# 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. 
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data_p21c_sq
_database_code_depnum_ccdc_archive 'CCDC 1477012'
_audit_update_record             
;
2016-06-17 deposited with the CCDC.
2016-06-30 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         
;
C28 H24 Co N6 O4, 3.5(C3 H7 N O)'
;
_chemical_formula_sum            'C38.50 H48.50 Co N9.50 O7.50'
_chemical_formula_weight         823.30

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'
Co Co 0.3494 0.9721 '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                   13.058(3)
_cell_length_b                   17.418(4)
_cell_length_c                   20.041(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.21(3)
_cell_angle_gamma                90
_cell_volume                     4329.8(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    43932
_cell_measurement_theta_min      1.585
_cell_measurement_theta_max      30.309

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.454
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.995
_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      100(2)
_diffrn_radiation_wavelength     0.7109
_diffrn_radiation_type           synchrotron
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 315r'
_diffrn_measurement_method       'Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43932
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.585
_diffrn_reflns_theta_max         30.039
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             12186
_reflns_number_gt                9097
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'BluIce (McPhillips et al., 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12186
_refine_ls_number_parameters     551
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0887
_refine_ls_wR_factor_ref         0.3118
_refine_ls_wR_factor_gt          0.2908
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_restrained_S_all      1.245
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 250 77 ' '
2 0.000 0.500 0.500 250 77 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
Electron count equates to approx. 1 DMF per formula unit.
Included in cell contents during refinement.
;

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
Co1 Co 0.66637(3) 0.17326(2) 0.71590(2) 0.04729(17) Uani 1 1 d . . . . .
O1 O 0.6744(2) 0.27755(11) 0.66030(12) 0.0542(5) Uani 1 1 d . . . . .
O2 O 0.6476(2) 0.27924(12) 0.76293(11) 0.0545(5) Uani 1 1 d . . . . .
O3 O 0.27502(16) -0.09385(13) 0.34143(11) 0.0508(5) Uani 1 1 d . . . . .
O4 O 0.1586(2) -0.15891(17) 0.25892(14) 0.0670(6) Uani 1 1 d . . . . .
N1 N 0.6621(2) 0.39768(13) 0.29915(12) 0.0456(5) Uani 1 1 d . . . . .
N2 N 0.63771(19) 0.51222(12) 0.52061(12) 0.0445(5) Uani 1 1 d . . . . .
N3 N 0.6287(2) 0.55380(12) 0.57505(14) 0.0520(6) Uani 1 1 d . . . . .
H3N H 0.6217 0.6040 0.5720 0.062 Uiso 1 1 calc R U . . .
N4 N 0.5016(2) 0.16105(13) 0.65833(13) 0.0474(5) Uani 1 1 d . . . . .
N5A N 0.1518(9) 0.0702(5) 0.4930(6) 0.0488(18) Uani 0.5 1 d . . P A 2
N5B N 0.1465(12) 0.0976(6) 0.4886(8) 0.069(3) Uani 0.5 1 d . . P B 1
N6A N 0.0489(9) 0.0514(7) 0.4546(8) 0.073(3) Uani 0.5 1 d . . P A 2
H6AN H -0.0056 0.0720 0.4652 0.087 Uiso 0.5 1 calc R U P A 2
N6B N 0.0455(11) 0.0849(7) 0.4488(9) 0.085(4) Uani 0.5 1 d . . P B 1
H6BN H -0.0086 0.1081 0.4578 0.102 Uiso 0.5 1 calc R U P B 1
C1 C 0.6433(2) 0.37029(15) 0.35617(15) 0.0462(6) Uani 1 1 d . . . . .
H1 H 0.6348 0.3164 0.3597 0.055 Uiso 1 1 calc R U . . .
C2 C 0.6353(2) 0.41593(14) 0.41027(15) 0.0457(6) Uani 1 1 d . . . . .
H2 H 0.6231 0.3932 0.4502 0.055 Uiso 1 1 calc R U . . .
C3 C 0.6452(2) 0.49574(14) 0.40678(14) 0.0447(5) Uani 1 1 d . . . . .
C4 C 0.6659(3) 0.52409(15) 0.34712(16) 0.0535(7) Uani 1 1 d . . . . .
H4 H 0.6745 0.5777 0.3420 0.064 Uiso 1 1 calc R U . . .
C5 C 0.6739(3) 0.47409(16) 0.29552(16) 0.0545(7) Uani 1 1 d . . . . .
H5 H 0.6883 0.4947 0.2555 0.065 Uiso 1 1 calc R U . . .
C6 C 0.6325(3) 0.54674(14) 0.46260(15) 0.0493(6) Uani 1 1 d . . . . .
C7 C 0.6141(4) 0.63192(17) 0.4502(2) 0.0673(9) Uani 1 1 d . . . . .
H7A H 0.5710 0.6513 0.4788 0.101 Uiso 1 1 calc R U . . .
H7B H 0.5757 0.6412 0.4004 0.101 Uiso 1 1 calc R U . . .
H7C H 0.6837 0.6585 0.4634 0.101 Uiso 1 1 calc R U . . .
C8 C 0.6308(2) 0.51554(14) 0.63626(15) 0.0448(5) Uani 1 1 d . . . . .
C9 C 0.6452(2) 0.43622(14) 0.64312(14) 0.0434(5) Uani 1 1 d . . . . .
H9 H 0.6552 0.4072 0.6055 0.052 Uiso 1 1 calc R U . . .
C10 C 0.6450(2) 0.39963(15) 0.70447(14) 0.0426(5) Uani 1 1 d . . . . .
C11 C 0.6320(2) 0.44140(18) 0.76095(16) 0.0511(6) Uani 1 1 d . . . . .
H11 H 0.6321 0.4163 0.8031 0.061 Uiso 1 1 calc R U . . .
C12 C 0.6189(3) 0.52065(18) 0.75379(17) 0.0536(7) Uani 1 1 d . . . . .
H12 H 0.6103 0.5498 0.7918 0.064 Uiso 1 1 calc R U . . .
C13 C 0.6181(2) 0.55779(16) 0.69294(16) 0.0496(6) Uani 1 1 d . . . . .
H13 H 0.6091 0.6119 0.6893 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6574(2) 0.31409(16) 0.70961(14) 0.0450(6) Uani 1 1 d . . . . .
C15 C 0.4700(3) 0.1093(3) 0.60656(16) 0.0635(9) Uani 1 1 d . . . . .
H15 H 0.5231 0.0786 0.5961 0.076 Uiso 1 1 calc R U . . .
C16 C 0.3637(3) 0.0989(4) 0.5680(2) 0.0896(16) Uani 1 1 d . . . . .
H16 H 0.3452 0.0619 0.5314 0.108 Uiso 1 1 calc R U . . .
C17 C 0.2822(3) 0.1419(3) 0.58172(17) 0.0645(9) Uani 1 1 d . . . . .
C18 C 0.3174(3) 0.19600(18) 0.63533(19) 0.0558(7) Uani 1 1 d . . . . .
H18 H 0.2666 0.2283 0.6467 0.067 Uiso 1 1 calc R U . . .
C19 C 0.4254(3) 0.20275(16) 0.6717(2) 0.0586(8) Uani 1 1 d . . . . .
H19 H 0.4466 0.2394 0.7086 0.070 Uiso 1 1 calc R U . . .
C20A C 0.1722(10) 0.1162(6) 0.5440(6) 0.057(2) Uani 0.5 1 d . . P A 2
C20B C 0.1644(10) 0.1459(7) 0.5391(7) 0.061(3) Uani 0.5 1 d . . P B 1
C21A C 0.0827(12) 0.1548(7) 0.5666(8) 0.082(3) Uani 0.5 1 d . . P A 2
H21A H 0.1150 0.1848 0.6094 0.123 Uiso 0.5 1 calc R U P A 2
H21B H 0.0352 0.1154 0.5758 0.123 Uiso 0.5 1 calc R U P A 2
H21C H 0.0408 0.1889 0.5291 0.123 Uiso 0.5 1 calc R U P A 2
C21B C 0.0789(10) 0.1930(9) 0.5553(9) 0.091(5) Uani 0.5 1 d . . P B 1
H21D H 0.1061 0.2451 0.5686 0.136 Uiso 0.5 1 calc R U P B 1
H21E H 0.0600 0.1693 0.5943 0.136 Uiso 0.5 1 calc R U P B 1
H21F H 0.0148 0.1952 0.5137 0.136 Uiso 0.5 1 calc R U P B 1
C22A C 0.0290(11) -0.0010(7) 0.3980(7) 0.069(3) Uani 0.5 1 d . . P A 2
C22B C 0.0275(9) 0.0344(8) 0.3929(8) 0.076(4) Uani 0.5 1 d . . P B 1
C23A C 0.1136(14) -0.0349(6) 0.3816(9) 0.050(3) Uani 0.5 1 d . . P A 2
H23A H 0.1860 -0.0242 0.4086 0.059 Uiso 0.5 1 calc R U P A 2
C23B C 0.1096(14) -0.0091(7) 0.3808(9) 0.055(3) Uani 0.5 1 d . . P B 1
H23B H 0.1810 -0.0050 0.4120 0.065 Uiso 0.5 1 calc R U P B 1
C24A C 0.0905(12) -0.0856(6) 0.3238(9) 0.052(2) Uani 0.5 1 d . . P A 2
C24B C 0.0884(11) -0.0583(6) 0.3237(8) 0.049(2) Uani 0.5 1 d . . P B 1
C25A C -0.0158(8) -0.1046(7) 0.2870(5) 0.071(2) Uani 0.5 1 d . . P A 2
H25A H -0.0313 -0.1411 0.2499 0.086 Uiso 0.5 1 calc R U P A 2
C25B C -0.0161(7) -0.0639(6) 0.2755(5) 0.064(2) Uani 0.5 1 d . . P B 1
H25B H -0.0309 -0.0972 0.2361 0.076 Uiso 0.5 1 calc R U P B 1
C26A C -0.1005(9) -0.0689(9) 0.3054(7) 0.088(3) Uani 0.5 1 d . . P A 2
H26A H -0.1734 -0.0797 0.2796 0.106 Uiso 0.5 1 calc R U P A 2
C26B C -0.0966(7) -0.0195(9) 0.2872(5) 0.083(3) Uani 0.5 1 d . . P B 1
H26B H -0.1681 -0.0228 0.2557 0.100 Uiso 0.5 1 calc R U P B 1
C27A C -0.0769(9) -0.0190(8) 0.3602(7) 0.087(3) Uani 0.5 1 d . . P A 2
H27A H -0.1340 0.0041 0.3730 0.104 Uiso 0.5 1 calc R U P A 2
C27B C -0.0741(8) 0.0297(9) 0.3443(6) 0.092(4) Uani 0.5 1 d . . P B 1
H27B H -0.1302 0.0611 0.3502 0.110 Uiso 0.5 1 calc R U P B 1
C28 C 0.1785(3) -0.1104(2) 0.30729(16) 0.0560(7) Uani 1 1 d . . . . .
O5 O 0.5782(3) 0.71213(13) 0.5931(2) 0.0998(11) Uani 1 1 d D . . . .
C29 C 0.6331(4) 0.7706(2) 0.5936(2) 0.0792(11) Uani 1 1 d D . . . .
H29 H 0.6766 0.7706 0.5634 0.095 Uiso 1 1 calc R U . . .
N7 N 0.6369(3) 0.83314(17) 0.63260(17) 0.0669(8) Uani 1 1 d D . . . .
C30 C 0.5747(6) 0.8379(3) 0.6793(3) 0.107(2) Uani 1 1 d D . . . .
H30A H 0.5874 0.8876 0.7034 0.161 Uiso 0.5 1 calc R U P . .
H30B H 0.4980 0.8329 0.6527 0.161 Uiso 0.5 1 calc R U P . .
H30C H 0.5957 0.7965 0.7140 0.161 Uiso 0.5 1 calc R U P . .
H30D H 0.5334 0.7904 0.6767 0.161 Uiso 0.5 1 calc R U P . .
H30E H 0.6227 0.8451 0.7274 0.161 Uiso 0.5 1 calc R U P . .
H30F H 0.5250 0.8815 0.6661 0.161 Uiso 0.5 1 calc R U P . .
C31 C 0.7023(5) 0.8979(3) 0.6294(3) 0.1009(17) Uani 1 1 d D . . . .
H31A H 0.6937 0.9376 0.6619 0.151 Uiso 0.5 1 calc R U P . .
H31B H 0.7781 0.8821 0.6427 0.151 Uiso 0.5 1 calc R U P . .
H31C H 0.6801 0.9184 0.5815 0.151 Uiso 0.5 1 calc R U P . .
H31D H 0.7409 0.8878 0.5955 0.151 Uiso 0.5 1 calc R U P . .
H31E H 0.6565 0.9433 0.6147 0.151 Uiso 0.5 1 calc R U P . .
H31F H 0.7545 0.9070 0.6759 0.151 Uiso 0.5 1 calc R U P . .
O6 O 0.4205(5) 0.9134(3) 0.5166(4) 0.096(2) Uiso 0.535(7) 1 d D . P C 1
C32 C 0.3706(5) 0.8532(4) 0.4937(4) 0.077(2) Uiso 0.535(7) 1 d D . P C 1
H32 H 0.3971 0.8226 0.4635 0.093 Uiso 0.535(7) 1 calc R U P C 1
N8 N 0.2833(5) 0.8276(3) 0.5078(4) 0.076(2) Uiso 0.535(7) 1 d D . P C 1
C33 C 0.2366(5) 0.8715(4) 0.5506(4) 0.0715(19) Uiso 0.535(7) 1 d D . P C 1
H33A H 0.1736 0.8444 0.5555 0.107 Uiso 0.268(3) 1 calc R U P C 1
H33B H 0.2897 0.8788 0.5971 0.107 Uiso 0.268(3) 1 calc R U P C 1
H33C H 0.2143 0.9217 0.5287 0.107 Uiso 0.268(3) 1 calc R U P C 1
H33D H 0.2782 0.9188 0.5653 0.107 Uiso 0.268(3) 1 calc R U P C 1
H33E H 0.1620 0.8845 0.5238 0.107 Uiso 0.268(3) 1 calc R U P C 1
H33F H 0.2374 0.8416 0.5921 0.107 Uiso 0.268(3) 1 calc R U P C 1
C34 C 0.2249(6) 0.7617(4) 0.4735(4) 0.083(2) Uiso 0.535(7) 1 d D . P C 1
H34A H 0.1638 0.7523 0.4909 0.124 Uiso 0.268(3) 1 calc R U P C 1
H34B H 0.1982 0.7708 0.4227 0.124 Uiso 0.268(3) 1 calc R U P C 1
H34C H 0.2726 0.7169 0.4832 0.124 Uiso 0.268(3) 1 calc R U P C 1
H34D H 0.2593 0.7410 0.4403 0.124 Uiso 0.268(3) 1 calc R U P C 1
H34E H 0.2249 0.7225 0.5085 0.124 Uiso 0.268(3) 1 calc R U P C 1
H34F H 0.1505 0.7765 0.4480 0.124 Uiso 0.268(3) 1 calc R U P C 1
O7 O 0.1686(5) 0.3387(4) 0.6786(3) 0.0776(15) Uiso 0.5 1 d D . P . .
C35 C 0.0893(7) 0.3736(9) 0.6397(6) 0.152(6) Uiso 0.5 1 d D . P . .
H35 H 0.0996 0.4007 0.6011 0.182 Uiso 0.5 1 calc R U P . .
N9 N -0.0088(5) 0.3767(6) 0.6468(5) 0.129(4) Uiso 0.5 1 d D . P . .
C36 C -0.0333(9) 0.3333(11) 0.6998(9) 0.213(12) Uiso 0.5 1 d D . P . .
H36A H -0.1085 0.3424 0.6974 0.320 Uiso 0.25 1 calc R U P . .
H36B H -0.0229 0.2785 0.6926 0.320 Uiso 0.25 1 calc R U P . .
H36C H 0.0144 0.3489 0.7461 0.320 Uiso 0.25 1 calc R U P . .
H36D H 0.0305 0.3042 0.7267 0.320 Uiso 0.25 1 calc R U P . .
H36E H -0.0551 0.3680 0.7314 0.320 Uiso 0.25 1 calc R U P . .
H36F H -0.0924 0.2976 0.6780 0.320 Uiso 0.25 1 calc R U P . .
C37 C -0.0898(9) 0.4281(11) 0.6063(10) 0.215(11) Uiso 0.5 1 d D . P . .
H37A H -0.1558 0.4215 0.6193 0.323 Uiso 0.25 1 calc R U P . .
H37B H -0.0642 0.4811 0.6158 0.323 Uiso 0.25 1 calc R U P . .
H37C H -0.1051 0.4169 0.5562 0.323 Uiso 0.25 1 calc R U P . .
H37D H -0.0610 0.4581 0.5749 0.323 Uiso 0.25 1 calc R U P . .
H37E H -0.1525 0.3986 0.5784 0.323 Uiso 0.25 1 calc R U P . .
H37F H -0.1116 0.4628 0.6379 0.323 Uiso 0.25 1 calc R U P . .
O8 O 0.1533(6) 0.8844(5) 0.5490(5) 0.119(3) Uiso 0.465(7) 1 d D . P C 2
C38 C 0.2085(7) 0.8334(4) 0.5334(7) 0.108(4) Uiso 0.465(7) 1 d D . P C 2
H38 H 0.1819 0.7823 0.5307 0.130 Uiso 0.465(7) 1 calc R U P C 2
N10 N 0.3014(5) 0.8437(4) 0.5200(5) 0.071(2) Uiso 0.465(7) 1 d D . P C 2
C39 C 0.3563(8) 0.9151(5) 0.5347(7) 0.107(4) Uiso 0.465(7) 1 d D . P C 2
H39A H 0.4226 0.9124 0.5217 0.160 Uiso 0.232(3) 1 calc R U P C 2
H39B H 0.3098 0.9558 0.5075 0.160 Uiso 0.232(3) 1 calc R U P C 2
H39C H 0.3744 0.9265 0.5849 0.160 Uiso 0.232(3) 1 calc R U P C 2
H39D H 0.3152 0.9507 0.5544 0.160 Uiso 0.232(3) 1 calc R U P C 2
H39E H 0.4281 0.9073 0.5686 0.160 Uiso 0.232(3) 1 calc R U P C 2
H39F H 0.3634 0.9366 0.4911 0.160 Uiso 0.232(3) 1 calc R U P C 2
C40 C 0.3546(8) 0.7823(5) 0.4969(7) 0.104(4) Uiso 0.465(7) 1 d D . P C 2
H40A H 0.4212 0.8014 0.4901 0.155 Uiso 0.232(3) 1 calc R U P C 2
H40B H 0.3720 0.7415 0.5324 0.155 Uiso 0.232(3) 1 calc R U P C 2
H40C H 0.3071 0.7618 0.4524 0.155 Uiso 0.232(3) 1 calc R U P C 2
H40D H 0.3124 0.7350 0.4932 0.155 Uiso 0.232(3) 1 calc R U P C 2
H40E H 0.3615 0.7950 0.4509 0.155 Uiso 0.232(3) 1 calc R U P C 2
H40F H 0.4264 0.7747 0.5308 0.155 Uiso 0.232(3) 1 calc R U P C 2


_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
Co1 O3 2.090(2) 3_656 ?
Co1 N1 2.091(2) 4_566 ?
Co1 N4 2.111(3) . ?
Co1 O2 2.121(2) . ?
Co1 O1 2.151(2) . ?
Co1 O4 2.196(3) 3_656 ?
Co1 C14 2.457(3) . ?
Co1 C28 2.471(4) 3_656 ?
O1 C14 1.253(3) . ?
O2 C14 1.269(3) . ?
O3 C28 1.266(4) . ?
O3 Co1 2.090(2) 3_656 ?
O4 C28 1.250(4) . ?
O4 Co1 2.196(3) 3_656 ?
N1 C1 1.331(4) . ?
N1 C5 1.344(3) . ?
N1 Co1 2.091(2) 4_565 ?
N2 C6 1.292(4) . ?
N2 N3 1.345(3) . ?
N3 C8 1.389(4) . ?
N4 C19 1.325(4) . ?
N4 C15 1.338(4) . ?
N5A C20A 1.260(16) . ?
N5A N6A 1.363(18) . ?
N5B N6B 1.33(2) . ?
N5B C20B 1.281(16) . ?
N6A C22A 1.415(15) . ?
N6B C22B 1.387(14) . ?
C1 C2 1.374(4) . ?
C2 C3 1.400(3) . ?
C3 C4 1.396(4) . ?
C3 C6 1.478(4) . ?
C4 C5 1.381(4) . ?
C6 C7 1.511(4) . ?
C8 C9 1.395(3) . ?
C8 C13 1.406(4) . ?
C9 C10 1.385(4) . ?
C10 C11 1.400(3) . ?
C10 C14 1.499(4) . ?
C11 C12 1.393(5) . ?
C12 C13 1.378(5) . ?
C15 C16 1.374(5) . ?
C16 C17 1.396(6) . ?
C17 C18 1.395(6) . ?
C17 C20A 1.469(14) . ?
C17 C20B 1.510(12) . ?
C18 C19 1.376(5) . ?
C20A C21A 1.534(17) . ?
C20B C21B 1.500(14) . ?
C22A C23A 1.380(18) . ?
C22A C27A 1.389(18) . ?
C22B C27B 1.381(16) . ?
C22B C23B 1.394(16) . ?
C23A C24A 1.411(18) . ?
C23B C24B 1.386(16) . ?
C24A C28 1.362(15) . ?
C24A C25A 1.393(18) . ?
C24B C25B 1.407(17) . ?
C24B C28 1.599(12) . ?
C25A C26A 1.415(16) . ?
C25B C26B 1.382(13) . ?
C26A C27A 1.358(17) . ?
C26B C27B 1.387(13) . ?
C28 Co1 2.472(4) 3_656 ?
O5 C29 1.244(5) . ?
C29 N7 1.333(4) . ?
N7 C30 1.421(5) . ?
N7 C31 1.429(5) . ?
O6 C32 1.244(5) . ?
C32 N8 1.334(4) . ?
N8 C33 1.421(5) . ?
N8 C34 1.429(5) . ?
O7 C35 1.243(5) . ?
C35 N9 1.333(4) . ?
N9 C36 1.421(5) . ?
N9 C37 1.429(5) . ?
O8 C38 1.244(5) . ?
C38 N10 1.333(4) . ?
N10 C39 1.421(5) . ?
N10 C40 1.429(5) . ?

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
O3 Co1 N1 98.80(9) 3_656 4_566 ?
O3 Co1 N4 96.83(10) 3_656 . ?
N1 Co1 N4 95.73(10) 4_566 . ?
O3 Co1 O2 158.91(9) 3_656 . ?
N1 Co1 O2 97.13(8) 4_566 . ?
N4 Co1 O2 95.22(10) . . ?
O3 Co1 O1 100.87(8) 3_656 . ?
N1 Co1 O1 158.49(9) 4_566 . ?
N4 Co1 O1 90.49(9) . . ?
O2 Co1 O1 61.73(8) . . ?
O3 Co1 O4 61.14(9) 3_656 3_656 ?
N1 Co1 O4 91.98(11) 4_566 3_656 ?
N4 Co1 O4 157.60(11) . 3_656 ?
O2 Co1 O4 104.67(10) . 3_656 ?
O1 Co1 O4 89.96(11) . 3_656 ?
O3 Co1 C14 130.73(9) 3_656 . ?
N1 Co1 C14 128.18(9) 4_566 . ?
N4 Co1 C14 92.76(9) . . ?
O2 Co1 C14 31.10(8) . . ?
O1 Co1 C14 30.64(8) . . ?
O4 Co1 C14 98.93(10) 3_656 . ?
O3 Co1 C28 30.80(10) 3_656 3_656 ?
N1 Co1 C28 96.67(10) 4_566 3_656 ?
N4 Co1 C28 127.48(11) . 3_656 ?
O2 Co1 C28 133.16(11) . 3_656 ?
O1 Co1 C28 95.79(10) . 3_656 ?
O4 Co1 C28 30.35(10) 3_656 3_656 ?
C14 Co1 C28 117.48(11) . 3_656 ?
C14 O1 Co1 88.32(17) . . ?
C14 O2 Co1 89.21(16) . . ?
C28 O3 Co1 91.5(2) . 3_656 ?
C28 O4 Co1 87.1(2) . 3_656 ?
C1 N1 C5 117.1(2) . . ?
C1 N1 Co1 122.12(17) . 4_565 ?
C5 N1 Co1 120.7(2) . 4_565 ?
C6 N2 N3 119.1(2) . . ?
N2 N3 C8 118.4(2) . . ?
C19 N4 C15 117.2(3) . . ?
C19 N4 Co1 122.4(2) . . ?
C15 N4 Co1 120.4(2) . . ?
C20A N5A N6A 122.1(10) . . ?
N6B N5B C20B 119.0(11) . . ?
N5A N6A C22A 120.6(9) . . ?
N5B N6B C22B 118.4(11) . . ?
N1 C1 C2 123.4(2) . . ?
C1 C2 C3 120.3(3) . . ?
C4 C3 C2 116.1(3) . . ?
C4 C3 C6 122.2(2) . . ?
C2 C3 C6 121.7(3) . . ?
C5 C4 C3 119.9(2) . . ?
N1 C5 C4 123.2(3) . . ?
N2 C6 C3 114.5(2) . . ?
N2 C6 C7 124.5(3) . . ?
C3 C6 C7 121.0(3) . . ?
N3 C8 C9 121.8(2) . . ?
N3 C8 C13 119.2(2) . . ?
C9 C8 C13 119.0(3) . . ?
C10 C9 C8 120.3(2) . . ?
C9 C10 C11 120.8(3) . . ?
C9 C10 C14 119.2(2) . . ?
C11 C10 C14 119.9(3) . . ?
C12 C11 C10 118.3(3) . . ?
C13 C12 C11 121.5(2) . . ?
C12 C13 C8 119.9(3) . . ?
O1 C14 O2 120.7(3) . . ?
O1 C14 C10 119.5(2) . . ?
O2 C14 C10 119.8(2) . . ?
O1 C14 Co1 61.04(14) . . ?
O2 C14 Co1 59.69(14) . . ?
C10 C14 Co1 176.8(2) . . ?
N4 C15 C16 122.5(4) . . ?
C15 C16 C17 121.1(4) . . ?
C18 C17 C16 115.2(3) . . ?
C18 C17 C20A 129.5(5) . . ?
C16 C17 C20A 114.7(5) . . ?
C18 C17 C20B 115.8(5) . . ?
C16 C17 C20B 128.2(5) . . ?
C19 C18 C17 120.1(3) . . ?
N4 C19 C18 123.8(3) . . ?
N5A C20A C17 122.4(9) . . ?
N5A C20A C21A 122.1(12) . . ?
C17 C20A C21A 115.3(10) . . ?
N5B C20B C21B 124.5(12) . . ?
N5B C20B C17 108.6(9) . . ?
C21B C20B C17 126.8(9) . . ?
C23A C22A C27A 120.5(12) . . ?
C23A C22A N6A 120.5(13) . . ?
C27A C22A N6A 119.0(11) . . ?
C27B C22B N6B 119.3(10) . . ?
C27B C22B C23B 117.8(11) . . ?
N6B C22B C23B 122.7(12) . . ?
C22A C23A C24A 118.8(15) . . ?
C24B C23B C22B 120.9(14) . . ?
C28 C24A C25A 124.9(11) . . ?
C28 C24A C23A 114.7(13) . . ?
C25A C24A C23A 120.4(13) . . ?
C23B C24B C25B 120.7(12) . . ?
C23B C24B C28 123.4(12) . . ?
C25B C24B C28 115.9(9) . . ?
C26A C25A C24A 119.2(10) . . ?
C26B C25B C24B 118.1(8) . . ?
C27A C26A C25A 119.6(10) . . ?
C25B C26B C27B 120.6(8) . . ?
C26A C27A C22A 121.4(10) . . ?
C22B C27B C26B 121.8(9) . . ?
O4 C28 O3 120.2(3) . . ?
O4 C28 C24A 114.6(6) . . ?
O3 C28 C24A 124.7(7) . . ?
O4 C28 C24B 123.7(6) . . ?
O3 C28 C24B 115.6(5) . . ?
O4 C28 Co1 62.53(19) . 3_656 ?
O3 C28 Co1 57.71(16) . 3_656 ?
C24A C28 Co1 171.9(6) . 3_656 ?
C24B C28 Co1 171.5(5) . 3_656 ?
O5 C29 N7 126.2(4) . . ?
C29 N7 C30 120.7(3) . . ?
C29 N7 C31 122.2(3) . . ?
C30 N7 C31 117.2(3) . . ?
O6 C32 N8 126.0(4) . . ?
C32 N8 C33 120.2(4) . . ?
C32 N8 C34 122.0(4) . . ?
C33 N8 C34 117.3(3) . . ?
O7 C35 N9 126.3(4) . . ?
C35 N9 C36 120.5(4) . . ?
C35 N9 C37 122.0(4) . . ?
C36 N9 C37 117.2(3) . . ?
O8 C38 N10 126.2(4) . . ?
C38 N10 C39 120.5(4) . . ?
C38 N10 C40 122.0(4) . . ?
C39 N10 C40 117.2(3) . . ?

_refine_diff_density_max         1.113
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.088




####################################################################### 
# 
# 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_1Cd-2DMF
_database_code_depnum_ccdc_archive 'CCDC 1477013'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 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         
;
C28 H24 Cd N6 O4, 2(C3 H7 N O)
;
_chemical_formula_sum            'C34 H38 Cd N8 O6'
_chemical_formula_weight         767.12

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'
Cd Cd -0.7830 1.1970 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.156(2)
_cell_length_b                   11.554(2)
_cell_length_c                   15.972(3)
_cell_angle_alpha                83.61(3)
_cell_angle_beta                 88.74(3)
_cell_angle_gamma                71.26(3)
_cell_volume                     1763.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    31962
_cell_measurement_theta_min      1.283
_cell_measurement_theta_max      27.930

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.674
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.967
_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     0.7109
_diffrn_radiation_type           synchrotron
_diffrn_source                   'MX1 Beamline, Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31962
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.283
_diffrn_reflns_theta_max         27.930
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8397
_reflns_number_gt                7671
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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+1.9777P] 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         8397
_refine_ls_number_parameters     502
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
Cd1 Cd 0.72256(2) 0.35600(2) 0.80863(2) 0.02443(6) Uani 1 1 d . . . . .
O1 O 1.19868(18) 0.60004(16) 0.33018(10) 0.0329(4) Uani 1 1 d . . . . .
O2 O 1.14538(17) 0.79170(15) 0.27125(10) 0.0283(3) Uani 1 1 d . . . . .
O3 O 0.60421(17) 0.23588(16) 0.89436(10) 0.0284(3) Uani 1 1 d . . . . .
O4 O 0.51037(17) 0.34774(16) 0.77593(11) 0.0318(4) Uani 1 1 d . . . . .
O5 O 0.6413(2) 1.1608(2) 0.54378(14) 0.0533(5) Uani 1 1 d . . . . .
O6 O 0.2679(6) -0.4392(5) 0.8986(3) 0.0510(15) Uani 0.425(6) 1 d . . P A 1
O6A O 0.0081(5) -0.3853(5) 0.7946(3) 0.0699(16) Uani 0.575(6) 1 d . . P A 2
N1 N 0.6600(2) 0.55874(18) 0.82942(12) 0.0278(4) Uani 1 1 d . . . . .
N2 N 0.7396(2) 0.81588(18) 0.65666(12) 0.0289(4) Uani 1 1 d . . . . .
N3 N 0.7648(2) 0.89410(19) 0.59280(13) 0.0356(5) Uani 1 1 d D . . . .
H3N H 0.726(3) 0.9746(4) 0.587(2) 0.053 Uiso 1 1 d D U . . .
N4 N 0.1127(2) -0.31659(18) 1.08782(12) 0.0282(4) Uani 1 1 d . . . . .
N5 N 0.0869(2) -0.04791(18) 0.89565(12) 0.0263(4) Uani 1 1 d . . . . .
N6 N 0.0866(2) 0.04657(19) 0.83710(12) 0.0285(4) Uani 1 1 d D . . . .
H6N H 0.0131(18) 0.081(3) 0.8040(14) 0.043 Uiso 1 1 d D U . . .
N7 N 0.4651(3) 1.3415(2) 0.53458(15) 0.0425(5) Uani 1 1 d . . . . .
N8 N 0.1847(19) -0.3319(13) 0.7717(9) 0.037(2) Uani 0.425(6) 1 d D . P A 1
N8A N 0.1786(16) -0.3074(12) 0.7538(8) 0.052(3) Uani 0.575(6) 1 d D . P A 2
C1 C 0.6006(3) 0.5945(2) 0.90283(15) 0.0323(5) Uani 1 1 d . . . . .
H1 H 0.5947 0.5336 0.9465 0.039 Uiso 1 1 calc R U . . .
C2 C 0.5484(3) 0.7166(2) 0.91630(14) 0.0319(5) Uani 1 1 d . . . . .
H2 H 0.5058 0.7398 0.9681 0.038 Uiso 1 1 calc R U . . .
C3 C 0.5591(2) 0.8051(2) 0.85263(15) 0.0301(5) Uani 1 1 d . . . . .
H3 H 0.5226 0.8898 0.8604 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6234(2) 0.7699(2) 0.77718(13) 0.0255(4) Uani 1 1 d . . . . .
C5 C 0.6717(2) 0.6440(2) 0.76917(13) 0.0260(4) Uani 1 1 d . . . . .
H5 H 0.7151 0.6180 0.7181 0.031 Uiso 1 1 calc R U . . .
C6 C 0.6411(3) 0.8599(2) 0.70827(14) 0.0294(5) Uani 1 1 d . . . . .
C7 C 0.5490(3) 0.9910(3) 0.70131(17) 0.0434(7) Uani 1 1 d . . . . .
H7B H 0.6030 1.0434 0.7148 0.065 Uiso 1 1 calc R U . . .
H7A H 0.4722 0.9993 0.7408 0.065 Uiso 1 1 calc R U . . .
H7C H 0.5116 1.0163 0.6437 0.065 Uiso 1 1 calc R U . . .
C8 C 0.8598(3) 0.8460(2) 0.53203(15) 0.0315(5) Uani 1 1 d . . . . .
C9 C 0.8872(3) 0.9283(2) 0.46843(16) 0.0367(6) Uani 1 1 d . . . . .
H9 H 0.8425 1.0142 0.4684 0.044 Uiso 1 1 calc R U . . .
C10 C 0.9793(3) 0.8843(2) 0.40582(15) 0.0338(5) Uani 1 1 d . . . . .
H10 H 0.9983 0.9409 0.3632 0.041 Uiso 1 1 calc R U . . .
C11 C 1.0455(2) 0.7585(2) 0.40362(13) 0.0271(4) Uani 1 1 d . . . . .
C12 C 1.0191(3) 0.6767(2) 0.46750(14) 0.0304(5) Uani 1 1 d . . . . .
H12 H 1.0645 0.5908 0.4674 0.036 Uiso 1 1 calc R U . . .
C13 C 0.9273(3) 0.7194(2) 0.53129(15) 0.0328(5) Uani 1 1 d . . . . .
H13 H 0.9102 0.6629 0.5746 0.039 Uiso 1 1 calc R U . . .
C14 C 1.1364(2) 0.7127(2) 0.33200(13) 0.0254(4) Uani 1 1 d . . . . .
C15 C 0.0238(2) -0.3824(2) 1.09018(15) 0.0306(5) Uani 1 1 d . . . . .
H15 H 0.0333 -0.4469 1.1343 0.037 Uiso 1 1 calc R U . . .
C16 C -0.0799(2) -0.3588(2) 1.03072(16) 0.0314(5) Uani 1 1 d . . . . .
H16 H -0.1410 -0.4064 1.0338 0.038 Uiso 1 1 calc R U . . .
C17 C -0.0944(2) -0.2647(2) 0.96621(15) 0.0293(5) Uani 1 1 d . . . . .
H17 H -0.1652 -0.2477 0.9245 0.035 Uiso 1 1 calc R U . . .
C18 C -0.0046(2) -0.1949(2) 0.96272(14) 0.0257(4) Uani 1 1 d . . . . .
C19 C 0.0975(2) -0.2254(2) 1.02594(14) 0.0276(4) Uani 1 1 d . . . . .
H19 H 0.1595 -0.1787 1.0248 0.033 Uiso 1 1 calc R U . . .
C20 C -0.0151(2) -0.0920(2) 0.89657(14) 0.0277(4) Uani 1 1 d . . . . .
C21 C -0.1389(3) -0.0456(3) 0.83834(17) 0.0390(6) Uani 1 1 d . . . . .
H21A H -0.2177 0.0075 0.8672 0.059 Uiso 1 1 calc R U . . .
H21B H -0.1630 -0.1155 0.8216 0.059 Uiso 1 1 calc R U . . .
H21C H -0.1170 0.0014 0.7881 0.059 Uiso 1 1 calc R U . . .
C22 C 0.1896(2) 0.1008(2) 0.84140(14) 0.0253(4) Uani 1 1 d . . . . .
C23 C 0.2913(2) 0.0641(2) 0.90548(13) 0.0245(4) Uani 1 1 d . . . . .
H23 H 0.2910 0.0008 0.9488 0.029 Uiso 1 1 calc R U . . .
C24 C 0.3925(2) 0.1211(2) 0.90515(13) 0.0242(4) Uani 1 1 d . . . . .
H24 H 0.4617 0.0957 0.9484 0.029 Uiso 1 1 calc R U . . .
C25 C 0.3948(2) 0.2149(2) 0.84261(14) 0.0245(4) Uani 1 1 d . . . . .
C26 C 0.2916(2) 0.2515(2) 0.77994(15) 0.0307(5) Uani 1 1 d . . . . .
H26 H 0.2908 0.3161 0.7374 0.037 Uiso 1 1 calc R U . . .
C27 C 0.1909(2) 0.1955(2) 0.77889(15) 0.0320(5) Uani 1 1 d . . . . .
H27 H 0.1218 0.2213 0.7355 0.038 Uiso 1 1 calc R U . . .
C28 C 0.5093(2) 0.2696(2) 0.83852(14) 0.0250(4) Uani 1 1 d . . . . .
C29 C 0.5691(3) 1.2527(3) 0.57457(17) 0.0382(6) Uani 1 1 d . . . . .
H29 H 0.5890 1.2608 0.6310 0.046 Uiso 1 1 calc R U . . .
C30 C 0.4262(5) 1.3348(4) 0.4489(2) 0.0732(11) Uani 1 1 d . . . . .
H30A H 0.4965 1.2665 0.4257 0.110 Uiso 1 1 calc R U . . .
H30B H 0.4203 1.4120 0.4143 0.110 Uiso 1 1 calc R U . . .
H30C H 0.3357 1.3215 0.4486 0.110 Uiso 1 1 calc R U . . .
C31 C 0.3749(4) 1.4427(3) 0.5767(2) 0.0546(8) Uani 1 1 d . . . . .
H31A H 0.2826 1.4333 0.5835 0.082 Uiso 1 1 calc R U . . .
H31B H 0.3668 1.5208 0.5428 0.082 Uiso 1 1 calc R U . . .
H31C H 0.4145 1.4420 0.6322 0.082 Uiso 1 1 calc R U . . .
C32 C 0.2521(15) -0.3538(13) 0.8449(8) 0.048(3) Uani 0.425(6) 1 d . . P A 1
H32 H 0.2934 -0.2942 0.8566 0.057 Uiso 0.425(6) 1 calc R U P A 1
C32A C 0.0572(6) -0.3239(5) 0.7467(3) 0.0431(13) Uani 0.575(6) 1 d . . P A 2
H32A H 0.0027 -0.2824 0.6982 0.052 Uiso 0.575(6) 1 calc R U P A 2
C33 C 0.1163(10) -0.4171(8) 0.7491(5) 0.056(2) Uani 0.425(6) 1 d D . P A 1
H33D H 0.1310 -0.4848 0.7943 0.084 Uiso 0.425(6) 1 calc R U P A 1
H33E H 0.1554 -0.4499 0.6967 0.084 Uiso 0.425(6) 1 calc R U P A 1
H33F H 0.0165 -0.3740 0.7410 0.084 Uiso 0.425(6) 1 calc R U P A 1
C33A C 0.2252(13) -0.2269(10) 0.6937(9) 0.133(7) Uani 0.575(6) 1 d D . P A 2
H33A H 0.3118 -0.2741 0.6684 0.200 Uiso 0.575(6) 1 calc R U P A 2
H33B H 0.2416 -0.1619 0.7224 0.200 Uiso 0.575(6) 1 calc R U P A 2
H33C H 0.1540 -0.1898 0.6496 0.200 Uiso 0.575(6) 1 calc R U P A 2
C34 C 0.1683(13) -0.2231(10) 0.7126(7) 0.063(3) Uani 0.425(6) 1 d D . P A 1
H34D H 0.2065 -0.1669 0.7377 0.095 Uiso 0.425(6) 1 calc R U P A 1
H34E H 0.0693 -0.1819 0.6995 0.095 Uiso 0.425(6) 1 calc R U P A 1
H34F H 0.2179 -0.2471 0.6607 0.095 Uiso 0.425(6) 1 calc R U P A 1
C34A C 0.2689(15) -0.3685(15) 0.8254(10) 0.111(7) Uani 0.575(6) 1 d D . P A 2
H34A H 0.2240 -0.4179 0.8623 0.167 Uiso 0.575(6) 1 calc R U P A 2
H34B H 0.2868 -0.3068 0.8569 0.167 Uiso 0.575(6) 1 calc R U P A 2
H34C H 0.3571 -0.4221 0.8056 0.167 Uiso 0.575(6) 1 calc R U P A 2


_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
Cd1 O4 2.2625(17) . ?
Cd1 N4 2.282(2) 2_657 ?
Cd1 N1 2.282(2) . ?
Cd1 O2 2.2971(18) 2_766 ?
Cd1 O1 2.3970(17) 2_766 ?
Cd1 O3 2.4130(17) . ?
Cd1 C28 2.674(2) . ?
Cd1 C14 2.693(2) 2_766 ?
O1 C14 1.254(3) . ?
O1 Cd1 2.3970(17) 2_766 ?
O2 C14 1.279(3) . ?
O2 Cd1 2.2971(18) 2_766 ?
O3 C28 1.263(3) . ?
O4 C28 1.272(3) . ?
O5 C29 1.227(4) . ?
O6 C32 1.204(12) . ?
O6A C32A 1.194(7) . ?
N1 C5 1.331(3) . ?
N1 C1 1.351(3) . ?
N2 C6 1.292(3) . ?
N2 N3 1.362(3) . ?
N3 C8 1.384(3) . ?
N4 C19 1.335(3) . ?
N4 C15 1.352(3) . ?
N4 Cd1 2.282(2) 2_657 ?
N5 C20 1.292(3) . ?
N5 N6 1.355(3) . ?
N6 C22 1.388(3) . ?
N7 C29 1.328(4) . ?
N7 C30 1.450(4) . ?
N7 C31 1.455(4) . ?
N8 C32 1.327(17) . ?
N8 C34 1.451(7) . ?
N8 C33 1.453(8) . ?
N8A C32A 1.315(13) . ?
N8A C33A 1.441(7) . ?
N8A C34A 1.449(8) . ?
C1 C2 1.378(4) . ?
C2 C3 1.388(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.398(3) . ?
C4 C6 1.477(3) . ?
C6 C7 1.496(3) . ?
C8 C9 1.399(3) . ?
C8 C13 1.402(4) . ?
C9 C10 1.378(3) . ?
C10 C11 1.395(3) . ?
C11 C12 1.394(3) . ?
C11 C14 1.489(3) . ?
C12 C13 1.388(3) . ?
C14 Cd1 2.693(2) 2_766 ?
C15 C16 1.374(4) . ?
C16 C17 1.386(3) . ?
C17 C18 1.394(3) . ?
C18 C19 1.397(3) . ?
C18 C20 1.479(3) . ?
C20 C21 1.497(3) . ?
C22 C27 1.400(3) . ?
C22 C23 1.401(3) . ?
C23 C24 1.386(3) . ?
C24 C25 1.396(3) . ?
C25 C26 1.395(3) . ?
C25 C28 1.489(3) . ?
C26 C27 1.376(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
O4 Cd1 N4 145.43(6) . 2_657 ?
O4 Cd1 N1 98.67(7) . . ?
N4 Cd1 N1 88.07(8) 2_657 . ?
O4 Cd1 O2 98.44(7) . 2_766 ?
N4 Cd1 O2 94.93(7) 2_657 2_766 ?
N1 Cd1 O2 144.79(6) . 2_766 ?
O4 Cd1 O1 99.56(7) . 2_766 ?
N4 Cd1 O1 114.29(7) 2_657 2_766 ?
N1 Cd1 O1 90.82(7) . 2_766 ?
O2 Cd1 O1 56.04(6) 2_766 2_766 ?
O4 Cd1 O3 56.41(6) . . ?
N4 Cd1 O3 90.03(6) 2_657 . ?
N1 Cd1 O3 115.56(7) . . ?
O2 Cd1 O3 99.54(6) 2_766 . ?
O1 Cd1 O3 145.26(6) 2_766 . ?
O4 Cd1 C28 28.33(6) . . ?
N4 Cd1 C28 118.04(7) 2_657 . ?
N1 Cd1 C28 110.77(7) . . ?
O2 Cd1 C28 98.68(6) 2_766 . ?
O1 Cd1 C28 123.31(7) 2_766 . ?
O3 Cd1 C28 28.15(6) . . ?
O4 Cd1 C14 101.10(7) . 2_766 ?
N4 Cd1 C14 105.63(7) 2_657 2_766 ?
N1 Cd1 C14 117.60(7) . 2_766 ?
O2 Cd1 C14 28.31(6) 2_766 2_766 ?
O1 Cd1 C14 27.76(6) 2_766 2_766 ?
O3 Cd1 C14 124.71(6) . 2_766 ?
C28 Cd1 C14 114.28(7) . 2_766 ?
C14 O1 Cd1 89.35(13) . 2_766 ?
C14 O2 Cd1 93.29(13) . 2_766 ?
C28 O3 Cd1 87.48(12) . . ?
C28 O4 Cd1 94.10(14) . . ?
C5 N1 C1 118.9(2) . . ?
C5 N1 Cd1 121.83(15) . . ?
C1 N1 Cd1 119.16(16) . . ?
C6 N2 N3 118.3(2) . . ?
N2 N3 C8 118.7(2) . . ?
C19 N4 C15 118.5(2) . . ?
C19 N4 Cd1 121.24(15) . 2_657 ?
C15 N4 Cd1 120.22(16) . 2_657 ?
C20 N5 N6 119.2(2) . . ?
N5 N6 C22 118.76(19) . . ?
C29 N7 C30 121.1(3) . . ?
C29 N7 C31 122.2(3) . . ?
C30 N7 C31 116.4(3) . . ?
C32 N8 C34 123.9(11) . . ?
C32 N8 C33 119.5(10) . . ?
C34 N8 C33 116.5(10) . . ?
C32A N8A C33A 122.4(10) . . ?
C32A N8A C34A 120.0(10) . . ?
C33A N8A C34A 117.6(13) . . ?
N1 C1 C2 122.1(2) . . ?
C1 C2 C3 118.7(2) . . ?
C2 C3 C4 120.2(2) . . ?
C3 C4 C5 116.9(2) . . ?
C3 C4 C6 122.4(2) . . ?
C5 C4 C6 120.67(19) . . ?
N1 C5 C4 123.32(19) . . ?
N2 C6 C4 114.9(2) . . ?
N2 C6 C7 124.4(2) . . ?
C4 C6 C7 120.7(2) . . ?
N3 C8 C9 117.8(2) . . ?
N3 C8 C13 122.9(2) . . ?
C9 C8 C13 119.3(2) . . ?
C10 C9 C8 119.8(2) . . ?
C9 C10 C11 121.4(2) . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 C14 120.7(2) . . ?
C10 C11 C14 120.5(2) . . ?
C13 C12 C11 120.6(2) . . ?
C12 C13 C8 120.2(2) . . ?
O1 C14 O2 121.2(2) . . ?
O1 C14 C11 121.1(2) . . ?
O2 C14 C11 117.7(2) . . ?
O1 C14 Cd1 62.89(12) . 2_766 ?
O2 C14 Cd1 58.40(11) . 2_766 ?
C11 C14 Cd1 173.77(16) . 2_766 ?
N4 C15 C16 122.1(2) . . ?
C15 C16 C17 119.2(2) . . ?
C16 C17 C18 119.8(2) . . ?
C17 C18 C19 117.0(2) . . ?
C17 C18 C20 122.8(2) . . ?
C19 C18 C20 120.2(2) . . ?
N4 C19 C18 123.4(2) . . ?
N5 C20 C18 114.9(2) . . ?
N5 C20 C21 125.3(2) . . ?
C18 C20 C21 119.8(2) . . ?
N6 C22 C27 118.2(2) . . ?
N6 C22 C23 122.5(2) . . ?
C27 C22 C23 119.4(2) . . ?
C24 C23 C22 119.4(2) . . ?
C23 C24 C25 121.5(2) . . ?
C26 C25 C24 118.4(2) . . ?
C26 C25 C28 120.0(2) . . ?
C24 C25 C28 121.5(2) . . ?
C27 C26 C25 121.0(2) . . ?
C26 C27 C22 120.4(2) . . ?
O3 C28 O4 121.7(2) . . ?
O3 C28 C25 120.45(19) . . ?
O4 C28 C25 117.8(2) . . ?
O3 C28 Cd1 64.36(11) . . ?
O4 C28 Cd1 57.56(11) . . ?
C25 C28 Cd1 171.49(15) . . ?
O5 C29 N7 124.7(3) . . ?
O6 C32 N8 128.6(13) . . ?
O6A C32A N8A 127.1(7) . . ?

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
N6 H6N O2 0.8800(11) 2.091(9) 2.944(3) 163(3) 2_666
N3 H3N O5 0.8801(11) 2.088(9) 2.951(3) 166(3) .

_refine_diff_density_max         0.470
_refine_diff_density_min         -1.760
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DMF
####################################################################### 
# 
# 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_1Zn-2DMF
_database_code_depnum_ccdc_archive 'CCDC 1477014'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 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         
;
C28 H24 N6 O4 Zn, 2(C3 H7 N O)
;
_chemical_formula_sum            'C34 H38 N8 O6 Zn'
_chemical_formula_weight         720.09

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.0203(4)
_cell_length_b                   11.3836(4)
_cell_length_c                   15.9371(5)
_cell_angle_alpha                82.8520(10)
_cell_angle_beta                 87.3960(10)
_cell_angle_gamma                72.5180(10)
_cell_volume                     1720.39(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5034
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.68

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.770
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6840
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(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            20475
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         27.621
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7924
_reflns_number_gt                6299
_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    ?
_computing_publication_material  ?
_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)+(0.0464P)²] 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         7924
_refine_ls_number_parameters     502
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
Zn1 Zn 0.72958(2) 0.35482(2) 0.80850(2) 0.01943(8) Uani 1 1 d . . . . .
O1 O 1.18885(15) 0.60230(13) 0.31653(9) 0.0285(3) Uani 1 1 d . . . . .
O2 O 1.14685(14) 0.79605(13) 0.26095(8) 0.0252(3) Uani 1 1 d . . . . .
O3 O 0.61299(14) 0.24639(13) 0.89283(9) 0.0260(3) Uani 1 1 d . . . . .
O4 O 0.53534(14) 0.34554(13) 0.76900(9) 0.0262(3) Uani 1 1 d . . . . .
O5 O 0.6465(2) 1.15517(15) 0.54243(11) 0.0472(5) Uani 1 1 d . . . . .
O6 O 0.2705(4) -0.4316(3) 0.8897(2) 0.0463(11) Uani 0.521(4) 1 d . . P A 1
O6A O 0.0119(4) -0.3660(4) 0.7987(3) 0.0564(14) Uani 0.479(4) 1 d . . P A 2
N1 N 0.66239(17) 0.54157(15) 0.82998(10) 0.0216(4) Uani 1 1 d . . . . .
N2 N 0.75071(18) 0.80792(15) 0.65989(10) 0.0225(4) Uani 1 1 d . . . . .
N3 N 0.77652(19) 0.88853(15) 0.59555(11) 0.0265(4) Uani 1 1 d D . . . .
H3N H 0.734(2) 0.9687(4) 0.5865(14) 0.040 Uiso 1 1 d D U . . .
N4 N 0.11549(17) -0.31928(15) 1.10016(10) 0.0214(4) Uani 1 1 d . . . . .
N5 N 0.09460(17) -0.05459(15) 0.90065(10) 0.0215(4) Uani 1 1 d . . . . .
N6 N 0.09591(17) 0.03981(16) 0.83974(10) 0.0232(4) Uani 1 1 d D . . . .
H6N H 0.0259(15) 0.0808(17) 0.8060(11) 0.035 Uiso 1 1 d D U . . .
N7 N 0.4691(2) 1.33383(19) 0.53405(12) 0.0392(5) Uani 1 1 d . . . . .
N8 N 0.1899(16) -0.3242(13) 0.7640(8) 0.0271(17) Uani 0.521(4) 1 d . . P A 1
N8A N 0.196(2) -0.2990(14) 0.7455(10) 0.036(3) Uani 0.479(4) 1 d . . P A 2
C1 C 0.6058(2) 0.57307(19) 0.90543(13) 0.0281(5) Uani 1 1 d . . . . .
H1 H 0.5989 0.5095 0.9485 0.034 Uiso 1 1 calc R U . . .
C2 C 0.5578(2) 0.69473(19) 0.92183(13) 0.0269(5) Uani 1 1 d . . . . .
H2 H 0.5167 0.7148 0.9751 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5702(2) 0.78737(19) 0.85968(12) 0.0225(4) Uani 1 1 d . . . . .
H3 H 0.5364 0.8718 0.8698 0.027 Uiso 1 1 calc R U . . .
C4 C 0.63235(19) 0.75659(17) 0.78210(11) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.6755(2) 0.63077(18) 0.77090(12) 0.0200(4) Uani 1 1 d . . . . .
H5 H 0.7165 0.6078 0.7182 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6531(2) 0.84990(18) 0.71376(12) 0.0208(4) Uani 1 1 d . . . . .
C7 C 0.5642(2) 0.98251(19) 0.70916(14) 0.0336(5) Uani 1 1 d . . . . .
H7A H 0.6219 1.0346 0.7206 0.050 Uiso 1 1 calc R U . . .
H7B H 0.4887 0.9901 0.7513 0.050 Uiso 1 1 calc R U . . .
H7C H 0.5241 1.0095 0.6525 0.050 Uiso 1 1 calc R U . . .
C8 C 0.8688(2) 0.84243(18) 0.53116(12) 0.0227(4) Uani 1 1 d . . . . .
C9 C 0.8928(2) 0.92687(19) 0.46551(13) 0.0278(5) Uani 1 1 d . . . . .
H9 H 0.8480 1.0131 0.4662 0.033 Uiso 1 1 calc R U . . .
C10 C 0.9813(2) 0.88533(19) 0.39965(13) 0.0261(5) Uani 1 1 d . . . . .
H10 H 0.9983 0.9437 0.3557 0.031 Uiso 1 1 calc R U . . .
C11 C 1.0463(2) 0.75914(18) 0.39626(12) 0.0208(4) Uani 1 1 d . . . . .
C12 C 1.0228(2) 0.67536(19) 0.46246(12) 0.0238(4) Uani 1 1 d . . . . .
H12 H 1.0670 0.5891 0.4614 0.029 Uiso 1 1 calc R U . . .
C13 C 0.9359(2) 0.71581(19) 0.52988(13) 0.0255(5) Uani 1 1 d . . . . .
H13 H 0.9221 0.6577 0.5750 0.031 Uiso 1 1 calc R U . . .
C14 C 1.1325(2) 0.71626(19) 0.32144(12) 0.0225(4) Uani 1 1 d . . . . .
C15 C 0.0267(2) -0.38864(18) 1.10520(13) 0.0253(5) Uani 1 1 d . . . . .
H15 H 0.0352 -0.4523 1.1510 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0753(2) -0.37037(19) 1.04646(13) 0.0269(5) Uani 1 1 d . . . . .
H16 H -0.1359 -0.4211 1.0514 0.032 Uiso 1 1 calc R U . . .
C17 C -0.0892(2) -0.27712(18) 0.97981(13) 0.0238(4) Uani 1 1 d . . . . .
H17 H -0.1592 -0.2637 0.9384 0.029 Uiso 1 1 calc R U . . .
C18 C 0.0002(2) -0.20287(18) 0.97365(12) 0.0216(4) Uani 1 1 d . . . . .
C19 C 0.1009(2) -0.22894(18) 1.03636(12) 0.0213(4) Uani 1 1 d . . . . .
H19 H 0.1627 -0.1795 1.0334 0.026 Uiso 1 1 calc R U . . .
C20 C -0.0095(2) -0.10000(18) 0.90525(12) 0.0220(4) Uani 1 1 d . . . . .
C21 C -0.1353(2) -0.0552(2) 0.84925(14) 0.0331(5) Uani 1 1 d . . . . .
H21A H -0.1565 0.0344 0.8332 0.050 Uiso 1 1 calc R U . . .
H21B H -0.2156 -0.0730 0.8797 0.050 Uiso 1 1 calc R U . . .
H21C H -0.1161 -0.0978 0.7983 0.050 Uiso 1 1 calc R U . . .
C22 C 0.2006(2) 0.09609(18) 0.84214(12) 0.0195(4) Uani 1 1 d . . . . .
C23 C 0.30084(19) 0.06204(17) 0.90551(12) 0.0190(4) Uani 1 1 d . . . . .
H23 H 0.2992 -0.0018 0.9496 0.023 Uiso 1 1 calc R U . . .
C24 C 0.4034(2) 0.12198(17) 0.90390(12) 0.0188(4) Uani 1 1 d . . . . .
H24 H 0.4712 0.0988 0.9475 0.023 Uiso 1 1 calc R U . . .
C25 C 0.4087(2) 0.21514(17) 0.83967(12) 0.0189(4) Uani 1 1 d . . . . .
C26 C 0.3082(2) 0.24800(18) 0.77670(13) 0.0237(4) Uani 1 1 d . . . . .
H26 H 0.3104 0.3115 0.7324 0.028 Uiso 1 1 calc R U . . .
C27 C 0.2055(2) 0.19020(19) 0.77727(13) 0.0246(4) Uani 1 1 d . . . . .
H27 H 0.1378 0.2141 0.7337 0.030 Uiso 1 1 calc R U . . .
C28 C 0.5247(2) 0.27258(18) 0.83435(12) 0.0210(4) Uani 1 1 d . . . . .
C29 C 0.5757(2) 1.2481(2) 0.57230(14) 0.0320(5) Uani 1 1 d . . . . .
H29 H 0.5990 1.2596 0.6272 0.038 Uiso 1 1 calc R U . . .
C30 C 0.4249(4) 1.3224(3) 0.4504(2) 0.0819(11) Uani 1 1 d . . . . .
H30A H 0.4890 1.2485 0.4292 0.123 Uiso 1 1 calc R U . . .
H30B H 0.4261 1.3961 0.4118 0.123 Uiso 1 1 calc R U . . .
H30C H 0.3299 1.3147 0.4540 0.123 Uiso 1 1 calc R U . . .
C31 C 0.3823(3) 1.4378(2) 0.57415(17) 0.0512(7) Uani 1 1 d . . . . .
H31A H 0.2879 1.4298 0.5829 0.077 Uiso 1 1 calc R U . . .
H31B H 0.3778 1.5151 0.5379 0.077 Uiso 1 1 calc R U . . .
H31C H 0.4225 1.4392 0.6288 0.077 Uiso 1 1 calc R U . . .
C32 C 0.2645(12) -0.3466(13) 0.8356(9) 0.0403(19) Uani 0.521(4) 1 d . . P A 1
H32 H 0.3160 -0.2913 0.8439 0.048 Uiso 0.521(4) 1 calc R U P A 1
C32A C 0.0661(6) -0.3115(5) 0.7451(3) 0.0368(14) Uani 0.479(4) 1 d . . P A 2
H32A H 0.0112 -0.2724 0.6966 0.044 Uiso 0.479(4) 1 calc R U P A 2
C33 C 0.1229(7) -0.4093(5) 0.7395(4) 0.0593(18) Uani 0.521(4) 1 d . . P A 1
H33A H 0.0213 -0.3752 0.7462 0.089 Uiso 0.521(4) 1 calc R U P A 1
H33B H 0.1558 -0.4886 0.7754 0.089 Uiso 0.521(4) 1 calc R U P A 1
H33C H 0.1456 -0.4223 0.6803 0.089 Uiso 0.521(4) 1 calc R U P A 1
C33A C 0.2510(11) -0.2288(11) 0.6849(8) 0.109(5) Uani 0.479(4) 1 d . . P A 2
H33D H 0.3414 -0.2797 0.6651 0.163 Uiso 0.479(4) 1 calc R U P A 2
H33E H 0.2640 -0.1581 0.7092 0.163 Uiso 0.479(4) 1 calc R U P A 2
H33F H 0.1864 -0.1985 0.6372 0.163 Uiso 0.479(4) 1 calc R U P A 2
C34 C 0.1792(9) -0.2132(7) 0.7034(5) 0.066(2) Uani 0.521(4) 1 d . . P A 1
H34A H 0.2309 -0.1626 0.7249 0.100 Uiso 0.521(4) 1 calc R U P A 1
H34B H 0.0807 -0.1646 0.6963 0.100 Uiso 0.521(4) 1 calc R U P A 1
H34C H 0.2191 -0.2383 0.6488 0.100 Uiso 0.521(4) 1 calc R U P A 1
C34A C 0.271(2) -0.362(2) 0.8197(14) 0.106(8) Uani 0.479(4) 1 d . . P A 2
H34D H 0.2246 -0.4202 0.8483 0.159 Uiso 0.479(4) 1 calc R U P A 2
H34E H 0.2742 -0.3013 0.8577 0.159 Uiso 0.479(4) 1 calc R U P A 2
H34F H 0.3671 -0.4073 0.8042 0.159 Uiso 0.479(4) 1 calc R U P A 2


_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
Zn1 N4 2.0914(17) 2_657 ?
Zn1 N1 2.0953(16) . ?
Zn1 O4 2.1088(14) . ?
Zn1 O1 2.1740(14) 2_766 ?
Zn1 O2 2.1860(14) 2_766 ?
Zn1 O3 2.2373(14) . ?
Zn1 C28 2.4985(19) . ?
Zn1 C14 2.5178(19) 2_766 ?
O1 C14 1.261(2) . ?
O1 Zn1 2.1741(14) 2_766 ?
O2 C14 1.274(2) . ?
O2 Zn1 2.1860(14) 2_766 ?
O3 C28 1.260(2) . ?
O4 C28 1.270(2) . ?
O5 C29 1.222(3) . ?
O6 C32 1.202(14) . ?
O6A C32A 1.199(6) . ?
N1 C5 1.329(2) . ?
N1 C1 1.349(2) . ?
N2 C6 1.291(2) . ?
N2 N3 1.358(2) . ?
N3 C8 1.393(2) . ?
N3 H3N 0.8800(10) . ?
N4 C19 1.333(2) . ?
N4 C15 1.350(2) . ?
N4 Zn1 2.0914(17) 2_657 ?
N5 C20 1.291(2) . ?
N5 N6 1.358(2) . ?
N6 C22 1.388(2) . ?
N6 H6N 0.8799(10) . ?
N7 C29 1.323(3) . ?
N7 C31 1.444(3) . ?
N7 C30 1.456(3) . ?
N8 C32 1.35(2) . ?
N8 C33 1.431(15) . ?
N8 C34 1.472(10) . ?
N8A C32A 1.356(17) . ?
N8A C33A 1.376(11) . ?
N8A C34A 1.42(2) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(3) . ?
C4 C6 1.477(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.393(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 C14 1.484(3) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 Zn1 2.5178(19) 2_766 ?
C15 C16 1.369(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.397(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(3) . ?
C18 C20 1.481(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.500(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.393(3) . ?
C22 C27 1.404(3) . ?
C23 C24 1.392(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(3) . ?
C25 C28 1.490(3) . ?
C26 C27 1.377(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32 0.9500 . ?
C32A H32A 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C33A H33D 0.9800 . ?
C33A H33E 0.9800 . ?
C33A H33F 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C34A H34D 0.9800 . ?
C34A H34E 0.9800 . ?
C34A H34F 0.9800 . ?

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
N4 Zn1 N1 89.82(6) 2_657 . ?
N4 Zn1 O4 151.30(6) 2_657 . ?
N1 Zn1 O4 96.93(6) . . ?
N4 Zn1 O1 110.58(6) 2_657 2_766 ?
N1 Zn1 O1 92.57(6) . 2_766 ?
O4 Zn1 O1 97.00(6) . 2_766 ?
N4 Zn1 O2 92.47(6) 2_657 2_766 ?
N1 Zn1 O2 151.84(6) . 2_766 ?
O4 Zn1 O2 94.42(5) . 2_766 ?
O1 Zn1 O2 60.44(5) 2_766 2_766 ?
N4 Zn1 O3 90.80(6) 2_657 . ?
N1 Zn1 O3 110.35(6) . . ?
O4 Zn1 O3 60.68(5) . . ?
O1 Zn1 O3 148.93(5) 2_766 . ?
O2 Zn1 O3 97.68(5) 2_766 . ?
N4 Zn1 C28 121.02(7) 2_657 . ?
N1 Zn1 C28 107.39(6) . . ?
O4 Zn1 C28 30.54(6) . . ?
O1 Zn1 C28 123.88(6) 2_766 . ?
O2 Zn1 C28 95.38(6) 2_766 . ?
O3 Zn1 C28 30.22(6) . . ?
N4 Zn1 C14 102.99(6) 2_657 2_766 ?
N1 Zn1 C14 122.19(6) . 2_766 ?
O4 Zn1 C14 96.90(6) . 2_766 ?
O1 Zn1 C14 30.05(6) 2_766 2_766 ?
O2 Zn1 C14 30.40(6) 2_766 2_766 ?
O3 Zn1 C14 125.25(6) . 2_766 ?
C28 Zn1 C14 112.47(6) . 2_766 ?
C14 O1 Zn1 90.25(12) . 2_766 ?
C14 O2 Zn1 89.36(12) . 2_766 ?
C28 O3 Zn1 86.43(11) . . ?
C28 O4 Zn1 91.94(12) . . ?
C5 N1 C1 118.68(17) . . ?
C5 N1 Zn1 121.42(12) . . ?
C1 N1 Zn1 119.90(14) . . ?
C6 N2 N3 118.42(17) . . ?
N2 N3 C8 119.06(16) . . ?
N2 N3 H3N 126.7(16) . . ?
C8 N3 H3N 113.9(16) . . ?
C19 N4 C15 118.33(17) . . ?
C19 N4 Zn1 121.80(13) . 2_657 ?
C15 N4 Zn1 119.87(14) . 2_657 ?
C20 N5 N6 119.39(17) . . ?
N5 N6 C22 118.09(16) . . ?
N5 N6 H6N 125.4(15) . . ?
C22 N6 H6N 114.8(15) . . ?
C29 N7 C31 123.0(2) . . ?
C29 N7 C30 121.1(2) . . ?
C31 N7 C30 115.7(2) . . ?
C32 N8 C33 122.6(10) . . ?
C32 N8 C34 121.6(12) . . ?
C33 N8 C34 115.7(11) . . ?
C32A N8A C33A 125.6(14) . . ?
C32A N8A C34A 112.2(11) . . ?
C33A N8A C34A 122.1(17) . . ?
N1 C1 C2 121.91(19) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 119.13(18) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 119.90(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 116.72(18) . . ?
C3 C4 C6 123.00(17) . . ?
C5 C4 C6 120.28(16) . . ?
N1 C5 C4 123.61(17) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
N2 C6 C4 115.06(17) . . ?
N2 C6 C7 124.03(18) . . ?
C4 C6 C7 120.91(17) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 117.99(18) . . ?
N3 C8 C13 122.50(18) . . ?
C9 C8 C13 119.51(18) . . ?
C10 C9 C8 120.03(19) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 121.22(19) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 118.41(18) . . ?
C12 C11 C14 121.39(18) . . ?
C10 C11 C14 120.13(18) . . ?
C13 C12 C11 121.05(19) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 119.75(19) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
O1 C14 O2 119.95(18) . . ?
O1 C14 C11 120.82(18) . . ?
O2 C14 C11 119.22(18) . . ?
O1 C14 Zn1 59.71(10) . 2_766 ?
O2 C14 Zn1 60.25(10) . 2_766 ?
C11 C14 Zn1 177.89(14) . 2_766 ?
N4 C15 C16 122.21(19) . . ?
N4 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C15 C16 C17 119.24(18) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 119.75(19) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 116.74(19) . . ?
C19 C18 C20 120.23(17) . . ?
C17 C18 C20 123.03(18) . . ?
N4 C19 C18 123.72(17) . . ?
N4 C19 H19 118.1 . . ?
C18 C19 H19 118.1 . . ?
N5 C20 C18 114.87(18) . . ?
N5 C20 C21 125.41(19) . . ?
C18 C20 C21 119.71(17) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C22 C23 122.69(18) . . ?
N6 C22 C27 118.15(18) . . ?
C23 C22 C27 119.16(17) . . ?
C24 C23 C22 119.74(18) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 121.24(18) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 118.43(17) . . ?
C24 C25 C28 121.19(18) . . ?
C26 C25 C28 120.23(18) . . ?
C27 C26 C25 121.26(18) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C22 120.17(19) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
O3 C28 O4 120.63(18) . . ?
O3 C28 C25 120.36(18) . . ?
O4 C28 C25 118.98(18) . . ?
O3 C28 Zn1 63.35(10) . . ?
O4 C28 Zn1 57.52(10) . . ?
C25 C28 Zn1 172.48(13) . . ?
O5 C29 N7 125.0(2) . . ?
O5 C29 H29 117.5 . . ?
N7 C29 H29 117.5 . . ?
N7 C30 H30A 109.5 . . ?
N7 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N7 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N7 C31 H31A 109.5 . . ?
N7 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N7 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O6 C32 N8 124.6(12) . . ?
O6 C32 H32 117.7 . . ?
N8 C32 H32 117.7 . . ?
O6A C32A N8A 127.6(7) . . ?
O6A C32A H32A 116.2 . . ?
N8A C32A H32A 116.2 . . ?
N8 C33 H33A 109.5 . . ?
N8 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
N8 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N8A C33A H33D 109.5 . . ?
N8A C33A H33E 109.5 . . ?
H33D C33A H33E 109.5 . . ?
N8A C33A H33F 109.5 . . ?
H33D C33A H33F 109.5 . . ?
H33E C33A H33F 109.5 . . ?
N8 C34 H34A 109.5 . . ?
N8 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N8 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N8A C34A H34D 109.5 . . ?
N8A C34A H34E 109.5 . . ?
H34D C34A H34E 109.5 . . ?
N8A C34A H34F 109.5 . . ?
H34D C34A H34F 109.5 . . ?
H34E C34A H34F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N O5 0.8800(10) 2.082(5) 2.952(2) 170(2) .
N6 H6N O2 0.8799(10) 2.107(4) 2.977(2) 170(2) 2_666

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.062


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DMF
####################################################################### 
# 
# 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_1CuDMF
_database_code_depnum_ccdc_archive 'CCDC 1477015'
_audit_update_record             
;
2016-06-17 deposited with the CCDC.
2016-06-30 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         'C28 H24 Cu N6 O4, C3 H7 N O'
_chemical_formula_sum            'C31 H31 Cu N7 O5'
_chemical_formula_weight         645.17

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'
Cu Cu 0.3201 1.2651 '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                   16.7033(17)
_cell_length_b                   9.3648(9)
_cell_length_c                   19.686(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.139(5)
_cell_angle_gamma                90
_cell_volume                     2926.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    564
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      21.58

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             1340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.800
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5419
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(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            6854
_diffrn_reflns_av_unetI/netI     0.1222
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.566
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        27.497
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3349
_reflns_number_gt                1764
_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    ?
_computing_publication_material  ?
_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)+(0.0517P)²] 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         3349
_refine_ls_number_parameters     225
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_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
Cu1 Cu 0.2500 0.7500 0.5000 0.0314(2) Uani 1 2 d S . P . .
O1 O 0.18767(18) 0.7023(3) 0.40221(14) 0.0355(7) Uani 1 1 d . . . . .
O2 O 0.31185(18) 0.6065(3) 0.40969(15) 0.0397(8) Uani 1 1 d . . . . .
O3 O 0.5077(6) 0.3808(9) 0.1774(5) 0.089(3) Uani 0.5 1 d . . P A -1
N1 N -0.2256(2) 0.5554(3) -0.03017(17) 0.0321(8) Uani 1 1 d . . . . .
N2 N -0.0004(2) 0.3827(3) 0.07561(17) 0.0311(8) Uani 1 1 d . . . . .
N3 N 0.0795(2) 0.3481(4) 0.11361(18) 0.0340(8) Uani 1 1 d D . . . .
H3N H 0.106(2) 0.273(2) 0.104(2) 0.051 Uiso 1 1 d D U . . .
N4 N 0.5000 0.5671(6) 0.2500 0.0513(15) Uani 1 2 d DS T P . .
C1 C -0.2834(3) 0.4788(5) -0.0798(2) 0.0465(12) Uani 1 1 d . . . . .
H1 H -0.3372 0.5195 -0.1026 0.056 Uiso 1 1 calc R U . . .
C2 C -0.2666(3) 0.3432(5) -0.0983(3) 0.0591(15) Uani 1 1 d . . . . .
H2 H -0.3085 0.2903 -0.1328 0.071 Uiso 1 1 calc R U . . .
C3 C -0.1881(3) 0.2847(5) -0.0661(2) 0.0501(13) Uani 1 1 d . . . . .
H3 H -0.1761 0.1907 -0.0782 0.060 Uiso 1 1 calc R U . . .
C4 C -0.1269(3) 0.3628(4) -0.0163(2) 0.0322(10) Uani 1 1 d . . . . .
C5 C -0.1505(3) 0.4970(4) 0.0003(2) 0.0307(9) Uani 1 1 d . . . . .
H5 H -0.1102 0.5507 0.0359 0.037 Uiso 1 1 calc R U . . .
C6 C -0.0413(3) 0.3104(4) 0.0196(2) 0.0319(10) Uani 1 1 d . . . . .
C7 C -0.0087(3) 0.1871(5) -0.0111(3) 0.0556(14) Uani 1 1 d . . . . .
H7A H -0.0101 0.2097 -0.0601 0.083 Uiso 1 1 calc R U . . .
H7B H -0.0438 0.1030 -0.0115 0.083 Uiso 1 1 calc R U . . .
H7C H 0.0495 0.1671 0.0180 0.083 Uiso 1 1 calc R U . . .
C8 C 0.1186(2) 0.4247(4) 0.1757(2) 0.0291(9) Uani 1 1 d . . . . .
C9 C 0.0784(3) 0.5351(4) 0.1984(2) 0.0331(10) Uani 1 1 d . . . . .
H9 H 0.0247 0.5669 0.1692 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1163(2) 0.5989(4) 0.2633(2) 0.0327(10) Uani 1 1 d . . . . .
H10 H 0.0872 0.6722 0.2793 0.039 Uiso 1 1 calc R U . . .
C11 C 0.1956(2) 0.5592(4) 0.3060(2) 0.0284(9) Uani 1 1 d . . . . .
C12 C 0.2378(3) 0.4540(5) 0.2808(2) 0.0379(11) Uani 1 1 d . . . . .
H12 H 0.2935 0.4280 0.3081 0.045 Uiso 1 1 calc R U . . .
C13 C 0.1996(3) 0.3871(5) 0.2166(2) 0.0394(11) Uani 1 1 d . . . . .
H13 H 0.2289 0.3148 0.2001 0.047 Uiso 1 1 calc R U . . .
C14 C 0.2353(3) 0.6261(4) 0.3769(2) 0.0296(10) Uani 1 1 d . . . . .
C15 C 0.5206(9) 0.497(2) 0.1968(9) 0.055(4) Uani 0.5 1 d D . P A -1
H15 H 0.5501 0.5524 0.1721 0.066 Uiso 0.5 1 calc R U P A -1
C16 C 0.5193(13) 0.7128(9) 0.263(2) 0.081(9) Uani 0.5 1 d . . P A -1
H16A H 0.5638 0.7396 0.2427 0.121 Uiso 0.5 1 calc R U P A -1
H16B H 0.5387 0.7301 0.3147 0.121 Uiso 0.5 1 calc R U P A -1
H16C H 0.4688 0.7701 0.2408 0.121 Uiso 0.5 1 calc R U P A -1
C17 C 0.4407(11) 0.506(2) 0.2794(13) 0.098(8) Uani 0.5 1 d . . P A -1
H17A H 0.3889 0.5634 0.2652 0.147 Uiso 0.5 1 calc R U P A -1
H17B H 0.4641 0.5051 0.3316 0.147 Uiso 0.5 1 calc R U P A -1
H17C H 0.4279 0.4086 0.2616 0.147 Uiso 0.5 1 calc R U P A -1


_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
Cu1 O1 1.934(3) . ?
Cu1 O1 1.934(3) 7_566 ?
Cu1 N1 1.997(3) 8_566 ?
Cu1 N1 1.997(3) 2 ?
O1 C14 1.279(5) . ?
O2 C14 1.254(5) . ?
O3 C15 1.15(2) . ?
N1 C5 1.329(5) . ?
N1 C1 1.347(5) . ?
N1 Cu1 1.997(3) 2 ?
N2 C6 1.292(5) . ?
N2 N3 1.352(4) . ?
N3 C8 1.392(5) . ?
N4 C15 1.369(16) . ?
N4 C16 1.407(11) . ?
N4 C17 1.412(18) . ?
C1 C2 1.374(6) . ?
C2 C3 1.378(6) . ?
C3 C4 1.386(5) . ?
C4 C5 1.386(5) . ?
C4 C6 1.467(5) . ?
C6 C7 1.485(6) . ?
C8 C9 1.380(5) . ?
C8 C13 1.387(5) . ?
C9 C10 1.374(5) . ?
C10 C11 1.380(5) . ?
C11 C12 1.389(5) . ?
C11 C14 1.485(5) . ?
C12 C13 1.377(5) . ?

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 Cu1 O1 180 . 7_566 ?
O1 Cu1 N1 90.64(12) . 8_566 ?
O1 Cu1 N1 89.36(12) 7_566 8_566 ?
O1 Cu1 N1 89.36(12) . 2 ?
O1 Cu1 N1 90.64(12) 7_566 2 ?
N1 Cu1 N1 180 8_566 2 ?
C14 O1 Cu1 108.0(2) . . ?
C5 N1 C1 118.1(4) . . ?
C5 N1 Cu1 119.5(3) . 2 ?
C1 N1 Cu1 122.4(3) . 2 ?
C6 N2 N3 121.0(3) . . ?
N2 N3 C8 118.3(3) . . ?
C15 N4 C16 121(2) . . ?
C15 N4 C17 119.6(8) . . ?
C16 N4 C17 118(2) . . ?
N1 C1 C2 121.7(4) . . ?
C1 C2 C3 119.3(4) . . ?
C2 C3 C4 120.2(4) . . ?
C3 C4 C5 116.4(4) . . ?
C3 C4 C6 124.0(4) . . ?
C5 C4 C6 119.7(4) . . ?
N1 C5 C4 124.4(4) . . ?
N2 C6 C4 114.4(4) . . ?
N2 C6 C7 126.2(4) . . ?
C4 C6 C7 119.3(4) . . ?
C9 C8 C13 119.1(4) . . ?
C9 C8 N3 121.9(4) . . ?
C13 C8 N3 119.0(4) . . ?
C10 C9 C8 119.8(4) . . ?
C9 C10 C11 121.7(4) . . ?
C10 C11 C12 118.1(4) . . ?
C10 C11 C14 121.4(4) . . ?
C12 C11 C14 120.5(4) . . ?
C13 C12 C11 120.6(4) . . ?
C12 C13 C8 120.5(4) . . ?
O2 C14 O1 122.7(4) . . ?
O2 C14 C11 120.5(4) . . ?
O1 C14 C11 116.9(4) . . ?
O3 C15 N4 130.2(17) . . ?

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
N3 H3N O2 0.8800(10) 2.151(7) 3.023(4) 171(3) 4_545

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.087



####################################################################### 
# 
# 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_1ZnH2O
_database_code_depnum_ccdc_archive 'CCDC 1477016'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_1ZnH2O              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.936 Note  
RESPONSE: Good quality single crystal could not be reobtained.
Synchrotron data with restricted rotation angle.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 N6 O4 Zn, H2 O'
_chemical_formula_sum            'C28 H26 N6 O5 Zn'
_chemical_formula_weight         591.92

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 0.0060 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'
Zn Zn 0.2910 1.4440 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.9650(16)
_cell_length_b                   8.0400(16)
_cell_length_c                   20.311(4)
_cell_angle_alpha                81.56(3)
_cell_angle_beta                 85.94(3)
_cell_angle_gamma                86.61(3)
_cell_volume                     1281.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    22507
_cell_measurement_theta_min      2.032
_cell_measurement_theta_max      28.683

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.011
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.970
_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     0.7109
_diffrn_radiation_type           synchrotron
_diffrn_source                   'MX1 Beamline, Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22507
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.032
_diffrn_reflns_theta_max         28.683
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             5833
_reflns_number_gt                4147
_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       'BluICE (McPhillips et al, 2001)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0629P)²+1.7427P] 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         5833
_refine_ls_number_parameters     375
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.042
_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
Zn1 Zn 0.77670(6) 0.77597(6) 0.75203(2) 0.02690(14) Uani 1 1 d . . . . .
O1 O 1.0185(3) 0.3025(3) 0.29425(13) 0.0311(6) Uani 1 1 d . . . . .
O2 O 1.1887(4) 0.4552(4) 0.34019(15) 0.0347(6) Uani 1 1 d . . . . .
O3 O 1.1704(4) 1.0075(4) 1.22062(15) 0.0361(7) Uani 1 1 d . . . . .
O4 O 1.0305(4) 1.1787(4) 1.14411(15) 0.0372(7) Uani 1 1 d . . . . .
O5 O 0.7862(4) 0.2039(4) 0.64730(16) 0.0436(8) Uani 1 1 d D . . . .
H1O H 0.806(7) 0.3056(19) 0.647(3) 0.065 Uiso 1 1 d D U . . .
H2O H 0.804(7) 0.151(5) 0.6851(11) 0.065 Uiso 1 1 d D U . . .
N1 N 0.5644(4) 0.8643(4) 0.70284(16) 0.0286(7) Uani 1 1 d . . . . .
N2 N 0.4868(4) 0.7718(4) 0.51667(15) 0.0268(7) Uani 1 1 d . . . . .
N3 N 0.4746(4) 0.7245(4) 0.45607(16) 0.0295(7) Uani 1 1 d D . . . .
H3N H 0.389(3) 0.746(6) 0.4303(15) 0.044 Uiso 1 1 d D U . . .
N4 N 0.6697(4) 0.5864(4) 0.81810(16) 0.0292(7) Uani 1 1 d . . . . .
N5 N 0.7680(4) 0.4931(4) 1.01414(15) 0.0267(7) Uani 1 1 d . . . . .
N6 N 0.8202(4) 0.4733(4) 1.07712(16) 0.0283(7) Uani 1 1 d D . . . .
H6N H 0.842(6) 0.371(2) 1.0972(19) 0.042 Uiso 1 1 d D U . . .
C1 C 0.4463(5) 0.9508(5) 0.7367(2) 0.0348(9) Uani 1 1 d . . . . .
H1 H 0.4677 0.9724 0.7800 0.042 Uiso 1 1 calc R U . . .
C1A C 1.0737(5) 1.0349(5) 1.17124(19) 0.0306(8) Uani 1 1 d . . . . .
C2 C 0.2955(5) 1.0090(5) 0.7104(2) 0.0350(9) Uani 1 1 d . . . . .
H2 H 0.2144 1.0699 0.7354 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2630(5) 0.9781(5) 0.6471(2) 0.0315(8) Uani 1 1 d . . . . .
H3 H 0.1589 1.0164 0.6287 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3837(5) 0.8909(5) 0.61104(19) 0.0269(8) Uani 1 1 d . . . . .
C5 C 0.5338(5) 0.8372(5) 0.64180(19) 0.0284(8) Uani 1 1 d . . . . .
H4 H 0.6183 0.7782 0.6177 0.034 Uiso 1 1 calc R U . . .
C6 C 0.3597(5) 0.8508(5) 0.5435(2) 0.0289(8) Uani 1 1 d . . . . .
C7 C 0.1969(5) 0.8993(6) 0.5119(2) 0.0373(10) Uani 1 1 d . . . . .
H7B H 0.1937 1.0195 0.4942 0.056 Uiso 1 1 calc R U . . .
H7A H 0.1030 0.8765 0.5453 0.056 Uiso 1 1 calc R U . . .
H7C H 0.1871 0.8335 0.4755 0.056 Uiso 1 1 calc R U . . .
C8 C 0.6147(5) 0.6445(5) 0.42744(19) 0.0262(8) Uani 1 1 d . . . . .
C9 C 0.5980(5) 0.5791(5) 0.36848(19) 0.0298(8) Uani 1 1 d . . . . .
H9 H 0.4923 0.5882 0.3490 0.036 Uiso 1 1 calc R U . . .
C10 C 0.7358(5) 0.5011(5) 0.33859(19) 0.0286(8) Uani 1 1 d . . . . .
H10 H 0.7229 0.4537 0.2992 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8927(5) 0.4904(5) 0.36486(19) 0.0282(8) Uani 1 1 d . . . . .
C12 C 0.9083(5) 0.5575(5) 0.42323(19) 0.0308(8) Uani 1 1 d . . . . .
H12 H 1.0154 0.5527 0.4414 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7709(5) 0.6312(5) 0.45538(19) 0.0301(8) Uani 1 1 d . . . . .
H13 H 0.7828 0.6724 0.4962 0.036 Uiso 1 1 calc R U . . .
C14 C 1.0433(5) 0.4118(5) 0.33203(19) 0.0293(8) Uani 1 1 d . . . . .
C15 C 0.5731(5) 0.4825(5) 0.7927(2) 0.0307(8) Uani 1 1 d . . . . .
H15 H 0.5474 0.5089 0.7472 0.037 Uiso 1 1 calc R U . . .
C16 C 0.5103(5) 0.3406(6) 0.8295(2) 0.0358(9) Uani 1 1 d . . . . .
H16 H 0.4443 0.2688 0.8098 0.043 Uiso 1 1 calc R U . . .
C17 C 0.5455(5) 0.3036(5) 0.8966(2) 0.0318(8) Uani 1 1 d . . . . .
H17 H 0.5019 0.2067 0.9233 0.038 Uiso 1 1 calc R U . . .
C18 C 0.6442(5) 0.4085(5) 0.92438(19) 0.0275(8) Uani 1 1 d . . . . .
C19 C 0.7044(5) 0.5490(5) 0.88236(19) 0.0287(8) Uani 1 1 d . . . . .
H19 H 0.7735 0.6215 0.9003 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6897(5) 0.3745(5) 0.99461(19) 0.0280(8) Uani 1 1 d . . . . .
C21 C 0.6372(6) 0.2150(5) 1.0366(2) 0.0366(9) Uani 1 1 d . . . . .
H21A H 0.6759 0.2105 1.0816 0.055 Uiso 1 1 calc R U . . .
H21B H 0.6871 0.1183 1.0166 0.055 Uiso 1 1 calc R U . . .
H21C H 0.5141 0.2117 1.0391 0.055 Uiso 1 1 calc R U . . .
C22 C 0.8879(5) 0.6104(5) 1.09840(19) 0.0258(7) Uani 1 1 d . . . . .
C23 C 0.9420(5) 0.5920(5) 1.16324(19) 0.0273(8) Uani 1 1 d . . . . .
H23 H 0.9339 0.4867 1.1912 0.033 Uiso 1 1 calc R U . . .
C24 C 1.0069(5) 0.7253(5) 1.18685(19) 0.0286(8) Uani 1 1 d . . . . .
H24 H 1.0478 0.7099 1.2303 0.034 Uiso 1 1 calc R U . . .
C25 C 1.0132(5) 0.8839(5) 1.14731(19) 0.0276(8) Uani 1 1 d . . . . .
C26 C 0.9570(5) 0.9001(5) 1.0836(2) 0.0313(8) Uani 1 1 d . . . . .
H26 H 0.9606 1.0066 1.0563 0.038 Uiso 1 1 calc R U . . .
C27 C 0.8957(5) 0.7664(5) 1.05832(19) 0.0286(8) Uani 1 1 d . . . . .
H27 H 0.8595 0.7809 1.0142 0.034 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
Zn1 O1 1.944(3) 2_766 ?
Zn1 O3 1.980(3) 2_777 ?
Zn1 N4 2.059(4) . ?
Zn1 N1 2.062(3) . ?
O1 C14 1.281(5) . ?
O1 Zn1 1.944(3) 2_766 ?
O2 C14 1.258(5) . ?
O3 C1A 1.293(5) . ?
O3 Zn1 1.980(3) 2_777 ?
O4 C1A 1.245(5) . ?
O5 H1O 0.8400(11) . ?
O5 H2O 0.8400(11) . ?
N1 C5 1.331(5) . ?
N1 C1 1.347(5) . ?
N2 C6 1.293(5) . ?
N2 N3 1.352(4) . ?
N3 C8 1.389(5) . ?
N3 H3N 0.8800(11) . ?
N4 C19 1.340(5) . ?
N4 C15 1.347(5) . ?
N5 C20 1.293(5) . ?
N5 N6 1.357(4) . ?
N6 C22 1.391(5) . ?
N6 H6N 0.8800(11) . ?
C1 C2 1.378(6) . ?
C1 H1 0.9500 . ?
C1A C25 1.490(5) . ?
C2 C3 1.390(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(5) . ?
C4 C6 1.482(5) . ?
C5 H4 0.9500 . ?
C6 C7 1.493(5) . ?
C7 H7B 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.394(5) . ?
C8 C13 1.396(5) . ?
C9 C10 1.379(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(5) . ?
C11 C14 1.485(5) . ?
C12 C13 1.382(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 C16 1.369(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.399(6) . ?
C18 C20 1.479(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.496(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.394(5) . ?
C22 C23 1.399(5) . ?
C23 C24 1.378(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.405(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(5) . ?
C26 C27 1.385(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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 Zn1 O3 105.63(13) 2_766 2_777 ?
O1 Zn1 N4 112.13(13) 2_766 . ?
O3 Zn1 N4 122.10(13) 2_777 . ?
O1 Zn1 N1 122.35(13) 2_766 . ?
O3 Zn1 N1 96.76(13) 2_777 . ?
N4 Zn1 N1 98.15(13) . . ?
C14 O1 Zn1 113.5(3) . 2_766 ?
C1A O3 Zn1 109.9(3) . 2_777 ?
H1O O5 H2O 109(5) . . ?
C5 N1 C1 118.3(3) . . ?
C5 N1 Zn1 125.0(3) . . ?
C1 N1 Zn1 116.6(3) . . ?
C6 N2 N3 119.3(3) . . ?
N2 N3 C8 118.1(3) . . ?
N2 N3 H3N 127(3) . . ?
C8 N3 H3N 114(3) . . ?
C19 N4 C15 118.2(4) . . ?
C19 N4 Zn1 124.4(3) . . ?
C15 N4 Zn1 116.9(3) . . ?
C20 N5 N6 119.7(3) . . ?
N5 N6 C22 117.9(3) . . ?
N5 N6 H6N 118(3) . . ?
C22 N6 H6N 120(3) . . ?
N1 C1 C2 122.0(4) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
O4 C1A O3 123.2(4) . . ?
O4 C1A C25 120.1(4) . . ?
O3 C1A C25 116.6(3) . . ?
C1 C2 C3 119.5(4) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 116.9(4) . . ?
C3 C4 C6 123.4(3) . . ?
C5 C4 C6 119.7(3) . . ?
N1 C5 C4 123.7(4) . . ?
N1 C5 H4 118.1 . . ?
C4 C5 H4 118.1 . . ?
N2 C6 C4 115.0(3) . . ?
N2 C6 C7 124.9(4) . . ?
C4 C6 C7 120.1(3) . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
N3 C8 C9 118.5(3) . . ?
N3 C8 C13 121.8(3) . . ?
C9 C8 C13 119.6(3) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 121.4(4) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 118.5(4) . . ?
C10 C11 C14 122.0(3) . . ?
C12 C11 C14 119.5(3) . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C8 119.5(4) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
O2 C14 O1 121.9(4) . . ?
O2 C14 C11 120.6(4) . . ?
O1 C14 C11 117.5(3) . . ?
N4 C15 C16 122.9(4) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C17 118.5(4) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 117.1(4) . . ?
C17 C18 C20 122.7(4) . . ?
C19 C18 C20 120.1(3) . . ?
N4 C19 C18 123.3(4) . . ?
N4 C19 H19 118.4 . . ?
C18 C19 H19 118.4 . . ?
N5 C20 C18 114.7(3) . . ?
N5 C20 C21 126.3(4) . . ?
C18 C20 C21 119.0(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C22 C27 122.0(3) . . ?
N6 C22 C23 118.5(3) . . ?
C27 C22 C23 119.4(3) . . ?
C24 C23 C22 120.5(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 118.0(4) . . ?
C26 C25 C1A 118.9(4) . . ?
C24 C25 C1A 123.1(3) . . ?
C25 C26 C27 122.3(4) . . ?
C25 C26 H26 118.9 . . ?
C27 C26 H26 118.9 . . ?
C26 C27 C22 119.2(4) . . ?
C26 C27 H27 120.4 . . ?
C22 C27 H27 120.4 . . ?

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
C6 N2 N3 C8 178.0(3) . . . . ?
C20 N5 N6 C22 -173.4(3) . . . . ?
C5 N1 C1 C2 1.0(6) . . . . ?
Zn1 N1 C1 C2 -176.8(3) . . . . ?
Zn1 O3 C1A O4 3.4(5) 2_777 . . . ?
Zn1 O3 C1A C25 -176.3(3) 2_777 . . . ?
N1 C1 C2 C3 0.1(7) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C2 C3 C4 C6 179.5(4) . . . . ?
C1 N1 C5 C4 -1.3(6) . . . . ?
Zn1 N1 C5 C4 176.2(3) . . . . ?
C3 C4 C5 N1 0.6(6) . . . . ?
C6 C4 C5 N1 -178.5(4) . . . . ?
N3 N2 C6 C4 177.7(3) . . . . ?
N3 N2 C6 C7 -1.4(6) . . . . ?
C3 C4 C6 N2 178.6(4) . . . . ?
C5 C4 C6 N2 -2.4(5) . . . . ?
C3 C4 C6 C7 -2.3(6) . . . . ?
C5 C4 C6 C7 176.7(4) . . . . ?
N2 N3 C8 C9 173.2(3) . . . . ?
N2 N3 C8 C13 -8.1(5) . . . . ?
N3 C8 C9 C10 179.2(4) . . . . ?
C13 C8 C9 C10 0.4(6) . . . . ?
C8 C9 C10 C11 -1.9(6) . . . . ?
C9 C10 C11 C12 1.3(6) . . . . ?
C9 C10 C11 C14 -178.0(4) . . . . ?
C10 C11 C12 C13 1.0(6) . . . . ?
C14 C11 C12 C13 -179.8(4) . . . . ?
C11 C12 C13 C8 -2.5(6) . . . . ?
N3 C8 C13 C12 -176.9(4) . . . . ?
C9 C8 C13 C12 1.8(6) . . . . ?
Zn1 O1 C14 O2 -3.6(5) 2_766 . . . ?
Zn1 O1 C14 C11 174.7(3) 2_766 . . . ?
C10 C11 C14 O2 153.5(4) . . . . ?
C12 C11 C14 O2 -25.7(6) . . . . ?
C10 C11 C14 O1 -24.8(6) . . . . ?
C12 C11 C14 O1 155.9(4) . . . . ?
C19 N4 C15 C16 -0.4(6) . . . . ?
Zn1 N4 C15 C16 172.4(3) . . . . ?
N4 C15 C16 C17 1.2(6) . . . . ?
C15 C16 C17 C18 -0.9(6) . . . . ?
C16 C17 C18 C19 0.0(6) . . . . ?
C16 C17 C18 C20 -178.4(4) . . . . ?
C15 N4 C19 C18 -0.6(6) . . . . ?
Zn1 N4 C19 C18 -172.8(3) . . . . ?
C17 C18 C19 N4 0.8(6) . . . . ?
C20 C18 C19 N4 179.3(3) . . . . ?
N6 N5 C20 C18 -178.1(3) . . . . ?
N6 N5 C20 C21 4.6(6) . . . . ?
C17 C18 C20 N5 -173.4(4) . . . . ?
C19 C18 C20 N5 8.2(5) . . . . ?
C17 C18 C20 C21 4.1(6) . . . . ?
C19 C18 C20 C21 -174.3(4) . . . . ?
N5 N6 C22 C27 3.0(6) . . . . ?
N5 N6 C22 C23 179.9(3) . . . . ?
N6 C22 C23 C24 -178.8(3) . . . . ?
C27 C22 C23 C24 -1.8(6) . . . . ?
C22 C23 C24 C25 2.7(6) . . . . ?
C23 C24 C25 C26 -1.9(6) . . . . ?
C23 C24 C25 C1A 176.8(4) . . . . ?
O4 C1A C25 C26 20.7(6) . . . . ?
O3 C1A C25 C26 -159.6(4) . . . . ?
O4 C1A C25 C24 -157.9(4) . . . . ?
O3 C1A C25 C24 21.8(6) . . . . ?
C24 C25 C26 C27 0.0(6) . . . . ?
C1A C25 C26 C27 -178.7(4) . . . . ?
C25 C26 C27 C22 0.9(7) . . . . ?
N6 C22 C27 C26 176.9(4) . . . . ?
C23 C22 C27 C26 0.0(6) . . . . ?

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
O5 H1O O2 0.8400(11) 1.983(13) 2.810(4) 168(6) 2_766
O5 H2O O3 0.8400(11) 2.153(8) 2.988(5) 173(5) 2_767
N6 H6N O4 0.8800(11) 2.24(2) 3.029(4) 149(4) 1_545
N3 H3N O5 0.8800(11) 2.159(8) 3.029(5) 170(3) 2_666

_refine_diff_density_max         0.946
_refine_diff_density_min         -1.093
_refine_diff_density_rms         0.100



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DMF:H2O
####################################################################### 
# 
# 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_3Zn
_database_code_depnum_ccdc_archive 'CCDC 1477017'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 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         'C28 H24 N6 O4 Zn, 1.5H2 O'
_chemical_formula_sum            'C28 H27 N6 O5.50 Zn'
_chemical_formula_weight         600.92

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'
Zn Zn 0.2910 1.4260 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_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'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   12.3440(17)
_cell_length_b                   12.3440(17)
_cell_length_c                   17.575(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2678.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    51837
_cell_measurement_theta_min      2.016
_cell_measurement_theta_max      30.047

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             1244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.970
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.981
_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     0.7108
_diffrn_radiation_type           synchrotron
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 315r'
_diffrn_measurement_method       'Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51837
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         30.047
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3833
_reflns_number_gt                3817
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.978

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'BluIce (McPhillips et al., 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1583 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3833
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.183 0.817 0.250 69 14 ' '
2 0.317 0.317 0.000 68 14 ' '
3 0.683 0.683 0.500 69 15 ' '
4 0.817 0.183 0.750 69 14 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
Electron count equates to 1.5 water per formula unit.
SQUEEZED solvent included in UNIT instruction.
2.5 H2O per formula unit found by microanalysis.
;

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
Zn1 Zn 0.51810(2) 0.48190(2) 0.7500 0.02648(14) Uani 1 2 d S T P . .
O1 O 0.47223(16) 0.50295(14) 0.63616(12) 0.0365(4) Uani 1 1 d . . . . .
O2 O 0.49077(16) 0.65046(14) 0.70459(10) 0.0334(3) Uani 1 1 d . . . . .
N1 N 0.50115(15) 1.31523(14) 0.74484(10) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.38553(14) 1.00375(14) 0.60682(10) 0.0248(3) Uani 1 1 d . . . . .
N3 N 0.33931(16) 0.95589(15) 0.54535(10) 0.0277(3) Uani 1 1 d . . . . .
H3N H 0.3059 0.9948 0.5106 0.033 Uiso 1 1 calc R U . . .
C1 C 0.45382(17) 1.26862(18) 0.68375(11) 0.0259(4) Uani 1 1 d . . . . .
H1 H 0.4309 1.3138 0.6430 0.031 Uiso 1 1 calc R U . . .
C2 C 0.43701(17) 1.15691(17) 0.67768(11) 0.0259(4) Uani 1 1 d . . . . .
C3 C 0.4723(2) 1.09319(19) 0.73908(14) 0.0356(5) Uani 1 1 d . . . . .
H3 H 0.4647 1.0167 0.7371 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5181(3) 1.1415(2) 0.80227(15) 0.0418(6) Uani 1 1 d . . . . .
H4 H 0.5408 1.0990 0.8444 0.050 Uiso 1 1 calc R U . . .
C5 C 0.5301(2) 1.2531(2) 0.80306(14) 0.0378(5) Uani 1 1 d . . . . .
H5 H 0.5603 1.2865 0.8469 0.045 Uiso 1 1 calc R U . . .
C6 C 0.38267(16) 1.10877(16) 0.61128(12) 0.0244(3) Uani 1 1 d . . . . .
C7 C 0.3298(2) 1.17931(19) 0.55266(13) 0.0323(4) Uani 1 1 d . . . . .
H7A H 0.3041 1.2461 0.5767 0.048 Uiso 1 1 calc R U . . .
H7B H 0.2683 1.1407 0.5301 0.048 Uiso 1 1 calc R U . . .
H7C H 0.3824 1.1972 0.5128 0.048 Uiso 1 1 calc R U . . .
C8 C 0.34595(17) 0.84399(17) 0.53860(10) 0.0256(4) Uani 1 1 d . . . . .
C9 C 0.40211(18) 0.78155(17) 0.59146(11) 0.0265(4) Uani 1 1 d . . . . .
H9 H 0.4369 0.8154 0.6334 0.032 Uiso 1 1 calc R U . . .
C10 C 0.40736(18) 0.66917(18) 0.58290(12) 0.0279(4) Uani 1 1 d . . . . .
C11 C 0.3588(2) 0.61798(18) 0.52039(12) 0.0322(4) Uani 1 1 d . . . . .
H11 H 0.3640 0.5417 0.5140 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3026(2) 0.6815(2) 0.46773(13) 0.0332(4) Uani 1 1 d . . . . .
H12 H 0.2682 0.6478 0.4256 0.040 Uiso 1 1 calc R U . . .
C13 C 0.29637(19) 0.79324(19) 0.47608(12) 0.0299(4) Uani 1 1 d . . . . .
H13 H 0.2585 0.8354 0.4395 0.036 Uiso 1 1 calc R U . . .
C14 C 0.46107(18) 0.60436(18) 0.64433(13) 0.0293(4) Uani 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
Zn1 N1 2.0699(18) 8_766 ?
Zn1 N1 2.0699(18) 1_545 ?
Zn1 O1 2.095(2) 8_666 ?
Zn1 O1 2.096(2) . ?
Zn1 O2 2.2539(17) . ?
Zn1 O2 2.2539(17) 8_666 ?
Zn1 C14 2.496(2) . ?
Zn1 C14 2.496(2) 8_666 ?
O1 C14 1.268(3) . ?
O2 C14 1.257(3) . ?
N1 C5 1.328(3) . ?
N1 C1 1.351(3) . ?
N1 Zn1 2.0699(18) 1_565 ?
N2 C6 1.299(2) . ?
N2 N3 1.357(2) . ?
N3 C8 1.389(3) . ?
C1 C2 1.399(3) . ?
C2 C3 1.405(3) . ?
C2 C6 1.471(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.386(3) . ?
C6 C7 1.499(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.405(3) . ?
C9 C10 1.397(3) . ?
C10 C11 1.402(3) . ?
C10 C14 1.498(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.389(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
N1 Zn1 N1 101.71(11) 8_766 1_545 ?
N1 Zn1 O1 93.11(7) 8_766 8_666 ?
N1 Zn1 O1 107.33(7) 1_545 8_666 ?
N1 Zn1 O1 107.33(7) 8_766 . ?
N1 Zn1 O1 93.10(7) 1_545 . ?
O1 Zn1 O1 147.63(10) 8_666 . ?
N1 Zn1 O2 94.07(7) 8_766 . ?
N1 Zn1 O2 152.49(7) 1_545 . ?
O1 Zn1 O2 94.02(7) 8_666 . ?
O1 Zn1 O2 60.46(6) . . ?
N1 Zn1 O2 152.49(7) 8_766 8_666 ?
N1 Zn1 O2 94.07(7) 1_545 8_666 ?
O1 Zn1 O2 60.46(6) 8_666 8_666 ?
O1 Zn1 O2 94.02(7) . 8_666 ?
O2 Zn1 O2 81.32(10) . 8_666 ?
N1 Zn1 C14 104.58(8) 8_766 . ?
N1 Zn1 C14 122.74(7) 1_545 . ?
O1 Zn1 C14 120.78(8) 8_666 . ?
O1 Zn1 C14 30.49(7) . . ?
O2 Zn1 C14 30.14(7) . . ?
O2 Zn1 C14 84.97(7) 8_666 . ?
N1 Zn1 C14 122.75(7) 8_766 8_666 ?
N1 Zn1 C14 104.58(8) 1_545 8_666 ?
O1 Zn1 C14 30.49(7) 8_666 8_666 ?
O1 Zn1 C14 120.78(8) . 8_666 ?
O2 Zn1 C14 84.97(7) . 8_666 ?
O2 Zn1 C14 30.14(7) 8_666 8_666 ?
C14 Zn1 C14 102.23(10) . 8_666 ?
C14 O1 Zn1 92.50(15) . . ?
C14 O2 Zn1 85.65(13) . . ?
C5 N1 C1 118.89(19) . . ?
C5 N1 Zn1 120.86(15) . 1_565 ?
C1 N1 Zn1 120.12(14) . 1_565 ?
C6 N2 N3 118.10(18) . . ?
N2 N3 C8 118.44(17) . . ?
N1 C1 C2 123.00(19) . . ?
C1 C2 C3 116.58(19) . . ?
C1 C2 C6 121.76(18) . . ?
C3 C2 C6 121.64(19) . . ?
C4 C3 C2 120.2(2) . . ?
C3 C4 C5 118.8(2) . . ?
N1 C5 C4 122.5(2) . . ?
N2 C6 C2 116.00(18) . . ?
N2 C6 C7 123.4(2) . . ?
C2 C6 C7 120.61(18) . . ?
N3 C8 C9 121.54(18) . . ?
N3 C8 C13 118.98(18) . . ?
C9 C8 C13 119.47(19) . . ?
C8 C9 C10 120.07(19) . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 C14 118.24(19) . . ?
C11 C10 C14 120.9(2) . . ?
C12 C11 C10 118.6(2) . . ?
C13 C12 C11 121.0(2) . . ?
C12 C13 C8 120.1(2) . . ?
O2 C14 O1 120.7(2) . . ?
O2 C14 C10 119.6(2) . . ?
O1 C14 C10 119.6(2) . . ?
O2 C14 Zn1 64.21(12) . . ?
O1 C14 Zn1 57.01(13) . . ?
C10 C14 Zn1 169.83(16) . . ?

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
N3 H3N O2 0.88 2.16 2.900(3) 140.9 4_464

_refine_diff_density_max         0.493
_refine_diff_density_min         -1.434
_refine_diff_density_rms         0.065



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DMF:H2O
####################################################################### 
# 
# 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_3Cd
_database_code_depnum_ccdc_archive 'CCDC 1477018'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 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         'C28 H24 Cd N6 O4, 1.5(H2 O)'
_chemical_formula_sum            'C28 H27 Cd N6 O5.50'
_chemical_formula_weight         647.95

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'
Cd Cd -0.7840 1.1970 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_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'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   12.4690(18)
_cell_length_b                   12.4690(18)
_cell_length_c                   17.439(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2711.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    54034
_cell_measurement_theta_min      2.008
_cell_measurement_theta_max      30.056

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             1316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.858
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.983
_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     0.7108
_diffrn_radiation_type           synchrotron
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 315r'
_diffrn_measurement_method       'Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54034
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.008
_diffrn_reflns_theta_max         30.056
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3908
_reflns_number_gt                3877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.994

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'BluIce (McPhillips et al., 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²+2.9093P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3908
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.163 0.837 0.250 69 16 ' '
2 0.337 0.337 0.000 68 16 ' '
3 0.663 0.663 0.500 69 16 ' '
4 0.837 0.163 0.750 69 16 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
Electron count calculates for 1.5 H2O per formula unit.
Solvent included in UNIT instruction.
Micro analysis shows 0.4 H2O per formula unit.
;

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
Cd1 Cd 0.51521(2) 0.48479(2) 0.7500 0.01846(7) Uani 1 2 d S T P . .
O1 O 0.4431(2) 0.50011(16) 0.62483(13) 0.0308(5) Uani 1 1 d . . . . .
O2 O 0.4821(2) 0.64713(17) 0.68945(13) 0.0267(4) Uani 1 1 d . . . . .
N1 N 0.5039(2) 1.30305(18) 0.73839(15) 0.0221(5) Uani 1 1 d . . . . .
N2 N 0.38042(18) 0.99951(19) 0.59786(13) 0.0185(5) Uani 1 1 d . . . . .
N3 N 0.3306(2) 0.9543(2) 0.53633(15) 0.0209(5) Uani 1 1 d . . . . .
H3N H 0.2981 0.9945 0.5020 0.025 Uiso 1 1 calc R U . . .
C1 C 0.4526(2) 1.2592(2) 0.67854(17) 0.0203(5) Uani 1 1 d . . . . .
H1 H 0.4237 1.3055 0.6405 0.024 Uiso 1 1 calc R U . . .
C2 C 0.4397(2) 1.1491(2) 0.66942(17) 0.0198(5) Uani 1 1 d . . . . .
C3 C 0.4823(3) 1.0830(2) 0.72679(18) 0.0284(6) Uani 1 1 d . . . . .
H3 H 0.4765 1.0072 0.7227 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5329(4) 1.1288(3) 0.7894(2) 0.0353(9) Uani 1 1 d . . . . .
H4 H 0.5610 1.0849 0.8291 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5420(3) 1.2386(3) 0.7934(2) 0.0306(7) Uani 1 1 d . . . . .
H5 H 0.5765 1.2696 0.8366 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3817(2) 1.1031(2) 0.60279(17) 0.0193(5) Uani 1 1 d . . . . .
C7 C 0.3305(3) 1.1751(3) 0.54494(19) 0.0247(6) Uani 1 1 d . . . . .
H7A H 0.3245 1.2477 0.5661 0.037 Uiso 1 1 calc R U . . .
H7B H 0.2588 1.1480 0.5324 0.037 Uiso 1 1 calc R U . . .
H7C H 0.3745 1.1769 0.4984 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3320(2) 0.8433(2) 0.52888(17) 0.0191(5) Uani 1 1 d . . . . .
C9 C 0.3865(2) 0.7784(2) 0.58118(17) 0.0194(5) Uani 1 1 d . . . . .
H9 H 0.4235 0.8099 0.6231 0.023 Uiso 1 1 calc R U . . .
C10 C 0.3868(2) 0.6676(2) 0.57191(17) 0.0207(5) Uani 1 1 d . . . . .
C11 C 0.3351(3) 0.6199(2) 0.50961(18) 0.0242(6) Uani 1 1 d . . . . .
H11 H 0.3370 0.5444 0.5026 0.029 Uiso 1 1 calc R U . . .
C12 C 0.2806(3) 0.6857(3) 0.45777(17) 0.0249(6) Uani 1 1 d . . . . .
H12 H 0.2443 0.6542 0.4155 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2784(2) 0.7960(3) 0.46682(17) 0.0217(6) Uani 1 1 d . . . . .
H13 H 0.2407 0.8395 0.4311 0.026 Uiso 1 1 calc R U . . .
C14 C 0.4413(2) 0.6004(2) 0.63137(17) 0.0207(5) Uani 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
Cd1 N1 2.280(2) 1_545 ?
Cd1 N1 2.280(2) 8_766 ?
Cd1 O2 2.320(2) . ?
Cd1 O2 2.320(2) 8_666 ?
Cd1 O1 2.369(2) . ?
Cd1 O1 2.369(2) 8_666 ?
Cd1 C14 2.685(3) 8_666 ?
Cd1 C14 2.685(3) . ?
O1 C14 1.256(3) . ?
O2 C14 1.274(4) . ?
N1 C5 1.339(4) . ?
N1 C1 1.341(4) . ?
N1 Cd1 2.280(2) 1_565 ?
N2 C6 1.295(4) . ?
N2 N3 1.362(3) . ?
N3 C8 1.389(4) . ?
N3 H3N 0.8800 . ?
C1 C2 1.391(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.402(4) . ?
C2 C6 1.484(4) . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.493(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.397(4) . ?
C8 C13 1.403(4) . ?
C9 C10 1.390(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(4) . ?
C10 C14 1.496(4) . ?
C11 C12 1.397(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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 Cd1 N1 97.50(12) 1_545 8_766 ?
N1 Cd1 O2 144.68(8) 1_545 . ?
N1 Cd1 O2 99.41(9) 8_766 . ?
N1 Cd1 O2 99.41(9) 1_545 8_666 ?
N1 Cd1 O2 144.68(8) 8_766 8_666 ?
O2 Cd1 O2 84.06(14) . 8_666 ?
N1 Cd1 O1 88.56(8) 1_545 . ?
N1 Cd1 O1 117.02(9) 8_766 . ?
O2 Cd1 O1 56.12(7) . . ?
O2 Cd1 O1 94.24(9) 8_666 . ?
N1 Cd1 O1 117.02(9) 1_545 8_666 ?
N1 Cd1 O1 88.56(8) 8_766 8_666 ?
O2 Cd1 O1 94.24(9) . 8_666 ?
O2 Cd1 O1 56.12(7) 8_666 8_666 ?
O1 Cd1 O1 142.01(11) . 8_666 ?
N1 Cd1 C14 112.13(9) 1_545 8_666 ?
N1 Cd1 C14 116.38(9) 8_766 8_666 ?
O2 Cd1 C14 87.45(9) . 8_666 ?
O2 Cd1 C14 28.31(8) 8_666 8_666 ?
O1 Cd1 C14 118.59(9) . 8_666 ?
O1 Cd1 C14 27.90(8) 8_666 8_666 ?
N1 Cd1 C14 116.38(9) 1_545 . ?
N1 Cd1 C14 112.13(9) 8_766 . ?
O2 Cd1 C14 28.32(8) . . ?
O2 Cd1 C14 87.45(9) 8_666 . ?
O1 Cd1 C14 27.90(8) . . ?
O1 Cd1 C14 118.59(9) 8_666 . ?
C14 Cd1 C14 102.99(12) 8_666 . ?
C14 O1 Cd1 90.20(18) . . ?
C14 O2 Cd1 91.96(17) . . ?
C5 N1 C1 118.8(3) . . ?
C5 N1 Cd1 120.8(2) . 1_565 ?
C1 N1 Cd1 120.28(19) . 1_565 ?
C6 N2 N3 118.1(2) . . ?
N2 N3 C8 118.7(3) . . ?
N2 N3 H3N 120.7 . . ?
C8 N3 H3N 120.7 . . ?
N1 C1 C2 123.2(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 117.1(3) . . ?
C1 C2 C6 121.8(3) . . ?
C3 C2 C6 121.1(3) . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
N2 C6 C2 116.3(3) . . ?
N2 C6 C7 123.3(3) . . ?
C2 C6 C7 120.3(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 121.5(3) . . ?
N3 C8 C13 119.0(3) . . ?
C9 C8 C13 119.5(3) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.8(3) . . ?
C9 C10 C14 118.4(3) . . ?
C11 C10 C14 120.7(3) . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C8 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
O1 C14 O2 121.3(3) . . ?
O1 C14 C10 120.2(3) . . ?
O2 C14 C10 118.5(3) . . ?
O1 C14 Cd1 61.90(15) . . ?
O2 C14 Cd1 59.72(15) . . ?
C10 C14 Cd1 172.1(2) . . ?

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
C6 N2 N3 C8 177.7(3) . . . . ?
C5 N1 C1 C2 -2.0(5) . . . . ?
Cd1 N1 C1 C2 -177.7(2) 1_565 . . . ?
N1 C1 C2 C3 0.6(5) . . . . ?
N1 C1 C2 C6 179.5(3) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C6 C2 C3 C4 -177.9(4) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C1 N1 C5 C4 1.9(6) . . . . ?
Cd1 N1 C5 C4 177.6(3) 1_565 . . . ?
C3 C4 C5 N1 -0.4(7) . . . . ?
N3 N2 C6 C2 -178.2(2) . . . . ?
N3 N2 C6 C7 0.6(4) . . . . ?
C1 C2 C6 N2 175.8(3) . . . . ?
C3 C2 C6 N2 -5.3(5) . . . . ?
C1 C2 C6 C7 -3.0(5) . . . . ?
C3 C2 C6 C7 175.9(3) . . . . ?
N2 N3 C8 C9 -2.4(4) . . . . ?
N2 N3 C8 C13 178.3(3) . . . . ?
N3 C8 C9 C10 -179.8(3) . . . . ?
C13 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 C11 1.6(5) . . . . ?
C8 C9 C10 C14 -176.9(3) . . . . ?
C9 C10 C11 C12 -1.7(5) . . . . ?
C14 C10 C11 C12 176.7(3) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C11 C12 C13 C8 0.2(5) . . . . ?
N3 C8 C13 C12 178.9(3) . . . . ?
C9 C8 C13 C12 -0.4(5) . . . . ?
Cd1 O1 C14 O2 6.3(3) . . . . ?
Cd1 O1 C14 C10 -171.3(2) . . . . ?
Cd1 O2 C14 O1 -6.4(3) . . . . ?
Cd1 O2 C14 C10 171.2(2) . . . . ?
C9 C10 C14 O1 -180.0(3) . . . . ?
C11 C10 C14 O1 1.6(4) . . . . ?
C9 C10 C14 O2 2.4(4) . . . . ?
C11 C10 C14 O2 -176.1(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
N3 H3N O2 0.88 2.19 2.952(3) 144.0 4_464

_refine_diff_density_max         1.057
_refine_diff_density_min         -1.454
_refine_diff_density_rms         0.072





_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DMF:H2O
####################################################################### 
# 
# 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_4Ni
_database_code_depnum_ccdc_archive 'CCDC 1477019'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 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         'C28 H24 N6 Ni O4, 7(H2 O)'
_chemical_formula_sum            'C28 H38 N6 Ni O11'
_chemical_formula_weight         693.35

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'
Ni Ni 0.3410 1.1070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
'y, x, -z'

_cell_length_a                   14.792(2)
_cell_length_b                   14.792(2)
_cell_length_c                   18.957(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3592.4(12)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    36501
_cell_measurement_theta_min      2.674
_cell_measurement_theta_max      30.052

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.961
_exptl_crystal_F_000             1092
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.450
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_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     0.7109
_diffrn_radiation_type           synchrotron
_diffrn_source                   'MX2 Beamline, Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 315r'
_diffrn_measurement_method       'Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36501
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.674
_diffrn_reflns_theta_max         30.052
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             6951
_reflns_number_gt                6771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.988

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'BluICE (McPhillips et al, 2001)'
_computing_cell_refinement       'XDS (Kasch, 1993)'
_computing_data_reduction        'XDS (Kasch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+0.2944P] 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 2969 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6951
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0762
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.021 -0.016 -0.003 1977 208 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
Electron count equates to 7 waters per formula unit.
SQUEEZED solvent included in UNIT instruction.
2 H2O per formula unit found by microanalysis.
;

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
Ni1 Ni 0.44428(2) 0.0000 0.3333 0.02682(7) Uani 1 2 d S T P . .
O1 O 0.60852(9) 0.12189(8) 0.32352(5) 0.0316(2) Uani 1 1 d . . . . .
O2 O 0.51224(8) 0.09540(8) 0.41790(5) 0.0312(2) Uani 1 1 d . . . . .
N1 N 1.30509(10) 0.90582(9) 0.38241(7) 0.0295(2) Uani 1 1 d . . . . .
N2 N 0.97476(10) 0.60617(10) 0.47103(7) 0.0313(2) Uani 1 1 d . . . . .
N3 N 0.89154(10) 0.53365(10) 0.50773(7) 0.0340(3) Uani 1 1 d D . . . .
H3N H 0.891(2) 0.540(2) 0.55386(17) 0.051 Uiso 1 1 d D U . . .
C1 C 1.29262(12) 0.92526(12) 0.44955(8) 0.0353(3) Uani 1 1 d . . . . .
H1 H 1.3472 0.9858 0.4715 0.042 Uiso 1 1 calc R U . . .
C2 C 1.20422(13) 0.86155(11) 0.48873(8) 0.0352(3) Uani 1 1 d . . . . .
H2 H 1.1981 0.8798 0.5358 0.042 Uiso 1 1 calc R U . . .
C3 C 1.12427(12) 0.77057(11) 0.45878(8) 0.0301(3) Uani 1 1 d . . . . .
C4 C 1.13717(13) 0.75074(12) 0.38894(8) 0.0393(4) Uani 1 1 d . . . . .
H4 H 1.0843 0.6901 0.3660 0.047 Uiso 1 1 calc R U . . .
C5 C 1.22675(14) 0.81912(13) 0.35282(9) 0.0388(3) Uani 1 1 d . . . . .
H5 H 1.2334 0.8044 0.3050 0.047 Uiso 1 1 calc R U . . .
C6 C 1.03279(12) 0.69655(12) 0.50042(8) 0.0318(3) Uani 1 1 d . . . . .
C7 C 1.01203(13) 0.72549(13) 0.57218(9) 0.0390(3) Uani 1 1 d . . . . .
H7A H 0.9409 0.7141 0.5737 0.058 Uiso 1 1 calc R U . . .
H7B H 1.0620 0.7992 0.5816 0.058 Uiso 1 1 calc R U . . .
H7C H 1.0197 0.6820 0.6080 0.058 Uiso 1 1 calc R U . . .
C8 C 0.82491(11) 0.43844(11) 0.47655(8) 0.0305(3) Uani 1 1 d . . . . .
C9 C 0.83910(12) 0.41429(12) 0.40723(8) 0.0354(3) Uani 1 1 d . . . . .
H9 H 0.8978 0.4625 0.3804 0.042 Uiso 1 1 calc R U . . .
C10 C 0.76652(12) 0.31947(12) 0.37868(8) 0.0347(3) Uani 1 1 d . . . . .
H10 H 0.7763 0.3024 0.3320 0.042 Uiso 1 1 calc R U . . .
C11 C 0.67942(11) 0.24846(11) 0.41684(8) 0.0290(3) Uani 1 1 d . . . . .
C12 C 0.66716(11) 0.27274(11) 0.48628(7) 0.0303(3) Uani 1 1 d . . . . .
H12 H 0.6083 0.2244 0.5130 0.036 Uiso 1 1 calc R U . . .
C13 C 0.73941(11) 0.36585(12) 0.51628(7) 0.0307(3) Uani 1 1 d . . . . .
H13 H 0.7314 0.3809 0.5638 0.037 Uiso 1 1 calc R U . . .
C14 C 0.59731(11) 0.15039(10) 0.38468(7) 0.0283(3) Uani 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
Ni1 O2 2.0381(10) 4 ?
Ni1 O2 2.0380(10) . ?
Ni1 N1 2.0438(12) 4_565 ?
Ni1 N1 2.0437(13) 1_445 ?
Ni1 O1 2.1927(12) . ?
Ni1 O1 2.1926(12) 4 ?
Ni1 C14 2.4465(14) 4 ?
Ni1 C14 2.4465(14) . ?
O1 C14 1.2726(17) . ?
O2 C14 1.2721(17) . ?
N1 C1 1.3379(19) . ?
N1 C5 1.3476(19) . ?
N1 Ni1 2.0438(13) 1_665 ?
N2 C6 1.2989(19) . ?
N2 N3 1.3526(17) . ?
N3 C8 1.3843(18) . ?
N3 H3N 0.8800(14) . ?
C1 C2 1.385(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.3931(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C3 C6 1.474(2) . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.503(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.4006(19) . ?
C8 C9 1.405(2) . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3904(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(2) . ?
C11 C14 1.4797(18) . ?
C12 C13 1.3751(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
O2 Ni1 O2 163.09(7) 4 . ?
O2 Ni1 N1 95.39(5) 4 4_565 ?
O2 Ni1 N1 95.86(5) . 4_565 ?
O2 Ni1 N1 95.86(5) 4 1_445 ?
O2 Ni1 N1 95.39(5) . 1_445 ?
N1 Ni1 N1 96.39(7) 4_565 1_445 ?
O2 Ni1 O1 104.94(4) 4 . ?
O2 Ni1 O1 62.43(4) . . ?
N1 Ni1 O1 90.31(5) 4_565 . ?
N1 Ni1 O1 157.45(4) 1_445 . ?
O2 Ni1 O1 62.43(4) 4 4 ?
O2 Ni1 O1 104.94(4) . 4 ?
N1 Ni1 O1 157.45(4) 4_565 4 ?
N1 Ni1 O1 90.32(5) 1_445 4 ?
O1 Ni1 O1 91.64(6) . 4 ?
O2 Ni1 C14 31.30(4) 4 4 ?
O2 Ni1 C14 135.73(5) . 4 ?
N1 Ni1 C14 126.69(5) 4_565 4 ?
N1 Ni1 C14 91.71(5) 1_445 4 ?
O1 Ni1 C14 101.48(5) . 4 ?
O1 Ni1 C14 31.23(4) 4 4 ?
O2 Ni1 C14 135.73(5) 4 . ?
O2 Ni1 C14 31.30(4) . . ?
N1 Ni1 C14 91.72(5) 4_565 . ?
N1 Ni1 C14 126.69(5) 1_445 . ?
O1 Ni1 C14 31.23(4) . . ?
O1 Ni1 C14 101.48(5) 4 . ?
C14 Ni1 C14 123.85(7) 4 . ?
C14 O1 Ni1 85.46(8) . . ?
C14 O2 Ni1 92.36(8) . . ?
C1 N1 C5 117.08(13) . . ?
C1 N1 Ni1 119.12(10) . 1_665 ?
C5 N1 Ni1 123.58(11) . 1_665 ?
C6 N2 N3 117.82(13) . . ?
N2 N3 C8 119.34(13) . . ?
N2 N3 H3N 118.8(18) . . ?
C8 N3 H3N 119.5(17) . . ?
N1 C1 C2 123.28(13) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 119.70(14) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 116.90(14) . . ?
C4 C3 C6 121.70(13) . . ?
C2 C3 C6 121.34(14) . . ?
C5 C4 C3 120.02(14) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 122.98(15) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
N2 C6 C3 115.08(14) . . ?
N2 C6 C7 123.87(14) . . ?
C3 C6 C7 121.04(13) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C13 117.46(13) . . ?
N3 C8 C9 122.49(13) . . ?
C13 C8 C9 120.03(13) . . ?
C10 C9 C8 119.06(13) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.30(13) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 119.04(12) . . ?
C10 C11 C14 121.50(13) . . ?
C12 C11 C14 119.39(12) . . ?
C13 C12 C11 120.68(13) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 119.82(13) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
O2 C14 O1 119.36(12) . . ?
O2 C14 C11 119.18(12) . . ?
O1 C14 C11 121.41(13) . . ?
O2 C14 Ni1 56.34(7) . . ?
O1 C14 Ni1 63.31(7) . . ?
C11 C14 Ni1 171.19(11) . . ?

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
N3 H3N O1 0.8800(14) 2.079(11) 2.8943(17) 154(2) 2_655

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.033



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DMF:H2O
####################################################################### 
# 
# 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_4Co
_database_code_depnum_ccdc_archive 'CCDC 1477020'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 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         'C28 H24 Co N6 O4, 16(H2 O)'
_chemical_formula_sum            'C28 H56 Co N6 O20'
_chemical_formula_weight         855.71

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'
Co Co 0.3494 0.9721 '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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'

_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'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
'y, x, -z'

_cell_length_a                   14.780(2)
_cell_length_b                   14.780(2)
_cell_length_c                   19.179(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3628.3(12)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    39046
_cell_measurement_theta_min      1.591
_cell_measurement_theta_max      31.879

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             1359
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.425
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3608
_exptl_absorpt_correction_T_max  0.4341
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7108
_diffrn_radiation_type           synchrotron
_diffrn_source                   'MX2 Beamline Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC 315R'
_diffrn_measurement_method       'Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39046
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.591
_diffrn_reflns_theta_max         31.879
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             7002
_reflns_number_gt                4601
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_max     0.840
_reflns_Friedel_fraction_full    0.986

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'BluIce (McPhillips et al, 2001)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²] 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 1626 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7002
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.022 -0.017 -0.003 2014 501 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
Electron count equates to 16 waters per formula unit.
SQUEEZED solvent included in UNIT instruction.
2 H2O per formula unit found by microanalysis.
;

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
Co1 Co 0.44643(3) 0.0000 0.3333 0.04534(13) Uani 1 2 d S T P . .
O1 O 0.61658(15) 0.12632(13) 0.32452(9) 0.0517(4) Uani 1 1 d . . . . .
O2 O 0.51608(14) 0.09742(12) 0.41622(9) 0.0529(5) Uani 1 1 d . . . . .
N1 N 1.30619(16) 0.90467(14) 0.38583(11) 0.0470(5) Uani 1 1 d . . . . .
N2 N 0.97493(17) 0.60896(17) 0.47385(11) 0.0508(5) Uani 1 1 d . . . . .
N3 N 0.89003(18) 0.53614(17) 0.51019(11) 0.0528(5) Uani 1 1 d D . . . .
H3N H 0.878(3) 0.536(3) 0.5551(4) 0.079 Uiso 1 1 d D U . . .
C1 C 1.29433(19) 0.9254(2) 0.45182(13) 0.0519(6) Uani 1 1 d . . . . .
H1 H 1.3493 0.9860 0.4732 0.062 Uiso 1 1 calc R U . . .
C2 C 1.2060(2) 0.86296(17) 0.49051(13) 0.0518(6) Uani 1 1 d . . . . .
H2 H 1.1999 0.8823 0.5368 0.062 Uiso 1 1 calc R U . . .
C3 C 1.1263(2) 0.77216(19) 0.46184(14) 0.0483(6) Uani 1 1 d . . . . .
C4 C 1.1388(2) 0.7503(2) 0.39319(13) 0.0579(7) Uani 1 1 d . . . . .
H4 H 1.0859 0.6889 0.3713 0.069 Uiso 1 1 calc R U . . .
C5 C 1.2272(2) 0.8173(2) 0.35719(15) 0.0584(7) Uani 1 1 d . . . . .
H5 H 1.2334 0.8016 0.3100 0.070 Uiso 1 1 calc R U . . .
C6 C 1.0341(2) 0.6997(2) 0.50312(13) 0.0497(6) Uani 1 1 d . . . . .
C7 C 1.0131(2) 0.7298(2) 0.57434(15) 0.0581(7) Uani 1 1 d . . . . .
H7A H 0.9376 0.6999 0.5807 0.087 Uiso 1 1 calc R U . . .
H7B H 1.0477 0.8061 0.5778 0.087 Uiso 1 1 calc R U . . .
H7C H 1.0403 0.7030 0.6105 0.087 Uiso 1 1 calc R U . . .
C8 C 0.8240(2) 0.4416(2) 0.47838(14) 0.0489(6) Uani 1 1 d . . . . .
C9 C 0.8406(2) 0.4188(2) 0.41000(14) 0.0553(7) Uani 1 1 d . . . . .
H9 H 0.9002 0.4675 0.3844 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7689(2) 0.3245(2) 0.38068(13) 0.0543(6) Uani 1 1 d . . . . .
H10 H 0.7794 0.3090 0.3343 0.065 Uiso 1 1 calc R U . . .
C11 C 0.6817(2) 0.25180(19) 0.41739(14) 0.0484(6) Uani 1 1 d . . . . .
C12 C 0.66768(19) 0.2749(2) 0.48614(13) 0.0477(6) Uani 1 1 d . . . . .
H12 H 0.6087 0.2256 0.5120 0.057 Uiso 1 1 calc R U . . .
C13 C 0.7387(2) 0.3685(2) 0.51644(14) 0.0492(6) Uani 1 1 d . . . . .
H13 H 0.7293 0.3829 0.5633 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6016(2) 0.15453(19) 0.38479(13) 0.0470(6) Uani 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
Co1 O2 2.0439(17) 4 ?
Co1 O2 2.0439(17) . ?
Co1 N1 2.092(2) 4_565 ?
Co1 N1 2.092(2) 1_445 ?
Co1 O1 2.2679(19) 4 ?
Co1 O1 2.2680(19) . ?
Co1 C14 2.492(3) . ?
Co1 C14 2.492(3) 4 ?
O1 C14 1.285(3) . ?
O2 C14 1.267(3) . ?
N1 C1 1.334(3) . ?
N1 C5 1.351(3) . ?
N1 Co1 2.092(2) 1_665 ?
N2 C6 1.306(3) . ?
N2 N3 1.367(3) . ?
N3 C8 1.384(3) . ?
N3 H3N 0.8801(14) . ?
C1 C2 1.379(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 C6 1.474(4) . ?
C4 C5 1.368(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.516(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.388(4) . ?
C8 C9 1.406(4) . ?
C9 C10 1.380(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.403(4) . ?
C11 C14 1.469(3) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
O2 Co1 O2 162.58(12) 4 . ?
O2 Co1 N1 94.63(8) 4 4_565 ?
O2 Co1 N1 96.75(8) . 4_565 ?
O2 Co1 N1 96.75(8) 4 1_445 ?
O2 Co1 N1 94.62(8) . 1_445 ?
N1 Co1 N1 98.29(12) 4_565 1_445 ?
O2 Co1 O1 61.14(7) 4 4 ?
O2 Co1 O1 105.75(7) . 4 ?
N1 Co1 O1 155.22(7) 4_565 4 ?
N1 Co1 O1 90.25(7) 1_445 4 ?
O2 Co1 O1 105.75(7) 4 . ?
O2 Co1 O1 61.15(7) . . ?
N1 Co1 O1 90.25(7) 4_565 . ?
N1 Co1 O1 155.22(7) 1_445 . ?
O1 Co1 O1 91.58(10) 4 . ?
O2 Co1 C14 136.24(9) 4 . ?
O2 Co1 C14 30.45(8) . . ?
N1 Co1 C14 91.70(8) 4_565 . ?
N1 Co1 C14 125.07(8) 1_445 . ?
O1 Co1 C14 102.37(8) 4 . ?
O1 Co1 C14 30.87(7) . . ?
O2 Co1 C14 30.44(8) 4 4 ?
O2 Co1 C14 136.24(9) . 4 ?
N1 Co1 C14 125.07(8) 4_565 4 ?
N1 Co1 C14 91.70(8) 1_445 4 ?
O1 Co1 C14 30.87(7) 4 4 ?
O1 Co1 C14 102.37(8) . 4 ?
C14 Co1 C14 124.98(12) . 4 ?
C14 O1 Co1 84.25(15) . . ?
C14 O2 Co1 94.74(15) . . ?
C1 N1 C5 117.1(2) . . ?
C1 N1 Co1 120.11(16) . 1_665 ?
C5 N1 Co1 122.67(18) . 1_665 ?
C6 N2 N3 118.0(2) . . ?
N2 N3 C8 118.5(2) . . ?
N2 N3 H3N 128(2) . . ?
C8 N3 H3N 113(2) . . ?
N1 C1 C2 123.1(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 117.1(2) . . ?
C2 C3 C6 121.4(2) . . ?
C4 C3 C6 121.5(2) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 122.9(3) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
N2 C6 C3 114.6(2) . . ?
N2 C6 C7 123.9(2) . . ?
C3 C6 C7 121.4(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C13 117.5(2) . . ?
N3 C8 C9 122.3(2) . . ?
C13 C8 C9 120.2(2) . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.5(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 118.8(2) . . ?
C10 C11 C14 121.6(2) . . ?
C12 C11 C14 119.5(2) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
O2 C14 O1 119.2(2) . . ?
O2 C14 C11 119.8(2) . . ?
O1 C14 C11 121.0(2) . . ?
O2 C14 Co1 54.82(12) . . ?
O1 C14 Co1 64.88(13) . . ?
C11 C14 Co1 171.0(2) . . ?

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
C6 N2 N3 C8 176.9(3) . . . . ?
C5 N1 C1 C2 -0.8(4) . . . . ?
Co1 N1 C1 C2 -176.8(2) 1_665 . . . ?
N1 C1 C2 C3 2.4(5) . . . . ?
C1 C2 C3 C4 -2.1(4) . . . . ?
C1 C2 C3 C6 175.6(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C6 C3 C4 C5 -177.4(3) . . . . ?
C1 N1 C5 C4 -1.1(4) . . . . ?
Co1 N1 C5 C4 174.7(2) 1_665 . . . ?
C3 C4 C5 N1 1.4(5) . . . . ?
N3 N2 C6 C3 177.6(2) . . . . ?
N3 N2 C6 C7 -1.3(4) . . . . ?
C2 C3 C6 N2 -168.1(3) . . . . ?
C4 C3 C6 N2 9.5(4) . . . . ?
C2 C3 C6 C7 10.8(4) . . . . ?
C4 C3 C6 C7 -171.6(3) . . . . ?
N2 N3 C8 C13 179.5(2) . . . . ?
N2 N3 C8 C9 -0.9(4) . . . . ?
N3 C8 C9 C10 -177.2(3) . . . . ?
C13 C8 C9 C10 2.3(4) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C9 C10 C11 C14 175.8(3) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C14 C11 C12 C13 -176.1(2) . . . . ?
C11 C12 C13 C8 1.2(4) . . . . ?
N3 C8 C13 C12 177.0(3) . . . . ?
C9 C8 C13 C12 -2.6(4) . . . . ?
Co1 O2 C14 O1 -8.4(2) . . . . ?
Co1 O2 C14 C11 171.4(2) . . . . ?
Co1 O1 C14 O2 7.6(2) . . . . ?
Co1 O1 C14 C11 -172.2(2) . . . . ?
C10 C11 C14 O2 -169.7(3) . . . . ?
C12 C11 C14 O2 6.9(4) . . . . ?
C10 C11 C14 O1 10.1(4) . . . . ?
C12 C11 C14 O1 -173.3(2) . . . . ?

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
N3 H3N O1 0.8801(14) 2.075(14) 2.894(3) 154(3) 2_655

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.034




_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DMF:H2O
####################################################################### 
# 
# 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_3py3bzH
_database_code_depnum_ccdc_archive 'CCDC 1477021'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 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         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.4840(19)
_cell_length_b                   14.148(3)
_cell_length_c                   9.994(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.45(3)
_cell_angle_gamma                90
_cell_volume                     1264.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12812
_cell_measurement_theta_min      2.597
_cell_measurement_theta_max      30.038

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.998
_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           synchrotron
_diffrn_source                   'MX 2 beamline, Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 315r'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12812
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_av_R_equivalents  0.1182
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.597
_diffrn_reflns_theta_max         30.038
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3679
_reflns_number_gt                3104
_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       'BluIce (McPhillips et al, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0955P)²+0.3671P] 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         3679
_refine_ls_number_parameters     179
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1734
_refine_ls_wR_factor_gt          0.1640
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O1 O 0.14265(12) 0.61208(8) 0.74556(11) 0.0219(3) Uani 1 1 d D . . . .
H1O H 0.0673(14) 0.6029(16) 0.770(2) 0.033 Uiso 1 1 d D U . . .
O2 O 0.21705(11) 0.70325(7) 0.93941(10) 0.0176(2) Uani 1 1 d . . . . .
N1 N 0.08688(12) 0.42575(8) 0.18045(11) 0.0145(2) Uani 1 1 d . . . . .
N2 N 0.42572(12) 0.59544(7) 0.41995(11) 0.0122(2) Uani 1 1 d . . . . .
N3 N 0.53272(12) 0.65013(8) 0.50958(11) 0.0136(2) Uani 1 1 d D . . . .
H3N H 0.6016(15) 0.6800(12) 0.4848(18) 0.020 Uiso 1 1 d D U . . .
C1 C 0.08225(15) 0.39754(9) 0.05059(13) 0.0159(3) Uani 1 1 d . . . . .
H1 H 0.0015 0.3590 -0.0041 0.019 Uiso 1 1 calc R U . . .
C2 C 0.19184(15) 0.42302(10) -0.00571(13) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.1873 0.4018 -0.0972 0.020 Uiso 1 1 calc R U . . .
C3 C 0.30862(15) 0.48025(9) 0.07445(13) 0.0155(3) Uani 1 1 d . . . . .
H3 H 0.3841 0.4992 0.0371 0.019 Uiso 1 1 calc R U . . .
C4 C 0.31538(13) 0.51000(9) 0.20963(12) 0.0121(2) Uani 1 1 d . . . . .
C5 C 0.19981(14) 0.47976(9) 0.25799(12) 0.0134(2) Uani 1 1 d . . . . .
H5 H 0.2021 0.4986 0.3499 0.016 Uiso 1 1 calc R U . . .
C6 C 0.43809(14) 0.56998(9) 0.30008(12) 0.0128(2) Uani 1 1 d . . . . .
C7 C 0.56551(17) 0.59614(11) 0.24892(15) 0.0214(3) Uani 1 1 d . . . . .
H7A H 0.5333 0.6464 0.1778 0.032 Uiso 1 1 calc R U . . .
H7B H 0.5958 0.5406 0.2065 0.032 Uiso 1 1 calc R U . . .
H7C H 0.6503 0.6184 0.3292 0.032 Uiso 1 1 calc R U . . .
C8 C 0.51180(14) 0.68287(9) 0.63308(12) 0.0120(2) Uani 1 1 d . . . . .
C9 C 0.38902(13) 0.65602(9) 0.67205(12) 0.0118(2) Uani 1 1 d . . . . .
H9 H 0.3179 0.6124 0.6153 0.014 Uiso 1 1 calc R U . . .
C10 C 0.37147(14) 0.69362(9) 0.79484(12) 0.0129(2) Uani 1 1 d . . . . .
C11 C 0.47673(15) 0.75614(9) 0.88100(13) 0.0158(3) Uani 1 1 d . . . . .
H11 H 0.4642 0.7815 0.9644 0.019 Uiso 1 1 calc R U . . .
C12 C 0.60021(15) 0.78068(10) 0.84285(13) 0.0161(3) Uani 1 1 d . . . . .
H12 H 0.6730 0.8227 0.9013 0.019 Uiso 1 1 calc R U . . .
C13 C 0.61848(14) 0.74458(9) 0.72032(13) 0.0144(3) Uani 1 1 d . . . . .
H13 H 0.7035 0.7618 0.6957 0.017 Uiso 1 1 calc R U . . .
C14 C 0.23586(14) 0.66976(9) 0.83332(12) 0.0139(3) Uani 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 C14 1.3040(16) . ?
O1 H1O 0.8401(10) . ?
O2 C14 1.2273(15) . ?
N1 C5 1.3338(17) . ?
N1 C1 1.3445(15) . ?
N2 C6 1.2932(15) . ?
N2 N3 1.3511(15) . ?
N3 C8 1.3929(15) . ?
N3 H3N 0.8800(10) . ?
C1 C2 1.3842(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3904(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3960(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.4038(17) . ?
C4 C6 1.4802(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.5067(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.3979(16) . ?
C8 C13 1.3996(18) . ?
C9 C10 1.3974(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3956(18) . ?
C10 C14 1.4985(17) . ?
C11 C12 1.3909(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3899(17) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
C14 O1 H1O 110.6(15) . . ?
C5 N1 C1 119.52(11) . . ?
C6 N2 N3 119.60(10) . . ?
N2 N3 C8 118.73(10) . . ?
N2 N3 H3N 123.5(12) . . ?
C8 N3 H3N 115.3(12) . . ?
N1 C1 C2 121.83(12) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 118.64(11) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 120.29(11) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 116.86(11) . . ?
C3 C4 C6 122.50(11) . . ?
C5 C4 C6 120.64(10) . . ?
N1 C5 C4 122.86(11) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
N2 C6 C4 115.47(11) . . ?
N2 C6 C7 125.19(12) . . ?
C4 C6 C7 119.34(10) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 122.29(11) . . ?
N3 C8 C13 118.21(11) . . ?
C9 C8 C13 119.50(11) . . ?
C10 C9 C8 119.67(11) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.88(11) . . ?
C11 C10 C14 118.89(11) . . ?
C9 C10 C14 120.20(11) . . ?
C12 C11 C10 118.92(11) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C13 C12 C11 120.87(12) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 120.12(11) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
O2 C14 O1 124.17(12) . . ?
O2 C14 C10 121.25(12) . . ?
O1 C14 C10 114.58(11) . . ?

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 0.8401(10) 1.739(3) 2.5776(15) 175(2) 3_566
N3 H3N O2 0.8800(10) 2.113(8) 2.9441(15) 157.3(17) 4_675

_refine_diff_density_max         0.574
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.082


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method THF
####################################################################### 
# 
# 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_3py4bzH
_database_code_depnum_ccdc_archive 'CCDC 1477022'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 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         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27

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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   9.801(2)
_cell_length_b                   13.736(3)
_cell_length_c                   14.268(3)
_cell_angle_alpha                79.99(3)
_cell_angle_beta                 80.75(3)
_cell_angle_gamma                85.00(3)
_cell_volume                     1863.5(7)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    38230
_cell_measurement_theta_min      2.933
_cell_measurement_theta_max      30.069

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.998
_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     0.7109
_diffrn_radiation_type           synchrotron
_diffrn_source                   'MX2 Beamline, Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 315r'
_diffrn_measurement_method       'Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38230
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.933
_diffrn_reflns_theta_max         30.069
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.923
_reflns_number_total             19833
_reflns_number_gt                18371
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_max     0.851
_reflns_Friedel_fraction_full    0.874

_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       'BluIce (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1142P)²+0.1121P] 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         19833
_refine_ls_number_parameters     1069
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1629
_refine_ls_wR_factor_gt          0.1590
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_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
O1A O 0.6057(2) 0.92136(17) -0.27751(13) 0.0261(4) Uani 1 1 d D . . . .
H14A H 0.646(4) 0.946(3) -0.3318(13) 0.039 Uiso 1 1 d D U . . .
O1B O 0.6919(2) 0.64895(15) 0.69194(13) 0.0231(4) Uani 1 1 d D . . . .
H14B H 0.663(4) 0.638(3) 0.7513(6) 0.035 Uiso 1 1 d D U . . .
O1C O 0.7051(2) 0.30472(17) 1.36625(13) 0.0265(4) Uani 1 1 d D . . . .
H14C H 0.673(4) 0.290(3) 1.4249(7) 0.040 Uiso 1 1 d D U . . .
O1D O 0.09357(19) 0.73487(13) 0.17209(14) 0.0213(4) Uani 1 1 d D . . . .
H14D H 0.094(4) 0.7970(3) 0.161(3) 0.032 Uiso 1 1 d D U . . .
O1E O 0.1041(2) 1.06230(14) 0.51240(16) 0.0253(4) Uani 1 1 d D . . . .
H14E H 0.111(4) 1.1238(5) 0.505(3) 0.038 Uiso 1 1 d D U . . .
O1F O 0.1918(2) 0.48857(13) 0.93631(15) 0.0241(4) Uani 1 1 d D . . . .
H14F H 0.184(4) 0.4272(5) 0.943(3) 0.036 Uiso 1 1 d D U . . .
O2A O 0.78344(19) 1.00649(14) -0.26279(13) 0.0203(3) Uani 1 1 d . . . . .
O2B O 0.53593(18) 0.54235(15) 0.68322(13) 0.0208(4) Uani 1 1 d . . . . .
O2C O 0.53245(19) 0.21563(15) 1.35093(13) 0.0211(4) Uani 1 1 d . . . . .
O2D O 0.28774(19) 0.74604(13) 0.23179(15) 0.0223(4) Uani 1 1 d . . . . .
O2E O 0.2693(2) 1.07296(14) 0.60106(15) 0.0244(4) Uani 1 1 d . . . . .
O2F O 0.0227(2) 0.47912(13) 0.85074(14) 0.0217(4) Uani 1 1 d . . . . .
N1A N 0.6915(2) 0.95813(19) 0.53999(16) 0.0229(4) Uani 1 1 d . . . . .
N1B N 0.6163(2) 0.59950(18) -0.12460(15) 0.0203(4) Uani 1 1 d . . . . .
N1C N 0.6259(2) 0.26028(18) 0.54823(16) 0.0224(4) Uani 1 1 d . . . . .
N1D N 0.0808(2) -0.07359(16) 0.14532(17) 0.0211(4) Uani 1 1 d . . . . .
N1E N 0.0884(2) 0.25480(16) 0.48289(17) 0.0205(4) Uani 1 1 d . . . . .
N1F N 0.2228(2) 1.29553(16) 0.94868(17) 0.0207(4) Uani 1 1 d . . . . .
N2A N 0.6020(2) 0.91104(16) 0.23422(15) 0.0172(4) Uani 1 1 d . . . . .
N2B N 0.7247(2) 0.61859(16) 0.18381(15) 0.0173(4) Uani 1 1 d . . . . .
N2C N 0.7190(2) 0.30555(16) 0.85376(15) 0.0175(4) Uani 1 1 d . . . . .
N2D N 0.2004(2) 0.22274(15) 0.23019(15) 0.0176(4) Uani 1 1 d . . . . .
N2E N 0.2026(2) 0.55302(16) 0.56813(16) 0.0184(4) Uani 1 1 d . . . . .
N2F N 0.1204(2) 1.00078(15) 0.85349(15) 0.0181(4) Uani 1 1 d . . . . .
N3A N 0.5284(2) 0.87312(17) 0.17740(15) 0.0186(4) Uani 1 1 d D . . . .
H11A H 0.469(3) 0.8268(18) 0.196(3) 0.028 Uiso 1 1 d D U . . .
N3B N 0.7991(2) 0.65474(17) 0.24149(15) 0.0196(4) Uani 1 1 d D . . . .
H11B H 0.872(2) 0.690(2) 0.220(3) 0.029 Uiso 1 1 d D U . . .
N3C N 0.7909(2) 0.34587(17) 0.91030(15) 0.0185(4) Uani 1 1 d D . . . .
H11C H 0.851(3) 0.3897(19) 0.883(2) 0.028 Uiso 1 1 d D U . . .
N3D N 0.2790(2) 0.27648(15) 0.26899(16) 0.0181(4) Uani 1 1 d D . . . .
H11D H 0.338(3) 0.255(3) 0.3095(19) 0.027 Uiso 1 1 d D U . . .
N3E N 0.2695(2) 0.60451(15) 0.61780(16) 0.0197(4) Uani 1 1 d D . . . .
H11E H 0.340(2) 0.580(3) 0.647(2) 0.029 Uiso 1 1 d D U . . .
N3F N 0.0481(2) 0.94724(15) 0.80957(16) 0.0187(4) Uani 1 1 d D . . . .
H11F H -0.027(2) 0.973(3) 0.785(2) 0.028 Uiso 1 1 d D U . . .
C1A C 0.7945(3) 1.0162(2) 0.49924(19) 0.0230(5) Uani 1 1 d . . . . .
H1A H 0.8420 1.0457 0.5391 0.028 Uiso 1 1 calc R U . . .
C1B C 0.5155(3) 0.5390(2) -0.08557(18) 0.0204(5) Uani 1 1 d . . . . .
H1B H 0.4648 0.5137 -0.1265 0.024 Uiso 1 1 calc R U . . .
C1C C 0.5339(3) 0.1936(2) 0.58943(18) 0.0205(5) Uani 1 1 d . . . . .
H1C H 0.4892 0.1618 0.5498 0.025 Uiso 1 1 calc R U . . .
C1D C -0.0083(3) -0.02205(19) 0.0907(2) 0.0214(5) Uani 1 1 d . . . . .
H1D H -0.0540 -0.0557 0.0530 0.026 Uiso 1 1 calc R U . . .
C1E C -0.0003(3) 0.30584(19) 0.42790(19) 0.0213(5) Uani 1 1 d . . . . .
H1E H -0.0489 0.2711 0.3929 0.026 Uiso 1 1 calc R U . . .
C1F C 0.3189(3) 1.24554(19) 0.99806(19) 0.0207(5) Uani 1 1 d . . . . .
H1F H 0.3644 1.2793 1.0358 0.025 Uiso 1 1 calc R U . . .
C2A C 0.8338(3) 1.0348(2) 0.4001(2) 0.0255(5) Uani 1 1 d . . . . .
H2A H 0.9073 1.0764 0.3724 0.031 Uiso 1 1 calc R U . . .
C2B C 0.4831(3) 0.5122(2) 0.01316(19) 0.0219(5) Uani 1 1 d . . . . .
H2B H 0.4104 0.4695 0.0395 0.026 Uiso 1 1 calc R U . . .
C2C C 0.5020(3) 0.16961(19) 0.68866(19) 0.0196(4) Uani 1 1 d . . . . .
H2C H 0.4357 0.1223 0.7167 0.023 Uiso 1 1 calc R U . . .
C2D C -0.0358(3) 0.07982(19) 0.08754(19) 0.0207(5) Uani 1 1 d . . . . .
H2D H -0.1009 0.1150 0.0494 0.025 Uiso 1 1 calc R U . . .
C2E C -0.0240(2) 0.40787(19) 0.41997(19) 0.0203(4) Uani 1 1 d . . . . .
H2E H -0.0872 0.4424 0.3800 0.024 Uiso 1 1 calc R U . . .
C2F C 0.3542(3) 1.14551(19) 0.9959(2) 0.0212(5) Uani 1 1 d . . . . .
H2F H 0.4229 1.1115 1.0316 0.025 Uiso 1 1 calc R U . . .
C3A C 0.7644(3) 0.9917(2) 0.34218(19) 0.0224(5) Uani 1 1 d . . . . .
H3A H 0.7896 1.0041 0.2742 0.027 Uiso 1 1 calc R U . . .
C3B C 0.5575(2) 0.54809(19) 0.07328(17) 0.0195(4) Uani 1 1 d . . . . .
H3B H 0.5375 0.5292 0.1411 0.023 Uiso 1 1 calc R U . . .
C3C C 0.5685(3) 0.21586(19) 0.74652(17) 0.0191(4) Uani 1 1 d . . . . .
H3C H 0.5481 0.2000 0.8146 0.023 Uiso 1 1 calc R U . . .
C3D C 0.0332(2) 0.12869(18) 0.14092(19) 0.0194(4) Uani 1 1 d . . . . .
H3D H 0.0148 0.1978 0.1403 0.023 Uiso 1 1 calc R U . . .
C3E C 0.0462(2) 0.45836(18) 0.47152(18) 0.0183(4) Uani 1 1 d . . . . .
H3E H 0.0315 0.5282 0.4672 0.022 Uiso 1 1 calc R U . . .
C3F C 0.2882(3) 1.09650(18) 0.94120(19) 0.0200(5) Uani 1 1 d . . . . .
H3F H 0.3120 1.0285 0.9382 0.024 Uiso 1 1 calc R U . . .
C4A C 0.6569(2) 0.92979(19) 0.38403(17) 0.0166(4) Uani 1 1 d . . . . .
C4B C 0.6625(3) 0.6125(2) 0.03301(17) 0.0159(4) Uani 1 1 d . . . . .
C4C C 0.6658(3) 0.28597(18) 0.70422(18) 0.0166(4) Uani 1 1 d . . . . .
C4D C 0.1303(2) 0.07633(18) 0.19598(18) 0.0180(4) Uani 1 1 d . . . . .
C4E C 0.1395(2) 0.40590(17) 0.53033(17) 0.0165(4) Uani 1 1 d . . . . .
C4F C 0.1857(2) 1.14758(18) 0.89006(17) 0.0171(4) Uani 1 1 d . . . . .
C5A C 0.6252(3) 0.9160(2) 0.48366(18) 0.0203(5) Uani 1 1 d . . . . .
H5A H 0.5526 0.8744 0.5135 0.024 Uiso 1 1 calc R U . . .
C5B C 0.6879(2) 0.63542(19) -0.06703(17) 0.0191(4) Uani 1 1 d . . . . .
H5B H 0.7593 0.6785 -0.0958 0.023 Uiso 1 1 calc R U . . .
C5C C 0.6901(3) 0.3051(2) 0.60402(17) 0.0203(5) Uani 1 1 d . . . . .
H5C H 0.7555 0.3522 0.5735 0.024 Uiso 1 1 calc R U . . .
C5D C 0.1488(3) -0.02595(18) 0.19646(19) 0.0196(5) Uani 1 1 d . . . . .
H5D H 0.2122 -0.0633 0.2347 0.024 Uiso 1 1 calc R U . . .
C5E C 0.1573(3) 0.30380(17) 0.53223(18) 0.0183(4) Uani 1 1 d . . . . .
H5E H 0.2214 0.2671 0.5703 0.022 Uiso 1 1 calc R U . . .
C5F C 0.1578(3) 1.24754(18) 0.89637(19) 0.0194(4) Uani 1 1 d . . . . .
H5F H 0.0893 1.2835 0.8619 0.023 Uiso 1 1 calc R U . . .
C6A C 0.5788(2) 0.88132(18) 0.32649(16) 0.0156(4) Uani 1 1 d . . . . .
C6B C 0.7439(2) 0.65458(18) 0.09355(16) 0.0159(4) Uani 1 1 d . . . . .
C6C C 0.7420(2) 0.33585(18) 0.76198(17) 0.0163(4) Uani 1 1 d . . . . .
C6D C 0.2148(2) 0.12699(17) 0.24744(17) 0.0171(4) Uani 1 1 d . . . . .
C6E C 0.2142(2) 0.45725(17) 0.58725(17) 0.0171(4) Uani 1 1 d . . . . .
C6F C 0.1066(2) 1.09633(18) 0.83518(18) 0.0179(4) Uani 1 1 d . . . . .
C7A C 0.4773(3) 0.8065(2) 0.37612(18) 0.0208(5) Uani 1 1 d . . . . .
H7A1 H 0.3882 0.8405 0.3964 0.031 Uiso 1 1 calc R U . . .
H7A2 H 0.5126 0.7678 0.4327 0.031 Uiso 1 1 calc R U . . .
H7A3 H 0.4649 0.7620 0.3317 0.031 Uiso 1 1 calc R U . . .
C7B C 0.8386(2) 0.73623(19) 0.04976(17) 0.0188(4) Uani 1 1 d . . . . .
H7B1 H 0.8290 0.7860 0.0923 0.028 Uiso 1 1 calc R U . . .
H7B2 H 0.8138 0.7671 -0.0130 0.028 Uiso 1 1 calc R U . . .
H7B3 H 0.9346 0.7087 0.0414 0.028 Uiso 1 1 calc R U . . .
C7C C 0.8412(3) 0.41327(19) 0.71579(18) 0.0203(5) Uani 1 1 d . . . . .
H7C1 H 0.8242 0.4700 0.7503 0.031 Uiso 1 1 calc R U . . .
H7C2 H 0.8279 0.4350 0.6485 0.031 Uiso 1 1 calc R U . . .
H7C3 H 0.9363 0.3855 0.7183 0.031 Uiso 1 1 calc R U . . .
C7D C 0.3126(3) 0.0668(2) 0.3090(2) 0.0256(5) Uani 1 1 d . . . . .
H7D1 H 0.3969 0.0470 0.2680 0.038 Uiso 1 1 calc R U . . .
H7D2 H 0.2681 0.0076 0.3451 0.038 Uiso 1 1 calc R U . . .
H7D3 H 0.3365 0.1066 0.3541 0.038 Uiso 1 1 calc R U . . .
C7E C 0.2935(3) 0.40038(18) 0.66349(19) 0.0208(4) Uani 1 1 d . . . . .
H7E1 H 0.3930 0.4007 0.6395 0.031 Uiso 1 1 calc R U . . .
H7E2 H 0.2658 0.3319 0.6791 0.031 Uiso 1 1 calc R U . . .
H7E3 H 0.2735 0.4315 0.7214 0.031 Uiso 1 1 calc R U . . .
C7F C 0.0169(3) 1.15433(19) 0.7664(2) 0.0219(5) Uani 1 1 d . . . . .
H7F1 H 0.0175 1.1192 0.7122 0.033 Uiso 1 1 calc R U . . .
H7F2 H 0.0527 1.2199 0.7426 0.033 Uiso 1 1 calc R U . . .
H7F3 H -0.0781 1.1617 0.7997 0.033 Uiso 1 1 calc R U . . .
C8A C 0.5592(2) 0.89993(18) 0.07884(17) 0.0158(4) Uani 1 1 d . . . . .
C8B C 0.7611(2) 0.63559(18) 0.34015(16) 0.0168(4) Uani 1 1 d . . . . .
C8C C 0.7567(2) 0.32175(18) 1.00919(17) 0.0160(4) Uani 1 1 d . . . . .
C8D C 0.2578(2) 0.37887(18) 0.25297(17) 0.0169(4) Uani 1 1 d . . . . .
C8E C 0.2518(2) 0.70692(17) 0.60196(17) 0.0172(4) Uani 1 1 d . . . . .
C8F C 0.0650(2) 0.84533(17) 0.82784(17) 0.0158(4) Uani 1 1 d . . . . .
C9A C 0.6532(2) 0.97253(18) 0.03741(17) 0.0167(4) Uani 1 1 d . . . . .
H9A H 0.6914 1.0084 0.0772 0.020 Uiso 1 1 calc R U . . .
C9B C 0.6593(3) 0.56971(19) 0.38304(17) 0.0175(4) Uani 1 1 d . . . . .
H9B H 0.6184 0.5335 0.3449 0.021 Uiso 1 1 calc R U . . .
C9C C 0.6607(2) 0.25120(19) 1.05092(17) 0.0181(4) Uani 1 1 d . . . . .
H9C H 0.6211 0.2160 1.0113 0.022 Uiso 1 1 calc R U . . .
C9D C 0.3326(2) 0.43448(18) 0.29874(18) 0.0171(4) Uani 1 1 d . . . . .
H9D H 0.3969 0.4020 0.3388 0.021 Uiso 1 1 calc R U . . .
C9E C 0.3268(2) 0.76065(18) 0.64973(18) 0.0180(4) Uani 1 1 d . . . . .
H9E H 0.3897 0.7269 0.6904 0.022 Uiso 1 1 calc R U . . .
C9F C -0.0096(2) 0.79041(18) 0.78104(18) 0.0169(4) Uani 1 1 d . . . . .
H9F H -0.0696 0.8236 0.7380 0.020 Uiso 1 1 calc R U . . .
C10A C 0.6901(2) 0.99184(19) -0.06182(17) 0.0176(4) Uani 1 1 d . . . . .
H10A H 0.7551 1.0401 -0.0893 0.021 Uiso 1 1 calc R U . . .
C10B C 0.6186(2) 0.55791(18) 0.48196(17) 0.0177(4) Uani 1 1 d . . . . .
H10B H 0.5488 0.5138 0.5112 0.021 Uiso 1 1 calc R U . . .
C10C C 0.6233(2) 0.23254(19) 1.14960(17) 0.0186(4) Uani 1 1 d . . . . .
H10C H 0.5572 0.1850 1.1772 0.022 Uiso 1 1 calc R U . . .
C10D C 0.3122(2) 0.53673(18) 0.28532(18) 0.0169(4) Uani 1 1 d . . . . .
H10D H 0.3633 0.5741 0.3162 0.020 Uiso 1 1 calc R U . . .
C10E C 0.3086(2) 0.86289(18) 0.63723(17) 0.0172(4) Uani 1 1 d . . . . .
H10E H 0.3593 0.8990 0.6696 0.021 Uiso 1 1 calc R U . . .
C10F C 0.0045(2) 0.68803(18) 0.79767(17) 0.0166(4) Uani 1 1 d . . . . .
H10F H -0.0455 0.6512 0.7656 0.020 Uiso 1 1 calc R U . . .
C11A C 0.6334(2) 0.94153(19) -0.12172(17) 0.0167(4) Uani 1 1 d . . . . .
C11B C 0.6786(2) 0.60982(19) 0.53920(17) 0.0167(4) Uani 1 1 d . . . . .
C11C C 0.6817(2) 0.28289(18) 1.20968(17) 0.0168(4) Uani 1 1 d . . . . .
C11D C 0.2178(2) 0.58550(17) 0.22705(17) 0.0159(4) Uani 1 1 d . . . . .
C11E C 0.2166(2) 0.91367(18) 0.57773(18) 0.0176(4) Uani 1 1 d . . . . .
C11F C 0.0920(2) 0.63826(17) 0.86147(17) 0.0161(4) Uani 1 1 d . . . . .
C12A C 0.5341(2) 0.87301(19) -0.08010(17) 0.0178(4) Uani 1 1 d . . . . .
H12A H 0.4914 0.8406 -0.1204 0.021 Uiso 1 1 calc R U . . .
C12B C 0.7840(2) 0.67270(18) 0.49654(17) 0.0176(4) Uani 1 1 d . . . . .
H12B H 0.8274 0.7067 0.5352 0.021 Uiso 1 1 calc R U . . .
C12C C 0.7821(2) 0.35021(19) 1.16828(17) 0.0181(4) Uani 1 1 d . . . . .
H12C H 0.8246 0.3831 1.2083 0.022 Uiso 1 1 calc R U . . .
C12D C 0.1437(2) 0.52998(17) 0.18163(18) 0.0176(4) Uani 1 1 d . . . . .
H12D H 0.0791 0.5628 0.1419 0.021 Uiso 1 1 calc R U . . .
C12E C 0.1412(2) 0.85944(18) 0.53134(18) 0.0184(4) Uani 1 1 d . . . . .
H12E H 0.0774 0.8934 0.4915 0.022 Uiso 1 1 calc R U . . .
C12F C 0.1688(2) 0.69327(18) 0.90596(17) 0.0168(4) Uani 1 1 d . . . . .
H12F H 0.2305 0.6599 0.9477 0.020 Uiso 1 1 calc R U . . .
C13A C 0.4971(2) 0.85180(18) 0.01874(17) 0.0167(4) Uani 1 1 d . . . . .
H13A H 0.4300 0.8049 0.0459 0.020 Uiso 1 1 calc R U . . .
C13B C 0.8255(2) 0.68550(19) 0.39730(17) 0.0179(4) Uani 1 1 d . . . . .
H13B H 0.8974 0.7280 0.3683 0.021 Uiso 1 1 calc R U . . .
C13C C 0.8202(3) 0.36951(19) 1.06898(17) 0.0184(4) Uani 1 1 d . . . . .
H13C H 0.8891 0.4149 1.0415 0.022 Uiso 1 1 calc R U . . .
C13D C 0.1631(3) 0.42752(18) 0.19365(18) 0.0182(4) Uani 1 1 d . . . . .
H13D H 0.1126 0.3905 0.1620 0.022 Uiso 1 1 calc R U . . .
C13E C 0.1583(2) 0.75675(18) 0.54264(18) 0.0185(4) Uani 1 1 d . . . . .
H13E H 0.1071 0.7207 0.5105 0.022 Uiso 1 1 calc R U . . .
C13F C 0.1559(2) 0.79582(18) 0.88971(18) 0.0178(4) Uani 1 1 d . . . . .
H13F H 0.2082 0.8326 0.9203 0.021 Uiso 1 1 calc R U . . .
C14A C 0.6813(2) 0.95977(19) -0.22730(17) 0.0171(4) Uani 1 1 d . . . . .
C14B C 0.6287(2) 0.59734(18) 0.64481(17) 0.0172(4) Uani 1 1 d . . . . .
C14C C 0.6333(2) 0.26397(19) 1.31509(17) 0.0181(4) Uani 1 1 d . . . . .
C14D C 0.2036(2) 0.69554(17) 0.21087(17) 0.0170(4) Uani 1 1 d . . . . .
C14E C 0.2007(2) 1.02318(18) 0.56536(18) 0.0184(4) Uani 1 1 d . . . . .
C14F C 0.0990(2) 0.52859(18) 0.88140(17) 0.0172(4) Uani 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
O1A C14A 1.308(3) . ?
O1B C14B 1.309(3) . ?
O1C C14C 1.311(3) . ?
O1D C14D 1.322(3) . ?
O1E C14E 1.326(3) . ?
O1F C14F 1.317(3) . ?
O2A C14A 1.228(3) . ?
O2B C14B 1.230(3) . ?
O2C C14C 1.230(3) . ?
O2D C14D 1.225(3) . ?
O2E C14E 1.221(3) . ?
O2F C14F 1.228(3) . ?
N1A C1A 1.336(3) . ?
N1A C5A 1.342(3) . ?
N1B C1B 1.335(3) . ?
N1B C5B 1.341(3) . ?
N1C C1C 1.335(3) . ?
N1C C5C 1.345(3) . ?
N1D C1D 1.338(4) . ?
N1D C5D 1.343(3) . ?
N1E C1E 1.336(3) . ?
N1E C5E 1.342(3) . ?
N1F C1F 1.337(3) . ?
N1F C5F 1.340(3) . ?
N2A C6A 1.298(3) . ?
N2A N3A 1.360(3) . ?
N2B C6B 1.287(3) . ?
N2B N3B 1.362(3) . ?
N2C C6C 1.293(3) . ?
N2C N3C 1.364(3) . ?
N2D C6D 1.295(3) . ?
N2D N3D 1.350(3) . ?
N2E C6E 1.295(3) . ?
N2E N3E 1.355(3) . ?
N2F C6F 1.292(3) . ?
N2F N3F 1.353(3) . ?
N3A C8A 1.381(3) . ?
N3B C8B 1.382(3) . ?
N3C C8C 1.385(3) . ?
N3D C8D 1.388(3) . ?
N3E C8E 1.385(3) . ?
N3F C8F 1.379(3) . ?
C1A C2A 1.390(4) . ?
C1B C2B 1.385(3) . ?
C1C C2C 1.387(4) . ?
C1D C2D 1.396(3) . ?
C1E C2E 1.388(3) . ?
C1F C2F 1.392(3) . ?
C2A C3A 1.384(3) . ?
C2B C3B 1.386(3) . ?
C2C C3C 1.392(3) . ?
C2D C3D 1.382(3) . ?
C2E C3E 1.385(3) . ?
C2F C3F 1.379(3) . ?
C3A C4A 1.403(3) . ?
C3B C4B 1.402(3) . ?
C3C C4C 1.405(3) . ?
C3D C4D 1.402(4) . ?
C3E C4E 1.407(3) . ?
C3F C4F 1.403(3) . ?
C4A C5A 1.388(3) . ?
C4A C6A 1.478(3) . ?
C4B C5B 1.393(3) . ?
C4B C6B 1.480(3) . ?
C4C C5C 1.393(3) . ?
C4C C6C 1.479(3) . ?
C4D C5D 1.400(3) . ?
C4D C6D 1.478(3) . ?
C4E C5E 1.394(3) . ?
C4E C6E 1.474(3) . ?
C4F C5F 1.392(3) . ?
C4F C6F 1.480(3) . ?
C6A C7A 1.499(3) . ?
C6B C7B 1.504(3) . ?
C6C C7C 1.497(3) . ?
C6D C7D 1.501(4) . ?
C6E C7E 1.506(4) . ?
C6F C7F 1.501(4) . ?
C8A C9A 1.404(3) . ?
C8A C13A 1.407(3) . ?
C8B C9B 1.399(3) . ?
C8B C13B 1.403(3) . ?
C8C C9C 1.399(3) . ?
C8C C13C 1.408(3) . ?
C8D C9D 1.404(3) . ?
C8D C13D 1.404(3) . ?
C8E C13E 1.401(3) . ?
C8E C9E 1.407(3) . ?
C8F C13F 1.405(3) . ?
C8F C9F 1.406(3) . ?
C9A C10A 1.388(3) . ?
C9B C10B 1.389(3) . ?
C9C C10C 1.381(3) . ?
C9D C10D 1.385(3) . ?
C9E C10E 1.384(3) . ?
C9F C10F 1.383(3) . ?
C10A C11A 1.394(3) . ?
C10B C11B 1.397(3) . ?
C10C C11C 1.405(3) . ?
C10D C11D 1.394(3) . ?
C10E C11E 1.397(3) . ?
C10F C11F 1.401(3) . ?
C11A C12A 1.402(3) . ?
C11A C14A 1.488(3) . ?
C11B C12B 1.398(3) . ?
C11B C14B 1.492(3) . ?
C11C C12C 1.398(3) . ?
C11C C14C 1.487(3) . ?
C11D C12D 1.396(3) . ?
C11D C14D 1.486(3) . ?
C11E C12E 1.401(3) . ?
C11E C14E 1.481(3) . ?
C11F C12F 1.400(3) . ?
C11F C14F 1.481(3) . ?
C12A C13A 1.384(3) . ?
C12B C13B 1.393(3) . ?
C12C C13C 1.391(3) . ?
C12D C13D 1.388(3) . ?
C12E C13E 1.390(3) . ?
C12F C13F 1.385(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
C1A N1A C5A 119.0(2) . . ?
C1B N1B C5B 119.4(2) . . ?
C1C N1C C5C 119.4(2) . . ?
C1D N1D C5D 119.4(2) . . ?
C1E N1E C5E 118.9(2) . . ?
C1F N1F C5F 118.9(2) . . ?
C6A N2A N3A 118.4(2) . . ?
C6B N2B N3B 117.3(2) . . ?
C6C N2C N3C 117.6(2) . . ?
C6D N2D N3D 119.3(2) . . ?
C6E N2E N3E 117.8(2) . . ?
C6F N2F N3F 118.9(2) . . ?
N2A N3A C8A 118.4(2) . . ?
N2B N3B C8B 119.38(19) . . ?
N2C N3C C8C 118.02(19) . . ?
N2D N3D C8D 118.4(2) . . ?
N2E N3E C8E 118.4(2) . . ?
N2F N3F C8F 118.7(2) . . ?
N1A C1A C2A 121.7(2) . . ?
N1B C1B C2B 121.6(2) . . ?
N1C C1C C2C 121.7(2) . . ?
N1D C1D C2D 121.7(2) . . ?
N1E C1E C2E 122.4(2) . . ?
N1F C1F C2F 121.9(2) . . ?
C3A C2A C1A 119.0(2) . . ?
C1B C2B C3B 119.5(2) . . ?
C1C C2C C3C 119.0(2) . . ?
C3D C2D C1D 118.9(2) . . ?
C3E C2E C1E 118.7(2) . . ?
C3F C2F C1F 119.0(2) . . ?
C2A C3A C4A 119.9(2) . . ?
C2B C3B C4B 119.3(2) . . ?
C2C C3C C4C 120.0(2) . . ?
C2D C3D C4D 120.1(2) . . ?
C2E C3E C4E 119.8(2) . . ?
C2F C3F C4F 119.7(2) . . ?
C5A C4A C3A 116.8(2) . . ?
C5A C4A C6A 120.5(2) . . ?
C3A C4A C6A 122.7(2) . . ?
C5B C4B C3B 117.2(2) . . ?
C5B C4B C6B 121.0(2) . . ?
C3B C4B C6B 121.8(2) . . ?
C5C C4C C3C 116.6(2) . . ?
C5C C4C C6C 121.0(2) . . ?
C3C C4C C6C 122.4(2) . . ?
C5D C4D C3D 117.0(2) . . ?
C5D C4D C6D 121.1(2) . . ?
C3D C4D C6D 121.8(2) . . ?
C5E C4E C3E 117.0(2) . . ?
C5E C4E C6E 121.9(2) . . ?
C3E C4E C6E 121.1(2) . . ?
C5F C4F C3F 117.1(2) . . ?
C5F C4F C6F 121.5(2) . . ?
C3F C4F C6F 121.4(2) . . ?
N1A C5A C4A 123.5(2) . . ?
N1B C5B C4B 123.0(2) . . ?
N1C C5C C4C 123.3(2) . . ?
N1D C5D C4D 122.9(2) . . ?
N1E C5E C4E 123.2(2) . . ?
N1F C5F C4F 123.3(2) . . ?
N2A C6A C4A 115.3(2) . . ?
N2A C6A C7A 124.9(2) . . ?
C4A C6A C7A 119.8(2) . . ?
N2B C6B C4B 115.7(2) . . ?
N2B C6B C7B 123.8(2) . . ?
C4B C6B C7B 120.4(2) . . ?
N2C C6C C4C 115.0(2) . . ?
N2C C6C C7C 123.3(2) . . ?
C4C C6C C7C 121.7(2) . . ?
N2D C6D C4D 114.5(2) . . ?
N2D C6D C7D 125.9(2) . . ?
C4D C6D C7D 119.5(2) . . ?
N2E C6E C4E 115.0(2) . . ?
N2E C6E C7E 123.7(2) . . ?
C4E C6E C7E 121.3(2) . . ?
N2F C6F C4F 114.4(2) . . ?
N2F C6F C7F 124.9(2) . . ?
C4F C6F C7F 120.7(2) . . ?
N3A C8A C9A 121.5(2) . . ?
N3A C8A C13A 119.1(2) . . ?
C9A C8A C13A 119.4(2) . . ?
N3B C8B C9B 121.5(2) . . ?
N3B C8B C13B 118.3(2) . . ?
C9B C8B C13B 120.1(2) . . ?
N3C C8C C9C 121.6(2) . . ?
N3C C8C C13C 119.1(2) . . ?
C9C C8C C13C 119.3(2) . . ?
N3D C8D C9D 118.5(2) . . ?
N3D C8D C13D 121.8(2) . . ?
C9D C8D C13D 119.6(2) . . ?
N3E C8E C13E 121.4(2) . . ?
N3E C8E C9E 118.4(2) . . ?
C13E C8E C9E 120.1(2) . . ?
N3F C8F C13F 122.0(2) . . ?
N3F C8F C9F 118.3(2) . . ?
C13F C8F C9F 119.7(2) . . ?
C10A C9A C8A 119.9(2) . . ?
C10B C9B C8B 119.2(2) . . ?
C10C C9C C8C 120.2(2) . . ?
C10D C9D C8D 119.9(2) . . ?
C10E C9E C8E 119.7(2) . . ?
C10F C9F C8F 120.0(2) . . ?
C9A C10A C11A 121.1(2) . . ?
C9B C10B C11B 121.1(2) . . ?
C9C C10C C11C 120.9(2) . . ?
C9D C10D C11D 120.8(2) . . ?
C9E C10E C11E 120.9(2) . . ?
C9F C10F C11F 120.5(2) . . ?
C10A C11A C12A 118.7(2) . . ?
C10A C11A C14A 119.7(2) . . ?
C12A C11A C14A 121.6(2) . . ?
C10B C11B C12B 119.4(2) . . ?
C10B C11B C14B 119.4(2) . . ?
C12B C11B C14B 121.2(2) . . ?
C12C C11C C10C 118.9(2) . . ?
C12C C11C C14C 122.1(2) . . ?
C10C C11C C14C 119.0(2) . . ?
C10D C11D C12D 119.1(2) . . ?
C10D C11D C14D 119.2(2) . . ?
C12D C11D C14D 121.6(2) . . ?
C10E C11E C12E 119.0(2) . . ?
C10E C11E C14E 119.4(2) . . ?
C12E C11E C14E 121.6(2) . . ?
C12F C11F C10F 119.3(2) . . ?
C12F C11F C14F 121.6(2) . . ?
C10F C11F C14F 119.0(2) . . ?
C13A C12A C11A 121.1(2) . . ?
C13B C12B C11B 120.0(2) . . ?
C13C C12C C11C 120.6(2) . . ?
C13D C12D C11D 121.0(2) . . ?
C13E C12E C11E 121.0(2) . . ?
C13F C12F C11F 120.7(2) . . ?
C12A C13A C8A 119.8(2) . . ?
C12B C13B C8B 120.0(2) . . ?
C12C C13C C8C 120.0(2) . . ?
C12D C13D C8D 119.5(2) . . ?
C12E C13E C8E 119.3(2) . . ?
C12F C13F C8F 119.8(2) . . ?
O2A C14A O1A 123.8(2) . . ?
O2A C14A C11A 122.1(2) . . ?
O1A C14A C11A 114.1(2) . . ?
O2B C14B O1B 123.6(2) . . ?
O2B C14B C11B 121.8(2) . . ?
O1B C14B C11B 114.6(2) . . ?
O2C C14C O1C 122.9(2) . . ?
O2C C14C C11C 122.6(2) . . ?
O1C C14C C11C 114.5(2) . . ?
O2D C14D O1D 122.5(2) . . ?
O2D C14D C11D 122.5(2) . . ?
O1D C14D C11D 115.00(19) . . ?
O2E C14E O1E 123.0(2) . . ?
O2E C14E C11E 123.3(2) . . ?
O1E C14E C11E 113.70(19) . . ?
O2F C14F O1F 122.8(2) . . ?
O2F C14F C11F 122.8(2) . . ?
O1F C14F C11F 114.5(2) . . ?

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
O1A H14A N1A 0.8401(15) 1.794(18) 2.580(3) 155(4) 1_554
O1B H14B N1B 0.8400(15) 1.756(7) 2.590(3) 172(4) 1_556
O1C H14C N1C 0.8401(15) 1.732(5) 2.569(3) 174(4) 1_556
O1D H14D N1D 0.8402(15) 1.749(5) 2.587(3) 175(4) 1_565
O1E H14E N1E 0.8400(15) 1.773(10) 2.599(3) 167(4) 1_565
O1F H14F N1F 0.8401(15) 1.805(12) 2.621(3) 163(4) 1_545
N3A H11A O2D 0.8802(15) 2.119(9) 2.979(3) 165(3) .
N3B H11B O1D 0.8800(15) 2.275(11) 3.127(3) 163(3) 1_655
N3C H11C O2F 0.8801(15) 2.110(11) 2.966(3) 164(3) 1_655
N3D H11D O2C 0.8800(15) 2.085(14) 2.910(3) 156(3) 1_554
N3E H11E O2B 0.8800(15) 2.065(10) 2.922(3) 165(3) .
N3F H11F O2A 0.8800(15) 2.073(8) 2.942(3) 169(3) 1_456
C5E H5E O2E 0.95 2.64 3.299(3) 126.9 1_545

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.063


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method THF
####################################################################### 
# 
# 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_4py3bzH-DMF
_database_code_depnum_ccdc_archive 'CCDC 1477023'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 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         'C14 H13 N3 O2, C3 H7 N O'
_chemical_formula_sum            'C17 H20 N4 O3'
_chemical_formula_weight         328.37

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.875(2)
_cell_length_b                   9.4220(19)
_cell_length_c                   18.577(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.92(3)
_cell_angle_gamma                90
_cell_volume                     1670.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    34489
_cell_measurement_theta_min      2.144
_cell_measurement_theta_max      31.837

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3779
_exptl_absorpt_correction_T_max  0.4341
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker AXS 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7108
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'MX1 beamline Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34489
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.144
_diffrn_reflns_theta_max         31.837
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5060
_reflns_number_gt                4297
_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       'BluICE (McPhillips et al, 2001)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0788P)²+0.5305P] 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         5060
_refine_ls_number_parameters     226
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
O1 O 0.07073(10) 1.07099(10) 0.41604(5) 0.0354(2) Uani 1 1 d D . . . .
H1O H 0.0144(14) 1.1353(13) 0.4204(10) 0.043 Uiso 1 1 d D U . . .
O2 O -0.04221(9) 1.08233(9) 0.29494(5) 0.02986(19) Uani 1 1 d . . . . .
O3 O 0.42705(11) 0.88621(10) 0.58065(5) 0.0363(2) Uani 1 1 d . . . . .
N1 N 0.91158(10) 0.26837(11) 0.44113(6) 0.0279(2) Uani 1 1 d . . . . .
N2 N 0.55643(9) 0.64190(10) 0.43538(5) 0.02202(18) Uani 1 1 d . . . . .
N3 N 0.46689(10) 0.74362(10) 0.44446(5) 0.02362(19) Uani 1 1 d D . . . .
H3N H 0.4664(16) 0.7791(15) 0.4882(4) 0.028 Uiso 1 1 d D U . . .
N4 N 0.35041(11) 1.03801(11) 0.65735(5) 0.0272(2) Uani 1 1 d . . . . .
C1 C 0.82029(12) 0.33910(12) 0.38685(6) 0.0261(2) Uani 1 1 d . . . . .
H1 H 0.8130 0.3132 0.3366 0.031 Uiso 1 1 calc R U . . .
C2 C 0.73670(12) 0.44764(12) 0.40073(6) 0.0240(2) Uani 1 1 d . . . . .
H2 H 0.6741 0.4954 0.3606 0.029 Uiso 1 1 calc R U . . .
C3 C 0.74496(11) 0.48701(11) 0.47478(6) 0.0216(2) Uani 1 1 d . . . . .
C4 C 0.84137(12) 0.41377(13) 0.53069(6) 0.0268(2) Uani 1 1 d . . . . .
H4 H 0.8524 0.4378 0.5815 0.032 Uiso 1 1 calc R U . . .
C5 C 0.92067(13) 0.30606(13) 0.51148(7) 0.0302(2) Uani 1 1 d . . . . .
H5 H 0.9847 0.2565 0.5503 0.036 Uiso 1 1 calc R U . . .
C6 C 0.65391(11) 0.59920(11) 0.49201(6) 0.0224(2) Uani 1 1 d . . . . .
C7 C 0.67469(13) 0.65370(14) 0.56997(6) 0.0308(2) Uani 1 1 d . . . . .
H7A H 0.6575 0.7562 0.5686 0.046 Uiso 1 1 calc R U . . .
H7B H 0.7710 0.6345 0.5986 0.046 Uiso 1 1 calc R U . . .
H7C H 0.6091 0.6060 0.5936 0.046 Uiso 1 1 calc R U . . .
C8 C 0.35927(11) 0.78223(11) 0.38300(6) 0.0208(2) Uani 1 1 d . . . . .
C9 C 0.26536(11) 0.88658(11) 0.39276(6) 0.0223(2) Uani 1 1 d . . . . .
H9 H 0.2783 0.9315 0.4398 0.027 Uiso 1 1 calc R U . . .
C10 C 0.15305(11) 0.92521(11) 0.33408(6) 0.0215(2) Uani 1 1 d . . . . .
C11 C 0.13378(12) 0.86098(12) 0.26462(6) 0.0250(2) Uani 1 1 d . . . . .
H11 H 0.0572 0.8873 0.2243 0.030 Uiso 1 1 calc R U . . .
C12 C 0.22831(12) 0.75779(12) 0.25514(6) 0.0266(2) Uani 1 1 d . . . . .
H12 H 0.2155 0.7135 0.2079 0.032 Uiso 1 1 calc R U . . .
C13 C 0.34109(12) 0.71814(11) 0.31337(6) 0.0238(2) Uani 1 1 d . . . . .
H13 H 0.4053 0.6481 0.3059 0.029 Uiso 1 1 calc R U . . .
C14 C 0.05078(11) 1.03458(11) 0.34603(6) 0.0237(2) Uani 1 1 d . . . . .
C15 C 0.35869(13) 0.98977(13) 0.59112(6) 0.0286(2) Uani 1 1 d . . . . .
H15 H 0.3074 1.0397 0.5483 0.034 Uiso 1 1 calc R U . . .
C16 C 0.27194(13) 1.16515(13) 0.66462(7) 0.0294(2) Uani 1 1 d . . . . .
H16A H 0.2323 1.2063 0.6152 0.044 Uiso 1 1 calc R U . . .
H16B H 0.3346 1.2342 0.6960 0.044 Uiso 1 1 calc R U . . .
H16C H 0.1960 1.1408 0.6875 0.044 Uiso 1 1 calc R U . . .
C17 C 0.42229(19) 0.96778(17) 0.72543(8) 0.0453(4) Uani 1 1 d . . . . .
H17A H 0.4634 0.8789 0.7136 0.068 Uiso 1 1 calc R U . . .
H17B H 0.3556 0.9471 0.7550 0.068 Uiso 1 1 calc R U . . .
H17C H 0.4967 1.0296 0.7540 0.068 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 C14 1.3098(14) . ?
O2 C14 1.2237(14) . ?
O3 C15 1.2301(15) . ?
N1 C5 1.3348(16) . ?
N1 C1 1.3437(15) . ?
N2 C6 1.2937(14) . ?
N2 N3 1.3438(12) . ?
N3 C8 1.3930(14) . ?
N4 C15 1.3338(15) . ?
N4 C17 1.4418(17) . ?
N4 C16 1.4518(15) . ?
C1 C2 1.3797(15) . ?
C2 C3 1.4066(15) . ?
C3 C4 1.3972(15) . ?
C3 C6 1.4754(14) . ?
C4 C5 1.3836(16) . ?
C6 C7 1.5000(15) . ?
C8 C9 1.3951(14) . ?
C8 C13 1.3966(14) . ?
C9 C10 1.3885(15) . ?
C10 C11 1.3933(15) . ?
C10 C14 1.4988(14) . ?
C11 C12 1.3900(15) . ?
C12 C13 1.3891(16) . ?

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
C5 N1 C1 117.76(10) . . ?
C6 N2 N3 119.71(9) . . ?
N2 N3 C8 118.10(9) . . ?
C15 N4 C17 121.30(11) . . ?
C15 N4 C16 121.87(10) . . ?
C17 N4 C16 116.81(10) . . ?
N1 C1 C2 123.05(10) . . ?
C1 C2 C3 119.44(10) . . ?
C4 C3 C2 116.98(10) . . ?
C4 C3 C6 121.95(9) . . ?
C2 C3 C6 121.07(9) . . ?
C5 C4 C3 119.54(10) . . ?
N1 C5 C4 123.22(10) . . ?
N2 C6 C3 114.44(9) . . ?
N2 C6 C7 124.53(10) . . ?
C3 C6 C7 121.02(9) . . ?
N3 C8 C9 118.02(9) . . ?
N3 C8 C13 122.36(9) . . ?
C9 C8 C13 119.60(10) . . ?
C10 C9 C8 120.40(10) . . ?
C9 C10 C11 120.28(10) . . ?
C9 C10 C14 119.76(9) . . ?
C11 C10 C14 119.95(10) . . ?
C12 C11 C10 119.02(10) . . ?
C13 C12 C11 121.29(10) . . ?
C12 C13 C8 119.40(10) . . ?
O2 C14 O1 124.38(10) . . ?
O2 C14 C10 122.51(10) . . ?
O1 C14 C10 113.10(9) . . ?
O3 C15 N4 125.63(12) . . ?

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 0.8403(10) 1.719(3) 2.5541(13) 172.6(18) 1_465
N3 H3N O3 0.8801(10) 2.112(3) 2.9788(13) 168.0(14) .

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DMF
####################################################################### 
# 
# 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_4py4bzH
_database_code_depnum_ccdc_archive 'CCDC 1477024'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-30 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         'C14 H13 N3 O2'
_chemical_formula_sum            'C14 H13 N3 O2'
_chemical_formula_weight         255.27

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   13.152(3)
_cell_length_b                   8.4410(17)
_cell_length_c                   11.502(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1276.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12177
_cell_measurement_theta_min      2.868
_cell_measurement_theta_max      30.055

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.998
_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     0.7109
_diffrn_radiation_type           synchrotron
_diffrn_source                   'MX2 Beamline, Australian Synchrotron'
_diffrn_measurement_device_type  'ADSC Quantum 315r'
_diffrn_measurement_method       'Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12177
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.868
_diffrn_reflns_theta_max         30.055
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3406
_reflns_number_gt                3310
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.976

_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       'BluIce (McPhillips et al, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+0.3468P] 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 
;
 Refined as a perfect inversion twin.
;
_refine_ls_number_reflns         3406
_refine_ls_number_parameters     179
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_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
O1 O 0.31805(11) 1.09331(16) 0.71971(14) 0.0222(3) Uani 1 1 d D . . . .
H1O H 0.2798(19) 1.172(2) 0.729(3) 0.033 Uiso 1 1 d D U . . .
O2 O 0.17794(10) 1.02169(15) 0.62291(14) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.28841(13) -0.16406(18) 0.28057(15) 0.0180(3) Uani 1 1 d . . . . .
N2 N 0.42389(12) 0.31129(18) 0.48043(15) 0.0170(3) Uani 1 1 d . . . . .
N3 N 0.47255(12) 0.42679(18) 0.53960(16) 0.0194(3) Uani 1 1 d D . . . .
H3N H 0.5366(7) 0.427(4) 0.562(3) 0.029 Uiso 1 1 d D U . . .
C1 C 0.25017(14) -0.0218(2) 0.30969(18) 0.0191(3) Uani 1 1 d . . . . .
H1 H 0.1811 0.0004 0.2918 0.023 Uiso 1 1 calc R U . . .
C2 C 0.30739(14) 0.0935(2) 0.36466(17) 0.0184(3) Uani 1 1 d . . . . .
H2 H 0.2778 0.1930 0.3831 0.022 Uiso 1 1 calc R U . . .
C3 C 0.40907(13) 0.06312(19) 0.39299(15) 0.0144(3) Uani 1 1 d . . . . .
C4 C 0.44826(14) -0.08517(19) 0.36148(17) 0.0163(3) Uani 1 1 d . . . . .
H4 H 0.5170 -0.1114 0.3781 0.020 Uiso 1 1 calc R U . . .
C5 C 0.38537(15) -0.1932(2) 0.30573(17) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.4130 -0.2931 0.2844 0.022 Uiso 1 1 calc R U . . .
C6 C 0.47144(13) 0.1817(2) 0.45528(16) 0.0155(3) Uani 1 1 d . . . . .
C7 C 0.57954(14) 0.1425(2) 0.48587(19) 0.0202(4) Uani 1 1 d . . . . .
H7A H 0.6132 0.2371 0.5168 0.030 Uiso 1 1 calc R U . . .
H7C H 0.6155 0.1064 0.4161 0.030 Uiso 1 1 calc R U . . .
H7B H 0.5805 0.0585 0.5447 0.030 Uiso 1 1 calc R U . . .
C8 C 0.41961(13) 0.5640(2) 0.56700(17) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.46966(13) 0.68059(19) 0.63273(16) 0.0166(3) Uani 1 1 d . . . . .
H9 H 0.5377 0.6641 0.6577 0.020 Uiso 1 1 calc R U . . .
C10 C 0.41961(13) 0.8193(2) 0.66098(17) 0.0160(3) Uani 1 1 d . . . . .
H10 H 0.4541 0.8986 0.7044 0.019 Uiso 1 1 calc R U . . .
C11 C 0.31887(13) 0.84478(19) 0.62651(17) 0.0149(3) Uani 1 1 d . . . . .
C12 C 0.26953(12) 0.7279(2) 0.56165(16) 0.0156(3) Uani 1 1 d . . . . .
H12 H 0.2012 0.7441 0.5376 0.019 Uiso 1 1 calc R U . . .
C13 C 0.31882(13) 0.5884(2) 0.53181(17) 0.0174(3) Uani 1 1 d . . . . .
H13 H 0.2844 0.5097 0.4877 0.021 Uiso 1 1 calc R U . . .
C14 C 0.26522(13) 0.9947(2) 0.65572(16) 0.0153(3) Uani 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 C14 1.310(2) . ?
O1 H1O 0.8400(14) . ?
O2 C14 1.230(2) . ?
N1 C5 1.331(3) . ?
N1 C1 1.344(2) . ?
N2 C6 1.293(2) . ?
N2 N3 1.350(2) . ?
N3 C8 1.388(2) . ?
N3 H3N 0.8800(14) . ?
C1 C2 1.383(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.400(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(2) . ?
C3 C6 1.479(2) . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.501(2) . ?
C7 H7A 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C13 1.401(2) . ?
C8 C9 1.405(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.400(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(2) . ?
C11 C14 1.488(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
C14 O1 H1O 105(2) . . ?
C5 N1 C1 118.00(15) . . ?
C6 N2 N3 119.63(15) . . ?
N2 N3 C8 118.64(14) . . ?
N2 N3 H3N 127(2) . . ?
C8 N3 H3N 114(2) . . ?
N1 C1 C2 122.60(17) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 119.83(16) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 117.03(15) . . ?
C2 C3 C6 121.24(15) . . ?
C4 C3 C6 121.72(15) . . ?
C5 C4 C3 119.15(16) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 123.38(16) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
N2 C6 C3 114.37(15) . . ?
N2 C6 C7 126.30(15) . . ?
C3 C6 C7 119.31(15) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
N3 C8 C13 122.11(15) . . ?
N3 C8 C9 118.15(15) . . ?
C13 C8 C9 119.74(15) . . ?
C10 C9 C8 119.80(15) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.95(16) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 118.86(15) . . ?
C12 C11 C14 120.09(15) . . ?
C10 C11 C14 121.04(15) . . ?
C13 C12 C11 120.97(15) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 119.68(15) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
O2 C14 O1 123.36(16) . . ?
O2 C14 C11 122.07(16) . . ?
O1 C14 C11 114.56(15) . . ?

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 0.8400(14) 1.753(8) 2.578(2) 167(4) 3_565
N3 H3N O2 0.8800(14) 2.033(7) 2.899(2) 168(3) 4_565
C7 H7A O2 0.98 2.52 3.492(2) 170.5 4_565
C9 H9 O2 0.95 2.45 3.230(2) 138.8 4_565

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.047



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method THF
