# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_sja25_07
_database_code_depnum_ccdc_archive 'CCDC 1049977'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;


_vrf_PLAT410_sja25_07            
;
RESPONSE: This is due to the extreme rigidity of the macrocyclic chelator
 forcing less favourable geometries and close interactions on the alkyl
 backbone between H6B and H11B. 
;



_vrf_PLAT230_sja25_07            
;
RESPONSE: here is some evidence for a very small amount (a few percent) of a 
second orientation of the ligand. Modelling of this disorder did not 
yield a significant improvement in the fit. The difference in the 
displacement parameters of N2 and C2 is a reflection of this 
small-scale unmodelled disorder. The ORTEP does not show a problem. 
;



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H28 Cl2 Mn N4'

_chemical_formula_sum            'C13 H28 Cl2 Mn N4'
_chemical_formula_weight         366.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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                   8.2471(9)
_cell_length_b                   13.794(2)
_cell_length_c                   15.1499(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.689(9)
_cell_angle_gamma                90
_cell_volume                     1715.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11723
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      32.85

_exptl_crystal_description       block
_exptl_crystal_colour            'pale pink'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.078
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23731
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.482
_diffrn_reflns_theta_max         30.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5019
_reflns_number_gt                3089
_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       'Stoe X-AREA'
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_solution    SHELXS-86
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0790P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5019
_refine_ls_number_parameters     181
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1417
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_restrained_S_all      0.933
_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
Mn1 Mn 0.21140(5) 0.18681(3) 0.76159(3) 0.02356(12) Uani 1 1 d . . . . .
C1 C 0.3558(4) 0.1029(3) 0.6018(2) 0.0403(8) Uani 1 1 d . . . . .
H1A H 0.4156 0.0562 0.5674 0.048 Uiso 1 1 calc R U . . .
H1B H 0.4036 0.1680 0.5950 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1703(5) 0.1041(3) 0.5646(3) 0.0519(10) Uani 1 1 d . U . . .
H2A H 0.1400 0.0391 0.5406 0.062 Uiso 1 1 calc R U . . .
H2B H 0.1552 0.1509 0.5149 0.062 Uiso 1 1 calc R U . . .
C4 C -0.0350(4) 0.0424(3) 0.6638(2) 0.0347(7) Uani 1 1 d . . . . .
H4A H -0.1486 0.0432 0.6357 0.042 Uiso 1 1 calc R U . . .
H4B H 0.0194 -0.0155 0.6418 0.042 Uiso 1 1 calc R U . . .
C5 C -0.0372(4) 0.0342(3) 0.7625(2) 0.0379(8) Uani 1 1 d . . . . .
H5A H -0.1019 0.0882 0.7838 0.045 Uiso 1 1 calc R U . . .
H5B H -0.0911 -0.0273 0.7765 0.045 Uiso 1 1 calc R U . . .
C6 C 0.1164(5) 0.0377(3) 0.9068(2) 0.0452(8) Uani 1 1 d . . . . .
H6A H 0.0632 -0.0233 0.9229 0.054 Uiso 1 1 calc R U . . .
H6B H 0.0437 0.0918 0.9200 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2717(5) 0.0479(3) 0.9647(3) 0.0529(10) Uani 1 1 d . . . . .
H7A H 0.2474 0.0405 1.0271 0.064 Uiso 1 1 calc R U . . .
H7B H 0.3439 -0.0065 0.9516 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3623(4) 0.1381(3) 0.9579(3) 0.0488(10) Uani 1 1 d . . . . .
H8A H 0.2919 0.1920 0.9744 0.059 Uiso 1 1 calc R U . . .
H8B H 0.4578 0.1361 1.0029 0.059 Uiso 1 1 calc R U . . .
C10 C 0.5377(4) 0.0931(3) 0.8404(2) 0.0355(7) Uani 1 1 d . . . . .
H10A H 0.5092 0.0265 0.8576 0.043 Uiso 1 1 calc R U . . .
H10B H 0.6488 0.1077 0.8682 0.043 Uiso 1 1 calc R U . . .
C11 C 0.5360(4) 0.0987(3) 0.7402(2) 0.0408(8) Uani 1 1 d . . . . .
H11A H 0.5673 0.1648 0.7231 0.049 Uiso 1 1 calc R U . . .
H11B H 0.6171 0.0527 0.7204 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3301(4) -0.0276(2) 0.7073(2) 0.0375(7) Uani 1 1 d . . . . .
H12A H 0.4322 -0.0656 0.7172 0.045 Uiso 1 1 calc R U . . .
H12B H 0.2700 -0.0511 0.6517 0.045 Uiso 1 1 calc R U . . .
C13 C 0.2259(4) -0.0477(2) 0.7848(2) 0.0379(7) Uani 1 1 d . . . . .
H13A H 0.1507 -0.1020 0.7680 0.045 Uiso 1 1 calc R U . . .
H13B H 0.2989 -0.0685 0.8372 0.045 Uiso 1 1 calc R U . . .
C3 C -0.0607(6) 0.2074(3) 0.6050(4) 0.0685(15) Uani 1 1 d . . . . .
H3A H 0.0003 0.2641 0.5877 0.103 Uiso 1 1 calc R U . . .
H3B H -0.1316 0.1839 0.5537 0.103 Uiso 1 1 calc R U . . .
H3C H -0.1273 0.2255 0.6526 0.103 Uiso 1 1 calc R U . . .
C9 C 0.5077(5) 0.2570(3) 0.8886(4) 0.0643(14) Uani 1 1 d . . . . .
H9A H 0.5508 0.2780 0.8337 0.096 Uiso 1 1 calc R U . . .
H9B H 0.4316 0.3058 0.9069 0.096 Uiso 1 1 calc R U . . .
H9C H 0.5978 0.2490 0.9353 0.096 Uiso 1 1 calc R U . . .
N3 N 0.3727(3) 0.0751(2) 0.69572(18) 0.0296(5) Uani 1 1 d . . . . .
N2 N 0.0515(3) 0.1321(2) 0.63600(19) 0.0370(6) Uani 1 1 d . U . . .
N1 N 0.1295(3) 0.03657(19) 0.80982(18) 0.0290(5) Uani 1 1 d . . . . .
N4 N 0.4208(3) 0.1625(2) 0.87303(18) 0.0311(6) Uani 1 1 d . . . . .
Cl2 Cl 0.02035(10) 0.27260(7) 0.84677(6) 0.0403(2) Uani 1 1 d . . . . .
Cl1 Cl 0.32049(10) 0.32682(6) 0.68665(6) 0.0385(2) 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
Mn1 N4 2.317(3) . ?
Mn1 N1 2.320(3) . ?
Mn1 N3 2.324(3) . ?
Mn1 N2 2.331(3) . ?
Mn1 Cl2 2.4396(9) . ?
Mn1 Cl1 2.4559(9) . ?
C1 N3 1.467(4) . ?
C1 C2 1.577(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.577(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C5 1.501(5) . ?
C4 N2 1.508(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.487(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.484(5) . ?
C6 C7 1.486(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.461(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N4 1.456(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 N4 1.479(4) . ?
C10 C11 1.517(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N3 1.482(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N3 1.474(4) . ?
C12 C13 1.547(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N1 1.479(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C3 N2 1.439(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C9 N4 1.495(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
N4 Mn1 N1 81.97(9) . . ?
N4 Mn1 N3 78.47(9) . . ?
N1 Mn1 N3 74.92(9) . . ?
N4 Mn1 N2 150.29(10) . . ?
N1 Mn1 N2 78.98(10) . . ?
N3 Mn1 N2 74.70(10) . . ?
N4 Mn1 Cl2 99.12(7) . . ?
N1 Mn1 Cl2 92.48(7) . . ?
N3 Mn1 Cl2 167.36(7) . . ?
N2 Mn1 Cl2 104.25(8) . . ?
N4 Mn1 Cl1 99.79(7) . . ?
N1 Mn1 Cl1 168.38(7) . . ?
N3 Mn1 Cl1 94.10(7) . . ?
N2 Mn1 Cl1 94.65(8) . . ?
Cl2 Mn1 Cl1 98.54(4) . . ?
N3 C1 C2 110.1(3) . . ?
N3 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N3 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C1 C2 N2 113.8(3) . . ?
C1 C2 H2A 108.8 . . ?
N2 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
N2 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C5 C4 N2 113.2(3) . . ?
C5 C4 H4A 108.9 . . ?
N2 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
N2 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C4 112.1(3) . . ?
N1 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C7 116.3(3) . . ?
N1 C6 H6A 108.2 . . ?
C7 C6 H6A 108.2 . . ?
N1 C6 H6B 108.2 . . ?
C7 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C8 C7 C6 117.1(4) . . ?
C8 C7 H7A 108.0 . . ?
C6 C7 H7A 108.0 . . ?
C8 C7 H7B 108.0 . . ?
C6 C7 H7B 108.0 . . ?
H7A C7 H7B 107.3 . . ?
N4 C8 C7 118.4(4) . . ?
N4 C8 H8A 107.7 . . ?
C7 C8 H8A 107.7 . . ?
N4 C8 H8B 107.7 . . ?
C7 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
N4 C10 C11 111.1(3) . . ?
N4 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
N4 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 C10 111.2(3) . . ?
N3 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N3 C12 C13 114.8(3) . . ?
N3 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
N3 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.5 . . ?
N1 C13 C12 114.0(3) . . ?
N1 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 N3 C12 111.5(3) . . ?
C1 N3 C11 112.3(3) . . ?
C12 N3 C11 111.9(3) . . ?
C1 N3 Mn1 103.9(2) . . ?
C12 N3 Mn1 115.7(2) . . ?
C11 N3 Mn1 101.1(2) . . ?
C3 N2 C4 112.1(3) . . ?
C3 N2 C2 112.1(4) . . ?
C4 N2 C2 109.5(3) . . ?
C3 N2 Mn1 109.0(3) . . ?
C4 N2 Mn1 106.41(19) . . ?
C2 N2 Mn1 107.43(19) . . ?
C13 N1 C6 110.8(3) . . ?
C13 N1 C5 110.7(3) . . ?
C6 N1 C5 108.9(3) . . ?
C13 N1 Mn1 116.16(19) . . ?
C6 N1 Mn1 110.8(2) . . ?
C5 N1 Mn1 98.74(19) . . ?
C8 N4 C10 115.5(3) . . ?
C8 N4 C9 105.0(3) . . ?
C10 N4 C9 107.4(3) . . ?
C8 N4 Mn1 112.9(2) . . ?
C10 N4 Mn1 108.28(19) . . ?
C9 N4 Mn1 107.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C1 C2 N2 31.2(4) . . . . ?
N2 C4 C5 N1 -56.4(4) . . . . ?
N1 C6 C7 C8 63.9(5) . . . . ?
C6 C7 C8 N4 -61.4(5) . . . . ?
N4 C10 C11 N3 -60.4(4) . . . . ?
N3 C12 C13 N1 24.4(4) . . . . ?
C2 C1 N3 C12 69.4(4) . . . . ?
C2 C1 N3 C11 -164.1(3) . . . . ?
C2 C1 N3 Mn1 -55.8(3) . . . . ?
C13 C12 N3 C1 -137.5(3) . . . . ?
C13 C12 N3 C11 95.9(3) . . . . ?
C13 C12 N3 Mn1 -19.1(3) . . . . ?
C10 C11 N3 C1 165.8(3) . . . . ?
C10 C11 N3 C12 -68.0(4) . . . . ?
C10 C11 N3 Mn1 55.7(3) . . . . ?
C5 C4 N2 C3 -100.9(4) . . . . ?
C5 C4 N2 C2 134.1(3) . . . . ?
C5 C4 N2 Mn1 18.2(3) . . . . ?
C1 C2 N2 C3 129.7(4) . . . . ?
C1 C2 N2 C4 -105.2(3) . . . . ?
C1 C2 N2 Mn1 10.0(4) . . . . ?
C12 C13 N1 C6 -145.7(3) . . . . ?
C12 C13 N1 C5 93.4(3) . . . . ?
C12 C13 N1 Mn1 -18.1(3) . . . . ?
C7 C6 N1 C13 62.6(4) . . . . ?
C7 C6 N1 C5 -175.3(3) . . . . ?
C7 C6 N1 Mn1 -67.8(4) . . . . ?
C4 C5 N1 C13 -63.3(4) . . . . ?
C4 C5 N1 C6 174.6(3) . . . . ?
C4 C5 N1 Mn1 59.0(3) . . . . ?
C7 C8 N4 C10 -61.6(4) . . . . ?
C7 C8 N4 C9 -179.6(3) . . . . ?
C7 C8 N4 Mn1 63.7(4) . . . . ?
C11 C10 N4 C8 155.8(3) . . . . ?
C11 C10 N4 C9 -87.6(3) . . . . ?
C11 C10 N4 Mn1 28.1(3) . . . . ?

_refine_diff_density_max         1.516
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.096



####################################################################### 
# 
# 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_sja17_07
_database_code_depnum_ccdc_archive 'CCDC 1049978'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_vrf_PLAT029_sja17_07            
;
RESPONSE: The crystal examined was a pseudo-merohedral twin. 
The data were treated with Rotax to deal with this. A portion 
of the data suspected to contain partially overlap from 
the two twin components was omitted. This led to a 
significant increase in the quality of the fit. 
;


_vrf_PLAT341_sja17_07            
;
RESPONSE: The crystal examined was a pseudo-merohedral twin. 
This leads to moderate precision in the determination of the
structure. The ORTEP plot shows there is no problem with 
the structure. 
;


_vrf_PLAT410_sja17_07            
;
RESPONSE: This is due to the extreme rigidity of the macrocyclic chelator
 forcing less favourable geometries and close interactions on the alkyl
 backbone between H7B and H13B. 
;


_vrf_RFACR01_sja17_07            
;
RESPONSE: The crystal examined was a pseudo-merohedral twin. 
The data were treated with Rotax to deal with this. This gave a much
better fit to the observed data, but the wR2 is still modest. 
;

_vrf_PLAT084_sja17_07            
;
RESPONSE: The crystal examined was a pseudo-merohedral twin. 
The data were treated with Rotax to deal with this. This gave a much
better fit to the observed data, but the wR2 is still modest. 
;


_vrf_PLAT234_sja17_07            
;
RESPONSE: The crystal examined was a pseudo-merohedral twin. 
This may be a reflection of imperfect deconvolution of scattering from 
the two twin domains. The ORTEP plots shows there is no serious problem. 
;



_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C13 H28 Cl2 Mn N4, F6 P
;
_chemical_formula_sum            'C13 H28 Cl2 F6 Mn N4 P'
_chemical_formula_weight         511.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   9.565(3)
_cell_length_b                   14.488(3)
_cell_length_c                   14.644(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.30(2)
_cell_angle_gamma                90
_cell_volume                     2027.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8690
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      29.75

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.054
_shelx_estimated_absorpt_T_min   0.621
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6601
_exptl_absorpt_correction_T_max  0.8632
_exptl_absorpt_process_details   
;
A face-index absorption correction was applied within the 
Stoe X-AREA suite.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       w-scans
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            9515
_diffrn_reflns_av_unetI/netI     0.1290
_diffrn_reflns_v_R_equivalents   0.1196
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.553
_diffrn_reflns_theta_max         25.613
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.889
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_Laue_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.889
_reflns_number_total             9515
_reflns_number_gt                4773
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'Stoe X-AREA'
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_solution    SHELXS-86
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component 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)+(0.1465P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9515
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1535
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.2704
_refine_ls_wR_factor_gt          0.2253
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_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
Mn1 Mn 0.06858(18) 0.50557(11) 0.24591(15) 0.0298(5) Uani 1 1 d . . . . .
Cl1 Cl -0.0049(5) 0.4088(3) 0.1323(3) 0.0583(12) Uani 1 1 d . . . . .
Cl2 Cl 0.0195(5) 0.3982(2) 0.3510(3) 0.0482(11) Uani 1 1 d . . . . .
N1 N 0.1188(11) 0.6110(8) 0.1544(8) 0.031(3) Uani 1 1 d . . . . .
C1 C 0.2040(15) 0.5683(10) 0.0848(10) 0.040(4) Uani 1 1 d . . . . .
H1A H 0.2397 0.6171 0.0444 0.048 Uiso 1 1 calc R U . . .
H1B H 0.1446 0.5262 0.0467 0.048 Uiso 1 1 calc R U . . .
C2 C 0.3280(16) 0.5140(10) 0.1274(10) 0.041(4) Uani 1 1 d . . . . .
H2A H 0.3495 0.4615 0.0869 0.049 Uiso 1 1 calc R U . . .
H2B H 0.4112 0.5546 0.1314 0.049 Uiso 1 1 calc R U . . .
N2 N 0.3001(10) 0.4778(6) 0.2206(8) 0.033(3) Uani 1 1 d . . . . .
C3 C 0.3298(15) 0.3766(8) 0.2266(12) 0.044(4) Uani 1 1 d . . . . .
H3A H 0.4297 0.3658 0.2186 0.065 Uiso 1 1 calc R U . . .
H3B H 0.2751 0.3442 0.1786 0.065 Uiso 1 1 calc R U . . .
H3C H 0.3042 0.3535 0.2865 0.065 Uiso 1 1 calc R U . . .
C4 C 0.3785(13) 0.5259(9) 0.2960(10) 0.034(3) Uani 1 1 d . . . . .
H4A H 0.4146 0.5852 0.2732 0.041 Uiso 1 1 calc R U . . .
H4B H 0.4595 0.4877 0.3166 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2869(14) 0.5439(9) 0.3759(11) 0.038(3) Uani 1 1 d . . . . .
H5A H 0.3395 0.5805 0.4229 0.046 Uiso 1 1 calc R U . . .
H5B H 0.2599 0.4846 0.4037 0.046 Uiso 1 1 calc R U . . .
N3 N 0.1567(13) 0.5962(7) 0.3435(8) 0.036(3) Uani 1 1 d . . . . .
C6 C 0.0671(16) 0.6108(10) 0.4233(10) 0.039(4) Uani 1 1 d . . . . .
H6A H 0.1163 0.6530 0.4670 0.047 Uiso 1 1 calc R U . . .
H6B H 0.0546 0.5510 0.4546 0.047 Uiso 1 1 calc R U . . .
C7 C -0.0770(17) 0.6511(12) 0.3978(11) 0.051(4) Uani 1 1 d . . . . .
H7A H -0.1245 0.6629 0.4555 0.061 Uiso 1 1 calc R U . . .
H7B H -0.0619 0.7119 0.3689 0.061 Uiso 1 1 calc R U . . .
C8 C -0.174(2) 0.5998(13) 0.3379(12) 0.066(5) Uani 1 1 d . . . . .
H8A H -0.1900 0.5390 0.3665 0.079 Uiso 1 1 calc R U . . .
H8B H -0.2647 0.6330 0.3363 0.079 Uiso 1 1 calc R U . . .
N4 N -0.1377(12) 0.5837(9) 0.2456(11) 0.057(4) Uani 1 1 d . . . . .
C9 C -0.2498(16) 0.5303(12) 0.1989(15) 0.066(6) Uani 1 1 d . . . . .
H9A H -0.3385 0.5638 0.2022 0.099 Uiso 1 1 calc R U . . .
H9B H -0.2580 0.4700 0.2285 0.099 Uiso 1 1 calc R U . . .
H9C H -0.2277 0.5216 0.1347 0.099 Uiso 1 1 calc R U . . .
C10 C -0.1150(15) 0.6714(10) 0.1898(11) 0.044(4) Uani 1 1 d . . . . .
H10A H -0.2053 0.6940 0.1630 0.052 Uiso 1 1 calc R U . . .
H10B H -0.0733 0.7204 0.2293 0.052 Uiso 1 1 calc R U . . .
C11 C -0.0170(16) 0.6465(10) 0.1150(10) 0.039(3) Uani 1 1 d . . . . .
H11A H -0.0612 0.5988 0.0749 0.047 Uiso 1 1 calc R U . . .
H11B H 0.0002 0.7017 0.0772 0.047 Uiso 1 1 calc R U . . .
C12 C 0.2036(15) 0.6869(9) 0.2009(9) 0.031(3) Uani 1 1 d . . . . .
H12A H 0.1723 0.7472 0.1756 0.038 Uiso 1 1 calc R U . . .
H12B H 0.3032 0.6789 0.1869 0.038 Uiso 1 1 calc R U . . .
C13 C 0.1905(15) 0.6882(9) 0.3051(10) 0.032(3) Uani 1 1 d . . . . .
H13A H 0.2797 0.7103 0.3340 0.039 Uiso 1 1 calc R U . . .
H13B H 0.1163 0.7325 0.3207 0.039 Uiso 1 1 calc R U . . .
P1 P 0.5291(3) 0.7515(4) 0.5104(3) 0.0382(9) Uani 1 1 d . . . . .
F1 F 0.5202(9) 0.7183(6) 0.4059(6) 0.049(2) Uani 1 1 d . . . . .
F2 F 0.6874(8) 0.7840(7) 0.4992(7) 0.066(3) Uani 1 1 d . . . . .
F3 F 0.3690(8) 0.7223(6) 0.5193(6) 0.053(3) Uani 1 1 d . . . . .
F4 F 0.5364(9) 0.7827(6) 0.6143(6) 0.052(3) Uani 1 1 d . . . . .
F5 F 0.4809(10) 0.8512(6) 0.4802(7) 0.056(2) Uani 1 1 d . . . . .
F6 F 0.5803(13) 0.6517(7) 0.5398(7) 0.075(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
Mn1 N3 2.093(12) . ?
Mn1 N1 2.100(12) . ?
Mn1 Cl2 2.250(4) . ?
Mn1 Cl1 2.266(5) . ?
Mn1 N4 2.275(12) . ?
Mn1 N2 2.296(10) . ?
N1 C1 1.466(17) . ?
N1 C11 1.491(18) . ?
N1 C12 1.512(17) . ?
C1 C2 1.54(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.496(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N2 C4 1.482(17) . ?
N2 C3 1.495(14) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.51(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N3 1.518(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N3 C13 1.487(16) . ?
N3 C6 1.491(18) . ?
C6 C7 1.53(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.46(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N4 1.43(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N4 C9 1.47(2) . ?
N4 C10 1.530(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.51(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.54(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
P1 F5 1.574(10) . ?
P1 F6 1.581(10) . ?
P1 F4 1.586(10) . ?
P1 F3 1.599(8) . ?
P1 F2 1.600(9) . ?
P1 F1 1.603(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Mn1 N1 83.3(4) . . ?
N3 Mn1 Cl2 93.2(3) . . ?
N1 Mn1 Cl2 176.5(4) . . ?
N3 Mn1 Cl1 173.8(3) . . ?
N1 Mn1 Cl1 93.1(3) . . ?
Cl2 Mn1 Cl1 90.43(16) . . ?
N3 Mn1 N4 90.8(5) . . ?
N1 Mn1 N4 81.8(4) . . ?
Cl2 Mn1 N4 98.1(4) . . ?
Cl1 Mn1 N4 93.6(4) . . ?
N3 Mn1 N2 81.7(4) . . ?
N1 Mn1 N2 77.2(4) . . ?
Cl2 Mn1 N2 102.6(3) . . ?
Cl1 Mn1 N2 92.6(3) . . ?
N4 Mn1 N2 158.3(4) . . ?
C1 N1 C11 112.1(11) . . ?
C1 N1 C12 108.4(11) . . ?
C11 N1 C12 111.5(10) . . ?
C1 N1 Mn1 106.5(8) . . ?
C11 N1 Mn1 106.2(8) . . ?
C12 N1 Mn1 111.9(8) . . ?
N1 C1 C2 112.1(12) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N2 C2 C1 112.8(11) . . ?
N2 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
N2 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 N2 C3 109.1(11) . . ?
C4 N2 C2 114.3(10) . . ?
C3 N2 C2 110.9(11) . . ?
C4 N2 Mn1 105.1(7) . . ?
C3 N2 Mn1 110.2(8) . . ?
C2 N2 Mn1 107.1(8) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 C5 111.5(10) . . ?
N2 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 N3 109.8(11) . . ?
C4 C5 H5A 109.7 . . ?
N3 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
N3 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C13 N3 C6 108.0(10) . . ?
C13 N3 C5 112.2(11) . . ?
C6 N3 C5 108.4(11) . . ?
C13 N3 Mn1 113.1(9) . . ?
C6 N3 Mn1 113.3(9) . . ?
C5 N3 Mn1 101.7(8) . . ?
N3 C6 C7 113.8(12) . . ?
N3 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
N3 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 120.0(15) . . ?
C8 C7 H7A 107.3 . . ?
C6 C7 H7A 107.3 . . ?
C8 C7 H7B 107.3 . . ?
C6 C7 H7B 107.3 . . ?
H7A C7 H7B 106.9 . . ?
N4 C8 C7 118.6(17) . . ?
N4 C8 H8A 107.7 . . ?
C7 C8 H8A 107.7 . . ?
N4 C8 H8B 107.7 . . ?
C7 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
C8 N4 C9 109.0(15) . . ?
C8 N4 C10 114.5(14) . . ?
C9 N4 C10 107.8(14) . . ?
C8 N4 Mn1 108.9(13) . . ?
C9 N4 Mn1 110.8(10) . . ?
C10 N4 Mn1 105.8(8) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N4 107.1(12) . . ?
C11 C10 H10A 110.3 . . ?
N4 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
N4 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
N1 C11 C10 110.9(12) . . ?
N1 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
N1 C12 C13 113.1(12) . . ?
N1 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N1 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N3 C13 C12 113.0(12) . . ?
N3 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
N3 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
F5 P1 F6 178.9(6) . . ?
F5 P1 F4 90.5(5) . . ?
F6 P1 F4 89.9(6) . . ?
F5 P1 F3 89.7(5) . . ?
F6 P1 F3 91.3(6) . . ?
F4 P1 F3 90.1(5) . . ?
F5 P1 F2 88.2(5) . . ?
F6 P1 F2 90.7(6) . . ?
F4 P1 F2 90.5(5) . . ?
F3 P1 F2 177.9(6) . . ?
F5 P1 F1 90.2(6) . . ?
F6 P1 F1 89.4(5) . . ?
F4 P1 F1 179.0(6) . . ?
F3 P1 F1 89.1(5) . . ?
F2 P1 F1 90.3(5) . . ?

_refine_diff_density_max         1.048
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.148

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_DGJ031
_database_code_depnum_ccdc_archive 'CCDC 1049979'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_vrf_PLAT410_DGJ031              
;
RESPONSE: This is due to the extreme rigidity of the macrocyclic chelator
 forcing less favourable geometries and close interactions on the alkyl
 backbone between H7B and H13B.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C13 H28 Cl2 Co N4, F6 P
;
_chemical_formula_sum            'C13 H28 Cl2 Co F6 N4 P'
_chemical_formula_weight         515.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   9.5547(7)
_cell_length_b                   14.1978(7)
_cell_length_c                   14.5613(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.613(6)
_cell_angle_gamma                90
_cell_volume                     1973.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10218
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      29.4

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.283
_shelx_estimated_absorpt_T_min   0.615
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6785
_exptl_absorpt_correction_T_max  0.8782
_exptl_absorpt_process_details   
;
A face-index absorption correction was applied
within the Stoe X-AREA software.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            15557
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.004
_diffrn_reflns_theta_max         29.190
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5307
_reflns_number_gt                3335
_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.

The crystal examined was found to be twinned. A second 
component related to the first by a 180 degree rotation 
about 0 0 1 direction was present. However, this was a minor
component and much of the data from the second component
was very weak. Refinement with two twin components did not
improve the refinement. The final refinement uses a single
twin component. 



;

_computing_data_collection       'Stoe X-AREA'
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Hydrogen atoms were located in difference Fourier maps. 
They were placed at geometrically calculated positions
but C-H bond distances were refined. Chemically similar
C-H bonds were constrained to be similar. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0703P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5307
_refine_ls_number_parameters     261
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   0.884
_refine_ls_restrained_S_all      0.882
_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
Co1 Co 0.07761(4) 0.51795(3) 0.24315(3) 0.02389(11) Uani 1 1 d . . . . .
Cl1 Cl 0.01081(9) 0.41694(5) 0.12770(5) 0.03391(19) Uani 1 1 d . . . . .
Cl2 Cl 0.02738(9) 0.40332(5) 0.34323(5) 0.03235(18) Uani 1 1 d . . . . .
N1 N 0.1185(3) 0.61849(17) 0.15671(17) 0.0264(5) Uani 1 1 d . . . . .
C1 C 0.2043(4) 0.5780(2) 0.0833(2) 0.0314(7) Uani 1 1 d D . . . .
H1A H 0.2522(8) 0.6286(8) 0.0520(5) 0.038 Uiso 1 1 calc DR U . . .
H1B H 0.1433(10) 0.5454(5) 0.0381(7) 0.038 Uiso 1 1 calc DR U . . .
C2 C 0.3122(4) 0.5090(2) 0.1250(2) 0.0354(7) Uani 1 1 d D . . . .
H2A H 0.3155(4) 0.4541(9) 0.0865(6) 0.043 Uiso 1 1 calc DR U . . .
H2B H 0.4032(15) 0.5380(5) 0.1266(2) 0.043 Uiso 1 1 calc DR U . . .
N2 N 0.2785(3) 0.47913(17) 0.22154(17) 0.0279(5) Uani 1 1 d . . . . .
C3 C 0.3090(4) 0.3762(2) 0.2319(2) 0.0352(7) Uani 1 1 d D . . . .
H3A H 0.412(2) 0.3631(4) 0.2151(17) 0.053 Uiso 1 1 calc DR U . . .
H3B H 0.241(2) 0.3380(7) 0.1882(15) 0.053 Uiso 1 1 calc DR U . . .
H3C H 0.295(3) 0.3559(6) 0.2997(13) 0.053 Uiso 1 1 calc DR U . . .
C4 C 0.3719(4) 0.5289(2) 0.2919(2) 0.0340(7) Uani 1 1 d D . . . .
H4A H 0.4062(7) 0.5877(9) 0.2663(4) 0.041 Uiso 1 1 calc DR U . . .
H4B H 0.4525(13) 0.4894(6) 0.3090(3) 0.041 Uiso 1 1 calc DR U . . .
C5 C 0.2893(4) 0.5493(2) 0.3752(2) 0.0326(7) Uani 1 1 d D . . . .
H5A H 0.2662(5) 0.4906(9) 0.4059(5) 0.039 Uiso 1 1 calc DR U . . .
H5B H 0.3445(9) 0.5884(6) 0.4185(7) 0.039 Uiso 1 1 calc DR U . . .
N3 N 0.1580(3) 0.59982(17) 0.34397(16) 0.0267(5) Uani 1 1 d . . . . .
C6 C 0.0732(4) 0.6113(2) 0.4271(2) 0.0317(7) Uani 1 1 d D . . . .
H6A H 0.1241(8) 0.6528(7) 0.4705(7) 0.038 Uiso 1 1 calc DR U . . .
H6B H 0.0647(4) 0.5499(9) 0.4567(5) 0.038 Uiso 1 1 calc DR U . . .
C7 C -0.0724(4) 0.6511(2) 0.4083(2) 0.0370(8) Uani 1 1 d D . . . .
H7A H -0.1171(8) 0.6591(3) 0.4674(9) 0.044 Uiso 1 1 calc DR U . . .
H7B H -0.0636(4) 0.7140(10) 0.3807(5) 0.044 Uiso 1 1 calc DR U . . .
C8 C -0.1680(4) 0.5921(2) 0.3457(2) 0.0364(8) Uani 1 1 d . . . . .
H8A H -0.1809(6) 0.5327(17) 0.3742(8) 0.044 Uiso 1 1 calc R U . . .
H8B H -0.257(3) 0.6222(9) 0.3404(3) 0.044 Uiso 1 1 calc R U . . .
N4 N -0.1189(3) 0.57534(18) 0.25086(18) 0.0307(6) Uani 1 1 d . . . . .
C9 C -0.2328(4) 0.5165(3) 0.2046(3) 0.0407(8) Uani 1 1 d D . . . .
H9A H -0.3307(18) 0.5491(11) 0.2126(16) 0.061 Uiso 1 1 calc DR U . . .
H9B H -0.2331(18) 0.4490(13) 0.2349(13) 0.061 Uiso 1 1 calc DR U . . .
H9C H -0.2143(16) 0.5101(16) 0.1341(13) 0.061 Uiso 1 1 calc DR U . . .
C10 C -0.1140(4) 0.6663(2) 0.1973(2) 0.0327(7) Uani 1 1 d D . . . .
H10A H -0.2084(15) 0.6835(4) 0.1742(4) 0.039 Uiso 1 1 calc DR U . . .
H10B H -0.0777(6) 0.7170(8) 0.2371(6) 0.039 Uiso 1 1 calc DR U . . .
C11 C -0.0204(4) 0.6527(2) 0.1183(2) 0.0311(7) Uani 1 1 d D . . . .
H11A H -0.0611(7) 0.6068(7) 0.0753(7) 0.037 Uiso 1 1 calc DR U . . .
H11B H -0.0090(4) 0.7119(9) 0.0859(5) 0.037 Uiso 1 1 calc DR U . . .
C12 C 0.2012(4) 0.6968(2) 0.2036(2) 0.0310(7) Uani 1 1 d D . . . .
H12A H 0.1672(6) 0.7574(9) 0.1792(4) 0.037 Uiso 1 1 calc DR U . . .
H12B H 0.3000(15) 0.6906(2) 0.1890(3) 0.037 Uiso 1 1 calc DR U . . .
C13 C 0.1903(4) 0.6965(2) 0.3073(2) 0.0316(7) Uani 1 1 d D . . . .
H13A H 0.2784(14) 0.7187(4) 0.3360(5) 0.038 Uiso 1 1 calc DR U . . .
H13B H 0.1168(12) 0.7401(7) 0.3240(3) 0.038 Uiso 1 1 calc DR U . . .
P1 P 0.53740(10) 0.75575(6) 0.51058(6) 0.03243(19) Uani 1 1 d . . . . .
F1 F 0.5332(2) 0.72108(16) 0.40580(14) 0.0442(5) Uani 1 1 d . . . . .
F2 F 0.6957(2) 0.78971(18) 0.50152(16) 0.0530(6) Uani 1 1 d . . . . .
F3 F 0.3776(2) 0.72353(14) 0.51931(14) 0.0409(5) Uani 1 1 d . . . . .
F4 F 0.5406(2) 0.79029(17) 0.61585(14) 0.0491(6) Uani 1 1 d . . . . .
F5 F 0.4845(3) 0.85736(15) 0.47851(16) 0.0507(6) Uani 1 1 d . . . . .
F6 F 0.5891(3) 0.65365(17) 0.54213(16) 0.0579(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 1.954(2) . ?
Co1 N3 1.998(2) . ?
Co1 N2 2.035(3) . ?
Co1 N4 2.055(3) . ?
Co1 Cl2 2.2509(8) . ?
Co1 Cl1 2.2785(8) . ?
N1 C1 1.491(4) . ?
N1 C11 1.498(4) . ?
N1 C12 1.508(4) . ?
C1 C2 1.527(5) . ?
C1 H1A 0.976(14) . ?
C1 H1B 0.976(14) . ?
C2 N2 1.517(4) . ?
C2 H2A 0.962(15) . ?
C2 H2B 0.962(15) . ?
N2 C3 1.496(4) . ?
N2 C4 1.504(4) . ?
C3 H3A 1.043(18) . ?
C3 H3B 1.043(18) . ?
C3 H3C 1.043(18) . ?
C4 C5 1.505(5) . ?
C4 H4A 0.977(15) . ?
C4 H4B 0.977(15) . ?
C5 N3 1.498(4) . ?
C5 H5A 0.977(15) . ?
C5 H5B 0.977(15) . ?
N3 C6 1.495(4) . ?
N3 C13 1.510(4) . ?
C6 C7 1.515(5) . ?
C6 H6A 0.978(15) . ?
C6 H6B 0.978(14) . ?
C7 C8 1.513(5) . ?
C7 H7A 0.984(15) . ?
C7 H7B 0.984(15) . ?
C8 N4 1.498(4) . ?
C8 H8A 0.95(3) . ?
C8 H8B 0.95(3) . ?
N4 C9 1.506(4) . ?
N4 C10 1.510(4) . ?
C9 H9A 1.055(18) . ?
C9 H9B 1.055(18) . ?
C9 H9C 1.055(18) . ?
C10 C11 1.500(5) . ?
C10 H10A 0.979(15) . ?
C10 H10B 0.979(15) . ?
C11 H11A 0.972(14) . ?
C11 H11B 0.972(14) . ?
C12 C13 1.519(4) . ?
C12 H12A 0.981(15) . ?
C12 H12B 0.981(15) . ?
C13 H13A 0.975(15) . ?
C13 H13B 0.975(15) . ?
P1 F5 1.592(2) . ?
P1 F6 1.592(2) . ?
P1 F2 1.599(2) . ?
P1 F1 1.602(2) . ?
P1 F3 1.604(2) . ?
P1 F4 1.608(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
N1 Co1 N3 88.10(10) . . ?
N1 Co1 N2 83.13(11) . . ?
N3 Co1 N2 86.42(11) . . ?
N1 Co1 N4 87.46(11) . . ?
N3 Co1 N4 92.91(11) . . ?
N2 Co1 N4 170.59(10) . . ?
N1 Co1 Cl2 179.11(8) . . ?
N3 Co1 Cl2 91.78(7) . . ?
N2 Co1 Cl2 97.74(8) . . ?
N4 Co1 Cl2 91.66(8) . . ?
N1 Co1 Cl1 92.41(8) . . ?
N3 Co1 Cl1 173.42(8) . . ?
N2 Co1 Cl1 87.13(8) . . ?
N4 Co1 Cl1 93.67(8) . . ?
Cl2 Co1 Cl1 87.81(3) . . ?
C1 N1 C11 111.4(2) . . ?
C1 N1 C12 108.4(3) . . ?
C11 N1 C12 111.5(2) . . ?
C1 N1 Co1 108.19(18) . . ?
C11 N1 Co1 106.09(19) . . ?
C12 N1 Co1 111.28(18) . . ?
N1 C1 C2 110.2(2) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N2 C2 C1 112.3(3) . . ?
N2 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N2 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C3 N2 C4 106.5(3) . . ?
C3 N2 C2 108.5(2) . . ?
C4 N2 C2 110.8(3) . . ?
C3 N2 Co1 115.5(2) . . ?
C4 N2 Co1 107.57(19) . . ?
C2 N2 Co1 108.01(19) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 C5 108.8(3) . . ?
N2 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N3 C5 C4 108.1(2) . . ?
N3 C5 H5A 110.1 . . ?
C4 C5 H5A 110.1 . . ?
N3 C5 H5B 110.1 . . ?
C4 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
C6 N3 C5 106.5(2) . . ?
C6 N3 C13 108.3(2) . . ?
C5 N3 C13 111.1(3) . . ?
C6 N3 Co1 117.0(2) . . ?
C5 N3 Co1 103.47(18) . . ?
C13 N3 Co1 110.32(18) . . ?
N3 C6 C7 114.9(3) . . ?
N3 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
N3 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C6 115.3(3) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
N4 C8 C7 116.0(3) . . ?
N4 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
N4 C8 H8B 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C8 N4 C9 104.5(3) . . ?
C8 N4 C10 111.0(2) . . ?
C9 N4 C10 106.4(3) . . ?
C8 N4 Co1 116.0(2) . . ?
C9 N4 Co1 113.5(2) . . ?
C10 N4 Co1 105.12(19) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N4 108.7(3) . . ?
C11 C10 H10A 110.0 . . ?
N4 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
N4 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
N1 C11 C10 107.8(2) . . ?
N1 C11 H11A 110.2 . . ?
C10 C11 H11A 110.2 . . ?
N1 C11 H11B 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
N1 C12 C13 113.0(2) . . ?
N1 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N1 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N3 C13 C12 112.2(2) . . ?
N3 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
F5 P1 F6 179.45(16) . . ?
F5 P1 F2 89.51(13) . . ?
F6 P1 F2 90.93(15) . . ?
F5 P1 F1 90.30(13) . . ?
F6 P1 F1 89.37(12) . . ?
F2 P1 F1 89.81(12) . . ?
F5 P1 F3 89.49(12) . . ?
F6 P1 F3 90.08(14) . . ?
F2 P1 F3 178.99(13) . . ?
F1 P1 F3 90.31(11) . . ?
F5 P1 F4 89.73(13) . . ?
F6 P1 F4 90.59(13) . . ?
F2 P1 F4 90.54(13) . . ?
F1 P1 F4 179.65(14) . . ?
F3 P1 F4 89.34(12) . . ?

_refine_diff_density_max         0.871
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.107

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_DGJ031b
_database_code_depnum_ccdc_archive 'CCDC 1049980'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_vrf_GOODF01_DGJ031b             
;
RESPONSE: The needle was weakly scattering. The data collection
undertaken was as long a reasonably practicable. The crystal did 
not scatter strongly beyond 40 degrees therefore a fair proportion
of weak data are included in the refinement. This is the reason
for the slightly low GooF. 
;

_vrf_PLAT026_DGJ031b             
;
RESPONSE: The needle was weakly scattering. The data collection
undertaken was as long a reasonably practicable. The crystal did 
not scatter strongly beyond 40 degrees therefore a fair proportion
of weak data are included in the refinement. 
;

_vrf_PLAT410_DGJ031b             
;
RESPONSE: This is due to the extreme rigidity of the macrocyclic chelator
 forcing less favourable geometries and close interactions on the alkyl
 backbone between H7A and H13A.
;





_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C13 H28 Cl2 Co N4, F6 P, C2 H3 N
;
_chemical_formula_sum            'C15 H31 Cl2 Co F6 N5 P'
_chemical_formula_weight         556.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   8.0397(8)
_cell_length_b                   30.477(3)
_cell_length_c                   8.9610(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.189(8)
_cell_angle_gamma                90
_cell_volume                     2189.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3982
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.75

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.164
_shelx_estimated_absorpt_T_min   0.721
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            7957
_diffrn_reflns_av_unetI/netI     0.1589
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         25.424
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3947
_reflns_number_gt                1673
_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       'Stoe X-AREA'
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3947
_refine_ls_number_parameters     277
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1360
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   0.765
_refine_ls_restrained_S_all      0.765
_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
Cl1 Cl 0.9589(2) 0.21152(5) 0.68761(17) 0.0526(4) Uani 1 1 d . . . . .
Cl2 Cl 1.2743(2) 0.18405(5) 0.51711(16) 0.0487(4) Uani 1 1 d . . . . .
Co1 Co 1.00095(12) 0.16709(2) 0.48830(8) 0.0377(2) Uani 1 1 d . . . . .
N1 N 0.7629(6) 0.15331(16) 0.4631(5) 0.0437(13) Uani 1 1 d . . . . .
C1 C 0.7044(8) 0.1410(2) 0.6115(6) 0.0499(17) Uani 1 1 d . . . . .
H1A H 0.6013 0.1233 0.5968 0.060 Uiso 1 1 calc R U . . .
H1B H 0.6779 0.1680 0.6670 0.060 Uiso 1 1 calc R U . . .
C2 C 0.8381(8) 0.1147(2) 0.7033(7) 0.0529(17) Uani 1 1 d . . . . .
H2A H 0.8012 0.0838 0.7098 0.064 Uiso 1 1 calc R U . . .
H2B H 0.8512 0.1267 0.8061 0.064 Uiso 1 1 calc R U . . .
N2 N 1.0073(7) 0.11610(16) 0.6341(5) 0.0467(14) Uani 1 1 d . . . . .
C3 C 1.1449(9) 0.11877(19) 0.7556(7) 0.057(2) Uani 1 1 d . . . . .
H3A H 1.1281 0.0963 0.8312 0.085 Uiso 1 1 calc R U . . .
H3B H 1.1443 0.1479 0.8022 0.085 Uiso 1 1 calc R U . . .
H3C H 1.2522 0.1139 0.7130 0.085 Uiso 1 1 calc R U . . .
C4 C 1.0359(9) 0.07428(19) 0.5493(7) 0.0537(18) Uani 1 1 d . . . . .
H4A H 1.1014 0.0533 0.6141 0.064 Uiso 1 1 calc R U . . .
H4B H 0.9278 0.0605 0.5166 0.064 Uiso 1 1 calc R U . . .
C5 C 1.1295(9) 0.08598(19) 0.4158(7) 0.0508(18) Uani 1 1 d . . . . .
H5A H 1.2440 0.0955 0.4487 0.061 Uiso 1 1 calc R U . . .
H5B H 1.1370 0.0601 0.3499 0.061 Uiso 1 1 calc R U . . .
N3 N 1.0381(6) 0.12240(16) 0.3326(5) 0.0454(13) Uani 1 1 d . . . . .
C6 C 1.1438(9) 0.1354(2) 0.2090(7) 0.0568(18) Uani 1 1 d . . . . .
H6A H 1.2578 0.1418 0.2529 0.068 Uiso 1 1 calc R U . . .
H6B H 1.1516 0.1102 0.1404 0.068 Uiso 1 1 calc R U . . .
C7 C 1.0824(9) 0.1744(2) 0.1193(7) 0.0583(18) Uani 1 1 d . . . . .
H7A H 0.9714 0.1672 0.0702 0.070 Uiso 1 1 calc R U . . .
H7B H 1.1588 0.1794 0.0392 0.070 Uiso 1 1 calc R U . . .
C8 C 1.0678(9) 0.2167(2) 0.2054(7) 0.0555(18) Uani 1 1 d . . . . .
H8A H 1.1809 0.2255 0.2453 0.067 Uiso 1 1 calc R U . . .
H8B H 1.0260 0.2397 0.1345 0.067 Uiso 1 1 calc R U . . .
N4 N 0.9576(6) 0.21557(15) 0.3321(5) 0.0426(13) Uani 1 1 d . . . . .
C9 C 0.9764(9) 0.26113(19) 0.3976(7) 0.0594(19) Uani 1 1 d . . . . .
H9A H 1.0905 0.2650 0.4421 0.089 Uiso 1 1 calc R U . . .
H9B H 0.8975 0.2650 0.4749 0.089 Uiso 1 1 calc R U . . .
H9C H 0.9535 0.2829 0.3183 0.089 Uiso 1 1 calc R U . . .
C10 C 0.7786(8) 0.20975(19) 0.2738(7) 0.0478(16) Uani 1 1 d . . . . .
H10A H 0.7718 0.1884 0.1904 0.057 Uiso 1 1 calc R U . . .
H10B H 0.7329 0.2381 0.2355 0.057 Uiso 1 1 calc R U . . .
C11 C 0.6783(8) 0.1934(2) 0.3984(7) 0.0525(17) Uani 1 1 d . . . . .
H11A H 0.6726 0.2163 0.4763 0.063 Uiso 1 1 calc R U . . .
H11B H 0.5632 0.1863 0.3590 0.063 Uiso 1 1 calc R U . . .
C12 C 0.7326(8) 0.11422(18) 0.3586(6) 0.0467(16) Uani 1 1 d . . . . .
H12A H 0.7143 0.0877 0.4190 0.056 Uiso 1 1 calc R U . . .
H12B H 0.6300 0.1195 0.2932 0.056 Uiso 1 1 calc R U . . .
C13 C 0.8739(8) 0.1060(2) 0.2634(7) 0.0506(17) Uani 1 1 d . . . . .
H13A H 0.8500 0.1205 0.1653 0.061 Uiso 1 1 calc R U . . .
H13B H 0.8826 0.0740 0.2452 0.061 Uiso 1 1 calc R U . . .
N100 N 0.5461(9) 0.1385(2) -0.0061(7) 0.080(2) Uani 1 1 d . . . . .
C100 C 0.5274(9) 0.1019(2) -0.0196(7) 0.0522(18) Uani 1 1 d . . . . .
C101 C 0.5055(9) 0.0543(2) -0.0333(7) 0.0615(19) Uani 1 1 d . . . . .
H10C H 0.6114 0.0407 -0.0556 0.092 Uiso 1 1 calc R U . . .
H10D H 0.4205 0.0479 -0.1143 0.092 Uiso 1 1 calc R U . . .
H10E H 0.4699 0.0425 0.0609 0.092 Uiso 1 1 calc DR U . . .
P1 P 0.5000 0.0000 0.5000 0.0498(6) Uani 1 2 d S . P . .
F1 F 0.4836(5) 0.02564(12) 0.3456(4) 0.0700(12) Uani 1 1 d D . . . .
F2 F 0.6965(4) 0.00785(11) 0.5118(4) 0.0695(11) Uani 1 1 d . . . . .
F3 F 0.4750(5) 0.04519(11) 0.5863(4) 0.0648(11) Uani 1 1 d . . . . .
P2 P 1.0000 0.0000 0.0000 0.0449(6) Uani 1 2 d S . P . .
F4 F 0.9280(6) 0.04810(11) -0.0316(4) 0.0761(13) Uani 1 1 d . . . . .
F5 F 1.1489(5) 0.01978(15) 0.1022(4) 0.0878(14) Uani 1 1 d . . . . .
F6 F 0.8909(5) -0.00293(12) 0.1421(4) 0.0657(10) 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
Cl1 Co1 2.2859(17) . ?
Cl2 Co1 2.2541(19) . ?
Co1 N1 1.956(5) . ?
Co1 N3 1.988(5) . ?
Co1 N2 2.029(5) . ?
Co1 N4 2.047(4) . ?
N1 C1 1.490(7) . ?
N1 C11 1.496(7) . ?
N1 C12 1.524(7) . ?
C1 C2 1.532(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.536(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N2 C3 1.496(7) . ?
N2 C4 1.510(7) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.502(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N3 1.500(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N3 C6 1.498(8) . ?
N3 C13 1.502(7) . ?
C6 C7 1.497(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.511(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N4 1.490(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N4 C10 1.505(7) . ?
N4 C9 1.511(7) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.509(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.491(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
N100 C100 1.129(7) . ?
C100 C101 1.467(9) . ?
C101 H10C 0.9800 . ?
C101 H10D 0.9800 . ?
C101 H10E 0.9800 . ?
P1 F1 1.586(3) 3_656 ?
P1 F1 1.586(3) . ?
P1 F2 1.594(4) 3_656 ?
P1 F2 1.594(4) . ?
P1 F3 1.600(3) . ?
P1 F3 1.600(3) 3_656 ?
P2 F5 1.573(4) 3_755 ?
P2 F5 1.573(4) . ?
P2 F4 1.594(3) . ?
P2 F4 1.594(3) 3_755 ?
P2 F6 1.601(3) . ?
P2 F6 1.601(3) 3_755 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 N3 88.1(2) . . ?
N1 Co1 N2 83.6(2) . . ?
N3 Co1 N2 85.9(2) . . ?
N1 Co1 N4 87.7(2) . . ?
N3 Co1 N4 92.4(2) . . ?
N2 Co1 N4 171.2(2) . . ?
N1 Co1 Cl2 179.14(15) . . ?
N3 Co1 Cl2 92.43(16) . . ?
N2 Co1 Cl2 97.09(15) . . ?
N4 Co1 Cl2 91.64(15) . . ?
N1 Co1 Cl1 91.04(15) . . ?
N3 Co1 Cl1 173.01(15) . . ?
N2 Co1 Cl1 87.07(15) . . ?
N4 Co1 Cl1 94.54(14) . . ?
Cl2 Co1 Cl1 88.46(6) . . ?
C1 N1 C11 112.7(5) . . ?
C1 N1 C12 107.8(5) . . ?
C11 N1 C12 110.7(4) . . ?
C1 N1 Co1 108.7(3) . . ?
C11 N1 Co1 106.4(4) . . ?
C12 N1 Co1 110.5(4) . . ?
N1 C1 C2 110.8(5) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C1 C2 N2 112.1(5) . . ?
C1 C2 H2A 109.2 . . ?
N2 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
N2 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C3 N2 C4 106.3(5) . . ?
C3 N2 C2 109.7(5) . . ?
C4 N2 C2 110.6(5) . . ?
C3 N2 Co1 114.2(4) . . ?
C4 N2 Co1 108.7(3) . . ?
C2 N2 Co1 107.5(3) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 N2 107.7(5) . . ?
C5 C4 H4A 110.2 . . ?
N2 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
N2 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
N3 C5 C4 108.4(5) . . ?
N3 C5 H5A 110.0 . . ?
C4 C5 H5A 110.0 . . ?
N3 C5 H5B 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C6 N3 C5 106.3(5) . . ?
C6 N3 C13 108.2(4) . . ?
C5 N3 C13 110.0(5) . . ?
C6 N3 Co1 117.4(4) . . ?
C5 N3 Co1 104.5(3) . . ?
C13 N3 Co1 110.2(4) . . ?
C7 C6 N3 115.1(6) . . ?
C7 C6 H6A 108.5 . . ?
N3 C6 H6A 108.5 . . ?
C7 C6 H6B 108.5 . . ?
N3 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C6 C7 C8 115.9(5) . . ?
C6 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
N4 C8 C7 116.3(5) . . ?
N4 C8 H8A 108.2 . . ?
C7 C8 H8A 108.2 . . ?
N4 C8 H8B 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
C8 N4 C10 110.2(4) . . ?
C8 N4 C9 103.1(5) . . ?
C10 N4 C9 108.0(5) . . ?
C8 N4 Co1 117.1(4) . . ?
C10 N4 Co1 105.2(3) . . ?
C9 N4 Co1 113.0(3) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 C11 109.4(5) . . ?
N4 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
N4 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
N1 C11 C10 107.7(5) . . ?
N1 C11 H11A 110.2 . . ?
C10 C11 H11A 110.2 . . ?
N1 C11 H11B 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C13 C12 N1 112.9(5) . . ?
C13 C12 H12A 109.0 . . ?
N1 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
N1 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 N3 113.0(5) . . ?
C12 C13 H13A 109.0 . . ?
N3 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
N3 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N100 C100 C101 178.5(7) . . ?
C100 C101 H10C 109.5 . . ?
C100 C101 H10D 109.5 . . ?
H10C C101 H10D 109.5 . . ?
C100 C101 H10E 109.5 . . ?
H10C C101 H10E 109.5 . . ?
H10D C101 H10E 109.5 . . ?
F1 P1 F1 180.0 3_656 . ?
F1 P1 F2 90.1(2) 3_656 3_656 ?
F1 P1 F2 89.8(2) . 3_656 ?
F1 P1 F2 89.9(2) 3_656 . ?
F1 P1 F2 90.1(2) . . ?
F2 P1 F2 180.0 3_656 . ?
F1 P1 F3 90.44(19) 3_656 . ?
F1 P1 F3 89.56(19) . . ?
F2 P1 F3 90.13(19) 3_656 . ?
F2 P1 F3 89.87(19) . . ?
F1 P1 F3 89.56(19) 3_656 3_656 ?
F1 P1 F3 90.45(19) . 3_656 ?
F2 P1 F3 89.87(19) 3_656 3_656 ?
F2 P1 F3 90.13(18) . 3_656 ?
F3 P1 F3 180.0 . 3_656 ?
F5 P2 F5 180.0 3_755 . ?
F5 P2 F4 89.9(2) 3_755 . ?
F5 P2 F4 90.1(2) . . ?
F5 P2 F4 90.1(2) 3_755 3_755 ?
F5 P2 F4 89.9(2) . 3_755 ?
F4 P2 F4 180.0 . 3_755 ?
F5 P2 F6 90.2(2) 3_755 . ?
F5 P2 F6 89.8(2) . . ?
F4 P2 F6 88.84(19) . . ?
F4 P2 F6 91.16(19) 3_755 . ?
F5 P2 F6 89.8(2) 3_755 3_755 ?
F5 P2 F6 90.2(2) . 3_755 ?
F4 P2 F6 91.16(19) . 3_755 ?
F4 P2 F6 88.85(19) 3_755 3_755 ?
F6 P2 F6 180.0 . 3_755 ?

_refine_diff_density_max         0.943
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.089

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_DGJ033
_database_code_depnum_ccdc_archive 'CCDC 1049981'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_vrf_PLAT410_DGJ033              
;
RESPONSE: This is due to the extreme rigidity of the macrocyclic chelator
 forcing less favourable geometries and close interactions on the alkyl
 backbone. This applies for the contacts H2B---H13A, H8A2---H14B, and 
 H13C---H14B. 
;


_vrf_PLAT341_DGJ033              
;
RESPONSE: There is intriguing disorder that arises from the asymmetry
present in the macrocylic chelator. The bond precision is a little 
lower than ideal, but not bad in this structure. 
;


_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C13 H28 Cl Cu N4, Cl, 2(H2 O)
;

_chemical_formula_sum            'C13 H32 Cl2 Cu N4 O2'
_chemical_formula_weight         410.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   7.2751(5)
_cell_length_b                   27.652(2)
_cell_length_c                   9.5242(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.512(6)
_cell_angle_gamma                90
_cell_volume                     1837.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8679
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      26.1

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             868
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.491
_shelx_estimated_absorpt_T_min   0.623
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.6635
_exptl_absorpt_correction_T_max  0.9236
_exptl_absorpt_process_details   
;
A face-indexed absorption correction was applied
within the Stoe X-AREA suite.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            10561
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.473
_diffrn_reflns_theta_max         25.646
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3461
_reflns_number_gt                2570
_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.


 Hydrogen atoms on the water molecules were located by 
difference Fourier methods and placed using chemically 
reasonable restraints. 
;

_computing_data_collection       'Stoe X-AREA'
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1146P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3461
_refine_ls_number_parameters     197
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1617
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      1.026
_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
Cu1 Cu 0.20036(8) 0.34920(2) 0.64969(5) 0.0288(2) Uani 1 1 d . . . . .
Cl1 Cl 0.09940(19) 0.27415(4) 0.68766(13) 0.0431(3) Uani 1 1 d . . . . .
N1 N 0.2356(6) 0.42096(14) 0.6120(4) 0.0342(8) Uani 1 1 d . . . . .
C1 C 0.1024(7) 0.42970(16) 0.4630(5) 0.0351(10) Uani 1 1 d D . . . .
H1A H 0.1263 0.4620 0.4268 0.042 Uiso 1 1 calc R U . . .
H1B H -0.0323 0.4284 0.4662 0.042 Uiso 1 1 calc R U . . .
C2 C 0.1390(8) 0.39071(16) 0.3635(5) 0.0408(12) Uani 1 1 d D . . . .
H2A H 0.0450 0.3936 0.2657 0.049 Uiso 1 1 calc R U . . .
H2B H 0.2691 0.3947 0.3517 0.049 Uiso 1 1 calc R U . . .
N2 N 0.1222(6) 0.34203(13) 0.4265(4) 0.0324(8) Uani 1 1 d . . . . .
C3 C -0.0769(8) 0.3246(2) 0.3641(5) 0.0509(14) Uani 1 1 d . . . . .
H3A H -0.1023 0.3198 0.2584 0.076 Uiso 1 1 calc R U . . .
H3B H -0.1667 0.3485 0.3825 0.076 Uiso 1 1 calc R U . . .
H3C H -0.0934 0.2938 0.4103 0.076 Uiso 1 1 calc R U . . .
C4 C 0.2552(9) 0.30627(19) 0.3917(6) 0.0520(14) Uani 1 1 d D . . . .
H4A H 0.2388 0.3051 0.2850 0.062 Uiso 1 1 calc R U . A 1
H4B H 0.2324 0.2736 0.4257 0.062 Uiso 1 1 calc R U . A 1
C5A C 0.4702(14) 0.3256(4) 0.4797(11) 0.0443(9) Uiso 0.5 1 d D U P B 1
H5A1 H 0.5611 0.2986 0.4837 0.053 Uiso 0.5 1 calc R U P B 1
H5A2 H 0.5047 0.3516 0.4204 0.053 Uiso 0.5 1 calc R U P B 1
C7 C 0.6005(14) 0.3128(4) 0.7529(10) 0.0393(15) Uani 0.5 1 d . . P B 1
H7A H 0.7323 0.3073 0.7465 0.047 Uiso 0.5 1 calc R U P B 1
H7B H 0.5323 0.2814 0.7370 0.047 Uiso 0.5 1 calc R U P B 1
C8A C 0.6094(16) 0.3325(4) 0.9100(12) 0.0409(13) Uiso 0.5 1 d . U P B 1
H8A1 H 0.6976 0.3114 0.9828 0.049 Uiso 0.5 1 calc R U P B 1
H8A2 H 0.6680 0.3651 0.9198 0.049 Uiso 0.5 1 calc R U P B 1
C9A C 0.4278(16) 0.3361(4) 0.9511(11) 0.0409(13) Uiso 0.5 1 d . U P B 1
H9A1 H 0.4617 0.3459 1.0553 0.049 Uiso 0.5 1 calc R U P B 1
H9A2 H 0.3728 0.3032 0.9449 0.049 Uiso 0.5 1 calc R U P B 1
C10A C 0.104(2) 0.3656(5) 0.9257(14) 0.053(2) Uiso 0.5 1 d . U P B 1
H10A H 0.0394 0.3345 0.8963 0.080 Uiso 0.5 1 calc R U P B 1
H10B H 0.0143 0.3920 0.8863 0.080 Uiso 0.5 1 calc R U P B 1
H10C H 0.1463 0.3677 1.0328 0.080 Uiso 0.5 1 calc R U P B 1
C11A C 0.3283(16) 0.4224(4) 0.8696(12) 0.0443(9) Uiso 0.5 1 d D U P B 1
H11A H 0.4648 0.4250 0.8717 0.053 Uiso 0.5 1 calc R U P B 1
H11B H 0.3120 0.4385 0.9582 0.053 Uiso 0.5 1 calc R U P B 1
C12A C 0.2018(17) 0.4473(5) 0.7320(14) 0.0443(9) Uiso 0.5 1 d D U P B 1
H12A H 0.0650 0.4455 0.7294 0.053 Uiso 0.5 1 calc R U P B 1
H12B H 0.2385 0.4816 0.7289 0.053 Uiso 0.5 1 calc R U P B 1
N3A N 0.5050(14) 0.3457(3) 0.6427(9) 0.0348(13) Uiso 0.5 1 d . U P B 1
C13A C 0.4384(19) 0.4333(5) 0.5917(12) 0.0443(9) Uiso 0.5 1 d . U P B 1
H13A H 0.4261 0.4382 0.4865 0.053 Uiso 0.5 1 calc R U P B 1
H13B H 0.4868 0.4638 0.6439 0.053 Uiso 0.5 1 calc R U P B 1
C5B C 0.4597(13) 0.3081(4) 0.4323(11) 0.0409(13) Uiso 0.5 1 d D U P B 2
H5B1 H 0.4997 0.3389 0.3965 0.049 Uiso 0.5 1 calc R U P B 2
H5B2 H 0.5074 0.2813 0.3833 0.049 Uiso 0.5 1 calc R U P B 2
C6 C 0.5518(14) 0.3045(3) 0.5957(10) 0.0393(15) Uani 0.5 1 d . . P B 2
H6A H 0.5158 0.2730 0.6296 0.047 Uiso 0.5 1 calc R U P B 2
H6B H 0.6927 0.3045 0.6138 0.047 Uiso 0.5 1 calc R U P B 2
C8B C 0.5668(17) 0.3275(4) 0.8371(13) 0.0443(9) Uiso 0.5 1 d D U P B 2
H8B1 H 0.7077 0.3315 0.8730 0.053 Uiso 0.5 1 calc R U P B 2
H8B2 H 0.5376 0.2927 0.8411 0.053 Uiso 0.5 1 calc R U P B 2
C9B C 0.4752(17) 0.3549(4) 0.9358(11) 0.0443(9) Uiso 0.5 1 d D U P B 2
H9B1 H 0.4817 0.3346 1.0229 0.053 Uiso 0.5 1 calc R U P B 2
H9B2 H 0.5515 0.3844 0.9703 0.053 Uiso 0.5 1 calc R U P B 2
C10B C 0.153(2) 0.3489(5) 0.9542(14) 0.053(2) Uiso 0.5 1 d . U P B 2
H10D H 0.1915 0.3627 1.0530 0.080 Uiso 0.5 1 calc R U P B 2
H10E H 0.1695 0.3137 0.9602 0.080 Uiso 0.5 1 calc R U P B 2
H10F H 0.0176 0.3565 0.9071 0.080 Uiso 0.5 1 calc R U P B 2
C11B C 0.2621(17) 0.4229(4) 0.8781(12) 0.0443(9) Uiso 0.5 1 d D U P B 2
H11C H 0.3936 0.4362 0.9120 0.053 Uiso 0.5 1 calc R U P B 2
H11D H 0.1931 0.4320 0.9500 0.053 Uiso 0.5 1 calc R U P B 2
C12B C 0.1584(18) 0.4437(6) 0.7278(14) 0.0443(9) Uiso 0.5 1 d D U P B 2
H12C H 0.0192 0.4373 0.7053 0.053 Uiso 0.5 1 calc R U P B 2
H12D H 0.1774 0.4792 0.7284 0.053 Uiso 0.5 1 calc R U P B 2
N3B N 0.5010(14) 0.3438(3) 0.6879(9) 0.0348(13) Uiso 0.5 1 d . U P B 2
C13B C 0.4340(19) 0.4332(5) 0.6344(12) 0.0443(9) Uiso 0.5 1 d . U P B 2
H13C H 0.4742 0.4536 0.7234 0.053 Uiso 0.5 1 calc R U P B 2
H13D H 0.4422 0.4536 0.5510 0.053 Uiso 0.5 1 calc R U P B 2
N4 N 0.2707(6) 0.36936(15) 0.8682(4) 0.0359(9) Uani 1 1 d . . . . .
C14 C 0.5795(8) 0.39293(19) 0.6509(7) 0.0487(13) Uani 1 1 d . . . . .
H14A H 0.6779 0.3935 0.5974 0.058 Uiso 1 1 calc R U . B 1
H14B H 0.6453 0.4001 0.7549 0.058 Uiso 1 1 calc R U . B 1
Cl2 Cl 0.58178(18) 0.43304(4) 0.26422(13) 0.0422(3) Uani 1 1 d . . . . .
O1W O 0.1946(5) 0.49242(15) 0.1825(4) 0.0464(9) Uani 1 1 d D . . . .
O2W O -0.1575(5) 0.44653(13) 0.0524(4) 0.0427(8) Uani 1 1 d D . . . .
H1D H 0.202(8) 0.5110(19) 0.116(5) 0.064 Uiso 1 1 d D U . . .
H1C H 0.297(5) 0.4771(19) 0.214(6) 0.064 Uiso 1 1 d D U . . .
H2C H -0.057(5) 0.457(2) 0.109(5) 0.064 Uiso 1 1 d D U . . .
H2D H -0.247(5) 0.444(2) 0.087(5) 0.064 Uiso 1 1 d 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 N1 2.046(4) . ?
Cu1 N2 2.048(3) . ?
Cu1 N4 2.073(4) . ?
Cu1 N3B 2.118(10) . ?
Cu1 N3A 2.238(10) . ?
Cu1 Cl1 2.2645(12) . ?
N1 C12A 1.434(16) . ?
N1 C13B 1.437(14) . ?
N1 C1 1.493(5) . ?
N1 C12B 1.511(15) . ?
N1 C13A 1.578(14) . ?
C1 C2 1.508(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.493(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N2 C3 1.482(6) . ?
N2 C4 1.485(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5B 1.428(10) . ?
C4 C5A 1.640(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5A N3A 1.600(13) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C7 N3A 1.414(12) . ?
C7 C8A 1.576(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8A C9A 1.484(15) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A N4 1.503(11) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A N4 1.471(14) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A N4 1.525(12) . ?
C11A C12A 1.533(11) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
N3A C14 1.407(10) . ?
C13A C14 1.513(14) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C5B C6 1.513(14) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6 N3B 1.506(12) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8B N3B 1.436(14) . ?
C8B C9B 1.502(11) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
C9B N4 1.498(12) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
C10B N4 1.459(13) . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B N4 1.485(12) . ?
C11B C12B 1.529(11) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
N3B C14 1.553(10) . ?
C13B C14 1.514(14) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
O1W H1D 0.832(19) . ?
O1W H1C 0.834(19) . ?
O2W H2C 0.825(19) . ?
O2W H2D 0.815(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N2 85.60(14) . . ?
N1 Cu1 N4 84.72(16) . . ?
N2 Cu1 N4 169.88(15) . . ?
N1 Cu1 N3B 85.6(3) . . ?
N2 Cu1 N3B 98.0(3) . . ?
N4 Cu1 N3B 84.2(3) . . ?
N1 Cu1 N3A 82.1(3) . . ?
N2 Cu1 N3A 87.1(2) . . ?
N4 Cu1 N3A 94.4(2) . . ?
N1 Cu1 Cl1 168.40(12) . . ?
N2 Cu1 Cl1 94.01(11) . . ?
N4 Cu1 Cl1 94.87(12) . . ?
N3B Cu1 Cl1 105.9(2) . . ?
N3A Cu1 Cl1 109.5(2) . . ?
C12A N1 C1 117.6(6) . . ?
C13B N1 C1 117.2(5) . . ?
C13B N1 C12B 111.1(7) . . ?
C1 N1 C12B 110.5(5) . . ?
C12A N1 C13A 111.4(7) . . ?
C1 N1 C13A 103.1(5) . . ?
C12A N1 Cu1 107.1(6) . . ?
C13B N1 Cu1 111.9(5) . . ?
C1 N1 Cu1 104.1(3) . . ?
C12B N1 Cu1 100.6(6) . . ?
C13A N1 Cu1 113.6(5) . . ?
N1 C1 C2 107.4(4) . . ?
N1 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
N1 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
N2 C2 C1 110.0(4) . . ?
N2 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C3 N2 C4 108.5(4) . . ?
C3 N2 C2 108.4(4) . . ?
C4 N2 C2 112.2(4) . . ?
C3 N2 Cu1 113.5(3) . . ?
C4 N2 Cu1 106.8(3) . . ?
C2 N2 Cu1 107.4(3) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5B C4 N2 127.6(6) . . ?
N2 C4 C5A 104.9(5) . . ?
N2 C4 H4A 110.8 . . ?
C5A C4 H4A 110.8 . . ?
N2 C4 H4B 110.8 . . ?
C5A C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
N3A C5A C4 118.3(8) . . ?
N3A C5A H5A1 107.7 . . ?
C4 C5A H5A1 107.7 . . ?
N3A C5A H5A2 107.7 . . ?
C4 C5A H5A2 107.7 . . ?
H5A1 C5A H5A2 107.1 . . ?
N3A C7 C8A 111.1(8) . . ?
N3A C7 H7A 109.4 . . ?
C8A C7 H7A 109.4 . . ?
N3A C7 H7B 109.4 . . ?
C8A C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9A C8A C7 118.3(9) . . ?
C9A C8A H8A1 107.7 . . ?
C7 C8A H8A1 107.7 . . ?
C9A C8A H8A2 107.7 . . ?
C7 C8A H8A2 107.7 . . ?
H8A1 C8A H8A2 107.1 . . ?
C8A C9A N4 120.3(8) . . ?
C8A C9A H9A1 107.3 . . ?
N4 C9A H9A1 107.3 . . ?
C8A C9A H9A2 107.3 . . ?
N4 C9A H9A2 107.3 . . ?
H9A1 C9A H9A2 106.9 . . ?
N4 C10A H10A 109.5 . . ?
N4 C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
N4 C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
N4 C11A C12A 109.1(9) . . ?
N4 C11A H11A 109.9 . . ?
C12A C11A H11A 109.9 . . ?
N4 C11A H11B 109.9 . . ?
C12A C11A H11B 109.9 . . ?
H11A C11A H11B 108.3 . . ?
N1 C12A C11A 104.9(10) . . ?
N1 C12A H12A 110.8 . . ?
C11A C12A H12A 110.8 . . ?
N1 C12A H12B 110.8 . . ?
C11A C12A H12B 110.8 . . ?
H12A C12A H12B 108.8 . . ?
C14 N3A C7 117.2(8) . . ?
C14 N3A C5A 109.2(7) . . ?
C7 N3A C5A 113.9(8) . . ?
C14 N3A Cu1 109.1(6) . . ?
C7 N3A Cu1 106.7(6) . . ?
C5A N3A Cu1 99.1(6) . . ?
C14 C13A N1 110.7(8) . . ?
C14 C13A H13A 109.5 . . ?
N1 C13A H13A 109.5 . . ?
C14 C13A H13B 109.5 . . ?
N1 C13A H13B 109.5 . . ?
H13A C13A H13B 108.1 . . ?
C4 C5B C6 113.5(8) . . ?
C4 C5B H5B1 108.9 . . ?
C6 C5B H5B1 108.9 . . ?
C4 C5B H5B2 108.9 . . ?
C6 C5B H5B2 108.9 . . ?
H5B1 C5B H5B2 107.7 . . ?
N3B C6 C5B 116.2(8) . . ?
N3B C6 H6A 108.2 . . ?
C5B C6 H6A 108.2 . . ?
N3B C6 H6B 108.2 . . ?
C5B C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
N3B C8B C9B 112.3(9) . . ?
N3B C8B H8B1 109.1 . . ?
C9B C8B H8B1 109.1 . . ?
N3B C8B H8B2 109.1 . . ?
C9B C8B H8B2 109.1 . . ?
H8B1 C8B H8B2 107.9 . . ?
N4 C9B C8B 115.4(8) . . ?
N4 C9B H9B1 108.4 . . ?
C8B C9B H9B1 108.4 . . ?
N4 C9B H9B2 108.4 . . ?
C8B C9B H9B2 108.4 . . ?
H9B1 C9B H9B2 107.5 . . ?
N4 C10B H10D 109.5 . . ?
N4 C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
N4 C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
N4 C11B C12B 109.6(9) . . ?
N4 C11B H11C 109.8 . . ?
C12B C11B H11C 109.8 . . ?
N4 C11B H11D 109.8 . . ?
C12B C11B H11D 109.8 . . ?
H11C C11B H11D 108.2 . . ?
N1 C12B C11B 109.8(10) . . ?
N1 C12B H12C 109.7 . . ?
C11B C12B H12C 109.7 . . ?
N1 C12B H12D 109.7 . . ?
C11B C12B H12D 109.7 . . ?
H12C C12B H12D 108.2 . . ?
C8B N3B C6 106.5(8) . . ?
C8B N3B C14 117.2(8) . . ?
C6 N3B C14 109.4(7) . . ?
C8B N3B Cu1 103.3(7) . . ?
C6 N3B Cu1 111.3(6) . . ?
C14 N3B Cu1 109.1(5) . . ?
N1 C13B C14 119.0(9) . . ?
N1 C13B H13C 107.6 . . ?
C14 C13B H13C 107.6 . . ?
N1 C13B H13D 107.6 . . ?
C14 C13B H13D 107.6 . . ?
H13C C13B H13D 107.0 . . ?
C10B N4 C11B 108.0(7) . . ?
C10B N4 C9B 109.0(7) . . ?
C11B N4 C9B 107.1(7) . . ?
C10A N4 C9A 110.3(7) . . ?
C10A N4 C11A 108.6(7) . . ?
C9A N4 C11A 114.7(7) . . ?
C10B N4 Cu1 116.3(6) . . ?
C10A N4 Cu1 111.1(6) . . ?
C11B N4 Cu1 109.2(5) . . ?
C9B N4 Cu1 106.9(4) . . ?
C9A N4 Cu1 107.3(4) . . ?
C11A N4 Cu1 104.9(4) . . ?
N3A C14 C13A 117.0(7) . . ?
C13B C14 N3B 112.1(7) . . ?
N3A C14 H14A 108.0 . . ?
C13A C14 H14A 108.0 . . ?
N3A C14 H14B 108.0 . . ?
C13A C14 H14B 108.0 . . ?
H14A C14 H14B 107.3 . . ?
H1D O1W H1C 110(3) . . ?
H2C O2W H2D 115(3) . . ?

_refine_diff_density_max         1.046
_refine_diff_density_min         -1.232
_refine_diff_density_rms         0.126

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_DGJ034
_database_code_depnum_ccdc_archive 'CCDC 1049982'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_vrf_PLAT341_DGJ034              
;
RESPONSE: The crystal examined was very weakly 
scattering and was twinned. This is reflected in the 
moderately good bond precision.    
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
2(C13 H30 Cl N4 O Zn), Cl4 Zn, C2 H3 N
;
_chemical_formula_sum            'C28 H63 Cl6 N9 O2 Zn3'
_chemical_formula_weight         966.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   8.7520(10)
_cell_length_b                   9.3289(10)
_cell_length_c                   14.889(2)
_cell_angle_alpha                72.755(10)
_cell_angle_beta                 89.362(10)
_cell_angle_gamma                63.372(8)
_cell_volume                     1027.2(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3555
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      22.15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             502
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.166
_shelx_estimated_absorpt_T_min   0.751
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.7182
_exptl_absorpt_correction_T_max  0.9255
_exptl_absorpt_process_details   
;
A face-index absorption correction was carried out
within the Stoe X-AREA suite (twinAbs).
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            11246
_diffrn_reflns_av_unetI/netI     0.2027
_diffrn_reflns_v_R_equivalents   0.1511
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.447
_diffrn_reflns_theta_max         25.620
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.911
_reflns_number_total             11246
_reflns_number_gt                5681
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.799
_reflns_Friedel_fraction_full    0.828

_reflns_special_details          
;
 _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.

 Some very weak reflections due to the second twin component
 were omitted from the the refinement. 
;

_computing_data_collection       'Stoe X-AREA'
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component 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)+(0.1567P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.31(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         11246
_refine_ls_number_parameters     447
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1637
_refine_ls_R_factor_gt           0.1012
_refine_ls_wR_factor_ref         0.2773
_refine_ls_wR_factor_gt          0.2497
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_restrained_S_all      0.898
_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 0.4781(5) 0.7329(5) 0.2125(3) 0.0474(12) Uani 1 1 d . . . . .
Cl1 Cl 0.4594(13) 0.6743(12) 0.3767(6) 0.061(3) Uani 1 1 d . . . . .
O1 O 0.314(3) 0.610(3) 0.2119(17) 0.060(7) Uani 1 1 d D . . . .
H1C H 0.25(3) 0.62(3) 0.166(14) 0.090 Uiso 1 1 d D U . . .
H1D H 0.29(4) 0.56(5) 0.263(11) 0.090 Uiso 1 1 d D U . . .
N1 N 0.502(4) 0.779(4) 0.0639(18) 0.051(7) Uani 1 1 d . . . . .
C1 C 0.540(5) 0.623(4) 0.049(2) 0.054(9) Uani 1 1 d . . . . .
H1A H 0.5651 0.6316 -0.0171 0.065 Uiso 1 1 calc R U . . .
H1B H 0.4357 0.6060 0.0551 0.065 Uiso 1 1 calc R U . . .
C2 C 0.695(5) 0.465(5) 0.119(3) 0.081(14) Uani 1 1 d . . . . .
H2A H 0.6783 0.3635 0.1296 0.097 Uiso 1 1 calc R U . . .
H2B H 0.8031 0.4448 0.0911 0.097 Uiso 1 1 calc R U . . .
N2 N 0.713(4) 0.491(4) 0.2164(19) 0.048(8) Uani 1 1 d . . . . .
C3 C 0.721(5) 0.346(5) 0.292(3) 0.065(11) Uani 1 1 d . . . . .
H3A H 0.6162 0.3359 0.2826 0.098 Uiso 1 1 calc R U . . .
H3B H 0.8221 0.2422 0.2898 0.098 Uiso 1 1 calc R U . . .
H3C H 0.7317 0.3606 0.3533 0.098 Uiso 1 1 calc R U . . .
C4 C 0.867(5) 0.509(5) 0.227(3) 0.067(13) Uani 1 1 d . . . . .
H4A H 0.9076 0.5350 0.1652 0.080 Uiso 1 1 calc R U . . .
H4B H 0.9603 0.4021 0.2710 0.080 Uiso 1 1 calc R U . . .
C5 C 0.821(5) 0.660(5) 0.270(2) 0.066(11) Uani 1 1 d . . . . .
H5A H 0.7950 0.6271 0.3353 0.079 Uiso 1 1 calc R U . . .
H5B H 0.9222 0.6810 0.2724 0.079 Uiso 1 1 calc R U . . .
N3 N 0.670(4) 0.818(3) 0.2095(18) 0.045(7) Uani 1 1 d . . . . .
C6 C 0.620(5) 0.948(5) 0.259(3) 0.065(10) Uani 1 1 d . . . . .
H6A H 0.7149 0.9769 0.2616 0.078 Uiso 1 1 calc R U . . .
H6B H 0.6046 0.8980 0.3245 0.078 Uiso 1 1 calc R U . . .
C7 C 0.454(6) 1.109(5) 0.209(3) 0.071(12) Uani 1 1 d . . . . .
H7A H 0.4456 1.1987 0.2353 0.086 Uiso 1 1 calc R U . . .
H7B H 0.4625 1.1477 0.1409 0.086 Uiso 1 1 calc R U . . .
C8 C 0.293(7) 1.092(6) 0.220(4) 0.099(19) Uani 1 1 d . . . . .
H8A H 0.1928 1.2076 0.1984 0.119 Uiso 1 1 calc R U . . .
H8B H 0.2918 1.0410 0.2885 0.119 Uiso 1 1 calc R U . . .
N4 N 0.267(4) 0.988(3) 0.167(2) 0.050(8) Uani 1 1 d . . . . .
C9 C 0.107(5) 0.999(5) 0.180(3) 0.078(14) Uani 1 1 d . . . . .
H9A H 0.0844 0.9327 0.1471 0.117 Uiso 1 1 calc R U . . .
H9B H 0.1047 0.9535 0.2485 0.117 Uiso 1 1 calc R U . . .
H9C H 0.0188 1.1176 0.1556 0.117 Uiso 1 1 calc R U . . .
C10 C 0.265(6) 1.057(4) 0.058(3) 0.072(12) Uani 1 1 d . . . . .
H10A H 0.1466 1.1446 0.0272 0.086 Uiso 1 1 calc R U . . .
H10B H 0.3422 1.1103 0.0450 0.086 Uiso 1 1 calc R U . . .
C11 C 0.325(5) 0.913(4) 0.017(3) 0.055(10) Uani 1 1 d . . . . .
H11A H 0.2442 0.8636 0.0273 0.066 Uiso 1 1 calc R U . . .
H11B H 0.3247 0.9568 -0.0522 0.066 Uiso 1 1 calc R U . . .
C12 C 0.639(5) 0.823(5) 0.038(3) 0.054(9) Uani 1 1 d . . . . .
H12A H 0.5968 0.9176 -0.0229 0.065 Uiso 1 1 calc R U . . .
H12B H 0.7368 0.7243 0.0278 0.065 Uiso 1 1 calc R U . . .
C13 C 0.703(5) 0.875(5) 0.112(3) 0.061(9) Uani 1 1 d . . . . .
H13A H 0.8289 0.8310 0.1134 0.073 Uiso 1 1 calc R U . . .
H13B H 0.6494 0.9999 0.0902 0.073 Uiso 1 1 calc R U . . .
Zn2 Zn 0.3520(4) 0.2201(4) 0.5601(3) 0.0441(11) Uani 1 1 d . . . . .
Cl2 Cl 0.2687(11) 0.3548(11) 0.3925(6) 0.053(2) Uani 1 1 d . . . . .
O2 O 0.501(3) 0.351(3) 0.5496(16) 0.059(7) Uani 1 1 d D . . . .
H2C H 0.47(5) 0.42(3) 0.494(8) 0.088 Uiso 1 1 d D U . . .
H2D H 0.49(5) 0.41(3) 0.588(16) 0.088 Uiso 1 1 d D U . . .
N5 N 0.434(4) 0.084(4) 0.7125(19) 0.048(7) Uani 1 1 d . . . . .
C21 C 0.618(4) 0.027(4) 0.724(2) 0.049(9) Uani 1 1 d . . . . .
H21A H 0.6672 -0.0499 0.7899 0.058 Uiso 1 1 calc R U . . .
H21B H 0.6376 0.1265 0.7151 0.058 Uiso 1 1 calc R U . . .
C22 C 0.715(4) -0.066(5) 0.655(2) 0.059(10) Uani 1 1 d . . . . .
H22A H 0.8135 -0.0426 0.6403 0.071 Uiso 1 1 calc R U . . .
H22B H 0.7608 -0.1895 0.6864 0.071 Uiso 1 1 calc R U . . .
N6 N 0.597(3) -0.010(3) 0.5628(17) 0.038(6) Uani 1 1 d . . . . .
C23 C 0.683(4) 0.029(4) 0.482(3) 0.054(9) Uani 1 1 d . . . . .
H23A H 0.7166 0.1144 0.4850 0.081 Uiso 1 1 calc R U . . .
H23B H 0.7870 -0.0750 0.4827 0.081 Uiso 1 1 calc R U . . .
H23C H 0.6050 0.0717 0.4227 0.081 Uiso 1 1 calc R U . . .
C24 C 0.546(4) -0.138(5) 0.559(3) 0.055(10) Uani 1 1 d . . . . .
H24A H 0.5689 -0.2197 0.6238 0.066 Uiso 1 1 calc R U . . .
H24B H 0.6177 -0.2021 0.5185 0.066 Uiso 1 1 calc R U . . .
C25 C 0.359(4) -0.061(4) 0.520(2) 0.051(9) Uani 1 1 d . . . . .
H25A H 0.3399 0.0055 0.4522 0.061 Uiso 1 1 calc R U . . .
H25B H 0.3269 -0.1519 0.5259 0.061 Uiso 1 1 calc R U . . .
N7 N 0.247(4) 0.051(4) 0.572(2) 0.059(9) Uani 1 1 d . . . . .
C26 C 0.066(4) 0.141(4) 0.525(2) 0.050(9) Uani 1 1 d . . . . .
H26A H 0.0249 0.0561 0.5317 0.060 Uiso 1 1 calc R U . . .
H26B H 0.0656 0.1913 0.4558 0.060 Uiso 1 1 calc R U . . .
C27 C -0.064(5) 0.282(5) 0.560(3) 0.067(11) Uani 1 1 d . . . . .
H27A H -0.1790 0.3285 0.5228 0.081 Uiso 1 1 calc R U . . .
H27B H -0.0717 0.2301 0.6268 0.081 Uiso 1 1 calc R U . . .
C28 C -0.032(4) 0.419(5) 0.554(3) 0.055(10) Uani 1 1 d . . . . .
H28A H -0.1311 0.4986 0.5766 0.066 Uiso 1 1 calc R U . . .
H28B H -0.0386 0.4765 0.4858 0.066 Uiso 1 1 calc R U . . .
N8 N 0.132(3) 0.400(3) 0.6047(19) 0.048(7) Uani 1 1 d . . . . .
C29 C 0.138(6) 0.556(5) 0.586(3) 0.092(16) Uani 1 1 d . . . . .
H29A H 0.1327 0.6074 0.5179 0.138 Uiso 1 1 calc R U . . .
H29B H 0.0405 0.6341 0.6093 0.138 Uiso 1 1 calc R U . . .
H29C H 0.2466 0.5350 0.6195 0.138 Uiso 1 1 calc R U . . .
C30 C 0.141(4) 0.323(5) 0.710(3) 0.058(10) Uani 1 1 d . . . . .
H30A H 0.0851 0.2485 0.7221 0.070 Uiso 1 1 calc R U . . .
H30B H 0.0810 0.4128 0.7385 0.070 Uiso 1 1 calc R U . . .
C31 C 0.338(5) 0.216(5) 0.754(2) 0.061(10) Uani 1 1 d . . . . .
H31A H 0.3903 0.2926 0.7443 0.073 Uiso 1 1 calc R U . . .
H31B H 0.3468 0.1626 0.8233 0.073 Uiso 1 1 calc R U . . .
C32 C 0.395(4) -0.058(5) 0.741(2) 0.056(9) Uani 1 1 d . . . . .
H32A H 0.3590 -0.0679 0.8048 0.068 Uiso 1 1 calc R U . . .
H32B H 0.5033 -0.1625 0.7470 0.068 Uiso 1 1 calc R U . . .
C33 C 0.256(4) -0.051(4) 0.675(3) 0.058(9) Uani 1 1 d . . . . .
H33A H 0.2817 -0.1673 0.6794 0.069 Uiso 1 1 calc R U . . .
H33B H 0.1421 0.0025 0.6965 0.069 Uiso 1 1 calc R U . . .
Zn3 Zn 0.7346(4) 0.3328(5) 0.8548(3) 0.0486(12) Uani 1 1 d . . . . .
Cl3 Cl 0.5699(13) 0.4829(12) 0.7058(7) 0.063(3) Uani 1 1 d . . . . .
Cl4 Cl 0.8431(12) 0.4990(14) 0.8792(7) 0.065(3) Uani 1 1 d . . . . .
Cl5 Cl 0.5552(11) 0.2987(12) 0.9588(7) 0.062(2) Uani 1 1 d . . . . .
Cl6 Cl 0.9439(12) 0.0791(12) 0.8525(8) 0.062(3) Uani 1 1 d . . . . .
N100 N 0.135(4) 0.590(5) 0.059(2) 0.075(10) Uani 1 1 d D . . . .
C100 C 0.139(5) 0.608(5) -0.021(3) 0.069(11) Uani 1 1 d . . . . .
C101 C 0.148(5) 0.646(5) -0.125(2) 0.070(11) Uani 1 1 d . . . . .
H10C H 0.1485 0.7551 -0.1513 0.105 Uiso 1 1 calc R U . . .
H10D H 0.0480 0.6504 -0.1573 0.105 Uiso 1 1 calc R U . . .
H10E H 0.2544 0.5563 -0.1357 0.105 Uiso 1 1 calc R 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
Zn1 N3 2.15(3) . ?
Zn1 N1 2.15(3) . ?
Zn1 N4 2.16(3) . ?
Zn1 O1 2.20(2) . ?
Zn1 N2 2.26(3) . ?
Zn1 Cl1 2.362(10) . ?
O1 H1C 0.86(3) . ?
O1 H1D 0.85(4) . ?
N1 C1 1.43(4) . ?
N1 C12 1.44(4) . ?
N1 C11 1.49(4) . ?
C1 C2 1.56(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.55(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N2 C4 1.45(5) . ?
N2 C3 1.45(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.60(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N3 1.49(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N3 C13 1.46(4) . ?
N3 C6 1.49(4) . ?
C6 C7 1.52(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.49(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N4 1.51(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N4 C9 1.38(4) . ?
N4 C10 1.55(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.51(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.53(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
Zn2 N7 2.12(3) . ?
Zn2 O2 2.13(3) . ?
Zn2 N8 2.16(2) . ?
Zn2 N5 2.19(3) . ?
Zn2 N6 2.24(3) . ?
Zn2 Cl2 2.387(8) . ?
O2 H2C 0.85(4) . ?
O2 H2D 0.85(4) . ?
N5 C21 1.44(4) . ?
N5 C31 1.45(5) . ?
N5 C32 1.46(4) . ?
C21 C22 1.54(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 N6 1.53(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N6 C23 1.46(4) . ?
N6 C24 1.47(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.50(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N7 1.48(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
N7 C26 1.48(4) . ?
N7 C33 1.53(4) . ?
C26 C27 1.53(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.40(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 N8 1.54(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
N8 C29 1.43(5) . ?
N8 C30 1.50(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.58(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.54(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
Zn3 Cl5 2.251(9) . ?
Zn3 Cl4 2.258(11) . ?
Zn3 Cl6 2.263(10) . ?
Zn3 Cl3 2.320(10) . ?
N100 C100 1.16(5) . ?
C100 C101 1.49(6) . ?
C101 H10C 0.9800 . ?
C101 H10D 0.9800 . ?
C101 H10E 0.9800 . ?

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
N3 Zn1 N1 82.1(11) . . ?
N3 Zn1 N4 93.0(11) . . ?
N1 Zn1 N4 84.9(11) . . ?
N3 Zn1 O1 171.1(11) . . ?
N1 Zn1 O1 94.7(10) . . ?
N4 Zn1 O1 95.1(11) . . ?
N3 Zn1 N2 81.4(10) . . ?
N1 Zn1 N2 78.7(10) . . ?
N4 Zn1 N2 163.2(10) . . ?
O1 Zn1 N2 89.8(10) . . ?
N3 Zn1 Cl1 97.5(7) . . ?
N1 Zn1 Cl1 178.3(8) . . ?
N4 Zn1 Cl1 96.8(8) . . ?
O1 Zn1 Cl1 85.5(7) . . ?
N2 Zn1 Cl1 99.6(7) . . ?
C1 N1 C12 110(3) . . ?
C1 N1 C11 110(3) . . ?
C12 N1 C11 116(3) . . ?
C1 N1 Zn1 104.7(19) . . ?
C12 N1 Zn1 113(2) . . ?
C11 N1 Zn1 103(2) . . ?
N1 C1 C2 114(3) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
N2 C2 C1 111(3) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 N2 C3 111(3) . . ?
C4 N2 C2 110(3) . . ?
C3 N2 C2 109(3) . . ?
C4 N2 Zn1 109(2) . . ?
C3 N2 Zn1 111(2) . . ?
C2 N2 Zn1 107(2) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 C5 108(3) . . ?
N2 C4 H4A 110.0 . . ?
C5 C4 H4A 110.0 . . ?
N2 C4 H4B 110.0 . . ?
C5 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
N3 C5 C4 111(3) . . ?
N3 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C13 N3 C6 114(3) . . ?
C13 N3 C5 112(3) . . ?
C6 N3 C5 108(3) . . ?
C13 N3 Zn1 110(2) . . ?
C6 N3 Zn1 110(2) . . ?
C5 N3 Zn1 101(2) . . ?
N3 C6 C7 113(3) . . ?
N3 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N3 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 115(4) . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 N4 116(4) . . ?
C7 C8 H8A 108.4 . . ?
N4 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
N4 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C9 N4 C8 106(4) . . ?
C9 N4 C10 107(3) . . ?
C8 N4 C10 113(3) . . ?
C9 N4 Zn1 115(3) . . ?
C8 N4 Zn1 111(2) . . ?
C10 N4 Zn1 105(2) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N4 110(3) . . ?
C11 C10 H10A 109.7 . . ?
N4 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
N4 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N1 C11 C10 110(3) . . ?
N1 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
N1 C12 C13 114(3) . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
N3 C13 C12 117(3) . . ?
N3 C13 H13A 107.9 . . ?
C12 C13 H13A 107.9 . . ?
N3 C13 H13B 107.9 . . ?
C12 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?
N7 Zn2 O2 169.6(10) . . ?
N7 Zn2 N8 94.0(11) . . ?
O2 Zn2 N8 95.8(10) . . ?
N7 Zn2 N5 82.5(11) . . ?
O2 Zn2 N5 95.0(10) . . ?
N8 Zn2 N5 84.3(10) . . ?
N7 Zn2 N6 82.1(10) . . ?
O2 Zn2 N6 87.5(9) . . ?
N8 Zn2 N6 162.1(9) . . ?
N5 Zn2 N6 77.8(9) . . ?
N7 Zn2 Cl2 95.6(8) . . ?
O2 Zn2 Cl2 86.5(6) . . ?
N8 Zn2 Cl2 98.0(7) . . ?
N5 Zn2 Cl2 177.1(8) . . ?
N6 Zn2 Cl2 99.8(7) . . ?
C21 N5 C31 114(3) . . ?
C21 N5 C32 111(3) . . ?
C31 N5 C32 114(3) . . ?
C21 N5 Zn2 103.7(19) . . ?
C31 N5 Zn2 103(2) . . ?
C32 N5 Zn2 110(2) . . ?
N5 C21 C22 115(3) . . ?
N5 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
N5 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
N6 C22 C21 112(3) . . ?
N6 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
N6 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C23 N6 C24 110(3) . . ?
C23 N6 C22 110(2) . . ?
C24 N6 C22 112(3) . . ?
C23 N6 Zn2 111.0(18) . . ?
C24 N6 Zn2 106.0(18) . . ?
C22 N6 Zn2 107.7(19) . . ?
N6 C23 H23A 109.5 . . ?
N6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N6 C24 C25 112(3) . . ?
N6 C24 H24A 109.2 . . ?
C25 C24 H24A 109.2 . . ?
N6 C24 H24B 109.2 . . ?
C25 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
N7 C25 C24 111(3) . . ?
N7 C25 H25A 109.3 . . ?
C24 C25 H25A 109.3 . . ?
N7 C25 H25B 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C25 N7 C26 110(3) . . ?
C25 N7 C33 111(2) . . ?
C26 N7 C33 109(2) . . ?
C25 N7 Zn2 102.4(19) . . ?
C26 N7 Zn2 112(2) . . ?
C33 N7 Zn2 113(2) . . ?
N7 C26 C27 117(3) . . ?
N7 C26 H26A 108.0 . . ?
C27 C26 H26A 108.0 . . ?
N7 C26 H26B 108.0 . . ?
C27 C26 H26B 108.0 . . ?
H26A C26 H26B 107.3 . . ?
C28 C27 C26 118(3) . . ?
C28 C27 H27A 107.9 . . ?
C26 C27 H27A 107.9 . . ?
C28 C27 H27B 107.9 . . ?
C26 C27 H27B 107.9 . . ?
H27A C27 H27B 107.2 . . ?
C27 C28 N8 124(3) . . ?
C27 C28 H28A 106.4 . . ?
N8 C28 H28A 106.4 . . ?
C27 C28 H28B 106.4 . . ?
N8 C28 H28B 106.4 . . ?
H28A C28 H28B 106.4 . . ?
C29 N8 C30 109(3) . . ?
C29 N8 C28 114(3) . . ?
C30 N8 C28 108(3) . . ?
C29 N8 Zn2 111(3) . . ?
C30 N8 Zn2 107.2(18) . . ?
C28 N8 Zn2 107(2) . . ?
N8 C29 H29A 109.5 . . ?
N8 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N8 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N8 C30 C31 108(2) . . ?
N8 C30 H30A 110.2 . . ?
C31 C30 H30A 110.2 . . ?
N8 C30 H30B 110.2 . . ?
C31 C30 H30B 110.2 . . ?
H30A C30 H30B 108.5 . . ?
N5 C31 C30 113(3) . . ?
N5 C31 H31A 109.1 . . ?
C30 C31 H31A 109.1 . . ?
N5 C31 H31B 109.1 . . ?
C30 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
N5 C32 C33 117(3) . . ?
N5 C32 H32A 108.1 . . ?
C33 C32 H32A 108.1 . . ?
N5 C32 H32B 108.1 . . ?
C33 C32 H32B 108.1 . . ?
H32A C32 H32B 107.3 . . ?
N7 C33 C32 111(3) . . ?
N7 C33 H33A 109.4 . . ?
C32 C33 H33A 109.4 . . ?
N7 C33 H33B 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
Cl5 Zn3 Cl4 112.7(4) . . ?
Cl5 Zn3 Cl6 111.0(4) . . ?
Cl4 Zn3 Cl6 112.3(4) . . ?
Cl5 Zn3 Cl3 107.1(4) . . ?
Cl4 Zn3 Cl3 104.4(4) . . ?
Cl6 Zn3 Cl3 108.9(4) . . ?
N100 C100 C101 174(4) . . ?
C100 C101 H10C 109.5 . . ?
C100 C101 H10D 109.5 . . ?
H10C C101 H10D 109.5 . . ?
C100 C101 H10E 109.5 . . ?
H10C C101 H10E 109.5 . . ?
H10D C101 H10E 109.5 . . ?

_refine_diff_density_max         1.257
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.151

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_sja23_09
_database_code_depnum_ccdc_archive 'CCDC 1049983'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_vrf_PLAT241_sja23_09            
;
RESPONSE: There is nothing abnormal about the displacement
parameter of C4. The adp of the nitrogen it is bonded to 
is rather smaller because it binds to the metal.     
;


_vrf_PLAT242_sja23_09            
;
RESPONSE: It is completely expected that the adp of the central 
zinc ion is smaller than those of the surrounding ligands. 
;



_vrf_PLAT250_sja23_09            
;
RESPONSE: In essence the structure is layered. In such cases
it is not uncommon that the displacement parameters within 
and perpendicular to the layer are different.    
;

_vrf_PLAT341_sja23_09            
;
RESPONSE: The ORTEP plot shows there is no serious problem with 
this structure. The C-C bond precision is acceptable. 
;

_vrf_PLAT410_sja23_09            
;
RESPONSE: This is due to the extreme rigidity of the macrocyclic chelator
 forcing less favourable geometries and close interactions on the alkyl
 backbone between H8B and H11B. 
;

_vrf_PLAT601_sja23_09            
;
RESPONSE: There is some evidence from the final difference Fourier maps
that there may be a partially occupied water molecule located within 
this region of space. However, if it is present, on average it is 
only partially occupied and its position is disordered.
;






_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C15 H33 N4 O3 Zn, F6 P
;
_chemical_formula_sum            'C15 H33 F6 N4 O3 P Zn'
_chemical_formula_weight         527.79

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c :H'
_space_group_name_Hall           'R 3 -2"c'

_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'
'-y, x-y, z'
'-y, -x, z+1/2'
'-x+y, -x, z'
'x, x-y, z+1/2'
'-x+y, y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, -x+1/3, z+1/3'
'x+2/3, x-y+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, -x+2/3, z+2/3'
'x+1/3, x-y+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'

_cell_length_a                   25.8872(12)
_cell_length_b                   25.8872(12)
_cell_length_c                   17.1214(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     9936.6(10)
_cell_formula_units_Z            18
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    35977
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      33.9

_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             4932
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.259
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   
;
Empirical absorption correction applied within Sortav 
(Blessing, 1995)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            54418
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.547
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6458
_reflns_number_gt                5468
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.999

_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       'Stoe X-AREA'
_computing_cell_refinement       'Stoe X-AREA'
_computing_data_reduction        'Stoe X-AREA'
_computing_structure_solution    SHELXS-86
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0748P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2346 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6458
_refine_ls_number_parameters     278
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6370(3) 0.0853(3) 0.8337(5) 0.0602(17) Uani 1 1 d . . . . .
H1A H 0.6542 0.0606 0.8516 0.072 Uiso 1 1 calc R U . . .
H1B H 0.6093 0.0641 0.7900 0.072 Uiso 1 1 calc R U . . .
C2 C 0.6027(3) 0.0940(3) 0.9014(5) 0.0620(18) Uani 1 1 d . . . . .
H2A H 0.5836 0.1167 0.8828 0.074 Uiso 1 1 calc R U . . .
H2B H 0.5709 0.0547 0.9204 0.074 Uiso 1 1 calc R U . . .
C3 C 0.6205(3) 0.1540(3) 1.0196(5) 0.0562(16) Uani 1 1 d . U . . .
H3A H 0.5924 0.1233 1.0564 0.067 Uiso 1 1 calc R U . . .
H3B H 0.5980 0.1691 0.9896 0.067 Uiso 1 1 calc R U . . .
C4 C 0.6703(4) 0.2057(4) 1.0661(4) 0.068(2) Uani 1 1 d . U . . .
H4A H 0.6585 0.2362 1.0749 0.082 Uiso 1 1 calc R U . . .
H4B H 0.6732 0.1904 1.1179 0.082 Uiso 1 1 calc R U . . .
C5 C 0.7713(4) 0.2169(4) 1.0665(4) 0.066(2) Uani 1 1 d . . . . .
H5A H 0.7467 0.1806 1.0979 0.079 Uiso 1 1 calc R U . . .
H5B H 0.7992 0.2488 1.1023 0.079 Uiso 1 1 calc R U . . .
C6 C 0.8065(3) 0.2043(4) 1.0070(4) 0.0576(16) Uani 1 1 d . . . . .
H6A H 0.8296 0.1885 1.0339 0.069 Uiso 1 1 calc R U . . .
H6B H 0.8351 0.2419 0.9806 0.069 Uiso 1 1 calc R U . . .
C7 C 0.8031(3) 0.1559(3) 0.8847(4) 0.0488(13) Uani 1 1 d . . . . .
H7A H 0.8264 0.1385 0.9067 0.059 Uiso 1 1 calc R U . . .
H7B H 0.8317 0.1967 0.8666 0.059 Uiso 1 1 calc R U . . .
C8 C 0.7687(4) 0.1197(4) 0.8167(5) 0.0624(18) Uani 1 1 d . . . . .
H8A H 0.7972 0.1166 0.7811 0.075 Uiso 1 1 calc R U . . .
H8B H 0.7409 0.0789 0.8359 0.075 Uiso 1 1 calc R U . . .
C9 C 0.7334(4) 0.1388(4) 0.7693(4) 0.0605(18) Uani 1 1 d . . . . .
H9A H 0.7614 0.1786 0.7473 0.073 Uiso 1 1 calc R U . . .
H9B H 0.7164 0.1109 0.7247 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6640(3) 0.0892(3) 1.0049(5) 0.061(2) Uani 1 1 d . . . . .
H10A H 0.6345 0.0468 0.9948 0.074 Uiso 1 1 calc R U . . .
H10B H 0.6640 0.0959 1.0619 0.074 Uiso 1 1 calc R U . . .
C11 C 0.7259(3) 0.0997(3) 0.9821(4) 0.0537(16) Uani 1 1 d . . . . .
H11A H 0.7454 0.0952 1.0293 0.064 Uiso 1 1 calc R U . . .
H11B H 0.7208 0.0685 0.9444 0.064 Uiso 1 1 calc R U . . .
C12 C 0.7587(5) 0.3000(4) 1.0305(5) 0.072(2) Uani 1 1 d . . . . .
H12A H 0.7322 0.3117 1.0051 0.108 Uiso 1 1 calc R U . . .
H12B H 0.7653 0.3136 1.0849 0.108 Uiso 1 1 calc R U . . .
H12C H 0.7970 0.3183 1.0028 0.108 Uiso 1 1 calc R U . . .
C14 C 0.8043(2) 0.3173(2) 0.8254(3) 0.0330(9) Uani 1 1 d . . . . .
C13 C 0.6613(4) 0.1689(4) 0.7479(4) 0.067(2) Uani 1 1 d . . . . .
H13A H 0.6939 0.2077 0.7306 0.100 Uiso 1 1 calc R U . . .
H13B H 0.6451 0.1420 0.7030 0.100 Uiso 1 1 calc R U . . .
H13C H 0.6297 0.1742 0.7715 0.100 Uiso 1 1 calc R U . . .
C15 C 0.8659(3) 0.3529(3) 0.7925(4) 0.0476(13) Uani 1 1 d . . . . .
H15A H 0.8951 0.3642 0.8347 0.071 Uiso 1 1 calc R U . . .
H15B H 0.8703 0.3889 0.7673 0.071 Uiso 1 1 calc R U . . .
H15C H 0.8725 0.3288 0.7539 0.071 Uiso 1 1 calc R U . . .
N1 N 0.6844(2) 0.1427(2) 0.8070(3) 0.0453(11) Uani 1 1 d . . . . .
N2 N 0.64394(19) 0.1263(2) 0.9649(3) 0.0388(9) Uani 1 1 d . . . . .
N3 N 0.7318(2) 0.2360(2) 1.0283(3) 0.0442(10) Uani 1 1 d . . . . .
N4 N 0.7662(2) 0.1597(2) 0.9467(3) 0.0421(10) Uani 1 1 d . . . . .
O2 O 0.79075(16) 0.26747(16) 0.8555(2) 0.0364(7) Uani 1 1 d . . . . .
O3 O 0.7692(2) 0.33754(18) 0.8222(3) 0.0502(10) Uani 1 1 d . . . . .
P1 P 0.75751(6) 0.05600(6) 1.21434(8) 0.0368(3) Uani 1 1 d . . . . .
F1 F 0.7283(4) -0.0120(2) 1.2374(4) 0.101(2) Uani 1 1 d . . . . .
F2 F 0.8143(2) 0.0725(3) 1.2657(4) 0.109(2) Uani 1 1 d . . . . .
F3 F 0.7010(2) 0.0440(4) 1.1683(4) 0.124(3) Uani 1 1 d . . . . .
F4 F 0.7277(4) 0.0622(4) 1.2922(4) 0.113(2) Uani 1 1 d . . . . .
F5 F 0.7854(4) 0.1237(2) 1.1944(5) 0.125(3) Uani 1 1 d . . . . .
F6 F 0.7867(5) 0.0498(5) 1.1404(3) 0.135(3) Uani 1 1 d . . . . .
Zn1 Zn 0.71673(2) 0.20049(2) 0.90718(3) 0.02404(11) Uani 1 1 d . . . . .
O1 O 0.67121(19) 0.24987(19) 0.8886(3) 0.0425(8) Uani 1 1 d D . . . .
H1C H 0.697(3) 0.280(3) 0.862(4) 0.064 Uiso 1 1 d D U . . .
H1D H 0.634(2) 0.239(4) 0.873(5) 0.064 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.449(9) . ?
C1 C2 1.546(11) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.459(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N2 1.482(8) . ?
C3 C4 1.537(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N3 1.525(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N3 1.489(9) . ?
C5 C6 1.507(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N4 1.511(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N4 1.463(8) . ?
C7 C8 1.481(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.480(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.472(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.471(8) . ?
C10 C11 1.534(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N4 1.499(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N3 1.443(9) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 O3 1.256(6) . ?
C14 O2 1.265(6) . ?
C14 C15 1.497(7) . ?
C13 N1 1.499(9) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Zn1 2.151(5) . ?
N2 Zn1 2.143(4) . ?
N3 Zn1 2.222(5) . ?
N4 Zn1 2.138(4) . ?
O2 Zn1 2.034(4) . ?
P1 F6 1.523(5) . ?
P1 F3 1.550(5) . ?
P1 F5 1.563(5) . ?
P1 F2 1.579(5) . ?
P1 F1 1.581(5) . ?
P1 F4 1.588(6) . ?
Zn1 O1 2.152(4) . ?
O1 H1C 0.86(5) . ?
O1 H1D 0.91(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 109.9(5) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N2 C2 C1 109.5(5) . . ?
N2 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N2 C3 C4 112.3(5) . . ?
N2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
N3 C4 C3 115.7(5) . . ?
N3 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
N3 C4 H4B 108.4 . . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.4 . . ?
N3 C5 C6 111.4(5) . . ?
N3 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N3 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 N4 111.5(6) . . ?
C5 C6 H6A 109.3 . . ?
N4 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
N4 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N4 C7 C8 114.0(6) . . ?
N4 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
N4 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 119.7(6) . . ?
C9 C8 H8A 107.4 . . ?
C7 C8 H8A 107.4 . . ?
C9 C8 H8B 107.4 . . ?
C7 C8 H8B 107.4 . . ?
H8A C8 H8B 106.9 . . ?
N1 C9 C8 118.7(7) . . ?
N1 C9 H9A 107.6 . . ?
C8 C9 H9A 107.6 . . ?
N1 C9 H9B 107.6 . . ?
C8 C9 H9B 107.6 . . ?
H9A C9 H9B 107.1 . . ?
N2 C10 C11 116.4(5) . . ?
N2 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
N2 C10 H10B 108.2 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 107.4 . . ?
N4 C11 C10 114.3(5) . . ?
N4 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
N4 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C14 O2 123.7(4) . . ?
O3 C14 C15 119.7(5) . . ?
O2 C14 C15 116.6(5) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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 . . ?
C1 N1 C9 112.6(6) . . ?
C1 N1 C13 110.6(6) . . ?
C9 N1 C13 106.7(6) . . ?
C1 N1 Zn1 107.3(4) . . ?
C9 N1 Zn1 110.4(4) . . ?
C13 N1 Zn1 109.2(4) . . ?
C2 N2 C10 111.6(6) . . ?
C2 N2 C3 112.8(5) . . ?
C10 N2 C3 112.7(5) . . ?
C2 N2 Zn1 103.6(4) . . ?
C10 N2 Zn1 111.1(4) . . ?
C3 N2 Zn1 104.3(4) . . ?
C12 N3 C5 110.6(6) . . ?
C12 N3 C4 111.1(7) . . ?
C5 N3 C4 111.0(6) . . ?
C12 N3 Zn1 112.5(4) . . ?
C5 N3 Zn1 106.3(4) . . ?
C4 N3 Zn1 105.1(4) . . ?
C7 N4 C11 111.4(5) . . ?
C7 N4 C6 108.9(5) . . ?
C11 N4 C6 111.8(5) . . ?
C7 N4 Zn1 112.1(4) . . ?
C11 N4 Zn1 111.1(4) . . ?
C6 N4 Zn1 101.2(4) . . ?
C14 O2 Zn1 135.1(3) . . ?
F6 P1 F3 91.4(5) . . ?
F6 P1 F5 87.8(5) . . ?
F3 P1 F5 88.6(4) . . ?
F6 P1 F2 92.7(5) . . ?
F3 P1 F2 174.8(5) . . ?
F5 P1 F2 88.4(4) . . ?
F6 P1 F1 94.4(5) . . ?
F3 P1 F1 91.4(4) . . ?
F5 P1 F1 177.8(5) . . ?
F2 P1 F1 91.4(4) . . ?
F6 P1 F4 179.1(4) . . ?
F3 P1 F4 89.5(5) . . ?
F5 P1 F4 92.6(5) . . ?
F2 P1 F4 86.5(4) . . ?
F1 P1 F4 85.2(4) . . ?
O2 Zn1 N4 90.98(16) . . ?
O2 Zn1 N2 174.50(17) . . ?
N4 Zn1 N2 83.52(18) . . ?
O2 Zn1 N1 96.83(18) . . ?
N4 Zn1 N1 91.7(2) . . ?
N2 Zn1 N1 83.3(2) . . ?
O2 Zn1 O1 89.52(15) . . ?
N4 Zn1 O1 169.13(19) . . ?
N2 Zn1 O1 95.90(17) . . ?
N1 Zn1 O1 99.01(19) . . ?
O2 Zn1 N3 99.07(18) . . ?
N4 Zn1 N3 83.3(2) . . ?
N2 Zn1 N3 80.46(19) . . ?
N1 Zn1 N3 163.41(19) . . ?
O1 Zn1 N3 85.86(18) . . ?
Zn1 O1 H1C 102(6) . . ?
Zn1 O1 H1D 133(6) . . ?
H1C O1 H1D 110(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -58.1(8) . . . . ?
N2 C3 C4 N3 24.1(9) . . . . ?
N3 C5 C6 N4 -54.2(9) . . . . ?
N4 C7 C8 C9 63.1(9) . . . . ?
C7 C8 C9 N1 -61.8(10) . . . . ?
N2 C10 C11 N4 22.0(10) . . . . ?
C2 C1 N1 C9 155.1(6) . . . . ?
C2 C1 N1 C13 -85.6(7) . . . . ?
C2 C1 N1 Zn1 33.5(7) . . . . ?
C8 C9 N1 C1 -64.1(8) . . . . ?
C8 C9 N1 C13 174.3(7) . . . . ?
C8 C9 N1 Zn1 55.8(8) . . . . ?
C1 C2 N2 C10 -71.0(7) . . . . ?
C1 C2 N2 C3 160.9(6) . . . . ?
C1 C2 N2 Zn1 48.6(7) . . . . ?
C11 C10 N2 C2 100.3(8) . . . . ?
C11 C10 N2 C3 -131.5(7) . . . . ?
C11 C10 N2 Zn1 -14.8(9) . . . . ?
C4 C3 N2 C2 -158.5(6) . . . . ?
C4 C3 N2 C10 73.9(7) . . . . ?
C4 C3 N2 Zn1 -46.7(6) . . . . ?
C6 C5 N3 C12 -99.4(8) . . . . ?
C6 C5 N3 C4 136.9(7) . . . . ?
C6 C5 N3 Zn1 23.1(8) . . . . ?
C3 C4 N3 C12 132.8(7) . . . . ?
C3 C4 N3 C5 -103.8(7) . . . . ?
C3 C4 N3 Zn1 10.8(8) . . . . ?
C8 C7 N4 C11 64.0(7) . . . . ?
C8 C7 N4 C6 -172.2(6) . . . . ?
C8 C7 N4 Zn1 -61.2(6) . . . . ?
C10 C11 N4 C7 -143.3(6) . . . . ?
C10 C11 N4 C6 94.6(7) . . . . ?
C10 C11 N4 Zn1 -17.6(8) . . . . ?
C5 C6 N4 C7 171.8(6) . . . . ?
C5 C6 N4 C11 -64.8(7) . . . . ?
C5 C6 N4 Zn1 53.6(6) . . . . ?
O3 C14 O2 Zn1 0.9(9) . . . . ?
C15 C14 O2 Zn1 -179.4(4) . . . . ?

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
O1 H1C O3 0.86(5) 1.85(5) 2.669(6) 160(8) .
O1 H1D O3 0.91(5) 1.82(5) 2.705(6) 166(8) 4_665

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.083

