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

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

data_compound1
_audit_block_doi                 10.5517/cc1km84l
_database_code_depnum_ccdc_archive 'CCDC 1448479'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 N3 O4 Zn'
_chemical_formula_weight         349.62

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   C2/C

loop_
_symmetry_equiv_pos_as_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                   27.509(3)
_cell_length_b                   7.6304(8)
_cell_length_c                   16.2294(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.061(5)
_cell_angle_gamma                90.00
_cell_volume                     2977.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5901
_cell_measurement_theta_min      2.8005
_cell_measurement_theta_max      28.235

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416
_exptl_absorpt_coefficient_mu    1.670
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8738
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13139
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         28.33
_reflns_number_total             3676
_reflns_number_gt                3099
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEXll'
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    WingX
_computing_publication_material  WingX

_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)+(0.0460P)²+2.4138P] 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         3676
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Zn1 Zn 0.164459(11) 0.23195(3) 0.159993(17) 0.02421(10) Uani 1 1 d . . .
N1 N 0.10038(8) 0.0833(3) 0.07337(14) 0.0302(4) Uani 1 1 d . . .
C1 C 0.07597(11) 0.0817(4) -0.01912(18) 0.0407(6) Uani 1 1 d . . .
H1 H 0.0792 0.1706 -0.0554 0.049 Uiso 1 1 calc R . .
N2 N 0.04619(9) -0.0631(3) -0.05419(16) 0.0443(6) Uani 1 1 d . . .
H2 H 0.0270 -0.0889 -0.1130 0.053 Uiso 1 1 calc R . .
C2 C 0.05110(10) -0.1649(4) 0.01956(18) 0.0338(5) Uani 1 1 d . . .
C3 C 0.08486(10) -0.0710(4) 0.09823(18) 0.0354(6) Uani 1 1 d . . .
H3 H 0.0958 -0.1059 0.1597 0.042 Uiso 1 1 calc R . .
C4 C 0.02483(10) -0.3356(4) 0.00826(19) 0.0363(6) Uani 1 1 d . . .
C5 C -0.01130(13) -0.4045(4) -0.0789(2) 0.0533(8) Uani 1 1 d . . .
H5 H -0.0193 -0.3412 -0.1330 0.064 Uiso 1 1 calc R . .
C6 C 0.03590(13) -0.4334(4) 0.0872(2) 0.0535(8) Uani 1 1 d . . .
H6 H 0.0602 -0.3897 0.1468 0.064 Uiso 1 1 calc R . .
O1 O 0.16701(8) 0.2184(2) 0.28147(12) 0.0365(4) Uani 1 1 d . . .
C7 C 0.18295(9) 0.0866(3) 0.33605(15) 0.0253(5) Uani 1 1 d . . .
O2 O 0.19325(8) -0.0593(2) 0.31560(11) 0.0378(4) Uani 1 1 d . . .
C8 C 0.18837(9) 0.1184(3) 0.43220(14) 0.0225(4) Uani 1 1 d . . .
C9 C 0.17456(9) 0.2798(3) 0.45341(16) 0.0235(4) Uani 1 1 d . . .
H9 H 0.1608 0.3673 0.4078 0.028 Uiso 1 1 calc R . .
C10 C 0.18111(9) 0.3122(3) 0.54278(15) 0.0220(4) Uani 1 1 d . . .
C11 C 0.20122(9) 0.1795(3) 0.61008(15) 0.0230(4) Uani 1 1 d . . .
H11 H 0.2050 0.1992 0.6695 0.028 Uiso 1 1 calc R . .
C12 C 0.21562(8) 0.0183(3) 0.58912(14) 0.0214(4) Uani 1 1 d . . .
C13 C 0.20902(9) -0.0131(3) 0.50033(15) 0.0228(4) Uani 1 1 d . . .
H13 H 0.2184 -0.1218 0.4861 0.027 Uiso 1 1 calc R . .
O3 O 0.17634(7) 0.5147(2) 0.65040(11) 0.0285(4) Uani 1 1 d . . .
C14 C 0.16823(9) 0.4894(3) 0.56633(16) 0.0253(5) Uani 1 1 d . . .
O4 O 0.15155(8) 0.6078(2) 0.50678(12) 0.0421(4) Uani 1 1 d . . .
N3 N 0.23402(8) -0.1178(2) 0.65933(12) 0.0249(4) Uani 1 1 d . . .
H3A H 0.2411 -0.2208 0.6464 0.030 Uiso 1 1 calc R . .
H3B H 0.2379 -0.0961 0.7142 0.030 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
Zn1 O1 1.9410(17) . ?
Zn1 O3 1.9791(16) 6_565 ?
Zn1 N1 1.9905(19) . ?
Zn1 N3 2.1075(18) 6 ?
N1 C1 1.313(3) . ?
N1 C3 1.378(3) . ?
C1 N2 1.327(3) . ?
N2 C2 1.378(3) . ?
C2 C3 1.362(3) . ?
C2 C4 1.457(4) . ?
C4 C5 1.378(4) . ?
C4 C6 1.384(4) . ?
C5 C6 1.384(4) 5_545 ?
C6 C5 1.384(4) 5_545 ?
O1 C7 1.269(3) . ?
C7 O2 1.234(3) . ?
C7 C8 1.513(3) . ?
C8 C9 1.381(3) . ?
C8 C13 1.394(3) . ?
C9 C10 1.394(3) . ?
C10 C11 1.392(3) . ?
C10 C14 1.494(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.383(3) . ?
C12 N3 1.440(3) . ?
O3 C14 1.286(3) . ?
O3 Zn1 1.9791(16) 6_566 ?
C14 O4 1.237(3) . ?
N3 Zn1 2.1075(18) 6_556 ?

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 101.90(7) . 6_565 ?
O1 Zn1 N1 105.65(8) . . ?
O3 Zn1 N1 128.63(8) 6_565 . ?
O1 Zn1 N3 113.47(7) . 6 ?
O3 Zn1 N3 102.60(7) 6_565 6 ?
N1 Zn1 N3 104.82(8) . 6 ?
C1 N1 C3 105.5(2) . . ?
C1 N1 Zn1 126.76(17) . . ?
C3 N1 Zn1 125.03(16) . . ?
N1 C1 N2 111.4(2) . . ?
C1 N2 C2 108.5(2) . . ?
C3 C2 N2 104.6(2) . . ?
C3 C2 C4 131.2(2) . . ?
N2 C2 C4 124.2(2) . . ?
C2 C3 N1 110.0(2) . . ?
C5 C4 C6 118.0(3) . . ?
C5 C4 C2 122.5(3) . . ?
C6 C4 C2 119.5(2) . . ?
C6 C5 C4 121.1(3) 5_545 . ?
C5 C6 C4 120.9(3) 5_545 . ?
C7 O1 Zn1 125.53(15) . . ?
O2 C7 O1 125.0(2) . . ?
O2 C7 C8 120.1(2) . . ?
O1 C7 C8 114.9(2) . . ?
C9 C8 C13 119.98(19) . . ?
C9 C8 C7 119.9(2) . . ?
C13 C8 C7 120.1(2) . . ?
C8 C9 C10 120.4(2) . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 C14 120.73(19) . . ?
C9 C10 C14 119.99(19) . . ?
C12 C11 C10 120.38(19) . . ?
C13 C12 C11 120.10(19) . . ?
C13 C12 N3 121.16(19) . . ?
C11 C12 N3 118.62(18) . . ?
C12 C13 C8 119.9(2) . . ?
C14 O3 Zn1 106.26(14) . 6_566 ?
O4 C14 O3 121.8(2) . . ?
O4 C14 C10 120.3(2) . . ?
O3 C14 C10 117.84(19) . . ?
C12 N3 Zn1 109.34(13) . 6_556 ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.072

# SQUEEZE RESULTS (APPEND TO CIF)
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
1 0.000 -0.194 0.250 130.2 24.6
2 0.000 0.152 0.750 130.2 24.6
3 0.500 0.089 0.250 130.2 24.6
4 0.500 -0.119 0.750 130.2 24.6
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_compound2
_audit_block_doi                 10.5517/cc1km85m
_database_code_depnum_ccdc_archive 'CCDC 1448480'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N5 O7 Zn'
_chemical_formula_weight         570.85

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   p2(1)/c

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

_cell_length_a                   10.2372(3)
_cell_length_b                   27.0204(7)
_cell_length_c                   8.7380(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.5680(10)
_cell_angle_gamma                90.00
_cell_volume                     2405.64(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6984
_cell_measurement_theta_min      2.5035
_cell_measurement_theta_max      28.1295

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    1.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8404
_exptl_absorpt_correction_T_max  0.9581
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21727
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         28.29
_reflns_number_total             5931
_reflns_number_gt                5103
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       'Bruker SMART APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    WingX
_computing_publication_material  WingX

_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)+(0.0559P)²+8.0151P] 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         5931
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1523
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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 0.42582(4) 0.432470(14) 0.30665(4) 0.01044(12) Uani 1 1 d . . .
N1 N 0.4371(3) 0.49505(10) 0.1910(3) 0.0121(5) Uani 1 1 d . . .
N2 N 0.3836(3) 0.55948(11) 0.0453(3) 0.0142(6) Uani 1 1 d . . .
H2 H 0.3460 0.5770 -0.0284 0.017 Uiso 1 1 calc R . .
C4 C 0.5086(3) 0.62859(13) 0.1841(4) 0.0142(6) Uani 1 1 d . . .
C7 C 0.5705(3) 0.72885(13) 0.2451(4) 0.0159(7) Uani 1 1 d . . .
C1 C 0.3644(3) 0.51152(13) 0.0671(4) 0.0141(6) Uani 1 1 d . . .
H1 H 0.3075 0.4919 0.0036 0.017 Uiso 1 1 calc R . .
C9 C 0.6075(4) 0.64209(14) 0.2983(4) 0.0198(7) Uani 1 1 d . . .
H9 H 0.6539 0.6175 0.3548 0.024 Uiso 1 1 calc R . .
C10 C 0.6003(3) 0.78122(13) 0.2753(4) 0.0162(7) Uani 1 1 d . . .
C2 C 0.4742(3) 0.57653(13) 0.1611(4) 0.0135(6) Uani 1 1 d . . .
C3 C 0.5074(3) 0.53570(13) 0.2506(4) 0.0131(6) Uani 1 1 d . . .
H3 H 0.5676 0.5354 0.3374 0.016 Uiso 1 1 calc R . .
C8 C 0.6376(4) 0.69096(14) 0.3288(4) 0.0201(7) Uani 1 1 d . . .
H8 H 0.7032 0.6989 0.4060 0.024 Uiso 1 1 calc R . .
C6 C 0.4733(4) 0.71526(14) 0.1293(4) 0.0208(8) Uani 1 1 d . . .
H6 H 0.4283 0.7398 0.0713 0.025 Uiso 1 1 calc R . .
C5 C 0.4423(4) 0.66629(14) 0.0989(4) 0.0194(7) Uani 1 1 d . . .
H5 H 0.3770 0.6583 0.0213 0.023 Uiso 1 1 calc R . .
C13 C 0.1753(3) 0.44174(12) 0.3724(4) 0.0115(6) Uani 1 1 d . . .
C19 C -0.0669(3) 0.43323(13) 0.3841(4) 0.0131(6) Uani 1 1 d . . .
H20 H -0.0766 0.4326 0.2772 0.016 Uiso 1 1 calc R . .
C20 C -0.0235(3) 0.43224(15) 0.8757(4) 0.0193(7) Uani 1 1 d . . .
C18 C -0.1772(3) 0.42810(13) 0.4657(4) 0.0132(6) Uani 1 1 d . . .
C14 C 0.0572(3) 0.43927(13) 0.4619(4) 0.0132(6) Uani 1 1 d . . .
C17 C -0.1627(3) 0.42885(13) 0.6256(4) 0.0147(7) Uani 1 1 d . . .
H18 H -0.2357 0.4255 0.6803 0.018 Uiso 1 1 calc R . .
C16 C -0.0376(3) 0.43472(13) 0.7041(4) 0.0146(7) Uani 1 1 d . . .
C15 C 0.0713(3) 0.44056(13) 0.6219(4) 0.0141(6) Uani 1 1 d . . .
H16 H 0.1539 0.4453 0.6741 0.017 Uiso 1 1 calc R . .
N3 N 0.6992(3) 0.79781(11) 0.3827(4) 0.0185(6) Uani 1 1 d . . .
H3A H 0.7511 0.7795 0.4417 0.022 Uiso 1 1 calc R . .
N4 N 0.6080(3) 0.86438(11) 0.2762(3) 0.0141(6) Uani 1 1 d . . .
C12 C 0.5448(3) 0.82340(13) 0.2101(4) 0.0155(7) Uani 1 1 d . . .
H13 H 0.4753 0.8242 0.1332 0.019 Uiso 1 1 calc R . .
O2 O 0.1614(2) 0.44161(10) 0.2294(3) 0.0164(5) Uani 1 1 d . . .
O1 O 0.2872(2) 0.44189(9) 0.4503(3) 0.0125(5) Uani 1 1 d . . .
O3 O 0.0889(3) 0.45084(12) 0.9381(3) 0.0261(6) Uani 1 1 d . . .
H14 H 0.0971 0.4449 1.0306 0.039 Uiso 1 1 calc R . .
O4 O -0.1037(3) 0.41326(14) 0.9502(3) 0.0345(8) Uani 1 1 d . . .
O5 O -0.4097(2) 0.43022(10) 0.4453(3) 0.0167(5) Uani 1 1 d . . .
C21 C -0.3091(3) 0.42046(13) 0.3765(4) 0.0138(6) Uani 1 1 d . . .
O6 O -0.3119(2) 0.40478(11) 0.2424(3) 0.0194(5) Uani 1 1 d . . .
C11 C 0.6998(4) 0.84725(14) 0.3785(4) 0.0192(7) Uani 1 1 d . . .
H11 H 0.7577 0.8670 0.4401 0.023 Uiso 1 1 calc R . .
C23 C 1.0357(6) 0.2580(4) 0.8219(7) 0.075(2) Uani 1 1 d . . .
O7 O 1.1191(3) 0.24799(15) 0.9153(4) 0.0442(9) Uani 1 1 d . . .
C22 C 1.0105(18) 0.3153(4) 0.7667(15) 0.204(9) Uani 1 1 d . . .
H25A H 1.0509 0.3373 0.8437 0.306 Uiso 1 1 calc R . .
H25B H 0.9179 0.3217 0.7524 0.306 Uiso 1 1 calc R . .
H25C H 1.0480 0.3207 0.6715 0.306 Uiso 1 1 calc R . .
N5 N 0.9439(4) 0.2366(2) 0.7433(5) 0.0625(17) Uani 1 1 d . . .
C25 C 0.9641(12) 0.1773(3) 0.7736(13) 0.124(4) Uani 1 1 d . . .
H23A H 1.0427 0.1719 0.8407 0.187 Uiso 1 1 calc R . .
H23B H 0.9712 0.1607 0.6775 0.187 Uiso 1 1 calc R . .
H23C H 0.8902 0.1643 0.8204 0.187 Uiso 1 1 calc R . .
C24 C 0.8367(8) 0.2437(6) 0.6405(10) 0.142(6) Uani 1 1 d . . .
H22A H 0.7632 0.2262 0.6742 0.213 Uiso 1 1 calc R . .
H22B H 0.8548 0.2316 0.5414 0.213 Uiso 1 1 calc R . .
H22C H 0.8168 0.2784 0.6335 0.213 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
Zn1 O5 1.977(2) 1_655 ?
Zn1 N1 1.979(3) . ?
Zn1 N4 1.995(3) 2_645 ?
Zn1 O1 2.001(2) . ?
N1 C1 1.330(4) . ?
N1 C3 1.387(4) . ?
N2 C1 1.327(5) . ?
N2 C2 1.383(4) . ?
C4 C5 1.398(5) . ?
C4 C9 1.399(5) . ?
C4 C2 1.459(5) . ?
C7 C6 1.398(5) . ?
C7 C8 1.399(5) . ?
C7 C10 1.466(5) . ?
C9 C8 1.376(5) . ?
C10 C12 1.373(5) . ?
C10 N3 1.387(4) . ?
C2 C3 1.376(5) . ?
C6 C5 1.380(5) . ?
C13 O2 1.244(4) . ?
C13 O1 1.274(4) . ?
C13 C14 1.504(4) . ?
C19 C14 1.391(4) . ?
C19 C18 1.399(4) . ?
C20 O4 1.211(5) . ?
C20 O3 1.323(4) . ?
C20 C16 1.494(5) . ?
C18 C17 1.391(5) . ?
C18 C21 1.506(4) . ?
C14 C15 1.392(5) . ?
C17 C16 1.402(4) . ?
C16 C15 1.392(5) . ?
N3 C11 1.336(5) . ?
N4 C11 1.317(4) . ?
N4 C12 1.380(4) . ?
N4 Zn1 1.995(3) 2_655 ?
O5 C21 1.270(4) . ?
O5 Zn1 1.977(2) 1_455 ?
C21 O6 1.244(4) . ?
C23 O7 1.154(7) . ?
C23 N5 1.251(8) . ?
C23 C22 1.636(13) . ?
N5 C24 1.362(8) . ?
N5 C25 1.634(11) . ?

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
O5 Zn1 N1 104.53(11) 1_655 . ?
O5 Zn1 N4 107.54(11) 1_655 2_645 ?
N1 Zn1 N4 128.28(12) . 2_645 ?
O5 Zn1 O1 103.47(10) 1_655 . ?
N1 Zn1 O1 106.96(11) . . ?
N4 Zn1 O1 103.68(11) 2_645 . ?
C1 N1 C3 105.6(3) . . ?
C1 N1 Zn1 130.3(2) . . ?
C3 N1 Zn1 122.6(2) . . ?
C1 N2 C2 108.6(3) . . ?
C5 C4 C9 118.1(3) . . ?
C5 C4 C2 122.0(3) . . ?
C9 C4 C2 119.9(3) . . ?
C6 C7 C8 117.7(3) . . ?
C6 C7 C10 120.3(3) . . ?
C8 C7 C10 122.0(3) . . ?
N2 C1 N1 111.4(3) . . ?
C8 C9 C4 121.4(3) . . ?
C12 C10 N3 105.0(3) . . ?
C12 C10 C7 131.0(3) . . ?
N3 C10 C7 124.0(3) . . ?
C3 C2 N2 105.0(3) . . ?
C3 C2 C4 130.6(3) . . ?
N2 C2 C4 123.9(3) . . ?
C2 C3 N1 109.3(3) . . ?
C9 C8 C7 120.8(3) . . ?
C5 C6 C7 121.7(3) . . ?
C6 C5 C4 120.4(3) . . ?
O2 C13 O1 123.1(3) . . ?
O2 C13 C14 120.2(3) . . ?
O1 C13 C14 116.7(3) . . ?
C14 C19 C18 120.5(3) . . ?
O4 C20 O3 123.2(3) . . ?
O4 C20 C16 123.7(3) . . ?
O3 C20 C16 113.1(3) . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 C21 121.6(3) . . ?
C19 C18 C21 118.5(3) . . ?
C19 C14 C15 119.6(3) . . ?
C19 C14 C13 119.6(3) . . ?
C15 C14 C13 120.7(3) . . ?
C18 C17 C16 119.7(3) . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 C20 121.3(3) . . ?
C17 C16 C20 118.7(3) . . ?
C14 C15 C16 120.3(3) . . ?
C11 N3 C10 108.0(3) . . ?
C11 N4 C12 106.1(3) . . ?
C11 N4 Zn1 131.1(3) . 2_655 ?
C12 N4 Zn1 122.0(2) . 2_655 ?
C10 C12 N4 109.5(3) . . ?
C13 O1 Zn1 108.7(2) . . ?
C21 O5 Zn1 113.4(2) . 1_455 ?
O6 C21 O5 124.8(3) . . ?
O6 C21 C18 118.1(3) . . ?
O5 C21 C18 117.0(3) . . ?
N4 C11 N3 111.4(3) . . ?
O7 C23 N5 138.2(10) . . ?
O7 C23 C22 121.0(9) . . ?
N5 C23 C22 100.8(8) . . ?
C23 N5 C24 144.1(10) . . ?
C23 N5 C25 106.7(7) . . ?
C24 N5 C25 109.1(8) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.987
_refine_diff_density_min         -1.234
_refine_diff_density_rms         0.209
####################################################################### 
# 
# 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_compound3
_audit_block_doi                 10.5517/cc1km86n
_database_code_depnum_ccdc_archive 'CCDC 1448481'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 N4 O6 Zn'
_chemical_formula_weight         471.72

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   P2/n

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

_cell_length_a                   11.3869(5)
_cell_length_b                   8.3323(4)
_cell_length_c                   13.9637(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.310(3)
_cell_angle_gamma                90.00
_cell_volume                     1316.84(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3028
_cell_measurement_theta_min      2.8525
_cell_measurement_theta_max      26.7085

_exptl_crystal_description       cubic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.968
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8300
_exptl_absorpt_correction_T_max  0.9094
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11438
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3250
_reflns_number_gt                2697
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEXll'
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    WingX
_computing_publication_material  WingX

_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)+(0.0586P)²+0.1149P] 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         3250
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.7500 0.65094(4) 0.7500 0.01250(13) Uani 1 2 d S . .
N1 N 0.63354(17) 0.5109(2) 0.67591(13) 0.0164(4) Uani 1 1 d . . .
C1 C 0.5174(2) 0.5297(3) 0.66729(16) 0.0195(5) Uani 1 1 d . . .
H1 H 0.4787 0.6176 0.6903 0.023 Uiso 1 1 calc R . .
N2 N 0.46336(17) 0.4044(2) 0.62069(14) 0.0192(4) Uani 1 1 d . . .
H2 H 0.3884 0.3931 0.6066 0.023 Uiso 1 1 calc R . .
C2 C 0.5488(2) 0.2976(3) 0.59948(15) 0.0153(5) Uani 1 1 d . . .
C3 C 0.6544(2) 0.3654(3) 0.63327(15) 0.0161(5) Uani 1 1 d . . .
H3 H 0.7284 0.3209 0.6284 0.019 Uiso 1 1 calc R . .
C4 C 0.5227(2) 0.1450(3) 0.54953(15) 0.0162(5) Uani 1 1 d . . .
C5 C 0.4244(2) 0.1298(3) 0.47947(16) 0.0172(5) Uani 1 1 d . . .
H5 H 0.3737 0.2162 0.4659 0.021 Uiso 1 1 calc R . .
C6 C 0.5966(2) 0.0139(3) 0.56918(15) 0.0163(5) Uani 1 1 d . . .
H6 H 0.6612 0.0227 0.6158 0.020 Uiso 1 1 calc R . .
O1 O 0.84495(15) 0.8106(2) 0.68701(11) 0.0193(4) Uani 1 1 d . . .
C7 C 0.8872(2) 0.7600(3) 0.60972(16) 0.0177(5) Uani 1 1 d . . .
O2 O 0.87774(17) 0.6203(2) 0.58192(12) 0.0246(4) Uani 1 1 d . . .
C8 C 0.9472(2) 0.8860(3) 0.55509(15) 0.0161(5) Uani 1 1 d . . .
C9 C 0.9540(2) 1.0475(3) 0.58529(15) 0.0174(5) Uani 1 1 d . . .
O3 O 0.91133(17) 1.1016(2) 0.66611(12) 0.0236(4) Uani 1 1 d . . .
H3A H 0.8868 1.0257 0.6955 0.035 Uiso 1 1 calc R . .
C10 C 0.9937(2) 0.8414(3) 0.47101(16) 0.0182(5) Uani 1 1 d . . .
H10 H 0.9896 0.7344 0.4519 0.022 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
Zn1 N1 1.9721(19) . ?
Zn1 N1 1.9721(19) 2_656 ?
Zn1 O1 1.9799(16) 2_656 ?
Zn1 O1 1.9799(16) . ?
N1 C1 1.324(3) . ?
N1 C3 1.383(3) . ?
C1 N2 1.343(3) . ?
N2 C2 1.375(3) . ?
C2 C3 1.365(3) . ?
C2 C4 1.465(3) . ?
C4 C6 1.388(3) . ?
C4 C5 1.408(3) . ?
C5 C6 1.384(3) 3_656 ?
C6 C5 1.384(3) 3_656 ?
O1 C7 1.299(3) . ?
C7 O2 1.228(3) . ?
C7 C8 1.505(3) . ?
C8 C10 1.390(3) . ?
C8 C9 1.409(3) . ?
C9 O3 1.354(3) . ?
C9 C10 1.391(3) 3_776 ?
C10 C9 1.391(3) 3_776 ?

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 107.44(11) . 2_656 ?
N1 Zn1 O1 105.19(7) . 2_656 ?
N1 Zn1 O1 122.20(7) 2_656 2_656 ?
N1 Zn1 O1 122.20(7) . . ?
N1 Zn1 O1 105.19(7) 2_656 . ?
O1 Zn1 O1 95.60(10) 2_656 . ?
C1 N1 C3 106.4(2) . . ?
C1 N1 Zn1 125.79(16) . . ?
C3 N1 Zn1 127.40(16) . . ?
N1 C1 N2 110.6(2) . . ?
C1 N2 C2 108.1(2) . . ?
C3 C2 N2 105.9(2) . . ?
C3 C2 C4 130.5(2) . . ?
N2 C2 C4 123.6(2) . . ?
C2 C3 N1 109.0(2) . . ?
C6 C4 C5 118.9(2) . . ?
C6 C4 C2 120.1(2) . . ?
C5 C4 C2 120.9(2) . . ?
C6 C5 C4 120.0(2) 3_656 . ?
C5 C6 C4 121.0(2) 3_656 . ?
C7 O1 Zn1 114.92(15) . . ?
O2 C7 O1 122.9(2) . . ?
O2 C7 C8 122.0(2) . . ?
O1 C7 C8 115.2(2) . . ?
C10 C8 C9 119.6(2) . . ?
C10 C8 C7 118.5(2) . . ?
C9 C8 C7 121.8(2) . . ?
O3 C9 C10 117.7(2) . 3_776 ?
O3 C9 C8 123.7(2) . . ?
C10 C9 C8 118.6(2) 3_776 . ?
C8 C10 C9 121.7(2) . 3_776 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.086

# SQUEEZE RESULTS (APPEND TO CIF)
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
1 0.250 -0.080 0.750 214.1 34.2
2 0.750 0.040 0.250 214.1 34.5
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_compound4
_audit_block_doi                 10.5517/cc1km87p
_database_code_depnum_ccdc_archive 'CCDC 1448482'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 N4 O6 Zn'
_chemical_formula_weight         547.81

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   P2(1)/n

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

_cell_length_a                   12.8815(9)
_cell_length_b                   15.2513(11)
_cell_length_c                   14.1699(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.331(4)
_cell_angle_gamma                90.00
_cell_volume                     2781.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5082
_cell_measurement_theta_min      2.485
_cell_measurement_theta_max      22.74995

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8364
_exptl_absorpt_correction_T_max  0.9551
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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       'omega and phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25004
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         28.33
_reflns_number_total             6832
_reflns_number_gt                4151
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEXll'
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    WingX
_computing_publication_material  WingX

_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)+(0.0539P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6832
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_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 0.14874(2) 0.76341(2) 0.25099(2) 0.03920(12) Uani 1 1 d . . .
N1 N 0.25641(16) 0.72481(15) 0.34888(16) 0.0456(6) Uani 1 1 d . . .
C1 C 0.3039(2) 0.77182(19) 0.4158(2) 0.0495(7) Uani 1 1 d . . .
H1 H 0.2915 0.8310 0.4262 0.059 Uiso 1 1 calc R . .
N2 N 0.37169(18) 0.72367(15) 0.46641(17) 0.0510(6) Uani 1 1 d . . .
H2 H 0.4099 0.7416 0.5137 0.061 Uiso 1 1 calc R . .
C2 C 0.3699(2) 0.64044(18) 0.4301(2) 0.0478(7) Uani 1 1 d . . .
C3 C 0.2983(2) 0.64223(18) 0.3579(2) 0.0508(7) Uani 1 1 d . . .
H3 H 0.2801 0.5946 0.3198 0.061 Uiso 1 1 calc R . .
C4 C 0.4375(2) 0.56955(18) 0.4666(2) 0.0510(7) Uani 1 1 d . . .
C5 C 0.4925(2) 0.5752(2) 0.5524(2) 0.0684(10) Uani 1 1 d . . .
H5 H 0.4884 0.6260 0.5885 0.082 Uiso 1 1 calc R . .
C6 C 0.4463(3) 0.4940(2) 0.4151(2) 0.0685(10) Uani 1 1 d . . .
H6 H 0.4105 0.4892 0.3570 0.082 Uiso 1 1 calc R . .
N3 N 0.22515(16) 0.80974(14) 0.14257(15) 0.0435(5) Uani 1 1 d . . .
C7 C 0.2195(3) 0.7844(2) 0.0556(2) 0.0618(9) Uani 1 1 d . . .
H7 H 0.1746 0.7409 0.0326 0.074 Uiso 1 1 calc R . .
N4 N 0.2857(2) 0.82772(19) 0.00240(18) 0.0728(8) Uani 1 1 d . . .
H4 H 0.2929 0.8205 -0.0572 0.087 Uiso 1 1 calc R . .
C8 C 0.3398(2) 0.8855(2) 0.0593(2) 0.0552(8) Uani 1 1 d . . .
C9 C 0.3012(2) 0.8731(2) 0.1471(2) 0.0517(7) Uani 1 1 d . . .
H9 H 0.3232 0.9030 0.2015 0.062 Uiso 1 1 calc R . .
C10 C 0.4215(2) 0.9434(2) 0.0283(2) 0.0604(8) Uani 1 1 d . . .
C11 C 0.4681(3) 0.9306(2) -0.0570(2) 0.0735(10) Uani 1 1 d . . .
H11 H 0.4473 0.8842 -0.0959 0.088 Uiso 1 1 calc R . .
C12 C 0.5457(3) 0.9867(2) -0.0845(2) 0.0743(11) Uani 1 1 d . . .
H12 H 0.5765 0.9774 -0.1418 0.089 Uiso 1 1 calc R . .
O1 O 0.04731(13) 0.84393(15) 0.30655(14) 0.0552(5) Uani 1 1 d . . .
C13 C 0.0870(2) 0.9153(2) 0.33064(19) 0.0509(8) Uani 1 1 d . . .
O2 O 0.18317(14) 0.93140(16) 0.32732(15) 0.0665(6) Uani 1 1 d . . .
C14 C 0.0195(2) 0.9867(2) 0.3653(2) 0.0518(7) Uani 1 1 d . . .
C15 C 0.0606(2) 1.0683(2) 0.3933(2) 0.0591(8) Uani 1 1 d . . .
C16 C -0.0049(2) 1.1327(2) 0.4256(3) 0.0711(9) Uani 1 1 d . . .
H16 H 0.0222 1.1863 0.4461 0.085 Uiso 1 1 calc R . .
C17 C -0.1105(2) 1.1175(2) 0.4275(2) 0.0654(9) Uani 1 1 d . . .
H17 H -0.1533 1.1617 0.4491 0.078 Uiso 1 1 calc R . .
C18 C -0.1552(2) 1.0382(2) 0.3982(2) 0.0511(7) Uani 1 1 d . . .
C19 C -0.0886(2) 0.9740(2) 0.3693(2) 0.0519(7) Uani 1 1 d . . .
H19 H -0.1161 0.9197 0.3517 0.062 Uiso 1 1 calc R . .
O5 O 0.16324(15) 1.08600(17) 0.39163(19) 0.0774(7) Uani 1 1 d . . .
H3A H 0.1935 1.0442 0.3688 0.116 Uiso 1 1 calc R . .
C20 C -0.2691(2) 1.0233(2) 0.3967(2) 0.0507(7) Uani 1 1 d . . .
C21 C -0.33764(19) 1.09134(19) 0.3745(2) 0.0499(7) Uani 1 1 d . . .
H21 H -0.3115 1.1476 0.3666 0.060 Uiso 1 1 calc R . .
C22 C -0.4441(2) 1.07763(19) 0.36394(19) 0.0470(7) Uani 1 1 d . . .
C23 C -0.4835(2) 0.9940(2) 0.3757(2) 0.0567(8) Uani 1 1 d . . .
C24 C -0.4168(2) 0.9266(2) 0.4044(3) 0.0682(9) Uani 1 1 d . . .
H24 H -0.4433 0.8714 0.4175 0.082 Uiso 1 1 calc R . .
C25 C -0.3117(2) 0.9416(2) 0.4133(2) 0.0647(9) Uani 1 1 d . . .
H25 H -0.2678 0.8955 0.4310 0.078 Uiso 1 1 calc R . .
O6 O -0.58657(15) 0.97472(16) 0.3611(2) 0.0822(7) Uani 1 1 d . . .
H6A H -0.6181 1.0191 0.3443 0.123 Uiso 1 1 calc R . .
C26 C -0.5118(2) 1.1547(2) 0.3383(2) 0.0500(7) Uani 1 1 d . . .
O4 O -0.48471(18) 1.22842(15) 0.36772(18) 0.0751(7) Uani 1 1 d . . .
O3 O -0.59334(14) 1.14252(14) 0.28939(14) 0.0617(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
Zn1 O1 1.9796(19) . ?
Zn1 N3 1.988(2) . ?
Zn1 N1 2.009(2) . ?
Zn1 O3 2.050(2) 2_445 ?
N1 C1 1.319(3) . ?
N1 C3 1.374(3) . ?
C1 N2 1.329(3) . ?
N2 C2 1.370(3) . ?
C2 C3 1.349(3) . ?
C2 C4 1.469(4) . ?
C4 C6 1.371(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.385(4) 3_666 ?
C6 C5 1.385(4) 3_666 ?
N3 C7 1.291(4) . ?
N3 C9 1.376(3) . ?
C7 N4 1.336(4) . ?
N4 C8 1.367(4) . ?
C8 C9 1.371(4) . ?
C8 C10 1.456(4) . ?
C10 C11 1.385(4) . ?
C10 C12 1.386(4) 3_675 ?
C11 C12 1.384(4) . ?
C12 C10 1.386(4) 3_675 ?
O1 C13 1.244(4) . ?
C13 O2 1.266(3) . ?
C13 C14 1.489(4) . ?
C14 C15 1.404(4) . ?
C14 C19 1.409(4) . ?
C15 O5 1.351(3) . ?
C15 C16 1.385(5) . ?
C16 C17 1.381(4) . ?
C17 C18 1.395(4) . ?
C18 C19 1.376(4) . ?
C18 C20 1.484(4) . ?
C20 C25 1.386(4) . ?
C20 C21 1.390(4) . ?
C21 C22 1.390(3) . ?
C22 C23 1.385(4) . ?
C22 C26 1.500(4) . ?
C23 O6 1.368(3) . ?
C23 C24 1.390(4) . ?
C24 C25 1.373(4) . ?
C26 O4 1.244(3) . ?
C26 O3 1.249(3) . ?
O3 Zn1 2.050(2) 2_455 ?

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 N3 116.26(9) . . ?
O1 Zn1 N1 110.82(9) . . ?
N3 Zn1 N1 106.74(9) . . ?
O1 Zn1 O3 116.17(9) . 2_445 ?
N3 Zn1 O3 106.36(9) . 2_445 ?
N1 Zn1 O3 98.73(8) . 2_445 ?
C1 N1 C3 105.2(2) . . ?
C1 N1 Zn1 128.59(19) . . ?
C3 N1 Zn1 126.18(18) . . ?
N1 C1 N2 111.3(2) . . ?
C1 N2 C2 108.0(2) . . ?
C3 C2 N2 105.5(2) . . ?
C3 C2 C4 131.2(3) . . ?
N2 C2 C4 123.3(2) . . ?
C2 C3 N1 110.1(2) . . ?
C6 C4 C5 118.0(3) . . ?
C6 C4 C2 119.5(2) . . ?
C5 C4 C2 122.5(2) . . ?
C6 C5 C4 120.5(3) 3_666 . ?
C4 C6 C5 121.5(3) . 3_666 ?
C7 N3 C9 105.5(2) . . ?
C7 N3 Zn1 128.37(19) . . ?
C9 N3 Zn1 126.00(19) . . ?
N3 C7 N4 112.2(3) . . ?
C7 N4 C8 108.0(2) . . ?
N4 C8 C9 104.5(2) . . ?
N4 C8 C10 124.8(3) . . ?
C9 C8 C10 130.6(3) . . ?
C8 C9 N3 109.8(2) . . ?
C11 C10 C12 118.5(3) . 3_675 ?
C11 C10 C8 121.5(3) . . ?
C12 C10 C8 120.0(3) 3_675 . ?
C12 C11 C10 120.1(3) . . ?
C11 C12 C10 121.4(3) . 3_675 ?
C13 O1 Zn1 112.39(17) . . ?
O1 C13 O2 123.5(3) . . ?
O1 C13 C14 119.4(2) . . ?
O2 C13 C14 117.1(3) . . ?
C15 C14 C19 118.1(3) . . ?
C15 C14 C13 121.6(3) . . ?
C19 C14 C13 120.2(3) . . ?
O5 C15 C16 118.4(3) . . ?
O5 C15 C14 121.9(3) . . ?
C16 C15 C14 119.7(3) . . ?
C17 C16 C15 120.1(3) . . ?
C16 C17 C18 122.3(3) . . ?
C19 C18 C17 116.8(3) . . ?
C19 C18 C20 121.0(3) . . ?
C17 C18 C20 122.2(3) . . ?
C18 C19 C14 122.9(3) . . ?
C25 C20 C21 117.2(2) . . ?
C25 C20 C18 122.3(3) . . ?
C21 C20 C18 120.5(3) . . ?
C20 C21 C22 121.8(3) . . ?
C23 C22 C21 119.3(3) . . ?
C23 C22 C26 122.7(2) . . ?
C21 C22 C26 118.0(3) . . ?
O6 C23 C22 122.5(3) . . ?
O6 C23 C24 118.0(3) . . ?
C22 C23 C24 119.5(3) . . ?
C25 C24 C23 119.9(3) . . ?
C24 C25 C20 122.0(3) . . ?
O4 C26 O3 122.6(3) . . ?
O4 C26 C22 118.4(2) . . ?
O3 C26 C22 119.0(3) . . ?
C26 O3 Zn1 107.23(19) . 2_455 ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.059

# SQUEEZE RESULTS (APPEND TO CIF)
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
1 -0.250 0.178 0.250 326.2 70.3
2 0.250 0.749 0.750 326.3 69.9
_platon_squeeze_details          
;
;
