# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1522972'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H28 Ag2 N4 O5, H2 O'
_chemical_formula_sum            'C36 H30 Ag2 N4 O6'
_chemical_formula_weight         830.38

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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.4010(17)
_cell_length_b                   9.3598(19)
_cell_length_c                   20.446(4)
_cell_angle_alpha                86.38(3)
_cell_angle_beta                 82.42(3)
_cell_angle_gamma                81.59(3)
_cell_volume                     1574.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    28159
_cell_measurement_theta_min      3.043
_cell_measurement_theta_max      27.551

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    1.299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8290
_exptl_absorpt_correction_T_max  0.8811
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            26717
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.54
_reflns_number_total             7057
_reflns_number_gt                5223
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0214P)²+4.1486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7057
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.33796(5) 0.48245(4) 0.472170(16) 0.04922(12) Uani 1 1 d . . .
Ag2 Ag 1.33174(4) 0.48732(5) -0.033231(17) 0.05636(13) Uani 1 1 d . . .
N1 N 0.4614(4) 0.3243(4) 0.40225(15) 0.0352(7) Uani 1 1 d . . .
N2 N 1.1543(4) 0.4174(4) 0.04207(16) 0.0396(8) Uani 1 1 d . . .
N3 N 0.1780(4) 0.6559(4) 0.52494(16) 0.0388(8) Uani 1 1 d . . .
N4 N -0.5084(4) 0.5711(4) 0.88857(16) 0.0406(8) Uani 1 1 d . . .
C1 C 0.4353(5) 0.1864(4) 0.4098(2) 0.0382(9) Uani 1 1 d . . .
H1 H 0.3649 0.1579 0.4463 0.046 Uiso 1 1 calc R . .
C2 C 0.5089(5) 0.0848(5) 0.3653(2) 0.0433(10) Uani 1 1 d . . .
H2 H 0.4881 -0.0114 0.3715 0.052 Uiso 1 1 calc R . .
C3 C 0.6132(5) 0.1253(5) 0.3118(2) 0.0409(10) Uani 1 1 d . . .
H3 H 0.6639 0.0569 0.2812 0.049 Uiso 1 1 calc R . .
C4 C 0.6428(5) 0.2681(4) 0.30336(17) 0.0314(8) Uani 1 1 d . . .
C5 C 0.5630(5) 0.3631(4) 0.35061(18) 0.0340(8) Uani 1 1 d . . .
H5 H 0.5817 0.4600 0.3459 0.041 Uiso 1 1 calc R . .
C6 C 0.7512(5) 0.3253(4) 0.24899(19) 0.0356(9) Uani 1 1 d . . .
H6 H 0.7702 0.4211 0.2517 0.043 Uiso 1 1 calc R . .
C7 C 0.8248(5) 0.2563(5) 0.1966(2) 0.0390(9) Uani 1 1 d . . .
H7 H 0.8058 0.1606 0.1933 0.047 Uiso 1 1 calc R . .
C8 C 0.9336(5) 0.3160(4) 0.14326(18) 0.0335(8) Uani 1 1 d . . .
C9 C 1.0158(6) 0.2283(5) 0.0939(2) 0.0456(11) Uani 1 1 d . . .
H9 H 0.9980 0.1315 0.0938 0.055 Uiso 1 1 calc R . .
C10 C 1.1220(6) 0.2814(5) 0.0455(2) 0.0484(11) Uani 1 1 d . . .
H10 H 1.1753 0.2190 0.0128 0.058 Uiso 1 1 calc R . .
C11 C 1.0751(5) 0.5039(5) 0.0881(2) 0.0440(10) Uani 1 1 d . . .
H11 H 1.0948 0.6005 0.0862 0.053 Uiso 1 1 calc R . .
C12 C 0.9643(5) 0.4587(5) 0.1390(2) 0.0437(10) Uani 1 1 d . . .
H12 H 0.9104 0.5242 0.1703 0.052 Uiso 1 1 calc R . .
C13 C 0.2057(5) 0.7935(5) 0.51852(19) 0.0396(9) Uani 1 1 d . . .
H13 H 0.2830 0.8206 0.4842 0.047 Uiso 1 1 calc R . .
C14 C 0.1245(6) 0.8970(5) 0.5606(2) 0.0444(10) Uani 1 1 d . . .
H14 H 0.1442 0.9936 0.5542 0.053 Uiso 1 1 calc R . .
C15 C 0.0140(5) 0.8573(4) 0.6122(2) 0.0419(10) Uani 1 1 d . . .
H15 H -0.0410 0.9263 0.6418 0.050 Uiso 1 1 calc R . .
C16 C -0.0154(5) 0.7135(4) 0.62026(18) 0.0325(8) Uani 1 1 d . . .
C17 C 0.0680(5) 0.6194(4) 0.57418(19) 0.0354(9) Uani 1 1 d . . .
H17 H 0.0460 0.5234 0.5776 0.043 Uiso 1 1 calc R . .
C18 C -0.1233(5) 0.6585(4) 0.67487(19) 0.0354(9) Uani 1 1 d . . .
H18 H -0.1401 0.5617 0.6736 0.042 Uiso 1 1 calc R . .
C19 C -0.1999(5) 0.7312(4) 0.72606(19) 0.0355(9) Uani 1 1 d . . .
H19 H -0.1842 0.8283 0.7273 0.043 Uiso 1 1 calc R . .
C20 C -0.3065(5) 0.6744(4) 0.78090(18) 0.0324(8) Uani 1 1 d . . .
C21 C -0.3902(5) 0.7648(5) 0.82890(19) 0.0394(9) Uani 1 1 d . . .
H21 H -0.3794 0.8636 0.8260 0.047 Uiso 1 1 calc R . .
C22 C -0.4887(5) 0.7108(5) 0.8808(2) 0.0456(11) Uani 1 1 d . . .
H22 H -0.5449 0.7750 0.9123 0.055 Uiso 1 1 calc R . .
C23 C -0.4276(6) 0.4829(5) 0.8423(2) 0.0447(10) Uani 1 1 d . . .
H23 H -0.4391 0.3843 0.8467 0.054 Uiso 1 1 calc R . .
C24 C -0.3294(5) 0.5295(4) 0.7890(2) 0.0415(10) Uani 1 1 d . . .
H24 H -0.2770 0.4635 0.7576 0.050 Uiso 1 1 calc R . .
O1 O 0.7433(5) 0.9578(4) 0.10649(16) 0.0605(9) Uani 1 1 d . . .
O2 O 0.9966(5) 0.8492(4) 0.09476(15) 0.0615(10) Uani 1 1 d . . .
O3 O 0.7822(4) 0.7311(4) 0.45033(14) 0.0562(9) Uani 1 1 d . . .
O4 O 0.5643(4) 0.6684(4) 0.41708(15) 0.0562(9) Uani 1 1 d . . .
C25 C 0.8387(5) 0.8304(4) 0.19969(18) 0.0313(8) Uani 1 1 d . . .
C26 C 0.6911(5) 0.7892(4) 0.22291(19) 0.0355(9) Uani 1 1 d . . .
H26 H 0.6130 0.7903 0.1938 0.043 Uiso 1 1 calc R . .
C27 C 0.6545(5) 0.7455(4) 0.28938(18) 0.0333(8) Uani 1 1 d . . .
H27 H 0.5525 0.7166 0.3035 0.040 Uiso 1 1 calc R . .
C28 C 0.7617(5) 0.7433(4) 0.33428(17) 0.0286(8) Uani 1 1 d . . .
C29 C 0.9221(5) 0.7769(4) 0.31161(18) 0.0291(8) Uani 1 1 d . . .
C30 C 0.9591(5) 0.8216(4) 0.24297(18) 0.0303(8) Uani 1 1 d . . .
C31 C 1.1172(5) 0.8595(4) 0.2217(2) 0.0380(9) Uani 1 1 d . . .
H31 H 1.1424 0.8931 0.1777 0.046 Uiso 1 1 calc R . .
C32 C 1.2315(5) 0.8481(5) 0.2634(2) 0.0442(10) Uani 1 1 d . . .
H32 H 1.3342 0.8744 0.2483 0.053 Uiso 1 1 calc R . .
C33 C 1.1977(5) 0.7974(5) 0.3293(2) 0.0436(10) Uani 1 1 d . . .
H33 H 1.2792 0.7859 0.3573 0.052 Uiso 1 1 calc R . .
C34 C 1.0476(5) 0.7651(4) 0.3525(2) 0.0362(9) Uani 1 1 d . . .
H34 H 1.0263 0.7339 0.3970 0.043 Uiso 1 1 calc R . .
C35 C 0.8627(6) 0.8832(4) 0.1273(2) 0.0397(10) Uani 1 1 d . . .
C36 C 0.6987(5) 0.7114(4) 0.40689(18) 0.0335(9) Uani 1 1 d . . .
O5 O 0.2580(5) 0.8760(5) 0.00692(18) 0.0908(15) Uani 1 1 d . . .
H1W H 0.2542 0.9338 -0.0268 0.136 Uiso 1 1 d R . .
H2W H 0.1676 0.8667 0.0298 0.136 Uiso 1 1 d R . .
O6 O 0.5262(5) 0.7870(4) 0.0674(2) 0.0845(13) Uani 1 1 d . . .
H3W H 0.4475 0.8234 0.0467 0.127 Uiso 1 1 d R . .
H4W H 0.5712 0.8420 0.0885 0.127 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 N1 2.176(3) . ?
Ag1 N3 2.192(3) . ?
Ag1 O3 2.701(3) 2_666 ?
Ag1 O4 2.746(3) 2_666 ?
Ag1 Ag1 3.1530(11) 2_666 ?
Ag2 N4 2.135(3) 1_754 ?
Ag2 N2 2.138(3) . ?
Ag2 O6 2.760(5) 2_765 ?
Ag2 Ag2 3.3385(11) 2_865 ?
N1 C5 1.334(5) . ?
N1 C1 1.337(5) . ?
N2 C11 1.326(6) . ?
N2 C10 1.336(6) . ?
N3 C17 1.337(5) . ?
N3 C13 1.338(5) . ?
N4 C22 1.339(6) . ?
N4 C23 1.343(6) . ?
N4 Ag2 2.135(3) 1_356 ?
C1 C2 1.378(6) . ?
C1 H1 0.9400 . ?
C2 C3 1.379(6) . ?
C2 H2 0.9400 . ?
C3 C4 1.391(6) . ?
C3 H3 0.9400 . ?
C4 C5 1.392(5) . ?
C4 C6 1.467(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.320(5) . ?
C6 H6 0.9400 . ?
C7 C8 1.466(5) . ?
C7 H7 0.9400 . ?
C8 C9 1.387(6) . ?
C8 C12 1.393(6) . ?
C9 C10 1.362(6) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.389(6) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.379(6) . ?
C13 H13 0.9400 . ?
C14 C15 1.381(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.399(6) . ?
C15 H15 0.9400 . ?
C16 C17 1.380(5) . ?
C16 C18 1.460(5) . ?
C17 H17 0.9400 . ?
C18 C19 1.325(5) . ?
C18 H18 0.9400 . ?
C19 C20 1.463(5) . ?
C19 H19 0.9400 . ?
C20 C21 1.386(5) . ?
C20 C24 1.395(6) . ?
C21 C22 1.374(6) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
C23 C24 1.366(6) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
O1 C35 1.243(5) . ?
O2 C35 1.238(5) . ?
O3 C36 1.240(5) . ?
O3 Ag1 2.701(3) 2_666 ?
O4 C36 1.242(5) . ?
O4 Ag1 2.746(3) 2_666 ?
C25 C26 1.369(5) . ?
C25 C30 1.420(6) . ?
C25 C35 1.527(5) . ?
C26 C27 1.402(5) . ?
C26 H26 0.9400 . ?
C27 C28 1.365(5) . ?
C27 H27 0.9400 . ?
C28 C29 1.439(5) . ?
C28 C36 1.535(5) . ?
C29 C34 1.418(5) . ?
C29 C30 1.446(5) . ?
C30 C31 1.430(5) . ?
C31 C32 1.356(6) . ?
C31 H31 0.9400 . ?
C32 C33 1.405(6) . ?
C32 H32 0.9400 . ?
C33 C34 1.357(6) . ?
C33 H33 0.9400 . ?
C34 H34 0.9400 . ?
O5 H1W 0.8500 . ?
O5 H2W 0.8500 . ?
O6 Ag2 2.760(5) 2_765 ?
O6 H3W 0.8500 . ?
O6 H4W 0.8499 . ?

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 Ag1 N3 166.96(13) . . ?
N1 Ag1 O3 89.98(11) . 2_666 ?
N3 Ag1 O3 94.11(12) . 2_666 ?
N1 Ag1 O4 95.92(12) . 2_666 ?
N3 Ag1 O4 95.99(12) . 2_666 ?
O3 Ag1 O4 47.70(10) 2_666 2_666 ?
N1 Ag1 Ag1 92.70(10) . 2_666 ?
N3 Ag1 Ag1 98.24(10) . 2_666 ?
O3 Ag1 Ag1 104.55(8) 2_666 2_666 ?
O4 Ag1 Ag1 57.06(7) 2_666 2_666 ?
N4 Ag2 N2 174.79(14) 1_754 . ?
N4 Ag2 O6 88.18(14) 1_754 2_765 ?
N2 Ag2 O6 95.52(14) . 2_765 ?
N4 Ag2 Ag2 74.80(10) 1_754 2_865 ?
N2 Ag2 Ag2 109.01(10) . 2_865 ?
O6 Ag2 Ag2 86.77(9) 2_765 2_865 ?
C5 N1 C1 118.6(3) . . ?
C5 N1 Ag1 120.8(3) . . ?
C1 N1 Ag1 120.6(2) . . ?
C11 N2 C10 117.0(4) . . ?
C11 N2 Ag2 122.4(3) . . ?
C10 N2 Ag2 120.6(3) . . ?
C17 N3 C13 118.0(3) . . ?
C17 N3 Ag1 118.3(3) . . ?
C13 N3 Ag1 122.4(3) . . ?
C22 N4 C23 116.8(3) . . ?
C22 N4 Ag2 123.4(3) . 1_356 ?
C23 N4 Ag2 119.7(3) . 1_356 ?
N1 C1 C2 121.7(4) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.6(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 116.9(3) . . ?
C5 C4 C6 118.0(4) . . ?
C3 C4 C6 125.1(4) . . ?
N1 C5 C4 123.7(4) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C7 C6 C4 126.8(4) . . ?
C7 C6 H6 116.6 . . ?
C4 C6 H6 116.6 . . ?
C6 C7 C8 125.6(4) . . ?
C6 C7 H7 117.2 . . ?
C8 C7 H7 117.2 . . ?
C9 C8 C12 116.1(4) . . ?
C9 C8 C7 120.1(4) . . ?
C12 C8 C7 123.8(4) . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
N2 C10 C9 123.5(4) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N2 C11 C12 123.2(4) . . ?
N2 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
C11 C12 C8 119.7(4) . . ?
C11 C12 H12 120.2 . . ?
C8 C12 H12 120.2 . . ?
N3 C13 C14 122.1(4) . . ?
N3 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 119.5(4) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 116.7(4) . . ?
C17 C16 C18 119.3(4) . . ?
C15 C16 C18 124.0(4) . . ?
N3 C17 C16 124.3(4) . . ?
N3 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
C19 C18 C16 126.6(4) . . ?
C19 C18 H18 116.7 . . ?
C16 C18 H18 116.7 . . ?
C18 C19 C20 126.2(4) . . ?
C18 C19 H19 116.9 . . ?
C20 C19 H19 116.9 . . ?
C21 C20 C24 116.1(3) . . ?
C21 C20 C19 120.6(4) . . ?
C24 C20 C19 123.3(4) . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
N4 C22 C21 123.0(4) . . ?
N4 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
N4 C23 C24 123.3(4) . . ?
N4 C23 H23 118.4 . . ?
C24 C23 H23 118.4 . . ?
C23 C24 C20 120.3(4) . . ?
C23 C24 H24 119.8 . . ?
C20 C24 H24 119.8 . . ?
C36 O3 Ag1 90.6(2) . 2_666 ?
C36 O4 Ag1 88.4(3) . 2_666 ?
C26 C25 C30 119.3(3) . . ?
C26 C25 C35 116.7(4) . . ?
C30 C25 C35 124.0(3) . . ?
C25 C26 C27 121.0(4) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C28 C27 C26 122.4(4) . . ?
C28 C27 H27 118.8 . . ?
C26 C27 H27 118.8 . . ?
C27 C28 C29 118.8(3) . . ?
C27 C28 C36 116.9(3) . . ?
C29 C28 C36 124.3(3) . . ?
C34 C29 C28 123.6(3) . . ?
C34 C29 C30 118.0(3) . . ?
C28 C29 C30 118.4(3) . . ?
C25 C30 C31 122.3(3) . . ?
C25 C30 C29 119.9(3) . . ?
C31 C30 C29 117.8(4) . . ?
C32 C31 C30 121.4(4) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C31 C32 C33 120.6(4) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C34 C33 C32 120.2(4) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C29 121.9(4) . . ?
C33 C34 H34 119.1 . . ?
C29 C34 H34 119.1 . . ?
O2 C35 O1 125.8(4) . . ?
O2 C35 C25 118.4(4) . . ?
O1 C35 C25 115.8(4) . . ?
O4 C36 O3 125.1(4) . . ?
O4 C36 C28 115.8(4) . . ?
O3 C36 C28 119.1(4) . . ?
H1W O5 H2W 116.1 . . ?
Ag2 O6 H3W 115.6 2_765 . ?
Ag2 O6 H4W 123.2 2_765 . ?
H3W O6 H4W 119.1 . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         1.447
_refine_diff_density_min         -1.254
_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_5
_database_code_depnum_ccdc_archive 'CCDC 1522975'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 N4'
_chemical_formula_sum            'C24 H20 N4'
_chemical_formula_weight         364.44

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.2988(19)
_cell_length_b                   10.402(2)
_cell_length_c                   10.241(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.58(3)
_cell_angle_gamma                90.00
_cell_volume                     984.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    18629
_cell_measurement_theta_min      3.048
_cell_measurement_theta_max      27.549

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9911
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17540
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.54
_reflns_number_total             2254
_reflns_number_gt                1658
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    'SHELXTL and Diamond'
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0641P)²+0.1916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2254
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.86882(17) 0.58529(18) 0.85026(18) 0.0789(5) Uani 1 1 d . . .
N2 N 0.7090(2) 0.20623(15) 0.16592(16) 0.0755(5) Uani 1 1 d . . .
C1 C 0.8028(2) 0.5252(2) 0.9401(2) 0.0772(6) Uani 1 1 d . . .
H1 H 0.8462 0.5274 1.0276 0.093 Uiso 1 1 calc R . .
C2 C 0.6748(2) 0.45966(19) 0.91365(16) 0.0651(5) Uani 1 1 d . . .
H2 H 0.6321 0.4183 0.9812 0.078 Uiso 1 1 calc R . .
C3 C 0.61029(16) 0.45589(16) 0.78546(14) 0.0510(4) Uani 1 1 d . . .
H3 H 0.5225 0.4116 0.7646 0.061 Uiso 1 1 calc R . .
C4 C 0.67524(14) 0.51750(14) 0.68774(13) 0.0411(3) Uani 1 1 d . . .
C5 C 0.80403(17) 0.58004(17) 0.72758(18) 0.0588(4) Uani 1 1 d . . .
H5 H 0.8497 0.6224 0.6625 0.071 Uiso 1 1 calc R . .
C6 C 0.61030(14) 0.52387(13) 0.54705(12) 0.0388(3) Uani 1 1 d . . .
H6 H 0.6830 0.5555 0.4913 0.047 Uiso 1 1 calc R . .
C7 C 0.53624(14) 0.40096(13) 0.48599(12) 0.0383(3) Uani 1 1 d . . .
H7 H 0.5256 0.3378 0.5566 0.046 Uiso 1 1 calc R . .
C8 C 0.59998(15) 0.33500(13) 0.37511(12) 0.0402(3) Uani 1 1 d . . .
C9 C 0.52173(18) 0.23995(15) 0.30363(16) 0.0550(4) Uani 1 1 d . . .
H9 H 0.4295 0.2164 0.3245 0.066 Uiso 1 1 calc R . .
C10 C 0.5800(2) 0.18041(17) 0.20204(18) 0.0684(5) Uani 1 1 d . . .
H10 H 0.5241 0.1168 0.1548 0.082 Uiso 1 1 calc R . .
C11 C 0.7829(2) 0.29628(18) 0.2342(2) 0.0703(5) Uani 1 1 d . . .
H11 H 0.8748 0.3175 0.2108 0.084 Uiso 1 1 calc R . .
C12 C 0.73442(17) 0.36190(16) 0.33839(17) 0.0552(4) Uani 1 1 d . . .
H12 H 0.7932 0.4246 0.3839 0.066 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.320(3) . ?
N1 C5 1.331(2) . ?
N2 C11 1.315(2) . ?
N2 C10 1.323(3) . ?
C1 C2 1.371(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.380(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.383(2) . ?
C4 C6 1.4985(19) . ?
C5 H5 0.9400 . ?
C6 C7 1.5495(18) . ?
C6 C7 1.5738(19) 3_666 ?
C6 H6 0.9900 . ?
C7 C8 1.5052(18) . ?
C7 C6 1.5738(19) 3_666 ?
C7 H7 0.9900 . ?
C8 C12 1.375(2) . ?
C8 C9 1.386(2) . ?
C9 C10 1.374(2) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.385(2) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.22(16) . . ?
C11 N2 C10 115.55(15) . . ?
N1 C1 C2 124.08(17) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 118.35(17) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.76(15) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 116.07(14) . . ?
C5 C4 C6 120.19(14) . . ?
C3 C4 C6 123.68(12) . . ?
N1 C5 C4 125.52(17) . . ?
N1 C5 H5 117.2 . . ?
C4 C5 H5 117.2 . . ?
C4 C6 C7 117.58(11) . . ?
C4 C6 C7 118.18(11) . 3_666 ?
C7 C6 C7 89.39(10) . 3_666 ?
C4 C6 H6 110.0 . . ?
C7 C6 H6 110.0 . . ?
C7 C6 H6 110.0 3_666 . ?
C8 C7 C6 119.03(11) . . ?
C8 C7 C6 118.06(11) . 3_666 ?
C6 C7 C6 90.61(10) . 3_666 ?
C8 C7 H7 109.2 . . ?
C6 C7 H7 109.2 . . ?
C6 C7 H7 109.2 3_666 . ?
C12 C8 C9 116.07(13) . . ?
C12 C8 C7 124.23(13) . . ?
C9 C8 C7 119.69(13) . . ?
C10 C9 C8 119.52(16) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
N2 C10 C9 124.67(17) . . ?
N2 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
N2 C11 C12 124.36(17) . . ?
N2 C11 H11 117.8 . . ?
C12 C11 H11 117.8 . . ?
C8 C12 C11 119.81(16) . . ?
C8 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1522973'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 N4'
_chemical_formula_sum            'C24 H20 N4'
_chemical_formula_weight         364.44

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   12.112(2)
_cell_length_b                   16.437(3)
_cell_length_c                   19.547(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3891.5(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    70182
_cell_measurement_theta_min      3.041
_cell_measurement_theta_max      27.551

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9866
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            68757
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4466
_reflns_number_gt                3384
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    'SHELXTL and Diamond'
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0628P)²+1.3653P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4466
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.00452(13) 0.50173(11) 0.78495(8) 0.0629(4) Uani 1 1 d . . .
N2 N 0.87084(12) 0.47120(9) 0.40624(7) 0.0541(3) Uani 1 1 d . . .
N3 N 0.81832(18) 0.71043(10) 0.85378(7) 0.0745(5) Uani 1 1 d . . .
N4 N 0.48928(15) 0.68199(14) 0.45741(9) 0.0795(6) Uani 1 1 d . . .
C1 C 0.94891(17) 0.44940(12) 0.82347(9) 0.0637(5) Uani 1 1 d . . .
H1 H 0.9856 0.4253 0.8607 0.076 Uiso 1 1 calc R . .
C2 C 0.84169(17) 0.42874(13) 0.81205(11) 0.0699(5) Uani 1 1 d . . .
H2 H 0.8056 0.3912 0.8407 0.084 Uiso 1 1 calc R . .
C3 C 0.78675(14) 0.46397(11) 0.75757(9) 0.0569(4) Uani 1 1 d . . .
H3 H 0.7129 0.4501 0.7486 0.068 Uiso 1 1 calc R . .
C4 C 0.84053(12) 0.51944(9) 0.71642(7) 0.0397(3) Uani 1 1 d . . .
C5 C 0.94981(13) 0.53541(10) 0.73251(8) 0.0499(4) Uani 1 1 d . . .
H5 H 0.9883 0.5725 0.7047 0.060 Uiso 1 1 calc R . .
C6 C 0.77856(11) 0.56365(9) 0.66125(7) 0.0387(3) Uani 1 1 d . . .
H6 H 0.7168 0.5289 0.6455 0.046 Uiso 1 1 calc R . .
C7 C 0.83741(11) 0.59945(9) 0.59807(7) 0.0380(3) Uani 1 1 d . . .
H7 H 0.9126 0.6166 0.6118 0.046 Uiso 1 1 calc R . .
C8 C 0.84573(11) 0.55331(9) 0.53194(7) 0.0393(3) Uani 1 1 d . . .
C9 C 0.91040(14) 0.58395(10) 0.47968(7) 0.0482(4) Uani 1 1 d . . .
H9 H 0.9475 0.6337 0.4853 0.058 Uiso 1 1 calc R . .
C10 C 0.92031(15) 0.54134(10) 0.41924(8) 0.0544(4) Uani 1 1 d . . .
H10 H 0.9653 0.5636 0.3849 0.065 Uiso 1 1 calc R . .
C11 C 0.80756(15) 0.44262(12) 0.45614(9) 0.0589(4) Uani 1 1 d . . .
H11 H 0.7701 0.3934 0.4485 0.071 Uiso 1 1 calc R . .
C12 C 0.79293(14) 0.48067(11) 0.51901(8) 0.0545(4) Uani 1 1 d . . .
H12 H 0.7473 0.4570 0.5525 0.065 Uiso 1 1 calc R . .
C13 C 0.9044(2) 0.75845(12) 0.84149(10) 0.0770(6) Uani 1 1 d . . .
H13 H 0.9434 0.7796 0.8791 0.092 Uiso 1 1 calc R . .
C14 C 0.9393(2) 0.77871(12) 0.77716(10) 0.0741(6) Uani 1 1 d . . .
H14 H 1.0002 0.8134 0.7710 0.089 Uiso 1 1 calc R . .
C15 C 0.88366(17) 0.74736(11) 0.72155(8) 0.0600(5) Uani 1 1 d . . .
H15 H 0.9060 0.7608 0.6769 0.072 Uiso 1 1 calc R . .
C16 C 0.79486(14) 0.69611(9) 0.73178(7) 0.0445(3) Uani 1 1 d . . .
C17 C 0.76600(17) 0.68076(11) 0.79959(8) 0.0592(4) Uani 1 1 d . . .
H17 H 0.7049 0.6468 0.8075 0.071 Uiso 1 1 calc R . .
C18 C 0.73236(12) 0.65187(9) 0.67688(7) 0.0428(3) Uani 1 1 d . . .
H18 H 0.6519 0.6513 0.6859 0.051 Uiso 1 1 calc R . .
C19 C 0.75871(12) 0.67592(9) 0.60180(7) 0.0420(3) Uani 1 1 d . . .
H19 H 0.8006 0.7276 0.5993 0.050 Uiso 1 1 calc R . .
C20 C 0.66319(13) 0.67504(10) 0.55274(8) 0.0459(3) Uani 1 1 d . . .
C21 C 0.66905(16) 0.72148(11) 0.49380(9) 0.0601(4) Uani 1 1 d . . .
H21 H 0.7329 0.7520 0.4843 0.072 Uiso 1 1 calc R . .
C22 C 0.58163(19) 0.72291(14) 0.44927(11) 0.0755(6) Uani 1 1 d . . .
H22 H 0.5882 0.7556 0.4100 0.091 Uiso 1 1 calc R . .
C23 C 0.48545(17) 0.63511(17) 0.51272(12) 0.0816(7) Uani 1 1 d . . .
H23 H 0.4219 0.6033 0.5193 0.098 Uiso 1 1 calc R . .
C24 C 0.56809(15) 0.62967(14) 0.56134(10) 0.0660(5) Uani 1 1 d . . .
H24 H 0.5597 0.5956 0.5996 0.079 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.327(2) . ?
N1 C5 1.340(2) . ?
N2 C10 1.324(2) . ?
N2 C11 1.327(2) . ?
N3 C17 1.327(2) . ?
N3 C13 1.329(3) . ?
N4 C22 1.315(3) . ?
N4 C23 1.328(3) . ?
C1 C2 1.361(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.379(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.386(2) . ?
C4 C6 1.501(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.5427(18) . ?
C6 C18 1.584(2) . ?
C6 H6 0.9900 . ?
C7 C8 1.5021(19) . ?
C7 C19 1.579(2) . ?
C7 H7 0.9900 . ?
C8 C12 1.378(2) . ?
C8 C9 1.382(2) . ?
C9 C10 1.379(2) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.379(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.381(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.394(2) . ?
C16 C18 1.501(2) . ?
C17 H17 0.9400 . ?
C18 C19 1.5532(19) . ?
C18 H18 0.9900 . ?
C19 C20 1.503(2) . ?
C19 H19 0.9900 . ?
C20 C24 1.382(3) . ?
C20 C21 1.384(2) . ?
C21 C22 1.371(3) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
C23 C24 1.383(3) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.79(16) . . ?
C10 N2 C11 115.39(14) . . ?
C17 N3 C13 116.64(16) . . ?
C22 N4 C23 115.14(17) . . ?
N1 C1 C2 123.58(17) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 118.76(17) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.91(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 116.36(14) . . ?
C3 C4 C6 120.18(14) . . ?
C5 C4 C6 123.29(13) . . ?
N1 C5 C4 124.59(15) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C4 C6 C7 121.92(12) . . ?
C4 C6 C18 118.76(11) . . ?
C7 C6 C18 88.19(10) . . ?
C4 C6 H6 108.7 . . ?
C7 C6 H6 108.7 . . ?
C18 C6 H6 108.7 . . ?
C8 C7 C6 121.82(12) . . ?
C8 C7 C19 118.82(11) . . ?
C6 C7 C19 89.30(10) . . ?
C8 C7 H7 108.4 . . ?
C6 C7 H7 108.4 . . ?
C19 C7 H7 108.4 . . ?
C12 C8 C9 116.30(14) . . ?
C12 C8 C7 124.36(13) . . ?
C9 C8 C7 119.34(13) . . ?
C10 C9 C8 119.84(15) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N2 C10 C9 124.58(16) . . ?
N2 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
N2 C11 C12 124.35(16) . . ?
N2 C11 H11 117.8 . . ?
C12 C11 H11 117.8 . . ?
C8 C12 C11 119.53(15) . . ?
C8 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N3 C13 C14 123.59(18) . . ?
N3 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
C13 C14 C15 118.8(2) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C16 119.65(16) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 116.33(15) . . ?
C15 C16 C18 125.78(13) . . ?
C17 C16 C18 117.75(15) . . ?
N3 C17 C16 124.94(18) . . ?
N3 C17 H17 117.5 . . ?
C16 C17 H17 117.5 . . ?
C16 C18 C19 116.66(12) . . ?
C16 C18 C6 113.78(12) . . ?
C19 C18 C6 88.75(10) . . ?
C16 C18 H18 111.9 . . ?
C19 C18 H18 111.9 . . ?
C6 C18 H18 111.9 . . ?
C20 C19 C18 116.25(12) . . ?
C20 C19 C7 115.31(12) . . ?
C18 C19 C7 88.00(10) . . ?
C20 C19 H19 111.8 . . ?
C18 C19 H19 111.8 . . ?
C7 C19 H19 111.8 . . ?
C24 C20 C21 116.20(16) . . ?
C24 C20 C19 124.69(15) . . ?
C21 C20 C19 119.11(15) . . ?
C22 C21 C20 119.90(19) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
N4 C22 C21 124.9(2) . . ?
N4 C22 H22 117.6 . . ?
C21 C22 H22 117.6 . . ?
N4 C23 C24 124.9(2) . . ?
N4 C23 H23 117.6 . . ?
C24 C23 H23 117.6 . . ?
C20 C24 C23 118.98(19) . . ?
C20 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1522971'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;

#========================================================================== 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2'
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P c'
_symmetry_space_group_name_Hall  'P -2yc'

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

_cell_length_a                   7.3773(15)
_cell_length_b                   5.7410(11)
_cell_length_c                   12.670(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.92(2)
_cell_angle_gamma                90.00
_cell_volume                     482.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    17010
_cell_measurement_theta_min      3.046
_cell_measurement_theta_max      27.5502

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9879
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17010
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.53
_reflns_number_total             2168
_reflns_number_gt                1806
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    'SHELXTL and Diamond'
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0516P)²+0.1091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         2168
_refine_ls_number_parameters     127
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1115
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.3380(5) 0.4999(7) 0.3488(3) 0.0713(10) Uani 1 1 d . . .
N2 N 0.4361(5) 0.8313(6) -0.0039(3) 0.0675(10) Uani 1 1 d . . .
C1 C -0.3097(5) 0.6777(6) 0.4289(3) 0.0506(8) Uani 1 1 d . . .
H1 H -0.3697 0.6721 0.4808 0.061 Uiso 1 1 calc R . .
C2 C -0.1965(5) 0.8528(7) 0.4293(3) 0.0554(9) Uani 1 1 d . . .
H2 H -0.1845 0.9785 0.4795 0.066 Uiso 1 1 calc R . .
C3 C -0.0936(5) 0.8665(6) 0.3615(3) 0.0509(8) Uani 1 1 d . . .
H3 H -0.0104 0.9950 0.3680 0.061 Uiso 1 1 calc R . .
C4 C -0.1145(4) 0.6885(5) 0.2837(2) 0.0441(8) Uani 1 1 d . . .
C5 C -0.2439(5) 0.5078(8) 0.2775(3) 0.0541(9) Uani 1 1 d . . .
H5 H -0.2670 0.3879 0.2226 0.065 Uiso 1 1 calc R . .
C6 C -0.0119(4) 0.6801(6) 0.2061(2) 0.0446(8) Uani 1 1 d . . .
H6 H -0.0555 0.5654 0.1473 0.054 Uiso 1 1 calc R . .
C7 C 0.1341(5) 0.8175(6) 0.2117(3) 0.0525(9) Uani 1 1 d . . .
H7 H 0.1769 0.9318 0.2708 0.063 Uiso 1 1 calc R . .
C8 C 0.2374(4) 0.8127(5) 0.1364(2) 0.0414(7) Uani 1 1 d . . .
C9 C 0.2130(5) 0.6352(6) 0.0569(3) 0.0510(9) Uani 1 1 d . . .
H9 H 0.1299 0.5074 0.0519 0.061 Uiso 1 1 calc R . .
C10 C 0.3100(5) 0.6451(6) -0.0147(3) 0.0558(9) Uani 1 1 d . . .
H10 H 0.2906 0.5271 -0.0700 0.067 Uiso 1 1 calc R . .
C11 C 0.4590(5) 0.9992(7) 0.0686(3) 0.0555(8) Uani 1 1 d . . .
H11 H 0.5432 1.1255 0.0730 0.067 Uiso 1 1 calc R . .
C12 C 0.3627(5) 0.9945(7) 0.1381(3) 0.0514(8) Uani 1 1 d . . .
H12 H 0.3814 1.1196 0.1897 0.062 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.360(4) . ?
N1 C1 1.389(5) . ?
N2 C11 1.290(5) . ?
N2 C10 1.384(5) . ?
C1 C2 1.306(5) . ?
C1 H1 0.9400 . ?
C2 C3 1.375(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.389(5) . ?
C4 C6 1.481(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.312(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.459(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.388(4) . ?
C8 C12 1.388(5) . ?
C9 C10 1.381(5) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.352(4) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?

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 120.3(3) . . ?
C11 N2 C10 121.4(3) . . ?
C2 C1 N1 117.4(3) . . ?
C2 C1 H1 121.3 . . ?
N1 C1 H1 121.3 . . ?
C1 C2 C3 124.6(3) . . ?
C1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 117.0(3) . . ?
C3 C4 C6 124.6(3) . . ?
C5 C4 C6 118.4(3) . . ?
N1 C5 C4 121.7(3) . . ?
N1 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C4 126.21(19) . . ?
C7 C6 H6 116.9 . . ?
C4 C6 H6 116.9 . . ?
C6 C7 C8 127.2(2) . . ?
C6 C7 H7 116.4 . . ?
C8 C7 H7 116.4 . . ?
C9 C8 C12 115.9(3) . . ?
C9 C8 C7 123.3(3) . . ?
C12 C8 C7 120.7(3) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 N2 119.1(3) . . ?
C9 C10 H10 120.5 . . ?
N2 C10 H10 120.5 . . ?
N2 C11 C12 120.4(3) . . ?
N2 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C8 122.8(3) . . ?
C11 C12 H12 118.6 . . ?
C8 C12 H12 118.6 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.028
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1522974'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-04-13 downloaded from the CCDC.
;

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H16 N2 O4 Zn), H2 O'
_chemical_formula_sum            'C48 H34 N4 O9 Zn2'
_chemical_formula_weight         941.57

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   13.855(3)
_cell_length_b                   11.031(2)
_cell_length_c                   14.277(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.23(3)
_cell_angle_gamma                90.00
_cell_volume                     2033.9(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    37169
_cell_measurement_theta_min      3.049
_cell_measurement_theta_max      27.560

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             964
_exptl_absorpt_coefficient_mu    1.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8256
_exptl_absorpt_correction_T_max  0.8856
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            36008
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.56
_reflns_number_total             4671
_reflns_number_gt                3516
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0473P)²+2.7066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4671
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.29166(3) 0.57209(3) 0.67908(3) 0.02726(13) Uani 1 1 d . . .
N1 N 0.3086(2) 0.7295(2) 0.6132(2) 0.0284(6) Uani 1 1 d . . .
N2 N 0.6745(2) 0.9009(2) 0.2351(2) 0.0303(6) Uani 1 1 d . . .
O1 O 0.3983(3) 0.4994(3) 0.7973(3) 0.0701(10) Uani 1 1 d . A .
O2 O 0.4740(6) 0.5038(9) 0.6910(6) 0.066(3) Uani 0.648(19) 1 d P A 1
O2' O 0.5141(10) 0.5747(15) 0.7557(18) 0.085(8) Uani 0.352(19) 1 d P A 2
O3 O 0.7289(3) 0.0632(3) 1.0927(3) 0.0685(10) Uani 1 1 d . . .
O4 O 0.7010(12) -0.0234(7) 0.9599(4) 0.188(9) Uani 0.669(13) 1 d P B 1
O4' O 0.8182(11) 0.0456(12) 1.0045(11) 0.084(7) Uani 0.331(13) 1 d P B 2
C1 C 0.2429(3) 0.8220(3) 0.6025(3) 0.0378(8) Uani 1 1 d . . .
H1 H 0.1980 0.8205 0.6385 0.045 Uiso 1 1 calc R . .
C2 C 0.2386(3) 0.9193(4) 0.5407(3) 0.0438(9) Uani 1 1 d . . .
H2 H 0.1916 0.9829 0.5347 0.053 Uiso 1 1 calc R . .
C3 C 0.3041(3) 0.9221(3) 0.4878(3) 0.0389(8) Uani 1 1 d . . .
H3 H 0.3002 0.9861 0.4431 0.047 Uiso 1 1 calc R . .
C4 C 0.3753(3) 0.8307(3) 0.5007(3) 0.0311(7) Uani 1 1 d . . .
C5 C 0.3744(3) 0.7368(3) 0.5647(3) 0.0334(8) Uani 1 1 d . . .
H5 H 0.4232 0.6744 0.5745 0.040 Uiso 1 1 calc R . .
C6 C 0.4501(3) 0.8253(3) 0.4494(3) 0.0410(9) Uani 1 1 d . . .
H6 H 0.5004 0.7638 0.4697 0.049 Uiso 1 1 calc R . .
C7 C 0.4532(3) 0.8986(3) 0.3776(3) 0.0385(9) Uani 1 1 d . . .
H7 H 0.4019 0.9589 0.3562 0.046 Uiso 1 1 calc R . .
C8 C 0.5283(3) 0.8951(3) 0.3284(3) 0.0330(8) Uani 1 1 d . . .
C9 C 0.5217(3) 0.9782(4) 0.2533(3) 0.0407(9) Uani 1 1 d . . .
H9 H 0.4672 1.0346 0.2329 0.049 Uiso 1 1 calc R . .
C10 C 0.5945(3) 0.9785(4) 0.2086(3) 0.0414(9) Uani 1 1 d . . .
H10 H 0.5879 1.0353 0.1576 0.050 Uiso 1 1 calc R . .
C11 C 0.6801(3) 0.8195(3) 0.3062(3) 0.0369(8) Uani 1 1 d . . .
H11 H 0.7353 0.7639 0.3252 0.044 Uiso 1 1 calc R . .
C12 C 0.6097(3) 0.8132(3) 0.3526(3) 0.0403(9) Uani 1 1 d . . .
H12 H 0.6164 0.7530 0.4011 0.048 Uiso 1 1 calc R . .
C13 C 0.5507(3) 0.3843(3) 0.8421(3) 0.0365(8) Uani 1 1 d . A .
C14 C 0.5295(3) 0.3352(4) 0.9199(3) 0.0445(9) Uani 1 1 d . . .
H14 H 0.4757 0.3679 0.9375 0.053 Uiso 1 1 calc R . .
C15 C 0.5868(3) 0.2359(4) 0.9748(3) 0.0521(11) Uani 1 1 d . . .
H15 H 0.5709 0.2045 1.0287 0.063 Uiso 1 1 calc R . .
C16 C 0.6644(4) 0.1848(4) 0.9513(3) 0.0520(11) Uani 1 1 d . B .
C17 C 0.6938(3) 0.2378(3) 0.8745(3) 0.0462(10) Uani 1 1 d . . .
C18 C 0.6366(3) 0.3406(3) 0.8192(3) 0.0384(8) Uani 1 1 d . . .
C19 C 0.6700(3) 0.3919(4) 0.7453(3) 0.0476(10) Uani 1 1 d . . .
H19 H 0.6337 0.4587 0.7082 0.057 Uiso 1 1 calc R . .
C20 C 0.7526(4) 0.3481(5) 0.7261(4) 0.0636(13) Uani 1 1 d . . .
H20 H 0.7727 0.3842 0.6764 0.076 Uiso 1 1 calc R . .
C21 C 0.8074(4) 0.2489(6) 0.7807(4) 0.0751(16) Uani 1 1 d . . .
H21 H 0.8647 0.2189 0.7674 0.090 Uiso 1 1 calc R . .
C22 C 0.7799(4) 0.1960(5) 0.8514(4) 0.0707(15) Uani 1 1 d . . .
H22 H 0.8184 0.1294 0.8868 0.085 Uiso 1 1 calc R . .
C23 C 0.4760(3) 0.4783(4) 0.7796(3) 0.0452(10) Uani 1 1 d . . .
C24 C 0.7137(5) 0.0708(5) 1.0070(3) 0.081(2) Uani 1 1 d . . .
O5 O 1.0000 0.0000 1.0000 0.144(3) Uani 1 2 d S . .
H1W H 1.0412 -0.0580 1.0024 0.217 Uiso 0.50 1 d PR . .
H2W H 0.9689 0.0241 1.0381 0.217 Uiso 0.50 1 d PR . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.931(3) 4_565 ?
Zn1 O1 1.968(3) . ?
Zn1 N1 2.029(3) . ?
Zn1 N2 2.074(3) 4_576 ?
N1 C5 1.332(4) . ?
N1 C1 1.340(4) . ?
N2 C11 1.337(4) . ?
N2 C10 1.343(5) . ?
N2 Zn1 2.074(3) 4_675 ?
O1 C23 1.214(5) . ?
O2 C23 1.287(7) . ?
O2' C23 1.287(12) . ?
O3 C24 1.166(5) . ?
O3 Zn1 1.931(3) 4_666 ?
O4 C24 1.215(8) . ?
O4' C24 1.487(12) . ?
C1 C2 1.377(5) . ?
C1 H1 0.9400 . ?
C2 C3 1.374(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.384(5) . ?
C4 C6 1.470(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.319(5) . ?
C6 H6 0.9400 . ?
C7 C8 1.452(5) . ?
C7 H7 0.9400 . ?
C8 C12 1.387(5) . ?
C8 C9 1.388(5) . ?
C9 C10 1.374(5) . ?
C9 H9 0.9400 . ?
C10 H10 0.9400 . ?
C11 C12 1.365(5) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.360(5) . ?
C13 C18 1.428(5) . ?
C13 C23 1.509(5) . ?
C14 C15 1.411(5) . ?
C14 H14 0.9400 . ?
C15 C16 1.359(6) . ?
C15 H15 0.9400 . ?
C16 C17 1.426(6) . ?
C16 C24 1.513(6) . ?
C17 C22 1.425(7) . ?
C17 C18 1.444(5) . ?
C18 C19 1.413(6) . ?
C19 C20 1.359(6) . ?
C19 H19 0.9400 . ?
C20 C21 1.398(8) . ?
C20 H20 0.9400 . ?
C21 C22 1.336(8) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
O5 H1W 0.8500 . ?
O5 H2W 0.8499 . ?

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 Zn1 O1 104.94(17) 4_565 . ?
O3 Zn1 N1 117.76(14) 4_565 . ?
O1 Zn1 N1 124.76(14) . . ?
O3 Zn1 N2 97.06(13) 4_565 4_576 ?
O1 Zn1 N2 100.20(13) . 4_576 ?
N1 Zn1 N2 107.11(11) . 4_576 ?
C5 N1 C1 117.4(3) . . ?
C5 N1 Zn1 120.6(2) . . ?
C1 N1 Zn1 121.1(2) . . ?
C11 N2 C10 117.2(3) . . ?
C11 N2 Zn1 123.4(2) . 4_675 ?
C10 N2 Zn1 118.9(2) . 4_675 ?
C23 O1 Zn1 110.2(3) . . ?
C24 O3 Zn1 126.5(3) . 4_666 ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 117.3(3) . . ?
C3 C4 C6 124.3(3) . . ?
C5 C4 C6 118.4(3) . . ?
N1 C5 C4 124.1(3) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C7 C6 C4 126.1(4) . . ?
C7 C6 H6 116.9 . . ?
C4 C6 H6 116.9 . . ?
C6 C7 C8 126.2(4) . . ?
C6 C7 H7 116.9 . . ?
C8 C7 H7 116.9 . . ?
C12 C8 C9 116.3(3) . . ?
C12 C8 C7 123.9(3) . . ?
C9 C8 C7 119.8(3) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
N2 C10 C9 122.6(3) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
N2 C11 C12 123.2(3) . . ?
N2 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
C11 C12 C8 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C8 C12 H12 119.8 . . ?
C14 C13 C18 119.8(3) . . ?
C14 C13 C23 116.9(4) . . ?
C18 C13 C23 123.2(4) . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 121.3(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.5(4) . . ?
C15 C16 C24 117.5(4) . . ?
C17 C16 C24 123.0(4) . . ?
C22 C17 C16 122.8(4) . . ?
C22 C17 C18 117.9(4) . . ?
C16 C17 C18 119.3(4) . . ?
C19 C18 C13 124.1(3) . . ?
C19 C18 C17 117.4(4) . . ?
C13 C18 C17 118.5(4) . . ?
C20 C19 C18 122.4(4) . . ?
C20 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
C19 C20 C21 119.5(5) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 121.2(5) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C17 121.7(5) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
O1 C23 O2' 112.2(7) . . ?
O1 C23 O2 117.3(4) . . ?
O2' C23 O2 54.8(9) . . ?
O1 C23 C13 118.6(4) . . ?
O2' C23 C13 117.7(6) . . ?
O2 C23 C13 119.8(4) . . ?
O3 C24 O4 117.0(6) . . ?
O3 C24 O4' 101.8(7) . . ?
O4 C24 O4' 76.9(8) . . ?
O3 C24 C16 119.1(4) . . ?
O4 C24 C16 118.2(5) . . ?
O4' C24 C16 113.7(6) . . ?
H1W O5 H2W 134.3 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.081
