# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_180605j
_database_code_depnum_ccdc_archive 'CCDC 1969111'
loop_
_audit_author_name
_audit_author_address
'Li zihan'
;Nanjing Tech University
China
;
_audit_update_record             
;
2019-11-30 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1,5-pentanediamine-Isophthalate
_chemical_name_common            ?
_chemical_melting_point          511.55
_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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   10.9462(9)
_cell_length_b                   13.6297(11)
_cell_length_c                   19.4386(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2900.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3272
_cell_measurement_theta_min      2.387
_cell_measurement_theta_max      28.245

_exptl_crystal_description       stick
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9608
_exptl_absorpt_correction_T_max  0.9851
_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            13154
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2562
_reflns_number_gt                1764
_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)+(0.0503P)²+0.9405P] 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       0.0051(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2562
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.53795(15) 0.33519(11) 0.09743(8) 0.0330(4) Uani 1 1 d . . .
H1A H 0.4616 0.3244 0.0836 0.050 Uiso 1 1 calc R . .
H1B H 0.5638 0.2843 0.1222 0.050 Uiso 1 1 calc R . .
H1C H 0.5861 0.3427 0.0609 0.050 Uiso 1 1 calc R . .
N2 N 0.57619(17) 0.88137(11) 0.09183(8) 0.0383(4) Uani 1 1 d . . .
H2A H 0.6435 0.8759 0.0664 0.058 Uiso 1 1 calc R . .
H2B H 0.5801 0.9360 0.1168 0.058 Uiso 1 1 calc R . .
H2C H 0.5111 0.8839 0.0645 0.058 Uiso 1 1 calc R . .
O1 O 0.29319(13) 0.26923(10) 0.06148(7) 0.0398(4) Uani 1 1 d . . .
O2 O 0.23060(14) 0.14090(10) -0.00029(6) 0.0400(4) Uani 1 1 d . . .
O3 O 0.35721(15) 0.21733(10) 0.31264(7) 0.0462(4) Uani 1 1 d . . .
O4 O 0.37477(14) 0.06661(10) 0.35522(7) 0.0424(4) Uani 1 1 d . . .
O5 O 0.90250(15) 0.35937(11) 0.51374(7) 0.0479(4) Uani 1 1 d . . .
H5C H 0.8390 0.3341 0.4959 0.058 Uiso 1 1 d R . .
H5D H 0.8847 0.3799 0.5538 0.058 Uiso 1 1 d R . .
C1 C 0.27130(17) 0.17930(15) 0.05447(10) 0.0307(5) Uani 1 1 d . . .
C2 C 0.35767(18) 0.12586(14) 0.30661(10) 0.0314(5) Uani 1 1 d . . .
C3 C 0.29181(17) 0.11157(13) 0.11489(9) 0.0283(4) Uani 1 1 d . . .
C4 C 0.31815(17) 0.14781(14) 0.17999(9) 0.0293(5) Uani 1 1 d . . .
H4 H 0.3264 0.2151 0.1863 0.035 Uiso 1 1 calc R . .
C5 C 0.33239(17) 0.08521(13) 0.23587(9) 0.0281(4) Uani 1 1 d . . .
C6 C 0.32068(19) -0.01516(14) 0.22554(10) 0.0353(5) Uani 1 1 d . . .
H6 H 0.3303 -0.0579 0.2624 0.042 Uiso 1 1 calc R . .
C7 C 0.2950(2) -0.05207(14) 0.16108(11) 0.0390(5) Uani 1 1 d . . .
H7 H 0.2872 -0.1194 0.1547 0.047 Uiso 1 1 calc R . .
C8 C 0.28081(18) 0.01066(14) 0.10607(10) 0.0346(5) Uani 1 1 d . . .
H8 H 0.2638 -0.0147 0.0627 0.042 Uiso 1 1 calc R . .
C9 C 0.5419(2) 0.42526(14) 0.14006(10) 0.0371(5) Uani 1 1 d . . .
H9A H 0.6144 0.4235 0.1688 0.044 Uiso 1 1 calc R . .
H9B H 0.4713 0.4263 0.1702 0.044 Uiso 1 1 calc R . .
C10 C 0.54344(19) 0.51776(14) 0.09787(10) 0.0360(5) Uani 1 1 d . . .
H10A H 0.4724 0.5185 0.0680 0.043 Uiso 1 1 calc R . .
H10B H 0.6156 0.5178 0.0689 0.043 Uiso 1 1 calc R . .
C11 C 0.54331(19) 0.61020(14) 0.14169(10) 0.0350(5) Uani 1 1 d . . .
H11A H 0.4675 0.6138 0.1674 0.042 Uiso 1 1 calc R . .
H11B H 0.6100 0.6071 0.1745 0.042 Uiso 1 1 calc R . .
C12 C 0.5569(2) 0.70147(14) 0.09779(11) 0.0392(5) Uani 1 1 d . . .
H12A H 0.6295 0.6948 0.0696 0.047 Uiso 1 1 calc R . .
H12B H 0.4872 0.7059 0.0671 0.047 Uiso 1 1 calc R . .
C13 C 0.5660(2) 0.79519(14) 0.13828(11) 0.0393(5) Uani 1 1 d . . .
H13A H 0.4941 0.8023 0.1671 0.047 Uiso 1 1 calc R . .
H13B H 0.6370 0.7924 0.1681 0.047 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 1.482(2) . ?
N2 C13 1.486(2) . ?
O1 C1 1.256(2) . ?
O2 C1 1.267(2) . ?
O3 C2 1.252(2) . ?
O4 C2 1.257(2) . ?
C1 C3 1.511(3) . ?
C2 C5 1.508(3) . ?
C3 C4 1.389(3) . ?
C3 C8 1.391(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.389(3) . ?
C6 C7 1.379(3) . ?
C7 C8 1.378(3) . ?
C9 C10 1.504(3) . ?
C10 C11 1.521(3) . ?
C11 C12 1.516(3) . ?
C12 C13 1.504(3) . ?

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
O1 C1 O2 124.14(18) . . ?
O1 C1 C3 118.92(17) . . ?
O2 C1 C3 116.93(17) . . ?
O3 C2 O4 124.74(18) . . ?
O3 C2 C5 116.77(17) . . ?
O4 C2 C5 118.47(17) . . ?
C4 C3 C8 118.81(17) . . ?
C4 C3 C1 121.46(17) . . ?
C8 C3 C1 119.70(17) . . ?
C3 C4 C5 121.14(17) . . ?
C6 C5 C4 118.77(17) . . ?
C6 C5 C2 120.71(17) . . ?
C4 C5 C2 120.50(16) . . ?
C7 C6 C5 120.63(18) . . ?
C8 C7 C6 120.11(18) . . ?
C7 C8 C3 120.54(18) . . ?
N1 C9 C10 112.94(16) . . ?
C9 C10 C11 112.89(16) . . ?
C12 C11 C10 111.38(16) . . ?
C13 C12 C11 114.14(17) . . ?
N2 C13 C12 111.01(16) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 'Reaction Crystallization'
_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_191125d
_database_code_depnum_ccdc_archive 'CCDC 1969113'
loop_
_audit_author_name
_audit_author_address
'Li zihan'
;Nanjing Tech University
China
;
_audit_update_record             
;
2019-11-30 deposited with the CCDC.	2020-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1,5-pentanediamine-Isophthalate
_chemical_name_common            1,5-diaminopentane-Isophthalate
_chemical_melting_point          509.05
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 N2 O4'
_chemical_formula_weight         268.31

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                   13.4758(12)
_cell_length_b                   11.6629(11)
_cell_length_c                   18.8817(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.974(4)
_cell_angle_gamma                90.00
_cell_volume                     2879.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1461
_cell_measurement_theta_min      2.752
_cell_measurement_theta_max      27.742

_exptl_crystal_description       rod
_exptl_crystal_colour            white/transparent
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_T_max  0.9909
_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            14270
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_sigmaI/netI    0.0950
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5066
_reflns_number_gt                2581
_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)+(0.0263P)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         5066
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.14026(17) -0.1579(2) 0.37970(12) 0.0490(7) Uani 1 1 d . . .
H1A H 0.1460 -0.1245 0.4229 0.073 Uiso 1 1 calc R . .
H1B H 0.1936 -0.2038 0.3818 0.073 Uiso 1 1 calc R . .
H1C H 0.0829 -0.1988 0.3683 0.073 Uiso 1 1 calc R . .
N2 N -0.04493(18) 0.3446(2) 0.47262(12) 0.0516(7) Uani 1 1 d . . .
H2A H -0.0450 0.4017 0.4414 0.077 Uiso 1 1 calc R . .
H2B H -0.0315 0.3721 0.5179 0.077 Uiso 1 1 calc R . .
H2C H -0.1060 0.3109 0.4623 0.077 Uiso 1 1 calc R . .
N3 N 0.41883(18) 0.6386(2) 0.58139(13) 0.0502(7) Uani 1 1 d . . .
H3A H 0.4267 0.6158 0.5381 0.075 Uiso 1 1 calc R . .
H3B H 0.4734 0.6786 0.6042 0.075 Uiso 1 1 calc R . .
H3C H 0.3633 0.6823 0.5752 0.075 Uiso 1 1 calc R . .
N4 N 0.49482(18) 0.1540(2) 0.53715(12) 0.0482(7) Uani 1 1 d . . .
H4A H 0.5512 0.1940 0.5561 0.072 Uiso 1 1 calc R . .
H4B H 0.4931 0.1361 0.4911 0.072 Uiso 1 1 calc R . .
H4C H 0.4948 0.0901 0.5629 0.072 Uiso 1 1 calc R . .
O1 O 0.40507(15) 0.55983(18) 0.43799(10) 0.0585(7) Uani 1 1 d . . .
O2 O 0.32755(15) 0.72617(19) 0.39856(11) 0.0572(6) Uani 1 1 d . . .
O3 O 0.08042(17) 0.72892(18) 0.15456(11) 0.0637(7) Uani 1 1 d . . .
O4 O 0.01636(15) 0.56442(17) 0.10160(10) 0.0546(6) Uani 1 1 d . . .
O5 O 0.47055(16) 0.95424(18) 0.89605(10) 0.0584(7) Uani 1 1 d . . .
O6 O 0.46263(16) 0.78876(19) 0.83468(11) 0.0584(6) Uani 1 1 d . . .
O7 O 0.24002(15) 0.76155(18) 0.57657(11) 0.0537(6) Uani 1 1 d . . .
O8 O 0.1785(2) 0.9251(2) 0.52242(12) 0.0957(10) Uani 1 1 d . . .
C1 C 0.3363(2) 0.6174(3) 0.39549(16) 0.0453(8) Uani 1 1 d . . .
C2 C 0.0705(2) 0.6218(3) 0.15450(16) 0.0418(8) Uani 1 1 d . . .
C3 C 0.2580(2) 0.5538(3) 0.33730(15) 0.0382(7) Uani 1 1 d . . .
C4 C 0.1997(2) 0.6128(2) 0.27644(15) 0.0379(7) Uani 1 1 d . . .
H4 H 0.2092 0.6912 0.2724 0.045 Uiso 1 1 calc R . .
C5 C 0.1278(2) 0.5563(2) 0.22195(14) 0.0361(7) Uani 1 1 d . . .
C6 C 0.1135(2) 0.4387(3) 0.23003(15) 0.0462(8) Uani 1 1 d . . .
H6 H 0.0646 0.3999 0.1950 0.055 Uiso 1 1 calc R . .
C7 C 0.1711(2) 0.3789(3) 0.28939(16) 0.0498(9) Uani 1 1 d . . .
H7 H 0.1615 0.3005 0.2936 0.060 Uiso 1 1 calc R . .
C8 C 0.2428(2) 0.4361(3) 0.34210(16) 0.0487(9) Uani 1 1 d . . .
H8 H 0.2816 0.3954 0.3815 0.058 Uiso 1 1 calc R . .
C9 C 0.4381(2) 0.8922(3) 0.83897(16) 0.0423(8) Uani 1 1 d . . .
C10 C 0.2266(2) 0.8694(3) 0.57672(17) 0.0504(9) Uani 1 1 d . . .
C11 C 0.3647(2) 0.9468(2) 0.77390(14) 0.0372(7) Uani 1 1 d . . .
C12 C 0.3336(2) 0.8878(2) 0.70760(15) 0.0391(8) Uani 1 1 d . . .
H12 H 0.3606 0.8155 0.7031 0.047 Uiso 1 1 calc R . .
C13 C 0.2630(2) 0.9349(3) 0.64788(14) 0.0386(8) Uani 1 1 d . . .
C14 C 0.2217(2) 1.0429(3) 0.65504(16) 0.0452(8) Uani 1 1 d . . .
H14 H 0.1744 1.0750 0.6159 0.054 Uiso 1 1 calc R . .
C15 C 0.2510(2) 1.1028(3) 0.72073(16) 0.0462(8) Uani 1 1 d . . .
H15 H 0.2229 1.1744 0.7255 0.055 Uiso 1 1 calc R . .
C16 C 0.3219(2) 1.0554(3) 0.77889(15) 0.0436(8) Uani 1 1 d . . .
H16 H 0.3417 1.0965 0.8222 0.052 Uiso 1 1 calc R . .
C17 C 0.1374(3) -0.0675(3) 0.32247(17) 0.0563(9) Uani 1 1 d . . .
H17A H 0.1203 -0.1035 0.2747 0.068 Uiso 1 1 calc R . .
H17B H 0.2051 -0.0342 0.3294 0.068 Uiso 1 1 calc R . .
C18 C 0.0611(2) 0.0276(3) 0.32399(16) 0.0569(9) Uani 1 1 d . . .
H18A H -0.0050 -0.0066 0.3226 0.068 Uiso 1 1 calc R . .
H18B H 0.0540 0.0740 0.2805 0.068 Uiso 1 1 calc R . .
C19 C 0.0908(3) 0.1053(3) 0.39089(17) 0.0646(11) Uani 1 1 d . . .
H19A H 0.1567 0.1398 0.3921 0.077 Uiso 1 1 calc R . .
H19B H 0.0984 0.0587 0.4344 0.077 Uiso 1 1 calc R . .
C20 C 0.0134(2) 0.2007(3) 0.39269(16) 0.0546(9) Uani 1 1 d . . .
H20A H 0.0161 0.2571 0.3554 0.066 Uiso 1 1 calc R . .
H20B H -0.0550 0.1686 0.3818 0.066 Uiso 1 1 calc R . .
C21 C 0.0353(3) 0.2586(3) 0.46633(17) 0.0629(10) Uani 1 1 d . . .
H21A H 0.0397 0.2008 0.5039 0.075 Uiso 1 1 calc R . .
H21B H 0.1010 0.2969 0.4749 0.075 Uiso 1 1 calc R . .
C22 C 0.4073(2) 0.5366(3) 0.62600(16) 0.0507(9) Uani 1 1 d . . .
H22A H 0.3943 0.5615 0.6719 0.061 Uiso 1 1 calc R . .
H22B H 0.4703 0.4928 0.6367 0.061 Uiso 1 1 calc R . .
C23 C 0.3196(2) 0.4606(3) 0.58590(17) 0.0540(9) Uani 1 1 d . . .
H23A H 0.3257 0.4491 0.5363 0.065 Uiso 1 1 calc R . .
H23B H 0.2554 0.5000 0.5836 0.065 Uiso 1 1 calc R . .
C24 C 0.3165(2) 0.3432(3) 0.62199(19) 0.0598(10) Uani 1 1 d . . .
H24A H 0.2524 0.3059 0.5991 0.072 Uiso 1 1 calc R . .
H24B H 0.3173 0.3550 0.6730 0.072 Uiso 1 1 calc R . .
C25 C 0.4052(2) 0.2621(3) 0.61752(16) 0.0505(9) Uani 1 1 d . . .
H25A H 0.4696 0.3006 0.6379 0.061 Uiso 1 1 calc R . .
H25B H 0.4021 0.1946 0.6469 0.061 Uiso 1 1 calc R . .
C26 C 0.4026(2) 0.2247(3) 0.53958(17) 0.0585(10) Uani 1 1 d . . .
H26A H 0.3412 0.1801 0.5204 0.070 Uiso 1 1 calc R . .
H26B H 0.4003 0.2919 0.5090 0.070 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 1.503(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C21 1.499(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N3 C22 1.487(3) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N4 C26 1.501(3) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
O1 C1 1.263(3) . ?
O2 C1 1.277(3) . ?
O3 C2 1.257(3) . ?
O4 C2 1.275(3) . ?
O5 C9 1.284(3) . ?
O6 C9 1.258(3) . ?
O7 C10 1.271(3) . ?
O8 C10 1.254(3) . ?
C1 C3 1.520(4) . ?
C2 C5 1.525(4) . ?
C3 C8 1.395(4) . ?
C3 C4 1.405(3) . ?
C4 C5 1.396(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(4) . ?
C6 C7 1.387(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C11 1.519(4) . ?
C10 C13 1.520(4) . ?
C11 C12 1.401(4) . ?
C11 C16 1.404(4) . ?
C12 C13 1.400(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(4) . ?
C14 C15 1.395(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.517(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.528(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.532(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.509(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.524(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.535(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.542(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.527(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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 . . ?
O1 C1 O2 124.1(3) . . ?
O1 C1 C3 118.4(3) . . ?
O2 C1 C3 117.5(3) . . ?
O3 C2 O4 124.3(3) . . ?
O3 C2 C5 117.7(3) . . ?
O4 C2 C5 118.0(3) . . ?
C8 C3 C4 118.2(3) . . ?
C8 C3 C1 121.4(3) . . ?
C4 C3 C1 120.4(3) . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 C2 120.0(3) . . ?
C6 C5 C2 121.8(2) . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C3 121.1(3) . . ?
C7 C8 H8 119.4 . . ?
C3 C8 H8 119.4 . . ?
O6 C9 O5 123.6(3) . . ?
O6 C9 C11 118.7(3) . . ?
O5 C9 C11 117.8(3) . . ?
O8 C10 O7 123.8(3) . . ?
O8 C10 C13 117.1(3) . . ?
O7 C10 C13 118.9(3) . . ?
C12 C11 C16 117.6(2) . . ?
C12 C11 C9 120.9(3) . . ?
C16 C11 C9 121.4(3) . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 C10 119.2(3) . . ?
C12 C13 C10 121.8(3) . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.5(3) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
N1 C17 C18 113.5(3) . . ?
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 114.0(3) . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 C20 114.0(3) . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 111.3(2) . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N2 C21 C20 112.8(2) . . ?
N2 C21 H21A 109.0 . . ?
C20 C21 H21A 109.0 . . ?
N2 C21 H21B 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
N3 C22 C23 111.0(2) . . ?
N3 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
N3 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 113.5(3) . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C25 114.7(3) . . ?
C23 C24 H24A 108.6 . . ?
C25 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
C25 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C26 C25 C24 113.0(2) . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
N4 C26 C25 111.1(2) . . ?
N4 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
N4 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 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 17.8(4) . . . . ?
O2 C1 C3 C8 -161.6(3) . . . . ?
O1 C1 C3 C4 -161.3(3) . . . . ?
O2 C1 C3 C4 19.3(4) . . . . ?
C8 C3 C4 C5 0.3(4) . . . . ?
C1 C3 C4 C5 179.5(3) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C3 C4 C5 C2 -176.4(3) . . . . ?
O3 C2 C5 C4 -9.0(4) . . . . ?
O4 C2 C5 C4 170.5(3) . . . . ?
O3 C2 C5 C6 173.4(3) . . . . ?
O4 C2 C5 C6 -7.1(4) . . . . ?
C4 C5 C6 C7 -1.9(5) . . . . ?
C2 C5 C6 C7 175.7(3) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
C6 C7 C8 C3 0.6(5) . . . . ?
C4 C3 C8 C7 -1.2(5) . . . . ?
C1 C3 C8 C7 179.6(3) . . . . ?
O6 C9 C11 C12 -7.0(4) . . . . ?
O5 C9 C11 C12 174.0(3) . . . . ?
O6 C9 C11 C16 170.0(3) . . . . ?
O5 C9 C11 C16 -8.9(4) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C9 C11 C12 C13 177.6(3) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C11 C12 C13 C10 -177.9(3) . . . . ?
O8 C10 C13 C14 15.5(5) . . . . ?
O7 C10 C13 C14 -159.8(3) . . . . ?
O8 C10 C13 C12 -167.4(3) . . . . ?
O7 C10 C13 C12 17.3(5) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C10 C13 C14 C15 177.6(3) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C14 C15 C16 C11 -0.9(5) . . . . ?
C12 C11 C16 C15 0.5(4) . . . . ?
C9 C11 C16 C15 -176.7(3) . . . . ?
N1 C17 C18 C19 69.3(4) . . . . ?
C17 C18 C19 C20 -179.6(3) . . . . ?
C18 C19 C20 C21 168.3(3) . . . . ?
C19 C20 C21 N2 -174.3(3) . . . . ?
N3 C22 C23 C24 168.9(3) . . . . ?
C22 C23 C24 C25 -68.7(4) . . . . ?
C23 C24 C25 C26 -66.1(4) . . . . ?
C24 C25 C26 N4 175.3(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         0.226
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.054
_exptl_crystal_recrystallization_method 
'Reaction Crystallization/Anti-solvent Crystallization'
_chemical_properties_physical    Moisture-sensitive,Heat-sensitive
