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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1441720'
_audit_update_record             
;
2016-08-01 deposited with the CCDC.
2016-08-02 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         'C22 H36 N6 O2 Zn2, 2(Cl O4)'
_chemical_formula_sum            'C22 H36 Cl2 N6 O10 Zn2'
_chemical_formula_weight         746.21

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.6370(10)
_cell_length_b                   17.0010(10)
_cell_length_c                   11.8120(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.5180(10)
_cell_angle_gamma                90
_cell_volume                     1516.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2841
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      24.07

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.819
_shelx_estimated_absorpt_T_min   0.594
_shelx_estimated_absorpt_T_max   0.701
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_T_max  0.683
_exptl_absorpt_process_details   sadabs
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8427
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.115
_diffrn_reflns_theta_max         25.093
_diffrn_reflns_theta_full        25.093
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2690
_reflns_number_gt                2272
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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 > 2sigma(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     
'w=1/[σ²(Fo²)+(0.1912P)²+0.7868P] 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_number_reflns         2690
_refine_ls_number_parameters     193
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.2444
_refine_ls_wR_factor_gt          0.2248
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_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 0.67228(7) 0.02661(3) 0.60449(4) 0.0291(3) Uani 1 1 d . . . . .
N2 N 0.6700(11) -0.0204(4) 0.7857(7) 0.076(2) Uani 1 1 d . . . . .
H2A H 0.5743 -0.0502 0.7864 0.091 Uiso 1 1 calc R U . . .
H2B H 0.7648 -0.0507 0.8053 0.091 Uiso 1 1 calc R U . . .
N3 N 0.6818(8) 0.1408(4) 0.7190(6) 0.0657(16) Uani 1 1 d . . . . .
O1 O 0.6032(7) -0.0690(3) 0.4777(4) 0.065 Uani 1 1 d . . . . .
O2 O 0.0513(12) 0.9036(5) 0.8444(8) 0.123(3) Uani 1 1 d . . . . .
O3 O 0.2840(10) 0.9047(5) 0.7372(8) 0.120(3) Uani 1 1 d . . . . .
O4 O 0.0294(11) 0.9780(4) 0.6766(7) 0.098(2) Uani 1 1 d . . . . .
O5 O 0.224(2) 1.0120(8) 0.8359(9) 0.178(6) Uani 1 1 d . . . . .
C1 C 0.3579(9) 0.1450(4) 0.5129(6) 0.0526(15) Uani 1 1 d . . . . .
C2 C 0.2594(10) 0.1742(5) 0.4123(7) 0.068(2) Uani 1 1 d . . . . .
H2 H 0.2203 0.1399 0.3525 0.082 Uiso 1 1 calc R U . . .
C3 C 0.2197(13) 0.2529(5) 0.4005(9) 0.080(2) Uani 1 1 d . . . . .
H3 H 0.1599 0.2719 0.3316 0.097 Uiso 1 1 calc R U . . .
C4 C 0.2689(14) 0.3042(5) 0.4916(10) 0.087(3) Uani 1 1 d . . . . .
H4 H 0.2389 0.3573 0.4857 0.104 Uiso 1 1 calc R U . . .
C5 C 0.3585(13) 0.2758(5) 0.5858(9) 0.082(2) Uani 1 1 d . . . . .
H5 H 0.3934 0.3108 0.6454 0.098 Uiso 1 1 calc R U . . .
C6 C 0.4047(11) 0.1986(4) 0.6032(7) 0.0627(18) Uani 1 1 d . . . . .
C7 C 0.4988(11) 0.1713(5) 0.7168(8) 0.077(2) Uani 1 1 d . . . . .
H7A H 0.5034 0.2149 0.7701 0.092 Uiso 1 1 calc R U . . .
H7B H 0.4281 0.1302 0.7448 0.092 Uiso 1 1 calc R U . . .
C9 C 0.6701(15) 0.0423(7) 0.8701(9) 0.093(3) Uani 1 1 d . . . . .
H9A H 0.7338 0.0250 0.9430 0.111 Uiso 1 1 calc R U . . .
H9B H 0.5492 0.0540 0.8806 0.111 Uiso 1 1 calc R U . . .
C10 C 0.7582(14) 0.1174(5) 0.8308(7) 0.079(2) Uani 1 1 d . . . . .
H10A H 0.7458 0.1597 0.8841 0.095 Uiso 1 1 calc R U . . .
H10B H 0.8836 0.1077 0.8320 0.095 Uiso 1 1 calc R U . . .
Cl1 Cl 0.1484(3) 0.95070(16) 0.7753(2) 0.0815(7) Uani 1 1 d . . . . .
N1 N 0.8704(11) 0.1079(5) 0.5304(7) 0.092(2) Uani 0.75 1 d . . P A 1
H1A H 0.9600 0.0799 0.5112 0.110 Uiso 0.75 1 calc R U P A 1
H1B H 0.8169 0.1326 0.4684 0.110 Uiso 0.75 1 calc R U P A 1
C11 C 0.7930(12) 0.2008(5) 0.6705(9) 0.081(3) Uani 0.75 1 d . . P A 1
H11A H 0.7189 0.2314 0.6129 0.097 Uiso 0.75 1 calc R U P A 1
H11B H 0.8434 0.2364 0.7309 0.097 Uiso 0.75 1 calc R U P A 1
C8 C 0.9349(16) 0.1646(7) 0.6196(12) 0.079(3) Uani 0.75 1 d . . P A 1
H8A H 1.0151 0.1382 0.6790 0.095 Uiso 0.75 1 calc R U P A 1
H8B H 1.0012 0.2053 0.5870 0.095 Uiso 0.75 1 calc R U P A 1
C8' C 0.820(6) 0.187(2) 0.550(3) 0.080(9) Uani 0.25 1 d . U P A 2
H8'A H 0.7114 0.1996 0.4997 0.096 Uiso 0.25 1 calc R U P A 2
H8'B H 0.9114 0.2227 0.5316 0.096 Uiso 0.25 1 calc R U P A 2
N1' N 0.8704(11) 0.1079(5) 0.5304(7) 0.092(2) Uani 0.25 1 d . . P A 2
H1'A H 0.9802 0.0987 0.5650 0.110 Uiso 0.25 1 calc R U P A 2
H1'B H 0.8663 0.0992 0.4558 0.110 Uiso 0.25 1 calc R U P A 2
C11' C 0.7930(12) 0.2008(5) 0.6705(9) 0.081(3) Uani 0.25 1 d . . P A 2
H11C H 0.7384 0.2520 0.6753 0.097 Uiso 0.25 1 calc R U P A 2
H11D H 0.9080 0.2025 0.7180 0.097 Uiso 0.25 1 calc R U P A 2


_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 O1 2.220(5) . ?
Zn1 N2 2.288(8) . ?
Zn1 O1 2.299(5) 3_656 ?
Zn1 N1' 2.314(8) . ?
Zn1 N1 2.314(8) . ?
Zn1 N3 2.361(6) . ?
N2 C9 1.459(14) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N3 C10 1.419(10) . ?
N3 C7 1.488(11) . ?
N3 C11' 1.495(10) . ?
N3 C11 1.495(10) . ?
O1 C1 1.326(8) 3_656 ?
O1 Zn1 2.299(5) 3_656 ?
O2 Cl1 1.427(8) . ?
O3 Cl1 1.423(8) . ?
O4 Cl1 1.444(8) . ?
O5 Cl1 1.345(9) . ?
C1 O1 1.326(8) 3_656 ?
C1 C2 1.401(10) . ?
C1 C6 1.409(10) . ?
C2 C3 1.373(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.309(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.498(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.546(15) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N1 C8 1.458(13) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C11 C8 1.453(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8' N1' 1.43(4) . ?
C8' C11' 1.48(4) . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
N1' H1'A 0.8900 . ?
N1' H1'B 0.8900 . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?

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 Zn1 N2 110.0(2) . . ?
O1 Zn1 O1 80.42(19) . 3_656 ?
N2 Zn1 O1 111.8(2) . 3_656 ?
O1 Zn1 N1' 106.6(2) . . ?
N2 Zn1 N1' 131.2(3) . . ?
O1 Zn1 N1' 105.2(3) 3_656 . ?
O1 Zn1 N1 106.6(2) . . ?
N2 Zn1 N1 131.2(3) . . ?
O1 Zn1 N1 105.2(3) 3_656 . ?
O1 Zn1 N3 166.5(2) . . ?
N2 Zn1 N3 75.8(2) . . ?
O1 Zn1 N3 86.2(2) 3_656 . ?
N1' Zn1 N3 76.1(3) . . ?
N1 Zn1 N3 76.1(3) . . ?
C9 N2 Zn1 112.6(6) . . ?
C9 N2 H2A 109.1 . . ?
Zn1 N2 H2A 109.1 . . ?
C9 N2 H2B 109.1 . . ?
Zn1 N2 H2B 109.1 . . ?
H2A N2 H2B 107.8 . . ?
C10 N3 C7 111.7(7) . . ?
C10 N3 C11' 111.7(7) . . ?
C7 N3 C11' 109.9(7) . . ?
C10 N3 C11 111.7(7) . . ?
C7 N3 C11 109.9(7) . . ?
C10 N3 Zn1 106.0(5) . . ?
C7 N3 Zn1 109.1(5) . . ?
C11' N3 Zn1 108.2(5) . . ?
C11 N3 Zn1 108.2(5) . . ?
C1 O1 Zn1 129.0(5) 3_656 . ?
C1 O1 Zn1 121.3(4) 3_656 3_656 ?
Zn1 O1 Zn1 99.58(19) . 3_656 ?
O1 C1 C2 120.1(6) 3_656 . ?
O1 C1 C6 122.6(7) 3_656 . ?
C2 C1 C6 117.2(7) . . ?
C3 C2 C1 121.0(8) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.1(9) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 118.2(8) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 125.0(9) . . ?
C4 C5 H5 117.5 . . ?
C6 C5 H5 117.5 . . ?
C5 C6 C1 118.5(8) . . ?
C5 C6 C7 120.7(8) . . ?
C1 C6 C7 120.8(7) . . ?
N3 C7 C6 116.6(7) . . ?
N3 C7 H7A 108.1 . . ?
C6 C7 H7A 108.1 . . ?
N3 C7 H7B 108.1 . . ?
C6 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
N2 C9 C10 110.8(8) . . ?
N2 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N3 C10 C9 111.9(8) . . ?
N3 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N3 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O5 Cl1 O3 108.6(8) . . ?
O5 Cl1 O2 110.4(6) . . ?
O3 Cl1 O2 109.7(5) . . ?
O5 Cl1 O4 110.4(8) . . ?
O3 Cl1 O4 108.8(5) . . ?
O2 Cl1 O4 108.9(5) . . ?
C8 N1 Zn1 107.0(6) . . ?
C8 N1 H1A 110.3 . . ?
Zn1 N1 H1A 110.3 . . ?
C8 N1 H1B 110.3 . . ?
Zn1 N1 H1B 110.3 . . ?
H1A N1 H1B 108.6 . . ?
C8 C11 N3 111.7(7) . . ?
C8 C11 H11A 109.3 . . ?
N3 C11 H11A 109.3 . . ?
C8 C11 H11B 109.3 . . ?
N3 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C8 N1 112.7(9) . . ?
C11 C8 H8A 109.0 . . ?
N1 C8 H8A 109.0 . . ?
C11 C8 H8B 109.0 . . ?
N1 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N1' C8' C11' 112(3) . . ?
N1' C8' H8'A 109.1 . . ?
C11' C8' H8'A 109.1 . . ?
N1' C8' H8'B 109.1 . . ?
C11' C8' H8'B 109.1 . . ?
H8'A C8' H8'B 107.9 . . ?
C8' N1' Zn1 107.2(17) . . ?
C8' N1' H1'A 110.3 . . ?
Zn1 N1' H1'A 110.3 . . ?
C8' N1' H1'B 110.3 . . ?
Zn1 N1' H1'B 110.3 . . ?
H1'A N1' H1'B 108.5 . . ?
C8' C11' N3 115.4(16) . . ?
C8' C11' H11C 108.4 . . ?
N3 C11' H11C 108.4 . . ?
C8' C11' H11D 108.4 . . ?
N3 C11' H11D 108.4 . . ?
H11C C11' H11D 107.5 . . ?

_refine_diff_density_max         2.101
_refine_diff_density_min         -1.504
_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_2
_database_code_depnum_ccdc_archive 'CCDC 1441721'
_audit_update_record             
;
2016-08-01 deposited with the CCDC.
2016-08-02 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         'C22 H36 Cu2 N6 O2, 2(Cl O4), 2(H2 O)'
_chemical_formula_sum            'C22 H40 Cl2 Cu2 N6 O12'
_chemical_formula_weight         778.58

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'
Cu Cu 0.3201 1.2651 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   16.857(2)
_cell_length_b                   10.4260(10)
_cell_length_c                   17.971(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.160(2)
_cell_angle_gamma                90
_cell_volume                     3145.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3528
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      24.17

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_F_000             1608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.590
_shelx_estimated_absorpt_T_min   0.630
_shelx_estimated_absorpt_T_max   0.731
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6302
_exptl_absorpt_correction_T_max  0.7313
_exptl_absorpt_process_details   sadabs
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14022
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.587
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5520
_reflns_number_gt                4174
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0899P)²+3.6920P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5520
_refine_ls_number_parameters     398
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1435
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.316
_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
Cu1 Cu 0.43632(3) 0.72128(5) 0.20208(3) 0.03821(19) Uani 1 1 d . . . . .
Cu2 Cu 0.58334(3) 0.89555(5) 0.22568(3) 0.03449(19) Uani 1 1 d . . . . .
C1 C 0.4391(3) 0.9652(4) 0.1173(3) 0.0358(10) Uani 1 1 d . . . . .
C2 C 0.3562(3) 0.9612(5) 0.1032(3) 0.0446(12) Uani 1 1 d . . . . .
H2 H 0.3281 0.8912 0.1191 0.054 Uiso 1 1 calc R U . . .
C3 C 0.3159(3) 1.0608(6) 0.0657(3) 0.0513(14) Uani 1 1 d . . . . .
H3 H 0.2607 1.0573 0.0573 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3556(3) 1.1644(5) 0.0408(3) 0.0518(14) Uani 1 1 d . . . . .
H4 H 0.3281 1.2312 0.0158 0.062 Uiso 1 1 calc R U . . .
C5 C 0.4380(3) 1.1674(5) 0.0537(3) 0.0483(13) Uani 1 1 d . . . . .
H5 H 0.4655 1.2374 0.0369 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4807(3) 1.0687(5) 0.0911(3) 0.0387(11) Uani 1 1 d . . . . .
C7 C 0.5735(3) 0.6659(5) 0.3215(3) 0.0373(11) Uani 1 1 d . . . . .
C8 C 0.5378(3) 0.5476(5) 0.3354(3) 0.0418(12) Uani 1 1 d . . . . .
C9 C 0.5559(3) 0.4900(6) 0.4049(3) 0.0548(15) Uani 1 1 d . . . . .
H9 H 0.5310 0.4133 0.4153 0.066 Uiso 1 1 calc R U . . .
C10 C 0.6093(4) 0.5433(7) 0.4583(3) 0.0634(17) Uani 1 1 d . . . . .
H10 H 0.6203 0.5032 0.5043 0.076 Uiso 1 1 calc R U . . .
C11 C 0.6463(3) 0.6558(6) 0.4433(3) 0.0542(14) Uani 1 1 d . . . . .
H11 H 0.6836 0.6910 0.4789 0.065 Uiso 1 1 calc R U . . .
C12 C 0.6292(3) 0.7173(5) 0.3764(3) 0.0458(12) Uani 1 1 d . . . . .
H12 H 0.6547 0.7941 0.3672 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5695(3) 1.0724(5) 0.0994(3) 0.0431(12) Uani 1 1 d . . . . .
H13A H 0.5867 1.1512 0.0771 0.052 Uiso 1 1 calc R U . . .
H13B H 0.5892 1.0016 0.0714 0.052 Uiso 1 1 calc R U . . .
C14 C 0.4831(3) 0.4835(5) 0.2761(3) 0.0450(12) Uani 1 1 d . . . . .
H14A H 0.5118 0.4704 0.2322 0.054 Uiso 1 1 calc R U . . .
H14B H 0.4687 0.3997 0.2941 0.054 Uiso 1 1 calc R U . . .
C15 C 0.7274(3) 0.9417(6) 0.1557(3) 0.0509(13) Uani 1 1 d . . . . .
H15A H 0.7113 0.9248 0.1034 0.061 Uiso 1 1 calc R U . . .
H15B H 0.7852 0.9416 0.1626 0.061 Uiso 1 1 calc R U . . .
C16 C 0.6962(3) 1.0686(5) 0.1775(3) 0.0500(13) Uani 1 1 d . . . . .
H16A H 0.7110 1.1336 0.1426 0.060 Uiso 1 1 calc R U . . .
H16B H 0.7199 1.0915 0.2269 0.060 Uiso 1 1 calc R U . . .
C17 C 0.5792(3) 1.1704(5) 0.2251(3) 0.0471(13) Uani 1 1 d . . . . .
H17A H 0.6096 1.2476 0.2174 0.057 Uiso 1 1 calc R U . . .
H17B H 0.5236 1.1884 0.2103 0.057 Uiso 1 1 calc R U . . .
C18 C 0.5887(3) 1.1350(5) 0.3051(3) 0.0527(14) Uani 1 1 d . . . . .
H18A H 0.6448 1.1287 0.3223 0.063 Uiso 1 1 calc R U . . .
H18B H 0.5647 1.1998 0.3346 0.063 Uiso 1 1 calc R U . . .
C20 C 0.3921(5) 0.4893(6) 0.1225(4) 0.0735(19) Uani 1 1 d . . . . .
H20A H 0.4398 0.4370 0.1241 0.088 Uiso 1 1 calc R U . . .
H20B H 0.3541 0.4561 0.0836 0.088 Uiso 1 1 calc R U . . .
C22 C 0.3188(4) 0.7139(6) 0.3081(4) 0.0673(17) Uani 1 1 d . . . . .
H22A H 0.2732 0.7028 0.2718 0.081 Uiso 1 1 calc R U . . .
H22B H 0.2999 0.7418 0.3549 0.081 Uiso 1 1 calc R U . . .
C23 C 0.3641(3) 0.5885(6) 0.3193(3) 0.0573(15) Uani 1 1 d . . . . .
H23A H 0.4014 0.5948 0.3635 0.069 Uiso 1 1 calc R U . . .
H23B H 0.3269 0.5199 0.3273 0.069 Uiso 1 1 calc R U . . .
C28 C 0.3573(4) 0.4828(6) 0.1966(3) 0.0600(16) Uani 1 1 d . . . . .
H28A H 0.3039 0.5180 0.1918 0.072 Uiso 1 1 calc R U . . .
H28B H 0.3542 0.3941 0.2124 0.072 Uiso 1 1 calc R U . . .
N1 N 0.5492(3) 1.0100(4) 0.3136(3) 0.0525(11) Uani 1 1 d . . . . .
H1A H 0.4966 1.0194 0.3104 0.063 Uiso 1 1 calc R U . . .
H1B H 0.5651 0.9749 0.3575 0.063 Uiso 1 1 calc R U . . .
N2 N 0.6071(2) 1.0652(4) 0.1777(2) 0.0374(9) Uani 1 1 d . . . . .
N3 N 0.6952(2) 0.8415(4) 0.2028(3) 0.0515(11) Uani 1 1 d . . . . .
H3A H 0.7265 0.8327 0.2451 0.062 Uiso 1 1 calc R U . . .
H3B H 0.6932 0.7666 0.1789 0.062 Uiso 1 1 calc R U . . .
N4 N 0.4119(5) 0.6243(5) 0.1057(3) 0.088(2) Uani 1 1 d . . . . .
H4A H 0.3711 0.6608 0.0789 0.106 Uiso 1 1 calc R U . . .
H4B H 0.4540 0.6265 0.0791 0.106 Uiso 1 1 calc R U . . .
N5 N 0.3728(3) 0.8084(5) 0.2817(3) 0.0618(13) Uani 1 1 d . . . . .
H5A H 0.4059 0.8366 0.3195 0.074 Uiso 1 1 calc R U . . .
H5B H 0.3454 0.8749 0.2618 0.074 Uiso 1 1 calc R U . . .
N6 N 0.4083(2) 0.5571(4) 0.2535(2) 0.0436(10) Uani 1 1 d . . . . .
O1 O 0.47961(19) 0.8702(3) 0.15500(19) 0.0427(8) Uani 1 1 d . . . . .
O2 O 0.5529(2) 0.7264(3) 0.25658(19) 0.0411(8) Uani 1 1 d . . . . .
O4 O 0.3130(6) 0.0783(9) 0.3951(5) 0.184(4) Uani 1 1 d . U . . .
O5 O 0.3057(5) 0.2735(7) 0.3540(4) 0.143(3) Uani 1 1 d . U . . .
O6 O 0.4258(3) 0.1997(6) 0.4044(3) 0.110(2) Uani 1 1 d . U . . .
O7 O 0.3713(4) 0.1276(7) 0.2891(3) 0.118(2) Uani 1 1 d . U . . .
O8 O 0.1780(4) 0.0494(6) 0.6786(3) 0.1080(15) Uani 1 1 d . U . . .
O9 O 0.2006(4) -0.1006(5) 0.5961(4) 0.1108(15) Uani 1 1 d . U . . .
O10 O 0.1913(4) 0.1051(6) 0.5569(4) 0.1102(15) Uani 1 1 d . U . . .
O11 O 0.0831(4) 0.0103(8) 0.5833(4) 0.1369(17) Uani 1 1 d . U . . .
O1W O 0.5363(5) 0.1763(9) 0.5587(4) 0.160(3) Uani 1 1 d . . . . .
H1WA H 0.5094 0.1953 0.5264 0.192 Uiso 1 1 d R U . . .
H1WB H 0.5820 0.1659 0.5417 0.192 Uiso 1 1 d R U . . .
O2W O 0.3610(7) 0.9531(12) 0.5268(5) 0.237(6) Uani 1 1 d . . . . .
H2WA H 0.3570 1.0145 0.4956 0.284 Uiso 1 1 d R U . . .
H2WB H 0.3147 0.9294 0.5363 0.284 Uiso 1 1 d R U . . .
Cl1 Cl 0.35467(9) 0.17073(14) 0.36033(9) 0.0586(4) Uani 1 1 d . . . . .
Cl2 Cl 0.16272(9) 0.01517(15) 0.60413(8) 0.0600(4) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.942(3) . ?
Cu1 N4 2.016(5) . ?
Cu1 N6 2.022(4) . ?
Cu1 N5 2.073(5) . ?
Cu1 O2 2.117(3) . ?
Cu2 O2 1.932(3) . ?
Cu2 N2 2.023(4) . ?
Cu2 N3 2.045(4) . ?
Cu2 O1 2.084(3) . ?
Cu2 N1 2.101(4) . ?
C1 O1 1.351(5) . ?
C1 C6 1.392(7) . ?
C1 C2 1.398(7) . ?
C2 C3 1.382(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(7) . ?
C5 H5 0.9300 . ?
C6 C13 1.491(7) . ?
C7 O2 1.345(6) . ?
C7 C8 1.404(7) . ?
C7 C12 1.406(7) . ?
C8 C9 1.394(7) . ?
C8 C14 1.503(7) . ?
C9 C10 1.374(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N2 1.492(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N6 1.501(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.479(7) . ?
C15 C16 1.489(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N2 1.504(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.479(8) . ?
C17 N2 1.491(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N1 1.477(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 N4 1.484(8) . ?
C20 C28 1.503(9) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C22 N5 1.449(8) . ?
C22 C23 1.518(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 N6 1.490(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C28 N6 1.492(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
O4 Cl1 1.376(7) . ?
O5 Cl1 1.352(6) . ?
O6 Cl1 1.408(5) . ?
O7 Cl1 1.408(6) . ?
O8 Cl2 1.387(5) . ?
O9 Cl2 1.379(6) . ?
O10 Cl2 1.380(6) . ?
O11 Cl2 1.362(6) . ?
O1W H1WA 0.7302 . ?
O1W H1WB 0.8613 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?

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 Cu1 N4 94.71(19) . . ?
O1 Cu1 N6 171.45(15) . . ?
N4 Cu1 N6 86.0(2) . . ?
O1 Cu1 N5 100.87(17) . . ?
N4 Cu1 N5 137.3(3) . . ?
N6 Cu1 N5 84.18(18) . . ?
O1 Cu1 O2 79.15(13) . . ?
N4 Cu1 O2 121.3(2) . . ?
N6 Cu1 O2 93.18(14) . . ?
N5 Cu1 O2 100.71(18) . . ?
O2 Cu2 N2 171.18(15) . . ?
O2 Cu2 N3 94.55(17) . . ?
N2 Cu2 N3 86.23(17) . . ?
O2 Cu2 O1 80.20(13) . . ?
N2 Cu2 O1 92.19(14) . . ?
N3 Cu2 O1 125.54(17) . . ?
O2 Cu2 N1 101.83(16) . . ?
N2 Cu2 N1 84.36(16) . . ?
N3 Cu2 N1 128.84(19) . . ?
O1 Cu2 N1 105.01(17) . . ?
O1 C1 C6 119.4(4) . . ?
O1 C1 C2 121.4(4) . . ?
C6 C1 C2 119.2(4) . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.4(5) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 122.0(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 118.7(5) . . ?
C1 C6 C13 121.2(4) . . ?
C5 C6 C13 120.0(5) . . ?
O2 C7 C8 119.0(4) . . ?
O2 C7 C12 122.3(5) . . ?
C8 C7 C12 118.7(5) . . ?
C9 C8 C7 118.4(5) . . ?
C9 C8 C14 120.9(5) . . ?
C7 C8 C14 120.7(4) . . ?
C10 C9 C8 121.9(6) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C11 C10 C9 119.4(5) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 120.7(5) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 120.8(5) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C6 C13 N2 115.5(4) . . ?
C6 C13 H13A 108.4 . . ?
N2 C13 H13A 108.4 . . ?
C6 C13 H13B 108.4 . . ?
N2 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
N6 C14 C8 114.3(4) . . ?
N6 C14 H14A 108.7 . . ?
C8 C14 H14A 108.7 . . ?
N6 C14 H14B 108.7 . . ?
C8 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
N3 C15 C16 108.7(4) . . ?
N3 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
N3 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 N2 110.9(4) . . ?
C15 C16 H16A 109.5 . . ?
N2 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 N2 111.0(4) . . ?
C18 C17 H17A 109.4 . . ?
N2 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
N2 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N1 C18 C17 108.1(4) . . ?
N1 C18 H18A 110.1 . . ?
C17 C18 H18A 110.1 . . ?
N1 C18 H18B 110.1 . . ?
C17 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
N4 C20 C28 109.6(5) . . ?
N4 C20 H20A 109.7 . . ?
C28 C20 H20A 109.7 . . ?
N4 C20 H20B 109.7 . . ?
C28 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
N5 C22 C23 107.8(5) . . ?
N5 C22 H22A 110.1 . . ?
C23 C22 H22A 110.1 . . ?
N5 C22 H22B 110.1 . . ?
C23 C22 H22B 110.1 . . ?
H22A C22 H22B 108.5 . . ?
N6 C23 C22 111.5(5) . . ?
N6 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
N6 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
N6 C28 C20 109.7(5) . . ?
N6 C28 H28A 109.7 . . ?
C20 C28 H28A 109.7 . . ?
N6 C28 H28B 109.7 . . ?
C20 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
C18 N1 Cu2 105.5(3) . . ?
C18 N1 H1A 110.6 . . ?
Cu2 N1 H1A 110.6 . . ?
C18 N1 H1B 110.6 . . ?
Cu2 N1 H1B 110.6 . . ?
H1A N1 H1B 108.8 . . ?
C17 N2 C13 111.9(4) . . ?
C17 N2 C16 110.5(4) . . ?
C13 N2 C16 109.6(4) . . ?
C17 N2 Cu2 108.4(3) . . ?
C13 N2 Cu2 111.3(3) . . ?
C16 N2 Cu2 105.0(3) . . ?
C15 N3 Cu2 108.2(3) . . ?
C15 N3 H3A 110.0 . . ?
Cu2 N3 H3A 110.0 . . ?
C15 N3 H3B 110.0 . . ?
Cu2 N3 H3B 110.0 . . ?
H3A N3 H3B 108.4 . . ?
C20 N4 Cu1 109.4(4) . . ?
C20 N4 H4A 109.8 . . ?
Cu1 N4 H4A 109.8 . . ?
C20 N4 H4B 109.8 . . ?
Cu1 N4 H4B 109.8 . . ?
H4A N4 H4B 108.2 . . ?
C22 N5 Cu1 107.9(4) . . ?
C22 N5 H5A 110.1 . . ?
Cu1 N5 H5A 110.1 . . ?
C22 N5 H5B 110.1 . . ?
Cu1 N5 H5B 110.1 . . ?
H5A N5 H5B 108.4 . . ?
C23 N6 C28 111.1(4) . . ?
C23 N6 C14 111.5(4) . . ?
C28 N6 C14 109.7(4) . . ?
C23 N6 Cu1 109.3(3) . . ?
C28 N6 Cu1 105.7(3) . . ?
C14 N6 Cu1 109.3(3) . . ?
C1 O1 Cu1 127.8(3) . . ?
C1 O1 Cu2 124.9(3) . . ?
Cu1 O1 Cu2 99.40(14) . . ?
C7 O2 Cu2 128.6(3) . . ?
C7 O2 Cu1 123.1(3) . . ?
Cu2 O2 Cu1 98.58(14) . . ?
H1WA O1W H1WB 105.2 . . ?
H2WA O2W H2WB 109.5 . . ?
O5 Cl1 O4 105.1(6) . . ?
O5 Cl1 O7 110.3(4) . . ?
O4 Cl1 O7 109.9(6) . . ?
O5 Cl1 O6 111.1(4) . . ?
O4 Cl1 O6 109.8(5) . . ?
O7 Cl1 O6 110.6(4) . . ?
O11 Cl2 O9 113.1(5) . . ?
O11 Cl2 O10 104.2(4) . . ?
O9 Cl2 O10 109.9(4) . . ?
O11 Cl2 O8 111.5(4) . . ?
O9 Cl2 O8 106.2(4) . . ?
O10 Cl2 O8 112.0(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 C3 178.7(5) . . . . ?
C6 C1 C2 C3 -2.0(7) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C3 C4 C5 C6 -0.1(8) . . . . ?
O1 C1 C6 C5 -178.6(4) . . . . ?
C2 C1 C6 C5 2.1(7) . . . . ?
O1 C1 C6 C13 4.2(7) . . . . ?
C2 C1 C6 C13 -175.1(5) . . . . ?
C4 C5 C6 C1 -1.1(8) . . . . ?
C4 C5 C6 C13 176.2(5) . . . . ?
O2 C7 C8 C9 -176.0(4) . . . . ?
C12 C7 C8 C9 3.6(7) . . . . ?
O2 C7 C8 C14 5.5(7) . . . . ?
C12 C7 C8 C14 -174.9(4) . . . . ?
C7 C8 C9 C10 -2.4(8) . . . . ?
C14 C8 C9 C10 176.1(5) . . . . ?
C8 C9 C10 C11 -0.2(9) . . . . ?
C9 C10 C11 C12 1.6(9) . . . . ?
C10 C11 C12 C7 -0.4(8) . . . . ?
O2 C7 C12 C11 177.3(5) . . . . ?
C8 C7 C12 C11 -2.3(7) . . . . ?
C1 C6 C13 N2 -59.1(6) . . . . ?
C5 C6 C13 N2 123.8(5) . . . . ?
C9 C8 C14 N6 117.5(5) . . . . ?
C7 C8 C14 N6 -64.0(6) . . . . ?
N3 C15 C16 N2 -51.5(6) . . . . ?
N2 C17 C18 N1 -53.0(6) . . . . ?
N5 C22 C23 N6 -47.7(7) . . . . ?
N4 C20 C28 N6 -48.1(7) . . . . ?
C17 C18 N1 Cu2 44.0(5) . . . . ?
C18 C17 N2 C13 156.7(4) . . . . ?
C18 C17 N2 C16 -80.9(5) . . . . ?
C18 C17 N2 Cu2 33.6(5) . . . . ?
C6 C13 N2 C17 -57.6(6) . . . . ?
C6 C13 N2 C16 179.5(4) . . . . ?
C6 C13 N2 Cu2 63.8(5) . . . . ?
C15 C16 N2 C17 158.9(4) . . . . ?
C15 C16 N2 C13 -77.4(5) . . . . ?
C15 C16 N2 Cu2 42.2(5) . . . . ?
C16 C15 N3 Cu2 33.3(5) . . . . ?
C28 C20 N4 Cu1 28.0(7) . . . . ?
C23 C22 N5 Cu1 42.8(6) . . . . ?
C22 C23 N6 C28 -88.3(6) . . . . ?
C22 C23 N6 C14 149.0(5) . . . . ?
C22 C23 N6 Cu1 28.0(6) . . . . ?
C20 C28 N6 C23 161.8(5) . . . . ?
C20 C28 N6 C14 -74.5(6) . . . . ?
C20 C28 N6 Cu1 43.3(6) . . . . ?
C8 C14 N6 C23 -54.5(6) . . . . ?
C8 C14 N6 C28 -178.0(4) . . . . ?
C8 C14 N6 Cu1 66.5(5) . . . . ?
C6 C1 O1 Cu1 176.2(3) . . . . ?
C2 C1 O1 Cu1 -4.5(6) . . . . ?
C6 C1 O1 Cu2 33.8(6) . . . . ?
C2 C1 O1 Cu2 -146.9(4) . . . . ?
C8 C7 O2 Cu2 173.5(3) . . . . ?
C12 C7 O2 Cu2 -6.1(7) . . . . ?
C8 C7 O2 Cu1 35.1(6) . . . . ?
C12 C7 O2 Cu1 -144.5(4) . . . . ?

_refine_diff_density_max         0.970
_refine_diff_density_min         -1.080
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1441722'
_audit_update_record             
;
2016-07-12 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H36 Cd2 N6 O2, 2(Cl O4), C2 H3 N'
_chemical_formula_sum            'C24 H39 Cd2 Cl2 N7 O10'
_chemical_formula_weight         881.32

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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                   11.6570(10)
_cell_length_b                   16.0490(10)
_cell_length_c                   17.4020(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3255.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5700
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      23.13

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1768
_exptl_absorpt_coefficient_mu    1.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_T_max  0.7491
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19585
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         26.02
_reflns_number_total             3535
_reflns_number_gt                3166
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.1472P)²+3.6450P] 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 (1983), 3535 Friedel pairs'
_refine_ls_abs_structure_Flack   0.41(7)
_refine_ls_number_reflns         3535
_refine_ls_number_parameters     443
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1883
_refine_ls_wR_factor_gt          0.1795
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.098
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.63808(8) -0.05758(6) 0.47554(5) 0.0454(3) Uani 1 1 d U . .
Cd2 Cd 0.48106(8) 0.09313(5) 0.50918(6) 0.0451(3) Uani 1 1 d U . .
N1 N 0.5437(7) 0.2132(5) 0.5215(6) 0.0353(19) Uani 1 1 d . . .
H1A H 0.6209 0.2129 0.5191 0.042 Uiso 1 1 calc R . .
H1B H 0.5171 0.2457 0.4833 0.042 Uiso 1 1 calc R . .
N2 N 0.3233(8) 0.0774(6) 0.4567(6) 0.040(2) Uani 1 1 d . . .
H2A H 0.3221 0.1039 0.4112 0.049 Uiso 1 1 calc R . .
H2B H 0.3097 0.0229 0.4485 0.049 Uiso 1 1 calc R . .
N3 N 0.3811(8) 0.1245(5) 0.6092(5) 0.0303(18) Uani 1 1 d . . .
N4 N 0.5566(9) -0.1431(6) 0.4097(6) 0.039(2) Uani 1 1 d . . .
H4A H 0.5280 -0.1837 0.4397 0.047 Uiso 1 1 calc R . .
H4B H 0.4978 -0.1187 0.3848 0.047 Uiso 1 1 calc R . .
N5 N 0.7602(8) -0.0971(6) 0.5515(5) 0.036(2) Uani 1 1 d . . .
H5A H 0.7607 -0.0633 0.5928 0.043 Uiso 1 1 calc R . .
H5B H 0.7431 -0.1489 0.5676 0.043 Uiso 1 1 calc R . .
N6 N 0.7757(6) -0.0718(5) 0.3933(5) 0.0236(16) Uani 1 1 d . . .
O1 O 0.6030(6) 0.0570(5) 0.4335(4) 0.0326(11) Uani 1 1 d U . .
O2 O 0.5257(6) -0.0152(4) 0.5580(4) 0.0252(13) Uani 1 1 d . . .
O7 O 0.1220(11) 0.7905(9) 0.4912(9) 0.088(4) Uani 1 1 d U . .
O8 O 0.3032(14) 0.7946(11) 0.4378(12) 0.107(5) Uani 1 1 d U . .
O9 O 0.1541(18) 0.8647(13) 0.3824(11) 0.125(6) Uani 1 1 d U . .
O10 O 0.233(3) 0.9077(17) 0.4937(16) 0.172(10) Uani 1 1 d U . .
C1 C 0.6429(8) 0.0952(6) 0.3715(5) 0.0222(16) Uani 1 1 d . . .
C2 C 0.5814(10) 0.1623(6) 0.3391(6) 0.032(2) Uani 1 1 d . . .
H2 H 0.5124 0.1788 0.3612 0.039 Uiso 1 1 calc R . .
C3 C 0.6218(11) 0.2039(7) 0.2748(6) 0.040(2) Uani 1 1 d . . .
H3 H 0.5794 0.2482 0.2552 0.047 Uiso 1 1 calc R . .
C4 C 0.7205(11) 0.1825(8) 0.2399(6) 0.041(3) Uani 1 1 d . . .
H4 H 0.7464 0.2113 0.1968 0.049 Uiso 1 1 calc R . .
C5 C 0.7849(10) 0.1136(6) 0.2711(6) 0.033(2) Uani 1 1 d . . .
H5 H 0.8518 0.0965 0.2467 0.040 Uiso 1 1 calc R . .
C6 C 0.7488(8) 0.0723(5) 0.3371(5) 0.0241(18) Uani 1 1 d . . .
C7 C 0.8283(9) 0.0092(6) 0.3723(6) 0.031(2) Uani 1 1 d . . .
H7A H 0.8904 -0.0013 0.3365 0.037 Uiso 1 1 calc R . .
H7B H 0.8617 0.0334 0.4182 0.037 Uiso 1 1 calc R . .
C8 C 0.7240(9) -0.1122(6) 0.3253(5) 0.028(2) Uani 1 1 d . . .
H8A H 0.7838 -0.1365 0.2937 0.033 Uiso 1 1 calc R . .
H8B H 0.6835 -0.0710 0.2948 0.033 Uiso 1 1 calc R . .
C9 C 0.6401(10) -0.1805(6) 0.3514(6) 0.033(2) Uani 1 1 d . . .
H9A H 0.5981 -0.2020 0.3075 0.039 Uiso 1 1 calc R . .
H9B H 0.6820 -0.2262 0.3747 0.039 Uiso 1 1 calc R . .
C10 C 0.8613(9) -0.1227(7) 0.4317(6) 0.033(2) Uani 1 1 d . . .
H10A H 0.9339 -0.1176 0.4049 0.039 Uiso 1 1 calc R . .
H10B H 0.8380 -0.1807 0.4296 0.039 Uiso 1 1 calc R . .
C11 C 0.8771(9) -0.0971(8) 0.5148(6) 0.042(3) Uani 1 1 d . . .
H11A H 0.9273 -0.1361 0.5410 0.050 Uiso 1 1 calc R . .
H11B H 0.9110 -0.0420 0.5177 0.050 Uiso 1 1 calc R . .
C12 C 0.4787(8) -0.0530(5) 0.6173(5) 0.0196(15) Uani 1 1 d . . .
C13 C 0.4282(9) -0.0078(7) 0.6778(6) 0.031(2) Uani 1 1 d . . .
C14 C 0.3761(10) -0.0498(8) 0.7383(6) 0.044(3) Uani 1 1 d . . .
H14 H 0.3409 -0.0191 0.7771 0.053 Uiso 1 1 calc R . .
C15 C 0.3751(10) -0.1373(9) 0.7427(7) 0.047(3) Uani 1 1 d . . .
H15 H 0.3385 -0.1646 0.7830 0.057 Uiso 1 1 calc R . .
C16 C 0.4320(11) -0.1834(7) 0.6831(7) 0.039(3) Uani 1 1 d . . .
H16 H 0.4360 -0.2412 0.6857 0.047 Uiso 1 1 calc R . .
C17 C 0.4808(11) -0.1416(6) 0.6221(6) 0.035(2) Uani 1 1 d . . .
H17 H 0.5160 -0.1719 0.5832 0.042 Uiso 1 1 calc R . .
C18 C 0.4289(12) 0.0852(8) 0.6789(6) 0.042(3) Uani 1 1 d . . .
H18A H 0.3853 0.1041 0.7231 0.051 Uiso 1 1 calc R . .
H18B H 0.5074 0.1041 0.6856 0.051 Uiso 1 1 calc R . .
C19 C 0.3894(13) 0.2169(7) 0.6161(9) 0.055(3) Uani 1 1 d U . .
H19A H 0.3344 0.2427 0.5817 0.066 Uiso 1 1 calc R . .
H19B H 0.3704 0.2335 0.6682 0.066 Uiso 1 1 calc R . .
C20 C 0.2356(10) 0.1122(10) 0.5080(11) 0.061(4) Uani 1 1 d . . .
H20A H 0.1618 0.0877 0.4957 0.074 Uiso 1 1 calc R . .
H20B H 0.2301 0.1718 0.4995 0.074 Uiso 1 1 calc R . .
C22 C 0.5055(12) 0.2464(7) 0.5971(8) 0.048(3) Uani 1 1 d . . .
H22A H 0.5586 0.2287 0.6367 0.057 Uiso 1 1 calc R . .
H22B H 0.5059 0.3069 0.5956 0.057 Uiso 1 1 calc R . .
C23 C 0.2636(9) 0.0958(8) 0.5929(7) 0.041(3) Uani 1 1 d . . .
H35A H 0.2096 0.1252 0.6254 0.049 Uiso 1 1 calc R . .
H35B H 0.2572 0.0367 0.6038 0.049 Uiso 1 1 calc R . .
Cl1 Cl 0.8465(3) 0.14771(17) 0.60176(16) 0.0402(6) Uani 1 1 d U . .
O3 O 0.798(3) 0.0780(15) 0.6393(14) 0.060(6) Uani 0.50(2) 1 d PU A 1
O4 O 0.966(2) 0.1412(18) 0.5980(19) 0.072(5) Uani 0.50(2) 1 d PU A 1
O5 O 0.801(2) 0.1533(16) 0.5241(12) 0.065(5) Uani 0.50(2) 1 d PU A 1
O6 O 0.823(2) 0.2241(15) 0.6418(16) 0.064(6) Uani 0.50(2) 1 d PU A 1
O3' O 0.751(3) 0.0946(17) 0.6198(18) 0.070(7) Uani 0.50(2) 1 d PU A 2
O4' O 0.948(2) 0.1294(18) 0.5533(18) 0.075(5) Uani 0.50(2) 1 d PU A 2
O5' O 0.947(3) 0.1472(19) 0.645(2) 0.085(6) Uani 0.50(2) 1 d PU A 2
O6' O 0.815(3) 0.2297(19) 0.599(2) 0.090(9) Uani 0.50(2) 1 d PU A 2
Cl2 Cl 0.2041(2) 0.84380(16) 0.45433(18) 0.0380(6) Uani 1 1 d . . .
C25 C 0.0775(11) 0.9946(12) 0.7448(9) 0.061(4) Uani 1 1 d . . .
N7 N 0.0902(13) 1.0286(13) 0.8013(10) 0.084(5) Uani 1 1 d . . .
C24 C 0.0566(18) 0.9498(13) 0.6781(10) 0.079(6) Uani 1 1 d . . .
H24A H 0.0824 0.9811 0.6343 0.119 Uiso 1 1 d R . .
H24B H 0.0981 0.8982 0.6809 0.119 Uiso 1 1 d R . .
H24C H -0.0239 0.9384 0.6730 0.119 Uiso 1 1 d 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
Cd1 O1 2.021(7) . ?
Cd1 N4 2.024(9) . ?
Cd1 N5 2.044(8) . ?
Cd1 O2 2.059(6) . ?
Cd1 N6 2.162(8) . ?
Cd1 Cd2 3.0891(12) . ?
Cd2 O2 2.004(6) . ?
Cd2 O1 2.023(7) . ?
Cd2 N2 2.069(9) . ?
Cd2 N1 2.072(8) . ?
Cd2 N3 2.154(8) . ?
N1 C22 1.488(16) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C20 1.467(18) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
N3 C23 1.473(15) . ?
N3 C18 1.477(15) . ?
N3 C19 1.492(14) . ?
N4 C9 1.528(14) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N5 C11 1.505(15) . ?
N5 H5A 0.9000 . ?
N5 H5B 0.9000 . ?
N6 C10 1.453(12) . ?
N6 C8 1.477(11) . ?
N6 C7 1.483(12) . ?
O1 C1 1.325(11) . ?
O2 C12 1.316(10) . ?
O7 Cl2 1.434(12) . ?
O8 Cl2 1.429(16) . ?
O9 Cl2 1.421(18) . ?
O10 Cl2 1.28(3) . ?
C1 C2 1.411(13) . ?
C1 C6 1.421(13) . ?
C2 C3 1.386(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.345(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.443(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.539(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.515(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.407(13) . ?
C12 C17 1.424(12) . ?
C13 C14 1.390(14) . ?
C13 C18 1.493(17) . ?
C14 C15 1.407(19) . ?
C14 H14 0.9300 . ?
C15 C16 1.436(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(15) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C22 1.47(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C23 1.54(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H35A 0.9700 . ?
C23 H35B 0.9700 . ?
Cl1 O6' 1.37(3) . ?
Cl1 O4 1.39(3) . ?
Cl1 O5' 1.40(3) . ?
Cl1 O3 1.41(2) . ?
Cl1 O6 1.44(2) . ?
Cl1 O3' 1.44(3) . ?
Cl1 O5 1.453(19) . ?
Cl1 O4' 1.48(3) . ?
C25 N7 1.13(2) . ?
C25 C24 1.39(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 Cd1 N4 108.4(4) . . ?
O1 Cd1 N5 131.1(4) . . ?
N4 Cd1 N5 118.9(4) . . ?
O1 Cd1 O2 79.8(3) . . ?
N4 Cd1 O2 108.7(3) . . ?
N5 Cd1 O2 95.4(3) . . ?
O1 Cd1 N6 90.4(3) . . ?
N4 Cd1 N6 84.3(3) . . ?
N5 Cd1 N6 83.0(3) . . ?
O2 Cd1 N6 165.6(3) . . ?
O1 Cd1 Cd2 40.2(2) . . ?
N4 Cd1 Cd2 111.1(3) . . ?
N5 Cd1 Cd2 122.2(3) . . ?
O2 Cd1 Cd2 39.85(17) . . ?
N6 Cd1 Cd2 130.4(2) . . ?
O2 Cd2 O1 81.1(3) . . ?
O2 Cd2 N2 108.2(4) . . ?
O1 Cd2 N2 107.6(4) . . ?
O2 Cd2 N1 132.2(3) . . ?
O1 Cd2 N1 94.9(3) . . ?
N2 Cd2 N1 118.2(4) . . ?
O2 Cd2 N3 90.0(3) . . ?
O1 Cd2 N3 166.7(3) . . ?
N2 Cd2 N3 84.5(4) . . ?
N1 Cd2 N3 83.7(4) . . ?
O2 Cd2 Cd1 41.18(17) . . ?
O1 Cd2 Cd1 40.2(2) . . ?
N2 Cd2 Cd1 110.3(3) . . ?
N1 Cd2 Cd1 122.6(3) . . ?
N3 Cd2 Cd1 131.0(2) . . ?
C22 N1 Cd2 108.6(7) . . ?
C22 N1 H1A 110.0 . . ?
Cd2 N1 H1A 110.0 . . ?
C22 N1 H1B 110.0 . . ?
Cd2 N1 H1B 110.0 . . ?
H1A N1 H1B 108.4 . . ?
C20 N2 Cd2 107.7(9) . . ?
C20 N2 H2A 110.2 . . ?
Cd2 N2 H2A 110.2 . . ?
C20 N2 H2B 110.2 . . ?
Cd2 N2 H2B 110.2 . . ?
H2A N2 H2B 108.5 . . ?
C23 N3 C18 112.1(9) . . ?
C23 N3 C19 112.7(10) . . ?
C18 N3 C19 109.5(10) . . ?
C23 N3 Cd2 105.9(7) . . ?
C18 N3 Cd2 111.1(6) . . ?
C19 N3 Cd2 105.2(7) . . ?
C9 N4 Cd1 110.1(7) . . ?
C9 N4 H4A 109.6 . . ?
Cd1 N4 H4A 109.6 . . ?
C9 N4 H4B 109.6 . . ?
Cd1 N4 H4B 109.6 . . ?
H4A N4 H4B 108.1 . . ?
C11 N5 Cd1 110.8(6) . . ?
C11 N5 H5A 109.5 . . ?
Cd1 N5 H5A 109.5 . . ?
C11 N5 H5B 109.5 . . ?
Cd1 N5 H5B 109.5 . . ?
H5A N5 H5B 108.1 . . ?
C10 N6 C8 113.6(7) . . ?
C10 N6 C7 108.8(8) . . ?
C8 N6 C7 110.9(7) . . ?
C10 N6 Cd1 105.3(6) . . ?
C8 N6 Cd1 105.9(6) . . ?
C7 N6 Cd1 112.2(5) . . ?
C1 O1 Cd1 130.1(6) . . ?
C1 O1 Cd2 130.1(6) . . ?
Cd1 O1 Cd2 99.6(3) . . ?
C12 O2 Cd2 128.6(6) . . ?
C12 O2 Cd1 131.2(5) . . ?
Cd2 O2 Cd1 99.0(3) . . ?
O1 C1 C2 120.0(9) . . ?
O1 C1 C6 121.9(8) . . ?
C2 C1 C6 118.1(9) . . ?
C3 C2 C1 121.2(10) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 122.1(11) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 118.1(9) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 121.3(10) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.1(9) . . ?
C5 C6 C7 118.2(9) . . ?
C1 C6 C7 122.5(8) . . ?
N6 C7 C6 115.8(8) . . ?
N6 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
N6 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
N6 C8 C9 109.7(8) . . ?
N6 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N6 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N4 C9 C8 108.6(8) . . ?
N4 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
N4 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
N6 C10 C11 111.7(8) . . ?
N6 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N6 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N5 C11 C10 107.2(8) . . ?
N5 C11 H11A 110.3 . . ?
C10 C11 H11A 110.3 . . ?
N5 C11 H11B 110.3 . . ?
C10 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
O2 C12 C13 121.5(8) . . ?
O2 C12 C17 119.9(9) . . ?
C13 C12 C17 118.5(9) . . ?
C14 C13 C12 120.0(10) . . ?
C14 C13 C18 118.5(10) . . ?
C12 C13 C18 121.5(9) . . ?
C13 C14 C15 121.9(11) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C16 118.1(10) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C17 C16 C15 119.7(11) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 121.6(11) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
N3 C18 C13 114.4(10) . . ?
N3 C18 H18A 108.7 . . ?
C13 C18 H18A 108.7 . . ?
N3 C18 H18B 108.7 . . ?
C13 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C22 C19 N3 111.2(9) . . ?
C22 C19 H19A 109.4 . . ?
N3 C19 H19A 109.4 . . ?
C22 C19 H19B 109.4 . . ?
N3 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
N2 C20 C23 111.8(10) . . ?
N2 C20 H20A 109.3 . . ?
C23 C20 H20A 109.3 . . ?
N2 C20 H20B 109.3 . . ?
C23 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C19 C22 N1 111.0(10) . . ?
C19 C22 H22A 109.4 . . ?
N1 C22 H22A 109.4 . . ?
C19 C22 H22B 109.4 . . ?
N1 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
N3 C23 C20 109.2(10) . . ?
N3 C23 H35A 109.8 . . ?
C20 C23 H35A 109.8 . . ?
N3 C23 H35B 109.8 . . ?
C20 C23 H35B 109.8 . . ?
H35A C23 H35B 108.3 . . ?
O6' Cl1 O4 110(2) . . ?
O6' Cl1 O5' 104(2) . . ?
O4 Cl1 O5' 35.5(14) . . ?
O6' Cl1 O3 132(2) . . ?
O4 Cl1 O3 111.2(17) . . ?
O5' Cl1 O3 94.9(18) . . ?
O6' Cl1 O6 31.2(15) . . ?
O4 Cl1 O6 106.1(17) . . ?
O5' Cl1 O6 84.5(18) . . ?
O3 Cl1 O6 112.0(15) . . ?
O6' Cl1 O3' 112(2) . . ?
O4 Cl1 O3' 137.5(18) . . ?
O5' Cl1 O3' 122.2(18) . . ?
O3 Cl1 O3' 28.3(12) . . ?
O6 Cl1 O3' 104.6(16) . . ?
O6' Cl1 O5 79.1(19) . . ?
O4 Cl1 O5 108.7(17) . . ?
O5' Cl1 O5 143.7(18) . . ?
O3 Cl1 O5 109.5(15) . . ?
O6 Cl1 O5 109.3(16) . . ?
O3' Cl1 O5 87.7(16) . . ?
O6' Cl1 O4' 112(2) . . ?
O4 Cl1 O4' 33.3(14) . . ?
O5' Cl1 O4' 68.5(17) . . ?
O3 Cl1 O4' 115.2(16) . . ?
O6 Cl1 O4' 126.7(16) . . ?
O3' Cl1 O4' 128.7(16) . . ?
O5 Cl1 O4' 76.7(16) . . ?
O10 Cl2 O9 113.0(16) . . ?
O10 Cl2 O8 109.7(16) . . ?
O9 Cl2 O8 106.6(12) . . ?
O10 Cl2 O7 114.5(15) . . ?
O9 Cl2 O7 105.1(11) . . ?
O8 Cl2 O7 107.4(10) . . ?
N7 C25 C24 176.2(18) . . ?
C25 C24 H24A 109.7 . . ?
C25 C24 H24B 108.4 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 110.3 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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 Cd1 Cd2 O2 -171.9(4) . . . . ?
N4 Cd1 Cd2 O2 94.2(4) . . . . ?
N5 Cd1 Cd2 O2 -54.5(5) . . . . ?
N6 Cd1 Cd2 O2 -164.9(4) . . . . ?
N4 Cd1 Cd2 O1 -93.9(4) . . . . ?
N5 Cd1 Cd2 O1 117.3(5) . . . . ?
O2 Cd1 Cd2 O1 171.9(4) . . . . ?
N6 Cd1 Cd2 O1 7.0(4) . . . . ?
O1 Cd1 Cd2 N2 93.5(4) . . . . ?
N4 Cd1 Cd2 N2 -0.5(4) . . . . ?
N5 Cd1 Cd2 N2 -149.2(5) . . . . ?
O2 Cd1 Cd2 N2 -94.7(4) . . . . ?
N6 Cd1 Cd2 N2 100.4(4) . . . . ?
O1 Cd1 Cd2 N1 -53.2(5) . . . . ?
N4 Cd1 Cd2 N1 -147.1(5) . . . . ?
N5 Cd1 Cd2 N1 64.1(5) . . . . ?
O2 Cd1 Cd2 N1 118.7(5) . . . . ?
N6 Cd1 Cd2 N1 -46.2(4) . . . . ?
O1 Cd1 Cd2 N3 -165.8(5) . . . . ?
N4 Cd1 Cd2 N3 100.3(5) . . . . ?
N5 Cd1 Cd2 N3 -48.4(5) . . . . ?
O2 Cd1 Cd2 N3 6.1(5) . . . . ?
N6 Cd1 Cd2 N3 -158.8(4) . . . . ?
O2 Cd2 N1 C22 -73.4(8) . . . . ?
O1 Cd2 N1 C22 -155.9(7) . . . . ?
N2 Cd2 N1 C22 91.2(8) . . . . ?
N3 Cd2 N1 C22 10.9(7) . . . . ?
Cd1 Cd2 N1 C22 -124.6(7) . . . . ?
O2 Cd2 N2 C20 100.1(8) . . . . ?
O1 Cd2 N2 C20 -173.7(7) . . . . ?
N1 Cd2 N2 C20 -67.9(9) . . . . ?
N3 Cd2 N2 C20 11.9(8) . . . . ?
Cd1 Cd2 N2 C20 143.8(7) . . . . ?
O2 Cd2 N3 C23 -93.1(7) . . . . ?
O1 Cd2 N3 C23 -140.8(13) . . . . ?
N2 Cd2 N3 C23 15.2(7) . . . . ?
N1 Cd2 N3 C23 134.4(7) . . . . ?
Cd1 Cd2 N3 C23 -97.1(7) . . . . ?
O2 Cd2 N3 C18 28.9(8) . . . . ?
O1 Cd2 N3 C18 -18.9(18) . . . . ?
N2 Cd2 N3 C18 137.1(8) . . . . ?
N1 Cd2 N3 C18 -103.6(8) . . . . ?
Cd1 Cd2 N3 C18 24.9(9) . . . . ?
O2 Cd2 N3 C19 147.3(9) . . . . ?
O1 Cd2 N3 C19 99.6(15) . . . . ?
N2 Cd2 N3 C19 -104.4(9) . . . . ?
N1 Cd2 N3 C19 14.8(9) . . . . ?
Cd1 Cd2 N3 C19 143.3(8) . . . . ?
O1 Cd1 N4 C9 98.9(7) . . . . ?
N5 Cd1 N4 C9 -68.4(8) . . . . ?
O2 Cd1 N4 C9 -175.9(6) . . . . ?
N6 Cd1 N4 C9 10.4(7) . . . . ?
Cd2 Cd1 N4 C9 141.7(6) . . . . ?
O1 Cd1 N5 C11 -73.1(8) . . . . ?
N4 Cd1 N5 C11 90.9(8) . . . . ?
O2 Cd1 N5 C11 -154.3(8) . . . . ?
N6 Cd1 N5 C11 11.3(8) . . . . ?
Cd2 Cd1 N5 C11 -122.7(7) . . . . ?
O1 Cd1 N6 C10 147.8(6) . . . . ?
N4 Cd1 N6 C10 -103.7(7) . . . . ?
N5 Cd1 N6 C10 16.3(6) . . . . ?
O2 Cd1 N6 C10 101.1(12) . . . . ?
Cd2 Cd1 N6 C10 143.3(5) . . . . ?
O1 Cd1 N6 C8 -91.5(6) . . . . ?
N4 Cd1 N6 C8 17.0(6) . . . . ?
N5 Cd1 N6 C8 137.0(6) . . . . ?
O2 Cd1 N6 C8 -138.2(10) . . . . ?
Cd2 Cd1 N6 C8 -96.0(6) . . . . ?
O1 Cd1 N6 C7 29.6(6) . . . . ?
N4 Cd1 N6 C7 138.1(7) . . . . ?
N5 Cd1 N6 C7 -101.9(7) . . . . ?
O2 Cd1 N6 C7 -17.1(15) . . . . ?
Cd2 Cd1 N6 C7 25.1(7) . . . . ?
N4 Cd1 O1 C1 -75.1(8) . . . . ?
N5 Cd1 O1 C1 90.1(9) . . . . ?
O2 Cd1 O1 C1 178.5(8) . . . . ?
N6 Cd1 O1 C1 9.1(8) . . . . ?
Cd2 Cd1 O1 C1 -176.2(10) . . . . ?
N4 Cd1 O1 Cd2 101.2(4) . . . . ?
N5 Cd1 O1 Cd2 -93.6(5) . . . . ?
O2 Cd1 O1 Cd2 -5.3(3) . . . . ?
N6 Cd1 O1 Cd2 -174.7(3) . . . . ?
O2 Cd2 O1 C1 -178.4(8) . . . . ?
N2 Cd2 O1 C1 75.3(8) . . . . ?
N1 Cd2 O1 C1 -46.4(8) . . . . ?
N3 Cd2 O1 C1 -129.8(13) . . . . ?
Cd1 Cd2 O1 C1 176.2(10) . . . . ?
O2 Cd2 O1 Cd1 5.4(3) . . . . ?
N2 Cd2 O1 Cd1 -100.9(4) . . . . ?
N1 Cd2 O1 Cd1 137.4(4) . . . . ?
N3 Cd2 O1 Cd1 53.9(15) . . . . ?
O1 Cd2 O2 C12 -174.0(8) . . . . ?
N2 Cd2 O2 C12 -68.3(8) . . . . ?
N1 Cd2 O2 C12 97.4(8) . . . . ?
N3 Cd2 O2 C12 15.9(8) . . . . ?
Cd1 Cd2 O2 C12 -168.7(9) . . . . ?
O1 Cd2 O2 Cd1 -5.3(3) . . . . ?
N2 Cd2 O2 Cd1 100.4(4) . . . . ?
N1 Cd2 O2 Cd1 -93.9(5) . . . . ?
N3 Cd2 O2 Cd1 -175.4(4) . . . . ?
O1 Cd1 O2 C12 173.6(8) . . . . ?
N4 Cd1 O2 C12 67.4(9) . . . . ?
N5 Cd1 O2 C12 -55.6(8) . . . . ?
N6 Cd1 O2 C12 -138.8(10) . . . . ?
Cd2 Cd1 O2 C12 168.2(10) . . . . ?
O1 Cd1 O2 Cd2 5.3(3) . . . . ?
N4 Cd1 O2 Cd2 -100.9(4) . . . . ?
N5 Cd1 O2 Cd2 136.2(4) . . . . ?
N6 Cd1 O2 Cd2 53.0(13) . . . . ?
Cd1 O1 C1 C2 159.3(7) . . . . ?
Cd2 O1 C1 C2 -15.8(13) . . . . ?
Cd1 O1 C1 C6 -22.5(13) . . . . ?
Cd2 O1 C1 C6 162.4(7) . . . . ?
O1 C1 C2 C3 179.2(9) . . . . ?
C6 C1 C2 C3 1.0(15) . . . . ?
C1 C2 C3 C4 0.5(17) . . . . ?
C2 C3 C4 C5 0.1(16) . . . . ?
C3 C4 C5 C6 -2.4(16) . . . . ?
C4 C5 C6 C1 3.9(14) . . . . ?
C4 C5 C6 C7 -171.7(9) . . . . ?
O1 C1 C6 C5 178.7(9) . . . . ?
C2 C1 C6 C5 -3.1(14) . . . . ?
O1 C1 C6 C7 -6.0(14) . . . . ?
C2 C1 C6 C7 172.2(9) . . . . ?
C10 N6 C7 C6 -175.7(8) . . . . ?
C8 N6 C7 C6 58.6(10) . . . . ?
Cd1 N6 C7 C6 -59.5(9) . . . . ?
C5 C6 C7 N6 -132.9(9) . . . . ?
C1 C6 C7 N6 51.6(12) . . . . ?
C10 N6 C8 C9 74.2(11) . . . . ?
C7 N6 C8 C9 -162.9(8) . . . . ?
Cd1 N6 C8 C9 -40.9(8) . . . . ?
Cd1 N4 C9 C8 -35.5(10) . . . . ?
N6 C8 C9 N4 51.8(11) . . . . ?
C8 N6 C10 C11 -157.2(9) . . . . ?
C7 N6 C10 C11 78.7(11) . . . . ?
Cd1 N6 C10 C11 -41.8(10) . . . . ?
Cd1 N5 C11 C10 -35.9(11) . . . . ?
N6 C10 C11 N5 52.9(13) . . . . ?
Cd2 O2 C12 C13 -31.9(12) . . . . ?
Cd1 O2 C12 C13 163.1(7) . . . . ?
Cd2 O2 C12 C17 149.6(8) . . . . ?
Cd1 O2 C12 C17 -15.4(13) . . . . ?
O2 C12 C13 C14 177.9(10) . . . . ?
C17 C12 C13 C14 -3.6(15) . . . . ?
O2 C12 C13 C18 -2.2(15) . . . . ?
C17 C12 C13 C18 176.4(11) . . . . ?
C12 C13 C14 C15 2.0(18) . . . . ?
C18 C13 C14 C15 -177.9(12) . . . . ?
C13 C14 C15 C16 1.3(19) . . . . ?
C14 C15 C16 C17 -3.1(18) . . . . ?
C15 C16 C17 C12 1.5(18) . . . . ?
O2 C12 C17 C16 -179.7(9) . . . . ?
C13 C12 C17 C16 1.8(16) . . . . ?
C23 N3 C18 C13 55.6(12) . . . . ?
C19 N3 C18 C13 -178.5(10) . . . . ?
Cd2 N3 C18 C13 -62.7(11) . . . . ?
C14 C13 C18 N3 -125.7(11) . . . . ?
C12 C13 C18 N3 54.3(15) . . . . ?
C23 N3 C19 C22 -154.1(11) . . . . ?
C18 N3 C19 C22 80.4(13) . . . . ?
Cd2 N3 C19 C22 -39.1(14) . . . . ?
Cd2 N2 C20 C23 -37.1(13) . . . . ?
N3 C19 C22 N1 51.8(15) . . . . ?
Cd2 N1 C22 C19 -36.1(12) . . . . ?
C18 N3 C23 C20 -159.6(10) . . . . ?
C19 N3 C23 C20 76.2(12) . . . . ?
Cd2 N3 C23 C20 -38.3(10) . . . . ?
N2 C20 C23 N3 52.5(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.784
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.217
####################################################################### 
# 
# 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_L3-Zn
_database_code_depnum_ccdc_archive 'CCDC 1492227'
_audit_update_record             
;
2016-08-01 deposited with the CCDC.
2016-08-02 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         'C19 H36 N3 O2 Zn, Cl O4, H2 O'
_chemical_formula_sum            'C19 H38 Cl N3 O7 Zn'
_chemical_formula_weight         521.34

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      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                   9.7985(8)
_cell_length_b                   13.1054(9)
_cell_length_c                   9.8329(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.233(3)
_cell_angle_gamma                90
_cell_volume                     1252.63(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4829
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.310
_exptl_absorpt_coefficient_mu    1.128
_shelx_estimated_absorpt_T_min   0.674
_shelx_estimated_absorpt_T_max   0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_T_max  0.7212
_exptl_absorpt_process_details   sadabs
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8382
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.603
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4228
_reflns_number_gt                3707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1283P)²+0.2237P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.14(3)
_chemical_absolute_configuration .ad
_refine_ls_number_reflns         4228
_refine_ls_number_parameters     285
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1950
_refine_ls_wR_factor_gt          0.1872
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.076
_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 0.26398(6) 0.22755(7) 0.59746(6) 0.03524(15) Uani 1 1 d . . . . .
C1 C 0.0985(7) 0.0976(5) 0.7414(7) 0.0440(17) Uani 1 1 d . . . . .
C2 C 0.1146(9) 0.0167(6) 0.8365(8) 0.059(2) Uani 1 1 d . . . . .
H2 H 0.1799 -0.0335 0.8275 0.070 Uiso 1 1 calc R U . . .
C3 C 0.0352(10) 0.0105(8) 0.9429(9) 0.075(3) Uani 1 1 d . . . . .
H3 H 0.0460 -0.0451 1.0022 0.090 Uiso 1 1 calc R U . . .
C4 C -0.0577(10) 0.0834(8) 0.9627(9) 0.075(3) Uani 1 1 d . . . . .
H4 H -0.1091 0.0785 1.0358 0.090 Uiso 1 1 calc R U . . .
C5 C -0.0763(8) 0.1660(8) 0.8731(8) 0.066(2) Uani 1 1 d . . . . .
H5 H -0.1392 0.2168 0.8879 0.080 Uiso 1 1 calc R U . . .
C6 C -0.0018(7) 0.1737(6) 0.7614(7) 0.0483(18) Uani 1 1 d . . . . .
C7 C -0.0276(7) 0.2584(6) 0.6615(9) 0.057(2) Uani 1 1 d . . . . .
H7A H -0.1002 0.3012 0.6887 0.068 Uiso 1 1 calc R U . . .
H7B H -0.0602 0.2299 0.5722 0.068 Uiso 1 1 calc R U . . .
C8 C 0.0681(9) 0.3956(6) 0.5320(10) 0.063(2) Uani 1 1 d . . . . .
H8A H 0.1297 0.4536 0.5459 0.075 Uiso 1 1 calc R U . . .
H8B H -0.0255 0.4207 0.5281 0.075 Uiso 1 1 calc R U . . .
C9 C 0.0866(9) 0.3435(7) 0.3955(11) 0.075(3) Uani 1 1 d . . . . .
H9A H 0.0185 0.2900 0.3766 0.090 Uiso 1 1 calc R U . . .
H9B H 0.0725 0.3930 0.3218 0.090 Uiso 1 1 calc R U . . .
C10 C 0.1433(9) 0.3755(6) 0.7777(9) 0.062(2) Uani 1 1 d . . . . .
H10A H 0.1225 0.3336 0.8538 0.074 Uiso 1 1 calc R U . . .
H10B H 0.0948 0.4398 0.7814 0.074 Uiso 1 1 calc R U . . .
C11 C 0.2984(8) 0.3954(5) 0.7907(9) 0.054(2) Uani 1 1 d . . . . .
H11A H 0.3169 0.4452 0.7224 0.065 Uiso 1 1 calc R U . . .
H11B H 0.3285 0.4243 0.8804 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3819(7) 0.2353(7) 0.8958(6) 0.0529(17) Uani 1 1 d . . . . .
H12A H 0.2880 0.2188 0.9090 0.063 Uiso 1 1 calc R U . . .
H12B H 0.4218 0.2739 0.9753 0.063 Uiso 1 1 calc R U . . .
C13 C 0.4614(10) 0.1374(7) 0.8893(8) 0.068(3) Uani 1 1 d . . . . .
H13A H 0.4242 0.0993 0.8098 0.101 Uiso 1 1 calc R U . . .
H13B H 0.4543 0.0978 0.9702 0.101 Uiso 1 1 calc R U . . .
H13C H 0.5563 0.1528 0.8836 0.101 Uiso 1 1 calc R U . . .
C14 C 0.5216(7) 0.3294(6) 0.7431(9) 0.053(2) Uani 1 1 d . . . . .
H14A H 0.5131 0.3699 0.6599 0.063 Uiso 1 1 calc R U . . .
H14B H 0.5701 0.2672 0.7253 0.063 Uiso 1 1 calc R U . . .
C15 C 0.6094(10) 0.3885(8) 0.8553(12) 0.083(3) Uani 1 1 d . . . . .
H15A H 0.5629 0.4504 0.8745 0.124 Uiso 1 1 calc R U . . .
H15B H 0.6963 0.4049 0.8253 0.124 Uiso 1 1 calc R U . . .
H15C H 0.6243 0.3476 0.9368 0.124 Uiso 1 1 calc R U . . .
C16 C 0.2263(8) 0.2262(10) 0.2835(7) 0.068(2) Uani 1 1 d . . . . .
H16A H 0.1914 0.2611 0.1993 0.082 Uiso 1 1 calc R U . . .
H16B H 0.3212 0.2077 0.2770 0.082 Uiso 1 1 calc R U . . .
C17 C 0.1479(10) 0.1334(10) 0.2921(10) 0.086(3) Uani 1 1 d . . . . .
H17A H 0.1792 0.0988 0.3763 0.129 Uiso 1 1 calc R U . . .
H17B H 0.1603 0.0899 0.2160 0.129 Uiso 1 1 calc R U . . .
H17C H 0.0522 0.1499 0.2897 0.129 Uiso 1 1 calc R U . . .
C18 C 0.3320(10) 0.3754(8) 0.3928(10) 0.082(3) Uani 1 1 d . . . . .
H18A H 0.4198 0.3402 0.4043 0.099 Uiso 1 1 calc R U . . .
H18B H 0.3317 0.4216 0.4698 0.099 Uiso 1 1 calc R U . . .
C19 C 0.3247(13) 0.4399(10) 0.2618(13) 0.121(4) Uani 1 1 d . . . . .
H19A H 0.3894 0.4142 0.2047 0.182 Uiso 1 1 calc R U . . .
H19B H 0.3466 0.5095 0.2857 0.182 Uiso 1 1 calc R U . . .
H19C H 0.2335 0.4363 0.2132 0.182 Uiso 1 1 calc R U . . .
N1 N 0.0969(6) 0.3239(4) 0.6490(7) 0.0501(16) Uani 1 1 d . . . . .
N2 N 0.3793(6) 0.3010(4) 0.7726(6) 0.0413(14) Uani 1 1 d . . . . .
N3 N 0.2244(6) 0.2999(6) 0.4010(6) 0.0493(17) Uani 1 1 d . . . . .
O1 O 0.1733(5) 0.1009(4) 0.6376(5) 0.0466(12) Uani 1 1 d . . . . .
O2 O 0.4305(10) 0.6328(8) 0.7420(14) 0.157(5) Uani 1 1 d . . . . .
O3 O 0.3358(11) 0.7338(10) 0.5769(9) 0.132(3) Uani 1 1 d . . . . .
O4 O 0.2026(10) 0.6355(9) 0.6994(18) 0.178(6) Uani 1 1 d . . . . .
O5 O 0.314(2) 0.7749(10) 0.7881(18) 0.260(9) Uani 1 1 d . . . . .
O1W O 0.4345(5) 0.1430(4) 0.5432(5) 0.0496(12) Uani 1 1 d . . . . .
H1WA H 0.4761 0.1635 0.4724 0.059 Uiso 1 1 d R U . . .
H1WB H 0.4385 0.0673 0.5547 0.059 Uiso 1 1 d R U . . .
O2W O 0.3182(7) 0.9547(4) 0.5337(8) 0.084(2) Uani 1 1 d . . . . .
H2WA H 0.3652 0.9068 0.5751 0.101 Uiso 1 1 d R U . . .
H2WB H 0.2618 0.9790 0.5845 0.101 Uiso 1 1 d R U . . .
Cl1 Cl 0.3181(2) 0.69216(14) 0.7056(2) 0.0616(5) 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
Zn1 O1 1.946(5) . ?
Zn1 O1W 2.129(5) . ?
Zn1 N3 2.143(6) . ?
Zn1 N2 2.163(6) . ?
Zn1 N1 2.177(6) . ?
C1 O1 1.331(9) . ?
C1 C2 1.409(11) . ?
C1 C6 1.431(10) . ?
C2 C3 1.383(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.351(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.482(11) . ?
C7 N1 1.510(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.485(11) . ?
C8 C9 1.536(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N3 1.461(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N1 1.457(10) . ?
C10 C11 1.532(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.492(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.484(9) . ?
C12 C13 1.506(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N2 1.506(9) . ?
C14 C15 1.523(12) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.446(16) . ?
C16 N3 1.508(12) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N3 1.456(12) . ?
C18 C19 1.534(14) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O2 Cl1 1.359(10) . ?
O3 Cl1 1.409(9) . ?
O4 Cl1 1.349(10) . ?
O5 Cl1 1.357(13) . ?
O1W H1WA 0.8908 . ?
O1W H1WB 0.9976 . ?
O2W H2WA 0.8511 . ?
O2W H2WB 0.8521 . ?

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 Zn1 O1W 89.99(19) . . ?
O1 Zn1 N3 121.6(2) . . ?
O1W Zn1 N3 93.6(2) . . ?
O1 Zn1 N2 115.1(2) . . ?
O1W Zn1 N2 94.8(2) . . ?
N3 Zn1 N2 122.5(2) . . ?
O1 Zn1 N1 94.1(2) . . ?
O1W Zn1 N1 175.9(2) . . ?
N3 Zn1 N1 84.1(2) . . ?
N2 Zn1 N1 83.6(2) . . ?
O1 C1 C2 120.5(7) . . ?
O1 C1 C6 122.4(6) . . ?
C2 C1 C6 117.1(7) . . ?
C3 C2 C1 121.3(8) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 121.4(9) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.7(9) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.9(9) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.6(7) . . ?
C5 C6 C7 120.8(7) . . ?
C1 C6 C7 119.6(6) . . ?
C6 C7 N1 114.1(6) . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
N1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C9 111.3(6) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N3 C9 C8 110.6(7) . . ?
N3 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N1 C10 C11 110.5(7) . . ?
N1 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C10 112.6(6) . . ?
N2 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N2 C12 C13 114.5(6) . . ?
N2 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
N2 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 116.0(7) . . ?
N2 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
N2 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 N3 115.8(7) . . ?
C17 C16 H16A 108.3 . . ?
N3 C16 H16A 108.3 . . ?
C17 C16 H16B 108.3 . . ?
N3 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
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 . . ?
N3 C18 C19 117.6(8) . . ?
N3 C18 H18A 107.9 . . ?
C19 C18 H18A 107.9 . . ?
N3 C18 H18B 107.9 . . ?
C19 C18 H18B 107.9 . . ?
H18A C18 H18B 107.2 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 N1 C8 112.8(6) . . ?
C10 N1 C7 111.1(6) . . ?
C8 N1 C7 110.3(6) . . ?
C10 N1 Zn1 108.1(4) . . ?
C8 N1 Zn1 105.2(5) . . ?
C7 N1 Zn1 109.2(4) . . ?
C12 N2 C11 109.8(6) . . ?
C12 N2 C14 112.3(5) . . ?
C11 N2 C14 109.7(5) . . ?
C12 N2 Zn1 110.2(4) . . ?
C11 N2 Zn1 103.4(4) . . ?
C14 N2 Zn1 111.1(4) . . ?
C18 N3 C9 113.8(7) . . ?
C18 N3 C16 108.3(7) . . ?
C9 N3 C16 108.9(6) . . ?
C18 N3 Zn1 107.5(5) . . ?
C9 N3 Zn1 105.5(5) . . ?
C16 N3 Zn1 112.9(6) . . ?
C1 O1 Zn1 119.6(4) . . ?
Zn1 O1W H1WA 119.3 . . ?
Zn1 O1W H1WB 120.6 . . ?
H1WA O1W H1WB 112.0 . . ?
H2WA O2W H2WB 110.3 . . ?
O4 Cl1 O5 112.4(11) . . ?
O4 Cl1 O2 110.1(7) . . ?
O5 Cl1 O2 112.5(10) . . ?
O4 Cl1 O3 111.7(9) . . ?
O5 Cl1 O3 104.1(9) . . ?
O2 Cl1 O3 105.7(8) . . ?

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 C3 -178.2(7) . . . . ?
C6 C1 C2 C3 1.0(11) . . . . ?
C1 C2 C3 C4 -2.2(13) . . . . ?
C2 C3 C4 C5 1.1(14) . . . . ?
C3 C4 C5 C6 1.1(13) . . . . ?
C4 C5 C6 C1 -2.2(12) . . . . ?
C4 C5 C6 C7 176.3(8) . . . . ?
O1 C1 C6 C5 -179.6(7) . . . . ?
C2 C1 C6 C5 1.1(10) . . . . ?
O1 C1 C6 C7 1.8(10) . . . . ?
C2 C1 C6 C7 -177.5(7) . . . . ?
C5 C6 C7 N1 121.0(8) . . . . ?
C1 C6 C7 N1 -60.4(9) . . . . ?
N1 C8 C9 N3 -55.8(10) . . . . ?
N1 C10 C11 N2 -53.8(9) . . . . ?
C11 C10 N1 C8 -84.1(8) . . . . ?
C11 C10 N1 C7 151.5(6) . . . . ?
C11 C10 N1 Zn1 31.8(7) . . . . ?
C9 C8 N1 C10 153.1(7) . . . . ?
C9 C8 N1 C7 -82.0(8) . . . . ?
C9 C8 N1 Zn1 35.5(7) . . . . ?
C6 C7 N1 C10 -63.3(8) . . . . ?
C6 C7 N1 C8 170.9(6) . . . . ?
C6 C7 N1 Zn1 55.8(7) . . . . ?
C13 C12 N2 C11 -179.8(6) . . . . ?
C13 C12 N2 C14 -57.6(8) . . . . ?
C13 C12 N2 Zn1 66.9(7) . . . . ?
C10 C11 N2 C12 -73.6(8) . . . . ?
C10 C11 N2 C14 162.7(6) . . . . ?
C10 C11 N2 Zn1 44.1(7) . . . . ?
C15 C14 N2 C12 -60.2(9) . . . . ?
C15 C14 N2 C11 62.0(9) . . . . ?
C15 C14 N2 Zn1 175.8(6) . . . . ?
C19 C18 N3 C9 -62.1(12) . . . . ?
C19 C18 N3 C16 59.1(12) . . . . ?
C19 C18 N3 Zn1 -178.6(8) . . . . ?
C8 C9 N3 C18 -74.5(9) . . . . ?
C8 C9 N3 C16 164.6(7) . . . . ?
C8 C9 N3 Zn1 43.2(8) . . . . ?
C17 C16 N3 C18 166.7(8) . . . . ?
C17 C16 N3 C9 -69.0(10) . . . . ?
C17 C16 N3 Zn1 47.8(8) . . . . ?
C2 C1 O1 Zn1 -132.8(6) . . . . ?
C6 C1 O1 Zn1 47.9(8) . . . . ?

_refine_diff_density_max         1.320
_refine_diff_density_min         -1.389
_refine_diff_density_rms         0.122

####################################################################### 
# 
# 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_R
_database_code_depnum_ccdc_archive 'CCDC 1492228'
_audit_update_record             
;
2016-08-01 deposited with the CCDC.
2016-08-02 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         'C9 H8 O3'
_chemical_formula_sum            'C9 H8 O3'
_chemical_formula_weight         164.15



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'
O O 0.0492 0.0322 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1207(5)
_cell_length_b                   7.5850(6)
_cell_length_c                   16.9844(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     788.51(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3701
_cell_measurement_theta_min      5.21
_cell_measurement_theta_max      68.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   0.4789
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.876
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2920
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         6.391
_diffrn_reflns_theta_max         65.494
_diffrn_reflns_theta_full        65.494
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             1281
_reflns_number_gt                1266
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.597
_reflns_Friedel_fraction_max     0.894
_reflns_Friedel_fraction_full    0.894

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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 > 2sigma(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     
'w=1/[σ²(Fo²)+(0.0341P)²+0.1194P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(7)
_chemical_absolute_configuration .ad
_refine_ls_number_reflns         1281
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.1731(3) 0.6229(2) 0.81908(10) 0.0240(4) Uani 1 1 d . . . . .
C2 C 0.3663(3) 0.7139(2) 0.80671(10) 0.0280(4) Uani 1 1 d . . . . .
H2 H 0.4398 0.7668 0.8499 0.034 Uiso 1 1 calc R U . . .
C3 C 0.1508(3) 0.5624(2) 0.68024(10) 0.0333(5) Uani 1 1 d . . . . .
H3 H 0.0768 0.5108 0.6368 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0644(3) 0.5474(2) 0.75557(10) 0.0284(4) Uani 1 1 d . . . . .
H4 H -0.0687 0.4856 0.7637 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4532(3) 0.7282(2) 0.73135(11) 0.0346(5) Uani 1 1 d . . . . .
H5 H 0.5865 0.7897 0.7231 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3447(4) 0.6525(2) 0.66838(11) 0.0361(5) Uani 1 1 d . . . . .
H6 H 0.4036 0.6623 0.6168 0.043 Uiso 1 1 calc R U . . .
C7 C 0.0905(3) 0.6000(2) 0.90174(10) 0.0251(4) Uani 1 1 d . . . . .
H7 H 0.1713 0.6812 0.9379 0.030 Uiso 1 1 calc R U . . .
C8 C 0.1024(3) 0.4126(2) 0.93328(10) 0.0293(4) Uani 1 1 d . . . . .
H8A H 0.1013 0.3255 0.8899 0.035 Uiso 1 1 calc R U . . .
H8B H 0.2352 0.3949 0.9656 0.035 Uiso 1 1 calc R U . . .
C9 C -0.2334(3) 0.5246(2) 0.95841(11) 0.0282(5) Uani 1 1 d . . . . .
O1 O -0.0932(2) 0.39903(17) 0.98069(7) 0.0329(4) Uani 1 1 d . . . . .
O2 O -0.4167(2) 0.5367(2) 0.98225(8) 0.0398(4) Uani 1 1 d . . . . .
O3 O -0.1435(2) 0.63585(16) 0.90660(7) 0.0302(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 C2 1.385(3) . ?
C1 C4 1.391(2) . ?
C1 C7 1.502(2) . ?
C2 C5 1.390(3) . ?
C2 H2 0.9500 . ?
C3 C6 1.384(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O3 1.460(2) . ?
C7 C8 1.521(2) . ?
C7 H7 1.0000 . ?
C8 O1 1.446(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O2 1.196(2) . ?
C9 O1 1.337(2) . ?
C9 O3 1.338(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
C2 C1 C4 119.72(16) . . ?
C2 C1 C7 119.12(15) . . ?
C4 C1 C7 121.09(15) . . ?
C1 C2 C5 120.33(17) . . ?
C1 C2 H2 119.8 . . ?
C5 C2 H2 119.8 . . ?
C6 C3 C4 120.05(17) . . ?
C6 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C1 119.92(17) . . ?
C3 C4 H4 120.0 . . ?
C1 C4 H4 120.0 . . ?
C6 C5 C2 119.73(18) . . ?
C6 C5 H5 120.1 . . ?
C2 C5 H5 120.1 . . ?
C3 C6 C5 120.25(17) . . ?
C3 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O3 C7 C1 111.19(14) . . ?
O3 C7 C8 101.60(14) . . ?
C1 C7 C8 114.91(14) . . ?
O3 C7 H7 109.6 . . ?
C1 C7 H7 109.6 . . ?
C8 C7 H7 109.6 . . ?
O1 C8 C7 102.89(14) . . ?
O1 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
O1 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
O2 C9 O1 124.11(18) . . ?
O2 C9 O3 124.08(19) . . ?
O1 C9 O3 111.81(15) . . ?
C9 O1 C8 108.84(13) . . ?
C9 O3 C7 108.87(14) . . ?

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
C4 C1 C2 C5 -0.8(3) . . . . ?
C7 C1 C2 C5 176.21(16) . . . . ?
C6 C3 C4 C1 0.0(3) . . . . ?
C2 C1 C4 C3 0.5(3) . . . . ?
C7 C1 C4 C3 -176.45(16) . . . . ?
C1 C2 C5 C6 0.6(3) . . . . ?
C4 C3 C6 C5 -0.1(3) . . . . ?
C2 C5 C6 C3 -0.2(3) . . . . ?
C2 C1 C7 O3 135.15(16) . . . . ?
C4 C1 C7 O3 -47.9(2) . . . . ?
C2 C1 C7 C8 -110.16(18) . . . . ?
C4 C1 C7 C8 66.8(2) . . . . ?
O3 C7 C8 O1 -23.62(16) . . . . ?
C1 C7 C8 O1 -143.76(15) . . . . ?
O2 C9 O1 C8 173.21(18) . . . . ?
O3 C9 O1 C8 -7.2(2) . . . . ?
C7 C8 O1 C9 19.72(18) . . . . ?
O2 C9 O3 C7 170.10(17) . . . . ?
O1 C9 O3 C7 -9.48(19) . . . . ?
C1 C7 O3 C9 143.50(14) . . . . ?
C8 C7 O3 C9 20.77(17) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1492229'
_audit_update_record             
;
2016-08-01 deposited with the CCDC.
2016-08-02 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         'C9 H8 O3'
_chemical_formula_sum            'C9 H8 O3'
_chemical_formula_weight         164.15


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'
O O 0.0492 0.0322 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1196(4)
_cell_length_b                   7.5799(5)
_cell_length_c                   16.9823(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     787.74(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3701
_cell_measurement_theta_min      5.21
_cell_measurement_theta_max      68.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   0.4789
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.877
_shelx_estimated_absorpt_T_min   0.798
_shelx_estimated_absorpt_T_max   0.831
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8398
_exptl_absorpt_correction_T_max  0.8926
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3846
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.209
_diffrn_reflns_theta_max         64.970
_diffrn_reflns_theta_full        64.970
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             1317
_reflns_number_gt                1306
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_max     0.972
_reflns_Friedel_fraction_full    0.972

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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 > 2sigma(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     
'w=1/[σ²(Fo²)+(0.0319P)²+0.1307P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.024(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 499 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(7)
_chemical_absolute_configuration .ad
_refine_ls_number_reflns         1317
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.7336(3) 0.4751(3) 0.54168(10) 0.0279(4) Uani 1 1 d . . . . .
C2 C 0.3976(3) 0.5873(2) 0.56666(10) 0.0296(4) Uani 1 1 d . . . . .
H2A H 0.2648 0.6050 0.5343 0.035 Uiso 1 1 calc R U . . .
H2B H 0.3987 0.6745 0.6101 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4096(3) 0.3999(2) 0.59821(10) 0.0251(4) Uani 1 1 d . . . . .
H3 H 0.3290 0.3186 0.5621 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3269(3) 0.3768(2) 0.68095(9) 0.0238(4) Uani 1 1 d . . . . .
C5 C 0.4354(3) 0.4526(2) 0.74444(10) 0.0284(4) Uani 1 1 d . . . . .
H5 H 0.5684 0.5145 0.7363 0.034 Uiso 1 1 calc R U . . .
C6 C 0.3493(3) 0.4376(2) 0.81973(10) 0.0337(4) Uani 1 1 d . . . . .
H6 H 0.4236 0.4892 0.8631 0.040 Uiso 1 1 calc R U . . .
C7 C 0.1555(4) 0.3478(2) 0.83166(11) 0.0361(5) Uani 1 1 d . . . . .
H7 H 0.0966 0.3382 0.8832 0.043 Uiso 1 1 calc R U . . .
C8 C 0.0470(3) 0.2717(3) 0.76859(11) 0.0345(5) Uani 1 1 d . . . . .
H8 H -0.0860 0.2098 0.7769 0.041 Uiso 1 1 calc R U . . .
C9 C 0.1333(3) 0.2863(2) 0.69332(10) 0.0280(4) Uani 1 1 d . . . . .
H9 H 0.0592 0.2340 0.6501 0.034 Uiso 1 1 calc R U . . .
O1 O 0.6435(2) 0.36433(16) 0.59337(7) 0.0303(3) Uani 1 1 d . . . . .
O2 O 0.5931(2) 0.60094(18) 0.51929(7) 0.0330(3) Uani 1 1 d . . . . .
O3 O 0.9170(2) 0.4632(2) 0.51787(8) 0.0398(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 O3 1.197(2) . ?
C1 O1 1.334(2) . ?
C1 O2 1.339(2) . ?
C2 O2 1.445(2) . ?
C2 C3 1.520(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.458(2) . ?
C3 C4 1.504(2) . ?
C3 H3 1.0000 . ?
C4 C9 1.385(3) . ?
C4 C5 1.391(2) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 H9 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
O3 C1 O1 124.25(19) . . ?
O3 C1 O2 124.04(18) . . ?
O1 C1 O2 111.71(14) . . ?
O2 C2 C3 102.88(14) . . ?
O2 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
O2 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
O1 C3 C4 111.20(14) . . ?
O1 C3 C2 101.54(14) . . ?
C4 C3 C2 114.94(14) . . ?
O1 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
C2 C3 H3 109.6 . . ?
C9 C4 C5 119.71(16) . . ?
C9 C4 C3 119.17(15) . . ?
C5 C4 C3 121.03(15) . . ?
C6 C5 C4 119.95(17) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 120.07(17) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.19(17) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 119.74(18) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 120.33(17) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C1 O1 C3 109.06(14) . . ?
C1 O2 C2 108.80(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
O2 C2 C3 O1 23.65(16) . . . . ?
O2 C2 C3 C4 143.79(15) . . . . ?
O1 C3 C4 C9 -135.45(16) . . . . ?
C2 C3 C4 C9 109.90(18) . . . . ?
O1 C3 C4 C5 47.9(2) . . . . ?
C2 C3 C4 C5 -66.7(2) . . . . ?
C9 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 C6 176.44(15) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C5 C4 C9 C8 0.3(3) . . . . ?
C3 C4 C9 C8 -176.37(16) . . . . ?
C7 C8 C9 C4 -0.1(3) . . . . ?
O3 C1 O1 C3 -170.12(17) . . . . ?
O2 C1 O1 C3 9.55(19) . . . . ?
C4 C3 O1 C1 -143.59(14) . . . . ?
C2 C3 O1 C1 -20.85(17) . . . . ?
O3 C1 O2 C2 -173.15(17) . . . . ?
O1 C1 O2 C2 7.19(19) . . . . ?
C3 C2 O2 C1 -19.73(18) . . . . ?

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
C3 H3 O3 1.00 2.59 3.385(2) 136.7 4_456
C2 H2A O3 0.99 2.40 3.197(2) 137.1 1_455
C2 H2A O2 0.99 2.63 3.345(2) 129.4 4_466
C3 H3 O3 1.00 2.59 3.385(2) 136.7 4_456
C2 H2A O3 0.99 2.40 3.197(2) 137.1 1_455
C2 H2A O2 0.99 2.63 3.345(2) 129.4 4_466

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.033

