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

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

data_p1818a
_database_code_depnum_ccdc_archive 'CCDC 1940949'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 O4, C10 H8 N2'
_chemical_formula_sum            'C18 H22 N2 O4'
_chemical_formula_weight         330.37

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

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

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

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

_cell_length_a                   8.9732(5)
_cell_length_b                   9.5401(5)
_cell_length_c                   10.9902(6)
_cell_angle_alpha                82.2592(19)
_cell_angle_beta                 72.1344(17)
_cell_angle_gamma                65.7070(16)
_cell_volume                     816.12(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9145
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.3

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.585
_exptl_crystal_size_mid          0.445
_exptl_crystal_size_min          0.202
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7166
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            22341
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.342
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4061
_reflns_number_gt                3327
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0652P)²+0.2272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4061
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O01 O 0.66901(10) 0.85892(10) -0.11396(8) 0.0261(2) Uani 1 1 d . . . . .
H01 H 0.722(2) 0.9155(18) -0.1801(15) 0.039 Uiso 1 1 d . U . . .
O02 O 0.45871(10) 0.96430(9) -0.20847(8) 0.02434(19) Uani 1 1 d . . . . .
O11 O -0.22186(11) 0.42463(10) 0.30657(8) 0.0277(2) Uani 1 1 d . . . . .
O12 O -0.45401(10) 0.55617(10) 0.24033(9) 0.0290(2) Uani 1 1 d . . . . .
H12 H -0.495(2) 0.4843(19) 0.2942(16) 0.043 Uiso 1 1 d . U . . .
C03 C 0.51999(13) 0.87947(12) -0.12826(10) 0.0174(2) Uani 1 1 d . . . . .
C04 C 0.43983(14) 0.78266(13) -0.03377(10) 0.0199(2) Uani 1 1 d . . . . .
H04A H 0.427557 0.809699 0.053648 0.024 Uiso 1 1 calc R U . . .
H04B H 0.518356 0.673276 -0.047266 0.024 Uiso 1 1 calc R U . . .
C05 C 0.26752(13) 0.79975(12) -0.04148(10) 0.0193(2) Uani 1 1 d . . . . .
H05A H 0.277899 0.773571 -0.128679 0.023 Uiso 1 1 calc R U . . .
H05B H 0.186699 0.908147 -0.025401 0.023 Uiso 1 1 calc R U . . .
C06 C 0.19762(13) 0.69579(12) 0.05558(10) 0.0175(2) Uani 1 1 d . . . . .
H06A H 0.276927 0.587418 0.036754 0.021 Uiso 1 1 calc R U . . .
H06B H 0.193702 0.718706 0.141996 0.021 Uiso 1 1 calc R U . . .
C07 C 0.02078(13) 0.71357(12) 0.05632(10) 0.0178(2) Uani 1 1 d . . . . .
H07A H 0.024411 0.690719 -0.030027 0.021 Uiso 1 1 calc R U . . .
H07B H -0.058848 0.821792 0.075501 0.021 Uiso 1 1 calc R U . . .
C08 C -0.04733(13) 0.60878(12) 0.15354(10) 0.0165(2) Uani 1 1 d . . . . .
H08A H 0.029672 0.500185 0.132985 0.020 Uiso 1 1 calc R U . . .
H08B H -0.048678 0.629408 0.239860 0.020 Uiso 1 1 calc R U . . .
C09 C -0.22583(13) 0.63324(12) 0.15406(10) 0.0175(2) Uani 1 1 d . . . . .
H09A H -0.302969 0.740583 0.179261 0.021 Uiso 1 1 calc R U . . .
H09B H -0.224836 0.619989 0.065966 0.021 Uiso 1 1 calc R U . . .
C10 C -0.29687(13) 0.52651(12) 0.24211(10) 0.0171(2) Uani 1 1 d . . . . .
N13 N 0.39295(12) 0.37713(11) 0.37387(9) 0.0212(2) Uani 1 1 d . . . . .
N24 N -0.15090(12) 0.00410(11) 0.72538(8) 0.0199(2) Uani 1 1 d . . . . .
C14 C 0.25158(14) 0.39800(13) 0.34503(10) 0.0219(2) Uani 1 1 d . . . . .
H14 H 0.223429 0.466690 0.276841 0.026 Uiso 1 1 calc R U . . .
C15 C 0.43230(14) 0.27827(13) 0.46879(11) 0.0217(2) Uani 1 1 d . . . . .
H15 H 0.533705 0.260785 0.489767 0.026 Uiso 1 1 calc R U . . .
C16 C 0.14294(14) 0.32559(12) 0.40846(10) 0.0197(2) Uani 1 1 d . . . . .
H16 H 0.043543 0.344591 0.383930 0.024 Uiso 1 1 calc R U . . .
C17 C 0.33181(14) 0.19987(13) 0.53820(10) 0.0193(2) Uani 1 1 d . . . . .
H17 H 0.364686 0.130439 0.604790 0.023 Uiso 1 1 calc R U . . .
C18 C 0.18196(13) 0.22430(11) 0.50898(9) 0.0152(2) Uani 1 1 d . . . . .
C19 C 0.06679(13) 0.14739(11) 0.58333(9) 0.0152(2) Uani 1 1 d . . . . .
C20 C -0.09944(14) 0.19737(12) 0.57508(10) 0.0187(2) Uani 1 1 d . . . . .
H20 H -0.141353 0.280992 0.520340 0.022 Uiso 1 1 calc R U . . .
C21 C 0.12006(14) 0.02355(13) 0.66548(10) 0.0198(2) Uani 1 1 d . . . . .
H21 H 0.231587 -0.013665 0.675258 0.024 Uiso 1 1 calc R U . . .
C22 C -0.20303(14) 0.12349(13) 0.64784(10) 0.0201(2) Uani 1 1 d . . . . .
H22 H -0.316432 0.159599 0.642194 0.024 Uiso 1 1 calc R U . . .
C23 C 0.00833(14) -0.04437(13) 0.73253(10) 0.0212(2) Uani 1 1 d . . . . .
H23 H 0.047280 -0.130012 0.786446 0.025 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O01 C03 1.3252(13) . ?
O01 H01 0.969(17) . ?
O02 C03 1.2138(13) . ?
O11 C10 1.2118(13) . ?
O12 C10 1.3251(13) . ?
O12 H12 0.959(18) . ?
C03 C04 1.5096(13) . ?
C04 C05 1.5145(14) . ?
C04 H04A 0.9900 . ?
C04 H04B 0.9900 . ?
C05 C06 1.5268(13) . ?
C05 H05A 0.9900 . ?
C05 H05B 0.9900 . ?
C06 C07 1.5224(14) . ?
C06 H06A 0.9900 . ?
C06 H06B 0.9900 . ?
C07 C08 1.5260(13) . ?
C07 H07A 0.9900 . ?
C07 H07B 0.9900 . ?
C08 C09 1.5190(14) . ?
C08 H08A 0.9900 . ?
C08 H08B 0.9900 . ?
C09 C10 1.5065(14) . ?
C09 H09A 0.9900 . ?
C09 H09B 0.9900 . ?
N13 C14 1.3309(14) . ?
N13 C15 1.3376(14) . ?
N24 C23 1.3330(14) . ?
N24 C22 1.3368(14) . ?
C14 C16 1.3860(14) . ?
C14 H14 0.9500 . ?
C15 C17 1.3905(15) . ?
C15 H15 0.9500 . ?
C16 C18 1.3957(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.3973(14) . ?
C17 H17 0.9500 . ?
C18 C19 1.4895(14) . ?
C19 C20 1.3952(14) . ?
C19 C21 1.3972(14) . ?
C20 C22 1.3898(14) . ?
C20 H20 0.9500 . ?
C21 C23 1.3859(15) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C03 O01 H01 109.5(10) . . ?
C10 O12 H12 110.1(10) . . ?
O02 C03 O01 123.62(9) . . ?
O02 C03 C04 125.18(9) . . ?
O01 C03 C04 111.19(9) . . ?
C03 C04 C05 115.17(9) . . ?
C03 C04 H04A 108.5 . . ?
C05 C04 H04A 108.5 . . ?
C03 C04 H04B 108.5 . . ?
C05 C04 H04B 108.5 . . ?
H04A C04 H04B 107.5 . . ?
C04 C05 C06 111.61(8) . . ?
C04 C05 H05A 109.3 . . ?
C06 C05 H05A 109.3 . . ?
C04 C05 H05B 109.3 . . ?
C06 C05 H05B 109.3 . . ?
H05A C05 H05B 108.0 . . ?
C07 C06 C05 113.90(8) . . ?
C07 C06 H06A 108.8 . . ?
C05 C06 H06A 108.8 . . ?
C07 C06 H06B 108.8 . . ?
C05 C06 H06B 108.8 . . ?
H06A C06 H06B 107.7 . . ?
C06 C07 C08 113.34(8) . . ?
C06 C07 H07A 108.9 . . ?
C08 C07 H07A 108.9 . . ?
C06 C07 H07B 108.9 . . ?
C08 C07 H07B 108.9 . . ?
H07A C07 H07B 107.7 . . ?
C09 C08 C07 111.74(8) . . ?
C09 C08 H08A 109.3 . . ?
C07 C08 H08A 109.3 . . ?
C09 C08 H08B 109.3 . . ?
C07 C08 H08B 109.3 . . ?
H08A C08 H08B 107.9 . . ?
C10 C09 C08 114.58(8) . . ?
C10 C09 H09A 108.6 . . ?
C08 C09 H09A 108.6 . . ?
C10 C09 H09B 108.6 . . ?
C08 C09 H09B 108.6 . . ?
H09A C09 H09B 107.6 . . ?
O11 C10 O12 123.09(10) . . ?
O11 C10 C09 125.36(10) . . ?
O12 C10 C09 111.55(9) . . ?
C14 N13 C15 117.33(9) . . ?
C23 N24 C22 117.52(9) . . ?
N13 C14 C16 123.96(10) . . ?
N13 C14 H14 118.0 . . ?
C16 C14 H14 118.0 . . ?
N13 C15 C17 123.11(10) . . ?
N13 C15 H15 118.4 . . ?
C17 C15 H15 118.4 . . ?
C14 C16 C18 118.92(10) . . ?
C14 C16 H16 120.5 . . ?
C18 C16 H16 120.5 . . ?
C15 C17 C18 119.30(9) . . ?
C15 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C16 C18 C17 117.36(9) . . ?
C16 C18 C19 121.20(9) . . ?
C17 C18 C19 121.43(9) . . ?
C20 C19 C21 117.28(9) . . ?
C20 C19 C18 121.36(9) . . ?
C21 C19 C18 121.36(9) . . ?
C22 C20 C19 119.27(9) . . ?
C22 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C23 C21 C19 119.24(10) . . ?
C23 C21 H21 120.4 . . ?
C19 C21 H21 120.4 . . ?
N24 C22 C20 123.21(10) . . ?
N24 C22 H22 118.4 . . ?
C20 C22 H22 118.4 . . ?
N24 C23 C21 123.47(10) . . ?
N24 C23 H23 118.3 . . ?
C21 C23 H23 118.3 . . ?

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
O02 C03 C04 C05 -1.54(16) . . . . ?
O01 C03 C04 C05 179.27(9) . . . . ?
C03 C04 C05 C06 178.96(9) . . . . ?
C04 C05 C06 C07 177.35(9) . . . . ?
C05 C06 C07 C08 179.88(9) . . . . ?
C06 C07 C08 C09 178.34(9) . . . . ?
C07 C08 C09 C10 176.39(9) . . . . ?
C08 C09 C10 O11 -2.09(16) . . . . ?
C08 C09 C10 O12 178.52(9) . . . . ?
C15 N13 C14 C16 1.02(17) . . . . ?
C14 N13 C15 C17 -0.95(17) . . . . ?
N13 C14 C16 C18 0.03(18) . . . . ?
N13 C15 C17 C18 -0.15(17) . . . . ?
C14 C16 C18 C17 -1.13(16) . . . . ?
C14 C16 C18 C19 177.91(10) . . . . ?
C15 C17 C18 C16 1.19(16) . . . . ?
C15 C17 C18 C19 -177.86(10) . . . . ?
C16 C18 C19 C20 -14.19(15) . . . . ?
C17 C18 C19 C20 164.83(10) . . . . ?
C16 C18 C19 C21 166.69(10) . . . . ?
C17 C18 C19 C21 -14.30(15) . . . . ?
C21 C19 C20 C22 0.18(15) . . . . ?
C18 C19 C20 C22 -178.99(9) . . . . ?
C20 C19 C21 C23 0.91(16) . . . . ?
C18 C19 C21 C23 -179.93(10) . . . . ?
C23 N24 C22 C20 0.35(16) . . . . ?
C19 C20 C22 N24 -0.85(17) . . . . ?
C22 N24 C23 C21 0.83(17) . . . . ?
C19 C21 C23 N24 -1.48(17) . . . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_p1908a
_database_code_depnum_ccdc_archive 'CCDC 1940951'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13.42 N2, 2(C7 H5.29 O3)'
_chemical_formula_sum            'C26 H24 N2 O6'
_chemical_formula_weight         460.47

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.6104(3)
_cell_length_b                   6.8302(2)
_cell_length_c                   19.1092(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.7599(14)
_cell_angle_gamma                90
_cell_volume                     1100.24(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7835
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      33.0

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.588
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7112
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            23889
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.439
_diffrn_reflns_theta_max         33.182
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4211
_reflns_number_gt                3186
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²+0.1085P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4211
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
N01 N 0.73030(8) 0.58847(10) 0.09281(4) 0.01906(15) Uani 1 1 d . . . . .
H01 H 0.773(3) 0.725(4) 0.1195(13) 0.052(10) Uiso 0.71(6) 1 d . . P . .
C02 C 0.62470(9) 0.23724(11) 0.02672(4) 0.01539(15) Uani 1 1 d . . . . .
C03 C 0.80467(10) 0.51051(12) 0.04433(5) 0.01954(17) Uani 1 1 d . . . . .
H03 H 0.893264 0.576786 0.032898 0.023 Uiso 1 1 calc R U . . .
C04 C 0.54871(10) 0.32136(12) 0.07716(4) 0.01843(16) Uani 1 1 d . . . . .
H04 H 0.459291 0.259278 0.089521 0.022 Uiso 1 1 calc R U . . .
C05 C 0.75529(9) 0.33564(12) 0.01054(4) 0.01863(16) Uani 1 1 d . . . . .
H05 H 0.809963 0.282569 -0.023551 0.022 Uiso 1 1 calc R U . . .
C06 C 0.57181(9) 0.04697(12) -0.01056(4) 0.01766(16) Uani 1 1 d . . . . .
H06A H 0.661231 -0.046836 -0.000429 0.021 Uiso 1 1 calc R U . . .
H06B H 0.547152 0.070619 -0.062762 0.021 Uiso 1 1 calc R U . . .
C07 C 0.60522(10) 0.49650(12) 0.10903(5) 0.02058(17) Uani 1 1 d . . . . .
H07 H 0.553426 0.553097 0.143519 0.025 Uiso 1 1 calc R U . . .
O08 O -0.18175(8) -0.09316(10) 0.15675(4) 0.02441(16) Uani 1 1 d . . . . .
H08 H -0.198747 -0.203293 0.137124 0.035(18) Uiso 0.29(6) 1 calc R . P . .
O09 O 0.17513(9) 0.21873(11) 0.09162(4) 0.03259(18) Uani 1 1 d . . . . .
H09 H 0.1176(17) 0.099(2) 0.0773(8) 0.049 Uiso 1 1 d . U . . .
O10 O -0.01051(8) -0.07269(10) 0.08396(4) 0.02809(17) Uani 1 1 d . . . . .
C11 C -0.01221(9) 0.18212(11) 0.16851(4) 0.01574(15) Uani 1 1 d . . . . .
C12 C -0.07903(10) 0.26103(12) 0.22299(4) 0.01935(16) Uani 1 1 d . . . . .
H12 H -0.161581 0.192182 0.238648 0.023 Uiso 1 1 calc R U . . .
C13 C 0.16054(11) 0.46517(14) 0.17675(5) 0.0263(2) Uani 1 1 d . . . . .
H13 H 0.242135 0.535729 0.161009 0.032 Uiso 1 1 calc R U . . .
C14 C -0.06965(10) -0.00678(12) 0.13372(4) 0.01799(16) Uani 1 1 d . . . . .
C15 C 0.10838(10) 0.28630(13) 0.14511(5) 0.02025(17) Uani 1 1 d . . . . .
C16 C -0.02670(11) 0.43863(14) 0.25466(5) 0.02575(19) Uani 1 1 d . . . . .
H16 H -0.072231 0.490621 0.291986 0.031 Uiso 1 1 calc R U . . .
C17 C 0.09348(11) 0.53951(14) 0.23095(5) 0.0278(2) Uani 1 1 d . . . . .
H17 H 0.129784 0.661088 0.252363 0.033 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N01 C07 1.3367(10) . ?
N01 C03 1.3393(11) . ?
N01 H01 1.09(3) . ?
C02 C04 1.3945(11) . ?
C02 C05 1.3976(11) . ?
C02 C06 1.5071(11) . ?
C03 C05 1.3828(11) . ?
C03 H03 0.9500 . ?
C04 C07 1.3849(11) . ?
C04 H04 0.9500 . ?
C05 H05 0.9500 . ?
C06 C06 1.5188(15) 3_655 ?
C06 H06A 0.9900 . ?
C06 H06B 0.9900 . ?
C07 H07 0.9500 . ?
O08 C14 1.2833(10) . ?
O08 H08 0.8400 . ?
O09 C15 1.3519(11) . ?
O09 H09 0.964(15) . ?
O10 C14 1.2504(10) . ?
C11 C12 1.3963(11) . ?
C11 C15 1.4049(11) . ?
C11 C14 1.4890(11) . ?
C12 C16 1.3891(12) . ?
C12 H12 0.9500 . ?
C13 C17 1.3812(14) . ?
C13 C15 1.3962(12) . ?
C13 H13 0.9500 . ?
C16 C17 1.3936(14) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C07 N01 C03 119.67(7) . . ?
C07 N01 H01 120.4(11) . . ?
C03 N01 H01 120.0(11) . . ?
C04 C02 C05 117.82(7) . . ?
C04 C02 C06 122.87(7) . . ?
C05 C02 C06 119.30(7) . . ?
N01 C03 C05 121.44(7) . . ?
N01 C03 H03 119.3 . . ?
C05 C03 H03 119.3 . . ?
C07 C04 C02 119.18(7) . . ?
C07 C04 H04 120.4 . . ?
C02 C04 H04 120.4 . . ?
C03 C05 C02 119.79(7) . . ?
C03 C05 H05 120.1 . . ?
C02 C05 H05 120.1 . . ?
C02 C06 C06 115.01(8) . 3_655 ?
C02 C06 H06A 108.5 . . ?
C06 C06 H06A 108.5 3_655 . ?
C02 C06 H06B 108.5 . . ?
C06 C06 H06B 108.5 3_655 . ?
H06A C06 H06B 107.5 . . ?
N01 C07 C04 122.11(8) . . ?
N01 C07 H07 118.9 . . ?
C04 C07 H07 118.9 . . ?
C14 O08 H08 109.5 . . ?
C15 O09 H09 103.3(9) . . ?
C12 C11 C15 119.04(7) . . ?
C12 C11 C14 121.17(7) . . ?
C15 C11 C14 119.77(7) . . ?
C16 C12 C11 121.03(8) . . ?
C16 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C17 C13 C15 119.98(8) . . ?
C17 C13 H13 120.0 . . ?
C15 C13 H13 120.0 . . ?
O10 C14 O08 123.14(8) . . ?
O10 C14 C11 120.12(7) . . ?
O08 C14 C11 116.73(7) . . ?
O09 C15 C13 118.52(8) . . ?
O09 C15 C11 121.57(8) . . ?
C13 C15 C11 119.91(8) . . ?
C12 C16 C17 119.12(8) . . ?
C12 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C13 C17 C16 120.91(8) . . ?
C13 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C07 N01 C03 C05 -0.22(13) . . . . ?
C05 C02 C04 C07 -0.21(12) . . . . ?
C06 C02 C04 C07 179.87(8) . . . . ?
N01 C03 C05 C02 0.26(13) . . . . ?
C04 C02 C05 C03 -0.03(12) . . . . ?
C06 C02 C05 C03 179.88(7) . . . . ?
C04 C02 C06 C06 0.32(14) . . . 3_655 ?
C05 C02 C06 C06 -179.59(9) . . . 3_655 ?
C03 N01 C07 C04 -0.04(13) . . . . ?
C02 C04 C07 N01 0.26(13) . . . . ?
C15 C11 C12 C16 -0.82(13) . . . . ?
C14 C11 C12 C16 -179.09(8) . . . . ?
C12 C11 C14 O10 178.43(8) . . . . ?
C15 C11 C14 O10 0.16(12) . . . . ?
C12 C11 C14 O08 -0.63(12) . . . . ?
C15 C11 C14 O08 -178.90(8) . . . . ?
C17 C13 C15 O09 179.22(8) . . . . ?
C17 C13 C15 C11 -0.05(13) . . . . ?
C12 C11 C15 O09 -178.70(8) . . . . ?
C14 C11 C15 O09 -0.39(13) . . . . ?
C12 C11 C15 C13 0.56(13) . . . . ?
C14 C11 C15 C13 178.86(8) . . . . ?
C11 C12 C16 C17 0.56(13) . . . . ?
C15 C13 C17 C16 -0.21(14) . . . . ?
C12 C16 C17 C13 -0.04(14) . . . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.253
_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_p1913a
_database_code_depnum_ccdc_archive 'CCDC 1940957'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2, C3 H4 O4'
_chemical_formula_sum            'C15 H14 N2 O4'
_chemical_formula_weight         286.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 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, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   9.5746(4)
_cell_length_b                   4.6618(2)
_cell_length_c                   16.1220(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.035(2)
_cell_angle_gamma                90
_cell_volume                     688.03(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5980
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      32.4

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.189
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7022
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            17981
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         33.188
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2640
_reflns_number_gt                2024
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2640
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1687
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_restrained_S_all      1.247
_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
O01 O 0.94327(8) -0.04232(18) 0.35945(5) 0.0394(2) Uani 1 1 d . . . . .
H01 H 0.8633(16) 0.088(3) 0.3760(10) 0.059 Uiso 1 1 d . U . . .
O02 O 0.77713(10) -0.0505(2) 0.23047(6) 0.0583(3) Uani 1 1 d . . . . .
C03 C 0.89362(10) -0.1222(2) 0.27869(6) 0.0324(2) Uani 1 1 d . . . . .
C04 C 1.000000 -0.3127(3) 0.250000 0.0387(3) Uani 1 2 d S T P . .
H04A H 1.053986 -0.437026 0.298626 0.046 Uiso 0.5 1 calc R U P . .
H04B H 0.946014 -0.437022 0.201373 0.046 Uiso 0.5 1 calc R U P . .
C05 C 0.49075(12) 0.9321(2) 0.46217(7) 0.0211(4) Uani 0.702(4) 1 d . . P A 1
H05 H 0.405941 0.976327 0.415961 0.025 Uiso 0.702(4) 1 calc R U P A 1
C06 C 0.5920(2) 0.7207(3) 0.44588(14) 0.0192(3) Uani 0.702(4) 1 d . . P A 1
C07 C 0.5593(2) 0.5958(4) 0.36417(14) 0.0256(4) Uani 0.702(4) 1 d . . P A 1
H07 H 0.472784 0.648849 0.320389 0.031 Uiso 0.702(4) 1 calc R U P A 1
C08 C 0.6532(4) 0.3933(8) 0.34661(19) 0.0252(5) Uani 0.702(4) 1 d . . P A 1
H08 H 0.629786 0.310561 0.290349 0.030 Uiso 0.702(4) 1 calc R U P A 1
N09 N 0.7727(9) 0.3130(16) 0.4051(5) 0.0250(9) Uani 0.702(4) 1 d . . P A 1
C10 C 0.8068(6) 0.4276(14) 0.4846(4) 0.0285(6) Uani 0.702(4) 1 d . . P A 1
H10 H 0.893503 0.366557 0.526859 0.034 Uiso 0.702(4) 1 calc R U P A 1
C11 C 0.7196(2) 0.6328(4) 0.50754(13) 0.0252(4) Uani 0.702(4) 1 d . . P A 1
H11 H 0.746601 0.711896 0.564342 0.030 Uiso 0.702(4) 1 calc R U P A 1
C12 C 0.5629(4) 0.9383(7) 0.51895(19) 0.0288(10) Uani 0.298(4) 1 d . . P A 2
H12 H 0.610862 0.994143 0.576992 0.035 Uiso 0.298(4) 1 calc R U P A 2
C13 C 0.6367(5) 0.7217(7) 0.4802(3) 0.0243(8) Uani 0.298(4) 1 d . . P A 2
C14 C 0.5830(6) 0.6344(11) 0.3954(3) 0.0308(11) Uani 0.298(4) 1 d . . P A 2
H14 H 0.495654 0.714514 0.358375 0.037 Uiso 0.298(4) 1 calc R U P A 2
C15 C 0.6581(12) 0.430(2) 0.3657(5) 0.0353(17) Uani 0.298(4) 1 d . . P A 2
H15 H 0.620979 0.371964 0.306890 0.042 Uiso 0.298(4) 1 calc R U P A 2
N16 N 0.788(2) 0.300(4) 0.4168(13) 0.028(2) Uani 0.298(4) 1 d . . P A 2
C17 C 0.8304(14) 0.391(3) 0.4980(9) 0.0292(15) Uani 0.298(4) 1 d . . P A 2
H17 H 0.914529 0.303880 0.536243 0.035 Uiso 0.298(4) 1 calc R U P A 2
C18 C 0.7629(6) 0.5981(13) 0.5303(4) 0.0345(10) Uani 0.298(4) 1 d . . P A 2
H18 H 0.803647 0.659189 0.588583 0.041 Uiso 0.298(4) 1 calc R 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
O01 C03 1.3029(11) . ?
O01 H01 1.071(17) . ?
O02 C03 1.2050(12) . ?
C03 C04 1.5218(13) . ?
C04 H04A 0.9900 . ?
C04 H04B 0.9900 . ?
C05 C05 1.340(2) 3_676 ?
C05 C06 1.4591(19) . ?
C05 H05 0.9500 . ?
C06 C07 1.3893(19) . ?
C06 C11 1.392(2) . ?
C07 C08 1.389(4) . ?
C07 H07 0.9500 . ?
C08 N09 1.306(9) . ?
C08 H08 0.9500 . ?
N09 C10 1.338(10) . ?
C10 C11 1.389(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C12 1.312(7) 3_676 ?
C12 C13 1.473(6) . ?
C12 H12 0.9500 . ?
C13 C18 1.368(5) . ?
C13 C14 1.374(6) . ?
C14 C15 1.362(10) . ?
C14 H14 0.9500 . ?
C15 N16 1.41(2) . ?
C15 H15 0.9500 . ?
N16 C17 1.32(2) . ?
C17 C18 1.349(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C03 O01 H01 109.5(7) . . ?
O02 C03 O01 124.28(10) . . ?
O02 C03 C04 122.76(8) . . ?
O01 C03 C04 112.95(7) . . ?
C03 C04 C03 108.60(11) 2_755 . ?
C03 C04 H04A 110.0 2_755 . ?
C03 C04 H04A 110.0 . . ?
C03 C04 H04B 110.0 2_755 . ?
C03 C04 H04B 110.0 . . ?
H04A C04 H04B 108.4 . . ?
C05 C05 C06 124.46(16) 3_676 . ?
C05 C05 H05 117.8 3_676 . ?
C06 C05 H05 117.8 . . ?
C07 C06 C11 117.45(15) . . ?
C07 C06 C05 118.45(18) . . ?
C11 C06 C05 124.10(16) . . ?
C08 C07 C06 119.89(18) . . ?
C08 C07 H07 120.1 . . ?
C06 C07 H07 120.1 . . ?
N09 C08 C07 122.0(3) . . ?
N09 C08 H08 119.0 . . ?
C07 C08 H08 119.0 . . ?
C10 N09 C08 119.6(5) . . ?
N09 C10 C11 122.2(4) . . ?
N09 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C06 118.9(3) . . ?
C10 C11 H11 120.6 . . ?
C06 C11 H11 120.6 . . ?
C12 C12 C13 126.3(4) 3_676 . ?
C12 C12 H12 116.8 3_676 . ?
C13 C12 H12 116.8 . . ?
C18 C13 C14 118.1(4) . . ?
C18 C13 C12 119.3(5) . . ?
C14 C13 C12 122.6(4) . . ?
C15 C14 C13 118.3(5) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
N16 C15 C14 124.1(9) . . ?
N16 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
C17 N16 C15 113.9(13) . . ?
N16 C17 C18 124.6(11) . . ?
N16 C17 H17 117.7 . . ?
C18 C17 H17 117.7 . . ?
C17 C18 C13 120.9(6) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O02 C03 C04 C03 93.23(11) . . . 2_755 ?
O01 C03 C04 C03 -85.52(8) . . . 2_755 ?
C05 C05 C06 C07 179.96(16) 3_676 . . . ?
C05 C05 C06 C11 0.6(2) 3_676 . . . ?
C11 C06 C07 C08 -0.5(3) . . . . ?
C05 C06 C07 C08 -179.8(2) . . . . ?
C06 C07 C08 N09 0.4(6) . . . . ?
C07 C08 N09 C10 0.1(10) . . . . ?
C08 N09 C10 C11 -0.6(11) . . . . ?
N09 C10 C11 C06 0.5(8) . . . . ?
C07 C06 C11 C10 0.1(4) . . . . ?
C05 C06 C11 C10 179.4(3) . . . . ?
C12 C12 C13 C18 -175.4(4) 3_676 . . . ?
C12 C12 C13 C14 3.7(6) 3_676 . . . ?
C18 C13 C14 C15 0.0(8) . . . . ?
C12 C13 C14 C15 -179.2(6) . . . . ?
C13 C14 C15 N16 0.6(15) . . . . ?
C14 C15 N16 C17 1(2) . . . . ?
C15 N16 C17 C18 -3(3) . . . . ?
N16 C17 C18 C13 4(2) . . . . ?
C14 C13 C18 C17 -1.9(11) . . . . ?
C12 C13 C18 C17 177.3(9) . . . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_p1914b
_database_code_depnum_ccdc_archive 'CCDC 1940955'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2, C2 O4, 6(H2 O)'
_chemical_formula_sum            'C14 H24 N2 O10'
_chemical_formula_weight         380.35

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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   16.3686(5)
_cell_length_b                   6.9285(2)
_cell_length_c                   9.5207(3)
_cell_angle_alpha                90
_cell_angle_beta                 123.4486(12)
_cell_angle_gamma                90
_cell_volume                     900.91(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6262
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      33.2

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7016
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            11525
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.564
_diffrn_reflns_theta_max         33.167
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1850
_reflns_number_gt                1629
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+0.2738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1850
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1094
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O01 O 0.62427(5) 0.500000 0.65874(9) 0.0273(2) Uani 1 2 d S T P . .
O02 O 0.49370(5) 0.500000 0.67762(9) 0.02429(18) Uani 1 2 d S T P . .
O03 O 0.78793(7) 0.500000 0.98202(11) 0.0324(2) Uani 1 2 d S T P . .
H03A H 0.7317(17) 0.500000 0.888(3) 0.049(5) Uiso 1 2 d S . P . .
H03B H 0.8204(19) 0.590(4) 0.987(3) 0.035(6) Uiso 0.5 1 d . . P . .
O04 O 0.93049(6) 0.75576(12) 1.03916(9) 0.03729(18) Uani 1 1 d . . . . .
H04A H 0.9478(12) 0.831(2) 1.120(2) 0.057(4) Uiso 1 1 d . . . . .
H04B H 0.973(2) 0.744(4) 1.025(3) 0.036(6) Uiso 0.5 1 d . . P . .
H04C H 0.889(2) 0.690(5) 1.020(4) 0.048(8) Uiso 0.5 1 d . . P . .
N05 N 0.71032(6) 0.500000 0.48040(11) 0.01935(17) Uani 1 2 d S T P . .
H05 H 0.6528(19) 0.500000 0.490(3) 0.069(7) Uiso 1 2 d S . P . .
C06 C 0.95282(6) 0.500000 0.43635(11) 0.01759(18) Uani 1 2 d S T P . .
H06 H 0.938190 0.500000 0.324930 0.021 Uiso 1 2 calc R U P . .
C07 C 0.87055(6) 0.500000 0.45715(11) 0.01562(17) Uani 1 2 d S T P . .
C08 C 0.53445(6) 0.500000 0.59750(11) 0.01690(18) Uani 1 2 d S T P . .
C09 C 0.88219(7) 0.500000 0.61442(12) 0.02054(19) Uani 1 2 d S T P . .
H09 H 0.945867 0.500000 0.714909 0.025 Uiso 1 2 calc R U P . .
C10 C 0.77538(7) 0.500000 0.31273(12) 0.02099(19) Uani 1 2 d S T P . .
H10 H 0.765077 0.500000 0.204283 0.025 Uiso 1 2 calc R U P . .
C11 C 0.80058(7) 0.500000 0.62226(13) 0.02157(19) Uani 1 2 d S T P . .
H11 H 0.808166 0.500000 0.728637 0.026 Uiso 1 2 calc R U P . .
C12 C 0.69666(7) 0.500000 0.32861(13) 0.0224(2) Uani 1 2 d S T P . .
H12 H 0.631996 0.500000 0.230559 0.027 Uiso 1 2 calc R U P . .


_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
O01 C08 1.2477(10) . ?
O02 C08 1.2600(10) . ?
O03 H03A 0.86(2) . ?
O03 H03B 0.80(3) . ?
O03 H03B 0.80(3) 6_565 ?
O04 H04A 0.842(17) . ?
O04 H04B 0.78(2) . ?
O04 H04C 0.75(4) . ?
N05 C12 1.3349(13) . ?
N05 C11 1.3443(13) . ?
N05 H05 1.00(2) . ?
C06 C06 1.3383(17) 5_766 ?
C06 C07 1.4653(12) . ?
C06 H06 0.9500 . ?
C07 C10 1.3986(13) . ?
C07 C09 1.4013(13) . ?
C08 C08 1.5526(18) 5_666 ?
C09 C11 1.3784(12) . ?
C09 H09 0.9500 . ?
C10 C12 1.3778(12) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H03A O03 H03B 110.7(19) . . ?
H03A O03 H03B 110.7(19) . 6_565 ?
H03B O03 H03B 102(4) . 6_565 ?
H04A O04 H04B 110(2) . . ?
H04A O04 H04C 114(2) . . ?
H04B O04 H04C 132(3) . . ?
C12 N05 C11 121.55(8) . . ?
C12 N05 H05 119.8(14) . . ?
C11 N05 H05 118.6(14) . . ?
C06 C06 C07 124.43(10) 5_766 . ?
C06 C06 H06 117.8 5_766 . ?
C07 C06 H06 117.8 . . ?
C10 C07 C09 118.18(8) . . ?
C10 C07 C06 118.41(8) . . ?
C09 C07 C06 123.41(8) . . ?
O01 C08 O02 126.71(9) . . ?
O01 C08 C08 116.81(9) . 5_666 ?
O02 C08 C08 116.48(9) . 5_666 ?
C11 C09 C07 119.52(9) . . ?
C11 C09 H09 120.2 . . ?
C07 C09 H09 120.2 . . ?
C12 C10 C07 119.63(9) . . ?
C12 C10 H10 120.2 . . ?
C07 C10 H10 120.2 . . ?
N05 C11 C09 120.45(9) . . ?
N05 C11 H11 119.8 . . ?
C09 C11 H11 119.8 . . ?
N05 C12 C10 120.67(9) . . ?
N05 C12 H12 119.7 . . ?
C10 C12 H12 119.7 . . ?

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
C06 C06 C07 C10 180.000(0) 5_766 . . . ?
C06 C06 C07 C09 0.000(0) 5_766 . . . ?
C10 C07 C09 C11 0.000(0) . . . . ?
C06 C07 C09 C11 180.000(0) . . . . ?
C09 C07 C10 C12 0.000(0) . . . . ?
C06 C07 C10 C12 180.000(0) . . . . ?
C12 N05 C11 C09 0.000(0) . . . . ?
C07 C09 C11 N05 0.000(0) . . . . ?
C11 N05 C12 C10 0.000(0) . . . . ?
C07 C10 C12 N05 0.000(0) . . . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.051

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

data_p1910a
_database_code_depnum_ccdc_archive 'CCDC 1940952'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11.56 N2, 2(C8 H5.22 O4)'
_chemical_formula_sum            'C28 H22 N2 O8'
_chemical_formula_weight         514.47

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.0785(6)
_cell_length_b                   4.9373(2)
_cell_length_c                   18.7535(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.176(3)
_cell_angle_gamma                90
_cell_volume                     1163.02(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7336
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      33.0

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            23067
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.262
_diffrn_reflns_theta_max         33.180
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4443
_reflns_number_gt                3359
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0789P)²+0.2765P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4443
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
O01 O 0.28469(6) 0.8816(2) 0.10663(7) 0.0457(3) Uani 1 1 d . . . . .
H01 H 0.3327(17) 0.759(5) 0.1483(13) 0.068 Uiso 1 1 d . U . . .
O02 O 0.29387(6) 1.2112(2) 0.03143(5) 0.0369(2) Uani 1 1 d . . . . .
C03 C 0.33937(8) 1.0503(2) 0.07875(6) 0.0229(2) Uani 1 1 d . . . . .
C04 C 0.46018(7) 1.0463(2) 0.10566(5) 0.01592(18) Uani 1 1 d . . . . .
C05 C 0.50737(8) 1.2323(2) 0.06832(6) 0.0248(2) Uani 1 1 d . . . . .
H05 H 0.462610 1.341312 0.030588 0.030 Uiso 1 1 calc R U . . .
C06 C 0.61637(8) 1.2642(2) 0.08398(7) 0.0245(2) Uani 1 1 d . . . . .
H06 H 0.645475 1.392120 0.057218 0.029 Uiso 1 1 calc R U . . .
C07 C 0.68251(7) 1.1083(2) 0.13888(6) 0.0200(2) Uani 1 1 d . . . . .
H07 H 0.757602 1.128352 0.150485 0.024 Uiso 1 1 calc R U . . .
C08 C 0.63821(7) 0.9227(2) 0.17677(6) 0.01816(19) Uani 1 1 d . . . . .
H08 H 0.684273 0.816527 0.214573 0.022 Uiso 1 1 calc R U . . .
C09 C 0.52781(7) 0.88491(18) 0.16161(5) 0.01389(17) Uani 1 1 d . . . . .
C10 C 0.49575(7) 0.6691(2) 0.20880(5) 0.01710(18) Uani 1 1 d . . . . .
O11 O 0.40028(6) 0.59773(18) 0.19884(5) 0.0281(2) Uani 1 1 d . . . . .
O12 O 0.57015(7) 0.56546(19) 0.25859(5) 0.0294(2) Uani 1 1 d . . . . .
H12 H 0.552(7) 0.46(3) 0.288(6) 0.05(3) Uiso 0.22(4) 1 d . . P . .
N13 N 0.52307(7) 0.18781(18) 0.33672(5) 0.01844(17) Uani 1 1 d . . . . .
H13 H 0.5364(16) 0.327(5) 0.3063(12) 0.022 Uiso 0.78(4) 1 d . U P . .
C14 C 0.60554(8) 0.0826(2) 0.38867(6) 0.01908(19) Uani 1 1 d . . . . .
H14 H 0.675342 0.148853 0.393517 0.023 Uiso 1 1 calc R U . . .
C15 C 0.42340(8) 0.1038(2) 0.32928(6) 0.0216(2) Uani 1 1 d . . . . .
H15 H 0.366146 0.184251 0.292708 0.026 Uiso 1 1 calc R U . . .
C16 C 0.59048(7) -0.1203(2) 0.43512(6) 0.01745(18) Uani 1 1 d . . . . .
H16 H 0.649406 -0.194089 0.471683 0.021 Uiso 1 1 calc R U . . .
C17 C 0.40293(8) -0.0980(2) 0.37411(6) 0.0199(2) Uani 1 1 d . . . . .
H17 H 0.331901 -0.156197 0.368535 0.024 Uiso 1 1 calc R U . . .
C18 C 0.48715(7) -0.21677(19) 0.42785(5) 0.01444(17) Uani 1 1 d . . . . .
C19 C 0.46308(7) -0.43057(18) 0.47473(5) 0.01540(18) Uani 1 1 d . . . . .
H19 H 0.390411 -0.473545 0.468929 0.018 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O01 C03 1.2989(14) . ?
O01 H01 1.05(2) . ?
O02 C03 1.2160(13) . ?
C03 C04 1.5189(13) . ?
C04 C05 1.3984(14) . ?
C04 C09 1.4145(13) . ?
C05 C06 1.3820(14) . ?
C05 H05 0.9500 . ?
C06 C07 1.3799(14) . ?
C06 H06 0.9500 . ?
C07 C08 1.3819(14) . ?
C07 H07 0.9500 . ?
C08 C09 1.4042(12) . ?
C08 H08 0.9500 . ?
C09 C10 1.5169(13) . ?
C10 O12 1.2547(12) . ?
C10 O11 1.2602(12) . ?
O12 H12 0.85(14) . ?
N13 C15 1.3377(13) . ?
N13 C14 1.3406(13) . ?
N13 H13 0.94(3) . ?
C14 C16 1.3769(14) . ?
C14 H14 0.9500 . ?
C15 C17 1.3771(14) . ?
C15 H15 0.9500 . ?
C16 C18 1.4034(13) . ?
C16 H16 0.9500 . ?
C17 C18 1.3980(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.4630(13) . ?
C19 C19 1.3383(18) 3_646 ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C03 O01 H01 112.8(12) . . ?
O02 C03 O01 120.02(10) . . ?
O02 C03 C04 120.23(10) . . ?
O01 C03 C04 119.75(9) . . ?
C05 C04 C09 117.99(8) . . ?
C05 C04 C03 112.85(8) . . ?
C09 C04 C03 129.16(8) . . ?
C06 C05 C04 122.78(9) . . ?
C06 C05 H05 118.6 . . ?
C04 C05 H05 118.6 . . ?
C07 C06 C05 119.35(9) . . ?
C07 C06 H06 120.3 . . ?
C05 C06 H06 120.3 . . ?
C06 C07 C08 119.20(9) . . ?
C06 C07 H07 120.4 . . ?
C08 C07 H07 120.4 . . ?
C07 C08 C09 122.61(9) . . ?
C07 C08 H08 118.7 . . ?
C09 C08 H08 118.7 . . ?
C08 C09 C04 118.07(8) . . ?
C08 C09 C10 114.27(8) . . ?
C04 C09 C10 127.66(8) . . ?
O12 C10 O11 121.81(9) . . ?
O12 C10 C09 115.94(8) . . ?
O11 C10 C09 122.24(9) . . ?
C10 O12 H12 116(6) . . ?
C15 N13 C14 121.27(9) . . ?
C15 N13 H13 120.3(12) . . ?
C14 N13 H13 118.4(12) . . ?
N13 C14 C16 120.91(9) . . ?
N13 C14 H14 119.5 . . ?
C16 C14 H14 119.5 . . ?
N13 C15 C17 120.67(9) . . ?
N13 C15 H15 119.7 . . ?
C17 C15 H15 119.7 . . ?
C14 C16 C18 119.28(9) . . ?
C14 C16 H16 120.4 . . ?
C18 C16 H16 120.4 . . ?
C15 C17 C18 119.71(9) . . ?
C15 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C16 118.13(9) . . ?
C17 C18 C19 118.54(8) . . ?
C16 C18 C19 123.31(8) . . ?
C19 C19 C18 124.16(10) 3_646 . ?
C19 C19 H19 117.9 3_646 . ?
C18 C19 H19 117.9 . . ?

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
O02 C03 C04 C05 -2.57(16) . . . . ?
O01 C03 C04 C05 177.64(12) . . . . ?
O02 C03 C04 C09 177.23(12) . . . . ?
O01 C03 C04 C09 -2.56(18) . . . . ?
C09 C04 C05 C06 -0.12(18) . . . . ?
C03 C04 C05 C06 179.71(11) . . . . ?
C04 C05 C06 C07 -0.32(19) . . . . ?
C05 C06 C07 C08 0.30(18) . . . . ?
C06 C07 C08 C09 0.16(17) . . . . ?
C07 C08 C09 C04 -0.59(15) . . . . ?
C07 C08 C09 C10 179.30(10) . . . . ?
C05 C04 C09 C08 0.55(15) . . . . ?
C03 C04 C09 C08 -179.24(10) . . . . ?
C05 C04 C09 C10 -179.32(10) . . . . ?
C03 C04 C09 C10 0.88(17) . . . . ?
C08 C09 C10 O12 4.85(14) . . . . ?
C04 C09 C10 O12 -175.28(10) . . . . ?
C08 C09 C10 O11 -175.19(10) . . . . ?
C04 C09 C10 O11 4.68(17) . . . . ?
C15 N13 C14 C16 1.47(16) . . . . ?
C14 N13 C15 C17 -1.30(16) . . . . ?
N13 C14 C16 C18 -0.20(16) . . . . ?
N13 C15 C17 C18 -0.12(17) . . . . ?
C15 C17 C18 C16 1.33(15) . . . . ?
C15 C17 C18 C19 179.96(10) . . . . ?
C14 C16 C18 C17 -1.17(15) . . . . ?
C14 C16 C18 C19 -179.73(10) . . . . ?
C17 C18 C19 C19 176.29(12) . . . 3_646 ?
C16 C18 C19 C19 -5.15(18) . . . 3_646 ?

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_p1922b
_database_code_depnum_ccdc_archive 'CCDC 1940953'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT097_p1922b              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.04 eA-3  
RESPONSE: Positive Residual Density from C08-C10 Bond
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2, 2(C2 H O4)'
_chemical_formula_sum            'C16 H14 N2 O8'
_chemical_formula_weight         362.29

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      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                   3.677(3)
_cell_length_b                   10.505(7)
_cell_length_c                   10.652(7)
_cell_angle_alpha                66.88(2)
_cell_angle_beta                 85.72(2)
_cell_angle_gamma                81.68(2)
_cell_volume                     374.4(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2654
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      31.87

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             188
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.111
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6566
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            8078
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_max         32.163
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2605
_reflns_number_gt                1820
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1067P)²+0.1052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2605
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1791
_refine_ls_wR_factor_gt          0.1621
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O01 O 0.3394(4) 0.29764(13) 0.08885(12) 0.0218(3) Uani 1 1 d . . . . .
H01 H 0.213(7) 0.376(3) 0.042(2) 0.033 Uiso 1 1 d . U . . .
O02 O 0.5320(4) 0.20119(12) 0.30212(12) 0.0224(3) Uani 1 1 d . . . . .
O03 O -0.0647(4) 0.50522(13) 0.14206(12) 0.0220(3) Uani 1 1 d . . . . .
O04 O 0.1343(4) 0.41792(12) 0.35752(12) 0.0203(3) Uani 1 1 d . . . . .
C05 C 0.3523(4) 0.29555(16) 0.21360(16) 0.0159(3) Uani 1 1 d . . . . .
C06 C 0.1182(4) 0.41921(16) 0.23957(16) 0.0152(3) Uani 1 1 d . . . . .
N07 N 0.5268(4) 0.25180(14) 0.56775(14) 0.0170(3) Uani 1 1 d . . . . .
H07 H 0.427(6) 0.297(2) 0.473(2) 0.020 Uiso 1 1 d . U . . .
C08 C 0.4683(4) 0.32142(17) 0.65120(16) 0.0174(3) Uani 1 1 d . . . . .
H08 H 0.334553 0.412251 0.619935 0.021 Uiso 1 1 calc R U . . .
C09 C 0.7110(5) 0.12276(17) 0.60803(16) 0.0184(3) Uani 1 1 d . . . . .
H09 H 0.748187 0.076501 0.546476 0.022 Uiso 1 1 calc R U . . .
C10 C 0.6013(5) 0.26173(17) 0.78152(16) 0.0178(3) Uani 1 1 d . . . . .
H10 H 0.564803 0.311986 0.839560 0.021 Uiso 1 1 calc R U . . .
C11 C 0.8462(5) 0.05713(16) 0.73798(15) 0.0165(3) Uani 1 1 d . . . . .
H11 H 0.975995 -0.034319 0.766673 0.020 Uiso 1 1 calc R U . . .
C12 C 0.7897(4) 0.12737(16) 0.82813(15) 0.0154(3) Uani 1 1 d . . . . .
C13 C 0.9174(5) 0.06543(16) 0.96962(15) 0.0175(3) Uani 1 1 d . . . . .
H13 H 0.880280 0.122092 1.021526 0.021 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O01 C05 1.325(2) . ?
O01 H01 0.86(3) . ?
O02 C05 1.216(2) . ?
O03 C06 1.2406(19) . ?
O04 C06 1.257(2) . ?
C05 C06 1.558(2) . ?
N07 C09 1.342(2) . ?
N07 C08 1.345(2) . ?
N07 H07 1.01(2) . ?
C08 C10 1.374(2) . ?
C08 H08 0.9500 . ?
C09 C11 1.376(2) . ?
C09 H09 0.9500 . ?
C10 C12 1.392(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.411(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.471(2) . ?
C13 C13 1.340(3) 2_757 ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C05 O01 H01 105.7(16) . . ?
O02 C05 O01 121.47(15) . . ?
O02 C05 C06 122.63(15) . . ?
O01 C05 C06 115.88(13) . . ?
O03 C06 O04 128.20(15) . . ?
O03 C06 C05 116.01(15) . . ?
O04 C06 C05 115.78(13) . . ?
C09 N07 C08 121.90(14) . . ?
C09 N07 H07 118.8(13) . . ?
C08 N07 H07 119.3(13) . . ?
N07 C08 C10 120.28(15) . . ?
N07 C08 H08 119.9 . . ?
C10 C08 H08 119.9 . . ?
N07 C09 C11 120.36(15) . . ?
N07 C09 H09 119.8 . . ?
C11 C09 H09 119.8 . . ?
C08 C10 C12 119.73(15) . . ?
C08 C10 H10 120.1 . . ?
C12 C10 H10 120.1 . . ?
C09 C11 C12 119.16(15) . . ?
C09 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C10 C12 C11 118.55(14) . . ?
C10 C12 C13 118.10(15) . . ?
C11 C12 C13 123.34(15) . . ?
C13 C13 C12 124.5(2) 2_757 . ?
C13 C13 H13 117.7 2_757 . ?
C12 C13 H13 117.7 . . ?

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
O02 C05 C06 O03 -176.94(16) . . . . ?
O01 C05 C06 O03 1.9(2) . . . . ?
O02 C05 C06 O04 2.0(3) . . . . ?
O01 C05 C06 O04 -179.18(14) . . . . ?
C09 N07 C08 C10 0.7(3) . . . . ?
C08 N07 C09 C11 0.2(3) . . . . ?
N07 C08 C10 C12 -1.5(3) . . . . ?
N07 C09 C11 C12 -0.2(3) . . . . ?
C08 C10 C12 C11 1.5(2) . . . . ?
C08 C10 C12 C13 -178.08(15) . . . . ?
C09 C11 C12 C10 -0.6(2) . . . . ?
C09 C11 C12 C13 178.90(16) . . . . ?
C10 C12 C13 C13 175.9(2) . . . 2_757 ?
C11 C12 C13 C13 -3.6(3) . . . 2_757 ?

_refine_diff_density_max         1.044
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_p1926b
_database_code_depnum_ccdc_archive 'CCDC 1940958'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT415_p1926b              
;
PROBLEM: Short Inter D-H..H-X       H11      ..H37B     .       1.88 Ang.  
RESPONSE: Due to disorder of dipyridine fragment and difficulty to locate hydrogen 
of acid, the hydrogen might be on the dipyridine in case of the minor conformation.
;
_vrf_PLAT230_p1926b              
;
PROBLEM: Hirshfeld Test Diff for    O24      --C22      .        7.4 s.u.  
RESPONSE: Due to disorder of dipyridine fragment
;
_vrf_PLAT430_p1926b              
;
PROBLEM: Short Inter D...A Contact  O24      ..N27B     .       2.79 Ang.  
RESPONSE: Nitrogen of minor conformation of dipyridine
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C12 H10 N2), 4(C7 H5 N O4)'
_chemical_formula_sum            'C64 H50 N10 O16'
_chemical_formula_weight         1215.14

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                   8.1387(7)
_cell_length_b                   9.6821(8)
_cell_length_c                   19.0927(16)
_cell_angle_alpha                102.620(3)
_cell_angle_beta                 90.125(3)
_cell_angle_gamma                107.580(3)
_cell_volume                     1395.8(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      33.1

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.383
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            62786
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         33.300
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10716
_reflns_number_gt                5935
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1011P)²+0.0554P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10716
_refine_ls_number_parameters     509
_refine_ls_number_restraints     649
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1890
_refine_ls_wR_factor_gt          0.1550
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      2.152
_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
O01 O 0.19660(15) 0.32265(14) -0.22017(6) 0.0402(3) Uani 1 1 d . U . . .
O02 O -0.07428(17) 0.20859(16) -0.21631(6) 0.0524(4) Uani 1 1 d . U . . .
N03 N 0.06903(16) 0.28221(14) -0.18721(6) 0.0297(3) Uani 1 1 d . U . . .
C04 C 0.08914(17) 0.32284(15) -0.10793(7) 0.0218(3) Uani 1 1 d . U . . .
C05 C 0.24676(17) 0.41522(15) -0.07453(7) 0.0235(3) Uani 1 1 d . U . . .
H05 H 0.340049 0.453913 -0.101783 0.028 Uiso 1 1 calc R U . . .
C06 C -0.05119(17) 0.26462(15) -0.07093(7) 0.0244(3) Uani 1 1 d . U . . .
H06 H -0.157141 0.200299 -0.095883 0.029 Uiso 1 1 calc R U . . .
C07 C 0.26453(17) 0.44978(15) 0.00020(7) 0.0230(3) Uani 1 1 d . U . . .
H07 H 0.371905 0.511862 0.024751 0.028 Uiso 1 1 calc R U . . .
C08 C -0.03281(17) 0.30291(15) 0.00389(7) 0.0239(3) Uani 1 1 d . U . . .
H08 H -0.128115 0.267140 0.030787 0.029 Uiso 1 1 calc R U . . .
C09 C 0.12517(16) 0.39361(14) 0.03936(7) 0.0203(2) Uani 1 1 d . U . . .
C10 C 0.14039(18) 0.42957(16) 0.11995(7) 0.0256(3) Uani 1 1 d . U . . .
O11 O 0.29793(13) 0.50355(13) 0.14814(5) 0.0357(3) Uani 1 1 d . U . . .
H11 H 0.298752 0.520178 0.193218 0.054 Uiso 1 1 calc R U . . .
O12 O 0.01637(14) 0.39206(13) 0.15470(5) 0.0369(3) Uani 1 1 d . U . . .
O13 O 0.61533(17) 0.95938(14) 1.30041(6) 0.0455(3) Uani 1 1 d . U . . .
O14 O 0.88306(18) 1.08415(16) 1.29384(6) 0.0527(3) Uani 1 1 d . U . . .
N15 N 0.73841(18) 1.00703(15) 1.26605(7) 0.0335(3) Uani 1 1 d . U . . .
C16 C 0.71170(18) 0.97006(15) 1.18699(7) 0.0244(3) Uani 1 1 d . U . . .
C17 C 0.55113(18) 0.88008(16) 1.15509(8) 0.0281(3) Uani 1 1 d . U . . .
H17 H 0.459738 0.842399 1.183397 0.034 Uiso 1 1 calc R U . . .
C18 C 0.84887(18) 1.02692(15) 1.14834(7) 0.0249(3) Uani 1 1 d . U . . .
H18 H 0.957460 1.088636 1.171914 0.030 Uiso 1 1 calc R U . . .
C19 C 0.52736(17) 0.84641(15) 1.08050(7) 0.0260(3) Uani 1 1 d . U . . .
H19 H 0.418253 0.785423 1.057147 0.031 Uiso 1 1 calc R U . . .
C20 C 0.82281(17) 0.99084(15) 1.07372(7) 0.0238(3) Uani 1 1 d . U . . .
H20 H 0.915161 1.027408 1.045600 0.029 Uiso 1 1 calc R U . . .
C21 C 0.66306(16) 0.90186(14) 1.03999(7) 0.0205(3) Uani 1 1 d . U . . .
C22 C 0.64225(18) 0.86714(15) 0.95896(7) 0.0252(3) Uani 1 1 d . U . . .
O23 O 0.48641(13) 0.78443(12) 0.93189(5) 0.0330(2) Uani 1 1 d . U . . .
H23 H 0.482852 0.768962 0.886796 0.049 Uiso 1 1 calc R U . . .
O24 O 0.76112(14) 0.91399(13) 0.92349(5) 0.0368(3) Uani 1 1 d . U . . .
N39 N -0.10164(15) 0.77021(14) 0.45517(7) 0.0341(3) Uani 1 1 d . U . . .
C40 C -0.00867(18) 0.82301(17) 0.51868(8) 0.0296(3) Uani 1 1 d . U . . .
H40 H -0.068171 0.812275 0.560886 0.035 Uiso 1 1 calc R U . . .
C41 C -0.01326(19) 0.78912(17) 0.39691(8) 0.0317(3) Uani 1 1 d . U . . .
H41 H -0.075507 0.753766 0.351066 0.038 Uiso 1 1 calc R U . . .
C42 C 0.16781(17) 0.89197(15) 0.52692(7) 0.0246(3) Uani 1 1 d . U . . .
H42 H 0.226155 0.927166 0.573563 0.029 Uiso 1 1 calc R U . . .
C43 C 0.16368(18) 0.85729(15) 0.39981(7) 0.0261(3) Uani 1 1 d . U . . .
H43 H 0.219341 0.868393 0.356779 0.031 Uiso 1 1 calc R U . . .
C44 C 0.25977(16) 0.90954(14) 0.46611(7) 0.0206(3) Uani 1 1 d . U . . .
C45 C 0.44761(16) 0.97712(14) 0.46994(7) 0.0211(3) Uani 1 1 d . U . . .
H45 H 0.499100 0.989413 0.426182 0.025 Uiso 1 1 calc R U . . .
C25 C 0.6127(2) 0.79224(19) 0.68432(8) 0.0250(3) Uani 0.9361(17) 1 d D U P A 1
H25 H 0.712442 0.841444 0.663084 0.030 Uiso 0.9361(17) 1 calc R U P A 1
C26 C 0.6129(2) 0.81192(19) 0.75887(9) 0.0278(3) Uani 0.9361(17) 1 d . U P A 1
H26 H 0.714521 0.874638 0.787588 0.033 Uiso 0.9361(17) 1 calc R U P A 1
N27 N 0.47600(19) 0.74616(16) 0.79154(7) 0.0255(3) Uani 0.9361(17) 1 d . U P A
1
C28 C 0.3329(2) 0.65802(18) 0.75052(8) 0.0262(3) Uani 0.9361(17) 1 d . U P A 1
H28 H 0.234645 0.611524 0.773358 0.031 Uiso 0.9361(17) 1 calc R U P A 1
C29 C 0.32317(19) 0.63229(18) 0.67612(8) 0.0248(3) Uani 0.9361(17) 1 d . U P A
1
H29 H 0.219928 0.568663 0.648810 0.030 Uiso 0.9361(17) 1 calc R U P A 1
C30 C 0.46610(19) 0.70044(18) 0.64132(8) 0.0194(3) Uani 0.9361(17) 1 d . U P A
1
C31 C 0.4657(2) 0.67943(17) 0.56265(8) 0.0212(3) Uani 0.9361(17) 1 d . U P A 1
H31 H 0.568770 0.729456 0.543673 0.025 Uiso 0.9361(17) 1 calc R U P A 1
C32 C 0.33234(19) 0.59584(16) 0.51564(7) 0.0216(3) Uani 0.9361(17) 1 d . U P A
1
H32 H 0.230397 0.543601 0.534564 0.026 Uiso 0.9361(17) 1 calc R U P A 1
C33 C 0.33001(19) 0.57794(17) 0.43754(8) 0.0191(3) Uani 0.9361(17) 1 d . U P A
1
C34 C 0.17859(19) 0.49247(17) 0.39489(9) 0.0239(3) Uani 0.9361(17) 1 d . U P A
1
H34 H 0.078700 0.444948 0.416562 0.029 Uiso 0.9361(17) 1 calc R U P A 1
C35 C 0.1742(2) 0.47702(18) 0.32078(9) 0.0261(3) Uani 0.9361(17) 1 d . U P A 1
H35 H 0.070073 0.418394 0.292659 0.031 Uiso 0.9361(17) 1 calc R U P A 1
N36 N 0.31074(19) 0.54150(15) 0.28759(6) 0.0244(3) Uani 0.9361(17) 1 d . U P A
1
C37 C 0.4578(2) 0.62210(18) 0.32798(8) 0.0233(3) Uani 0.9361(17) 1 d . U P A 1
H37 H 0.556091 0.666915 0.304645 0.028 Uiso 0.9361(17) 1 calc R U P A 1
C38 C 0.4727(2) 0.64279(19) 0.40227(8) 0.0208(3) Uani 0.9361(17) 1 d D U P A 1
H38 H 0.579104 0.700654 0.428846 0.025 Uiso 0.9361(17) 1 calc R U P A 1
C25B C 0.592(2) 0.784(2) 0.6602(8) 0.030(3) Uani 0.0639(17) 1 d DG U P A 2
H25B H 0.651921 0.811852 0.620328 0.036 Uiso 0.0639(17) 1 calc R U P A 2
C26B C 0.6703(17) 0.8444(18) 0.7296(9) 0.032(3) Uani 0.0639(17) 1 d DG U P A 2
H26B H 0.783094 0.914202 0.737075 0.039 Uiso 0.0639(17) 1 calc R U P A 2
N27B N 0.583(2) 0.8031(19) 0.7879(7) 0.031(3) Uani 0.0639(17) 1 d G U P A 2
C28B C 0.418(2) 0.701(2) 0.7770(8) 0.024(3) Uani 0.0639(17) 1 d G U P A 2
H28B H 0.358507 0.672742 0.816868 0.029 Uiso 0.0639(17) 1 calc R U P A 2
C29B C 0.3401(17) 0.6402(19) 0.7076(10) 0.023(2) Uani 0.0639(17) 1 d G U P A 2
H29B H 0.227332 0.570390 0.700123 0.027 Uiso 0.0639(17) 1 calc R U P A 2
C30B C 0.427(2) 0.681(2) 0.6492(7) 0.021(3) Uani 0.0639(17) 1 d G U P A 2
C31B C 0.384(3) 0.644(3) 0.5704(13) 0.026(3) Uani 0.0639(17) 1 d . U P A 2
H31B H 0.261968 0.598316 0.563783 0.032 Uiso 0.0639(17) 1 calc R U P A 2
C32B C 0.426(3) 0.644(3) 0.5194(13) 0.026(3) Uani 0.0639(17) 1 d . U P A 2
H32B H 0.547863 0.690148 0.526168 0.032 Uiso 0.0639(17) 1 calc R U P A 2
C33B C 0.382(2) 0.605(2) 0.4381(7) 0.024(3) Uani 0.0639(17) 1 d G U P A 2
C34B C 0.215(2) 0.507(2) 0.4253(8) 0.025(3) Uani 0.0639(17) 1 d G U P A 2
H34B H 0.152920 0.476226 0.464154 0.030 Uiso 0.0639(17) 1 calc R U P A 2
C35B C 0.1379(15) 0.4545(16) 0.3555(10) 0.025(3) Uani 0.0639(17) 1 d G U P A 2
H35B H 0.023434 0.387746 0.346734 0.030 Uiso 0.0639(17) 1 calc R U P A 2
N36B N 0.229(2) 0.4996(19) 0.2986(7) 0.025(2) Uani 0.0639(17) 1 d G U P A 2
C37B C 0.396(2) 0.597(2) 0.3114(8) 0.019(2) Uani 0.0639(17) 1 d G U P A 2
H37B H 0.458073 0.628091 0.272513 0.023 Uiso 0.0639(17) 1 calc R U P A 2
C38B C 0.4730(17) 0.650(2) 0.3812(9) 0.017(3) Uani 0.0639(17) 1 d G U P A 2
H38B H 0.587562 0.716574 0.389933 0.020 Uiso 0.0639(17) 1 calc R 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
O01 N03 1.2216(16) . ?
O02 N03 1.2244(17) . ?
N03 C04 1.4739(17) . ?
C04 C05 1.3807(19) . ?
C04 C06 1.3819(18) . ?
C05 C07 1.3892(18) . ?
C05 H05 0.9500 . ?
C06 C08 1.3909(19) . ?
C06 H06 0.9500 . ?
C07 C09 1.3965(17) . ?
C07 H07 0.9500 . ?
C08 C09 1.3919(19) . ?
C08 H08 0.9500 . ?
C09 C10 1.4977(18) . ?
C10 O12 1.2157(16) . ?
C10 O11 1.3116(17) . ?
O11 H11 0.8400 . ?
O13 N15 1.2258(17) . ?
O14 N15 1.2321(18) . ?
N15 C16 1.4729(18) . ?
C16 C18 1.3798(18) . ?
C16 C17 1.384(2) . ?
C17 C19 1.3890(19) . ?
C17 H17 0.9500 . ?
C18 C20 1.3904(19) . ?
C18 H18 0.9500 . ?
C19 C21 1.3905(17) . ?
C19 H19 0.9500 . ?
C20 C21 1.3873(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.5074(18) . ?
C22 O24 1.2134(17) . ?
C22 O23 1.3115(16) . ?
O23 H23 0.8400 . ?
N39 C40 1.3400(19) . ?
N39 C41 1.342(2) . ?
C40 C42 1.3811(19) . ?
C40 H40 0.9500 . ?
C41 C43 1.386(2) . ?
C41 H41 0.9500 . ?
C42 C44 1.3966(17) . ?
C42 H42 0.9500 . ?
C43 C44 1.3952(19) . ?
C43 H43 0.9500 . ?
C44 C45 1.4646(18) . ?
C45 C45 1.337(3) 2_676 ?
C45 H45 0.9500 . ?
C25 C30 1.387(2) . ?
C25 C26 1.394(2) . ?
C25 H25 0.9500 . ?
C26 N27 1.336(2) . ?
C26 H26 0.9500 . ?
N27 C28 1.342(2) . ?
C28 C29 1.385(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.400(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.471(2) . ?
C31 C32 1.336(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.4625(19) . ?
C32 H32 0.9500 . ?
C33 C38 1.394(2) . ?
C33 C34 1.397(2) . ?
C34 C35 1.389(2) . ?
C34 H34 0.9500 . ?
C35 N36 1.3356(19) . ?
C35 H35 0.9500 . ?
N36 C37 1.3437(19) . ?
C37 C38 1.388(2) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C25B C26B 1.3900 . ?
C25B C30B 1.3900 . ?
C25B H25B 0.9500 . ?
C26B N27B 1.3900 . ?
C26B H26B 0.9500 . ?
N27B C28B 1.3900 . ?
C28B C29B 1.3900 . ?
C28B H28B 0.9500 . ?
C29B C30B 1.3900 . ?
C29B H29B 0.9500 . ?
C30B C31B 1.48(3) . ?
C31B C32B 1.03(4) . ?
C31B H31B 0.9500 . ?
C32B C33B 1.53(3) . ?
C32B H32B 0.9500 . ?
C33B C34B 1.3900 . ?
C33B C38B 1.3900 . ?
C34B C35B 1.3900 . ?
C34B H34B 0.9500 . ?
C35B N36B 1.3900 . ?
C35B H35B 0.9500 . ?
N36B C37B 1.3900 . ?
C37B C38B 1.3900 . ?
C37B H37B 0.9500 . ?
C38B H38B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O01 N03 O02 123.69(13) . . ?
O01 N03 C04 118.17(12) . . ?
O02 N03 C04 118.14(12) . . ?
C05 C04 C06 123.46(12) . . ?
C05 C04 N03 118.63(11) . . ?
C06 C04 N03 117.91(12) . . ?
C04 C05 C07 117.86(12) . . ?
C04 C05 H05 121.1 . . ?
C07 C05 H05 121.1 . . ?
C04 C06 C08 118.08(13) . . ?
C04 C06 H06 121.0 . . ?
C08 C06 H06 121.0 . . ?
C05 C07 C09 120.25(13) . . ?
C05 C07 H07 119.9 . . ?
C09 C07 H07 119.9 . . ?
C06 C08 C09 120.02(12) . . ?
C06 C08 H08 120.0 . . ?
C09 C08 H08 120.0 . . ?
C08 C09 C07 120.31(12) . . ?
C08 C09 C10 118.29(11) . . ?
C07 C09 C10 121.40(12) . . ?
O12 C10 O11 124.36(13) . . ?
O12 C10 C09 121.97(13) . . ?
O11 C10 C09 113.66(11) . . ?
C10 O11 H11 109.5 . . ?
O13 N15 O14 123.79(13) . . ?
O13 N15 C16 118.07(13) . . ?
O14 N15 C16 118.14(13) . . ?
C18 C16 C17 123.21(12) . . ?
C18 C16 N15 118.13(13) . . ?
C17 C16 N15 118.66(12) . . ?
C16 C17 C19 118.12(12) . . ?
C16 C17 H17 120.9 . . ?
C19 C17 H17 120.9 . . ?
C16 C18 C20 117.76(13) . . ?
C16 C18 H18 121.1 . . ?
C20 C18 H18 121.1 . . ?
C17 C19 C21 120.08(13) . . ?
C17 C19 H19 120.0 . . ?
C21 C19 H19 120.0 . . ?
C21 C20 C18 120.54(12) . . ?
C21 C20 H20 119.7 . . ?
C18 C20 H20 119.7 . . ?
C20 C21 C19 120.28(12) . . ?
C20 C21 C22 118.16(11) . . ?
C19 C21 C22 121.56(12) . . ?
O24 C22 O23 124.47(13) . . ?
O24 C22 C21 121.64(13) . . ?
O23 C22 C21 113.89(12) . . ?
C22 O23 H23 109.5 . . ?
C40 N39 C41 115.99(12) . . ?
N39 C40 C42 124.42(13) . . ?
N39 C40 H40 117.8 . . ?
C42 C40 H40 117.8 . . ?
N39 C41 C43 123.76(13) . . ?
N39 C41 H41 118.1 . . ?
C43 C41 H41 118.1 . . ?
C40 C42 C44 119.44(12) . . ?
C40 C42 H42 120.3 . . ?
C44 C42 H42 120.3 . . ?
C41 C43 C44 119.80(13) . . ?
C41 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
C43 C44 C42 116.58(12) . . ?
C43 C44 C45 120.51(11) . . ?
C42 C44 C45 122.91(11) . . ?
C45 C45 C44 125.23(15) 2_676 . ?
C45 C45 H45 117.4 2_676 . ?
C44 C45 H45 117.4 . . ?
C30 C25 C26 119.65(14) . . ?
C30 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
N27 C26 C25 122.65(15) . . ?
N27 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C26 N27 C28 118.23(13) . . ?
N27 C28 C29 122.48(14) . . ?
N27 C28 H28 118.8 . . ?
C29 C28 H28 118.8 . . ?
C28 C29 C30 119.74(14) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C25 C30 C29 117.24(14) . . ?
C25 C30 C31 119.73(14) . . ?
C29 C30 C31 123.02(14) . . ?
C32 C31 C30 125.45(14) . . ?
C32 C31 H31 117.3 . . ?
C30 C31 H31 117.3 . . ?
C31 C32 C33 125.56(14) . . ?
C31 C32 H32 117.2 . . ?
C33 C32 H32 117.2 . . ?
C38 C33 C34 117.13(13) . . ?
C38 C33 C32 123.33(14) . . ?
C34 C33 C32 119.54(14) . . ?
C35 C34 C33 119.97(13) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
N36 C35 C34 122.46(14) . . ?
N36 C35 H35 118.8 . . ?
C34 C35 H35 118.8 . . ?
C35 N36 C37 118.07(13) . . ?
N36 C37 C38 122.93(14) . . ?
N36 C37 H37 118.5 . . ?
C38 C37 H37 118.5 . . ?
C37 C38 C33 119.43(14) . . ?
C37 C38 H38 120.3 . . ?
C33 C38 H38 120.3 . . ?
C26B C25B C30B 120.0 . . ?
C26B C25B H25B 120.0 . . ?
C30B C25B H25B 120.0 . . ?
N27B C26B C25B 120.0 . . ?
N27B C26B H26B 120.0 . . ?
C25B C26B H26B 120.0 . . ?
C28B N27B C26B 120.0 . . ?
N27B C28B C29B 120.0 . . ?
N27B C28B H28B 120.0 . . ?
C29B C28B H28B 120.0 . . ?
C30B C29B C28B 120.0 . . ?
C30B C29B H29B 120.0 . . ?
C28B C29B H29B 120.0 . . ?
C29B C30B C25B 120.0 . . ?
C29B C30B C31B 134.4(16) . . ?
C25B C30B C31B 105.6(16) . . ?
C32B C31B C30B 148(3) . . ?
C32B C31B H31B 106.0 . . ?
C30B C31B H31B 106.0 . . ?
C31B C32B C33B 148(3) . . ?
C31B C32B H32B 105.8 . . ?
C33B C32B H32B 105.8 . . ?
C34B C33B C38B 120.0 . . ?
C34B C33B C32B 107.0(15) . . ?
C38B C33B C32B 132.9(15) . . ?
C33B C34B C35B 120.0 . . ?
C33B C34B H34B 120.0 . . ?
C35B C34B H34B 120.0 . . ?
N36B C35B C34B 120.0 . . ?
N36B C35B H35B 120.0 . . ?
C34B C35B H35B 120.0 . . ?
C35B N36B C37B 120.0 . . ?
N36B C37B C38B 120.0 . . ?
N36B C37B H37B 120.0 . . ?
C38B C37B H37B 120.0 . . ?
C37B C38B C33B 120.0 . . ?
C37B C38B H38B 120.0 . . ?
C33B C38B H38B 120.0 . . ?

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
O01 N03 C04 C05 5.55(19) . . . . ?
O02 N03 C04 C05 -175.15(13) . . . . ?
O01 N03 C04 C06 -173.74(13) . . . . ?
O02 N03 C04 C06 5.6(2) . . . . ?
C06 C04 C05 C07 0.6(2) . . . . ?
N03 C04 C05 C07 -178.65(12) . . . . ?
C05 C04 C06 C08 0.9(2) . . . . ?
N03 C04 C06 C08 -179.89(12) . . . . ?
C04 C05 C07 C09 -0.9(2) . . . . ?
C04 C06 C08 C09 -2.0(2) . . . . ?
C06 C08 C09 C07 1.7(2) . . . . ?
C06 C08 C09 C10 -178.76(12) . . . . ?
C05 C07 C09 C08 -0.2(2) . . . . ?
C05 C07 C09 C10 -179.72(12) . . . . ?
C08 C09 C10 O12 -6.0(2) . . . . ?
C07 C09 C10 O12 173.56(13) . . . . ?
C08 C09 C10 O11 173.83(12) . . . . ?
C07 C09 C10 O11 -6.62(19) . . . . ?
O13 N15 C16 C18 178.30(13) . . . . ?
O14 N15 C16 C18 -1.6(2) . . . . ?
O13 N15 C16 C17 -1.8(2) . . . . ?
O14 N15 C16 C17 178.22(14) . . . . ?
C18 C16 C17 C19 -0.4(2) . . . . ?
N15 C16 C17 C19 179.79(13) . . . . ?
C17 C16 C18 C20 -0.2(2) . . . . ?
N15 C16 C18 C20 179.67(12) . . . . ?
C16 C17 C19 C21 0.4(2) . . . . ?
C16 C18 C20 C21 0.7(2) . . . . ?
C18 C20 C21 C19 -0.6(2) . . . . ?
C18 C20 C21 C22 179.69(12) . . . . ?
C17 C19 C21 C20 0.1(2) . . . . ?
C17 C19 C21 C22 179.74(12) . . . . ?
C20 C21 C22 O24 0.5(2) . . . . ?
C19 C21 C22 O24 -179.11(13) . . . . ?
C20 C21 C22 O23 -178.97(12) . . . . ?
C19 C21 C22 O23 1.37(19) . . . . ?
C41 N39 C40 C42 -0.8(2) . . . . ?
C40 N39 C41 C43 0.6(2) . . . . ?
N39 C40 C42 C44 -0.1(2) . . . . ?
N39 C41 C43 C44 0.5(2) . . . . ?
C41 C43 C44 C42 -1.4(2) . . . . ?
C41 C43 C44 C45 177.85(13) . . . . ?
C40 C42 C44 C43 1.20(19) . . . . ?
C40 C42 C44 C45 -178.03(13) . . . . ?
C43 C44 C45 C45 -176.04(16) . . . 2_676 ?
C42 C44 C45 C45 3.2(2) . . . 2_676 ?
C30 C25 C26 N27 -0.4(2) . . . . ?
C25 C26 N27 C28 -0.1(2) . . . . ?
C26 N27 C28 C29 0.5(2) . . . . ?
N27 C28 C29 C30 -0.4(2) . . . . ?
C26 C25 C30 C29 0.5(2) . . . . ?
C26 C25 C30 C31 -179.95(16) . . . . ?
C28 C29 C30 C25 -0.1(2) . . . . ?
C28 C29 C30 C31 -179.65(15) . . . . ?
C25 C30 C31 C32 -179.05(15) . . . . ?
C29 C30 C31 C32 0.5(3) . . . . ?
C30 C31 C32 C33 178.25(14) . . . . ?
C31 C32 C33 C38 2.8(2) . . . . ?
C31 C32 C33 C34 -176.94(15) . . . . ?
C38 C33 C34 C35 -1.0(2) . . . . ?
C32 C33 C34 C35 178.84(14) . . . . ?
C33 C34 C35 N36 -0.1(2) . . . . ?
C34 C35 N36 C37 1.1(2) . . . . ?
C35 N36 C37 C38 -1.0(2) . . . . ?
N36 C37 C38 C33 0.0(2) . . . . ?
C34 C33 C38 C37 1.0(2) . . . . ?
C32 C33 C38 C37 -178.81(15) . . . . ?
C30B C25B C26B N27B 0.0 . . . . ?
C25B C26B N27B C28B 0.0 . . . . ?
C26B N27B C28B C29B 0.0 . . . . ?
N27B C28B C29B C30B 0.0 . . . . ?
C28B C29B C30B C25B 0.0 . . . . ?
C28B C29B C30B C31B -178(3) . . . . ?
C26B C25B C30B C29B 0.0 . . . . ?
C26B C25B C30B C31B 178.6(19) . . . . ?
C29B C30B C31B C32B -165(4) . . . . ?
C25B C30B C31B C32B 17(5) . . . . ?
C30B C31B C32B C33B 180(3) . . . . ?
C31B C32B C33B C34B -14(5) . . . . ?
C31B C32B C33B C38B 164(4) . . . . ?
C38B C33B C34B C35B 0.0 . . . . ?
C32B C33B C34B C35B 178.4(17) . . . . ?
C33B C34B C35B N36B 0.0 . . . . ?
C34B C35B N36B C37B 0.0 . . . . ?
C35B N36B C37B C38B 0.0 . . . . ?
N36B C37B C38B C33B 0.0 . . . . ?
C34B C33B C38B C37B 0.0 . . . . ?
C32B C33B C38B C37B -178(2) . . . . ?

_refine_diff_density_max         0.477
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_p1907a
_database_code_depnum_ccdc_archive 'CCDC 1940954'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H18 O4, C12 H10 N2'
_chemical_formula_sum            'C22 H28 N2 O4'
_chemical_formula_weight         384.46

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

_space_group_crystal_system      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                   9.5773(5)
_cell_length_b                   10.7505(6)
_cell_length_c                   10.9564(6)
_cell_angle_alpha                96.199(2)
_cell_angle_beta                 97.7308(19)
_cell_angle_gamma                113.7266(18)
_cell_volume                     1006.87(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      33.2

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7111
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            35723
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.369
_diffrn_reflns_theta_max         33.210
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7668
_reflns_number_gt                5433
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0812P)²+0.1281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7668
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
O01 O 1.43550(8) 0.45735(7) 0.70709(7) 0.02671(16) Uani 1 1 d . . . . .
O02 O 0.07175(8) -0.46189(7) 0.25214(8) 0.03071(18) Uani 1 1 d . . . . .
H02 H -0.0281(19) -0.4944(15) 0.2085(14) 0.046 Uiso 1 1 d . U . . .
O03 O 1.48148(8) 0.63473(7) 0.60425(7) 0.02807(17) Uani 1 1 d . . . . .
H03 H 1.5755(18) 0.6744(15) 0.6566(14) 0.042 Uiso 1 1 d . U . . .
O04 O 0.11426(9) -0.26853(8) 0.17523(8) 0.03409(19) Uani 1 1 d . . . . .
C07 C 0.97186(9) 0.25284(9) 0.46623(8) 0.01838(17) Uani 1 1 d . . . . .
H07A H 0.923708 0.316515 0.486647 0.022 Uiso 1 1 calc R U . . .
H07B H 0.988829 0.255967 0.379241 0.022 Uiso 1 1 calc R U . . .
C08 C 0.32222(9) -0.28301(8) 0.31536(8) 0.01832(16) Uani 1 1 d . . . . .
H08A H 0.367868 -0.346695 0.288244 0.022 Uiso 1 1 calc R U . . .
H08B H 0.315002 -0.286543 0.404317 0.022 Uiso 1 1 calc R U . . .
C09 C 0.43169(10) -0.13740(9) 0.30579(8) 0.01861(17) Uani 1 1 d . . . . .
H09A H 0.386056 -0.072992 0.330761 0.022 Uiso 1 1 calc R U . . .
H09B H 0.443842 -0.133658 0.217767 0.022 Uiso 1 1 calc R U . . .
C10 C 0.85958(10) 0.10680(9) 0.47343(9) 0.02081(18) Uani 1 1 d . . . . .
H10A H 0.841635 0.103932 0.560187 0.025 Uiso 1 1 calc R U . . .
H10B H 0.908242 0.043285 0.453997 0.025 Uiso 1 1 calc R U . . .
C12 C 1.23497(10) 0.44956(9) 0.54296(9) 0.02045(17) Uani 1 1 d . . . . .
H12A H 1.249213 0.449982 0.455143 0.025 Uiso 1 1 calc R U . . .
H12B H 1.182090 0.509890 0.561102 0.025 Uiso 1 1 calc R U . . .
C14 C 0.59115(10) -0.09149(9) 0.38916(9) 0.02017(17) Uani 1 1 d . . . . .
H14A H 0.578013 -0.097992 0.476680 0.024 Uiso 1 1 calc R U . . .
H14B H 0.637033 -0.155253 0.362823 0.024 Uiso 1 1 calc R U . . .
C15 C 1.12915(10) 0.30363(9) 0.55436(9) 0.02001(17) Uani 1 1 d . . . . .
H15A H 1.113442 0.301405 0.641722 0.024 Uiso 1 1 calc R U . . .
H15B H 1.178929 0.241292 0.533888 0.024 Uiso 1 1 calc R U . . .
C16 C 1.39312(10) 0.51114(9) 0.62729(8) 0.01850(16) Uani 1 1 d . . . . .
C18 C 0.70298(10) 0.05538(9) 0.38423(8) 0.01829(16) Uani 1 1 d . . . . .
H18A H 0.653596 0.118039 0.404716 0.022 Uiso 1 1 calc R U . . .
H18B H 0.721220 0.060055 0.297673 0.022 Uiso 1 1 calc R U . . .
C20 C 0.16031(10) -0.33431(9) 0.23914(8) 0.01894(17) Uani 1 1 d . . . . .
N05 N 0.22118(9) 0.58820(8) -0.13036(8) 0.02320(17) Uani 1 1 d . . . . .
N06 N 1.23818(9) 1.22781(8) 0.24953(7) 0.02112(16) Uani 1 1 d . . . . .
C11 C 0.30115(11) 0.70929(10) -0.16271(9) 0.02374(19) Uani 1 1 d . . . . .
H11 H 0.251504 0.736337 -0.229022 0.028 Uiso 1 1 calc R U . . .
C13 C 1.16804(10) 1.09410(10) 0.25686(9) 0.02334(19) Uani 1 1 d . . . . .
H13 H 1.223620 1.056978 0.308599 0.028 Uiso 1 1 calc R U . . .
C17 C 1.00996(10) 1.19787(9) 0.10627(8) 0.01989(17) Uani 1 1 d . . . . .
H17 H 0.958948 1.237369 0.053078 0.024 Uiso 1 1 calc R U . . .
C19 C 0.93545(10) 1.05919(9) 0.11628(8) 0.01732(16) Uani 1 1 d . . . . .
C21 C 0.29267(11) 0.55139(10) -0.03726(9) 0.02528(19) Uani 1 1 d . . . . .
H21 H 0.237692 0.464939 -0.013677 0.030 Uiso 1 1 calc R U . . .
C22 C 0.77632(10) 0.97480(9) 0.04644(8) 0.01953(17) Uani 1 1 d . . . . .
H22 H 0.733744 1.013981 -0.013612 0.023 Uiso 1 1 calc R U . . .
C23 C 1.15956(10) 1.27798(9) 0.17475(8) 0.02064(17) Uani 1 1 d . . . . .
H23 H 1.208026 1.372689 0.168045 0.025 Uiso 1 1 calc R U . . .
C24 C 0.52730(10) 0.76042(9) -0.00685(8) 0.01853(16) Uani 1 1 d . . . . .
C25 C 0.44392(11) 0.63377(10) 0.02679(9) 0.02255(18) Uani 1 1 d . . . . .
H25 H 0.489999 0.603870 0.092985 0.027 Uiso 1 1 calc R U . . .
C26 C 0.45234(10) 0.79787(10) -0.10525(9) 0.02302(19) Uani 1 1 d . . . . .
H26 H 0.504473 0.882874 -0.132221 0.028 Uiso 1 1 calc R U . . .
C27 C 1.01910(10) 1.00664(9) 0.19341(9) 0.02195(18) Uani 1 1 d . . . . .
H27 H 0.974274 0.912335 0.202045 0.026 Uiso 1 1 calc R U . . .
C28 C 0.68684(10) 0.84684(10) 0.06109(8) 0.02120(18) Uani 1 1 d . . . . .
H28 H 0.730582 0.808327 0.121029 0.025 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O01 C16 1.2108(11) . ?
O02 C20 1.3264(11) . ?
O02 H02 0.915(16) . ?
O03 C16 1.3305(11) . ?
O03 H03 0.906(16) . ?
O04 C20 1.2083(11) . ?
C07 C10 1.5226(12) . ?
C07 C15 1.5273(12) . ?
C07 H07A 0.9900 . ?
C07 H07B 0.9900 . ?
C08 C20 1.5067(11) . ?
C08 C09 1.5181(11) . ?
C08 H08A 0.9900 . ?
C08 H08B 0.9900 . ?
C09 C14 1.5268(12) . ?
C09 H09A 0.9900 . ?
C09 H09B 0.9900 . ?
C10 C18 1.5271(12) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 C16 1.5069(11) . ?
C12 C15 1.5169(12) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C18 1.5219(12) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N05 C11 1.3331(12) . ?
N05 C21 1.3354(13) . ?
N06 C23 1.3362(12) . ?
N06 C13 1.3366(12) . ?
C11 C26 1.3840(12) . ?
C11 H11 0.9500 . ?
C13 C27 1.3838(12) . ?
C13 H13 0.9500 . ?
C17 C23 1.3913(12) . ?
C17 C19 1.3943(12) . ?
C17 H17 0.9500 . ?
C19 C27 1.4001(12) . ?
C19 C22 1.4680(11) . ?
C21 C25 1.3910(13) . ?
C21 H21 0.9500 . ?
C22 C28 1.3373(13) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.3928(13) . ?
C24 C26 1.3992(12) . ?
C24 C28 1.4678(12) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O02 H02 113.0(9) . . ?
C16 O03 H03 112.0(9) . . ?
C10 C07 C15 113.58(7) . . ?
C10 C07 H07A 108.8 . . ?
C15 C07 H07A 108.8 . . ?
C10 C07 H07B 108.8 . . ?
C15 C07 H07B 108.8 . . ?
H07A C07 H07B 107.7 . . ?
C20 C08 C09 114.85(7) . . ?
C20 C08 H08A 108.6 . . ?
C09 C08 H08A 108.6 . . ?
C20 C08 H08B 108.6 . . ?
C09 C08 H08B 108.6 . . ?
H08A C08 H08B 107.5 . . ?
C08 C09 C14 111.56(7) . . ?
C08 C09 H09A 109.3 . . ?
C14 C09 H09A 109.3 . . ?
C08 C09 H09B 109.3 . . ?
C14 C09 H09B 109.3 . . ?
H09A C09 H09B 108.0 . . ?
C07 C10 C18 113.59(7) . . ?
C07 C10 H10A 108.8 . . ?
C18 C10 H10A 108.8 . . ?
C07 C10 H10B 108.8 . . ?
C18 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C16 C12 C15 115.49(7) . . ?
C16 C12 H12A 108.4 . . ?
C15 C12 H12A 108.4 . . ?
C16 C12 H12B 108.4 . . ?
C15 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C18 C14 C09 113.04(7) . . ?
C18 C14 H14A 109.0 . . ?
C09 C14 H14A 109.0 . . ?
C18 C14 H14B 109.0 . . ?
C09 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C12 C15 C07 110.90(7) . . ?
C12 C15 H15A 109.5 . . ?
C07 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C07 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
O01 C16 O03 123.64(8) . . ?
O01 C16 C12 125.16(8) . . ?
O03 C16 C12 111.19(7) . . ?
C14 C18 C10 113.91(7) . . ?
C14 C18 H18A 108.8 . . ?
C10 C18 H18A 108.8 . . ?
C14 C18 H18B 108.8 . . ?
C10 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
O04 C20 O02 123.46(8) . . ?
O04 C20 C08 125.16(8) . . ?
O02 C20 C08 111.36(7) . . ?
C11 N05 C21 117.42(8) . . ?
C23 N06 C13 117.43(8) . . ?
N05 C11 C26 123.78(8) . . ?
N05 C11 H11 118.1 . . ?
C26 C11 H11 118.1 . . ?
N06 C13 C27 123.75(8) . . ?
N06 C13 H13 118.1 . . ?
C27 C13 H13 118.1 . . ?
C23 C17 C19 119.52(8) . . ?
C23 C17 H17 120.2 . . ?
C19 C17 H17 120.2 . . ?
C17 C19 C27 117.24(8) . . ?
C17 C19 C22 119.83(8) . . ?
C27 C19 C22 122.93(8) . . ?
N05 C21 C25 123.04(9) . . ?
N05 C21 H21 118.5 . . ?
C25 C21 H21 118.5 . . ?
C28 C22 C19 124.84(8) . . ?
C28 C22 H22 117.6 . . ?
C19 C22 H22 117.6 . . ?
N06 C23 C17 123.00(8) . . ?
N06 C23 H23 118.5 . . ?
C17 C23 H23 118.5 . . ?
C25 C24 C26 117.21(8) . . ?
C25 C24 C28 119.24(8) . . ?
C26 C24 C28 123.56(8) . . ?
C24 C25 C21 119.51(8) . . ?
C24 C25 H25 120.2 . . ?
C21 C25 H25 120.2 . . ?
C11 C26 C24 119.04(8) . . ?
C11 C26 H26 120.5 . . ?
C24 C26 H26 120.5 . . ?
C13 C27 C19 119.02(8) . . ?
C13 C27 H27 120.5 . . ?
C19 C27 H27 120.5 . . ?
C22 C28 C24 126.03(8) . . ?
C22 C28 H28 117.0 . . ?
C24 C28 H28 117.0 . . ?

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
C20 C08 C09 C14 177.98(7) . . . . ?
C15 C07 C10 C18 -179.33(8) . . . . ?
C08 C09 C14 C18 -178.70(7) . . . . ?
C16 C12 C15 C07 179.19(8) . . . . ?
C10 C07 C15 C12 -179.78(8) . . . . ?
C15 C12 C16 O01 -5.48(14) . . . . ?
C15 C12 C16 O03 175.37(8) . . . . ?
C09 C14 C18 C10 176.17(8) . . . . ?
C07 C10 C18 C14 178.95(8) . . . . ?
C09 C08 C20 O04 -1.03(14) . . . . ?
C09 C08 C20 O02 179.95(8) . . . . ?
C21 N05 C11 C26 -0.21(16) . . . . ?
C23 N06 C13 C27 -1.10(15) . . . . ?
C23 C17 C19 C27 -1.88(13) . . . . ?
C23 C17 C19 C22 178.66(8) . . . . ?
C11 N05 C21 C25 0.69(16) . . . . ?
C17 C19 C22 C28 -170.97(9) . . . . ?
C27 C19 C22 C28 9.61(15) . . . . ?
C13 N06 C23 C17 0.42(14) . . . . ?
C19 C17 C23 N06 1.09(14) . . . . ?
C26 C24 C25 C21 -0.07(14) . . . . ?
C28 C24 C25 C21 180.00(9) . . . . ?
N05 C21 C25 C24 -0.55(16) . . . . ?
N05 C11 C26 C24 -0.39(16) . . . . ?
C25 C24 C26 C11 0.51(14) . . . . ?
C28 C24 C26 C11 -179.57(9) . . . . ?
N06 C13 C27 C19 0.25(16) . . . . ?
C17 C19 C27 C13 1.26(14) . . . . ?
C22 C19 C27 C13 -179.31(9) . . . . ?
C19 C22 C28 C24 179.67(8) . . . . ?
C25 C24 C28 C22 -174.28(9) . . . . ?
C26 C24 C28 C22 5.80(15) . . . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_p1823c
_database_code_depnum_ccdc_archive 'CCDC 1940950'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2, C7 H7 N O2'
_chemical_formula_sum            'C19 H17 N3 O2'
_chemical_formula_weight         319.35

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                   8.4722(8)
_cell_length_b                   8.6319(8)
_cell_length_c                   11.8009(12)
_cell_angle_alpha                108.849(3)
_cell_angle_beta                 98.114(3)
_cell_angle_gamma                97.134(3)
_cell_volume                     795.17(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6414
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      28.2

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.541
_exptl_crystal_size_mid          0.366
_exptl_crystal_size_min          0.166
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            14502
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0337
_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       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.469
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3941
_reflns_number_gt                2925
_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.8152P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3941
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1516
_refine_ls_wR_factor_gt          0.1379
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
O01A O 0.3097(2) 0.25824(18) 0.88631(15) 0.0324(4) Uani 0.871(3) 1 d . . P A 1
H01A H 0.290309 0.172583 0.904794 0.049 Uiso 0.871(3) 1 calc R U P A 1
O02A O 0.4674(2) 0.10847(19) 0.77601(16) 0.0313(4) Uani 0.871(3) 1 d . . P A 1
C03A C 0.4140(3) 0.2376(4) 0.8129(3) 0.0212(5) Uani 0.871(3) 1 d . . P A 1
C04A C 0.4599(3) 0.3839(3) 0.7760(2) 0.0193(5) Uani 0.871(3) 1 d . . P A 1
C05A C 0.4040(3) 0.5327(4) 0.8250(3) 0.0231(5) Uani 0.871(3) 1 d . . P A 1
H05A H 0.337176 0.542073 0.884228 0.028 Uiso 0.871(3) 1 calc R U P A 1
C06A C 0.4450(3) 0.6662(3) 0.7878(2) 0.0231(5) Uani 0.871(3) 1 d . . P A 1
H06A H 0.405516 0.766165 0.821565 0.028 Uiso 0.871(3) 1 calc R U P A 1
C07A C 0.5581(4) 0.3716(4) 0.6886(3) 0.0241(6) Uani 0.871(3) 1 d . . P A 1
H07A H 0.597457 0.271517 0.655081 0.029 Uiso 0.871(3) 1 calc R U P A 1
C08A C 0.5979(3) 0.5056(3) 0.6509(3) 0.0246(6) Uani 0.871(3) 1 d . . P A 1
H08A H 0.662538 0.495274 0.590210 0.030 Uiso 0.871(3) 1 calc R U P A 1
C09A C 0.5442(3) 0.6563(4) 0.7010(3) 0.0229(6) Uani 0.871(3) 1 d . . P A 1
N10A N 0.5865(3) 0.7894(3) 0.6658(3) 0.0312(6) Uani 0.871(3) 1 d . . P A 1
H10A H 0.561(5) 0.880(6) 0.707(4) 0.037 Uiso 0.871(3) 1 d . U P A 1
H10B H 0.660(5) 0.785(4) 0.622(3) 0.037 Uiso 0.871(3) 1 d . U P A 1
N11A N 0.1878(4) -0.0167(3) 0.9197(3) 0.0260(6) Uani 0.871(3) 1 d . . P A 1
C12A C 0.2508(4) -0.0638(4) 1.0119(3) 0.0266(7) Uani 0.871(3) 1 d . . P A 1
H12A H 0.346249 0.003862 1.066412 0.032 Uiso 0.871(3) 1 calc R U P A 1
C13A C 0.0528(4) -0.1162(5) 0.8425(3) 0.0288(8) Uani 0.871(3) 1 d . . P A 1
H13A H 0.007173 -0.086396 0.775976 0.035 Uiso 0.871(3) 1 calc R U P A 1
C14A C 0.1840(3) -0.2062(4) 1.0318(2) 0.0224(6) Uani 0.871(3) 1 d . . P A 1
H14A H 0.232665 -0.233609 1.098720 0.027 Uiso 0.871(3) 1 calc R U P A 1
C15A C -0.0222(4) -0.2602(3) 0.8562(3) 0.0271(6) Uani 0.871(3) 1 d . . P A 1
H15A H -0.117955 -0.325295 0.800656 0.033 Uiso 0.871(3) 1 calc R U P A 1
C16A C 0.0439(4) -0.3087(3) 0.9519(3) 0.0189(5) Uani 0.871(3) 1 d . . P A 1
C17A C -0.0341(3) -0.4612(3) 0.9647(2) 0.0210(4) Uani 0.871(3) 1 d . . P A 1
H17A H -0.137(3) -0.508(3) 0.915(2) 0.025 Uiso 0.871(3) 1 d . U P A 1
O01B O 0.7106(16) 0.7562(18) 0.6302(14) 0.042(4) Uiso 0.129(3) 1 d . . P A 2
H01B H 0.727122 0.843475 0.613312 0.063 Uiso 0.129(3) 1 calc R U P A 2
O02B O 0.531(2) 0.890(3) 0.7214(19) 0.049(5) Uiso 0.129(3) 1 d . . P A 2
C03B C 0.591(3) 0.763(4) 0.694(2) 0.034(7) Uiso 0.129(3) 1 d . . P A 2
C04B C 0.542(4) 0.624(4) 0.722(3) 0.039(8) Uiso 0.129(3) 1 d . . P A 2
C05B C 0.595(2) 0.467(3) 0.6751(18) 0.024(5) Uiso 0.129(3) 1 d . . P A 2
H05B H 0.666805 0.449648 0.618812 0.029 Uiso 0.129(3) 1 calc R U P A 2
C06B C 0.541(5) 0.355(5) 0.713(3) 0.048(11) Uiso 0.129(3) 1 d . . P A 2
H06B H 0.572663 0.252700 0.671855 0.058 Uiso 0.129(3) 1 calc R U P A 2
C07B C 0.438(2) 0.617(3) 0.8068(16) 0.024(4) Uiso 0.129(3) 1 d . . P A 2
H07B H 0.390899 0.711237 0.840782 0.029 Uiso 0.129(3) 1 calc R U P A 2
C08B C 0.406(4) 0.490(3) 0.840(3) 0.041(8) Uiso 0.129(3) 1 d . . P A 2
H08B H 0.342770 0.502162 0.901436 0.049 Uiso 0.129(3) 1 calc R U P A 2
C09B C 0.4525(19) 0.338(2) 0.7942(14) 0.013(4) Uiso 0.129(3) 1 d . . P A 2
N10B N 0.421(4) 0.201(4) 0.822(3) 0.064(11) Uiso 0.129(3) 1 d . . P A 2
H10C H 0.459592 0.112247 0.785738 0.077 Uiso 0.129(3) 1 calc R U P A 2
H10D H 0.360792 0.200147 0.877122 0.077 Uiso 0.129(3) 1 calc R U P A 2
N11B N 0.149(3) -0.039(3) 0.8891(19) 0.020(5) Uiso 0.129(3) 1 d . . P A 2
C12B C 0.031(4) -0.161(4) 0.839(3) 0.041(9) Uiso 0.129(3) 1 d . . P A 2
H12B H -0.041045 -0.162471 0.769344 0.049 Uiso 0.129(3) 1 calc R U P A 2
C13B C 0.225(3) -0.039(4) 0.991(3) 0.034(7) Uiso 0.129(3) 1 d . . P A 2
H13B H 0.307803 0.053841 1.035422 0.041 Uiso 0.129(3) 1 calc R U P A 2
C14B C 0.004(3) -0.285(3) 0.880(3) 0.036(7) Uiso 0.129(3) 1 d . . P A 2
H14B H -0.079541 -0.377927 0.835742 0.043 Uiso 0.129(3) 1 calc R U P A 2
C15B C 0.200(3) -0.152(3) 1.040(2) 0.031(6) Uiso 0.129(3) 1 d . . P A 2
H15B H 0.260989 -0.138572 1.117409 0.037 Uiso 0.129(3) 1 calc R U P A 2
C16B C 0.092(3) -0.283(3) 0.982(2) 0.031(6) Uiso 0.129(3) 1 d . . P A 2
C17B C 0.043(3) -0.445(3) 1.017(3) 0.061(6) Uiso 0.129(3) 1 d . . P A 2
H17B H 0.111723 -0.438668 1.089261 0.073 Uiso 0.129(3) 1 calc R U P A 2
N18 N 0.8497(2) 1.0340(2) 0.61374(17) 0.0343(4) Uani 1 1 d . . . . .
C19 C 0.7765(3) 1.0283(2) 0.5048(2) 0.0345(5) Uani 1 1 d . . . . .
H19 H 0.698958 0.931935 0.456095 0.041 Uiso 1 1 calc R U . . .
C20 C 0.8066(2) 1.1547(2) 0.45807(19) 0.0311(4) Uani 1 1 d . . . . .
H20 H 0.750137 1.143563 0.379567 0.037 Uiso 1 1 calc R U . . .
C21 C 0.9572(3) 1.1727(3) 0.6792(2) 0.0341(5) Uani 1 1 d . . . . .
H21 H 1.010592 1.180932 0.757853 0.041 Uiso 1 1 calc R U . . .
C22 C 0.9958(2) 1.3045(2) 0.64012(18) 0.0307(4) Uani 1 1 d . . . . .
H22 H 1.073994 1.399282 0.690720 0.037 Uiso 1 1 calc R U . . .
C23 C 0.9188(2) 1.2969(2) 0.52562(18) 0.0262(4) Uani 1 1 d . . . . .
C24 C 0.9470(2) 1.4300(2) 0.47405(19) 0.0305(4) Uani 1 1 d . . . . .
H24 H 0.880(3) 1.415(3) 0.389(2) 0.037 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O01A C03A 1.311(4) . ?
O01A H01A 0.8400 . ?
O02A C03A 1.226(4) . ?
C03A C04A 1.489(4) . ?
C04A C07A 1.400(5) . ?
C04A C05A 1.399(4) . ?
C05A C06A 1.383(4) . ?
C05A H05A 0.9500 . ?
C06A C09A 1.402(4) . ?
C06A H06A 0.9500 . ?
C07A C08A 1.388(4) . ?
C07A H07A 0.9500 . ?
C08A C09A 1.405(4) . ?
C08A H08A 0.9500 . ?
C09A N10A 1.367(4) . ?
N10A H10A 0.85(5) . ?
N10A H10B 0.86(4) . ?
N11A C12A 1.345(5) . ?
N11A C13A 1.353(5) . ?
C12A C14A 1.392(4) . ?
C12A H12A 0.9500 . ?
C13A C15A 1.392(4) . ?
C13A H13A 0.9500 . ?
C14A C16A 1.401(4) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.395(4) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.461(3) . ?
C17A C17A 1.341(4) 2_547 ?
C17A H17A 0.94(3) . ?
O01B C03B 1.34(3) . ?
O01B H01B 0.8400 . ?
O02B C03B 1.23(4) . ?
C03B C04B 1.37(3) . ?
C04B C07B 1.43(3) . ?
C04B C05B 1.44(4) . ?
C05B C06B 1.25(3) . ?
C05B H05B 0.9500 . ?
C06B C09B 1.33(4) . ?
C06B H06B 0.9500 . ?
C07B C08B 1.29(3) . ?
C07B H07B 0.9500 . ?
C08B C09B 1.38(3) . ?
C08B H08B 0.9500 . ?
C09B N10B 1.33(3) . ?
N10B H10C 0.8800 . ?
N10B H10D 0.8800 . ?
N11B C12B 1.28(3) . ?
N11B C13B 1.28(3) . ?
C12B C14B 1.32(4) . ?
C12B H12B 0.9500 . ?
C13B C15B 1.30(3) . ?
C13B H13B 0.9500 . ?
C14B C16B 1.31(3) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.28(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.60(4) . ?
C17B C17B 1.04(5) 2_547 ?
C17B H17B 0.9500 . ?
N18 C19 1.329(3) . ?
N18 C21 1.340(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C23 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.393(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.473(3) . ?
C24 C24 1.319(4) 2_786 ?
C24 H24 1.04(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
C03A O01A H01A 109.5 . . ?
O02A C03A O01A 123.2(3) . . ?
O02A C03A C04A 122.7(3) . . ?
O01A C03A C04A 114.1(3) . . ?
C07A C04A C05A 119.2(3) . . ?
C07A C04A C03A 119.5(3) . . ?
C05A C04A C03A 121.3(3) . . ?
C06A C05A C04A 120.5(2) . . ?
C06A C05A H05A 119.7 . . ?
C04A C05A H05A 119.7 . . ?
C05A C06A C09A 121.0(2) . . ?
C05A C06A H06A 119.5 . . ?
C09A C06A H06A 119.5 . . ?
C08A C07A C04A 120.0(3) . . ?
C08A C07A H07A 120.0 . . ?
C04A C07A H07A 120.0 . . ?
C07A C08A C09A 121.1(3) . . ?
C07A C08A H08A 119.5 . . ?
C09A C08A H08A 119.5 . . ?
N10A C09A C06A 120.8(3) . . ?
N10A C09A C08A 121.1(3) . . ?
C06A C09A C08A 118.2(3) . . ?
C09A N10A H10A 115(3) . . ?
C09A N10A H10B 118(2) . . ?
H10A N10A H10B 123(4) . . ?
C12A N11A C13A 117.0(3) . . ?
N11A C12A C14A 123.7(3) . . ?
N11A C12A H12A 118.2 . . ?
C14A C12A H12A 118.2 . . ?
N11A C13A C15A 123.0(3) . . ?
N11A C13A H13A 118.5 . . ?
C15A C13A H13A 118.5 . . ?
C12A C14A C16A 119.1(3) . . ?
C12A C14A H14A 120.4 . . ?
C16A C14A H14A 120.4 . . ?
C16A C15A C13A 119.7(3) . . ?
C16A C15A H15A 120.1 . . ?
C13A C15A H15A 120.1 . . ?
C15A C16A C14A 117.4(2) . . ?
C15A C16A C17A 119.4(3) . . ?
C14A C16A C17A 123.1(3) . . ?
C17A C17A C16A 124.8(3) 2_547 . ?
C17A C17A H17A 120.2(15) 2_547 . ?
C16A C17A H17A 114.9(15) . . ?
C03B O01B H01B 109.5 . . ?
O02B C03B O01B 119(3) . . ?
O02B C03B C04B 125(3) . . ?
O01B C03B C04B 117(2) . . ?
C07B C04B C05B 110(2) . . ?
C07B C04B C03B 125(3) . . ?
C05B C04B C03B 125(3) . . ?
C06B C05B C04B 116(3) . . ?
C06B C05B H05B 122.0 . . ?
C04B C05B H05B 122.0 . . ?
C05B C06B C09B 138(4) . . ?
C05B C06B H06B 110.9 . . ?
C09B C06B H06B 110.9 . . ?
C08B C07B C04B 124(2) . . ?
C08B C07B H07B 118.1 . . ?
C04B C07B H07B 118.1 . . ?
C07B C08B C09B 127(3) . . ?
C07B C08B H08B 116.6 . . ?
C09B C08B H08B 116.6 . . ?
N10B C09B C06B 126(3) . . ?
N10B C09B C08B 130(3) . . ?
C06B C09B C08B 105(3) . . ?
C09B N10B H10C 120.0 . . ?
C09B N10B H10D 120.0 . . ?
H10C N10B H10D 120.0 . . ?
C12B N11B C13B 113(3) . . ?
N11B C12B C14B 123(3) . . ?
N11B C12B H12B 118.6 . . ?
C14B C12B H12B 118.6 . . ?
N11B C13B C15B 127(3) . . ?
N11B C13B H13B 116.4 . . ?
C15B C13B H13B 116.4 . . ?
C12B C14B C16B 121(3) . . ?
C12B C14B H14B 119.5 . . ?
C16B C14B H14B 119.5 . . ?
C16B C15B C13B 119(3) . . ?
C16B C15B H15B 120.4 . . ?
C13B C15B H15B 120.4 . . ?
C15B C16B C14B 116(3) . . ?
C15B C16B C17B 130(2) . . ?
C14B C16B C17B 114(3) . . ?
C17B C17B C16B 139(5) 2_547 . ?
C17B C17B H17B 110.4 2_547 . ?
C16B C17B H17B 110.4 . . ?
C19 N18 C21 115.83(16) . . ?
N18 C19 C20 123.85(19) . . ?
N18 C19 H19 118.1 . . ?
C20 C19 H19 118.1 . . ?
C23 C20 C19 120.03(19) . . ?
C23 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
N18 C21 C22 124.47(19) . . ?
N18 C21 H21 117.8 . . ?
C22 C21 H21 117.8 . . ?
C21 C22 C23 119.19(18) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C20 C23 C22 116.62(17) . . ?
C20 C23 C24 118.78(18) . . ?
C22 C23 C24 124.59(18) . . ?
C24 C24 C23 125.6(2) 2_786 . ?
C24 C24 H24 115.4(13) 2_786 . ?
C23 C24 H24 119.0(13) . . ?

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
O02A C03A C04A C07A 5.1(4) . . . . ?
O01A C03A C04A C07A -173.9(2) . . . . ?
O02A C03A C04A C05A -176.4(2) . . . . ?
O01A C03A C04A C05A 4.7(3) . . . . ?
C07A C04A C05A C06A -0.1(4) . . . . ?
C03A C04A C05A C06A -178.7(2) . . . . ?
C04A C05A C06A C09A -0.4(4) . . . . ?
C05A C04A C07A C08A -0.4(4) . . . . ?
C03A C04A C07A C08A 178.2(2) . . . . ?
C04A C07A C08A C09A 1.4(4) . . . . ?
C05A C06A C09A N10A -179.0(3) . . . . ?
C05A C06A C09A C08A 1.3(4) . . . . ?
C07A C08A C09A N10A 178.5(3) . . . . ?
C07A C08A C09A C06A -1.8(4) . . . . ?
C13A N11A C12A C14A -0.7(5) . . . . ?
C12A N11A C13A C15A 1.0(5) . . . . ?
N11A C12A C14A C16A 0.5(4) . . . . ?
N11A C13A C15A C16A -1.2(5) . . . . ?
C13A C15A C16A C14A 0.9(4) . . . . ?
C13A C15A C16A C17A -179.1(2) . . . . ?
C12A C14A C16A C15A -0.6(4) . . . . ?
C12A C14A C16A C17A 179.4(2) . . . . ?
C15A C16A C17A C17A 165.4(3) . . . 2_547 ?
C14A C16A C17A C17A -14.6(4) . . . 2_547 ?
O02B C03B C04B C07B -12(4) . . . . ?
O01B C03B C04B C07B 168(2) . . . . ?
O02B C03B C04B C05B 171(3) . . . . ?
O01B C03B C04B C05B -9(4) . . . . ?
C07B C04B C05B C06B 1(3) . . . . ?
C03B C04B C05B C06B 179(3) . . . . ?
C04B C05B C06B C09B -6(6) . . . . ?
C05B C04B C07B C08B 3(3) . . . . ?
C03B C04B C07B C08B -174(3) . . . . ?
C04B C07B C08B C09B -5(4) . . . . ?
C05B C06B C09B N10B -175(4) . . . . ?
C05B C06B C09B C08B 4(5) . . . . ?
C07B C08B C09B N10B -179(3) . . . . ?
C07B C08B C09B C06B 2(4) . . . . ?
C13B N11B C12B C14B -9(4) . . . . ?
C12B N11B C13B C15B 5(4) . . . . ?
N11B C12B C14B C16B 6(5) . . . . ?
N11B C13B C15B C16B 2(5) . . . . ?
C13B C15B C16B C14B -6(4) . . . . ?
C13B C15B C16B C17B 177(2) . . . . ?
C12B C14B C16B C15B 2(4) . . . . ?
C12B C14B C16B C17B -180(2) . . . . ?
C15B C16B C17B C17B 176(5) . . . 2_547 ?
C14B C16B C17B C17B -2(6) . . . 2_547 ?
C21 N18 C19 C20 0.4(3) . . . . ?
N18 C19 C20 C23 0.2(3) . . . . ?
C19 N18 C21 C22 -0.7(3) . . . . ?
N18 C21 C22 C23 0.5(3) . . . . ?
C19 C20 C23 C22 -0.4(3) . . . . ?
C19 C20 C23 C24 -179.35(19) . . . . ?
C21 C22 C23 C20 0.1(3) . . . . ?
C21 C22 C23 C24 178.96(19) . . . . ?
C20 C23 C24 C24 -177.9(3) . . . 2_786 ?
C22 C23 C24 C24 3.2(4) . . . 2_786 ?

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.051

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

data_p1823a
_database_code_depnum_ccdc_archive 'CCDC 1940956'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT353_p1823a              
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N14      - H64      .       1.41 Ang.  
RESPONSE: H64 of water (O64) is hydrogen bonded to N14
;
_vrf_PLAT771_p1823a              
;
PROBLEM: Suspect N-H Bond in CIF: N14      --H64       ..       1.41 Ang.  
RESPONSE: H64 of water (O64) is hydrogen bonded to N14
;
_vrf_PLAT306_p1823a              
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O64 Check 
RESPONSE: Only one hydrogen bondend hydrogen per water molecule could be located (H63,H64) 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C12 H10 N2), 2(C7 H7 N O2), 2(H2 O)'
_chemical_formula_sum            'C50 H48 N8 O6'
_chemical_formula_weight         856.96

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                   11.4554(6)
_cell_length_b                   14.1808(7)
_cell_length_c                   15.2055(8)
_cell_angle_alpha                104.905(2)
_cell_angle_beta                 94.946(2)
_cell_angle_gamma                111.852(2)
_cell_volume                     2169.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.6

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.575
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            7876
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.357
_diffrn_reflns_theta_max         25.685
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             7876
_reflns_number_gt                5641
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0868P)²+1.2368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7876
_refine_ls_number_parameters     603
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
N01 N 0.7272(3) 0.4266(2) 0.4001(2) 0.0266(7) Uani 1 1 d . . . . .
C02 C 0.6140(4) 0.4094(3) 0.3512(2) 0.0262(8) Uani 1 1 d . . . . .
H02 H 0.611081 0.416166 0.290531 0.031 Uiso 1 1 calc R U . . .
C03 C 0.7287(4) 0.4168(3) 0.4846(3) 0.0301(9) Uani 1 1 d . . . . .
H03 H 0.808179 0.429609 0.520742 0.036 Uiso 1 1 calc R U . . .
C04 C 0.5023(3) 0.3826(3) 0.3841(2) 0.0267(9) Uani 1 1 d . . . . .
H04 H 0.424313 0.370816 0.346744 0.032 Uiso 1 1 calc R U . . .
C05 C 0.6207(4) 0.3890(3) 0.5224(3) 0.0311(9) Uani 1 1 d . . . . .
H05 H 0.626258 0.381056 0.582613 0.037 Uiso 1 1 calc R U . . .
C06 C 0.5045(4) 0.3727(3) 0.4732(2) 0.0234(8) Uani 1 1 d . . . . .
C07 C 0.3913(4) 0.3452(3) 0.5164(2) 0.0269(9) Uani 1 1 d . . . . .
H07 H 0.403368 0.339504 0.577061 0.032 Uiso 1 1 calc R U . . .
C08 C 0.2744(4) 0.3279(3) 0.4778(2) 0.0246(8) Uani 1 1 d . . . . .
H08 H 0.261965 0.333908 0.417273 0.030 Uiso 1 1 calc R U . . .
C09 C 0.1614(4) 0.2998(3) 0.5217(2) 0.0248(8) Uani 1 1 d . . . . .
C10 C 0.0431(4) 0.2741(3) 0.4701(3) 0.0310(9) Uani 1 1 d . . . . .
H10 H 0.034588 0.274842 0.407642 0.037 Uiso 1 1 calc R U . . .
C11 C 0.1670(3) 0.2986(3) 0.6130(3) 0.0285(9) Uani 1 1 d . . . . .
H11 H 0.247184 0.317641 0.651556 0.034 Uiso 1 1 calc R U . . .
C12 C -0.0632(4) 0.2472(3) 0.5103(3) 0.0343(9) Uani 1 1 d . . . . .
H12 H -0.144190 0.229343 0.473342 0.041 Uiso 1 1 calc R U . . .
C13 C 0.0553(4) 0.2695(3) 0.6476(3) 0.0317(9) Uani 1 1 d . . . . .
H13 H 0.060841 0.267105 0.709689 0.038 Uiso 1 1 calc R U . . .
N14 N -0.0598(3) 0.2445(3) 0.5975(2) 0.0302(8) Uani 1 1 d . . . . .
N15 N 0.2729(3) 0.4723(2) -0.0959(2) 0.0235(7) Uani 1 1 d . . . . .
C16 C 0.2351(4) 0.5256(3) -0.1450(2) 0.0255(8) Uani 1 1 d . . . . .
H16 H 0.188885 0.487835 -0.207183 0.031 Uiso 1 1 calc R U . . .
C17 C 0.3343(4) 0.5265(3) -0.0079(2) 0.0271(9) Uani 1 1 d . . . . .
H17 H 0.360977 0.489883 0.028287 0.032 Uiso 1 1 calc R U . . .
C18 C 0.2600(3) 0.6326(3) -0.1098(2) 0.0232(8) Uani 1 1 d . . . . .
H18 H 0.233538 0.667392 -0.148108 0.028 Uiso 1 1 calc R U . . .
C19 C 0.3608(3) 0.6327(3) 0.0328(2) 0.0236(8) Uani 1 1 d . . . . .
H19 H 0.404360 0.667282 0.095923 0.028 Uiso 1 1 calc R U . . .
C20 C 0.3245(3) 0.6899(3) -0.0175(2) 0.0191(8) Uani 1 1 d . . . . .
C21 C 0.3537(3) 0.8030(3) 0.0260(2) 0.0207(8) Uani 1 1 d . . . . .
H21 H 0.403722 0.835987 0.087422 0.025 Uiso 1 1 calc R U . . .
C22 C 0.3164(3) 0.8636(3) -0.0130(2) 0.0217(8) Uani 1 1 d . . . . .
H22 H 0.263909 0.829734 -0.073537 0.026 Uiso 1 1 calc R U . . .
C23 C 0.3487(3) 0.9777(3) 0.0288(2) 0.0222(8) Uani 1 1 d . . . . .
C24 C 0.3045(4) 1.0314(3) -0.0215(3) 0.0306(9) Uani 1 1 d . . . . .
H24 H 0.251947 0.993595 -0.081845 0.037 Uiso 1 1 calc R U . . .
C25 C 0.4254(4) 1.0398(3) 0.1164(2) 0.0271(9) Uani 1 1 d . . . . .
H25 H 0.458497 1.007961 0.154239 0.033 Uiso 1 1 calc R U . . .
C26 C 0.3371(4) 1.1395(3) 0.0163(3) 0.0346(10) Uani 1 1 d . . . . .
H26 H 0.305146 1.173708 -0.019701 0.042 Uiso 1 1 calc R U . . .
C27 C 0.4533(4) 1.1481(3) 0.1484(3) 0.0287(9) Uani 1 1 d . . . . .
H27 H 0.506162 1.188179 0.208310 0.034 Uiso 1 1 calc R U . . .
N28 N 0.4109(3) 1.1996(3) 0.1007(2) 0.0290(7) Uani 1 1 d . . . . .
N29 N 0.3724(3) 0.1050(2) 0.3738(2) 0.0272(7) Uani 1 1 d . . . . .
C30 C 0.2649(3) 0.0966(3) 0.3236(2) 0.0258(8) Uani 1 1 d . . . . .
H30 H 0.269997 0.112885 0.266865 0.031 Uiso 1 1 calc R U . . .
C31 C 0.3608(4) 0.0833(3) 0.4538(3) 0.0307(9) Uani 1 1 d . . . . .
H31 H 0.435878 0.090239 0.491615 0.037 Uiso 1 1 calc R U . . .
C32 C 0.1472(3) 0.0655(3) 0.3495(2) 0.0246(8) Uani 1 1 d . . . . .
H32 H 0.073920 0.060266 0.310738 0.030 Uiso 1 1 calc R U . . .
C33 C 0.2471(3) 0.0514(3) 0.4854(2) 0.0247(8) Uani 1 1 d . . . . .
H33 H 0.244947 0.036047 0.542624 0.030 Uiso 1 1 calc R U . . .
C34 C 0.1362(3) 0.0421(3) 0.4322(2) 0.0199(7) Uani 1 1 d . . . . .
C35 C 0.0109(3) 0.0087(3) 0.4600(2) 0.0215(8) Uani 1 1 d . . . . .
H35 H -0.061033 -0.001468 0.416762 0.026 Uiso 1 1 calc R U . . .
N36 N 0.0742(3) 0.8628(3) 0.1225(2) 0.0324(8) Uani 1 1 d . . . . .
C37 C 0.0060(4) 0.7937(3) 0.0400(3) 0.0326(9) Uani 1 1 d . . . . .
H37 H -0.032714 0.819395 -0.000715 0.039 Uiso 1 1 calc R U . . .
C38 C 0.1294(4) 0.8243(3) 0.1779(3) 0.0329(9) Uani 1 1 d . . . . .
H38 H 0.179773 0.871356 0.237037 0.039 Uiso 1 1 calc R U . . .
C39 C -0.0127(3) 0.6879(3) 0.0091(3) 0.0279(9) Uani 1 1 d . . . . .
H39 H -0.062972 0.643081 -0.050736 0.033 Uiso 1 1 calc R U . . .
C40 C 0.1163(4) 0.7194(3) 0.1528(2) 0.0294(8) Uani 1 1 d . . . . .
H40 H 0.157404 0.696282 0.194549 0.035 Uiso 1 1 calc R U . . .
C41 C 0.0437(3) 0.6475(3) 0.0672(2) 0.0203(8) Uani 1 1 d . . . . .
C42 C 0.0300(3) 0.5370(2) 0.0409(2) 0.0206(8) Uani 1 1 d . . . . .
H42 H 0.067578 0.516009 0.086370 0.025 Uiso 1 1 calc R U . . .
O43 O 0.2514(2) 0.2740(2) 0.83790(17) 0.0282(6) Uani 1 1 d . . . . .
H43 H 0.260(4) 0.348(3) 0.856(3) 0.042 Uiso 1 1 d . U . . .
O44 O 0.4284(2) 0.35064(18) 0.78508(17) 0.0291(6) Uani 1 1 d . . . . .
C45 C 0.3454(3) 0.2704(3) 0.7947(2) 0.0216(8) Uani 1 1 d . . . . .
C46 C 0.3449(3) 0.1630(3) 0.7583(2) 0.0196(8) Uani 1 1 d . . . . .
C47 C 0.4485(3) 0.1526(3) 0.7211(2) 0.0215(8) Uani 1 1 d . . . . .
H47 H 0.516947 0.214528 0.718099 0.026 Uiso 1 1 calc R U . . .
C48 C 0.2430(3) 0.0700(3) 0.7596(2) 0.0207(8) Uani 1 1 d . . . . .
H48 H 0.171433 0.075353 0.784234 0.025 Uiso 1 1 calc R U . . .
C49 C 0.4531(3) 0.0548(3) 0.6887(2) 0.0236(8) Uani 1 1 d . . . . .
H49 H 0.525383 0.050055 0.664767 0.028 Uiso 1 1 calc R U . . .
C50 C 0.2458(3) -0.0294(3) 0.7255(2) 0.0233(8) Uani 1 1 d . . . . .
H50 H 0.175348 -0.091710 0.725607 0.028 Uiso 1 1 calc R U . . .
C51 C 0.3522(3) -0.0388(3) 0.6905(2) 0.0206(8) Uani 1 1 d . . . . .
N52 N 0.3560(3) -0.1374(2) 0.6564(2) 0.0282(7) Uani 1 1 d . . . . .
H52A H 0.429(4) -0.140(3) 0.640(2) 0.034 Uiso 1 1 d . U . . .
H52B H 0.296(4) -0.192(3) 0.671(3) 0.034 Uiso 1 1 d . U . . .
O53 O -0.0592(3) 0.4655(2) 0.33729(17) 0.0286(6) Uani 1 1 d . . . . .
H53 H -0.135(4) 0.454(3) 0.360(3) 0.043 Uiso 1 1 d . U . . .
O54 O -0.1367(2) 0.28697(19) 0.28414(18) 0.0305(6) Uani 1 1 d . . . . .
C55 C -0.0510(3) 0.3756(3) 0.2946(2) 0.0194(8) Uani 1 1 d . . . . .
C56 C 0.0676(3) 0.3890(3) 0.2594(2) 0.0197(7) Uani 1 1 d . . . . .
C57 C 0.0930(3) 0.2988(3) 0.2225(2) 0.0214(8) Uani 1 1 d . . . . .
H57 H 0.031730 0.229818 0.218430 0.026 Uiso 1 1 calc R U . . .
C58 C 0.1586(3) 0.4894(3) 0.2637(2) 0.0208(8) Uani 1 1 d . . . . .
H58 H 0.143044 0.551226 0.289094 0.025 Uiso 1 1 calc R U . . .
C59 C 0.2059(3) 0.3091(3) 0.1921(2) 0.0199(8) Uani 1 1 d . . . . .
H59 H 0.222090 0.247218 0.168513 0.024 Uiso 1 1 calc R U . . .
C60 C 0.2703(3) 0.5004(3) 0.2316(2) 0.0209(8) Uani 1 1 d . . . . .
H60 H 0.329808 0.569143 0.233710 0.025 Uiso 1 1 calc R U . . .
C61 C 0.2971(3) 0.4094(3) 0.1954(2) 0.0212(8) Uani 1 1 d . . . . .
N62 N 0.4073(3) 0.4179(3) 0.1647(2) 0.0259(7) Uani 1 1 d . . . . .
H62A H 0.425(3) 0.357(3) 0.148(2) 0.031 Uiso 1 1 d . U . . .
H62B H 0.470(3) 0.485(3) 0.176(2) 0.031 Uiso 1 1 d . U . . .
O63 O 0.0310(3) 0.0425(3) 0.1099(3) 0.0675(11) Uani 1 1 d . U . . .
O64 O 0.3079(3) 0.7867(3) 0.3833(3) 0.0914(14) Uani 1 1 d . U . . .
H63 H 0.045(4) -0.003(4) 0.122(3) 0.056(14) Uiso 1 1 d . . . . .
H64 H -0.181(10) 0.240(8) 0.614(7) 0.27(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
N01 C03 1.327(5) . ?
N01 C02 1.342(4) . ?
C02 C04 1.370(5) . ?
C02 H02 0.9500 . ?
C03 C05 1.376(5) . ?
C03 H03 0.9500 . ?
C04 C06 1.395(5) . ?
C04 H04 0.9500 . ?
C05 C06 1.377(5) . ?
C05 H05 0.9500 . ?
C06 C07 1.472(5) . ?
C07 C08 1.320(5) . ?
C07 H07 0.9500 . ?
C08 C09 1.476(5) . ?
C08 H08 0.9500 . ?
C09 C10 1.374(5) . ?
C09 C11 1.388(5) . ?
C10 C12 1.379(5) . ?
C10 H10 0.9500 . ?
C11 C13 1.385(5) . ?
C11 H11 0.9500 . ?
C12 N14 1.334(5) . ?
C12 H12 0.9500 . ?
C13 N14 1.337(4) . ?
C13 H13 0.9500 . ?
N14 H64 1.41(11) . ?
N15 C17 1.335(4) . ?
N15 C16 1.339(4) . ?
C16 C18 1.380(5) . ?
C16 H16 0.9500 . ?
C17 C19 1.376(5) . ?
C17 H17 0.9500 . ?
C18 C20 1.402(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.463(4) . ?
C21 C22 1.328(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.465(5) . ?
C22 H22 0.9500 . ?
C23 C25 1.393(5) . ?
C23 C24 1.393(5) . ?
C24 C26 1.380(5) . ?
C24 H24 0.9500 . ?
C25 C27 1.385(5) . ?
C25 H25 0.9500 . ?
C26 N28 1.343(5) . ?
C26 H26 0.9500 . ?
C27 N28 1.330(4) . ?
C27 H27 0.9500 . ?
N29 C31 1.334(5) . ?
N29 C30 1.340(4) . ?
C30 C32 1.381(5) . ?
C30 H30 0.9500 . ?
C31 C33 1.383(5) . ?
C31 H31 0.9500 . ?
C32 C34 1.385(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.471(5) . ?
C35 C35 1.326(6) 2_556 ?
C35 H35 0.9500 . ?
N36 C37 1.331(5) . ?
N36 C38 1.344(5) . ?
C37 C39 1.378(5) . ?
C37 H37 0.9500 . ?
C38 C40 1.383(5) . ?
C38 H38 0.9500 . ?
C39 C41 1.402(5) . ?
C39 H39 0.9500 . ?
C40 C41 1.387(5) . ?
C40 H40 0.9500 . ?
C41 C42 1.457(4) . ?
C42 C42 1.328(6) 2_565 ?
C42 H42 0.9500 . ?
O43 C45 1.319(4) . ?
O43 H43 0.98(4) . ?
O44 C45 1.235(4) . ?
C45 C46 1.477(4) . ?
C46 C47 1.397(5) . ?
C46 C48 1.405(5) . ?
C47 C49 1.370(5) . ?
C47 H47 0.9500 . ?
C48 C50 1.384(4) . ?
C48 H48 0.9500 . ?
C49 C51 1.407(5) . ?
C49 H49 0.9500 . ?
C50 C51 1.408(5) . ?
C50 H50 0.9500 . ?
C51 N52 1.379(4) . ?
N52 H52A 0.91(4) . ?
N52 H52B 0.92(4) . ?
O53 C55 1.316(4) . ?
O53 H53 0.94(4) . ?
O54 C55 1.233(4) . ?
C55 C56 1.467(5) . ?
C56 C58 1.398(5) . ?
C56 C57 1.404(5) . ?
C57 C59 1.381(5) . ?
C57 H57 0.9500 . ?
C58 C60 1.378(4) . ?
C58 H58 0.9500 . ?
C59 C61 1.401(4) . ?
C59 H59 0.9500 . ?
C60 C61 1.421(4) . ?
C60 H60 0.9500 . ?
C61 N62 1.357(4) . ?
N62 H62A 0.94(3) . ?
N62 H62B 0.91(4) . ?
O63 H63 0.78(5) . ?

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
C03 N01 C02 117.2(3) . . ?
N01 C02 C04 123.3(3) . . ?
N01 C02 H02 118.3 . . ?
C04 C02 H02 118.3 . . ?
N01 C03 C05 123.1(4) . . ?
N01 C03 H03 118.4 . . ?
C05 C03 H03 118.4 . . ?
C02 C04 C06 119.3(3) . . ?
C02 C04 H04 120.3 . . ?
C06 C04 H04 120.3 . . ?
C03 C05 C06 120.1(4) . . ?
C03 C05 H05 120.0 . . ?
C06 C05 H05 120.0 . . ?
C05 C06 C04 117.0(3) . . ?
C05 C06 C07 118.7(3) . . ?
C04 C06 C07 124.3(3) . . ?
C08 C07 C06 125.5(3) . . ?
C08 C07 H07 117.3 . . ?
C06 C07 H07 117.3 . . ?
C07 C08 C09 125.0(3) . . ?
C07 C08 H08 117.5 . . ?
C09 C08 H08 117.5 . . ?
C10 C09 C11 117.3(3) . . ?
C10 C09 C08 118.6(3) . . ?
C11 C09 C08 124.1(3) . . ?
C09 C10 C12 119.1(4) . . ?
C09 C10 H10 120.4 . . ?
C12 C10 H10 120.4 . . ?
C13 C11 C09 119.9(3) . . ?
C13 C11 H11 120.0 . . ?
C09 C11 H11 120.0 . . ?
N14 C12 C10 124.4(4) . . ?
N14 C12 H12 117.8 . . ?
C10 C12 H12 117.8 . . ?
N14 C13 C11 122.8(4) . . ?
N14 C13 H13 118.6 . . ?
C11 C13 H13 118.6 . . ?
C12 N14 C13 116.5(3) . . ?
C12 N14 H64 104(4) . . ?
C13 N14 H64 138(4) . . ?
C17 N15 C16 117.1(3) . . ?
N15 C16 C18 123.3(3) . . ?
N15 C16 H16 118.4 . . ?
C18 C16 H16 118.4 . . ?
N15 C17 C19 123.2(3) . . ?
N15 C17 H17 118.4 . . ?
C19 C17 H17 118.4 . . ?
C16 C18 C20 119.8(3) . . ?
C16 C18 H18 120.1 . . ?
C20 C18 H18 120.1 . . ?
C17 C19 C20 120.5(3) . . ?
C17 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C18 116.0(3) . . ?
C19 C20 C21 120.3(3) . . ?
C18 C20 C21 123.7(3) . . ?
C22 C21 C20 125.6(3) . . ?
C22 C21 H21 117.2 . . ?
C20 C21 H21 117.2 . . ?
C21 C22 C23 126.0(3) . . ?
C21 C22 H22 117.0 . . ?
C23 C22 H22 117.0 . . ?
C25 C23 C24 115.9(3) . . ?
C25 C23 C22 124.5(3) . . ?
C24 C23 C22 119.5(3) . . ?
C26 C24 C23 119.9(4) . . ?
C26 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C27 C25 C23 120.0(3) . . ?
C27 C25 H25 120.0 . . ?
C23 C25 H25 120.0 . . ?
N28 C26 C24 124.3(3) . . ?
N28 C26 H26 117.9 . . ?
C24 C26 H26 117.9 . . ?
N28 C27 C25 124.3(4) . . ?
N28 C27 H27 117.8 . . ?
C25 C27 H27 117.8 . . ?
C27 N28 C26 115.6(3) . . ?
C31 N29 C30 115.8(3) . . ?
N29 C30 C32 123.8(3) . . ?
N29 C30 H30 118.1 . . ?
C32 C30 H30 118.1 . . ?
N29 C31 C33 124.6(3) . . ?
N29 C31 H31 117.7 . . ?
C33 C31 H31 117.7 . . ?
C30 C32 C34 119.8(3) . . ?
C30 C32 H32 120.1 . . ?
C34 C32 H32 120.1 . . ?
C31 C33 C34 119.0(3) . . ?
C31 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
C32 C34 C33 117.0(3) . . ?
C32 C34 C35 120.0(3) . . ?
C33 C34 C35 123.0(3) . . ?
C35 C35 C34 126.0(4) 2_556 . ?
C35 C35 H35 117.0 2_556 . ?
C34 C35 H35 117.0 . . ?
C37 N36 C38 115.9(3) . . ?
N36 C37 C39 125.1(3) . . ?
N36 C37 H37 117.4 . . ?
C39 C37 H37 117.4 . . ?
N36 C38 C40 123.1(4) . . ?
N36 C38 H38 118.5 . . ?
C40 C38 H38 118.5 . . ?
C37 C39 C41 118.9(3) . . ?
C37 C39 H39 120.5 . . ?
C41 C39 H39 120.5 . . ?
C38 C40 C41 120.6(3) . . ?
C38 C40 H40 119.7 . . ?
C41 C40 H40 119.7 . . ?
C40 C41 C39 116.3(3) . . ?
C40 C41 C42 120.6(3) . . ?
C39 C41 C42 123.2(3) . . ?
C42 C42 C41 126.0(4) 2_565 . ?
C42 C42 H42 117.0 2_565 . ?
C41 C42 H42 117.0 . . ?
C45 O43 H43 108(2) . . ?
O44 C45 O43 122.7(3) . . ?
O44 C45 C46 122.0(3) . . ?
O43 C45 C46 115.3(3) . . ?
C47 C46 C48 118.4(3) . . ?
C47 C46 C45 119.5(3) . . ?
C48 C46 C45 122.1(3) . . ?
C49 C47 C46 121.3(3) . . ?
C49 C47 H47 119.4 . . ?
C46 C47 H47 119.4 . . ?
C50 C48 C46 120.7(3) . . ?
C50 C48 H48 119.6 . . ?
C46 C48 H48 119.6 . . ?
C47 C49 C51 120.8(3) . . ?
C47 C49 H49 119.6 . . ?
C51 C49 H49 119.6 . . ?
C48 C50 C51 120.5(3) . . ?
C48 C50 H50 119.7 . . ?
C51 C50 H50 119.7 . . ?
N52 C51 C49 120.7(3) . . ?
N52 C51 C50 121.0(3) . . ?
C49 C51 C50 118.3(3) . . ?
C51 N52 H52A 119(2) . . ?
C51 N52 H52B 115(2) . . ?
H52A N52 H52B 123(3) . . ?
C55 O53 H53 112(2) . . ?
O54 C55 O53 122.6(3) . . ?
O54 C55 C56 122.6(3) . . ?
O53 C55 C56 114.7(3) . . ?
C58 C56 C57 118.5(3) . . ?
C58 C56 C55 122.1(3) . . ?
C57 C56 C55 119.3(3) . . ?
C59 C57 C56 120.8(3) . . ?
C59 C57 H57 119.6 . . ?
C56 C57 H57 119.6 . . ?
C60 C58 C56 121.2(3) . . ?
C60 C58 H58 119.4 . . ?
C56 C58 H58 119.4 . . ?
C57 C59 C61 121.0(3) . . ?
C57 C59 H59 119.5 . . ?
C61 C59 H59 119.5 . . ?
C58 C60 C61 120.4(3) . . ?
C58 C60 H60 119.8 . . ?
C61 C60 H60 119.8 . . ?
N62 C61 C59 120.2(3) . . ?
N62 C61 C60 121.7(3) . . ?
C59 C61 C60 118.1(3) . . ?
C61 N62 H62A 119(2) . . ?
C61 N62 H62B 118(2) . . ?
H62A N62 H62B 121(3) . . ?

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
C03 N01 C02 C04 -0.1(5) . . . . ?
C02 N01 C03 C05 0.8(6) . . . . ?
N01 C02 C04 C06 0.3(6) . . . . ?
N01 C03 C05 C06 -1.8(6) . . . . ?
C03 C05 C06 C04 1.9(5) . . . . ?
C03 C05 C06 C07 -178.8(3) . . . . ?
C02 C04 C06 C05 -1.2(5) . . . . ?
C02 C04 C06 C07 179.5(3) . . . . ?
C05 C06 C07 C08 179.7(4) . . . . ?
C04 C06 C07 C08 -1.0(6) . . . . ?
C06 C07 C08 C09 179.7(3) . . . . ?
C07 C08 C09 C10 -173.9(4) . . . . ?
C07 C08 C09 C11 6.7(6) . . . . ?
C11 C09 C10 C12 -0.9(5) . . . . ?
C08 C09 C10 C12 179.7(3) . . . . ?
C10 C09 C11 C13 1.7(5) . . . . ?
C08 C09 C11 C13 -179.0(3) . . . . ?
C09 C10 C12 N14 0.3(6) . . . . ?
C09 C11 C13 N14 -1.8(6) . . . . ?
C10 C12 N14 C13 -0.4(6) . . . . ?
C11 C13 N14 C12 1.1(6) . . . . ?
C17 N15 C16 C18 1.9(5) . . . . ?
C16 N15 C17 C19 -0.7(5) . . . . ?
N15 C16 C18 C20 -2.0(6) . . . . ?
N15 C17 C19 C20 -0.4(6) . . . . ?
C17 C19 C20 C18 0.4(5) . . . . ?
C17 C19 C20 C21 -179.6(3) . . . . ?
C16 C18 C20 C19 0.7(5) . . . . ?
C16 C18 C20 C21 -179.3(3) . . . . ?
C19 C20 C21 C22 -175.2(4) . . . . ?
C18 C20 C21 C22 4.9(6) . . . . ?
C20 C21 C22 C23 -177.9(3) . . . . ?
C21 C22 C23 C25 0.6(6) . . . . ?
C21 C22 C23 C24 178.7(4) . . . . ?
C25 C23 C24 C26 -0.2(5) . . . . ?
C22 C23 C24 C26 -178.4(3) . . . . ?
C24 C23 C25 C27 0.0(5) . . . . ?
C22 C23 C25 C27 178.0(3) . . . . ?
C23 C24 C26 N28 0.2(6) . . . . ?
C23 C25 C27 N28 0.3(6) . . . . ?
C25 C27 N28 C26 -0.3(6) . . . . ?
C24 C26 N28 C27 0.0(6) . . . . ?
C31 N29 C30 C32 -1.3(5) . . . . ?
C30 N29 C31 C33 1.5(5) . . . . ?
N29 C30 C32 C34 0.6(5) . . . . ?
N29 C31 C33 C34 -1.0(6) . . . . ?
C30 C32 C34 C33 -0.1(5) . . . . ?
C30 C32 C34 C35 -179.8(3) . . . . ?
C31 C33 C34 C32 0.2(5) . . . . ?
C31 C33 C34 C35 179.9(3) . . . . ?
C32 C34 C35 C35 -174.9(4) . . . 2_556 ?
C33 C34 C35 C35 5.4(6) . . . 2_556 ?
C38 N36 C37 C39 1.0(6) . . . . ?
C37 N36 C38 C40 -0.8(6) . . . . ?
N36 C37 C39 C41 -0.3(6) . . . . ?
N36 C38 C40 C41 0.0(6) . . . . ?
C38 C40 C41 C39 0.7(5) . . . . ?
C38 C40 C41 C42 180.0(3) . . . . ?
C37 C39 C41 C40 -0.5(5) . . . . ?
C37 C39 C41 C42 -179.8(3) . . . . ?
C40 C41 C42 C42 -175.6(4) . . . 2_565 ?
C39 C41 C42 C42 3.6(6) . . . 2_565 ?
O44 C45 C46 C47 7.2(5) . . . . ?
O43 C45 C46 C47 -172.7(3) . . . . ?
O44 C45 C46 C48 -172.6(3) . . . . ?
O43 C45 C46 C48 7.5(5) . . . . ?
C48 C46 C47 C49 -1.8(5) . . . . ?
C45 C46 C47 C49 178.4(3) . . . . ?
C47 C46 C48 C50 0.5(5) . . . . ?
C45 C46 C48 C50 -179.7(3) . . . . ?
C46 C47 C49 C51 1.2(5) . . . . ?
C46 C48 C50 C51 1.3(5) . . . . ?
C47 C49 C51 N52 178.9(3) . . . . ?
C47 C49 C51 C50 0.7(5) . . . . ?
C48 C50 C51 N52 179.9(3) . . . . ?
C48 C50 C51 C49 -1.9(5) . . . . ?
O54 C55 C56 C58 173.7(3) . . . . ?
O53 C55 C56 C58 -5.7(5) . . . . ?
O54 C55 C56 C57 -8.1(5) . . . . ?
O53 C55 C56 C57 172.6(3) . . . . ?
C58 C56 C57 C59 0.8(5) . . . . ?
C55 C56 C57 C59 -177.5(3) . . . . ?
C57 C56 C58 C60 0.7(5) . . . . ?
C55 C56 C58 C60 178.9(3) . . . . ?
C56 C57 C59 C61 -1.3(5) . . . . ?
C56 C58 C60 C61 -1.6(5) . . . . ?
C57 C59 C61 N62 -179.7(3) . . . . ?
C57 C59 C61 C60 0.4(5) . . . . ?
C58 C60 C61 N62 -178.9(3) . . . . ?
C58 C60 C61 C59 1.0(5) . . . . ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_p1812d
_database_code_depnum_ccdc_archive 'CCDC 1940959'
loop_
_audit_author_name
_audit_author_address
'P. Tinnemans' 'Radboud University Nijmegen'
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2, C6 H6 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29

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

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

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

_cell_length_a                   7.5267(6)
_cell_length_b                   9.8209(7)
_cell_length_c                   18.1895(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.747(3)
_cell_angle_gamma                90
_cell_volume                     1344.43(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.8

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.562
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6799
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker D8 Quest Apex3'
_diffrn_radiation_detector       Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            50251
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.357
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6665
_reflns_number_gt                5315
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

_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       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        SAINT,SADABS-2014/5
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON, Shelxle'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2138 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6665
_refine_ls_number_parameters     373
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_restrained_S_all      0.883
_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
O01 O 0.2589(3) -0.0063(2) 0.87569(13) 0.0365(5) Uani 1 1 d . . . . .
H01 H 0.317(5) 0.069(4) 0.856(2) 0.055 Uiso 1 1 d . U . . .
O02 O 0.5561(2) 1.1157(2) 0.57012(11) 0.0302(4) Uani 1 1 d . . . . .
H02 H 0.545(5) 1.028(4) 0.5920(19) 0.045 Uiso 1 1 d . U . . .
O03 O 0.8674(3) -0.1183(2) 0.92968(11) 0.0304(5) Uani 1 1 d . . . . .
H03 H 0.877(5) -0.034(4) 0.908(2) 0.046 Uiso 1 1 d . U . . .
O04 O 1.1693(3) 1.0128(2) 0.62253(12) 0.0315(5) Uani 1 1 d . . . . .
H04 H 1.120(5) 0.935(4) 0.642(2) 0.047 Uiso 1 1 d . U . . .
N05 N 0.5361(3) 0.8571(2) 0.63688(13) 0.0277(5) Uani 1 1 d . . . . .
N06 N 0.4035(3) 0.2183(2) 0.80822(14) 0.0313(5) Uani 1 1 d . . . . .
N07 N 0.9050(3) 0.1433(2) 0.86469(12) 0.0287(5) Uani 1 1 d . . . . .
C08 C 0.5088(3) 0.6016(3) 0.70474(13) 0.0190(5) Uani 1 1 d . . . . .
N09 N 1.0470(3) 0.7805(2) 0.68919(15) 0.0327(6) Uani 1 1 d . . . . .
C10 C 0.8611(3) 1.0603(3) 0.59774(13) 0.0211(5) Uani 1 1 d . . . . .
H10 H 0.826678 0.976784 0.619711 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4818(3) 0.4669(2) 0.74036(14) 0.0202(5) Uani 1 1 d . . . . .
C12 C 0.5647(3) -0.0584(3) 0.90145(13) 0.0219(5) Uani 1 1 d . . . . .
H12 H 0.601588 0.025696 0.880879 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8997(3) 0.2840(3) 0.75631(14) 0.0237(5) Uani 1 1 d . . . . .
H13 H 0.875331 0.291301 0.705087 0.028 Uiso 1 1 calc R U . . .
C14 C 0.9956(3) 0.3770(3) 0.87088(14) 0.0260(6) Uani 1 1 d . . . . .
H14 H 1.038367 0.450253 0.900248 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6905(3) -0.1485(3) 0.92961(13) 0.0224(5) Uani 1 1 d . . . . .
C16 C 0.7318(3) 1.1477(3) 0.56871(14) 0.0222(5) Uani 1 1 d . . . . .
C17 C 0.4244(4) 0.3543(3) 0.69963(15) 0.0272(6) Uani 1 1 d . . . . .
H17 H 0.411892 0.360213 0.647693 0.033 Uiso 1 1 calc R U . . .
C18 C 0.7815(4) 1.2716(3) 0.53726(13) 0.0248(5) Uani 1 1 d . . . . .
H18 H 0.694200 1.332586 0.518348 0.030 Uiso 1 1 calc R U . . .
C19 C 0.9907(3) 0.5296(3) 0.75934(13) 0.0208(5) Uani 1 1 d . . . . .
C20 C 1.0403(3) 1.0951(3) 0.59464(13) 0.0215(5) Uani 1 1 d . . . . .
C21 C 0.3294(4) -0.2146(3) 0.93340(14) 0.0268(6) Uani 1 1 d . . . . .
H21 H 0.206800 -0.236991 0.935361 0.032 Uiso 1 1 calc R U . . .
C22 C 0.9612(4) 1.3039(3) 0.53421(13) 0.0262(6) Uani 1 1 d . . . . .
H22 H 0.995810 1.387309 0.512179 0.031 Uiso 1 1 calc R U . . .
C23 C 0.5641(4) 0.7421(3) 0.59995(15) 0.0320(6) Uani 1 1 d . . . . .
H23 H 0.593622 0.748718 0.549458 0.038 Uiso 1 1 calc R U . . .
C24 C 0.8737(4) 0.1617(3) 0.79280(15) 0.0273(6) Uani 1 1 d . . . . .
H24 H 0.831070 0.086344 0.764997 0.033 Uiso 1 1 calc R U . . .
C25 C 0.6373(4) -0.2733(3) 0.95860(14) 0.0268(6) Uani 1 1 d . . . . .
H25 H 0.722838 -0.336301 0.976851 0.032 Uiso 1 1 calc R U . . .
C26 C 0.5528(4) 0.6137(3) 0.63077(14) 0.0292(6) Uani 1 1 d . . . . .
H26 H 0.574709 0.534847 0.601989 0.035 Uiso 1 1 calc R U . . .
C27 C 1.0914(3) 1.2178(3) 0.56237(13) 0.0245(5) Uani 1 1 d . . . . .
H27 H 1.213350 1.242004 0.559755 0.029 Uiso 1 1 calc R U . . .
C28 C 0.4571(4) -0.3040(3) 0.96038(14) 0.0286(6) Uani 1 1 d . . . . .
H28 H 0.420474 -0.388525 0.980609 0.034 Uiso 1 1 calc R U . . .
C29 C 1.0283(4) 0.5367(3) 0.68448(14) 0.0267(6) Uani 1 1 d . . . . .
H29 H 1.035961 0.455909 0.656007 0.032 Uiso 1 1 calc R U . . .
C30 C 0.3861(4) 0.2341(3) 0.73561(16) 0.0315(6) Uani 1 1 d . . . . .
H30 H 0.345253 0.158859 0.707221 0.038 Uiso 1 1 calc R U . . .
C31 C 0.5049(4) 0.4495(3) 0.81556(14) 0.0245(5) Uani 1 1 d . . . . .
H31 H 0.547985 0.522224 0.845261 0.029 Uiso 1 1 calc R U . . .
C32 C 0.9622(3) 0.3962(3) 0.79597(14) 0.0204(5) Uani 1 1 d . . . . .
C33 C 0.9660(3) 0.2510(3) 0.90213(15) 0.0292(6) Uani 1 1 d . . . . .
H33 H 0.990508 0.240302 0.953176 0.035 Uiso 1 1 calc R U . . .
C34 C 0.4838(3) 0.7211(3) 0.74366(14) 0.0249(5) Uani 1 1 d . . . . .
H34 H 0.457591 0.717903 0.794579 0.030 Uiso 1 1 calc R U . . .
C35 C 1.0544(4) 0.6627(3) 0.65208(17) 0.0319(6) Uani 1 1 d . . . . .
H35 H 1.078768 0.665797 0.600987 0.038 Uiso 1 1 calc R U . . .
C36 C 0.9810(4) 0.6518(3) 0.79742(16) 0.0294(6) Uani 1 1 d . . . . .
H36 H 0.953759 0.652462 0.848275 0.035 Uiso 1 1 calc R U . . .
C37 C 0.4973(4) 0.8455(3) 0.70806(16) 0.0289(6) Uani 1 1 d . . . . .
H37 H 0.478093 0.926254 0.735581 0.035 Uiso 1 1 calc R U . . .
C38 C 0.4646(4) 0.3251(3) 0.84681(16) 0.0302(6) Uani 1 1 d . . . . .
H38 H 0.481123 0.314816 0.898380 0.036 Uiso 1 1 calc R U . . .
C39 C 0.3847(3) -0.0909(3) 0.90323(14) 0.0241(5) Uani 1 1 d . . . . .
C40 C 1.0113(4) 0.7727(3) 0.76050(18) 0.0352(7) Uani 1 1 d . . . . .
H40 H 1.006185 0.855092 0.787752 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O01 C39 1.351(3) . ?
O01 H01 0.93(4) . ?
O02 C16 1.360(3) . ?
O02 H02 0.95(4) . ?
O03 C15 1.364(3) . ?
O03 H03 0.92(4) . ?
O04 C20 1.357(3) . ?
O04 H04 0.93(4) . ?
N05 C23 1.332(4) . ?
N05 C37 1.336(4) . ?
N06 C30 1.335(4) . ?
N06 C38 1.340(4) . ?
N07 C24 1.338(4) . ?
N07 C33 1.336(4) . ?
C08 C34 1.385(4) . ?
C08 C26 1.395(3) . ?
C08 C11 1.488(3) . ?
N09 C40 1.331(4) . ?
N09 C35 1.341(4) . ?
C10 C20 1.394(3) . ?
C10 C16 1.395(4) . ?
C10 H10 0.9500 . ?
C11 C31 1.387(4) . ?
C11 C17 1.397(4) . ?
C12 C39 1.393(4) . ?
C12 C15 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C24 1.387(4) . ?
C13 C32 1.395(4) . ?
C13 H13 0.9500 . ?
C14 C33 1.381(4) . ?
C14 C32 1.395(4) . ?
C14 H14 0.9500 . ?
C15 C25 1.395(4) . ?
C16 C18 1.398(4) . ?
C17 C30 1.382(4) . ?
C17 H17 0.9500 . ?
C18 C22 1.391(4) . ?
C18 H18 0.9500 . ?
C19 C36 1.388(4) . ?
C19 C29 1.396(4) . ?
C19 C32 1.487(4) . ?
C20 C27 1.397(4) . ?
C21 C28 1.387(4) . ?
C21 C39 1.399(4) . ?
C21 H21 0.9500 . ?
C22 C27 1.387(4) . ?
C22 H22 0.9500 . ?
C23 C26 1.384(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C28 1.390(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C35 1.385(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C38 1.383(4) . ?
C31 H31 0.9500 . ?
C33 H33 0.9500 . ?
C34 C37 1.387(4) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C40 1.384(4) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C40 H40 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C39 O01 H01 108(3) . . ?
C16 O02 H02 108(2) . . ?
C15 O03 H03 106(2) . . ?
C20 O04 H04 110(2) . . ?
C23 N05 C37 117.1(2) . . ?
C30 N06 C38 117.2(2) . . ?
C24 N07 C33 116.5(2) . . ?
C34 C08 C26 117.2(2) . . ?
C34 C08 C11 120.7(2) . . ?
C26 C08 C11 122.1(2) . . ?
C40 N09 C35 116.8(3) . . ?
C20 C10 C16 120.3(2) . . ?
C20 C10 H10 119.9 . . ?
C16 C10 H10 119.9 . . ?
C31 C11 C17 117.3(2) . . ?
C31 C11 C08 121.5(2) . . ?
C17 C11 C08 121.1(2) . . ?
C39 C12 C15 120.3(2) . . ?
C39 C12 H12 119.9 . . ?
C15 C12 H12 119.9 . . ?
C24 C13 C32 119.0(2) . . ?
C24 C13 H13 120.5 . . ?
C32 C13 H13 120.5 . . ?
C33 C14 C32 119.7(3) . . ?
C33 C14 H14 120.2 . . ?
C32 C14 H14 120.2 . . ?
O03 C15 C25 118.4(2) . . ?
O03 C15 C12 121.5(2) . . ?
C25 C15 C12 120.1(2) . . ?
O02 C16 C18 118.3(2) . . ?
O02 C16 C10 121.6(2) . . ?
C18 C16 C10 120.1(2) . . ?
C30 C17 C11 119.4(2) . . ?
C30 C17 H17 120.3 . . ?
C11 C17 H17 120.3 . . ?
C22 C18 C16 118.7(2) . . ?
C22 C18 H18 120.7 . . ?
C16 C18 H18 120.7 . . ?
C36 C19 C29 117.2(2) . . ?
C36 C19 C32 122.0(2) . . ?
C29 C19 C32 120.9(2) . . ?
O04 C20 C27 118.2(2) . . ?
O04 C20 C10 121.8(2) . . ?
C27 C20 C10 120.0(2) . . ?
C28 C21 C39 118.7(2) . . ?
C28 C21 H21 120.6 . . ?
C39 C21 H21 120.6 . . ?
C27 C22 C18 121.9(3) . . ?
C27 C22 H22 119.0 . . ?
C18 C22 H22 119.0 . . ?
N05 C23 C26 123.9(2) . . ?
N05 C23 H23 118.1 . . ?
C26 C23 H23 118.1 . . ?
N07 C24 C13 124.1(3) . . ?
N07 C24 H24 118.0 . . ?
C13 C24 H24 118.0 . . ?
C15 C25 C28 119.0(2) . . ?
C15 C25 H25 120.5 . . ?
C28 C25 H25 120.5 . . ?
C23 C26 C08 119.0(3) . . ?
C23 C26 H26 120.5 . . ?
C08 C26 H26 120.5 . . ?
C22 C27 C20 119.0(2) . . ?
C22 C27 H27 120.5 . . ?
C20 C27 H27 120.5 . . ?
C21 C28 C25 121.7(3) . . ?
C21 C28 H28 119.1 . . ?
C25 C28 H28 119.1 . . ?
C35 C29 C19 119.4(3) . . ?
C35 C29 H29 120.3 . . ?
C19 C29 H29 120.3 . . ?
N06 C30 C17 123.3(3) . . ?
N06 C30 H30 118.3 . . ?
C17 C30 H30 118.3 . . ?
C38 C31 C11 119.3(2) . . ?
C38 C31 H31 120.4 . . ?
C11 C31 H31 120.4 . . ?
C14 C32 C13 117.0(2) . . ?
C14 C32 C19 122.1(2) . . ?
C13 C32 C19 120.9(2) . . ?
N07 C33 C14 123.8(2) . . ?
N07 C33 H33 118.1 . . ?
C14 C33 H33 118.1 . . ?
C08 C34 C37 119.8(2) . . ?
C08 C34 H34 120.1 . . ?
C37 C34 H34 120.1 . . ?
N09 C35 C29 123.3(3) . . ?
N09 C35 H35 118.3 . . ?
C29 C35 H35 118.3 . . ?
C19 C36 C40 119.3(3) . . ?
C19 C36 H36 120.4 . . ?
C40 C36 H36 120.4 . . ?
N05 C37 C34 123.1(3) . . ?
N05 C37 H37 118.5 . . ?
C34 C37 H37 118.5 . . ?
N06 C38 C31 123.5(3) . . ?
N06 C38 H38 118.3 . . ?
C31 C38 H38 118.3 . . ?
O01 C39 C12 121.8(2) . . ?
O01 C39 C21 118.0(2) . . ?
C12 C39 C21 120.2(2) . . ?
N09 C40 C36 124.0(3) . . ?
N09 C40 H40 118.0 . . ?
C36 C40 H40 118.0 . . ?

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
C34 C08 C11 C31 -27.4(3) . . . . ?
C26 C08 C11 C31 155.2(2) . . . . ?
C34 C08 C11 C17 149.7(3) . . . . ?
C26 C08 C11 C17 -27.7(4) . . . . ?
C39 C12 C15 O03 -178.9(2) . . . . ?
C39 C12 C15 C25 1.2(4) . . . . ?
C20 C10 C16 O02 179.2(2) . . . . ?
C20 C10 C16 C18 -0.9(4) . . . . ?
C31 C11 C17 C30 2.8(4) . . . . ?
C08 C11 C17 C30 -174.4(2) . . . . ?
O02 C16 C18 C22 -178.7(2) . . . . ?
C10 C16 C18 C22 1.4(4) . . . . ?
C16 C10 C20 O04 179.8(2) . . . . ?
C16 C10 C20 C27 0.0(4) . . . . ?
C16 C18 C22 C27 -1.0(4) . . . . ?
C37 N05 C23 C26 0.9(4) . . . . ?
C33 N07 C24 C13 -0.4(4) . . . . ?
C32 C13 C24 N07 0.0(4) . . . . ?
O03 C15 C25 C28 178.6(2) . . . . ?
C12 C15 C25 C28 -1.5(4) . . . . ?
N05 C23 C26 C08 0.3(4) . . . . ?
C34 C08 C26 C23 -1.8(4) . . . . ?
C11 C08 C26 C23 175.7(2) . . . . ?
C18 C22 C27 C20 0.1(4) . . . . ?
O04 C20 C27 C22 -179.4(2) . . . . ?
C10 C20 C27 C22 0.4(4) . . . . ?
C39 C21 C28 C25 0.5(4) . . . . ?
C15 C25 C28 C21 0.7(4) . . . . ?
C36 C19 C29 C35 0.2(4) . . . . ?
C32 C19 C29 C35 -179.9(2) . . . . ?
C38 N06 C30 C17 -1.3(4) . . . . ?
C11 C17 C30 N06 -1.1(4) . . . . ?
C17 C11 C31 C38 -2.3(4) . . . . ?
C08 C11 C31 C38 174.9(2) . . . . ?
C33 C14 C32 C13 -0.1(4) . . . . ?
C33 C14 C32 C19 179.7(2) . . . . ?
C24 C13 C32 C14 0.3(4) . . . . ?
C24 C13 C32 C19 -179.5(2) . . . . ?
C36 C19 C32 C14 -26.7(4) . . . . ?
C29 C19 C32 C14 153.5(2) . . . . ?
C36 C19 C32 C13 153.1(3) . . . . ?
C29 C19 C32 C13 -26.8(4) . . . . ?
C24 N07 C33 C14 0.7(4) . . . . ?
C32 C14 C33 N07 -0.4(4) . . . . ?
C26 C08 C34 C37 2.1(4) . . . . ?
C11 C08 C34 C37 -175.5(2) . . . . ?
C40 N09 C35 C29 -0.5(4) . . . . ?
C19 C29 C35 N09 0.6(4) . . . . ?
C29 C19 C36 C40 -1.1(4) . . . . ?
C32 C19 C36 C40 179.1(3) . . . . ?
C23 N05 C37 C34 -0.7(4) . . . . ?
C08 C34 C37 N05 -0.9(4) . . . . ?
C30 N06 C38 C31 1.8(4) . . . . ?
C11 C31 C38 N06 0.0(4) . . . . ?
C15 C12 C39 O01 -179.3(2) . . . . ?
C15 C12 C39 C21 0.0(4) . . . . ?
C28 C21 C39 O01 178.5(2) . . . . ?
C28 C21 C39 C12 -0.8(4) . . . . ?
C35 N09 C40 C36 -0.4(4) . . . . ?
C19 C36 C40 N09 1.2(5) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.041

