# Electronic Supplementary Material (ESI) for ChemComm.
# 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_LJB_1_310K
_database_code_depnum_ccdc_archive 'CCDC 1441452'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn'
_chemical_formula_sum            'C22 H18 N2 O6 Zn'
_chemical_formula_weight         471.75

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   18.972(2)
_cell_length_b                   7.8309(9)
_cell_length_c                   13.6741(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2031.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    310(2)
_cell_measurement_reflns_used    2574
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      24.57


_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.553
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5444
_exptl_absorpt_correction_T_max  0.8005
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      310(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10474
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3940
_reflns_number_gt                3279
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0465P)²+0.8119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3940
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.39087(2) 1.05796(5) 0.81927(3) 0.02310(13) Uani 1 1 d . . .
O1 O 0.47214(16) 0.9453(4) 0.8784(2) 0.0332(8) Uani 1 1 d . . .
O2 O 0.5010(2) 0.7823(6) 0.7522(3) 0.0646(12) Uani 1 1 d . . .
O3 O 0.7671(2) 0.6748(6) 0.7418(3) 0.0658(13) Uani 1 1 d . . .
O4 O 0.80942(16) 0.5557(4) 0.8764(2) 0.0371(8) Uani 1 1 d . . .
O5 O 0.69761(19) 0.7330(6) 1.1941(2) 0.0564(11) Uani 1 1 d . . .
O6 O 0.59799(16) 0.8786(5) 1.1843(2) 0.0373(8) Uani 1 1 d . . .
N1 N 0.39631(19) 1.2688(5) 0.9090(3) 0.0296(9) Uani 1 1 d . . .
N2 N 0.3262(2) 1.7797(6) 1.5687(3) 0.0460(11) Uani 1 1 d . . .
H2 H 0.3142 1.7806 1.6293 0.055 Uiso 1 1 calc R . .
C1 C 0.5129(2) 0.8440(6) 0.8330(3) 0.0301(10) Uani 1 1 d . . .
C2 C 0.5794(2) 0.7965(6) 0.8869(3) 0.0257(9) Uani 1 1 d . . .
C3 C 0.6388(2) 0.7418(5) 0.8370(3) 0.0255(10) Uani 1 1 d . . .
H3 H 0.6378 0.7363 0.7690 0.031 Uiso 1 1 calc R . .
C4 C 0.6998(2) 0.6950(6) 0.8861(3) 0.0279(10) Uani 1 1 d . . .
C5 C 0.7635(2) 0.6383(5) 0.8287(4) 0.0310(10) Uani 1 1 d . . .
C6 C 0.7016(2) 0.7041(6) 0.9877(3) 0.0285(10) Uani 1 1 d . . .
H6 H 0.7414 0.6677 1.0216 0.034 Uiso 1 1 calc R . .
C7 C 0.6441(2) 0.7675(6) 1.0381(3) 0.0265(10) Uani 1 1 d . . .
C8 C 0.6486(2) 0.7913(6) 1.1472(3) 0.0313(11) Uani 1 1 d . . .
C9 C 0.5839(2) 0.8138(6) 0.9879(3) 0.0276(10) Uani 1 1 d . . .
H9 H 0.5456 0.8573 1.0224 0.033 Uiso 1 1 calc R . .
C10 C 0.3865(2) 1.4298(6) 0.8788(3) 0.0341(11) Uani 1 1 d . . .
H10 H 0.3765 1.4495 0.8132 0.041 Uiso 1 1 calc R . .
C11 C 0.3907(3) 1.5680(6) 0.9418(4) 0.0361(11) Uani 1 1 d . . .
H11 H 0.3828 1.6779 0.9185 0.043 Uiso 1 1 calc R . .
C12 C 0.4067(3) 1.5425(6) 1.0393(3) 0.0363(11) Uani 1 1 d . . .
C13 C 0.4179(3) 1.3767(6) 1.0699(3) 0.0376(11) Uani 1 1 d . . .
H13 H 0.4293 1.3542 1.1347 0.045 Uiso 1 1 calc R . .
C14 C 0.4119(3) 1.2446(6) 1.0036(3) 0.0351(11) Uani 1 1 d . . .
H14 H 0.4191 1.1336 1.0256 0.042 Uiso 1 1 calc R . .
C15 C 0.4111(3) 1.6907(7) 1.1091(4) 0.0522(16) Uani 1 1 d . . .
H15A H 0.3861 1.7867 1.0807 0.063 Uiso 1 1 calc R . .
H15B H 0.4602 1.7237 1.1155 0.063 Uiso 1 1 calc R . .
C16 C 0.3814(3) 1.6581(9) 1.2114(4) 0.0547(16) Uani 1 1 d . . .
H16A H 0.3326 1.6222 1.2058 0.066 Uiso 1 1 calc R . .
H16B H 0.4076 1.5658 1.2418 0.066 Uiso 1 1 calc R . .
C17 C 0.3851(4) 1.8070(11) 1.2732(5) 0.079(3) Uani 1 1 d . . .
H17A H 0.3556 1.8950 1.2447 0.095 Uiso 1 1 calc R . .
H17B H 0.4332 1.8488 1.2723 0.095 Uiso 1 1 calc R . .
C18 C 0.3632(3) 1.7836(9) 1.3789(4) 0.0527(17) Uani 1 1 d . . .
C19 C 0.2971(3) 1.8165(10) 1.4054(4) 0.070(2) Uani 1 1 d . . .
H19 H 0.2632 1.8379 1.3578 0.084 Uiso 1 1 calc R . .
C20 C 0.2788(3) 1.8192(10) 1.5023(4) 0.0641(18) Uani 1 1 d . . .
H20 H 0.2333 1.8486 1.5210 0.077 Uiso 1 1 calc R . .
C21 C 0.3911(3) 1.7390(10) 1.5459(4) 0.0579(18) Uani 1 1 d . . .
H21 H 0.4234 1.7115 1.5946 0.069 Uiso 1 1 calc R . .
C22 C 0.4109(3) 1.7372(11) 1.4500(5) 0.070(2) Uani 1 1 d . . .
H22 H 0.4564 1.7049 1.4328 0.084 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 O6 1.922(3) 2_674 ?
Zn1 O4 1.947(3) 4_465 ?
Zn1 O1 1.952(3) . ?
Zn1 N1 2.059(4) . ?
O1 C1 1.271(5) . ?
O2 C1 1.227(6) . ?
O3 C5 1.225(6) . ?
O4 C5 1.265(5) . ?
O4 Zn1 1.947(3) 4_565 ?
O5 C8 1.218(6) . ?
O6 C8 1.283(5) . ?
O6 Zn1 1.922(3) 2_675 ?
N1 C10 1.340(6) . ?
N1 C14 1.341(6) . ?
N2 C21 1.309(7) . ?
N2 C20 1.315(7) . ?
C1 C2 1.507(6) . ?
C2 C3 1.386(6) . ?
C2 C9 1.391(6) . ?
C3 C4 1.387(6) . ?
C4 C6 1.392(6) . ?
C4 C5 1.508(6) . ?
C6 C7 1.383(6) . ?
C7 C9 1.381(6) . ?
C7 C8 1.506(6) . ?
C10 C11 1.386(7) . ?
C11 C12 1.382(7) . ?
C12 C13 1.380(7) . ?
C12 C15 1.505(7) . ?
C13 C14 1.380(7) . ?
C15 C16 1.530(7) . ?
C16 C17 1.441(9) . ?
C17 C18 1.515(8) . ?
C18 C19 1.330(8) . ?
C18 C22 1.378(9) . ?
C19 C20 1.371(8) . ?
C21 C22 1.364(8) . ?

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
O6 Zn1 O4 126.18(13) 2_674 4_465 ?
O6 Zn1 O1 115.31(13) 2_674 . ?
O4 Zn1 O1 104.73(14) 4_465 . ?
O6 Zn1 N1 111.06(15) 2_674 . ?
O4 Zn1 N1 99.63(14) 4_465 . ?
O1 Zn1 N1 94.35(13) . . ?
C1 O1 Zn1 124.1(3) . . ?
C5 O4 Zn1 125.0(3) . 4_565 ?
C8 O6 Zn1 115.8(3) . 2_675 ?
C10 N1 C14 117.5(4) . . ?
C10 N1 Zn1 124.3(3) . . ?
C14 N1 Zn1 118.2(3) . . ?
C21 N2 C20 122.4(5) . . ?
O2 C1 O1 125.0(4) . . ?
O2 C1 C2 119.8(4) . . ?
O1 C1 C2 115.1(4) . . ?
C3 C2 C9 118.0(4) . . ?
C3 C2 C1 121.1(4) . . ?
C9 C2 C1 120.9(4) . . ?
C4 C3 C2 121.5(4) . . ?
C3 C4 C6 119.4(4) . . ?
C3 C4 C5 119.7(4) . . ?
C6 C4 C5 121.0(4) . . ?
O3 C5 O4 125.5(4) . . ?
O3 C5 C4 118.7(4) . . ?
O4 C5 C4 115.7(5) . . ?
C7 C6 C4 119.8(4) . . ?
C9 C7 C6 119.9(4) . . ?
C9 C7 C8 120.5(4) . . ?
C6 C7 C8 119.5(4) . . ?
O5 C8 O6 124.2(4) . . ?
O5 C8 C7 121.2(4) . . ?
O6 C8 C7 114.5(4) . . ?
C7 C9 C2 121.3(4) . . ?
N1 C10 C11 122.4(4) . . ?
C12 C11 C10 120.0(4) . . ?
C13 C12 C11 117.5(4) . . ?
C13 C12 C15 121.6(5) . . ?
C11 C12 C15 120.8(5) . . ?
C14 C13 C12 119.6(4) . . ?
N1 C14 C13 123.1(4) . . ?
C12 C15 C16 115.5(5) . . ?
C17 C16 C15 112.5(5) . . ?
C16 C17 C18 116.6(7) . . ?
C19 C18 C22 118.6(5) . . ?
C19 C18 C17 119.7(6) . . ?
C22 C18 C17 121.7(6) . . ?
C18 C19 C20 120.4(6) . . ?
N2 C20 C19 119.4(5) . . ?
N2 C21 C22 119.3(6) . . ?
C21 C22 C18 119.7(6) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_LJB_1_310K-R
_database_code_depnum_ccdc_archive 'CCDC 1441453'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn'
_chemical_formula_sum            'C22 H18 N2 O6 Zn'
_chemical_formula_weight         471.75

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   18.973(2)
_cell_length_b                   7.8316(9)
_cell_length_c                   13.6758(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2032.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    310(2)
_cell_measurement_reflns_used    2608
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      24.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.553
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5444
_exptl_absorpt_correction_T_max  0.8006
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      310(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10539
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.98
_reflns_number_total             3946
_reflns_number_gt                3281
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0475P)²+0.6766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3946
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.39089(2) 1.05800(5) 0.81522(3) 0.02328(13) Uani 1 1 d . . .
O1 O 0.47215(16) 0.9448(4) 0.8744(2) 0.0334(8) Uani 1 1 d . . .
O2 O 0.5012(2) 0.7826(6) 0.7481(3) 0.0654(13) Uani 1 1 d . . .
O3 O 0.7669(2) 0.6748(6) 0.7375(3) 0.0664(13) Uani 1 1 d . . .
O4 O 0.80952(17) 0.5553(4) 0.8723(2) 0.0373(8) Uani 1 1 d . . .
O5 O 0.69777(19) 0.7327(6) 1.1903(2) 0.0551(10) Uani 1 1 d . . .
O6 O 0.59811(16) 0.8782(5) 1.1807(2) 0.0369(8) Uani 1 1 d . . .
N1 N 0.39624(19) 1.2688(5) 0.9052(3) 0.0288(8) Uani 1 1 d . . .
N2 N 0.3263(2) 1.7793(6) 1.5649(3) 0.0471(11) Uani 1 1 d . . .
H2 H 0.3142 1.7809 1.6254 0.057 Uiso 1 1 calc R . .
C1 C 0.5130(2) 0.8433(6) 0.8289(3) 0.0321(10) Uani 1 1 d . . .
C2 C 0.5799(2) 0.7968(6) 0.8827(3) 0.0274(10) Uani 1 1 d . . .
C3 C 0.6389(2) 0.7416(5) 0.8331(3) 0.0255(10) Uani 1 1 d . . .
H3 H 0.6378 0.7359 0.7652 0.031 Uiso 1 1 calc R . .
C4 C 0.7000(2) 0.6943(6) 0.8823(3) 0.0277(10) Uani 1 1 d . . .
C5 C 0.7636(2) 0.6380(6) 0.8250(4) 0.0322(10) Uani 1 1 d . . .
C6 C 0.7011(2) 0.7037(6) 0.9836(3) 0.0282(10) Uani 1 1 d . . .
H6 H 0.7406 0.6659 1.0176 0.034 Uiso 1 1 calc R . .
C7 C 0.6442(2) 0.7685(5) 1.0342(3) 0.0264(10) Uani 1 1 d . . .
C8 C 0.6486(2) 0.7910(6) 1.1437(3) 0.0299(10) Uani 1 1 d . . .
C9 C 0.5841(2) 0.8143(6) 0.9839(3) 0.0261(9) Uani 1 1 d . . .
H9 H 0.5457 0.8576 1.0181 0.031 Uiso 1 1 calc R . .
C10 C 0.3867(2) 1.4297(6) 0.8748(3) 0.0341(11) Uani 1 1 d . . .
H10 H 0.3770 1.4497 0.8091 0.041 Uiso 1 1 calc R . .
C11 C 0.3909(3) 1.5678(6) 0.9384(4) 0.0374(11) Uani 1 1 d . . .
H11 H 0.3831 1.6777 0.9149 0.045 Uiso 1 1 calc R . .
C12 C 0.4065(3) 1.5434(6) 1.0356(3) 0.0356(11) Uani 1 1 d . . .
C13 C 0.4179(3) 1.3769(7) 1.0657(3) 0.0390(12) Uani 1 1 d . . .
H13 H 0.4298 1.3545 1.1304 0.047 Uiso 1 1 calc R . .
C14 C 0.4117(3) 1.2446(6) 1.0000(3) 0.0349(11) Uani 1 1 d . . .
H14 H 0.4186 1.1337 1.0223 0.042 Uiso 1 1 calc R . .
C15 C 0.4112(3) 1.6912(7) 1.1054(4) 0.0535(16) Uani 1 1 d . . .
H15A H 0.3865 1.7876 1.0768 0.064 Uiso 1 1 calc R . .
H15B H 0.4603 1.7232 1.1119 0.064 Uiso 1 1 calc R . .
C16 C 0.3811(3) 1.6594(9) 1.2077(4) 0.0547(16) Uani 1 1 d . . .
H16A H 0.3323 1.6239 1.2019 0.066 Uiso 1 1 calc R . .
H16B H 0.4071 1.5672 1.2383 0.066 Uiso 1 1 calc R . .
C17 C 0.3848(4) 1.8077(11) 1.2687(5) 0.077(3) Uani 1 1 d . . .
H17A H 0.3550 1.8954 1.2405 0.093 Uiso 1 1 calc R . .
H17B H 0.4329 1.8501 1.2675 0.093 Uiso 1 1 calc R . .
C18 C 0.3632(3) 1.7825(9) 1.3747(4) 0.0552(18) Uani 1 1 d . . .
C19 C 0.2968(3) 1.8165(10) 1.4013(4) 0.069(2) Uani 1 1 d . . .
H19 H 0.2628 1.8392 1.3540 0.083 Uiso 1 1 calc R . .
C20 C 0.2788(3) 1.8179(10) 1.4979(4) 0.0649(18) Uani 1 1 d . . .
H20 H 0.2331 1.8460 1.5166 0.078 Uiso 1 1 calc R . .
C21 C 0.3915(3) 1.7385(10) 1.5425(4) 0.0588(18) Uani 1 1 d . . .
H21 H 0.4238 1.7111 1.5912 0.071 Uiso 1 1 calc R . .
C22 C 0.4108(3) 1.7373(11) 1.4460(5) 0.074(2) Uani 1 1 d . . .
H22 H 0.4564 1.7058 1.4286 0.089 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 O6 1.917(3) 2_674 ?
Zn1 O4 1.944(3) 4_465 ?
Zn1 O1 1.954(3) . ?
Zn1 N1 2.061(4) . ?
O1 C1 1.273(5) . ?
O2 C1 1.223(6) . ?
O3 C5 1.232(6) . ?
O4 C5 1.264(5) . ?
O4 Zn1 1.945(3) 4_565 ?
O5 C8 1.219(5) . ?
O6 C8 1.281(5) . ?
O6 Zn1 1.917(3) 2_675 ?
N1 C10 1.339(6) . ?
N1 C14 1.344(6) . ?
N2 C21 1.312(7) . ?
N2 C20 1.320(7) . ?
C1 C2 1.511(6) . ?
C2 C3 1.378(6) . ?
C2 C9 1.393(6) . ?
C3 C4 1.390(6) . ?
C4 C6 1.388(6) . ?
C4 C5 1.505(6) . ?
C6 C7 1.379(6) . ?
C7 C9 1.380(6) . ?
C7 C8 1.510(6) . ?
C10 C11 1.389(7) . ?
C11 C12 1.375(7) . ?
C12 C13 1.384(7) . ?
C12 C15 1.503(7) . ?
C13 C14 1.376(7) . ?
C15 C16 1.531(8) . ?
C16 C17 1.431(9) . ?
C17 C18 1.519(8) . ?
C18 C19 1.340(8) . ?
C18 C22 1.375(9) . ?
C19 C20 1.365(8) . ?
C21 C22 1.370(8) . ?

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
O6 Zn1 O4 126.20(13) 2_674 4_465 ?
O6 Zn1 O1 115.43(13) 2_674 . ?
O4 Zn1 O1 104.68(14) 4_465 . ?
O6 Zn1 N1 111.01(15) 2_674 . ?
O4 Zn1 N1 99.48(14) 4_465 . ?
O1 Zn1 N1 94.44(13) . . ?
C1 O1 Zn1 124.2(3) . . ?
C5 O4 Zn1 125.1(3) . 4_565 ?
C8 O6 Zn1 115.9(3) . 2_675 ?
C10 N1 C14 117.5(4) . . ?
C10 N1 Zn1 124.2(3) . . ?
C14 N1 Zn1 118.3(3) . . ?
C21 N2 C20 122.5(5) . . ?
O2 C1 O1 124.9(4) . . ?
O2 C1 C2 120.0(4) . . ?
O1 C1 C2 115.1(4) . . ?
C3 C2 C9 118.3(4) . . ?
C3 C2 C1 121.1(4) . . ?
C9 C2 C1 120.5(4) . . ?
C2 C3 C4 121.5(4) . . ?
C6 C4 C3 118.9(4) . . ?
C6 C4 C5 121.5(4) . . ?
C3 C4 C5 119.6(4) . . ?
O3 C5 O4 125.6(4) . . ?
O3 C5 C4 118.6(4) . . ?
O4 C5 C4 115.9(5) . . ?
C7 C6 C4 120.5(4) . . ?
C6 C7 C9 119.5(4) . . ?
C6 C7 C8 119.8(4) . . ?
C9 C7 C8 120.6(4) . . ?
O5 C8 O6 124.4(4) . . ?
O5 C8 C7 121.1(4) . . ?
O6 C8 C7 114.4(4) . . ?
C7 C9 C2 121.1(4) . . ?
N1 C10 C11 122.1(4) . . ?
C12 C11 C10 120.6(4) . . ?
C11 C12 C13 116.9(4) . . ?
C11 C12 C15 121.3(5) . . ?
C13 C12 C15 121.8(5) . . ?
C14 C13 C12 120.1(4) . . ?
N1 C14 C13 122.8(4) . . ?
C12 C15 C16 115.7(5) . . ?
C17 C16 C15 112.5(5) . . ?
C16 C17 C18 116.0(7) . . ?
C19 C18 C22 118.4(5) . . ?
C19 C18 C17 119.2(7) . . ?
C22 C18 C17 122.2(6) . . ?
C18 C19 C20 120.0(6) . . ?
N2 C20 C19 120.0(5) . . ?
N2 C21 C22 118.6(6) . . ?
C21 C22 C18 120.4(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_LJB_1_H2O_100K
_database_code_depnum_ccdc_archive 'CCDC 1441454'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O7 Zn'
_chemical_formula_weight         489.77

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n


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

_cell_length_a                   19.1246(11)
_cell_length_b                   7.8040(5)
_cell_length_c                   13.7839(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2057.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5604
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.95

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.445
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6077
_exptl_absorpt_correction_T_max  0.7945
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10608
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.97
_reflns_number_total             3994
_reflns_number_gt                3801
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0219P)²+0.7448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(9)
_refine_ls_number_reflns         3994
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.001

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 0.386947(11) -0.04765(3) 0.20775(2) 0.00813(8) Uani 1 1 d . . .
O1 O 0.46732(9) 0.0607(2) 0.14521(13) 0.0115(4) Uani 1 1 d . . .
O2 O 0.49857(10) 0.2254(3) 0.27058(14) 0.0191(4) Uani 1 1 d . . .
O3 O 0.76247(10) 0.3106(3) 0.28683(15) 0.0229(5) Uani 1 1 d . . .
O4 O 0.80691(9) 0.4267(2) 0.15287(14) 0.0157(4) Uani 1 1 d . . .
O5 O 0.69889(10) 0.2522(3) -0.16579(14) 0.0189(4) Uani 1 1 d . . .
O6 O 0.59948(9) 0.1038(3) -0.15732(14) 0.0134(4) Uani 1 1 d . . .
N1 N 0.38823(10) -0.2577(3) 0.11787(17) 0.0123(5) Uani 1 1 d . . .
N2 N 0.33075(12) -0.7772(3) -0.54319(17) 0.0202(5) Uani 1 1 d . . .
H2 H 0.3161 -0.7826 -0.6036 0.024 Uiso 1 1 calc R . .
C1 C 0.50939(12) 0.1617(3) 0.19043(17) 0.0102(6) Uani 1 1 d . . .
C2 C 0.57667(12) 0.1998(3) 0.13650(19) 0.0101(5) Uani 1 1 d . . .
C3 C 0.63524(12) 0.2524(3) 0.18880(17) 0.0092(6) Uani 1 1 d . . .
H3 H 0.6327 0.2609 0.2575 0.011 Uiso 1 1 calc R . .
C4 C 0.69747(13) 0.2926(3) 0.1415(2) 0.0117(5) Uani 1 1 d . . .
C5 C 0.75998(11) 0.3480(3) 0.1992(2) 0.0118(5) Uani 1 1 d . . .
C6 C 0.70093(13) 0.2805(3) 0.04069(19) 0.0117(5) Uani 1 1 d . . .
H6 H 0.7424 0.3136 0.0077 0.014 Uiso 1 1 calc R . .
C7 C 0.64357(13) 0.2198(3) -0.01189(19) 0.0104(5) Uani 1 1 d . . .
C8 C 0.64925(13) 0.1935(3) -0.11934(18) 0.0107(5) Uani 1 1 d . . .
C9 C 0.58159(13) 0.1780(3) 0.03727(18) 0.0097(5) Uani 1 1 d . . .
H9 H 0.5428 0.1343 0.0021 0.012 Uiso 1 1 calc R . .
C10 C 0.38183(13) -0.4219(4) 0.1454(2) 0.0146(6) Uani 1 1 d . . .
H10 H 0.3720 -0.4461 0.2115 0.017 Uiso 1 1 calc R . .
C11 C 0.38901(13) -0.5573(4) 0.0815(2) 0.0164(6) Uani 1 1 d . . .
H11 H 0.3828 -0.6716 0.1036 0.020 Uiso 1 1 calc R . .
C12 C 0.40535(14) -0.5259(4) -0.0158(2) 0.0154(6) Uani 1 1 d . . .
C13 C 0.41219(14) -0.3556(4) -0.0438(2) 0.0172(6) Uani 1 1 d . . .
H13 H 0.4234 -0.3277 -0.1090 0.021 Uiso 1 1 calc R . .
C14 C 0.40270(14) -0.2274(4) 0.0236(2) 0.0153(6) Uani 1 1 d . . .
H14 H 0.4065 -0.1118 0.0027 0.018 Uiso 1 1 calc R . .
C15 C 0.41618(16) -0.6705(4) -0.0867(2) 0.0203(6) Uani 1 1 d . . .
H15A H 0.3935 -0.7745 -0.0602 0.024 Uiso 1 1 calc R . .
H15B H 0.4669 -0.6942 -0.0911 0.024 Uiso 1 1 calc R . .
C16 C 0.38838(14) -0.6399(4) -0.1884(2) 0.0195(6) Uani 1 1 d . . .
H16A H 0.3372 -0.6219 -0.1857 0.023 Uiso 1 1 calc R . .
H16B H 0.4100 -0.5352 -0.2157 0.023 Uiso 1 1 calc R . .
C17 C 0.4045(2) -0.7912(5) -0.2535(2) 0.0314(8) Uani 1 1 d . . .
H17A H 0.4558 -0.8062 -0.2565 0.038 Uiso 1 1 calc R . .
H17B H 0.3846 -0.8958 -0.2236 0.038 Uiso 1 1 calc R . .
C18 C 0.37676(16) -0.7761(4) -0.3558(2) 0.0229(7) Uani 1 1 d . . .
C19 C 0.30637(16) -0.7996(4) -0.3758(2) 0.0274(7) Uani 1 1 d . . .
H19 H 0.2738 -0.8155 -0.3246 0.033 Uiso 1 1 calc R . .
C20 C 0.28426(16) -0.7994(5) -0.4716(2) 0.0285(8) Uani 1 1 d . . .
H20 H 0.2362 -0.8150 -0.4864 0.034 Uiso 1 1 calc R . .
C21 C 0.39775(16) -0.7474(4) -0.5266(2) 0.0231(7) Uani 1 1 d . . .
H21 H 0.4291 -0.7293 -0.5791 0.028 Uiso 1 1 calc R . .
C22 C 0.42186(16) -0.7430(4) -0.4314(2) 0.0256(7) Uani 1 1 d . . .
H22 H 0.4695 -0.7170 -0.4185 0.031 Uiso 1 1 calc R . .
O1W O 0.70378(15) 0.0146(4) 0.3745(2) 0.0568(8) Uani 1 1 d . . .
H1W1 H 0.7188 0.1284 0.3811 0.050 Uiso 1 1 d . . .
H2W1 H 0.7461 -0.0457 0.3743 0.050 Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O6 1.9284(19) 2_655 ?
Zn1 O4 1.9510(18) 4_455 ?
Zn1 O1 1.9547(18) . ?
Zn1 N1 2.055(2) . ?
O1 C1 1.288(3) . ?
O2 C1 1.229(3) . ?
O3 C5 1.244(4) . ?
O4 C5 1.261(3) . ?
O4 Zn1 1.9510(18) 4 ?
O5 C8 1.233(3) . ?
O6 C8 1.292(3) . ?
O6 Zn1 1.9284(19) 2_654 ?
N1 C10 1.342(4) . ?
N1 C14 1.349(4) . ?
N2 C21 1.322(4) . ?
N2 C20 1.340(4) . ?
C1 C2 1.515(3) . ?
C2 C9 1.381(4) . ?
C2 C3 1.394(3) . ?
C3 C4 1.393(3) . ?
C4 C6 1.395(4) . ?
C4 C5 1.499(3) . ?
C6 C7 1.397(4) . ?
C7 C9 1.404(4) . ?
C7 C8 1.499(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.399(4) . ?
C12 C13 1.390(4) . ?
C12 C15 1.506(4) . ?
C13 C14 1.377(4) . ?
C15 C16 1.519(4) . ?
C16 C17 1.514(4) . ?
C17 C18 1.511(4) . ?
C18 C22 1.377(5) . ?
C18 C19 1.386(4) . ?
C19 C20 1.386(4) . ?
C21 C22 1.392(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O4 126.12(8) 2_655 4_455 ?
O6 Zn1 O1 114.70(8) 2_655 . ?
O4 Zn1 O1 103.69(8) 4_455 . ?
O6 Zn1 N1 113.49(9) 2_655 . ?
O4 Zn1 N1 99.30(8) 4_455 . ?
O1 Zn1 N1 94.01(8) . . ?
C1 O1 Zn1 122.88(16) . . ?
C5 O4 Zn1 126.71(19) . 4 ?
C8 O6 Zn1 114.49(16) . 2_654 ?
C10 N1 C14 117.3(3) . . ?
C10 N1 Zn1 126.2(2) . . ?
C14 N1 Zn1 116.28(19) . . ?
C21 N2 C20 122.6(3) . . ?
O2 C1 O1 125.3(2) . . ?
O2 C1 C2 120.3(2) . . ?
O1 C1 C2 114.4(2) . . ?
C9 C2 C3 119.6(2) . . ?
C9 C2 C1 121.3(2) . . ?
C3 C2 C1 119.1(2) . . ?
C4 C3 C2 120.7(2) . . ?
C3 C4 C6 119.4(2) . . ?
C3 C4 C5 119.9(2) . . ?
C6 C4 C5 120.7(2) . . ?
O3 C5 O4 125.4(2) . . ?
O3 C5 C4 118.5(2) . . ?
O4 C5 C4 116.1(3) . . ?
C4 C6 C7 120.2(2) . . ?
C6 C7 C9 119.4(2) . . ?
C6 C7 C8 120.1(2) . . ?
C9 C7 C8 120.4(2) . . ?
O5 C8 O6 123.9(2) . . ?
O5 C8 C7 121.2(2) . . ?
O6 C8 C7 114.9(2) . . ?
C2 C9 C7 120.4(2) . . ?
N1 C10 C11 122.7(3) . . ?
C10 C11 C12 120.0(3) . . ?
C13 C12 C11 117.0(3) . . ?
C13 C12 C15 121.6(3) . . ?
C11 C12 C15 121.4(3) . . ?
C14 C13 C12 119.7(3) . . ?
N1 C14 C13 123.3(3) . . ?
C12 C15 C16 115.6(2) . . ?
C17 C16 C15 110.7(2) . . ?
C18 C17 C16 114.9(3) . . ?
C22 C18 C19 118.9(3) . . ?
C22 C18 C17 120.1(3) . . ?
C19 C18 C17 121.0(3) . . ?
C20 C19 C18 119.0(3) . . ?
N2 C20 C19 120.0(3) . . ?
N2 C21 C22 119.2(3) . . ?
C18 C22 C21 120.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_LJB_1_H2O_120K
_database_code_depnum_ccdc_archive 'CCDC 1441455'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O7 Zn'
_chemical_formula_weight         489.77

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   19.1221(11)
_cell_length_b                   7.8119(5)
_cell_length_c                   13.7812(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2058.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5502
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6079
_exptl_absorpt_correction_T_max  0.7946
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10650
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.02
_reflns_number_total             4011
_reflns_number_gt                3816
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0192P)²+0.7181P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.020(9)
_refine_ls_number_reflns         4011
_refine_ls_number_parameters     289
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.101
_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 0.386933(11) -0.04737(3) 0.19363(2) 0.00929(8) Uani 1 1 d . . .
O1 O 0.46733(9) 0.0607(2) 0.13111(13) 0.0130(4) Uani 1 1 d . . .
O2 O 0.49864(10) 0.2253(3) 0.25648(14) 0.0221(5) Uani 1 1 d . . .
O3 O 0.76275(10) 0.3097(3) 0.27252(15) 0.0250(5) Uani 1 1 d . . .
O4 O 0.80689(9) 0.4267(2) 0.13888(14) 0.0176(4) Uani 1 1 d . . .
O5 O 0.69899(10) 0.2516(3) -0.17987(14) 0.0221(4) Uani 1 1 d . . .
O6 O 0.59962(9) 0.1037(3) -0.17143(14) 0.0152(4) Uani 1 1 d . . .
N1 N 0.38818(10) -0.2574(3) 0.10360(16) 0.0128(5) Uani 1 1 d . . .
N2 N 0.33066(12) -0.7764(3) -0.55714(17) 0.0224(5) Uani 1 1 d . . .
H2 H 0.3160 -0.7816 -0.6176 0.027 Uiso 1 1 calc R . .
C1 C 0.50937(12) 0.1614(3) 0.17644(17) 0.0116(6) Uani 1 1 d . . .
C2 C 0.57684(12) 0.1991(3) 0.12270(19) 0.0110(5) Uani 1 1 d . . .
C3 C 0.63547(12) 0.2517(3) 0.17469(16) 0.0099(6) Uani 1 1 d . . .
H3 H 0.6330 0.2600 0.2434 0.012 Uiso 1 1 calc R . .
C4 C 0.69751(13) 0.2923(3) 0.1274(2) 0.0134(5) Uani 1 1 d . . .
C5 C 0.76004(11) 0.3470(3) 0.1850(2) 0.0131(5) Uani 1 1 d . . .
C6 C 0.70100(13) 0.2801(3) 0.02646(18) 0.0129(5) Uani 1 1 d . . .
H6 H 0.7425 0.3132 -0.0065 0.015 Uiso 1 1 calc R . .
C7 C 0.64377(13) 0.2192(3) -0.0261(2) 0.0127(5) Uani 1 1 d . . .
C8 C 0.64909(13) 0.1927(3) -0.13352(18) 0.0127(5) Uani 1 1 d . . .
C9 C 0.58175(13) 0.1779(3) 0.02309(18) 0.0114(5) Uani 1 1 d . . .
H9 H 0.5428 0.1350 -0.0122 0.014 Uiso 1 1 calc R . .
C10 C 0.38198(14) -0.4215(4) 0.1314(2) 0.0169(6) Uani 1 1 d . . .
H10 H 0.3723 -0.4457 0.1976 0.020 Uiso 1 1 calc R . .
C11 C 0.38920(13) -0.5565(4) 0.0673(2) 0.0180(6) Uani 1 1 d . . .
H11 H 0.3832 -0.6708 0.0894 0.022 Uiso 1 1 calc R . .
C12 C 0.40525(14) -0.5254(4) -0.0299(2) 0.0168(6) Uani 1 1 d . . .
C13 C 0.41189(14) -0.3552(4) -0.0579(2) 0.0185(6) Uani 1 1 d . . .
H13 H 0.4229 -0.3273 -0.1233 0.022 Uiso 1 1 calc R . .
C14 C 0.40239(14) -0.2272(4) 0.0098(2) 0.0166(6) Uani 1 1 d . . .
H14 H 0.4061 -0.1116 -0.0111 0.020 Uiso 1 1 calc R . .
C15 C 0.41621(17) -0.6692(4) -0.1006(2) 0.0230(6) Uani 1 1 d . . .
H15A H 0.3937 -0.7733 -0.0741 0.028 Uiso 1 1 calc R . .
H15B H 0.4670 -0.6924 -0.1050 0.028 Uiso 1 1 calc R . .
C16 C 0.38838(14) -0.6395(4) -0.2026(2) 0.0216(6) Uani 1 1 d . . .
H16A H 0.3372 -0.6212 -0.1999 0.026 Uiso 1 1 calc R . .
H16B H 0.4101 -0.5351 -0.2301 0.026 Uiso 1 1 calc R . .
C17 C 0.4042(2) -0.7906(5) -0.2674(2) 0.0338(9) Uani 1 1 d . . .
H17A H 0.3841 -0.8947 -0.2375 0.041 Uiso 1 1 calc R . .
H17B H 0.4556 -0.8062 -0.2702 0.041 Uiso 1 1 calc R . .
C18 C 0.37676(16) -0.7754(4) -0.3700(2) 0.0248(7) Uani 1 1 d . . .
C19 C 0.30642(16) -0.7988(4) -0.3899(2) 0.0301(7) Uani 1 1 d . . .
H19 H 0.2738 -0.8148 -0.3387 0.036 Uiso 1 1 calc R . .
C20 C 0.28427(16) -0.7986(5) -0.4859(2) 0.0309(8) Uani 1 1 d . . .
H20 H 0.2362 -0.8143 -0.5008 0.037 Uiso 1 1 calc R . .
C21 C 0.39793(16) -0.7468(4) -0.5405(2) 0.0262(7) Uani 1 1 d . . .
H21 H 0.4293 -0.7290 -0.5930 0.031 Uiso 1 1 calc R . .
C22 C 0.42182(16) -0.7421(4) -0.4453(2) 0.0278(7) Uani 1 1 d . . .
H22 H 0.4694 -0.7159 -0.4323 0.033 Uiso 1 1 calc R . .
O1W O 0.70418(16) 0.0151(4) 0.3612(2) 0.0612(9) Uani 1 1 d D . .
H2W1 H 0.7363 -0.0653 0.3466 0.050 Uiso 1 1 d D . .
H1W1 H 0.7171 0.1112 0.3274 0.050 Uiso 1 1 d 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 O6 1.9282(19) 2_655 ?
Zn1 O4 1.9495(18) 4_455 ?
Zn1 O1 1.9541(17) . ?
Zn1 N1 2.057(2) . ?
O1 C1 1.287(3) . ?
O2 C1 1.228(3) . ?
O3 C5 1.242(4) . ?
O4 C5 1.263(3) . ?
O4 Zn1 1.9495(18) 4 ?
O5 C8 1.237(3) . ?
O6 C8 1.285(3) . ?
O6 Zn1 1.9282(19) 2_654 ?
N1 C14 1.342(4) . ?
N1 C10 1.343(4) . ?
N2 C21 1.327(4) . ?
N2 C20 1.335(4) . ?
C1 C2 1.517(3) . ?
C2 C9 1.386(4) . ?
C2 C3 1.393(3) . ?
C3 C4 1.390(3) . ?
C4 C6 1.396(4) . ?
C4 C5 1.498(3) . ?
C6 C7 1.396(4) . ?
C7 C9 1.404(4) . ?
C7 C8 1.498(4) . ?
C10 C11 1.383(4) . ?
C11 C12 1.395(4) . ?
C12 C13 1.390(4) . ?
C12 C15 1.502(4) . ?
C13 C14 1.380(4) . ?
C15 C16 1.521(4) . ?
C16 C17 1.511(4) . ?
C17 C18 1.512(4) . ?
C18 C22 1.374(5) . ?
C18 C19 1.385(4) . ?
C19 C20 1.389(4) . ?
C21 C22 1.390(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O4 126.04(8) 2_655 4_455 ?
O6 Zn1 O1 114.77(8) 2_655 . ?
O4 Zn1 O1 103.78(8) 4_455 . ?
O6 Zn1 N1 113.46(9) 2_655 . ?
O4 Zn1 N1 99.28(8) 4_455 . ?
O1 Zn1 N1 93.99(8) . . ?
C1 O1 Zn1 122.80(16) . . ?
C5 O4 Zn1 126.92(19) . 4 ?
C8 O6 Zn1 114.68(16) . 2_654 ?
C14 N1 C10 117.4(2) . . ?
C14 N1 Zn1 116.29(18) . . ?
C10 N1 Zn1 126.0(2) . . ?
C21 N2 C20 122.7(3) . . ?
O2 C1 O1 125.5(2) . . ?
O2 C1 C2 120.1(2) . . ?
O1 C1 C2 114.4(2) . . ?
C9 C2 C3 119.4(2) . . ?
C9 C2 C1 121.2(2) . . ?
C3 C2 C1 119.4(2) . . ?
C4 C3 C2 120.9(2) . . ?
C3 C4 C6 119.5(2) . . ?
C3 C4 C5 119.8(2) . . ?
C6 C4 C5 120.6(2) . . ?
O3 C5 O4 125.1(2) . . ?
O3 C5 C4 118.8(2) . . ?
O4 C5 C4 116.1(3) . . ?
C4 C6 C7 120.2(2) . . ?
C6 C7 C9 119.3(2) . . ?
C6 C7 C8 120.4(2) . . ?
C9 C7 C8 120.2(2) . . ?
O5 C8 O6 124.0(2) . . ?
O5 C8 C7 120.7(2) . . ?
O6 C8 C7 115.2(2) . . ?
C2 C9 C7 120.5(2) . . ?
N1 C10 C11 122.5(3) . . ?
C10 C11 C12 120.1(3) . . ?
C13 C12 C11 117.0(3) . . ?
C13 C12 C15 121.4(3) . . ?
C11 C12 C15 121.5(3) . . ?
C14 C13 C12 119.5(3) . . ?
N1 C14 C13 123.4(3) . . ?
C12 C15 C16 115.9(2) . . ?
C17 C16 C15 110.9(2) . . ?
C16 C17 C18 114.9(3) . . ?
C22 C18 C19 118.9(3) . . ?
C22 C18 C17 120.2(3) . . ?
C19 C18 C17 120.8(3) . . ?
C18 C19 C20 119.0(3) . . ?
N2 C20 C19 119.9(3) . . ?
N2 C21 C22 119.1(3) . . ?
C18 C22 C21 120.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_LJB_1_H2O_140K
_database_code_depnum_ccdc_archive 'CCDC 1441456'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O7 Zn'
_chemical_formula_weight         489.77

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   19.1203(11)
_cell_length_b                   7.8191(4)
_cell_length_c                   13.7785(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2059.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    5391
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6075
_exptl_absorpt_correction_T_max  0.7947
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10643
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4005
_reflns_number_gt                3814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0185P)²+0.6630P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(10)
_refine_ls_number_reflns         4005
_refine_ls_number_parameters     289
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.111
_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 0.386891(11) -0.04704(3) 0.20194(2) 0.01017(8) Uani 1 1 d . . .
O1 O 0.46744(9) 0.0608(2) 0.13944(13) 0.0141(4) Uani 1 1 d . . .
O2 O 0.49876(10) 0.2250(3) 0.26472(15) 0.0249(5) Uani 1 1 d . . .
O3 O 0.76291(10) 0.3090(3) 0.28059(15) 0.0280(5) Uani 1 1 d . . .
O4 O 0.80689(9) 0.4265(2) 0.14752(14) 0.0187(4) Uani 1 1 d . . .
O5 O 0.69900(10) 0.2512(3) -0.17170(15) 0.0241(5) Uani 1 1 d . . .
O6 O 0.59969(9) 0.1033(3) -0.16324(14) 0.0171(4) Uani 1 1 d . . .
N1 N 0.38807(10) -0.2569(3) 0.11193(17) 0.0140(5) Uani 1 1 d . . .
N2 N 0.33076(13) -0.7757(3) -0.54888(18) 0.0250(6) Uani 1 1 d . . .
H2 H 0.3160 -0.7808 -0.6093 0.030 Uiso 1 1 calc R . .
C1 C 0.50959(12) 0.1610(3) 0.18480(17) 0.0124(6) Uani 1 1 d . . .
C2 C 0.57683(12) 0.1986(3) 0.13095(19) 0.0113(5) Uani 1 1 d . . .
C3 C 0.63547(12) 0.2514(3) 0.18314(17) 0.0109(6) Uani 1 1 d . . .
H3 H 0.6331 0.2598 0.2518 0.013 Uiso 1 1 calc R . .
C4 C 0.69756(13) 0.2918(3) 0.13550(19) 0.0136(5) Uani 1 1 d . . .
C5 C 0.76019(11) 0.3466(3) 0.1936(2) 0.0144(5) Uani 1 1 d . . .
C6 C 0.70099(13) 0.2792(3) 0.03479(18) 0.0134(5) Uani 1 1 d . . .
H6 H 0.7425 0.3117 0.0017 0.016 Uiso 1 1 calc R . .
C7 C 0.64382(13) 0.2193(3) -0.0175(2) 0.0136(5) Uani 1 1 d . . .
C8 C 0.64942(13) 0.1927(3) -0.12507(18) 0.0136(5) Uani 1 1 d . . .
C9 C 0.58183(13) 0.1778(3) 0.03143(18) 0.0123(5) Uani 1 1 d . . .
H9 H 0.5429 0.1351 -0.0040 0.015 Uiso 1 1 calc R . .
C10 C 0.38219(14) -0.4209(4) 0.1395(2) 0.0178(6) Uani 1 1 d . . .
H10 H 0.3727 -0.4452 0.2058 0.021 Uiso 1 1 calc R . .
C11 C 0.38930(14) -0.5557(4) 0.0758(2) 0.0192(6) Uani 1 1 d . . .
H11 H 0.3832 -0.6698 0.0981 0.023 Uiso 1 1 calc R . .
C12 C 0.40544(14) -0.5244(4) -0.0215(2) 0.0172(6) Uani 1 1 d . . .
C13 C 0.41181(14) -0.3548(4) -0.0495(2) 0.0198(6) Uani 1 1 d . . .
H13 H 0.4226 -0.3269 -0.1149 0.024 Uiso 1 1 calc R . .
C14 C 0.40245(15) -0.2271(4) 0.0181(2) 0.0183(6) Uani 1 1 d . . .
H14 H 0.4064 -0.1118 -0.0028 0.022 Uiso 1 1 calc R . .
C15 C 0.41658(17) -0.6687(4) -0.0922(2) 0.0252(7) Uani 1 1 d . . .
H15A H 0.3941 -0.7728 -0.0657 0.030 Uiso 1 1 calc R . .
H15B H 0.4674 -0.6916 -0.0968 0.030 Uiso 1 1 calc R . .
C16 C 0.38853(14) -0.6385(4) -0.1942(2) 0.0224(6) Uani 1 1 d . . .
H16A H 0.3373 -0.6210 -0.1913 0.027 Uiso 1 1 calc R . .
H16B H 0.4100 -0.5338 -0.2215 0.027 Uiso 1 1 calc R . .
C17 C 0.4047(2) -0.7896(5) -0.2595(2) 0.0341(9) Uani 1 1 d . . .
H17A H 0.4561 -0.8043 -0.2624 0.041 Uiso 1 1 calc R . .
H17B H 0.3849 -0.8940 -0.2297 0.041 Uiso 1 1 calc R . .
C18 C 0.37719(16) -0.7746(4) -0.3617(2) 0.0247(7) Uani 1 1 d . . .
C19 C 0.30678(17) -0.7980(5) -0.3815(2) 0.0337(8) Uani 1 1 d . . .
H19 H 0.2741 -0.8137 -0.3302 0.040 Uiso 1 1 calc R . .
C20 C 0.28488(16) -0.7983(5) -0.4774(2) 0.0343(8) Uani 1 1 d . . .
H20 H 0.2368 -0.8147 -0.4922 0.041 Uiso 1 1 calc R . .
C21 C 0.39803(16) -0.7458(5) -0.5322(2) 0.0295(8) Uani 1 1 d . . .
H21 H 0.4294 -0.7274 -0.5847 0.035 Uiso 1 1 calc R . .
C22 C 0.42205(16) -0.7417(4) -0.4371(2) 0.0304(7) Uani 1 1 d . . .
H22 H 0.4697 -0.7161 -0.4243 0.036 Uiso 1 1 calc R . .
O1W O 0.70429(16) 0.0151(4) 0.3695(2) 0.0656(9) Uani 1 1 d D . .
H2W1 H 0.7328 -0.0720 0.3531 0.050 Uiso 1 1 d D . .
H1W1 H 0.7130 0.0982 0.3257 0.050 Uiso 1 1 d 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 O6 1.926(2) 2_655 ?
Zn1 O4 1.9468(18) 4_455 ?
Zn1 O1 1.9557(18) . ?
Zn1 N1 2.057(2) . ?
O1 C1 1.286(3) . ?
O2 C1 1.227(3) . ?
O3 C5 1.236(4) . ?
O4 C5 1.261(3) . ?
O4 Zn1 1.9469(18) 4 ?
O5 C8 1.233(3) . ?
O6 C8 1.292(3) . ?
O6 Zn1 1.926(2) 2_654 ?
N1 C14 1.342(4) . ?
N1 C10 1.343(4) . ?
N2 C21 1.327(4) . ?
N2 C20 1.331(4) . ?
C1 C2 1.513(3) . ?
C2 C9 1.384(4) . ?
C2 C3 1.394(3) . ?
C3 C4 1.393(3) . ?
C4 C6 1.393(4) . ?
C4 C5 1.503(3) . ?
C6 C7 1.391(4) . ?
C7 C9 1.402(4) . ?
C7 C8 1.500(4) . ?
C10 C11 1.378(4) . ?
C11 C12 1.398(4) . ?
C12 C13 1.387(4) . ?
C12 C15 1.506(4) . ?
C13 C14 1.377(4) . ?
C15 C16 1.522(4) . ?
C16 C17 1.517(4) . ?
C17 C18 1.508(4) . ?
C18 C22 1.372(5) . ?
C18 C19 1.386(4) . ?
C19 C20 1.386(4) . ?
C21 C22 1.388(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O4 125.92(8) 2_655 4_455 ?
O6 Zn1 O1 114.72(8) 2_655 . ?
O4 Zn1 O1 103.91(8) 4_455 . ?
O6 Zn1 N1 113.45(9) 2_655 . ?
O4 Zn1 N1 99.35(8) 4_455 . ?
O1 Zn1 N1 94.01(8) . . ?
C1 O1 Zn1 122.84(16) . . ?
C5 O4 Zn1 127.04(19) . 4 ?
C8 O6 Zn1 114.71(16) . 2_654 ?
C14 N1 C10 117.1(3) . . ?
C14 N1 Zn1 116.41(18) . . ?
C10 N1 Zn1 126.2(2) . . ?
C21 N2 C20 122.3(3) . . ?
O2 C1 O1 125.4(2) . . ?
O2 C1 C2 120.3(2) . . ?
O1 C1 C2 114.4(2) . . ?
C9 C2 C3 119.3(2) . . ?
C9 C2 C1 121.4(2) . . ?
C3 C2 C1 119.2(2) . . ?
C4 C3 C2 120.6(2) . . ?
C6 C4 C3 119.6(2) . . ?
C6 C4 C5 120.9(2) . . ?
C3 C4 C5 119.5(2) . . ?
O3 C5 O4 125.2(2) . . ?
O3 C5 C4 118.8(2) . . ?
O4 C5 C4 116.0(3) . . ?
C7 C6 C4 120.2(2) . . ?
C6 C7 C9 119.5(2) . . ?
C6 C7 C8 120.2(2) . . ?
C9 C7 C8 120.2(2) . . ?
O5 C8 O6 123.7(2) . . ?
O5 C8 C7 121.2(2) . . ?
O6 C8 C7 115.1(2) . . ?
C2 C9 C7 120.5(2) . . ?
N1 C10 C11 122.8(3) . . ?
C10 C11 C12 119.9(3) . . ?
C13 C12 C11 117.0(3) . . ?
C13 C12 C15 121.6(3) . . ?
C11 C12 C15 121.4(3) . . ?
C14 C13 C12 119.6(3) . . ?
N1 C14 C13 123.5(3) . . ?
C12 C15 C16 115.6(2) . . ?
C17 C16 C15 110.8(2) . . ?
C18 C17 C16 115.0(3) . . ?
C22 C18 C19 118.9(3) . . ?
C22 C18 C17 120.2(3) . . ?
C19 C18 C17 120.9(3) . . ?
C18 C19 C20 118.8(3) . . ?
N2 C20 C19 120.4(3) . . ?
N2 C21 C22 119.2(3) . . ?
C18 C22 C21 120.2(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_LJB_1_H2O_160K
_database_code_depnum_ccdc_archive 'CCDC 1441457'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O7 Zn'
_chemical_formula_weight         489.77

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   19.1211(10)
_cell_length_b                   7.8289(4)
_cell_length_c                   13.7769(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2062.36(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    5329
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6078
_exptl_absorpt_correction_T_max  0.7949
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10672
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4017
_reflns_number_gt                3801
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0241P)²+0.3962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(9)
_refine_ls_number_reflns         4017
_refine_ls_number_parameters     289
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.011
_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 0.386852(11) -0.04673(3) 0.19967(2) 0.01132(8) Uani 1 1 d . . .
O1 O 0.46735(9) 0.0609(2) 0.13720(13) 0.0155(4) Uani 1 1 d . . .
O2 O 0.49877(10) 0.2246(3) 0.26244(15) 0.0272(5) Uani 1 1 d . . .
O3 O 0.76315(10) 0.3080(3) 0.27823(15) 0.0307(5) Uani 1 1 d . . .
O4 O 0.80680(9) 0.4262(2) 0.14516(14) 0.0216(4) Uani 1 1 d . . .
O5 O 0.69908(10) 0.2502(3) -0.17385(15) 0.0266(5) Uani 1 1 d . . .
O6 O 0.59975(9) 0.1035(3) -0.16565(14) 0.0189(4) Uani 1 1 d . . .
N1 N 0.38812(10) -0.2567(3) 0.10984(17) 0.0156(5) Uani 1 1 d . . .
N2 N 0.33104(13) -0.7752(3) -0.55103(17) 0.0269(6) Uani 1 1 d . . .
H2 H 0.3163 -0.7800 -0.6115 0.032 Uiso 1 1 calc R . .
C1 C 0.50959(12) 0.1607(3) 0.18253(17) 0.0145(6) Uani 1 1 d . . .
C2 C 0.57691(12) 0.1988(3) 0.12845(19) 0.0126(5) Uani 1 1 d . . .
C3 C 0.63553(11) 0.2504(3) 0.18084(16) 0.0116(6) Uani 1 1 d . . .
H3 H 0.6331 0.2580 0.2496 0.014 Uiso 1 1 calc R . .
C4 C 0.69762(13) 0.2909(3) 0.13337(19) 0.0146(5) Uani 1 1 d . . .
C5 C 0.76013(11) 0.3461(3) 0.1912(2) 0.0160(5) Uani 1 1 d . . .
C6 C 0.70113(13) 0.2788(3) 0.03262(18) 0.0142(5) Uani 1 1 d . . .
H6 H 0.7426 0.3118 -0.0005 0.017 Uiso 1 1 calc R . .
C7 C 0.64376(13) 0.2184(3) -0.0196(2) 0.0146(5) Uani 1 1 d . . .
C8 C 0.64938(13) 0.1922(3) -0.12744(18) 0.0150(5) Uani 1 1 d . . .
C9 C 0.58197(13) 0.1771(3) 0.02922(18) 0.0137(5) Uani 1 1 d . . .
H9 H 0.5432 0.1337 -0.0061 0.016 Uiso 1 1 calc R . .
C10 C 0.38197(14) -0.4203(4) 0.1374(2) 0.0204(6) Uani 1 1 d . . .
H10 H 0.3721 -0.4444 0.2036 0.024 Uiso 1 1 calc R . .
C11 C 0.38937(14) -0.5550(4) 0.0736(2) 0.0218(6) Uani 1 1 d . . .
H11 H 0.3835 -0.6690 0.0959 0.026 Uiso 1 1 calc R . .
C12 C 0.40551(14) -0.5239(4) -0.0236(2) 0.0191(6) Uani 1 1 d . . .
C13 C 0.41185(14) -0.3539(4) -0.0515(2) 0.0210(6) Uani 1 1 d . . .
H13 H 0.4228 -0.3262 -0.1169 0.025 Uiso 1 1 calc R . .
C14 C 0.40228(14) -0.2262(4) 0.0156(2) 0.0190(6) Uani 1 1 d . . .
H14 H 0.4058 -0.1109 -0.0054 0.023 Uiso 1 1 calc R . .
C15 C 0.41657(17) -0.6677(4) -0.0942(2) 0.0267(7) Uani 1 1 d . . .
H15A H 0.3941 -0.7715 -0.0676 0.032 Uiso 1 1 calc R . .
H15B H 0.4674 -0.6907 -0.0987 0.032 Uiso 1 1 calc R . .
C16 C 0.38873(14) -0.6385(4) -0.1963(2) 0.0257(7) Uani 1 1 d . . .
H16A H 0.3375 -0.6209 -0.1936 0.031 Uiso 1 1 calc R . .
H16B H 0.4102 -0.5340 -0.2237 0.031 Uiso 1 1 calc R . .
C17 C 0.4048(2) -0.7888(5) -0.2617(2) 0.0371(9) Uani 1 1 d . . .
H17A H 0.4562 -0.8039 -0.2644 0.045 Uiso 1 1 calc R . .
H17B H 0.3848 -0.8931 -0.2320 0.045 Uiso 1 1 calc R . .
C18 C 0.37744(16) -0.7732(4) -0.3639(2) 0.0262(7) Uani 1 1 d . . .
C19 C 0.30715(16) -0.7972(5) -0.3839(2) 0.0352(8) Uani 1 1 d . . .
H19 H 0.2745 -0.8128 -0.3327 0.042 Uiso 1 1 calc R . .
C20 C 0.28520(16) -0.7981(5) -0.4796(2) 0.0389(9) Uani 1 1 d . . .
H20 H 0.2372 -0.8151 -0.4944 0.047 Uiso 1 1 calc R . .
C21 C 0.39797(16) -0.7454(5) -0.5344(2) 0.0315(8) Uani 1 1 d . . .
H21 H 0.4293 -0.7274 -0.5869 0.038 Uiso 1 1 calc R . .
C22 C 0.42201(16) -0.7408(5) -0.4393(2) 0.0327(8) Uani 1 1 d . . .
H22 H 0.4697 -0.7148 -0.4265 0.039 Uiso 1 1 calc R . .
O1W O 0.70426(16) 0.0135(4) 0.3666(2) 0.0678(9) Uani 1 1 d D . .
H2W1 H 0.7398 -0.0617 0.3556 0.050 Uiso 1 1 d D . .
H1W1 H 0.7192 0.1150 0.3415 0.050 Uiso 1 1 d 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 O6 1.9250(19) 2_655 ?
Zn1 O4 1.9486(19) 4_455 ?
Zn1 O1 1.9544(18) . ?
Zn1 N1 2.058(2) . ?
O1 C1 1.286(3) . ?
O2 C1 1.227(3) . ?
O3 C5 1.237(4) . ?
O4 C5 1.262(3) . ?
O4 Zn1 1.9486(19) 4 ?
O5 C8 1.232(3) . ?
O6 C8 1.288(3) . ?
O6 Zn1 1.9250(19) 2_654 ?
N1 C10 1.341(4) . ?
N1 C14 1.347(4) . ?
N2 C21 1.321(4) . ?
N2 C20 1.330(4) . ?
C1 C2 1.517(3) . ?
C2 C9 1.381(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.392(3) . ?
C4 C6 1.393(4) . ?
C4 C5 1.500(3) . ?
C6 C7 1.395(3) . ?
C7 C9 1.397(4) . ?
C7 C8 1.504(4) . ?
C10 C11 1.380(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.390(4) . ?
C12 C15 1.503(4) . ?
C13 C14 1.375(4) . ?
C15 C16 1.521(4) . ?
C16 C17 1.512(4) . ?
C17 C18 1.508(4) . ?
C18 C22 1.367(5) . ?
C18 C19 1.385(4) . ?
C19 C20 1.384(4) . ?
C21 C22 1.390(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O4 125.99(8) 2_655 4_455 ?
O6 Zn1 O1 114.78(8) 2_655 . ?
O4 Zn1 O1 103.90(8) 4_455 . ?
O6 Zn1 N1 113.19(9) 2_655 . ?
O4 Zn1 N1 99.45(8) 4_455 . ?
O1 Zn1 N1 94.03(8) . . ?
C1 O1 Zn1 122.88(16) . . ?
C5 O4 Zn1 127.08(19) . 4 ?
C8 O6 Zn1 114.85(16) . 2_654 ?
C10 N1 C14 117.4(3) . . ?
C10 N1 Zn1 126.3(2) . . ?
C14 N1 Zn1 116.11(18) . . ?
C21 N2 C20 122.3(3) . . ?
O2 C1 O1 125.3(2) . . ?
O2 C1 C2 120.2(2) . . ?
O1 C1 C2 114.5(2) . . ?
C9 C2 C3 119.5(2) . . ?
C9 C2 C1 121.4(2) . . ?
C3 C2 C1 119.0(2) . . ?
C4 C3 C2 120.6(2) . . ?
C3 C4 C6 119.6(2) . . ?
C3 C4 C5 119.7(2) . . ?
C6 C4 C5 120.7(2) . . ?
O3 C5 O4 125.0(2) . . ?
O3 C5 C4 118.8(2) . . ?
O4 C5 C4 116.1(3) . . ?
C4 C6 C7 119.9(2) . . ?
C6 C7 C9 119.7(2) . . ?
C6 C7 C8 120.0(2) . . ?
C9 C7 C8 120.3(2) . . ?
O5 C8 O6 123.7(2) . . ?
O5 C8 C7 121.2(2) . . ?
O6 C8 C7 115.1(2) . . ?
C2 C9 C7 120.5(2) . . ?
N1 C10 C11 122.7(3) . . ?
C10 C11 C12 120.0(3) . . ?
C13 C12 C11 116.9(3) . . ?
C13 C12 C15 121.7(3) . . ?
C11 C12 C15 121.5(3) . . ?
C14 C13 C12 119.9(3) . . ?
N1 C14 C13 123.1(3) . . ?
C12 C15 C16 115.9(2) . . ?
C17 C16 C15 111.3(2) . . ?
C18 C17 C16 115.0(3) . . ?
C22 C18 C19 118.6(3) . . ?
C22 C18 C17 120.6(3) . . ?
C19 C18 C17 120.8(3) . . ?
C20 C19 C18 119.0(3) . . ?
N2 C20 C19 120.3(3) . . ?
N2 C21 C22 119.2(3) . . ?
C18 C22 C21 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_LJB_1_H2O_180K
_database_code_depnum_ccdc_archive 'CCDC 1441458'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O7 Zn'
_chemical_formula_weight         489.77

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   19.1196(10)
_cell_length_b                   7.8379(4)
_cell_length_c                   13.7729(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2063.97(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5215
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6074
_exptl_absorpt_correction_T_max  0.7951
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10711
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.01
_reflns_number_total             4032
_reflns_number_gt                3813
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0179P)²+0.5330P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(9)
_refine_ls_number_reflns         4032
_refine_ls_number_parameters     289
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.009
_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 0.386824(11) -0.04644(3) 0.20599(2) 0.01226(8) Uani 1 1 d . . .
O1 O 0.46737(9) 0.0611(2) 0.14365(13) 0.0172(4) Uani 1 1 d . . .
O2 O 0.49892(10) 0.2239(3) 0.26891(15) 0.0294(5) Uani 1 1 d . . .
O3 O 0.76330(10) 0.3071(3) 0.28435(15) 0.0336(5) Uani 1 1 d . . .
O4 O 0.80682(9) 0.4257(2) 0.15155(14) 0.0231(4) Uani 1 1 d . . .
O5 O 0.69904(10) 0.2499(3) -0.16718(14) 0.0293(5) Uani 1 1 d . . .
O6 O 0.59979(9) 0.1033(3) -0.15920(14) 0.0204(4) Uani 1 1 d . . .
N1 N 0.38798(10) -0.2564(3) 0.11601(17) 0.0172(5) Uani 1 1 d . . .
N2 N 0.33128(13) -0.7741(3) -0.54461(17) 0.0287(6) Uani 1 1 d . . .
H2 H 0.3164 -0.7788 -0.6050 0.034 Uiso 1 1 calc R . .
C1 C 0.50956(12) 0.1604(3) 0.18871(17) 0.0149(6) Uani 1 1 d . . .
C2 C 0.57693(12) 0.1981(3) 0.13500(19) 0.0131(5) Uani 1 1 d . . .
C3 C 0.63555(11) 0.2499(3) 0.18706(16) 0.0125(6) Uani 1 1 d . . .
H3 H 0.6331 0.2579 0.2558 0.015 Uiso 1 1 calc R . .
C4 C 0.69781(12) 0.2902(3) 0.13978(19) 0.0155(5) Uani 1 1 d . . .
C5 C 0.76030(11) 0.3455(3) 0.1974(2) 0.0168(5) Uani 1 1 d . . .
C6 C 0.70109(13) 0.2774(3) 0.03906(18) 0.0166(5) Uani 1 1 d . . .
H6 H 0.7426 0.3095 0.0059 0.020 Uiso 1 1 calc R . .
C7 C 0.64382(13) 0.2178(3) -0.01325(19) 0.0153(5) Uani 1 1 d . . .
C8 C 0.64930(13) 0.1916(3) -0.12100(18) 0.0165(5) Uani 1 1 d . . .
C9 C 0.58181(13) 0.1766(3) 0.03582(18) 0.0148(5) Uani 1 1 d . . .
H9 H 0.5429 0.1337 0.0005 0.018 Uiso 1 1 calc R . .
C10 C 0.38219(14) -0.4199(4) 0.1435(2) 0.0215(6) Uani 1 1 d . . .
H10 H 0.3726 -0.4439 0.2098 0.026 Uiso 1 1 calc R . .
C11 C 0.38945(14) -0.5542(4) 0.0802(2) 0.0232(6) Uani 1 1 d . . .
H11 H 0.3836 -0.6680 0.1026 0.028 Uiso 1 1 calc R . .
C12 C 0.40540(14) -0.5230(4) -0.0171(2) 0.0207(6) Uani 1 1 d . . .
C13 C 0.41187(14) -0.3541(4) -0.0454(2) 0.0233(6) Uani 1 1 d . . .
H13 H 0.4230 -0.3265 -0.1108 0.028 Uiso 1 1 calc R . .
C14 C 0.40211(14) -0.2265(4) 0.02201(19) 0.0207(6) Uani 1 1 d . . .
H14 H 0.4055 -0.1114 0.0009 0.025 Uiso 1 1 calc R . .
C15 C 0.41694(17) -0.6669(4) -0.0880(2) 0.0294(7) Uani 1 1 d . . .
H15A H 0.3948 -0.7711 -0.0615 0.035 Uiso 1 1 calc R . .
H15B H 0.4678 -0.6890 -0.0925 0.035 Uiso 1 1 calc R . .
C16 C 0.38894(14) -0.6375(4) -0.1899(2) 0.0267(7) Uani 1 1 d . . .
H16A H 0.3376 -0.6211 -0.1871 0.032 Uiso 1 1 calc R . .
H16B H 0.4100 -0.5326 -0.2172 0.032 Uiso 1 1 calc R . .
C17 C 0.4056(2) -0.7875(5) -0.2552(2) 0.0377(9) Uani 1 1 d . . .
H17A H 0.4571 -0.8011 -0.2583 0.045 Uiso 1 1 calc R . .
H17B H 0.3862 -0.8922 -0.2254 0.045 Uiso 1 1 calc R . .
C18 C 0.37784(16) -0.7724(4) -0.3572(2) 0.0274(7) Uani 1 1 d . . .
C19 C 0.30751(16) -0.7969(5) -0.3775(2) 0.0381(8) Uani 1 1 d . . .
H19 H 0.2749 -0.8130 -0.3262 0.046 Uiso 1 1 calc R . .
C20 C 0.28537(16) -0.7976(5) -0.4730(2) 0.0416(9) Uani 1 1 d . . .
H20 H 0.2373 -0.8149 -0.4876 0.050 Uiso 1 1 calc R . .
C21 C 0.39812(17) -0.7441(5) -0.5282(2) 0.0350(8) Uani 1 1 d . . .
H21 H 0.4293 -0.7258 -0.5808 0.042 Uiso 1 1 calc R . .
C22 C 0.42250(16) -0.7396(5) -0.4330(2) 0.0362(8) Uani 1 1 d . . .
H22 H 0.4702 -0.7138 -0.4205 0.043 Uiso 1 1 calc R . .
O1W O 0.70413(16) 0.0124(4) 0.3730(2) 0.0722(9) Uani 1 1 d D . .
H2W1 H 0.7414 -0.0598 0.3614 0.050 Uiso 1 1 d D . .
H1W1 H 0.7183 0.1119 0.3462 0.050 Uiso 1 1 d 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 O6 1.9265(19) 2_655 ?
Zn1 O4 1.9487(18) 4_455 ?
Zn1 O1 1.9543(17) . ?
Zn1 N1 2.060(2) . ?
O1 C1 1.281(3) . ?
O2 C1 1.228(3) . ?
O3 C5 1.237(4) . ?
O4 C5 1.259(3) . ?
O4 Zn1 1.9486(18) 4 ?
O5 C8 1.232(3) . ?
O6 C8 1.285(3) . ?
O6 Zn1 1.9265(19) 2_654 ?
N1 C10 1.340(4) . ?
N1 C14 1.343(4) . ?
N2 C21 1.319(4) . ?
N2 C20 1.333(4) . ?
C1 C2 1.514(3) . ?
C2 C9 1.379(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.393(3) . ?
C4 C6 1.392(4) . ?
C4 C5 1.498(3) . ?
C6 C7 1.392(3) . ?
C7 C9 1.402(4) . ?
C7 C8 1.502(4) . ?
C10 C11 1.374(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.386(4) . ?
C12 C15 1.508(4) . ?
C13 C14 1.377(4) . ?
C15 C16 1.519(4) . ?
C16 C17 1.514(4) . ?
C17 C18 1.508(4) . ?
C18 C22 1.373(5) . ?
C18 C19 1.386(4) . ?
C19 C20 1.382(4) . ?
C21 C22 1.391(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O4 125.98(8) 2_655 4_455 ?
O6 Zn1 O1 114.74(8) 2_655 . ?
O4 Zn1 O1 103.90(8) 4_455 . ?
O6 Zn1 N1 113.16(9) 2_655 . ?
O4 Zn1 N1 99.49(8) 4_455 . ?
O1 Zn1 N1 94.11(8) . . ?
C1 O1 Zn1 123.04(16) . . ?
C5 O4 Zn1 127.18(19) . 4 ?
C8 O6 Zn1 114.92(16) . 2_654 ?
C10 N1 C14 117.1(2) . . ?
C10 N1 Zn1 126.3(2) . . ?
C14 N1 Zn1 116.27(18) . . ?
C21 N2 C20 122.4(3) . . ?
O2 C1 O1 125.3(2) . . ?
O2 C1 C2 120.1(2) . . ?
O1 C1 C2 114.7(2) . . ?
C9 C2 C3 119.4(2) . . ?
C9 C2 C1 121.2(2) . . ?
C3 C2 C1 119.4(2) . . ?
C2 C3 C4 120.9(2) . . ?
C6 C4 C3 119.2(2) . . ?
C6 C4 C5 120.8(2) . . ?
C3 C4 C5 120.0(2) . . ?
O3 C5 O4 125.1(2) . . ?
O3 C5 C4 118.6(2) . . ?
O4 C5 C4 116.3(3) . . ?
C7 C6 C4 120.3(2) . . ?
C6 C7 C9 119.5(2) . . ?
C6 C7 C8 120.2(2) . . ?
C9 C7 C8 120.3(2) . . ?
O5 C8 O6 123.8(2) . . ?
O5 C8 C7 120.9(2) . . ?
O6 C8 C7 115.3(2) . . ?
C2 C9 C7 120.4(2) . . ?
N1 C10 C11 123.0(3) . . ?
C10 C11 C12 119.8(3) . . ?
C13 C12 C11 117.2(3) . . ?
C13 C12 C15 121.3(3) . . ?
C11 C12 C15 121.5(3) . . ?
C14 C13 C12 119.5(3) . . ?
N1 C14 C13 123.4(3) . . ?
C12 C15 C16 115.7(2) . . ?
C17 C16 C15 110.9(2) . . ?
C18 C17 C16 114.7(3) . . ?
C22 C18 C19 118.5(3) . . ?
C22 C18 C17 120.3(3) . . ?
C19 C18 C17 121.2(3) . . ?
C20 C19 C18 119.3(3) . . ?
N2 C20 C19 120.1(3) . . ?
N2 C21 C22 119.4(3) . . ?
C18 C22 C21 120.2(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_LJB_1_H2O_200K
_database_code_depnum_ccdc_archive 'CCDC 1441459'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O7 Zn'
_chemical_formula_weight         489.77

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   19.1195(9)
_cell_length_b                   7.8491(4)
_cell_length_c                   13.7716(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2066.72(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5128
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6078
_exptl_absorpt_correction_T_max  0.7953
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10737
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4039
_reflns_number_gt                3812
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0220P)²+0.5192P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.023(9)
_refine_ls_number_reflns         4039
_refine_ls_number_parameters     289
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.064
_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 0.386801(11) -0.04610(3) 0.18583(2) 0.01323(8) Uani 1 1 d . . .
O1 O 0.46744(9) 0.0608(2) 0.12342(13) 0.0187(4) Uani 1 1 d . . .
O2 O 0.49905(10) 0.2233(3) 0.24873(15) 0.0324(5) Uani 1 1 d . . .
O3 O 0.76372(10) 0.3059(3) 0.26425(15) 0.0358(5) Uani 1 1 d . . .
O4 O 0.80686(9) 0.4254(2) 0.13167(14) 0.0244(5) Uani 1 1 d . . .
O5 O 0.69927(10) 0.2491(3) -0.18740(15) 0.0313(5) Uani 1 1 d . . .
O6 O 0.59982(9) 0.1032(3) -0.17940(14) 0.0225(4) Uani 1 1 d . . .
N1 N 0.38784(10) -0.2557(3) 0.09594(16) 0.0178(5) Uani 1 1 d . . .
N2 N 0.33141(13) -0.7731(3) -0.56445(17) 0.0304(6) Uani 1 1 d . . .
H2 H 0.3166 -0.7773 -0.6249 0.036 Uiso 1 1 calc R . .
C1 C 0.50964(12) 0.1600(3) 0.16860(17) 0.0168(6) Uani 1 1 d . . .
C2 C 0.57704(12) 0.1973(3) 0.11497(19) 0.0142(5) Uani 1 1 d . . .
C3 C 0.63558(11) 0.2491(3) 0.16730(16) 0.0139(6) Uani 1 1 d . . .
H3 H 0.6332 0.2571 0.2361 0.017 Uiso 1 1 calc R . .
C4 C 0.69792(13) 0.2896(3) 0.11948(19) 0.0171(5) Uani 1 1 d . . .
C5 C 0.76056(11) 0.3447(3) 0.1775(2) 0.0179(5) Uani 1 1 d . . .
C6 C 0.70124(13) 0.2770(3) 0.01889(18) 0.0175(5) Uani 1 1 d . . .
H6 H 0.7428 0.3091 -0.0142 0.021 Uiso 1 1 calc R . .
C7 C 0.64388(13) 0.2175(3) -0.03351(19) 0.0163(5) Uani 1 1 d . . .
C8 C 0.64941(13) 0.1908(3) -0.14113(18) 0.0181(5) Uani 1 1 d . . .
C9 C 0.58180(13) 0.1765(3) 0.01544(18) 0.0155(5) Uani 1 1 d . . .
H9 H 0.5428 0.1342 -0.0199 0.019 Uiso 1 1 calc R . .
C10 C 0.38216(14) -0.4190(4) 0.1238(2) 0.0227(6) Uani 1 1 d . . .
H10 H 0.3726 -0.4432 0.1901 0.027 Uiso 1 1 calc R . .
C11 C 0.38970(14) -0.5533(4) 0.0596(2) 0.0244(6) Uani 1 1 d . . .
H11 H 0.3840 -0.6670 0.0819 0.029 Uiso 1 1 calc R . .
C12 C 0.40555(15) -0.5226(4) -0.0371(2) 0.0216(6) Uani 1 1 d . . .
C13 C 0.41158(14) -0.3534(4) -0.0654(2) 0.0242(6) Uani 1 1 d . . .
H13 H 0.4223 -0.3258 -0.1309 0.029 Uiso 1 1 calc R . .
C14 C 0.40200(15) -0.2259(4) 0.0021(2) 0.0223(6) Uani 1 1 d . . .
H14 H 0.4056 -0.1110 -0.0190 0.027 Uiso 1 1 calc R . .
C15 C 0.41698(18) -0.6662(4) -0.1077(2) 0.0313(7) Uani 1 1 d . . .
H15A H 0.3948 -0.7701 -0.0810 0.038 Uiso 1 1 calc R . .
H15B H 0.4678 -0.6883 -0.1123 0.038 Uiso 1 1 calc R . .
C16 C 0.38887(15) -0.6370(4) -0.2096(2) 0.0293(7) Uani 1 1 d . . .
H16A H 0.3375 -0.6217 -0.2068 0.035 Uiso 1 1 calc R . .
H16B H 0.4096 -0.5317 -0.2368 0.035 Uiso 1 1 calc R . .
C17 C 0.4061(2) -0.7861(5) -0.2753(2) 0.0407(9) Uani 1 1 d . . .
H17A H 0.4576 -0.7985 -0.2784 0.049 Uiso 1 1 calc R . .
H17B H 0.3871 -0.8912 -0.2456 0.049 Uiso 1 1 calc R . .
C18 C 0.37815(16) -0.7715(4) -0.3776(2) 0.0285(7) Uani 1 1 d . . .
C19 C 0.30796(17) -0.7957(5) -0.3975(2) 0.0407(8) Uani 1 1 d . . .
H19 H 0.2754 -0.8117 -0.3462 0.049 Uiso 1 1 calc R . .
C20 C 0.28569(17) -0.7964(5) -0.4932(2) 0.0442(9) Uani 1 1 d . . .
H20 H 0.2376 -0.8135 -0.5079 0.053 Uiso 1 1 calc R . .
C21 C 0.39818(17) -0.7441(5) -0.5480(2) 0.0360(8) Uani 1 1 d . . .
H21 H 0.4295 -0.7265 -0.6006 0.043 Uiso 1 1 calc R . .
C22 C 0.42243(16) -0.7395(5) -0.4534(2) 0.0376(8) Uani 1 1 d . . .
H22 H 0.4702 -0.7140 -0.4410 0.045 Uiso 1 1 calc R . .
O1W O 0.70426(16) 0.0126(4) 0.3529(2) 0.0740(10) Uani 1 1 d D . .
H2W1 H 0.7347 -0.0677 0.3358 0.050 Uiso 1 1 d D . .
H1W1 H 0.7137 0.1022 0.3140 0.050 Uiso 1 1 d 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 O6 1.9264(19) 2_655 ?
Zn1 O4 1.9468(18) 4_455 ?
Zn1 O1 1.9546(18) . ?
Zn1 N1 2.059(2) . ?
O1 C1 1.282(3) . ?
O2 C1 1.227(3) . ?
O3 C5 1.234(4) . ?
O4 C5 1.258(3) . ?
O4 Zn1 1.9469(18) 4 ?
O5 C8 1.235(3) . ?
O6 C8 1.284(3) . ?
O6 Zn1 1.9264(19) 2_654 ?
N1 C14 1.341(4) . ?
N1 C10 1.343(4) . ?
N2 C21 1.317(4) . ?
N2 C20 1.326(4) . ?
C1 C2 1.514(3) . ?
C2 C9 1.383(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.398(3) . ?
C4 C6 1.390(4) . ?
C4 C5 1.503(3) . ?
C6 C7 1.393(3) . ?
C7 C9 1.403(4) . ?
C7 C8 1.501(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.388(4) . ?
C12 C15 1.505(4) . ?
C13 C14 1.378(4) . ?
C15 C16 1.520(4) . ?
C16 C17 1.515(4) . ?
C17 C18 1.512(4) . ?
C18 C22 1.367(5) . ?
C18 C19 1.383(4) . ?
C19 C20 1.385(4) . ?
C21 C22 1.383(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O4 125.92(8) 2_655 4_455 ?
O6 Zn1 O1 114.76(8) 2_655 . ?
O4 Zn1 O1 104.00(8) 4_455 . ?
O6 Zn1 N1 113.08(9) 2_655 . ?
O4 Zn1 N1 99.55(8) 4_455 . ?
O1 Zn1 N1 94.08(8) . . ?
C1 O1 Zn1 122.94(16) . . ?
C5 O4 Zn1 127.24(19) . 4 ?
C8 O6 Zn1 114.96(17) . 2_654 ?
C14 N1 C10 117.3(2) . . ?
C14 N1 Zn1 116.27(18) . . ?
C10 N1 Zn1 126.2(2) . . ?
C21 N2 C20 122.4(3) . . ?
O2 C1 O1 125.3(2) . . ?
O2 C1 C2 120.1(2) . . ?
O1 C1 C2 114.6(2) . . ?
C9 C2 C3 119.6(2) . . ?
C9 C2 C1 121.1(2) . . ?
C3 C2 C1 119.2(2) . . ?
C2 C3 C4 120.5(2) . . ?
C6 C4 C3 119.5(2) . . ?
C6 C4 C5 120.9(2) . . ?
C3 C4 C5 119.6(2) . . ?
O3 C5 O4 125.1(2) . . ?
O3 C5 C4 118.8(2) . . ?
O4 C5 C4 116.0(3) . . ?
C4 C6 C7 120.3(2) . . ?
C6 C7 C9 119.6(2) . . ?
C6 C7 C8 120.2(2) . . ?
C9 C7 C8 120.1(2) . . ?
O5 C8 O6 123.8(2) . . ?
O5 C8 C7 120.8(2) . . ?
O6 C8 C7 115.4(2) . . ?
C2 C9 C7 120.3(2) . . ?
N1 C10 C11 122.5(3) . . ?
C10 C11 C12 120.2(3) . . ?
C11 C12 C13 117.0(3) . . ?
C11 C12 C15 121.5(3) . . ?
C13 C12 C15 121.5(3) . . ?
C14 C13 C12 119.6(3) . . ?
N1 C14 C13 123.4(3) . . ?
C12 C15 C16 115.6(2) . . ?
C17 C16 C15 111.0(2) . . ?
C18 C17 C16 114.9(3) . . ?
C22 C18 C19 118.4(3) . . ?
C22 C18 C17 120.5(3) . . ?
C19 C18 C17 121.1(3) . . ?
C18 C19 C20 119.2(3) . . ?
N2 C20 C19 120.0(3) . . ?
N2 C21 C22 119.5(3) . . ?
C18 C22 C21 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_LJB_1_H2O_220K
_database_code_depnum_ccdc_archive 'CCDC 1441460'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O7 Zn'
_chemical_formula_weight         489.77

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   19.1176(9)
_cell_length_b                   7.8572(4)
_cell_length_c                   13.7712(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2068.58(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    4994
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6074
_exptl_absorpt_correction_T_max  0.7955
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10746
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.01
_reflns_number_total             4043
_reflns_number_gt                3795
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0246P)²+0.3985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(10)
_refine_ls_number_reflns         4043
_refine_ls_number_parameters     289
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0703
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.008
_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 0.386774(12) -0.04587(3) 0.19025(2) 0.01456(8) Uani 1 1 d . . .
C5 C 0.76070(12) 0.3443(3) 0.1820(2) 0.0199(5) Uani 1 1 d . . .
C3 C 0.63574(12) 0.2493(3) 0.17147(17) 0.0155(6) Uani 1 1 d . . .
H3 H 0.6333 0.2576 0.2395 0.019 Uiso 1 1 calc R . .
C9 C 0.58185(13) 0.1763(3) 0.01989(19) 0.0176(5) Uani 1 1 d . . .
H9 H 0.5433 0.1343 -0.0151 0.021 Uiso 1 1 calc R . .
C6 C 0.70123(13) 0.2768(4) 0.02345(19) 0.0192(6) Uani 1 1 d . . .
H6 H 0.7423 0.3087 -0.0093 0.023 Uiso 1 1 calc R . .
O4 O 0.80680(10) 0.4252(3) 0.13594(15) 0.0271(5) Uani 1 1 d . . .
O3 O 0.76384(11) 0.3056(3) 0.26850(16) 0.0399(6) Uani 1 1 d . . .
C7 C 0.64387(13) 0.2173(3) -0.0290(2) 0.0172(5) Uani 1 1 d . . .
C4 C 0.69789(13) 0.2892(3) 0.1243(2) 0.0184(6) Uani 1 1 d . . .
C2 C 0.57696(12) 0.1972(3) 0.11956(19) 0.0153(5) Uani 1 1 d . . .
C8 C 0.64936(13) 0.1908(4) -0.13685(19) 0.0193(6) Uani 1 1 d . . .
C1 C 0.50971(12) 0.1599(3) 0.17313(18) 0.0180(6) Uani 1 1 d . . .
O2 O 0.49907(11) 0.2230(3) 0.25304(16) 0.0363(6) Uani 1 1 d . . .
O5 O 0.69913(11) 0.2489(3) -0.18279(15) 0.0343(5) Uani 1 1 d . . .
O6 O 0.59987(10) 0.1029(3) -0.17505(15) 0.0240(4) Uani 1 1 d . . .
O1 O 0.46750(9) 0.0608(2) 0.12801(14) 0.0200(4) Uani 1 1 d . . .
N1 N 0.38801(11) -0.2556(3) 0.10047(17) 0.0194(5) Uani 1 1 d . . .
C14 C 0.40213(15) -0.2263(4) 0.0064(2) 0.0243(6) Uani 1 1 d . . .
H14 H 0.4057 -0.1128 -0.0145 0.029 Uiso 1 1 calc R . .
C10 C 0.38231(15) -0.4187(4) 0.1281(2) 0.0251(7) Uani 1 1 d . . .
H10 H 0.3727 -0.4426 0.1936 0.030 Uiso 1 1 calc R . .
C13 C 0.41163(15) -0.3529(4) -0.0608(2) 0.0264(6) Uani 1 1 d . . .
H13 H 0.4220 -0.3254 -0.1256 0.032 Uiso 1 1 calc R . .
C12 C 0.40589(15) -0.5220(4) -0.0326(2) 0.0243(6) Uani 1 1 d . . .
C11 C 0.38994(15) -0.5525(4) 0.0644(2) 0.0266(7) Uani 1 1 d . . .
H11 H 0.3844 -0.6648 0.0866 0.032 Uiso 1 1 calc R . .
C15 C 0.41717(19) -0.6650(4) -0.1035(2) 0.0342(7) Uani 1 1 d . . .
H15A H 0.3953 -0.7678 -0.0770 0.041 Uiso 1 1 calc R . .
H15B H 0.4675 -0.6869 -0.1080 0.041 Uiso 1 1 calc R . .
C16 C 0.38915(15) -0.6368(4) -0.2055(2) 0.0318(7) Uani 1 1 d . . .
H16A H 0.3383 -0.6216 -0.2027 0.038 Uiso 1 1 calc R . .
H16B H 0.4096 -0.5327 -0.2325 0.038 Uiso 1 1 calc R . .
C17 C 0.4062(2) -0.7850(5) -0.2707(2) 0.0443(10) Uani 1 1 d . . .
H17A H 0.3875 -0.8890 -0.2412 0.053 Uiso 1 1 calc R . .
H17B H 0.4572 -0.7972 -0.2739 0.053 Uiso 1 1 calc R . .
C22 C 0.42235(17) -0.7381(5) -0.4486(3) 0.0405(8) Uani 1 1 d . . .
H22 H 0.4695 -0.7120 -0.4362 0.049 Uiso 1 1 calc R . .
C18 C 0.37818(16) -0.7708(4) -0.3730(3) 0.0311(8) Uani 1 1 d . . .
C19 C 0.30804(18) -0.7951(5) -0.3929(3) 0.0452(9) Uani 1 1 d . . .
H19 H 0.2758 -0.8108 -0.3421 0.054 Uiso 1 1 calc R . .
N2 N 0.33161(14) -0.7727(4) -0.56010(18) 0.0344(6) Uani 1 1 d . . .
H2 H 0.3168 -0.7773 -0.6198 0.041 Uiso 1 1 calc R . .
C21 C 0.39812(18) -0.7431(5) -0.5439(3) 0.0413(9) Uani 1 1 d . . .
H21 H 0.4290 -0.7255 -0.5961 0.050 Uiso 1 1 calc R . .
C20 C 0.28604(17) -0.7958(6) -0.4886(3) 0.0472(10) Uani 1 1 d . . .
H20 H 0.2385 -0.8129 -0.5030 0.057 Uiso 1 1 calc R . .
O1W O 0.70426(17) 0.0122(5) 0.3565(3) 0.0784(10) Uani 1 1 d D . .
H2W1 H 0.7377 -0.0653 0.3472 0.050 Uiso 1 1 d D . .
H1W1 H 0.7226 0.1095 0.3301 0.050 Uiso 1 1 d 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 O6 1.925(2) 2_655 ?
Zn1 O4 1.9485(19) 4_455 ?
Zn1 O1 1.9543(18) . ?
Zn1 N1 2.061(2) . ?
C5 O3 1.230(4) . ?
C5 O4 1.258(3) . ?
C5 C4 1.504(3) . ?
C3 C4 1.390(3) . ?
C3 C2 1.393(3) . ?
C9 C2 1.386(4) . ?
C9 C7 1.401(4) . ?
C6 C7 1.394(4) . ?
C6 C4 1.394(4) . ?
O4 Zn1 1.9485(19) 4 ?
C7 C8 1.504(4) . ?
C2 C1 1.511(3) . ?
C8 O5 1.230(3) . ?
C8 O6 1.284(3) . ?
C1 O2 1.224(3) . ?
C1 O1 1.282(3) . ?
O6 Zn1 1.925(2) 2_654 ?
N1 C10 1.341(4) . ?
N1 C14 1.343(4) . ?
C14 C13 1.371(4) . ?
C10 C11 1.376(4) . ?
C13 C12 1.388(4) . ?
C12 C11 1.392(4) . ?
C12 C15 1.504(4) . ?
C15 C16 1.520(4) . ?
C16 C17 1.507(4) . ?
C17 C18 1.512(5) . ?
C22 C18 1.365(5) . ?
C22 C21 1.393(5) . ?
C18 C19 1.382(4) . ?
C19 C20 1.383(5) . ?
N2 C21 1.312(4) . ?
N2 C20 1.328(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O4 125.96(8) 2_655 4_455 ?
O6 Zn1 O1 114.69(8) 2_655 . ?
O4 Zn1 O1 104.03(9) 4_455 . ?
O6 Zn1 N1 112.99(9) 2_655 . ?
O4 Zn1 N1 99.67(9) 4_455 . ?
O1 Zn1 N1 94.07(8) . . ?
O3 C5 O4 125.4(2) . . ?
O3 C5 C4 118.6(2) . . ?
O4 C5 C4 116.0(3) . . ?
C4 C3 C2 121.1(2) . . ?
C2 C9 C7 120.4(2) . . ?
C7 C6 C4 120.2(2) . . ?
C5 O4 Zn1 127.0(2) . 4 ?
C6 C7 C9 119.6(2) . . ?
C6 C7 C8 120.2(2) . . ?
C9 C7 C8 120.1(2) . . ?
C3 C4 C6 119.3(2) . . ?
C3 C4 C5 120.1(2) . . ?
C6 C4 C5 120.7(2) . . ?
C9 C2 C3 119.3(2) . . ?
C9 C2 C1 121.2(2) . . ?
C3 C2 C1 119.5(2) . . ?
O5 C8 O6 124.0(3) . . ?
O5 C8 C7 120.7(2) . . ?
O6 C8 C7 115.3(2) . . ?
O2 C1 O1 125.2(2) . . ?
O2 C1 C2 120.1(2) . . ?
O1 C1 C2 114.6(2) . . ?
C8 O6 Zn1 114.97(17) . 2_654 ?
C1 O1 Zn1 123.03(17) . . ?
C10 N1 C14 117.0(3) . . ?
C10 N1 Zn1 126.4(2) . . ?
C14 N1 Zn1 116.36(19) . . ?
N1 C14 C13 123.6(3) . . ?
N1 C10 C11 122.7(3) . . ?
C14 C13 C12 119.7(3) . . ?
C13 C12 C11 116.8(3) . . ?
C13 C12 C15 121.5(3) . . ?
C11 C12 C15 121.7(3) . . ?
C10 C11 C12 120.2(3) . . ?
C12 C15 C16 116.1(3) . . ?
C17 C16 C15 111.2(3) . . ?
C16 C17 C18 114.9(3) . . ?
C18 C22 C21 120.5(3) . . ?
C22 C18 C19 118.4(3) . . ?
C22 C18 C17 120.4(3) . . ?
C19 C18 C17 121.2(4) . . ?
C18 C19 C20 119.0(3) . . ?
C21 N2 C20 122.3(3) . . ?
N2 C21 C22 119.2(3) . . ?
N2 C20 C19 120.5(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_LJB_1_H2O_240K
_database_code_depnum_ccdc_archive 'CCDC 1441461'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O7 Zn'
_chemical_formula_weight         489.77

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   19.1136(9)
_cell_length_b                   7.8642(4)
_cell_length_c                   13.7696(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2069.75(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    4878
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_T_max  0.7956
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10748
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4041
_reflns_number_gt                3783
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0298P)²+0.3787P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(10)
_refine_ls_number_reflns         4041
_refine_ls_number_parameters     289
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.019
_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 0.386740(12) -0.04567(3) 0.18817(3) 0.01591(9) Uani 1 1 d . . .
O1 O 0.46748(10) 0.0609(2) 0.12604(14) 0.0220(4) Uani 1 1 d . . .
O2 O 0.49928(11) 0.2228(3) 0.25088(16) 0.0396(6) Uani 1 1 d . . .
O3 O 0.76408(12) 0.3055(3) 0.26602(17) 0.0436(6) Uani 1 1 d . . .
O4 O 0.80688(10) 0.4251(3) 0.13390(16) 0.0292(5) Uani 1 1 d . . .
O5 O 0.69910(11) 0.2487(3) -0.18492(16) 0.0377(6) Uani 1 1 d . . .
O6 O 0.59993(10) 0.1028(3) -0.17711(15) 0.0266(5) Uani 1 1 d . . .
N1 N 0.38815(11) -0.2554(3) 0.09805(18) 0.0209(5) Uani 1 1 d . . .
N2 N 0.33173(14) -0.7718(4) -0.5619(2) 0.0383(7) Uani 1 1 d . . .
H2 H 0.3170 -0.7762 -0.6216 0.046 Uiso 1 1 calc R . .
C1 C 0.50988(12) 0.1593(4) 0.17118(19) 0.0200(6) Uani 1 1 d . . .
C2 C 0.57720(13) 0.1969(3) 0.1173(2) 0.0171(5) Uani 1 1 d . . .
C3 C 0.63579(12) 0.2486(3) 0.16941(18) 0.0171(6) Uani 1 1 d . . .
H3 H 0.6334 0.2563 0.2374 0.021 Uiso 1 1 calc R . .
C4 C 0.69802(13) 0.2891(4) 0.1220(2) 0.0197(6) Uani 1 1 d . . .
C5 C 0.76067(12) 0.3443(3) 0.1797(2) 0.0213(6) Uani 1 1 d . . .
C6 C 0.70119(13) 0.2765(4) 0.02115(19) 0.0202(6) Uani 1 1 d . . .
H6 H 0.7422 0.3084 -0.0118 0.024 Uiso 1 1 calc R . .
C7 C 0.64379(14) 0.2168(3) -0.0311(2) 0.0195(6) Uani 1 1 d . . .
C8 C 0.64924(14) 0.1909(4) -0.13880(19) 0.0215(6) Uani 1 1 d . . .
C9 C 0.58184(13) 0.1761(3) 0.01795(19) 0.0182(6) Uani 1 1 d . . .
H9 H 0.5432 0.1345 -0.0170 0.022 Uiso 1 1 calc R . .
C10 C 0.38248(15) -0.4181(4) 0.1261(2) 0.0262(7) Uani 1 1 d . . .
H10 H 0.3730 -0.4417 0.1917 0.031 Uiso 1 1 calc R . .
C11 C 0.39008(15) -0.5521(4) 0.0622(2) 0.0287(7) Uani 1 1 d . . .
H11 H 0.3845 -0.6644 0.0843 0.034 Uiso 1 1 calc R . .
C12 C 0.40591(16) -0.5214(4) -0.0346(2) 0.0260(6) Uani 1 1 d . . .
C13 C 0.41176(16) -0.3527(4) -0.0628(2) 0.0291(7) Uani 1 1 d . . .
H13 H 0.4223 -0.3252 -0.1276 0.035 Uiso 1 1 calc R . .
C14 C 0.40212(16) -0.2266(4) 0.0044(2) 0.0258(6) Uani 1 1 d . . .
H14 H 0.4055 -0.1131 -0.0165 0.031 Uiso 1 1 calc R . .
C15 C 0.4171(2) -0.6642(4) -0.1054(2) 0.0366(8) Uani 1 1 d . . .
H15A H 0.3951 -0.7668 -0.0789 0.044 Uiso 1 1 calc R . .
H15B H 0.4675 -0.6863 -0.1098 0.044 Uiso 1 1 calc R . .
C16 C 0.38925(16) -0.6361(5) -0.2074(2) 0.0355(8) Uani 1 1 d . . .
H16A H 0.3384 -0.6204 -0.2047 0.043 Uiso 1 1 calc R . .
H16B H 0.4099 -0.5322 -0.2344 0.043 Uiso 1 1 calc R . .
C17 C 0.4060(2) -0.7841(5) -0.2730(3) 0.0486(11) Uani 1 1 d . . .
H17A H 0.4570 -0.7969 -0.2762 0.058 Uiso 1 1 calc R . .
H17B H 0.3870 -0.8878 -0.2437 0.058 Uiso 1 1 calc R . .
C18 C 0.37827(17) -0.7696(4) -0.3749(3) 0.0343(8) Uani 1 1 d . . .
C19 C 0.30818(18) -0.7942(6) -0.3952(3) 0.0489(10) Uani 1 1 d . . .
H19 H 0.2759 -0.8100 -0.3445 0.059 Uiso 1 1 calc R . .
C20 C 0.28595(19) -0.7954(6) -0.4907(3) 0.0529(11) Uani 1 1 d . . .
H20 H 0.2384 -0.8130 -0.5053 0.063 Uiso 1 1 calc R . .
C21 C 0.39799(19) -0.7423(6) -0.5458(3) 0.0462(10) Uani 1 1 d . . .
H21 H 0.4289 -0.7247 -0.5980 0.055 Uiso 1 1 calc R . .
C22 C 0.42232(18) -0.7372(5) -0.4508(3) 0.0449(9) Uani 1 1 d . . .
H22 H 0.4695 -0.7112 -0.4386 0.054 Uiso 1 1 calc R . .
O1W O 0.70399(19) 0.0121(5) 0.3540(3) 0.0865(11) Uani 1 1 d D . .
H2W1 H 0.7382 -0.0621 0.3479 0.050 Uiso 1 1 d D . .
H1W1 H 0.7269 0.1139 0.3521 0.050 Uiso 1 1 d 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 O6 1.926(2) 2_655 ?
Zn1 O4 1.946(2) 4_455 ?
Zn1 O1 1.9532(19) . ?
Zn1 N1 2.064(2) . ?
O1 C1 1.282(3) . ?
O2 C1 1.223(4) . ?
O3 C5 1.229(4) . ?
O4 C5 1.257(3) . ?
O4 Zn1 1.946(2) 4 ?
O5 C8 1.232(3) . ?
O6 C8 1.283(3) . ?
O6 Zn1 1.926(2) 2_654 ?
N1 C14 1.336(4) . ?
N1 C10 1.341(4) . ?
N2 C21 1.306(5) . ?
N2 C20 1.326(5) . ?
C1 C2 1.514(3) . ?
C2 C9 1.381(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.394(4) . ?
C4 C6 1.394(4) . ?
C4 C5 1.501(4) . ?
C6 C7 1.393(4) . ?
C7 C9 1.400(4) . ?
C7 C8 1.501(4) . ?
C10 C11 1.381(4) . ?
C11 C12 1.387(5) . ?
C12 C13 1.386(4) . ?
C12 C15 1.503(4) . ?
C13 C14 1.369(4) . ?
C15 C16 1.518(4) . ?
C16 C17 1.508(5) . ?
C17 C18 1.504(5) . ?
C18 C22 1.366(5) . ?
C18 C19 1.382(5) . ?
C19 C20 1.383(5) . ?
C21 C22 1.389(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O4 125.96(9) 2_655 4_455 ?
O6 Zn1 O1 114.67(8) 2_655 . ?
O4 Zn1 O1 104.03(9) 4_455 . ?
O6 Zn1 N1 113.02(10) 2_655 . ?
O4 Zn1 N1 99.72(9) 4_455 . ?
O1 Zn1 N1 93.96(8) . . ?
C1 O1 Zn1 123.12(18) . . ?
C5 O4 Zn1 127.2(2) . 4 ?
C8 O6 Zn1 115.14(18) . 2_654 ?
C14 N1 C10 117.1(3) . . ?
C14 N1 Zn1 116.6(2) . . ?
C10 N1 Zn1 126.0(2) . . ?
C21 N2 C20 122.7(3) . . ?
O2 C1 O1 125.3(2) . . ?
O2 C1 C2 120.0(2) . . ?
O1 C1 C2 114.7(2) . . ?
C9 C2 C3 119.6(2) . . ?
C9 C2 C1 121.1(2) . . ?
C3 C2 C1 119.3(2) . . ?
C2 C3 C4 120.8(2) . . ?
C3 C4 C6 119.2(2) . . ?
C3 C4 C5 120.0(2) . . ?
C6 C4 C5 120.9(2) . . ?
O3 C5 O4 125.0(2) . . ?
O3 C5 C4 118.8(2) . . ?
O4 C5 C4 116.2(3) . . ?
C7 C6 C4 120.3(2) . . ?
C6 C7 C9 119.6(3) . . ?
C6 C7 C8 120.1(2) . . ?
C9 C7 C8 120.3(2) . . ?
O5 C8 O6 123.7(3) . . ?
O5 C8 C7 120.9(2) . . ?
O6 C8 C7 115.4(2) . . ?
C2 C9 C7 120.3(2) . . ?
N1 C10 C11 122.4(3) . . ?
C10 C11 C12 120.1(3) . . ?
C13 C12 C11 117.0(3) . . ?
C13 C12 C15 121.4(3) . . ?
C11 C12 C15 121.6(3) . . ?
C14 C13 C12 119.5(3) . . ?
N1 C14 C13 123.8(3) . . ?
C12 C15 C16 116.2(3) . . ?
C17 C16 C15 111.6(3) . . ?
C18 C17 C16 115.2(3) . . ?
C22 C18 C19 118.0(3) . . ?
C22 C18 C17 120.7(3) . . ?
C19 C18 C17 121.3(4) . . ?
C18 C19 C20 119.4(3) . . ?
N2 C20 C19 119.9(3) . . ?
N2 C21 C22 119.3(3) . . ?
C18 C22 C21 120.6(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_LJB_1_H2O_260K
_database_code_depnum_ccdc_archive 'CCDC 1441462'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O7 Zn'
_chemical_formula_weight         489.77

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   19.1062(9)
_cell_length_b                   7.8702(4)
_cell_length_c                   13.7665(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2070.06(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    4709
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      25.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_T_max  0.7956
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10710
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.97
_reflns_number_total             4025
_reflns_number_gt                3731
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0332P)²+0.5360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(11)
_refine_ls_number_reflns         4025
_refine_ls_number_parameters     289
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.012
_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 0.386747(12) -0.04555(4) 0.18522(3) 0.01747(9) Uani 1 1 d . . .
O1 O 0.46751(10) 0.0611(2) 0.12316(15) 0.0244(5) Uani 1 1 d . . .
O2 O 0.49934(12) 0.2225(4) 0.24790(18) 0.0433(7) Uani 1 1 d . . .
O3 O 0.76431(13) 0.3050(4) 0.26276(18) 0.0469(7) Uani 1 1 d . . .
O4 O 0.80689(11) 0.4251(3) 0.13075(17) 0.0314(5) Uani 1 1 d . . .
O5 O 0.69894(12) 0.2482(3) -0.18796(17) 0.0421(6) Uani 1 1 d . . .
O6 O 0.59997(11) 0.1029(3) -0.18017(16) 0.0287(5) Uani 1 1 d . . .
N1 N 0.38820(12) -0.2551(3) 0.09542(19) 0.0228(5) Uani 1 1 d . . .
N2 N 0.33169(15) -0.7710(4) -0.5650(2) 0.0415(7) Uani 1 1 d . . .
H2 H 0.3172 -0.7754 -0.6241 0.050 Uiso 1 1 calc R . .
C1 C 0.50995(13) 0.1594(4) 0.1684(2) 0.0221(7) Uani 1 1 d . . .
C2 C 0.57723(14) 0.1964(4) 0.1143(2) 0.0192(6) Uani 1 1 d . . .
C3 C 0.63595(13) 0.2487(3) 0.16637(18) 0.0184(6) Uani 1 1 d . . .
H3 H 0.6335 0.2570 0.2337 0.022 Uiso 1 1 calc R . .
C4 C 0.69816(14) 0.2887(4) 0.1191(2) 0.0215(6) Uani 1 1 d . . .
C5 C 0.76091(13) 0.3441(4) 0.1766(3) 0.0241(6) Uani 1 1 d . . .
C6 C 0.70134(14) 0.2764(4) 0.0180(2) 0.0220(6) Uani 1 1 d . . .
H6 H 0.7419 0.3085 -0.0146 0.026 Uiso 1 1 calc R . .
C7 C 0.64403(14) 0.2163(4) -0.0342(2) 0.0205(6) Uani 1 1 d . . .
C8 C 0.64925(15) 0.1905(4) -0.1417(2) 0.0236(6) Uani 1 1 d . . .
C9 C 0.58182(14) 0.1758(4) 0.0150(2) 0.0192(6) Uani 1 1 d . . .
H9 H 0.5435 0.1348 -0.0195 0.023 Uiso 1 1 calc R . .
C10 C 0.38293(16) -0.4173(4) 0.1230(2) 0.0295(7) Uani 1 1 d . . .
H10 H 0.3738 -0.4409 0.1880 0.035 Uiso 1 1 calc R . .
C11 C 0.39046(16) -0.5516(4) 0.0594(3) 0.0320(8) Uani 1 1 d . . .
H11 H 0.3852 -0.6625 0.0814 0.038 Uiso 1 1 calc R . .
C12 C 0.40589(17) -0.5208(4) -0.0378(2) 0.0281(7) Uani 1 1 d . . .
C13 C 0.41192(17) -0.3525(4) -0.0660(2) 0.0309(7) Uani 1 1 d . . .
H13 H 0.4224 -0.3252 -0.1301 0.037 Uiso 1 1 calc R . .
C14 C 0.40231(17) -0.2265(4) 0.0015(2) 0.0291(7) Uani 1 1 d . . .
H14 H 0.4058 -0.1143 -0.0192 0.035 Uiso 1 1 calc R . .
C15 C 0.4173(2) -0.6636(5) -0.1090(3) 0.0405(9) Uani 1 1 d . . .
H15A H 0.3958 -0.7654 -0.0828 0.049 Uiso 1 1 calc R . .
H15B H 0.4672 -0.6847 -0.1137 0.049 Uiso 1 1 calc R . .
C16 C 0.38922(17) -0.6357(5) -0.2103(3) 0.0381(9) Uani 1 1 d . . .
H16A H 0.3389 -0.6202 -0.2072 0.046 Uiso 1 1 calc R . .
H16B H 0.4095 -0.5330 -0.2371 0.046 Uiso 1 1 calc R . .
C17 C 0.4058(3) -0.7838(6) -0.2760(3) 0.0533(12) Uani 1 1 d . . .
H17A H 0.4562 -0.7972 -0.2790 0.064 Uiso 1 1 calc R . .
H17B H 0.3867 -0.8863 -0.2472 0.064 Uiso 1 1 calc R . .
C18 C 0.37825(19) -0.7687(5) -0.3781(3) 0.0378(9) Uani 1 1 d . . .
C19 C 0.3085(2) -0.7943(6) -0.3983(3) 0.0530(11) Uani 1 1 d . . .
H19 H 0.2766 -0.8110 -0.3481 0.064 Uiso 1 1 calc R . .
C20 C 0.2861(2) -0.7950(7) -0.4937(3) 0.0580(12) Uani 1 1 d . . .
H20 H 0.2391 -0.8123 -0.5079 0.070 Uiso 1 1 calc R . .
C21 C 0.3981(2) -0.7406(6) -0.5485(3) 0.0505(11) Uani 1 1 d . . .
H21 H 0.4288 -0.7225 -0.6000 0.061 Uiso 1 1 calc R . .
C22 C 0.42211(19) -0.7358(6) -0.4532(3) 0.0493(10) Uani 1 1 d . . .
H22 H 0.4687 -0.7097 -0.4409 0.059 Uiso 1 1 calc R . .
O1W O 0.7045(2) 0.0112(5) 0.3510(3) 0.0929(13) Uani 1 1 d D . .
H2W1 H 0.7407 -0.0607 0.3392 0.050 Uiso 1 1 d D . .
H1W1 H 0.7192 0.1200 0.3403 0.050 Uiso 1 1 d 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 O6 1.924(2) 2_655 ?
Zn1 O4 1.946(2) 4_455 ?
Zn1 O1 1.953(2) . ?
Zn1 N1 2.061(3) . ?
O1 C1 1.282(3) . ?
O2 C1 1.219(4) . ?
O3 C5 1.227(4) . ?
O4 C5 1.256(4) . ?
O4 Zn1 1.946(2) 4 ?
O5 C8 1.230(4) . ?
O6 C8 1.282(4) . ?
O6 Zn1 1.924(2) 2_654 ?
N1 C10 1.336(4) . ?
N1 C14 1.340(4) . ?
N2 C21 1.310(5) . ?
N2 C20 1.326(5) . ?
C1 C2 1.514(4) . ?
C2 C9 1.379(4) . ?
C2 C3 1.393(4) . ?
C3 C4 1.391(4) . ?
C4 C6 1.396(4) . ?
C4 C5 1.502(4) . ?
C6 C7 1.392(4) . ?
C7 C9 1.405(4) . ?
C7 C8 1.496(4) . ?
C10 C11 1.380(5) . ?
C11 C12 1.391(5) . ?
C12 C13 1.385(5) . ?
C12 C15 1.507(5) . ?
C13 C14 1.372(5) . ?
C15 C16 1.510(5) . ?
C16 C17 1.510(5) . ?
C17 C18 1.504(5) . ?
C18 C22 1.357(6) . ?
C18 C19 1.377(5) . ?
C19 C20 1.381(5) . ?
C21 C22 1.391(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O4 126.06(9) 2_655 4_455 ?
O6 Zn1 O1 114.70(9) 2_655 . ?
O4 Zn1 O1 103.97(10) 4_455 . ?
O6 Zn1 N1 112.83(10) 2_655 . ?
O4 Zn1 N1 99.74(10) 4_455 . ?
O1 Zn1 N1 94.07(9) . . ?
C1 O1 Zn1 123.12(19) . . ?
C5 O4 Zn1 127.0(2) . 4 ?
C8 O6 Zn1 115.32(19) . 2_654 ?
C10 N1 C14 116.8(3) . . ?
C10 N1 Zn1 126.4(2) . . ?
C14 N1 Zn1 116.5(2) . . ?
C21 N2 C20 122.2(3) . . ?
O2 C1 O1 125.2(3) . . ?
O2 C1 C2 120.3(3) . . ?
O1 C1 C2 114.5(2) . . ?
C9 C2 C3 119.6(2) . . ?
C9 C2 C1 121.2(2) . . ?
C3 C2 C1 119.2(2) . . ?
C4 C3 C2 120.9(3) . . ?
C3 C4 C6 119.2(3) . . ?
C3 C4 C5 120.0(3) . . ?
C6 C4 C5 120.7(3) . . ?
O3 C5 O4 125.2(3) . . ?
O3 C5 C4 118.6(3) . . ?
O4 C5 C4 116.2(3) . . ?
C7 C6 C4 120.2(3) . . ?
C6 C7 C9 119.6(3) . . ?
C6 C7 C8 120.2(3) . . ?
C9 C7 C8 120.2(2) . . ?
O5 C8 O6 123.4(3) . . ?
O5 C8 C7 120.9(3) . . ?
O6 C8 C7 115.6(2) . . ?
C2 C9 C7 120.3(3) . . ?
N1 C10 C11 122.9(3) . . ?
C10 C11 C12 120.0(3) . . ?
C13 C12 C11 117.0(3) . . ?
C13 C12 C15 121.3(3) . . ?
C11 C12 C15 121.7(3) . . ?
C14 C13 C12 119.4(3) . . ?
N1 C14 C13 124.0(3) . . ?
C12 C15 C16 116.1(3) . . ?
C17 C16 C15 111.6(3) . . ?
C18 C17 C16 115.2(3) . . ?
C22 C18 C19 118.2(4) . . ?
C22 C18 C17 120.8(4) . . ?
C19 C18 C17 121.0(4) . . ?
C18 C19 C20 119.5(4) . . ?
N2 C20 C19 120.1(3) . . ?
N2 C21 C22 119.2(4) . . ?
C18 C22 C21 120.7(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_LJB_1_H2O_260K-R
_database_code_depnum_ccdc_archive 'CCDC 1441463'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O7 Zn'
_chemical_formula_weight         489.77

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   19.1073(9)
_cell_length_b                   7.8706(4)
_cell_length_c                   13.7668(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2070.33(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    4719
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      25.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_T_max  0.7956
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10740
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4032
_reflns_number_gt                3744
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0318P)²+0.5490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.020(11)
_refine_ls_number_reflns         4032
_refine_ls_number_parameters     289
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.020
_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 0.386763(12) -0.04559(3) 0.20302(3) 0.01742(9) Uani 1 1 d . . .
O1 O 0.46756(11) 0.0612(2) 0.14107(15) 0.0248(5) Uani 1 1 d . . .
C3 C 0.63596(13) 0.2486(3) 0.18430(18) 0.0187(6) Uani 1 1 d . . .
H3 H 0.6336 0.2562 0.2516 0.022 Uiso 1 1 calc R . .
C1 C 0.50992(13) 0.1591(4) 0.1862(2) 0.0215(7) Uani 1 1 d . . .
C2 C 0.57727(13) 0.1971(3) 0.1321(2) 0.0180(6) Uani 1 1 d . . .
O2 O 0.49941(12) 0.2220(4) 0.26609(18) 0.0428(7) Uani 1 1 d . . .
C9 C 0.58172(14) 0.1756(4) 0.0330(2) 0.0201(6) Uani 1 1 d . . .
H9 H 0.5435 0.1337 -0.0014 0.024 Uiso 1 1 calc R . .
C5 C 0.76077(13) 0.3440(4) 0.1945(3) 0.0234(6) Uani 1 1 d . . .
C6 C 0.70127(14) 0.2761(4) 0.0360(2) 0.0224(6) Uani 1 1 d . . .
H6 H 0.7419 0.3073 0.0034 0.027 Uiso 1 1 calc R . .
C8 C 0.64910(15) 0.1902(4) -0.1240(2) 0.0235(6) Uani 1 1 d . . .
C4 C 0.69817(14) 0.2889(4) 0.1368(2) 0.0215(6) Uani 1 1 d . . .
C7 C 0.64383(14) 0.2168(4) -0.0162(2) 0.0208(6) Uani 1 1 d . . .
O6 O 0.59982(11) 0.1030(3) -0.16253(16) 0.0292(5) Uani 1 1 d . . .
O4 O 0.80695(11) 0.4250(3) 0.14867(16) 0.0312(5) Uani 1 1 d . . .
N1 N 0.38820(12) -0.2550(3) 0.11321(19) 0.0226(5) Uani 1 1 d . . .
O3 O 0.76427(13) 0.3056(4) 0.28059(18) 0.0467(7) Uani 1 1 d . . .
O5 O 0.69907(12) 0.2482(3) -0.16985(17) 0.0417(6) Uani 1 1 d . . .
C12 C 0.40600(17) -0.5208(4) -0.0199(2) 0.0284(7) Uani 1 1 d . . .
C11 C 0.39043(16) -0.5512(4) 0.0770(3) 0.0316(8) Uani 1 1 d . . .
H11 H 0.3851 -0.6622 0.0990 0.038 Uiso 1 1 calc R . .
C10 C 0.38279(16) -0.4176(4) 0.1407(2) 0.0293(7) Uani 1 1 d . . .
H10 H 0.3734 -0.4414 0.2055 0.035 Uiso 1 1 calc R . .
C14 C 0.40223(17) -0.2265(4) 0.0194(2) 0.0283(7) Uani 1 1 d . . .
H14 H 0.4056 -0.1143 -0.0013 0.034 Uiso 1 1 calc R . .
C13 C 0.41193(17) -0.3521(4) -0.0480(2) 0.0315(7) Uani 1 1 d . . .
H13 H 0.4224 -0.3247 -0.1121 0.038 Uiso 1 1 calc R . .
C15 C 0.4171(2) -0.6636(5) -0.0908(3) 0.0396(8) Uani 1 1 d . . .
H15A H 0.3954 -0.7651 -0.0645 0.047 Uiso 1 1 calc R . .
H15B H 0.4670 -0.6855 -0.0953 0.047 Uiso 1 1 calc R . .
C16 C 0.38916(17) -0.6360(5) -0.1926(3) 0.0380(9) Uani 1 1 d . . .
H16A H 0.3388 -0.6206 -0.1898 0.046 Uiso 1 1 calc R . .
H16B H 0.4095 -0.5334 -0.2194 0.046 Uiso 1 1 calc R . .
C18 C 0.37814(19) -0.7684(5) -0.3605(3) 0.0374(9) Uani 1 1 d . . .
C17 C 0.4059(3) -0.7839(6) -0.2580(3) 0.0518(12) Uani 1 1 d . . .
H17A H 0.3868 -0.8864 -0.2292 0.062 Uiso 1 1 calc R . .
H17B H 0.4563 -0.7971 -0.2610 0.062 Uiso 1 1 calc R . .
N2 N 0.33167(16) -0.7709(4) -0.5472(2) 0.0412(7) Uani 1 1 d . . .
H2 H 0.3171 -0.7747 -0.6062 0.049 Uiso 1 1 calc R . .
C21 C 0.3980(2) -0.7414(6) -0.5307(3) 0.0485(10) Uani 1 1 d . . .
H21 H 0.4287 -0.7246 -0.5823 0.058 Uiso 1 1 calc R . .
C20 C 0.2861(2) -0.7952(7) -0.4758(3) 0.0577(12) Uani 1 1 d . . .
H20 H 0.2391 -0.8126 -0.4901 0.069 Uiso 1 1 calc R . .
C19 C 0.3081(2) -0.7947(6) -0.3806(3) 0.0524(11) Uani 1 1 d . . .
H19 H 0.2763 -0.8118 -0.3304 0.063 Uiso 1 1 calc R . .
C22 C 0.4223(2) -0.7353(6) -0.4355(3) 0.0502(10) Uani 1 1 d . . .
H22 H 0.4688 -0.7085 -0.4232 0.060 Uiso 1 1 calc R . .
O1W O 0.7046(2) 0.0123(6) 0.3692(3) 0.0944(13) Uani 1 1 d D . .
H1W1 H 0.7194 0.1079 0.3330 0.050 Uiso 1 1 d D . .
H2W1 H 0.7403 -0.0647 0.3598 0.050 Uiso 1 1 d 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 O6 1.922(2) 2_655 ?
Zn1 O4 1.946(2) 4_455 ?
Zn1 O1 1.954(2) . ?
Zn1 N1 2.061(3) . ?
O1 C1 1.279(3) . ?
C3 C2 1.393(4) . ?
C3 C4 1.393(4) . ?
C1 O2 1.223(4) . ?
C1 C2 1.517(4) . ?
C2 C9 1.377(4) . ?
C9 C7 1.404(4) . ?
C5 O3 1.225(4) . ?
C5 O4 1.258(4) . ?
C5 C4 1.499(4) . ?
C6 C7 1.392(4) . ?
C6 C4 1.393(4) . ?
C8 O5 1.232(4) . ?
C8 O6 1.280(4) . ?
C8 C7 1.502(4) . ?
O6 Zn1 1.922(2) 2_654 ?
O4 Zn1 1.946(2) 4 ?
N1 C14 1.338(4) . ?
N1 C10 1.338(4) . ?
C12 C11 1.387(5) . ?
C12 C13 1.388(5) . ?
C12 C15 1.504(5) . ?
C11 C10 1.377(5) . ?
C14 C13 1.369(5) . ?
C15 C16 1.515(5) . ?
C16 C17 1.506(5) . ?
C18 C22 1.358(6) . ?
C18 C19 1.382(5) . ?
C18 C17 1.512(5) . ?
N2 C21 1.308(5) . ?
N2 C20 1.327(5) . ?
C21 C22 1.391(5) . ?
C20 C19 1.377(6) . ?

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
O6 Zn1 O4 126.11(9) 2_655 4_455 ?
O6 Zn1 O1 114.58(9) 2_655 . ?
O4 Zn1 O1 103.98(10) 4_455 . ?
O6 Zn1 N1 112.83(10) 2_655 . ?
O4 Zn1 N1 99.78(10) 4_455 . ?
O1 Zn1 N1 94.10(9) . . ?
C1 O1 Zn1 123.18(19) . . ?
C2 C3 C4 120.7(2) . . ?
O2 C1 O1 125.3(3) . . ?
O2 C1 C2 120.1(3) . . ?
O1 C1 C2 114.6(2) . . ?
C9 C2 C3 119.8(2) . . ?
C9 C2 C1 121.0(2) . . ?
C3 C2 C1 119.1(2) . . ?
C2 C9 C7 120.1(3) . . ?
O3 C5 O4 124.8(3) . . ?
O3 C5 C4 119.0(3) . . ?
O4 C5 C4 116.2(3) . . ?
C7 C6 C4 120.3(3) . . ?
O5 C8 O6 123.8(3) . . ?
O5 C8 C7 120.4(3) . . ?
O6 C8 C7 115.8(2) . . ?
C6 C4 C3 119.2(2) . . ?
C6 C4 C5 121.0(3) . . ?
C3 C4 C5 119.9(3) . . ?
C6 C7 C9 119.6(3) . . ?
C6 C7 C8 120.3(3) . . ?
C9 C7 C8 120.1(2) . . ?
C8 O6 Zn1 115.26(19) . 2_654 ?
C5 O4 Zn1 127.2(2) . 4 ?
C14 N1 C10 116.6(3) . . ?
C14 N1 Zn1 116.6(2) . . ?
C10 N1 Zn1 126.5(2) . . ?
C11 C12 C13 116.8(3) . . ?
C11 C12 C15 121.7(3) . . ?
C13 C12 C15 121.5(3) . . ?
C10 C11 C12 120.2(3) . . ?
N1 C10 C11 122.8(3) . . ?
N1 C14 C13 124.1(3) . . ?
C14 C13 C12 119.4(3) . . ?
C12 C15 C16 116.3(3) . . ?
C17 C16 C15 111.6(3) . . ?
C22 C18 C19 118.6(4) . . ?
C22 C18 C17 120.5(4) . . ?
C19 C18 C17 120.9(4) . . ?
C16 C17 C18 114.9(3) . . ?
C21 N2 C20 122.2(3) . . ?
N2 C21 C22 119.5(4) . . ?
N2 C20 C19 120.3(4) . . ?
C20 C19 C18 119.1(4) . . ?
C18 C22 C21 120.2(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_LJB_1_100K
_database_code_depnum_ccdc_archive 'CCDC 1441464'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn'
_chemical_formula_sum            'C22 H18 N2 O6 Zn'
_chemical_formula_weight         471.75

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   18.9732(17)
_cell_length_b                   7.7530(7)
_cell_length_c                   13.6972(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2014.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3511
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5446
_exptl_absorpt_correction_T_max  0.7991
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10386
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.96
_reflns_number_total             3896
_reflns_number_gt                3529
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0437P)²+0.5124P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3896
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.391383(17) 1.06107(4) 0.79732(3) 0.00912(11) Uani 1 1 d . . .
O1 O 0.47157(13) 0.9432(3) 0.85724(17) 0.0126(5) Uani 1 1 d . . .
O2 O 0.49815(14) 0.7705(3) 0.73162(19) 0.0202(6) Uani 1 1 d . . .
O3 O 0.76456(13) 0.6646(4) 0.71963(19) 0.0229(6) Uani 1 1 d . . .
O4 O 0.80919(13) 0.5491(3) 0.85581(18) 0.0140(6) Uani 1 1 d . . .
O5 O 0.69756(14) 0.7296(4) 1.17294(18) 0.0196(6) Uani 1 1 d . . .
O6 O 0.59671(13) 0.8782(3) 1.16211(18) 0.0140(5) Uani 1 1 d . . .
N1 N 0.39830(15) 1.2741(4) 0.8867(2) 0.0125(6) Uani 1 1 d . . .
N2 N 0.32511(16) 1.7903(4) 1.5485(2) 0.0176(7) Uani 1 1 d . . .
H2 H 0.3141 1.7911 1.6109 0.021 Uiso 1 1 calc R . .
C1 C 0.51120(17) 0.8346(4) 0.8116(3) 0.0129(8) Uani 1 1 d . . .
C2 C 0.57783(18) 0.7868(4) 0.8656(3) 0.0102(7) Uani 1 1 d . . .
C3 C 0.63660(17) 0.7296(4) 0.8155(2) 0.0102(8) Uani 1 1 d . . .
H3 H 0.6351 0.7214 0.7463 0.012 Uiso 1 1 calc R . .
C4 C 0.69820(18) 0.6837(5) 0.8650(3) 0.0125(7) Uani 1 1 d . . .
C5 C 0.76175(16) 0.6289(4) 0.8076(3) 0.0131(7) Uani 1 1 d . . .
C6 C 0.70027(18) 0.6950(4) 0.9661(2) 0.0103(7) Uani 1 1 d . . .
H6 H 0.7410 0.6578 1.0005 0.012 Uiso 1 1 calc R . .
C7 C 0.64274(18) 0.7606(4) 1.0172(2) 0.0113(7) Uani 1 1 d . . .
C8 C 0.64773(18) 0.7875(4) 1.1262(3) 0.0126(8) Uani 1 1 d . . .
C9 C 0.58227(19) 0.8076(5) 0.9668(2) 0.0111(7) Uani 1 1 d . . .
H9 H 0.5434 0.8546 1.0015 0.013 Uiso 1 1 calc R . .
C10 C 0.38668(18) 1.4373(5) 0.8571(3) 0.0138(8) Uani 1 1 d . . .
H10 H 0.3762 1.4578 0.7902 0.017 Uiso 1 1 calc R . .
C11 C 0.38944(19) 1.5761(5) 0.9203(3) 0.0153(8) Uani 1 1 d . . .
H11 H 0.3797 1.6890 0.8970 0.018 Uiso 1 1 calc R . .
C12 C 0.40648(19) 1.5504(5) 1.0177(3) 0.0145(8) Uani 1 1 d . . .
C13 C 0.42048(19) 1.3817(5) 1.0478(3) 0.0146(8) Uani 1 1 d . . .
H13 H 0.4333 1.3585 1.1135 0.018 Uiso 1 1 calc R . .
C14 C 0.41543(19) 1.2495(5) 0.9810(3) 0.0138(8) Uani 1 1 d . . .
H14 H 0.4245 1.1352 1.0026 0.017 Uiso 1 1 calc R . .
C15 C 0.4093(2) 1.7004(5) 1.0878(3) 0.0190(9) Uani 1 1 d . . .
H15A H 0.3821 1.7973 1.0595 0.023 Uiso 1 1 calc R . .
H15B H 0.4589 1.7386 1.0939 0.023 Uiso 1 1 calc R . .
C16 C 0.3806(2) 1.6626(5) 1.1901(3) 0.0175(8) Uani 1 1 d . . .
H16A H 0.3321 1.6160 1.1852 0.021 Uiso 1 1 calc R . .
H16B H 0.4105 1.5753 1.2226 0.021 Uiso 1 1 calc R . .
C17 C 0.3802(2) 1.8284(5) 1.2494(3) 0.0210(10) Uani 1 1 d . . .
H17A H 0.4277 1.8808 1.2468 0.025 Uiso 1 1 calc R . .
H17B H 0.3467 1.9106 1.2192 0.025 Uiso 1 1 calc R . .
C18 C 0.3598(2) 1.8022(5) 1.3551(3) 0.0165(9) Uani 1 1 d . . .
C19 C 0.2914(2) 1.8332(6) 1.3853(3) 0.0252(9) Uani 1 1 d . . .
H19 H 0.2557 1.8589 1.3389 0.030 Uiso 1 1 calc R . .
C20 C 0.2756(2) 1.8263(6) 1.4833(3) 0.0257(10) Uani 1 1 d . . .
H20 H 0.2287 1.8476 1.5044 0.031 Uiso 1 1 calc R . .
C21 C 0.3911(2) 1.7530(6) 1.5223(3) 0.0202(10) Uani 1 1 d . . .
H21 H 0.4253 1.7239 1.5703 0.024 Uiso 1 1 calc R . .
C22 C 0.4090(2) 1.7571(6) 1.4252(3) 0.0231(9) Uani 1 1 d . . .
H22 H 0.4556 1.7286 1.4059 0.028 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 O6 1.924(2) 2_674 ?
Zn1 O4 1.950(2) 4_465 ?
Zn1 O1 1.955(2) . ?
Zn1 N1 2.060(3) . ?
O1 C1 1.291(4) . ?
O2 C1 1.228(4) . ?
O3 C5 1.238(5) . ?
O4 C5 1.276(4) . ?
O4 Zn1 1.950(2) 4_565 ?
O5 C8 1.227(4) . ?
O6 C8 1.294(4) . ?
O6 Zn1 1.924(2) 2_675 ?
N1 C14 1.345(5) . ?
N1 C10 1.347(5) . ?
N2 C20 1.325(5) . ?
N2 C21 1.334(5) . ?
C1 C2 1.510(5) . ?
C2 C3 1.382(5) . ?
C2 C9 1.398(5) . ?
C3 C4 1.398(5) . ?
C4 C6 1.388(5) . ?
C4 C5 1.501(5) . ?
C6 C7 1.393(5) . ?
C7 C9 1.388(5) . ?
C7 C8 1.510(5) . ?
C10 C11 1.382(5) . ?
C11 C12 1.388(5) . ?
C12 C13 1.397(5) . ?
C12 C15 1.508(5) . ?
C13 C14 1.378(5) . ?
C15 C16 1.532(5) . ?
C16 C17 1.521(5) . ?
C17 C18 1.512(5) . ?
C18 C19 1.382(5) . ?
C18 C22 1.384(6) . ?
C19 C20 1.376(5) . ?
C21 C22 1.374(6) . ?

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
O6 Zn1 O4 126.61(10) 2_674 4_465 ?
O6 Zn1 O1 115.27(10) 2_674 . ?
O4 Zn1 O1 104.19(10) 4_465 . ?
O6 Zn1 N1 111.62(11) 2_674 . ?
O4 Zn1 N1 99.09(11) 4_465 . ?
O1 Zn1 N1 94.34(11) . . ?
C1 O1 Zn1 123.7(2) . . ?
C5 O4 Zn1 124.3(2) . 4_565 ?
C8 O6 Zn1 114.3(2) . 2_675 ?
C14 N1 C10 117.5(3) . . ?
C14 N1 Zn1 118.2(3) . . ?
C10 N1 Zn1 124.3(3) . . ?
C20 N2 C21 122.0(3) . . ?
O2 C1 O1 125.4(3) . . ?
O2 C1 C2 120.4(3) . . ?
O1 C1 C2 114.2(3) . . ?
C3 C2 C9 118.7(3) . . ?
C3 C2 C1 120.7(3) . . ?
C9 C2 C1 120.5(3) . . ?
C2 C3 C4 121.0(3) . . ?
C6 C4 C3 119.5(3) . . ?
C6 C4 C5 121.2(3) . . ?
C3 C4 C5 119.3(3) . . ?
O3 C5 O4 125.6(3) . . ?
O3 C5 C4 118.8(3) . . ?
O4 C5 C4 115.7(3) . . ?
C4 C6 C7 120.2(3) . . ?
C9 C7 C6 119.5(3) . . ?
C9 C7 C8 120.5(3) . . ?
C6 C7 C8 119.9(3) . . ?
O5 C8 O6 125.3(3) . . ?
O5 C8 C7 120.9(3) . . ?
O6 C8 C7 113.8(3) . . ?
C7 C9 C2 120.9(3) . . ?
N1 C10 C11 122.4(3) . . ?
C10 C11 C12 120.0(3) . . ?
C11 C12 C13 117.5(3) . . ?
C11 C12 C15 120.6(3) . . ?
C13 C12 C15 121.8(3) . . ?
C14 C13 C12 119.2(3) . . ?
N1 C14 C13 123.3(4) . . ?
C12 C15 C16 114.9(3) . . ?
C17 C16 C15 109.2(3) . . ?
C18 C17 C16 113.6(4) . . ?
C19 C18 C22 118.0(4) . . ?
C19 C18 C17 120.2(4) . . ?
C22 C18 C17 121.7(4) . . ?
C20 C19 C18 119.3(4) . . ?
N2 C20 C19 120.8(4) . . ?
N2 C21 C22 119.1(4) . . ?
C21 C22 C18 120.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.96
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_LJB_1_130K
_database_code_depnum_ccdc_archive 'CCDC 1441465'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn'
_chemical_formula_sum            'C22 H18 N2 O6 Zn'
_chemical_formula_weight         471.75

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   18.9781(18)
_cell_length_b                   7.7660(8)
_cell_length_c                   13.6963(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2018.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3374
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5446
_exptl_absorpt_correction_T_max  0.7994
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10380
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.97
_reflns_number_total             3901
_reflns_number_gt                3491
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0441P)²+0.4249P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3901
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.391223(17) 1.06039(4) 0.81412(3) 0.01066(11) Uani 1 1 d . . .
O1 O 0.47167(13) 0.9428(3) 0.87392(18) 0.0149(6) Uani 1 1 d . . .
O2 O 0.49851(14) 0.7720(4) 0.7484(2) 0.0252(6) Uani 1 1 d . . .
O3 O 0.76494(14) 0.6663(4) 0.7367(2) 0.0292(7) Uani 1 1 d . . .
O4 O 0.80921(13) 0.5501(3) 0.87234(18) 0.0170(6) Uani 1 1 d . . .
O5 O 0.69755(14) 0.7301(4) 1.18980(18) 0.0241(6) Uani 1 1 d . . .
O6 O 0.59676(13) 0.8784(4) 1.17906(18) 0.0170(6) Uani 1 1 d . . .
N1 N 0.39820(15) 1.2729(4) 0.9033(2) 0.0131(7) Uani 1 1 d . . .
N2 N 0.32531(17) 1.7886(4) 1.5652(2) 0.0220(8) Uani 1 1 d . . .
H2 H 0.3141 1.7881 1.6275 0.026 Uiso 1 1 calc R . .
C1 C 0.51146(18) 0.8355(4) 0.8287(3) 0.0137(8) Uani 1 1 d . . .
C2 C 0.57788(18) 0.7883(5) 0.8823(3) 0.0130(7) Uani 1 1 d . . .
C3 C 0.63669(17) 0.7315(4) 0.8321(2) 0.0120(8) Uani 1 1 d . . .
H3 H 0.6352 0.7238 0.7630 0.014 Uiso 1 1 calc R . .
C4 C 0.69832(18) 0.6854(5) 0.8818(3) 0.0138(8) Uani 1 1 d . . .
C5 C 0.76204(17) 0.6303(4) 0.8245(3) 0.0147(7) Uani 1 1 d . . .
C6 C 0.70047(18) 0.6963(5) 0.9828(2) 0.0138(8) Uani 1 1 d . . .
H6 H 0.7412 0.6593 1.0172 0.017 Uiso 1 1 calc R . .
C7 C 0.64308(18) 0.7612(5) 1.0338(3) 0.0136(8) Uani 1 1 d . . .
C8 C 0.64795(18) 0.7877(5) 1.1427(3) 0.0138(8) Uani 1 1 d . . .
C9 C 0.58210(19) 0.8082(5) 0.9835(2) 0.0130(7) Uani 1 1 d . . .
H9 H 0.5431 0.8541 1.0184 0.016 Uiso 1 1 calc R . .
C10 C 0.38663(19) 1.4355(5) 0.8735(3) 0.0170(8) Uani 1 1 d . . .
H10 H 0.3762 1.4558 0.8066 0.020 Uiso 1 1 calc R . .
C11 C 0.3894(2) 1.5747(5) 0.9369(3) 0.0181(8) Uani 1 1 d . . .
H11 H 0.3796 1.6874 0.9135 0.022 Uiso 1 1 calc R . .
C12 C 0.40647(19) 1.5497(5) 1.0350(3) 0.0156(8) Uani 1 1 d . . .
C13 C 0.42031(19) 1.3811(5) 1.0646(3) 0.0164(8) Uani 1 1 d . . .
H13 H 0.4335 1.3579 1.1302 0.020 Uiso 1 1 calc R . .
C14 C 0.4147(2) 1.2477(5) 0.9978(3) 0.0167(8) Uani 1 1 d . . .
H14 H 0.4229 1.1333 1.0197 0.020 Uiso 1 1 calc R . .
C15 C 0.4095(2) 1.6990(6) 1.1045(3) 0.0233(10) Uani 1 1 d . . .
H15A H 0.3824 1.7959 1.0761 0.028 Uiso 1 1 calc R . .
H15B H 0.4591 1.7367 1.1107 0.028 Uiso 1 1 calc R . .
C16 C 0.3807(2) 1.6616(5) 1.2065(3) 0.0203(9) Uani 1 1 d . . .
H16A H 0.3320 1.6164 1.2016 0.024 Uiso 1 1 calc R . .
H16B H 0.4102 1.5733 1.2388 0.024 Uiso 1 1 calc R . .
C17 C 0.3810(2) 1.8264(6) 1.2669(3) 0.0250(11) Uani 1 1 d . . .
H17A H 0.4287 1.8773 1.2646 0.030 Uiso 1 1 calc R . .
H17B H 0.3480 1.9098 1.2368 0.030 Uiso 1 1 calc R . .
C18 C 0.3603(2) 1.8002(6) 1.3722(3) 0.0192(9) Uani 1 1 d . . .
C19 C 0.2921(2) 1.8315(6) 1.4020(3) 0.0317(11) Uani 1 1 d . . .
H19 H 0.2565 1.8567 1.3553 0.038 Uiso 1 1 calc R . .
C20 C 0.2760(2) 1.8260(7) 1.4995(3) 0.0316(11) Uani 1 1 d . . .
H20 H 0.2292 1.8491 1.5204 0.038 Uiso 1 1 calc R . .
C21 C 0.3911(2) 1.7519(6) 1.5392(3) 0.0244(10) Uani 1 1 d . . .
H21 H 0.4253 1.7241 1.5874 0.029 Uiso 1 1 calc R . .
C22 C 0.4090(2) 1.7548(6) 1.4429(3) 0.0270(10) Uani 1 1 d . . .
H22 H 0.4556 1.7252 1.4240 0.032 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 O6 1.923(3) 2_674 ?
Zn1 O4 1.948(3) 4_465 ?
Zn1 O1 1.958(2) . ?
Zn1 N1 2.057(3) . ?
O1 C1 1.283(4) . ?
O2 C1 1.231(4) . ?
O3 C5 1.236(5) . ?
O4 C5 1.272(4) . ?
O4 Zn1 1.948(3) 4_565 ?
O5 C8 1.226(4) . ?
O6 C8 1.299(4) . ?
O6 Zn1 1.923(3) 2_675 ?
N1 C10 1.346(5) . ?
N1 C14 1.346(5) . ?
N2 C21 1.329(5) . ?
N2 C20 1.330(5) . ?
C1 C2 1.504(5) . ?
C2 C3 1.383(5) . ?
C2 C9 1.397(5) . ?
C3 C4 1.400(5) . ?
C4 C6 1.387(5) . ?
C4 C5 1.504(5) . ?
C6 C7 1.388(5) . ?
C7 C9 1.395(5) . ?
C7 C8 1.509(5) . ?
C10 C11 1.388(5) . ?
C11 C12 1.395(5) . ?
C12 C13 1.396(5) . ?
C12 C15 1.502(5) . ?
C13 C14 1.386(5) . ?
C15 C16 1.528(5) . ?
C16 C17 1.523(6) . ?
C17 C18 1.509(5) . ?
C18 C19 1.378(6) . ?
C18 C22 1.384(6) . ?
C19 C20 1.371(6) . ?
C21 C22 1.362(6) . ?

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
O6 Zn1 O4 126.68(11) 2_674 4_465 ?
O6 Zn1 O1 115.15(11) 2_674 . ?
O4 Zn1 O1 104.25(11) 4_465 . ?
O6 Zn1 N1 111.42(12) 2_674 . ?
O4 Zn1 N1 99.30(11) 4_465 . ?
O1 Zn1 N1 94.33(11) . . ?
C1 O1 Zn1 124.0(2) . . ?
C5 O4 Zn1 124.5(2) . 4_565 ?
C8 O6 Zn1 114.5(2) . 2_675 ?
C10 N1 C14 117.8(3) . . ?
C10 N1 Zn1 124.2(3) . . ?
C14 N1 Zn1 118.0(3) . . ?
C21 N2 C20 121.8(3) . . ?
O2 C1 O1 125.0(3) . . ?
O2 C1 C2 120.4(3) . . ?
O1 C1 C2 114.6(3) . . ?
C3 C2 C9 118.8(3) . . ?
C3 C2 C1 120.8(3) . . ?
C9 C2 C1 120.4(3) . . ?
C2 C3 C4 121.0(3) . . ?
C6 C4 C3 119.6(3) . . ?
C6 C4 C5 121.0(3) . . ?
C3 C4 C5 119.4(3) . . ?
O3 C5 O4 125.5(3) . . ?
O3 C5 C4 118.6(3) . . ?
O4 C5 C4 115.9(4) . . ?
C4 C6 C7 120.0(3) . . ?
C6 C7 C9 119.9(3) . . ?
C6 C7 C8 119.9(3) . . ?
C9 C7 C8 120.2(3) . . ?
O5 C8 O6 124.8(3) . . ?
O5 C8 C7 121.2(3) . . ?
O6 C8 C7 114.0(3) . . ?
C7 C9 C2 120.5(3) . . ?
N1 C10 C11 122.4(4) . . ?
C10 C11 C12 120.2(4) . . ?
C11 C12 C13 117.0(3) . . ?
C11 C12 C15 120.8(4) . . ?
C13 C12 C15 122.2(3) . . ?
C14 C13 C12 119.7(3) . . ?
N1 C14 C13 122.9(4) . . ?
C12 C15 C16 114.8(3) . . ?
C17 C16 C15 109.6(3) . . ?
C18 C17 C16 113.9(4) . . ?
C19 C18 C22 117.7(4) . . ?
C19 C18 C17 120.2(4) . . ?
C22 C18 C17 122.0(4) . . ?
C20 C19 C18 119.5(4) . . ?
N2 C20 C19 120.6(4) . . ?
N2 C21 C22 119.3(4) . . ?
C21 C22 C18 121.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.709
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_LJB_1_160K
_database_code_depnum_ccdc_archive 'CCDC 1441466'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn'
_chemical_formula_sum            'C22 H18 N2 O6 Zn'
_chemical_formula_weight         471.75

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   18.976(2)
_cell_length_b                   7.7768(8)
_cell_length_c                   13.6920(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2020.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    3215
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.81

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.259
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_T_max  0.7996
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10418
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.97
_reflns_number_total             3908
_reflns_number_gt                3475
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0408P)²+0.5885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3908
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.391105(17) 1.05973(5) 0.79469(3) 0.01258(11) Uani 1 1 d . . .
O1 O 0.47142(14) 0.9432(3) 0.85439(18) 0.0187(6) Uani 1 1 d . . .
O2 O 0.49904(15) 0.7732(4) 0.7285(2) 0.0305(7) Uani 1 1 d . . .
O3 O 0.76516(15) 0.6686(4) 0.7173(2) 0.0337(8) Uani 1 1 d . . .
O4 O 0.80915(14) 0.5514(3) 0.85297(18) 0.0198(6) Uani 1 1 d . . .
O5 O 0.69739(15) 0.7305(4) 1.17022(19) 0.0292(7) Uani 1 1 d . . .
O6 O 0.59713(13) 0.8786(4) 1.15945(18) 0.0199(6) Uani 1 1 d . . .
N1 N 0.39770(15) 1.2720(4) 0.8840(2) 0.0166(7) Uani 1 1 d . . .
N2 N 0.32559(18) 1.7867(4) 1.5456(2) 0.0245(8) Uani 1 1 d . . .
H2 H 0.3142 1.7856 1.6079 0.029 Uiso 1 1 calc R . .
C1 C 0.51152(18) 0.8361(5) 0.8090(3) 0.0167(8) Uani 1 1 d . . .
C2 C 0.57811(18) 0.7898(5) 0.8627(3) 0.0143(8) Uani 1 1 d . . .
C3 C 0.63685(18) 0.7329(4) 0.8125(2) 0.0149(8) Uani 1 1 d . . .
H3 H 0.6354 0.7252 0.7433 0.018 Uiso 1 1 calc R . .
C4 C 0.69829(18) 0.6867(5) 0.8619(3) 0.0153(8) Uani 1 1 d . . .
C5 C 0.76199(17) 0.6320(4) 0.8048(3) 0.0169(8) Uani 1 1 d . . .
C6 C 0.70029(19) 0.6980(5) 0.9634(2) 0.0158(8) Uani 1 1 d . . .
H6 H 0.7411 0.6612 0.9978 0.019 Uiso 1 1 calc R . .
C7 C 0.64321(19) 0.7625(5) 1.0144(2) 0.0146(8) Uani 1 1 d . . .
C8 C 0.64796(19) 0.7888(5) 1.1235(3) 0.0179(8) Uani 1 1 d . . .
C9 C 0.58245(19) 0.8083(5) 0.9638(2) 0.0151(8) Uani 1 1 d . . .
H9 H 0.5433 0.8530 0.9988 0.018 Uiso 1 1 calc R . .
C10 C 0.38641(19) 1.4347(5) 0.8544(3) 0.0180(8) Uani 1 1 d . . .
H10 H 0.3758 1.4551 0.7876 0.022 Uiso 1 1 calc R . .
C11 C 0.3897(2) 1.5736(5) 0.9176(3) 0.0208(9) Uani 1 1 d . . .
H11 H 0.3806 1.6863 0.8941 0.025 Uiso 1 1 calc R . .
C12 C 0.4063(2) 1.5482(5) 1.0151(3) 0.0189(8) Uani 1 1 d . . .
C13 C 0.4201(2) 1.3800(5) 1.0451(3) 0.0200(8) Uani 1 1 d . . .
H13 H 0.4333 1.3569 1.1107 0.024 Uiso 1 1 calc R . .
C14 C 0.4145(2) 1.2478(5) 0.9786(3) 0.0179(8) Uani 1 1 d . . .
H14 H 0.4229 1.1337 1.0006 0.021 Uiso 1 1 calc R . .
C15 C 0.4098(2) 1.6981(6) 1.0854(3) 0.0266(10) Uani 1 1 d . . .
H15A H 0.3831 1.7955 1.0570 0.032 Uiso 1 1 calc R . .
H15B H 0.4595 1.7347 1.0915 0.032 Uiso 1 1 calc R . .
C16 C 0.3808(2) 1.6613(6) 1.1878(3) 0.0233(9) Uani 1 1 d . . .
H16A H 0.3321 1.6165 1.1828 0.028 Uiso 1 1 calc R . .
H16B H 0.4101 1.5729 1.2202 0.028 Uiso 1 1 calc R . .
C17 C 0.3812(3) 1.8238(6) 1.2473(3) 0.0296(12) Uani 1 1 d . . .
H17A H 0.3481 1.9070 1.2173 0.036 Uiso 1 1 calc R . .
H17B H 0.4289 1.8747 1.2447 0.036 Uiso 1 1 calc R . .
C18 C 0.3609(2) 1.7982(6) 1.3527(3) 0.0253(10) Uani 1 1 d . . .
C19 C 0.2927(2) 1.8290(7) 1.3822(3) 0.0379(12) Uani 1 1 d . . .
H19 H 0.2571 1.8530 1.3354 0.045 Uiso 1 1 calc R . .
C20 C 0.2766(2) 1.8246(7) 1.4805(3) 0.0370(12) Uani 1 1 d . . .
H20 H 0.2299 1.8490 1.5015 0.044 Uiso 1 1 calc R . .
C21 C 0.3916(2) 1.7502(7) 1.5202(3) 0.0309(12) Uani 1 1 d . . .
H21 H 0.4257 1.7226 1.5685 0.037 Uiso 1 1 calc R . .
C22 C 0.4095(2) 1.7529(7) 1.4233(3) 0.0333(11) Uani 1 1 d . . .
H22 H 0.4561 1.7231 1.4043 0.040 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 O6 1.926(3) 2_674 ?
Zn1 O4 1.950(3) 4_465 ?
Zn1 O1 1.952(3) . ?
Zn1 N1 2.058(3) . ?
O1 C1 1.288(4) . ?
O2 C1 1.229(5) . ?
O3 C5 1.234(5) . ?
O4 C5 1.276(4) . ?
O4 Zn1 1.950(3) 4_565 ?
O5 C8 1.222(4) . ?
O6 C8 1.289(4) . ?
O6 Zn1 1.926(3) 2_675 ?
N1 C10 1.346(5) . ?
N1 C14 1.347(5) . ?
N2 C20 1.321(5) . ?
N2 C21 1.330(6) . ?
C1 C2 1.505(5) . ?
C2 C3 1.382(5) . ?
C2 C9 1.394(5) . ?
C3 C4 1.395(5) . ?
C4 C6 1.394(5) . ?
C4 C5 1.500(5) . ?
C6 C7 1.383(5) . ?
C7 C9 1.392(5) . ?
C7 C8 1.511(5) . ?
C10 C11 1.385(5) . ?
C11 C12 1.385(6) . ?
C12 C13 1.396(6) . ?
C12 C15 1.513(6) . ?
C13 C14 1.378(5) . ?
C15 C16 1.533(5) . ?
C16 C17 1.503(6) . ?
C17 C18 1.507(5) . ?
C18 C19 1.376(6) . ?
C18 C22 1.382(6) . ?
C19 C20 1.381(6) . ?
C21 C22 1.371(6) . ?

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
O6 Zn1 O4 126.60(11) 2_674 4_465 ?
O6 Zn1 O1 115.31(11) 2_674 . ?
O4 Zn1 O1 104.22(11) 4_465 . ?
O6 Zn1 N1 111.40(12) 2_674 . ?
O4 Zn1 N1 99.25(11) 4_465 . ?
O1 Zn1 N1 94.35(11) . . ?
C1 O1 Zn1 124.0(2) . . ?
C5 O4 Zn1 124.5(3) . 4_565 ?
C8 O6 Zn1 114.5(2) . 2_675 ?
C10 N1 C14 117.3(3) . . ?
C10 N1 Zn1 124.4(3) . . ?
C14 N1 Zn1 118.3(3) . . ?
C20 N2 C21 122.3(4) . . ?
O2 C1 O1 125.2(3) . . ?
O2 C1 C2 120.3(3) . . ?
O1 C1 C2 114.5(3) . . ?
C3 C2 C9 118.6(3) . . ?
C3 C2 C1 120.7(3) . . ?
C9 C2 C1 120.6(3) . . ?
C2 C3 C4 121.1(3) . . ?
C6 C4 C3 119.3(3) . . ?
C6 C4 C5 121.0(3) . . ?
C3 C4 C5 119.6(3) . . ?
O3 C5 O4 125.5(3) . . ?
O3 C5 C4 118.7(3) . . ?
O4 C5 C4 115.8(4) . . ?
C7 C6 C4 120.4(3) . . ?
C6 C7 C9 119.4(3) . . ?
C6 C7 C8 120.1(3) . . ?
C9 C7 C8 120.5(3) . . ?
O5 C8 O6 125.2(4) . . ?
O5 C8 C7 120.9(3) . . ?
O6 C8 C7 114.0(3) . . ?
C7 C9 C2 121.1(3) . . ?
N1 C10 C11 122.5(3) . . ?
C12 C11 C10 120.1(4) . . ?
C11 C12 C13 117.3(4) . . ?
C11 C12 C15 120.8(4) . . ?
C13 C12 C15 121.8(3) . . ?
C14 C13 C12 119.4(3) . . ?
N1 C14 C13 123.3(4) . . ?
C12 C15 C16 114.9(3) . . ?
C17 C16 C15 109.7(4) . . ?
C16 C17 C18 114.0(4) . . ?
C19 C18 C22 117.8(4) . . ?
C19 C18 C17 119.9(4) . . ?
C22 C18 C17 122.2(4) . . ?
C18 C19 C20 119.4(4) . . ?
N2 C20 C19 120.4(4) . . ?
N2 C21 C22 118.9(4) . . ?
C21 C22 C18 121.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_LJB__1_190K
_database_code_depnum_ccdc_archive 'CCDC 1441467'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn'
_chemical_formula_sum            'C22 H18 N2 O6 Zn'
_chemical_formula_weight         471.75

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   18.977(2)
_cell_length_b                   7.7881(9)
_cell_length_c                   13.6890(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2023.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3096
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.79

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5448
_exptl_absorpt_correction_T_max  0.7998
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10419
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.97
_reflns_number_total             3911
_reflns_number_gt                3449
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0464P)²+0.2676P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3911
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001

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 0.390979(18) 1.05932(5) 0.78267(3) 0.01448(11) Uani 1 1 d . . .
O1 O 0.47151(13) 0.9434(3) 0.84246(19) 0.0203(6) Uani 1 1 d . . .
O2 O 0.49913(16) 0.7754(4) 0.7166(2) 0.0362(8) Uani 1 1 d . . .
O3 O 0.76558(15) 0.6698(5) 0.7052(2) 0.0402(8) Uani 1 1 d . . .
O4 O 0.80920(14) 0.5521(3) 0.84052(19) 0.0231(6) Uani 1 1 d . . .
O5 O 0.69780(15) 0.7318(4) 1.15830(19) 0.0341(7) Uani 1 1 d . . .
O6 O 0.59728(14) 0.8784(4) 1.14789(19) 0.0235(6) Uani 1 1 d . . .
N1 N 0.39736(16) 1.2710(4) 0.8720(2) 0.0188(7) Uani 1 1 d . . .
N2 N 0.32568(18) 1.7863(4) 1.5333(2) 0.0289(8) Uani 1 1 d . . .
H2 H 0.3143 1.7874 1.5956 0.035 Uiso 1 1 calc R . .
C1 C 0.51173(19) 0.8380(5) 0.7974(3) 0.0192(8) Uani 1 1 d . . .
C2 C 0.57844(19) 0.7909(5) 0.8512(3) 0.0172(8) Uani 1 1 d . . .
C3 C 0.63760(18) 0.7350(4) 0.8008(2) 0.0154(8) Uani 1 1 d . . .
H3 H 0.6363 0.7284 0.7315 0.019 Uiso 1 1 calc R . .
C4 C 0.69854(19) 0.6889(5) 0.8501(3) 0.0175(8) Uani 1 1 d . . .
C5 C 0.76230(17) 0.6334(5) 0.7924(3) 0.0202(8) Uani 1 1 d . . .
C6 C 0.70056(19) 0.6987(5) 0.9515(3) 0.0184(8) Uani 1 1 d . . .
H6 H 0.7412 0.6610 0.9860 0.022 Uiso 1 1 calc R . .
C7 C 0.64327(19) 0.7635(5) 1.0020(3) 0.0166(8) Uani 1 1 d . . .
C8 C 0.6480(2) 0.7893(5) 1.1112(3) 0.0197(9) Uani 1 1 d . . .
C9 C 0.58261(19) 0.8092(5) 0.9519(3) 0.0162(8) Uani 1 1 d . . .
H9 H 0.5434 0.8535 0.9869 0.019 Uiso 1 1 calc R . .
C10 C 0.3864(2) 1.4332(5) 0.8423(3) 0.0217(9) Uani 1 1 d . . .
H10 H 0.3758 1.4533 0.7754 0.026 Uiso 1 1 calc R . .
C11 C 0.3897(2) 1.5729(5) 0.9054(3) 0.0237(9) Uani 1 1 d . . .
H11 H 0.3806 1.6854 0.8818 0.028 Uiso 1 1 calc R . .
C12 C 0.4065(2) 1.5475(5) 1.0033(3) 0.0217(9) Uani 1 1 d . . .
C13 C 0.4195(2) 1.3795(5) 1.0330(3) 0.0224(9) Uani 1 1 d . . .
H13 H 0.4320 1.3564 1.0989 0.027 Uiso 1 1 calc R . .
C14 C 0.4142(2) 1.2468(5) 0.9668(3) 0.0213(8) Uani 1 1 d . . .
H14 H 0.4228 1.1331 0.9889 0.026 Uiso 1 1 calc R . .
C15 C 0.4096(3) 1.6962(6) 1.0733(3) 0.0312(11) Uani 1 1 d . . .
H15A H 0.3827 1.7930 1.0449 0.037 Uiso 1 1 calc R . .
H15B H 0.4593 1.7336 1.0792 0.037 Uiso 1 1 calc R . .
C16 C 0.3810(2) 1.6599(6) 1.1756(3) 0.0280(10) Uani 1 1 d . . .
H16A H 0.3322 1.6160 1.1709 0.034 Uiso 1 1 calc R . .
H16B H 0.4102 1.5709 1.2077 0.034 Uiso 1 1 calc R . .
C17 C 0.3821(3) 1.8212(7) 1.2356(3) 0.0369(13) Uani 1 1 d . . .
H17A H 0.3497 1.9056 1.2055 0.044 Uiso 1 1 calc R . .
H17B H 0.4301 1.8704 1.2334 0.044 Uiso 1 1 calc R . .
C18 C 0.3612(2) 1.7964(6) 1.3411(3) 0.0302(11) Uani 1 1 d . . .
C19 C 0.2937(2) 1.8265(7) 1.3701(3) 0.0430(13) Uani 1 1 d . . .
H19 H 0.2584 1.8498 1.3227 0.052 Uiso 1 1 calc R . .
C20 C 0.2766(2) 1.8232(7) 1.4675(3) 0.0413(12) Uani 1 1 d . . .
H20 H 0.2297 1.8473 1.4877 0.050 Uiso 1 1 calc R . .
C21 C 0.3912(2) 1.7478(7) 1.5083(3) 0.0350(12) Uani 1 1 d . . .
H21 H 0.4250 1.7186 1.5567 0.042 Uiso 1 1 calc R . .
C22 C 0.4094(2) 1.7508(7) 1.4114(4) 0.0401(12) Uani 1 1 d . . .
H22 H 0.4560 1.7209 1.3926 0.048 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 O6 1.921(3) 2_674 ?
Zn1 O4 1.947(3) 4_465 ?
Zn1 O1 1.955(3) . ?
Zn1 N1 2.056(3) . ?
O1 C1 1.280(4) . ?
O2 C1 1.232(5) . ?
O3 C5 1.227(5) . ?
O4 C5 1.276(5) . ?
O4 Zn1 1.947(3) 4_565 ?
O5 C8 1.228(5) . ?
O6 C8 1.289(5) . ?
O6 Zn1 1.921(3) 2_675 ?
N1 C10 1.343(5) . ?
N1 C14 1.349(5) . ?
N2 C21 1.324(6) . ?
N2 C20 1.328(6) . ?
C1 C2 1.510(5) . ?
C2 C9 1.388(5) . ?
C2 C3 1.388(5) . ?
C3 C4 1.386(5) . ?
C4 C6 1.391(5) . ?
C4 C5 1.508(5) . ?
C6 C7 1.384(5) . ?
C7 C9 1.387(5) . ?
C7 C8 1.511(5) . ?
C10 C11 1.391(6) . ?
C11 C12 1.390(6) . ?
C12 C13 1.392(6) . ?
C12 C15 1.504(6) . ?
C13 C14 1.379(5) . ?
C15 C16 1.529(6) . ?
C16 C17 1.501(6) . ?
C17 C18 1.510(6) . ?
C18 C19 1.361(6) . ?
C18 C22 1.375(7) . ?
C19 C20 1.373(6) . ?
C21 C22 1.370(6) . ?

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
O6 Zn1 O4 126.58(11) 2_674 4_465 ?
O6 Zn1 O1 115.36(11) 2_674 . ?
O4 Zn1 O1 104.30(12) 4_465 . ?
O6 Zn1 N1 111.21(13) 2_674 . ?
O4 Zn1 N1 99.36(12) 4_465 . ?
O1 Zn1 N1 94.32(11) . . ?
C1 O1 Zn1 124.1(2) . . ?
C5 O4 Zn1 124.6(3) . 4_565 ?
C8 O6 Zn1 115.0(2) . 2_675 ?
C10 N1 C14 117.3(3) . . ?
C10 N1 Zn1 124.4(3) . . ?
C14 N1 Zn1 118.3(3) . . ?
C21 N2 C20 122.2(4) . . ?
O2 C1 O1 124.8(3) . . ?
O2 C1 C2 120.3(3) . . ?
O1 C1 C2 114.9(3) . . ?
C9 C2 C3 118.7(3) . . ?
C9 C2 C1 120.5(3) . . ?
C3 C2 C1 120.8(3) . . ?
C4 C3 C2 120.9(3) . . ?
C3 C4 C6 119.6(3) . . ?
C3 C4 C5 119.3(3) . . ?
C6 C4 C5 121.1(3) . . ?
O3 C5 O4 125.5(3) . . ?
O3 C5 C4 118.9(3) . . ?
O4 C5 C4 115.6(4) . . ?
C7 C6 C4 119.8(3) . . ?
C6 C7 C9 119.9(3) . . ?
C6 C7 C8 119.7(3) . . ?
C9 C7 C8 120.3(3) . . ?
O5 C8 O6 124.5(4) . . ?
O5 C8 C7 121.1(3) . . ?
O6 C8 C7 114.3(3) . . ?
C2 C9 C7 120.8(3) . . ?
N1 C10 C11 122.7(4) . . ?
C12 C11 C10 119.9(4) . . ?
C11 C12 C13 117.1(4) . . ?
C11 C12 C15 120.9(4) . . ?
C13 C12 C15 122.0(4) . . ?
C14 C13 C12 119.9(4) . . ?
N1 C14 C13 123.0(4) . . ?
C12 C15 C16 115.3(4) . . ?
C17 C16 C15 110.0(4) . . ?
C16 C17 C18 114.4(4) . . ?
C19 C18 C22 117.8(4) . . ?
C19 C18 C17 120.3(5) . . ?
C22 C18 C17 121.9(5) . . ?
C18 C19 C20 120.2(4) . . ?
N2 C20 C19 119.8(4) . . ?
N2 C21 C22 118.9(4) . . ?
C21 C22 C18 121.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_LJB_1_220K
_database_code_depnum_ccdc_archive 'CCDC 1441468'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn'
_chemical_formula_sum            'C22 H18 N2 O6 Zn'
_chemical_formula_weight         471.75

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   18.983(2)
_cell_length_b                   7.8009(9)
_cell_length_c                   13.6902(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2027.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    2703
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.27

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.551
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5448
_exptl_absorpt_correction_T_max  0.8002
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10089
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.97
_reflns_number_total             3916
_reflns_number_gt                3385
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0448P)²+0.4408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3916
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.390927(19) 1.05893(5) 0.80534(3) 0.01645(12) Uani 1 1 d . . .
O1 O 0.47146(15) 0.9439(3) 0.86477(19) 0.0236(7) Uani 1 1 d . . .
O2 O 0.49979(18) 0.7769(5) 0.7391(2) 0.0426(9) Uani 1 1 d . . .
O3 O 0.76605(17) 0.6713(5) 0.7279(2) 0.0470(10) Uani 1 1 d . . .
O4 O 0.80904(15) 0.5528(4) 0.8630(2) 0.0265(7) Uani 1 1 d . . .
O5 O 0.69771(17) 0.7317(5) 1.1806(2) 0.0394(8) Uani 1 1 d . . .
O6 O 0.59738(15) 0.8785(4) 1.1703(2) 0.0264(7) Uani 1 1 d . . .
N1 N 0.39725(17) 1.2702(4) 0.8948(2) 0.0201(7) Uani 1 1 d . . .
N2 N 0.3257(2) 1.7834(5) 1.5557(3) 0.0327(9) Uani 1 1 d . . .
H2 H 0.3140 1.7834 1.6171 0.039 Uiso 1 1 calc R . .
C1 C 0.5117(2) 0.8391(5) 0.8196(3) 0.0230(9) Uani 1 1 d . . .
C2 C 0.5786(2) 0.7929(5) 0.8730(3) 0.0192(8) Uani 1 1 d . . .
C3 C 0.6376(2) 0.7365(5) 0.8232(3) 0.0198(9) Uani 1 1 d . . .
H3 H 0.6363 0.7291 0.7547 0.024 Uiso 1 1 calc R . .
C4 C 0.6990(2) 0.6906(5) 0.8724(3) 0.0199(8) Uani 1 1 d . . .
C5 C 0.76250(19) 0.6348(5) 0.8155(3) 0.0225(9) Uani 1 1 d . . .
C6 C 0.7008(2) 0.7005(5) 0.9740(3) 0.0202(9) Uani 1 1 d . . .
H6 H 0.7411 0.6638 1.0081 0.024 Uiso 1 1 calc R . .
C7 C 0.6435(2) 0.7645(5) 1.0248(3) 0.0180(8) Uani 1 1 d . . .
C8 C 0.6481(2) 0.7901(5) 1.1338(3) 0.0227(9) Uani 1 1 d . . .
C9 C 0.5831(2) 0.8108(5) 0.9746(3) 0.0194(8) Uani 1 1 d . . .
H9 H 0.5445 0.8551 1.0094 0.023 Uiso 1 1 calc R . .
C10 C 0.3862(2) 1.4323(5) 0.8652(3) 0.0247(9) Uani 1 1 d . . .
H10 H 0.3757 1.4523 0.7990 0.030 Uiso 1 1 calc R . .
C11 C 0.3896(2) 1.5715(6) 0.9281(3) 0.0266(10) Uani 1 1 d . . .
H11 H 0.3807 1.6827 0.9048 0.032 Uiso 1 1 calc R . .
C12 C 0.4064(2) 1.5458(6) 1.0258(3) 0.0241(9) Uani 1 1 d . . .
C13 C 0.4188(2) 1.3798(6) 1.0559(3) 0.0275(10) Uani 1 1 d . . .
H13 H 0.4308 1.3573 1.1213 0.033 Uiso 1 1 calc R . .
C14 C 0.4135(2) 1.2460(5) 0.9895(3) 0.0243(9) Uani 1 1 d . . .
H14 H 0.4216 1.1336 1.0115 0.029 Uiso 1 1 calc R . .
C15 C 0.4100(3) 1.6946(6) 1.0957(4) 0.0359(12) Uani 1 1 d . . .
H15A H 0.3838 1.7908 1.0674 0.043 Uiso 1 1 calc R . .
H15B H 0.4593 1.7302 1.1018 0.043 Uiso 1 1 calc R . .
C16 C 0.3811(3) 1.6597(7) 1.1976(3) 0.0357(12) Uani 1 1 d . . .
H16A H 0.3325 1.6184 1.1927 0.043 Uiso 1 1 calc R . .
H16B H 0.4093 1.5702 1.2292 0.043 Uiso 1 1 calc R . .
C17 C 0.3830(3) 1.8193(8) 1.2584(4) 0.0465(16) Uani 1 1 d . . .
H17A H 0.3516 1.9045 1.2289 0.056 Uiso 1 1 calc R . .
H17B H 0.4309 1.8661 1.2569 0.056 Uiso 1 1 calc R . .
C18 C 0.3615(3) 1.7937(7) 1.3641(3) 0.0352(13) Uani 1 1 d . . .
C19 C 0.2945(3) 1.8248(8) 1.3923(3) 0.0491(14) Uani 1 1 d . . .
H19 H 0.2596 1.8488 1.3455 0.059 Uiso 1 1 calc R . .
C20 C 0.2778(3) 1.8211(8) 1.4898(4) 0.0479(14) Uani 1 1 d . . .
H20 H 0.2315 1.8458 1.5097 0.057 Uiso 1 1 calc R . .
C21 C 0.3910(3) 1.7456(8) 1.5311(4) 0.0413(14) Uani 1 1 d . . .
H21 H 0.4243 1.7178 1.5794 0.050 Uiso 1 1 calc R . .
C22 C 0.4100(3) 1.7472(8) 1.4343(4) 0.0477(14) Uani 1 1 d . . .
H22 H 0.4560 1.7167 1.4159 0.057 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 O6 1.925(3) 2_674 ?
Zn1 O4 1.949(3) 4_465 ?
Zn1 O1 1.951(3) . ?
Zn1 N1 2.056(3) . ?
O1 C1 1.278(5) . ?
O2 C1 1.225(5) . ?
O3 C5 1.234(5) . ?
O4 C5 1.270(5) . ?
O4 Zn1 1.949(3) 4_565 ?
O5 C8 1.227(5) . ?
O6 C8 1.285(5) . ?
O6 Zn1 1.925(3) 2_675 ?
N1 C10 1.345(5) . ?
N1 C14 1.346(5) . ?
N2 C20 1.313(6) . ?
N2 C21 1.318(6) . ?
C1 C2 1.509(5) . ?
C2 C3 1.383(5) . ?
C2 C9 1.401(5) . ?
C3 C4 1.392(5) . ?
C4 C6 1.394(5) . ?
C4 C5 1.500(5) . ?
C6 C7 1.385(5) . ?
C7 C9 1.383(5) . ?
C7 C8 1.508(5) . ?
C10 C11 1.388(6) . ?
C11 C12 1.389(6) . ?
C12 C13 1.380(6) . ?
C12 C15 1.506(6) . ?
C13 C14 1.388(6) . ?
C15 C16 1.524(6) . ?
C16 C17 1.498(7) . ?
C17 C18 1.516(6) . ?
C18 C19 1.350(7) . ?
C18 C22 1.379(8) . ?
C19 C20 1.372(7) . ?
C21 C22 1.373(7) . ?

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
O6 Zn1 O4 126.45(12) 2_674 4_465 ?
O6 Zn1 O1 115.27(12) 2_674 . ?
O4 Zn1 O1 104.50(12) 4_465 . ?
O6 Zn1 N1 111.22(13) 2_674 . ?
O4 Zn1 N1 99.44(12) 4_465 . ?
O1 Zn1 N1 94.28(12) . . ?
C1 O1 Zn1 124.1(3) . . ?
C5 O4 Zn1 124.9(3) . 4_565 ?
C8 O6 Zn1 115.1(3) . 2_675 ?
C10 N1 C14 117.3(4) . . ?
C10 N1 Zn1 124.4(3) . . ?
C14 N1 Zn1 118.3(3) . . ?
C20 N2 C21 121.7(4) . . ?
O2 C1 O1 125.3(4) . . ?
O2 C1 C2 119.8(4) . . ?
O1 C1 C2 114.9(4) . . ?
C3 C2 C9 118.1(4) . . ?
C3 C2 C1 121.3(3) . . ?
C9 C2 C1 120.6(4) . . ?
C2 C3 C4 121.5(3) . . ?
C3 C4 C6 119.3(3) . . ?
C3 C4 C5 119.8(4) . . ?
C6 C4 C5 121.0(4) . . ?
O3 C5 O4 125.2(4) . . ?
O3 C5 C4 118.8(4) . . ?
O4 C5 C4 116.0(4) . . ?
C7 C6 C4 120.1(3) . . ?
C9 C7 C6 119.7(3) . . ?
C9 C7 C8 120.3(3) . . ?
C6 C7 C8 120.0(3) . . ?
O5 C8 O6 124.8(4) . . ?
O5 C8 C7 120.7(4) . . ?
O6 C8 C7 114.4(3) . . ?
C7 C9 C2 121.2(4) . . ?
N1 C10 C11 122.8(4) . . ?
C10 C11 C12 119.7(4) . . ?
C13 C12 C11 117.6(4) . . ?
C13 C12 C15 121.7(4) . . ?
C11 C12 C15 120.7(4) . . ?
C12 C13 C14 119.8(4) . . ?
N1 C14 C13 122.9(4) . . ?
C12 C15 C16 115.3(4) . . ?
C17 C16 C15 110.6(4) . . ?
C16 C17 C18 114.4(5) . . ?
C19 C18 C22 118.4(5) . . ?
C19 C18 C17 120.2(5) . . ?
C22 C18 C17 121.3(5) . . ?
C18 C19 C20 119.5(5) . . ?
N2 C20 C19 120.8(5) . . ?
N2 C21 C22 119.4(5) . . ?
C21 C22 C18 120.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_LJB_1_250K
_database_code_depnum_ccdc_archive 'CCDC 1441469'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn'
_chemical_formula_sum            'C22 H18 N2 O6 Zn'
_chemical_formula_weight         471.75

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   18.9745(19)
_cell_length_b                   7.8080(8)
_cell_length_c                   13.6816(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2027.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    2839
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5442
_exptl_absorpt_correction_T_max  0.8001
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10515
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.97
_reflns_number_total             3927
_reflns_number_gt                3322
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0514P)²+0.4998P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3927
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.39088(2) 1.05857(5) 0.79067(3) 0.01855(13) Uani 1 1 d . . .
O1 O 0.47175(15) 0.9442(4) 0.8500(2) 0.0263(7) Uani 1 1 d . . .
O2 O 0.50023(19) 0.7786(5) 0.7242(3) 0.0504(10) Uani 1 1 d . . .
O3 O 0.76641(18) 0.6718(6) 0.7132(2) 0.0523(11) Uani 1 1 d . . .
O4 O 0.80934(16) 0.5541(4) 0.8482(2) 0.0293(8) Uani 1 1 d . . .
O5 O 0.69765(18) 0.7330(5) 1.1659(2) 0.0444(9) Uani 1 1 d . . .
O6 O 0.59779(16) 0.8790(4) 1.1559(2) 0.0303(7) Uani 1 1 d . . .
N1 N 0.39662(18) 1.2696(5) 0.8806(3) 0.0246(8) Uani 1 1 d . . .
N2 N 0.3260(2) 1.7818(5) 1.5408(3) 0.0377(10) Uani 1 1 d . . .
H2 H 0.3141 1.7820 1.6022 0.045 Uiso 1 1 calc R . .
C1 C 0.5122(2) 0.8403(5) 0.8045(3) 0.0243(10) Uani 1 1 d . . .
C2 C 0.5791(2) 0.7942(5) 0.8583(3) 0.0210(9) Uani 1 1 d . . .
C3 C 0.6381(2) 0.7382(5) 0.8085(3) 0.0221(10) Uani 1 1 d . . .
H3 H 0.6369 0.7314 0.7400 0.027 Uiso 1 1 calc R . .
C4 C 0.6990(2) 0.6918(5) 0.8575(3) 0.0209(9) Uani 1 1 d . . .
C5 C 0.7628(2) 0.6362(5) 0.8008(4) 0.0254(9) Uani 1 1 d . . .
C6 C 0.7009(2) 0.7013(6) 0.9595(3) 0.0233(9) Uani 1 1 d . . .
H6 H 0.7411 0.6642 0.9936 0.028 Uiso 1 1 calc R . .
C7 C 0.6438(2) 0.7650(5) 1.0100(3) 0.0206(9) Uani 1 1 d . . .
C8 C 0.6484(2) 0.7903(6) 1.1191(3) 0.0252(10) Uani 1 1 d . . .
C9 C 0.5833(2) 0.8118(6) 0.9595(3) 0.0223(9) Uani 1 1 d . . .
H9 H 0.5446 0.8560 0.9941 0.027 Uiso 1 1 calc R . .
C10 C 0.3865(2) 1.4317(6) 0.8506(3) 0.0272(10) Uani 1 1 d . . .
H10 H 0.3765 1.4518 0.7843 0.033 Uiso 1 1 calc R . .
C11 C 0.3901(2) 1.5707(6) 0.9138(4) 0.0316(11) Uani 1 1 d . . .
H11 H 0.3814 1.6820 0.8905 0.038 Uiso 1 1 calc R . .
C12 C 0.4067(2) 1.5447(6) 1.0111(3) 0.0274(10) Uani 1 1 d . . .
C13 C 0.4189(2) 1.3788(6) 1.0413(3) 0.0300(10) Uani 1 1 d . . .
H13 H 0.4312 1.3561 1.1066 0.036 Uiso 1 1 calc R . .
C14 C 0.4128(3) 1.2466(6) 0.9751(3) 0.0289(10) Uani 1 1 d . . .
H14 H 0.4205 1.1343 0.9974 0.035 Uiso 1 1 calc R . .
C15 C 0.4109(3) 1.6931(7) 1.0811(4) 0.0408(13) Uani 1 1 d . . .
H15A H 0.3855 1.7903 1.0525 0.049 Uiso 1 1 calc R . .
H15B H 0.4604 1.7268 1.0878 0.049 Uiso 1 1 calc R . .
C16 C 0.3810(3) 1.6590(8) 1.1830(4) 0.0417(13) Uani 1 1 d . . .
H16A H 0.3322 1.6193 1.1775 0.050 Uiso 1 1 calc R . .
H16B H 0.4085 1.5686 1.2149 0.050 Uiso 1 1 calc R . .
C17 C 0.3833(4) 1.8162(8) 1.2434(4) 0.0537(19) Uani 1 1 d . . .
H17A H 0.3517 1.9015 1.2144 0.064 Uiso 1 1 calc R . .
H17B H 0.4312 1.8630 1.2413 0.064 Uiso 1 1 calc R . .
C18 C 0.3624(3) 1.7896(8) 1.3498(4) 0.0410(14) Uani 1 1 d . . .
C19 C 0.2955(3) 1.8219(9) 1.3778(4) 0.0551(16) Uani 1 1 d . . .
H19 H 0.2609 1.8456 1.3306 0.066 Uiso 1 1 calc R . .
C20 C 0.2782(3) 1.8202(9) 1.4750(4) 0.0523(16) Uani 1 1 d . . .
H20 H 0.2319 1.8465 1.4946 0.063 Uiso 1 1 calc R . .
C21 C 0.3909(3) 1.7433(9) 1.5173(4) 0.0459(15) Uani 1 1 d . . .
H21 H 0.4240 1.7154 1.5658 0.055 Uiso 1 1 calc R . .
C22 C 0.4099(3) 1.7445(9) 1.4207(4) 0.0558(17) Uani 1 1 d . . .
H22 H 0.4561 1.7139 1.4028 0.067 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 O6 1.919(3) 2_674 ?
Zn1 O4 1.946(3) 4_465 ?
Zn1 O1 1.952(3) . ?
Zn1 N1 2.059(4) . ?
O1 C1 1.279(5) . ?
O2 C1 1.221(5) . ?
O3 C5 1.233(6) . ?
O4 C5 1.269(5) . ?
O4 Zn1 1.946(3) 4_565 ?
O5 C8 1.217(5) . ?
O6 C8 1.287(5) . ?
O6 Zn1 1.919(3) 2_675 ?
N1 C10 1.344(6) . ?
N1 C14 1.341(5) . ?
N2 C21 1.307(7) . ?
N2 C20 1.313(7) . ?
C1 C2 1.510(5) . ?
C2 C3 1.383(6) . ?
C2 C9 1.393(6) . ?
C3 C4 1.383(5) . ?
C4 C6 1.397(5) . ?
C4 C5 1.502(5) . ?
C6 C7 1.379(6) . ?
C7 C9 1.389(6) . ?
C7 C8 1.508(6) . ?
C10 C11 1.389(6) . ?
C11 C12 1.383(7) . ?
C12 C13 1.379(6) . ?
C12 C15 1.505(7) . ?
C13 C14 1.378(6) . ?
C15 C16 1.529(7) . ?
C16 C17 1.480(8) . ?
C17 C18 1.524(7) . ?
C18 C19 1.349(8) . ?
C18 C22 1.369(8) . ?
C19 C20 1.371(7) . ?
C21 C22 1.370(8) . ?

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
O6 Zn1 O4 126.34(13) 2_674 4_465 ?
O6 Zn1 O1 115.33(13) 2_674 . ?
O4 Zn1 O1 104.46(13) 4_465 . ?
O6 Zn1 N1 111.40(14) 2_674 . ?
O4 Zn1 N1 99.33(13) 4_465 . ?
O1 Zn1 N1 94.35(13) . . ?
C1 O1 Zn1 124.0(3) . . ?
C5 O4 Zn1 125.1(3) . 4_565 ?
C8 O6 Zn1 115.4(3) . 2_675 ?
C10 N1 C14 116.9(4) . . ?
C10 N1 Zn1 124.3(3) . . ?
C14 N1 Zn1 118.8(3) . . ?
C21 N2 C20 122.3(4) . . ?
O2 C1 O1 125.2(4) . . ?
O2 C1 C2 120.1(4) . . ?
O1 C1 C2 114.7(4) . . ?
C3 C2 C9 118.3(4) . . ?
C3 C2 C1 121.1(4) . . ?
C9 C2 C1 120.6(4) . . ?
C4 C3 C2 121.4(4) . . ?
C3 C4 C6 119.4(4) . . ?
C3 C4 C5 119.9(4) . . ?
C6 C4 C5 120.7(4) . . ?
O3 C5 O4 124.9(4) . . ?
O3 C5 C4 118.8(4) . . ?
O4 C5 C4 116.3(4) . . ?
C7 C6 C4 120.0(4) . . ?
C6 C7 C9 119.7(4) . . ?
C6 C7 C8 119.8(4) . . ?
C9 C7 C8 120.4(4) . . ?
O5 C8 O6 124.4(4) . . ?
O5 C8 C7 121.1(4) . . ?
O6 C8 C7 114.4(4) . . ?
C7 C9 C2 121.1(4) . . ?
N1 C10 C11 122.6(4) . . ?
C12 C11 C10 119.7(4) . . ?
C13 C12 C11 117.6(4) . . ?
C13 C12 C15 121.6(4) . . ?
C11 C12 C15 120.8(4) . . ?
C12 C13 C14 119.5(4) . . ?
N1 C14 C13 123.5(4) . . ?
C12 C15 C16 115.3(4) . . ?
C17 C16 C15 110.7(5) . . ?
C16 C17 C18 114.3(5) . . ?
C19 C18 C22 117.8(5) . . ?
C19 C18 C17 119.4(6) . . ?
C22 C18 C17 122.7(5) . . ?
C18 C19 C20 120.0(5) . . ?
N2 C20 C19 120.1(5) . . ?
N2 C21 C22 119.0(5) . . ?
C18 C22 C21 120.8(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_LJB_1_280K
_database_code_depnum_ccdc_archive 'CCDC 1441470'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N2 O6 Zn'
_chemical_formula_sum            'C22 H18 N2 O6 Zn'
_chemical_formula_weight         471.75

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n

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

_cell_length_a                   18.9725(19)
_cell_length_b                   7.8178(8)
_cell_length_c                   13.6767(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2028.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    280(2)
_cell_measurement_reflns_used    2744
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5445
_exptl_absorpt_correction_T_max  0.8003
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      280(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10535
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.97
_reflns_number_total             3932
_reflns_number_gt                3327
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour 2001)'
_computing_publication_material  ?

_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)+(0.0457P)²+0.5419P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3932
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_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 0.390868(19) 1.05822(5) 0.79770(3) 0.02100(12) Uani 1 1 d . . .
O1 O 0.47188(15) 0.9447(4) 0.8571(2) 0.0295(7) Uani 1 1 d . . .
O2 O 0.50065(19) 0.7807(5) 0.7309(2) 0.0588(11) Uani 1 1 d . . .
O3 O 0.76655(18) 0.6734(6) 0.7202(2) 0.0594(12) Uani 1 1 d . . .
O4 O 0.80941(15) 0.5548(4) 0.8553(2) 0.0331(8) Uani 1 1 d . . .
O5 O 0.69765(18) 0.7331(5) 1.1728(2) 0.0498(10) Uani 1 1 d . . .
O6 O 0.59758(16) 0.8786(4) 1.1629(2) 0.0347(7) Uani 1 1 d . . .
N1 N 0.39629(18) 1.2690(5) 0.8877(2) 0.0265(8) Uani 1 1 d . . .
N2 N 0.3259(2) 1.7814(5) 1.5476(3) 0.0412(10) Uani 1 1 d . . .
H2 H 0.3140 1.7836 1.6082 0.049 Uiso 1 1 calc R . .
C1 C 0.5125(2) 0.8420(6) 0.8113(3) 0.0289(10) Uani 1 1 d . . .
C2 C 0.5793(2) 0.7958(6) 0.8657(3) 0.0252(9) Uani 1 1 d . . .
C3 C 0.6385(2) 0.7406(5) 0.8156(3) 0.0242(9) Uani 1 1 d . . .
H3 H 0.6374 0.7355 0.7477 0.029 Uiso 1 1 calc R . .
C4 C 0.6994(2) 0.6929(5) 0.8645(3) 0.0243(9) Uani 1 1 d . . .
C5 C 0.7633(2) 0.6377(5) 0.8077(4) 0.0288(9) Uani 1 1 d . . .
C6 C 0.7011(2) 0.7025(6) 0.9659(3) 0.0262(9) Uani 1 1 d . . .
H6 H 0.7408 0.6652 0.9997 0.031 Uiso 1 1 calc R . .
C7 C 0.6440(2) 0.7671(5) 1.0171(3) 0.0247(9) Uani 1 1 d . . .
C8 C 0.6484(2) 0.7905(6) 1.1263(3) 0.0292(10) Uani 1 1 d . . .
C9 C 0.5835(2) 0.8128(6) 0.9662(3) 0.0244(9) Uani 1 1 d . . .
H9 H 0.5451 0.8559 1.0004 0.029 Uiso 1 1 calc R . .
C10 C 0.3866(2) 1.4307(6) 0.8576(3) 0.0308(10) Uani 1 1 d . . .
H10 H 0.3768 1.4506 0.7919 0.037 Uiso 1 1 calc R . .
C11 C 0.3906(2) 1.5688(6) 0.9206(3) 0.0328(10) Uani 1 1 d . . .
H11 H 0.3826 1.6788 0.8973 0.039 Uiso 1 1 calc R . .
C12 C 0.4066(2) 1.5436(6) 1.0183(3) 0.0325(10) Uani 1 1 d . . .
C13 C 0.4181(2) 1.3772(6) 1.0488(3) 0.0333(10) Uani 1 1 d . . .
H13 H 0.4298 1.3544 1.1135 0.040 Uiso 1 1 calc R . .
C14 C 0.4122(2) 1.2456(6) 0.9823(3) 0.0327(10) Uani 1 1 d . . .
H14 H 0.4196 1.1345 1.0043 0.039 Uiso 1 1 calc R . .
C15 C 0.4107(3) 1.6912(7) 1.0880(4) 0.0480(15) Uani 1 1 d . . .
H15A H 0.3857 1.7871 1.0595 0.058 Uiso 1 1 calc R . .
H15B H 0.4598 1.7245 1.0944 0.058 Uiso 1 1 calc R . .
C16 C 0.3810(3) 1.6592(8) 1.1906(4) 0.0486(14) Uani 1 1 d . . .
H16A H 0.3324 1.6222 1.1853 0.058 Uiso 1 1 calc R . .
H16B H 0.4075 1.5681 1.2217 0.058 Uiso 1 1 calc R . .
C17 C 0.3844(4) 1.8122(9) 1.2514(4) 0.064(2) Uani 1 1 d . . .
H17A H 0.3543 1.8990 1.2227 0.077 Uiso 1 1 calc R . .
H17B H 0.4323 1.8555 1.2502 0.077 Uiso 1 1 calc R . .
C18 C 0.3627(3) 1.7864(8) 1.3571(3) 0.0452(15) Uani 1 1 d . . .
C19 C 0.2960(3) 1.8202(10) 1.3846(4) 0.0640(18) Uani 1 1 d . . .
H19 H 0.2619 1.8444 1.3378 0.077 Uiso 1 1 calc R . .
C20 C 0.2787(3) 1.8188(9) 1.4814(4) 0.0575(16) Uani 1 1 d . . .
H20 H 0.2329 1.8446 1.5005 0.069 Uiso 1 1 calc R . .
C21 C 0.3909(3) 1.7406(9) 1.5247(4) 0.0517(16) Uani 1 1 d . . .
H21 H 0.4234 1.7124 1.5731 0.062 Uiso 1 1 calc R . .
C22 C 0.4102(3) 1.7403(10) 1.4280(4) 0.068(2) Uani 1 1 d . . .
H22 H 0.4557 1.7086 1.4103 0.082 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 O6 1.921(3) 2_674 ?
Zn1 O4 1.947(3) 4_465 ?
Zn1 O1 1.952(3) . ?
Zn1 N1 2.059(3) . ?
O1 C1 1.276(5) . ?
O2 C1 1.221(5) . ?
O3 C5 1.231(6) . ?
O4 C5 1.268(5) . ?
O4 Zn1 1.947(3) 4_565 ?
O5 C8 1.217(5) . ?
O6 C8 1.286(5) . ?
O6 Zn1 1.921(3) 2_675 ?
N1 C14 1.342(5) . ?
N1 C10 1.342(6) . ?
N2 C20 1.307(7) . ?
N2 C21 1.312(7) . ?
C1 C2 1.514(5) . ?
C2 C9 1.383(5) . ?
C2 C3 1.385(5) . ?
C3 C4 1.385(5) . ?
C4 C6 1.390(5) . ?
C4 C5 1.503(5) . ?
C6 C7 1.385(6) . ?
C7 C9 1.388(6) . ?
C7 C8 1.507(6) . ?
C10 C11 1.384(6) . ?
C11 C12 1.384(6) . ?
C12 C13 1.383(7) . ?
C12 C15 1.499(7) . ?
C13 C14 1.377(6) . ?
C15 C16 1.534(7) . ?
C16 C17 1.458(8) . ?
C17 C18 1.517(7) . ?
C18 C19 1.345(8) . ?
C18 C22 1.372(8) . ?
C19 C20 1.365(7) . ?
C21 C22 1.373(8) . ?

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
O6 Zn1 O4 126.55(13) 2_674 4_465 ?
O6 Zn1 O1 115.24(12) 2_674 . ?
O4 Zn1 O1 104.49(13) 4_465 . ?
O6 Zn1 N1 111.25(14) 2_674 . ?
O4 Zn1 N1 99.25(13) 4_465 . ?
O1 Zn1 N1 94.34(13) . . ?
C1 O1 Zn1 123.8(3) . . ?
C5 O4 Zn1 124.9(3) . 4_565 ?
C8 O6 Zn1 115.2(3) . 2_675 ?
C14 N1 C10 117.1(4) . . ?
C14 N1 Zn1 118.6(3) . . ?
C10 N1 Zn1 124.3(3) . . ?
C20 N2 C21 122.3(4) . . ?
O2 C1 O1 125.3(4) . . ?
O2 C1 C2 120.2(4) . . ?
O1 C1 C2 114.5(4) . . ?
C9 C2 C3 118.3(4) . . ?
C9 C2 C1 120.9(4) . . ?
C3 C2 C1 120.8(4) . . ?
C4 C3 C2 121.5(4) . . ?
C3 C4 C6 119.1(4) . . ?
C3 C4 C5 120.1(4) . . ?
C6 C4 C5 120.8(4) . . ?
O3 C5 O4 125.5(4) . . ?
O3 C5 C4 118.5(4) . . ?
O4 C5 C4 116.0(4) . . ?
C7 C6 C4 120.4(4) . . ?
C6 C7 C9 119.1(4) . . ?
C6 C7 C8 120.1(4) . . ?
C9 C7 C8 120.8(4) . . ?
O5 C8 O6 124.7(4) . . ?
O5 C8 C7 121.1(4) . . ?
O6 C8 C7 114.2(4) . . ?
C2 C9 C7 121.4(4) . . ?
N1 C10 C11 122.4(4) . . ?
C10 C11 C12 120.2(4) . . ?
C13 C12 C11 117.3(4) . . ?
C13 C12 C15 121.6(4) . . ?
C11 C12 C15 121.0(5) . . ?
C14 C13 C12 119.4(4) . . ?
N1 C14 C13 123.6(4) . . ?
C12 C15 C16 115.9(4) . . ?
C17 C16 C15 111.8(5) . . ?
C16 C17 C18 115.0(6) . . ?
C19 C18 C22 118.1(5) . . ?
C19 C18 C17 119.7(6) . . ?
C22 C18 C17 122.0(6) . . ?
C18 C19 C20 119.7(5) . . ?
N2 C20 C19 120.6(5) . . ?
N2 C21 C22 118.7(5) . . ?
C18 C22 C21 120.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.057
