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

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

data_cm1340
_database_code_depnum_ccdc_archive 'CCDC 1498806'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '1,2-di(pyridin-2-yl)-ethanone oxime'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 N6 O2'
_chemical_formula_sum            'C24 H22 N6 O2'
_chemical_formula_weight         426.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   7.3692(7)
_cell_length_b                   12.7821(12)
_cell_length_c                   13.2426(13)
_cell_angle_alpha                61.872(4)
_cell_angle_beta                 81.346(5)
_cell_angle_gamma                75.593(4)
_cell_volume                     1064.66(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      28.80

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7054
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS v2008/1 (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            23332
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.845
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4318
_reflns_number_gt                3874
_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       'APEX2 v.2010.1-2 (Bruker Nonius, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        'SAINT v.7.68a (Bruker, 2010)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0399P)²+0.3928P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4318
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O1 O 0.79225(11) 0.84712(7) 0.38097(7) 0.02134(18) Uani 1 1 d . . . . .
H1O H 0.8572 0.8878 0.3894 0.032 Uiso 1 1 calc R U . . .
N1 N 0.57869(15) 0.78615(9) 0.10615(9) 0.0283(2) Uani 1 1 d . . . . .
C4 C 0.7895(2) 0.92287(13) 0.03825(11) 0.0338(3) Uani 1 1 d . . . . .
H4 H 0.8676 0.9611 0.0552 0.041 Uiso 1 1 calc R U . . .
O2 O 0.42802(11) 0.72368(7) 0.61637(6) 0.02150(18) Uani 1 1 d . . . . .
H2O H 0.4907 0.6832 0.5834 0.032 Uiso 1 1 calc R U . . .
N2 N 0.80178(13) 0.87169(8) 0.26628(8) 0.0196(2) Uani 1 1 d . . . . .
C3 C 0.7741(2) 0.94613(14) -0.07310(12) 0.0400(3) Uani 1 1 d . . . . .
H3 H 0.8427 0.9996 -0.1339 0.048 Uiso 1 1 calc R U . . .
N3 N 0.63923(13) 0.57941(8) 0.52938(8) 0.0190(2) Uani 1 1 d . . . . .
C2 C 0.6577(2) 0.89075(12) -0.09476(11) 0.0361(3) Uani 1 1 d . . . . .
H2 H 0.6422 0.9064 -0.1709 0.043 Uiso 1 1 calc R U . . .
C1 C 0.5639(2) 0.81203(13) -0.00362(12) 0.0349(3) Uani 1 1 d . . . . .
H1 H 0.4841 0.7737 -0.0192 0.042 Uiso 1 1 calc R U . . .
N4 N 0.18131(15) 0.69075(9) 0.96883(9) 0.0275(2) Uani 1 1 d . . . . .
C5 C 0.68926(16) 0.84256(10) 0.12588(10) 0.0211(2) Uani 1 1 d . . . . .
N5 N 0.39473(13) 0.64599(8) 0.73111(8) 0.0191(2) Uani 1 1 d . . . . .
C6 C 0.69451(15) 0.81831(9) 0.24698(9) 0.0181(2) Uani 1 1 d . . . . .
N6 N -0.01251(12) 1.00606(8) 0.63406(8) 0.01660(19) Uani 1 1 d . . . . .
C7 C 0.56884(15) 0.74147(10) 0.33782(9) 0.0191(2) Uani 1 1 d . . . . .
H7A H 0.4691 0.7351 0.2998 0.023 Uiso 1 1 calc R U . . .
H7B H 0.5075 0.7830 0.3847 0.023 Uiso 1 1 calc R U . . .
C8 C 0.66845(15) 0.61510(10) 0.41647(9) 0.0177(2) Uani 1 1 d . . . . .
C9 C 0.77982(16) 0.53757(11) 0.37446(10) 0.0233(2) Uani 1 1 d . . . . .
H9 H 0.7971 0.5636 0.2942 0.028 Uiso 1 1 calc R U . . .
C10 C 0.86505(17) 0.42203(11) 0.45114(11) 0.0265(3) Uani 1 1 d . . . . .
H10 H 0.9428 0.3684 0.4240 0.032 Uiso 1 1 calc R U . . .
C11 C 0.83577(16) 0.38562(10) 0.56751(11) 0.0250(3) Uani 1 1 d . . . . .
H11 H 0.8933 0.3072 0.6218 0.030 Uiso 1 1 calc R U . . .
C12 C 0.72054(16) 0.46661(10) 0.60253(10) 0.0227(2) Uani 1 1 d . . . . .
H12 H 0.6976 0.4413 0.6824 0.027 Uiso 1 1 calc R U . . .
C16 C 0.28145(16) 0.50275(10) 0.95732(10) 0.0231(2) Uani 1 1 d . . . . .
H16 H 0.3302 0.4617 0.9121 0.028 Uiso 1 1 calc R U . . .
C15 C 0.23663(17) 0.43911(11) 1.07235(10) 0.0263(3) Uani 1 1 d . . . . .
H15 H 0.2549 0.3533 1.1077 0.032 Uiso 1 1 calc R U . . .
C14 C 0.16463(18) 0.50211(12) 1.13560(10) 0.0281(3) Uani 1 1 d . . . . .
H14 H 0.1340 0.4605 1.2151 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1386(2) 0.62673(12) 1.08030(11) 0.0320(3) Uani 1 1 d . . . . .
H13 H 0.0875 0.6697 1.1237 0.038 Uiso 1 1 calc R U . . .
C17 C 0.25355(15) 0.62882(10) 0.90889(9) 0.0188(2) Uani 1 1 d . . . . .
C18 C 0.30158(15) 0.70383(10) 0.78612(9) 0.0176(2) Uani 1 1 d . . . . .
C19 C 0.23744(15) 0.83963(10) 0.73400(9) 0.0177(2) Uani 1 1 d . . . . .
H19A H 0.3308 0.8776 0.6738 0.021 Uiso 1 1 calc R U . . .
H19B H 0.2331 0.8658 0.7940 0.021 Uiso 1 1 calc R U . . .
C20 C 0.04696(14) 0.88514(9) 0.68206(9) 0.0156(2) Uani 1 1 d . . . . .
C21 C -0.06041(15) 0.80977(10) 0.68242(9) 0.0184(2) Uani 1 1 d . . . . .
H21 H -0.0146 0.7246 0.7152 0.022 Uiso 1 1 calc R U . . .
C22 C -0.23536(16) 0.85983(11) 0.63443(10) 0.0209(2) Uani 1 1 d . . . . .
H22 H -0.3106 0.8096 0.6339 0.025 Uiso 1 1 calc R U . . .
C23 C -0.29824(15) 0.98449(10) 0.58733(9) 0.0205(2) Uani 1 1 d . . . . .
H23 H -0.4186 1.0214 0.5556 0.025 Uiso 1 1 calc R U . . .
C24 C -0.18100(15) 1.05368(10) 0.58782(9) 0.0186(2) Uani 1 1 d . . . . .
H24 H -0.2223 1.1392 0.5536 0.022 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
O1 N2 1.3926(12) . ?
N1 C5 1.3365(15) . ?
N1 C1 1.3456(17) . ?
C4 C3 1.3770(19) . ?
C4 C5 1.3937(17) . ?
O2 N5 1.3933(12) . ?
N2 C6 1.2843(14) . ?
C3 C2 1.374(2) . ?
N3 C8 1.3412(14) . ?
N3 C12 1.3432(15) . ?
C2 C1 1.377(2) . ?
N4 C17 1.3401(15) . ?
N4 C13 1.3406(16) . ?
C5 C6 1.4877(16) . ?
N5 C18 1.2858(14) . ?
C6 C7 1.5076(15) . ?
N6 C24 1.3373(14) . ?
N6 C20 1.3437(14) . ?
C7 C8 1.5121(15) . ?
C8 C9 1.3939(16) . ?
C9 C10 1.3868(17) . ?
C10 C11 1.3827(18) . ?
C11 C12 1.3800(17) . ?
C16 C15 1.3802(17) . ?
C16 C17 1.3967(16) . ?
C15 C14 1.3861(18) . ?
C14 C13 1.3786(18) . ?
C17 C18 1.4879(15) . ?
C18 C19 1.5077(15) . ?
C19 C20 1.5129(15) . ?
C20 C21 1.3885(15) . ?
C21 C22 1.3886(16) . ?
C22 C23 1.3875(16) . ?
C23 C24 1.3842(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 117.07(11) . . ?
C3 C4 C5 119.24(13) . . ?
C6 N2 O1 112.12(9) . . ?
C2 C3 C4 118.90(13) . . ?
C8 N3 C12 118.70(10) . . ?
C3 C2 C1 118.48(12) . . ?
N1 C1 C2 123.88(13) . . ?
C17 N4 C13 117.40(11) . . ?
N1 C5 C4 122.41(11) . . ?
N1 C5 C6 116.15(10) . . ?
C4 C5 C6 121.40(11) . . ?
C18 N5 O2 111.97(9) . . ?
N2 C6 C5 116.26(10) . . ?
N2 C6 C7 123.51(10) . . ?
C5 C6 C7 120.10(10) . . ?
C24 N6 C20 118.63(9) . . ?
C6 C7 C8 114.40(9) . . ?
N3 C8 C9 121.36(10) . . ?
N3 C8 C7 116.60(9) . . ?
C9 C8 C7 122.01(10) . . ?
C10 C9 C8 119.21(11) . . ?
C11 C10 C9 119.36(11) . . ?
C12 C11 C10 118.05(11) . . ?
N3 C12 C11 123.30(11) . . ?
C15 C16 C17 118.60(11) . . ?
C16 C15 C14 119.12(11) . . ?
C13 C14 C15 118.36(11) . . ?
N4 C13 C14 123.75(12) . . ?
N4 C17 C16 122.75(10) . . ?
N4 C17 C18 115.32(10) . . ?
C16 C17 C18 121.92(10) . . ?
N5 C18 C17 116.31(10) . . ?
N5 C18 C19 124.45(10) . . ?
C17 C18 C19 119.23(9) . . ?
C18 C19 C20 113.67(9) . . ?
N6 C20 C21 121.58(10) . . ?
N6 C20 C19 114.79(9) . . ?
C21 C20 C19 123.63(10) . . ?
C20 C21 C22 119.47(10) . . ?
C23 C22 C21 118.80(10) . . ?
C24 C23 C22 118.24(10) . . ?
N6 C24 C23 123.25(10) . . ?

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
C5 C4 C3 C2 1.0(2) . . . . ?
C4 C3 C2 C1 -1.3(2) . . . . ?
C5 N1 C1 C2 1.1(2) . . . . ?
C3 C2 C1 N1 0.3(2) . . . . ?
C1 N1 C5 C4 -1.44(18) . . . . ?
C1 N1 C5 C6 176.43(11) . . . . ?
C3 C4 C5 N1 0.4(2) . . . . ?
C3 C4 C5 C6 -177.33(12) . . . . ?
O1 N2 C6 C5 177.80(9) . . . . ?
O1 N2 C6 C7 1.84(15) . . . . ?
N1 C5 C6 N2 179.48(10) . . . . ?
C4 C5 C6 N2 -2.63(17) . . . . ?
N1 C5 C6 C7 -4.41(15) . . . . ?
C4 C5 C6 C7 173.48(11) . . . . ?
N2 C6 C7 C8 -78.79(14) . . . . ?
C5 C6 C7 C8 105.40(12) . . . . ?
C12 N3 C8 C9 0.34(15) . . . . ?
C12 N3 C8 C7 178.12(9) . . . . ?
C6 C7 C8 N3 128.79(10) . . . . ?
C6 C7 C8 C9 -53.43(14) . . . . ?
N3 C8 C9 C10 -1.30(16) . . . . ?
C7 C8 C9 C10 -178.97(10) . . . . ?
C8 C9 C10 C11 0.87(17) . . . . ?
C9 C10 C11 C12 0.47(17) . . . . ?
C8 N3 C12 C11 1.10(16) . . . . ?
C10 C11 C12 N3 -1.51(17) . . . . ?
C17 C16 C15 C14 0.41(18) . . . . ?
C16 C15 C14 C13 0.73(19) . . . . ?
C17 N4 C13 C14 -0.1(2) . . . . ?
C15 C14 C13 N4 -0.9(2) . . . . ?
C13 N4 C17 C16 1.32(18) . . . . ?
C13 N4 C17 C18 -179.00(11) . . . . ?
C15 C16 C17 N4 -1.49(17) . . . . ?
C15 C16 C17 C18 178.85(10) . . . . ?
O2 N5 C18 C17 178.26(8) . . . . ?
O2 N5 C18 C19 -0.76(14) . . . . ?
N4 C17 C18 N5 170.59(10) . . . . ?
C16 C17 C18 N5 -9.73(15) . . . . ?
N4 C17 C18 C19 -10.35(14) . . . . ?
C16 C17 C18 C19 169.34(10) . . . . ?
N5 C18 C19 C20 88.85(13) . . . . ?
C17 C18 C19 C20 -90.14(12) . . . . ?
C24 N6 C20 C21 1.33(15) . . . . ?
C24 N6 C20 C19 -178.92(9) . . . . ?
C18 C19 C20 N6 -179.39(9) . . . . ?
C18 C19 C20 C21 0.36(15) . . . . ?
N6 C20 C21 C22 -1.46(16) . . . . ?
C19 C20 C21 C22 178.81(10) . . . . ?
C20 C21 C22 C23 -0.07(16) . . . . ?
C21 C22 C23 C24 1.62(16) . . . . ?
C20 N6 C24 C23 0.34(16) . . . . ?
C22 C23 C24 N6 -1.82(17) . . . . ?

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 H1O N6 0.84 1.88 2.6949(12) 164.7 2_676
O2 H2O N3 0.84 1.85 2.6806(12) 172.6 .

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_cm14106
_database_code_depnum_ccdc_archive 'CCDC 1498807'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '1,2-di(pyridin-2-yl)-ethanone oxime'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 N3 O'
_chemical_formula_sum            'C12 H11 N3 O'
_chemical_formula_weight         213.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.1571(7)
_cell_length_b                   13.7528(13)
_cell_length_c                   8.6319(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1087.07(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7244
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      30.45

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3421
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS v2008/1 (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            16000
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.672
_diffrn_reflns_theta_max         26.000
_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 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2110
_reflns_number_gt                1954
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.983

_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       'APEX2 v.2010.1-2 (Bruker Nonius, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        'SAINT v.7.68a (Bruker, 2010)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.1116P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2110
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1644
_refine_ls_wR_factor_gt          0.1620
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.102
_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
O1 O 0.9634(2) 0.39225(18) 0.4459(3) 0.0502(6) Uani 1 1 d . . . . .
H1O H 0.9976 0.3546 0.3784 0.075 Uiso 1 1 calc R U . . .
N1 N 0.5289(3) 0.5165(2) 0.6213(3) 0.0513(7) Uani 1 1 d . . . . .
C1 C 0.3831(4) 0.5208(3) 0.6215(4) 0.0559(9) Uani 1 1 d . . . . .
H1 H 0.3380 0.5764 0.6661 0.067 Uiso 1 1 calc R U . . .
N2 N 0.8114(3) 0.38380(18) 0.4490(4) 0.0457(6) Uani 1 1 d . . . . .
C2 C 0.2940(4) 0.4490(3) 0.5606(4) 0.0542(8) Uani 1 1 d . . . . .
H2 H 0.1908 0.4559 0.5613 0.065 Uiso 1 1 calc R U . . .
C3 C 0.3594(4) 0.3671(3) 0.4986(4) 0.0537(8) Uani 1 1 d . . . . .
H3 H 0.3015 0.3156 0.4583 0.064 Uiso 1 1 calc R U . . .
N3 N 0.9688(3) 0.6620(2) 0.6545(4) 0.0537(7) Uani 1 1 d . . . . .
C4 C 0.5105(4) 0.3610(3) 0.4961(4) 0.0490(7) Uani 1 1 d . . . . .
H4 H 0.5581 0.3057 0.4538 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5909(3) 0.4382(2) 0.5574(4) 0.0439(7) Uani 1 1 d . . . . .
C6 C 0.7533(3) 0.4399(2) 0.5499(4) 0.0441(7) Uani 1 1 d . . . . .
C7 C 0.8375(3) 0.5091(2) 0.6518(4) 0.0456(7) Uani 1 1 d . . . . .
H7A H 0.9226 0.4744 0.6958 0.055 Uiso 1 1 calc R U . . .
H7B H 0.7743 0.5293 0.7391 0.055 Uiso 1 1 calc R U . . .
C9 C 0.8634(4) 0.6176(3) 0.4129(4) 0.0542(8) Uani 1 1 d . . . . .
H9 H 0.8075 0.5729 0.3535 0.065 Uiso 1 1 calc R U . . .
C8 C 0.8912(3) 0.5993(2) 0.5687(4) 0.0446(7) Uani 1 1 d . . . . .
C10 C 0.9173(5) 0.7009(3) 0.3456(4) 0.0617(10) Uani 1 1 d . . . . .
H10 H 0.8991 0.7139 0.2392 0.074 Uiso 1 1 calc R U . . .
C11 C 0.9974(5) 0.7649(3) 0.4327(6) 0.0640(9) Uani 1 1 d . . . . .
H11 H 1.0357 0.8229 0.3887 0.077 Uiso 1 1 calc R U . . .
C12 C 1.0206(5) 0.7422(3) 0.5871(5) 0.0628(10) Uani 1 1 d . . . . .
H12 H 1.0763 0.7861 0.6482 0.075 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
O1 N2 1.397(3) . ?
N1 C5 1.336(4) . ?
N1 C1 1.336(4) . ?
C1 C2 1.385(5) . ?
N2 C6 1.279(4) . ?
C2 C3 1.384(5) . ?
C3 C4 1.386(5) . ?
N3 C12 1.335(5) . ?
N3 C8 1.340(4) . ?
C4 C5 1.396(4) . ?
C5 C6 1.489(4) . ?
C6 C7 1.508(4) . ?
C7 C8 1.515(4) . ?
C9 C10 1.376(5) . ?
C9 C8 1.391(5) . ?
C10 C11 1.372(6) . ?
C11 C12 1.385(7) . ?

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
C5 N1 C1 117.4(3) . . ?
N1 C1 C2 123.8(3) . . ?
C6 N2 O1 112.2(2) . . ?
C3 C2 C1 118.2(3) . . ?
C2 C3 C4 119.1(3) . . ?
C12 N3 C8 118.6(3) . . ?
C3 C4 C5 118.4(3) . . ?
N1 C5 C4 123.0(3) . . ?
N1 C5 C6 115.5(3) . . ?
C4 C5 C6 121.5(3) . . ?
N2 C6 C5 115.8(3) . . ?
N2 C6 C7 124.4(3) . . ?
C5 C6 C7 119.7(3) . . ?
C6 C7 C8 114.0(3) . . ?
C10 C9 C8 119.5(3) . . ?
N3 C8 C9 121.0(3) . . ?
N3 C8 C7 115.9(3) . . ?
C9 C8 C7 123.1(3) . . ?
C11 C10 C9 119.7(4) . . ?
C10 C11 C12 117.7(4) . . ?
N3 C12 C11 123.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.4(6) . . . . ?
N1 C1 C2 C3 1.4(6) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C1 N1 C5 C4 -1.9(5) . . . . ?
C1 N1 C5 C6 175.9(3) . . . . ?
C3 C4 C5 N1 1.6(5) . . . . ?
C3 C4 C5 C6 -176.1(3) . . . . ?
O1 N2 C6 C5 177.9(2) . . . . ?
O1 N2 C6 C7 1.3(4) . . . . ?
N1 C5 C6 N2 -158.5(3) . . . . ?
C4 C5 C6 N2 19.3(4) . . . . ?
N1 C5 C6 C7 18.2(4) . . . . ?
C4 C5 C6 C7 -163.9(3) . . . . ?
N2 C6 C7 C8 75.1(4) . . . . ?
C5 C6 C7 C8 -101.3(3) . . . . ?
C12 N3 C8 C9 -0.7(5) . . . . ?
C12 N3 C8 C7 179.2(3) . . . . ?
C10 C9 C8 N3 0.6(5) . . . . ?
C10 C9 C8 C7 -179.4(3) . . . . ?
C6 C7 C8 N3 -178.9(3) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C12 0.0(7) . . . . ?
C8 N3 C12 C11 0.6(6) . . . . ?
C10 C11 C12 N3 -0.2(7) . . . . ?

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 H1O N3 0.84 1.97 2.696(4) 144.0 2_764

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_cm15073_sq
_database_code_depnum_ccdc_archive 'CCDC 1498808'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 Br2 N6 Ni O2, 0.5(C2 H6 O), 0.5(H2 O)'
_chemical_formula_sum            'C25 H28 Br2 N6 Ni O3'
_chemical_formula_weight         679.06

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   14.0794(9)
_cell_length_b                   13.7668(10)
_cell_length_c                   14.7078(9)
_cell_angle_alpha                90
_cell_angle_beta                 116.071(3)
_cell_angle_gamma                90
_cell_volume                     2560.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      29.39

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.919
_shelx_estimated_absorpt_T_min   0.429
_shelx_estimated_absorpt_T_max   0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3699
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS v2008/1 (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            39384
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.137
_diffrn_reflns_theta_max         26.000
_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             5030
_reflns_number_gt                4175
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 v.2010.1-2 (Bruker Nonius, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        'SAINT v.7.68a (Bruker, 2010)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          
;Disordered solvent addressed using SQUEEZE - 2 voids/cell each 105A and
34 electrons. 16 electrons per formula unit = 0.5(EtOH)+0.5(H2O) (18 e), SQUEEZE
;
# start Validation Reply Form
_vrf_CHEMW03_cm15073_sq          
;
PROBLEM: WARNING: The ratio of given/expected molecular weight as
RESPONSE: Disordered solvent addressed using SQUEEZE - 2 voids/cell 
each 105A and 34 electrons. 16 electrons per formula unit = 
0.5(EtOH)+0.5(H2O) (18 e). These were included in the UNIT atom count.
;

# end Validation Reply Form
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5030
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
Ni1 Ni 0.69119(3) 0.38492(3) 0.43227(3) 0.03233(13) Uani 1 1 d . . . . .
Br1 Br 0.60407(3) 0.51861(2) 0.29165(2) 0.04152(12) Uani 1 1 d . . . . .
Br2 Br 0.78927(3) 0.50616(2) 0.57621(2) 0.03976(12) Uani 1 1 d . . . . .
C1 C 0.5635(3) 0.2277(2) 0.2786(2) 0.0397(7) Uani 1 1 d . . . . .
H1 H 0.5137 0.2338 0.3057 0.048 Uiso 1 1 calc R U . . .
C2 C 0.5421(3) 0.1640(3) 0.1989(3) 0.0469(8) Uani 1 1 d . . . . .
H2 H 0.4787 0.1269 0.1716 0.056 Uiso 1 1 calc R U . . .
C3 C 0.6152(3) 0.1554(3) 0.1597(3) 0.0499(9) Uani 1 1 d . . . . .
H3 H 0.6017 0.1136 0.1040 0.060 Uiso 1 1 calc R U . . .
C4 C 0.7075(3) 0.2081(3) 0.2025(2) 0.0455(8) Uani 1 1 d . . . . .
H4 H 0.7588 0.2020 0.1771 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7255(3) 0.2702(2) 0.2828(2) 0.0379(7) Uani 1 1 d . . . . .
C6 C 0.8226(2) 0.3274(2) 0.3351(2) 0.0365(7) Uani 1 1 d . . . . .
C7 C 0.9095(3) 0.3266(2) 0.3017(2) 0.0403(7) Uani 1 1 d . . . . .
H7A H 0.9171 0.2601 0.2801 0.048 Uiso 1 1 calc R U . . .
H7B H 0.9771 0.3445 0.3597 0.048 Uiso 1 1 calc R U . . .
C8 C 0.8873(2) 0.3973(2) 0.2143(2) 0.0373(7) Uani 1 1 d . . . . .
C9 C 0.8037(3) 0.4612(2) 0.1780(2) 0.0444(8) Uani 1 1 d . . . . .
H9 H 0.7546 0.4625 0.2062 0.053 Uiso 1 1 calc R U . . .
C10 C 0.7921(3) 0.5236(3) 0.1001(3) 0.0471(8) Uani 1 1 d . . . . .
H10 H 0.7342 0.5674 0.0731 0.057 Uiso 1 1 calc R U . . .
C11 C 0.8662(3) 0.5209(2) 0.0624(3) 0.0457(8) Uani 1 1 d . . . . .
H11 H 0.8616 0.5641 0.0102 0.055 Uiso 1 1 calc R U . . .
C12 C 0.9468(3) 0.4543(3) 0.1021(2) 0.0439(8) Uani 1 1 d . . . . .
H12 H 0.9972 0.4521 0.0754 0.053 Uiso 1 1 calc R U . . .
O1 O 0.91253(16) 0.43549(17) 0.45859(16) 0.0415(5) Uani 1 1 d . . . . .
H1B H 0.9069 0.4661 0.5070 0.062 Uiso 0.5 1 d R U P . .
H1C H 0.9175 0.4767 0.4169 0.062 Uiso 0.5 1 d R U P . .
N1 N 0.6517(2) 0.28076(19) 0.31863(18) 0.0359(6) Uani 1 1 d . . . . .
N2 N 0.8239(2) 0.37843(18) 0.40806(19) 0.0360(6) Uani 1 1 d . . . . .
N3 N 0.9583(2) 0.39175(19) 0.1769(2) 0.0406(6) Uani 1 1 d . . . . .
C13 C 0.8064(2) 0.2225(2) 0.5832(2) 0.0370(7) Uani 1 1 d . . . . .
H13 H 0.8597 0.2288 0.5605 0.044 Uiso 1 1 calc R U . . .
C14 C 0.8238(3) 0.1581(2) 0.6615(2) 0.0412(7) Uani 1 1 d . . . . .
H14 H 0.8867 0.1206 0.6911 0.049 Uiso 1 1 calc R U . . .
C15 C 0.7463(3) 0.1501(2) 0.6951(2) 0.0419(8) Uani 1 1 d . . . . .
H15 H 0.7563 0.1083 0.7499 0.050 Uiso 1 1 calc R U . . .
C16 C 0.6548(3) 0.2034(2) 0.6484(2) 0.0378(7) Uani 1 1 d . . . . .
H16 H 0.6006 0.1980 0.6701 0.045 Uiso 1 1 calc R U . . .
C17 C 0.6423(2) 0.2651(2) 0.5692(2) 0.0348(7) Uani 1 1 d . . . . .
C18 C 0.5455(2) 0.3242(2) 0.5123(2) 0.0358(7) Uani 1 1 d . . . . .
C19 C 0.4464(3) 0.3135(2) 0.5255(2) 0.0400(7) Uani 1 1 d . . . . .
H19A H 0.4116 0.3777 0.5163 0.048 Uiso 1 1 calc R U . . .
H19B H 0.4650 0.2914 0.5953 0.048 Uiso 1 1 calc R U . . .
C20 C 0.3691(3) 0.2417(2) 0.4508(2) 0.0385(7) Uani 1 1 d . . . . .
C21 C 0.2680(3) 0.2317(2) 0.4450(3) 0.0465(8) Uani 1 1 d . . . . .
H21 H 0.2469 0.2694 0.4871 0.056 Uiso 1 1 calc R U . . .
C22 C 0.1992(3) 0.1660(3) 0.3769(3) 0.0520(9) Uani 1 1 d . . . . .
H22 H 0.1298 0.1578 0.3713 0.062 Uiso 1 1 calc R U . . .
C23 C 0.2327(3) 0.1126(2) 0.3170(3) 0.0517(9) Uani 1 1 d . . . . .
H23 H 0.1868 0.0673 0.2691 0.062 Uiso 1 1 calc R U . . .
C24 C 0.3339(3) 0.1265(2) 0.3283(2) 0.0457(8) Uani 1 1 d . . . . .
H24 H 0.3567 0.0894 0.2871 0.055 Uiso 1 1 calc R U . . .
N4 N 0.7196(2) 0.27582(18) 0.53839(18) 0.0332(5) Uani 1 1 d . . . . .
N5 N 0.5555(2) 0.38317(18) 0.44938(18) 0.0348(6) Uani 1 1 d . . . . .
N6 N 0.4025(2) 0.18941(19) 0.39408(19) 0.0410(6) Uani 1 1 d . . . . .
O2 O 0.46695(16) 0.43867(17) 0.39316(16) 0.0404(5) Uani 1 1 d . . . . .
H2O H 0.4808 0.4776 0.3566 0.061 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
Ni1 N5 2.033(3) . ?
Ni1 N2 2.052(3) . ?
Ni1 N4 2.074(2) . ?
Ni1 N1 2.084(3) . ?
Ni1 Br2 2.5701(5) . ?
Ni1 Br1 2.6343(5) . ?
C1 N1 1.334(4) . ?
C1 C2 1.388(4) . ?
C2 C3 1.387(5) . ?
C3 C4 1.375(5) . ?
C4 C5 1.389(4) . ?
C5 N1 1.363(4) . ?
C5 C6 1.468(5) . ?
C6 N2 1.276(4) . ?
C6 C7 1.505(4) . ?
C7 C8 1.532(4) . ?
C8 N3 1.337(4) . ?
C8 C9 1.376(4) . ?
C9 C10 1.382(5) . ?
C10 C11 1.382(5) . ?
C11 C12 1.374(5) . ?
C12 N3 1.350(4) . ?
O1 N2 1.383(3) . ?
C13 N4 1.326(4) . ?
C13 C14 1.387(4) . ?
C14 C15 1.385(5) . ?
C15 C16 1.375(5) . ?
C16 C17 1.389(4) . ?
C17 N4 1.358(4) . ?
C17 C18 1.490(4) . ?
C18 N5 1.285(4) . ?
C18 C19 1.498(4) . ?
C19 C20 1.523(4) . ?
C20 N6 1.335(4) . ?
C20 C21 1.395(4) . ?
C21 C22 1.381(5) . ?
C22 C23 1.381(5) . ?
C23 C24 1.374(5) . ?
C24 N6 1.341(4) . ?
N5 O2 1.384(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Ni1 N2 175.90(10) . . ?
N5 Ni1 N4 77.25(10) . . ?
N2 Ni1 N4 102.11(10) . . ?
N5 Ni1 N1 99.04(10) . . ?
N2 Ni1 N1 76.89(10) . . ?
N4 Ni1 N1 90.03(10) . . ?
N5 Ni1 Br2 95.72(7) . . ?
N2 Ni1 Br2 88.32(7) . . ?
N4 Ni1 Br2 89.68(7) . . ?
N1 Ni1 Br2 164.80(7) . . ?
N5 Ni1 Br1 88.10(7) . . ?
N2 Ni1 Br1 92.26(7) . . ?
N4 Ni1 Br1 164.98(7) . . ?
N1 Ni1 Br1 89.03(7) . . ?
Br2 Ni1 Br1 95.118(18) . . ?
N1 C1 C2 122.2(3) . . ?
C3 C2 C1 118.6(3) . . ?
C4 C3 C2 119.3(3) . . ?
C3 C4 C5 119.7(3) . . ?
N1 C5 C4 120.7(3) . . ?
N1 C5 C6 115.6(3) . . ?
C4 C5 C6 123.7(3) . . ?
N2 C6 C5 113.7(3) . . ?
N2 C6 C7 124.4(3) . . ?
C5 C6 C7 121.9(3) . . ?
C6 C7 C8 112.0(3) . . ?
N3 C8 C9 123.0(3) . . ?
N3 C8 C7 113.3(3) . . ?
C9 C8 C7 123.7(3) . . ?
C8 C9 C10 119.2(3) . . ?
C11 C10 C9 118.8(3) . . ?
C12 C11 C10 118.4(3) . . ?
N3 C12 C11 123.6(3) . . ?
C1 N1 C5 119.4(3) . . ?
C1 N1 Ni1 126.8(2) . . ?
C5 N1 Ni1 113.8(2) . . ?
C6 N2 O1 116.2(3) . . ?
C6 N2 Ni1 119.5(2) . . ?
O1 N2 Ni1 123.89(18) . . ?
C8 N3 C12 117.1(3) . . ?
N4 C13 C14 123.7(3) . . ?
C15 C14 C13 117.8(3) . . ?
C16 C15 C14 119.4(3) . . ?
C15 C16 C17 119.4(3) . . ?
N4 C17 C16 121.5(3) . . ?
N4 C17 C18 115.0(3) . . ?
C16 C17 C18 123.5(3) . . ?
N5 C18 C17 112.7(3) . . ?
N5 C18 C19 124.0(3) . . ?
C17 C18 C19 123.3(3) . . ?
C18 C19 C20 112.4(2) . . ?
N6 C20 C21 122.7(3) . . ?
N6 C20 C19 117.7(3) . . ?
C21 C20 C19 119.6(3) . . ?
C22 C21 C20 118.7(3) . . ?
C21 C22 C23 119.0(3) . . ?
C24 C23 C22 118.4(3) . . ?
N6 C24 C23 123.9(3) . . ?
C13 N4 C17 118.1(3) . . ?
C13 N4 Ni1 127.3(2) . . ?
C17 N4 Ni1 114.4(2) . . ?
C18 N5 O2 115.1(3) . . ?
C18 N5 Ni1 120.2(2) . . ?
O2 N5 Ni1 124.62(18) . . ?
C20 N6 C24 117.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 1.7(5) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 N1 -1.2(5) . . . . ?
C3 C4 C5 C6 178.3(3) . . . . ?
N1 C5 C6 N2 0.7(4) . . . . ?
C4 C5 C6 N2 -178.8(3) . . . . ?
N1 C5 C6 C7 -177.5(3) . . . . ?
C4 C5 C6 C7 3.0(5) . . . . ?
N2 C6 C7 C8 -95.0(4) . . . . ?
C5 C6 C7 C8 82.9(4) . . . . ?
C6 C7 C8 N3 -174.2(3) . . . . ?
C6 C7 C8 C9 6.5(5) . . . . ?
N3 C8 C9 C10 -0.6(5) . . . . ?
C7 C8 C9 C10 178.6(3) . . . . ?
C8 C9 C10 C11 -1.2(5) . . . . ?
C9 C10 C11 C12 1.8(5) . . . . ?
C10 C11 C12 N3 -0.7(5) . . . . ?
C2 C1 N1 C5 -2.3(5) . . . . ?
C2 C1 N1 Ni1 176.2(2) . . . . ?
C4 C5 N1 C1 2.9(4) . . . . ?
C6 C5 N1 C1 -176.7(3) . . . . ?
C4 C5 N1 Ni1 -175.8(2) . . . . ?
C6 C5 N1 Ni1 4.7(3) . . . . ?
C5 C6 N2 O1 -178.6(2) . . . . ?
C7 C6 N2 O1 -0.5(4) . . . . ?
C5 C6 N2 Ni1 -6.0(4) . . . . ?
C7 C6 N2 Ni1 172.0(2) . . . . ?
C9 C8 N3 C12 1.8(5) . . . . ?
C7 C8 N3 C12 -177.5(3) . . . . ?
C11 C12 N3 C8 -1.1(5) . . . . ?
N4 C13 C14 C15 -0.7(5) . . . . ?
C13 C14 C15 C16 1.9(5) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 N4 -1.6(5) . . . . ?
C15 C16 C17 C18 178.7(3) . . . . ?
N4 C17 C18 N5 -6.4(4) . . . . ?
C16 C17 C18 N5 173.3(3) . . . . ?
N4 C17 C18 C19 172.0(3) . . . . ?
C16 C17 C18 C19 -8.3(5) . . . . ?
N5 C18 C19 C20 86.1(4) . . . . ?
C17 C18 C19 C20 -92.1(3) . . . . ?
C18 C19 C20 N6 8.4(4) . . . . ?
C18 C19 C20 C21 -172.6(3) . . . . ?
N6 C20 C21 C22 -0.9(5) . . . . ?
C19 C20 C21 C22 -179.9(3) . . . . ?
C20 C21 C22 C23 0.0(5) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C22 C23 C24 N6 -0.2(5) . . . . ?
C14 C13 N4 C17 -1.6(4) . . . . ?
C14 C13 N4 Ni1 172.7(2) . . . . ?
C16 C17 N4 C13 2.8(4) . . . . ?
C18 C17 N4 C13 -177.5(3) . . . . ?
C16 C17 N4 Ni1 -172.3(2) . . . . ?
C18 C17 N4 Ni1 7.4(3) . . . . ?
C17 C18 N5 O2 178.9(2) . . . . ?
C19 C18 N5 O2 0.5(4) . . . . ?
C17 C18 N5 Ni1 2.2(3) . . . . ?
C19 C18 N5 Ni1 -176.2(2) . . . . ?
C21 C20 N6 C24 1.2(5) . . . . ?
C19 C20 N6 C24 -179.8(3) . . . . ?
C23 C24 N6 C20 -0.6(5) . . . . ?

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 O1 0.86 2.59 2.840(4) 98.2 3_766
O1 H1B Br2 0.86 2.36 3.097(2) 144.0 .
O2 H2O Br1 0.84 2.39 3.115(2) 145.1 .

_refine_diff_density_max         0.725
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.120



####################################################################### 
# 
# 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_cm14021_sq
_database_code_depnum_ccdc_archive 'CCDC 1498809'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H30 N9 Ni O3, 2(Cl O4), 3(C2 H6 O)'
_chemical_formula_sum            'C42 H48 Cl2 N9 Ni O14'
_chemical_formula_weight         1032.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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                   11.9564(7)
_cell_length_b                   19.5919(12)
_cell_length_c                   20.5409(12)
_cell_angle_alpha                90
_cell_angle_beta                 104.883(3)
_cell_angle_gamma                90
_cell_volume                     4650.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      30.53

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             2148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.608
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6675
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS v2008, (Sheldrick, 2008)'
_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  'Bruker-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            80448
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.557
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9132
_reflns_number_gt                7009
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 v.2010.1-2 (Bruker Nonius, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        'SAINT v.7.68a (Bruker, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury (Macrae at al., 2008)'
_computing_publication_material  'PublCIF (Westrip, 2010)'
_refine_special_details          
;Disordered solvent addressed using SQUEEZE - 2 voids/cell each 520A and
149 electrons. 78.5 electrons per formula unit = 3 EtOH (78 e), SQUEEZE
;
# start Validation Reply Form
_vrf_CHEMW03_cm14021_sq          
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: Disordered solvent addressed using SQUEEZE - 2 voids/cell 
each 520A and 149 electrons. So 78.5 electrons per formula unit 
= 3 EtOH (78 e). These were included in the UNIT atom count.
(EtOH was the reaction & crystallisation solvent)
;
# end Validation Reply Form 
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+3.0302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9132
_refine_ls_number_parameters     541
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.012
_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
Ni1 Ni 0.50226(3) 0.21525(2) 0.10837(2) 0.01971(9) Uani 1 1 d . . . . .
N1 N 0.44247(17) 0.12285(10) 0.06684(9) 0.0230(4) Uani 1 1 d . . . . .
C1 C 0.4239(2) 0.06734(12) 0.09991(12) 0.0281(5) Uani 1 1 d . . . . .
H1 H 0.4430 0.0684 0.1477 0.034 Uiso 1 1 calc R U . . .
C2 C 0.3776(2) 0.00823(13) 0.06701(14) 0.0376(6) Uani 1 1 d . . . . .
H2 H 0.3645 -0.0305 0.0918 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3509(3) 0.00649(14) -0.00189(15) 0.0410(7) Uani 1 1 d . . . . .
H3 H 0.3195 -0.0337 -0.0254 0.049 Uiso 1 1 calc R U . . .
C4 C 0.3701(2) 0.06388(13) -0.03713(13) 0.0341(6) Uani 1 1 d . . . . .
H4 H 0.3527 0.0634 -0.0849 0.041 Uiso 1 1 calc R U . . .
C5 C 0.4149(2) 0.12154(12) -0.00136(11) 0.0235(5) Uani 1 1 d . . . . .
C6 C 0.43462(19) 0.18600(12) -0.03406(11) 0.0208(5) Uani 1 1 d . . . . .
N2 N 0.46025(16) 0.23742(9) 0.00573(9) 0.0208(4) Uani 1 1 d . . . . .
O1 O 0.48282(15) 0.29670(8) -0.02508(8) 0.0259(4) Uani 1 1 d . . . . .
H1O H 0.470(2) 0.3301(15) -0.0034(14) 0.039 Uiso 1 1 d . U . . .
C7 C 0.4298(2) 0.18856(12) -0.10751(11) 0.0238(5) Uani 1 1 d . . . . .
H7A H 0.4077 0.2351 -0.1248 0.029 Uiso 1 1 calc R U . . .
H7B H 0.3695 0.1566 -0.1322 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5441(2) 0.16997(11) -0.12085(11) 0.0221(5) Uani 1 1 d . . . . .
C9 C 0.5493(2) 0.14685(13) -0.18371(11) 0.0287(5) Uani 1 1 d . . . . .
H9 H 0.4803 0.1409 -0.2185 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6551(2) 0.13257(14) -0.19526(12) 0.0339(6) Uani 1 1 d . . . . .
H10 H 0.6600 0.1166 -0.2381 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7541(2) 0.14170(13) -0.14395(12) 0.0326(6) Uani 1 1 d . . . . .
H11 H 0.8284 0.1333 -0.1509 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7421(2) 0.16331(13) -0.08249(12) 0.0298(6) Uani 1 1 d . . . . .
H12 H 0.8100 0.1686 -0.0468 0.036 Uiso 1 1 calc R U . . .
N3 N 0.63974(17) 0.17731(10) -0.07018(9) 0.0238(4) Uani 1 1 d . . . . .
N4 N 0.56566(17) 0.18591(9) 0.20739(9) 0.0225(4) Uani 1 1 d . . . . .
C13 C 0.5076(2) 0.17886(12) 0.25426(12) 0.0281(5) Uani 1 1 d . . . . .
H13 H 0.4254 0.1796 0.2408 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5622(2) 0.17048(12) 0.32195(12) 0.0319(6) Uani 1 1 d . . . . .
H14 H 0.5182 0.1641 0.3539 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6802(2) 0.17146(12) 0.34197(12) 0.0321(6) Uani 1 1 d . . . . .
H15 H 0.7193 0.1684 0.3884 0.039 Uiso 1 1 calc R U . . .
C16 C 0.7425(2) 0.17703(12) 0.29368(11) 0.0279(5) Uani 1 1 d . . . . .
H16 H 0.8247 0.1769 0.3063 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6822(2) 0.18280(11) 0.22678(11) 0.0232(5) Uani 1 1 d . . . . .
C18 C 0.7412(2) 0.18627(11) 0.17165(11) 0.0218(5) Uani 1 1 d . . . . .
N5 N 0.67312(17) 0.19458(10) 0.11272(9) 0.0222(4) Uani 1 1 d . . . . .
O2 O 0.73034(15) 0.20024(9) 0.06219(8) 0.0292(4) Uani 1 1 d . . . . .
H2O H 0.683(3) 0.1932(16) 0.0245(16) 0.044 Uiso 1 1 d . U . . .
C19 C 0.8699(2) 0.18385(13) 0.18656(12) 0.0274(5) Uani 1 1 d . . . . .
H19A H 0.8931 0.1715 0.1451 0.033 Uiso 1 1 calc R U . . .
H19B H 0.8998 0.1483 0.2209 0.033 Uiso 1 1 calc R U . . .
C20 C 0.9219(2) 0.25179(13) 0.21207(11) 0.0262(5) Uani 1 1 d . . . . .
C21 C 1.0352(2) 0.25708(15) 0.25015(13) 0.0348(6) Uani 1 1 d . . . . .
H21 H 1.0816 0.2174 0.2620 0.042 Uiso 1 1 calc R U . . .
C22 C 1.0797(3) 0.32030(16) 0.27059(15) 0.0435(7) Uani 1 1 d . . . . .
H22 H 1.1575 0.3247 0.2966 0.052 Uiso 1 1 calc R U . . .
C23 C 1.0114(2) 0.37739(15) 0.25330(14) 0.0404(7) Uani 1 1 d . . . . .
H23 H 1.0408 0.4217 0.2667 0.048 Uiso 1 1 calc R U . . .
C24 C 0.8991(2) 0.36814(14) 0.21593(13) 0.0337(6) Uani 1 1 d . . . . .
H24 H 0.8511 0.4072 0.2042 0.040 Uiso 1 1 calc R U . . .
N6 N 0.85395(18) 0.30673(11) 0.19530(10) 0.0290(5) Uani 1 1 d . . . . .
N7 N 0.34470(18) 0.25129(10) 0.11664(9) 0.0257(4) Uani 1 1 d . . . . .
C25 C 0.2467(2) 0.21640(14) 0.10905(13) 0.0344(6) Uani 1 1 d . . . . .
H25 H 0.2481 0.1684 0.1029 0.041 Uiso 1 1 calc R U . . .
C26 C 0.1430(3) 0.24704(16) 0.10977(15) 0.0422(7) Uani 1 1 d . . . . .
H26 H 0.0746 0.2206 0.1042 0.051 Uiso 1 1 calc R U . . .
C27 C 0.1405(3) 0.31627(16) 0.11869(14) 0.0412(7) Uani 1 1 d . . . . .
H27 H 0.0699 0.3386 0.1185 0.049 Uiso 1 1 calc R U . . .
C28 C 0.2416(2) 0.35332(14) 0.12793(12) 0.0343(6) Uani 1 1 d . . . . .
H28 H 0.2419 0.4012 0.1353 0.041 Uiso 1 1 calc R U . . .
C29 C 0.3429(2) 0.31959(13) 0.12621(11) 0.0263(5) Uani 1 1 d . . . . .
C30 C 0.4535(2) 0.35511(12) 0.13267(10) 0.0244(5) Uani 1 1 d . . . . .
N8 N 0.54025(17) 0.31634(10) 0.13320(9) 0.0226(4) Uani 1 1 d . . . . .
O3 O 0.64120(15) 0.35090(8) 0.13376(8) 0.0283(4) Uani 1 1 d . . . . .
H3O H 0.698(3) 0.3228(16) 0.1465(15) 0.042 Uiso 1 1 d . U . . .
C31 C 0.4590(2) 0.43141(12) 0.13272(12) 0.0323(6) Uani 1 1 d . . . . .
H31A H 0.5407 0.4465 0.1457 0.039 Uiso 1 1 calc R U . . .
H31B H 0.4199 0.4499 0.1660 0.039 Uiso 1 1 calc R U . . .
C32 C 0.4005(2) 0.45807(12) 0.06341(12) 0.0277(5) Uani 1 1 d . . . . .
C33 C 0.3473(3) 0.52094(14) 0.05521(15) 0.0416(7) Uani 1 1 d . . . . .
H33 H 0.3453 0.5478 0.0934 0.050 Uiso 1 1 calc R U . . .
C34 C 0.2970(3) 0.54463(15) -0.00860(16) 0.0488(8) Uani 1 1 d . . . . .
H34 H 0.2609 0.5882 -0.0152 0.059 Uiso 1 1 calc R U . . .
C35 C 0.3002(3) 0.50403(15) -0.06269(15) 0.0445(7) Uani 1 1 d . . . . .
H35 H 0.2661 0.5189 -0.1074 0.053 Uiso 1 1 calc R U . . .
C36 C 0.3534(2) 0.44170(14) -0.05092(13) 0.0356(6) Uani 1 1 d . . . . .
H36 H 0.3549 0.4139 -0.0885 0.043 Uiso 1 1 calc R U . . .
N9 N 0.40360(18) 0.41786(10) 0.01094(10) 0.0289(5) Uani 1 1 d . . . . .
Cl1 Cl 0.22582(7) 0.06996(4) 0.24854(4) 0.0517(2) Uani 1 1 d D . . . .
O11 O 0.3073(4) 0.0208(2) 0.2764(2) 0.164(2) Uani 1 1 d D . . . .
O12 O 0.1221(3) 0.0463(2) 0.2586(2) 0.1446(18) Uani 1 1 d D . . . .
O13 O 0.2228(4) 0.0766(2) 0.18149(16) 0.1309(15) Uani 1 1 d D . . . .
O14 O 0.2561(2) 0.13237(14) 0.28288(17) 0.0878(9) Uani 1 1 d D . . . .
Cl2 Cl 0.71849(5) -0.00197(3) 0.23029(3) 0.03176(15) Uani 1 1 d D . . . .
O21 O 0.71008(17) -0.07312(9) 0.21426(10) 0.0421(5) Uani 1 1 d D . . . .
O22 O 0.6153(2) 0.02199(11) 0.24300(12) 0.0597(6) Uani 1 1 d D . . . .
O23 O 0.8060(3) 0.00690(15) 0.29045(18) 0.1204(15) Uani 1 1 d D . . . .
O24 O 0.7409(3) 0.03504(12) 0.17690(15) 0.0978(11) Uani 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.0501(19) . ?
Ni1 N7 2.059(2) . ?
Ni1 N4 2.0616(18) . ?
Ni1 N5 2.062(2) . ?
Ni1 N8 2.0662(19) . ?
Ni1 N2 2.0838(18) . ?
N1 C1 1.331(3) . ?
N1 C5 1.355(3) . ?
C1 C2 1.383(4) . ?
C2 C3 1.369(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.379(3) . ?
C5 C6 1.477(3) . ?
C6 N2 1.284(3) . ?
C6 C7 1.496(3) . ?
N2 O1 1.382(2) . ?
C7 C8 1.506(3) . ?
C8 N3 1.342(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.375(4) . ?
C10 C11 1.379(4) . ?
C11 C12 1.373(3) . ?
C12 N3 1.340(3) . ?
N4 C13 1.331(3) . ?
N4 C17 1.349(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.365(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.383(3) . ?
C17 C18 1.481(3) . ?
C18 N5 1.284(3) . ?
C18 C19 1.491(3) . ?
N5 O2 1.386(2) . ?
C19 C20 1.505(3) . ?
C20 N6 1.340(3) . ?
C20 C21 1.383(4) . ?
C21 C22 1.371(4) . ?
C22 C23 1.376(4) . ?
C23 C24 1.378(4) . ?
C24 N6 1.342(3) . ?
N7 C25 1.331(3) . ?
N7 C29 1.354(3) . ?
C25 C26 1.381(4) . ?
C26 C27 1.370(4) . ?
C27 C28 1.381(4) . ?
C28 C29 1.388(4) . ?
C29 C30 1.470(4) . ?
C30 N8 1.283(3) . ?
C30 C31 1.496(3) . ?
N8 O3 1.381(3) . ?
C31 C32 1.509(3) . ?
C32 N9 1.343(3) . ?
C32 C33 1.377(4) . ?
C33 C34 1.375(4) . ?
C34 C35 1.375(4) . ?
C35 C36 1.369(4) . ?
C36 N9 1.342(3) . ?
Cl1 O13 1.375(3) . ?
Cl1 O11 1.385(3) . ?
Cl1 O12 1.389(3) . ?
Cl1 O14 1.412(3) . ?
Cl2 O24 1.397(2) . ?
Cl2 O22 1.406(2) . ?
Cl2 O23 1.410(3) . ?
Cl2 O21 1.4300(18) . ?

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 Ni1 N7 96.22(8) . . ?
N1 Ni1 N4 99.48(7) . . ?
N7 Ni1 N4 97.27(7) . . ?
N1 Ni1 N5 94.60(8) . . ?
N7 Ni1 N5 168.80(8) . . ?
N4 Ni1 N5 78.07(7) . . ?
N1 Ni1 N8 168.56(7) . . ?
N7 Ni1 N8 78.39(8) . . ?
N4 Ni1 N8 91.26(7) . . ?
N5 Ni1 N8 91.44(8) . . ?
N1 Ni1 N2 78.19(7) . . ?
N7 Ni1 N2 91.38(7) . . ?
N4 Ni1 N2 171.25(8) . . ?
N5 Ni1 N2 93.64(7) . . ?
N8 Ni1 N2 91.75(7) . . ?
C1 N1 C5 119.0(2) . . ?
C1 N1 Ni1 126.55(16) . . ?
C5 N1 Ni1 114.40(15) . . ?
N1 C1 C2 122.2(2) . . ?
C3 C2 C1 118.9(2) . . ?
C2 C3 C4 119.6(2) . . ?
C5 C4 C3 118.7(2) . . ?
N1 C5 C4 121.6(2) . . ?
N1 C5 C6 115.4(2) . . ?
C4 C5 C6 122.9(2) . . ?
N2 C6 C5 114.92(19) . . ?
N2 C6 C7 123.8(2) . . ?
C5 C6 C7 121.2(2) . . ?
C6 N2 O1 114.26(18) . . ?
C6 N2 Ni1 115.89(15) . . ?
O1 N2 Ni1 127.86(13) . . ?
C6 C7 C8 111.93(19) . . ?
N3 C8 C9 121.7(2) . . ?
N3 C8 C7 117.73(19) . . ?
C9 C8 C7 120.6(2) . . ?
C10 C9 C8 119.4(2) . . ?
C9 C10 C11 119.3(2) . . ?
C12 C11 C10 118.1(2) . . ?
N3 C12 C11 123.5(2) . . ?
C12 N3 C8 117.98(19) . . ?
C13 N4 C17 118.2(2) . . ?
C13 N4 Ni1 127.92(17) . . ?
C17 N4 Ni1 113.21(14) . . ?
N4 C13 C14 122.6(2) . . ?
C15 C14 C13 119.0(2) . . ?
C14 C15 C16 119.2(2) . . ?
C17 C16 C15 118.5(2) . . ?
N4 C17 C16 122.2(2) . . ?
N4 C17 C18 115.50(19) . . ?
C16 C17 C18 122.3(2) . . ?
N5 C18 C17 114.6(2) . . ?
N5 C18 C19 124.7(2) . . ?
C17 C18 C19 120.7(2) . . ?
C18 N5 O2 113.63(19) . . ?
C18 N5 Ni1 116.54(15) . . ?
O2 N5 Ni1 128.74(14) . . ?
C18 C19 C20 110.8(2) . . ?
N6 C20 C21 121.8(2) . . ?
N6 C20 C19 116.9(2) . . ?
C21 C20 C19 121.3(2) . . ?
C22 C21 C20 119.2(3) . . ?
C21 C22 C23 119.8(3) . . ?
C22 C23 C24 117.8(3) . . ?
N6 C24 C23 123.3(3) . . ?
C20 N6 C24 118.1(2) . . ?
C25 N7 C29 118.6(2) . . ?
C25 N7 Ni1 127.66(18) . . ?
C29 N7 Ni1 113.55(16) . . ?
N7 C25 C26 122.8(3) . . ?
C27 C26 C25 118.8(3) . . ?
C26 C27 C28 119.4(3) . . ?
C27 C28 C29 119.0(3) . . ?
N7 C29 C28 121.4(2) . . ?
N7 C29 C30 115.7(2) . . ?
C28 C29 C30 122.9(2) . . ?
N8 C30 C29 115.3(2) . . ?
N8 C30 C31 123.8(2) . . ?
C29 C30 C31 120.7(2) . . ?
C30 N8 O3 114.35(19) . . ?
C30 N8 Ni1 116.07(16) . . ?
O3 N8 Ni1 127.45(14) . . ?
C30 C31 C32 109.6(2) . . ?
N9 C32 C33 122.3(2) . . ?
N9 C32 C31 116.9(2) . . ?
C33 C32 C31 120.8(2) . . ?
C34 C33 C32 119.6(3) . . ?
C33 C34 C35 118.6(3) . . ?
C36 C35 C34 118.8(3) . . ?
N9 C36 C35 123.5(3) . . ?
C36 N9 C32 117.2(2) . . ?
O13 Cl1 O11 108.3(3) . . ?
O13 Cl1 O12 112.8(3) . . ?
O11 Cl1 O12 105.5(3) . . ?
O13 Cl1 O14 110.8(2) . . ?
O11 Cl1 O14 109.4(2) . . ?
O12 Cl1 O14 109.8(2) . . ?
O24 Cl2 O22 109.10(17) . . ?
O24 Cl2 O23 112.0(2) . . ?
O22 Cl2 O23 106.57(19) . . ?
O24 Cl2 O21 109.98(13) . . ?
O22 Cl2 O21 110.80(13) . . ?
O23 Cl2 O21 108.32(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.2(4) . . . . ?
Ni1 N1 C1 C2 176.58(19) . . . . ?
N1 C1 C2 C3 0.6(4) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C1 N1 C5 C4 -1.1(3) . . . . ?
Ni1 N1 C5 C4 -177.96(19) . . . . ?
C1 N1 C5 C6 178.0(2) . . . . ?
Ni1 N1 C5 C6 1.1(3) . . . . ?
C3 C4 C5 N1 1.3(4) . . . . ?
C3 C4 C5 C6 -177.7(2) . . . . ?
N1 C5 C6 N2 -9.0(3) . . . . ?
C4 C5 C6 N2 170.0(2) . . . . ?
N1 C5 C6 C7 168.3(2) . . . . ?
C4 C5 C6 C7 -12.7(4) . . . . ?
C5 C6 N2 O1 177.60(18) . . . . ?
C7 C6 N2 O1 0.4(3) . . . . ?
C5 C6 N2 Ni1 12.4(3) . . . . ?
C7 C6 N2 Ni1 -164.84(17) . . . . ?
N2 C6 C7 C8 91.3(3) . . . . ?
C5 C6 C7 C8 -85.7(3) . . . . ?
C6 C7 C8 N3 -22.7(3) . . . . ?
C6 C7 C8 C9 158.0(2) . . . . ?
N3 C8 C9 C10 -1.6(4) . . . . ?
C7 C8 C9 C10 177.7(2) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 1.6(4) . . . . ?
C10 C11 C12 N3 -1.4(4) . . . . ?
C11 C12 N3 C8 -0.2(4) . . . . ?
C9 C8 N3 C12 1.8(3) . . . . ?
C7 C8 N3 C12 -177.5(2) . . . . ?
C17 N4 C13 C14 1.9(3) . . . . ?
Ni1 N4 C13 C14 -168.37(17) . . . . ?
N4 C13 C14 C15 2.0(4) . . . . ?
C13 C14 C15 C16 -3.5(4) . . . . ?
C14 C15 C16 C17 1.3(4) . . . . ?
C13 N4 C17 C16 -4.3(3) . . . . ?
Ni1 N4 C17 C16 167.39(17) . . . . ?
C13 N4 C17 C18 176.0(2) . . . . ?
Ni1 N4 C17 C18 -12.4(2) . . . . ?
C15 C16 C17 N4 2.7(3) . . . . ?
C15 C16 C17 C18 -177.6(2) . . . . ?
N4 C17 C18 N5 2.7(3) . . . . ?
C16 C17 C18 N5 -177.1(2) . . . . ?
N4 C17 C18 C19 179.6(2) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 N5 O2 177.74(18) . . . . ?
C19 C18 N5 O2 1.0(3) . . . . ?
C17 C18 N5 Ni1 8.6(3) . . . . ?
C19 C18 N5 Ni1 -168.11(17) . . . . ?
N5 C18 C19 C20 98.9(3) . . . . ?
C17 C18 C19 C20 -77.7(3) . . . . ?
C18 C19 C20 N6 -23.3(3) . . . . ?
C18 C19 C20 C21 157.6(2) . . . . ?
N6 C20 C21 C22 -0.9(4) . . . . ?
C19 C20 C21 C22 178.1(2) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
C22 C23 C24 N6 -0.6(4) . . . . ?
C21 C20 N6 C24 0.7(3) . . . . ?
C19 C20 N6 C24 -178.3(2) . . . . ?
C23 C24 N6 C20 0.0(4) . . . . ?
C29 N7 C25 C26 0.8(4) . . . . ?
Ni1 N7 C25 C26 -174.0(2) . . . . ?
N7 C25 C26 C27 0.0(4) . . . . ?
C25 C26 C27 C28 -1.2(4) . . . . ?
C26 C27 C28 C29 1.6(4) . . . . ?
C25 N7 C29 C28 -0.3(3) . . . . ?
Ni1 N7 C29 C28 175.22(17) . . . . ?
C25 N7 C29 C30 -178.7(2) . . . . ?
Ni1 N7 C29 C30 -3.2(2) . . . . ?
C27 C28 C29 N7 -0.9(3) . . . . ?
C27 C28 C29 C30 177.4(2) . . . . ?
N7 C29 C30 N8 -4.7(3) . . . . ?
C28 C29 C30 N8 176.9(2) . . . . ?
N7 C29 C30 C31 170.5(2) . . . . ?
C28 C29 C30 C31 -7.9(3) . . . . ?
C29 C30 N8 O3 174.98(17) . . . . ?
C31 C30 N8 O3 -0.1(3) . . . . ?
C29 C30 N8 Ni1 10.3(2) . . . . ?
C31 C30 N8 Ni1 -164.72(17) . . . . ?
N8 C30 C31 C32 105.1(3) . . . . ?
C29 C30 C31 C32 -69.7(3) . . . . ?
C30 C31 C32 N9 -29.9(3) . . . . ?
C30 C31 C32 C33 150.4(2) . . . . ?
N9 C32 C33 C34 -1.2(4) . . . . ?
C31 C32 C33 C34 178.5(3) . . . . ?
C32 C33 C34 C35 0.8(5) . . . . ?
C33 C34 C35 C36 -0.1(5) . . . . ?
C34 C35 C36 N9 -0.3(4) . . . . ?
C35 C36 N9 C32 0.0(4) . . . . ?
C33 C32 N9 C36 0.8(4) . . . . ?
C31 C32 N9 C36 -178.9(2) . . . . ?

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 H1O N9 0.83(3) 1.95(3) 2.728(3) 157(3) .
O2 H2O N3 0.85(3) 1.91(3) 2.693(2) 154(3) .
O3 H3O N6 0.86(3) 1.90(3) 2.677(3) 149(3) .

_refine_diff_density_max         0.783
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_cm14030
_database_code_depnum_ccdc_archive 'CCDC 1498810'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 N6 O2 Cu, 2 (Cl O4)'
_chemical_formula_sum            'C24 H22 Cl2 Cu N6 O10'
_chemical_formula_weight         688.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   6.9995(9)
_cell_length_b                   13.0502(15)
_cell_length_c                   15.8518(19)
_cell_angle_alpha                69.489(7)
_cell_angle_beta                 77.659(8)
_cell_angle_gamma                82.462(7)
_cell_volume                     1322.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2833
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      30.19

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             702
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.099
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6594
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS v2008/1 (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            26733
_diffrn_reflns_av_unetI/netI     0.1158
_diffrn_reflns_av_R_equivalents  0.1255
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.985
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             5126
_reflns_number_gt                3243
_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       'APEX2 v.2010.1-2 (Bruker Nonius, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        'SAINT v.7.68a (Bruker, 2010)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0565P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5126
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.66773(8) 0.14604(4) 0.18760(4) 0.02104(17) Uani 1 1 d . . . . .
O1 O 0.5207(4) 0.1935(2) 0.35850(19) 0.0232(7) Uani 1 1 d . . . . .
H1O H 0.5396 0.1249 0.3757 0.035 Uiso 0.5 1 calc R U P . .
N1 N 0.7100(5) 0.2969(3) 0.0946(2) 0.0207(8) Uani 1 1 d . . . . .
C1 C 0.7936(6) 0.3251(4) 0.0063(3) 0.0262(11) Uani 1 1 d . . . . .
H1 H 0.8385 0.2686 -0.0193 0.031 Uiso 1 1 calc R U . . .
O2 O 0.6219(4) 0.0004(2) 0.38030(19) 0.0255(7) Uani 1 1 d . . . . .
H2O H 0.5790 0.0619 0.3845 0.038 Uiso 0.5 1 calc R U P . .
N2 N 0.5868(5) 0.2355(3) 0.2678(2) 0.0207(8) Uani 1 1 d . . . . .
C2 C 0.8182(7) 0.4327(4) -0.0498(3) 0.0338(12) Uani 1 1 d . . . . .
H2 H 0.8748 0.4493 -0.1128 0.041 Uiso 1 1 calc R U . . .
N4 N 0.7104(5) 0.0390(3) 0.1200(2) 0.0209(8) Uani 1 1 d . . . . .
C4 C 0.6733(7) 0.4874(4) 0.0790(3) 0.0290(11) Uani 1 1 d . . . . .
H4 H 0.6300 0.5432 0.1056 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7594(7) 0.5146(4) -0.0131(3) 0.0334(12) Uani 1 1 d . . . . .
H3 H 0.7772 0.5890 -0.0499 0.040 Uiso 1 1 calc R U . . .
N3 N 0.5115(6) 0.3719(3) 0.4409(3) 0.0282(9) Uani 1 1 d . . . . .
N5 N 0.6617(5) 0.0074(3) 0.2919(2) 0.0212(8) Uani 1 1 d . . . . .
C5 C 0.6515(6) 0.3787(3) 0.1311(3) 0.0221(10) Uani 1 1 d . . . . .
C7 C 0.4725(7) 0.4134(4) 0.2834(3) 0.0279(11) Uani 1 1 d . . . . .
H7A H 0.3415 0.3872 0.3160 0.033 Uiso 1 1 calc R U . . .
H7B H 0.4535 0.4886 0.2406 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5886(7) 0.4168(3) 0.3524(3) 0.0253(11) Uani 1 1 d . . . . .
C9 C 0.7627(8) 0.4672(4) 0.3242(3) 0.0370(13) Uani 1 1 d . . . . .
H9 H 0.8135 0.4979 0.2607 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5702(6) 0.3401(3) 0.2293(3) 0.0223(10) Uani 1 1 d . . . . .
N6 N 0.8215(6) -0.2197(3) 0.4994(3) 0.0264(9) Uani 1 1 d . . . . .
H6 H 0.721(7) -0.257(4) 0.515(3) 0.040 Uiso 1 1 d . U . . .
C20 C 0.8846(7) -0.1741(3) 0.4092(3) 0.0244(11) Uani 1 1 d . . . . .
C19 C 0.7662(7) -0.1867(3) 0.3449(3) 0.0285(11) Uani 1 1 d . . . . .
H19A H 0.8368 -0.2401 0.3158 0.034 Uiso 1 1 calc R U . . .
H19B H 0.6391 -0.2163 0.3803 0.034 Uiso 1 1 calc R U . . .
C18 C 0.7293(6) -0.0797(3) 0.2716(3) 0.0240(10) Uani 1 1 d . . . . .
C17 C 0.7509(6) -0.0652(4) 0.1741(3) 0.0225(10) Uani 1 1 d . . . . .
C16 C 0.7920(7) -0.1513(4) 0.1404(3) 0.0294(11) Uani 1 1 d . . . . .
H16 H 0.8205 -0.2235 0.1793 0.035 Uiso 1 1 calc R U . . .
C13 C 0.7063(6) 0.0573(4) 0.0316(3) 0.0242(10) Uani 1 1 d . . . . .
H13 H 0.6737 0.1295 -0.0060 0.029 Uiso 1 1 calc R U . . .
C22 C 1.1520(7) -0.1081(4) 0.4437(4) 0.0318(12) Uani 1 1 d . . . . .
H22 H 1.2685 -0.0696 0.4237 0.038 Uiso 1 1 calc R U . . .
C23 C 1.0800(7) -0.1538(4) 0.5353(3) 0.0324(12) Uani 1 1 d . . . . .
H23 H 1.1451 -0.1464 0.5795 0.039 Uiso 1 1 calc R U . . .
C24 C 0.9146(7) -0.2097(4) 0.5623(3) 0.0300(11) Uani 1 1 d . . . . .
H24 H 0.8641 -0.2419 0.6256 0.036 Uiso 1 1 calc R U . . .
C14 C 0.7478(7) -0.0251(4) -0.0062(3) 0.0296(11) Uani 1 1 d . . . . .
H14 H 0.7467 -0.0092 -0.0693 0.036 Uiso 1 1 calc R U . . .
C15 C 0.7906(7) -0.1302(4) 0.0478(3) 0.0312(12) Uani 1 1 d . . . . .
H15 H 0.8190 -0.1878 0.0225 0.037 Uiso 1 1 calc R U . . .
C12 C 0.6110(8) 0.3795(4) 0.5019(3) 0.0326(12) Uani 1 1 d . . . . .
H12 H 0.5566 0.3490 0.5651 0.039 Uiso 1 1 calc R U . . .
C21 C 1.0531(7) -0.1185(3) 0.3802(3) 0.0274(11) Uani 1 1 d . . . . .
H21 H 1.1021 -0.0871 0.3165 0.033 Uiso 1 1 calc R U . . .
C11 C 0.7859(8) 0.4284(4) 0.4796(4) 0.0355(12) Uani 1 1 d . . . . .
H11 H 0.8501 0.4308 0.5259 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8652(8) 0.4735(4) 0.3885(4) 0.0376(13) Uani 1 1 d . . . . .
H10 H 0.9860 0.5079 0.3698 0.045 Uiso 1 1 calc R U . . .
Cl1 Cl 1.16594(16) 0.17984(8) 0.19429(7) 0.0229(3) Uani 1 1 d . . . . .
O4 O 1.2470(6) 0.1082(3) 0.2708(3) 0.0540(11) Uani 1 1 d . . . . .
O3 O 1.3195(5) 0.2102(3) 0.1163(3) 0.0512(11) Uani 1 1 d . . . . .
O5 O 1.0256(4) 0.1233(3) 0.1755(2) 0.0352(8) Uani 1 1 d . . . . .
O6 O 1.0752(5) 0.2752(3) 0.2136(2) 0.0381(9) Uani 1 1 d . . . . .
Cl2 Cl 0.3140(2) 0.72110(10) 0.21848(8) 0.0381(3) Uani 1 1 d . . . . .
O7 O 0.2496(7) 0.8318(3) 0.1919(3) 0.0830(16) Uani 1 1 d . . . . .
O8 O 0.4294(6) 0.6958(3) 0.1424(3) 0.0553(11) Uani 1 1 d . . . . .
O9 O 0.4310(10) 0.6968(6) 0.2838(3) 0.144(3) Uani 1 1 d . . . . .
O10 O 0.1555(8) 0.6580(4) 0.2534(5) 0.136(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
Cu1 N2 1.964(3) . ?
Cu1 N5 1.976(4) . ?
Cu1 N4 1.998(3) . ?
Cu1 N1 2.017(3) . ?
Cu1 O5 2.458(3) . ?
Cu1 O3 2.810(4) 1_455 ?
O1 N2 1.346(4) . ?
N1 C1 1.335(5) . ?
N1 C5 1.364(5) . ?
C1 C2 1.383(6) . ?
O2 N5 1.341(4) . ?
N2 C6 1.287(5) . ?
C2 C3 1.368(6) . ?
N4 C13 1.342(5) . ?
N4 C17 1.361(5) . ?
C4 C5 1.379(6) . ?
C4 C3 1.392(6) . ?
N3 C8 1.337(6) . ?
N3 C12 1.343(6) . ?
N5 C18 1.292(5) . ?
C5 C6 1.466(6) . ?
C7 C6 1.507(6) . ?
C7 C8 1.511(6) . ?
C8 C9 1.374(7) . ?
C9 C10 1.394(7) . ?
N6 C20 1.340(6) . ?
N6 C24 1.351(6) . ?
C20 C21 1.374(6) . ?
C20 C19 1.505(6) . ?
C19 C18 1.505(6) . ?
C18 C17 1.465(6) . ?
C17 C16 1.379(6) . ?
C16 C15 1.398(6) . ?
C13 C14 1.377(6) . ?
C22 C23 1.370(7) . ?
C22 C21 1.388(6) . ?
C23 C24 1.360(6) . ?
C14 C15 1.372(6) . ?
C12 C11 1.375(7) . ?
C11 C10 1.374(7) . ?
Cl1 O6 1.422(3) . ?
Cl1 O4 1.424(3) . ?
Cl1 O3 1.428(4) . ?
Cl1 O5 1.438(3) . ?
Cl2 O10 1.369(5) . ?
Cl2 O9 1.381(5) . ?
Cl2 O7 1.397(4) . ?
Cl2 O8 1.417(4) . ?

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
N2 Cu1 N5 92.94(14) . . ?
N2 Cu1 N4 169.78(15) . . ?
N5 Cu1 N4 80.29(14) . . ?
N2 Cu1 N1 80.03(14) . . ?
N5 Cu1 N1 168.15(14) . . ?
N4 Cu1 N1 107.88(14) . . ?
N2 Cu1 O5 103.30(13) . . ?
N5 Cu1 O5 85.76(13) . . ?
N4 Cu1 O5 83.96(12) . . ?
N1 Cu1 O5 86.60(13) . . ?
N2 Cu1 O3 91.33(12) . 1_455 ?
N5 Cu1 O3 115.12(13) . 1_455 ?
N4 Cu1 O3 84.73(12) . 1_455 ?
N1 Cu1 O3 74.85(12) . 1_455 ?
O5 Cu1 O3 154.09(11) . 1_455 ?
C1 N1 C5 117.8(4) . . ?
C1 N1 Cu1 129.1(3) . . ?
C5 N1 Cu1 113.0(3) . . ?
N1 C1 C2 123.3(4) . . ?
C6 N2 O1 118.2(3) . . ?
C6 N2 Cu1 117.4(3) . . ?
O1 N2 Cu1 123.6(2) . . ?
C3 C2 C1 118.8(5) . . ?
C13 N4 C17 118.5(4) . . ?
C13 N4 Cu1 129.0(3) . . ?
C17 N4 Cu1 112.5(3) . . ?
C5 C4 C3 119.3(4) . . ?
C2 C3 C4 119.1(4) . . ?
C8 N3 C12 116.8(4) . . ?
C18 N5 O2 118.6(4) . . ?
C18 N5 Cu1 115.9(3) . . ?
O2 N5 Cu1 124.7(2) . . ?
N1 C5 C4 121.7(4) . . ?
N1 C5 C6 114.2(4) . . ?
C4 C5 C6 124.1(4) . . ?
C6 C7 C8 113.1(4) . . ?
N3 C8 C9 122.2(4) . . ?
N3 C8 C7 117.1(4) . . ?
C9 C8 C7 120.7(4) . . ?
C8 C9 C10 120.3(5) . . ?
N2 C6 C5 114.4(4) . . ?
N2 C6 C7 121.0(4) . . ?
C5 C6 C7 124.6(4) . . ?
C20 N6 C24 122.2(4) . . ?
N6 C20 C21 118.6(4) . . ?
N6 C20 C19 118.0(4) . . ?
C21 C20 C19 123.5(4) . . ?
C18 C19 C20 112.1(4) . . ?
N5 C18 C17 114.0(4) . . ?
N5 C18 C19 121.1(4) . . ?
C17 C18 C19 124.8(4) . . ?
N4 C17 C16 122.1(4) . . ?
N4 C17 C18 114.7(4) . . ?
C16 C17 C18 123.0(4) . . ?
C17 C16 C15 118.5(4) . . ?
N4 C13 C14 122.1(4) . . ?
C23 C22 C21 119.4(5) . . ?
C24 C23 C22 119.3(5) . . ?
N6 C24 C23 120.3(5) . . ?
C15 C14 C13 119.7(4) . . ?
C14 C15 C16 119.1(4) . . ?
N3 C12 C11 124.7(5) . . ?
C20 C21 C22 120.2(4) . . ?
C10 C11 C12 118.2(5) . . ?
C11 C10 C9 117.8(5) . . ?
O6 Cl1 O4 109.7(2) . . ?
O6 Cl1 O3 109.7(2) . . ?
O4 Cl1 O3 108.9(3) . . ?
O6 Cl1 O5 110.54(19) . . ?
O4 Cl1 O5 109.1(2) . . ?
O3 Cl1 O5 109.0(2) . . ?
Cl1 O5 Cu1 133.38(18) . . ?
O10 Cl2 O9 109.3(5) . . ?
O10 Cl2 O7 109.4(3) . . ?
O9 Cl2 O7 111.0(4) . . ?
O10 Cl2 O8 110.1(3) . . ?
O9 Cl2 O8 106.9(3) . . ?
O7 Cl2 O8 110.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -1.9(6) . . . . ?
Cu1 N1 C1 C2 -178.2(3) . . . . ?
N1 C1 C2 C3 1.9(7) . . . . ?
C1 C2 C3 C4 -1.3(7) . . . . ?
C5 C4 C3 C2 0.8(7) . . . . ?
C1 N1 C5 C4 1.3(6) . . . . ?
Cu1 N1 C5 C4 178.2(3) . . . . ?
C1 N1 C5 C6 -177.1(4) . . . . ?
Cu1 N1 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 N1 -0.8(7) . . . . ?
C3 C4 C5 C6 177.5(4) . . . . ?
C12 N3 C8 C9 1.0(6) . . . . ?
C12 N3 C8 C7 -177.1(3) . . . . ?
C6 C7 C8 N3 -112.4(4) . . . . ?
C6 C7 C8 C9 69.5(5) . . . . ?
N3 C8 C9 C10 -0.4(7) . . . . ?
C7 C8 C9 C10 177.6(4) . . . . ?
O1 N2 C6 C5 178.2(3) . . . . ?
Cu1 N2 C6 C5 -11.4(5) . . . . ?
O1 N2 C6 C7 -2.3(6) . . . . ?
Cu1 N2 C6 C7 168.1(3) . . . . ?
N1 C5 C6 N2 7.4(5) . . . . ?
C4 C5 C6 N2 -171.0(4) . . . . ?
N1 C5 C6 C7 -172.0(4) . . . . ?
C4 C5 C6 C7 9.6(7) . . . . ?
C8 C7 C6 N2 68.3(6) . . . . ?
C8 C7 C6 C5 -112.3(5) . . . . ?
C24 N6 C20 C21 2.1(6) . . . . ?
C24 N6 C20 C19 -177.8(4) . . . . ?
N6 C20 C19 C18 132.3(4) . . . . ?
C21 C20 C19 C18 -47.7(6) . . . . ?
O2 N5 C18 C17 174.8(3) . . . . ?
Cu1 N5 C18 C17 -15.1(5) . . . . ?
O2 N5 C18 C19 -1.1(6) . . . . ?
Cu1 N5 C18 C19 169.1(3) . . . . ?
C20 C19 C18 N5 -49.9(6) . . . . ?
C20 C19 C18 C17 134.7(4) . . . . ?
C13 N4 C17 C16 1.5(6) . . . . ?
Cu1 N4 C17 C16 -177.7(3) . . . . ?
C13 N4 C17 C18 -173.0(4) . . . . ?
Cu1 N4 C17 C18 7.7(5) . . . . ?
N5 C18 C17 N4 4.6(6) . . . . ?
C19 C18 C17 N4 -179.8(4) . . . . ?
N5 C18 C17 C16 -169.9(4) . . . . ?
C19 C18 C17 C16 5.8(7) . . . . ?
N4 C17 C16 C15 -0.3(7) . . . . ?
C18 C17 C16 C15 173.8(4) . . . . ?
C17 N4 C13 C14 -2.1(6) . . . . ?
Cu1 N4 C13 C14 177.0(3) . . . . ?
C21 C22 C23 C24 0.9(7) . . . . ?
C20 N6 C24 C23 -1.2(6) . . . . ?
C22 C23 C24 N6 -0.3(7) . . . . ?
N4 C13 C14 C15 1.5(7) . . . . ?
C13 C14 C15 C16 -0.2(7) . . . . ?
C17 C16 C15 C14 -0.3(7) . . . . ?
C8 N3 C12 C11 -1.0(6) . . . . ?
N6 C20 C21 C22 -1.5(6) . . . . ?
C19 C20 C21 C22 178.5(4) . . . . ?
C23 C22 C21 C20 0.0(6) . . . . ?
N3 C12 C11 C10 0.5(7) . . . . ?
C12 C11 C10 C9 0.2(7) . . . . ?
C8 C9 C10 C11 -0.2(7) . . . . ?
O6 Cl1 O5 Cu1 -8.3(3) . . . . ?
O4 Cl1 O5 Cu1 112.4(3) . . . . ?
O3 Cl1 O5 Cu1 -128.9(3) . . . . ?

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 H1O O2 0.84 1.63 2.449(4) 163.0 .
O2 H2O O1 0.84 1.64 2.449(4) 162.2 .
N6 H6 N3 0.85(5) 2.19(5) 3.038(6) 172(5) 2_656

_refine_diff_density_max         0.700
_refine_diff_density_min         -0.597
_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_cm14105_sq
_database_code_depnum_ccdc_archive 'CCDC 1498811'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 Cl Cu N6 O8, 1.33(C2 H6 O)'
_chemical_formula_sum            'C26.67 H23.33 Cl Cu N6 O9.33'
_chemical_formula_weight         676.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

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

_cell_length_a                   34.878(4)
_cell_length_b                   34.878(4)
_cell_length_c                   12.477(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     13144(5)
_cell_formula_units_Z            18
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8777
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      24.08

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             6228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.904
_shelx_estimated_absorpt_T_min   0.840
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2951
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS v2008/1 (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            78840
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.1610
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.336
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5721
_reflns_number_gt                3625
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 v.2010.1-2 (Bruker Nonius, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        'SAINT v.7.68a (Bruker, 2010)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          
;Disordered solvent addressed using SQUEEZE - 3 voids/cell 918, 922, 924A 
and 208 electrons each = 8 EtOH each(208 e), SQUEEZE
;
# start Validation Reply Form
_vrf_CHEMW03_cm14105_sq          
;
PROBLEM: WARNING: The ratio of given/expected molecular weight as
RESPONSE: Disordered solvent addressed using SQUEEZE - 3 voids/cell 
918, 922, 924 A3 and 208 electrons each = 8 EtOH each(208 e)
These were included in the UNIT atom count (= 1.333 EtOH per molecule).
(EtOH was the reaction & crystallisation solvent)
;
# end Validation Reply Form

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   diifmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5721
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_restrained_S_all      0.825
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.61504(2) 0.76057(2) 0.62015(3) 0.05423(13) Uani 1 1 d . . . . .
Cl1 Cl 0.71034(2) 0.74907(2) 0.52266(6) 0.0598(2) Uani 1 1 d . . . . .
N1 N 0.56320(7) 0.72114(7) 0.52438(19) 0.0541(6) Uani 1 1 d . . . . .
O1 O 0.55635(7) 0.80688(7) 0.73470(17) 0.0665(6) Uani 1 1 d . . . . .
H1O H 0.5785 0.8189 0.7755 0.100 Uiso 1 1 calc R U . . .
C1 C 0.56240(10) 0.69006(9) 0.4588(2) 0.0573(7) Uani 1 1 d . . . . .
H1 H 0.5890 0.6891 0.4498 0.069 Uiso 1 1 calc R U . . .
N2 N 0.55850(8) 0.77506(7) 0.6730(2) 0.0557(6) Uani 1 1 d . . . . .
O2 O 0.45730(7) 0.74928(7) 0.66691(19) 0.0714(6) Uani 1 1 d . . . . .
C2 C 0.52516(10) 0.65951(10) 0.4039(2) 0.0628(8) Uani 1 1 d . . . . .
H2 H 0.5263 0.6383 0.3582 0.075 Uiso 1 1 calc R U . . .
C3 C 0.48623(10) 0.66043(11) 0.4169(3) 0.0696(9) Uani 1 1 d . . . . .
H3 H 0.4600 0.6398 0.3804 0.084 Uiso 1 1 calc R U . . .
O3 O 0.72803(7) 0.86637(7) 0.72694(19) 0.0720(6) Uani 1 1 d . . . . .
N3 N 0.52863(9) 0.81188(9) 0.4571(2) 0.0702(7) Uani 1 1 d . . . . .
C4 C 0.48630(10) 0.69204(10) 0.4842(3) 0.0631(8) Uani 1 1 d . . . . .
H4 H 0.4599 0.6933 0.4940 0.076 Uiso 1 1 calc R U . . .
O4 O 0.69992(7) 0.79297(6) 0.86956(18) 0.0692(6) Uani 1 1 d . . . . .
N4 N 0.64233(7) 0.81694(7) 0.5332(2) 0.0557(6) Uani 1 1 d . . . . .
C5 C 0.52437(9) 0.72159(9) 0.5369(2) 0.0540(7) Uani 1 1 d . . . . .
O5 O 0.66559(7) 0.73419(7) 0.48883(19) 0.0794(7) Uani 1 1 d . . . . .
N5 N 0.66501(7) 0.79640(7) 0.71207(19) 0.0557(6) Uani 1 1 d . . . . .
C6 C 0.52566(9) 0.75541(9) 0.6094(2) 0.0528(7) Uani 1 1 d . . . . .
O6 O 0.70966(7) 0.73195(7) 0.62825(17) 0.0697(6) Uani 1 1 d . . . . .
N6 N 0.60827(7) 0.71229(8) 0.71962(18) 0.0547(6) Uani 1 1 d . . . . .
O7 O 0.73167(8) 0.73444(8) 0.44831(19) 0.0837(7) Uani 1 1 d . . . . .
C7 C 0.48842(10) 0.76627(10) 0.6052(3) 0.0577(7) Uani 1 1 d . . . . .
C8 C 0.49341(10) 0.79886(9) 0.5214(3) 0.0601(8) Uani 1 1 d . . . . .
O8 O 0.73400(7) 0.79708(7) 0.52507(18) 0.0705(6) Uani 1 1 d . . . . .
C9 C 0.46351(11) 0.81379(10) 0.5133(3) 0.0688(9) Uani 1 1 d . . . . .
H9 H 0.4380 0.8021 0.5577 0.083 Uiso 1 1 calc R U . . .
C10 C 0.47212(13) 0.84631(12) 0.4382(3) 0.0848(11) Uani 1 1 d . . . . .
H10 H 0.4530 0.8583 0.4320 0.102 Uiso 1 1 calc R U . . .
C11 C 0.50831(13) 0.86111(13) 0.3730(3) 0.0903(12) Uani 1 1 d . . . . .
H11 H 0.5149 0.8836 0.3214 0.108 Uiso 1 1 calc R U . . .
C12 C 0.53507(12) 0.84246(13) 0.3839(3) 0.0887(11) Uani 1 1 d . . . . .
H12 H 0.5595 0.8520 0.3365 0.106 Uiso 1 1 calc R U . . .
C15 C 0.68911(11) 0.89809(10) 0.4316(3) 0.0678(9) Uani 1 1 d . . . . .
H15 H 0.7055 0.9258 0.3962 0.081 Uiso 1 1 calc R U . . .
C14 C 0.65036(11) 0.86471(10) 0.3874(3) 0.0650(8) Uani 1 1 d . . . . .
H14 H 0.6395 0.8690 0.3213 0.078 Uiso 1 1 calc R U . . .
C13 C 0.62785(10) 0.82500(10) 0.4414(3) 0.0598(8) Uani 1 1 d . . . . .
H13 H 0.6008 0.8023 0.4121 0.072 Uiso 1 1 calc R U . . .
C16 C 0.70361(11) 0.89053(10) 0.5283(3) 0.0666(8) Uani 1 1 d . . . . .
H16 H 0.7298 0.9133 0.5607 0.080 Uiso 1 1 calc R U . . .
C17 C 0.67989(9) 0.84983(9) 0.5775(2) 0.0565(7) Uani 1 1 d . . . . .
C18 C 0.69444(10) 0.83896(10) 0.6815(3) 0.0614(8) Uani 1 1 d . . . . .
C19 C 0.67149(10) 0.77628(10) 0.7978(2) 0.0576(7) Uani 1 1 d . . . . .
C20 C 0.63927(9) 0.72723(9) 0.7982(2) 0.0544(7) Uani 1 1 d . . . . .
C22 C 0.61403(10) 0.65414(10) 0.8615(3) 0.0658(8) Uani 1 1 d . . . . .
H22 H 0.6160 0.6341 0.9095 0.079 Uiso 1 1 calc R U . . .
C21 C 0.64245(10) 0.69924(10) 0.8707(3) 0.0612(8) Uani 1 1 d . . . . .
H21 H 0.6639 0.7107 0.9263 0.073 Uiso 1 1 calc R U . . .
C23 C 0.58264(10) 0.63892(10) 0.7806(3) 0.0658(8) Uani 1 1 d . . . . .
H23 H 0.5628 0.6081 0.7723 0.079 Uiso 1 1 calc R U . . .
C24 C 0.58027(9) 0.66860(10) 0.7124(2) 0.0588(8) Uani 1 1 d . . . . .
H24 H 0.5581 0.6578 0.6585 0.071 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
Cu1 N5 1.933(2) . ?
Cu1 N6 2.009(2) . ?
Cu1 N4 2.019(2) . ?
Cu1 N1 2.025(2) . ?
Cu1 N2 2.362(2) . ?
Cu1 O5 2.874(2) . ?
Cl1 O7 1.433(2) . ?
Cl1 O5 1.440(2) . ?
Cl1 O6 1.442(2) . ?
Cl1 O8 1.450(2) . ?
N1 C1 1.347(3) . ?
N1 C5 1.371(3) . ?
O1 N2 1.383(3) . ?
O1 H1O 0.8400 . ?
C1 C2 1.381(4) . ?
C1 H1 0.9500 . ?
N2 C6 1.276(3) . ?
O2 C7 1.216(3) . ?
C2 C3 1.384(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
O3 C18 1.220(3) . ?
N3 C12 1.335(4) . ?
N3 C8 1.342(4) . ?
C4 C5 1.374(4) . ?
C4 H4 0.9500 . ?
O4 C19 1.243(3) . ?
N4 C13 1.337(4) . ?
N4 C17 1.355(3) . ?
C5 C6 1.470(4) . ?
N5 C19 1.359(4) . ?
N5 C18 1.371(4) . ?
C6 C7 1.525(4) . ?
N6 C24 1.340(3) . ?
N6 C20 1.356(3) . ?
C7 C8 1.490(4) . ?
C8 C9 1.383(4) . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C15 C14 1.383(4) . ?
C15 C16 1.384(5) . ?
C15 H15 0.9500 . ?
C14 C13 1.379(4) . ?
C14 H14 0.9500 . ?
C13 H13 0.9500 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.509(4) . ?
C19 C20 1.506(4) . ?
C20 C21 1.375(4) . ?
C22 C21 1.382(4) . ?
C22 C23 1.384(4) . ?
C22 H22 0.9500 . ?
C21 H21 0.9500 . ?
C23 C24 1.374(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Cu1 N6 82.27(10) . . ?
N5 Cu1 N4 81.69(10) . . ?
N6 Cu1 N4 161.61(9) . . ?
N5 Cu1 N1 177.83(10) . . ?
N6 Cu1 N1 96.00(9) . . ?
N4 Cu1 N1 99.81(10) . . ?
N5 Cu1 N2 105.98(9) . . ?
N6 Cu1 N2 104.26(9) . . ?
N4 Cu1 N2 88.80(9) . . ?
N1 Cu1 N2 75.68(9) . . ?
N5 Cu1 O5 92.64(8) . . ?
N6 Cu1 O5 85.27(8) . . ?
N4 Cu1 O5 86.54(8) . . ?
N1 Cu1 O5 85.90(8) . . ?
N2 Cu1 O5 159.94(7) . . ?
O7 Cl1 O5 110.12(15) . . ?
O7 Cl1 O6 110.35(14) . . ?
O5 Cl1 O6 109.16(13) . . ?
O7 Cl1 O8 109.10(14) . . ?
O5 Cl1 O8 108.12(14) . . ?
O6 Cl1 O8 109.96(13) . . ?
C1 N1 C5 117.1(2) . . ?
C1 N1 Cu1 123.8(2) . . ?
C5 N1 Cu1 118.48(18) . . ?
N2 O1 H1O 109.5 . . ?
N1 C1 C2 123.7(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C6 N2 O1 112.5(2) . . ?
C6 N2 Cu1 109.43(18) . . ?
O1 N2 Cu1 135.50(17) . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C12 N3 C8 116.0(3) . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C13 N4 C17 118.6(3) . . ?
C13 N4 Cu1 128.4(2) . . ?
C17 N4 Cu1 113.0(2) . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 116.4(2) . . ?
C4 C5 C6 121.8(3) . . ?
Cl1 O5 Cu1 116.44(13) . . ?
C19 N5 C18 123.4(3) . . ?
C19 N5 Cu1 117.52(19) . . ?
C18 N5 Cu1 118.7(2) . . ?
N2 C6 C5 118.3(3) . . ?
N2 C6 C7 122.4(3) . . ?
C5 C6 C7 119.4(3) . . ?
C24 N6 C20 118.2(3) . . ?
C24 N6 Cu1 128.7(2) . . ?
C20 N6 Cu1 112.82(18) . . ?
O2 C7 C8 123.5(3) . . ?
O2 C7 C6 121.4(3) . . ?
C8 C7 C6 115.1(3) . . ?
N3 C8 C9 124.4(3) . . ?
N3 C8 C7 114.6(3) . . ?
C9 C8 C7 121.1(3) . . ?
C8 C9 C10 117.5(3) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 118.4(4) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
N3 C12 C11 124.0(4) . . ?
N3 C12 H12 118.0 . . ?
C11 C12 H12 118.0 . . ?
C14 C15 C16 119.0(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C14 C13 118.4(3) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
N4 C13 C14 123.0(3) . . ?
N4 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
N4 C17 C16 121.2(3) . . ?
N4 C17 C18 116.3(3) . . ?
C16 C17 C18 122.5(3) . . ?
O3 C18 N5 128.7(3) . . ?
O3 C18 C17 121.0(3) . . ?
N5 C18 C17 110.3(3) . . ?
O4 C19 N5 128.6(3) . . ?
O4 C19 C20 119.8(3) . . ?
N5 C19 C20 111.5(3) . . ?
N6 C20 C21 122.3(3) . . ?
N6 C20 C19 115.6(3) . . ?
C21 C20 C19 122.0(3) . . ?
C21 C22 C23 118.5(3) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C20 C21 C22 119.1(3) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C24 C23 C22 119.7(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
N6 C24 C23 122.1(3) . . ?
N6 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?

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 H1O O3 0.84 2.47 3.147(3) 138.1 16_666
O1 H1O O4 0.84 1.93 2.645(3) 141.9 16_666

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_cm1302
_database_code_depnum_ccdc_archive 'CCDC 1518717'
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H33 Co N9 O3, 3(Cl O4)'
_chemical_formula_sum            'C36 H33 Cl3 Co N9 O15'
_chemical_formula_weight         996.99

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   17.9821(6)
_cell_length_b                   17.9821(6)
_cell_length_c                   22.4936(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6299.0(6)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      27.89

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_F_000             3060
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.680
_shelx_estimated_absorpt_T_min   0.848
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS v2008, (Sheldrick, 2008)'
_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  'Bruker-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            32851
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.182
_diffrn_reflns_theta_max         28.398
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3328
_reflns_number_gt                3057
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_max     0.993
_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       'APEX2 v.2010.1-2 (Bruker Nonius, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        'SAINT v.7.68a (Bruker, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  'PublCIF (Westrip, 2010)'
_refine_special_details          
'Refined as a 2-component inversion twin., 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)+(0.0414P)²+2.6212P] 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 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.40(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3328
_refine_ls_number_parameters     225
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.089
_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
Co1 Co 0.666667 0.333333 0.10846(4) 0.02094(14) Uani 1 3 d S T P . .
O1 O 0.78677(14) 0.36577(13) 0.20139(10) 0.0318(5) Uani 1 1 d D . . . .
H1O H 0.790(3) 0.410(2) 0.2087(17) 0.038 Uiso 1 1 d D U . . .
N1 N 0.66395(15) 0.23986(15) 0.06320(10) 0.0232(5) Uani 1 1 d . . . . .
C1 C 0.62268(19) 0.20589(19) 0.01213(13) 0.0291(6) Uani 1 1 d . . . . .
H1 H 0.586311 0.225105 -0.003849 0.035 Uiso 1 1 calc R U . . .
N2 N 0.74757(15) 0.32019(15) 0.15553(11) 0.0241(5) Uani 1 1 d . . . . .
C2 C 0.6313(2) 0.1442(2) -0.01788(15) 0.0356(7) Uani 1 1 d . . . . .
H2 H 0.602774 0.122461 -0.054745 0.043 Uiso 1 1 calc R U . . .
N3 N 0.69614(17) 0.18853(16) 0.25463(11) 0.0318(5) Uani 1 1 d . . . . .
C3 C 0.6819(2) 0.1139(2) 0.00624(16) 0.0372(7) Uani 1 1 d . . . . .
H3 H 0.688564 0.071114 -0.013875 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7226(2) 0.14650(19) 0.05977(15) 0.0317(6) Uani 1 1 d . . . . .
H4 H 0.756376 0.125318 0.077469 0.038 Uiso 1 1 calc R U . . .
C5 C 0.71382(17) 0.21080(18) 0.08760(12) 0.0245(5) Uani 1 1 d . . . . .
C6 C 0.75739(18) 0.25480(18) 0.14142(13) 0.0253(5) Uani 1 1 d . . . . .
C7 C 0.81067(19) 0.2323(2) 0.18011(14) 0.0300(6) Uani 1 1 d . . . . .
H7A H 0.867880 0.284095 0.185196 0.036 Uiso 1 1 calc R U . . .
H7B H 0.819124 0.188431 0.159566 0.036 Uiso 1 1 calc R U . . .
C8 C 0.77310(19) 0.19875(18) 0.24067(13) 0.0298(6) Uani 1 1 d . . . . .
C9 C 0.8161(2) 0.1780(2) 0.28204(16) 0.0402(8) Uani 1 1 d . . . . .
H9 H 0.870847 0.185052 0.272891 0.048 Uiso 1 1 calc R U . . .
C10 C 0.7791(2) 0.1467(2) 0.33719(17) 0.0502(10) Uani 1 1 d . . . . .
H10 H 0.808391 0.132164 0.365995 0.060 Uiso 1 1 calc R U . . .
C11 C 0.6992(3) 0.1366(3) 0.35012(17) 0.0504(9) Uani 1 1 d . . . . .
H11 H 0.673447 0.115539 0.387843 0.060 Uiso 1 1 calc R U . . .
C12 C 0.6579(3) 0.1573(3) 0.30776(16) 0.0448(8) Uani 1 1 d . . . . .
H12 H 0.602672 0.149848 0.315651 0.054 Uiso 1 1 calc R U . . .
O2 O 0.31414(19) -0.04537(17) 0.02433(15) 0.0617(9) Uani 1 1 d D . . . .
O3 O 0.43169(17) 0.0811(2) -0.00983(13) 0.0593(8) Uani 1 1 d D . . . .
Cl1A Cl 0.3449(7) 0.0454(8) 0.0089(6) 0.043(2) Uani 0.45(3) 1 d D . P A 1
O4A O 0.2945(6) 0.0424(9) -0.0392(6) 0.079(4) Uani 0.55(3) 1 d D . P A 1
O5A O 0.3311(19) 0.0890(11) 0.0530(12) 0.124(9) Uani 0.45(3) 1 d D . P A 1
Cl1B Cl 0.3472(4) 0.0418(6) 0.0155(4) 0.0270(11) Uani 0.55(3) 1 d D . P A 2
O4B O 0.2936(9) 0.0651(10) -0.0115(13) 0.104(6) Uani 0.45(3) 1 d D . P A 2
O5B O 0.3608(10) 0.0776(8) 0.0735(4) 0.070(3) Uani 0.55(3) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N2 1.907(2) . ?
Co1 N2 1.907(2) 3_665 ?
Co1 N2 1.907(2) 2_655 ?
Co1 N1 1.945(2) . ?
Co1 N1 1.945(2) 2_655 ?
Co1 N1 1.945(2) 3_665 ?
O1 N2 1.286(3) . ?
N1 C1 1.338(4) . ?
N1 C5 1.359(4) . ?
C1 C2 1.372(4) . ?
N2 C6 1.312(4) . ?
C2 C3 1.385(5) . ?
N3 C8 1.339(4) . ?
N3 C12 1.353(4) . ?
C3 C4 1.378(5) . ?
C4 C5 1.392(4) . ?
C5 C6 1.444(4) . ?
C6 C7 1.492(4) . ?
C7 C8 1.506(4) . ?
C8 C9 1.376(4) . ?
C9 C10 1.387(5) . ?
C10 C11 1.386(6) . ?
C11 C12 1.370(5) . ?
O2 Cl1B 1.385(10) . ?
O2 Cl1A 1.479(13) . ?
O3 Cl1A 1.422(11) . ?
O3 Cl1B 1.434(8) . ?
Cl1A O5A 1.362(13) . ?
Cl1A O4A 1.394(15) . ?
Cl1B O4B 1.371(12) . ?
Cl1B O5B 1.420(10) . ?

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
N2 Co1 N2 92.16(10) . 3_665 ?
N2 Co1 N2 92.16(10) . 2_655 ?
N2 Co1 N2 92.16(10) 3_665 2_655 ?
N2 Co1 N1 82.79(10) . . ?
N2 Co1 N1 90.10(10) 3_665 . ?
N2 Co1 N1 174.54(11) 2_655 . ?
N2 Co1 N1 90.10(10) . 2_655 ?
N2 Co1 N1 174.54(11) 3_665 2_655 ?
N2 Co1 N1 82.79(10) 2_655 2_655 ?
N1 Co1 N1 95.11(9) . 2_655 ?
N2 Co1 N1 174.54(11) . 3_665 ?
N2 Co1 N1 82.79(10) 3_665 3_665 ?
N2 Co1 N1 90.11(10) 2_655 3_665 ?
N1 Co1 N1 95.11(9) . 3_665 ?
N1 Co1 N1 95.11(9) 2_655 3_665 ?
C1 N1 C5 119.5(2) . . ?
C1 N1 Co1 127.8(2) . . ?
C5 N1 Co1 112.63(18) . . ?
N1 C1 C2 122.1(3) . . ?
O1 N2 C6 119.2(2) . . ?
O1 N2 Co1 125.11(18) . . ?
C6 N2 Co1 115.4(2) . . ?
C1 C2 C3 119.2(3) . . ?
C8 N3 C12 122.7(3) . . ?
C4 C3 C2 119.3(3) . . ?
C3 C4 C5 119.3(3) . . ?
N1 C5 C4 120.6(3) . . ?
N1 C5 C6 114.2(2) . . ?
C4 C5 C6 125.2(3) . . ?
N2 C6 C5 114.5(3) . . ?
N2 C6 C7 119.6(3) . . ?
C5 C6 C7 125.9(3) . . ?
C6 C7 C8 114.6(3) . . ?
N3 C8 C9 119.1(3) . . ?
N3 C8 C7 119.5(3) . . ?
C9 C8 C7 121.4(3) . . ?
C8 C9 C10 119.6(3) . . ?
C11 C10 C9 119.8(3) . . ?
C12 C11 C10 119.1(3) . . ?
N3 C12 C11 119.7(4) . . ?
O5A Cl1A O4A 107(2) . . ?
O5A Cl1A O3 115.5(13) . . ?
O4A Cl1A O3 109.4(11) . . ?
O5A Cl1A O2 112.9(12) . . ?
O4A Cl1A O2 105.2(10) . . ?
O3 Cl1A O2 106.7(7) . . ?
O4B Cl1B O2 116.1(9) . . ?
O4B Cl1B O5B 104.9(17) . . ?
O2 Cl1B O5B 105.2(8) . . ?
O4B Cl1B O3 114.0(13) . . ?
O2 Cl1B O3 111.3(5) . . ?
O5B Cl1B O3 104.0(8) . . ?

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 H1O N3 0.79(3) 1.90(3) 2.646(3) 158(4) 2_655
O1 H1O N3 0.79(3) 1.90(3) 2.646(3) 158(4) 2_655

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_cm1378cd_sq
_database_code_depnum_ccdc_archive 'CCDC 1518718'
_audit_update_record             
;
2016-11-25 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C72 H63 Fe3 N18 O6, 4(PF6), 2(C2 H6 O), 3(H2 O)'
_chemical_formula_sum            'C76 H81 F24 Fe3 N18 O11 P4'
_chemical_formula_weight         2170.01

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'
F F 0.0171 0.0103 '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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   13.0092(7)
_cell_length_b                   14.3276(7)
_cell_length_c                   15.0070(8)
_cell_angle_alpha                91.302(3)
_cell_angle_beta                 113.159(3)
_cell_angle_gamma                111.623(3)
_cell_volume                     2344.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9871
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.74

_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_F_000             1105
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.639
_shelx_estimated_absorpt_T_min   0.827
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS v2008, (Sheldrick, 2008)'
_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  'Bruker-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            48623
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.070
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9548
_reflns_number_gt                7826
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 v.2010.1-2 (Bruker Nonius, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        'SAINT v.7.68a (Bruker, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  'PublCIF (Westrip, 2010)'
_refine_special_details          
;Disordered solvent addressed using SQUEEZE - 1 void/cell 194A and
40 electrons. Not added to UNIT., SQUEEZE
;
_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+2.1981P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9548
_refine_ls_number_parameters     674
_refine_ls_number_restraints     223
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.031
_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
Fe1 Fe 0.85453(3) 0.65718(2) 0.39961(3) 0.02721(11) Uani 1 1 d . . . . .
Fe2 Fe 1.000000 0.500000 0.500000 0.02730(13) Uani 1 2 d S . P . .
O1 O 0.97034(16) 0.53344(12) 0.36398(13) 0.0315(4) Uani 1 1 d . . . . .
O2 O 1.05881(15) 0.64683(12) 0.56007(14) 0.0321(4) Uani 1 1 d . . . . .
O3 O 0.82413(15) 0.47087(13) 0.47372(13) 0.0294(4) Uani 1 1 d . . . . .
N1 N 0.9405(2) 0.78977(16) 0.37092(16) 0.0331(5) Uani 1 1 d . . . . .
N2 N 0.95502(19) 0.62143(15) 0.35472(16) 0.0296(4) Uani 1 1 d . . . . .
N3 N 1.0806(2) 0.50653(18) 0.20034(19) 0.0407(5) Uani 1 1 d . . . . .
H3N H 1.148725 0.515899 0.252195 0.049 Uiso 1 1 calc R U . . .
N4 N 0.77813(19) 0.71288(15) 0.46492(16) 0.0305(4) Uani 1 1 d . . . . .
N5 N 0.96816(18) 0.67973(14) 0.53354(16) 0.0287(4) Uani 1 1 d . . . . .
N6 N 1.1938(2) 0.8902(2) 0.7126(2) 0.0528(7) Uani 1 1 d . . . . .
N7 N 0.7124(2) 0.61510(16) 0.26849(16) 0.0312(5) Uani 1 1 d . . . . .
N8 N 0.77211(18) 0.51742(15) 0.40241(15) 0.0271(4) Uani 1 1 d . . . . .
N9 N 0.5145(2) 0.18772(18) 0.20397(19) 0.0430(6) Uani 0.5 1 d . . P A 1
O5 O 0.3619(4) 0.0773(3) 0.2770(3) 0.1053(12) Uani 0.5 1 d D . P B 1
H5C H 0.414(6) 0.106(11) 0.255(7) 0.158 Uiso 0.5 1 d D U P C 1
H5D H 0.293(4) 0.071(5) 0.229(3) 0.158 Uiso 0.5 1 d D U P D 1
N9' N 0.5145(2) 0.18772(18) 0.20397(19) 0.0430(6) Uani 0.5 1 d . . P A 2
H9' H 0.463884 0.164636 0.231567 0.052 Uiso 0.5 1 calc R U P A 2
O5' O 0.3619(4) 0.0773(3) 0.2770(3) 0.1053(12) Uani 0.5 1 d D . P E 2
H5C' H 0.373(5) 0.027(3) 0.258(4) 0.158 Uiso 0.5 1 d D U P F 2
H5D' H 0.293(4) 0.071(5) 0.229(3) 0.158 Uiso 0.5 1 d D U P G 2
O6 O 0.1871(5) -0.0384(4) 0.1062(5) 0.0729(16) Uani 0.5 1 d D . P . .
H6D H 0.140(7) -0.015(6) 0.108(8) 0.109 Uiso 0.5 1 d D U P . .
H6C H 0.165(8) -0.098(2) 0.106(8) 0.109 Uiso 0.5 1 d D U P . .
C1 C 0.9336(3) 0.8798(2) 0.3864(2) 0.0398(6) Uani 1 1 d . . . . .
H1 H 0.890644 0.886078 0.423176 0.048 Uiso 1 1 calc R U . . .
C2 C 0.9868(3) 0.9632(2) 0.3506(3) 0.0512(8) Uani 1 1 d . . . . .
H2 H 0.981258 1.025929 0.363662 0.061 Uiso 1 1 calc R U . . .
C3 C 1.0480(4) 0.9551(2) 0.2960(3) 0.0584(9) Uani 1 1 d . . . . .
H3 H 1.082395 1.011044 0.268950 0.070 Uiso 1 1 calc R U . . .
C4 C 1.0584(3) 0.8642(2) 0.2813(3) 0.0512(8) Uani 1 1 d . . . . .
H4 H 1.101006 0.856954 0.244572 0.061 Uiso 1 1 calc R U . . .
C5 C 1.0059(3) 0.7836(2) 0.3209(2) 0.0383(6) Uani 1 1 d . . . . .
C6 C 1.0169(2) 0.6864(2) 0.3166(2) 0.0361(6) Uani 1 1 d . . . . .
C7 C 1.1000(3) 0.6642(2) 0.2814(2) 0.0434(7) Uani 1 1 d . . . . .
H7A H 1.143252 0.725133 0.259634 0.052 Uiso 1 1 calc R U . . .
H7B H 1.162415 0.650960 0.336955 0.052 Uiso 1 1 calc R U . . .
C8 C 1.0318(3) 0.5741(2) 0.1979(2) 0.0387(6) Uani 1 1 d . . . . .
C9 C 0.9242(3) 0.5582(3) 0.1175(2) 0.0489(7) Uani 1 1 d . . . . .
H9 H 0.887278 0.605053 0.113487 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8697(3) 0.4736(3) 0.0422(3) 0.0529(8) Uani 1 1 d . . . . .
H10 H 0.794642 0.461760 -0.012957 0.064 Uiso 1 1 calc R U . . .
C11 C 0.9247(3) 0.4065(3) 0.0475(2) 0.0496(7) Uani 1 1 d . . . . .
H11 H 0.888643 0.348758 -0.004021 0.060 Uiso 1 1 calc R U . . .
C12 C 1.0310(3) 0.4246(2) 0.1275(2) 0.0453(7) Uani 1 1 d . . . . .
H12 H 1.070439 0.379586 0.132266 0.054 Uiso 1 1 calc R U . . .
C13 C 0.6737(2) 0.7265(2) 0.4237(2) 0.0375(6) Uani 1 1 d . . . . .
H13 H 0.627509 0.707242 0.353926 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6307(3) 0.7672(2) 0.4781(2) 0.0453(7) Uani 1 1 d . . . . .
H14 H 0.557404 0.777143 0.446028 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6948(3) 0.7932(2) 0.5790(2) 0.0459(7) Uani 1 1 d . . . . .
H15 H 0.665712 0.820216 0.617783 0.055 Uiso 1 1 calc R U . . .
C16 C 0.8026(3) 0.7796(2) 0.6236(2) 0.0373(6) Uani 1 1 d . . . . .
H16 H 0.848201 0.796915 0.693447 0.045 Uiso 1 1 calc R U . . .
C17 C 0.8431(2) 0.74026(18) 0.56482(19) 0.0307(5) Uani 1 1 d . . . . .
C18 C 0.9525(2) 0.72007(17) 0.60311(19) 0.0300(5) Uani 1 1 d . . . . .
C19 C 1.0312(3) 0.7354(2) 0.7110(2) 0.0357(6) Uani 1 1 d . . . . .
H19A H 1.076392 0.691115 0.720625 0.043 Uiso 1 1 calc R U . . .
H19B H 0.977888 0.713323 0.745602 0.043 Uiso 1 1 calc R U . . .
C20 C 1.1226(3) 0.8452(2) 0.7574(2) 0.0404(6) Uani 1 1 d . . . . .
C21 C 1.1325(3) 0.8942(3) 0.8416(3) 0.0553(8) Uani 1 1 d . . . . .
H21 H 1.081150 0.860442 0.872183 0.066 Uiso 1 1 calc R U . . .
C22 C 1.2209(4) 0.9960(3) 0.8821(3) 0.0712(12) Uani 1 1 d . . . . .
H22 H 1.229105 1.032675 0.939810 0.085 Uiso 1 1 calc R U . . .
C23 C 1.2938(4) 1.0404(3) 0.8371(3) 0.0716(12) Uani 1 1 d . . . . .
H23 H 1.354886 1.108413 0.863696 0.086 Uiso 1 1 calc R U . . .
C24 C 1.2786(3) 0.9867(3) 0.7536(3) 0.0670(10) Uani 1 1 d . . . . .
H24 H 1.330195 1.018790 0.722792 0.080 Uiso 1 1 calc R U . . .
C25 C 0.6859(3) 0.6712(2) 0.1991(2) 0.0395(6) Uani 1 1 d . . . . .
H25 H 0.745056 0.738311 0.208211 0.047 Uiso 1 1 calc R U . . .
C26 C 0.5761(3) 0.6350(2) 0.1152(2) 0.0459(7) Uani 1 1 d . . . . .
H26 H 0.560251 0.676829 0.067902 0.055 Uiso 1 1 calc R U . . .
C27 C 0.4900(3) 0.5379(2) 0.1009(2) 0.0450(7) Uani 1 1 d . . . . .
H27 H 0.413190 0.512526 0.044283 0.054 Uiso 1 1 calc R U . . .
C28 C 0.5161(3) 0.4781(2) 0.1690(2) 0.0397(6) Uani 1 1 d . . . . .
H28 H 0.458204 0.410180 0.159423 0.048 Uiso 1 1 calc R U . . .
C29 C 0.6280(2) 0.51759(19) 0.25231(19) 0.0320(5) Uani 1 1 d . . . . .
C30 C 0.6677(2) 0.46092(18) 0.32829(19) 0.0300(5) Uani 1 1 d . . . . .
C31 C 0.6003(3) 0.34753(19) 0.3184(2) 0.0374(6) Uani 1 1 d . . . . .
H31A H 0.514488 0.332262 0.305525 0.045 Uiso 1 1 calc R U . . .
H31B H 0.638824 0.327453 0.381641 0.045 Uiso 1 1 calc R U . . .
C32 C 0.6001(2) 0.28416(19) 0.2363(2) 0.0344(6) Uani 1 1 d . . . . .
C33 C 0.6811(3) 0.3194(2) 0.1951(2) 0.0422(7) Uani 1 1 d . . . . .
H33 H 0.743941 0.386874 0.219284 0.051 Uiso 1 1 calc R U . . .
C34 C 0.6707(3) 0.2560(2) 0.1178(2) 0.0480(7) Uani 1 1 d . . . . .
H34 H 0.725921 0.279982 0.088373 0.058 Uiso 1 1 calc R U . . .
C35 C 0.5799(3) 0.1582(2) 0.0841(2) 0.0502(8) Uani 1 1 d . . . . .
H35 H 0.569836 0.114261 0.030119 0.060 Uiso 1 1 calc R U . . .
C36 C 0.5051(3) 0.1261(2) 0.1300(2) 0.0518(8) Uani 1 1 d . . . . .
H36 H 0.444190 0.057780 0.109041 0.062 Uiso 1 1 calc R U . A 1
P1 P -0.16357(8) -0.23576(6) -0.04259(7) 0.0509(2) Uani 1 1 d D . . . .
F1 F -0.2256(2) -0.35732(17) -0.0649(2) 0.0852(8) Uani 1 1 d D . . . .
F2 F -0.0986(3) -0.11651(18) -0.0170(3) 0.1159(12) Uani 1 1 d D . . . .
F3 F -0.1493(4) -0.2397(3) -0.1403(2) 0.1336(13) Uani 1 1 d D . . . .
F4 F -0.0334(2) -0.24292(18) 0.0093(2) 0.0891(8) Uani 1 1 d D . . . .
F5 F -0.1673(4) -0.2374(3) 0.0604(3) 0.1388(14) Uani 1 1 d D . . . .
F6 F -0.2901(2) -0.2305(2) -0.0911(3) 0.1211(13) Uani 1 1 d D . . . .
P2 P 0.37493(8) -0.21364(7) 0.19685(7) 0.0522(2) Uani 1 1 d D U . . .
F7 F 0.5099(2) -0.2076(2) 0.24441(19) 0.0822(7) Uani 1 1 d D U . . .
F8 F 0.2389(2) -0.2208(2) 0.1503(2) 0.0903(8) Uani 1 1 d D U . . .
F9 F 0.3666(8) -0.2387(8) 0.0947(4) 0.129(3) Uani 0.6 1 d D U P H 1
F10 F 0.3066(6) -0.3297(4) 0.1927(6) 0.116(2) Uani 0.6 1 d D U P H 1
F11 F 0.3826(6) -0.1938(8) 0.3058(4) 0.139(3) Uani 0.6 1 d D U P H 1
F12 F 0.4328(6) -0.0967(4) 0.2005(9) 0.143(3) Uani 0.6 1 d D U P H 1
F9' F 0.4059(9) -0.1315(8) 0.1323(7) 0.089(3) Uani 0.4 1 d D U P H 2
F10' F 0.3469(9) -0.2963(7) 0.1094(7) 0.095(3) Uani 0.4 1 d D U P H 2
F11' F 0.3467(7) -0.2985(7) 0.2572(7) 0.086(2) Uani 0.4 1 d D U P H 2
F12' F 0.4041(11) -0.1298(7) 0.2776(6) 0.110(3) Uani 0.4 1 d D U P H 2
O4 O 1.23233(19) 0.49562(18) 0.37574(17) 0.0475(5) Uani 1 1 d . . . . .
H4A H 1.213(4) 0.509(3) 0.418(3) 0.071 Uiso 1 1 d . U . . .
C37 C 1.3564(3) 0.5079(3) 0.4179(2) 0.0465(7) Uani 1 1 d . . . . .
H37A H 1.367387 0.459585 0.463207 0.056 Uiso 1 1 calc R U . . .
H37B H 1.410955 0.578492 0.456178 0.056 Uiso 1 1 calc R U . . .
C38 C 1.3880(3) 0.4872(3) 0.3358(3) 0.0541(8) Uani 1 1 d . . . . .
H38A H 1.473120 0.494436 0.363659 0.081 Uiso 1 1 calc R U . . .
H38B H 1.378453 0.536225 0.292087 0.081 Uiso 1 1 calc R U . . .
H38C H 1.333199 0.417432 0.298023 0.081 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
Fe1 N2 1.896(2) . ?
Fe1 N5 1.900(2) . ?
Fe1 N8 1.902(2) . ?
Fe1 N1 1.974(2) . ?
Fe1 N4 1.975(2) . ?
Fe1 N7 1.979(2) . ?
Fe2 O2 2.0022(16) 2_766 ?
Fe2 O2 2.0022(16) . ?
Fe2 O1 2.0264(18) . ?
Fe2 O1 2.0265(18) 2_766 ?
Fe2 O3 2.0355(16) . ?
Fe2 O3 2.0355(16) 2_766 ?
O1 N2 1.349(3) . ?
O2 N5 1.349(3) . ?
O3 N8 1.358(3) . ?
N1 C1 1.346(3) . ?
N1 C5 1.361(4) . ?
N2 C6 1.295(3) . ?
N3 C8 1.334(4) . ?
N3 C12 1.348(4) . ?
N4 C13 1.344(3) . ?
N4 C17 1.359(3) . ?
N5 C18 1.300(3) . ?
N6 C20 1.339(4) . ?
N6 C24 1.345(4) . ?
N7 C25 1.344(4) . ?
N7 C29 1.364(3) . ?
N8 C30 1.303(3) . ?
N9 C36 1.340(4) . ?
N9 C32 1.340(3) . ?
N9' C36 1.340(4) . ?
N9' C32 1.340(3) . ?
C1 C2 1.381(4) . ?
C2 C3 1.376(5) . ?
C3 C4 1.380(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.453(4) . ?
C6 C7 1.497(4) . ?
C7 C8 1.494(4) . ?
C8 C9 1.375(4) . ?
C9 C10 1.387(5) . ?
C10 C11 1.380(5) . ?
C11 C12 1.355(5) . ?
C13 C14 1.378(4) . ?
C14 C15 1.371(5) . ?
C15 C16 1.387(4) . ?
C16 C17 1.391(4) . ?
C17 C18 1.453(4) . ?
C18 C19 1.494(4) . ?
C19 C20 1.515(4) . ?
C20 C21 1.368(4) . ?
C21 C22 1.412(5) . ?
C22 C23 1.356(6) . ?
C23 C24 1.361(6) . ?
C25 C26 1.380(4) . ?
C26 C27 1.372(5) . ?
C27 C28 1.371(4) . ?
C28 C29 1.390(4) . ?
C29 C30 1.454(4) . ?
C30 C31 1.506(3) . ?
C31 C32 1.512(4) . ?
C32 C33 1.372(4) . ?
C33 C34 1.388(4) . ?
C34 C35 1.376(4) . ?
C35 C36 1.359(5) . ?
P1 F6 1.548(3) . ?
P1 F3 1.551(3) . ?
P1 F2 1.559(2) . ?
P1 F5 1.565(3) . ?
P1 F1 1.588(2) . ?
P1 F4 1.606(3) . ?
P2 F12' 1.514(7) . ?
P2 F9 1.519(6) . ?
P2 F12 1.553(5) . ?
P2 F11' 1.554(6) . ?
P2 F10 1.557(5) . ?
P2 F10' 1.579(7) . ?
P2 F9' 1.579(7) . ?
P2 F7 1.581(2) . ?
P2 F8 1.587(2) . ?
P2 F11 1.610(5) . ?
O4 C37 1.421(3) . ?
C37 C38 1.499(4) . ?

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
N2 Fe1 N5 91.23(9) . . ?
N2 Fe1 N8 89.65(8) . . ?
N5 Fe1 N8 90.24(9) . . ?
N2 Fe1 N1 80.50(9) . . ?
N5 Fe1 N1 97.40(9) . . ?
N8 Fe1 N1 167.62(9) . . ?
N2 Fe1 N4 169.64(9) . . ?
N5 Fe1 N4 80.58(9) . . ?
N8 Fe1 N4 96.66(8) . . ?
N1 Fe1 N4 94.20(9) . . ?
N2 Fe1 N7 95.36(9) . . ?
N5 Fe1 N7 168.64(9) . . ?
N8 Fe1 N7 80.58(9) . . ?
N1 Fe1 N7 92.81(9) . . ?
N4 Fe1 N7 93.77(9) . . ?
O2 Fe2 O2 180.0 2_766 . ?
O2 Fe2 O1 88.24(7) 2_766 . ?
O2 Fe2 O1 91.76(7) . . ?
O2 Fe2 O1 91.76(7) 2_766 2_766 ?
O2 Fe2 O1 88.24(7) . 2_766 ?
O1 Fe2 O1 180.00(12) . 2_766 ?
O2 Fe2 O3 88.09(7) 2_766 . ?
O2 Fe2 O3 91.91(7) . . ?
O1 Fe2 O3 91.10(7) . . ?
O1 Fe2 O3 88.90(7) 2_766 . ?
O2 Fe2 O3 91.91(7) 2_766 2_766 ?
O2 Fe2 O3 88.09(7) . 2_766 ?
O1 Fe2 O3 88.90(7) . 2_766 ?
O1 Fe2 O3 91.10(7) 2_766 2_766 ?
O3 Fe2 O3 180.00(11) . 2_766 ?
N2 O1 Fe2 112.77(14) . . ?
N5 O2 Fe2 113.08(13) . . ?
N8 O3 Fe2 112.97(13) . . ?
C1 N1 C5 117.8(2) . . ?
C1 N1 Fe1 128.8(2) . . ?
C5 N1 Fe1 113.09(17) . . ?
C6 N2 O1 117.5(2) . . ?
C6 N2 Fe1 118.72(17) . . ?
O1 N2 Fe1 123.75(15) . . ?
C8 N3 C12 123.4(3) . . ?
C13 N4 C17 118.0(2) . . ?
C13 N4 Fe1 128.68(19) . . ?
C17 N4 Fe1 113.32(17) . . ?
C18 N5 O2 118.2(2) . . ?
C18 N5 Fe1 119.41(18) . . ?
O2 N5 Fe1 122.10(15) . . ?
C20 N6 C24 118.0(3) . . ?
C25 N7 C29 117.8(2) . . ?
C25 N7 Fe1 128.89(19) . . ?
C29 N7 Fe1 113.18(17) . . ?
C30 N8 O3 118.0(2) . . ?
C30 N8 Fe1 119.27(18) . . ?
O3 N8 Fe1 122.30(15) . . ?
C36 N9 C32 120.7(3) . . ?
C36 N9' C32 120.7(3) . . ?
N1 C1 C2 122.2(3) . . ?
C3 C2 C1 119.7(3) . . ?
C2 C3 C4 118.8(3) . . ?
C3 C4 C5 119.2(3) . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 C6 113.1(2) . . ?
C4 C5 C6 124.8(3) . . ?
N2 C6 C5 113.3(2) . . ?
N2 C6 C7 121.7(2) . . ?
C5 C6 C7 124.8(2) . . ?
C8 C7 C6 112.3(2) . . ?
N3 C8 C9 118.0(3) . . ?
N3 C8 C7 117.7(3) . . ?
C9 C8 C7 124.2(3) . . ?
C8 C9 C10 119.9(3) . . ?
C11 C10 C9 119.8(3) . . ?
C12 C11 C10 118.8(3) . . ?
N3 C12 C11 119.9(3) . . ?
N4 C13 C14 122.9(3) . . ?
C15 C14 C13 119.3(3) . . ?
C14 C15 C16 119.1(3) . . ?
C15 C16 C17 119.1(3) . . ?
N4 C17 C16 121.6(2) . . ?
N4 C17 C18 114.2(2) . . ?
C16 C17 C18 124.2(2) . . ?
N5 C18 C17 112.5(2) . . ?
N5 C18 C19 124.1(2) . . ?
C17 C18 C19 123.2(2) . . ?
C18 C19 C20 113.5(2) . . ?
N6 C20 C21 122.4(3) . . ?
N6 C20 C19 116.4(3) . . ?
C21 C20 C19 121.2(3) . . ?
C20 C21 C22 118.4(4) . . ?
C23 C22 C21 118.8(4) . . ?
C22 C23 C24 119.4(3) . . ?
N6 C24 C23 123.0(4) . . ?
N7 C25 C26 122.6(3) . . ?
C27 C26 C25 119.4(3) . . ?
C28 C27 C26 119.2(3) . . ?
C27 C28 C29 119.4(3) . . ?
N7 C29 C28 121.6(3) . . ?
N7 C29 C30 113.8(2) . . ?
C28 C29 C30 124.6(2) . . ?
N8 C30 C29 112.6(2) . . ?
N8 C30 C31 123.8(2) . . ?
C29 C30 C31 123.4(2) . . ?
C30 C31 C32 113.1(2) . . ?
N9' C32 C33 119.7(3) . . ?
N9 C32 C33 119.7(3) . . ?
N9' C32 C31 116.1(2) . . ?
N9 C32 C31 116.1(2) . . ?
C33 C32 C31 124.2(2) . . ?
C32 C33 C34 119.7(3) . . ?
C35 C34 C33 119.5(3) . . ?
C36 C35 C34 118.3(3) . . ?
N9' C36 C35 122.0(3) . . ?
N9 C36 C35 122.0(3) . . ?
F6 P1 F3 94.2(2) . . ?
F6 P1 F2 90.26(16) . . ?
F3 P1 F2 92.0(2) . . ?
F6 P1 F5 91.8(2) . . ?
F3 P1 F5 173.5(2) . . ?
F2 P1 F5 90.4(2) . . ?
F6 P1 F1 91.61(14) . . ?
F3 P1 F1 89.05(19) . . ?
F2 P1 F1 177.79(17) . . ?
F5 P1 F1 88.4(2) . . ?
F6 P1 F4 178.68(19) . . ?
F3 P1 F4 86.8(2) . . ?
F2 P1 F4 90.51(15) . . ?
F5 P1 F4 87.2(2) . . ?
F1 P1 F4 87.59(13) . . ?
F9 P2 F12 92.1(5) . . ?
F12' P2 F11' 92.9(5) . . ?
F9 P2 F10 89.8(5) . . ?
F12 P2 F10 174.9(4) . . ?
F12' P2 F10' 176.8(6) . . ?
F11' P2 F10' 90.2(5) . . ?
F12' P2 F9' 90.1(5) . . ?
F11' P2 F9' 176.6(5) . . ?
F10' P2 F9' 86.7(5) . . ?
F12' P2 F7 92.9(4) . . ?
F9 P2 F7 89.5(4) . . ?
F12 P2 F7 87.1(3) . . ?
F11' P2 F7 85.6(3) . . ?
F10 P2 F7 97.6(3) . . ?
F10' P2 F7 87.0(4) . . ?
F9' P2 F7 92.7(4) . . ?
F12' P2 F8 87.0(5) . . ?
F9 P2 F8 91.1(4) . . ?
F12 P2 F8 93.5(3) . . ?
F11' P2 F8 93.6(3) . . ?
F10 P2 F8 81.8(3) . . ?
F10' P2 F8 93.2(4) . . ?
F9' P2 F8 88.2(4) . . ?
F7 P2 F8 179.11(15) . . ?
F9 P2 F11 176.7(6) . . ?
F12 P2 F11 91.1(5) . . ?
F10 P2 F11 87.1(4) . . ?
F7 P2 F11 89.7(3) . . ?
F8 P2 F11 89.7(3) . . ?
O4 C37 C38 108.4(3) . . ?

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
N3 H3N O4 0.88 1.84 2.647(3) 152.1 .
N9' H9' O5' 0.88 1.82 2.669(5) 160.8 .
O5 H5C N9 0.85(2) 1.83(4) 2.669(5) 168(14) .
O5 H5D O6 0.871(14) 2.01(5) 2.633(8) 128(5) .
O5' H5C' F12' 0.853(19) 2.42(3) 3.210(9) 154(5) .
O6 H6D F2 0.81(2) 2.45(8) 2.975(7) 123(8) 2
O6 H6C F4 0.80(2) 2.46(8) 3.042(5) 131(9) .
O6 H6C F8 0.80(2) 2.29(6) 2.957(6) 142(9) .
O4 H4A O3 0.81(4) 1.91(4) 2.718(3) 173(4) 2_766

_refine_diff_density_max         0.811
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.068



