Uiso 1 1 calc R U . . .
H14A H 0.9042 0.2623 0.5002 0.062 Uiso 1 1 calc R U . . .
C5 C 0.2124(2) 0.16212(16) 0.3749(2) 0.0579(6) Uani 1 1 d . . . . .
H5 H 0.1245 0.1496 0.3936 0.069 Uiso 1 1 calc R U . . .
N3 N 0.7638(2) 0.53301(14) 0.49720(17) 0.0672(6) Uani 1 1 d . . . . .
C6 C 0.2471(2) 0.13199(15) 0.2719(2) 0.0542(6) Uani 1 1 d . . . . .
H6 H 0.1837 0.0993 0.2217 0.065 Uiso 1 1 calc R U . . .
C4 C 0.3041(2) 0.21017(14) 0.45044(19) 0.0514(6) Uani 1 1 d . . . . .
H4 H 0.2794 0.2297 0.5200 0.062 Uiso 1 1 calc R U . . .
C10 C 0.7535(3) 0.44494(17) 0.5123(2) 0.0644(7) Uani 1 1 d . . . . .
H10 H 0.6932 0.4074 0.4655 0.077 Uiso 1 1 calc R U . . .
O1 O 0.42008(16) 0.12211(11) 0.14430(13) 0.0614(5) Uani 1 1 d . . . . .
H1 H 0.3567 0.0945 0.1061 0.092 Uiso 1 1 calc R U . . .
O4 O 0.74180(15) 0.14650(11) 0.75886(14) 0.0596(5) Uani 1 1 d . . . . .
O3 O 0.88857(15) 0.07875(11) 0.41907(14) 0.0645(5) Uani 1 1 d . . . . .
O2 O 0.53295(15) 0.27463(12) 0.49347(14) 0.0670(5) Uani 1 1 d . . . . .
H2A H 0.4957 0.3034 0.5406 0.101 Uiso 1 1 calc R U . . .
N1 N 0.83940(17) 0.41513(11) 0.60230(15) 0.0484(5) Uani 1 1 d . . . . .
C11 C 0.8630(3) 0.56113(18) 0.5827(2) 0.0602(7) Uani 1 1 d . . . . .
N2 N 0.81520(16) 0.11306(11) 0.58880(15) 0.0434(4) Uani 1 1 d . . . . .
H11 H 0.893(2) 0.6226(16) 0.5939(19) 0.069(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
C16 C18 1.374(3) . ?
C16 C9 1.407(3) . ?
C16 C17 1.480(3) . ?
C9 C9 1.413(4) 3_656 ?
C9 C8 1.413(3) . ?
C17 O4 1.216(2) . ?
C17 N2 1.399(3) . ?
C19 C8 1.375(3) . ?
C19 C18 1.394(3) 3_656 ?
C8 C7 1.475(3) . ?
C1 O1 1.365(2) . ?
C1 C2 1.380(3) . ?
C1 C6 1.382(3) . ?
C18 C19 1.394(3) 3_656 ?
C3 O2 1.367(2) . ?
C3 C2 1.378(3) . ?
C3 C4 1.383(3) . ?
C7 O3 1.222(2) . ?
C7 N2 1.393(3) . ?
C13 N1 1.467(3) . ?
C13 C14 1.509(3) . ?
C15 N2 1.472(2) . ?
C15 C14 1.523(3) . ?
C12 C11 1.340(3) . ?
C12 N1 1.364(3) . ?
C5 C4 1.370(3) . ?
C5 C6 1.376(3) . ?
N3 C10 1.308(3) . ?
N3 C11 1.364(3) . ?
C10 N1 1.335(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
C18 C16 C9 120.39(18) . . ?
C18 C16 C17 120.0(2) . . ?
C9 C16 C17 119.62(18) . . ?
C16 C9 C9 119.6(2) . 3_656 ?
C16 C9 C8 121.47(17) . . ?
C9 C9 C8 119.0(2) 3_656 . ?
O4 C17 N2 120.31(19) . . ?
O4 C17 C16 122.5(2) . . ?
N2 C17 C16 117.2(2) . . ?
C8 C19 C18 121.03(19) . 3_656 ?
C19 C8 C9 119.95(18) . . ?
C19 C8 C7 120.72(19) . . ?
C9 C8 C7 119.31(19) . . ?
O1 C1 C2 117.43(19) . . ?
O1 C1 C6 122.4(2) . . ?
C2 C1 C6 120.2(2) . . ?
C16 C18 C19 120.1(2) . 3_656 ?
O2 C3 C2 116.94(18) . . ?
O2 C3 C4 122.5(2) . . ?
C2 C3 C4 120.6(2) . . ?
C3 C2 C1 119.71(19) . . ?
O3 C7 N2 120.28(19) . . ?
O3 C7 C8 122.0(2) . . ?
N2 C7 C8 117.73(18) . . ?
N1 C13 C14 113.00(18) . . ?
N2 C15 C14 112.80(17) . . ?
C11 C12 N1 106.5(2) . . ?
C13 C14 C15 112.55(18) . . ?
C4 C5 C6 121.5(2) . . ?
C10 N3 C11 104.9(2) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C4 C3 118.9(2) . . ?
N3 C10 N1 112.3(2) . . ?
C10 N1 C12 106.26(18) . . ?
C10 N1 C13 125.95(19) . . ?
C12 N1 C13 127.75(18) . . ?
C12 C11 N3 110.0(2) . . ?
C7 N2 C17 124.60(17) . . ?
C7 N2 C15 117.23(17) . . ?
C17 N2 C15 118.16(17) . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.040

