# Electronic Supplementary Material (ESI) for ChemComm.
# 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_coagcucl2_mono
_database_code_depnum_ccdc_archive 'CCDC 1517413'
_audit_update_record             
;
2016-11-15 deposited with the CCDC.
2017-01-20 downloaded from the CCDC.
;
_audit_creation_date             2016-11-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N3 O'
_chemical_formula_sum            'C14 H15 N3 O'
_chemical_formula_weight         241.29
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.5946(6)
_cell_length_b                   24.212(3)
_cell_length_c                   5.7315(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.629(4)
_cell_angle_gamma                90
_cell_volume                     610.94(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2692
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.746
_cell_measurement_theta_min      3.365
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0786 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.9247.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.124
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7874
_diffrn_reflns_point_group_measured_fraction_full 0.873
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.309
_diffrn_reflns_theta_min         3.366
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          None
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.546
_reflns_Friedel_fraction_full    0.746
_reflns_Friedel_fraction_max     0.562
_reflns_number_gt                2680
_reflns_number_total             3670
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 769 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+0.0977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1218
_refine_special_details          None
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.0475(3) 0.08230(7) 0.6486(3) 0.0210(4) Uani 1 1 d . . . . .
C2 C 0.7123(5) 0.18802(10) 1.0401(4) 0.0181(5) Uani 1 1 d . . . . .
C3 C 0.3216(5) 0.07660(10) 0.6610(4) 0.0162(5) Uani 1 1 d . . . . .
N4 N 0.4103(4) 0.04520(9) 0.4995(4) 0.0191(4) Uani 1 1 d . . . . .
H4 H 0.6038 0.0371 0.5268 0.023 Uiso 1 1 calc R . . . .
N5 N 0.5472(4) 0.10055(9) 0.8367(4) 0.0211(5) Uani 1 1 d . . . . .
H5 H 0.7362 0.0915 0.8480 0.025 Uiso 1 1 calc R . . . .
C6 C 0.0230(5) -0.02703(10) 0.3146(5) 0.0180(5) Uani 1 1 d . . . . .
C7 C 0.7167(6) 0.22204(13) 0.8457(5) 0.0281(6) Uani 1 1 d . . . . .
H7 H 0.5762 0.2166 0.6898 0.034 Uiso 1 1 calc R . . . .
C8 C 0.4916(6) 0.14060(11) 1.0077(5) 0.0241(6) Uani 1 1 d . . . . .
H8A H 0.5138 0.1225 1.1668 0.029 Uiso 1 1 calc R . . . .
H8B H 0.2812 0.1547 0.9467 0.029 Uiso 1 1 calc R . . . .
C9 C 0.1912(6) 0.02468(11) 0.2815(4) 0.0209(5) Uani 1 1 d . . . . .
H9A H 0.2983 0.0172 0.1576 0.025 Uiso 1 1 calc R . . . .
H9B H 0.0403 0.0541 0.2166 0.025 Uiso 1 1 calc R . . . .
C10 C 0.9194(6) 0.19856(11) 1.2629(5) 0.0242(6) Uani 1 1 d . . . . .
H10 H 0.9137 0.1760 1.3972 0.029 Uiso 1 1 calc R . . . .
C11 C -0.1959(6) -0.04860(12) 0.1159(5) 0.0274(6) Uani 1 1 d . . . . .
H11 H -0.2364 -0.0304 -0.0370 0.033 Uiso 1 1 calc R . . . .
C12 C -0.2972(7) -0.12209(12) 0.3554(6) 0.0376(8) Uani 1 1 d . . . . .
H12 H -0.4073 -0.1545 0.3696 0.045 Uiso 1 1 calc R . . . .
C13 C 0.0773(7) -0.05421(12) 0.5337(5) 0.0290(6) Uani 1 1 d . . . . .
H13 H 0.2254 -0.0401 0.6725 0.035 Uiso 1 1 calc R . . . .
C14 C 1.1300(7) 0.27103(13) 1.1106(6) 0.0347(7) Uani 1 1 d . . . . .
H14 H 1.2754 0.2999 1.1334 0.042 Uiso 1 1 calc R . . . .
N15 N 1.1292(6) 0.23896(12) 1.3005(5) 0.0387(7) Uani 1 1 d . . . . .
C16 C -0.0800(8) -0.10176(13) 0.5554(5) 0.0360(7) Uani 1 1 d . . . . .
H16 H -0.0384 -0.1203 0.7075 0.043 Uiso 1 1 calc R . . . .
C17 C -0.3545(7) -0.09530(12) 0.1346(6) 0.0346(7) Uani 1 1 d . . . . .
H17 H -0.5037 -0.1093 -0.0039 0.042 Uiso 1 1 calc R . . . .
C18 C 0.9282(7) 0.26374(13) 0.8831(6) 0.0350(7) Uani 1 1 d . . . . .
H18 H 0.9351 0.2874 0.7527 0.042 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.248(3) . ?
C2 C7 1.390(4) . ?
C2 C8 1.508(3) . ?
C2 C10 1.381(3) . ?
C3 N4 1.348(3) . ?
C3 N5 1.352(3) . ?
N4 C9 1.450(3) . ?
N5 C8 1.452(3) . ?
C6 C9 1.512(4) . ?
C6 C11 1.388(3) . ?
C6 C13 1.376(4) . ?
C7 C18 1.375(4) . ?
C10 N15 1.347(4) . ?
C11 C17 1.366(4) . ?
C12 C16 1.377(4) . ?
C12 C17 1.379(5) . ?
C13 C16 1.384(4) . ?
C14 N15 1.338(4) . ?
C14 C18 1.378(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C2 C8 121.1(2) . . ?
C10 C2 C7 117.9(2) . . ?
C10 C2 C8 121.1(2) . . ?
O1 C3 N4 121.4(2) . . ?
O1 C3 N5 122.8(2) . . ?
N4 C3 N5 115.81(18) . . ?
C3 N4 C9 120.89(19) . . ?
C3 N5 C8 122.9(2) . . ?
C11 C6 C9 119.0(2) . . ?
C13 C6 C9 123.0(2) . . ?
C13 C6 C11 117.9(2) . . ?
C18 C7 C2 118.8(3) . . ?
N5 C8 C2 110.5(2) . . ?
N4 C9 C6 115.4(2) . . ?
N15 C10 C2 123.7(3) . . ?
C17 C11 C6 121.7(3) . . ?
C16 C12 C17 119.9(3) . . ?
C6 C13 C16 121.1(3) . . ?
N15 C14 C18 122.5(3) . . ?
C14 N15 C10 117.4(2) . . ?
C12 C16 C13 119.7(3) . . ?
C11 C17 C12 119.7(3) . . ?
C7 C18 C14 119.7(3) . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_cozn_a
_database_code_depnum_ccdc_archive 'CCDC 1517412'
_audit_update_record             
;
2016-11-15 deposited with the CCDC.
2017-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26 Cl2 N6 O2 Zn'
_chemical_formula_weight         590.80

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'
Cl Cl 0.1484 0.1585 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   12.4837(7)
_cell_length_b                   23.7851(13)
_cell_length_c                   8.6713(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2574.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3804
_cell_measurement_theta_min      2.849
_cell_measurement_theta_max      33.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.611
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.166
_exptl_absorpt_coefficient_mu    1.198
_shelx_estimated_absorpt_T_min   0.528
_shelx_estimated_absorpt_T_max   0.826
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48921
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.500
_diffrn_reflns_theta_max         35.608
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5717
_reflns_number_gt                4179
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0369P)²+1.0271P] 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_number_reflns         5717
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.32246(2) 0.2500 0.31153(3) 0.01444(6) Uani 1 2 d S T P . .
Cl1 Cl 0.17798(4) 0.2500 0.46013(6) 0.01892(10) Uani 1 2 d S T P . .
O1 O 0.79203(9) 0.46520(4) 0.39289(11) 0.0210(2) Uani 1 1 d . . . . .
N1 N 0.40829(9) 0.32054(5) 0.36879(14) 0.0161(2) Uani 1 1 d . . . . .
C1 C 0.49738(10) 0.33395(6) 0.29049(16) 0.0171(3) Uani 1 1 d . . . . .
H1 H 0.5243 0.3078 0.2173 0.020 Uiso 1 1 calc R U . . .
Cl2 Cl 0.29705(4) 0.2500 0.05790(6) 0.02622(11) Uani 1 2 d S T P . .
N2 N 0.68217(10) 0.45007(6) 0.18765(15) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.55216(10) 0.38418(6) 0.31110(15) 0.0165(2) Uani 1 1 d . . . . .
N3 N 0.78725(10) 0.52828(5) 0.19381(14) 0.0182(2) Uani 1 1 d . . . . .
C3 C 0.50934(10) 0.42301(6) 0.41390(16) 0.0179(3) Uani 1 1 d . . . . .
H3 H 0.5426 0.4586 0.4278 0.021 Uiso 1 1 calc R U . . .
C4 C 0.41773(10) 0.40930(6) 0.49585(16) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.3877 0.4353 0.5669 0.021 Uiso 1 1 calc R U . . .
C5 C 0.37051(10) 0.35740(6) 0.47318(16) 0.0164(2) Uani 1 1 d . . . . .
H5 H 0.3096 0.3475 0.5330 0.020 Uiso 1 1 calc R U . . .
C6 C 0.65724(11) 0.39218(6) 0.22813(19) 0.0213(3) Uani 1 1 d . . . . .
H6A H 0.7155 0.3774 0.2942 0.026 Uiso 1 1 calc R U . . .
H6B H 0.6561 0.3694 0.1325 0.026 Uiso 1 1 calc R U . . .
C7 C 0.75688(10) 0.47999(6) 0.26598(16) 0.0160(2) Uani 1 1 d . . . . .
C8 C 0.85895(11) 0.56905(6) 0.25146(16) 0.0165(2) Uani 1 1 d . . . . .
C9 C 0.94604(11) 0.55597(7) 0.34506(16) 0.0207(3) Uani 1 1 d . . . . .
H9 H 0.9584 0.5182 0.3760 0.025 Uiso 1 1 calc R U . . .
C10 C 1.01481(13) 0.59859(8) 0.39304(18) 0.0285(3) Uani 1 1 d . . . . .
H10 H 1.0729 0.5899 0.4596 0.034 Uiso 1 1 calc R U . . .
C11 C 0.99939(14) 0.65349(8) 0.3447(2) 0.0344(4) Uani 1 1 d . . . . .
H11 H 1.0471 0.6823 0.3768 0.041 Uiso 1 1 calc R U . . .
C12 C 0.91379(14) 0.66593(7) 0.2491(2) 0.0326(4) Uani 1 1 d . . . . .
H12 H 0.9037 0.7034 0.2141 0.039 Uiso 1 1 calc R U . . .
C13 C 0.84285(12) 0.62441(6) 0.20387(18) 0.0230(3) Uani 1 1 d . . . . .
H13 H 0.7833 0.6336 0.1405 0.028 Uiso 1 1 calc R U . . .
H3N H 0.7612(14) 0.5341(7) 0.104(2) 0.017(4) Uiso 1 1 d . . . . .
H2N H 0.6645(15) 0.4613(9) 0.096(2) 0.031(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.0517(11) 8_565 ?
Zn1 N1 2.0518(11) . ?
Zn1 Cl1 2.2166(5) . ?
Zn1 Cl2 2.2221(6) . ?
O1 C7 1.2358(17) . ?
N1 C1 1.3415(17) . ?
N1 C5 1.3454(17) . ?
C1 C2 1.3881(19) . ?
C1 H1 0.9500 . ?
N2 C7 1.3555(18) . ?
N2 C6 1.4548(19) . ?
N2 H2N 0.86(2) . ?
C2 C3 1.3906(19) . ?
C2 C6 1.5081(19) . ?
N3 C7 1.3619(18) . ?
N3 C8 1.4113(18) . ?
N3 H3N 0.856(18) . ?
C3 C4 1.3853(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3821(19) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.392(2) . ?
C8 C13 1.394(2) . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N1 109.72(6) 8_565 . ?
N1 Zn1 Cl1 106.51(3) 8_565 . ?
N1 Zn1 Cl1 106.51(3) . . ?
N1 Zn1 Cl2 108.30(3) 8_565 . ?
N1 Zn1 Cl2 108.30(3) . . ?
Cl1 Zn1 Cl2 117.34(2) . . ?
C1 N1 C5 118.44(12) . . ?
C1 N1 Zn1 120.32(9) . . ?
C5 N1 Zn1 120.84(9) . . ?
N1 C1 C2 123.21(12) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C7 N2 C6 121.54(13) . . ?
C7 N2 H2N 118.3(13) . . ?
C6 N2 H2N 117.3(13) . . ?
C1 C2 C3 117.70(12) . . ?
C1 C2 C6 118.40(12) . . ?
C3 C2 C6 123.80(12) . . ?
C7 N3 C8 126.39(12) . . ?
C7 N3 H3N 116.7(12) . . ?
C8 N3 H3N 116.9(12) . . ?
C4 C3 C2 119.33(13) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 119.30(12) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 121.89(12) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
N2 C6 C2 114.88(12) . . ?
N2 C6 H6A 108.5 . . ?
C2 C6 H6A 108.5 . . ?
N2 C6 H6B 108.5 . . ?
C2 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
O1 C7 N2 122.76(13) . . ?
O1 C7 N3 123.40(13) . . ?
N2 C7 N3 113.82(13) . . ?
C9 C8 C13 119.76(13) . . ?
C9 C8 N3 123.25(13) . . ?
C13 C8 N3 116.91(13) . . ?
C8 C9 C10 119.55(15) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.69(16) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.34(15) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 120.75(16) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 119.87(15) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 Cl1 0.95 2.82 3.7138(14) 157.7 6_656
C5 H5 Cl1 0.95 2.91 3.5093(14) 122.1 .
C6 H6B Cl1 0.99 2.96 3.7641(15) 138.5 6_656
C9 H9 O1 0.95 2.43 2.9205(18) 111.6 .
N3 H3N O1 0.856(18) 1.947(18) 2.7950(16) 170.9(17) 2_664
N2 H2N O1 0.86(2) 2.54(2) 3.2707(17) 142.5(17) 2_664

_refine_diff_density_max         0.769
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.088



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
