# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_ZAIL-OTs
_database_code_depnum_ccdc_archive 'CCDC 1528715'
_audit_update_record             
;
2017-01-20 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 N2 O5 S Zn'
_chemical_formula_sum            'C19 H22 N2 O5 S Zn'
_chemical_formula_weight         455.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_chemical_absolute_configuration .

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

_cell_length_a                   8.2326(2)
_cell_length_b                   13.5545(3)
_cell_length_c                   17.4759(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1950.11(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3087
_cell_measurement_theta_min      6.00
_cell_measurement_theta_max      68.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    3.046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5285
_exptl_absorpt_correction_T_max  0.5953
_exptl_absorpt_process_details   Crysalispro

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Supernova (Cu) X-Ray source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4663
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.94
_diffrn_reflns_theta_max         67.98
_reflns_number_total             3087
_reflns_number_gt                3016
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0775P)²+1.7833P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         3087
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.491(2) -0.1211(9) 0.8873(7) 0.152(6) Uani 1 1 d . . .
H1A H 0.5290 -0.1762 0.8580 0.228 Uiso 1 1 calc R . .
H1B H 0.4168 -0.0828 0.8569 0.228 Uiso 1 1 calc R . .
H1C H 0.4355 -0.1446 0.9322 0.228 Uiso 1 1 calc R . .
C2 C 0.6555(19) -0.0474(11) 0.9146(9) 0.169(8) Uani 1 1 d . . .
H2A H 0.7310 -0.0852 0.9456 0.203 Uiso 1 1 calc R . .
H2B H 0.7125 -0.0232 0.8698 0.203 Uiso 1 1 calc R . .
C3 C 0.5890(12) 0.0345(6) 0.9585(5) 0.093(3) Uani 1 1 d . . .
C4 C 0.582(2) 0.0302(12) 1.0355(6) 0.202(10) Uani 1 1 d . . .
H4A H 0.6553 -0.0194 1.0538 0.303 Uiso 1 1 calc R . .
H4B H 0.4730 0.0139 1.0510 0.303 Uiso 1 1 calc R . .
H4C H 0.6111 0.0931 1.0566 0.303 Uiso 1 1 calc R . .
C5 C 0.4819(6) 0.1106(3) 0.9108(3) 0.0331(9) Uani 1 1 d D . .
C6 C 0.3897(5) 0.1815(3) 0.9637(2) 0.0256(8) Uani 1 1 d . . .
C7 C 0.0310(6) 0.3164(3) 1.2182(2) 0.0299(9) Uani 1 1 d . . .
C8 C 0.0057(5) -0.0903(3) 1.2372(2) 0.0274(8) Uani 1 1 d . . .
C9 C -0.1124(5) -0.0248(4) 1.2147(3) 0.0325(10) Uani 1 1 d . . .
H9 H -0.2201 -0.0360 1.2283 0.039 Uiso 1 1 calc R . .
C10 C -0.0715(5) 0.0587(3) 1.1715(3) 0.0319(10) Uani 1 1 d . . .
H10 H -0.1536 0.1016 1.1564 0.038 Uiso 1 1 calc R . .
C11 C 0.1951(5) 0.0151(4) 1.1728(3) 0.0361(11) Uani 1 1 d . . .
H11 H 0.3018 0.0277 1.1584 0.043 Uiso 1 1 calc R . .
C12 C 0.1644(6) -0.0684(4) 1.2153(3) 0.0410(11) Uani 1 1 d . . .
H12 H 0.2493 -0.1099 1.2294 0.049 Uiso 1 1 calc R . .
C13 C 0.433(2) 0.1023(9) 1.5181(5) 0.152(7) Uani 1 1 d . . .
H13A H 0.4503 0.0323 1.5176 0.228 Uiso 1 1 calc R . .
H13B H 0.3278 0.1163 1.5394 0.228 Uiso 1 1 calc R . .
H13C H 0.5151 0.1335 1.5485 0.228 Uiso 1 1 calc R . .
C14 C 0.4408(15) 0.1421(6) 1.4360(4) 0.095(3) Uani 1 1 d . . .
C15 C 0.4249(17) 0.2423(6) 1.4207(4) 0.119(4) Uani 1 1 d . . .
H15 H 0.4046 0.2852 1.4611 0.143 Uiso 1 1 calc R . .
C16 C 0.4380(12) 0.2799(5) 1.3483(4) 0.081(3) Uani 1 1 d . . .
H16 H 0.4251 0.3471 1.3396 0.097 Uiso 1 1 calc R . .
C17 C 0.4706(7) 0.2163(4) 1.2883(3) 0.0433(12) Uani 1 1 d . . .
C18 C 0.4830(9) 0.1158(4) 1.3024(3) 0.0568(16) Uani 1 1 d . . .
H18 H 0.5000 0.0726 1.2618 0.068 Uiso 1 1 calc R . .
C19 C 0.4709(13) 0.0798(6) 1.3737(4) 0.084(3) Uani 1 1 d . . .
H19 H 0.4827 0.0124 1.3819 0.101 Uiso 1 1 calc R . .
N1 N 0.0812(4) 0.0786(3) 1.1513(2) 0.0266(8) Uani 1 1 d . . .
N2 N 0.0941(4) 0.3342(3) 1.1400(2) 0.0251(7) Uani 1 1 d . . .
O1 O 0.2704(4) 0.1452(2) 0.99816(17) 0.0307(7) Uani 1 1 d . . .
O2 O 0.4389(4) 0.2683(2) 0.97028(18) 0.0310(7) Uani 1 1 d . . .
O3 O 0.3795(3) 0.2011(3) 1.14848(18) 0.0348(7) Uani 1 1 d . . .
O4 O 0.4352(4) 0.3644(3) 1.1976(2) 0.0413(8) Uani 1 1 d . . .
O5 O 0.6560(4) 0.2497(3) 1.1726(2) 0.0518(9) Uani 1 1 d . . .
S2 S 0.48882(12) 0.26291(8) 1.19410(6) 0.0303(2) Uani 1 1 d . . .
Zn1 Zn 0.15366(6) 0.20017(4) 1.08627(3) 0.02372(16) Uani 1 1 d . . .
H2C H 0.189(6) 0.372(4) 1.151(3) 0.028(12) Uiso 1 1 d . . .
H5 H 0.400(5) 0.086(4) 0.877(3) 0.037(15) Uiso 1 1 d D . .
H7 H -0.071(8) 0.306(5) 1.216(4) 0.055(18) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.75(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.456(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.349(13) . ?
C3 C5 1.592(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N2 1.484(6) 3_557 ?
C5 C6 1.534(6) . ?
C5 H5 0.95(2) . ?
C6 O2 1.250(6) . ?
C6 O1 1.253(5) . ?
C7 N2 1.482(5) . ?
C7 C8 1.516(6) 4_557 ?
C7 H7 0.85(7) . ?
C8 C9 1.374(6) . ?
C8 C12 1.394(7) . ?
C8 C7 1.516(6) 4_547 ?
C9 C10 1.403(6) . ?
C9 H9 0.9300 . ?
C10 N1 1.333(6) . ?
C10 H10 0.9300 . ?
C11 N1 1.328(6) . ?
C11 C12 1.377(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.534(10) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.390(12) . ?
C14 C19 1.399(11) . ?
C15 C16 1.368(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(8) . ?
C17 S2 1.769(5) . ?
C18 C19 1.342(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N1 Zn1 2.089(4) . ?
N2 C5 1.484(6) 3_457 ?
N2 Zn1 2.102(4) . ?
N2 H2C 0.95(5) . ?
O1 Zn1 1.962(3) . ?
O2 Zn1 2.070(3) 3_557 ?
O3 S2 1.465(3) . ?
O3 Zn1 2.154(3) . ?
O4 S2 1.446(4) . ?
O5 S2 1.438(4) . ?
Zn1 O2 2.070(3) 3_457 ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 106.7(10) . . ?
C3 C2 H2A 110.4 . . ?
C1 C2 H2A 110.4 . . ?
C3 C2 H2B 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C4 C3 C2 120.6(9) . . ?
C4 C3 C5 121.7(6) . . ?
C2 C3 C5 115.3(9) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 110.6(3) 3_557 . ?
N2 C5 C3 107.2(4) 3_557 . ?
C6 C5 C3 111.4(4) . . ?
N2 C5 H5 104(3) 3_557 . ?
C6 C5 H5 104(3) . . ?
C3 C5 H5 119(4) . . ?
O2 C6 O1 125.4(4) . . ?
O2 C6 C5 119.0(4) . . ?
O1 C6 C5 115.5(4) . . ?
N2 C7 C8 114.2(4) . 4_557 ?
N2 C7 H7 109(4) . . ?
C8 C7 H7 89(5) 4_557 . ?
C9 C8 C12 116.6(4) . . ?
C9 C8 C7 123.0(4) . 4_547 ?
C12 C8 C7 120.4(4) . 4_547 ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
N1 C10 C9 122.2(4) . . ?
N1 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
N1 C11 C12 123.8(4) . . ?
N1 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C11 C12 C8 119.7(4) . . ?
C11 C12 H12 120.2 . . ?
C8 C12 H12 120.2 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 117.2(6) . . ?
C15 C14 C13 121.2(8) . . ?
C19 C14 C13 121.5(8) . . ?
C16 C15 C14 122.3(7) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 119.0(7) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C18 119.4(5) . . ?
C16 C17 S2 119.9(5) . . ?
C18 C17 S2 120.7(4) . . ?
C19 C18 C17 121.1(6) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C14 121.1(7) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C11 N1 C10 117.4(4) . . ?
C11 N1 Zn1 117.7(3) . . ?
C10 N1 Zn1 125.0(3) . . ?
C7 N2 C5 114.5(4) . 3_457 ?
C7 N2 Zn1 110.7(3) . . ?
C5 N2 Zn1 108.3(3) 3_457 . ?
C7 N2 H2C 101(3) . . ?
C5 N2 H2C 111(3) 3_457 . ?
Zn1 N2 H2C 112(3) . . ?
C6 O1 Zn1 127.7(3) . . ?
C6 O2 Zn1 115.3(3) . 3_557 ?
S2 O3 Zn1 143.9(2) . . ?
O5 S2 O4 114.9(2) . . ?
O5 S2 O3 112.0(2) . . ?
O4 S2 O3 112.3(2) . . ?
O5 S2 C17 106.2(3) . . ?
O4 S2 C17 105.9(2) . . ?
O3 S2 C17 104.5(2) . . ?
O1 Zn1 O2 97.01(13) . 3_457 ?
O1 Zn1 N1 105.52(14) . . ?
O2 Zn1 N1 100.29(14) 3_457 . ?
O1 Zn1 N2 142.43(14) . . ?
O2 Zn1 N2 80.55(13) 3_457 . ?
N1 Zn1 N2 111.82(14) . . ?
O1 Zn1 O3 88.58(13) . . ?
O2 Zn1 O3 167.71(13) 3_457 . ?
N1 Zn1 O3 88.65(14) . . ?
N2 Zn1 O3 88.34(13) . . ?

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
C1 C2 C3 C4 94.6(17) . . . . ?
C1 C2 C3 C5 -68.0(11) . . . . ?
C4 C3 C5 N2 127.2(14) . . . 3_557 ?
C2 C3 C5 N2 -70.4(10) . . . 3_557 ?
C4 C3 C5 C6 6.1(16) . . . . ?
C2 C3 C5 C6 168.5(9) . . . . ?
N2 C5 C6 O2 -14.5(6) 3_557 . . . ?
C3 C5 C6 O2 104.6(6) . . . . ?
N2 C5 C6 O1 166.8(4) 3_557 . . . ?
C3 C5 C6 O1 -74.1(6) . . . . ?
C12 C8 C9 C10 0.6(7) . . . . ?
C7 C8 C9 C10 -178.1(4) 4_547 . . . ?
C8 C9 C10 N1 -0.8(8) . . . . ?
N1 C11 C12 C8 0.9(9) . . . . ?
C9 C8 C12 C11 -0.6(8) . . . . ?
C7 C8 C12 C11 178.1(5) 4_547 . . . ?
C19 C14 C15 C16 0(2) . . . . ?
C13 C14 C15 C16 177.4(13) . . . . ?
C14 C15 C16 C17 -1.0(19) . . . . ?
C15 C16 C17 C18 2.5(13) . . . . ?
C15 C16 C17 S2 -179.8(9) . . . . ?
C16 C17 C18 C19 -2.9(12) . . . . ?
S2 C17 C18 C19 179.4(7) . . . . ?
C17 C18 C19 C14 1.8(15) . . . . ?
C15 C14 C19 C18 -0.3(18) . . . . ?
C13 C14 C19 C18 -177.8(12) . . . . ?
C12 C11 N1 C10 -1.0(8) . . . . ?
C12 C11 N1 Zn1 -179.6(4) . . . . ?
C9 C10 N1 C11 1.0(7) . . . . ?
C9 C10 N1 Zn1 179.4(4) . . . . ?
C8 C7 N2 C5 -60.6(5) 4_557 . . 3_457 ?
C8 C7 N2 Zn1 176.6(3) 4_557 . . . ?
O2 C6 O1 Zn1 -13.7(6) . . . . ?
C5 C6 O1 Zn1 164.9(3) . . . . ?
O1 C6 O2 Zn1 173.8(3) . . . 3_557 ?
C5 C6 O2 Zn1 -4.8(5) . . . 3_557 ?
Zn1 O3 S2 O5 -135.7(3) . . . . ?
Zn1 O3 S2 O4 -4.6(4) . . . . ?
Zn1 O3 S2 C17 109.7(4) . . . . ?
C16 C17 S2 O5 112.7(6) . . . . ?
C18 C17 S2 O5 -69.6(6) . . . . ?
C16 C17 S2 O4 -9.9(7) . . . . ?
C18 C17 S2 O4 167.8(5) . . . . ?
C16 C17 S2 O3 -128.7(6) . . . . ?
C18 C17 S2 O3 49.0(6) . . . . ?
C6 O1 Zn1 O2 111.2(4) . . . 3_457 ?
C6 O1 Zn1 N1 -146.0(4) . . . . ?
C6 O1 Zn1 N2 27.6(5) . . . . ?
C6 O1 Zn1 O3 -57.8(4) . . . . ?
C11 N1 Zn1 O1 54.6(4) . . . . ?
C10 N1 Zn1 O1 -123.8(4) . . . . ?
C11 N1 Zn1 O2 154.9(4) . . . 3_457 ?
C10 N1 Zn1 O2 -23.5(4) . . . 3_457 ?
C11 N1 Zn1 N2 -121.2(4) . . . . ?
C10 N1 Zn1 N2 60.4(4) . . . . ?
C11 N1 Zn1 O3 -33.6(4) . . . . ?
C10 N1 Zn1 O3 148.0(4) . . . . ?
C7 N2 Zn1 O1 -166.2(3) . . . . ?
C5 N2 Zn1 O1 67.5(4) 3_457 . . . ?
C7 N2 Zn1 O2 104.6(3) . . . 3_457 ?
C5 N2 Zn1 O2 -21.7(3) 3_457 . . 3_457 ?
C7 N2 Zn1 N1 7.2(3) . . . . ?
C5 N2 Zn1 N1 -119.1(3) 3_457 . . . ?
C7 N2 Zn1 O3 -80.7(3) . . . . ?
C5 N2 Zn1 O3 153.0(3) 3_457 . . . ?
S2 O3 Zn1 O1 128.1(4) . . . . ?
S2 O3 Zn1 O2 10.6(9) . . . 3_457 ?
S2 O3 Zn1 N1 -126.4(4) . . . . ?
S2 O3 Zn1 N2 -14.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        67.98
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         1.170
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_ZAIL-Cl
_database_code_depnum_ccdc_archive 'CCDC 1528711'
_audit_update_record             
;
2017-01-20 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 Cl N2 O3 Zn'
_chemical_formula_sum            'C12 H17 Cl N2 O3 Zn'
_chemical_formula_weight         338.10

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.2031(2)
_cell_length_b                   13.9957(6)
_cell_length_c                   16.9125(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1468.29(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2306
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.859
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_T_max  0.716
_exptl_absorpt_process_details   Crysalispro
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Supernova (Mo) X-Ray source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3440
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.150
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.891
_reflns_number_total             2306
_reflns_number_gt                1965
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.523
_reflns_Friedel_fraction_max     0.742
_reflns_Friedel_fraction_full    0.742

_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-2016/4 (Sheldrick, 2016)'
_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)+(0.0190P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(17)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2306
_refine_ls_number_parameters     184
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0600
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.946
_refine_ls_shift/su_max          0.002
_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 0.6173(10) 0.5025(4) 0.4264(3) 0.0313(14) Uani 1 1 d . . . . .
C2 C 0.4027(9) 0.4553(4) 0.4491(3) 0.0266(13) Uani 1 1 d D . . . .
C3 C 0.3416(9) 0.3764(4) 0.3890(3) 0.0328(14) Uani 1 1 d D . . . .
C4 C 0.5370(10) 0.3207(4) 0.3613(4) 0.068(2) Uani 1 1 d . . . . .
H4A H 0.641039 0.363951 0.339262 0.102 Uiso 1 1 calc R U . . .
H4B H 0.599697 0.287482 0.405275 0.102 Uiso 1 1 calc R U . . .
H4C H 0.493941 0.275379 0.321686 0.102 Uiso 1 1 calc R U . . .
C5 C 0.1725(10) 0.3083(4) 0.4245(4) 0.0526(18) Uani 1 1 d . . . . .
H5A H 0.237911 0.272645 0.467435 0.063 Uiso 1 1 calc R U . . .
H5B H 0.055272 0.345772 0.446459 0.063 Uiso 1 1 calc R U . . .
C6 C 0.0809(11) 0.2379(5) 0.3637(4) 0.074(2) Uani 1 1 d . . . . .
H6A H -0.023353 0.197308 0.388855 0.110 Uiso 1 1 calc R U . . .
H6B H 0.012970 0.272751 0.321648 0.110 Uiso 1 1 calc R U . . .
H6C H 0.195637 0.199613 0.342627 0.110 Uiso 1 1 calc R U . . .
C7 C 0.2644(10) 0.5919(3) 0.5237(2) 0.0317(14) Uani 1 1 d . . . . .
H7A H 0.148623 0.638453 0.524183 0.038 Uiso 1 1 calc R U . . .
H7B H 0.399234 0.626666 0.519779 0.038 Uiso 1 1 calc R U . . .
C8 C 0.2617(10) 0.5383(3) 0.6008(3) 0.0269(13) Uani 1 1 d . . . . .
C9 C 0.0806(10) 0.4868(4) 0.6239(3) 0.0323(15) Uani 1 1 d . . . . .
H9 H -0.038421 0.482700 0.590662 0.039 Uiso 1 1 calc R U . . .
C10 C 0.0789(9) 0.4419(4) 0.6966(3) 0.0329(14) Uani 1 1 d . . . . .
H10 H -0.045544 0.410006 0.712317 0.039 Uiso 1 1 calc R U . . .
C11 C 0.4221(9) 0.4907(4) 0.7227(3) 0.0311(14) Uani 1 1 d . . . . .
H11 H 0.541463 0.491615 0.755930 0.037 Uiso 1 1 calc R U . . .
C12 C 0.4329(8) 0.5398(4) 0.6517(3) 0.0311(13) Uani 1 1 d . . . . .
H12 H 0.556695 0.573808 0.638681 0.037 Uiso 1 1 calc R U . . .
N1 N 0.2406(8) 0.5312(3) 0.4525(2) 0.0242(10) Uani 1 1 d D . . . .
N2 N 0.2484(8) 0.4422(3) 0.7452(2) 0.0261(11) Uani 1 1 d . . . . .
O1 O 0.7840(7) 0.4771(3) 0.4599(2) 0.0459(10) Uani 1 1 d . . . . .
O2 O 0.6050(6) 0.5642(3) 0.3709(2) 0.0369(10) Uani 1 1 d . . . . .
O3 O 0.5482(6) 0.3342(3) 0.8588(3) 0.0480(11) Uani 1 1 d . . . . .
ZN1 Zn 0.21671(10) 0.37919(4) 0.85461(3) 0.02744(17) Uani 1 1 d . . . . .
CL1 Cl 0.1063(3) 0.22798(10) 0.85807(10) 0.0583(5) Uani 1 1 d . . . . .
H1 H 0.107(5) 0.506(3) 0.454(3) 0.019(15) Uiso 1 1 d D . . . .
H2 H 0.418(7) 0.428(3) 0.4948(15) 0.008(12) Uiso 1 1 d D . . . .
H3 H 0.287(7) 0.407(3) 0.3503(19) 0.026(14) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.232(6) . ?
C1 O2 1.278(6) . ?
C1 C2 1.534(8) . ?
C2 N1 1.463(7) . ?
C2 C3 1.548(7) . ?
C2 H2 0.87(2) . ?
C3 C4 1.516(8) . ?
C3 C5 1.539(8) . ?
C3 H3 0.85(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.533(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N1 1.481(6) . ?
C7 C8 1.504(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C12 1.368(7) . ?
C8 C9 1.391(7) . ?
C9 C10 1.381(7) . ?
C9 H9 0.9300 . ?
C10 N2 1.335(6) . ?
C10 H10 0.9300 . ?
C11 N2 1.329(7) . ?
C11 C12 1.384(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 ZN1 2.094(4) 2_564 ?
N1 H1 0.90(2) . ?
N2 ZN1 2.059(4) . ?
O2 ZN1 2.165(4) 2_564 ?
O3 ZN1 2.152(4) . ?
ZN1 N1 2.094(4) 2_565 ?
ZN1 O2 2.165(4) 2_565 ?
ZN1 CL1 2.2251(16) . ?

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 125.7(5) . . ?
O1 C1 C2 119.3(5) . . ?
O2 C1 C2 115.0(5) . . ?
N1 C2 C1 107.1(4) . . ?
N1 C2 C3 112.0(4) . . ?
C1 C2 C3 110.8(4) . . ?
N1 C2 H2 111(3) . . ?
C1 C2 H2 109(3) . . ?
C3 C2 H2 107(3) . . ?
C4 C3 C5 110.3(5) . . ?
C4 C3 C2 112.0(5) . . ?
C5 C3 C2 110.6(4) . . ?
C4 C3 H3 110(3) . . ?
C5 C3 H3 110(3) . . ?
C2 C3 H3 104(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 112.9(5) . . ?
C6 C5 H5A 109.0 . . ?
C3 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C3 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 114.7(4) . . ?
N1 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C12 C8 C9 117.2(4) . . ?
C12 C8 C7 122.0(5) . . ?
C9 C8 C7 120.7(5) . . ?
C10 C9 C8 119.5(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
N2 C10 C9 122.7(5) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
N2 C11 C12 122.8(5) . . ?
N2 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C8 C12 C11 120.1(5) . . ?
C8 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C2 N1 C7 112.3(4) . . ?
C2 N1 ZN1 108.5(3) . 2_564 ?
C7 N1 ZN1 106.6(3) . 2_564 ?
C2 N1 H1 111(3) . . ?
C7 N1 H1 107(3) . . ?
ZN1 N1 H1 112(3) 2_564 . ?
C11 N2 C10 117.6(4) . . ?
C11 N2 ZN1 123.6(4) . . ?
C10 N2 ZN1 118.5(4) . . ?
C1 O2 ZN1 113.3(4) . 2_564 ?
N2 ZN1 N1 116.19(16) . 2_565 ?
N2 ZN1 O3 93.66(17) . . ?
N1 ZN1 O3 91.62(17) 2_565 . ?
N2 ZN1 O2 92.62(16) . 2_565 ?
N1 ZN1 O2 78.27(16) 2_565 2_565 ?
O3 ZN1 O2 169.69(15) . 2_565 ?
N2 ZN1 CL1 117.43(12) . . ?
N1 ZN1 CL1 126.02(12) 2_565 . ?
O3 ZN1 CL1 90.87(11) . . ?
O2 ZN1 CL1 93.48(11) 2_565 . ?

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
O1 C1 C2 N1 138.5(5) . . . . ?
O2 C1 C2 N1 -43.6(6) . . . . ?
O1 C1 C2 C3 -99.0(6) . . . . ?
O2 C1 C2 C3 78.8(6) . . . . ?
N1 C2 C3 C4 157.6(5) . . . . ?
C1 C2 C3 C4 38.0(7) . . . . ?
N1 C2 C3 C5 -78.9(6) . . . . ?
C1 C2 C3 C5 161.5(5) . . . . ?
C4 C3 C5 C6 -64.1(7) . . . . ?
C2 C3 C5 C6 171.4(5) . . . . ?
N1 C7 C8 C12 119.3(5) . . . . ?
N1 C7 C8 C9 -62.3(7) . . . . ?
C12 C8 C9 C10 1.4(8) . . . . ?
C7 C8 C9 C10 -177.1(4) . . . . ?
C8 C9 C10 N2 -2.8(8) . . . . ?
C9 C8 C12 C11 0.5(8) . . . . ?
C7 C8 C12 C11 179.0(5) . . . . ?
N2 C11 C12 C8 -1.2(8) . . . . ?
C1 C2 N1 C7 -74.2(5) . . . . ?
C3 C2 N1 C7 164.2(4) . . . . ?
C1 C2 N1 ZN1 43.4(4) . . . 2_564 ?
C3 C2 N1 ZN1 -78.2(4) . . . 2_564 ?
C8 C7 N1 C2 -55.3(6) . . . . ?
C8 C7 N1 ZN1 -174.0(4) . . . 2_564 ?
C12 C11 N2 C10 0.0(8) . . . . ?
C12 C11 N2 ZN1 -174.0(4) . . . . ?
C9 C10 N2 C11 2.0(8) . . . . ?
C9 C10 N2 ZN1 176.4(4) . . . . ?
O1 C1 O2 ZN1 -161.5(5) . . . 2_564 ?
C2 C1 O2 ZN1 20.8(5) . . . 2_564 ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.061

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

data_ZAIL-OAc
_database_code_depnum_ccdc_archive 'CCDC 1528714'
_audit_update_record             
;
2017-01-20 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N2 O5 Zn, O'
_chemical_formula_sum            'C14 H22 N2 O6 Zn'
_chemical_formula_weight         379.70

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.166(5)
_cell_length_b                   15.763(5)
_cell_length_c                   17.831(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1733.1(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2861
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.447
_shelx_estimated_absorpt_T_min   0.705
_shelx_estimated_absorpt_T_max   0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_process_details   Crysalispro
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Supernova X-Ray (Mo) source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4137
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.450
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             2861
_reflns_number_gt                2669
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_max     0.851
_reflns_Friedel_fraction_full    0.851

_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-2016/4 (Sheldrick, 2016)'
_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)+(0.1225P)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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2861
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1715
_refine_ls_wR_factor_gt          0.1667
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
C1 C -0.0768(12) -0.0391(4) 0.1025(4) 0.0330(15) Uani 1 1 d . . . . .
C2 C 0.1360(11) -0.0773(4) 0.0777(4) 0.0281(14) Uani 1 1 d . . . . .
H2 H 0.126373 -0.091905 0.024414 0.034 Uiso 1 1 calc R U . . .
C3 C 0.1917(12) -0.1579(4) 0.1227(4) 0.0353(16) Uani 1 1 d . . . . .
H3 H 0.247247 -0.140584 0.171881 0.042 Uiso 1 1 calc R U . . .
C4 C -0.0111(16) -0.2113(6) 0.1349(6) 0.059(2) Uani 1 1 d . . . . .
H4A H -0.125912 -0.175878 0.153370 0.088 Uiso 1 1 calc R U . . .
H4B H 0.019197 -0.255127 0.170795 0.088 Uiso 1 1 calc R U . . .
H4C H -0.054288 -0.236537 0.088249 0.088 Uiso 1 1 calc R U . . .
C5 C 0.3673(15) -0.2076(5) 0.0829(5) 0.053(2) Uani 1 1 d . . . . .
H5A H 0.491265 -0.170656 0.075322 0.063 Uiso 1 1 calc R U . . .
H5B H 0.314033 -0.224123 0.033895 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4434(19) -0.2875(6) 0.1247(6) 0.071(3) Uani 1 1 d . . . . .
H6A H 0.563807 -0.312283 0.098527 0.106 Uiso 1 1 calc R U . . .
H6B H 0.326574 -0.327733 0.127044 0.106 Uiso 1 1 calc R U . . .
H6C H 0.487181 -0.272558 0.174647 0.106 Uiso 1 1 calc R U . . .
C7 C 0.3018(13) 0.0552(4) 0.0308(3) 0.0351(16) Uani 1 1 d . . . . .
H7A H 0.429182 0.090545 0.037400 0.042 Uiso 1 1 calc R U . . .
H7B H 0.175731 0.090433 0.040330 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2940(12) 0.0262(4) -0.0506(3) 0.0315(15) Uani 1 1 d . . . . .
C9 C 0.1174(14) 0.0486(5) -0.0944(4) 0.0456(19) Uani 1 1 d . . . . .
H9 H 0.002818 0.078966 -0.073718 0.055 Uiso 1 1 calc R U . . .
C10 C 0.1135(13) 0.0256(7) -0.1679(4) 0.051(2) Uani 1 1 d . . . . .
H10 H -0.007547 0.039901 -0.196300 0.061 Uiso 1 1 calc R U . . .
C11 C 0.4434(12) -0.0378(5) -0.1589(4) 0.0347(15) Uani 1 1 d . . . . .
H11 H 0.556408 -0.067728 -0.181069 0.042 Uiso 1 1 calc R U . . .
C12 C 0.4578(13) -0.0180(5) -0.0849(4) 0.0365(16) Uani 1 1 d . . . . .
H12 H 0.579017 -0.034365 -0.057464 0.044 Uiso 1 1 calc R U . . .
C13 C 0.236(2) 0.2363(5) 0.1736(5) 0.060(2) Uani 1 1 d . . . . .
C14 C 0.093(2) 0.3147(6) 0.1673(7) 0.089(4) Uani 1 1 d . . . . .
H14A H -0.056046 0.297501 0.162070 0.134 Uiso 1 1 calc R U . . .
H14B H 0.135085 0.347150 0.124190 0.134 Uiso 1 1 calc R U . . .
H14C H 0.108252 0.348692 0.211607 0.134 Uiso 1 1 calc R U . . .
N1 N 0.3075(10) -0.0133(3) 0.0880(3) 0.0281(13) Uani 1 1 d . . . . .
H1 H 0.450721 -0.040191 0.089349 0.034 Uiso 1 1 calc R U . . .
N3 N 0.2732(10) -0.0159(4) -0.2009(3) 0.0333(13) Uani 1 1 d . . . . .
O1 O -0.2405(8) -0.0534(3) 0.0671(3) 0.0481(13) Uani 1 1 d . . . . .
O2 O -0.0682(8) 0.0068(3) 0.1625(3) 0.0415(12) Uani 1 1 d . . . . .
O3 O 0.5698(8) 0.0883(3) 0.2043(3) 0.0421(12) Uani 1 1 d . . . . .
H3A H 0.666599 0.054503 0.178893 0.063 Uiso 1 1 d R U . . .
H3B H 0.597083 0.142576 0.188083 0.063 Uiso 1 1 d R U . . .
O4 O 0.1348(10) 0.1687(3) 0.1820(3) 0.0519(15) Uani 1 1 d . . . . .
O5 O 0.4367(14) 0.2438(5) 0.1708(5) 0.087(2) Uani 1 1 d . . . . .
O6 O 0.621(5) 0.2404(14) 0.0246(8) 0.37(2) Uani 1 1 d . . . . .
ZN01 Zn 0.24546(12) 0.05219(4) 0.18885(3) 0.0295(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.212(9) . ?
C1 O2 1.293(8) . ?
C1 C2 1.510(10) . ?
C2 N1 1.473(9) . ?
C2 C3 1.542(9) . ?
C2 H2 0.9800 . ?
C3 C5 1.513(11) . ?
C3 C4 1.522(11) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.538(11) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N1 1.486(8) . ?
C7 C8 1.522(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C12 1.370(11) . ?
C8 C9 1.385(10) . ?
C9 C10 1.360(10) . ?
C9 H9 0.9300 . ?
C10 N3 1.321(10) . ?
C10 H10 0.9300 . ?
C11 N3 1.335(9) . ?
C11 C12 1.359(10) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O5 1.244(15) . ?
C13 O4 1.244(12) . ?
C13 C14 1.523(13) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 ZN01 2.109(5) . ?
N1 H1 0.9800 . ?
N3 ZN01 2.050(5) 2_554 ?
O2 ZN01 2.115(6) . ?
O3 ZN01 2.097(5) . ?
O3 H3A 0.9193 . ?
O3 H3B 0.9180 . ?
O4 ZN01 1.963(5) . ?
ZN01 N3 2.050(5) 2 ?

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 124.8(7) . . ?
O1 C1 C2 119.8(6) . . ?
O2 C1 C2 115.4(6) . . ?
N1 C2 C1 108.3(5) . . ?
N1 C2 C3 109.9(5) . . ?
C1 C2 C3 111.7(5) . . ?
N1 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C5 C3 C4 111.6(6) . . ?
C5 C3 C2 110.0(6) . . ?
C4 C3 C2 110.3(6) . . ?
C5 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 114.5(7) . . ?
C3 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
C3 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 115.8(5) . . ?
N1 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C12 C8 C9 117.2(6) . . ?
C12 C8 C7 123.7(7) . . ?
C9 C8 C7 119.0(6) . . ?
C10 C9 C8 119.3(7) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N3 C10 C9 123.3(7) . . ?
N3 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
N3 C11 C12 122.5(7) . . ?
N3 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C8 120.1(7) . . ?
C11 C12 H12 119.9 . . ?
C8 C12 H12 119.9 . . ?
O5 C13 O4 125.8(9) . . ?
O5 C13 C14 119.9(10) . . ?
O4 C13 C14 114.3(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 N1 C7 113.3(5) . . ?
C2 N1 ZN01 108.1(4) . . ?
C7 N1 ZN01 103.0(4) . . ?
C2 N1 H1 110.7 . . ?
C7 N1 H1 110.7 . . ?
ZN01 N1 H1 110.7 . . ?
C10 N3 C11 117.6(6) . . ?
C10 N3 ZN01 121.6(5) . 2_554 ?
C11 N3 ZN01 120.7(5) . 2_554 ?
C1 O2 ZN01 114.2(5) . . ?
ZN01 O3 H3A 113.4 . . ?
ZN01 O3 H3B 112.7 . . ?
H3A O3 H3B 105.5 . . ?
C13 O4 ZN01 129.4(7) . . ?
O4 ZN01 N3 107.5(2) . 2 ?
O4 ZN01 O3 94.9(2) . . ?
N3 ZN01 O3 90.2(2) 2 . ?
O4 ZN01 N1 117.9(2) . . ?
N3 ZN01 N1 133.7(2) 2 . ?
O3 ZN01 N1 94.1(2) . . ?
O4 ZN01 O2 89.1(2) . . ?
N3 ZN01 O2 93.8(2) 2 . ?
O3 ZN01 O2 173.16(17) . . ?
N1 ZN01 O2 79.1(2) . . ?

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
O1 C1 C2 N1 140.3(6) . . . . ?
O2 C1 C2 N1 -40.7(7) . . . . ?
O1 C1 C2 C3 -98.5(7) . . . . ?
O2 C1 C2 C3 80.5(7) . . . . ?
N1 C2 C3 C5 -75.7(7) . . . . ?
C1 C2 C3 C5 164.0(6) . . . . ?
N1 C2 C3 C4 160.7(6) . . . . ?
C1 C2 C3 C4 40.4(8) . . . . ?
C4 C3 C5 C6 -59.8(10) . . . . ?
C2 C3 C5 C6 177.4(8) . . . . ?
N1 C7 C8 C12 -64.5(9) . . . . ?
N1 C7 C8 C9 118.8(7) . . . . ?
C12 C8 C9 C10 0.6(12) . . . . ?
C7 C8 C9 C10 177.4(8) . . . . ?
C8 C9 C10 N3 -1.5(15) . . . . ?
N3 C11 C12 C8 0.0(11) . . . . ?
C9 C8 C12 C11 0.2(11) . . . . ?
C7 C8 C12 C11 -176.5(6) . . . . ?
C1 C2 N1 C7 -74.4(6) . . . . ?
C3 C2 N1 C7 163.3(5) . . . . ?
C1 C2 N1 ZN01 39.1(5) . . . . ?
C3 C2 N1 ZN01 -83.2(6) . . . . ?
C8 C7 N1 C2 -51.1(8) . . . . ?
C8 C7 N1 ZN01 -167.6(5) . . . . ?
C9 C10 N3 C11 1.6(14) . . . . ?
C9 C10 N3 ZN01 178.0(8) . . . 2_554 ?
C12 C11 N3 C10 -0.8(12) . . . . ?
C12 C11 N3 ZN01 -177.3(6) . . . 2_554 ?
O1 C1 O2 ZN01 -160.5(6) . . . . ?
C2 C1 O2 ZN01 20.5(7) . . . . ?
O5 C13 O4 ZN01 -3.1(15) . . . . ?
C14 C13 O4 ZN01 177.4(7) . . . . ?

_refine_diff_density_max         0.612
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.117

####################################################################### 
# 
# 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_ZAIL-N3
_database_code_depnum_ccdc_archive 'CCDC 1528712'
_audit_update_record             
;
2017-01-20 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 N5 O2 Zn'
_chemical_formula_sum            'C12 H17 N5 O2 Zn'
_chemical_formula_weight         328.68

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'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   'P 61'
_symmetry_space_group_name_Hall  'P 61'
_chemical_absolute_configuration .

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'

_cell_length_a                   17.764(3)
_cell_length_b                   17.764(3)
_cell_length_c                   10.4098(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2844.7(7)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2732
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1020
_exptl_absorpt_coefficient_mu    1.302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7283
_exptl_absorpt_correction_T_max  0.7900
_exptl_absorpt_process_details   Crysalispro'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Supernova (Mo) X-Ray source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7358
_diffrn_reflns_av_R_equivalents  0.1607
_diffrn_reflns_av_sigmaI/netI    0.1708
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2732
_reflns_number_gt                1783
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1184P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(5)
_refine_ls_number_reflns         2732
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0864
_refine_ls_wR_factor_ref         0.2485
_refine_ls_wR_factor_gt          0.2175
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4699(8) -0.0558(7) -0.0593(10) 0.029(3) Uani 1 1 d . . .
C2 C 0.4538(8) -0.1100(8) 0.0590(11) 0.038(3) Uani 1 1 d . . .
H2 H 0.4724 -0.1520 0.0383 0.045 Uiso 1 1 calc R . .
C3 C 0.3580(9) -0.1634(9) 0.0973(11) 0.048(4) Uani 1 1 d . . .
H3 H 0.3275 -0.1914 0.0175 0.058 Uiso 1 1 calc R . .
C4 C 0.3184(11) -0.1096(11) 0.1395(17) 0.070(4) Uani 1 1 d . . .
H4A H 0.3580 -0.0663 0.1999 0.085 Uiso 1 1 calc R . .
H4B H 0.2652 -0.1474 0.1857 0.085 Uiso 1 1 calc R . .
C5 C 0.2972(13) -0.0633(14) 0.0364(19) 0.092(6) Uani 1 1 d . . .
H5A H 0.2697 -0.1020 -0.0347 0.138 Uiso 1 1 calc R . .
H5B H 0.3498 -0.0133 0.0076 0.138 Uiso 1 1 calc R . .
H5C H 0.2586 -0.0452 0.0706 0.138 Uiso 1 1 calc R . .
C6 C 0.3385(10) -0.2391(10) 0.1886(13) 0.071(5) Uani 1 1 d . . .
H6A H 0.3701 -0.2670 0.1611 0.106 Uiso 1 1 calc R . .
H6B H 0.2773 -0.2803 0.1875 0.106 Uiso 1 1 calc R . .
H6C H 0.3559 -0.2172 0.2742 0.106 Uiso 1 1 calc R . .
C7 C 0.5894(8) -0.0620(7) 0.1846(12) 0.035(3) Uani 1 1 d . . .
H7A H 0.6245 -0.0217 0.2515 0.042 Uiso 1 1 calc R . .
H7B H 0.6227 -0.0439 0.1055 0.042 Uiso 1 1 calc R . .
C8 C 0.7257(9) 0.2147(8) 0.1924(11) 0.052(4) Uani 1 1 d . . .
H8 H 0.7011 0.2170 0.2700 0.063 Uiso 1 1 calc R . .
C9 C 0.8120(9) 0.2745(9) 0.1706(13) 0.054(4) Uani 1 1 d . . .
H9 H 0.8451 0.3131 0.2352 0.065 Uiso 1 1 calc R . .
C10 C 0.8496(9) 0.2773(8) 0.0521(12) 0.046(3) Uani 1 1 d . . .
C11 C 0.7970(8) 0.2107(7) -0.0310(14) 0.047(3) Uani 1 1 d . . .
H11 H 0.8189 0.2072 -0.1105 0.057 Uiso 1 1 calc R . .
C12 C 0.7153(9) 0.1512(8) 0.0003(12) 0.050(4) Uani 1 1 d . . .
H12 H 0.6843 0.1054 -0.0565 0.060 Uiso 1 1 calc R . .
N1 N 0.5096(6) -0.0569(5) 0.1677(9) 0.030(2) Uani 1 1 d . . .
H1 H 0.4779 -0.0758 0.2413 0.037 Uiso 1 1 calc R . .
N2 N 0.6758(6) 0.1534(6) 0.1072(8) 0.036(2) Uani 1 1 d . . .
N3 N 0.4717(10) 0.1255(9) 0.1384(14) 0.071(4) Uani 1 1 d . . .
N4 N 0.4239(11) 0.1106(9) 0.2374(15) 0.069(4) Uani 1 1 d . . .
N5 N 0.3755(14) 0.0926(13) 0.3215(19) 0.119(8) Uani 1 1 d . . .
O1 O 0.5173(5) 0.0275(5) -0.0515(8) 0.0349(19) Uani 1 1 d . . .
O2 O 0.5679(6) 0.0953(6) 0.3403(9) 0.044(2) Uani 1 1 d . . .
Zn1 Zn 0.54720(9) 0.07359(7) 0.14199(16) 0.0332(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 1.250(14) 4_654 ?
C1 O1 1.289(13) . ?
C1 C2 1.500(16) . ?
C2 N1 1.488(14) . ?
C2 C3 1.531(17) . ?
C3 C4 1.51(2) . ?
C3 C6 1.538(18) . ?
C4 C5 1.51(2) . ?
C7 N1 1.477(14) . ?
C7 C10 1.485(16) 2_545 ?
C8 N2 1.339(15) . ?
C8 C9 1.379(19) . ?
C9 C10 1.392(19) . ?
C10 C11 1.384(18) . ?
C10 C7 1.485(17) 6_664 ?
C11 C12 1.340(17) . ?
C12 N2 1.326(15) . ?
N1 Zn1 2.083(8) . ?
N2 Zn1 2.030(9) . ?
N3 N4 1.28(2) . ?
N3 Zn1 1.972(12) . ?
N4 N5 1.16(2) . ?
O1 Zn1 2.139(8) . ?
O2 C1 1.250(14) 4_655 ?
O2 Zn1 2.098(9) . ?

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
O2 C1 O1 123.8(10) 4_654 . ?
O2 C1 C2 116.7(10) 4_654 . ?
O1 C1 C2 119.4(10) . . ?
N1 C2 C1 111.4(10) . . ?
N1 C2 C3 112.1(11) . . ?
C1 C2 C3 114.0(11) . . ?
C4 C3 C2 114.2(12) . . ?
C4 C3 C6 113.7(12) . . ?
C2 C3 C6 113.4(12) . . ?
C3 C4 C5 117.4(15) . . ?
N1 C7 C10 113.5(10) . 2_545 ?
N2 C8 C9 123.2(12) . . ?
C8 C9 C10 120.1(13) . . ?
C11 C10 C9 114.6(12) . . ?
C11 C10 C7 123.6(12) . 6_664 ?
C9 C10 C7 121.8(12) . 6_664 ?
C12 C11 C10 121.7(13) . . ?
N2 C12 C11 124.1(12) . . ?
C7 N1 C2 114.0(9) . . ?
C7 N1 Zn1 107.5(6) . . ?
C2 N1 Zn1 110.5(7) . . ?
C12 N2 C8 115.8(10) . . ?
C12 N2 Zn1 123.8(8) . . ?
C8 N2 Zn1 120.4(8) . . ?
N4 N3 Zn1 115.1(11) . . ?
N5 N4 N3 175(2) . . ?
C1 O1 Zn1 113.2(7) . . ?
C1 O2 Zn1 136.3(8) 4_655 . ?
N3 Zn1 N2 117.5(5) . . ?
N3 Zn1 N1 127.4(5) . . ?
N2 Zn1 N1 115.0(4) . . ?
N3 Zn1 O2 91.7(5) . . ?
N2 Zn1 O2 90.8(4) . . ?
N1 Zn1 O2 90.5(3) . . ?
N3 Zn1 O1 93.7(5) . . ?
N2 Zn1 O1 94.4(3) . . ?
N1 Zn1 O1 79.3(3) . . ?
O2 Zn1 O1 169.8(3) . . ?

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
O2 C1 C2 N1 173.8(10) 4_654 . . . ?
O1 C1 C2 N1 -9.4(16) . . . . ?
O2 C1 C2 C3 -58.1(15) 4_654 . . . ?
O1 C1 C2 C3 118.6(13) . . . . ?
N1 C2 C3 C4 61.4(16) . . . . ?
C1 C2 C3 C4 -66.3(15) . . . . ?
N1 C2 C3 C6 -71.0(15) . . . . ?
C1 C2 C3 C6 161.3(11) . . . . ?
C2 C3 C4 C5 75.1(18) . . . . ?
C6 C3 C4 C5 -152.7(15) . . . . ?
N2 C8 C9 C10 5(2) . . . . ?
C8 C9 C10 C11 -7(2) . . . . ?
C8 C9 C10 C7 170.8(14) . . . 6_664 ?
C9 C10 C11 C12 3(2) . . . . ?
C7 C10 C11 C12 -175.0(14) 6_664 . . . ?
C10 C11 C12 N2 5(2) . . . . ?
C10 C7 N1 C2 -63.8(14) 2_545 . . . ?
C10 C7 N1 Zn1 173.4(8) 2_545 . . . ?
C1 C2 N1 C7 -97.4(12) . . . . ?
C3 C2 N1 C7 133.6(11) . . . . ?
C1 C2 N1 Zn1 23.7(12) . . . . ?
C3 C2 N1 Zn1 -105.4(10) . . . . ?
C11 C12 N2 C8 -7(2) . . . . ?
C11 C12 N2 Zn1 170.7(12) . . . . ?
C9 C8 N2 C12 2(2) . . . . ?
C9 C8 N2 Zn1 -175.5(12) . . . . ?
Zn1 N3 N4 N5 -104(20) . . . . ?
O2 C1 O1 Zn1 166.8(9) 4_654 . . . ?
C2 C1 O1 Zn1 -9.7(13) . . . . ?
N4 N3 Zn1 N2 -127.8(12) . . . . ?
N4 N3 Zn1 N1 55.9(14) . . . . ?
N4 N3 Zn1 O2 -36.0(13) . . . . ?
N4 N3 Zn1 O1 135.3(12) . . . . ?
C12 N2 Zn1 N3 -108.6(12) . . . . ?
C8 N2 Zn1 N3 69.2(11) . . . . ?
C12 N2 Zn1 N1 68.1(11) . . . . ?
C8 N2 Zn1 N1 -114.1(10) . . . . ?
C12 N2 Zn1 O2 159.0(11) . . . . ?
C8 N2 Zn1 O2 -23.2(11) . . . . ?
C12 N2 Zn1 O1 -12.1(11) . . . . ?
C8 N2 Zn1 O1 165.6(10) . . . . ?
C7 N1 Zn1 N3 -170.8(8) . . . . ?
C2 N1 Zn1 N3 64.3(10) . . . . ?
C7 N1 Zn1 N2 12.8(8) . . . . ?
C2 N1 Zn1 N2 -112.0(8) . . . . ?
C7 N1 Zn1 O2 -78.3(8) . . . . ?
C2 N1 Zn1 O2 156.8(8) . . . . ?
C7 N1 Zn1 O1 102.7(8) . . . . ?
C2 N1 Zn1 O1 -22.2(8) . . . . ?
C1 O2 Zn1 N3 86.5(12) 4_655 . . . ?
C1 O2 Zn1 N2 -156.0(12) 4_655 . . . ?
C1 O2 Zn1 N1 -41.0(12) 4_655 . . . ?
C1 O2 Zn1 O1 -35(3) 4_655 . . . ?
C1 O1 Zn1 N3 -109.3(8) . . . . ?
C1 O1 Zn1 N2 132.7(8) . . . . ?
C1 O1 Zn1 N1 18.1(8) . . . . ?
C1 O1 Zn1 O2 12(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.126
####################################################################### 
# 
# 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_ZAIL-Br
_database_code_depnum_ccdc_archive 'CCDC 1528710'
_audit_update_record             
;
2017-01-20 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H19 Br N2 O3 Zn'
_chemical_formula_sum            'C12 H19 Br N2 O3 Zn'
_chemical_formula_weight         384.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.2078(6)
_cell_length_b                   14.2553(11)
_cell_length_c                   17.0701(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1510.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2238
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      25.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    4.276
_shelx_estimated_absorpt_T_min   0.427
_shelx_estimated_absorpt_T_max   0.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.373
_exptl_absorpt_correction_T_max  0.463
_exptl_absorpt_process_details   Crysalispro
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Supernova (Mo) X-Ray source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3427
_diffrn_reflns_av_unetI/netI     0.1936
_diffrn_reflns_av_R_equivalents  0.1499
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.097
_diffrn_reflns_theta_max         24.981
_diffrn_reflns_theta_full        24.981
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.838
_reflns_number_total             2238
_reflns_number_gt                1117
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.450
_reflns_Friedel_fraction_max     0.630
_reflns_Friedel_fraction_full    0.629

_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-2016/4 (Sheldrick, 2016)'
_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)+(0.1176P)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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.14(6)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2238
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1519
_refine_ls_R_factor_gt           0.0997
_refine_ls_wR_factor_ref         0.2708
_refine_ls_wR_factor_gt          0.2160
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.002
_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 0.111(3) -0.5048(14) -0.5778(11) 0.040(5) Uani 1 1 d . . . . .
C2 C -0.101(3) -0.5530(13) -0.5503(11) 0.037(4) Uani 1 1 d . . . . .
H2 H -0.083292 -0.579362 -0.497678 0.044 Uiso 1 1 calc R U . . .
C3 C -0.159(3) -0.6307(13) -0.6089(13) 0.044(5) Uani 1 1 d . . . . .
H3 H -0.214377 -0.598202 -0.655295 0.052 Uiso 1 1 calc R U . . .
C4 C 0.043(4) -0.684(2) -0.6372(18) 0.089(9) Uani 1 1 d . . . . .
H4A H 0.169537 -0.654607 -0.616418 0.133 Uiso 1 1 calc R U . . .
H4B H 0.048174 -0.683043 -0.693375 0.133 Uiso 1 1 calc R U . . .
H4C H 0.036002 -0.747881 -0.619330 0.133 Uiso 1 1 calc R U . . .
C5 C -0.339(4) -0.6918(16) -0.581(2) 0.082(10) Uani 1 1 d . . . . .
H5A H -0.293237 -0.722074 -0.532981 0.099 Uiso 1 1 calc R U . . .
H5B H -0.460185 -0.651799 -0.568298 0.099 Uiso 1 1 calc R U . . .
C6 C -0.415(4) -0.766(2) -0.6361(18) 0.097(10) Uani 1 1 d . . . . .
H6A H -0.512088 -0.738730 -0.673637 0.146 Uiso 1 1 calc R U . . .
H6B H -0.489123 -0.813933 -0.607152 0.146 Uiso 1 1 calc R U . . .
H6C H -0.294283 -0.792870 -0.662865 0.146 Uiso 1 1 calc R U . . .
C7 C -0.240(3) -0.4154(14) -0.4793(11) 0.042(4) Uani 1 1 d . . . . .
H7A H -0.102108 -0.383747 -0.484066 0.050 Uiso 1 1 calc R U . . .
H7B H -0.350616 -0.367389 -0.480461 0.050 Uiso 1 1 calc R U . . .
C8 C -0.247(3) -0.4606(15) -0.4021(10) 0.045(5) Uani 1 1 d . . . . .
C9 C -0.076(3) -0.4600(14) -0.3544(12) 0.043(5) Uani 1 1 d . . . . .
H9 H 0.050208 -0.431058 -0.371189 0.052 Uiso 1 1 calc R U . . .
C10 C -0.420(3) -0.4994(17) -0.7814(14) 0.054(6) Uani 1 1 d . . . . .
H10 H -0.537401 -0.505972 -0.748126 0.064 Uiso 1 1 calc R U . . .
C11 C -0.080(4) -0.4472(16) -0.8041(10) 0.046(5) Uani 1 1 d . . . . .
H11 H 0.045225 -0.418716 -0.786190 0.055 Uiso 1 1 calc R U . . .
C12 C -0.078(3) -0.4827(17) -0.8763(12) 0.051(5) Uani 1 1 d . . . . .
H12 H 0.037380 -0.470493 -0.909657 0.061 Uiso 1 1 calc R U . . .
N1 N -0.269(2) -0.4759(11) -0.5494(8) 0.038(4) Uani 1 1 d . . . . .
H1 H -0.414017 -0.502582 -0.550400 0.046 Uiso 1 1 calc R U . . .
N2 N -0.243(3) -0.4491(11) -0.7570(9) 0.045(4) Uani 1 1 d . . . . .
O1 O 0.102(2) -0.4464(11) -0.6307(8) 0.055(4) Uani 1 1 d . . . . .
O2 O 0.276(2) -0.5263(11) -0.5383(8) 0.052(4) Uani 1 1 d . . . . .
O3 O -0.550(2) -0.3482(10) -0.6437(11) 0.059(4) Uani 1 1 d . . . . .
H3A H -0.628803 -0.380650 -0.676842 0.088 Uiso 1 1 d R U . . .
H3B H -0.603783 -0.356900 -0.596493 0.088 Uiso 1 1 d R U . . .
ZN1 Zn -0.2181(3) -0.38934(15) -0.64744(14) 0.0413(7) Uani 1 1 d . . . . .
BR1 Br -0.1001(4) -0.23114(17) -0.64327(18) 0.0694(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.23(2) . ?
C1 O2 1.26(2) . ?
C1 C2 1.56(3) . ?
C2 N1 1.51(2) . ?
C2 C3 1.53(3) . ?
C2 H2 0.9800 . ?
C3 C5 1.50(3) . ?
C3 C4 1.54(3) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.49(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.47(3) . ?
C7 N1 1.49(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.34(3) . ?
C8 C12 1.42(3) 2_445 ?
C9 C10 1.37(3) 2_445 ?
C9 H9 0.9300 . ?
C10 N2 1.37(3) . ?
C10 C9 1.37(3) 2_444 ?
C10 H10 0.9300 . ?
C11 N2 1.29(3) . ?
C11 C12 1.33(3) . ?
C11 H11 0.9300 . ?
C12 C8 1.42(3) 2_444 ?
C12 H12 0.9300 . ?
N1 ZN1 2.103(16) . ?
N1 H1 0.9800 . ?
N2 ZN1 2.061(16) . ?
O1 ZN1 2.169(14) . ?
O3 ZN1 2.142(13) . ?
O3 H3A 0.8802 . ?
O3 H3B 0.8814 . ?
ZN1 BR1 2.372(3) . ?

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 126.5(19) . . ?
O1 C1 C2 118.7(18) . . ?
O2 C1 C2 114.6(17) . . ?
N1 C2 C3 111.9(13) . . ?
N1 C2 C1 105.3(15) . . ?
C3 C2 C1 108.5(15) . . ?
N1 C2 H2 110.3 . . ?
C3 C2 H2 110.3 . . ?
C1 C2 H2 110.3 . . ?
C5 C3 C2 112.7(19) . . ?
C5 C3 C4 114.7(19) . . ?
C2 C3 C4 111.9(17) . . ?
C5 C3 H3 105.5 . . ?
C2 C3 H3 105.5 . . ?
C4 C3 H3 105.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 117(2) . . ?
C6 C5 H5A 108.1 . . ?
C3 C5 H5A 108.1 . . ?
C6 C5 H5B 108.1 . . ?
C3 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 117.6(16) . . ?
C8 C7 H7A 107.9 . . ?
N1 C7 H7A 107.9 . . ?
C8 C7 H7B 107.9 . . ?
N1 C7 H7B 107.9 . . ?
H7A C7 H7B 107.2 . . ?
C9 C8 C12 114.9(16) . 2_445 ?
C9 C8 C7 121.3(19) . . ?
C12 C8 C7 123.4(18) 2_445 . ?
C8 C9 C10 122.2(18) . 2_445 ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 2_445 . ?
N2 C10 C9 120.7(19) . 2_444 ?
N2 C10 H10 119.7 . . ?
C9 C10 H10 119.7 2_444 . ?
N2 C11 C12 125(2) . . ?
N2 C11 H11 117.4 . . ?
C12 C11 H11 117.4 . . ?
C11 C12 C8 119.5(19) . 2_444 ?
C11 C12 H12 120.2 . . ?
C8 C12 H12 120.2 2_444 . ?
C7 N1 C2 110.4(13) . . ?
C7 N1 ZN1 106.4(11) . . ?
C2 N1 ZN1 108.4(11) . . ?
C7 N1 H1 110.5 . . ?
C2 N1 H1 110.5 . . ?
ZN1 N1 H1 110.5 . . ?
C11 N2 C10 116.5(16) . . ?
C11 N2 ZN1 119.8(13) . . ?
C10 N2 ZN1 123.4(14) . . ?
C1 O1 ZN1 113.1(13) . . ?
ZN1 O3 H3A 111.8 . . ?
ZN1 O3 H3B 110.7 . . ?
H3A O3 H3B 107.6 . . ?
N2 ZN1 N1 117.9(6) . . ?
N2 ZN1 O3 93.9(7) . . ?
N1 ZN1 O3 89.7(6) . . ?
N2 ZN1 O1 91.9(6) . . ?
N1 ZN1 O1 79.1(5) . . ?
O3 ZN1 O1 168.8(6) . . ?
N2 ZN1 BR1 116.3(5) . . ?
N1 ZN1 BR1 125.4(4) . . ?
O3 ZN1 BR1 92.0(4) . . ?
O1 ZN1 BR1 93.9(4) . . ?

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
O1 C1 C2 N1 -40(2) . . . . ?
O2 C1 C2 N1 134.6(15) . . . . ?
O1 C1 C2 C3 79(2) . . . . ?
O2 C1 C2 C3 -105.4(18) . . . . ?
N1 C2 C3 C5 -74(2) . . . . ?
C1 C2 C3 C5 170(2) . . . . ?
N1 C2 C3 C4 155.0(19) . . . . ?
C1 C2 C3 C4 39(2) . . . . ?
C2 C3 C5 C6 176(2) . . . . ?
C4 C3 C5 C6 -54(3) . . . . ?
N1 C7 C8 C9 117(2) . . . . ?
N1 C7 C8 C12 -55(3) . . . 2_445 ?
C12 C8 C9 C10 -8(3) 2_445 . . 2_445 ?
C7 C8 C9 C10 179(2) . . . 2_445 ?
N2 C11 C12 C8 -10(4) . . . 2_444 ?
C8 C7 N1 C2 -57(2) . . . . ?
C8 C7 N1 ZN1 -174.6(14) . . . . ?
C3 C2 N1 C7 165.6(16) . . . . ?
C1 C2 N1 C7 -76.8(17) . . . . ?
C3 C2 N1 ZN1 -78.3(16) . . . . ?
C1 C2 N1 ZN1 39.4(14) . . . . ?
C12 C11 N2 C10 6(3) . . . . ?
C12 C11 N2 ZN1 -179.4(18) . . . . ?
C9 C10 N2 C11 -4(3) 2_444 . . . ?
C9 C10 N2 ZN1 -178.0(16) 2_444 . . . ?
O2 C1 O1 ZN1 -155.0(16) . . . . ?
C2 C1 O1 ZN1 19.5(19) . . . . ?

_refine_diff_density_max         0.897
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.196

####################################################################### 
# 
# 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_IL
_database_code_depnum_ccdc_archive 'CCDC 1528709'
_audit_update_record             
;
2017-01-20 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 N2 O2'
_chemical_formula_sum            'C12 H18 N2 O2'
_chemical_formula_weight         222.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   7.7667(3)
_cell_length_b                   5.8151(2)
_cell_length_c                   13.6758(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.312(4)
_cell_angle_gamma                90
_cell_volume                     603.45(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1573
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   Crysalispro
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Supernova (Mo) X-Ray source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2231
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.049
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.739
_diffrn_reflns_point_group_measured_fraction_full 0.739
_reflns_number_total             1573
_reflns_number_gt                1500
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.338
_reflns_Friedel_fraction_max     0.418
_reflns_Friedel_fraction_full    0.418

_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-2016/4 (Sheldrick, 2016)'
_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)+(0.0305P)²+0.2222P] 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_abs_structure_details 
;
 Flack x determined using 355 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1573
_refine_ls_number_parameters     147
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.163
_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
C1 C -0.0197(4) -0.1436(7) -0.5983(3) 0.0431(9) Uani 1 1 d . . . . .
H1 H 0.050729 -0.015870 -0.577683 0.052 Uiso 1 1 calc R U . . .
C2 C -0.1917(4) -0.1411(6) -0.5859(2) 0.0390(8) Uani 1 1 d . . . . .
H2 H -0.233893 -0.015871 -0.555752 0.047 Uiso 1 1 calc R U . . .
C3 C -0.2996(4) -0.3242(6) -0.6182(2) 0.0298(7) Uani 1 1 d . . . . .
C4 C -0.2283(4) -0.5086(6) -0.6596(2) 0.0388(8) Uani 1 1 d . . . . .
H4 H -0.296522 -0.637362 -0.681801 0.047 Uiso 1 1 calc R U . . .
C5 C -0.0546(5) -0.4985(7) -0.6673(3) 0.0415(8) Uani 1 1 d . . . . .
H5 H -0.007609 -0.624301 -0.694441 0.050 Uiso 1 1 calc R U . . .
C6 C -0.4879(4) -0.3259(7) -0.6057(2) 0.0360(8) Uani 1 1 d . . . . .
H6A H -0.507861 -0.464753 -0.570413 0.043 Uiso 1 1 calc R U . . .
H6B H -0.505977 -0.195645 -0.564776 0.043 Uiso 1 1 calc R U . . .
C7 C -0.5971(4) -0.1272(5) -0.7730(2) 0.0275(7) Uani 1 1 d . . . . .
H7 H -0.474638 -0.131598 -0.780860 0.033 Uiso 1 1 calc R U . . .
C8 C -0.6281(4) 0.1086(6) -0.7303(2) 0.0328(7) Uani 1 1 d . . . . .
C9 C -0.7157(4) -0.1766(6) -0.8760(2) 0.0368(8) Uani 1 1 d . . . . .
H9 H -0.713677 -0.343113 -0.886723 0.044 Uiso 1 1 calc R U . . .
C10 C -0.6431(6) -0.0632(8) -0.9587(3) 0.0575(12) Uani 1 1 d . . . . .
H10A H -0.650214 0.102300 -0.951733 0.069 Uiso 1 1 calc R U . . .
H10B H -0.519466 -0.103223 -0.949977 0.069 Uiso 1 1 calc R U . . .
C11 C -0.7363(6) -0.1289(11) -1.0632(3) 0.0761(15) Uani 1 1 d . . . . .
H11A H -0.673481 -0.066737 -1.110542 0.114 Uiso 1 1 calc R U . . .
H11B H -0.853970 -0.068345 -1.076625 0.114 Uiso 1 1 calc R U . . .
H11C H -0.740765 -0.293387 -1.069106 0.114 Uiso 1 1 calc R U . . .
C12 C -0.9053(5) -0.1095(10) -0.8797(3) 0.0622(12) Uani 1 1 d . . . . .
H12A H -0.944446 -0.179218 -0.824633 0.093 Uiso 1 1 calc R U . . .
H12B H -0.977922 -0.161411 -0.941549 0.093 Uiso 1 1 calc R U . . .
H12C H -0.913701 0.054729 -0.875257 0.093 Uiso 1 1 calc R U . . .
N1 N 0.0495(3) -0.3192(6) -0.6381(2) 0.0395(7) Uani 1 1 d . . . . .
N2 N -0.6192(3) -0.3154(5) -0.70208(18) 0.0279(6) Uani 1 1 d . . . . .
H2A H -0.725682 -0.301501 -0.688386 0.034 Uiso 1 1 calc R U . . .
H2B H -0.616718 -0.449150 -0.733407 0.034 Uiso 1 1 calc R U . . .
O1 O -0.5928(3) 0.2740(4) -0.78123(18) 0.0468(7) Uani 1 1 d . . . . .
O2 O -0.6828(4) 0.1202(4) -0.65223(19) 0.0541(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.324(5) . ?
C1 C2 1.382(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 C6 1.508(4) . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.328(5) . ?
C5 H5 0.9300 . ?
C6 N2 1.485(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.496(4) . ?
C7 C8 1.529(4) . ?
C7 C9 1.537(4) . ?
C7 H7 0.9800 . ?
C8 O2 1.233(4) . ?
C8 O1 1.252(4) . ?
C9 C12 1.513(5) . ?
C9 C10 1.519(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.507(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?

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 123.1(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 117.7(3) . . ?
C2 C3 C6 120.6(3) . . ?
C4 C3 C6 121.6(3) . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 123.7(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
N2 C6 C3 113.4(2) . . ?
N2 C6 H6A 108.9 . . ?
C3 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C3 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N2 C7 C8 111.1(2) . . ?
N2 C7 C9 109.2(2) . . ?
C8 C7 C9 113.9(3) . . ?
N2 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
C9 C7 H7 107.5 . . ?
O2 C8 O1 126.6(3) . . ?
O2 C8 C7 119.4(3) . . ?
O1 C8 C7 114.0(3) . . ?
C12 C9 C10 112.1(3) . . ?
C12 C9 C7 111.8(3) . . ?
C10 C9 C7 110.9(3) . . ?
C12 C9 H9 107.2 . . ?
C10 C9 H9 107.2 . . ?
C7 C9 H9 107.2 . . ?
C11 C10 C9 114.6(4) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
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 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 C5 117.0(3) . . ?
C6 N2 C7 116.9(2) . . ?
C6 N2 H2A 108.1 . . ?
C7 N2 H2A 108.1 . . ?
C6 N2 H2B 108.1 . . ?
C7 N2 H2B 108.1 . . ?
H2A N2 H2B 107.3 . . ?

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 -1.9(5) . . . . ?
C1 C2 C3 C4 2.0(5) . . . . ?
C1 C2 C3 C6 -179.9(3) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C6 C3 C4 C5 -178.8(3) . . . . ?
C3 C4 C5 N1 -0.8(5) . . . . ?
C2 C3 C6 N2 113.0(3) . . . . ?
C4 C3 C6 N2 -69.0(4) . . . . ?
N2 C7 C8 O2 -7.2(4) . . . . ?
C9 C7 C8 O2 116.5(3) . . . . ?
N2 C7 C8 O1 172.6(3) . . . . ?
C9 C7 C8 O1 -63.7(3) . . . . ?
N2 C7 C9 C12 79.7(4) . . . . ?
C8 C7 C9 C12 -45.0(4) . . . . ?
N2 C7 C9 C10 -154.4(3) . . . . ?
C8 C7 C9 C10 80.9(4) . . . . ?
C12 C9 C10 C11 -62.4(5) . . . . ?
C7 C9 C10 C11 171.9(4) . . . . ?
C2 C1 N1 C5 0.3(5) . . . . ?
C4 C5 N1 C1 1.0(5) . . . . ?
C3 C6 N2 C7 -51.7(4) . . . . ?
C8 C7 N2 C6 -66.6(3) . . . . ?
C9 C7 N2 C6 167.0(3) . . . . ?

_refine_diff_density_max         0.128
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.034

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

data_ZAIL-NO3
_database_code_depnum_ccdc_archive 'CCDC 1528713'
_audit_update_record             
;
2017-01-20 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H19 N3 O6 Zn'
_chemical_formula_sum            'C12 H19 N3 O6 Zn'
_chemical_formula_weight         366.67

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   6.1863(3)
_cell_length_b                   16.8458(7)
_cell_length_c                   15.5108(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.948(6)
_cell_angle_gamma                90
_cell_volume                     1604.56(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4482
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      25.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.561
_shelx_estimated_absorpt_T_min   0.687
_shelx_estimated_absorpt_T_max   0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_T_max  0.755
_exptl_absorpt_process_details   Crysalispro
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Supernova (Mo) X-Ray source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5942
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.909
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_point_group_measured_fraction_full 0.792
_reflns_number_total             4482
_reflns_number_gt                3743
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.529
_reflns_Friedel_fraction_max     0.569
_reflns_Friedel_fraction_full    0.569

_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-2016/4 (Sheldrick, 2016)'
_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)+(0.1058P)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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4482
_refine_ls_number_parameters     403
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1949
_refine_ls_wR_factor_gt          0.1838
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.4067(18) 0.6427(8) 0.5115(8) 0.036(3) Uani 1 1 d . . . . .
C2 C 0.1893(17) 0.6094(7) 0.4688(7) 0.031(3) Uani 1 1 d . . . . .
H2 H 0.211933 0.553878 0.453235 0.037 Uiso 1 1 calc R U . . .
C3 C 0.101(2) 0.6534(9) 0.3878(8) 0.045(3) Uani 1 1 d . . . . .
H3 H 0.034208 0.703170 0.404120 0.054 Uiso 1 1 calc R U . . .
C4 C 0.285(3) 0.6725(13) 0.3326(13) 0.080(6) Uani 1 1 d . . . . .
H4A H 0.395511 0.702927 0.366521 0.120 Uiso 1 1 calc R U . . .
H4B H 0.227205 0.702535 0.282409 0.120 Uiso 1 1 calc R U . . .
H4C H 0.346638 0.623913 0.314400 0.120 Uiso 1 1 calc R U . . .
C5 C -0.078(2) 0.6013(10) 0.3335(9) 0.054(4) Uani 1 1 d . . . . .
H5A H -0.010211 0.552784 0.316352 0.065 Uiso 1 1 calc R U . . .
H5B H -0.187036 0.586661 0.370520 0.065 Uiso 1 1 calc R U . . .
C6 C -0.188(3) 0.6409(16) 0.2543(10) 0.086(7) Uani 1 1 d . . . . .
H6A H -0.080873 0.657696 0.218254 0.129 Uiso 1 1 calc R U . . .
H6B H -0.267600 0.686159 0.270843 0.129 Uiso 1 1 calc R U . . .
H6C H -0.286594 0.604195 0.222657 0.129 Uiso 1 1 calc R U . . .
C7 C 0.062(2) 0.5434(8) 0.5970(8) 0.044(3) Uani 1 1 d . . . . .
H7A H -0.041469 0.548429 0.638723 0.052 Uiso 1 1 calc R U . . .
H7B H 0.207379 0.546238 0.628674 0.052 Uiso 1 1 calc R U . . .
C8 C 0.189(3) 0.8711(8) 0.5365(12) 0.066(5) Uani 1 1 d . . . . .
H8 H 0.322732 0.858554 0.567960 0.079 Uiso 1 1 calc R U . . .
C9 C 0.162(2) 0.9429(9) 0.4940(13) 0.071(5) Uani 1 1 d . . . . .
H9 H 0.277595 0.978618 0.497303 0.086 Uiso 1 1 calc R U . . .
C10 C -0.033(2) 0.9627(8) 0.4468(8) 0.038(3) Uani 1 1 d . . . . .
C11 C -0.194(2) 0.9090(8) 0.4439(9) 0.049(4) Uani 1 1 d . . . . .
H11 H -0.327765 0.919332 0.411579 0.059 Uiso 1 1 calc R U . . .
C12 C -0.162(2) 0.8384(8) 0.4889(9) 0.047(3) Uani 1 1 d . . . . .
H12 H -0.277762 0.803280 0.487836 0.056 Uiso 1 1 calc R U . . .
C13 C 0.4167(19) 0.3710(7) 0.0019(9) 0.036(3) Uani 1 1 d . . . . .
C14 C 0.1980(18) 0.3420(7) -0.0417(8) 0.033(3) Uani 1 1 d . . . . .
H14 H 0.217680 0.290125 -0.068297 0.040 Uiso 1 1 calc R U . . .
C15 C 0.0998(19) 0.4001(8) -0.1124(8) 0.040(3) Uani 1 1 d . . . . .
H15 H 0.021932 0.440772 -0.083151 0.048 Uiso 1 1 calc R U . . .
C16 C -0.073(3) 0.3559(12) -0.1757(10) 0.071(5) Uani 1 1 d . . . . .
H16A H 0.000267 0.316255 -0.207068 0.085 Uiso 1 1 calc R U . . .
H16B H -0.171553 0.328131 -0.141963 0.085 Uiso 1 1 calc R U . . .
C17 C -0.203(4) 0.407(2) -0.2393(13) 0.148(14) Uani 1 1 d . . . . .
H17A H -0.110183 0.429011 -0.278850 0.221 Uiso 1 1 calc R U . . .
H17B H -0.265710 0.449689 -0.209416 0.221 Uiso 1 1 calc R U . . .
H17C H -0.316442 0.376635 -0.271165 0.221 Uiso 1 1 calc R U . . .
C18 C 0.258(4) 0.4424(18) -0.1606(14) 0.142(13) Uani 1 1 d . . . . .
H18A H 0.338032 0.404527 -0.190601 0.213 Uiso 1 1 calc R U . . .
H18B H 0.357876 0.472021 -0.120506 0.213 Uiso 1 1 calc R U . . .
H18C H 0.181859 0.478060 -0.201908 0.213 Uiso 1 1 calc R U . . .
C19 C 0.092(2) 0.2595(7) 0.0758(9) 0.038(3) Uani 1 1 d . . . . .
H19A H -0.001181 0.259357 0.121838 0.046 Uiso 1 1 calc R U . . .
H19B H 0.241415 0.260336 0.103201 0.046 Uiso 1 1 calc R U . . .
C20 C 0.056(2) 0.1824(7) 0.0260(9) 0.039(3) Uani 1 1 d . . . . .
C21 C -0.1469(19) 0.1656(7) -0.0201(9) 0.039(3) Uani 1 1 d . . . . .
H21 H -0.259153 0.202532 -0.022163 0.047 Uiso 1 1 calc R U . . .
C22 C 0.2100(19) 0.1255(7) 0.0290(8) 0.040(3) Uani 1 1 d . . . . .
H22 H 0.345750 0.133810 0.060529 0.048 Uiso 1 1 calc R U . . .
C23 C -0.166(2) 0.5552(7) 0.0144(9) 0.043(3) Uani 1 1 d . . . . .
H23 H -0.277116 0.517823 0.013350 0.052 Uiso 1 1 calc R U . . .
C24 C 0.180(2) 0.5942(8) 0.0624(9) 0.046(4) Uani 1 1 d . . . . .
H24 H 0.313362 0.585321 0.095165 0.055 Uiso 1 1 calc R U . . .
N1 N 0.0330(15) 0.6111(6) 0.5355(6) 0.027(2) Uani 1 1 d . . . . .
H1 H -0.116390 0.610700 0.506106 0.033 Uiso 1 1 calc R U . . .
N2 N 0.0221(17) 0.8187(6) 0.5326(8) 0.040(3) Uani 1 1 d . . . . .
N3 N 0.2978(17) 0.7197(10) 0.7673(7) 0.046(3) Uani 1 1 d . . . . .
N4 N 0.0517(14) 0.3327(6) 0.0263(6) 0.024(2) Uani 1 1 d . . . . .
H4 H -0.100082 0.333851 -0.000495 0.029 Uiso 1 1 calc R U . . .
N5 N 0.0309(15) 0.5374(6) 0.0590(7) 0.032(2) Uani 1 1 d . . . . .
N6 N 0.2977(19) 0.4210(9) 0.2746(7) 0.048(3) Uani 1 1 d . . . . .
O1 O 0.5761(14) 0.6144(6) 0.4931(7) 0.059(3) Uani 1 1 d . . . . .
O2 O 0.3960(12) 0.7023(5) 0.5642(5) 0.035(2) Uani 1 1 d . . . . .
O3 O -0.2084(12) 0.7207(7) 0.6581(5) 0.037(2) Uani 1 1 d . . . . .
H3A H -0.234968 0.675132 0.678929 0.055 Uiso 1 1 d R U . . .
H3B H -0.201557 0.755369 0.698741 0.055 Uiso 1 1 d R U . . .
O4 O 0.2329(16) 0.7777(7) 0.7203(6) 0.047(2) Uani 1 1 d . . . . .
O5 O 0.3857(16) 0.7279(9) 0.8417(6) 0.069(3) Uani 1 1 d . . . . .
O6 O 0.5837(14) 0.3478(7) -0.0268(7) 0.056(3) Uani 1 1 d . . . . .
O7 O 0.4142(12) 0.4176(6) 0.0656(5) 0.036(2) Uani 1 1 d . . . . .
O8 O -0.1906(12) 0.4151(5) 0.1659(5) 0.034(2) Uani 1 1 d . . . . .
H8A H -0.203387 0.367307 0.182693 0.051 Uiso 1 1 d R U . . .
H8B H -0.193027 0.446290 0.209081 0.051 Uiso 1 1 d R U . . .
O9 O 0.2333(16) 0.3559(7) 0.2403(7) 0.052(3) Uani 1 1 d . . . . .
O10 O 0.2769(17) 0.4804(6) 0.2271(7) 0.053(3) Uani 1 1 d . . . . .
O11 O 0.377(2) 0.4234(10) 0.3543(7) 0.098(5) Uani 1 1 d . . . . .
O36 O 0.252(2) 0.6515(8) 0.7376(9) 0.077(4) Uani 1 1 d . . . . .
ZN1 Zn 0.0867(2) 0.71679(6) 0.60593(8) 0.0319(4) Uani 1 1 d . . . . .
ZN2 Zn 0.1084(2) 0.42824(7) 0.11359(8) 0.0296(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.217(14) . ?
C1 O2 1.302(15) . ?
C1 C2 1.532(15) . ?
C2 N1 1.499(15) . ?
C2 C3 1.506(17) . ?
C2 H2 0.9800 . ?
C3 C4 1.54(2) . ?
C3 C5 1.572(18) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.49(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N1 1.483(16) . ?
C7 C10 1.521(17) 2_546 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.356(18) . ?
C8 C9 1.38(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.342(19) . ?
C10 C7 1.521(17) 2_556 ?
C11 C12 1.381(19) . ?
C11 H11 0.9300 . ?
C12 N2 1.294(17) . ?
C12 H12 0.9300 . ?
C13 O6 1.237(14) . ?
C13 O7 1.265(15) . ?
C13 C14 1.518(16) . ?
C14 N4 1.478(14) . ?
C14 C15 1.539(17) . ?
C14 H14 0.9800 . ?
C15 C18 1.49(2) . ?
C15 C16 1.553(19) . ?
C15 H15 0.9800 . ?
C16 C17 1.47(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N4 1.459(16) . ?
C19 C20 1.514(17) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C22 1.349(17) . ?
C20 C21 1.396(17) . ?
C21 C24 1.372(17) 2_545 ?
C21 H21 0.9300 . ?
C22 C23 1.372(17) 2_545 ?
C22 H22 0.9300 . ?
C23 N5 1.361(15) . ?
C23 C22 1.372(17) 2 ?
C23 H23 0.9300 . ?
C24 N5 1.324(16) . ?
C24 C21 1.372(17) 2 ?
C24 H24 0.9300 . ?
N1 ZN1 2.094(10) . ?
N1 H1 0.9800 . ?
N2 ZN1 2.071(11) . ?
N3 O5 1.223(13) . ?
N3 O4 1.254(17) . ?
N3 O36 1.26(2) . ?
N4 ZN2 2.106(10) . ?
N4 H4 0.9800 . ?
N5 ZN2 2.057(10) . ?
N6 O10 1.240(17) . ?
N6 O9 1.262(17) . ?
N6 O11 1.274(14) . ?
O2 ZN1 2.107(8) . ?
O3 ZN1 2.085(8) . ?
O3 H3A 0.8566 . ?
O3 H3B 0.8568 . ?
O4 ZN1 2.151(9) . ?
O7 ZN2 2.122(8) . ?
O8 ZN2 2.120(7) . ?
O8 H8A 0.8522 . ?
O8 H8B 0.8525 . ?
O9 ZN2 2.361(10) . ?
O10 ZN2 2.125(11) . ?
O36 ZN1 2.433(14) . ?

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 124.1(11) . . ?
O1 C1 C2 119.4(11) . . ?
O2 C1 C2 116.4(10) . . ?
N1 C2 C3 111.5(9) . . ?
N1 C2 C1 107.5(9) . . ?
C3 C2 C1 113.1(10) . . ?
N1 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
C1 C2 H2 108.2 . . ?
C2 C3 C4 110.3(11) . . ?
C2 C3 C5 109.5(11) . . ?
C4 C3 C5 109.7(12) . . ?
C2 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C5 C3 H3 109.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 114.4(15) . . ?
C6 C5 H5A 108.7 . . ?
C3 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C3 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C10 113.7(10) . 2_546 ?
N1 C7 H7A 108.8 . . ?
C10 C7 H7A 108.8 2_546 . ?
N1 C7 H7B 108.8 . . ?
C10 C7 H7B 108.8 2_546 . ?
H7A C7 H7B 107.7 . . ?
N2 C8 C9 120.1(15) . . ?
N2 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 121.0(14) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 117.1(12) . . ?
C11 C10 C7 122.7(12) . 2_556 ?
C9 C10 C7 120.2(13) . 2_556 ?
C10 C11 C12 120.1(13) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N2 C12 C11 123.4(13) . . ?
N2 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
O6 C13 O7 124.6(12) . . ?
O6 C13 C14 118.5(12) . . ?
O7 C13 C14 117.0(10) . . ?
N4 C14 C13 107.8(9) . . ?
N4 C14 C15 110.7(9) . . ?
C13 C14 C15 111.5(10) . . ?
N4 C14 H14 108.9 . . ?
C13 C14 H14 108.9 . . ?
C15 C14 H14 108.9 . . ?
C18 C15 C14 115.9(14) . . ?
C18 C15 C16 111.0(13) . . ?
C14 C15 C16 109.2(11) . . ?
C18 C15 H15 106.8 . . ?
C14 C15 H15 106.8 . . ?
C16 C15 H15 106.8 . . ?
C17 C16 C15 114.8(19) . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 C19 C20 116.8(10) . . ?
N4 C19 H19A 108.1 . . ?
C20 C19 H19A 108.1 . . ?
N4 C19 H19B 108.1 . . ?
C20 C19 H19B 108.1 . . ?
H19A C19 H19B 107.3 . . ?
C22 C20 C21 117.5(11) . . ?
C22 C20 C19 122.2(11) . . ?
C21 C20 C19 120.2(11) . . ?
C24 C21 C20 119.5(11) 2_545 . ?
C24 C21 H21 120.2 2_545 . ?
C20 C21 H21 120.2 . . ?
C20 C22 C23 120.0(11) . 2_545 ?
C20 C22 H22 120.0 . . ?
C23 C22 H22 120.0 2_545 . ?
N5 C23 C22 123.4(11) . 2 ?
N5 C23 H23 118.3 . . ?
C22 C23 H23 118.3 2 . ?
N5 C24 C21 123.6(12) . 2 ?
N5 C24 H24 118.2 . . ?
C21 C24 H24 118.2 2 . ?
C7 N1 C2 112.9(9) . . ?
C7 N1 ZN1 108.6(7) . . ?
C2 N1 ZN1 107.6(7) . . ?
C7 N1 H1 109.2 . . ?
C2 N1 H1 109.2 . . ?
ZN1 N1 H1 109.2 . . ?
C12 N2 C8 118.2(12) . . ?
C12 N2 ZN1 126.8(9) . . ?
C8 N2 ZN1 114.8(9) . . ?
O5 N3 O4 122.4(15) . . ?
O5 N3 O36 120.2(15) . . ?
O4 N3 O36 117.1(11) . . ?
C19 N4 C14 112.6(10) . . ?
C19 N4 ZN2 107.7(7) . . ?
C14 N4 ZN2 108.0(7) . . ?
C19 N4 H4 109.5 . . ?
C14 N4 H4 109.5 . . ?
ZN2 N4 H4 109.5 . . ?
C24 N5 C23 115.9(10) . . ?
C24 N5 ZN2 120.3(8) . . ?
C23 N5 ZN2 123.8(8) . . ?
O10 N6 O9 116.4(11) . . ?
O10 N6 O11 123.4(15) . . ?
O9 N6 O11 120.2(15) . . ?
C1 O2 ZN1 113.5(7) . . ?
ZN1 O3 H3A 109.6 . . ?
ZN1 O3 H3B 109.8 . . ?
H3A O3 H3B 109.1 . . ?
N3 O4 ZN1 100.4(8) . . ?
C13 O7 ZN2 115.0(8) . . ?
ZN2 O8 H8A 109.5 . . ?
ZN2 O8 H8B 109.6 . . ?
H8A O8 H8B 109.4 . . ?
N6 O9 ZN2 87.6(8) . . ?
N6 O10 ZN2 99.4(9) . . ?
N3 O36 ZN1 87.0(9) . . ?
N2 ZN1 O3 93.9(4) . . ?
N2 ZN1 N1 114.2(4) . . ?
O3 ZN1 N1 98.0(4) . . ?
N2 ZN1 O2 92.8(4) . . ?
O3 ZN1 O2 173.2(4) . . ?
N1 ZN1 O2 80.4(4) . . ?
N2 ZN1 O4 95.3(4) . . ?
O3 ZN1 O4 88.0(3) . . ?
N1 ZN1 O4 149.3(4) . . ?
O2 ZN1 O4 90.1(4) . . ?
N2 ZN1 O36 150.4(5) . . ?
O3 ZN1 O36 89.2(4) . . ?
N1 ZN1 O36 94.4(4) . . ?
O2 ZN1 O36 84.3(4) . . ?
O4 ZN1 O36 55.4(4) . . ?
N5 ZN2 N4 114.0(4) . . ?
N5 ZN2 O8 94.6(4) . . ?
N4 ZN2 O8 94.7(3) . . ?
N5 ZN2 O7 96.0(4) . . ?
N4 ZN2 O7 78.2(4) . . ?
O8 ZN2 O7 169.0(4) . . ?
N5 ZN2 O10 92.2(4) . . ?
N4 ZN2 O10 151.2(4) . . ?
O8 ZN2 O10 95.1(4) . . ?
O7 ZN2 O10 87.5(4) . . ?
N5 ZN2 O9 147.2(4) . . ?
N4 ZN2 O9 98.8(4) . . ?
O8 ZN2 O9 80.8(3) . . ?
O7 ZN2 O9 91.8(3) . . ?
O10 ZN2 O9 56.3(4) . . ?

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
O1 C1 C2 N1 143.5(12) . . . . ?
O2 C1 C2 N1 -38.5(14) . . . . ?
O1 C1 C2 C3 -93.0(14) . . . . ?
O2 C1 C2 C3 85.0(13) . . . . ?
N1 C2 C3 C4 163.1(12) . . . . ?
C1 C2 C3 C4 41.8(16) . . . . ?
N1 C2 C3 C5 -76.0(12) . . . . ?
C1 C2 C3 C5 162.7(10) . . . . ?
C2 C3 C5 C6 176.3(13) . . . . ?
C4 C3 C5 C6 -62.5(18) . . . . ?
N2 C8 C9 C10 0(3) . . . . ?
C8 C9 C10 C11 0(3) . . . . ?
C8 C9 C10 C7 177.8(16) . . . 2_556 ?
C9 C10 C11 C12 2(2) . . . . ?
C7 C10 C11 C12 -176.4(13) 2_556 . . . ?
C10 C11 C12 N2 -3(2) . . . . ?
O6 C13 C14 N4 145.2(12) . . . . ?
O7 C13 C14 N4 -34.7(14) . . . . ?
O6 C13 C14 C15 -93.2(14) . . . . ?
O7 C13 C14 C15 86.9(13) . . . . ?
N4 C14 C15 C18 153.6(15) . . . . ?
C13 C14 C15 C18 33.6(19) . . . . ?
N4 C14 C15 C16 -80.3(12) . . . . ?
C13 C14 C15 C16 159.7(11) . . . . ?
C18 C15 C16 C17 -60(2) . . . . ?
C14 C15 C16 C17 171.6(14) . . . . ?
N4 C19 C20 C22 126.9(14) . . . . ?
N4 C19 C20 C21 -57.8(17) . . . . ?
C22 C20 C21 C24 -2(2) . . . 2_545 ?
C19 C20 C21 C24 -177.6(13) . . . 2_545 ?
C21 C20 C22 C23 2(2) . . . 2_545 ?
C19 C20 C22 C23 177.3(13) . . . 2_545 ?
C10 C7 N1 C2 -59.4(14) 2_546 . . . ?
C10 C7 N1 ZN1 -178.6(9) 2_546 . . . ?
C3 C2 N1 C7 155.1(11) . . . . ?
C1 C2 N1 C7 -80.4(11) . . . . ?
C3 C2 N1 ZN1 -85.1(10) . . . . ?
C1 C2 N1 ZN1 39.3(10) . . . . ?
C11 C12 N2 C8 2(2) . . . . ?
C11 C12 N2 ZN1 177.6(11) . . . . ?
C9 C8 N2 C12 -1(2) . . . . ?
C9 C8 N2 ZN1 -176.6(14) . . . . ?
C20 C19 N4 C14 -62.4(14) . . . . ?
C20 C19 N4 ZN2 178.7(9) . . . . ?
C13 C14 N4 C19 -79.1(12) . . . . ?
C15 C14 N4 C19 158.7(10) . . . . ?
C13 C14 N4 ZN2 39.6(10) . . . . ?
C15 C14 N4 ZN2 -82.5(10) . . . . ?
C21 C24 N5 C23 -4(2) 2 . . . ?
C21 C24 N5 ZN2 173.2(11) 2 . . . ?
C22 C23 N5 C24 3(2) 2 . . . ?
C22 C23 N5 ZN2 -173.4(10) 2 . . . ?
O1 C1 O2 ZN1 -165.1(11) . . . . ?
C2 C1 O2 ZN1 16.9(13) . . . . ?
O5 N3 O4 ZN1 -177.1(11) . . . . ?
O36 N3 O4 ZN1 -3.3(14) . . . . ?
O6 C13 O7 ZN2 -168.7(10) . . . . ?
C14 C13 O7 ZN2 11.2(13) . . . . ?
O10 N6 O9 ZN2 -4.3(12) . . . . ?
O11 N6 O9 ZN2 175.1(13) . . . . ?
O9 N6 O10 ZN2 4.8(14) . . . . ?
O11 N6 O10 ZN2 -174.5(13) . . . . ?
O5 N3 O36 ZN1 176.8(11) . . . . ?
O4 N3 O36 ZN1 2.9(12) . . . . ?

_refine_diff_density_max         0.605
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.126

