# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1a_100K
_database_code_depnum_ccdc_archive 'CCDC 1970253'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
;
hexamethylenetetramine hydrogen succinate succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H13 N4, C4 H5 O4, C4 H6 O4'
_chemical_formula_sum            'C14 H24 N4 O8'
_chemical_formula_weight         376.37

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                   9.6037(4)
_cell_length_b                   9.8432(4)
_cell_length_c                   10.2613(4)
_cell_angle_alpha                68.903(1)
_cell_angle_beta                 83.980(1)
_cell_angle_gamma                68.045(1)
_cell_volume                     838.87(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7081
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.36

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.097
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            15036
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.129
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3442
_reflns_number_gt                3044
_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 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0372P)²+0.4606P] 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         3442
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.59398(11) -0.40090(12) 0.29830(10) 0.0200(2) Uani 1 1 d . . . . .
H1 H 0.685(2) -0.450(2) 0.335(2) 0.037(5) Uiso 1 1 d . . . . .
H13 H 0.059(2) 0.160(3) 0.383(2) 0.050(6) Uiso 1 1 d . . . . .
O2 O 0.53260(11) -0.32776(12) 0.48514(11) 0.0235(2) Uani 1 1 d . . . . .
C3 C 0.49648(14) -0.33041(14) 0.37694(13) 0.0129(3) Uani 1 1 d . . . . .
C4 C 0.33904(14) -0.25892(15) 0.31588(14) 0.0145(3) Uani 1 1 d . . . . .
H4A H 0.297239 -0.342225 0.337178 0.017 Uiso 1 1 calc R U . . .
H4B H 0.342139 -0.212897 0.212985 0.017 Uiso 1 1 calc R U . . .
C5 C 0.23525(14) -0.13306(15) 0.37118(13) 0.0128(3) Uani 1 1 d . . . . .
H5A H 0.232873 -0.178963 0.474156 0.015 Uiso 1 1 calc R U . . .
H5B H 0.276790 -0.049477 0.349304 0.015 Uiso 1 1 calc R U . . .
H9 H 0.070(2) -0.265(3) 0.175(2) 0.046(6) Uiso 1 1 d . . . . .
C6 C 0.07559(14) -0.06113(15) 0.31059(13) 0.0124(3) Uani 1 1 d . . . . .
O7 O 0.02554(10) -0.13285(11) 0.26090(11) 0.0194(2) Uani 1 1 d . . . . .
O8 O -0.00608(10) 0.07228(10) 0.31794(10) 0.0158(2) Uani 1 1 d . . . . .
O9 O 0.10497(11) -0.33556(12) 0.13367(11) 0.0220(2) Uani 1 1 d . . . . .
O10 O -0.13861(11) -0.27541(13) 0.09058(13) 0.0300(3) Uani 1 1 d . . . . .
C11 C -0.00765(15) -0.34509(15) 0.07742(14) 0.0160(3) Uani 1 1 d . . . . .
C12 C 0.04776(15) -0.45093(16) -0.00795(15) 0.0180(3) Uani 1 1 d . . . . .
H12A H 0.152852 -0.521176 0.021602 0.022 Uiso 1 1 calc R U . . .
H12B H 0.046879 -0.386592 -0.107711 0.022 Uiso 1 1 calc R U . . .
O13 O 0.10067(10) 0.21081(11) 0.42487(10) 0.0165(2) Uani 1 1 d . . . . .
O14 O -0.12745(10) 0.39558(11) 0.37901(10) 0.0188(2) Uani 1 1 d . . . . .
C15 C 0.00016(14) 0.34376(14) 0.42768(13) 0.0127(3) Uani 1 1 d . . . . .
C16 C 0.05894(14) 0.42402(14) 0.49699(14) 0.0150(3) Uani 1 1 d . . . . .
H16B H 0.145467 0.446009 0.445041 0.018 Uiso 1 1 calc R U . . .
H16A H 0.095311 0.352751 0.593247 0.018 Uiso 1 1 calc R U . . .
N17 N -0.52767(12) 0.33642(13) 0.14723(12) 0.0152(2) Uani 1 1 d . . . . .
C18 C -0.60393(15) 0.24024(16) 0.24904(14) 0.0177(3) Uani 1 1 d . . . . .
H18A H -0.616584 0.264302 0.336259 0.021 Uiso 1 1 calc R U . . .
H18B H -0.705120 0.267187 0.210923 0.021 Uiso 1 1 calc R U . . .
N19 N -0.51929(13) 0.07211(13) 0.28139(12) 0.0170(2) Uani 1 1 d . . . . .
C20 C -0.49951(16) 0.03873(16) 0.14990(14) 0.0179(3) Uani 1 1 d . . . . .
H20A H -0.441560 -0.073961 0.170137 0.022 Uiso 1 1 calc R U . . .
H20B H -0.599233 0.063243 0.110151 0.022 Uiso 1 1 calc R U . . .
N21 N -0.42059(12) 0.13044(12) 0.04649(11) 0.0143(2) Uani 1 1 d . . . . .
C22 C -0.50740(15) 0.29756(15) 0.01856(14) 0.0156(3) Uani 1 1 d . . . . .
H22A H -0.607122 0.325288 -0.023024 0.019 Uiso 1 1 calc R U . . .
H22B H -0.454662 0.360360 -0.050018 0.019 Uiso 1 1 calc R U . . .
N23 N -0.28979(12) 0.12665(13) 0.23834(12) 0.0143(2) Uani 1 1 d . . . . .
H23 H -0.194(2) 0.104(2) 0.2718(19) 0.031(5) Uiso 1 1 d . . . . .
C24 C -0.27373(14) 0.08995(15) 0.10430(14) 0.0154(3) Uani 1 1 d . . . . .
H24A H -0.218639 0.150003 0.035795 0.019 Uiso 1 1 calc R U . . .
H24B H -0.215605 -0.022681 0.124382 0.019 Uiso 1 1 calc R U . . .
C25 C -0.38188(14) 0.29901(15) 0.20570(15) 0.0159(3) Uani 1 1 d . . . . .
H25A H -0.394165 0.324281 0.292270 0.019 Uiso 1 1 calc R U . . .
H25B H -0.328879 0.362443 0.138297 0.019 Uiso 1 1 calc R U . . .
C26 C -0.37342(15) 0.03237(16) 0.34110(14) 0.0173(3) Uani 1 1 d . . . . .
H26A H -0.315282 -0.080559 0.363082 0.021 Uiso 1 1 calc R U . . .
H26B H -0.385533 0.054925 0.429041 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
O1 C3 1.3298(16) . ?
O1 H1 0.87(2) . ?
O2 C3 1.2092(16) . ?
C3 C4 1.5032(17) . ?
C4 C5 1.5213(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5199(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O7 1.2464(15) . ?
C6 O8 1.2783(15) . ?
O9 C11 1.3257(16) . ?
O9 H9 0.88(2) . ?
O10 C11 1.2069(17) . ?
C11 C12 1.5102(18) . ?
C12 C12 1.523(3) 2_545 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O13 C15 1.3122(15) . ?
O13 H13 0.97(2) . ?
O14 C15 1.2203(16) . ?
C15 C16 1.5069(17) . ?
C16 C16 1.519(2) 2_566 ?
C16 H16B 0.9900 . ?
C16 H16A 0.9900 . ?
N17 C25 1.4448(16) . ?
N17 C18 1.4731(17) . ?
N17 C22 1.4770(17) . ?
C18 N19 1.4714(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N19 C26 1.4452(16) . ?
N19 C20 1.4776(17) . ?
C20 N21 1.4726(17) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N21 C24 1.4440(16) . ?
N21 C22 1.4726(16) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N23 C26 1.5143(17) . ?
N23 C25 1.5179(16) . ?
N23 C24 1.5224(16) . ?
N23 H23 0.935(19) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 113.3(13) . . ?
O2 C3 O1 122.98(12) . . ?
O2 C3 C4 125.24(12) . . ?
O1 C3 C4 111.77(11) . . ?
C3 C4 C5 113.19(10) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 113.44(10) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O7 C6 O8 121.80(11) . . ?
O7 C6 C5 120.90(11) . . ?
O8 C6 C5 117.24(11) . . ?
C11 O9 H9 110.0(13) . . ?
O10 C11 O9 124.16(12) . . ?
O10 C11 C12 124.02(12) . . ?
O9 C11 C12 111.80(11) . . ?
C11 C12 C12 112.42(14) . 2_545 ?
C11 C12 H12A 109.1 . . ?
C12 C12 H12A 109.1 2_545 . ?
C11 C12 H12B 109.1 . . ?
C12 C12 H12B 109.1 2_545 . ?
H12A C12 H12B 107.9 . . ?
C15 O13 H13 111.3(13) . . ?
O14 C15 O13 122.88(11) . . ?
O14 C15 C16 124.09(11) . . ?
O13 C15 C16 113.03(10) . . ?
C15 C16 C16 112.81(13) . 2_566 ?
C15 C16 H16B 109.0 . . ?
C16 C16 H16B 109.0 2_566 . ?
C15 C16 H16A 109.0 . . ?
C16 C16 H16A 109.0 2_566 . ?
H16B C16 H16A 107.8 . . ?
C25 N17 C18 108.65(10) . . ?
C25 N17 C22 109.01(10) . . ?
C18 N17 C22 108.63(10) . . ?
N19 C18 N17 112.00(10) . . ?
N19 C18 H18A 109.2 . . ?
N17 C18 H18A 109.2 . . ?
N19 C18 H18B 109.2 . . ?
N17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C26 N19 C18 109.02(10) . . ?
C26 N19 C20 109.15(11) . . ?
C18 N19 C20 108.48(10) . . ?
N21 C20 N19 111.82(10) . . ?
N21 C20 H20A 109.3 . . ?
N19 C20 H20A 109.3 . . ?
N21 C20 H20B 109.3 . . ?
N19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C24 N21 C22 109.56(10) . . ?
C24 N21 C20 108.59(10) . . ?
C22 N21 C20 108.57(10) . . ?
N21 C22 N17 111.78(10) . . ?
N21 C22 H22A 109.3 . . ?
N17 C22 H22A 109.3 . . ?
N21 C22 H22B 109.3 . . ?
N17 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C26 N23 C25 108.62(10) . . ?
C26 N23 C24 108.43(10) . . ?
C25 N23 C24 108.82(10) . . ?
C26 N23 H23 112.8(11) . . ?
C25 N23 H23 109.8(11) . . ?
C24 N23 H23 108.3(11) . . ?
N21 C24 N23 109.71(10) . . ?
N21 C24 H24A 109.7 . . ?
N23 C24 H24A 109.7 . . ?
N21 C24 H24B 109.7 . . ?
N23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
N17 C25 N23 109.94(10) . . ?
N17 C25 H25A 109.7 . . ?
N23 C25 H25A 109.7 . . ?
N17 C25 H25B 109.7 . . ?
N23 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
N19 C26 N23 109.61(10) . . ?
N19 C26 H26A 109.7 . . ?
N23 C26 H26A 109.7 . . ?
N19 C26 H26B 109.7 . . ?
N23 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O14 0.87(2) 1.85(2) 2.6682(13) 157.3(19) 1_645 yes
O13 H13 O8 0.97(2) 1.58(2) 2.5442(12) 178(2) . yes
O9 H9 O7 0.88(2) 1.73(2) 2.6069(13) 173(2) . yes
N23 H23 O8 0.935(19) 1.796(19) 2.7275(14) 174.0(17) . yes

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.219
_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_2a_100K
_database_code_depnum_ccdc_archive 'CCDC 1970255'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '4,4-bipyridinium bis(hydrogen oxalate)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N2, 2(C2 H O4)'
_chemical_formula_sum            'C14 H12 N2 O8'
_chemical_formula_weight         336.26

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                   3.6795(7)
_cell_length_b                   9.855(2)
_cell_length_c                   10.425(2)
_cell_angle_alpha                116.097(2)
_cell_angle_beta                 97.436(2)
_cell_angle_gamma                97.188(2)
_cell_volume                     329.5(1)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4463
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.31

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_F_000             174
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9530
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            9229
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.224
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1630
_reflns_number_gt                1477
_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 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0573P)²+0.1505P] 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         1630
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6734(2) 0.87663(10) 0.57872(9) 0.0157(2) Uani 1 1 d . . . . .
H1 H 0.822(6) 0.948(2) 0.564(2) 0.039(5) Uiso 1 1 d . . . . .
O2 O 0.3327(3) 0.64045(10) 0.45325(9) 0.0168(2) Uani 1 1 d . . . . .
C3 C 0.5425(3) 0.74693(13) 0.45613(12) 0.0113(2) Uani 1 1 d . . . . .
C4 C 0.6754(3) 0.74061(13) 0.31840(12) 0.0104(2) Uani 1 1 d . . . . .
O5 O 0.8981(2) 0.85680(10) 0.33624(9) 0.0153(2) Uani 1 1 d . . . . .
O6 O 0.5474(2) 0.61836(9) 0.20239(9) 0.0138(2) Uani 1 1 d . . . . .
N7 N 0.0668(3) 0.36962(11) 0.15214(11) 0.0109(2) Uani 1 1 d . . . . .
H7 H 0.239(6) 0.477(2) 0.192(2) 0.044(6) Uiso 1 1 d . . . . .
C8 C -0.0405(3) 0.31378(13) 0.24091(12) 0.0135(2) Uani 1 1 d . . . . .
H8 H 0.036423 0.374605 0.343753 0.016 Uiso 1 1 calc R U . . .
C9 C -0.2627(3) 0.16786(13) 0.18300(12) 0.0123(2) Uani 1 1 d . . . . .
H9 H -0.335726 0.128275 0.246114 0.015 Uiso 1 1 calc R U . . .
C10 C -0.3799(3) 0.07868(12) 0.03185(12) 0.0089(2) Uani 1 1 d . . . . .
C11 C -0.2627(3) 0.14149(13) -0.05705(12) 0.0110(2) Uani 1 1 d . . . . .
H11 H -0.338022 0.084157 -0.160261 0.013 Uiso 1 1 calc R U . . .
C12 C -0.0365(3) 0.28747(13) 0.00630(12) 0.0114(2) Uani 1 1 d . . . . .
H12 H 0.045841 0.329594 -0.053760 0.014 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3223(13) . ?
O1 H1 0.92(2) . ?
O2 C3 1.2091(14) . ?
C3 C4 1.5541(16) . ?
C4 O5 1.2474(14) . ?
C4 O6 1.2509(14) . ?
N7 C12 1.3424(15) . ?
N7 C8 1.3429(15) . ?
N7 H7 1.03(2) . ?
C8 C9 1.3840(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.3973(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.4035(15) . ?
C10 C10 1.492(2) 2_455 ?
C11 C12 1.3859(15) . ?
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
C3 O1 H1 111.5(13) . . ?
O2 C3 O1 121.21(10) . . ?
O2 C3 C4 122.74(10) . . ?
O1 C3 C4 116.06(10) . . ?
O5 C4 O6 127.60(11) . . ?
O5 C4 C3 116.59(10) . . ?
O6 C4 C3 115.81(10) . . ?
C12 N7 C8 121.74(10) . . ?
C12 N7 H7 116.1(12) . . ?
C8 N7 H7 122.2(12) . . ?
N7 C8 C9 120.19(10) . . ?
N7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 120.09(11) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 117.92(10) . . ?
C9 C10 C10 120.58(12) . 2_455 ?
C11 C10 C10 121.50(12) . 2_455 ?
C12 C11 C10 119.74(10) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N7 C12 C11 120.31(10) . . ?
N7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O5 0.92(2) 2.21(2) 2.6944(13) 112.3(15) . yes
O1 H1 O5 0.92(2) 1.82(2) 2.5935(13) 140.5(18) 2_776 yes
N7 H7 O6 1.03(2) 1.64(2) 2.6376(13) 161(2) . yes

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_1a_RT
_database_code_depnum_ccdc_archive 'CCDC 1970254'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
;
hexamethylenetetramine hydrogen succinate succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H13 N4, C4 H5 O4, C4 H6 O4'
_chemical_formula_sum            'C14 H24 N4 O8'
_chemical_formula_weight         376.37

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                   9.6812(2)
_cell_length_b                   9.8923(2)
_cell_length_c                   10.3777(3)
_cell_angle_alpha                70.346(1)
_cell_angle_beta                 83.328(1)
_cell_angle_gamma                67.442(1)
_cell_volume                     864.26(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7277
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.61

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9591
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            21393
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         28.335
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4299
_reflns_number_gt                3172
_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 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0512P)²+0.4707P] 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         4299
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.09623(16) 0.90178(18) 0.70460(16) 0.0539(4) Uani 1 1 d . . . . .
H1 H -0.183(3) 0.946(3) 0.667(3) 0.078(9) Uiso 1 1 d . . . . .
H9 H 0.429(3) 0.767(4) 0.818(3) 0.098(10) Uiso 1 1 d . . . . .
O2 O -0.03187(17) 0.8230(2) 0.52357(16) 0.0641(5) Uani 1 1 d . . . . .
C3 C 0.00259(19) 0.82913(19) 0.62750(18) 0.0342(4) Uani 1 1 d . . . . .
C4 C 0.15748(19) 0.7605(2) 0.6862(2) 0.0391(4) Uani 1 1 d . . . . .
H4A H 0.152612 0.720117 0.784988 0.047 Uiso 1 1 calc R U . . .
H4B H 0.197522 0.841562 0.664922 0.047 Uiso 1 1 calc R U . . .
C5 C 0.26359(18) 0.6325(2) 0.6338(2) 0.0359(4) Uani 1 1 d . . . . .
H5A H 0.222931 0.552077 0.654242 0.043 Uiso 1 1 calc R U . . .
H5B H 0.269030 0.673303 0.535060 0.043 Uiso 1 1 calc R U . . .
C6 C 0.41952(18) 0.5619(2) 0.69347(19) 0.0345(4) Uani 1 1 d . . . . .
O7 O 0.46698(15) 0.63291(17) 0.74413(18) 0.0555(4) Uani 1 1 d . . . . .
O8 O 0.50209(13) 0.43014(15) 0.68365(15) 0.0445(3) Uani 1 1 d . . . . .
O9 O 0.39264(18) 0.8437(2) 0.8620(2) 0.0725(6) Uani 1 1 d . . . . .
O10 O 0.63024(19) 0.7748(2) 0.9102(3) 0.0894(7) Uani 1 1 d . . . . .
C11 C 0.5020(2) 0.8524(2) 0.9169(2) 0.0493(5) Uani 1 1 d . . . . .
C12 C 0.4487(3) 0.9692(4) 0.9908(4) 0.0796(9) Uani 1 1 d . . . . .
H12B H 0.362157 1.054278 0.941437 0.096 Uiso 1 1 calc R U . . .
H12A H 0.415089 0.922237 1.080399 0.096 Uiso 1 1 calc R U . . .
O13 O 0.40180(14) 0.28829(15) 0.57664(16) 0.0452(4) Uani 1 1 d . . . . .
H13 H 0.442(3) 0.336(3) 0.620(3) 0.086(9) Uiso 1 1 d . . . . .
O14 O 0.62582(14) 0.10341(16) 0.62056(17) 0.0518(4) Uani 1 1 d . . . . .
C15 C 0.50092(18) 0.15471(19) 0.57342(18) 0.0328(4) Uani 1 1 d . . . . .
C16 C 0.44298(19) 0.0759(2) 0.5040(2) 0.0400(4) Uani 1 1 d . . . . .
H16A H 0.409879 0.144025 0.411962 0.048 Uiso 1 1 calc R U . . .
H16B H 0.356757 0.058220 0.553112 0.048 Uiso 1 1 calc R U . . .
N17 N 1.01854(18) 0.16973(18) 0.84428(17) 0.0454(4) Uani 1 1 d . . . . .
C18 C 1.0926(2) 0.2644(3) 0.7460(2) 0.0528(5) Uani 1 1 d . . . . .
H18A H 1.103610 0.242318 0.660272 0.063 Uiso 1 1 calc R U . . .
H18B H 1.191813 0.237409 0.780396 0.063 Uiso 1 1 calc R U . . .
N19 N 1.0086(2) 0.4295(2) 0.72108(17) 0.0492(4) Uani 1 1 d . . . . .
C20 C 0.9891(3) 0.4610(3) 0.8518(2) 0.0529(5) Uani 1 1 d . . . . .
H20A H 1.086472 0.437215 0.888489 0.064 Uiso 1 1 calc R U . . .
H20B H 0.931907 0.569999 0.836220 0.064 Uiso 1 1 calc R U . . .
N21 N 0.91237(18) 0.37042(18) 0.95201(16) 0.0406(4) Uani 1 1 d . . . . .
C22 C 0.9992(2) 0.2061(2) 0.9729(2) 0.0474(5) Uani 1 1 d . . . . .
H22A H 0.948534 0.144851 1.038059 0.057 Uiso 1 1 calc R U . . .
H22B H 1.096706 0.178769 1.011206 0.057 Uiso 1 1 calc R U . . .
N23 N 0.78243(17) 0.37605(18) 0.76389(17) 0.0404(4) Uani 1 1 d . . . . .
H23 H 0.687(3) 0.400(3) 0.730(2) 0.065(7) Uiso 1 1 d . . . . .
C24 C 0.7669(2) 0.4100(2) 0.8982(2) 0.0440(5) Uani 1 1 d . . . . .
H24A H 0.709032 0.518731 0.883422 0.053 Uiso 1 1 calc R U . . .
H24B H 0.714479 0.350681 0.963303 0.053 Uiso 1 1 calc R U . . .
C25 C 0.8743(2) 0.2067(2) 0.7894(2) 0.0461(5) Uani 1 1 d . . . . .
H25A H 0.823310 0.144956 0.853439 0.055 Uiso 1 1 calc R U . . .
H25B H 0.886151 0.183159 0.704410 0.055 Uiso 1 1 calc R U . . .
C26 C 0.8636(2) 0.4692(2) 0.6651(2) 0.0498(5) Uani 1 1 d . . . . .
H26A H 0.875087 0.448494 0.578710 0.060 Uiso 1 1 calc R U . . .
H26B H 0.806323 0.578438 0.648163 0.060 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.324(2) . ?
O1 H1 0.85(3) . ?
O2 C3 1.192(2) . ?
C3 C4 1.494(2) . ?
C4 C5 1.513(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.506(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.238(2) . ?
C6 O8 1.272(2) . ?
O9 C11 1.303(3) . ?
O9 H9 0.95(3) . ?
O10 C11 1.191(3) . ?
C11 C12 1.496(3) . ?
C12 C12 1.407(5) 2_677 ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
O13 C15 1.3106(19) . ?
O13 H13 0.96(3) . ?
O14 C15 1.208(2) . ?
C15 C16 1.499(2) . ?
C16 C16 1.508(3) 2_656 ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
N17 C25 1.435(3) . ?
N17 C18 1.461(3) . ?
N17 C22 1.470(3) . ?
C18 N19 1.463(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N19 C26 1.440(3) . ?
N19 C20 1.468(3) . ?
C20 N21 1.463(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
N21 C24 1.436(2) . ?
N21 C22 1.467(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N23 C26 1.501(3) . ?
N23 C25 1.510(2) . ?
N23 C24 1.518(2) . ?
N23 H23 0.94(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 110.6(19) . . ?
O2 C3 O1 122.37(17) . . ?
O2 C3 C4 125.78(16) . . ?
O1 C3 C4 111.84(15) . . ?
C3 C4 C5 113.88(15) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 114.17(14) . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
O7 C6 O8 121.67(16) . . ?
O7 C6 C5 120.98(15) . . ?
O8 C6 C5 117.26(15) . . ?
C11 O9 H9 110.7(19) . . ?
O10 C11 O9 123.77(19) . . ?
O10 C11 C12 123.7(2) . . ?
O9 C11 C12 112.50(18) . . ?
C12 C12 C11 117.3(3) 2_677 . ?
C12 C12 H12B 108.0 2_677 . ?
C11 C12 H12B 108.0 . . ?
C12 C12 H12A 108.0 2_677 . ?
C11 C12 H12A 108.0 . . ?
H12B C12 H12A 107.2 . . ?
C15 O13 H13 110.9(17) . . ?
O14 C15 O13 122.61(16) . . ?
O14 C15 C16 124.51(15) . . ?
O13 C15 C16 112.87(14) . . ?
C15 C16 C16 113.54(19) . 2_656 ?
C15 C16 H16A 108.9 . . ?
C16 C16 H16A 108.9 2_656 . ?
C15 C16 H16B 108.9 . . ?
C16 C16 H16B 108.9 2_656 . ?
H16A C16 H16B 107.7 . . ?
C25 N17 C18 108.49(16) . . ?
C25 N17 C22 109.22(16) . . ?
C18 N17 C22 108.94(17) . . ?
N17 C18 N19 111.99(15) . . ?
N17 C18 H18A 109.2 . . ?
N19 C18 H18A 109.2 . . ?
N17 C18 H18B 109.2 . . ?
N19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C26 N19 C18 108.69(16) . . ?
C26 N19 C20 109.00(18) . . ?
C18 N19 C20 108.80(17) . . ?
N21 C20 N19 112.08(16) . . ?
N21 C20 H20A 109.2 . . ?
N19 C20 H20A 109.2 . . ?
N21 C20 H20B 109.2 . . ?
N19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C24 N21 C20 108.62(16) . . ?
C24 N21 C22 109.23(16) . . ?
C20 N21 C22 108.48(16) . . ?
N21 C22 N17 111.73(15) . . ?
N21 C22 H22A 109.3 . . ?
N17 C22 H22A 109.3 . . ?
N21 C22 H22B 109.3 . . ?
N17 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C26 N23 C25 108.76(15) . . ?
C26 N23 C24 108.63(15) . . ?
C25 N23 C24 108.60(15) . . ?
C26 N23 H23 111.6(15) . . ?
C25 N23 H23 109.7(15) . . ?
C24 N23 H23 109.4(15) . . ?
N21 C24 N23 109.77(14) . . ?
N21 C24 H24A 109.7 . . ?
N23 C24 H24A 109.7 . . ?
N21 C24 H24B 109.7 . . ?
N23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
N17 C25 N23 109.77(15) . . ?
N17 C25 H25A 109.7 . . ?
N23 C25 H25A 109.7 . . ?
N17 C25 H25B 109.7 . . ?
N23 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
N19 C26 N23 109.58(15) . . ?
N19 C26 H26A 109.8 . . ?
N23 C26 H26A 109.8 . . ?
N19 C26 H26B 109.8 . . ?
N23 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?

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
O2 C3 C4 C5 -21.1(3) . . . . ?
O1 C3 C4 C5 159.64(17) . . . . ?
C3 C4 C5 C6 -179.47(16) . . . . ?
C4 C5 C6 O7 -21.5(3) . . . . ?
C4 C5 C6 O8 161.75(17) . . . . ?
O10 C11 C12 C12 23.9(6) . . . 2_677 ?
O9 C11 C12 C12 -156.8(4) . . . 2_677 ?
O14 C15 C16 C16 -0.7(3) . . . 2_656 ?
O13 C15 C16 C16 178.4(2) . . . 2_656 ?
C25 N17 C18 N19 61.1(2) . . . . ?
C22 N17 C18 N19 -57.7(2) . . . . ?
N17 C18 N19 C26 -61.1(2) . . . . ?
N17 C18 N19 C20 57.5(2) . . . . ?
C26 N19 C20 N21 60.6(2) . . . . ?
C18 N19 C20 N21 -57.8(2) . . . . ?
N19 C20 N21 C24 -60.5(2) . . . . ?
N19 C20 N21 C22 58.1(2) . . . . ?
C24 N21 C22 N17 60.2(2) . . . . ?
C20 N21 C22 N17 -58.0(2) . . . . ?
C25 N17 C22 N21 -60.4(2) . . . . ?
C18 N17 C22 N21 58.0(2) . . . . ?
C20 N21 C24 N23 59.2(2) . . . . ?
C22 N21 C24 N23 -58.9(2) . . . . ?
C26 N23 C24 N21 -59.4(2) . . . . ?
C25 N23 C24 N21 58.7(2) . . . . ?
C18 N17 C25 N23 -59.3(2) . . . . ?
C22 N17 C25 N23 59.3(2) . . . . ?
C26 N23 C25 N17 59.2(2) . . . . ?
C24 N23 C25 N17 -58.9(2) . . . . ?
C18 N19 C26 N23 59.3(2) . . . . ?
C20 N19 C26 N23 -59.2(2) . . . . ?
C25 N23 C26 N19 -58.9(2) . . . . ?
C24 N23 C26 N19 59.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O14 0.85(3) 1.89(3) 2.6902(19) 155(3) 1_465 yes
O9 H9 O7 0.95(3) 1.65(3) 2.593(2) 171(3) . yes
O13 H13 O8 0.96(3) 1.59(3) 2.5473(18) 175(3) . yes
N23 H23 O8 0.94(3) 1.79(3) 2.731(2) 174(2) . yes

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.046

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

data_2a_RT
_database_code_depnum_ccdc_archive 'CCDC 1970257'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '4,4-bipyridinium bis(hydrogen oxalate)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N2, 2(C2 H O4)'
_chemical_formula_sum            'C14 H12 N2 O8'
_chemical_formula_weight         336.26

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                   3.7614(3)
_cell_length_b                   9.8932(7)
_cell_length_c                   10.4498(7)
_cell_angle_alpha                116.121(1)
_cell_angle_beta                 96.721(1)
_cell_angle_gamma                98.409(1)
_cell_volume                     338.11(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2579
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             174
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            5441
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.217
_diffrn_reflns_theta_max         28.412
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1679
_reflns_number_gt                1462
_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 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0767P)²+0.0605P] 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         1679
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3229(3) 0.12529(12) 0.42171(11) 0.0425(3) Uani 1 1 d . . . . .
H1 H 0.172(6) 0.056(2) 0.435(2) 0.058(6) Uiso 1 1 d . . . . .
O2 O 0.6625(3) 0.36032(12) 0.54678(12) 0.0467(3) Uani 1 1 d . . . . .
C3 C 0.4549(4) 0.25376(15) 0.54385(14) 0.0294(3) Uani 1 1 d . . . . .
C4 C 0.3274(4) 0.25881(14) 0.68123(13) 0.0268(3) Uani 1 1 d . . . . .
O5 O 0.1096(3) 0.14192(11) 0.66370(11) 0.0415(3) Uani 1 1 d . . . . .
O6 O 0.4552(3) 0.38024(11) 0.79675(11) 0.0364(3) Uani 1 1 d . . . . .
N7 N 0.9346(3) 0.63060(12) 0.84844(12) 0.0279(3) Uani 1 1 d . . . . .
H7 H 0.758(6) 0.523(3) 0.810(3) 0.068(7) Uiso 1 1 d . . . . .
C8 C 1.0442(4) 0.68630(15) 0.76027(15) 0.0357(3) Uani 1 1 d . . . . .
H8 H 0.970693 0.626659 0.659852 0.043 Uiso 1 1 calc R U . . .
C9 C 1.2661(4) 0.83206(15) 0.81813(14) 0.0312(3) Uani 1 1 d . . . . .
H9 H 1.339803 0.870800 0.756594 0.037 Uiso 1 1 calc R U . . .
C10 C 1.3800(3) 0.92120(12) 0.96810(12) 0.0209(3) Uani 1 1 d . . . . .
C11 C 1.2596(4) 0.85835(14) 1.05600(14) 0.0278(3) Uani 1 1 d . . . . .
H11 H 1.330802 0.914617 1.156784 0.033 Uiso 1 1 calc R U . . .
C12 C 1.0345(4) 0.71241(14) 0.99282(14) 0.0287(3) Uani 1 1 d . . . . .
H12 H 0.952329 0.671073 1.051376 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3152(15) . ?
O1 H1 0.89(2) . ?
O2 C3 1.2029(16) . ?
C3 C4 1.5488(19) . ?
C4 O5 1.2422(15) . ?
C4 O6 1.2449(15) . ?
N7 C12 1.3326(17) . ?
N7 C8 1.3387(18) . ?
N7 H7 1.04(2) . ?
C8 C9 1.3797(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.3902(17) . ?
C9 H9 0.9300 . ?
C10 C11 1.3976(16) . ?
C10 C10 1.491(2) 2_877 ?
C11 C12 1.3818(17) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 111.8(14) . . ?
O2 C3 O1 121.10(12) . . ?
O2 C3 C4 122.69(12) . . ?
O1 C3 C4 116.22(11) . . ?
O5 C4 O6 127.51(12) . . ?
O5 C4 C3 116.53(11) . . ?
O6 C4 C3 115.96(11) . . ?
C12 N7 C8 121.73(11) . . ?
C12 N7 H7 115.4(14) . . ?
C8 N7 H7 122.8(14) . . ?
N7 C8 C9 120.11(12) . . ?
N7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 120.23(12) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 117.73(11) . . ?
C9 C10 C10 120.72(13) . 2_877 ?
C11 C10 C10 121.55(13) . 2_877 ?
C12 C11 C10 119.85(12) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N7 C12 C11 120.35(12) . . ?
N7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?

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
O2 C3 C4 O5 179.28(13) . . . . ?
O1 C3 C4 O5 -0.65(19) . . . . ?
O2 C3 C4 O6 -0.6(2) . . . . ?
O1 C3 C4 O6 179.49(12) . . . . ?
C12 N7 C8 C9 -0.1(2) . . . . ?
N7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C8 C9 C10 C10 179.94(14) . . . 2_877 ?
C9 C10 C11 C12 -0.15(19) . . . . ?
C10 C10 C11 C12 179.41(13) 2_877 . . . ?
C8 N7 C12 C11 -0.6(2) . . . . ?
C10 C11 C12 N7 0.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O5 0.89(2) 2.21(2) 2.6857(14) 112.7(17) . yes
O1 H1 O5 0.89(2) 1.84(2) 2.5993(14) 142(2) 2_556 yes
N7 H7 O6 1.04(2) 1.62(3) 2.6392(14) 163(2) . yes

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_1b_RT
_database_code_depnum_ccdc_archive 'CCDC 1970258'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2020-08-17 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT245_1b_RT               
;
PROBLEM: U(iso) H7 Smaller than U(eq) O7B by 0.077 Ang**2
RESPONSE: There is positional disorder in one of the carboxylic acid 
groups, which was modelled according to the electron density map. 
The acidic hydrogen atoms were placed according to the 
difference map and appeared in the same positions for both parts.
;
_vrf_PLAT250_1b_RT               
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor .... 4.8 Note
RESPONSE: There is positional disorder in one of the carboxylic acid 
groups, which was modelled according to the electron density map. 
The acidic hydrogen atoms were placed according to the 
difference map and appeared in the same positions for both parts.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
;
hexamethylenetetramine succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 O4, C6 H12 N4'
_chemical_formula_sum            'C10 H18 N4 O4'
_chemical_formula_weight         258.28

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

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

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

_cell_length_a                   6.017(1)
_cell_length_b                   18.340(3)
_cell_length_c                   11.778(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.387(3)
_cell_angle_gamma                90
_cell_volume                     1282.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8408
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.21

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9158
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            25453
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.075
_diffrn_reflns_theta_max         28.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3199
_reflns_number_gt                2611
_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 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_computing_publication_material  ?
_refine_special_details          
;
Positional disorder in one of the carboxylic acid groups was 
modelled according to the electron density map. 
However, the acidic hydrogen atom for both parts has 
the same coordinates.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+0.9119P] 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         3199
_refine_ls_number_parameters     199
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.1862
_refine_ls_wR_factor_gt          0.1771
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2772(5) 0.44987(12) 0.8829(3) 0.1226(13) Uani 1 1 d . . . . .
H1 H 1.330(8) 0.408(3) 0.927(4) 0.162(19) Uiso 1 1 d . . . . .
O2 O 1.0546(3) 0.37321(9) 0.77905(16) 0.0724(6) Uani 1 1 d . . . . .
C3 C 1.1171(4) 0.43315(12) 0.7986(2) 0.0630(7) Uani 1 1 d . . . . .
C4 C 1.0214(7) 0.49985(17) 0.7341(4) 0.1208(18) Uani 1 1 d . . . . .
H4A H 1.005259 0.537435 0.790114 0.145 Uiso 1 1 calc R U . . .
H4B H 1.131307 0.517216 0.688621 0.145 Uiso 1 1 calc R U . . .
C5 C 0.8119(5) 0.49283(17) 0.6598(3) 0.0905(11) Uani 1 1 d . . . . .
H5A H 0.697761 0.482967 0.707180 0.109 Uiso 1 1 calc R U . A 1
H5B H 0.820744 0.450167 0.612074 0.109 Uiso 1 1 calc R U . A 1
C6B C 0.731(3) 0.5552(8) 0.5819(17) 0.099(5) Uani 0.394(18) 1 d . . P B 1
H7 H 0.510(6) 0.620(2) 0.549(3) 0.109(12) Uiso 1 1 d . . . . .
N9 N 1.4837(3) 0.33961(9) 1.00328(14) 0.0427(4) Uani 1 1 d . . . . .
C10 C 1.4540(4) 0.33710(13) 1.12591(18) 0.0501(5) Uani 1 1 d . . . . .
H10A H 1.497176 0.383743 1.161672 0.060 Uiso 1 1 calc R U . . .
H10B H 1.296216 0.329040 1.130149 0.060 Uiso 1 1 calc R U . . .
N11 N 1.5883(3) 0.27959(9) 1.18928(13) 0.0437(4) Uani 1 1 d . . . . .
C12 C 1.5236(4) 0.20938(12) 1.13406(19) 0.0524(5) Uani 1 1 d . . . . .
H12A H 1.366379 0.199770 1.137689 0.063 Uiso 1 1 calc R U . . .
H12B H 1.612726 0.170870 1.175661 0.063 Uiso 1 1 calc R U . . .
N13 N 1.5575(3) 0.20867(9) 1.01254(15) 0.0460(4) Uani 1 1 d . . . . .
C14 C 1.4187(3) 0.26772(11) 0.95162(17) 0.0444(5) Uani 1 1 d . . . . .
H14A H 1.437197 0.268024 0.871331 0.053 Uiso 1 1 calc R U . . .
H14B H 1.261162 0.258594 0.954992 0.053 Uiso 1 1 calc R U . . .
N15 N 1.8660(3) 0.29454(11) 1.06204(16) 0.0488(4) Uani 1 1 d . . . . .
C16 C 1.7257(4) 0.35113(13) 1.00021(19) 0.0525(5) Uani 1 1 d . . . . .
H16A H 1.749686 0.351929 0.920755 0.063 Uiso 1 1 calc R U . . .
H16B H 1.770823 0.398159 1.034016 0.063 Uiso 1 1 calc R U . . .
C17 C 1.7969(4) 0.22459(14) 1.0091(2) 0.0554(6) Uani 1 1 d . . . . .
H17A H 1.889566 0.186267 1.049103 0.066 Uiso 1 1 calc R U . . .
H17B H 1.821336 0.224941 0.929715 0.066 Uiso 1 1 calc R U . . .
C18 C 1.8259(3) 0.29243(11) 1.18148(17) 0.0448(5) Uani 1 1 d . . . . .
H18A H 1.873170 0.338342 1.218643 0.054 Uiso 1 1 calc R U . . .
H18B H 1.916707 0.254005 1.222354 0.054 Uiso 1 1 calc R U . . .
O7B O 0.558(3) 0.5780(7) 0.6181(12) 0.186(8) Uani 0.394(18) 1 d . . P B 1
O8B O 0.813(4) 0.5886(14) 0.516(3) 0.239(13) Uani 0.394(18) 1 d . . P B 1
O7A O 0.5245(7) 0.5798(2) 0.5885(5) 0.0635(16) Uani 0.606(18) 1 d . . P B 2
O8A O 0.8714(10) 0.6064(5) 0.5731(8) 0.111(3) Uani 0.606(18) 1 d . . P B 2
C6A C 0.7425(12) 0.5693(5) 0.6083(6) 0.0489(16) Uani 0.606(18) 1 d . . P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.302(3) . ?
O1 H1 0.94(5) . ?
O2 C3 1.172(3) . ?
C3 C4 1.504(3) . ?
C4 C5 1.418(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6B 1.497(15) . ?
C5 C6A 1.558(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6B O8B 1.16(3) . ?
C6B O7B 1.26(2) . ?
N9 C14 1.478(2) . ?
N9 C16 1.478(3) . ?
N9 C10 1.485(3) . ?
C10 N11 1.458(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N11 C12 1.466(3) . ?
N11 C18 1.467(3) . ?
C12 N13 1.478(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N13 C17 1.477(3) . ?
N13 C14 1.480(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N15 C16 1.456(3) . ?
N15 C17 1.457(3) . ?
N15 C18 1.466(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
O7B H7 1.12(4) . ?
O7A C6A 1.308(9) . ?
O7A H7 0.87(5) . ?
O8A C6A 1.159(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 112(3) . . ?
O2 C3 O1 123.0(2) . . ?
O2 C3 C4 125.4(2) . . ?
O1 C3 C4 111.6(2) . . ?
C5 C4 C3 117.8(3) . . ?
C5 C4 H4A 107.9 . . ?
C3 C4 H4A 107.9 . . ?
C5 C4 H4B 107.9 . . ?
C3 C4 H4B 107.9 . . ?
H4A C4 H4B 107.2 . . ?
C4 C5 C6B 118.5(7) . . ?
C4 C5 C6A 108.3(4) . . ?
C4 C5 H5A 107.7 . . ?
C6B C5 H5A 107.7 . . ?
C4 C5 H5B 107.7 . . ?
C6B C5 H5B 107.7 . . ?
H5A C5 H5B 107.1 . . ?
O8B C6B O7B 121.2(16) . . ?
O8B C6B C5 132.8(19) . . ?
O7B C6B C5 104.6(17) . . ?
C14 N9 C16 108.23(17) . . ?
C14 N9 C10 107.89(16) . . ?
C16 N9 C10 107.68(15) . . ?
N11 C10 N9 112.07(15) . . ?
N11 C10 H10A 109.2 . . ?
N9 C10 H10A 109.2 . . ?
N11 C10 H10B 109.2 . . ?
N9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 N11 C12 108.86(16) . . ?
C10 N11 C18 108.45(16) . . ?
C12 N11 C18 107.72(17) . . ?
N11 C12 N13 111.63(16) . . ?
N11 C12 H12A 109.3 . . ?
N13 C12 H12A 109.3 . . ?
N11 C12 H12B 109.3 . . ?
N13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C17 N13 C12 108.29(16) . . ?
C17 N13 C14 108.52(17) . . ?
C12 N13 C14 107.88(17) . . ?
N9 C14 N13 111.29(15) . . ?
N9 C14 H14A 109.4 . . ?
N13 C14 H14A 109.4 . . ?
N9 C14 H14B 109.4 . . ?
N13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 N15 C17 108.19(17) . . ?
C16 N15 C18 109.04(17) . . ?
C17 N15 C18 107.89(17) . . ?
N15 C16 N9 112.28(16) . . ?
N15 C16 H16A 109.1 . . ?
N9 C16 H16A 109.1 . . ?
N15 C16 H16B 109.1 . . ?
N9 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
N15 C17 N13 111.94(16) . . ?
N15 C17 H17A 109.2 . . ?
N13 C17 H17A 109.2 . . ?
N15 C17 H17B 109.2 . . ?
N13 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
N15 C18 N11 112.26(15) . . ?
N15 C18 H18A 109.2 . . ?
N11 C18 H18A 109.2 . . ?
N15 C18 H18B 109.2 . . ?
N11 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C6B O7B H7 96(2) . . ?
C6A O7A H7 103(3) . . ?
O8A C6A O7A 124.1(7) . . ?
O8A C6A C5 121.1(7) . . ?
O7A C6A C5 113.5(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
O2 C3 C4 C5 13.7(7) . . . . ?
O1 C3 C4 C5 -164.5(4) . . . . ?
C3 C4 C5 C6B -171.0(10) . . . . ?
C3 C4 C5 C6A 177.1(4) . . . . ?
C4 C5 C6B O8B 52(3) . . . . ?
C4 C5 C6B O7B -113.7(14) . . . . ?
C14 N9 C10 N11 58.3(2) . . . . ?
C16 N9 C10 N11 -58.3(2) . . . . ?
N9 C10 N11 C12 -58.3(2) . . . . ?
N9 C10 N11 C18 58.6(2) . . . . ?
C10 N11 C12 N13 58.8(2) . . . . ?
C18 N11 C12 N13 -58.6(2) . . . . ?
N11 C12 N13 C17 58.1(2) . . . . ?
N11 C12 N13 C14 -59.2(2) . . . . ?
C16 N9 C14 N13 57.4(2) . . . . ?
C10 N9 C14 N13 -58.9(2) . . . . ?
C17 N13 C14 N9 -57.5(2) . . . . ?
C12 N13 C14 N9 59.6(2) . . . . ?
C17 N15 C16 N9 59.4(2) . . . . ?
C18 N15 C16 N9 -57.7(2) . . . . ?
C14 N9 C16 N15 -58.7(2) . . . . ?
C10 N9 C16 N15 57.6(2) . . . . ?
C16 N15 C17 N13 -59.2(2) . . . . ?
C18 N15 C17 N13 58.6(2) . . . . ?
C12 N13 C17 N15 -58.2(2) . . . . ?
C14 N13 C17 N15 58.7(2) . . . . ?
C16 N15 C18 N11 57.6(2) . . . . ?
C17 N15 C18 N11 -59.7(2) . . . . ?
C10 N11 C18 N15 -57.9(2) . . . . ?
C12 N11 C18 N15 59.7(2) . . . . ?
C4 C5 C6A O8A 45.1(9) . . . . ?
C4 C5 C6A O7A -147.6(7) . . . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.409
_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_1c_RT
_database_code_depnum_ccdc_archive 'CCDC 1970259'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
;
bis-hexamethylenetetramine succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 O4, 2(C6 H12 N4)'
_chemical_formula_sum            'C16 H30 N8 O4'
_chemical_formula_weight         398.48

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   21.847(1)
_cell_length_b                   6.9981(4)
_cell_length_c                   26.359(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.170(1)
_cell_angle_gamma                90
_cell_volume                     3939.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7220
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.98

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9406
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            38167
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.581
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4898
_reflns_number_gt                3557
_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 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0866P)²+3.0071P] 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         4898
_refine_ls_number_parameters     334
_refine_ls_number_restraints     270
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1802
_refine_ls_wR_factor_gt          0.1627
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.037
_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
O1A O 0.2851(3) 0.8592(8) 0.4036(3) 0.073(2) Uani 0.529(13) 1 d . . P A 1
O2A O 0.2299(3) 0.5954(11) 0.3922(4) 0.076(2) Uani 0.529(13) 1 d . . P A 1
C3A C 0.2690(7) 0.6722(19) 0.4119(5) 0.050(3) Uani 0.529(13) 1 d . . P A 1
C4A C 0.3085(6) 0.5988(12) 0.4662(3) 0.080(3) Uani 0.529(13) 1 d . . P A 1
H4A1 H 0.350505 0.651140 0.471929 0.096 Uiso 0.529(13) 1 calc R U P A 1
H4A2 H 0.289134 0.643766 0.493928 0.096 Uiso 0.529(13) 1 calc R U P A 1
C5A C 0.3118(5) 0.3882(16) 0.4676(5) 0.052(2) Uani 0.529(13) 1 d . . P A 1
H5A1 H 0.311978 0.341669 0.432964 0.062 Uiso 0.529(13) 1 calc R U P A 1
H5A2 H 0.274584 0.338820 0.477544 0.062 Uiso 0.529(13) 1 calc R U P A 1
C6A C 0.3729(8) 0.306(2) 0.5072(5) 0.037(2) Uani 0.529(13) 1 d . . P A 1
O7A O 0.3986(6) 0.402(2) 0.5390(5) 0.066(2) Uani 0.529(13) 1 d . . P A 1
O8A O 0.3730(8) 0.120(3) 0.5036(6) 0.050(2) Uani 0.529(13) 1 d . . P A 1
N9 N 0.03718(7) 0.5426(2) 0.42318(5) 0.0376(3) Uani 1 1 d . . . . .
C10 C -0.00133(9) 0.4028(2) 0.38827(8) 0.0467(4) Uani 1 1 d . . . . .
H10A H 0.025875 0.321423 0.373003 0.056 Uiso 1 1 calc R U . . .
H10B H -0.023575 0.322492 0.408357 0.056 Uiso 1 1 calc R U . . .
N11 N -0.04649(7) 0.4959(2) 0.34691(6) 0.0477(4) Uani 1 1 d . . . . .
C12 C -0.01165(10) 0.6147(3) 0.31743(7) 0.0499(5) Uani 1 1 d . . . . .
H12A H -0.040893 0.677599 0.289651 0.060 Uiso 1 1 calc R U . . .
H12B H 0.015313 0.533777 0.301761 0.060 Uiso 1 1 calc R U . . .
N13 N 0.02649(7) 0.7592(2) 0.34939(6) 0.0450(4) Uani 1 1 d . . . . .
C14 C 0.07010(8) 0.6616(3) 0.39122(8) 0.0451(4) Uani 1 1 d . . . . .
H14A H 0.095372 0.756008 0.413149 0.054 Uiso 1 1 calc R U . . .
H14B H 0.098003 0.581546 0.376312 0.054 Uiso 1 1 calc R U . . .
C15 C -0.00497(10) 0.6692(3) 0.44484(7) 0.0513(5) Uani 1 1 d . . . . .
H15A H -0.027360 0.594116 0.465986 0.062 Uiso 1 1 calc R U . . .
H15B H 0.019821 0.763735 0.467066 0.062 Uiso 1 1 calc R U . . .
N16 N -0.05012(8) 0.7665(2) 0.40425(6) 0.0492(4) Uani 1 1 d . . . . .
C17 C -0.01497(9) 0.8776(2) 0.37304(8) 0.0488(5) Uani 1 1 d . . . . .
H17A H -0.044199 0.943700 0.345889 0.059 Uiso 1 1 calc R U . . .
H17B H 0.009768 0.973361 0.394861 0.059 Uiso 1 1 calc R U . . .
C18 C -0.08603(9) 0.6223(3) 0.37056(9) 0.0552(5) Uani 1 1 d . . . . .
H18A H -0.115904 0.685720 0.343304 0.066 Uiso 1 1 calc R U . . .
H18B H -0.109451 0.546073 0.390635 0.066 Uiso 1 1 calc R U . . .
N19 N 0.19800(6) 0.03192(19) 0.33258(5) 0.0375(3) Uani 1 1 d . . . . .
C20 C 0.23785(8) 0.1560(3) 0.30755(8) 0.0441(4) Uani 1 1 d . . . . .
H20A H 0.259484 0.247214 0.332798 0.053 Uiso 1 1 calc R U . . .
H20B H 0.269216 0.078193 0.296248 0.053 Uiso 1 1 calc R U . . .
N21 N 0.20187(6) 0.2592(2) 0.26311(6) 0.0402(3) Uani 1 1 d . . . . .
C22 C 0.16979(9) 0.1186(3) 0.22563(7) 0.0450(4) Uani 1 1 d . . . . .
H22A H 0.200745 0.041286 0.213612 0.054 Uiso 1 1 calc R U . . .
H22B H 0.145308 0.185038 0.195855 0.054 Uiso 1 1 calc R U . . .
N23 N 0.12844(6) -0.0065(2) 0.24779(6) 0.0387(3) Uani 1 1 d . . . . .
C24 C 0.16567(8) -0.1043(2) 0.29265(7) 0.0394(4) Uani 1 1 d . . . . .
H24A H 0.196583 -0.184302 0.281428 0.047 Uiso 1 1 calc R U . . .
H24B H 0.138606 -0.186601 0.307828 0.047 Uiso 1 1 calc R U . . .
C25 C 0.14990(9) 0.1532(3) 0.34837(7) 0.0445(4) Uani 1 1 d . . . . .
H25A H 0.122763 0.073883 0.364299 0.053 Uiso 1 1 calc R U . . .
H25B H 0.170204 0.244904 0.374073 0.053 Uiso 1 1 calc R U . . .
N26 N 0.11211(7) 0.2554(2) 0.30439(6) 0.0417(4) Uani 1 1 d . . . . .
C27 C 0.15419(9) 0.3734(2) 0.28089(7) 0.0422(4) Uani 1 1 d . . . . .
H27A H 0.129737 0.442687 0.251659 0.051 Uiso 1 1 calc R U . . .
H27B H 0.174703 0.466310 0.306130 0.051 Uiso 1 1 calc R U . . .
C28 C 0.08265(7) 0.1142(3) 0.26574(8) 0.0450(4) Uani 1 1 d . . . . .
H28A H 0.054911 0.033905 0.280778 0.054 Uiso 1 1 calc R U . . .
H28B H 0.057471 0.180277 0.236243 0.054 Uiso 1 1 calc R U . . .
O1B O 0.2540(7) 0.8595(10) 0.4217(2) 0.096(3) Uani 0.471(13) 1 d . . P A 2
O2B O 0.2534(6) 0.5951(12) 0.3779(2) 0.083(3) Uani 0.471(13) 1 d . . P A 2
C3B C 0.2777(7) 0.692(2) 0.4183(6) 0.044(2) Uani 0.471(13) 1 d . . P A 2
C4B C 0.3293(3) 0.5944(11) 0.4520(3) 0.0487(17) Uani 0.471(13) 1 d . . P A 2
H4B1 H 0.366172 0.612287 0.437494 0.058 Uiso 0.471(13) 1 calc R U P A 2
H4B2 H 0.337211 0.659427 0.485270 0.058 Uiso 0.471(13) 1 calc R U P A 2
C5B C 0.3244(6) 0.3954(15) 0.4619(4) 0.0399(18) Uani 0.471(13) 1 d . . P A 2
H5B1 H 0.281697 0.370495 0.465197 0.048 Uiso 0.471(13) 1 calc R U P A 2
H5B2 H 0.330742 0.326746 0.431461 0.048 Uiso 0.471(13) 1 calc R U P A 2
C6B C 0.3636(9) 0.318(2) 0.5043(7) 0.042(2) Uani 0.471(13) 1 d . . P A 2
O7B O 0.4149(5) 0.4030(19) 0.5287(5) 0.056(2) Uani 0.471(13) 1 d . . P A 2
O8B O 0.3627(10) 0.128(3) 0.5131(8) 0.057(3) Uani 0.471(13) 1 d . . P A 2
H1 H 0.246(2) 0.909(6) 0.3844(18) 0.169(17) Uiso 1 1 d . . . . .
H8 H 0.4002(14) 0.077(4) 0.5302(12) 0.087(9) 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
O1A C3A 1.385(14) . ?
O1A H1 0.96(5) . ?
O2A C3A 1.048(15) . ?
C3A C4A 1.594(14) . ?
C4A C5A 1.476(14) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A C6A 1.617(18) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A O7A 1.13(2) . ?
C6A O8A 1.30(2) . ?
O8A H8 0.87(4) . ?
N9 C14 1.475(2) . ?
N9 C15 1.476(2) . ?
N9 C10 1.478(2) . ?
C10 N11 1.461(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N11 C12 1.457(3) . ?
N11 C18 1.464(3) . ?
C12 N13 1.460(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N13 C17 1.461(3) . ?
N13 C14 1.465(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N16 1.462(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
N16 C18 1.459(3) . ?
N16 C17 1.462(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N19 C25 1.477(2) . ?
N19 C20 1.480(2) . ?
N19 C24 1.484(2) . ?
C20 N21 1.457(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
N21 C22 1.464(2) . ?
N21 C27 1.466(2) . ?
C22 N23 1.465(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N23 C24 1.457(2) . ?
N23 C28 1.462(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N26 1.461(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
N26 C27 1.466(2) . ?
N26 C28 1.467(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
O1B C3B 1.293(17) . ?
O1B H1 1.02(5) . ?
O2B C3B 1.279(15) . ?
C3B C4B 1.451(17) . ?
C4B C5B 1.425(14) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B C6B 1.370(19) . ?
C5B H5B1 0.9700 . ?
C5B H5B2 0.9700 . ?
C6B O7B 1.31(2) . ?
C6B O8B 1.35(2) . ?
O8B H8 0.92(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3A O1A H1 102(3) . . ?
O2A C3A O1A 127.9(12) . . ?
O2A C3A C4A 120.6(13) . . ?
O1A C3A C4A 109.8(9) . . ?
C5A C4A C3A 111.0(8) . . ?
C5A C4A H4A1 109.4 . . ?
C3A C4A H4A1 109.4 . . ?
C5A C4A H4A2 109.4 . . ?
C3A C4A H4A2 109.4 . . ?
H4A1 C4A H4A2 108.0 . . ?
C4A C5A C6A 113.8(10) . . ?
C4A C5A H5A1 108.8 . . ?
C6A C5A H5A1 108.8 . . ?
C4A C5A H5A2 108.8 . . ?
C6A C5A H5A2 108.8 . . ?
H5A1 C5A H5A2 107.7 . . ?
O7A C6A O8A 129.8(14) . . ?
O7A C6A C5A 118.8(15) . . ?
O8A C6A C5A 108.9(14) . . ?
C6A O8A H8 107(3) . . ?
C14 N9 C15 107.51(14) . . ?
C14 N9 C10 107.46(14) . . ?
C15 N9 C10 108.54(15) . . ?
N11 C10 N9 112.08(14) . . ?
N11 C10 H10A 109.2 . . ?
N9 C10 H10A 109.2 . . ?
N11 C10 H10B 109.2 . . ?
N9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 N11 C10 107.81(14) . . ?
C12 N11 C18 107.68(15) . . ?
C10 N11 C18 108.54(15) . . ?
N11 C12 N13 112.72(14) . . ?
N11 C12 H12A 109.0 . . ?
N13 C12 H12A 109.0 . . ?
N11 C12 H12B 109.0 . . ?
N13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 N13 C17 108.02(14) . . ?
C12 N13 C14 108.22(14) . . ?
C17 N13 C14 107.87(14) . . ?
N13 C14 N9 112.03(13) . . ?
N13 C14 H14A 109.2 . . ?
N9 C14 H14A 109.2 . . ?
N13 C14 H14B 109.2 . . ?
N9 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N16 C15 N9 112.11(14) . . ?
N16 C15 H15A 109.2 . . ?
N9 C15 H15A 109.2 . . ?
N16 C15 H15B 109.2 . . ?
N9 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C18 N16 C15 108.45(16) . . ?
C18 N16 C17 107.69(15) . . ?
C15 N16 C17 107.84(15) . . ?
N13 C17 N16 112.64(14) . . ?
N13 C17 H17A 109.1 . . ?
N16 C17 H17A 109.1 . . ?
N13 C17 H17B 109.1 . . ?
N16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
N16 C18 N11 112.77(14) . . ?
N16 C18 H18A 109.0 . . ?
N11 C18 H18A 109.0 . . ?
N16 C18 H18B 109.0 . . ?
N11 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C25 N19 C20 107.99(13) . . ?
C25 N19 C24 107.97(13) . . ?
C20 N19 C24 107.31(13) . . ?
N21 C20 N19 112.39(12) . . ?
N21 C20 H20A 109.1 . . ?
N19 C20 H20A 109.1 . . ?
N21 C20 H20B 109.1 . . ?
N19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
C20 N21 C22 108.04(14) . . ?
C20 N21 C27 108.20(14) . . ?
C22 N21 C27 108.10(13) . . ?
N21 C22 N23 112.35(13) . . ?
N21 C22 H22A 109.1 . . ?
N23 C22 H22A 109.1 . . ?
N21 C22 H22B 109.1 . . ?
N23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?
C24 N23 C28 108.16(14) . . ?
C24 N23 C22 108.59(13) . . ?
C28 N23 C22 107.79(14) . . ?
N23 C24 N19 111.98(13) . . ?
N23 C24 H24A 109.2 . . ?
N19 C24 H24A 109.2 . . ?
N23 C24 H24B 109.2 . . ?
N19 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
N26 C25 N19 111.99(13) . . ?
N26 C25 H25A 109.2 . . ?
N19 C25 H25A 109.2 . . ?
N26 C25 H25B 109.2 . . ?
N19 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C25 N26 C27 108.13(14) . . ?
C25 N26 C28 108.23(14) . . ?
C27 N26 C28 107.95(14) . . ?
N21 C27 N26 112.30(13) . . ?
N21 C27 H27A 109.1 . . ?
N26 C27 H27A 109.1 . . ?
N21 C27 H27B 109.1 . . ?
N26 C27 H27B 109.1 . . ?
H27A C27 H27B 107.9 . . ?
N23 C28 N26 112.57(12) . . ?
N23 C28 H28A 109.1 . . ?
N26 C28 H28A 109.1 . . ?
N23 C28 H28B 109.1 . . ?
N26 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C3B O1B H1 103(3) . . ?
O2B C3B O1B 115.8(12) . . ?
O2B C3B C4B 113.2(13) . . ?
O1B C3B C4B 130.9(13) . . ?
C5B C4B C3B 119.5(9) . . ?
C5B C4B H4B1 107.5 . . ?
C3B C4B H4B1 107.5 . . ?
C5B C4B H4B2 107.5 . . ?
C3B C4B H4B2 107.5 . . ?
H4B1 C4B H4B2 107.0 . . ?
C6B C5B C4B 118.6(11) . . ?
C6B C5B H5B1 107.7 . . ?
C4B C5B H5B1 107.7 . . ?
C6B C5B H5B2 107.7 . . ?
C4B C5B H5B2 107.7 . . ?
H5B1 C5B H5B2 107.1 . . ?
O7B C6B O8B 114.0(16) . . ?
O7B C6B C5B 122.8(14) . . ?
O8B C6B C5B 120.1(16) . . ?
C6B O8B H8 115(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
O2A C3A C4A C5A 36(2) . . . . ?
O1A C3A C4A C5A -157.9(12) . . . . ?
C3A C4A C5A C6A 154.0(12) . . . . ?
C4A C5A C6A O7A 19.5(19) . . . . ?
C4A C5A C6A O8A -176.8(12) . . . . ?
C14 N9 C10 N11 -58.86(19) . . . . ?
C15 N9 C10 N11 57.1(2) . . . . ?
N9 C10 N11 C12 59.1(2) . . . . ?
N9 C10 N11 C18 -57.3(2) . . . . ?
C10 N11 C12 N13 -58.9(2) . . . . ?
C18 N11 C12 N13 58.03(19) . . . . ?
N11 C12 N13 C17 -58.06(19) . . . . ?
N11 C12 N13 C14 58.5(2) . . . . ?
C12 N13 C14 N9 -58.0(2) . . . . ?
C17 N13 C14 N9 58.63(19) . . . . ?
C15 N9 C14 N13 -58.55(19) . . . . ?
C10 N9 C14 N13 58.12(19) . . . . ?
C14 N9 C15 N16 58.7(2) . . . . ?
C10 N9 C15 N16 -57.3(2) . . . . ?
N9 C15 N16 C18 57.7(2) . . . . ?
N9 C15 N16 C17 -58.7(2) . . . . ?
C12 N13 C17 N16 57.91(18) . . . . ?
C14 N13 C17 N16 -58.86(18) . . . . ?
C18 N16 C17 N13 -57.94(18) . . . . ?
C15 N16 C17 N13 58.91(19) . . . . ?
C15 N16 C18 N11 -58.3(2) . . . . ?
C17 N16 C18 N11 58.2(2) . . . . ?
C12 N11 C18 N16 -58.3(2) . . . . ?
C10 N11 C18 N16 58.2(2) . . . . ?
C25 N19 C20 N21 -57.60(18) . . . . ?
C24 N19 C20 N21 58.56(18) . . . . ?
N19 C20 N21 C22 -58.88(18) . . . . ?
N19 C20 N21 C27 57.93(18) . . . . ?
C20 N21 C22 N23 58.39(18) . . . . ?
C27 N21 C22 N23 -58.48(18) . . . . ?
N21 C22 N23 C24 -58.44(19) . . . . ?
N21 C22 N23 C28 58.52(18) . . . . ?
C28 N23 C24 N19 -58.41(17) . . . . ?
C22 N23 C24 N19 58.31(18) . . . . ?
C25 N19 C24 N23 58.15(17) . . . . ?
C20 N19 C24 N23 -58.03(17) . . . . ?
C20 N19 C25 N26 57.82(18) . . . . ?
C24 N19 C25 N26 -57.91(18) . . . . ?
N19 C25 N26 C27 -58.63(19) . . . . ?
N19 C25 N26 C28 58.07(18) . . . . ?
C20 N21 C27 N26 -58.66(18) . . . . ?
C22 N21 C27 N26 58.11(18) . . . . ?
C25 N26 C27 N21 59.06(18) . . . . ?
C28 N26 C27 N21 -57.82(17) . . . . ?
C24 N23 C28 N26 58.80(18) . . . . ?
C22 N23 C28 N26 -58.44(18) . . . . ?
C25 N26 C28 N23 -58.61(18) . . . . ?
C27 N26 C28 N23 58.21(18) . . . . ?
O2B C3B C4B C5B -42.2(18) . . . . ?
O1B C3B C4B C5B 140.2(18) . . . . ?
C3B C4B C5B C6B -161.1(16) . . . . ?
C4B C5B C6B O7B -17(3) . . . . ?
C4B C5B C6B O8B -176.1(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A^a H1 N19 0.96(5) 1.77(5) 2.661(4) 155(4) 1_565 yes
O1B^b H1 N19 1.02(5) 1.77(5) 2.694(5) 149(4) 1_565 yes
O8A^a H8 N9 0.87(4) 1.84(3) 2.695(19) 169(3) 7_556 yes
O8B^b H8 N9 0.92(4) 1.84(3) 2.73(2) 165(3) 7_556 yes

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.173
_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_1b_100K
_database_code_depnum_ccdc_archive 'CCDC 1970256'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
;
hexamethylenetetramine succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 O4, C6 H12 N4'
_chemical_formula_sum            'C10 H18 N4 O4'
_chemical_formula_weight         258.28

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

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

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

_cell_length_a                   5.8215(8)
_cell_length_b                   18.363(2)
_cell_length_c                   11.592(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.266(2)
_cell_angle_gamma                90
_cell_volume                     1219.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.27

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9303
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            23862
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3017
_reflns_number_gt                2680
_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 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0466P)²+0.6624P] 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         3017
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.76430(19) 0.54071(5) 0.39615(9) 0.0341(3) Uani 1 1 d . . . . .
H1 H 0.836(4) 0.5815(12) 0.4364(18) 0.055(6) Uiso 1 1 d . . . . .
O2 O 0.56080(19) 0.62294(5) 0.28084(9) 0.0391(3) Uani 1 1 d . . . . .
C3 C 0.60267(19) 0.56043(6) 0.30748(10) 0.0175(2) Uani 1 1 d . . . . .
H7 H 0.123(4) 0.3639(12) 0.0514(19) 0.061(6) Uiso 1 1 d . . . . .
N9 N 0.01259(16) 0.15430(5) -0.01018(8) 0.01438(19) Uani 1 1 d . . . . .
C10 C -0.23955(19) 0.15176(6) -0.00441(9) 0.0169(2) Uani 1 1 d . . . . .
H10A H -0.306468 0.105593 -0.039601 0.020 Uiso 1 1 calc R U . . .
H10B H -0.258837 0.152428 0.078724 0.020 Uiso 1 1 calc R U . . .
N11 N -0.36786(15) 0.21312(5) -0.06603(8) 0.0150(2) Uani 1 1 d . . . . .
C12 C -0.26683(19) 0.28109(6) -0.01245(9) 0.0164(2) Uani 1 1 d . . . . .
H12A H -0.286763 0.282781 0.070557 0.020 Uiso 1 1 calc R U . . .
H12B H -0.351608 0.323046 -0.053510 0.020 Uiso 1 1 calc R U . . .
N13 N -0.01480(16) 0.28729(5) -0.01834(8) 0.01429(19) Uani 1 1 d . . . . .
C14 C 0.10792(18) 0.22391(5) 0.04254(9) 0.0137(2) Uani 1 1 d . . . . .
H14A H 0.092577 0.225089 0.126210 0.016 Uiso 1 1 calc R U . . .
H14B H 0.276072 0.226984 0.038459 0.016 Uiso 1 1 calc R U . . .
N15 N -0.08703(16) 0.21633(5) -0.19977(8) 0.0150(2) Uani 1 1 d . . . . .
C16 C 0.0353(2) 0.15449(6) -0.13611(9) 0.0181(2) Uani 1 1 d . . . . .
H16A H 0.202739 0.156691 -0.142065 0.022 Uiso 1 1 calc R U . . .
H16B H -0.029290 0.108530 -0.173084 0.022 Uiso 1 1 calc R U . . .
C17 C 0.0100(2) 0.28405(6) -0.14349(9) 0.0179(2) Uani 1 1 d . . . . .
H17A H -0.071457 0.326197 -0.185659 0.022 Uiso 1 1 calc R U . . .
H17B H 0.177359 0.287503 -0.149097 0.022 Uiso 1 1 calc R U . . .
C18 C -0.33533(18) 0.21216(5) -0.18942(9) 0.0140(2) Uani 1 1 d . . . . .
H18A H -0.403444 0.166844 -0.227260 0.017 Uiso 1 1 calc R U . . .
H18B H -0.419906 0.253854 -0.231418 0.017 Uiso 1 1 calc R U . . .
C4A C 0.472(3) 0.4921(9) 0.2495(14) 0.0204(10) Uani 0.502(2) 1 d . . P A 2
H4A1 H 0.570224 0.467032 0.200387 0.025 Uiso 0.502(2) 1 calc R U P A 2
H4A2 H 0.442842 0.457786 0.311232 0.025 Uiso 0.502(2) 1 calc R U P A 2
C5A C 0.2414(4) 0.51387(12) 0.1744(2) 0.0207(5) Uani 0.502(2) 1 d . . P A 2
H5A1 H 0.146042 0.540198 0.223592 0.025 Uiso 0.502(2) 1 calc R U P A 2
H5A2 H 0.272013 0.547576 0.112205 0.025 Uiso 0.502(2) 1 calc R U P A 2
C6A C 0.1049(4) 0.44894(12) 0.11813(18) 0.0168(5) Uani 0.502(2) 1 d . . P A 2
O7A O 0.2366(8) 0.3978(3) 0.0837(4) 0.0220(8) Uani 0.502(2) 1 d . . P A 2
O8A O -0.1064(3) 0.44513(9) 0.10498(15) 0.0235(4) Uani 0.502(2) 1 d . . P A 2
C4B C 0.478(3) 0.4999(9) 0.2419(14) 0.0204(10) Uani 0.498(2) 1 d . . P A 1
H4B1 H 0.351922 0.483884 0.283361 0.025 Uiso 0.498(2) 1 calc R U P A 1
H4B2 H 0.587735 0.458600 0.243021 0.025 Uiso 0.498(2) 1 calc R U P A 1
C5B C 0.3690(4) 0.51631(12) 0.11317(19) 0.0178(5) Uani 0.498(2) 1 d . . P A 1
H5B1 H 0.250935 0.555213 0.112099 0.021 Uiso 0.498(2) 1 calc R U P A 1
H5B2 H 0.492779 0.535360 0.072835 0.021 Uiso 0.498(2) 1 calc R U P A 1
C6B C 0.2544(4) 0.45177(12) 0.04450(19) 0.0166(5) Uani 0.498(2) 1 d . . P A 1
O7B O 0.1894(9) 0.3996(3) 0.1114(4) 0.0241(9) Uani 0.498(2) 1 d . . P A 1
O8B O 0.2198(3) 0.44906(10) -0.06132(15) 0.0283(5) Uani 0.498(2) 1 d . . P A 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3147(14) . ?
O1 H1 0.94(2) . ?
O2 C3 1.2023(14) . ?
C3 C4B 1.465(18) . ?
C3 C4A 1.557(18) . ?
N9 C14 1.4814(13) . ?
N9 C10 1.4819(14) . ?
N9 C16 1.4892(14) . ?
C10 N11 1.4654(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N11 C12 1.4695(13) . ?
N11 C18 1.4760(13) . ?
C12 N13 1.4853(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N13 C14 1.4775(13) . ?
N13 C17 1.4845(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N15 C16 1.4676(14) . ?
N15 C17 1.4696(13) . ?
N15 C18 1.4736(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C4A C5A 1.518(16) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A C6A 1.515(3) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A O8A 1.214(3) . ?
C6A O7A 1.318(5) . ?
O7A H7 0.94(2) . ?
C4B C5B 1.544(15) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5B C6B 1.515(3) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B O8B 1.208(3) . ?
C6B O7B 1.329(5) . ?
O7B H7 0.98(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
C3 O1 H1 111.2(13) . . ?
O2 C3 O1 123.23(10) . . ?
O2 C3 C4B 122.2(6) . . ?
O1 C3 C4B 114.6(6) . . ?
O2 C3 C4A 126.7(5) . . ?
O1 C3 C4A 110.0(5) . . ?
C14 N9 C10 108.05(8) . . ?
C14 N9 C16 108.07(8) . . ?
C10 N9 C16 107.83(8) . . ?
N11 C10 N9 112.13(8) . . ?
N11 C10 H10A 109.2 . . ?
N9 C10 H10A 109.2 . . ?
N11 C10 H10B 109.2 . . ?
N9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 N11 C12 108.43(8) . . ?
C10 N11 C18 108.72(8) . . ?
C12 N11 C18 107.99(8) . . ?
N11 C12 N13 111.71(8) . . ?
N11 C12 H12A 109.3 . . ?
N13 C12 H12A 109.3 . . ?
N11 C12 H12B 109.3 . . ?
N13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 N13 C17 108.20(8) . . ?
C14 N13 C12 108.37(8) . . ?
C17 N13 C12 108.10(8) . . ?
N13 C14 N9 111.65(8) . . ?
N13 C14 H14A 109.3 . . ?
N9 C14 H14A 109.3 . . ?
N13 C14 H14B 109.3 . . ?
N9 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 N15 C17 108.53(8) . . ?
C16 N15 C18 108.31(8) . . ?
C17 N15 C18 108.23(8) . . ?
N15 C16 N9 112.01(8) . . ?
N15 C16 H16A 109.2 . . ?
N9 C16 H16A 109.2 . . ?
N15 C16 H16B 109.2 . . ?
N9 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N15 C17 N13 111.78(8) . . ?
N15 C17 H17A 109.3 . . ?
N13 C17 H17A 109.3 . . ?
N15 C17 H17B 109.3 . . ?
N13 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
N15 C18 N11 112.04(8) . . ?
N15 C18 H18A 109.2 . . ?
N11 C18 H18A 109.2 . . ?
N15 C18 H18B 109.2 . . ?
N11 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C5A C4A C3 110.5(10) . . ?
C5A C4A H4A1 109.6 . . ?
C3 C4A H4A1 109.6 . . ?
C5A C4A H4A2 109.6 . . ?
C3 C4A H4A2 109.6 . . ?
H4A1 C4A H4A2 108.1 . . ?
C6A C5A C4A 112.5(7) . . ?
C6A C5A H5A1 109.1 . . ?
C4A C5A H5A1 109.1 . . ?
C6A C5A H5A2 109.1 . . ?
C4A C5A H5A2 109.1 . . ?
H5A1 C5A H5A2 107.8 . . ?
O8A C6A O7A 123.5(3) . . ?
O8A C6A C5A 122.8(2) . . ?
O7A C6A C5A 113.7(3) . . ?
C6A O7A H7 100.8(14) . . ?
C3 C4B C5B 115.7(10) . . ?
C3 C4B H4B1 108.4 . . ?
C5B C4B H4B1 108.4 . . ?
C3 C4B H4B2 108.4 . . ?
C5B C4B H4B2 108.4 . . ?
H4B1 C4B H4B2 107.4 . . ?
C6B C5B C4B 114.9(7) . . ?
C6B C5B H5B1 108.5 . . ?
C4B C5B H5B1 108.5 . . ?
C6B C5B H5B2 108.5 . . ?
C4B C5B H5B2 108.5 . . ?
H5B1 C5B H5B2 107.5 . . ?
O8B C6B O7B 123.3(3) . . ?
O8B C6B C5B 122.9(2) . . ?
O7B C6B C5B 113.7(3) . . ?
C6B O7B H7 100.6(14) . . ?

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
C14 N9 C10 N11 58.66(11) . . . . ?
C16 N9 C10 N11 -57.92(11) . . . . ?
N9 C10 N11 C12 -59.06(11) . . . . ?
N9 C10 N11 C18 58.12(11) . . . . ?
C10 N11 C12 N13 58.73(11) . . . . ?
C18 N11 C12 N13 -58.91(11) . . . . ?
N11 C12 N13 C14 -58.50(11) . . . . ?
N11 C12 N13 C17 58.55(11) . . . . ?
C17 N13 C14 N9 -58.73(11) . . . . ?
C12 N13 C14 N9 58.26(10) . . . . ?
C10 N9 C14 N13 -58.14(10) . . . . ?
C16 N9 C14 N13 58.28(11) . . . . ?
C17 N15 C16 N9 58.60(11) . . . . ?
C18 N15 C16 N9 -58.69(11) . . . . ?
C14 N9 C16 N15 -58.25(11) . . . . ?
C10 N9 C16 N15 58.32(11) . . . . ?
C16 N15 C17 N13 -58.86(11) . . . . ?
C18 N15 C17 N13 58.48(11) . . . . ?
C14 N13 C17 N15 58.91(11) . . . . ?
C12 N13 C17 N15 -58.25(11) . . . . ?
C16 N15 C18 N11 58.38(10) . . . . ?
C17 N15 C18 N11 -59.10(10) . . . . ?
C10 N11 C18 N15 -58.17(10) . . . . ?
C12 N11 C18 N15 59.29(10) . . . . ?
O2 C3 C4A C5A -14.9(14) . . . . ?
O1 C3 C4A C5A 162.2(7) . . . . ?
C3 C4A C5A C6A -178.7(6) . . . . ?
C4A C5A C6A O8A 143.2(7) . . . . ?
C4A C5A C6A O7A -37.6(7) . . . . ?
O2 C3 C4B C5B 24.3(15) . . . . ?
O1 C3 C4B C5B -155.0(8) . . . . ?
C3 C4B C5B C6B 176.2(8) . . . . ?
C4B C5B C6B O8B -158.8(8) . . . . ?
C4B C5B C6B O7B 23.1(8) . . . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.046

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

data_2b_100K
_database_code_depnum_ccdc_archive 'CCDC 1970262'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2020-08-17 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT353_2b_100K             
;
PROBLEM: Long N-H (N0.87,N1.01A) N16 - H1_a . 1.24 Ang.
RESPONSE: Acidic hydrogen atoms were placed according to 
the difference map. Carbon-oxygen bond lengths, as well 
as angles at the heterocyclic nitrogen atom, indicate 
that this material is a co-crystal, and hydrogen atoms
 have been placed accordingly. This results in some long 
N-H bonds due to very strong hydrogen bonds between the 
acid and the base.
;
_vrf_PLAT780_2b_100K             
;
PROBLEM: Coordinates do not Form a Properly Connected Set Please Do !
RESPONSE: Acidic hydrogen atoms were placed according to 
the difference map. Carbon-oxygen bond lengths, as well 
as angles at the heterocyclic nitrogen atom, indicate 
that this material is a co-crystal, and hydrogen atoms
 have been placed accordingly. This results in some long 
N-H bonds due to very strong hydrogen bonds between the 
acid and the base.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '4,4-bipyridine oxalic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H8 N2), 2(C2 H2 O4)'
_chemical_formula_sum            'C24 H20 N4 O8'
_chemical_formula_weight         492.44

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                   8.740(1)
_cell_length_b                   9.849(1)
_cell_length_c                   13.663(2)
_cell_angle_alpha                73.285(2)
_cell_angle_beta                 72.292(2)
_cell_angle_gamma                72.343(2)
_cell_volume                     1042.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.34

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8768
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            25165
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.602
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5192
_reflns_number_gt                4440
_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 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'
_computing_publication_material  ?
_refine_special_details          
;
Acidic hydrogen atoms were placed according to the difference map. Carbon-oxygen
bond lengths, as well as angles at the heterocyclic nitrogen atom, indicate 
that this material is a co-crystal, and hydrogen atoms have been placed 
accordingly. This results in some long N-H bonds due to very strong 
hydrogen bonds between the acid and the base.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1196P)²+0.4187P] 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         5192
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1795
_refine_ls_wR_factor_gt          0.1713
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.71322(11) 0.39577(10) 0.36648(8) 0.0143(2) Uani 1 1 d . . . . .
H1 H 0.773(5) 0.503(4) 0.372(3) 0.106(13) Uiso 1 1 d . . . . .
O2 O 0.46616(12) 0.55562(11) 0.37629(8) 0.0164(2) Uani 1 1 d . . . . .
C3 C 0.55431(16) 0.43525(14) 0.37063(10) 0.0105(3) Uani 1 1 d . . . . .
C4 C 0.48581(16) 0.30720(14) 0.36973(10) 0.0112(3) Uani 1 1 d . . . . .
O5 O 0.56315(13) 0.18126(11) 0.39186(9) 0.0209(3) Uani 1 1 d . . . . .
O6 O 0.34444(12) 0.34966(10) 0.34640(8) 0.0156(2) Uani 1 1 d . . . . .
H6 H 0.306(4) 0.250(3) 0.354(2) 0.078(10) Uiso 1 1 d . . . . .
H24 H 1.066(5) 0.574(5) 0.126(3) 0.122(15) Uiso 1 1 d . . . . .
H19 H 0.616(5) 0.341(4) 0.112(3) 0.114(14) Uiso 1 1 d . . . . .
N7 N 0.21819(13) 0.14138(12) 0.36123(8) 0.0103(2) Uani 1 1 d . . . . .
C8 C 0.08129(15) 0.17746(13) 0.32521(10) 0.0098(3) Uani 1 1 d . . . . .
H8 H 0.040760 0.276311 0.293512 0.012 Uiso 1 1 calc R U . . .
C9 C -0.00265(15) 0.07436(13) 0.33299(10) 0.0099(3) Uani 1 1 d . . . . .
H9 H -0.100756 0.102806 0.308360 0.012 Uiso 1 1 calc R U . . .
C10 C 0.05825(15) -0.07142(13) 0.37731(9) 0.0079(2) Uani 1 1 d . . . . .
C11 C 0.20121(15) -0.10720(13) 0.41511(10) 0.0097(3) Uani 1 1 d . . . . .
H11 H 0.245596 -0.205237 0.446512 0.012 Uiso 1 1 calc R U . . .
C12 C 0.27659(15) 0.00235(13) 0.40600(10) 0.0105(3) Uani 1 1 d . . . . .
H12 H 0.372588 -0.021828 0.432284 0.013 Uiso 1 1 calc R U . . .
C13 C -0.02395(15) -0.18528(13) 0.38034(9) 0.0088(2) Uani 1 1 d . . . . .
C14 C -0.19082(15) -0.15111(14) 0.37764(10) 0.0118(3) Uani 1 1 d . . . . .
H14 H -0.256162 -0.054319 0.376795 0.014 Uiso 1 1 calc R U . . .
C15 C -0.25905(15) -0.26003(14) 0.37621(10) 0.0127(3) Uani 1 1 d . . . . .
H15 H -0.372275 -0.236125 0.374827 0.015 Uiso 1 1 calc R U . . .
N16 N -0.17176(14) -0.39787(13) 0.37670(9) 0.0120(2) Uani 1 1 d . . . . .
C17 C -0.01287(15) -0.43146(13) 0.38023(10) 0.0113(3) Uani 1 1 d . . . . .
H17 H 0.048882 -0.529339 0.381067 0.014 Uiso 1 1 calc R U . . .
C18 C 0.06577(15) -0.32973(13) 0.38271(10) 0.0100(3) Uani 1 1 d . . . . .
H18 H 0.178441 -0.357841 0.385969 0.012 Uiso 1 1 calc R U . . .
O19 O 0.65433(11) 0.43179(10) 0.11771(8) 0.0140(2) Uani 1 1 d . . . . .
O20 O 0.89769(12) 0.26984(10) 0.11888(8) 0.0139(2) Uani 1 1 d . . . . .
C21 C 0.80947(15) 0.39198(13) 0.11966(9) 0.0082(3) Uani 1 1 d . . . . .
C22 C 0.87690(15) 0.51901(13) 0.12372(9) 0.0083(3) Uani 1 1 d . . . . .
O23 O 0.78727(11) 0.64038(10) 0.12675(8) 0.0125(2) Uani 1 1 d . . . . .
O24 O 1.03249(11) 0.47908(10) 0.12397(8) 0.0122(2) Uani 1 1 d . . . . .
N25 N 1.14901(13) 0.68403(12) 0.12679(8) 0.0091(2) Uani 1 1 d . . . . .
C26 C 1.07083(15) 0.82540(14) 0.10844(10) 0.0103(3) Uani 1 1 d . . . . .
H26 H 0.963938 0.851964 0.095073 0.012 Uiso 1 1 calc R U . . .
C27 C 1.14113(15) 0.93410(13) 0.10835(10) 0.0098(3) Uani 1 1 d . . . . .
H27 H 1.082218 1.033406 0.096061 0.012 Uiso 1 1 calc R U . . .
C28 C 1.29996(14) 0.89646(13) 0.12655(9) 0.0066(2) Uani 1 1 d . . . . .
C29 C 1.37899(15) 0.74868(13) 0.14628(10) 0.0091(3) Uani 1 1 d . . . . .
H29 H 1.486270 0.718375 0.159451 0.011 Uiso 1 1 calc R U . . .
C30 C 1.29913(15) 0.64647(13) 0.14644(10) 0.0097(3) Uani 1 1 d . . . . .
H30 H 1.353031 0.545950 0.161050 0.012 Uiso 1 1 calc R U . . .
C31 C 1.38109(14) 1.00991(13) 0.12465(9) 0.0070(2) Uani 1 1 d . . . . .
C32 C 1.53013(15) 0.97266(13) 0.15607(10) 0.0102(3) Uani 1 1 d . . . . .
H32 H 1.581365 0.873213 0.179381 0.012 Uiso 1 1 calc R U . . .
C33 C 1.60174(16) 1.08200(14) 0.15279(10) 0.0112(3) Uani 1 1 d . . . . .
H33 H 1.701653 1.055663 0.175154 0.013 Uiso 1 1 calc R U . . .
N34 N 1.53528(13) 1.22350(12) 0.11925(8) 0.0096(2) Uani 1 1 d . . . . .
C35 C 1.39429(15) 1.26034(13) 0.08790(10) 0.0104(3) Uani 1 1 d . . . . .
H35 H 1.347907 1.360620 0.063150 0.013 Uiso 1 1 calc R U . . .
C36 C 1.31334(15) 1.15771(13) 0.09018(10) 0.0094(3) Uani 1 1 d . . . . .
H36 H 1.212545 1.187922 0.068413 0.011 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3117(15) . ?
O1 H1 1.34(4) . ?
O2 C3 1.2113(16) . ?
C3 C4 1.5557(17) . ?
C4 O5 1.2193(16) . ?
C4 O6 1.2855(16) . ?
O6 H6 1.10(3) . ?
N7 C12 1.3393(16) . ?
N7 C8 1.3415(16) . ?
N7 H6 1.46(3) . ?
C8 C9 1.3866(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3942(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.4046(16) . ?
C10 C13 1.4896(16) . ?
C11 C12 1.3848(16) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.3972(17) . ?
C13 C14 1.4034(17) . ?
C14 C15 1.3834(17) . ?
C14 H14 0.9500 . ?
C15 N16 1.3396(17) . ?
C15 H15 0.9500 . ?
N16 C17 1.3390(16) . ?
C17 C18 1.3888(16) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O19 C21 1.2985(15) . ?
O19 H19 1.07(4) . ?
O20 C21 1.2171(15) . ?
C21 C22 1.5565(18) . ?
C22 O23 1.2185(15) . ?
C22 O24 1.2968(15) . ?
O24 H24 1.07(4) . ?
N25 C30 1.3390(16) . ?
N25 C26 1.3396(16) . ?
N25 H24 1.48(4) . ?
C26 C27 1.3862(17) . ?
C26 H26 0.9500 . ?
C27 C28 1.4039(16) . ?
C27 H27 0.9500 . ?
C28 C29 1.3950(17) . ?
C28 C31 1.4848(17) . ?
C29 C30 1.3872(16) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.3941(17) . ?
C31 C32 1.4055(16) . ?
C32 C33 1.3846(17) . ?
C32 H32 0.9500 . ?
C33 N34 1.3390(17) . ?
C33 H33 0.9500 . ?
N34 C35 1.3394(16) . ?
C35 C36 1.3876(16) . ?
C35 H35 0.9500 . ?
C36 H36 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
C3 O1 H1 113.0(16) . . ?
O2 C3 O1 125.69(12) . . ?
O2 C3 C4 122.01(11) . . ?
O1 C3 C4 112.29(10) . . ?
O5 C4 O6 126.33(12) . . ?
O5 C4 C3 120.39(11) . . ?
O6 C4 C3 113.26(11) . . ?
C4 O6 H6 106.0(16) . . ?
C12 N7 C8 119.66(10) . . ?
C12 N7 H6 118.4(12) . . ?
C8 N7 H6 122.0(12) . . ?
N7 C8 C9 121.78(11) . . ?
N7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 119.39(11) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 118.08(11) . . ?
C9 C10 C13 120.26(11) . . ?
C11 C10 C13 121.62(11) . . ?
C12 C11 C10 119.11(11) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N7 C12 C11 121.96(11) . . ?
N7 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C18 C13 C14 117.95(11) . . ?
C18 C13 C10 120.36(11) . . ?
C14 C13 C10 121.66(11) . . ?
C15 C14 C13 119.23(12) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
N16 C15 C14 122.59(12) . . ?
N16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C17 N16 C15 118.46(11) . . ?
N16 C17 C18 123.00(11) . . ?
N16 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
C17 C18 C13 118.75(11) . . ?
C17 C18 H18 120.6 . . ?
C13 C18 H18 120.6 . . ?
C21 O19 H19 110(2) . . ?
O20 C21 O19 125.79(11) . . ?
O20 C21 C22 121.35(12) . . ?
O19 C21 C22 112.86(11) . . ?
O23 C22 O24 126.32(11) . . ?
O23 C22 C21 121.14(12) . . ?
O24 C22 C21 112.54(11) . . ?
C22 O24 H24 106(2) . . ?
C30 N25 C26 119.01(10) . . ?
C30 N25 H24 122.0(16) . . ?
C26 N25 H24 118.9(16) . . ?
N25 C26 C27 122.01(11) . . ?
N25 C26 H26 119.0 . . ?
C27 C26 H26 119.0 . . ?
C26 C27 C28 119.56(11) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C29 C28 C27 117.63(11) . . ?
C29 C28 C31 121.18(11) . . ?
C27 C28 C31 121.20(11) . . ?
C30 C29 C28 119.23(11) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
N25 C30 C29 122.54(11) . . ?
N25 C30 H30 118.7 . . ?
C29 C30 H30 118.7 . . ?
C36 C31 C32 117.38(11) . . ?
C36 C31 C28 121.19(11) . . ?
C32 C31 C28 121.43(11) . . ?
C33 C32 C31 119.50(11) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
N34 C33 C32 122.40(11) . . ?
N34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C33 N34 C35 118.68(11) . . ?
N34 C35 C36 122.55(11) . . ?
N34 C35 H35 118.7 . . ?
C36 C35 H35 118.7 . . ?
C35 C36 C31 119.49(11) . . ?
C35 C36 H36 120.3 . . ?
C31 C36 H36 120.3 . . ?

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
O2 C3 C4 O5 -160.48(14) . . . . ?
O1 C3 C4 O5 18.43(17) . . . . ?
O2 C3 C4 O6 18.11(18) . . . . ?
O1 C3 C4 O6 -162.98(11) . . . . ?
C12 N7 C8 C9 0.05(19) . . . . ?
N7 C8 C9 C10 -1.42(19) . . . . ?
C8 C9 C10 C11 1.69(18) . . . . ?
C8 C9 C10 C13 -176.16(11) . . . . ?
C9 C10 C11 C12 -0.69(18) . . . . ?
C13 C10 C11 C12 177.13(11) . . . . ?
C8 N7 C12 C11 1.01(19) . . . . ?
C10 C11 C12 N7 -0.67(19) . . . . ?
C9 C10 C13 C18 153.64(12) . . . . ?
C11 C10 C13 C18 -24.13(17) . . . . ?
C9 C10 C13 C14 -24.36(17) . . . . ?
C11 C10 C13 C14 157.87(12) . . . . ?
C18 C13 C14 C15 -0.73(18) . . . . ?
C10 C13 C14 C15 177.31(11) . . . . ?
C13 C14 C15 N16 -0.39(19) . . . . ?
C14 C15 N16 C17 0.98(19) . . . . ?
C15 N16 C17 C18 -0.43(19) . . . . ?
N16 C17 C18 C13 -0.69(19) . . . . ?
C14 C13 C18 C17 1.23(17) . . . . ?
C10 C13 C18 C17 -176.84(10) . . . . ?
O20 C21 C22 O23 -178.42(11) . . . . ?
O19 C21 C22 O23 1.36(18) . . . . ?
O20 C21 C22 O24 1.24(18) . . . . ?
O19 C21 C22 O24 -178.98(9) . . . . ?
C30 N25 C26 C27 0.51(18) . . . . ?
N25 C26 C27 C28 0.88(19) . . . . ?
C26 C27 C28 C29 -1.31(18) . . . . ?
C26 C27 C28 C31 178.57(11) . . . . ?
C27 C28 C29 C30 0.41(17) . . . . ?
C31 C28 C29 C30 -179.46(11) . . . . ?
C26 N25 C30 C29 -1.47(18) . . . . ?
C28 C29 C30 N25 1.00(19) . . . . ?
C29 C28 C31 C36 170.60(10) . . . . ?
C27 C28 C31 C36 -9.27(19) . . . . ?
C29 C28 C31 C32 -8.50(19) . . . . ?
C27 C28 C31 C32 171.62(11) . . . . ?
C36 C31 C32 C33 0.70(18) . . . . ?
C28 C31 C32 C33 179.84(11) . . . . ?
C31 C32 C33 N34 -0.9(2) . . . . ?
C32 C33 N34 C35 0.09(19) . . . . ?
C33 N34 C35 C36 0.89(19) . . . . ?
N34 C35 C36 C31 -1.04(19) . . . . ?
C32 C31 C36 C35 0.21(18) . . . . ?
C28 C31 C36 C35 -178.93(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6 N7 1.10(3) 1.46(3) 2.5425(14) 166(3) . yes
O24 H24 N25 1.07(4) 1.48(4) 2.5354(14) 167(4) . yes
O19 H19 N34 1.07(4) 1.50(4) 2.5588(14) 169(4) 1_445 yes

_refine_diff_density_max         1.026
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.114

####################################################################### 
# 
# 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_2b_RT
_database_code_depnum_ccdc_archive 'CCDC 1970261'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2020-08-17 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT353_2b_RT               
;
PROBLEM: Long N-H (N0.87,N1.01A) N16 - H1_b . 1.12 Ang.
RESPONSE: Acidic hydrogen atoms were placed according to 
the difference map. Carbon-oxygen bond lengths, as well as 
angles at the heterocyclic nitrogen atom, indicate that 
this material is a co-crystal, and hydrogen atoms have 
been placed accordingly. This results in some long N-H 
bonds due to very strong hydrogen bonds between the 
acid and the base.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '4,4-bipyridine oxalic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H8 N2), 2(C2 H2 O4)'
_chemical_formula_sum            'C24 H20 N4 O8'
_chemical_formula_weight         492.44

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                   8.7731(5)
_cell_length_b                   9.8652(5)
_cell_length_c                   13.9929(7)
_cell_angle_alpha                73.741(2)
_cell_angle_beta                 72.890(2)
_cell_angle_gamma                72.483(2)
_cell_volume                     1079.2(1)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7354
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.27

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.198
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8925
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'INCOATEC I\ms 3.0'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_detector                 'charge integrating pixel array detector'
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'multilayer mirror optics'

_diffrn_reflns_number            42048
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.214
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5389
_reflns_number_gt                2798
_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 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'
_computing_publication_material  ?
_refine_special_details          
;
Acidic hydrogen atoms were placed according to the difference map. Carbon-oxygen
bond lengths, as well as angles at the heterocyclic nitrogen atom, indicate 
that this material is a co-crystal, and hydrogen atoms have been placed 
accordingly. This results in some long N-H bonds due to very strong 
hydrogen bonds between the acid and the base.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1471P)²+0.6337P] 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         5389
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0936
_refine_ls_wR_factor_ref         0.2930
_refine_ls_wR_factor_gt          0.2370
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2139(3) 0.6025(2) 0.6314(2) 0.0523(7) Uani 1 1 d . . . . .
H1 H -0.283(5) 0.487(5) 0.627(3) 0.094(15) Uiso 1 1 d . . . . .
O2 O 0.0295(3) 0.4437(3) 0.6255(2) 0.0586(7) Uani 1 1 d . . . . .
C3 C -0.0560(4) 0.5643(3) 0.6286(2) 0.0391(7) Uani 1 1 d . . . . .
C4 C 0.0101(4) 0.6916(3) 0.6295(2) 0.0399(7) Uani 1 1 d . . . . .
O5 O -0.0642(3) 0.8156(3) 0.6088(2) 0.0716(9) Uani 1 1 d . . . . .
O6 O 0.1526(3) 0.6495(3) 0.6514(2) 0.0562(7) Uani 1 1 d . . . . .
H6 H 0.184(4) 0.745(4) 0.638(2) 0.053(10) Uiso 1 1 d . . . . .
N7 N 0.2804(3) 0.8582(3) 0.63745(19) 0.0382(6) Uani 1 1 d . . . . .
C8 C 0.4162(4) 0.8232(3) 0.6724(2) 0.0376(7) Uani 1 1 d . . . . .
H8 H 0.456770 0.726757 0.701989 0.045 Uiso 1 1 calc R U . . .
C9 C 0.4981(3) 0.9263(3) 0.6659(2) 0.0345(7) Uani 1 1 d . . . . .
H9 H 0.593195 0.899160 0.690193 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4374(3) 1.0707(3) 0.6228(2) 0.0295(6) Uani 1 1 d . . . . .
C11 C 0.2966(4) 1.1049(3) 0.5856(2) 0.0379(7) Uani 1 1 d . . . . .
H11 H 0.253502 1.200139 0.555029 0.045 Uiso 1 1 calc R U . . .
C12 C 0.2220(4) 0.9961(3) 0.5947(2) 0.0389(7) Uani 1 1 d . . . . .
H12 H 0.127644 1.019543 0.570068 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5209(3) 1.1842(3) 0.6208(2) 0.0322(7) Uani 1 1 d . . . . .
C14 C 0.6855(4) 1.1516(4) 0.6241(2) 0.0418(8) Uani 1 1 d . . . . .
H14 H 0.748733 1.056888 0.625651 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7544(4) 1.2585(4) 0.6250(3) 0.0455(8) Uani 1 1 d . . . . .
H15 H 0.864432 1.234335 0.627337 0.055 Uiso 1 1 calc R U . . .
N16 N 0.6692(3) 1.3961(3) 0.6226(2) 0.0413(7) Uani 1 1 d . . . . .
C17 C 0.5117(4) 1.4297(3) 0.6185(3) 0.0441(8) Uani 1 1 d . . . . .
H17 H 0.452224 1.525555 0.616616 0.053 Uiso 1 1 calc R U . . .
C18 C 0.4326(4) 1.3280(3) 0.6168(2) 0.0393(7) Uani 1 1 d . . . . .
H18 H 0.323080 1.355524 0.613015 0.047 Uiso 1 1 calc R U . . .
O19 O 0.8424(3) 0.5676(2) 0.8844(2) 0.0508(7) Uani 1 1 d . . . . .
H19 H 0.874(8) 0.655(7) 0.881(5) 0.16(3) Uiso 1 1 d . . . . .
H24 H 0.440(7) 0.442(6) 0.876(4) 0.13(2) Uiso 1 1 d . . . . .
O20 O 0.6038(3) 0.7297(2) 0.8783(2) 0.0496(6) Uani 1 1 d . . . . .
C21 C 0.6908(3) 0.6078(3) 0.8797(2) 0.0323(7) Uani 1 1 d . . . . .
C22 C 0.6239(3) 0.4810(3) 0.8760(2) 0.0311(6) Uani 1 1 d . . . . .
O23 O 0.7111(3) 0.3603(2) 0.87441(19) 0.0462(6) Uani 1 1 d . . . . .
O24 O 0.4705(3) 0.5208(2) 0.87398(19) 0.0460(6) Uani 1 1 d . . . . .
N25 N 0.3502(3) 0.3152(3) 0.87138(18) 0.0345(6) Uani 1 1 d . . . . .
C26 C 0.4270(4) 0.1750(3) 0.8901(2) 0.0391(7) Uani 1 1 d . . . . .
H26 H 0.531102 0.149113 0.903199 0.047 Uiso 1 1 calc R U . . .
C27 C 0.3562(3) 0.0669(3) 0.8908(2) 0.0382(7) Uani 1 1 d . . . . .
H27 H 0.413753 -0.029912 0.902899 0.046 Uiso 1 1 calc R U . . .
C28 C 0.1991(3) 0.1021(3) 0.87329(19) 0.0262(6) Uani 1 1 d . . . . .
C29 C 0.1220(3) 0.2494(3) 0.8535(2) 0.0346(7) Uani 1 1 d . . . . .
H29 H 0.017309 0.279178 0.840917 0.042 Uiso 1 1 calc R U . . .
C30 C 0.2020(4) 0.3510(3) 0.8525(2) 0.0385(7) Uani 1 1 d . . . . .
H30 H 0.149549 0.448983 0.838042 0.046 Uiso 1 1 calc R U . . .
C31 C 0.1192(3) -0.0108(3) 0.87593(19) 0.0281(6) Uani 1 1 d . . . . .
C32 C 0.1858(3) -0.1576(3) 0.9091(2) 0.0357(7) Uani 1 1 d . . . . .
H32 H 0.284774 -0.187289 0.929253 0.043 Uiso 1 1 calc R U . . .
C33 C 0.1049(4) -0.2590(3) 0.9119(2) 0.0396(7) Uani 1 1 d . . . . .
H33 H 0.150201 -0.356567 0.935870 0.047 Uiso 1 1 calc R U . . .
N34 N -0.0350(3) -0.2239(3) 0.88203(19) 0.0355(6) Uani 1 1 d . . . . .
C35 C -0.1011(4) -0.0841(3) 0.8498(3) 0.0423(8) Uani 1 1 d . . . . .
H35 H -0.199528 -0.058627 0.829440 0.051 Uiso 1 1 calc R U . . .
C36 C -0.0291(4) 0.0250(3) 0.8454(2) 0.0382(7) Uani 1 1 d . . . . .
H36 H -0.078778 0.121691 0.822316 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.313(3) . ?
O1 H1 1.46(5) . ?
O2 C3 1.205(4) . ?
C3 C4 1.538(4) . ?
C4 O5 1.200(4) . ?
C4 O6 1.292(4) . ?
O6 H6 1.01(4) . ?
N7 C12 1.332(4) . ?
N7 C8 1.333(4) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(4) . ?
C10 C13 1.502(4) . ?
C11 C12 1.377(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.391(4) . ?
C13 C14 1.393(4) . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 N16 1.335(4) . ?
C15 H15 0.9300 . ?
N16 C17 1.336(4) . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
O19 C21 1.285(3) . ?
O19 H19 0.97(7) . ?
O20 C21 1.213(3) . ?
C21 C22 1.552(4) . ?
C22 O23 1.209(3) . ?
C22 O24 1.290(3) . ?
O24 H24 0.88(6) . ?
N25 C30 1.326(4) . ?
N25 C26 1.332(4) . ?
C26 C27 1.384(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.394(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.392(4) . ?
C28 C31 1.471(4) . ?
C29 C30 1.382(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.388(4) . ?
C31 C36 1.402(4) . ?
C32 C33 1.377(4) . ?
C32 H32 0.9300 . ?
C33 N34 1.328(4) . ?
C33 H33 0.9300 . ?
N34 C35 1.329(4) . ?
C35 C36 1.381(4) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 115.0(17) . . ?
O2 C3 O1 124.6(3) . . ?
O2 C3 C4 122.9(3) . . ?
O1 C3 C4 112.5(3) . . ?
O5 C4 O6 125.3(3) . . ?
O5 C4 C3 121.8(3) . . ?
O6 C4 C3 112.8(3) . . ?
C4 O6 H6 102.0(19) . . ?
C12 N7 C8 119.4(3) . . ?
N7 C8 C9 121.7(3) . . ?
N7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 117.9(3) . . ?
C9 C10 C13 119.6(3) . . ?
C11 C10 C13 122.5(3) . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N7 C12 C11 122.2(3) . . ?
N7 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C18 C13 C14 117.6(3) . . ?
C18 C13 C10 119.8(3) . . ?
C14 C13 C10 122.6(3) . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N16 C15 C14 122.3(3) . . ?
N16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 N16 C17 118.3(3) . . ?
N16 C17 C18 123.1(3) . . ?
N16 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
C17 C18 C13 118.5(3) . . ?
C17 C18 H18 120.7 . . ?
C13 C18 H18 120.7 . . ?
C21 O19 H19 106(4) . . ?
O20 C21 O19 126.1(3) . . ?
O20 C21 C22 121.2(3) . . ?
O19 C21 C22 112.7(2) . . ?
O23 C22 O24 125.9(3) . . ?
O23 C22 C21 121.5(3) . . ?
O24 C22 C21 112.5(2) . . ?
C22 O24 H24 107(4) . . ?
C30 N25 C26 118.6(2) . . ?
N25 C26 C27 121.9(3) . . ?
N25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C28 120.4(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 116.5(2) . . ?
C29 C28 C31 121.9(2) . . ?
C27 C28 C31 121.6(3) . . ?
C30 C29 C28 119.6(3) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
N25 C30 C29 123.0(3) . . ?
N25 C30 H30 118.5 . . ?
C29 C30 H30 118.5 . . ?
C32 C31 C36 116.6(3) . . ?
C32 C31 C28 122.0(2) . . ?
C36 C31 C28 121.4(3) . . ?
C33 C32 C31 119.8(3) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
N34 C33 C32 123.1(3) . . ?
N34 C33 H33 118.5 . . ?
C32 C33 H33 118.5 . . ?
C33 N34 C35 118.2(3) . . ?
N34 C35 C36 122.5(3) . . ?
N34 C35 H35 118.7 . . ?
C36 C35 H35 118.7 . . ?
C35 C36 C31 119.7(3) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 O5 162.3(4) . . . . ?
O1 C3 C4 O5 -17.7(5) . . . . ?
O2 C3 C4 O6 -15.7(5) . . . . ?
O1 C3 C4 O6 164.3(3) . . . . ?
C12 N7 C8 C9 0.3(5) . . . . ?
N7 C8 C9 C10 0.6(5) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C8 C9 C10 C13 176.7(3) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C13 C10 C11 C12 -176.7(3) . . . . ?
C8 N7 C12 C11 -0.4(5) . . . . ?
C10 C11 C12 N7 -0.4(5) . . . . ?
C9 C10 C13 C18 -154.7(3) . . . . ?
C11 C10 C13 C18 23.2(4) . . . . ?
C9 C10 C13 C14 24.5(4) . . . . ?
C11 C10 C13 C14 -157.6(3) . . . . ?
C18 C13 C14 C15 1.1(5) . . . . ?
C10 C13 C14 C15 -178.1(3) . . . . ?
C13 C14 C15 N16 -0.1(5) . . . . ?
C14 C15 N16 C17 -0.5(5) . . . . ?
C15 N16 C17 C18 0.2(5) . . . . ?
N16 C17 C18 C13 0.8(5) . . . . ?
C14 C13 C18 C17 -1.3(5) . . . . ?
C10 C13 C18 C17 177.9(3) . . . . ?
O20 C21 C22 O23 177.9(3) . . . . ?
O19 C21 C22 O23 -2.3(4) . . . . ?
O20 C21 C22 O24 -1.6(4) . . . . ?
O19 C21 C22 O24 178.3(2) . . . . ?
C30 N25 C26 C27 -0.2(5) . . . . ?
N25 C26 C27 C28 -1.2(5) . . . . ?
C26 C27 C28 C29 1.4(4) . . . . ?
C26 C27 C28 C31 -178.5(3) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
C31 C28 C29 C30 179.6(3) . . . . ?
C26 N25 C30 C29 1.3(5) . . . . ?
C28 C29 C30 N25 -1.1(5) . . . . ?
C29 C28 C31 C32 -171.1(3) . . . . ?
C27 C28 C31 C32 8.8(4) . . . . ?
C29 C28 C31 C36 8.5(4) . . . . ?
C27 C28 C31 C36 -171.6(3) . . . . ?
C36 C31 C32 C33 -0.9(4) . . . . ?
C28 C31 C32 C33 178.8(3) . . . . ?
C31 C32 C33 N34 1.5(5) . . . . ?
C32 C33 N34 C35 -1.4(5) . . . . ?
C33 N34 C35 C36 0.7(5) . . . . ?
N34 C35 C36 C31 -0.1(5) . . . . ?
C32 C31 C36 C35 0.2(4) . . . . ?
C28 C31 C36 C35 -179.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6 N7 1.01(4) 1.59(4) 2.563(3) 160(3) . yes
O19 H19 N34 0.97(7) 1.63(7) 2.581(3) 166(6) 1_665 yes
O24 H24 N25 0.88(6) 1.70(6) 2.566(3) 168(6) . yes

_refine_diff_density_max         0.686
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_1c_100K
_database_code_depnum_ccdc_archive 'CCDC 1970260'
loop_
_audit_author_name
_audit_author_address
'Jean Lombard'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            
;
bis-hexamethylenetetramine succinic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 O4, 2(C6 H12 N4)'
_chemical_formula_sum            'C16 H30 N8 O4'
_chemical_formula_weight         398.48

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   21.654(3)
_cell_length_b                   6.948(1)
_cell_length_c                   25.748(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.148(2)
_cell_angle_gamma                90
_cell_volume                     3800.7(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      28.32

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9234
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            36844
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.612
_diffrn_reflns_theta_max         28.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4758
_reflns_number_gt                4243
_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 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0648P)²+4.2093P] 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         4758
_refine_ls_number_parameters     326
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
H1 H 0.4018(11) 0.071(3) 0.5315(9) 0.053(7) Uiso 1 1 d . . . . .
C3B C 0.3732(8) 0.314(3) 0.5055(10) 0.0094(11) Uani 0.414(4) 1 d . . P A 1
C4B C 0.3173(8) 0.386(3) 0.4603(7) 0.0155(10) Uani 0.414(4) 1 d . . P A 1
H4B1 H 0.331046 0.381983 0.425796 0.019 Uiso 0.414(4) 1 calc R U P A 1
H4B2 H 0.280952 0.298118 0.458200 0.019 Uiso 0.414(4) 1 calc R U P A 1
N9 N 0.30408(5) 0.46204(15) 0.66699(4) 0.0182(2) Uani 1 1 d . . . . .
C10 C 0.35367(6) 0.33951(18) 0.65164(5) 0.0194(3) Uani 1 1 d . . . . .
H10A H 0.333810 0.244216 0.624992 0.023 Uiso 1 1 calc R U . . .
H10B H 0.382099 0.420882 0.635151 0.023 Uiso 1 1 calc R U . . .
H7B H 0.226(3) 0.919(8) 0.3957(16) 0.046(16) Uiso 0.414(4) 1 d D . P A 1
N11 N 0.39075(5) 0.23765(15) 0.69727(4) 0.0148(2) Uani 1 1 d . . . . .
C12 C 0.34731(5) 0.11867(16) 0.72117(5) 0.0145(2) Uani 1 1 d . . . . .
H12A H 0.327362 0.021767 0.695046 0.017 Uiso 1 1 calc R U . . .
H12B H 0.371544 0.048957 0.752034 0.017 Uiso 1 1 calc R U . . .
N13 N 0.29794(5) 0.23380(15) 0.73839(4) 0.0173(2) Uani 1 1 d . . . . .
C14 C 0.26286(6) 0.33621(18) 0.69223(6) 0.0225(3) Uani 1 1 d . . . . .
H14A H 0.229737 0.415695 0.703317 0.027 Uiso 1 1 calc R U . . .
H14B H 0.241906 0.241261 0.665958 0.027 Uiso 1 1 calc R U . . .
C15 C 0.33510(5) 0.60147(17) 0.70770(5) 0.0149(2) Uani 1 1 d . . . . .
H15A H 0.363527 0.685681 0.692031 0.018 Uiso 1 1 calc R U . . .
H15B H 0.302608 0.683834 0.718717 0.018 Uiso 1 1 calc R U . . .
N16 N 0.37138(4) 0.50423(14) 0.75437(4) 0.0135(2) Uani 1 1 d . . . . .
C17 C 0.32877(6) 0.37744(18) 0.77682(5) 0.0186(2) Uani 1 1 d . . . . .
H17A H 0.353020 0.310239 0.808131 0.022 Uiso 1 1 calc R U . . .
H17B H 0.296173 0.456676 0.788768 0.022 Uiso 1 1 calc R U . . .
C18 C 0.41883(5) 0.38229(17) 0.73660(5) 0.0153(2) Uani 1 1 d . . . . .
H18A H 0.443996 0.315805 0.767626 0.018 Uiso 1 1 calc R U . . .
H18B H 0.447725 0.464958 0.720992 0.018 Uiso 1 1 calc R U . . .
N19 N 0.53824(5) 0.05170(14) 0.42552(4) 0.0129(2) Uani 1 1 d . . . . .
C20 C 0.49634(6) 0.18304(18) 0.44852(5) 0.0175(2) Uani 1 1 d . . . . .
H20A H 0.473982 0.108308 0.471924 0.021 Uiso 1 1 calc R U . . .
H20B H 0.522292 0.281635 0.470403 0.021 Uiso 1 1 calc R U . . .
N21 N 0.44996(5) 0.27911(15) 0.40758(4) 0.0172(2) Uani 1 1 d . . . . .
C22 C 0.48476(6) 0.38868(17) 0.37356(5) 0.0176(2) Uani 1 1 d . . . . .
H22A H 0.454313 0.454873 0.345625 0.021 Uiso 1 1 calc R U . . .
H22B H 0.510552 0.488432 0.395099 0.021 Uiso 1 1 calc R U . . .
N23 N 0.52606(5) 0.26580(15) 0.34851(4) 0.0161(2) Uani 1 1 d . . . . .
C24 C 0.57072(5) 0.16919(18) 0.39070(5) 0.0159(2) Uani 1 1 d . . . . .
H24A H 0.597212 0.267238 0.412345 0.019 Uiso 1 1 calc R U . . .
H24B H 0.598741 0.085031 0.374566 0.019 Uiso 1 1 calc R U . . .
C25 C 0.49802(6) -0.09139(17) 0.39157(5) 0.0157(2) Uani 1 1 d . . . . .
H25A H 0.525161 -0.178106 0.375258 0.019 Uiso 1 1 calc R U . . .
H25B H 0.475559 -0.170711 0.413929 0.019 Uiso 1 1 calc R U . . .
N26 N 0.45189(5) -0.00001(15) 0.34968(4) 0.0161(2) Uani 1 1 d . . . . .
C27 C 0.48689(6) 0.11720(18) 0.31729(4) 0.0172(2) Uani 1 1 d . . . . .
H27A H 0.514150 0.031804 0.300708 0.021 Uiso 1 1 calc R U . . .
H27B H 0.456601 0.180037 0.288564 0.021 Uiso 1 1 calc R U . . .
C28 C 0.41275(6) 0.13093(19) 0.37480(5) 0.0189(3) Uani 1 1 d . . . . .
H28A H 0.381519 0.194431 0.346903 0.023 Uiso 1 1 calc R U . . .
H28B H 0.389377 0.054697 0.397144 0.023 Uiso 1 1 calc R U . . .
O1A O 0.3655(7) 0.129(4) 0.5072(6) 0.026(3) Uani 0.414(4) 1 d . . P A 1
O2A O 0.3968(5) 0.402(2) 0.5382(5) 0.0228(15) Uani 0.414(4) 1 d . . P A 1
C5A C 0.32717(12) 0.5991(3) 0.45343(10) 0.0202(5) Uani 0.586(4) 1 d . . P A 2
H5A1 H 0.332047 0.679588 0.485706 0.024 Uiso 0.586(4) 1 calc R U P A 2
H5A2 H 0.367364 0.603190 0.440552 0.024 Uiso 0.586(4) 1 calc R U P A 2
C6A C 0.2752(2) 0.6823(8) 0.4114(2) 0.0148(8) Uani 0.586(4) 1 d . . P A 2
O7B O 0.24322(15) 0.8635(4) 0.42766(10) 0.0294(9) Uani 0.414(4) 1 d D . P A 1
O8B O 0.2309(3) 0.5910(13) 0.3892(3) 0.0212(12) Uani 0.414(4) 1 d . . P A 1
O1B O 0.3661(5) 0.107(3) 0.5067(5) 0.0210(14) Uani 0.586(4) 1 d . . P A 2
O2B O 0.4110(3) 0.3992(14) 0.5325(4) 0.0201(9) Uani 0.586(4) 1 d . . P A 2
C5B C 0.2964(2) 0.5913(5) 0.47025(13) 0.0251(9) Uani 0.414(4) 1 d . . P A 1
H5B1 H 0.269897 0.587913 0.497517 0.030 Uiso 0.414(4) 1 calc R U P A 1
H5B2 H 0.334094 0.670120 0.484195 0.030 Uiso 0.414(4) 1 calc R U P A 1
C6B C 0.2600(3) 0.6850(12) 0.4208(3) 0.0144(11) Uani 0.414(4) 1 d . . P A 1
O7A O 0.28129(9) 0.8689(2) 0.40539(8) 0.0302(6) Uani 0.586(4) 1 d D . P A 2
O8A O 0.2448(3) 0.5981(10) 0.3788(2) 0.0345(12) Uani 0.586(4) 1 d . . P A 2
C4A C 0.3135(6) 0.3919(19) 0.4674(5) 0.0155(10) Uani 0.586(4) 1 d . . P A 2
H4A1 H 0.273880 0.390168 0.481172 0.019 Uiso 0.586(4) 1 calc R U P A 2
H4A2 H 0.306604 0.314262 0.434569 0.019 Uiso 0.586(4) 1 calc R U P A 2
C3A C 0.3624(5) 0.300(2) 0.5061(7) 0.0094(11) Uani 0.586(4) 1 d . . P A 2
H7A H 0.2489(19) 0.917(7) 0.3803(17) 0.068(15) Uiso 0.586(4) 1 d D . 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
C3B O2A 1.08(3) . ?
C3B O1A 1.30(4) . ?
C3B C4B 1.59(3) . ?
C4B C5B 1.531(19) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
N9 C10 1.4825(17) . ?
N9 C14 1.4859(17) . ?
N9 C15 1.4886(15) . ?
C10 N11 1.4701(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N11 C18 1.4721(15) . ?
N11 C12 1.4733(15) . ?
C12 N13 1.4706(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N13 C14 1.4651(17) . ?
N13 C17 1.4715(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N16 1.4673(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
N16 C18 1.4712(15) . ?
N16 C17 1.4723(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N19 C24 1.4861(15) . ?
N19 C20 1.4880(15) . ?
N19 C25 1.4889(15) . ?
C20 N21 1.4684(15) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N21 C28 1.4692(16) . ?
N21 C22 1.4731(16) . ?
C22 N23 1.4723(16) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N23 C24 1.4696(15) . ?
N23 C27 1.4724(15) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N26 1.4654(15) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N26 C28 1.4753(16) . ?
N26 C27 1.4757(15) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
O1A H1 0.99(3) . ?
C5A C6A 1.517(6) . ?
C5A C4A 1.527(13) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A O8A 1.125(8) . ?
C6A O7A 1.315(6) . ?
O7B C6B 1.313(8) . ?
O7B H7B 0.92(3) . ?
O8B C6B 1.134(10) . ?
O1B C3A 1.34(3) . ?
O1B H1 0.94(2) . ?
O2B C3A 1.331(14) . ?
C5B C6B 1.509(8) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
O7A H7A 0.92(3) . ?
C4A C3A 1.45(2) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2A C3B O1A 125(2) . . ?
O2A C3B C4B 125(2) . . ?
O1A C3B C4B 104.5(16) . . ?
C5B C4B C3B 112.1(14) . . ?
C5B C4B H4B1 109.2 . . ?
C3B C4B H4B1 109.2 . . ?
C5B C4B H4B2 109.2 . . ?
C3B C4B H4B2 109.2 . . ?
H4B1 C4B H4B2 107.9 . . ?
C10 N9 C14 107.82(10) . . ?
C10 N9 C15 108.05(9) . . ?
C14 N9 C15 107.59(10) . . ?
N11 C10 N9 112.04(10) . . ?
N11 C10 H10A 109.2 . . ?
N9 C10 H10A 109.2 . . ?
N11 C10 H10B 109.2 . . ?
N9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 N11 C18 108.07(9) . . ?
C10 N11 C12 108.05(9) . . ?
C18 N11 C12 107.93(9) . . ?
N13 C12 N11 112.38(9) . . ?
N13 C12 H12A 109.1 . . ?
N11 C12 H12A 109.1 . . ?
N13 C12 H12B 109.1 . . ?
N11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C14 N13 C12 108.22(10) . . ?
C14 N13 C17 108.22(10) . . ?
C12 N13 C17 108.04(9) . . ?
N13 C14 N9 112.31(9) . . ?
N13 C14 H14A 109.1 . . ?
N9 C14 H14A 109.1 . . ?
N13 C14 H14B 109.1 . . ?
N9 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
N16 C15 N9 111.98(9) . . ?
N16 C15 H15A 109.2 . . ?
N9 C15 H15A 109.2 . . ?
N16 C15 H15B 109.2 . . ?
N9 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 N16 C18 107.82(9) . . ?
C15 N16 C17 108.66(9) . . ?
C18 N16 C17 107.81(9) . . ?
N13 C17 N16 112.28(10) . . ?
N13 C17 H17A 109.1 . . ?
N16 C17 H17A 109.1 . . ?
N13 C17 H17B 109.1 . . ?
N16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
N16 C18 N11 112.74(9) . . ?
N16 C18 H18A 109.0 . . ?
N11 C18 H18A 109.0 . . ?
N16 C18 H18B 109.0 . . ?
N11 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C24 N19 C20 107.42(9) . . ?
C24 N19 C25 107.69(9) . . ?
C20 N19 C25 108.10(9) . . ?
N21 C20 N19 112.22(9) . . ?
N21 C20 H20A 109.2 . . ?
N19 C20 H20A 109.2 . . ?
N21 C20 H20B 109.2 . . ?
N19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 N21 C28 108.48(10) . . ?
C20 N21 C22 107.71(10) . . ?
C28 N21 C22 107.90(9) . . ?
N23 C22 N21 112.62(9) . . ?
N23 C22 H22A 109.1 . . ?
N21 C22 H22A 109.1 . . ?
N23 C22 H22B 109.1 . . ?
N21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 N23 C22 108.04(9) . . ?
C24 N23 C27 108.10(9) . . ?
C22 N23 C27 108.14(9) . . ?
N23 C24 N19 112.10(9) . . ?
N23 C24 H24A 109.2 . . ?
N19 C24 H24A 109.2 . . ?
N23 C24 H24B 109.2 . . ?
N19 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
N26 C25 N19 112.39(9) . . ?
N26 C25 H25A 109.1 . . ?
N19 C25 H25A 109.1 . . ?
N26 C25 H25B 109.1 . . ?
N19 C25 H25B 109.1 . . ?
H25A C25 H25B 107.9 . . ?
C25 N26 C28 108.19(9) . . ?
C25 N26 C27 107.68(9) . . ?
C28 N26 C27 107.99(10) . . ?
N23 C27 N26 112.51(9) . . ?
N23 C27 H27A 109.1 . . ?
N26 C27 H27A 109.1 . . ?
N23 C27 H27B 109.1 . . ?
N26 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
N21 C28 N26 112.71(9) . . ?
N21 C28 H28A 109.0 . . ?
N26 C28 H28A 109.0 . . ?
N21 C28 H28B 109.0 . . ?
N26 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C3B O1A H1 109(2) . . ?
C6A C5A C4A 112.2(5) . . ?
C6A C5A H5A1 109.2 . . ?
C4A C5A H5A1 109.2 . . ?
C6A C5A H5A2 109.2 . . ?
C4A C5A H5A2 109.2 . . ?
H5A1 C5A H5A2 107.9 . . ?
O8A C6A O7A 118.9(5) . . ?
O8A C6A C5A 125.5(5) . . ?
O7A C6A C5A 112.5(4) . . ?
C6B O7B H7B 110(4) . . ?
C3A O1B H1 108(2) . . ?
C6B C5B C4B 112.5(8) . . ?
C6B C5B H5B1 109.1 . . ?
C4B C5B H5B1 109.1 . . ?
C6B C5B H5B2 109.1 . . ?
C4B C5B H5B2 109.1 . . ?
H5B1 C5B H5B2 107.8 . . ?
O8B C6B O7B 120.7(7) . . ?
O8B C6B C5B 118.9(8) . . ?
O7B C6B C5B 114.1(5) . . ?
C6A O7A H7A 111(3) . . ?
C3A C4A C5A 115.4(9) . . ?
C3A C4A H4A1 108.4 . . ?
C5A C4A H4A1 108.4 . . ?
C3A C4A H4A2 108.4 . . ?
C5A C4A H4A2 108.4 . . ?
H4A1 C4A H4A2 107.5 . . ?
O2B C3A O1B 118.1(13) . . ?
O2B C3A C4A 121.5(13) . . ?
O1B C3A C4A 118.8(12) . . ?

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
O2A C3B C4B C5B -5(2) . . . . ?
O1A C3B C4B C5B 150.2(15) . . . . ?
C14 N9 C10 N11 -58.10(13) . . . . ?
C15 N9 C10 N11 57.91(13) . . . . ?
N9 C10 N11 C18 -57.95(12) . . . . ?
N9 C10 N11 C12 58.60(12) . . . . ?
C10 N11 C12 N13 -58.79(12) . . . . ?
C18 N11 C12 N13 57.85(12) . . . . ?
N11 C12 N13 C14 58.59(12) . . . . ?
N11 C12 N13 C17 -58.38(12) . . . . ?
C12 N13 C14 N9 -58.15(13) . . . . ?
C17 N13 C14 N9 58.70(13) . . . . ?
C10 N9 C14 N13 57.95(13) . . . . ?
C15 N9 C14 N13 -58.38(13) . . . . ?
C10 N9 C15 N16 -58.32(12) . . . . ?
C14 N9 C15 N16 57.84(12) . . . . ?
N9 C15 N16 C18 58.51(12) . . . . ?
N9 C15 N16 C17 -58.09(12) . . . . ?
C14 N13 C17 N16 -58.31(13) . . . . ?
C12 N13 C17 N16 58.66(13) . . . . ?
C15 N16 C17 N13 58.25(12) . . . . ?
C18 N16 C17 N13 -58.35(12) . . . . ?
C15 N16 C18 N11 -59.02(12) . . . . ?
C17 N16 C18 N11 58.13(12) . . . . ?
C10 N11 C18 N16 58.74(12) . . . . ?
C12 N11 C18 N16 -57.89(12) . . . . ?
C24 N19 C20 N21 58.76(12) . . . . ?
C25 N19 C20 N21 -57.19(13) . . . . ?
N19 C20 N21 C28 57.70(13) . . . . ?
N19 C20 N21 C22 -58.85(13) . . . . ?
C20 N21 C22 N23 58.82(12) . . . . ?
C28 N21 C22 N23 -58.11(12) . . . . ?
N21 C22 N23 C24 -58.73(12) . . . . ?
N21 C22 N23 C27 58.04(12) . . . . ?
C22 N23 C24 N19 58.47(12) . . . . ?
C27 N23 C24 N19 -58.33(12) . . . . ?
C20 N19 C24 N23 -58.40(12) . . . . ?
C25 N19 C24 N23 57.83(12) . . . . ?
C24 N19 C25 N26 -58.29(12) . . . . ?
C20 N19 C25 N26 57.48(12) . . . . ?
N19 C25 N26 C28 -57.83(12) . . . . ?
N19 C25 N26 C27 58.66(12) . . . . ?
C24 N23 C27 N26 59.00(12) . . . . ?
C22 N23 C27 N26 -57.74(12) . . . . ?
C25 N26 C27 N23 -59.03(12) . . . . ?
C28 N26 C27 N23 57.59(12) . . . . ?
C20 N21 C28 N26 -58.34(13) . . . . ?
C22 N21 C28 N26 58.08(12) . . . . ?
C25 N26 C28 N21 58.35(13) . . . . ?
C27 N26 C28 N21 -57.93(12) . . . . ?
C4A C5A C6A O8A -31.1(6) . . . . ?
C4A C5A C6A O7A 169.4(5) . . . . ?
C3B C4B C5B C6B 161.1(9) . . . . ?
C4B C5B C6B O8B 29.9(9) . . . . ?
C4B C5B C6B O7B -177.8(8) . . . . ?
C6A C5A C4A C3A 177.8(8) . . . . ?
C5A C4A C3A O2B 8.9(16) . . . . ?
C5A C4A C3A O1B -156.0(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O7B^a H7B^a N9 0.92(3) 1.82(3) 2.737(3) 177(6) 7_566 yes
C5B^a H5B1^a O7B^a 0.99 2.03 2.936(5) 151.2 7_566 yes
O7A^b H7A^b N9 0.92(3) 1.72(3) 2.6340(19) 171(5) 7_566 yes

_refine_diff_density_max         0.504
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.062

