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

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1438600'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-11-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            KHC-053
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O8 Zn2'
_chemical_formula_iupac          ?
_chemical_formula_weight         543.09

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6305(8)
_cell_length_b                   13.3200(10)
_cell_length_c                   16.2613(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.408(4)
_cell_angle_gamma                90
_cell_volume                     2197.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.5229
_cell_measurement_theta_max      26.1572
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096

_exptl_absorpt_coefficient_mu    2.232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.84

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            62550
_diffrn_reflns_av_R_equivalents  0.2053
_diffrn_reflns_av_unetI/netI     0.1149
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         28.91
_diffrn_reflns_theta_full        28.91
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             5571
_reflns_number_gt                2623
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1686
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_gt          0.1791
_refine_ls_wR_factor_ref         0.2190
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_number_reflns         5571
_refine_ls_number_parameters     288
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1133P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.825
_refine_diff_density_min         -0.505
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.038(3)

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

# start Validation Reply Form
_vrf_RINTA01_I                   
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Data were not of the highest quality.
;
_vrf_PLAT020_I                   
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.205 Report
RESPONSE: Data were not of the highest quality.
;
# end Validation Reply Form

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.35406(8) 0.64690(6) 0.33336(4) 0.0588(3) Uani d . . . 1 . .
Zn Zn2 0.56079(7) 0.70704(6) 0.51920(4) 0.0563(3) Uani d . . . 1 . .
O O11 0.2490(5) 0.5963(4) 0.4032(3) 0.0732(14) Uani d . . . 1 . .
O O12 0.3951(5) 0.6420(4) 0.5279(3) 0.0668(13) Uani d . . . 1 . .
O O13 0.5057(5) 0.5629(4) 0.3300(3) 0.0713(13) Uani d . . . 1 . .
O O14 0.6414(5) 0.6106(4) 0.4574(3) 0.0688(13) Uani d . . . 1 . .
O O21 0.4425(5) 0.7723(3) 0.3781(3) 0.0665(13) Uani d . . . 1 . .
O O22 0.2430(5) 0.8299(4) 0.3207(4) 0.0827(16) Uani d . . . 1 . .
O O23 0.5278(5) 0.8473(4) 0.5761(3) 0.0726(14) Uani d . . . 1 . .
O O24 0.7019(5) 0.8273(4) 0.5328(3) 0.0667(12) Uani d . . . 1 . .
N N31 0.2391(5) 0.6386(4) 0.2108(3) 0.0536(13) Uani d . . . 1 . .
N N32 0.6750(5) 0.6592(4) 0.6463(3) 0.0572(14) Uani d . . . 1 . .
C C11 0.2896(6) 0.6018(5) 0.4837(4) 0.0545(16) Uani d . . . 1 . .
C C12 0.2023(6) 0.5586(6) 0.5343(4) 0.0614(17) Uani d . . . 1 . .
H H12A 0.1464 0.6114 0.5453 0.074 Uiso calc U . R 1 . .
H H12B 0.1457 0.5072 0.5001 0.074 Uiso calc U . R 1 . .
C C13 0.7172(6) 0.4860(5) 0.3811(4) 0.0641(18) Uani d . . . 1 . .
H H13A 0.7758 0.521 0.3551 0.077 Uiso calc U . R 1 . .
H H13B 0.6753 0.4321 0.3425 0.077 Uiso calc U . R 1 . .
C C14 0.6129(6) 0.5578(5) 0.3896(4) 0.0537(16) Uani d . . . 1 . .
C C21 0.3594(7) 0.8449(5) 0.3577(4) 0.0592(17) Uani d . . . 1 . .
C C22 0.4105(7) 0.9506(5) 0.3759(5) 0.0697(19) Uani d . . . 1 . .
H H22A 0.4368 0.9746 0.3272 0.084 Uiso calc U . R 1 . .
H H22B 0.4883 0.95 0.4258 0.084 Uiso calc U . R 1 . .
C C23 0.6896(7) 0.9768(6) 0.6075(6) 0.089(3) Uani d . . . 1 . .
H H23A 0.7307 1.0086 0.5684 0.107 Uiso calc U . R 1 . .
H H23B 0.758 0.9653 0.6615 0.107 Uiso calc U . R 1 . .
C C24 0.6369(7) 0.8783(5) 0.5710(4) 0.0581(17) Uani d . . . 1 . .
C C31 0.1077(7) 0.6440(6) 0.1890(5) 0.073(2) Uani d . . . 1 . .
H H31 0.0681 0.6454 0.2328 0.088 Uiso calc U . R 1 . .
C C32 0.0286(8) 0.6475(7) 0.1058(6) 0.096(3) Uani d . . . 1 . .
H H32 -0.0623 0.6519 0.0946 0.115 Uiso calc U . R 1 . .
C C33 0.0828(9) 0.6447(6) 0.0361(4) 0.081(3) Uani d . . D 1 . .
C C34 0.2183(10) 0.6407(7) 0.0610(5) 0.090(3) Uani d . . . 1 . .
H H34 0.2615 0.6402 0.019 0.109 Uiso calc U . R 1 . .
C C35 0.2921(7) 0.6375(6) 0.1475(4) 0.070(2) Uani d . . . 1 . .
H H35 0.3835 0.6344 0.1612 0.084 Uiso calc U . R 1 . .
C C36 0.0333(12) 0.6455(9) -0.0508(4) 0.047(3) Uiso d . P D 0.5 A 1
C C37 0.9484(17) 0.649(2) 0.8849(14) 0.152(10) Uiso d . P D 0.5 B 1
C C36* -0.0274(15) 0.6470(19) -0.0320(11) 0.121(8) Uiso d . P D 0.5 A 2
C C37* 0.8903(14) 0.6453(10) 0.9051(4) 0.054(3) Uiso d . P D 0.5 B 2
C C38 0.8355(10) 0.6517(6) 0.8187(4) 0.090(3) Uani d . . D 1 . .
C C39 0.7047(10) 0.6628(7) 0.7953(5) 0.090(3) Uani d . . . 1 . .
H H39 0.6641 0.6664 0.8386 0.108 Uiso calc U . R 1 . .
C C310 0.6252(8) 0.6695(6) 0.7102(4) 0.077(2) Uani d . . . 1 . .
H H310 0.5354 0.6816 0.6987 0.092 Uiso calc U . R 1 . .
C C311 0.8020(8) 0.6432(6) 0.6648(5) 0.078(2) Uani d . . . 1 . .
H H311 0.8364 0.6351 0.6189 0.094 Uiso calc U . R 1 . .
C C312 0.8886(10) 0.6376(6) 0.7466(6) 0.101(3) Uani d . . . 1 . .
H H312 0.9778 0.6253 0.7556 0.121 Uiso calc U . R 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 O11 . 1.936(5) ?
Zn1 O21 . 1.948(4) ?
Zn1 O13 . 1.976(5) ?
Zn1 N31 . 2.004(5) ?
Zn2 O14 . 1.977(5) ?
Zn2 O12 . 2.006(5) ?
Zn2 N32 . 2.157(5) ?
Zn2 O23 . 2.160(5) ?
Zn2 O24 . 2.160(5) ?
Zn2 O21 . 2.424(5) ?
Zn2 C24 . 2.482(7) ?
O11 C11 . 1.252(7) ?
O12 C11 . 1.256(7) ?
O13 C14 . 1.258(7) ?
O14 C14 . 1.265(7) ?
O21 C21 . 1.285(8) ?
O22 C21 . 1.219(7) ?
O23 C24 . 1.257(8) ?
O24 C24 . 1.258(8) ?
N31 C35 . 1.314(8) ?
N31 C31 . 1.336(8) ?
N32 C310 . 1.307(9) ?
N32 C311 . 1.309(9) ?
C11 C12 . 1.526(9) ?
C12 C13 3_666 1.508(8) ?
C13 C14 . 1.502(9) ?
C13 C12 3_666 1.508(8) ?
C21 C22 . 1.506(9) ?
C22 C23 3_676 1.521(10) ?
C23 C24 . 1.479(10) ?
C23 C22 3_676 1.521(10) ?
C31 C32 . 1.364(11) ?
C32 C33 . 1.416(13) ?
C33 C36* . 1.351(2) ?
C33 C36 . 1.353(2) ?
C33 C34 . 1.375(12) ?
C34 C35 . 1.392(10) ?
C36 C37 1_454 1.160(12) ?
C37 C36 1_656 1.160(12) ?
C37 C38 . 1.351(2) ?
C36* C37* 1_454 1.130(11) ?
C37* C36* 1_656 1.130(11) ?
C37* C38 . 1.352(2) ?
C38 C39 . 1.336(13) ?
C38 C312 . 1.457(13) ?
C39 C310 . 1.392(10) ?
C311 C312 . 1.375(11) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11 Zn1 O21 . . 112.2(2) ?
O11 Zn1 O13 . . 115.9(2) ?
O21 Zn1 O13 . . 100.9(2) ?
O11 Zn1 N31 . . 106.1(2) ?
O21 Zn1 N31 . . 120.1(2) ?
O13 Zn1 N31 . . 101.58(19) ?
O14 Zn2 O12 . . 106.2(2) ?
O14 Zn2 N32 . . 95.2(2) ?
O12 Zn2 N32 . . 93.4(2) ?
O14 Zn2 O23 . . 158.5(2) ?
O12 Zn2 O23 . . 94.88(19) ?
N32 Zn2 O23 . . 87.85(19) ?
O14 Zn2 O24 . . 98.1(2) ?
O12 Zn2 O24 . . 155.6(2) ?
N32 Zn2 O24 . . 86.94(19) ?
O23 Zn2 O24 . . 60.75(18) ?
O14 Zn2 O21 . . 86.14(17) ?
O12 Zn2 O21 . . 90.22(17) ?
N32 Zn2 O21 . . 175.65(18) ?
O23 Zn2 O21 . . 89.44(16) ?
O24 Zn2 O21 . . 88.77(16) ?
O14 Zn2 C24 . . 128.5(2) ?
O12 Zn2 C24 . . 125.3(2) ?
N32 Zn2 C24 . . 85.0(2) ?
O23 Zn2 C24 . . 30.43(19) ?
O24 Zn2 C24 . . 30.44(19) ?
O21 Zn2 C24 . . 90.91(18) ?
C11 O11 Zn1 . . 121.0(4) ?
C11 O12 Zn2 . . 142.8(4) ?
C14 O13 Zn1 . . 124.5(4) ?
C14 O14 Zn2 . . 140.9(4) ?
C21 O21 Zn1 . . 109.4(4) ?
C21 O21 Zn2 . . 129.5(4) ?
Zn1 O21 Zn2 . . 95.83(18) ?
C24 O23 Zn2 . . 89.1(4) ?
C24 O24 Zn2 . . 89.1(4) ?
C35 N31 C31 . . 116.8(6) ?
C35 N31 Zn1 . . 120.2(4) ?
C31 N31 Zn1 . . 122.6(5) ?
C310 N32 C311 . . 118.0(6) ?
C310 N32 Zn2 . . 119.0(5) ?
C311 N32 Zn2 . . 120.9(5) ?
O11 C11 O12 . . 126.3(6) ?
O11 C11 C12 . . 117.9(6) ?
O12 C11 C12 . . 115.8(5) ?
C13 C12 C11 3_666 . 111.7(5) ?
C14 C13 C12 . 3_666 113.6(5) ?
O13 C14 O14 . . 124.6(6) ?
O13 C14 C13 . . 119.1(6) ?
O14 C14 C13 . . 116.3(6) ?
O22 C21 O21 . . 121.4(7) ?
O22 C21 C22 . . 120.2(7) ?
O21 C21 C22 . . 118.2(6) ?
C21 C22 C23 . 3_676 113.5(6) ?
C24 C23 C22 . 3_676 115.8(6) ?
O23 C24 O24 . . 120.6(7) ?
O23 C24 C23 . . 120.7(7) ?
O24 C24 C23 . . 118.7(7) ?
O23 C24 Zn2 . . 60.5(4) ?
O24 C24 Zn2 . . 60.5(4) ?
C23 C24 Zn2 . . 175.7(6) ?
N31 C31 C32 . . 123.4(7) ?
C31 C32 C33 . . 121.0(8) ?
C36* C33 C34 . . 144.8(13) ?
C36 C33 C34 . . 110.7(9) ?
C36* C33 C32 . . 101.2(13) ?
C36 C33 C32 . . 135.3(10) ?
C34 C33 C32 . . 114.0(6) ?
C33 C34 C35 . . 121.5(7) ?
N31 C35 C34 . . 123.2(7) ?
C37 C36 C33 1_454 . 154.(2) ?
C36 C37 C38 1_656 . 170.(3) ?
C37* C36* C33 1_454 . 171.(3) ?
C36* C37* C38 1_656 . 156.(2) ?
C39 C38 C37 . . 146.2(16) ?
C39 C38 C37* . . 113.0(11) ?
C39 C38 C312 . . 113.9(6) ?
C37 C38 C312 . . 99.9(16) ?
C37* C38 C312 . . 132.6(11) ?
C38 C39 C310 . . 124.1(8) ?
N32 C310 C39 . . 120.9(8) ?
N32 C311 C312 . . 125.2(8) ?
C311 C312 C38 . . 117.6(8) ?

####################################################################### 
# 
# 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_ye343c2cr_sqd
_database_code_depnum_ccdc_archive 'CCDC 1438601'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-11-18 downloaded from the CCDC.
;

_audit_creation_method           'APEX2 v2014.1-1'
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 N2 O4.50 Zn'
_chemical_formula_weight         369.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   8.8979(3)
_cell_length_b                   21.4587(7)
_cell_length_c                   13.4851(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.7804(16)
_cell_angle_gamma                90
_cell_volume                     2556.80(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.4324
_cell_measurement_theta_max      26.0011

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.960
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.976
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36532
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.587
_diffrn_reflns_theta_max         28.231
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3063
_reflns_number_gt                2545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0868P)²+0.5359P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3063
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.5000 0.64732(2) 0.7500 0.03429(17) Uani 1 2 d S T P . .
O11 O 0.6028(2) 0.70593(9) 0.84632(14) 0.0499(5) Uani 1 1 d . . . . .
O12 O 0.7071(3) 0.62298(11) 0.9219(2) 0.0691(7) Uani 1 1 d . . . . .
N21 N 0.3533(2) 0.59490(11) 0.81818(17) 0.0428(5) Uani 1 1 d . . . . .
C11 C 0.6871(3) 0.67905(13) 0.9168(2) 0.0440(6) Uani 1 1 d . . . . .
C12 C 0.7610(3) 0.72009(14) 0.9967(2) 0.0478(6) Uani 1 1 d . . . . .
H12 H 0.8284 0.7016 1.0460 0.057 Uiso 1 1 calc R U . . .
C21 C 0.3977(4) 0.54151(14) 0.8652(2) 0.0535(7) Uani 1 1 d . . . . .
H21 H 0.4952 0.5270 0.8610 0.064 Uiso 1 1 calc R U . . .
C22 C 0.3041(4) 0.50750(15) 0.9193(3) 0.0603(8) Uani 1 1 d . . . . .
H22 H 0.3383 0.4706 0.9503 0.072 Uiso 1 1 calc R U . . .
C23 C 0.1598(4) 0.52854(15) 0.9274(3) 0.0568(8) Uani 1 1 d . . . . .
C24 C 0.1143(3) 0.58322(19) 0.8781(3) 0.0659(9) Uani 1 1 d . . . . .
H24 H 0.0178 0.5990 0.8819 0.079 Uiso 1 1 calc R U . . .
C25 C 0.2128(3) 0.61410(17) 0.8233(3) 0.0569(8) Uani 1 1 d . . . . .
H25 H 0.1792 0.6499 0.7886 0.068 Uiso 1 1 calc R U . . .
C26 C 0.0672(4) 0.49230(17) 0.9908(3) 0.0658(9) Uani 1 1 d . . . . .
H26 H 0.1084 0.4558 1.0194 0.079 Uiso 1 1 calc R U . . .
O1W O 1.0000 0.7375(4) 0.7500 0.109(3) Uani 0.5 2 d S T P . .


_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 O11 1.9558(19) 2_656 ?
Zn1 O11 1.9558(19) . ?
Zn1 N21 2.024(2) 2_656 ?
Zn1 N21 2.024(2) . ?
O11 C11 1.276(3) . ?
O12 C11 1.217(4) . ?
N21 C25 1.326(4) . ?
N21 C21 1.346(4) . ?
C11 C12 1.484(4) . ?
C12 C12 1.303(6) 7_667 ?
C21 C22 1.380(4) . ?
C22 C23 1.377(5) . ?
C23 C24 1.385(5) . ?
C23 C26 1.477(4) . ?
C24 C25 1.380(4) . ?
C26 C26 1.293(7) 5_567 ?

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
O11 Zn1 O11 99.96(12) 2_656 . ?
O11 Zn1 N21 109.38(9) 2_656 2_656 ?
O11 Zn1 N21 112.50(9) . 2_656 ?
O11 Zn1 N21 112.50(9) 2_656 . ?
O11 Zn1 N21 109.38(9) . . ?
N21 Zn1 N21 112.50(13) 2_656 . ?
C11 O11 Zn1 113.04(18) . . ?
C25 N21 C21 117.8(2) . . ?
C25 N21 Zn1 120.9(2) . . ?
C21 N21 Zn1 121.16(19) . . ?
O12 C11 O11 123.9(3) . . ?
O12 C11 C12 119.8(2) . . ?
O11 C11 C12 116.3(2) . . ?
C12 C12 C11 125.3(3) 7_667 . ?
N21 C21 C22 122.5(3) . . ?
C23 C22 C21 119.7(3) . . ?
C22 C23 C24 117.5(3) . . ?
C22 C23 C26 117.5(3) . . ?
C24 C23 C26 124.9(3) . . ?
C25 C24 C23 119.7(3) . . ?
N21 C25 C24 122.7(3) . . ?
C26 C26 C23 124.7(4) 5_567 . ?

_refine_diff_density_max         0.734
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.071

# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.081 0.250 0.078 577 136 ' '
2 0.032 0.750 0.140 577 136 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1438602'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-11-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            CIH065R
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O4 Zn'
_chemical_formula_iupac          ?
_chemical_formula_weight         391.71

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1425(2)
_cell_length_b                   9.1496(2)
_cell_length_c                   11.5118(3)
_cell_angle_alpha                97.1850(16)
_cell_angle_beta                 96.2776(17)
_cell_angle_gamma                102.7454(16)
_cell_volume                     821.58(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6589
_cell_measurement_theta_min      2.3097
_cell_measurement_theta_max      26.0183
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404

_exptl_absorpt_coefficient_mu    1.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            19976
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_unetI/netI     0.0781
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2789
_reflns_number_gt                2141
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1590
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         2789
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²+1.2231P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.484
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.092(9)

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C11 0.1452(8) 0.1466(7) 0.2168(5) 0.0481(16) Uani d . . . 1 . .
C C12 -0.0032(10) 0.1524(9) 0.1307(6) 0.064(2) Uani d . . . 1 . .
H H12A -0.106 0.1163 0.1644 0.077 Uiso calc U . R 1 . .
H H12B 0.0035 0.2577 0.1224 0.077 Uiso calc U . R 1 . .
C C13 -0.0199(13) 0.0685(11) 0.0163(7) 0.096(3) Uani d . . . 1 . .
H H13A -0.1386 0.0533 -0.016 0.115 Uiso calc U . R 1 . .
H H13B 0.0437 0.138 -0.029 0.115 Uiso calc U . R 1 . .
C C21 0.7201(7) 0.1874(6) 0.4479(5) 0.0348(12) Uani d . . . 1 . .
C C22 0.8614(7) 0.3072(6) 0.4175(5) 0.0389(13) Uani d . . . 1 . .
H H22A 0.82 0.3431 0.3467 0.047 Uiso calc U . R 1 . .
H H22B 0.9543 0.2616 0.3997 0.047 Uiso calc U . R 1 . .
C C23 0.9289(7) 0.4422(6) 0.5155(5) 0.0394(13) Uani d . . . 1 . .
H H23A 0.8368 0.4896 0.5321 0.047 Uiso calc U . R 1 . .
H H23B 0.9684 0.4064 0.5868 0.047 Uiso calc U . R 1 . .
C C31 0.4806(8) -0.0871(7) 0.1524(5) 0.0444(14) Uani d . . . 1 . .
H H31 0.5589 0.0061 0.1718 0.053 Uiso calc U . R 1 . .
C C32 0.4857(9) -0.1769(8) 0.0483(5) 0.0541(17) Uani d . . . 1 . .
H H32 0.5649 -0.1432 -0.0007 0.065 Uiso calc U . R 1 . .
C C33 0.3743(9) -0.3157(8) 0.0167(5) 0.0539(17) Uani d . . . 1 . .
C C34 0.2614(10) -0.3596(7) 0.0951(6) 0.0559(17) Uani d . . . 1 . .
H H34 0.1847 -0.4538 0.0783 0.067 Uiso calc U . R 1 . .
C C35 0.2628(9) -0.2621(7) 0.1997(5) 0.0504(16) Uani d . . . 1 . .
H H35 0.1866 -0.2937 0.2512 0.06 Uiso calc U . R 1 . .
C C36 0.3842(10) -0.4043(9) -0.0980(6) 0.065(2) Uani d . . . 1 . .
H H36 0.4682 -0.362 -0.1408 0.078 Uiso calc U . R 1 . .
C C37 0.2868(10) 0.4646(8) 0.8556(6) 0.0613(19) Uani d . . . 1 . .
H H37 0.2004 0.4226 0.8967 0.074 Uiso calc U . R 1 . .
C C38 0.3026(8) 0.3770(7) 0.7425(5) 0.0476(15) Uani d . . . 1 . .
C C39 0.4242(8) 0.4236(7) 0.6705(6) 0.0524(16) Uani d . . . 1 . .
H H39 0.5018 0.517 0.6919 0.063 Uiso calc U . R 1 . .
C C310 0.4302(8) 0.3314(6) 0.5672(5) 0.0446(14) Uani d . . . 1 . .
H H310 0.5117 0.3654 0.5199 0.053 Uiso calc U . R 1 . .
C C311 0.2042(7) 0.1516(6) 0.6024(5) 0.0423(14) Uani d . . . 1 . .
H H311 0.1276 0.058 0.5793 0.051 Uiso calc U . R 1 . .
C C312 0.1901(8) 0.2382(7) 0.7058(6) 0.0476(15) Uani d . . . 1 . .
H H312 0.1054 0.2034 0.7506 0.057 Uiso calc U . R 1 . .
N N31 0.3696(6) -0.1259(5) 0.2276(4) 0.0386(11) Uani d . . . 1 . .
N N32 0.3234(6) 0.1952(5) 0.5323(4) 0.0383(11) Uani d . . . 1 . .
O O11 0.1221(6) 0.0547(5) 0.2897(4) 0.0556(12) Uani d . . . 1 . .
O O12 0.2879(8) 0.2235(8) 0.2130(6) 0.101(2) Uani d . . . 1 . .
O O21 0.5848(5) 0.1451(5) 0.3752(3) 0.0488(11) Uani d . . . 1 . .
O O22 0.2553(5) -0.1394(4) 0.4559(3) 0.0460(10) Uani d . . . 1 . .
Zn Zn1 0.34326(8) 0.03989(7) 0.37668(6) 0.0361(3) Uani d . . . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C11 O12 . 1.227(8) ?
C11 O11 . 1.261(8) ?
C11 C12 . 1.491(9) ?
C12 C13 . 1.416(10) ?
C13 C13 2 1.380(14) ?
C21 O22 2_656 1.254(7) ?
C21 O21 . 1.262(7) ?
C21 C22 . 1.508(7) ?
C22 C23 . 1.522(7) ?
C23 C23 2_766 1.494(11) ?
C31 N31 . 1.341(7) ?
C31 C32 . 1.376(8) ?
C32 C33 . 1.368(10) ?
C33 C34 . 1.389(10) ?
C33 C36 . 1.481(9) ?
C34 C35 . 1.403(8) ?
C35 N31 . 1.331(7) ?
C36 C37 1_544 1.296(10) ?
C37 C36 1_566 1.296(10) ?
C37 C38 . 1.475(8) ?
C38 C312 . 1.378(9) ?
C38 C39 . 1.389(9) ?
C39 C310 . 1.381(8) ?
C310 N32 . 1.338(7) ?
C311 N32 . 1.354(7) ?
C311 C312 . 1.376(8) ?
N31 Zn1 . 2.206(4) ?
N32 Zn1 . 2.187(4) ?
O11 Zn1 . 2.003(5) ?
O21 Zn1 . 1.993(4) ?
O22 C21 2_656 1.254(7) ?
O22 Zn1 . 2.008(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O12 C11 O11 . . 120.6(7) ?
O12 C11 C12 . . 121.0(7) ?
O11 C11 C12 . . 118.3(6) ?
C13 C12 C11 . . 116.8(6) ?
C13 C13 C12 2 . 128.9(10) ?
O22 C21 O21 2_656 . 125.0(5) ?
O22 C21 C22 2_656 . 117.7(5) ?
O21 C21 C22 . . 117.3(5) ?
C21 C22 C23 . . 113.7(4) ?
C23 C23 C22 2_766 . 112.8(6) ?
N31 C31 C32 . . 123.9(6) ?
C33 C32 C31 . . 120.1(6) ?
C32 C33 C34 . . 116.8(5) ?
C32 C33 C36 . . 117.1(7) ?
C34 C33 C36 . . 126.2(7) ?
C33 C34 C35 . . 120.2(6) ?
N31 C35 C34 . . 122.2(6) ?
C37 C36 C33 1_544 . 126.1(8) ?
C36 C37 C38 1_566 . 124.9(8) ?
C312 C38 C39 . . 117.4(5) ?
C312 C38 C37 . . 117.9(6) ?
C39 C38 C37 . . 124.7(6) ?
C310 C39 C38 . . 120.1(6) ?
N32 C310 C39 . . 122.7(6) ?
N32 C311 C312 . . 123.6(5) ?
C311 C312 C38 . . 119.4(6) ?
C35 N31 C31 . . 116.8(5) ?
C35 N31 Zn1 . . 121.6(4) ?
C31 N31 Zn1 . . 121.1(4) ?
C310 N32 C311 . . 116.7(5) ?
C310 N32 Zn1 . . 123.3(4) ?
C311 N32 Zn1 . . 119.9(4) ?
C11 O11 Zn1 . . 111.4(4) ?
C21 O21 Zn1 . . 137.2(4) ?
C21 O22 Zn1 2_656 . 140.2(4) ?
O21 Zn1 O11 . . 133.3(2) ?
O21 Zn1 O22 . . 127.76(19) ?
O11 Zn1 O22 . . 98.50(18) ?
O21 Zn1 N32 . . 92.09(16) ?
O11 Zn1 N32 . . 93.38(17) ?
O22 Zn1 N32 . . 90.70(16) ?
O21 Zn1 N31 . . 87.72(17) ?
O11 Zn1 N31 . . 89.47(17) ?
O22 Zn1 N31 . . 86.46(16) ?
N32 Zn1 N31 . . 176.25(18) ?

####################################################################### 
# 
# 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_ye376pnna_sqd
_database_code_depnum_ccdc_archive 'CCDC 1438604'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-11-18 downloaded from the CCDC.
;

_audit_creation_method           'APEX2 v2014.1-1'
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 N2 O4 Zn'
_chemical_formula_weight         387.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

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

_cell_length_a                   12.396(3)
_cell_length_b                   13.262(3)
_cell_length_c                   15.772(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2592.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    71
_cell_measurement_theta_min      3.5428
_cell_measurement_theta_max      15.1350

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.993
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.963
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76212
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_av_R_equivalents  0.1297
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_max         28.596
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3200
_reflns_number_gt                1276
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.250 0.107 0.750 552 48 ' '
2 0.250 0.634 0.250 552 48 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1276P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3200
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2084
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.2263
_refine_ls_wR_factor_gt          0.1912
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_restrained_S_all      0.859
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.9645(5) 0.3227(5) 0.1291(3) 0.0947(15) Uani 1 1 d . . . . .
C12 C 1.0119(5) 0.3822(4) 0.0575(3) 0.1103(17) Uani 1 1 d . . . . .
H12 H 1.0698 0.3558 0.0273 0.132 Uiso 1 1 calc R U . . .
C13 C 0.9732(5) 0.4714(4) 0.0364(3) 0.1171(19) Uani 1 1 d . . . . .
H13 H 0.9146 0.4988 0.0651 0.140 Uiso 1 1 calc R U . . .
C21 C 0.7260(5) 0.3150(3) 0.4051(3) 0.1007(16) Uani 1 1 d . . . . .
H21 H 0.7677 0.2663 0.4322 0.121 Uiso 1 1 calc R U . . .
C22 C 0.6541(5) 0.3686(4) 0.4530(3) 0.1042(16) Uani 1 1 d . . . . .
H22 H 0.6482 0.3565 0.5109 0.125 Uiso 1 1 calc R U . . .
C23 C 0.5901(3) 0.4411(3) 0.4149(3) 0.0785(12) Uani 1 1 d . . . . .
C24 C 0.6041(4) 0.4553(4) 0.3290(3) 0.0969(15) Uani 1 1 d . . . . .
H24 H 0.5634 0.5032 0.3003 0.116 Uiso 1 1 calc R U . . .
C25 C 0.6778(4) 0.3987(3) 0.2867(3) 0.0837(12) Uani 1 1 d . . . . .
H25 H 0.6855 0.4099 0.2288 0.100 Uiso 1 1 calc R U . . .
C26 C 0.5136(4) 0.5086(3) 0.4623(3) 0.0986(15) Uani 1 1 d . . . . .
H26 H 0.4855 0.5649 0.4350 0.118 Uiso 1 1 calc R U . . .
N21 N 0.7399(3) 0.3281(2) 0.3222(2) 0.0767(10) Uani 1 1 d . . . . .
O11 O 0.8930(3) 0.3633(2) 0.1737(2) 0.1067(11) Uani 1 1 d . . . . .
O12 O 0.9950(4) 0.2324(3) 0.1389(3) 0.1271(14) Uani 1 1 d . . . . .
Zn1 Zn 0.85136(7) 0.2500 0.2500 0.0817(4) Uani 1 2 d S T P . .


_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
C11 O11 1.252(6) . ?
C11 O12 1.265(6) . ?
C11 C12 1.498(7) . ?
C11 Zn1 2.556(5) . ?
C12 C13 1.318(7) . ?
C13 C13 1.527(10) 5_765 ?
C21 N21 1.332(5) . ?
C21 C22 1.368(6) . ?
C22 C23 1.383(6) . ?
C23 C24 1.379(6) . ?
C23 C26 1.503(7) . ?
C24 C25 1.358(6) . ?
C25 N21 1.334(5) . ?
C26 C26 1.257(10) 5_666 ?
N21 Zn1 2.068(3) . ?
O11 Zn1 1.993(3) . ?
Zn1 O11 1.993(3) 4 ?
Zn1 N21 2.068(3) 4 ?
Zn1 C11 2.556(5) 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
O11 C11 O12 123.4(5) . . ?
O11 C11 C12 118.3(5) . . ?
O12 C11 C12 118.3(6) . . ?
O11 C11 Zn1 49.8(2) . . ?
O12 C11 Zn1 73.5(3) . . ?
C12 C11 Zn1 167.5(5) . . ?
C13 C12 C11 121.4(5) . . ?
C12 C13 C13 118.6(7) . 5_765 ?
N21 C21 C22 124.0(4) . . ?
C21 C22 C23 119.7(4) . . ?
C24 C23 C22 116.7(4) . . ?
C24 C23 C26 119.1(4) . . ?
C22 C23 C26 124.0(4) . . ?
C25 C24 C23 119.5(4) . . ?
N21 C25 C24 124.7(4) . . ?
C26 C26 C23 122.0(6) 5_666 . ?
C21 N21 C25 115.4(4) . . ?
C21 N21 Zn1 124.2(3) . . ?
C25 N21 Zn1 120.4(3) . . ?
C11 O11 Zn1 101.5(3) . . ?
O11 Zn1 O11 150.0(2) . 4 ?
O11 Zn1 N21 97.34(14) . . ?
O11 Zn1 N21 102.62(14) 4 . ?
O11 Zn1 N21 102.62(14) . 4 ?
O11 Zn1 N21 97.34(14) 4 4 ?
N21 Zn1 N21 96.17(18) . 4 ?
O11 Zn1 C11 28.70(15) . . ?
O11 Zn1 C11 126.35(19) 4 . ?
N21 Zn1 C11 126.01(18) . . ?
N21 Zn1 C11 98.34(14) 4 . ?
O11 Zn1 C11 126.4(2) . 4 ?
O11 Zn1 C11 28.70(15) 4 4 ?
N21 Zn1 C11 98.34(14) . 4 ?
N21 Zn1 C11 126.01(18) 4 4 ?
C11 Zn1 C11 113.5(3) . 4 ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_ye527c2c_sqd
_database_code_depnum_ccdc_archive 'CCDC 1481289'
_audit_update_record             
;
2016-05-23 deposited with the CCDC.
2016-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 N2 O4 Zn'
_chemical_formula_weight         361.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   8.8583(2)
_cell_length_b                   21.4370(5)
_cell_length_c                   13.5925(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.7932(12)
_cell_angle_gamma                90
_cell_volume                     2567.97(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      2.4247
_cell_measurement_theta_max      26.0554

_exptl_crystal_description       rod
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.935
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.969
_shelx_estimated_absorpt_T_min   0.773
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43787
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.563
_diffrn_reflns_theta_max         28.404
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3173
_reflns_number_gt                2604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+0.8133P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3173
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.113 0.250 0.067 638 158 ' '
2 0.031 0.750 0.120 638 158 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6907(2) 0.67976(10) 0.91481(15) 0.0485(5) Uani 1 1 d . . . . .
C2 C 0.7610(2) 0.72004(10) 0.99578(15) 0.0527(5) Uani 1 1 d . . . . .
H2 H 0.8261 0.7010 1.0447 0.063 Uiso 1 1 calc R U . . .
C3 C 0.4007(3) 0.54496(11) 0.86730(17) 0.0604(6) Uani 1 1 d . . . . .
H3 H 0.4998 0.5314 0.8637 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3085(3) 0.51002(12) 0.9204(2) 0.0686(7) Uani 1 1 d . . . . .
H4 H 0.3448 0.4735 0.9512 0.082 Uiso 1 1 calc R U . . .
C5 C 0.1625(3) 0.52892(12) 0.92794(19) 0.0685(7) Uani 1 1 d . . . . .
C6 C 0.1145(3) 0.58294(14) 0.8783(2) 0.0844(9) Uani 1 1 d . . . . .
H6 H 0.0160 0.5973 0.8810 0.101 Uiso 1 1 calc R U . . .
C7 C 0.2128(3) 0.61511(13) 0.8251(2) 0.0732(8) Uani 1 1 d . . . . .
H7 H 0.1778 0.6507 0.7909 0.088 Uiso 1 1 calc R U . . .
C8 C 0.0672(3) 0.49182(14) 0.9898(2) 0.0822(8) Uani 1 1 d . . . . .
H8 H 0.1063 0.4543 1.0157 0.099 Uiso 1 1 calc R U . . .
N1 N 0.35581(18) 0.59758(8) 0.82035(12) 0.0492(4) Uani 1 1 d . . . . .
O1 O 0.7128(2) 0.62343(8) 0.91808(13) 0.0752(5) Uani 1 1 d . . . . .
O2 O 0.60820(17) 0.70693(6) 0.84530(10) 0.0556(4) Uani 1 1 d . . . . .
Zn1 Zn 0.5000 0.65141(2) 0.7500 0.03868(12) Uani 1 2 d S T P . .


_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
C1 O1 1.223(3) . ?
C1 O2 1.275(2) . ?
C1 C2 1.485(3) . ?
C2 C2 1.306(4) 7_667 ?
C2 H2 0.9300 . ?
C3 N1 1.337(3) . ?
C3 C4 1.366(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(4) . ?
C5 C8 1.482(3) . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.330(3) . ?
C7 H7 0.9300 . ?
C8 C8 1.298(5) 5_567 ?
C8 H8 0.9300 . ?
N1 Zn1 2.0308(16) . ?
O2 Zn1 1.9398(14) . ?
Zn1 O2 1.9398(14) 2_656 ?
Zn1 N1 2.0307(16) 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 123.74(19) . . ?
O1 C1 C2 119.57(18) . . ?
O2 C1 C2 116.69(18) . . ?
C2 C2 C1 125.6(2) 7_667 . ?
C2 C2 H2 117.2 7_667 . ?
C1 C2 H2 117.2 . . ?
N1 C3 C4 123.3(2) . . ?
N1 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 117.2(2) . . ?
C4 C5 C8 118.7(2) . . ?
C6 C5 C8 124.1(2) . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
N1 C7 C6 122.8(2) . . ?
N1 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C8 C8 C5 124.3(3) 5_567 . ?
C8 C8 H8 117.9 5_567 . ?
C5 C8 H8 117.9 . . ?
C7 N1 C3 117.05(18) . . ?
C7 N1 Zn1 120.65(15) . . ?
C3 N1 Zn1 122.24(14) . . ?
C1 O2 Zn1 114.96(13) . . ?
O2 Zn1 O2 104.30(8) . 2_656 ?
O2 Zn1 N1 111.79(7) . 2_656 ?
O2 Zn1 N1 109.03(7) 2_656 2_656 ?
O2 Zn1 N1 109.03(7) . . ?
O2 Zn1 N1 111.80(7) 2_656 . ?
N1 Zn1 N1 110.74(10) 2_656 . ?

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_ye541Pnna
_database_code_depnum_ccdc_archive 'CCDC 1481290'
_audit_update_record             
;
2016-05-23 deposited with the CCDC.
2016-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 I0.1 N2 O4 Zn'
_chemical_formula_weight         400.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

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

_cell_length_a                   12.471(3)
_cell_length_b                   13.306(3)
_cell_length_c                   15.711(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2607.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      2.4247
_cell_measurement_theta_max      26.0554

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.020
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62046
_diffrn_reflns_av_unetI/netI     0.1182
_diffrn_reflns_av_R_equivalents  0.4013
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.426
_diffrn_reflns_theta_max         25.229
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.929
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.929
_reflns_number_total             2197
_reflns_number_gt                871
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+3.0800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2197
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2318
_refine_ls_R_factor_gt           0.0894
_refine_ls_wR_factor_ref         0.2079
_refine_ls_wR_factor_gt          0.1491
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_RINTA01_ye541Pnna           
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Data were not of the highest quality. 
;
_vrf_PLAT020_ye541Pnna           
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.401 Report
RESPONSE: Data were not of the highest quality.
;
_vrf_PLAT601_ye541Pnna           
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        280 Ang3  
RESPONSE: Data were not of the highest quality. The possible solvent molecules were highly disordered, so they could not be refined.
;
_vrf_PLAT230_ye541Pnna           
;
PROBLEM: Hirshfeld Test Diff for    C23    --  C26     ..        7.7 s.u.  
RESPONSE: Data were not of the highest quality.
;
_vrf_PLAT911_ye541Pnna           
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.600        160 Report
RESPONSE: Data were not of the highest quality. 250 Most disagreeable reflections were omitted.
;
# end Validation Reply Form

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.9678(11) 0.3197(8) 0.1291(6) 0.112(3) Uani 1 1 d . . . . .
C12 C 1.0107(9) 0.3821(8) 0.0582(6) 0.122(4) Uani 1 1 d . . . . .
H12 H 1.0674 0.3554 0.0272 0.146 Uiso 1 1 calc R U . . .
C13 C 0.9760(9) 0.4718(7) 0.0353(5) 0.117(4) Uani 1 1 d . . . . .
H13 H 0.9190 0.5003 0.0649 0.141 Uiso 1 1 calc R U . . .
C21 C 0.7260(9) 0.3134(6) 0.4072(5) 0.111(3) Uani 1 1 d . . . . .
H21 H 0.7674 0.2654 0.4349 0.133 Uiso 1 1 calc R U . . .
C22 C 0.6529(9) 0.3686(7) 0.4536(5) 0.107(3) Uani 1 1 d . . . . .
H22 H 0.6445 0.3569 0.5116 0.128 Uiso 1 1 calc R U . . .
C23 C 0.5926(8) 0.4411(6) 0.4138(6) 0.090(3) Uani 1 1 d . . . . .
C24 C 0.6048(8) 0.4558(7) 0.3294(6) 0.099(3) Uani 1 1 d . . . . .
H24 H 0.5645 0.5043 0.3012 0.119 Uiso 1 1 calc R U . . .
C25 C 0.6756(9) 0.3997(7) 0.2872(6) 0.103(3) Uani 1 1 d . . . . .
H25 H 0.6820 0.4112 0.2290 0.124 Uiso 1 1 calc R U . . .
C26 C 0.5137(10) 0.5055(7) 0.4613(5) 0.117(3) Uani 1 1 d . . . . .
H26 H 0.4822 0.5581 0.4314 0.140 Uiso 1 1 calc R U . . .
N21 N 0.7391(6) 0.3273(5) 0.3214(4) 0.086(2) Uani 1 1 d . . . . .
O11 O 0.8924(7) 0.3631(5) 0.1733(4) 0.123(2) Uani 1 1 d . . . . .
O12 O 0.9919(7) 0.2324(4) 0.1405(4) 0.137(3) Uani 1 1 d . . . . .
Zn1 Zn 0.85009(12) 0.2500 0.2500 0.0870(6) Uani 1 2 d S T P . .
I1 I 0.887(4) 0.278(4) 0.852(3) 0.39(2) Uiso 0.05 1 d . . P . .


_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
C11 O12 1.213(11) . ?
C11 O11 1.304(11) . ?
C11 C12 1.489(12) . ?
C11 Zn1 2.573(11) . ?
C12 C13 1.320(12) . ?
C12 H12 0.9300 . ?
C13 C13 1.467(17) 5_765 ?
C13 H13 0.9300 . ?
C21 N21 1.371(9) . ?
C21 C22 1.379(11) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.349(11) . ?
C23 C26 1.503(12) . ?
C24 C25 1.333(11) . ?
C24 H24 0.9300 . ?
C25 N21 1.359(10) . ?
C25 H25 0.9300 . ?
C26 C26 1.272(16) 5_666 ?
C26 H26 0.9300 . ?
N21 Zn1 2.057(7) . ?
O11 Zn1 1.999(5) . ?
O12 Zn1 2.479(8) . ?
Zn1 O11 1.999(5) 4 ?
Zn1 N21 2.057(7) 4 ?
Zn1 O12 2.479(8) 4 ?
Zn1 C11 2.573(11) 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
O12 C11 O11 121.7(10) . . ?
O12 C11 C12 123.7(11) . . ?
O11 C11 C12 114.2(10) . . ?
O12 C11 Zn1 71.8(6) . . ?
O11 C11 Zn1 49.9(4) . . ?
C12 C11 Zn1 163.4(10) . . ?
C13 C12 C11 126.2(10) . . ?
C13 C12 H12 116.9 . . ?
C11 C12 H12 116.9 . . ?
C12 C13 C13 122.3(12) . 5_765 ?
C12 C13 H13 118.8 . . ?
C13 C13 H13 118.8 5_765 . ?
N21 C21 C22 121.8(8) . . ?
N21 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 119.7(8) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C24 C23 C22 119.2(9) . . ?
C24 C23 C26 118.6(9) . . ?
C22 C23 C26 122.2(9) . . ?
C25 C24 C23 118.9(9) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 N21 125.9(9) . . ?
C24 C25 H25 117.1 . . ?
N21 C25 H25 117.1 . . ?
C26 C26 C23 125.8(13) 5_666 . ?
C26 C26 H26 117.1 5_666 . ?
C23 C26 H26 117.1 . . ?
C25 N21 C21 114.5(8) . . ?
C25 N21 Zn1 122.1(6) . . ?
C21 N21 Zn1 123.3(7) . . ?
C11 O11 Zn1 100.2(6) . . ?
C11 O12 Zn1 80.5(7) . . ?
O11 Zn1 O11 149.4(5) 4 . ?
O11 Zn1 N21 97.5(3) 4 4 ?
O11 Zn1 N21 103.0(3) . 4 ?
O11 Zn1 N21 103.0(3) 4 . ?
O11 Zn1 N21 97.5(3) . . ?
N21 Zn1 N21 95.4(4) 4 . ?
O11 Zn1 O12 99.1(3) 4 . ?
O11 Zn1 O12 57.6(2) . . ?
N21 Zn1 O12 93.1(3) 4 . ?
N21 Zn1 O12 154.9(2) . . ?
O11 Zn1 O12 57.6(2) 4 4 ?
O11 Zn1 O12 99.1(3) . 4 ?
N21 Zn1 O12 154.9(2) 4 4 ?
N21 Zn1 O12 93.1(3) . 4 ?
O12 Zn1 O12 88.9(3) . 4 ?
O11 Zn1 C11 124.5(4) 4 . ?
O11 Zn1 C11 29.9(3) . . ?
N21 Zn1 C11 99.3(3) 4 . ?
N21 Zn1 C11 127.3(3) . . ?
O12 Zn1 C11 27.7(3) . . ?
O12 Zn1 C11 94.1(3) 4 . ?
O11 Zn1 C11 29.9(3) 4 4 ?
O11 Zn1 C11 124.5(4) . 4 ?
N21 Zn1 C11 127.3(3) 4 4 ?
N21 Zn1 C11 99.3(3) . 4 ?
O12 Zn1 C11 94.1(3) . 4 ?
O12 Zn1 C11 27.7(3) 4 4 ?
C11 Zn1 C11 110.5(6) . 4 ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

