# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_(RS-ETI)2_ZnCl2
_database_code_depnum_ccdc_archive 'CCDC 1857803'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2018-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H28 Cl2 N4 O4 Zn'
_chemical_formula_sum            'C16 H28 Cl2 N4 O4 Zn'
_chemical_formula_weight         476.69
_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'
Cl Cl 0.1484 0.1585 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.6678(6)
_cell_length_b                   6.9371(2)
_cell_length_c                   18.0628(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.515(3)
_cell_angle_gamma                90
_cell_volume                     2213.06(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1744
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0290
_cell_measurement_theta_min      3.8650
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.789
_exptl_absorpt_coefficient_mu    1.378
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4853
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.487
_diffrn_reflns_theta_min         3.341
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  19.00   1.00    7.50    --  -16.52 -99.00 150.00   28
  2  ω      3.00  88.00   1.00    7.50    --   17.77   0.00 -90.00   85
  3  ω    -18.00  77.00   1.00    7.50    --   17.77  19.00   0.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0331871000
_diffrn_orient_matrix_UB_12      -0.0446593000
_diffrn_orient_matrix_UB_13      -0.0131473000
_diffrn_orient_matrix_UB_21      -0.0202555000
_diffrn_orient_matrix_UB_22      -0.0293490000
_diffrn_orient_matrix_UB_23      -0.0324588000
_diffrn_orient_matrix_UB_31      0.0101592000
_diffrn_orient_matrix_UB_32      0.0871943000
_diffrn_orient_matrix_UB_33      -0.0177186000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2118
_reflns_number_total             2561
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.056
_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)+(0.0350P)²+2.0796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2C,H2D), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Zn1 Zn 0.500000 0.28832(6) 0.750000 0.03416(14) Uani 1 2 d S T P . .
Cl1 Cl 0.43218(5) 0.12734(13) 0.66668(5) 0.0744(3) Uani 1 1 d . . . . .
O1 O 0.56966(11) 0.4644(3) 0.69897(11) 0.0483(5) Uani 1 1 d . . . . .
N1 N 0.60765(12) 0.6639(3) 0.60909(11) 0.0368(5) Uani 1 1 d . . . . .
O2 O 0.66928(12) 0.3963(4) 0.52430(13) 0.0700(7) Uani 1 1 d . . . . .
N2 N 0.78588(13) 0.4177(4) 0.57457(15) 0.0567(7) Uani 1 1 d . . . . .
H2A H 0.803110 0.329179 0.546262 0.068 Uiso 1 1 calc R . . . .
H2B H 0.815471 0.472821 0.606675 0.068 Uiso 1 1 calc R . . . .
C1 C 0.55459(14) 0.5768(4) 0.64654(14) 0.0372(6) Uani 1 1 d . . . . .
C5 C 0.68805(14) 0.6273(4) 0.62231(14) 0.0385(6) Uani 1 1 d . . . . .
H5 H 0.693924 0.575135 0.672564 0.046 Uiso 1 1 calc R . . . .
C6 C 0.71348(15) 0.4695(4) 0.56870(16) 0.0432(6) Uani 1 1 d . . . . .
C2 C 0.47825(16) 0.6356(4) 0.61747(17) 0.0518(7) Uani 1 1 d . . . . .
H2C H 0.452354 0.713471 0.653523 0.062 Uiso 1 1 calc R . . . .
H2D H 0.447480 0.523415 0.605659 0.062 Uiso 1 1 calc R . . . .
C3 C 0.49326(17) 0.7513(4) 0.54849(17) 0.0519(7) Uani 1 1 d . . . . .
H3A H 0.466239 0.872930 0.549367 0.062 Uiso 1 1 calc R . . . .
H3B H 0.477148 0.680338 0.504552 0.062 Uiso 1 1 calc R . . . .
C4 C 0.57796(17) 0.7852(5) 0.54890(17) 0.0569(8) Uani 1 1 d . . . . .
H4A H 0.599045 0.747541 0.502016 0.068 Uiso 1 1 calc R . . . .
H4B H 0.589638 0.919821 0.558112 0.068 Uiso 1 1 calc R . . . .
C7 C 0.73445(18) 0.8125(4) 0.61973(19) 0.0569(8) Uani 1 1 d . . . . .
H7A H 0.787795 0.780553 0.624737 0.068 Uiso 1 1 calc R . . . .
H7B H 0.726169 0.873542 0.571893 0.068 Uiso 1 1 calc R . . . .
C8 C 0.7142(3) 0.9538(6) 0.6803(2) 0.0921(13) Uani 1 1 d . . . . .
H8A H 0.746614 1.064656 0.677886 0.138 Uiso 1 1 calc GR . . . .
H8B H 0.720898 0.892922 0.727721 0.138 Uiso 1 1 calc GR . . . .
H8C H 0.662437 0.993207 0.673469 0.138 Uiso 1 1 calc GR . . . .


_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 Cl1 2.2028(8) . ?
Zn1 Cl1 2.2028(8) 2_656 ?
Zn1 O1 1.9790(18) . ?
Zn1 O1 1.9790(18) 2_656 ?
O1 C1 1.250(3) . ?
N1 C1 1.317(3) . ?
N1 C5 1.456(3) . ?
N1 C4 1.461(3) . ?
O2 C6 1.215(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C6 1.330(3) . ?
C1 C2 1.491(4) . ?
C5 H5 0.9800 . ?
C5 C6 1.537(4) . ?
C5 C7 1.525(4) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C2 C3 1.511(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.515(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.518(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
Cl1 Zn1 Cl1 119.08(5) 2_656 . ?
O1 Zn1 Cl1 109.18(7) . . ?
O1 Zn1 Cl1 109.17(7) 2_656 2_656 ?
O1 Zn1 Cl1 107.30(6) 2_656 . ?
O1 Zn1 Cl1 107.30(6) . 2_656 ?
O1 Zn1 O1 103.77(12) 2_656 . ?
C1 O1 Zn1 127.97(18) . . ?
C1 N1 C5 122.7(2) . . ?
C1 N1 C4 113.6(2) . . ?
C5 N1 C4 123.5(2) . . ?
H2A N2 H2B 120.0 . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
O1 C1 N1 122.3(2) . . ?
O1 C1 C2 127.6(2) . . ?
N1 C1 C2 110.1(2) . . ?
N1 C5 H5 107.2 . . ?
N1 C5 C6 108.7(2) . . ?
N1 C5 C7 111.7(2) . . ?
C6 C5 H5 107.2 . . ?
C7 C5 H5 107.2 . . ?
C7 C5 C6 114.5(2) . . ?
O2 C6 N2 122.7(3) . . ?
O2 C6 C5 121.3(2) . . ?
N2 C6 C5 116.0(2) . . ?
C1 C2 H2C 110.7 . . ?
C1 C2 H2D 110.7 . . ?
C1 C2 C3 105.0(2) . . ?
H2C C2 H2D 108.8 . . ?
C3 C2 H2C 110.7 . . ?
C3 C2 H2D 110.7 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C2 C3 C4 105.9(2) . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
N1 C4 C3 104.5(2) . . ?
N1 C4 H4A 110.9 . . ?
N1 C4 H4B 110.9 . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C5 C7 H7A 109.1 . . ?
C5 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C5 112.6(3) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.122
_oxdiff_exptl_absorpt_empirical_full_min 0.911
####################################################################### 
# 
# 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_S-Eti_ZnCl2
_database_code_depnum_ccdc_archive 'CCDC 1857804'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2018-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H28 Cl4 N4 O4 Zn2'
_chemical_formula_sum            'C16 H28 Cl4 N4 O4 Zn2'
_chemical_formula_weight         612.96
_chemical_absolute_configuration rm
_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'
Cl Cl 0.1484 0.1585 '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'

_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                   6.3692(3)
_cell_length_b                   11.6771(4)
_cell_length_c                   17.1077(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.496(4)
_cell_angle_gamma                90
_cell_volume                     1258.40(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1929
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9890
_cell_measurement_theta_min      3.6140
_shelx_estimated_absorpt_T_max   0.781
_shelx_estimated_absorpt_T_min   0.719
_exptl_absorpt_coefficient_mu    2.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6011
_diffrn_reflns_point_group_measured_fraction_full 0.843
_diffrn_reflns_point_group_measured_fraction_max 0.682
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.109
_diffrn_reflns_theta_min         3.234
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00   3.00   1.00    9.21    --  -16.52 -99.00-120.00   28
  2  ω    -38.00  44.00   1.00    9.21    --  -16.52  19.00 -30.00   82
  3  ω    -85.00  21.00   1.00    9.21    --  -16.52 -19.00 120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0464626000
_diffrn_orient_matrix_UB_12      0.0222871000
_diffrn_orient_matrix_UB_13      0.0320038000
_diffrn_orient_matrix_UB_21      -0.1010683000
_diffrn_orient_matrix_UB_22      -0.0004704000
_diffrn_orient_matrix_UB_23      -0.0238164000
_diffrn_orient_matrix_UB_31      -0.0175306000
_diffrn_orient_matrix_UB_32      -0.0565144000
_diffrn_orient_matrix_UB_33      0.0128382000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.529
_reflns_Friedel_fraction_full    0.670
_reflns_Friedel_fraction_max     0.495
_reflns_number_gt                4031
_reflns_number_total             4612
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 
;
 Flack x determined using 1288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4612
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.001
_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)+(0.0420P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0922
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C7(H7A,H7B), C2(H2C,H2D), C4(H4C,H4D),
 C11(H11A,H11B), C3(H3A,H3B), C15(H15A,H15B)
2.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N2(H2A,H2B)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Zn2 Zn 0.03048(10) 0.38968(6) 0.15068(4) 0.02843(18) Uani 1 1 d . . . . .
Zn1 Zn 0.06238(12) 0.42778(6) 0.63200(4) 0.0340(2) Uani 1 1 d . . . . .
Cl4 Cl 0.1024(3) 0.51394(16) 0.06172(11) 0.0441(4) Uani 1 1 d . . . . .
Cl3 Cl -0.3161(3) 0.36649(15) 0.15096(13) 0.0505(5) Uani 1 1 d . . . . .
Cl2 Cl -0.1421(3) 0.58573(17) 0.61669(12) 0.0486(5) Uani 1 1 d . . . . .
Cl1 Cl -0.0937(3) 0.26783(16) 0.65798(12) 0.0507(5) Uani 1 1 d . . . . .
O1 O 0.8316(7) 0.7343(4) 0.8462(3) 0.0324(11) Uani 1 1 d . . . . .
O2 O 0.3195(7) 0.4570(4) 0.7103(3) 0.0414(12) Uani 1 1 d . . . . .
O3 O 0.1559(7) 0.4306(4) 0.2608(2) 0.0377(11) Uani 1 1 d . . . . .
O4 O 0.2022(8) 0.3994(5) 0.5367(3) 0.0481(12) Uani 1 1 d . . . . .
N3 N 0.3952(9) 0.4982(5) 0.3614(3) 0.0317(13) Uani 1 1 d . . . . .
N1 N 0.6100(8) 0.5966(5) 0.8796(3) 0.0293(12) Uani 1 1 d . . . . .
C1 C 0.7296(10) 0.6893(5) 0.8943(4) 0.0287(14) Uani 1 1 d . . . . .
C9 C 0.3022(10) 0.4977(5) 0.2853(4) 0.0264(14) Uani 1 1 d . . . . .
N4 N 0.1342(11) 0.5617(5) 0.4675(4) 0.0475(16) Uani 1 1 d . . . . .
H4A H 0.058699 0.588969 0.500845 0.057 Uiso 1 1 calc R . . . .
H4B H 0.152264 0.600952 0.426447 0.057 Uiso 1 1 calc R . . . .
C6 C 0.3725(11) 0.5349(6) 0.7589(4) 0.0332(15) Uani 1 1 d . . . . .
C10 C 0.3995(11) 0.5871(6) 0.2398(4) 0.0389(17) Uani 1 1 d . . . . .
H10A H 0.297373 0.646682 0.222095 0.047 Uiso 1 1 calc R . . . .
H10B H 0.450097 0.553828 0.194083 0.047 Uiso 1 1 calc R . . . .
C14 C 0.2216(11) 0.4603(6) 0.4791(4) 0.0362(16) Uani 1 1 d . . . . .
N2 N 0.2516(10) 0.6217(5) 0.7689(4) 0.0512(18) Uani 1 1 d . . . . .
H2A H 0.127985 0.627407 0.741107 0.061 Uiso 1 1 calc R . . . .
H2B H 0.295217 0.673454 0.803235 0.061 Uiso 1 1 calc R . . . .
C12 C 0.5656(13) 0.5831(7) 0.3769(5) 0.050(2) Uani 1 1 d . . . . .
H12A H 0.698231 0.547026 0.399107 0.060 Uiso 1 1 calc R . . . .
H12B H 0.530428 0.641326 0.413329 0.060 Uiso 1 1 calc R . . . .
C5 C 0.5960(11) 0.5296(6) 0.8072(4) 0.0326(15) Uani 1 1 d . . . . .
H5 H 0.693233 0.564748 0.774806 0.039 Uiso 1 1 calc R . . . .
C7 C 0.6662(11) 0.4046(6) 0.8211(4) 0.0446(18) Uani 1 1 d . . . . .
H7A H 0.577091 0.367995 0.855082 0.054 Uiso 1 1 calc R . . . .
H7B H 0.647143 0.364295 0.770986 0.054 Uiso 1 1 calc R . . . .
C2 C 0.7221(11) 0.7277(6) 0.9782(4) 0.0354(16) Uani 1 1 d . . . . .
H2C H 0.687729 0.808507 0.979870 0.042 Uiso 1 1 calc R . . . .
H2D H 0.857281 0.714379 1.011217 0.042 Uiso 1 1 calc R . . . .
C13 C 0.3477(10) 0.4132(6) 0.4179(3) 0.0367(16) Uani 1 1 d . . . . .
H13 H 0.257578 0.355549 0.387768 0.044 Uiso 1 1 calc R . . . .
C4 C 0.5157(13) 0.5562(6) 0.9483(4) 0.0454(19) Uani 1 1 d . . . . .
H4C H 0.587160 0.487922 0.970967 0.055 Uiso 1 1 calc R . . . .
H4D H 0.365750 0.539701 0.933665 0.055 Uiso 1 1 calc R . . . .
C11 C 0.5815(14) 0.6346(8) 0.2969(6) 0.067(3) Uani 1 1 d . . . . .
H11A H 0.572258 0.717401 0.299174 0.080 Uiso 1 1 calc R . . . .
H11B H 0.715856 0.614164 0.280325 0.080 Uiso 1 1 calc R . . . .
C3 C 0.5493(15) 0.6555(7) 1.0053(5) 0.053(2) Uani 1 1 d . . . . .
H3A H 0.592946 0.628357 1.058852 0.063 Uiso 1 1 calc R . . . .
H3B H 0.419688 0.699581 1.003909 0.063 Uiso 1 1 calc R . . . .
C8 C 0.8972(13) 0.3955(9) 0.8589(5) 0.068(3) Uani 1 1 d . . . . .
H8A H 0.984170 0.439906 0.829015 0.103 Uiso 1 1 calc GR . . . .
H8B H 0.941020 0.316786 0.859541 0.103 Uiso 1 1 calc GR . . . .
H8C H 0.912175 0.423976 0.912096 0.103 Uiso 1 1 calc GR . . . .
C15 C 0.5463(14) 0.3505(8) 0.4569(5) 0.061(3) Uani 1 1 d . . . . .
H15A H 0.507050 0.293673 0.493494 0.073 Uiso 1 1 calc R . . . .
H15B H 0.642330 0.404671 0.486639 0.073 Uiso 1 1 calc R . . . .
C16 C 0.6583(18) 0.2919(9) 0.3947(7) 0.086(4) Uani 1 1 d . . . . .
H16A H 0.562365 0.239288 0.364675 0.130 Uiso 1 1 calc GR . . . .
H16B H 0.780037 0.250930 0.420350 0.130 Uiso 1 1 calc GR . . . .
H16C H 0.702950 0.348560 0.359980 0.130 Uiso 1 1 calc GR . . . .


_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
Zn2 Cl4 2.1996(19) . ?
Zn2 Cl3 2.2249(18) . ?
Zn2 O1 2.013(4) 2_646 ?
Zn2 O3 1.993(4) . ?
Zn1 Cl2 2.251(2) . ?
Zn1 Cl1 2.192(2) . ?
Zn1 O2 1.985(5) . ?
Zn1 O4 1.997(5) . ?
O1 C1 1.239(8) . ?
O2 C6 1.246(8) . ?
O3 C9 1.242(7) . ?
O4 C14 1.237(8) . ?
N3 C9 1.349(8) . ?
N3 C12 1.465(9) . ?
N3 C13 1.448(9) . ?
N1 C1 1.326(8) . ?
N1 C5 1.457(8) . ?
N1 C4 1.475(9) . ?
C1 C2 1.511(9) . ?
C9 C10 1.490(9) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C14 1.311(8) . ?
C6 N2 1.299(9) . ?
C6 C5 1.538(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.507(11) . ?
C14 C13 1.514(9) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.512(12) . ?
C5 H5 0.9800 . ?
C5 C7 1.535(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.521(9) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C2 C3 1.512(11) . ?
C13 H13 0.9800 . ?
C13 C15 1.527(9) . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C4 C3 1.511(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.528(12) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
Cl4 Zn2 Cl3 112.96(8) . . ?
O1 Zn2 Cl4 118.56(14) 2_646 . ?
O1 Zn2 Cl3 108.63(14) 2_646 . ?
O3 Zn2 Cl4 113.60(14) . . ?
O3 Zn2 Cl3 106.65(14) . . ?
O3 Zn2 O1 94.54(19) . 2_646 ?
Cl1 Zn1 Cl2 116.73(8) . . ?
O2 Zn1 Cl2 110.07(15) . . ?
O2 Zn1 Cl1 111.29(16) . . ?
O2 Zn1 O4 99.0(2) . . ?
O4 Zn1 Cl2 111.18(16) . . ?
O4 Zn1 Cl1 107.10(17) . . ?
C1 O1 Zn2 129.4(4) . 2_656 ?
C6 O2 Zn1 133.7(5) . . ?
C9 O3 Zn2 130.2(4) . . ?
C14 O4 Zn1 131.6(5) . . ?
C9 N3 C12 112.6(6) . . ?
C9 N3 C13 122.4(5) . . ?
C13 N3 C12 124.4(5) . . ?
C1 N1 C5 124.2(6) . . ?
C1 N1 C4 113.6(5) . . ?
C5 N1 C4 121.6(5) . . ?
O1 C1 N1 124.2(6) . . ?
O1 C1 C2 126.8(6) . . ?
N1 C1 C2 109.0(6) . . ?
O3 C9 N3 121.9(6) . . ?
O3 C9 C10 128.0(6) . . ?
N3 C9 C10 110.1(6) . . ?
H4A N4 H4B 120.0 . . ?
C14 N4 H4A 120.0 . . ?
C14 N4 H4B 120.0 . . ?
O2 C6 N2 123.4(7) . . ?
O2 C6 C5 117.9(6) . . ?
N2 C6 C5 118.7(6) . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C9 C10 C11 105.0(6) . . ?
H10A C10 H10B 108.8 . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
O4 C14 N4 123.4(7) . . ?
O4 C14 C13 117.9(6) . . ?
N4 C14 C13 118.7(6) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N3 C12 H12A 110.8 . . ?
N3 C12 H12B 110.8 . . ?
N3 C12 C11 104.6(6) . . ?
H12A C12 H12B 108.9 . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
N1 C5 C6 111.8(6) . . ?
N1 C5 H5 106.9 . . ?
N1 C5 C7 113.5(6) . . ?
C6 C5 H5 106.9 . . ?
C7 C5 C6 110.3(5) . . ?
C7 C5 H5 106.9 . . ?
C5 C7 H7A 109.2 . . ?
C5 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C5 112.0(7) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C1 C2 H2C 110.8 . . ?
C1 C2 H2D 110.8 . . ?
C1 C2 C3 104.6(6) . . ?
H2C C2 H2D 108.9 . . ?
C3 C2 H2C 110.8 . . ?
C3 C2 H2D 110.8 . . ?
N3 C13 C14 113.4(6) . . ?
N3 C13 H13 106.5 . . ?
N3 C13 C15 112.3(6) . . ?
C14 C13 H13 106.5 . . ?
C14 C13 C15 111.2(6) . . ?
C15 C13 H13 106.5 . . ?
N1 C4 H4C 111.1 . . ?
N1 C4 H4D 111.1 . . ?
N1 C4 C3 103.5(6) . . ?
H4C C4 H4D 109.0 . . ?
C3 C4 H4C 111.1 . . ?
C3 C4 H4D 111.1 . . ?
C10 C11 C12 107.0(7) . . ?
C10 C11 H11A 110.3 . . ?
C10 C11 H11B 110.3 . . ?
C12 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C4 C3 C2 105.7(6) . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 C16 110.6(7) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.285
_oxdiff_exptl_absorpt_empirical_full_min 0.884
