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

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

data_20161213NGDY_0m
_database_code_depnum_ccdc_archive 'CCDC 1818541'
loop_
_audit_author_name
_audit_author_address

'Pengpeng Yang, Sen Wang, Zihan Li, Qingqing Li, Xiaojie Li, Hanjie Ying, Qiao Chen'
'Nanjing Tech University'
_audit_update_record             
;
2018-01-22 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '1,5-Diaminopentane adipate'
_chemical_name_common            
'Cadavarine adipate;Pentane-1,5-diamine adipate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H24 N2 O4? 2 H2O'
_chemical_formula_sum            'C11 H28 N2 O6'
_chemical_formula_weight         284.35

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

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

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

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

_cell_length_a                   20.435(2)
_cell_length_b                   4.6351(6)
_cell_length_c                   17.7856(19)
_cell_angle_alpha                90
_cell_angle_beta                 116.068(3)
_cell_angle_gamma                90
_cell_volume                     1513.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3170
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.59

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5030
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.540
_diffrn_reflns_theta_max         24.979
_diffrn_reflns_theta_full        24.979
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1338
_reflns_number_gt                1187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+1.1257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1338
_refine_ls_number_parameters     88
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      22.880
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36448(7) 0.2501(3) 0.15979(9) 0.0220(3) Uani 1 1 d . . . . .
H1D H 0.3714 0.1265 0.1199 0.026 Uiso 1 1 calc R U . . .
H1E H 0.3575 0.1276 0.1999 0.026 Uiso 1 1 calc R U . . .
C2 C 0.43186(7) 0.4347(3) 0.20514(9) 0.0216(3) Uani 1 1 d . . . . .
H2A H 0.4251 0.5561 0.2456 0.026 Uiso 1 1 calc R U . . .
H2B H 0.4382 0.5595 0.1651 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5000 0.2523(4) 0.2500 0.0230(5) Uani 1 2 d S T P . .
H3A H 0.5063 0.1291 0.2096 0.028 Uiso 0.5 1 calc DR U P . .
H3B H 0.4937 0.1291 0.2904 0.028 Uiso 0.5 1 calc DR U P . .
C5 C 0.03086(7) 0.5512(3) -0.00990(8) 0.0195(3) Uani 1 1 d . . . . .
H5A H 0.0546 0.3845 -0.0200 0.023 Uiso 1 1 calc R U . . .
H5B H 0.0105 0.6653 -0.0608 0.023 Uiso 1 1 calc R U . . .
C6 C 0.08728(7) 0.7304(3) 0.06014(9) 0.0201(3) Uani 1 1 d . . . . .
H6A H 0.1087 0.6122 0.1102 0.024 Uiso 1 1 calc R U . . .
H6B H 0.0627 0.8905 0.0719 0.024 Uiso 1 1 calc R U . . .
C7 C 0.14832(7) 0.8500(3) 0.04230(8) 0.0179(3) Uani 1 1 d . . . . .
N1 N 0.29846(6) 0.4308(3) 0.11506(7) 0.0192(3) Uani 1 1 d . . . . .
H1A H 0.2930 0.5494 0.1513 0.029 Uiso 1 1 calc R U . . .
H1B H 0.2595 0.3176 0.0916 0.029 Uiso 1 1 calc R U . . .
H1C H 0.3034 0.5336 0.0756 0.029 Uiso 1 1 calc R U . . .
O1 O 0.15807(6) 0.7478(2) -0.01648(6) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.18673(6) 1.0486(3) 0.08956(7) 0.0342(3) Uani 1 1 d . . . . .
O3 O 0.20475(6) 0.1997(2) 0.23966(6) 0.0301(3) Uani 1 1 d D . . . .
H3C H 0.1914 0.1595 0.1877 0.036 Uiso 1 1 d R U . . .
H3D H 0.2288 0.3510 0.2465 0.036 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4871(18) . ?
C1 C2 1.5173(19) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C2 C3 1.5211(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C2 1.5211(18) 2_655 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.5194(19) . ?
C5 C5 1.526(3) 5_565 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.5205(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O1 1.2409(17) . ?
C7 O2 1.2611(18) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O3 H3C 0.8613 . ?
O3 H3D 0.8335 . ?

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
N1 C1 C2 111.40(12) . . ?
N1 C1 H1D 109.3 . . ?
C2 C1 H1D 109.3 . . ?
N1 C1 H1E 109.3 . . ?
C2 C1 H1E 109.3 . . ?
H1D C1 H1E 108.0 . . ?
C1 C2 C3 111.92(12) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C2 112.48(17) . 2_655 ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 2_655 . ?
C2 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 2_655 . ?
H3A C3 H3B 107.8 . . ?
C6 C5 C5 112.77(14) . 5_565 ?
C6 C5 H5A 109.0 . . ?
C5 C5 H5A 109.0 5_565 . ?
C6 C5 H5B 109.0 . . ?
C5 C5 H5B 109.0 5_565 . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 115.14(12) . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
O1 C7 O2 123.83(13) . . ?
O1 C7 C6 119.13(12) . . ?
O2 C7 C6 117.04(12) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
H3C O3 H3D 103.1 . . ?

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
N1 C1 C2 C3 -179.07(10) . . . . ?
C1 C2 C3 C2 179.29(13) . . . 2_655 ?
C5 C5 C6 C7 -177.33(15) 5_565 . . . ?
C5 C6 C7 O1 -15.72(19) . . . . ?
C5 C6 C7 O2 164.83(13) . . . . ?

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
O3 H3D O3 0.83 2.06 2.8858(13) 174.1 4
O3 H3C O2 0.86 1.78 2.6246(15) 165.8 1_545
N1 H1C O1 0.89 1.87 2.7296(15) 163.2 7_565
N1 H1B O2 0.89 1.93 2.7653(15) 156.0 1_545
N1 H1A O3 0.89 2.04 2.8955(16) 160.0 4
C1 H1D O1 0.97 2.40 3.3172(18) 156.6 7
C1 H1D O1 0.97 2.40 3.3172(18) 156.6 7
N1 H1A O3 0.89 2.04 2.8955(16) 160.0 4
N1 H1B O2 0.89 1.93 2.7653(15) 156.0 1_545
N1 H1C O1 0.89 1.87 2.7296(15) 163.2 7_565
O3 H3C O2 0.86 1.78 2.6246(15) 165.8 1_545
O3 H3D O3 0.83 2.06 2.8858(13) 174.1 4

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
