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

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

data_as
_database_code_depnum_ccdc_archive 'CCDC 1520353'
_audit_update_record             
;
2016-12-02 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 N2 O4 Zn'
_chemical_formula_weight         303.61

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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'

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

_cell_length_a                   12.487(10)
_cell_length_b                   12.487(10)
_cell_length_c                   9.776(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1524(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1040
_cell_measurement_theta_min      2.307
_cell_measurement_theta_max      21.425

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.618
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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 Smart Aepex CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8999
_diffrn_reflns_av_unetI/netI     0.1591
_diffrn_reflns_av_R_equivalents  0.1390
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.631
_diffrn_reflns_theta_max         23.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.842
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.839
_reflns_number_total             2306
_reflns_number_gt                1095
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.836

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-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)+(0.1661P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 372 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.10(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2306
_refine_ls_number_parameters     151
_refine_ls_number_restraints     260
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.1094
_refine_ls_wR_factor_ref         0.2786
_refine_ls_wR_factor_gt          0.2513
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.878
_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
N2 N 0.9410(19) 0.5631(19) 0.251(3) 0.079(7) Uani 1 1 d . U . . .
H2C H 0.9724 0.5793 0.1626 0.095 Uiso 1 1 d R U . . .
N1 N 0.6706(14) 0.8564(11) 0.101(2) 0.080(7) Uani 1 1 d G U . . .
C1 C 0.7523(15) 0.8082(15) 0.026(2) 0.093(9) Uani 1 1 d G U . . .
H1A H 0.7746 0.8379 -0.0561 0.112 Uiso 1 1 calc R U . . .
C2 C 0.8007(14) 0.7156(16) 0.075(2) 0.085(8) Uani 1 1 d G U . . .
H2A H 0.8554 0.6833 0.0256 0.101 Uiso 1 1 calc R U . . .
C3 C 0.7674(16) 0.6712(13) 0.199(2) 0.085(8) Uani 1 1 d G U . . .
C4 C 0.6857(15) 0.7194(14) 0.273(2) 0.096(8) Uani 1 1 d G U . . .
H4A H 0.6634 0.6897 0.3553 0.116 Uiso 1 1 d R U . . .
C5 C 0.6373(12) 0.8120(13) 0.224(2) 0.072(7) Uani 1 1 d G U . . .
H5A H 0.5826 0.8443 0.2736 0.086 Uiso 1 1 d R U . . .
C6 C 0.812(2) 0.576(2) 0.242(3) 0.067(7) Uani 1 1 d . U . . .
H6A H 0.7869 0.5198 0.1810 0.081 Uiso 1 1 d R U . . .
H6B H 0.7838 0.5601 0.3318 0.081 Uiso 1 1 d R U . . .
C7 C 0.985(3) 0.640(3) 0.358(3) 0.078(7) Uani 1 1 d . U . . .
H7A H 0.9301 0.6910 0.3873 0.093 Uiso 1 1 d R U . . .
C8 C 1.079(3) 0.697(3) 0.305(4) 0.127(14) Uani 1 1 d . U . . .
H8A H 1.1032 0.7403 0.3619 0.191 Uiso 1 1 d R U . . .
H8B H 1.0606 0.7337 0.2221 0.191 Uiso 1 1 d R U . . .
H8C H 1.1354 0.6462 0.2861 0.191 Uiso 1 1 d R U . . .
C9 C 1.017(2) 0.566(2) 0.476(3) 0.059(6) Uani 1 1 d . U . . .
C10 C 0.644(2) 1.174(3) -0.0267(8) 0.112(11) Uani 1 1 d D U . . .
C11 C 0.714(5) 1.267(3) -0.046(7) 0.30(4) Uani 1 1 d D U . . .
H11A H 0.6699 1.3273 -0.0697 0.456 Uiso 1 1 d R U . . .
H11B H 0.7449 1.2543 -0.1175 0.456 Uiso 1 1 d R U . . .
H11C H 0.7518 1.2828 0.0377 0.456 Uiso 1 1 d R U . . .
O1 O 1.0525(19) 0.6269(17) 0.577(3) 0.091(6) Uani 1 1 d . U . . .
O2 O 1.0207(13) 0.4747(13) 0.469(2) 0.053(4) Uani 1 1 d . U . . .
O3 O 0.6848(17) 1.0988(18) 0.024(2) 0.097(6) Uani 1 1 d D U . . .
O4 O 0.551(2) 1.174(3) -0.062(3) 0.146(11) Uani 1 1 d D U . . .
Zn1 Zn 0.5902(2) 0.9842(3) 0.0279(18) 0.0635(10) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C7 1.52(3) . ?
N2 C6 1.62(3) . ?
N2 Zn1 2.01(2) 4_565 ?
N2 H2C 0.9700 . ?
N1 C1 1.3900 . ?
N1 C5 1.3900 . ?
N1 Zn1 2.015(12) . ?
C1 C2 1.3900 . ?
C1 H1A 0.9300 . ?
C2 C3 1.3900 . ?
C2 H2A 0.9300 . ?
C3 C6 1.38(3) . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.47(4) . ?
C7 C9 1.53(4) . ?
C7 H7A 0.9800 . ?
C8 H8A 0.8366 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O2 1.15(3) . ?
C9 O1 1.32(3) . ?
C10 O3 1.17(2) . ?
C10 O4 1.21(2) . ?
C10 C11 1.47(3) . ?
C10 Zn1 2.52(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.8171 . ?
C11 H11C 0.9600 . ?
O1 Zn1 2.070(19) 3_755 ?
O2 Zn1 2.083(15) 4_565 ?
O3 Zn1 1.86(2) . ?
Zn1 N2 2.01(2) 3_654 ?
Zn1 O1 2.070(19) 4_574 ?
Zn1 O2 2.083(15) 3_654 ?

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
C7 N2 C6 110(2) . . ?
C7 N2 Zn1 114.6(17) . 4_565 ?
C6 N2 Zn1 111.5(17) . 4_565 ?
C7 N2 H2C 109.4 . . ?
C6 N2 H2C 109.4 . . ?
Zn1 N2 H2C 102.0 4_565 . ?
C1 N1 C5 120.0 . . ?
C1 N1 Zn1 121.6(8) . . ?
C5 N1 Zn1 118.2(9) . . ?
C2 C1 N1 120.0 . . ?
C2 C1 H1A 120.0 . . ?
N1 C1 H1A 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C6 C3 C4 120.8(15) . . ?
C6 C3 C2 119.1(14) . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C4 C5 N1 120.0 . . ?
C4 C5 H5A 120.0 . . ?
N1 C5 H5A 120.0 . . ?
C3 C6 N2 120(2) . . ?
C3 C6 H6A 107.4 . . ?
N2 C6 H6A 107.0 . . ?
C3 C6 H6B 107.4 . . ?
N2 C6 H6B 107.3 . . ?
H6A C6 H6B 106.9 . . ?
C8 C7 N2 111(3) . . ?
C8 C7 C9 110(3) . . ?
N2 C7 C9 103(2) . . ?
C8 C7 H7A 110.5 . . ?
N2 C7 H7A 111.3 . . ?
C9 C7 H7A 110.5 . . ?
C7 C8 H8A 111.6 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.7 . . ?
H8A C8 H8C 107.0 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 O1 127(2) . . ?
O2 C9 C7 124(2) . . ?
O1 C9 C7 108(2) . . ?
O3 C10 O4 123(3) . . ?
O3 C10 C11 116(3) . . ?
O4 C10 C11 122(4) . . ?
O3 C10 Zn1 43.7(16) . . ?
O4 C10 Zn1 79(2) . . ?
C11 C10 Zn1 159(3) . . ?
C10 C11 H11A 108.0 . . ?
C10 C11 H11B 103.1 . . ?
H11A C11 H11B 102.4 . . ?
C10 C11 H11C 110.0 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 122.8 . . ?
C9 O1 Zn1 120.7(16) . 3_755 ?
C9 O2 Zn1 115.6(14) . 4_565 ?
C10 O3 Zn1 110(2) . . ?
O3 Zn1 N1 107.5(9) . . ?
O3 Zn1 N2 144.3(11) . 3_654 ?
N1 Zn1 N2 108.0(9) . 3_654 ?
O3 Zn1 O1 90.5(9) . 4_574 ?
N1 Zn1 O1 92.8(7) . 4_574 ?
N2 Zn1 O1 91.5(8) 3_654 4_574 ?
O3 Zn1 O2 95.7(7) . 3_654 ?
N1 Zn1 O2 93.0(6) . 3_654 ?
N2 Zn1 O2 78.7(7) 3_654 3_654 ?
O1 Zn1 O2 169.9(7) 4_574 3_654 ?
O3 Zn1 C10 25.8(8) . . ?
N1 Zn1 C10 133.3(9) . . ?
N2 Zn1 C10 118.7(11) 3_654 . ?
O1 Zn1 C10 87.0(8) 4_574 . ?
O2 Zn1 C10 95.1(7) 3_654 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.0 . . . . ?
Zn1 N1 C1 C2 -175.3(13) . . . . ?
N1 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C6 176(2) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C6 C3 C4 C5 -176(2) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 N1 0.0 . . . . ?
C1 N1 C5 C4 0.0 . . . . ?
Zn1 N1 C5 C4 175.5(13) . . . . ?
C4 C3 C6 N2 -130.8(18) . . . . ?
C2 C3 C6 N2 53(3) . . . . ?
C7 N2 C6 C3 64(3) . . . . ?
Zn1 N2 C6 C3 -168.1(17) 4_565 . . . ?
C6 N2 C7 C8 -134(3) . . . . ?
Zn1 N2 C7 C8 100(3) 4_565 . . . ?
C6 N2 C7 C9 108(2) . . . . ?
Zn1 N2 C7 C9 -18(3) 4_565 . . . ?
C8 C7 C9 O2 -107(4) . . . . ?
N2 C7 C9 O2 11(4) . . . . ?
C8 C7 C9 O1 64(3) . . . . ?
N2 C7 C9 O1 -177(2) . . . . ?
O2 C9 O1 Zn1 -48(4) . . . 3_755 ?
C7 C9 O1 Zn1 140.9(19) . . . 3_755 ?
O1 C9 O2 Zn1 -168(2) . . . 4_565 ?
C7 C9 O2 Zn1 2(4) . . . 4_565 ?
O4 C10 O3 Zn1 5(3) . . . . ?
C11 C10 O3 Zn1 -175(3) . . . . ?
C10 O3 Zn1 N1 175.0(16) . . . . ?
C10 O3 Zn1 N2 -11(2) . . . 3_654 ?
C10 O3 Zn1 O1 81.9(17) . . . 4_574 ?
C10 O3 Zn1 O2 -90.0(17) . . . 3_654 ?

_refine_diff_density_max         1.745
_refine_diff_density_min         -1.765
_refine_diff_density_rms         0.221


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.029 277 83 ' '
2 0.500 0.500 -0.021 245 77 ' '
_platon_squeeze_details          ?

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_bs
_database_code_depnum_ccdc_archive 'CCDC 1520354'
_audit_update_record             
;
2016-12-02 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 N2 O4 Zn'
_chemical_formula_weight         303.61

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      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

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

_cell_length_a                   12.800(3)
_cell_length_b                   12.800(3)
_cell_length_c                   9.984(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1635.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2210
_cell_measurement_theta_min      2.261
_cell_measurement_theta_max      21.08

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.507
_shelx_estimated_absorpt_T_min   0.817
_shelx_estimated_absorpt_T_max   0.864
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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 Smart Aepex CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11714
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.591
_diffrn_reflns_theta_max         25.240
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2963
_reflns_number_gt                2414
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.994

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-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)+(0.0799P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.023(17)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2963
_refine_ls_number_parameters     165
_refine_ls_number_restraints     249
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.003
_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
C1 C 0.7518(7) 0.6940(7) 1.0363(12) 0.061(2) Uani 1 1 d . U . . .
H1 H 0.7332 0.6671 1.1195 0.073 Uiso 1 1 calc R U . . .
C2 C 0.7008(8) 0.7818(8) 0.9920(10) 0.061(2) Uani 1 1 d . U . . .
H2 H 0.6497 0.8128 1.0450 0.074 Uiso 1 1 calc R U . . .
C3 C 0.7256(7) 0.8246(8) 0.8675(9) 0.054(2) Uani 1 1 d . U . . .
C4 C 0.8044(7) 0.7753(7) 0.7961(10) 0.060(2) Uani 1 1 d . U . . .
H4 H 0.8242 0.8004 0.7124 0.072 Uiso 1 1 calc R U . . .
C5 C 0.8526(8) 0.6896(8) 0.8494(10) 0.058(2) Uani 1 1 d . U . . .
H5 H 0.9073 0.6599 0.8013 0.070 Uiso 1 1 calc R U . . .
C6 C 0.6816(6) 0.9259(7) 0.8216(8) 0.049(2) Uani 1 1 d . U . . .
H6A H 0.7090 0.9405 0.7330 0.058 Uiso 1 1 calc R U . . .
H6B H 0.7068 0.9803 0.8809 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5154(8) 0.8645(7) 0.7140(8) 0.0492(19) Uani 1 1 d . U . . .
H7 H 0.5657 0.8118 0.6836 0.059 Uiso 1 1 calc R U . . .
C8 C 0.4191(11) 0.8094(9) 0.7762(14) 0.097(4) Uani 1 1 d . U . . .
H8A H 0.4421 0.7551 0.8356 0.145 Uiso 1 1 calc R U . . .
H8B H 0.3772 0.7797 0.7062 0.145 Uiso 1 1 calc R U . . .
H8C H 0.3784 0.8594 0.8254 0.145 Uiso 1 1 calc R U . . .
C9 C 0.4780(6) 0.9289(7) 0.5943(8) 0.0416(18) Uani 1 1 d . U . . .
C10 C 0.8590(15) 0.3268(13) 1.1020(17) 0.105(4) Uani 1 1 d . U . . .
C11 C 0.830(2) 0.2169(17) 1.117(3) 0.211(9) Uani 1 1 d . U . . .
H11A H 0.7552 0.2106 1.1172 0.316 Uiso 1 1 calc R U . . .
H11B H 0.8571 0.1907 1.2005 0.316 Uiso 1 1 calc R U . . .
H11C H 0.8584 0.1771 1.0445 0.316 Uiso 1 1 calc R U . . .
N1 N 0.8261(6) 0.6450(6) 0.9680(7) 0.0489(17) Uani 1 1 d . U . . .
N2 N 0.5655(5) 0.9329(5) 0.8156(7) 0.0440(15) Uani 1 1 d . U . . .
H2D H 0.5416 0.9115 0.8959 0.053 Uiso 1 1 d R U . . .
O1 O 0.4780(4) 1.0261(4) 0.5996(6) 0.0419(12) Uani 1 1 d . U . . .
O2 O 0.4455(5) 0.8753(5) 0.4954(6) 0.0522(14) Uani 1 1 d . U . . .
O3 O 0.8107(6) 0.3937(6) 1.0452(10) 0.086(2) Uani 1 1 d . U . . .
O4 O 0.9528(10) 0.3363(10) 1.1403(14) 0.143(4) Uani 1 1 d . U . . .
Zn1 Zn 0.90972(7) 0.51723(7) 1.04161(7) 0.0401(3) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.327(11) . ?
C1 C2 1.374(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(12) . ?
C3 C6 1.486(12) . ?
C4 C5 1.367(12) . ?
C4 H4 0.9300 . ?
C5 N1 1.357(11) . ?
C5 H5 0.9300 . ?
C6 N2 1.490(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.485(10) . ?
C7 C9 1.529(12) . ?
C7 C8 1.550(14) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O1 1.246(9) . ?
C9 O2 1.272(10) . ?
C10 O3 1.199(18) . ?
C10 O4 1.266(18) . ?
C10 C11 1.46(2) . ?
C10 Zn1 2.594(16) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N1 Zn1 2.089(7) . ?
N2 Zn1 2.121(6) 4_574 ?
N2 H2D 0.9000 . ?
O1 Zn1 2.145(6) 4_574 ?
O2 Zn1 2.136(6) 3_654 ?
O3 Zn1 2.026(7) . ?
Zn1 N2 2.121(6) 3_755 ?
Zn1 O2 2.136(6) 4_565 ?
Zn1 O1 2.145(6) 3_755 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 124.2(10) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 120.0(9) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 116.4(8) . . ?
C4 C3 C6 120.9(8) . . ?
C2 C3 C6 122.1(8) . . ?
C5 C4 C3 119.6(9) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 124.3(8) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C3 C6 N2 116.3(8) . . ?
C3 C6 H6A 108.2 . . ?
N2 C6 H6A 108.2 . . ?
C3 C6 H6B 108.2 . . ?
N2 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
N2 C7 C9 110.6(7) . . ?
N2 C7 C8 109.7(8) . . ?
C9 C7 C8 108.1(9) . . ?
N2 C7 H7 109.5 . . ?
C9 C7 H7 109.5 . . ?
C8 C7 H7 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 O2 124.8(8) . . ?
O1 C9 C7 120.4(7) . . ?
O2 C9 C7 114.7(7) . . ?
O3 C10 O4 124.3(15) . . ?
O3 C10 C11 127.3(18) . . ?
O4 C10 C11 107.6(19) . . ?
O3 C10 Zn1 49.3(7) . . ?
O4 C10 Zn1 75.1(10) . . ?
C11 C10 Zn1 172.6(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 C5 115.4(7) . . ?
C1 N1 Zn1 123.8(6) . . ?
C5 N1 Zn1 120.5(6) . . ?
C7 N2 C6 115.0(7) . . ?
C7 N2 Zn1 110.9(5) . 4_574 ?
C6 N2 Zn1 110.6(5) . 4_574 ?
C7 N2 H2D 106.4 . . ?
C6 N2 H2D 106.6 . . ?
Zn1 N2 H2D 106.9 4_574 . ?
C9 O1 Zn1 114.8(5) . 4_574 ?
C9 O2 Zn1 123.7(5) . 3_654 ?
C10 O3 Zn1 104.1(9) . . ?
O3 Zn1 N1 107.2(3) . . ?
O3 Zn1 N2 145.0(3) . 3_755 ?
N1 Zn1 N2 107.4(3) . 3_755 ?
O3 Zn1 O2 91.6(3) . 4_565 ?
N1 Zn1 O2 93.1(2) . 4_565 ?
N2 Zn1 O2 91.3(2) 3_755 4_565 ?
O3 Zn1 O1 94.1(3) . 3_755 ?
N1 Zn1 O1 93.7(2) . 3_755 ?
N2 Zn1 O1 78.8(2) 3_755 3_755 ?
O2 Zn1 O1 169.3(2) 4_565 3_755 ?
O3 Zn1 C10 26.6(4) . . ?
N1 Zn1 C10 133.6(5) . . ?
N2 Zn1 C10 119.0(5) 3_755 . ?
O2 Zn1 C10 86.4(4) 4_565 . ?
O1 Zn1 C10 94.8(4) 3_755 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.4(16) . . . . ?
C1 C2 C3 C4 -1.5(15) . . . . ?
C1 C2 C3 C6 -173.0(9) . . . . ?
C2 C3 C4 C5 0.0(15) . . . . ?
C6 C3 C4 C5 171.6(9) . . . . ?
C3 C4 C5 N1 2.9(16) . . . . ?
C4 C3 C6 N2 131.0(9) . . . . ?
C2 C3 C6 N2 -57.9(12) . . . . ?
N2 C7 C9 O1 -10.1(12) . . . . ?
C8 C7 C9 O1 110.0(9) . . . . ?
N2 C7 C9 O2 171.9(7) . . . . ?
C8 C7 C9 O2 -68.0(11) . . . . ?
C2 C1 N1 C5 2.2(15) . . . . ?
C2 C1 N1 Zn1 175.9(8) . . . . ?
C4 C5 N1 C1 -3.8(15) . . . . ?
C4 C5 N1 Zn1 -177.8(8) . . . . ?
C9 C7 N2 C6 -105.5(8) . . . . ?
C8 C7 N2 C6 135.4(9) . . . . ?
C9 C7 N2 Zn1 20.9(9) . . . 4_574 ?
C8 C7 N2 Zn1 -98.2(8) . . . 4_574 ?
C3 C6 N2 C7 -66.3(9) . . . . ?
C3 C6 N2 Zn1 167.1(6) . . . 4_574 ?
O2 C9 O1 Zn1 171.5(7) . . . 4_574 ?
C7 C9 O1 Zn1 -6.3(10) . . . 4_574 ?
O1 C9 O2 Zn1 45.0(12) . . . 3_654 ?
C7 C9 O2 Zn1 -137.2(6) . . . 3_654 ?
O4 C10 O3 Zn1 -4(2) . . . . ?
C11 C10 O3 Zn1 -172(2) . . . . ?

_refine_diff_density_max         0.698
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.076


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.023 267 75 ' '
2 0.500 0.500 -0.028 316 80 ' '
_platon_squeeze_details          ?

_shelxl_version_number           2013-2

