# 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_1Cd
_database_code_depnum_ccdc_archive 'CCDC 1444051'
_audit_update_record             
;
2015-12-23 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 Br Cd N6 O4'
_chemical_formula_weight         673.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   9.9720(10)
_cell_length_b                   18.5568(18)
_cell_length_c                   13.9793(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.826(2)
_cell_angle_gamma                90.00
_cell_volume                     2511.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5358
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.10

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    2.506
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5404
_exptl_absorpt_correction_T_max  0.9286
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_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  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14403
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5452
_reflns_number_gt                4620
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0371P)²+1.0076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5452
_refine_ls_number_parameters     423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0755
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.85866(2) 0.110789(10) 0.670198(15) 0.01701(7) Uani 1 1 d . . .
Br1 Br 1.27629(3) -0.247258(18) 0.65113(3) 0.03532(10) Uani 1 1 d . . .
N1 N 0.7035(2) 0.08209(13) 0.52662(18) 0.0215(5) Uani 1 1 d . . .
N2 N 0.6246(2) 0.02707(13) 0.38463(17) 0.0207(5) Uani 1 1 d . . .
N3 N 0.6064(3) 0.23039(13) 0.05077(18) 0.0209(5) Uani 1 1 d . . .
N4 N 0.5098(2) 0.32546(13) 0.10063(18) 0.0216(5) Uani 1 1 d . . .
N5 N 0.1126(2) 0.07305(14) -0.02586(19) 0.0241(6) Uani 1 1 d . . .
N6 N -0.0135(2) 0.11494(13) -0.16646(18) 0.0217(5) Uani 1 1 d . . .
O1 O 1.0017(2) 0.00354(10) 0.64945(16) 0.0236(5) Uani 1 1 d . . .
O2 O 0.8228(2) -0.01528(10) 0.71462(15) 0.0225(4) Uani 1 1 d . . .
O3 O 0.7184(2) -0.26645(11) 0.80585(19) 0.0335(6) Uani 1 1 d . . .
O4 O 0.8425(2) -0.35630(11) 0.77062(17) 0.0267(5) Uani 1 1 d . . .
C1 C 0.9249(3) -0.03699(15) 0.6856(2) 0.0190(6) Uani 1 1 d . . .
C2 C 0.9608(3) -0.11654(14) 0.6970(2) 0.0179(6) Uani 1 1 d . . .
C3 C 1.0794(3) -0.14148(15) 0.6725(2) 0.0190(6) Uani 1 1 d . . .
C4 C 1.1139(3) -0.21374(16) 0.6845(2) 0.0214(6) Uani 1 1 d . . .
C5 C 1.0308(3) -0.26179(16) 0.7182(2) 0.0211(6) Uani 1 1 d . . .
C6 C 0.9108(3) -0.23729(15) 0.7414(2) 0.0177(6) Uani 1 1 d . . .
C7 C 0.8769(3) -0.16438(15) 0.7317(2) 0.0189(6) Uani 1 1 d . . .
H7 H 0.7975 -0.1478 0.7485 0.023 Uiso 1 1 calc R . .
C8 C 0.8177(3) -0.29024(15) 0.7758(2) 0.0207(6) Uani 1 1 d . . .
C9 C 0.5645(3) 0.09671(18) 0.4928(2) 0.0266(7) Uani 1 1 d . . .
C10 C 0.5152(3) 0.06314(18) 0.4058(2) 0.0270(7) Uani 1 1 d . . .
C11 C 0.7357(3) 0.03994(15) 0.4601(2) 0.0204(6) Uani 1 1 d . . .
C12 C 0.6244(3) -0.01928(17) 0.2990(2) 0.0250(7) Uani 1 1 d . . .
C13 C 0.5543(3) 0.01760(15) 0.2039(2) 0.0193(6) Uani 1 1 d . . .
C14 C 0.6235(3) 0.06602(16) 0.1576(2) 0.0218(6) Uani 1 1 d . . .
C15 C 0.5563(3) 0.10144(15) 0.0719(2) 0.0201(6) Uani 1 1 d . . .
C16 C 0.4167(3) 0.08745(16) 0.0324(2) 0.0199(6) Uani 1 1 d . . .
C17 C 0.3462(3) 0.03976(15) 0.0793(2) 0.0203(6) Uani 1 1 d . . .
C18 C 0.4155(3) 0.00447(16) 0.1639(2) 0.0199(6) Uani 1 1 d . . .
C19 C 0.6313(3) 0.15550(17) 0.0237(3) 0.0265(7) Uani 1 1 d . . .
C20 C 0.5057(3) 0.25478(17) 0.0912(2) 0.0244(7) Uani 1 1 d . . .
C21 C 0.6188(3) 0.34705(17) 0.0633(2) 0.0253(7) Uani 1 1 d . . .
C22 C 0.6784(3) 0.28940(17) 0.0319(3) 0.0279(7) Uani 1 1 d . . .
C23 C 0.1945(3) 0.02214(19) 0.0435(3) 0.0299(7) Uani 1 1 d . . .
C24 C 0.0694(3) 0.06314(18) -0.1236(2) 0.0244(7) Uani 1 1 d . . .
C25 C -0.0234(3) 0.16106(19) -0.0912(2) 0.0281(7) Uani 1 1 d . . .
C26 C 0.0542(3) 0.13606(19) -0.0048(2) 0.0297(7) Uani 1 1 d . . .
H3 H 1.138(3) -0.1085(17) 0.646(3) 0.030(9) Uiso 1 1 d . . .
H6 H 1.058(3) -0.3117(17) 0.726(2) 0.018(8) Uiso 1 1 d . . .
H9 H 0.515(4) 0.1284(18) 0.526(3) 0.032(9) Uiso 1 1 d . . .
H10 H 0.430(4) 0.0609(18) 0.369(3) 0.035(10) Uiso 1 1 d . . .
H11 H 0.822(3) 0.0195(15) 0.460(2) 0.015(8) Uiso 1 1 d . . .
H12A H 0.576(3) -0.0619(17) 0.305(2) 0.023(8) Uiso 1 1 d . . .
H12B H 0.723(3) -0.0311(17) 0.305(2) 0.024(8) Uiso 1 1 d . . .
H14 H 0.715(3) 0.0776(17) 0.182(2) 0.025(9) Uiso 1 1 d . . .
H16 H 0.371(3) 0.1111(16) -0.022(3) 0.023(8) Uiso 1 1 d . . .
H18 H 0.371(3) -0.0268(18) 0.194(2) 0.023(9) Uiso 1 1 d . . .
H19A H 0.604(3) 0.1516(17) -0.050(3) 0.028(9) Uiso 1 1 d . . .
H19B H 0.726(4) 0.1482(18) 0.040(3) 0.032(9) Uiso 1 1 d . . .
H20 H 0.445(3) 0.2241(18) 0.113(3) 0.030(9) Uiso 1 1 d . . .
H21 H 0.635(3) 0.3944(16) 0.056(2) 0.017(8) Uiso 1 1 d . . .
H22 H 0.750(3) 0.2857(15) 0.005(2) 0.015(8) Uiso 1 1 d . . .
H23A H 0.185(3) -0.0236(19) 0.013(3) 0.030(9) Uiso 1 1 d . . .
H23B H 0.147(4) 0.0202(18) 0.100(3) 0.037(10) Uiso 1 1 d . . .
H24 H 0.101(3) 0.0221(19) -0.155(2) 0.031(9) Uiso 1 1 d . . .
H25 H -0.074(4) 0.2037(19) -0.103(3) 0.032(10) Uiso 1 1 d . . .
H26 H 0.071(4) 0.1525(19) 0.058(3) 0.039(10) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.285(2) . ?
Cd1 N4 2.306(2) 4_666 ?
Cd1 N6 2.335(2) 1_656 ?
Cd1 O4 2.423(2) 2_656 ?
Cd1 O3 2.452(2) 2_656 ?
Cd1 O2 2.468(2) . ?
Cd1 O1 2.506(2) . ?
Br1 C4 1.894(3) . ?
N1 C11 1.313(4) . ?
N1 C9 1.380(4) . ?
N2 C11 1.356(4) . ?
N2 C10 1.371(4) . ?
N2 C12 1.473(4) . ?
N3 C20 1.343(4) . ?
N3 C22 1.369(4) . ?
N3 C19 1.477(4) . ?
N4 C20 1.318(4) . ?
N4 C21 1.373(4) . ?
N4 Cd1 2.306(2) 4_565 ?
N5 C24 1.343(4) . ?
N5 C26 1.369(4) . ?
N5 C23 1.457(4) . ?
N6 C24 1.315(4) . ?
N6 C25 1.378(4) . ?
N6 Cd1 2.335(2) 1_454 ?
O1 C1 1.262(3) . ?
O2 C1 1.249(4) . ?
O3 C8 1.246(4) . ?
O3 Cd1 2.452(2) 2_646 ?
O4 C8 1.256(3) . ?
O4 Cd1 2.424(2) 2_646 ?
C1 C2 1.518(4) . ?
C2 C7 1.385(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.98(3) . ?
C4 C5 1.375(4) . ?
C5 C6 1.388(4) . ?
C5 H6 0.97(3) . ?
C6 C7 1.393(4) . ?
C6 C8 1.508(4) . ?
C7 H7 0.9300 . ?
C9 C10 1.350(4) . ?
C9 H9 0.95(4) . ?
C10 H10 0.89(3) . ?
C11 H11 0.94(3) . ?
C12 C13 1.510(4) . ?
C12 H12A 0.94(3) . ?
C12 H12B 1.00(3) . ?
C13 C18 1.385(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.389(4) . ?
C14 H14 0.92(3) . ?
C15 C16 1.394(4) . ?
C15 C19 1.504(4) . ?
C16 C17 1.388(4) . ?
C16 H16 0.90(3) . ?
C17 C18 1.384(4) . ?
C17 C23 1.511(4) . ?
C18 H18 0.89(3) . ?
C19 H19A 1.00(3) . ?
C19 H19B 0.93(3) . ?
C20 H20 0.93(3) . ?
C21 C22 1.347(4) . ?
C21 H21 0.90(3) . ?
C22 H22 0.89(3) . ?
C23 H23A 0.94(3) . ?
C23 H23B 1.01(4) . ?
C24 H24 0.97(3) . ?
C25 C26 1.352(5) . ?
C25 H25 0.93(3) . ?
C26 H26 0.90(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
N1 Cd1 N4 97.05(9) . 4_666 ?
N1 Cd1 N6 164.43(9) . 1_656 ?
N4 Cd1 N6 97.84(9) 4_666 1_656 ?
N1 Cd1 O4 85.22(8) . 2_656 ?
N4 Cd1 O4 133.81(8) 4_666 2_656 ?
N6 Cd1 O4 87.76(8) 1_656 2_656 ?
N1 Cd1 O3 99.67(9) . 2_656 ?
N4 Cd1 O3 80.71(8) 4_666 2_656 ?
N6 Cd1 O3 87.22(9) 1_656 2_656 ?
O4 Cd1 O3 53.67(7) 2_656 2_656 ?
N1 Cd1 O2 83.78(8) . . ?
N4 Cd1 O2 137.81(8) 4_666 . ?
N6 Cd1 O2 82.14(8) 1_656 . ?
O4 Cd1 O2 88.37(7) 2_656 . ?
O3 Cd1 O2 141.00(7) 2_656 . ?
N1 Cd1 O1 89.89(8) . . ?
N4 Cd1 O1 84.90(7) 4_666 . ?
N6 Cd1 O1 86.93(8) 1_656 . ?
O4 Cd1 O1 141.29(7) 2_656 . ?
O3 Cd1 O1 163.57(7) 2_656 . ?
O2 Cd1 O1 52.91(7) . . ?
C11 N1 C9 105.7(3) . . ?
C11 N1 Cd1 122.2(2) . . ?
C9 N1 Cd1 132.0(2) . . ?
C11 N2 C10 106.9(3) . . ?
C11 N2 C12 125.2(3) . . ?
C10 N2 C12 127.9(3) . . ?
C20 N3 C22 106.9(3) . . ?
C20 N3 C19 127.8(3) . . ?
C22 N3 C19 125.2(3) . . ?
C20 N4 C21 105.1(3) . . ?
C20 N4 Cd1 123.0(2) . 4_565 ?
C21 N4 Cd1 131.8(2) . 4_565 ?
C24 N5 C26 106.6(3) . . ?
C24 N5 C23 125.5(3) . . ?
C26 N5 C23 127.6(3) . . ?
C24 N6 C25 105.0(3) . . ?
C24 N6 Cd1 123.9(2) . 1_454 ?
C25 N6 Cd1 130.2(2) . 1_454 ?
C1 O1 Cd1 90.58(17) . . ?
C1 O2 Cd1 92.62(17) . . ?
C8 O3 Cd1 90.98(17) . 2_646 ?
C8 O4 Cd1 92.08(18) . 2_646 ?
O2 C1 O1 123.9(3) . . ?
O2 C1 C2 118.0(3) . . ?
O1 C1 C2 118.1(3) . . ?
C7 C2 C3 119.7(3) . . ?
C7 C2 C1 120.9(3) . . ?
C3 C2 C1 119.5(3) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 119.9(19) . . ?
C2 C3 H3 120.4(19) . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 Br1 119.5(2) . . ?
C3 C4 Br1 119.4(2) . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H6 119.0(18) . . ?
C6 C5 H6 121.6(18) . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 C8 119.5(3) . . ?
C7 C6 C8 120.7(3) . . ?
C2 C7 C6 120.2(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
O3 C8 O4 123.3(3) . . ?
O3 C8 C6 118.5(3) . . ?
O4 C8 C6 118.2(3) . . ?
C10 C9 N1 109.7(3) . . ?
C10 C9 H9 127(2) . . ?
N1 C9 H9 123(2) . . ?
C9 C10 N2 106.4(3) . . ?
C9 C10 H10 130(2) . . ?
N2 C10 H10 124(2) . . ?
N1 C11 N2 111.3(3) . . ?
N1 C11 H11 128.2(18) . . ?
N2 C11 H11 120.5(18) . . ?
N2 C12 C13 111.2(2) . . ?
N2 C12 H12A 109(2) . . ?
C13 C12 H12A 108.5(19) . . ?
N2 C12 H12B 104.5(18) . . ?
C13 C12 H12B 114.5(19) . . ?
H12A C12 H12B 109(3) . . ?
C18 C13 C14 119.1(3) . . ?
C18 C13 C12 118.9(3) . . ?
C14 C13 C12 121.9(3) . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 123(2) . . ?
C15 C14 H14 116(2) . . ?
C14 C15 C16 118.9(3) . . ?
C14 C15 C19 120.9(3) . . ?
C16 C15 C19 120.2(3) . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 120(2) . . ?
C15 C16 H16 120(2) . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 C23 115.9(3) . . ?
C16 C17 C23 124.1(3) . . ?
C13 C18 C17 120.6(3) . . ?
C13 C18 H18 119(2) . . ?
C17 C18 H18 120(2) . . ?
N3 C19 C15 112.4(3) . . ?
N3 C19 H19A 108.0(19) . . ?
C15 C19 H19A 111.7(19) . . ?
N3 C19 H19B 107(2) . . ?
C15 C19 H19B 112(2) . . ?
H19A C19 H19B 105(3) . . ?
N4 C20 N3 111.7(3) . . ?
N4 C20 H20 126(2) . . ?
N3 C20 H20 123(2) . . ?
C22 C21 N4 110.1(3) . . ?
C22 C21 H21 129(2) . . ?
N4 C21 H21 121(2) . . ?
C21 C22 N3 106.3(3) . . ?
C21 C22 H22 131.6(19) . . ?
N3 C22 H22 122.1(19) . . ?
N5 C23 C17 116.0(3) . . ?
N5 C23 H23A 108(2) . . ?
C17 C23 H23A 109(2) . . ?
N5 C23 H23B 104(2) . . ?
C17 C23 H23B 112(2) . . ?
H23A C23 H23B 108(3) . . ?
N6 C24 N5 112.2(3) . . ?
N6 C24 H24 127(2) . . ?
N5 C24 H24 121(2) . . ?
C26 C25 N6 109.8(3) . . ?
C26 C25 H25 128(2) . . ?
N6 C25 H25 122(2) . . ?
C25 C26 N5 106.4(3) . . ?
C25 C26 H26 133(2) . . ?
N5 C26 H26 121(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.103
####################################################################### 
# 
# 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_2Ni
_database_code_depnum_ccdc_archive 'CCDC 1444052'
_audit_update_record             
;
2015-12-23 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H42 Br2 N12 Ni2 O8'
_chemical_formula_weight         1240.22

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'

_symmetry_cell_setting           TRICLINIC
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.478(3)
_cell_length_b                   13.541(4)
_cell_length_c                   17.986(5)
_cell_angle_alpha                90.459(6)
_cell_angle_beta                 90.614(6)
_cell_angle_gamma                103.389(5)
_cell_volume                     2482.1(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1125
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      23.45

_exptl_crystal_description       'THIN PLATES'
_exptl_crystal_colour            GREEN
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    2.438
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7585
_exptl_absorpt_correction_T_max  0.9529
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17811
_diffrn_reflns_av_R_equivalents  0.1195
_diffrn_reflns_av_sigmaI/netI    0.2185
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8651
_reflns_number_gt                3979
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1145P)²+6.9417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8651
_refine_ls_number_parameters     680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2100
_refine_ls_R_factor_gt           0.1058
_refine_ls_wR_factor_ref         0.2906
_refine_ls_wR_factor_gt          0.2463
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.12131(17) 0.30873(14) 0.11953(9) 0.0309(5) Uani 1 1 d . . .
Ni2 Ni 0.38800(17) 0.18573(13) 0.60606(9) 0.0299(5) Uani 1 1 d . . .
Br1 Br 0.74790(16) 0.15348(14) 0.25119(9) 0.0554(5) Uani 1 1 d . . .
Br2 Br -0.22300(16) 0.31630(14) 0.70112(9) 0.0522(5) Uani 1 1 d . . .
N1 N -0.0107(11) 0.3780(8) 0.1707(6) 0.032(3) Uani 1 1 d . . .
N2 N -0.1007(11) 0.4350(9) 0.2658(6) 0.034(3) Uani 1 1 d . . .
N3 N 0.3630(11) 0.5223(9) 0.4406(6) 0.032(3) Uani 1 1 d . . .
N4 N 0.4900(11) 0.6654(8) 0.3942(6) 0.032(3) Uani 1 1 d . . .
N5 N -0.1427(12) 0.0909(9) 0.4648(6) 0.038(3) Uani 1 1 d . . .
N6 N -0.2456(11) -0.0506(9) 0.4106(6) 0.034(3) Uani 1 1 d . . .
N7 N 0.5025(11) 0.1204(9) 0.6737(6) 0.035(3) Uani 1 1 d . . .
N8 N 0.5964(11) 0.0675(9) 0.7720(6) 0.037(3) Uani 1 1 d . . .
N9 N 0.6222(12) 0.4197(8) 0.9461(7) 0.036(3) Uani 1 1 d . . .
N10 N 0.7401(11) 0.5568(9) 0.8945(6) 0.037(3) Uani 1 1 d . . .
N11 N 0.1195(12) -0.0197(11) 0.9212(8) 0.052(4) Uani 1 1 d . . .
N12 N -0.0035(11) -0.1622(8) 0.8770(6) 0.032(3) Uani 1 1 d . . .
O1 O 0.3024(10) 0.2331(9) 0.1346(5) 0.054(3) Uani 1 1 d . . .
O2 O 0.2010(9) 0.2897(8) 0.2248(5) 0.040(3) Uani 1 1 d . . .
O3 O 0.4871(10) 0.1512(7) 0.5080(5) 0.034(2) Uani 1 1 d . . .
O4 O 0.3223(10) 0.2215(8) 0.4894(5) 0.041(3) Uani 1 1 d . . .
O5 O 0.2569(9) 0.2331(7) 0.6705(5) 0.039(2) Uani 1 1 d . . .
O6 O 0.3602(10) 0.2691(9) 0.7802(6) 0.052(3) Uani 1 1 d . . .
O7 O 0.1014(9) 0.3043(7) 1.0054(5) 0.038(2) Uani 1 1 d . . .
O8 O -0.1000(12) 0.3279(10) 0.9888(6) 0.070(4) Uani 1 1 d . . .
C1 C 0.2911(14) 0.2509(11) 0.2023(8) 0.036(4) Uani 1 1 d . . .
C2 C 0.3881(15) 0.2284(10) 0.2584(7) 0.034(4) Uani 1 1 d . . .
C3 C 0.5031(14) 0.2101(11) 0.2337(8) 0.038(4) Uani 1 1 d . . .
H3 H 0.5235 0.2155 0.1835 0.046 Uiso 1 1 calc R . .
C4 C 0.5896(13) 0.1831(11) 0.2850(8) 0.037(4) Uani 1 1 d . . .
C5 C 0.5613(14) 0.1785(11) 0.3591(8) 0.040(4) Uani 1 1 d . . .
H5 H 0.6208 0.1628 0.3931 0.048 Uiso 1 1 calc R . .
C6 C 0.4444(13) 0.1972(10) 0.3836(8) 0.032(3) Uani 1 1 d . . .
C7 C 0.3564(13) 0.2234(10) 0.3333(8) 0.033(3) Uani 1 1 d . . .
H7 H 0.2782 0.2371 0.3494 0.040 Uiso 1 1 calc R . .
C8 C 0.4123(14) 0.1903(11) 0.4651(8) 0.036(4) Uani 1 1 d . . .
C9 C 0.2623(15) 0.2574(11) 0.7388(9) 0.041(4) Uani 1 1 d . . .
C10 C 0.1381(13) 0.2758(10) 0.7731(7) 0.029(3) Uani 1 1 d . . .
C11 C 0.0286(14) 0.2806(10) 0.7295(8) 0.037(4) Uani 1 1 d . . .
H11 H 0.0279 0.2669 0.6787 0.044 Uiso 1 1 calc R . .
C12 C -0.0781(12) 0.3057(10) 0.7617(8) 0.031(3) Uani 1 1 d . . .
C13 C -0.0829(12) 0.3190(11) 0.8365(8) 0.034(4) Uani 1 1 d . . .
H13 H -0.1555 0.3358 0.8580 0.041 Uiso 1 1 calc R . .
C14 C 0.0226(15) 0.3070(11) 0.8807(8) 0.038(4) Uani 1 1 d . . .
C15 C 0.1327(13) 0.2862(10) 0.8496(7) 0.032(3) Uani 1 1 d . . .
H15 H 0.2028 0.2791 0.8796 0.038 Uiso 1 1 calc R . .
C16 C 0.0095(17) 0.3166(11) 0.9656(7) 0.039(4) Uani 1 1 d . . .
C17 C -0.1145(16) 0.4158(13) 0.1466(8) 0.051(5) Uani 1 1 d . . .
H17 H -0.1430 0.4165 0.0975 0.061 Uiso 1 1 calc R . .
C18 C -0.1677(18) 0.4513(13) 0.2050(8) 0.057(5) Uani 1 1 d . . .
H18 H -0.2386 0.4819 0.2038 0.069 Uiso 1 1 calc R . .
C19 C -0.0031(15) 0.3937(11) 0.2416(8) 0.040(4) Uani 1 1 d . . .
H19 H 0.0617 0.3785 0.2722 0.048 Uiso 1 1 calc R . .
C20 C -0.1203(15) 0.4622(11) 0.3430(8) 0.041(4) Uani 1 1 d . . .
H20A H -0.2137 0.4449 0.3525 0.049 Uiso 1 1 calc R . .
H20B H -0.0905 0.5353 0.3484 0.049 Uiso 1 1 calc R . .
C21 C -0.0550(13) 0.4150(10) 0.3999(7) 0.030(3) Uiso 1 1 d . . .
C22 C 0.0786(14) 0.4605(11) 0.4199(8) 0.038(4) Uani 1 1 d . . .
H22 H 0.1210 0.5222 0.3995 0.045 Uiso 1 1 calc R . .
C23 C 0.1442(13) 0.4114(11) 0.4700(8) 0.033(3) Uani 1 1 d . . .
C24 C 0.0787(15) 0.3191(11) 0.5022(8) 0.039(4) Uani 1 1 d . . .
H24 H 0.1221 0.2870 0.5365 0.047 Uiso 1 1 calc R . .
C25 C -0.0483(14) 0.2773(10) 0.4828(8) 0.034(3) Uani 1 1 d . . .
C26 C -0.1142(15) 0.3227(11) 0.4309(8) 0.039(4) Uani 1 1 d . . .
H26 H -0.1994 0.2907 0.4167 0.047 Uiso 1 1 calc R . .
C27 C 0.2872(15) 0.4566(12) 0.4931(8) 0.050(4) Uani 1 1 d . . .
H27A H 0.2877 0.4940 0.5394 0.060 Uiso 1 1 calc R . .
H27B H 0.3294 0.4013 0.5027 0.060 Uiso 1 1 calc R . .
C28 C 0.4118(15) 0.4996(11) 0.3752(9) 0.046(4) Uani 1 1 d . . .
H28 H 0.3976 0.4356 0.3531 0.055 Uiso 1 1 calc R . .
C29 C 0.4844(15) 0.5861(12) 0.3481(9) 0.049(4) Uani 1 1 d . . .
H29 H 0.5263 0.5907 0.3025 0.059 Uiso 1 1 calc R . .
C30 C 0.4111(14) 0.6226(13) 0.4490(8) 0.041(4) Uani 1 1 d . . .
H30 H 0.3914 0.6593 0.4895 0.049 Uiso 1 1 calc R . .
C31 C -0.1159(16) 0.1778(11) 0.5174(8) 0.048(4) Uani 1 1 d . . .
H31A H -0.0614 0.1633 0.5579 0.057 Uiso 1 1 calc R . .
H31B H -0.1982 0.1851 0.5383 0.057 Uiso 1 1 calc R . .
C32 C -0.2554(15) 0.0237(10) 0.4580(8) 0.037(4) Uani 1 1 d . . .
H32 H -0.3315 0.0274 0.4828 0.044 Uiso 1 1 calc R . .
C33 C -0.1167(15) -0.0233(13) 0.3859(8) 0.048(4) Uani 1 1 d . . .
H33 H -0.0794 -0.0598 0.3517 0.057 Uiso 1 1 calc R . .
C34 C -0.0555(18) 0.0632(12) 0.4191(9) 0.058(5) Uani 1 1 d . . .
H34 H 0.0310 0.0979 0.4120 0.070 Uiso 1 1 calc R . .
C35 C 0.5938(16) 0.0716(12) 0.6525(8) 0.047(4) Uani 1 1 d . . .
H35 H 0.6153 0.0634 0.6032 0.057 Uiso 1 1 calc R . .
C36 C 0.6499(15) 0.0365(11) 0.7094(8) 0.041(4) Uani 1 1 d . . .
H36 H 0.7131 -0.0016 0.7073 0.050 Uiso 1 1 calc R . .
C37 C 0.5081(15) 0.1175(11) 0.7470(9) 0.044(4) Uani 1 1 d . . .
H37 H 0.4565 0.1470 0.7780 0.053 Uiso 1 1 calc R . .
C38 C 0.6241(15) 0.0459(12) 0.8503(8) 0.046(4) Uani 1 1 d . . .
H38A H 0.7164 0.0724 0.8617 0.055 Uiso 1 1 calc R . .
H38B H 0.6036 -0.0269 0.8580 0.055 Uiso 1 1 calc R . .
C39 C 0.5416(17) 0.0951(12) 0.9015(8) 0.047(4) Uani 1 1 d . . .
C40 C 0.5965(16) 0.1897(12) 0.9315(8) 0.046(4) Uani 1 1 d . . .
H40 H 0.6851 0.2181 0.9243 0.055 Uiso 1 1 calc R . .
C41 C 0.5230(14) 0.2435(12) 0.9719(8) 0.040(4) Uani 1 1 d . . .
C42 C 0.3931(16) 0.1946(13) 0.9823(8) 0.052(5) Uani 1 1 d . . .
H42 H 0.3402 0.2294 1.0080 0.062 Uiso 1 1 calc R . .
C43 C 0.3358(15) 0.0959(12) 0.9565(8) 0.042(4) Uani 1 1 d . . .
C44 C 0.4164(16) 0.0476(12) 0.9141(8) 0.049(4) Uani 1 1 d . . .
H44 H 0.3828 -0.0172 0.8947 0.059 Uiso 1 1 calc R . .
C45 C 0.5789(17) 0.3451(12) 1.0044(9) 0.056(5) Uani 1 1 d . . .
H45A H 0.5133 0.3661 1.0345 0.067 Uiso 1 1 calc R . .
H45B H 0.6528 0.3420 1.0366 0.067 Uiso 1 1 calc R . .
C46 C 0.5724(17) 0.4252(13) 0.8792(10) 0.057(5) Uani 1 1 d . . .
H46 H 0.5010 0.3789 0.8585 0.069 Uiso 1 1 calc R . .
C47 C 0.641(2) 0.5080(14) 0.8456(11) 0.077(6) Uani 1 1 d . . .
H47 H 0.6255 0.5293 0.7981 0.092 Uiso 1 1 calc R . .
C48 C 0.7236(17) 0.4995(11) 0.9533(9) 0.051(5) Uani 1 1 d . . .
H48 H 0.7768 0.5129 0.9956 0.061 Uiso 1 1 calc R . .
C49 C 0.1959(16) 0.0565(13) 0.9745(10) 0.068(6) Uani 1 1 d . . .
H49A H 0.1543 0.1134 0.9773 0.081 Uiso 1 1 calc R . .
H49B H 0.1909 0.0262 1.0233 0.081 Uiso 1 1 calc R . .
C50 C 0.0713(17) 0.0027(12) 0.8552(10) 0.054(5) Uani 1 1 d . . .
H50 H 0.0887 0.0652 0.8317 0.065 Uiso 1 1 calc R . .
C51 C -0.0060(15) -0.0834(13) 0.8312(9) 0.049(4) Uani 1 1 d . . .
H51 H -0.0564 -0.0894 0.7879 0.059 Uiso 1 1 calc R . .
C52 C 0.0786(14) -0.1190(12) 0.9296(9) 0.047(4) Uani 1 1 d . . .
H52 H 0.1053 -0.1543 0.9687 0.056 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O7 2.059(9) 1_554 ?
Ni1 N1 2.063(11) . ?
Ni1 N10 2.069(12) 2_666 ?
Ni1 N12 2.082(11) 2_556 ?
Ni1 O2 2.103(9) . ?
Ni1 O1 2.370(11) . ?
Ni2 O5 2.017(9) . ?
Ni2 N7 2.045(11) . ?
Ni2 N6 2.093(11) 2_556 ?
Ni2 N4 2.123(11) 2_666 ?
Ni2 O3 2.159(9) . ?
Ni2 O4 2.292(9) . ?
Br1 C4 1.899(14) . ?
Br2 C12 1.892(12) . ?
N1 C19 1.290(16) . ?
N1 C17 1.372(17) . ?
N2 C18 1.341(18) . ?
N2 C19 1.348(17) . ?
N2 C20 1.463(17) . ?
N3 C30 1.340(18) . ?
N3 C28 1.348(17) . ?
N3 C27 1.421(17) . ?
N4 C30 1.340(17) . ?
N4 C29 1.341(17) . ?
N4 Ni2 2.123(11) 2_666 ?
N5 C32 1.318(17) . ?
N5 C34 1.350(19) . ?
N5 C31 1.477(17) . ?
N6 C32 1.335(17) . ?
N6 C33 1.393(17) . ?
N6 Ni2 2.093(11) 2_556 ?
N7 C37 1.320(18) . ?
N7 C35 1.339(18) . ?
N8 C37 1.343(17) . ?
N8 C36 1.369(17) . ?
N8 C38 1.480(18) . ?
N9 C46 1.316(19) . ?
N9 C48 1.333(17) . ?
N9 C45 1.464(19) . ?
N10 C48 1.306(18) . ?
N10 C47 1.39(2) . ?
N10 Ni1 2.069(12) 2_666 ?
N11 C52 1.323(18) . ?
N11 C50 1.35(2) . ?
N11 C49 1.487(19) . ?
N12 C52 1.310(18) . ?
N12 C51 1.358(18) . ?
N12 Ni1 2.082(11) 2_556 ?
O1 C1 1.251(15) . ?
O2 C1 1.251(16) . ?
O3 C8 1.294(17) . ?
O4 C8 1.204(16) . ?
O5 C9 1.268(17) . ?
O6 C9 1.239(17) . ?
O7 C16 1.237(17) . ?
O7 Ni1 2.059(9) 1_556 ?
O8 C16 1.266(17) . ?
C1 C2 1.506(19) . ?
C2 C3 1.363(19) . ?
C2 C7 1.390(18) . ?
C3 C4 1.395(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(19) . ?
C5 C6 1.382(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(18) . ?
C6 C8 1.506(19) . ?
C7 H7 0.9300 . ?
C9 C10 1.516(19) . ?
C10 C15 1.386(18) . ?
C10 C11 1.397(18) . ?
C11 C12 1.375(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.358(18) . ?
C13 C14 1.395(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(19) . ?
C14 C16 1.543(18) . ?
C15 H15 0.9300 . ?
C17 C18 1.33(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.457(19) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C26 1.385(18) . ?
C21 C22 1.433(19) . ?
C22 C23 1.391(19) . ?
C22 H22 0.9300 . ?
C23 C24 1.411(18) . ?
C23 C27 1.533(19) . ?
C24 C25 1.361(19) . ?
C24 H24 0.9300 . ?
C25 C26 1.383(19) . ?
C25 C31 1.511(18) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.339(19) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32 0.9300 . ?
C33 C34 1.33(2) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.320(19) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 C39 1.52(2) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C44 1.34(2) . ?
C39 C40 1.38(2) . ?
C40 C41 1.38(2) . ?
C40 H40 0.9300 . ?
C41 C42 1.38(2) . ?
C41 C45 1.48(2) . ?
C42 C43 1.40(2) . ?
C42 H42 0.9300 . ?
C43 C44 1.41(2) . ?
C43 C49 1.48(2) . ?
C44 H44 0.9300 . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.34(2) . ?
C46 H46 0.9300 . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C51 1.32(2) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?

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
O7 Ni1 N1 112.7(4) 1_554 . ?
O7 Ni1 N10 86.3(4) 1_554 2_666 ?
N1 Ni1 N10 94.0(4) . 2_666 ?
O7 Ni1 N12 89.0(4) 1_554 2_556 ?
N1 Ni1 N12 95.8(4) . 2_556 ?
N10 Ni1 N12 170.1(4) 2_666 2_556 ?
O7 Ni1 O2 158.4(4) 1_554 . ?
N1 Ni1 O2 88.8(4) . . ?
N10 Ni1 O2 90.7(4) 2_666 . ?
N12 Ni1 O2 90.5(4) 2_556 . ?
O7 Ni1 O1 100.5(4) 1_554 . ?
N1 Ni1 O1 146.7(4) . . ?
N10 Ni1 O1 85.8(4) 2_666 . ?
N12 Ni1 O1 86.6(4) 2_556 . ?
O2 Ni1 O1 57.9(4) . . ?
O5 Ni2 N7 107.8(4) . . ?
O5 Ni2 N6 87.3(4) . 2_556 ?
N7 Ni2 N6 94.0(5) . 2_556 ?
O5 Ni2 N4 90.7(4) . 2_666 ?
N7 Ni2 N4 97.8(4) . 2_666 ?
N6 Ni2 N4 168.1(4) 2_556 2_666 ?
O5 Ni2 O3 160.2(4) . . ?
N7 Ni2 O3 91.9(4) . . ?
N6 Ni2 O3 89.2(4) 2_556 . ?
N4 Ni2 O3 88.8(4) 2_666 . ?
O5 Ni2 O4 101.7(4) . . ?
N7 Ni2 O4 150.2(4) . . ?
N6 Ni2 O4 83.0(4) 2_556 . ?
N4 Ni2 O4 85.9(4) 2_666 . ?
O3 Ni2 O4 58.6(4) . . ?
C19 N1 C17 105.6(12) . . ?
C19 N1 Ni1 119.7(10) . . ?
C17 N1 Ni1 134.7(10) . . ?
C18 N2 C19 106.2(12) . . ?
C18 N2 C20 128.2(13) . . ?
C19 N2 C20 125.4(12) . . ?
C30 N3 C28 104.2(11) . . ?
C30 N3 C27 126.2(12) . . ?
C28 N3 C27 129.4(13) . . ?
C30 N4 C29 101.6(13) . . ?
C30 N4 Ni2 126.8(10) . 2_666 ?
C29 N4 Ni2 131.0(10) . 2_666 ?
C32 N5 C34 108.4(12) . . ?
C32 N5 C31 125.1(13) . . ?
C34 N5 C31 126.5(13) . . ?
C32 N6 C33 104.4(12) . . ?
C32 N6 Ni2 125.2(9) . 2_556 ?
C33 N6 Ni2 129.7(10) . 2_556 ?
C37 N7 C35 103.4(12) . . ?
C37 N7 Ni2 129.7(10) . . ?
C35 N7 Ni2 126.9(10) . . ?
C37 N8 C36 105.1(12) . . ?
C37 N8 C38 127.1(12) . . ?
C36 N8 C38 127.7(12) . . ?
C46 N9 C48 106.3(13) . . ?
C46 N9 C45 129.5(14) . . ?
C48 N9 C45 124.1(13) . . ?
C48 N10 C47 104.0(14) . . ?
C48 N10 Ni1 127.1(10) . 2_666 ?
C47 N10 Ni1 128.8(12) . 2_666 ?
C52 N11 C50 106.8(14) . . ?
C52 N11 C49 128.4(16) . . ?
C50 N11 C49 124.7(16) . . ?
C52 N12 C51 102.4(13) . . ?
C52 N12 Ni1 125.3(10) . 2_556 ?
C51 N12 Ni1 131.3(11) . 2_556 ?
C1 O1 Ni1 84.4(9) . . ?
C1 O2 Ni1 96.7(9) . . ?
C8 O3 Ni2 91.8(8) . . ?
C8 O4 Ni2 88.0(9) . . ?
C9 O5 Ni2 130.5(10) . . ?
C16 O7 Ni1 129.9(9) . 1_556 ?
O1 C1 O2 120.9(14) . . ?
O1 C1 C2 120.6(13) . . ?
O2 C1 C2 118.5(12) . . ?
C3 C2 C7 121.8(13) . . ?
C3 C2 C1 118.8(12) . . ?
C7 C2 C1 119.4(13) . . ?
C2 C3 C4 118.9(13) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.4(13) . . ?
C5 C4 Br1 120.1(11) . . ?
C3 C4 Br1 119.5(11) . . ?
C4 C5 C6 120.2(14) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 120.3(13) . . ?
C5 C6 C8 120.1(13) . . ?
C7 C6 C8 119.6(13) . . ?
C6 C7 C2 118.4(13) . . ?
C6 C7 H7 120.8 . . ?
C2 C7 H7 120.8 . . ?
O4 C8 O3 121.5(13) . . ?
O4 C8 C6 121.3(14) . . ?
O3 C8 C6 117.2(13) . . ?
O6 C9 O5 126.1(14) . . ?
O6 C9 C10 116.8(14) . . ?
O5 C9 C10 117.1(14) . . ?
C15 C10 C11 119.4(13) . . ?
C15 C10 C9 119.0(13) . . ?
C11 C10 C9 121.6(13) . . ?
C12 C11 C10 119.9(12) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.9(12) . . ?
C13 C12 Br2 119.8(10) . . ?
C11 C12 Br2 119.2(10) . . ?
C12 C13 C14 119.1(13) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 121.2(13) . . ?
C15 C14 C16 121.6(13) . . ?
C13 C14 C16 117.3(13) . . ?
C14 C15 C10 119.2(13) . . ?
C14 C15 H15 120.4 . . ?
C10 C15 H15 120.4 . . ?
O7 C16 O8 125.4(12) . . ?
O7 C16 C14 117.8(13) . . ?
O8 C16 C14 116.5(14) . . ?
C18 C17 N1 109.0(13) . . ?
C18 C17 H17 125.5 . . ?
N1 C17 H17 125.5 . . ?
C17 C18 N2 107.6(15) . . ?
C17 C18 H18 126.2 . . ?
N2 C18 H18 126.2 . . ?
N1 C19 N2 111.6(13) . . ?
N1 C19 H19 124.2 . . ?
N2 C19 H19 124.2 . . ?
N2 C20 C21 116.6(12) . . ?
N2 C20 H20A 108.1 . . ?
C21 C20 H20A 108.1 . . ?
N2 C20 H20B 108.1 . . ?
C21 C20 H20B 108.1 . . ?
H20A C20 H20B 107.3 . . ?
C26 C21 C22 118.6(13) . . ?
C26 C21 C20 122.0(13) . . ?
C22 C21 C20 119.2(13) . . ?
C23 C22 C21 119.2(13) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 120.3(13) . . ?
C22 C23 C27 121.4(13) . . ?
C24 C23 C27 118.3(13) . . ?
C25 C24 C23 119.6(14) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 121.2(13) . . ?
C24 C25 C31 118.6(14) . . ?
C26 C25 C31 120.2(13) . . ?
C25 C26 C21 121.0(13) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
N3 C27 C23 115.4(12) . . ?
N3 C27 H27A 108.4 . . ?
C23 C27 H27A 108.4 . . ?
N3 C27 H27B 108.4 . . ?
C23 C27 H27B 108.4 . . ?
H27A C27 H27B 107.5 . . ?
C29 C28 N3 107.4(13) . . ?
C29 C28 H28 126.3 . . ?
N3 C28 H28 126.3 . . ?
C28 C29 N4 112.4(15) . . ?
C28 C29 H29 123.8 . . ?
N4 C29 H29 123.8 . . ?
N4 C30 N3 114.4(13) . . ?
N4 C30 H30 122.8 . . ?
N3 C30 H30 122.8 . . ?
N5 C31 C25 113.9(12) . . ?
N5 C31 H31A 108.8 . . ?
C25 C31 H31A 108.8 . . ?
N5 C31 H31B 108.8 . . ?
C25 C31 H31B 108.8 . . ?
H31A C31 H31B 107.7 . . ?
N5 C32 N6 110.9(13) . . ?
N5 C32 H32 124.5 . . ?
N6 C32 H32 124.5 . . ?
C34 C33 N6 109.2(15) . . ?
C34 C33 H33 125.4 . . ?
N6 C33 H33 125.4 . . ?
C33 C34 N5 107.1(15) . . ?
C33 C34 H34 126.5 . . ?
N5 C34 H34 126.5 . . ?
C36 C35 N7 112.5(13) . . ?
C36 C35 H35 123.7 . . ?
N7 C35 H35 123.7 . . ?
C35 C36 N8 106.2(13) . . ?
C35 C36 H36 126.9 . . ?
N8 C36 H36 126.9 . . ?
N7 C37 N8 112.7(14) . . ?
N7 C37 H37 123.6 . . ?
N8 C37 H37 123.6 . . ?
N8 C38 C39 109.5(11) . . ?
N8 C38 H38A 109.8 . . ?
C39 C38 H38A 109.8 . . ?
N8 C38 H38B 109.8 . . ?
C39 C38 H38B 109.8 . . ?
H38A C38 H38B 108.2 . . ?
C44 C39 C40 121.7(17) . . ?
C44 C39 C38 119.5(15) . . ?
C40 C39 C38 118.7(15) . . ?
C39 C40 C41 121.7(15) . . ?
C39 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C40 C41 C42 115.6(14) . . ?
C40 C41 C45 122.9(14) . . ?
C42 C41 C45 121.4(15) . . ?
C41 C42 C43 124.3(16) . . ?
C41 C42 H42 117.9 . . ?
C43 C42 H42 117.9 . . ?
C42 C43 C44 116.4(14) . . ?
C42 C43 C49 116.0(15) . . ?
C44 C43 C49 127.6(14) . . ?
C39 C44 C43 120.1(15) . . ?
C39 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
N9 C45 C41 110.9(12) . . ?
N9 C45 H45A 109.5 . . ?
C41 C45 H45A 109.5 . . ?
N9 C45 H45B 109.5 . . ?
C41 C45 H45B 109.5 . . ?
H45A C45 H45B 108.1 . . ?
N9 C46 C47 109.0(16) . . ?
N9 C46 H46 125.5 . . ?
C47 C46 H46 125.5 . . ?
C46 C47 N10 107.9(17) . . ?
C46 C47 H47 126.0 . . ?
N10 C47 H47 126.0 . . ?
N10 C48 N9 112.7(13) . . ?
N10 C48 H48 123.7 . . ?
N9 C48 H48 123.7 . . ?
C43 C49 N11 115.6(14) . . ?
C43 C49 H49A 108.4 . . ?
N11 C49 H49A 108.4 . . ?
C43 C49 H49B 108.4 . . ?
N11 C49 H49B 108.4 . . ?
H49A C49 H49B 107.4 . . ?
C51 C50 N11 105.2(15) . . ?
C51 C50 H50 127.4 . . ?
N11 C50 H50 127.4 . . ?
C50 C51 N12 112.4(16) . . ?
C50 C51 H51 123.8 . . ?
N12 C51 H51 123.8 . . ?
N12 C52 N11 112.9(15) . . ?
N12 C52 H52 123.6 . . ?
N11 C52 H52 123.6 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.407
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.151
####################################################################### 
# 
# 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_3CC
_database_code_depnum_ccdc_archive 'CCDC 1444053'
_audit_update_record             
;
2015-12-23 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N9 O7'
_chemical_formula_weight         547.50

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'

_symmetry_cell_setting           ORTHORHOMBIC
_symmetry_space_group_name_H-M   Pca21

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

_cell_length_a                   23.224(3)
_cell_length_b                   4.5446(5)
_cell_length_c                   23.134(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2441.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1392
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      19.69

_exptl_crystal_description       PLATES
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_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  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11436
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4121
_reflns_number_gt                3366
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0689P)²+2.2550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(3)
_refine_ls_number_reflns         4121
_refine_ls_number_parameters     362
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_ref         0.1819
_refine_ls_wR_factor_gt          0.1722
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.139
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.26949(18) -0.0887(10) 0.09307(19) 0.0235(11) Uani 1 1 d . . .
N2 N 0.33314(18) 0.2068(10) 0.0583(2) 0.0271(11) Uani 1 1 d . . .
N3 N -0.01220(18) 0.0767(9) 0.06832(19) 0.0207(10) Uani 1 1 d . . .
N4 N -0.07923(17) 0.4081(10) 0.0535(2) 0.0262(11) Uani 1 1 d . . .
N5 N 0.0987(2) 0.2978(10) 0.3076(2) 0.0256(11) Uani 1 1 d . . .
C17 C 0.0577(3) 0.0264(16) 0.3725(3) 0.0438(17) Uani 1 1 d . . .
H17 H 0.0321 -0.0998 0.3909 0.053 Uiso 1 1 calc R . .
N7 N 0.4199(3) 0.3871(16) 0.2396(3) 0.0603(19) Uani 1 1 d . . .
N8 N 0.3822(2) 0.5236(13) 0.4437(3) 0.0410(14) Uani 1 1 d . . .
N9 N 0.2634(2) -0.1712(12) 0.3407(3) 0.0390(13) Uani 1 1 d . . .
O1 O 0.3231(2) 0.0000(15) 0.2362(2) 0.0697(17) Uani 1 1 d . . .
H1 H 0.3513 -0.0641 0.2191 0.105 Uiso 1 1 calc R . .
O2 O 0.4051(5) 0.330(2) 0.1931(3) 0.172(5) Uani 1 1 d . . .
O3 O 0.4559(4) 0.541(4) 0.2422(3) 0.256(9) Uani 1 1 d . . .
O4 O 0.4205(2) 0.7099(11) 0.4440(2) 0.0599(15) Uani 1 1 d . . .
O5 O 0.3537(2) 0.4553(12) 0.4869(2) 0.0603(15) Uani 1 1 d . . .
O6 O 0.2458(2) -0.2478(12) 0.3881(2) 0.0560(14) Uani 1 1 d . . .
O7 O 0.2446(3) -0.2763(14) 0.2959(2) 0.081(2) Uani 1 1 d . . .
C1 C 0.1764(2) -0.0969(12) 0.1469(2) 0.0215(12) Uani 1 1 d . . .
C2 C 0.1284(2) -0.1674(11) 0.1148(2) 0.0225(12) Uani 1 1 d . . .
H2 H 0.1316 -0.3015 0.0846 0.027 Uiso 1 1 calc R . .
C3 C 0.0753(2) -0.0422(12) 0.1268(2) 0.0225(12) Uani 1 1 d . . .
C4 C 0.0716(2) 0.1688(12) 0.1701(2) 0.0201(12) Uani 1 1 d . . .
H4A H 0.0366 0.2627 0.1768 0.024 Uiso 1 1 calc R . .
C5 C 0.1193(2) 0.2419(11) 0.2036(2) 0.0180(11) Uani 1 1 d . . .
C6 C 0.1716(2) 0.1100(12) 0.1916(2) 0.0219(12) Uani 1 1 d . . .
H6A H 0.2038 0.1590 0.2133 0.026 Uiso 1 1 calc R . .
C7 C 0.2334(2) -0.2490(13) 0.1354(3) 0.0305(14) Uani 1 1 d . . .
H7A H 0.2544 -0.2671 0.1714 0.037 Uiso 1 1 calc R . .
H7B H 0.2261 -0.4458 0.1209 0.037 Uiso 1 1 calc R . .
C8 C 0.3098(2) 0.0985(12) 0.1060(2) 0.0243(13) Uani 1 1 d . . .
H8 H 0.3207 0.1491 0.1434 0.029 Uiso 1 1 calc R . .
C9 C 0.3062(2) 0.0769(15) 0.0128(3) 0.0355(15) Uani 1 1 d . . .
H9 H 0.3139 0.1108 -0.0260 0.043 Uiso 1 1 calc R . .
C10 C 0.2662(3) -0.1099(14) 0.0339(3) 0.0331(15) Uani 1 1 d . . .
H10 H 0.2414 -0.2289 0.0127 0.040 Uiso 1 1 calc R . .
C11 C 0.0220(2) -0.1496(13) 0.0962(3) 0.0289(14) Uani 1 1 d . . .
H11A H 0.0335 -0.2920 0.0671 0.035 Uiso 1 1 calc R . .
H11B H -0.0021 -0.2512 0.1240 0.035 Uiso 1 1 calc R . .
C12 C -0.0044(2) 0.1851(13) 0.0130(2) 0.0284(14) Uani 1 1 d . . .
H12 H 0.0240 0.1303 -0.0131 0.034 Uiso 1 1 calc R . .
C13 C -0.0464(2) 0.3864(12) 0.0046(3) 0.0292(14) Uani 1 1 d . . .
H13 H -0.0521 0.4934 -0.0292 0.035 Uiso 1 1 calc R . .
C14 C -0.0575(2) 0.2186(12) 0.0900(3) 0.0255(13) Uani 1 1 d . . .
H14 H -0.0721 0.1863 0.1269 0.031 Uiso 1 1 calc R . .
C15 C 0.1126(2) 0.4515(12) 0.2533(2) 0.0227(12) Uani 1 1 d . . .
H15A H 0.1480 0.5615 0.2583 0.027 Uiso 1 1 calc R . .
H15B H 0.0821 0.5906 0.2445 0.027 Uiso 1 1 calc R . .
C16 C 0.0538(3) 0.1183(13) 0.3172(3) 0.0304(14) Uani 1 1 d . . .
H16 H 0.0253 0.0670 0.2908 0.036 Uiso 1 1 calc R . .
N6 N 0.1056(3) 0.1494(13) 0.3972(2) 0.0506(16) Uani 1 1 d . . .
C18 C 0.1288(3) 0.3104(15) 0.3570(3) 0.0392(17) Uani 1 1 d . . .
H18 H 0.1621 0.4210 0.3619 0.047 Uiso 1 1 calc R . .
C19 C 0.3385(3) 0.1114(15) 0.2824(3) 0.0408(17) Uani 1 1 d . . .
C20 C 0.3850(3) 0.3157(14) 0.2898(3) 0.0353(15) Uani 1 1 d . . .
C21 C 0.4004(2) 0.4434(14) 0.3408(3) 0.0356(15) Uani 1 1 d . . .
H21 H 0.4315 0.5717 0.3426 0.043 Uiso 1 1 calc R . .
C22 C 0.3686(2) 0.3783(13) 0.3904(3) 0.0287(13) Uani 1 1 d . . .
C23 C 0.3253(2) 0.1752(13) 0.3888(2) 0.0280(13) Uani 1 1 d . . .
H23 H 0.3060 0.1258 0.4226 0.034 Uiso 1 1 calc R . .
C24 C 0.3098(2) 0.0424(12) 0.3374(2) 0.0263(13) 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
N1 C8 1.300(7) . ?
N1 C10 1.373(7) . ?
N1 C7 1.479(7) . ?
N2 C8 1.325(7) . ?
N2 C9 1.358(7) . ?
N3 C14 1.332(7) . ?
N3 C12 1.382(7) . ?
N3 C11 1.451(7) . ?
N4 C14 1.307(7) . ?
N4 C13 1.367(7) . ?
N5 C18 1.341(7) . ?
N5 C16 1.344(7) . ?
N5 C15 1.472(7) . ?
C17 C16 1.350(9) . ?
C17 N6 1.370(9) . ?
C17 H17 0.9300 . ?
N7 O3 1.091(9) . ?
N7 O2 1.159(9) . ?
N7 C20 1.453(8) . ?
N8 O4 1.228(7) . ?
N8 O5 1.238(7) . ?
N8 C22 1.434(8) . ?
N9 O6 1.221(7) . ?
N9 O7 1.222(7) . ?
N9 C24 1.453(7) . ?
O1 C19 1.235(8) . ?
O1 H1 0.8200 . ?
C1 C2 1.378(7) . ?
C1 C6 1.403(7) . ?
C1 C7 1.517(8) . ?
C2 C3 1.385(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(8) . ?
C3 C11 1.508(8) . ?
C4 C5 1.393(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(7) . ?
C5 C15 1.501(8) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9300 . ?
C9 C10 1.350(8) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.352(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16 0.9300 . ?
N6 C18 1.300(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.434(9) . ?
C19 C24 1.470(8) . ?
C20 C21 1.364(9) . ?
C21 C22 1.396(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(8) . ?
C23 C24 1.380(8) . ?
C23 H23 0.9300 . ?

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
C8 N1 C10 108.4(5) . . ?
C8 N1 C7 125.3(5) . . ?
C10 N1 C7 126.3(5) . . ?
C8 N2 C9 107.2(5) . . ?
C14 N3 C12 106.2(4) . . ?
C14 N3 C11 127.6(5) . . ?
C12 N3 C11 126.3(4) . . ?
C14 N4 C13 105.7(5) . . ?
C18 N5 C16 106.8(5) . . ?
C18 N5 C15 126.4(5) . . ?
C16 N5 C15 126.8(5) . . ?
C16 C17 N6 108.9(6) . . ?
C16 C17 H17 125.6 . . ?
N6 C17 H17 125.6 . . ?
O3 N7 O2 115.0(7) . . ?
O3 N7 C20 121.7(7) . . ?
O2 N7 C20 121.7(7) . . ?
O4 N8 O5 123.9(6) . . ?
O4 N8 C22 118.8(6) . . ?
O5 N8 C22 117.4(5) . . ?
O6 N9 O7 122.1(5) . . ?
O6 N9 C24 119.1(5) . . ?
O7 N9 C24 118.8(6) . . ?
C19 O1 H1 109.5 . . ?
C2 C1 C6 119.2(5) . . ?
C2 C1 C7 120.4(5) . . ?
C6 C1 C7 120.3(5) . . ?
C1 C2 C3 121.2(5) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 119.0(5) . . ?
C2 C3 C11 120.2(5) . . ?
C4 C3 C11 120.7(5) . . ?
C3 C4 C5 121.0(5) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 118.9(5) . . ?
C6 C5 C15 121.4(5) . . ?
C4 C5 C15 119.7(4) . . ?
C5 C6 C1 120.7(5) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
N1 C7 C1 112.7(4) . . ?
N1 C7 H7A 109.1 . . ?
C1 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C1 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 N2 110.2(5) . . ?
N1 C8 H8 124.9 . . ?
N2 C8 H8 124.9 . . ?
C10 C9 N2 108.1(5) . . ?
C10 C9 H9 125.9 . . ?
N2 C9 H9 125.9 . . ?
C9 C10 N1 106.1(5) . . ?
C9 C10 H10 127.0 . . ?
N1 C10 H10 127.0 . . ?
N3 C11 C3 115.4(5) . . ?
N3 C11 H11A 108.4 . . ?
C3 C11 H11A 108.4 . . ?
N3 C11 H11B 108.4 . . ?
C3 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 N3 106.3(5) . . ?
C13 C12 H12 126.9 . . ?
N3 C12 H12 126.9 . . ?
C12 C13 N4 109.3(5) . . ?
C12 C13 H13 125.3 . . ?
N4 C13 H13 125.3 . . ?
N4 C14 N3 112.4(5) . . ?
N4 C14 H14 123.8 . . ?
N3 C14 H14 123.8 . . ?
N5 C15 C5 112.0(4) . . ?
N5 C15 H15A 109.2 . . ?
C5 C15 H15A 109.2 . . ?
N5 C15 H15B 109.2 . . ?
C5 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N5 C16 C17 107.0(6) . . ?
N5 C16 H16 126.5 . . ?
C17 C16 H16 126.5 . . ?
C18 N6 C17 105.5(6) . . ?
N6 C18 N5 111.8(6) . . ?
N6 C18 H18 124.1 . . ?
N5 C18 H18 124.1 . . ?
O1 C19 C20 125.9(6) . . ?
O1 C19 C24 122.0(6) . . ?
C20 C19 C24 112.1(5) . . ?
C21 C20 C19 125.1(6) . . ?
C21 C20 N7 116.8(6) . . ?
C19 C20 N7 118.0(6) . . ?
C20 C21 C22 118.9(6) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 120.6(6) . . ?
C23 C22 N8 119.9(5) . . ?
C21 C22 N8 119.5(5) . . ?
C22 C23 C24 120.8(5) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 N9 116.1(5) . . ?
C23 C24 C19 122.3(5) . . ?
N9 C24 C19 121.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.065
