# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2PZH-PZ2COO-3H2O
_database_code_depnum_ccdc_archive 'CCDC 1473719'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 N2 O4, 2(C4 H11 N2), 3(H2 O)'
_chemical_formula_sum            'C14 H36 N6 O7'
_chemical_formula_weight         400.49

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                   30.854(5)
_cell_length_b                   7.3079(13)
_cell_length_c                   9.1538(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.466(3)
_cell_angle_gamma                90
_cell_volume                     2007.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2311
_cell_measurement_theta_min      4.37
_cell_measurement_theta_max      30.43
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 with CCD area detector'
_diffrn_measurement_method       '/w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7910
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.715
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1974
_reflns_number_gt                1817
_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-2014/7 (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)+(0.0450P)²+1.2111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1974
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35808(2) 0.13715(10) 0.98480(9) 0.02036(19) Uani 1 1 d . . . . .
O2 O 0.32502(2) 0.29722(10) 0.78048(8) 0.01851(19) Uani 1 1 d . . . . .
N1 N 0.28329(3) 0.18297(14) 0.93126(10) 0.0219(2) Uani 1 1 d . . . . .
N2 N 0.37835(3) 0.20317(12) 0.60520(10) 0.0146(2) Uani 1 1 d . . . . .
H2N H 0.3719(4) 0.085(2) 0.5724(15) 0.025(3) Uiso 1 1 d . . . . .
H1N H 0.3637(5) 0.227(2) 0.6828(17) 0.032(4) Uiso 1 1 d . . . . .
N3 N 0.43066(3) 0.33976(12) 0.40982(10) 0.0179(2) Uani 1 1 d . . . . .
H3N H 0.4434(5) 0.3233(18) 0.3331(16) 0.025(3) Uiso 1 1 d . . . . .
C1 C 0.32392(3) 0.20729(13) 0.89720(11) 0.0143(2) Uani 1 1 d . . . . .
C2 C 0.27759(4) 0.10100(16) 1.07075(12) 0.0214(3) Uani 1 1 d . . . . .
H2A H 0.3062 0.0598 1.1298 0.026 Uiso 1 1 calc R U . . .
H2B H 0.2581 -0.0045 1.0482 0.026 Uiso 1 1 calc R U . . .
C3 C 0.24233(3) 0.26050(17) 0.83940(12) 0.0214(3) Uani 1 1 d . . . . .
H3A H 0.2210 0.1633 0.8049 0.026 Uiso 1 1 calc R U . . .
H3B H 0.2487 0.3198 0.7519 0.026 Uiso 1 1 calc R U . . .
C4 C 0.35910(3) 0.32851(15) 0.47829(11) 0.0173(2) Uani 1 1 d . . . . .
H4A H 0.3621 0.4543 0.5131 0.021 Uiso 1 1 calc R U . . .
H4B H 0.3276 0.3026 0.4415 0.021 Uiso 1 1 calc R U . . .
C5 C 0.38287(4) 0.30391(15) 0.35232(11) 0.0191(2) Uani 1 1 d . . . . .
H5A H 0.3785 0.1801 0.3135 0.023 Uiso 1 1 calc R U . . .
H5B H 0.3707 0.3879 0.2710 0.023 Uiso 1 1 calc R U . . .
C6 C 0.44977(3) 0.20616(14) 0.52756(12) 0.0180(2) Uani 1 1 d . . . . .
H6A H 0.4816 0.2263 0.5618 0.022 Uiso 1 1 calc R U . . .
H6B H 0.4451 0.0831 0.4873 0.022 Uiso 1 1 calc R U . . .
C7 C 0.42759(3) 0.22708(15) 0.65820(11) 0.0163(2) Uani 1 1 d . . . . .
H7A H 0.4394 0.1363 0.7345 0.020 Uiso 1 1 calc R U . . .
H7B H 0.4340 0.3474 0.7027 0.020 Uiso 1 1 calc R U . . .
O1W O 0.43939(3) 0.31053(12) 0.05191(10) 0.0253(2) Uani 1 1 d . . . . .
H1W H 0.4376(5) 0.413(2) 0.0029(18) 0.042(4) Uiso 1 1 d . . . . .
H2W H 0.4119(6) 0.261(2) 0.0212(17) 0.043(4) Uiso 1 1 d . . . . .
O2W O 0.5000 0.09970(16) 0.2500 0.0247(3) Uani 1 2 d S T P . .
H3W H 0.4821(6) 0.172(2) 0.1820(18) 0.046(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2740(13) . ?
O2 C1 1.2616(13) . ?
N1 C1 1.3719(14) . ?
N1 C2 1.4577(13) . ?
N1 C3 1.4596(13) . ?
N2 C4 1.4900(13) . ?
N2 C7 1.4936(13) . ?
N3 C5 1.4691(14) . ?
N3 C6 1.4719(14) . ?
C2 C3 1.5212(16) 7_557 ?
C3 C2 1.5212(16) 7_557 ?
C4 C5 1.5146(14) . ?
C6 C7 1.5176(14) . ?

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
C1 N1 C2 123.74(9) . . ?
C1 N1 C3 122.22(9) . . ?
C2 N1 C3 113.53(8) . . ?
C4 N2 C7 111.84(8) . . ?
C5 N3 C6 109.97(8) . . ?
O2 C1 O1 124.14(9) . . ?
O2 C1 N1 117.79(9) . . ?
O1 C1 N1 118.08(9) . . ?
N1 C2 C3 110.28(9) . 7_557 ?
N1 C3 C2 110.58(9) . 7_557 ?
N2 C4 C5 110.17(8) . . ?
N3 C5 C4 109.25(8) . . ?
N3 C6 C7 109.44(8) . . ?
N2 C7 C6 110.09(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O1 0.921(15) 1.816(15) 2.7331(12) 173.0(12) 6
N2 H1N O2 0.942(16) 1.729(16) 2.6427(12) 162.6(13) .
N3 H3N O1W 0.890(15) 2.549(15) 3.3560(14) 151.0(11) .
N3 H3N O2W 0.890(15) 2.629(14) 3.3545(11) 139.3(11) .
C7 H7A O2W 0.97 2.52 3.2444(14) 131.0 5_656
O1W H1W N3 0.869(18) 1.986(18) 2.8517(13) 173.4(15) 6_565
O1W H2W O1 0.905(18) 1.852(18) 2.7494(12) 171.2(15) 1_554
O2W H3W O1W 0.902(16) 1.856(16) 2.7532(11) 172.6(16) .

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_PZ-H2O
_database_code_depnum_ccdc_archive 'CCDC 1473720'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'piperazine monohydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H10 N2, H2 O'
_chemical_formula_sum            'C4 H12 N2 O'
_chemical_formula_weight         104.16

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

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

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

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

_cell_length_a                   9.856(3)
_cell_length_b                   6.681(2)
_cell_length_c                   9.172(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.778(4)
_cell_angle_gamma                90
_cell_volume                     571.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3311
_cell_measurement_theta_min      4.37
_cell_measurement_theta_max      30.53

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.255
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker with CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4625
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.368
_diffrn_reflns_theta_max         25.966
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1114
_reflns_number_gt                1032
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0508P)²+0.2207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1114
_refine_ls_number_parameters     80
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22313(9) 0.08354(12) 0.64085(9) 0.0187(2) Uani 1 1 d . . . . .
H1O H 0.268(2) 0.089(3) 0.576(2) 0.048(5) Uiso 1 1 d . . . . .
H2O H 0.141(2) 0.148(3) 0.600(2) 0.063(6) Uiso 1 1 d . . . . .
N1 N 0.37871(10) 0.12048(14) 0.42187(11) 0.0170(3) Uani 1 1 d . . . . .
H1N H 0.3343(15) 0.206(2) 0.3470(17) 0.021(3) Uiso 1 1 d . . . . .
N2 N 0.04297(10) 0.70430(14) 0.52549(10) 0.0164(3) Uani 1 1 d . . . . .
H2N H 0.0940(18) 0.799(3) 0.5649(19) 0.042(5) Uiso 1 1 d . . . . .
C1 C 0.11639(11) 0.56583(16) 0.45136(12) 0.0142(3) Uani 1 1 d . . . . .
H1A H 0.1978 0.5058 0.5287 0.017 Uiso 1 1 calc R U . . .
H1B H 0.1516 0.6387 0.3794 0.017 Uiso 1 1 calc R U . . .
C2 C -0.01342(11) 0.59708(16) 0.63351(12) 0.0146(3) Uani 1 1 d . . . . .
H2A H -0.0629 0.6902 0.6801 0.017 Uiso 1 1 calc R U . . .
H2B H 0.0651 0.5378 0.7149 0.017 Uiso 1 1 calc R U . . .
C3 C 0.40913(11) -0.06672(17) 0.35418(12) 0.0171(3) Uani 1 1 d . . . . .
H3A H 0.4685 -0.0390 0.2903 0.021 Uiso 1 1 calc R U . . .
H3B H 0.3202 -0.1261 0.2898 0.021 Uiso 1 1 calc R U . . .
C4 C 0.51389(12) 0.21145(16) 0.51829(12) 0.0182(3) Uani 1 1 d . . . . .
H4A H 0.4941 0.3355 0.5626 0.022 Uiso 1 1 calc R U . . .
H4B H 0.5741 0.2418 0.4558 0.022 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.4694(15) . ?
N1 C4 1.4725(15) . ?
N2 C2 1.4691(14) . ?
N2 C1 1.4692(14) . ?
C1 C2 1.5204(15) 3_566 ?
C2 C1 1.5204(15) 3_566 ?
C3 C4 1.5190(15) 3_656 ?
C4 C3 1.5190(15) 3_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C4 109.68(9) . . ?
C2 N2 C1 110.78(9) . . ?
N2 C1 C2 109.91(9) . 3_566 ?
N2 C2 C1 109.80(9) . 3_566 ?
N1 C3 C4 109.62(9) . 3_656 ?
N1 C4 C3 109.32(9) . 3_656 ?

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
O1 H1O N1 0.86(2) 2.05(2) 2.9033(14) 176.5(18) .
O1 H2O N2 0.89(2) 2.06(2) 2.9393(14) 171.6(19) 3_566
N1 H1N O1 0.890(15) 2.330(16) 3.2187(14) 176.5(13) 4_565
N2 H2N O1 0.819(19) 2.267(19) 3.0793(14) 171.9(16) 1_565

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_PZHCOO-3H2O
_database_code_depnum_ccdc_archive 'CCDC 1473721'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'piperazinium carbaxamide trihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 N2 O2, 3(H2 O)'
_chemical_formula_sum            'C5 H16 N2 O5'
_chemical_formula_weight         184.20

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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   8.163(2)
_cell_length_b                   18.627(5)
_cell_length_c                   5.9869(17)
_cell_angle_alpha                90
_cell_angle_beta                 110.214(4)
_cell_angle_gamma                90
_cell_volume                     854.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2981
_cell_measurement_theta_max      28.64
_cell_measurement_theta_min      3.84

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0508 before and 0.0345 after correction.
The Ratio of minimum to maximum transmission is 0.9213.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            4516
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.187
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             1638
_reflns_number_gt                1568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_max     0.946
_reflns_Friedel_fraction_full    0.959

_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-2014/7 (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)+(0.0333P)²+0.3737P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1638
_refine_ls_number_parameters     141
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0636
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3482(2) 0.15844(9) 0.1541(3) 0.0169(4) Uani 1 1 d . . . . .
O2 O 0.1841(2) 0.15793(9) 0.3882(3) 0.0168(4) Uani 1 1 d . . . . .
N1 N 0.3079(3) 0.26089(9) 0.3286(4) 0.0163(4) Uani 1 1 d . . . . .
N2 N 0.2356(3) 0.41003(9) 0.2539(4) 0.0138(4) Uani 1 1 d . . . . .
H1N H 0.167(4) 0.4454(17) 0.161(6) 0.026(8) Uiso 1 1 d . . . . .
H2N H 0.332(4) 0.4341(16) 0.363(6) 0.025(8) Uiso 1 1 d . . . . .
C1 C 0.2785(3) 0.18877(11) 0.2883(4) 0.0125(5) Uani 1 1 d . . . . .
C2 C 0.4053(3) 0.30360(12) 0.2148(4) 0.0147(5) Uani 1 1 d . . . . .
H2A H 0.4361 0.2742 0.1015 0.018 Uiso 1 1 calc R U . . .
H2B H 0.5124 0.3206 0.3337 0.018 Uiso 1 1 calc R U . . .
C3 C 0.2972(3) 0.36708(13) 0.0876(4) 0.0148(5) Uani 1 1 d . . . . .
H3A H 0.3669 0.3973 0.0231 0.018 Uiso 1 1 calc R U . . .
H3B H 0.1974 0.3501 -0.0439 0.018 Uiso 1 1 calc R U . . .
C4 C 0.1397(3) 0.36467(13) 0.3742(4) 0.0155(5) Uani 1 1 d . . . . .
H4A H 0.0315 0.3477 0.2575 0.019 Uiso 1 1 calc R U . . .
H4B H 0.1108 0.3932 0.4910 0.019 Uiso 1 1 calc R U . . .
C5 C 0.2505(3) 0.30107(12) 0.4959(4) 0.0146(5) Uani 1 1 d . . . . .
H5A H 0.3515 0.3179 0.6261 0.018 Uiso 1 1 calc R U . . .
H5B H 0.1833 0.2699 0.5615 0.018 Uiso 1 1 calc R U . . .
O1W O 0.4871(2) 0.45733(10) 0.6680(3) 0.0170(4) Uani 1 1 d . . . . .
H1W H 0.553(4) 0.4915(16) 0.690(5) 0.018(8) Uiso 1 1 d . . . . .
H2W H 0.556(5) 0.4241(19) 0.735(7) 0.032(9) Uiso 1 1 d . . . . .
O2W O 0.5014(2) 0.02970(10) 0.3418(3) 0.0170(4) Uani 1 1 d . . . . .
H4W H 0.419(4) 0.0012(19) 0.328(6) 0.036(10) Uiso 1 1 d . . . . .
H3W H 0.445(5) 0.074(2) 0.273(7) 0.052(12) Uiso 1 1 d . . . . .
O3W O 0.2281(2) 0.06976(8) 0.7675(4) 0.0158(4) Uani 1 1 d . . . . .
H5W H 0.218(6) 0.099(2) 0.654(8) 0.052(12) Uiso 1 1 d . . . . .
H6W H 0.251(4) 0.0951(17) 0.892(7) 0.026(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.267(3) . ?
O2 C1 1.265(3) . ?
N1 C1 1.371(3) . ?
N1 C2 1.450(3) . ?
N1 C5 1.452(3) . ?
N2 C3 1.494(3) . ?
N2 C4 1.495(3) . ?
C2 C3 1.514(3) . ?
C4 C5 1.516(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
C1 N1 C2 123.1(2) . . ?
C1 N1 C5 123.21(19) . . ?
C2 N1 C5 113.66(17) . . ?
C3 N2 C4 111.80(16) . . ?
O2 C1 O1 125.31(18) . . ?
O2 C1 N1 117.4(2) . . ?
O1 C1 N1 117.3(2) . . ?
N1 C2 C3 110.25(18) . . ?
N2 C3 C2 110.78(19) . . ?
N2 C4 C5 110.37(19) . . ?
N1 C5 C4 110.64(19) . . ?

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
N2 H1N O2W 0.92(3) 2.54(3) 3.098(3) 119(2) 3_455
N2 H1N O2W 0.92(3) 1.98(3) 2.783(3) 146(3) 4_454
N2 H2N O1W 0.95(3) 1.88(3) 2.760(3) 154(3) .
O1W H1W O3W 0.81(3) 1.98(3) 2.793(3) 175(3) 3
O1W H2W O2 0.84(4) 1.90(4) 2.733(3) 172(3) 4
O2W H4W O3W 0.84(3) 1.98(4) 2.814(3) 175(3) 2_554
O2W H3W O1 0.97(4) 1.79(4) 2.758(3) 177.5(17) .
O3W H5W O2 0.85(5) 1.87(5) 2.724(3) 176(4) .
O3W H6W O1 0.85(4) 1.90(4) 2.735(3) 167(3) 1_556

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_PZH-PZCOO
_database_code_depnum_ccdc_archive 'CCDC 1473722'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N2 O2, C4 H11 N2'
_chemical_formula_sum            'C9 H20 N4 O2'
_chemical_formula_weight         216.29

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.194(3)
_cell_length_b                   9.572(5)
_cell_length_c                   18.884(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1119.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1649
_cell_measurement_theta_min      4.26
_cell_measurement_theta_max      22.26

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            9568
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.258
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2193
_reflns_number_gt                1782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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-2014/7 (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)+(0.0507P)²+0.0647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.9(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2193
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7013(3) 0.2379(2) 0.59611(10) 0.0269(5) Uani 1 1 d . . . . .
O2 O 0.3504(3) 0.2498(2) 0.62540(10) 0.0232(5) Uani 1 1 d . . . . .
N1 N 0.6010(4) 0.2012(3) 0.70890(12) 0.0225(6) Uani 1 1 d . . . . .
N2 N 0.6926(4) 0.0540(3) 0.83421(13) 0.0219(6) Uani 1 1 d . . . . .
H1N H 0.703(5) -0.030(4) 0.8571(17) 0.028(9) Uiso 1 1 d . . . . .
C1 C 0.5486(5) 0.2315(3) 0.64020(14) 0.0191(6) Uani 1 1 d . . . . .
C2 C 0.8231(4) 0.1876(3) 0.73289(16) 0.0236(7) Uani 1 1 d . . . . .
H2A H 0.8615 0.2670 0.7622 0.028 Uiso 1 1 calc R U . . .
H2B H 0.9195 0.1856 0.6924 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8461(5) 0.0545(3) 0.77491(16) 0.0253(7) Uani 1 1 d . . . . .
H3A H 0.8188 -0.0253 0.7445 0.030 Uiso 1 1 calc R U . . .
H3B H 0.9923 0.0469 0.7929 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4710(5) 0.0629(3) 0.80723(16) 0.0228(7) Uani 1 1 d . . . . .
H4A H 0.3701 0.0617 0.8465 0.027 Uiso 1 1 calc R U . . .
H4B H 0.4409 -0.0171 0.7773 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4428(5) 0.1959(3) 0.76524(15) 0.0231(7) Uani 1 1 d . . . . .
H5A H 0.2985 0.1992 0.7453 0.028 Uiso 1 1 calc R U . . .
H5B H 0.4606 0.2760 0.7961 0.028 Uiso 1 1 calc R U . . .
N3 N 0.7685(4) 0.6880(3) 0.43920(13) 0.0233(6) Uani 1 1 d . . . . .
H2N H 0.792(5) 0.760(3) 0.4064(18) 0.029(9) Uiso 1 1 d . . . . .
N4 N 0.7335(4) 0.4081(3) 0.48700(13) 0.0191(6) Uani 1 1 d . . . . .
H3N H 0.777(5) 0.349(4) 0.4447(19) 0.040(10) Uiso 1 1 d . . . . .
H4N H 0.709(5) 0.337(4) 0.5260(18) 0.030(9) Uiso 1 1 d . . . . .
C6 C 0.9633(5) 0.6041(3) 0.44882(16) 0.0227(7) Uani 1 1 d . . . . .
H6A H 1.0829 0.6638 0.4623 0.027 Uiso 1 1 calc R U . . .
H6B H 1.0004 0.5579 0.4048 0.027 Uiso 1 1 calc R U . . .
C7 C 0.9230(5) 0.4970(3) 0.50566(15) 0.0229(7) Uani 1 1 d . . . . .
H7A H 1.0499 0.4387 0.5112 0.028 Uiso 1 1 calc R U . . .
H7B H 0.8962 0.5438 0.5504 0.028 Uiso 1 1 calc R U . . .
C8 C 0.5384(5) 0.4934(3) 0.47084(16) 0.0220(6) Uani 1 1 d . . . . .
H8A H 0.4887 0.5397 0.5135 0.026 Uiso 1 1 calc R U . . .
H8B H 0.4234 0.4332 0.4540 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5913(5) 0.6010(3) 0.41522(16) 0.0237(7) Uani 1 1 d . . . . .
H9A H 0.6310 0.5547 0.3714 0.028 Uiso 1 1 calc R U . . .
H9B H 0.4655 0.6586 0.4061 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.262(3) . ?
O2 C1 1.271(3) . ?
N1 C1 1.368(3) . ?
N1 C5 1.447(4) . ?
N1 C2 1.454(4) . ?
N2 C4 1.466(4) . ?
N2 C3 1.469(4) . ?
C2 C3 1.508(4) . ?
C4 C5 1.510(4) . ?
N3 C9 1.450(4) . ?
N3 C6 1.461(4) . ?
N4 C8 1.490(4) . ?
N4 C7 1.492(4) . ?
C6 C7 1.505(4) . ?
C8 C9 1.507(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 122.9(2) . . ?
C1 N1 C2 122.6(2) . . ?
C5 N1 C2 114.1(2) . . ?
C4 N2 C3 109.9(2) . . ?
O1 C1 O2 124.9(3) . . ?
O1 C1 N1 117.3(3) . . ?
O2 C1 N1 117.8(2) . . ?
N1 C2 C3 109.3(3) . . ?
N2 C3 C2 110.0(3) . . ?
N2 C4 C5 109.9(3) . . ?
N1 C5 C4 109.7(2) . . ?
C9 N3 C6 110.4(2) . . ?
C8 N4 C7 112.0(2) . . ?
N3 C6 C7 109.0(2) . . ?
N4 C7 C6 110.5(2) . . ?
N4 C8 C9 109.9(2) . . ?
N3 C9 C8 109.8(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N O2 0.92(3) 2.16(3) 3.022(4) 157(3) 3_646
N3 H2N N2 0.94(3) 2.24(3) 3.176(4) 172(3) 2_664
N4 H3N O2 1.02(4) 1.69(4) 2.704(3) 180(3) 4_556
N4 H4N O1 1.01(3) 1.63(4) 2.635(3) 170(3) .
C6 H6A N3 0.97 2.61 3.465(4) 147.7 4_566
C8 H8B O1 0.97 2.34 3.295(4) 168.8 4_456

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.044

