# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_190719e
_database_code_depnum_ccdc_archive 'CCDC 2006387'
loop_
_audit_author_name
_audit_author_address
'Li zihan'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-05-28 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'1,5-Pentanediamine acidephtalique;1,5-Pentanediamine 1,2-phthalicacid'
_chemical_name_common            '1,5-Diaminopentane acidephtalique;'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H24 N2 O6'
_chemical_formula_weight         304.34

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   7.0825(7)
_cell_length_b                   12.6540(11)
_cell_length_c                   17.5329(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.762(2)
_cell_angle_gamma                90.00
_cell_volume                     1563.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1315
_cell_measurement_theta_min      2.335
_cell_measurement_theta_max      23.666

_exptl_crystal_description       ?
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2761
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0832
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2761
_reflns_number_gt                1594
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0352P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2761
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4962(4) 1.05724(19) 0.79093(11) 0.0355(7) Uani 1 1 d . . .
H1A H 0.4034 1.0223 0.8106 0.053 Uiso 1 1 calc R . .
H1B H 0.4857 1.1259 0.8005 0.053 Uiso 1 1 calc R . .
H1C H 0.6079 1.0339 0.8121 0.053 Uiso 1 1 calc R . .
N2 N 0.5789(4) 0.6997(2) 0.45343(13) 0.0449(8) Uani 1 1 d . . .
H2A H 0.6959 0.6828 0.4730 0.067 Uiso 1 1 calc R . .
H2B H 0.5741 0.7017 0.4025 0.067 Uiso 1 1 calc R . .
H2C H 0.4975 0.6516 0.4674 0.067 Uiso 1 1 calc R . .
O1 O 0.4729(4) 0.26475(17) 0.82913(11) 0.0543(7) Uani 1 1 d . . .
O2 O 0.5078(4) 0.30889(17) 0.70976(10) 0.0552(7) Uani 1 1 d . . .
O3 O 0.3254(3) 0.49626(17) 0.62995(10) 0.0415(6) Uani 1 1 d . . .
O4 O 0.6372(3) 0.52314(19) 0.63137(11) 0.0486(6) Uani 1 1 d . . .
O5 O 0.2613(3) 0.58148(17) 0.49051(10) 0.0516(7) Uani 1 1 d . . .
H5C H 0.2867 0.5493 0.5328 0.062 Uiso 1 1 d R . .
H5D H 0.2977 0.5434 0.4548 0.062 Uiso 1 1 d R . .
O6 O 0.5442(3) 0.20393(18) 0.98227(11) 0.0661(8) Uani 1 1 d . . .
H6C H 0.5261 0.2234 0.9357 0.079 Uiso 1 1 d R . .
H6D H 0.4514 0.1653 0.9920 0.079 Uiso 1 1 d R . .
C1 C 0.4934(4) 0.3317(2) 0.77739(16) 0.0328(8) Uani 1 1 d . . .
C2 C 0.4873(5) 0.5122(2) 0.66336(15) 0.0320(7) Uani 1 1 d . . .
C3 C 0.5028(4) 0.4462(2) 0.80190(14) 0.0269(7) Uani 1 1 d . . .
C4 C 0.5029(4) 0.5288(2) 0.74904(14) 0.0258(7) Uani 1 1 d . . .
C5 C 0.5130(5) 0.6318(3) 0.77413(15) 0.0406(9) Uani 1 1 d . . .
H5 H 0.5128 0.6862 0.7384 0.049 Uiso 1 1 calc R . .
C6 C 0.5233(5) 0.6563(3) 0.85129(16) 0.0451(9) Uani 1 1 d . . .
H6 H 0.5291 0.7264 0.8674 0.054 Uiso 1 1 calc R . .
C7 C 0.5249(5) 0.5757(3) 0.90360(16) 0.0411(8) Uani 1 1 d . . .
H7 H 0.5332 0.5910 0.9557 0.049 Uiso 1 1 calc R . .
C8 C 0.5143(4) 0.4720(3) 0.87917(15) 0.0356(8) Uani 1 1 d . . .
H8 H 0.5148 0.4182 0.9153 0.043 Uiso 1 1 calc R . .
C9 C 0.4821(4) 1.0398(2) 0.70668(14) 0.0327(7) Uani 1 1 d . . .
H9A H 0.5831 1.0785 0.6857 0.039 Uiso 1 1 calc R . .
H9B H 0.3623 1.0682 0.6839 0.039 Uiso 1 1 calc R . .
C10 C 0.4948(4) 0.9246(2) 0.68462(14) 0.0336(8) Uani 1 1 d . . .
H10A H 0.3899 0.8858 0.7027 0.040 Uiso 1 1 calc R . .
H10B H 0.6122 0.8947 0.7086 0.040 Uiso 1 1 calc R . .
C11 C 0.4886(4) 0.9142(2) 0.59779(15) 0.0365(8) Uani 1 1 d . . .
H11A H 0.3650 0.9377 0.5751 0.044 Uiso 1 1 calc R . .
H11B H 0.5827 0.9614 0.5799 0.044 Uiso 1 1 calc R . .
C12 C 0.5238(5) 0.8044(2) 0.56896(15) 0.0396(8) Uani 1 1 d . . .
H12A H 0.4242 0.7574 0.5825 0.047 Uiso 1 1 calc R . .
H12B H 0.6439 0.7783 0.5932 0.047 Uiso 1 1 calc R . .
C13 C 0.5279(5) 0.8048(2) 0.48243(15) 0.0418(9) Uani 1 1 d . . .
H13A H 0.4042 0.8253 0.4582 0.050 Uiso 1 1 calc R . .
H13B H 0.6195 0.8567 0.4687 0.050 Uiso 1 1 calc R . .


_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
N1 C9 1.487(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C13 1.482(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
O1 C1 1.260(3) . ?
O2 C1 1.234(3) . ?
O3 C2 1.251(4) . ?
O4 C2 1.257(4) . ?
O5 H5C 0.8499 . ?
O5 H5D 0.8501 . ?
O6 H6C 0.8500 . ?
O6 H6D 0.8500 . ?
C1 C3 1.511(4) . ?
C2 C4 1.510(3) . ?
C3 C8 1.388(3) . ?
C3 C4 1.397(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.513(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.524(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.509(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.520(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 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
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C13 N2 H2A 109.5 . . ?
C13 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C13 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
H5C O5 H5D 108.6 . . ?
H6C O6 H6D 108.3 . . ?
O2 C1 O1 124.1(3) . . ?
O2 C1 C3 119.4(3) . . ?
O1 C1 C3 116.4(2) . . ?
O3 C2 O4 125.8(2) . . ?
O3 C2 C4 117.4(3) . . ?
O4 C2 C4 116.6(3) . . ?
C8 C3 C4 117.9(3) . . ?
C8 C3 C1 120.0(3) . . ?
C4 C3 C1 122.1(2) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 C2 116.5(3) . . ?
C3 C4 C2 123.5(3) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 121.5(3) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
N1 C9 C10 113.4(2) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 110.0(2) . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C10 115.1(3) . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 C13 110.6(3) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N2 C13 C12 111.6(2) . . ?
N2 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C3 C8 -170.7(3) . . . . ?
O1 C1 C3 C8 8.5(4) . . . . ?
O2 C1 C3 C4 8.4(5) . . . . ?
O1 C1 C3 C4 -172.4(3) . . . . ?
C8 C3 C4 C5 -0.4(4) . . . . ?
C1 C3 C4 C5 -179.6(3) . . . . ?
C8 C3 C4 C2 -178.8(3) . . . . ?
C1 C3 C4 C2 2.1(5) . . . . ?
O3 C2 C4 C5 -98.1(3) . . . . ?
O4 C2 C4 C5 77.0(4) . . . . ?
O3 C2 C4 C3 80.3(4) . . . . ?
O4 C2 C4 C3 -104.7(4) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C2 C4 C5 C6 178.5(3) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C3 0.4(5) . . . . ?
C4 C3 C8 C7 0.2(5) . . . . ?
C1 C3 C8 C7 179.4(3) . . . . ?
N1 C9 C10 C11 -177.3(2) . . . . ?
C9 C10 C11 C12 173.0(3) . . . . ?
C10 C11 C12 C13 -176.0(3) . . . . ?
C11 C12 C13 N2 175.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.090
_chemical_properties_physical    Moisture-sensitive,Hygroscopic,Heat-sensitive
####################################################################### 
# 
# 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_190719f
_database_code_depnum_ccdc_archive 'CCDC 2006389'
loop_
_audit_author_name
_audit_author_address
'Li zihan'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-05-28 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1,5-Pentanediamine 1,2-phthalicacid'
_chemical_name_common            
'1,5-Pentanediamine1,2-dicarboxybenzene; 1,2-dicarboxybenzene acidephtalique'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H26 N2 O7'
_chemical_formula_weight         322.36

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   11.6407(9)
_cell_length_b                   10.0447(8)
_cell_length_c                   14.8138(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.974(4)
_cell_angle_gamma                90.00
_cell_volume                     1638.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1805
_cell_measurement_theta_min      2.495
_cell_measurement_theta_max      22.154

_exptl_crystal_description       ?
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9550
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7931
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2887
_reflns_number_gt                1682
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0459P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2887
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.64237(17) 0.2467(2) 0.53343(13) 0.0435(6) Uani 1 1 d . . .
H1A H 0.6920 0.2485 0.5935 0.065 Uiso 1 1 calc R . .
H1B H 0.5702 0.2153 0.5319 0.065 Uiso 1 1 calc R . .
H1C H 0.6337 0.3287 0.5094 0.065 Uiso 1 1 calc R . .
N2 N 1.13288(17) 0.2050(2) 0.32037(14) 0.0483(6) Uani 1 1 d . . .
H2A H 1.0937 0.2634 0.2758 0.072 Uiso 1 1 calc R . .
H2B H 1.1796 0.1536 0.2979 0.072 Uiso 1 1 calc R . .
H2C H 1.1789 0.2483 0.3718 0.072 Uiso 1 1 calc R . .
O1 O 0.51555(17) 0.8703(2) 0.32330(14) 0.0660(6) Uani 1 1 d . . .
O2 O 0.60040(17) 0.81503(19) 0.47566(13) 0.0595(6) Uani 1 1 d . . .
O3 O 0.61959(14) 0.49361(17) 0.44112(12) 0.0517(5) Uani 1 1 d . . .
O4 O 0.77058(16) 0.5661(2) 0.56609(12) 0.0593(5) Uani 1 1 d . . .
O5 O 0.62339(14) 0.48956(17) 0.67191(10) 0.0532(5) Uani 1 1 d . . .
H5C H 0.6677 0.5130 0.6390 0.064 Uiso 1 1 d R . .
H5D H 0.5494 0.4949 0.6369 0.064 Uiso 1 1 d R . .
O6 O 0.62494(16) 0.9230(2) 0.65275(12) 0.0694(6) Uani 1 1 d . . .
H6C H 0.6105 0.8966 0.5956 0.083 Uiso 1 1 d R . .
H6D H 0.5770 0.9868 0.6529 0.083 Uiso 1 1 d R . .
O7 O 0.82374(16) 0.2178(2) 0.71231(12) 0.0634(6) Uani 1 1 d . . .
H7C H 0.8388 0.1463 0.7448 0.076 Uiso 1 1 d R . .
H7D H 0.8385 0.2832 0.7508 0.076 Uiso 1 1 d R . .
C1 C 0.5990(2) 0.8191(3) 0.3908(2) 0.0445(7) Uani 1 1 d . . .
C2 C 0.7121(2) 0.5634(3) 0.47873(18) 0.0401(6) Uani 1 1 d . . .
C3 C 0.7054(2) 0.7596(3) 0.36885(15) 0.0350(6) Uani 1 1 d . . .
C4 C 0.76049(19) 0.6424(2) 0.41249(15) 0.0339(6) Uani 1 1 d . . .
C5 C 0.8611(2) 0.5946(3) 0.39197(17) 0.0446(7) Uani 1 1 d . . .
H5 H 0.8975 0.5159 0.4202 0.054 Uiso 1 1 calc R . .
C6 C 0.9082(2) 0.6611(3) 0.33091(19) 0.0523(8) Uani 1 1 d . . .
H6 H 0.9762 0.6277 0.3185 0.063 Uiso 1 1 calc R . .
C7 C 0.8548(2) 0.7766(3) 0.28829(18) 0.0530(8) Uani 1 1 d . . .
H7 H 0.8870 0.8224 0.2474 0.064 Uiso 1 1 calc R . .
C8 C 0.7534(2) 0.8250(3) 0.30606(16) 0.0449(7) Uani 1 1 d . . .
H8 H 0.7164 0.9023 0.2757 0.054 Uiso 1 1 calc R . .
C9 C 0.6944(2) 0.1591(3) 0.47587(17) 0.0425(7) Uani 1 1 d . . .
H9A H 0.6374 0.1512 0.4117 0.051 Uiso 1 1 calc R . .
H9B H 0.7082 0.0710 0.5040 0.051 Uiso 1 1 calc R . .
C10 C 0.8122(2) 0.2154(3) 0.47186(18) 0.0438(7) Uani 1 1 d . . .
H10A H 0.8675 0.2254 0.5365 0.053 Uiso 1 1 calc R . .
H10B H 0.7972 0.3033 0.4433 0.053 Uiso 1 1 calc R . .
C11 C 0.87258(19) 0.1311(2) 0.41602(16) 0.0392(6) Uani 1 1 d . . .
H11A H 0.8145 0.1120 0.3537 0.047 Uiso 1 1 calc R . .
H11B H 0.8974 0.0471 0.4489 0.047 Uiso 1 1 calc R . .
C12 C 0.9824(2) 0.1993(3) 0.40373(17) 0.0446(7) Uani 1 1 d . . .
H12A H 0.9573 0.2847 0.3730 0.054 Uiso 1 1 calc R . .
H12B H 1.0406 0.2164 0.4664 0.054 Uiso 1 1 calc R . .
C13 C 1.0439(2) 0.1215(3) 0.34627(17) 0.0432(6) Uani 1 1 d . . .
H13A H 1.0851 0.0453 0.3830 0.052 Uiso 1 1 calc R . .
H13B H 0.9835 0.0887 0.2887 0.052 Uiso 1 1 calc R . .


_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
N1 C9 1.484(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C13 1.477(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
O1 C1 1.255(3) . ?
O2 C1 1.252(3) . ?
O3 C2 1.254(3) . ?
O4 C2 1.251(3) . ?
O5 H5C 0.8500 . ?
O5 H5D 0.8500 . ?
O6 H6C 0.8500 . ?
O6 H6D 0.8500 . ?
O7 H7C 0.8500 . ?
O7 H7D 0.8500 . ?
C1 C3 1.503(3) . ?
C2 C4 1.506(3) . ?
C3 C4 1.395(3) . ?
C3 C8 1.395(3) . ?
C4 C5 1.388(3) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.502(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.508(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.513(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.499(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 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
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C13 N2 H2A 109.5 . . ?
C13 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C13 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
H5C O5 H5D 108.4 . . ?
H6C O6 H6D 108.6 . . ?
H7C O7 H7D 108.3 . . ?
O2 C1 O1 124.6(2) . . ?
O2 C1 C3 117.5(3) . . ?
O1 C1 C3 117.9(2) . . ?
O4 C2 O3 124.8(2) . . ?
O4 C2 C4 118.0(2) . . ?
O3 C2 C4 117.0(2) . . ?
C4 C3 C8 118.9(2) . . ?
C4 C3 C1 121.5(2) . . ?
C8 C3 C1 119.6(2) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 C2 118.8(2) . . ?
C3 C4 C2 122.3(2) . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 119.9(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
N1 C9 C10 110.39(19) . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 113.9(2) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 112.0(2) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 114.2(2) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
N2 C13 C12 110.9(2) . . ?
N2 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?

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 C1 C3 C4 39.0(3) . . . . ?
O1 C1 C3 C4 -141.6(2) . . . . ?
O2 C1 C3 C8 -138.7(2) . . . . ?
O1 C1 C3 C8 40.7(3) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
C1 C3 C4 C5 -177.8(2) . . . . ?
C8 C3 C4 C2 -178.0(2) . . . . ?
C1 C3 C4 C2 4.3(3) . . . . ?
O4 C2 C4 C5 74.6(3) . . . . ?
O3 C2 C4 C5 -101.5(3) . . . . ?
O4 C2 C4 C3 -107.4(3) . . . . ?
O3 C2 C4 C3 76.5(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C2 C4 C5 C6 178.9(2) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C6 C7 C8 C3 1.5(4) . . . . ?
C4 C3 C8 C7 -1.2(3) . . . . ?
C1 C3 C8 C7 176.6(2) . . . . ?
N1 C9 C10 C11 179.0(2) . . . . ?
C9 C10 C11 C12 173.1(2) . . . . ?
C10 C11 C12 C13 -178.4(2) . . . . ?
C11 C12 C13 N2 168.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.055
_chemical_properties_physical    Moisture-sensitive,Hygroscopic,Heat-sensitive
####################################################################### 
# 
# 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_200603e
_database_code_depnum_ccdc_archive 'CCDC 2008099'
loop_
_audit_author_name
_audit_author_address
'Li zihan'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-06-05 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1,5-pentanediamine 1,2-phthalicacid'
_chemical_name_common            
'1,5-pentanediamine 1,2-dicarboxybenzene?1,5-diaminopentane 1,2-phthalicacid'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H22 N2 O5'
_chemical_formula_weight         286.33

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.6089(9)
_cell_length_b                   8.0476(8)
_cell_length_c                   19.0084(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.378(3)
_cell_angle_gamma                90.00
_cell_volume                     1441.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1754
_cell_measurement_theta_min      2.608
_cell_measurement_theta_max      27.593

_exptl_crystal_description       Stick
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6729
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_av_sigmaI/netI    0.1012
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2537
_reflns_number_gt                1412
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1146P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2537
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2166
_refine_ls_wR_factor_gt          0.1969
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2400(3) 0.3041(4) 0.19415(17) 0.0420(9) Uani 1 1 d . . .
H1A H 0.2095 0.2038 0.1785 0.063 Uiso 1 1 calc R . .
H1B H 0.1663 0.3667 0.1994 0.063 Uiso 1 1 calc R . .
H1C H 0.2996 0.2946 0.2362 0.063 Uiso 1 1 calc R . .
N2 N 0.8923(3) 0.2691(4) 0.05184(19) 0.0473(9) Uani 1 1 d . . .
H2A H 0.9352 0.3140 0.0933 0.071 Uiso 1 1 calc R . .
H2B H 0.9392 0.2967 0.0176 0.071 Uiso 1 1 calc R . .
H2C H 0.8914 0.1590 0.0562 0.071 Uiso 1 1 calc R . .
O1 O 0.9934(3) 0.4669(3) 0.17797(15) 0.0462(8) Uani 1 1 d . . .
O2 O 1.0718(3) 0.7255(3) 0.18052(15) 0.0485(8) Uani 1 1 d . . .
O3 O 0.9123(3) 0.6902(3) 0.02949(15) 0.0466(8) Uani 1 1 d . . .
O4 O 0.8129(3) 0.9387(3) 0.01055(17) 0.0565(9) Uani 1 1 d . . .
O5 O 0.1333(4) 1.0239(4) 0.12330(19) 0.0845(12) Uani 1 1 d . . .
H5C H 0.1157 0.9258 0.1356 0.101 Uiso 1 1 d R . .
H5D H 0.1485 1.0214 0.0807 0.101 Uiso 1 1 d R . .
C1 C 0.9747(4) 0.6209(5) 0.1729(2) 0.0355(9) Uani 1 1 d . . .
C2 C 0.8367(4) 0.8042(5) 0.0438(2) 0.0377(9) Uani 1 1 d . . .
C3 C 0.8262(4) 0.6799(4) 0.1627(2) 0.0330(9) Uani 1 1 d . . .
C4 C 0.7632(4) 0.7755(4) 0.1052(2) 0.0317(9) Uani 1 1 d . . .
C5 C 0.6265(4) 0.8346(4) 0.1011(2) 0.0407(10) Uani 1 1 d . . .
H5 H 0.5839 0.8985 0.0620 0.049 Uiso 1 1 calc R . .
C6 C 0.5538(4) 0.7997(5) 0.1542(3) 0.0494(12) Uani 1 1 d . . .
H6 H 0.4628 0.8416 0.1518 0.059 Uiso 1 1 calc R . .
C7 C 0.6151(4) 0.7032(5) 0.2107(2) 0.0471(11) Uani 1 1 d . . .
H7 H 0.5652 0.6773 0.2465 0.057 Uiso 1 1 calc R . .
C8 C 0.7494(4) 0.6446(5) 0.2148(2) 0.0395(10) Uani 1 1 d . . .
H8 H 0.7902 0.5792 0.2538 0.047 Uiso 1 1 calc R . .
C9 C 0.3141(4) 0.3828(5) 0.1417(2) 0.0437(10) Uani 1 1 d . . .
H9A H 0.2537 0.3789 0.0944 0.052 Uiso 1 1 calc R . .
H9B H 0.3327 0.4985 0.1544 0.052 Uiso 1 1 calc R . .
C10 C 0.4494(4) 0.2979(5) 0.1398(2) 0.0455(11) Uani 1 1 d . . .
H10A H 0.4312 0.1798 0.1332 0.055 Uiso 1 1 calc R . .
H10B H 0.5126 0.3126 0.1859 0.055 Uiso 1 1 calc R . .
C11 C 0.5224(4) 0.3574(5) 0.0825(2) 0.0394(10) Uani 1 1 d . . .
H11A H 0.5282 0.4777 0.0842 0.047 Uiso 1 1 calc R . .
H11B H 0.4670 0.3260 0.0361 0.047 Uiso 1 1 calc R . .
C12 C 0.6694(4) 0.2864(5) 0.0905(2) 0.0410(10) Uani 1 1 d . . .
H12A H 0.7252 0.3236 0.1359 0.049 Uiso 1 1 calc R . .
H12B H 0.6629 0.1663 0.0926 0.049 Uiso 1 1 calc R . .
C13 C 0.7465(4) 0.3306(4) 0.0329(2) 0.0397(10) Uani 1 1 d . . .
H13A H 0.6992 0.2816 -0.0121 0.048 Uiso 1 1 calc R . .
H13B H 0.7470 0.4503 0.0270 0.048 Uiso 1 1 calc R . .


_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
N1 C9 1.477(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C13 1.462(5) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
O1 C1 1.253(4) . ?
O2 C1 1.243(4) . ?
O3 C2 1.233(4) . ?
O4 C2 1.251(4) . ?
O5 H5C 0.8499 . ?
O5 H5D 0.8501 . ?
C1 C3 1.480(5) . ?
C2 C4 1.497(5) . ?
C3 C4 1.376(5) . ?
C3 C8 1.377(5) . ?
C4 C5 1.385(5) . ?
C5 C6 1.365(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.361(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.361(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.475(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.487(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.503(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.481(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 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
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C13 N2 H2A 109.5 . . ?
C13 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C13 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
H5C O5 H5D 108.6 . . ?
O2 C1 O1 124.6(3) . . ?
O2 C1 C3 118.6(3) . . ?
O1 C1 C3 116.6(3) . . ?
O3 C2 O4 126.1(4) . . ?
O3 C2 C4 116.5(3) . . ?
O4 C2 C4 117.4(3) . . ?
C4 C3 C8 118.2(3) . . ?
C4 C3 C1 123.0(3) . . ?
C8 C3 C1 118.7(3) . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 C2 120.3(3) . . ?
C5 C4 C2 119.5(3) . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 119.7(4) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.0(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 121.6(4) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
C10 C9 N1 111.2(3) . . ?
C10 C9 H9A 109.4 . . ?
N1 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
N1 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C11 114.4(3) . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 112.0(3) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 115.6(3) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
N2 C13 C12 109.3(3) . . ?
N2 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
N2 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?

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 C1 C3 C4 62.1(5) . . . . ?
O1 C1 C3 C4 -122.6(4) . . . . ?
O2 C1 C3 C8 -114.7(4) . . . . ?
O1 C1 C3 C8 60.6(5) . . . . ?
C8 C3 C4 C5 0.6(5) . . . . ?
C1 C3 C4 C5 -176.2(3) . . . . ?
C8 C3 C4 C2 -174.3(3) . . . . ?
C1 C3 C4 C2 8.9(5) . . . . ?
O3 C2 C4 C3 32.4(5) . . . . ?
O4 C2 C4 C3 -149.5(3) . . . . ?
O3 C2 C4 C5 -142.4(3) . . . . ?
O4 C2 C4 C5 35.6(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C2 C4 C5 C6 175.3(3) . . . . ?
C4 C5 C6 C7 -1.4(6) . . . . ?
C5 C6 C7 C8 1.3(6) . . . . ?
C6 C7 C8 C3 -0.3(6) . . . . ?
C4 C3 C8 C7 -0.7(6) . . . . ?
C1 C3 C8 C7 176.3(3) . . . . ?
N1 C9 C10 C11 173.4(3) . . . . ?
C9 C10 C11 C12 170.9(3) . . . . ?
C10 C11 C12 C13 176.2(3) . . . . ?
C11 C12 C13 N2 173.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.079
_chemical_properties_physical    Moisture-sensitive,Hygroscopic,Heat-sensitive
####################################################################### 
# 
# 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_191206d
_database_code_depnum_ccdc_archive 'CCDC 2006386'
loop_
_audit_author_name
_audit_author_address
'Li zihan'
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-05-28 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1,5-Pentanediamine1,2-phthalicacid
_chemical_name_common            
'1,5-Diaminopentane 1,2-phthalicacid?1,5-Pentanediamineacidephtalique'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H26 N2 O8'
_chemical_formula_weight         434.44

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   11.3309(9)
_cell_length_b                   12.4114(11)
_cell_length_c                   14.7248(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.451(2)
_cell_angle_gamma                90.00
_cell_volume                     2070.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2615
_cell_measurement_theta_min      2.432
_cell_measurement_theta_max      28.799

_exptl_crystal_description       ?
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9502
_exptl_absorpt_correction_T_max  0.9664
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5100
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2889
_reflns_number_gt                2627
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0250(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.2(9)
_refine_ls_number_reflns         2889
_refine_ls_number_parameters     283
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3974(2) 0.75382(18) 0.52142(15) 0.0365(5) Uani 1 1 d . . .
H1A H 0.3659 0.8173 0.5356 0.055 Uiso 1 1 calc R . .
H1B H 0.4190 0.7197 0.5720 0.055 Uiso 1 1 calc R . .
H1C H 0.3443 0.7143 0.4914 0.055 Uiso 1 1 calc R . .
N2 N 0.3648(2) 0.72212(18) 0.10637(15) 0.0392(6) Uani 1 1 d . . .
H2A H 0.4111 0.7555 0.0668 0.059 Uiso 1 1 calc R . .
H2B H 0.3146 0.6794 0.0767 0.059 Uiso 1 1 calc R . .
H2C H 0.4088 0.6828 0.1441 0.059 Uiso 1 1 calc R . .
O1 O 0.4813(2) 0.64525(15) 0.66717(14) 0.0526(6) Uani 1 1 d . . .
O2 O 0.48755(19) 0.48026(14) 0.61436(13) 0.0407(5) Uani 1 1 d . . .
O3 O 0.74794(19) 0.40043(15) 0.60976(13) 0.0435(5) Uani 1 1 d . . .
O4 O 0.62583(19) 0.27451(15) 0.65871(13) 0.0429(5) Uani 1 1 d . . .
H4 H 0.6415 0.2459 0.6101 0.064 Uiso 1 1 calc R . .
O5 O -0.0181(2) 0.6824(2) 0.46743(15) 0.0608(6) Uani 1 1 d . . .
O6 O 0.16460(18) 0.66956(15) 0.51843(13) 0.0428(5) Uani 1 1 d . . .
O7 O 0.37837(18) 0.53207(14) 0.47442(13) 0.0390(5) Uani 1 1 d . . .
H7 H 0.4062 0.5093 0.5223 0.059 Uiso 1 1 calc R . .
O8 O 0.23121(19) 0.42346(15) 0.50851(13) 0.0445(5) Uani 1 1 d . . .
C1 C 0.5124(2) 0.5513(2) 0.67199(17) 0.0323(6) Uani 1 1 d . . .
C2 C 0.6787(3) 0.3658(2) 0.66422(18) 0.0335(6) Uani 1 1 d . . .
C3 C 0.5844(2) 0.5162(2) 0.75199(17) 0.0314(6) Uani 1 1 d . . .
C4 C 0.6558(2) 0.42622(19) 0.74944(17) 0.0307(6) Uani 1 1 d . . .
C5 C 0.7190(3) 0.3969(2) 0.82603(19) 0.0400(7) Uani 1 1 d . . .
H5 H 0.7668 0.3360 0.8247 0.048 Uiso 1 1 calc R . .
C6 C 0.7121(3) 0.4563(3) 0.9034(2) 0.0475(8) Uani 1 1 d . . .
H6 H 0.7552 0.4359 0.9546 0.057 Uiso 1 1 calc R . .
C7 C 0.6420(3) 0.5458(3) 0.9063(2) 0.0474(8) Uani 1 1 d . . .
H7A H 0.6372 0.5863 0.9593 0.057 Uiso 1 1 calc R . .
C8 C 0.5789(3) 0.5754(2) 0.83097(18) 0.0400(7) Uani 1 1 d . . .
H8 H 0.5316 0.6366 0.8330 0.048 Uiso 1 1 calc R . .
C9 C 0.0839(3) 0.6528(2) 0.46044(19) 0.0345(6) Uani 1 1 d . . .
C10 C 0.2763(3) 0.49080(19) 0.46132(17) 0.0301(6) Uani 1 1 d . . .
C11 C 0.1210(2) 0.59678(19) 0.37668(17) 0.0316(6) Uani 1 1 d . . .
C12 C 0.2157(2) 0.52653(19) 0.37573(16) 0.0291(6) Uani 1 1 d . . .
C13 C 0.2495(3) 0.4787(2) 0.29694(19) 0.0391(7) Uani 1 1 d . . .
H13 H 0.3126 0.4308 0.2973 0.047 Uiso 1 1 calc R . .
C14 C 0.1912(3) 0.5004(2) 0.2170(2) 0.0451(8) Uani 1 1 d . . .
H14 H 0.2152 0.4680 0.1632 0.054 Uiso 1 1 calc R . .
C15 C 0.0983(3) 0.5696(3) 0.2169(2) 0.0484(8) Uani 1 1 d . . .
H15 H 0.0587 0.5848 0.1629 0.058 Uiso 1 1 calc R . .
C16 C 0.0626(3) 0.6170(2) 0.29558(19) 0.0410(7) Uani 1 1 d . . .
H16 H -0.0018 0.6634 0.2947 0.049 Uiso 1 1 calc R . .
C17 C 0.5010(3) 0.7707(3) 0.4641(2) 0.0497(8) Uani 1 1 d . . .
H17A H 0.5321 0.7012 0.4459 0.060 Uiso 1 1 calc R . .
H17B H 0.5617 0.8072 0.4993 0.060 Uiso 1 1 calc R . .
C18 C 0.4738(3) 0.8355(3) 0.3810(2) 0.0518(8) Uani 1 1 d . . .
H18A H 0.5475 0.8542 0.3520 0.062 Uiso 1 1 calc R . .
H18B H 0.4364 0.9022 0.3996 0.062 Uiso 1 1 calc R . .
C19 C 0.3954(3) 0.7812(2) 0.3122(2) 0.0417(7) Uani 1 1 d . . .
H19A H 0.4320 0.7147 0.2925 0.050 Uiso 1 1 calc R . .
H19B H 0.3206 0.7633 0.3401 0.050 Uiso 1 1 calc R . .
C20 C 0.3737(3) 0.8522(2) 0.23162(19) 0.0422(7) Uani 1 1 d . . .
H20A H 0.4492 0.8716 0.2057 0.051 Uiso 1 1 calc R . .
H20B H 0.3363 0.9181 0.2521 0.051 Uiso 1 1 calc R . .
C21 C 0.2982(3) 0.8028(2) 0.1586(2) 0.0428(7) Uani 1 1 d . . .
H21A H 0.2301 0.7687 0.1859 0.051 Uiso 1 1 calc R . .
H21B H 0.2700 0.8588 0.1179 0.051 Uiso 1 1 calc R . .


_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
N1 C17 1.467(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C21 1.474(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
O1 C1 1.220(3) . ?
O2 C1 1.254(3) . ?
O3 C2 1.205(3) . ?
O4 C2 1.284(3) . ?
O4 H4 0.8200 . ?
O5 C9 1.218(4) . ?
O6 C9 1.264(3) . ?
O7 C10 1.279(4) . ?
O7 H7 0.8200 . ?
O8 C10 1.203(3) . ?
C1 C3 1.493(4) . ?
C2 C4 1.486(4) . ?
C3 C8 1.378(4) . ?
C3 C4 1.379(4) . ?
C4 C5 1.380(4) . ?
C5 C6 1.360(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.365(4) . ?
C7 H7A 0.9300 . ?
C8 H8 0.9300 . ?
C9 C11 1.480(4) . ?
C10 C12 1.498(4) . ?
C11 C12 1.382(4) . ?
C11 C16 1.384(4) . ?
C12 C13 1.361(4) . ?
C13 C14 1.372(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.494(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.501(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.497(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.501(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 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
C17 N1 H1A 109.5 . . ?
C17 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C17 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C21 N2 H2A 109.5 . . ?
C21 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C21 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C2 O4 H4 109.5 . . ?
C10 O7 H7 109.5 . . ?
O1 C1 O2 124.7(2) . . ?
O1 C1 C3 118.7(2) . . ?
O2 C1 C3 116.5(2) . . ?
O3 C2 O4 125.3(3) . . ?
O3 C2 C4 120.1(2) . . ?
O4 C2 C4 114.5(2) . . ?
C8 C3 C4 119.0(2) . . ?
C8 C3 C1 118.8(2) . . ?
C4 C3 C1 122.1(2) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 C2 122.5(2) . . ?
C5 C4 C2 117.7(2) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7A 120.2 . . ?
C6 C7 H7A 120.2 . . ?
C7 C8 C3 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
O5 C9 O6 125.2(3) . . ?
O5 C9 C11 119.2(3) . . ?
O6 C9 C11 115.5(3) . . ?
O8 C10 O7 125.4(3) . . ?
O8 C10 C12 119.9(2) . . ?
O7 C10 C12 114.6(2) . . ?
C12 C11 C16 118.1(3) . . ?
C12 C11 C9 122.1(2) . . ?
C16 C11 C9 119.8(3) . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 C10 117.2(2) . . ?
C11 C12 C10 121.9(2) . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N1 C17 C18 112.7(3) . . ?
N1 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
N1 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 115.3(2) . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18B 108.4 . . ?
C19 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C18 111.3(2) . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C21 114.6(2) . . ?
C19 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
C19 C20 H20B 108.6 . . ?
C21 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
N2 C21 C20 111.1(3) . . ?
N2 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
N2 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C3 C8 22.9(4) . . . . ?
O2 C1 C3 C8 -156.6(3) . . . . ?
O1 C1 C3 C4 -157.4(3) . . . . ?
O2 C1 C3 C4 23.1(4) . . . . ?
C8 C3 C4 C5 0.6(4) . . . . ?
C1 C3 C4 C5 -179.1(2) . . . . ?
C8 C3 C4 C2 -172.1(3) . . . . ?
C1 C3 C4 C2 8.2(4) . . . . ?
O3 C2 C4 C3 77.8(4) . . . . ?
O4 C2 C4 C3 -106.7(3) . . . . ?
O3 C2 C4 C5 -95.1(3) . . . . ?
O4 C2 C4 C5 80.4(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C2 C4 C5 C6 172.7(3) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C6 C7 C8 C3 0.3(5) . . . . ?
C4 C3 C8 C7 -0.6(4) . . . . ?
C1 C3 C8 C7 179.1(3) . . . . ?
O5 C9 C11 C12 -154.7(3) . . . . ?
O6 C9 C11 C12 27.9(4) . . . . ?
O5 C9 C11 C16 27.4(4) . . . . ?
O6 C9 C11 C16 -150.0(3) . . . . ?
C16 C11 C12 C13 -0.2(4) . . . . ?
C9 C11 C12 C13 -178.2(2) . . . . ?
C16 C11 C12 C10 -173.5(2) . . . . ?
C9 C11 C12 C10 8.6(4) . . . . ?
O8 C10 C12 C13 -96.3(3) . . . . ?
O7 C10 C12 C13 79.5(3) . . . . ?
O8 C10 C12 C11 77.1(3) . . . . ?
O7 C10 C12 C11 -107.1(3) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C10 C12 C13 C14 174.4(3) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C11 0.9(5) . . . . ?
C12 C11 C16 C15 -0.6(4) . . . . ?
C9 C11 C16 C15 177.3(3) . . . . ?
N1 C17 C18 C19 -68.0(4) . . . . ?
C17 C18 C19 C20 -179.7(3) . . . . ?
C18 C19 C20 C21 178.7(3) . . . . ?
C19 C20 C21 N2 -75.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037
_exptl_crystal_recrystallization_method 'Reaction Crystallization'
_chemical_properties_physical    Moisture-sensitive,Hygroscopic,Heat-sensitive
####################################################################### 
# 
# 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_210827c
_database_code_depnum_ccdc_archive 'CCDC 2106410'
loop_
_audit_author_name
_audit_author_address
'Li zihan'
;Nanjing Tech University
China
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'1,5-pentanediamine-o-Phthalic acid salt; 1,5-pentanediamine-1,2-Phthalic acid salt'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H26 N2 O8'
_chemical_formula_weight         434.44

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   15.2457(12)
_cell_length_b                   18.4249(14)
_cell_length_c                   8.4299(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.730(5)
_cell_angle_gamma                90.00
_cell_volume                     2214.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1809
_cell_measurement_theta_min      2.707
_cell_measurement_theta_max      28.554

_exptl_crystal_description       plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5226
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1940
_reflns_number_gt                1179
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0548P)²+1.3625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1940
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.23935(15) 0.43672(11) 1.0964(3) 0.0439(6) Uani 1 1 d . . .
H1A H 0.2158 0.4077 1.1558 0.066 Uiso 1 1 calc R . .
H1B H 0.2820 0.4660 1.1668 0.066 Uiso 1 1 calc R . .
H1C H 0.2661 0.4100 1.0382 0.066 Uiso 1 1 calc R . .
O1 O 0.15316(17) 0.04697(10) 0.2012(3) 0.0748(7) Uani 1 1 d . . .
O2 O 0.17699(18) 0.14918(11) 0.0884(3) 0.0800(8) Uani 1 1 d . . .
O3 O 0.17060(16) 0.27877(10) 0.1188(3) 0.0679(7) Uani 1 1 d . . .
H3 H 0.1679 0.2348 0.1030 0.102 Uiso 1 1 calc R . .
O4 O 0.15121(16) 0.35766(10) 0.2965(3) 0.0672(7) Uani 1 1 d . . .
C1 C 0.1546(2) 0.11448(15) 0.2008(4) 0.0482(7) Uani 1 1 d . . .
C2 C 0.15165(18) 0.29341(14) 0.2538(3) 0.0428(7) Uani 1 1 d . . .
C3 C 0.12768(17) 0.15621(13) 0.3348(3) 0.0382(6) Uani 1 1 d . . .
C4 C 0.12885(17) 0.23335(14) 0.3600(3) 0.0394(7) Uani 1 1 d . . .
C5 C 0.1065(2) 0.26014(17) 0.4970(4) 0.0589(8) Uani 1 1 d . . .
H5 H 0.1082 0.3100 0.5155 0.071 Uiso 1 1 calc R . .
C6 C 0.0817(2) 0.2145(2) 0.6060(4) 0.0729(10) Uani 1 1 d . . .
H6 H 0.0676 0.2338 0.6960 0.087 Uiso 1 1 calc R . .
C7 C 0.0784(2) 0.1401(2) 0.5796(4) 0.0698(10) Uani 1 1 d . . .
H7 H 0.0610 0.1092 0.6506 0.084 Uiso 1 1 calc R . .
C8 C 0.10119(19) 0.11231(16) 0.4460(4) 0.0548(8) Uani 1 1 d . . .
H8 H 0.0988 0.0623 0.4296 0.066 Uiso 1 1 calc R . .
C9 C 0.16265(19) 0.48101(14) 0.9767(3) 0.0445(7) Uani 1 1 d . . .
H9A H 0.1878 0.5096 0.9061 0.053 Uiso 1 1 calc R . .
H9B H 0.1389 0.5144 1.0411 0.053 Uiso 1 1 calc R . .
C10 C 0.0821(2) 0.43473(14) 0.8637(3) 0.0488(7) Uani 1 1 d . . .
H10A H 0.0600 0.4034 0.9343 0.059 Uiso 1 1 calc R . .
H10B H 0.1048 0.4040 0.7931 0.059 Uiso 1 1 calc R . .
C11 C 0.0000 0.4803(2) 0.7500 0.0471(10) Uani 1 2 d S . .
H11A H -0.0222 0.5113 0.8209 0.056 Uiso 0.50 1 calc PR . .
H11B H 0.0222 0.5113 0.6791 0.056 Uiso 0.50 1 calc PR . .


_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
N1 C9 1.489(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O1 C1 1.244(3) . ?
O2 C1 1.285(3) . ?
O3 C2 1.298(3) . ?
O3 H3 0.8200 . ?
O4 C2 1.238(3) . ?
C1 C3 1.538(4) . ?
C2 C4 1.538(4) . ?
C3 C8 1.402(4) . ?
C3 C4 1.436(4) . ?
C4 C5 1.405(4) . ?
C5 C6 1.392(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.522(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.529(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C10 1.529(3) 2_556 ?
C11 H11A 0.9700 . ?
C11 H11B 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
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 O3 H3 109.5 . . ?
O1 C1 O2 120.6(3) . . ?
O1 C1 C3 119.2(3) . . ?
O2 C1 C3 120.2(2) . . ?
O4 C2 O3 118.7(2) . . ?
O4 C2 C4 119.5(2) . . ?
O3 C2 C4 121.8(2) . . ?
C8 C3 C4 117.6(2) . . ?
C8 C3 C1 114.7(2) . . ?
C4 C3 C1 127.7(2) . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 C2 113.4(2) . . ?
C3 C4 C2 128.2(2) . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 119.3(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C3 122.9(3) . . ?
C7 C8 H8 118.5 . . ?
C3 C8 H8 118.5 . . ?
N1 C9 C10 112.6(2) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 112.6(2) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C10 113.4(3) 2_556 . ?
C10 C11 H11A 108.9 2_556 . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 2_556 . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C3 C8 -1.4(4) . . . . ?
O2 C1 C3 C8 177.6(3) . . . . ?
O1 C1 C3 C4 177.1(3) . . . . ?
O2 C1 C3 C4 -4.0(4) . . . . ?
C8 C3 C4 C5 2.0(4) . . . . ?
C1 C3 C4 C5 -176.4(2) . . . . ?
C8 C3 C4 C2 -177.7(2) . . . . ?
C1 C3 C4 C2 3.9(4) . . . . ?
O4 C2 C4 C5 1.8(4) . . . . ?
O3 C2 C4 C5 -177.5(3) . . . . ?
O4 C2 C4 C3 -178.4(3) . . . . ?
O3 C2 C4 C3 2.2(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C2 C4 C5 C6 178.6(3) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
C6 C7 C8 C3 -0.1(5) . . . . ?
C4 C3 C8 C7 -1.4(4) . . . . ?
C1 C3 C8 C7 177.2(3) . . . . ?
N1 C9 C10 C11 175.68(18) . . . . ?
C9 C10 C11 C10 -179.6(3) . . . 2_556 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.043
_chemical_properties_physical    Moisture-sensitive,Heat-sensitive
####################################################################### 
# 
# 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_190719g
_database_code_depnum_ccdc_archive 'CCDC 2006384'
loop_
_audit_author_name
_audit_author_address
Lizihan
;Nanjing Tech University
China
;
_audit_update_record             
;
2020-05-28 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1,5-Pentanediamine 1,2-phthalicacid'
_chemical_name_common            
'1,5-Diaminopentane 1,2-phthalicacid?1,5-Pentanediamine1,2-dicarboxybenzene'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H44 N4 O9'
_chemical_formula_weight         568.66

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4676(8)
_cell_length_b                   11.6199(9)
_cell_length_c                   14.6569(11)
_cell_angle_alpha                90.3490(10)
_cell_angle_beta                 99.391(2)
_cell_angle_gamma                109.501(3)
_cell_volume                     1496.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2615
_cell_measurement_theta_min      2.318
_cell_measurement_theta_max      25.883

_exptl_crystal_description       ?
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9586
_exptl_absorpt_correction_T_max  0.9721
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7584
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5185
_reflns_number_gt                3477
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1015P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5185
_refine_ls_number_parameters     372
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1737
_refine_ls_wR_factor_gt          0.1574
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.144
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6855(2) -0.32288(18) 0.40813(14) 0.0418(5) Uani 1 1 d . . .
H1A H 0.7393 -0.3071 0.3625 0.063 Uiso 1 1 calc R . .
H1B H 0.6053 -0.3907 0.3925 0.063 Uiso 1 1 calc R . .
H1C H 0.7434 -0.3331 0.4595 0.063 Uiso 1 1 calc R . .
N2 N 0.8762(3) 0.34251(19) 0.55328(16) 0.0515(6) Uani 1 1 d . . .
H2A H 0.9137 0.3350 0.6118 0.077 Uiso 1 1 calc R . .
H2B H 0.8354 0.4015 0.5512 0.077 Uiso 1 1 calc R . .
H2C H 0.9506 0.3614 0.5201 0.077 Uiso 1 1 calc R . .
N3 N 0.7473(3) 0.4305(2) 0.25589(16) 0.0515(6) Uani 1 1 d . . .
H3A H 0.8466 0.4462 0.2740 0.077 Uiso 1 1 calc R . .
H3B H 0.7011 0.4169 0.3050 0.077 Uiso 1 1 calc R . .
H3C H 0.7321 0.4942 0.2280 0.077 Uiso 1 1 calc R . .
N4 N 0.6930(3) 0.4100(2) -0.20922(15) 0.0488(6) Uani 1 1 d . A .
H4A H 0.7605 0.3742 -0.2165 0.073 Uiso 1 1 calc R . .
H4B H 0.6807 0.4537 -0.2577 0.073 Uiso 1 1 calc R . .
H4C H 0.6043 0.3530 -0.2051 0.073 Uiso 1 1 calc R . .
O1 O 0.5589(2) 0.36993(18) 0.38687(13) 0.0531(5) Uani 1 1 d . . .
O2 O 0.4099(2) 0.48386(15) 0.36545(13) 0.0473(5) Uani 1 1 d . . .
O3 O 0.1202(2) 0.39347(16) 0.45139(13) 0.0487(5) Uani 1 1 d . . .
O4 O 0.0467(2) 0.43312(18) 0.30661(14) 0.0550(5) Uani 1 1 d . . .
O5 O 1.1295(2) 0.7271(2) 0.25093(15) 0.0692(6) Uani 1 1 d . . .
O6 O 0.9145(2) 0.7158(2) 0.29552(14) 0.0637(6) Uani 1 1 d . . .
O7 O 0.6178(2) 0.58968(19) 0.17813(15) 0.0615(6) Uani 1 1 d . . .
O8 O 0.6018(3) 0.7722(2) 0.19540(17) 0.0730(7) Uani 1 1 d . . .
O9 O 0.6310(4) 1.0125(3) 0.1853(4) 0.1621(18) Uani 1 1 d . . .
H9 H 0.6464 0.9472 0.1895 0.243 Uiso 1 1 calc R . .
C1 C 0.4315(3) 0.3824(2) 0.36548(16) 0.0358(6) Uani 1 1 d . . .
C2 C 0.1028(3) 0.3751(2) 0.36471(19) 0.0383(6) Uani 1 1 d . . .
C3 C 0.2932(3) 0.2687(2) 0.33613(16) 0.0360(6) Uani 1 1 d . . .
C4 C 0.1439(3) 0.2692(2) 0.32929(16) 0.0359(6) Uani 1 1 d . . .
C5 C 0.0219(3) 0.1637(2) 0.29374(18) 0.0442(6) Uani 1 1 d . . .
H5 H -0.0772 0.1643 0.2870 0.053 Uiso 1 1 calc R . .
C6 C 0.0480(4) 0.0583(2) 0.26842(19) 0.0532(8) Uani 1 1 d . . .
H6 H -0.0339 -0.0114 0.2450 0.064 Uiso 1 1 calc R . .
C7 C 0.1943(4) 0.0560(3) 0.27775(19) 0.0522(7) Uani 1 1 d . . .
H7 H 0.2114 -0.0153 0.2621 0.063 Uiso 1 1 calc R . .
C8 C 0.3155(3) 0.1609(2) 0.31064(18) 0.0449(7) Uani 1 1 d . . .
H8 H 0.4142 0.1597 0.3159 0.054 Uiso 1 1 calc R . .
C9 C 0.9973(3) 0.7327(2) 0.23585(19) 0.0436(6) Uani 1 1 d . . .
C10 C 0.6622(3) 0.7010(3) 0.16748(19) 0.0471(7) Uani 1 1 d . . .
C11 C 0.9387(3) 0.7644(2) 0.14022(18) 0.0417(6) Uani 1 1 d . . .
C12 C 0.7868(3) 0.7528(2) 0.11090(18) 0.0431(6) Uani 1 1 d . . .
C13 C 0.7434(4) 0.7866(3) 0.0223(2) 0.0625(9) Uani 1 1 d . . .
H13 H 0.6425 0.7805 0.0028 0.075 Uiso 1 1 calc R . .
C14 C 0.8446(5) 0.8283(3) -0.0362(2) 0.0772(10) Uani 1 1 d . . .
H14 H 0.8116 0.8478 -0.0956 0.093 Uiso 1 1 calc R . .
C15 C 0.9938(5) 0.8417(3) -0.0083(2) 0.0743(10) Uani 1 1 d . . .
H15 H 1.0632 0.8717 -0.0479 0.089 Uiso 1 1 calc R . .
C16 C 1.0420(4) 0.8104(3) 0.0795(2) 0.0575(8) Uani 1 1 d . . .
H16 H 1.1441 0.8199 0.0985 0.069 Uiso 1 1 calc R . .
C17 C 0.6326(3) -0.2186(2) 0.42471(18) 0.0404(6) Uani 1 1 d . . .
H17A H 0.5717 -0.2375 0.4734 0.049 Uiso 1 1 calc R . .
H17B H 0.5679 -0.2092 0.3688 0.049 Uiso 1 1 calc R . .
C18 C 0.7615(3) -0.0988(2) 0.45213(18) 0.0424(6) Uani 1 1 d . . .
H18A H 0.8237 -0.0795 0.4041 0.051 Uiso 1 1 calc R . .
H18B H 0.8252 -0.1066 0.5090 0.051 Uiso 1 1 calc R . .
C19 C 0.7002(3) 0.0043(2) 0.4662(2) 0.0472(7) Uani 1 1 d . . .
H19A H 0.6282 -0.0205 0.5085 0.057 Uiso 1 1 calc R . .
H19B H 0.6453 0.0167 0.4073 0.057 Uiso 1 1 calc R . .
C20 C 0.8225(3) 0.1255(2) 0.50435(19) 0.0424(6) Uani 1 1 d . . .
H20A H 0.8755 0.1144 0.5643 0.051 Uiso 1 1 calc R . .
H20B H 0.8961 0.1499 0.4630 0.051 Uiso 1 1 calc R . .
C21 C 0.7574(3) 0.2252(2) 0.5146(2) 0.0565(8) Uani 1 1 d . . .
H21A H 0.7060 0.2373 0.4545 0.068 Uiso 1 1 calc R . .
H21B H 0.6825 0.2002 0.5550 0.068 Uiso 1 1 calc R . .
C22 C 0.6842(4) 0.3214(3) 0.1907(3) 0.0750(10) Uani 1 1 d . . .
H22A H 0.5768 0.3069 0.1694 0.090 Uiso 1 1 calc R . .
H22B H 0.6930 0.2510 0.2232 0.090 Uiso 1 1 calc R . .
C23 C 0.7613(6) 0.3327(5) 0.1091(3) 0.1051(16) Uani 1 1 d . A .
H23A H 0.7391 0.2510 0.0818 0.126 Uiso 1 1 calc R . .
H23B H 0.8702 0.3659 0.1312 0.126 Uiso 1 1 calc R . .
C24 C 0.7216(5) 0.4107(4) 0.0324(3) 0.0899(12) Uani 1 1 d DU . .
H24A H 0.7013 0.4761 0.0633 0.108 Uiso 0.470(5) 1 calc PR A 1
H24B H 0.6251 0.3599 -0.0035 0.108 Uiso 0.470(5) 1 calc PR A 1
H24C H 0.6162 0.4051 0.0280 0.108 Uiso 0.530(5) 1 d PR A 2
H24D H 0.7843 0.4954 0.0494 0.108 Uiso 0.530(5) 1 d PR A 2
C25 C 0.8236(8) 0.4734(7) -0.0404(4) 0.0636(12) Uani 0.470(5) 1 d PDU A 1
H25A H 0.8928 0.5525 -0.0132 0.076 Uiso 0.470(5) 1 calc PR A 1
H25B H 0.8849 0.4241 -0.0511 0.076 Uiso 0.470(5) 1 calc PR A 1
C25' C 0.7451(8) 0.3802(6) -0.0484(4) 0.0636(12) Uani 0.530(5) 1 d PD A 2
H25C H 0.6654 0.3045 -0.0735 0.076 Uiso 0.530(5) 1 calc PR A 2
H25D H 0.8415 0.3658 -0.0405 0.076 Uiso 0.530(5) 1 calc PR A 2
C26 C 0.7479(4) 0.4905(4) -0.1246(3) 0.0849(11) Uani 1 1 d DU . .
H26A H 0.8129 0.5674 -0.1431 0.102 Uiso 0.470(5) 1 calc PR A 1
H26B H 0.6589 0.5061 -0.1108 0.102 Uiso 0.470(5) 1 calc PR A 1
H26C H 0.6792 0.5335 -0.1146 0.102 Uiso 0.530(5) 1 d PR A 2
H26D H 0.8494 0.5489 -0.1229 0.102 Uiso 0.530(5) 1 d PR A 2
C27 C 0.4893(6) 0.9925(5) 0.1444(5) 0.154(3) Uani 1 1 d . . .
H27A H 0.4211 0.9325 0.1762 0.231 Uiso 1 1 calc R . .
H27B H 0.4761 0.9631 0.0811 0.231 Uiso 1 1 calc R . .
H27C H 0.4675 1.0674 0.1460 0.231 Uiso 1 1 calc R . .


_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
N1 C17 1.490(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C21 1.485(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N3 C22 1.473(4) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N4 C26 1.461(4) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
O1 C1 1.252(3) . ?
O2 C1 1.262(3) . ?
O3 C2 1.262(3) . ?
O4 C2 1.249(3) . ?
O5 C9 1.259(3) . ?
O6 C9 1.242(3) . ?
O7 C10 1.239(3) . ?
O8 C10 1.252(3) . ?
O9 C27 1.320(5) . ?
O9 H9 0.8200 . ?
C1 C3 1.516(3) . ?
C2 C4 1.520(3) . ?
C3 C8 1.396(3) . ?
C3 C4 1.403(3) . ?
C4 C5 1.399(3) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C11 1.516(4) . ?
C10 C12 1.514(4) . ?
C11 C12 1.392(4) . ?
C11 C16 1.405(4) . ?
C12 C13 1.396(4) . ?
C13 C14 1.361(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.512(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.521(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.526(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.500(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.485(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.526(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25' 1.308(6) . ?
C24 C25 1.574(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C24 H24D 0.9700 . ?
C25 C26 1.374(7) . ?
C25 H24D 1.4677 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H26D 1.5032 . ?
C25' C26 1.702(7) . ?
C25' H25C 0.9700 . ?
C25' H25D 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C26 H26D 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N1 H1A 109.5 . . ?
C17 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C17 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C21 N2 H2A 109.5 . . ?
C21 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C21 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C22 N3 H3A 109.5 . . ?
C22 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C22 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C26 N4 H4A 109.5 . . ?
C26 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C26 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C27 O9 H9 109.5 . . ?
O1 C1 O2 124.4(2) . . ?
O1 C1 C3 118.4(2) . . ?
O2 C1 C3 117.2(2) . . ?
O4 C2 O3 124.6(2) . . ?
O4 C2 C4 118.1(2) . . ?
O3 C2 C4 117.1(2) . . ?
C8 C3 C4 118.8(2) . . ?
C8 C3 C1 118.6(2) . . ?
C4 C3 C1 122.6(2) . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 C2 116.3(2) . . ?
C3 C4 C2 124.2(2) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C3 121.6(3) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
O6 C9 O5 123.4(3) . . ?
O6 C9 C11 118.8(2) . . ?
O5 C9 C11 117.8(3) . . ?
O7 C10 O8 123.3(3) . . ?
O7 C10 C12 118.8(2) . . ?
O8 C10 C12 117.6(3) . . ?
C12 C11 C16 118.6(3) . . ?
C12 C11 C9 122.5(2) . . ?
C16 C11 C9 118.9(3) . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 C10 124.4(2) . . ?
C13 C12 C10 116.9(2) . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N1 C17 C18 113.3(2) . . ?
N1 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
N1 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 110.8(2) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 C20 114.1(2) . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C21 C20 C19 112.2(2) . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
N2 C21 C20 112.2(2) . . ?
N2 C21 H21A 109.2 . . ?
C20 C21 H21A 109.2 . . ?
N2 C21 H21B 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
N3 C22 C23 113.3(3) . . ?
N3 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
N3 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 C24 117.7(3) . . ?
C22 C23 H23A 107.9 . . ?
C24 C23 H23A 107.9 . . ?
C22 C23 H23B 107.9 . . ?
C24 C23 H23B 107.9 . . ?
H23A C23 H23B 107.2 . . ?
C25' C24 C23 113.2(4) . . ?
C25' C24 C25 42.9(4) . . ?
C23 C24 C25 126.2(4) . . ?
C25' C24 H24A 140.2 . . ?
C23 C24 H24A 105.8 . . ?
C25 C24 H24A 105.8 . . ?
C25' C24 H24B 71.5 . . ?
C23 C24 H24B 105.8 . . ?
C25 C24 H24B 105.8 . . ?
H24A C24 H24B 106.2 . . ?
C25' C24 H24C 109.7 . . ?
C23 C24 H24C 109.5 . . ?
C25 C24 H24C 123.5 . . ?
H24A C24 H24C 62.5 . . ?
H24B C24 H24C 44.3 . . ?
C25' C24 H24D 108.5 . . ?
C23 C24 H24D 108.2 . . ?
C25 C24 H24D 65.6 . . ?
H24A C24 H24D 48.9 . . ?
H24B C24 H24D 142.4 . . ?
H24C C24 H24D 107.6 . . ?
C26 C25 C24 116.3(5) . . ?
C26 C25 H24D 124.5 . . ?
C24 C25 H24D 37.0 . . ?
C26 C25 H25A 108.2 . . ?
C24 C25 H25A 108.2 . . ?
H24D C25 H25A 71.6 . . ?
C26 C25 H25B 108.2 . . ?
C24 C25 H25B 108.2 . . ?
H24D C25 H25B 125.2 . . ?
H25A C25 H25B 107.4 . . ?
C26 C25 H26D 39.1 . . ?
C24 C25 H26D 150.9 . . ?
H24D C25 H26D 132.9 . . ?
H25A C25 H26D 76.7 . . ?
H25B C25 H26D 96.9 . . ?
C24 C25' C26 112.0(5) . . ?
C24 C25' H25C 109.2 . . ?
C26 C25' H25C 109.2 . . ?
C24 C25' H25D 109.2 . . ?
C26 C25' H25D 109.2 . . ?
H25C C25' H25D 107.9 . . ?
C25 C26 N4 129.4(4) . . ?
C25 C26 C25' 39.4(4) . . ?
N4 C26 C25' 97.3(3) . . ?
C25 C26 H26A 104.9 . . ?
N4 C26 H26A 104.9 . . ?
C25' C26 H26A 142.8 . . ?
C25 C26 H26B 104.9 . . ?
N4 C26 H26B 104.9 . . ?
C25' C26 H26B 96.5 . . ?
H26A C26 H26B 105.8 . . ?
C25 C26 H26C 109.1 . . ?
N4 C26 H26C 112.5 . . ?
C25' C26 H26C 111.9 . . ?
H26A C26 H26C 86.7 . . ?
H26B C26 H26C 19.2 . . ?
C25 C26 H26D 77.7 . . ?
N4 C26 H26D 112.6 . . ?
C25' C26 H26D 112.4 . . ?
H26A C26 H26D 31.1 . . ?
H26B C26 H26D 128.0 . . ?
H26C C26 H26D 109.7 . . ?
O9 C27 H27A 109.5 . . ?
O9 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O9 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C3 C8 -16.6(3) . . . . ?
O2 C1 C3 C8 162.5(2) . . . . ?
O1 C1 C3 C4 166.6(2) . . . . ?
O2 C1 C3 C4 -14.3(3) . . . . ?
C8 C3 C4 C5 -2.6(3) . . . . ?
C1 C3 C4 C5 174.2(2) . . . . ?
C8 C3 C4 C2 172.8(2) . . . . ?
C1 C3 C4 C2 -10.4(4) . . . . ?
O4 C2 C4 C5 -72.0(3) . . . . ?
O3 C2 C4 C5 104.2(3) . . . . ?
O4 C2 C4 C3 112.5(3) . . . . ?
O3 C2 C4 C3 -71.3(3) . . . . ?
C3 C4 C5 C6 2.2(4) . . . . ?
C2 C4 C5 C6 -173.5(2) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C8 -1.5(4) . . . . ?
C6 C7 C8 C3 1.1(4) . . . . ?
C4 C3 C8 C7 1.0(4) . . . . ?
C1 C3 C8 C7 -176.0(2) . . . . ?
O6 C9 C11 C12 -12.5(4) . . . . ?
O5 C9 C11 C12 168.7(2) . . . . ?
O6 C9 C11 C16 165.8(2) . . . . ?
O5 C9 C11 C16 -13.0(4) . . . . ?
C16 C11 C12 C13 0.3(4) . . . . ?
C9 C11 C12 C13 178.6(2) . . . . ?
C16 C11 C12 C10 177.9(3) . . . . ?
C9 C11 C12 C10 -3.8(4) . . . . ?
O7 C10 C12 C11 -71.6(4) . . . . ?
O8 C10 C12 C11 113.5(3) . . . . ?
O7 C10 C12 C13 106.0(3) . . . . ?
O8 C10 C12 C13 -68.9(3) . . . . ?
C11 C12 C13 C14 1.2(5) . . . . ?
C10 C12 C13 C14 -176.6(3) . . . . ?
C12 C13 C14 C15 -2.0(5) . . . . ?
C13 C14 C15 C16 1.3(6) . . . . ?
C14 C15 C16 C11 0.2(5) . . . . ?
C12 C11 C16 C15 -1.0(4) . . . . ?
C9 C11 C16 C15 -179.4(3) . . . . ?
N1 C17 C18 C19 178.9(2) . . . . ?
C17 C18 C19 C20 173.6(2) . . . . ?
C18 C19 C20 C21 178.4(2) . . . . ?
C19 C20 C21 N2 179.0(2) . . . . ?
N3 C22 C23 C24 -76.9(5) . . . . ?
C22 C23 C24 C25' -155.3(5) . . . . ?
C22 C23 C24 C25 157.1(5) . . . . ?
C25' C24 C25 C26 65.5(6) . . . . ?
C23 C24 C25 C26 151.4(5) . . . . ?
C23 C24 C25' C26 -164.1(4) . . . . ?
C25 C24 C25' C26 -45.3(5) . . . . ?
C24 C25 C26 N4 -91.0(6) . . . . ?
C24 C25 C26 C25' -48.6(5) . . . . ?
C24 C25' C26 C25 60.7(6) . . . . ?
C24 C25' C26 N4 -151.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.047
_chemical_properties_physical    Air-sensitive,Hygroscopic,Heat-sensitive
