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

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

data_j11
_database_code_depnum_ccdc_archive 'CCDC 1423968'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2015-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H28 N4'
_chemical_formula_weight         445.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   10.4431(6)
_cell_length_b                   16.6727(9)
_cell_length_c                   14.0282(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.453(4)
_cell_angle_gamma                90.00
_cell_volume                     2409.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2993
_cell_measurement_theta_min      4.15
_cell_measurement_theta_max      65.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             948
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9199
_exptl_absorpt_correction_T_max  0.9456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD ApexII'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14491
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.15
_diffrn_reflns_theta_max         67.51
_reflns_number_total             4216
_reflns_number_gt                2781
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0830P)²+0.2893P] 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         4216
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1436
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001

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
C6 C 0.2496(2) -0.02160(12) -0.08584(15) 0.0584(5) Uani 1 1 d . . .
N3 N 0.5346(2) 0.22470(11) -0.00975(14) 0.0720(5) Uani 1 1 d . . .
N2 N 0.8228(2) 0.50855(11) 0.09467(14) 0.0745(6) Uani 1 1 d . . .
N4 N -0.0068(3) -0.20878(15) -0.2125(2) 0.1092(9) Uani 1 1 d . . .
C1 C 0.0922(3) -0.18399(16) -0.2528(2) 0.0875(8) Uani 1 1 d . . .
H1 H 0.1051 -0.2080 -0.3103 0.105 Uiso 1 1 calc R . .
C2 C 0.1772(2) -0.12467(14) -0.21467(18) 0.0722(6) Uani 1 1 d . . .
H2 H 0.2449 -0.1099 -0.2465 0.087 Uiso 1 1 calc R . .
C3 C 0.1624(2) -0.08667(13) -0.12879(16) 0.0637(6) Uani 1 1 d . . .
C11 C 0.2688(2) -0.00621(13) 0.01313(16) 0.0685(6) Uani 1 1 d . . .
H11 H 0.2268 -0.0377 0.0532 0.082 Uiso 1 1 calc R . .
C10 C 0.3490(2) 0.05499(13) 0.05249(17) 0.0688(6) Uani 1 1 d . . .
H10 H 0.3616 0.0636 0.1189 0.083 Uiso 1 1 calc R . .
C9 C 0.4109(2) 0.10378(12) -0.00498(16) 0.0598(5) Uani 1 1 d . . .
C12 C 0.4961(2) 0.16892(13) 0.03820(17) 0.0655(6) Uani 1 1 d . . .
H12 H 0.5228 0.1687 0.1048 0.079 Uiso 1 1 calc R . .
C13 C 0.6174(2) 0.28636(13) 0.04259(18) 0.0684(6) Uani 1 1 d . . .
H13 H 0.6473 0.2680 0.1089 0.082 Uiso 1 1 calc R . .
C14 C 0.5403(2) 0.36269(14) 0.04528(19) 0.0739(6) Uani 1 1 d . . .
H14A H 0.4697 0.3533 0.0809 0.089 Uiso 1 1 calc R . .
H14B H 0.5029 0.3779 -0.0201 0.089 Uiso 1 1 calc R . .
C15 C 0.6245(2) 0.43108(14) 0.0926(2) 0.0766(7) Uani 1 1 d . . .
H15A H 0.5729 0.4797 0.0897 0.092 Uiso 1 1 calc R . .
H15B H 0.6540 0.4184 0.1601 0.092 Uiso 1 1 calc R . .
C16 C 0.7407(3) 0.44566(14) 0.04365(18) 0.0745(7) Uani 1 1 d . . .
H16 H 0.7108 0.4627 -0.0231 0.089 Uiso 1 1 calc R . .
C19 C 0.8154(2) 0.57722(14) 0.05739(18) 0.0703(6) Uani 1 1 d . . .
H19 H 0.7595 0.5846 -0.0008 0.084 Uiso 1 1 calc R . .
C20 C 0.8905(2) 0.64680(13) 0.10095(17) 0.0648(6) Uani 1 1 d . . .
C21 C 1.0060(2) 0.63693(13) 0.16566(17) 0.0672(6) Uani 1 1 d . . .
H21 H 1.0343 0.5855 0.1844 0.081 Uiso 1 1 calc R . .
C22 C 1.0782(2) 0.70180(13) 0.20200(17) 0.0669(6) Uani 1 1 d . . .
H22 H 1.1553 0.6936 0.2444 0.080 Uiso 1 1 calc R . .
C23 C 1.0384(2) 0.78017(12) 0.17666(16) 0.0595(5) Uani 1 1 d . . .
C26 C 1.1191(2) 0.85035(12) 0.21328(16) 0.0597(5) Uani 1 1 d . . .
C27 C 1.2528(2) 0.84471(14) 0.24015(18) 0.0726(6) Uani 1 1 d . . .
H27 H 1.2944 0.7960 0.2346 0.087 Uiso 1 1 calc R . .
C28 C 1.3241(3) 0.91115(15) 0.2749(2) 0.0806(7) Uani 1 1 d . . .
H28 H 1.4133 0.9054 0.2929 0.097 Uiso 1 1 calc R . .
N1 N 1.2722(2) 0.98339(13) 0.28429(16) 0.0864(6) Uani 1 1 d . . .
C5 C -0.0217(3) -0.1726(2) -0.1301(2) 0.1096(11) Uani 1 1 d . . .
H5 H -0.0903 -0.1891 -0.1001 0.131 Uiso 1 1 calc R . .
C7 C 0.3150(2) 0.02713(12) -0.14322(16) 0.0609(5) Uani 1 1 d . . .
H7 H 0.3058 0.0172 -0.2092 0.073 Uiso 1 1 calc R . .
C8 C 0.3920(2) 0.08884(12) -0.10450(16) 0.0627(5) Uani 1 1 d . . .
H8 H 0.4323 0.1214 -0.1446 0.075 Uiso 1 1 calc R . .
C18 C 0.7335(3) 0.30077(16) -0.0066(2) 0.0926(9) Uani 1 1 d . . .
H18A H 0.7042 0.3145 -0.0738 0.111 Uiso 1 1 calc R . .
H18B H 0.7846 0.2521 -0.0045 0.111 Uiso 1 1 calc R . .
C17 C 0.8182(3) 0.36897(16) 0.0432(2) 0.0940(9) Uani 1 1 d . . .
H17A H 0.8524 0.3536 0.1092 0.113 Uiso 1 1 calc R . .
H17B H 0.8910 0.3780 0.0096 0.113 Uiso 1 1 calc R . .
C25 C 0.8498(2) 0.72339(14) 0.07589(19) 0.0738(7) Uani 1 1 d . . .
H25 H 0.7733 0.7310 0.0325 0.089 Uiso 1 1 calc R . .
C24 C 0.9209(2) 0.78974(13) 0.11425(19) 0.0713(6) Uani 1 1 d . . .
H24 H 0.8898 0.8411 0.0981 0.086 Uiso 1 1 calc R . .
C29 C 1.1441(3) 0.98827(15) 0.25781(19) 0.0805(7) Uani 1 1 d . . .
H29 H 1.1049 1.0377 0.2635 0.097 Uiso 1 1 calc R . .
C30 C 1.0663(2) 0.92515(13) 0.22270(18) 0.0695(6) Uani 1 1 d . . .
H30 H 0.9774 0.9328 0.2051 0.083 Uiso 1 1 calc R . .
C4 C 0.0579(3) -0.11254(17) -0.0867(2) 0.0893(8) Uani 1 1 d . . .
H4 H 0.0418 -0.0894 -0.0295 0.107 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
C6 C11 1.394(3) . ?
C6 C7 1.399(3) . ?
C6 C3 1.480(3) . ?
N3 C12 1.252(3) . ?
N3 C13 1.461(3) . ?
N2 C19 1.256(3) . ?
N2 C16 1.465(3) . ?
N4 C1 1.323(4) . ?
N4 C5 1.335(4) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C11 C10 1.377(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.379(3) . ?
C10 H10 0.9300 . ?
C9 C8 1.400(3) . ?
C9 C12 1.470(3) . ?
C12 H12 0.9300 . ?
C13 C18 1.509(3) . ?
C13 C14 1.509(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.524(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.509(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.513(3) . ?
C16 H16 0.9800 . ?
C19 C20 1.476(3) . ?
C19 H19 0.9300 . ?
C20 C25 1.373(3) . ?
C20 C21 1.395(3) . ?
C21 C22 1.368(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.399(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.394(3) . ?
C23 C26 1.484(3) . ?
C26 C30 1.378(3) . ?
C26 C27 1.389(3) . ?
C27 C28 1.378(3) . ?
C27 H27 0.9300 . ?
C28 N1 1.336(3) . ?
C28 H28 0.9300 . ?
N1 C29 1.330(3) . ?
C5 C4 1.379(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.362(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C18 C17 1.536(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C25 C24 1.391(3) . ?
C25 H25 0.9300 . ?
C24 H24 0.9300 . ?
C29 C30 1.371(3) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C4 H4 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
C11 C6 C7 117.55(19) . . ?
C11 C6 C3 121.3(2) . . ?
C7 C6 C3 121.19(19) . . ?
C12 N3 C13 117.9(2) . . ?
C19 N2 C16 117.3(2) . . ?
C1 N4 C5 116.1(2) . . ?
N4 C1 C2 123.9(3) . . ?
N4 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 115.6(2) . . ?
C4 C3 C6 121.8(2) . . ?
C2 C3 C6 122.5(2) . . ?
C10 C11 C6 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C9 C10 C11 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 C12 120.3(2) . . ?
C8 C9 C12 121.3(2) . . ?
N3 C12 C9 123.6(2) . . ?
N3 C12 H12 118.2 . . ?
C9 C12 H12 118.2 . . ?
N3 C13 C18 109.6(2) . . ?
N3 C13 C14 109.40(19) . . ?
C18 C13 C14 110.4(2) . . ?
N3 C13 H13 109.1 . . ?
C18 C13 H13 109.1 . . ?
C14 C13 H13 109.1 . . ?
C13 C14 C15 111.71(19) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 111.8(2) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N2 C16 C15 110.1(2) . . ?
N2 C16 C17 109.7(2) . . ?
C15 C16 C17 109.6(2) . . ?
N2 C16 H16 109.2 . . ?
C15 C16 H16 109.2 . . ?
C17 C16 H16 109.2 . . ?
N2 C19 C20 123.5(2) . . ?
N2 C19 H19 118.2 . . ?
C20 C19 H19 118.2 . . ?
C25 C20 C21 118.3(2) . . ?
C25 C20 C19 120.3(2) . . ?
C21 C20 C19 121.4(2) . . ?
C22 C21 C20 120.9(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 121.4(2) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 117.4(2) . . ?
C24 C23 C26 121.22(19) . . ?
C22 C23 C26 121.35(19) . . ?
C30 C26 C27 115.8(2) . . ?
C30 C26 C23 122.3(2) . . ?
C27 C26 C23 121.96(19) . . ?
C28 C27 C26 120.1(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
N1 C28 C27 123.7(2) . . ?
N1 C28 H28 118.1 . . ?
C27 C28 H28 118.1 . . ?
C29 N1 C28 115.7(2) . . ?
N4 C5 C4 124.2(3) . . ?
N4 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C13 C18 C17 110.8(2) . . ?
C13 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C16 C17 C18 111.0(2) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C20 C25 C24 121.2(2) . . ?
C20 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C24 C23 120.7(2) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
N1 C29 C30 124.2(2) . . ?
N1 C29 H29 117.9 . . ?
C30 C29 H29 117.9 . . ?
C29 C30 C26 120.4(2) . . ?
C29 C30 H30 119.8 . . ?
C26 C30 H30 119.8 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?

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 N4 C1 C2 0.0(5) . . . . ?
N4 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C6 -178.9(2) . . . . ?
C11 C6 C3 C4 27.4(3) . . . . ?
C7 C6 C3 C4 -152.1(2) . . . . ?
C11 C6 C3 C2 -154.2(2) . . . . ?
C7 C6 C3 C2 26.3(3) . . . . ?
C7 C6 C11 C10 0.2(3) . . . . ?
C3 C6 C11 C10 -179.3(2) . . . . ?
C6 C11 C10 C9 1.1(4) . . . . ?
C11 C10 C9 C8 -1.0(3) . . . . ?
C11 C10 C9 C12 179.9(2) . . . . ?
C13 N3 C12 C9 179.0(2) . . . . ?
C10 C9 C12 N3 -165.4(2) . . . . ?
C8 C9 C12 N3 15.5(3) . . . . ?
C12 N3 C13 C18 132.2(2) . . . . ?
C12 N3 C13 C14 -106.6(2) . . . . ?
N3 C13 C14 C15 -175.8(2) . . . . ?
C18 C13 C14 C15 -55.1(3) . . . . ?
C13 C14 C15 C16 55.8(3) . . . . ?
C19 N2 C16 C15 -102.4(3) . . . . ?
C19 N2 C16 C17 136.9(2) . . . . ?
C14 C15 C16 N2 -176.7(2) . . . . ?
C14 C15 C16 C17 -56.0(3) . . . . ?
C16 N2 C19 C20 179.1(2) . . . . ?
N2 C19 C20 C25 -158.8(3) . . . . ?
N2 C19 C20 C21 23.3(4) . . . . ?
C25 C20 C21 C22 -1.1(4) . . . . ?
C19 C20 C21 C22 176.8(2) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
C21 C22 C23 C24 1.1(3) . . . . ?
C21 C22 C23 C26 -177.7(2) . . . . ?
C24 C23 C26 C30 27.1(3) . . . . ?
C22 C23 C26 C30 -154.1(2) . . . . ?
C24 C23 C26 C27 -152.8(2) . . . . ?
C22 C23 C26 C27 26.0(3) . . . . ?
C30 C26 C27 C28 0.9(4) . . . . ?
C23 C26 C27 C28 -179.2(2) . . . . ?
C26 C27 C28 N1 -0.6(4) . . . . ?
C27 C28 N1 C29 0.2(4) . . . . ?
C1 N4 C5 C4 0.3(5) . . . . ?
C11 C6 C7 C8 -1.8(3) . . . . ?
C3 C6 C7 C8 177.7(2) . . . . ?
C6 C7 C8 C9 2.0(3) . . . . ?
C10 C9 C8 C7 -0.6(3) . . . . ?
C12 C9 C8 C7 178.54(19) . . . . ?
N3 C13 C18 C17 176.6(2) . . . . ?
C14 C13 C18 C17 56.0(3) . . . . ?
N2 C16 C17 C18 177.9(2) . . . . ?
C15 C16 C17 C18 57.0(3) . . . . ?
C13 C18 C17 C16 -57.8(3) . . . . ?
C21 C20 C25 C24 -0.4(4) . . . . ?
C19 C20 C25 C24 -178.4(2) . . . . ?
C20 C25 C24 C23 2.4(4) . . . . ?
C22 C23 C24 C25 -2.7(4) . . . . ?
C26 C23 C24 C25 176.2(2) . . . . ?
C28 N1 C29 C30 -0.1(4) . . . . ?
N1 C29 C30 C26 0.4(4) . . . . ?
C27 C26 C30 C29 -0.8(3) . . . . ?
C23 C26 C30 C29 179.3(2) . . . . ?
N4 C5 C4 C3 -0.6(5) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C6 C3 C4 C5 179.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        67.51
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.033
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CHCl3
_database_code_depnum_ccdc_archive 'CCDC 1423969'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2015-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H30 Cl6 I2 N4 Zn'
_chemical_formula_weight         1002.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   19.7541(13)
_cell_length_b                   7.1001(5)
_cell_length_c                   28.463(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.329(4)
_cell_angle_gamma                90.00
_cell_volume                     3789.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4723
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      65.47

_exptl_crystal_description       block
_exptl_crystal_colour            white-yellow
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1952
_exptl_absorpt_coefficient_mu    17.809
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4696
_exptl_absorpt_correction_T_max  0.5361
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10881
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         4.72
_diffrn_reflns_theta_max         66.31
_reflns_number_total             3271
_reflns_number_gt                2975
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0395P)²+51.3585P] 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         3271
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.5000 1.18932(17) 0.2500 0.0225(3) Uani 1 2 d S . .
I1 I 0.60619(2) 1.36653(7) 0.307691(19) 0.03576(17) Uani 1 1 d . . .
Cl1 Cl 0.90589(10) 0.1774(3) 0.06613(8) 0.0428(5) Uani 1 1 d . . .
Cl2 Cl 0.95161(10) 0.5654(3) 0.08511(7) 0.0396(4) Uani 1 1 d . . .
Cl3 Cl 1.02680(10) 0.3102(3) 0.03933(8) 0.0472(5) Uani 1 1 d . . .
N1 N 0.4554(3) 1.0014(8) 0.2869(2) 0.0242(12) Uani 1 1 d . . .
C3 C 0.3896(4) 1.0238(10) 0.2917(3) 0.0277(15) Uani 1 1 d . . .
H3 H 0.3653 1.1394 0.2812 0.033 Uiso 1 1 calc R . .
C4 C 0.3567(4) 0.8887(11) 0.3107(3) 0.0308(16) Uani 1 1 d . . .
H4 H 0.3108 0.9118 0.3135 0.037 Uiso 1 1 calc R . .
C5 C 0.3903(4) 0.7165(10) 0.3260(2) 0.0251(14) Uani 1 1 d . . .
C6 C 0.3575(4) 0.5621(10) 0.3463(2) 0.0259(14) Uani 1 1 d . . .
C7 C 0.4004(4) 0.4376(10) 0.3820(2) 0.0247(14) Uani 1 1 d . . .
H7 H 0.4507 0.4518 0.3925 0.030 Uiso 1 1 calc R . .
C8 C 0.3708(4) 0.2975(10) 0.4018(3) 0.0262(14) Uani 1 1 d . . .
H8 H 0.4007 0.2158 0.4259 0.031 Uiso 1 1 calc R . .
C9 C 0.2964(4) 0.2723(10) 0.3868(3) 0.0260(14) Uani 1 1 d . . .
C10 C 0.2545(4) 0.3915(12) 0.3514(3) 0.0355(17) Uani 1 1 d . . .
H10 H 0.2043 0.3737 0.3402 0.043 Uiso 1 1 calc R . .
C11 C 0.2837(4) 0.5361(11) 0.3317(3) 0.0314(16) Uani 1 1 d . . .
H11 H 0.2534 0.6188 0.3081 0.038 Uiso 1 1 calc R . .
C12 C 0.2637(4) 0.1244(10) 0.4090(3) 0.0264(14) Uani 1 1 d . . .
H12 H 0.2148 0.0956 0.3935 0.032 Uiso 1 1 calc R . .
N2 N 0.2970(3) 0.0345(8) 0.4473(2) 0.0253(12) Uani 1 1 d . . .
C14 C 0.2564(3) -0.1086(10) 0.4638(3) 0.0249(14) Uani 1 1 d . . .
H14 H 0.2079 -0.1186 0.4388 0.030 Uiso 1 1 calc R . .
C15 C 0.2932(4) -0.2980(9) 0.4679(3) 0.0251(14) Uani 1 1 d . . .
H15A H 0.3423 -0.2883 0.4912 0.030 Uiso 1 1 calc R . .
H15B H 0.2963 -0.3350 0.4351 0.030 Uiso 1 1 calc R . .
C16 C 0.2519(4) -0.4490(10) 0.4863(3) 0.0257(14) Uani 1 1 d . . .
H16A H 0.2042 -0.4663 0.4617 0.031 Uiso 1 1 calc R . .
H16B H 0.2776 -0.5705 0.4901 0.031 Uiso 1 1 calc R . .
C17 C 0.4582(4) 0.6962(11) 0.3215(2) 0.0280(15) Uani 1 1 d . . .
H17 H 0.4835 0.5816 0.3314 0.034 Uiso 1 1 calc R . .
C18 C 0.4885(3) 0.8367(10) 0.3031(2) 0.0260(14) Uani 1 1 d . . .
H18 H 0.5354 0.8187 0.3016 0.031 Uiso 1 1 calc R . .
C19 C 0.9427(4) 0.3730(12) 0.0441(3) 0.0342(17) Uani 1 1 d . . .
H19 H 0.9103 0.4095 0.0107 0.041 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
Zn1 N1 2.060(6) 2_655 ?
Zn1 N1 2.060(6) . ?
Zn1 I1 2.5521(8) . ?
Zn1 I1 2.5521(8) 2_655 ?
Cl1 C19 1.771(8) . ?
Cl2 C19 1.769(8) . ?
Cl3 C19 1.766(7) . ?
N1 C18 1.348(9) . ?
N1 C3 1.357(9) . ?
C3 C4 1.363(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(10) . ?
C4 H4 0.9500 . ?
C5 C17 1.394(10) . ?
C5 C6 1.480(10) . ?
C6 C11 1.396(10) . ?
C6 C7 1.411(9) . ?
C7 C8 1.362(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.406(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(11) . ?
C9 C12 1.475(10) . ?
C10 C11 1.379(11) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 N2 1.255(9) . ?
C12 H12 0.9500 . ?
N2 C14 1.461(8) . ?
C14 C15 1.516(9) . ?
C14 C16 1.533(9) 7_546 ?
C14 H14 1.0000 . ?
C15 C16 1.536(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C14 1.533(9) 7_546 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.350(10) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19 1.0000 . ?

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 Zn1 N1 99.3(3) 2_655 . ?
N1 Zn1 I1 104.51(15) 2_655 . ?
N1 Zn1 I1 112.83(15) . . ?
N1 Zn1 I1 112.83(15) 2_655 2_655 ?
N1 Zn1 I1 104.52(15) . 2_655 ?
I1 Zn1 I1 120.92(5) . 2_655 ?
C18 N1 C3 116.4(6) . . ?
C18 N1 Zn1 119.8(4) . . ?
C3 N1 Zn1 123.5(5) . . ?
N1 C3 C4 123.2(7) . . ?
N1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 120.1(6) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C17 116.0(7) . . ?
C4 C5 C6 123.2(6) . . ?
C17 C5 C6 120.7(6) . . ?
C11 C6 C7 117.7(7) . . ?
C11 C6 C5 121.8(6) . . ?
C7 C6 C5 120.5(6) . . ?
C8 C7 C6 121.1(6) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.8(6) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 118.2(7) . . ?
C10 C9 C12 120.6(6) . . ?
C8 C9 C12 121.2(6) . . ?
C9 C10 C11 121.6(7) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C6 120.6(7) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
N2 C12 C9 123.6(6) . . ?
N2 C12 H12 118.2 . . ?
C9 C12 H12 118.2 . . ?
C12 N2 C14 116.2(6) . . ?
N2 C14 C15 110.1(5) . . ?
N2 C14 C16 109.9(5) . 7_546 ?
C15 C14 C16 110.8(6) . 7_546 ?
N2 C14 H14 108.7 . . ?
C15 C14 H14 108.7 . . ?
C16 C14 H14 108.7 7_546 . ?
C14 C15 C16 110.6(5) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C14 C16 C15 110.6(6) 7_546 . ?
C14 C16 H16A 109.5 7_546 . ?
C15 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 7_546 . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C5 121.0(7) . . ?
C18 C17 H17 119.5 . . ?
C5 C17 H17 119.5 . . ?
N1 C18 C17 123.1(6) . . ?
N1 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
Cl3 C19 Cl2 110.2(4) . . ?
Cl3 C19 Cl1 109.3(4) . . ?
Cl2 C19 Cl1 109.8(4) . . ?
Cl3 C19 H19 109.2 . . ?
Cl2 C19 H19 109.2 . . ?
Cl1 C19 H19 109.2 . . ?

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
N1 Zn1 N1 C18 34.4(4) 2_655 . . . ?
I1 Zn1 N1 C18 -75.7(5) . . . . ?
I1 Zn1 N1 C18 151.1(5) 2_655 . . . ?
N1 Zn1 N1 C3 -138.3(6) 2_655 . . . ?
I1 Zn1 N1 C3 111.6(5) . . . . ?
I1 Zn1 N1 C3 -21.6(6) 2_655 . . . ?
C18 N1 C3 C4 -1.3(10) . . . . ?
Zn1 N1 C3 C4 171.6(6) . . . . ?
N1 C3 C4 C5 -0.6(12) . . . . ?
C3 C4 C5 C17 1.2(10) . . . . ?
C3 C4 C5 C6 -179.0(7) . . . . ?
C4 C5 C6 C11 30.1(11) . . . . ?
C17 C5 C6 C11 -150.2(7) . . . . ?
C4 C5 C6 C7 -148.6(7) . . . . ?
C17 C5 C6 C7 31.1(10) . . . . ?
C11 C6 C7 C8 -0.2(11) . . . . ?
C5 C6 C7 C8 178.6(6) . . . . ?
C6 C7 C8 C9 0.3(11) . . . . ?
C7 C8 C9 C10 0.8(11) . . . . ?
C7 C8 C9 C12 -178.2(7) . . . . ?
C8 C9 C10 C11 -2.0(12) . . . . ?
C12 C9 C10 C11 177.0(7) . . . . ?
C9 C10 C11 C6 2.1(12) . . . . ?
C7 C6 C11 C10 -1.0(11) . . . . ?
C5 C6 C11 C10 -179.7(7) . . . . ?
C10 C9 C12 N2 -166.6(7) . . . . ?
C8 C9 C12 N2 12.4(11) . . . . ?
C9 C12 N2 C14 -179.3(6) . . . . ?
C12 N2 C14 C15 124.2(7) . . . . ?
C12 N2 C14 C16 -113.5(7) . . . 7_546 ?
N2 C14 C15 C16 178.8(6) . . . . ?
C16 C14 C15 C16 57.0(8) 7_546 . . . ?
C14 C15 C16 C14 -56.9(8) . . . 7_546 ?
C4 C5 C17 C18 -0.1(10) . . . . ?
C6 C5 C17 C18 -179.8(6) . . . . ?
C3 N1 C18 C17 2.5(10) . . . . ?
Zn1 N1 C18 C17 -170.7(5) . . . . ?
C5 C17 C18 N1 -1.9(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        66.31
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         1.552
_refine_diff_density_min         -0.971
_refine_diff_density_rms         0.134
