# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_HT_Salt
_database_code_depnum_ccdc_archive 'CCDC 2233083'
loop_
_audit_author_name
_audit_author_address
'Devin J. Angevine'
;University at Buffalo
United States of America
;
_audit_update_record             
;
2022-12-28 deposited with the CCDC.	2023-03-17 downloaded from the CCDC.
;
_audit_creation_date             2022-11-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
devinang@buffalo.edu
jbb6@buffalo.edu
_chemical_name_common            ?
_chemical_name_systematic        'Salt 7 (293 K)'
_chemical_formula_moiety         'C10 H15 N2, C7 H5 O4'
_chemical_formula_sum            'C17 H20 N2 O4'
_chemical_formula_weight         316.35
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7196(5)
_cell_length_b                   11.7045(7)
_cell_length_c                   9.4241(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.980(2)
_cell_angle_gamma                90
_cell_volume                     805.21(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2974
_cell_measurement_temperature    293
_cell_measurement_theta_max      21.47
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1526 before and 0.0411 after correction.
The Ratio of minimum to maximum transmission is 0.9182.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16130
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.412
_diffrn_reflns_theta_min         2.285
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3041
_reflns_number_total             4019
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4019
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.0145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H7A,H7B} of C7, {H9A,H9B} of C9, {H8A,H8B} of C8
 At 1.5 times of:
  All C(H,H,H) groups, {H3A,H4} of C14
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C16(H16), C1(H1A), C3(H3), C2(H2), C15(H15), C14(H14)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4632(2) 0.49824(14) 0.28949(18) 0.0535(4) Uani 1 1 d . . . . .
N1 N 0.2580(3) 0.42800(17) 0.4568(2) 0.0513(5) Uani 1 1 d . . . . .
O2 O 0.2009(3) 0.5576(2) 0.1289(3) 0.0789(6) Uani 1 1 d . . . . .
O3 O 0.7652(3) 0.5660(2) 0.2693(3) 0.0764(6) Uani 1 1 d . . . . .
C11 C 0.3720(3) 0.5569(2) 0.1759(3) 0.0489(5) Uani 1 1 d . . . . .
O4 O 0.1983(4) 0.6945(3) -0.0783(3) 0.1116(11) Uani 1 1 d . . . . .
C4 C 0.5628(3) 0.3776(2) 0.6491(3) 0.0510(6) Uani 1 1 d . . . . .
C12 C 0.4756(3) 0.6262(2) 0.0995(2) 0.0474(5) Uani 1 1 d . . . . .
N2 N 0.8747(3) 0.3989(3) 0.6523(3) 0.0761(7) Uani 1 1 d . . . . .
C5 C 0.7004(4) 0.3699(3) 0.5843(3) 0.0608(7) Uani 1 1 d . . . . .
H5 H 0.668518 0.342639 0.486513 0.073 Uiso 1 1 calc R U . . .
C13 C 0.6669(3) 0.6296(2) 0.1511(3) 0.0548(6) Uani 1 1 d . . . . .
C6 C 0.3693(4) 0.3402(2) 0.5675(3) 0.0548(6) Uani 1 1 d . . . . .
H6 H 0.308281 0.326057 0.642168 0.066 Uiso 1 1 calc R U . . .
C17 C 0.3822(4) 0.6940(3) -0.0252(3) 0.0693(8) Uani 1 1 d . . . . .
C16 C 0.4776(7) 0.7629(3) -0.0929(4) 0.0904(11) Uani 1 1 d . . . . .
H16 H 0.415145 0.807019 -0.175879 0.108 Uiso 1 1 calc R U . . .
C9 C 0.0906(4) 0.3642(3) 0.3601(4) 0.0699(8) Uani 1 1 d . . . . .
H9A H -0.012546 0.377140 0.395430 0.084 Uiso 1 1 calc R U . . .
H9B H 0.057456 0.389167 0.256532 0.084 Uiso 1 1 calc R U . . .
C1 C 0.9168(5) 0.4366(3) 0.7916(4) 0.0796(9) Uani 1 1 d . . . . .
H1A H 1.037827 0.456931 0.841548 0.095 Uiso 1 1 calc R U . . .
C3 C 0.6145(4) 0.4181(3) 0.7944(3) 0.0706(8) Uani 1 1 d . . . . .
H3 H 0.528195 0.425479 0.843442 0.085 Uiso 1 1 calc R U . . .
C7 C 0.3428(4) 0.2357(2) 0.4675(4) 0.0741(8) Uani 1 1 d . . . . .
H7A H 0.420572 0.239379 0.404885 0.089 Uiso 1 1 calc R U . . .
H7B H 0.370466 0.166288 0.526886 0.089 Uiso 1 1 calc R U . . .
C10 C 0.2150(4) 0.5337(3) 0.5232(4) 0.0768(9) Uani 1 1 d . . . . .
H10A H 0.141613 0.515681 0.585094 0.115 Uiso 1 1 calc R U . . .
H10B H 0.148714 0.584768 0.444582 0.115 Uiso 1 1 calc R U . . .
H10C H 0.326765 0.569483 0.583065 0.115 Uiso 1 1 calc R U . . .
C2 C 0.7941(5) 0.4476(3) 0.8662(4) 0.0857(10) Uani 1 1 d . . . . .
H2 H 0.830904 0.474531 0.964388 0.103 Uiso 1 1 calc R U . . .
C15 C 0.6649(7) 0.7658(3) -0.0370(4) 0.0893(11) Uani 1 1 d . . . . .
H15 H 0.728142 0.813956 -0.081481 0.107 Uiso 1 1 calc R U . . .
C8 C 0.1429(5) 0.2398(3) 0.3733(5) 0.0913(11) Uani 1 1 d . . . . .
H8A H 0.124818 0.207176 0.274932 0.110 Uiso 1 1 calc R U . . .
H8B H 0.069272 0.197500 0.421337 0.110 Uiso 1 1 calc R U . . .
C14 C 0.7617(5) 0.7000(3) 0.0824(4) 0.0777(9) Uani 1 1 d . . . . .
H14 H 0.889072 0.702252 0.117202 0.093 Uiso 1 1 calc R U . . .
H3A H 0.679(6) 0.527(4) 0.299(5) 0.117 Uiso 1 1 d . U . . .
H4 H 0.155(6) 0.644(4) -0.010(5) 0.117 Uiso 1 1 d . U . . .
H1 H 0.325(4) 0.447(3) 0.398(3) 0.068(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.274(3) . ?
N1 C6 1.517(3) . ?
N1 C9 1.514(3) . ?
N1 C10 1.471(4) . ?
N1 H1 0.90(3) . ?
O2 C11 1.249(3) . ?
O3 C13 1.349(3) . ?
O3 H3A 0.92(5) . ?
C11 C12 1.480(3) . ?
O4 C17 1.343(4) . ?
O4 H4 1.01(5) . ?
C4 C5 1.390(4) . ?
C4 C6 1.505(4) . ?
C4 C3 1.379(4) . ?
C12 C13 1.397(3) . ?
C12 C17 1.407(4) . ?
N2 C5 1.332(4) . ?
N2 C1 1.322(4) . ?
C5 H5 0.9300 . ?
C13 C14 1.394(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.517(4) . ?
C17 C16 1.381(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.369(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.504(5) . ?
C1 H1A 0.9300 . ?
C1 C2 1.357(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.375(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.511(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2 H2 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.367(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C14 H14 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
C6 N1 H1 106(2) . . ?
C9 N1 C6 105.1(2) . . ?
C9 N1 H1 107.6(19) . . ?
C10 N1 C6 115.7(2) . . ?
C10 N1 C9 113.9(2) . . ?
C10 N1 H1 108(2) . . ?
C13 O3 H3A 105(3) . . ?
O1 C11 C12 117.8(2) . . ?
O2 C11 O1 122.2(2) . . ?
O2 C11 C12 120.0(2) . . ?
C17 O4 H4 107(2) . . ?
C5 C4 C6 122.0(2) . . ?
C3 C4 C5 116.3(2) . . ?
C3 C4 C6 121.7(2) . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 C17 118.2(2) . . ?
C17 C12 C11 120.3(2) . . ?
C1 N2 C5 116.5(3) . . ?
C4 C5 H5 117.7 . . ?
N2 C5 C4 124.7(3) . . ?
N2 C5 H5 117.7 . . ?
O3 C13 C12 121.3(2) . . ?
O3 C13 C14 118.1(3) . . ?
C14 C13 C12 120.7(3) . . ?
N1 C6 H6 108.1 . . ?
C4 C6 N1 113.59(19) . . ?
C4 C6 H6 108.1 . . ?
C4 C6 C7 117.6(2) . . ?
C7 C6 N1 100.8(2) . . ?
C7 C6 H6 108.1 . . ?
O4 C17 C12 120.4(3) . . ?
O4 C17 C16 118.9(3) . . ?
C16 C17 C12 120.6(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 H16 120.3 . . ?
N1 C9 H9A 110.6 . . ?
N1 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
C8 C9 N1 105.9(2) . . ?
C8 C9 H9A 110.6 . . ?
C8 C9 H9B 110.6 . . ?
N2 C1 H1A 118.0 . . ?
N2 C1 C2 124.0(3) . . ?
C2 C1 H1A 118.0 . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C6 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C8 C7 C6 104.2(3) . . ?
C8 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C16 C15 H15 119.0 . . ?
C14 C15 C16 122.0(3) . . ?
C14 C15 H15 119.0 . . ?
C9 C8 C7 106.0(3) . . ?
C9 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
C7 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14 120.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7B O1 0.97 2.66 3.603(3) 164.6 2_646 yes
C8 H8A O4 0.97 2.58 3.192(4) 120.9 2_545 yes
O3 H3A O1 0.92(5) 1.68(5) 2.528(3) 152(4) . yes
O4 H4 O2 1.01(5) 1.60(5) 2.521(4) 149(4) . yes
N1 H1 O1 0.90(3) 1.80(3) 2.701(3) 175(3) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 C13 -1.3(3) . . . . ?
O1 C11 C12 C17 -179.1(2) . . . . ?
N1 C6 C7 C8 -41.4(3) . . . . ?
N1 C9 C8 C7 -4.2(4) . . . . ?
O2 C11 C12 C13 178.5(2) . . . . ?
O2 C11 C12 C17 0.7(4) . . . . ?
O3 C13 C14 C15 -179.6(3) . . . . ?
C11 C12 C13 O3 2.7(4) . . . . ?
C11 C12 C13 C14 -176.6(2) . . . . ?
C11 C12 C17 O4 -1.5(4) . . . . ?
C11 C12 C17 C16 177.0(3) . . . . ?
O4 C17 C16 C15 178.0(3) . . . . ?
C4 C6 C7 C8 -165.4(2) . . . . ?
C4 C3 C2 C1 0.4(5) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C12 C17 C16 C15 -0.5(5) . . . . ?
N2 C1 C2 C3 -0.1(6) . . . . ?
C5 C4 C6 N1 -80.6(3) . . . . ?
C5 C4 C6 C7 36.7(3) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C5 N2 C1 C2 -0.4(5) . . . . ?
C13 C12 C17 O4 -179.4(3) . . . . ?
C13 C12 C17 C16 -0.9(4) . . . . ?
C6 N1 C9 C8 -22.0(3) . . . . ?
C6 C4 C5 N2 -178.2(3) . . . . ?
C6 C4 C3 C2 177.7(3) . . . . ?
C6 C7 C8 C9 28.7(4) . . . . ?
C17 C12 C13 O3 -179.4(2) . . . . ?
C17 C12 C13 C14 1.3(4) . . . . ?
C17 C16 C15 C14 1.7(6) . . . . ?
C16 C15 C14 C13 -1.3(5) . . . . ?
C9 N1 C6 C4 165.7(2) . . . . ?
C9 N1 C6 C7 39.0(3) . . . . ?
C1 N2 C5 C4 0.5(5) . . . . ?
C3 C4 C5 N2 -0.1(4) . . . . ?
C3 C4 C6 N1 101.5(3) . . . . ?
C3 C4 C6 C7 -141.2(3) . . . . ?
C10 N1 C6 C4 -67.8(3) . . . . ?
C10 N1 C6 C7 165.5(2) . . . . ?
C10 N1 C9 C8 -149.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LT_Salt
_database_code_depnum_ccdc_archive 'CCDC 2233084'
loop_
_audit_author_name
_audit_author_address
'Angevine D.J.'
;University at Buffalo
United States of America
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-03-17 downloaded from the CCDC.
;
_audit_creation_date             2022-11-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
devinang@buffalo.edu
jbb6@buffalo.edu
# LT_salt note loop start
#Level B ADDSYM alerts were observed in the cifcheck for the LT_salt due to 
#potential B21 symmetry. The possibility of a B-face centered system was 
#ruled out using the combination of screw axes, angles and centroid 
#distances, and calculated precession images thus reaffirming the correct 
#assignment as a P21 lattice system.Further details can be found in the 
#manuscript text.
# LT_salt note loop end

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 N2, C7 H5 O4'
_chemical_formula_sum            'C17 H20 N2 O4'
_chemical_formula_weight         316.35
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9691(4)
_cell_length_b                   11.5520(4)
_cell_length_c                   13.8196(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.9950(10)
_cell_angle_gamma                90
_cell_volume                     1556.76(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6299
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1064 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.9619.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28199
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.366
_diffrn_reflns_theta_min         2.088
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                7118
_reflns_number_total             7777
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         7777
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.0326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0874
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C19(H19A,H19B), C17(H17A,H17B), C18(H18A,H18B), C7(H7A,H7B),
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15), C11(H11), C2(H2), C13(H13), C31(H31), C1(H1A), C3(H3A),
 C12(H12), C25(H25), C32(H32), C33(H33), C24(H24), C26(H26)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61799(12) 1.24804(11) -0.09272(9) 0.0161(3) Uani 1 1 d . . . . .
O6 O 0.87879(12) 0.75389(10) -0.41539(9) 0.0154(3) Uani 1 1 d . . . . .
O2 O 0.83587(13) 1.19216(13) -0.04709(9) 0.0213(3) Uani 1 1 d . . . . .
O5 O 0.66758(13) 0.68880(13) -0.47462(9) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.46564(13) 1.16873(12) -0.24874(9) 0.0192(3) Uani 1 1 d . . . . .
O4 O 0.94158(13) 1.06147(14) -0.15893(12) 0.0272(3) Uani 1 1 d . . . . .
O8 O 1.01106(13) 0.69017(12) -0.24597(9) 0.0211(3) Uani 1 1 d . . . . .
O7 O 0.55837(14) 0.54263(14) -0.37842(12) 0.0278(3) Uani 1 1 d . . . . .
N3 N 0.34980(15) 0.83113(13) -0.09193(11) 0.0155(3) Uani 1 1 d . . . . .
N1 N 0.86398(15) 0.81797(13) 0.39493(11) 0.0146(3) Uani 1 1 d . . . . .
N4 N 0.77241(16) 0.84963(15) 0.10730(12) 0.0221(4) Uani 1 1 d . . . . .
N2 N 1.26491(16) 0.84807(15) 0.61800(12) 0.0220(4) Uani 1 1 d . . . . .
C21 C 0.77450(17) 0.69215(16) -0.40799(12) 0.0140(3) Uani 1 1 d . . . . .
C28 C 0.72240(17) 1.19043(16) -0.10694(12) 0.0146(3) Uani 1 1 d . . . . .
C22 C 0.78352(17) 0.62072(16) -0.31745(12) 0.0141(3) Uani 1 1 d . . . . .
C34 C 0.57715(17) 1.11057(15) -0.26453(12) 0.0146(3) Uani 1 1 d . . . . .
C29 C 0.70532(17) 1.12004(16) -0.19877(13) 0.0138(3) Uani 1 1 d . . . . .
C30 C 0.81729(18) 1.05699(17) -0.22009(14) 0.0185(4) Uani 1 1 d . . . . .
C14 C 0.60249(18) 0.87974(16) -0.04320(13) 0.0164(4) Uani 1 1 d . . . . .
C4 C 1.11251(18) 0.86779(16) 0.45837(13) 0.0154(3) Uani 1 1 d . . . . .
C27 C 0.67370(18) 0.54723(16) -0.30756(14) 0.0188(4) Uani 1 1 d . . . . .
C23 C 0.90289(18) 0.62091(15) -0.24135(13) 0.0156(3) Uani 1 1 d . . . . .
C5 C 1.14521(18) 0.88038(17) 0.56078(13) 0.0176(4) Uani 1 1 d . . . . .
H5 H 1.079792 0.913339 0.591455 0.021 Uiso 1 1 calc R U . . .
C6 C 0.97657(17) 0.90710(15) 0.39720(12) 0.0148(3) Uani 1 1 d . . . . .
H6 H 0.987848 0.919766 0.329225 0.018 Uiso 1 1 calc R U . . .
C15 C 0.64591(18) 0.88000(17) 0.05952(13) 0.0177(4) Uani 1 1 d . . . . .
H15 H 0.583314 0.902615 0.097264 0.021 Uiso 1 1 calc R U . . .
C16 C 0.46095(18) 0.92021(16) -0.09294(13) 0.0159(4) Uani 1 1 d . . . . .
H16 H 0.461928 0.938907 -0.161956 0.019 Uiso 1 1 calc R U . . .
C11 C 0.86063(18) 0.81780(17) 0.05111(15) 0.0227(4) Uani 1 1 d . . . . .
H11 H 0.949227 0.797644 0.082744 0.027 Uiso 1 1 calc R U . . .
C2 C 1.33733(19) 0.78678(18) 0.47075(15) 0.0240(4) Uani 1 1 d . . . . .
H2 H 1.405414 0.755075 0.441993 0.029 Uiso 1 1 calc R U . . .
C13 C 0.69653(19) 0.84488(17) -0.09881(14) 0.0203(4) Uani 1 1 d . . . . .
H13 H 0.671635 0.842844 -0.167487 0.024 Uiso 1 1 calc R U . . .
C9 C 0.73042(18) 0.88114(16) 0.35374(14) 0.0186(4) Uani 1 1 d . . . . .
H9A H 0.660598 0.860154 0.390091 0.022 Uiso 1 1 calc R U . . .
H9B H 0.697387 0.862295 0.284487 0.022 Uiso 1 1 calc R U . . .
C31 C 0.8008(2) 0.98708(17) -0.30371(15) 0.0228(4) Uani 1 1 d . . . . .
H31 H 0.874894 0.946045 -0.317496 0.027 Uiso 1 1 calc R U . . .
C1 C 1.35828(18) 0.80232(17) 0.57178(15) 0.0224(4) Uani 1 1 d . . . . .
H1A H 1.442194 0.779729 0.610167 0.027 Uiso 1 1 calc R U . . .
C3 C 1.21180(18) 0.81975(17) 0.41312(13) 0.0196(4) Uani 1 1 d . . . . .
H3A H 1.194301 0.809796 0.344867 0.023 Uiso 1 1 calc R U . . .
C19 C 0.21620(18) 0.89606(17) -0.12429(14) 0.0204(4) Uani 1 1 d . . . . .
H19A H 0.147558 0.867347 -0.089814 0.024 Uiso 1 1 calc R U . . .
H19B H 0.181808 0.887581 -0.194928 0.024 Uiso 1 1 calc R U . . .
C17 C 0.40252(18) 1.02385(16) -0.04697(14) 0.0183(4) Uani 1 1 d . . . . .
H17A H 0.446534 1.095188 -0.060516 0.022 Uiso 1 1 calc R U . . .
H17B H 0.414047 1.014560 0.024038 0.022 Uiso 1 1 calc R U . . .
C12 C 0.8279(2) 0.81313(18) -0.05106(16) 0.0251(4) Uani 1 1 d . . . . .
H12 H 0.892249 0.789307 -0.086887 0.030 Uiso 1 1 calc R U . . .
C18 C 0.25041(19) 1.02346(17) -0.09754(14) 0.0222(4) Uani 1 1 d . . . . .
H18A H 0.234651 1.071277 -0.156513 0.027 Uiso 1 1 calc R U . . .
H18B H 0.194600 1.052345 -0.053058 0.027 Uiso 1 1 calc R U . . .
C7 C 0.90962(18) 1.01423(16) 0.43046(14) 0.0203(4) Uani 1 1 d . . . . .
H7A H 0.957152 1.084170 0.417989 0.024 Uiso 1 1 calc R U . . .
H7B H 0.907602 1.010227 0.500253 0.024 Uiso 1 1 calc R U . . .
C25 C 0.8035(2) 0.47720(17) -0.15287(14) 0.0235(4) Uani 1 1 d . . . . .
H25 H 0.810533 0.428358 -0.098546 0.028 Uiso 1 1 calc R U . . .
C32 C 0.6731(2) 0.97913(17) -0.36627(14) 0.0223(4) Uani 1 1 d . . . . .
H32 H 0.662390 0.931964 -0.421890 0.027 Uiso 1 1 calc R U . . .
C33 C 0.5609(2) 1.03952(16) -0.34817(13) 0.0199(4) Uani 1 1 d . . . . .
H33 H 0.475964 1.032978 -0.390987 0.024 Uiso 1 1 calc R U . . .
C24 C 0.9127(2) 0.54871(17) -0.15904(13) 0.0206(4) Uani 1 1 d . . . . .
H24 H 0.991387 0.548733 -0.109222 0.025 Uiso 1 1 calc R U . . .
C26 C 0.6838(2) 0.47593(17) -0.22497(15) 0.0237(4) Uani 1 1 d . . . . .
H26 H 0.611228 0.428123 -0.218330 0.028 Uiso 1 1 calc R U . . .
C20 C 0.3587(2) 0.72520(17) -0.15076(13) 0.0219(4) Uani 1 1 d . . . . .
H20A H 0.347307 0.745357 -0.219376 0.033 Uiso 1 1 calc R U . . .
H20B H 0.287814 0.672097 -0.142529 0.033 Uiso 1 1 calc R U . . .
H20C H 0.446646 0.689515 -0.128483 0.033 Uiso 1 1 calc R U . . .
C10 C 0.8801(2) 0.70957(16) 0.34126(13) 0.0207(4) Uani 1 1 d . . . . .
H10A H 0.878468 0.726935 0.273085 0.031 Uiso 1 1 calc R U . . .
H10B H 0.806391 0.657644 0.345506 0.031 Uiso 1 1 calc R U . . .
H10C H 0.965994 0.673878 0.370391 0.031 Uiso 1 1 calc R U . . .
C8 C 0.7648(2) 1.00969(17) 0.36630(16) 0.0268(4) Uani 1 1 d . . . . .
H8A H 0.700201 1.049046 0.398648 0.032 Uiso 1 1 calc R U . . .
H8B H 0.762364 1.045877 0.302616 0.032 Uiso 1 1 calc R U . . .
H1 H 0.864(3) 0.797(3) 0.461(2) 0.040 Uiso 1 1 d . U . . .
H3 H 0.359(3) 0.806(3) -0.028(2) 0.040 Uiso 1 1 d . U . . .
H4 H 0.927(3) 1.106(3) -0.1056(19) 0.040 Uiso 1 1 d . U . . .
H8 H 0.983(3) 0.725(2) -0.305(2) 0.040 Uiso 1 1 d . U . . .
H3B H 0.500(3) 1.211(3) -0.1893(19) 0.040 Uiso 1 1 d . U . . .
H7 H 0.575(3) 0.594(3) -0.4229(19) 0.040 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C28 1.284(2) . ?
O6 C21 1.282(2) . ?
O2 C28 1.255(2) . ?
O5 C21 1.256(2) . ?
O3 C34 1.355(2) . ?
O3 H3B 0.95(3) . ?
O4 C30 1.348(2) . ?
O4 H4 0.93(3) . ?
O8 C23 1.355(2) . ?
O8 H8 0.90(3) . ?
O7 C27 1.347(2) . ?
O7 H7 0.90(3) . ?
N3 C16 1.514(2) . ?
N3 C19 1.513(2) . ?
N3 C20 1.482(2) . ?
N3 H3 0.92(3) . ?
N1 C6 1.519(2) . ?
N1 C9 1.521(2) . ?
N1 C10 1.481(2) . ?
N1 H1 0.94(3) . ?
N4 C15 1.343(2) . ?
N4 C11 1.340(3) . ?
N2 C5 1.340(2) . ?
N2 C1 1.342(3) . ?
C21 C22 1.486(2) . ?
C28 C29 1.487(2) . ?
C22 C27 1.414(2) . ?
C22 C23 1.415(2) . ?
C34 C29 1.410(2) . ?
C34 C33 1.399(2) . ?
C29 C30 1.414(2) . ?
C30 C31 1.391(3) . ?
C14 C15 1.395(2) . ?
C14 C16 1.510(2) . ?
C14 C13 1.390(3) . ?
C4 C5 1.392(2) . ?
C4 C6 1.510(2) . ?
C4 C3 1.391(3) . ?
C27 C26 1.394(3) . ?
C23 C24 1.397(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9800 . ?
C6 C7 1.522(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9800 . ?
C16 C17 1.526(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.380(3) . ?
C2 C3 1.390(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.387(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.526(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.386(3) . ?
C1 H1A 0.9300 . ?
C3 H3A 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.538(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.532(2) . ?
C12 H12 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.530(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.384(3) . ?
C25 C26 1.386(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.384(3) . ?
C33 H33 0.9300 . ?
C24 H24 0.9300 . ?
C26 H26 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 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
C34 O3 H3B 103.1(16) . . ?
C30 O4 H4 104.0(16) . . ?
C23 O8 H8 101.8(17) . . ?
C27 O7 H7 102.9(16) . . ?
C16 N3 H3 107.3(18) . . ?
C19 N3 C16 105.14(13) . . ?
C19 N3 H3 110.4(17) . . ?
C20 N3 C16 115.39(14) . . ?
C20 N3 C19 113.36(14) . . ?
C20 N3 H3 105.2(18) . . ?
C6 N1 C9 105.55(13) . . ?
C6 N1 H1 107.5(17) . . ?
C9 N1 H1 108.2(16) . . ?
C10 N1 C6 115.26(14) . . ?
C10 N1 C9 113.32(14) . . ?
C10 N1 H1 106.7(18) . . ?
C11 N4 C15 116.70(17) . . ?
C5 N2 C1 116.71(16) . . ?
O6 C21 C22 117.90(15) . . ?
O5 C21 O6 122.50(16) . . ?
O5 C21 C22 119.59(16) . . ?
O1 C28 C29 117.46(15) . . ?
O2 C28 O1 122.62(16) . . ?
O2 C28 C29 119.92(15) . . ?
C27 C22 C21 120.14(15) . . ?
C27 C22 C23 118.53(16) . . ?
C23 C22 C21 121.29(15) . . ?
O3 C34 C29 121.45(15) . . ?
O3 C34 C33 117.78(15) . . ?
C33 C34 C29 120.77(16) . . ?
C34 C29 C28 121.34(15) . . ?
C34 C29 C30 118.34(16) . . ?
C30 C29 C28 120.27(15) . . ?
O4 C30 C29 120.80(16) . . ?
O4 C30 C31 118.52(16) . . ?
C31 C30 C29 120.66(17) . . ?
C15 C14 C16 121.70(16) . . ?
C13 C14 C15 117.45(17) . . ?
C13 C14 C16 120.80(16) . . ?
C5 C4 C6 122.06(16) . . ?
C3 C4 C5 117.41(16) . . ?
C3 C4 C6 120.51(15) . . ?
O7 C27 C22 120.95(16) . . ?
O7 C27 C26 118.51(16) . . ?
C26 C27 C22 120.53(17) . . ?
O8 C23 C22 121.37(15) . . ?
O8 C23 C24 117.98(16) . . ?
C24 C23 C22 120.65(17) . . ?
N2 C5 C4 124.21(17) . . ?
N2 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N1 C6 H6 108.2 . . ?
N1 C6 C7 100.89(13) . . ?
C4 C6 N1 112.40(14) . . ?
C4 C6 H6 108.2 . . ?
C4 C6 C7 118.32(15) . . ?
C7 C6 H6 108.2 . . ?
N4 C15 C14 124.10(17) . . ?
N4 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
N3 C16 H16 108.3 . . ?
N3 C16 C17 100.71(13) . . ?
C14 C16 N3 113.69(14) . . ?
C14 C16 H16 108.3 . . ?
C14 C16 C17 117.06(15) . . ?
C17 C16 H16 108.3 . . ?
N4 C11 H11 118.0 . . ?
N4 C11 C12 123.94(17) . . ?
C12 C11 H11 118.0 . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.24(18) . . ?
C3 C2 H2 120.9 . . ?
C14 C13 H13 120.3 . . ?
C12 C13 C14 119.47(17) . . ?
C12 C13 H13 120.3 . . ?
N1 C9 H9A 110.7 . . ?
N1 C9 H9B 110.7 . . ?
N1 C9 C8 105.42(14) . . ?
H9A C9 H9B 108.8 . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.42(17) . . ?
C32 C31 H31 120.3 . . ?
N2 C1 C2 123.97(17) . . ?
N2 C1 H1A 118.0 . . ?
C2 C1 H1A 118.0 . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 C4 119.45(16) . . ?
C2 C3 H3A 120.3 . . ?
N3 C19 H19A 110.7 . . ?
N3 C19 H19B 110.7 . . ?
N3 C19 C18 105.41(14) . . ?
H19A C19 H19B 108.8 . . ?
C18 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
C16 C17 H17A 111.0 . . ?
C16 C17 H17B 111.0 . . ?
C16 C17 C18 103.60(15) . . ?
H17A C17 H17B 109.0 . . ?
C18 C17 H17A 111.0 . . ?
C18 C17 H17B 111.0 . . ?
C11 C12 C13 118.34(17) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C19 C18 H18A 110.7 . . ?
C19 C18 H18B 110.7 . . ?
C17 C18 C19 105.15(15) . . ?
C17 C18 H18A 110.7 . . ?
C17 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?
C6 C7 H7A 111.3 . . ?
C6 C7 H7B 111.3 . . ?
C6 C7 C8 102.55(15) . . ?
H7A C7 H7B 109.2 . . ?
C8 C7 H7A 111.3 . . ?
C8 C7 H7B 111.3 . . ?
C24 C25 H25 118.9 . . ?
C24 C25 C26 122.18(17) . . ?
C26 C25 H25 118.9 . . ?
C31 C32 H32 119.1 . . ?
C33 C32 C31 121.73(17) . . ?
C33 C32 H32 119.1 . . ?
C34 C33 H33 120.5 . . ?
C32 C33 C34 119.08(17) . . ?
C32 C33 H33 120.5 . . ?
C23 C24 H24 120.5 . . ?
C25 C24 C23 118.93(17) . . ?
C25 C24 H24 120.5 . . ?
C27 C26 H26 120.4 . . ?
C25 C26 C27 119.17(17) . . ?
C25 C26 H26 120.4 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C8 C7 105.18(15) . . ?
C9 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
C7 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?

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
C11 H11 O2 0.93 2.60 3.367(2) 140.2 2_745 yes
C31 H31 O6 0.93 2.60 3.278(2) 129.7 . yes
C17 H17A O1 0.97 2.56 3.505(2) 164.7 . yes
C7 H7A O6 0.97 2.56 3.513(2) 168.0 2_755 yes
C20 H20A N2 0.96 2.52 3.444(2) 160.7 1_454 yes
C8 H8A O7 0.97 2.54 3.283(2) 133.8 2_655 yes
N1 H1 O6 0.94(3) 1.76(3) 2.6981(19) 175(2) 1_556 yes
N1 H1 O5 0.94(3) 2.63(3) 3.283(2) 127(2) 1_556 yes
N3 H3 O1 0.92(3) 1.77(3) 2.6825(19) 176(3) 2_645 yes
O4 H4 O2 0.93(3) 1.67(3) 2.5408(19) 154(2) . yes
O8 H8 O6 0.90(3) 1.69(3) 2.5454(17) 157(3) . yes
O3 H3B O1 0.95(3) 1.64(3) 2.5364(17) 155(2) . yes
O7 H7 O5 0.90(3) 1.68(3) 2.531(2) 157(2) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C28 C29 C34 -4.2(2) . . . . ?
O1 C28 C29 C30 178.36(16) . . . . ?
O6 C21 C22 C27 -177.23(16) . . . . ?
O6 C21 C22 C23 0.3(2) . . . . ?
O2 C28 C29 C34 176.09(16) . . . . ?
O2 C28 C29 C30 -1.4(3) . . . . ?
O5 C21 C22 C27 1.6(3) . . . . ?
O5 C21 C22 C23 179.13(16) . . . . ?
O3 C34 C29 C28 2.6(3) . . . . ?
O3 C34 C29 C30 -179.87(16) . . . . ?
O3 C34 C33 C32 179.93(17) . . . . ?
O4 C30 C31 C32 178.47(17) . . . . ?
O8 C23 C24 C25 -179.94(17) . . . . ?
O7 C27 C26 C25 178.11(17) . . . . ?
N3 C16 C17 C18 -43.02(16) . . . . ?
N3 C19 C18 C17 -2.2(2) . . . . ?
N1 C6 C7 C8 -44.77(17) . . . . ?
N1 C9 C8 C7 -9.7(2) . . . . ?
N4 C11 C12 C13 1.0(3) . . . . ?
C21 C22 C27 O7 -1.6(3) . . . . ?
C21 C22 C27 C26 177.02(17) . . . . ?
C21 C22 C23 O8 3.1(3) . . . . ?
C21 C22 C23 C24 -176.60(17) . . . . ?
C28 C29 C30 O4 -1.4(3) . . . . ?
C28 C29 C30 C31 177.29(17) . . . . ?
C22 C27 C26 C25 -0.5(3) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C34 C29 C30 O4 -178.96(16) . . . . ?
C34 C29 C30 C31 -0.3(3) . . . . ?
C29 C34 C33 C32 -0.6(3) . . . . ?
C29 C30 C31 C32 -0.2(3) . . . . ?
C30 C31 C32 C33 0.3(3) . . . . ?
C14 C16 C17 C18 -166.79(15) . . . . ?
C14 C13 C12 C11 -0.2(3) . . . . ?
C4 C6 C7 C8 -167.75(15) . . . . ?
C27 C22 C23 O8 -179.35(17) . . . . ?
C27 C22 C23 C24 1.0(3) . . . . ?
C23 C22 C27 O7 -179.18(16) . . . . ?
C23 C22 C27 C26 -0.6(3) . . . . ?
C5 N2 C1 C2 -0.3(3) . . . . ?
C5 C4 C6 N1 -83.1(2) . . . . ?
C5 C4 C6 C7 33.9(2) . . . . ?
C5 C4 C3 C2 0.0(3) . . . . ?
C6 N1 C9 C8 -18.43(18) . . . . ?
C6 C4 C5 N2 -179.21(17) . . . . ?
C6 C4 C3 C2 178.47(17) . . . . ?
C6 C7 C8 C9 34.05(19) . . . . ?
C15 N4 C11 C12 -1.0(3) . . . . ?
C15 C14 C16 N3 -79.2(2) . . . . ?
C15 C14 C16 C17 37.7(2) . . . . ?
C15 C14 C13 C12 -0.5(3) . . . . ?
C16 N3 C19 C18 -25.01(18) . . . . ?
C16 C14 C15 N4 -177.04(18) . . . . ?
C16 C14 C13 C12 177.08(17) . . . . ?
C16 C17 C18 C19 28.16(18) . . . . ?
C11 N4 C15 C14 0.2(3) . . . . ?
C13 C14 C15 N4 0.5(3) . . . . ?
C13 C14 C16 N3 103.34(19) . . . . ?
C13 C14 C16 C17 -139.79(18) . . . . ?
C9 N1 C6 C4 166.26(14) . . . . ?
C9 N1 C6 C7 39.27(16) . . . . ?
C31 C32 C33 C34 0.1(3) . . . . ?
C1 N2 C5 C4 0.9(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C3 C4 C5 N2 -0.8(3) . . . . ?
C3 C4 C6 N1 98.57(19) . . . . ?
C3 C4 C6 C7 -144.42(17) . . . . ?
C3 C2 C1 N2 -0.4(3) . . . . ?
C19 N3 C16 C14 168.22(15) . . . . ?
C19 N3 C16 C17 42.16(16) . . . . ?
C33 C34 C29 C28 -176.83(17) . . . . ?
C33 C34 C29 C30 0.7(3) . . . . ?
C24 C25 C26 C27 1.3(3) . . . . ?
C26 C25 C24 C23 -0.9(3) . . . . ?
C20 N3 C16 C14 -66.11(19) . . . . ?
C20 N3 C16 C17 167.83(14) . . . . ?
C20 N3 C19 C18 -151.93(15) . . . . ?
C10 N1 C6 C4 -67.89(18) . . . . ?
C10 N1 C6 C7 165.12(14) . . . . ?
C10 N1 C9 C8 -145.47(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
