# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_5
_database_code_depnum_ccdc_archive 'CCDC 861142'
_audit_update_record             
;
2012-01-05 deposited with the CCDC.
2016-06-30 downloaded from the CCDC.
;
#TrackingRef '5.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H42 Br4 N6 O Zn2'
_chemical_formula_sum            'C39 H42 Br4 N6 O Zn2'
_chemical_formula_weight         1061.17

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'
Zn Zn 0.2839 1.4301 '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                   8.7790(18)
_cell_length_b                   13.826(3)
_cell_length_c                   17.180(3)
_cell_angle_alpha                83.27(3)
_cell_angle_beta                 83.26(3)
_cell_angle_gamma                88.18(3)
_cell_volume                     2056.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1052
_exptl_absorpt_coefficient_mu    5.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.237
_exptl_absorpt_correction_T_max  0.543
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11447
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_sigmaI/netI    0.1543
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.01
_reflns_number_total             7268
_reflns_number_gt                3886
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0337P)²+0.0000P] 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         7074
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1283
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
C39 C 0.6979(12) 0.3737(8) 0.2768(7) 0.095(4) Uani 1 1 d . . .
H39A H 0.7252 0.3166 0.3100 0.143 Uiso 1 1 calc R . .
H39B H 0.6984 0.3582 0.2237 0.143 Uiso 1 1 calc R . .
H39C H 0.5973 0.3963 0.2956 0.143 Uiso 1 1 calc R . .
Br2 Br 0.66739(14) 0.53867(7) 0.82081(7) 0.0811(4) Uani 1 1 d . . .
Br4 Br 0.19043(11) 0.89033(6) 0.52519(6) 0.0573(3) Uani 1 1 d . . .
Zn2 Zn 0.15770(10) 0.74200(6) 0.46782(6) 0.0335(3) Uani 1 1 d . . .
Br3 Br 0.02730(10) 0.61809(6) 0.56174(5) 0.0472(3) Uani 1 1 d . . .
Zn1 Zn 0.65663(11) 0.69208(7) 0.87472(6) 0.0423(3) Uani 1 1 d . . .
Br1 Br 0.42351(11) 0.74531(8) 0.94641(7) 0.0736(4) Uani 1 1 d . . .
C15 C 0.7664(10) 0.8017(6) 0.7199(5) 0.045(2) Uani 1 1 d . . .
N6 N 0.3856(7) 0.6861(5) 0.4686(4) 0.0350(17) Uani 1 1 d . . .
C34 C 0.4262(9) 0.6189(5) 0.4193(5) 0.034(2) Uani 1 1 d . . .
N2 N 0.7839(8) 0.6471(5) 0.9706(4) 0.0457(19) Uani 1 1 d . . .
C28 C -0.0569(9) 0.7333(6) 0.3452(5) 0.034(2) Uani 1 1 d . . .
N1 N 0.8995(7) 0.7582(4) 0.8335(4) 0.0374(18) Uani 1 1 d . . .
N5 N -0.0344(7) 0.7861(4) 0.4029(4) 0.0368(17) Uani 1 1 d . . .
C25 C 0.2857(8) 0.8454(6) 0.2937(5) 0.036(2) Uani 1 1 d . . .
H25 H 0.2293 0.8681 0.3374 0.043 Uiso 1 1 calc R . .
C32 C -0.1375(10) 0.8566(6) 0.4229(5) 0.046(2) Uani 1 1 d . . .
H32 H -0.1200 0.8945 0.4622 0.055 Uiso 1 1 calc R . .
C35 C 0.5700(9) 0.5747(6) 0.4156(6) 0.049(3) Uani 1 1 d . . .
H35 H 0.5995 0.5306 0.3795 0.058 Uiso 1 1 calc R . .
N4 N 0.2098(7) 0.6800(4) 0.3497(4) 0.0336(17) Uani 1 1 d . . .
N3 N 0.6359(8) 0.7845(4) 0.7681(4) 0.0412(18) Uani 1 1 d . . .
C21 C 0.4476(9) 0.8785(6) 0.1710(5) 0.042(2) Uani 1 1 d . . .
C36 C 0.6684(10) 0.5983(6) 0.4673(6) 0.048(3) Uani 1 1 d . . .
H36 H 0.7648 0.5683 0.4668 0.057 Uiso 1 1 calc R . .
C9 C 0.9373(11) 0.6547(6) 0.9581(6) 0.045(2) Uani 1 1 d . . .
C33 C 0.3044(9) 0.5938(5) 0.3725(5) 0.041(2) Uani 1 1 d . . .
H33A H 0.3511 0.5671 0.3255 0.049 Uiso 1 1 calc R . .
H33B H 0.2396 0.5444 0.4034 0.049 Uiso 1 1 calc R . .
C38 C 0.4833(9) 0.7071(6) 0.5170(5) 0.042(2) Uani 1 1 d . . .
H38 H 0.4534 0.7531 0.5514 0.050 Uiso 1 1 calc R . .
C24 C 0.2935(9) 0.7471(5) 0.2867(5) 0.035(2) Uani 1 1 d . . .
C37 C 0.6272(9) 0.6644(6) 0.5190(6) 0.047(3) Uani 1 1 d . . .
H37 H 0.6930 0.6802 0.5541 0.056 Uiso 1 1 calc R . .
C23 C 0.3794(12) 0.7167(6) 0.2235(5) 0.064(3) Uani 1 1 d . . .
H23 H 0.3872 0.6505 0.2180 0.077 Uiso 1 1 calc R . .
C31 C -0.2666(11) 0.8726(7) 0.3858(6) 0.060(3) Uani 1 1 d . . .
H31 H -0.3382 0.9202 0.4001 0.071 Uiso 1 1 calc R . .
C22 C 0.4556(11) 0.7824(7) 0.1669(6) 0.069(3) Uani 1 1 d . . .
H22 H 0.5148 0.7592 0.1242 0.083 Uiso 1 1 calc R . .
C26 C 0.3609(9) 0.9098(6) 0.2363(5) 0.046(2) Uani 1 1 d . . .
H26 H 0.3536 0.9761 0.2414 0.056 Uiso 1 1 calc R . .
C27 C 0.0618(9) 0.6539(6) 0.3283(5) 0.044(2) Uani 1 1 d . . .
H27A H 0.0290 0.5928 0.3583 0.053 Uiso 1 1 calc R . .
H27B H 0.0714 0.6453 0.2727 0.053 Uiso 1 1 calc R . .
C13 C 0.7184(12) 0.6098(6) 1.0423(6) 0.059(3) Uani 1 1 d . . .
H13 H 0.6123 0.6042 1.0512 0.071 Uiso 1 1 calc R . .
C12 C 0.8048(15) 0.5800(7) 1.1019(6) 0.074(3) Uani 1 1 d . . .
H12 H 0.7576 0.5556 1.1513 0.088 Uiso 1 1 calc R . .
C20 C 0.5384(10) 0.9497(6) 0.1102(5) 0.072(3) Uani 1 1 d . . .
H20A H 0.6413 0.9528 0.1235 0.108 Uiso 1 1 calc R . .
H20B H 0.4906 1.0131 0.1099 0.108 Uiso 1 1 calc R . .
H20C H 0.5409 0.9281 0.0590 0.108 Uiso 1 1 calc R . .
C5 C 0.9185(9) 0.8576(6) 0.8525(5) 0.038(2) Uani 1 1 d . . .
C19 C 0.5060(11) 0.8258(6) 0.7450(6) 0.057(3) Uani 1 1 d . . .
H19 H 0.4159 0.8168 0.7791 0.068 Uiso 1 1 calc R . .
C18 C 0.4993(12) 0.8812(7) 0.6730(6) 0.063(3) Uani 1 1 d . . .
H18 H 0.4066 0.9055 0.6570 0.075 Uiso 1 1 calc R . .
C8 C 1.0020(9) 0.6876(6) 0.8741(5) 0.046(2) Uani 1 1 d . . .
H8A H 1.1007 0.7172 0.8741 0.055 Uiso 1 1 calc R . .
H8B H 1.0184 0.6313 0.8451 0.055 Uiso 1 1 calc R . .
C17 C 0.6349(13) 0.8989(7) 0.6264(6) 0.070(3) Uani 1 1 d . . .
H17 H 0.6355 0.9391 0.5790 0.084 Uiso 1 1 calc R . .
C14 C 0.9046(9) 0.7518(6) 0.7499(5) 0.053(3) Uani 1 1 d . . .
H14A H 0.9073 0.6840 0.7403 0.063 Uiso 1 1 calc R . .
H14B H 0.9967 0.7823 0.7223 0.063 Uiso 1 1 calc R . .
C6 C 0.8258(10) 0.8921(6) 0.9127(5) 0.051(3) Uani 1 1 d . . .
H6 H 0.7510 0.8523 0.9419 0.061 Uiso 1 1 calc R . .
C16 C 0.7712(12) 0.8580(7) 0.6486(6) 0.064(3) Uani 1 1 d . . .
H16 H 0.8631 0.8683 0.6162 0.076 Uiso 1 1 calc R . .
C4 C 1.0291(10) 0.9162(6) 0.8093(6) 0.071(3) Uani 1 1 d . . .
H4 H 1.0955 0.8929 0.7692 0.085 Uiso 1 1 calc R . .
C3 C 1.0395(12) 1.0116(7) 0.8269(7) 0.088(4) Uani 1 1 d . . .
H3 H 1.1093 1.0530 0.7956 0.106 Uiso 1 1 calc R . .
C29 C -0.1814(10) 0.7459(6) 0.3055(5) 0.049(2) Uani 1 1 d . . .
H29 H -0.1943 0.7084 0.2653 0.059 Uiso 1 1 calc R . .
C30 C -0.2895(11) 0.8166(7) 0.3265(7) 0.065(3) Uani 1 1 d . . .
H30 H -0.3772 0.8263 0.3009 0.078 Uiso 1 1 calc R . .
C10 C 1.0277(11) 0.6261(6) 1.0156(6) 0.053(3) Uani 1 1 d . . .
H10 H 1.1334 0.6331 1.0060 0.064 Uiso 1 1 calc R . .
C11 C 0.9607(14) 0.5863(7) 1.0889(7) 0.066(3) Uani 1 1 d . . .
H11 H 1.0210 0.5643 1.1286 0.079 Uiso 1 1 calc R . .
O1 O 0.8054(9) 0.4477(6) 0.2781(5) 0.102(3) Uani 1 1 d . . .
H1 H 0.7597 0.4980 0.2888 0.153 Uiso 1 1 calc R . .
C7 C 0.8420(10) 0.9864(6) 0.9308(5) 0.052(3) Uani 1 1 d . . .
H7 H 0.7783 1.0094 0.9721 0.062 Uiso 1 1 calc R . .
C2 C 0.9512(11) 1.0456(6) 0.8881(6) 0.053(3) Uani 1 1 d . . .
C1 C 0.9618(11) 1.1507(6) 0.9049(6) 0.079(3) Uani 1 1 d . . .
H1A H 1.0658 1.1640 0.9117 0.118 Uiso 1 1 calc R . .
H1B H 0.8962 1.1607 0.9521 0.118 Uiso 1 1 calc R . .
H1C H 0.9303 1.1938 0.8614 0.118 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
C39 O1 1.418(11) . ?
Br2 Zn1 2.4068(15) . ?
Br4 Zn2 2.4162(14) . ?
Zn2 N6 2.123(6) . ?
Zn2 N5 2.163(7) . ?
Zn2 N4 2.286(6) . ?
Zn2 Br3 2.4274(15) . ?
Zn1 N2 2.121(7) . ?
Zn1 N3 2.129(6) . ?
Zn1 N1 2.346(6) . ?
Zn1 Br1 2.4027(15) . ?
C15 N3 1.343(9) . ?
C15 C16 1.369(11) . ?
C15 C14 1.491(11) . ?
N6 C38 1.323(10) . ?
N6 C34 1.342(10) . ?
C34 C35 1.382(10) . ?
C34 C33 1.483(11) . ?
N2 C9 1.344(10) . ?
N2 C13 1.348(10) . ?
C28 N5 1.334(10) . ?
C28 C29 1.351(10) . ?
C28 C27 1.519(10) . ?
N1 C14 1.444(10) . ?
N1 C5 1.468(9) . ?
N1 C8 1.476(9) . ?
N5 C32 1.355(9) . ?
C25 C26 1.370(10) . ?
C25 C24 1.378(10) . ?
C32 C31 1.364(11) . ?
C35 C36 1.381(12) . ?
N4 C27 1.459(9) . ?
N4 C33 1.472(8) . ?
N4 C24 1.481(9) . ?
N3 C19 1.340(10) . ?
C21 C22 1.338(11) . ?
C21 C26 1.385(11) . ?
C21 C20 1.519(10) . ?
C36 C37 1.359(12) . ?
C9 C10 1.354(11) . ?
C9 C8 1.512(11) . ?
C38 C37 1.379(10) . ?
C24 C23 1.349(10) . ?
C23 C22 1.378(12) . ?
C31 C30 1.385(13) . ?
C13 C12 1.363(12) . ?
C12 C11 1.365(13) . ?
C5 C6 1.361(10) . ?
C5 C4 1.376(10) . ?
C19 C18 1.383(11) . ?
C18 C17 1.366(12) . ?
C17 C16 1.383(12) . ?
C6 C7 1.392(11) . ?
C4 C3 1.394(12) . ?
C3 C2 1.353(12) . ?
C29 C30 1.390(12) . ?
C10 C11 1.384(13) . ?
C7 C2 1.368(11) . ?
C2 C1 1.522(11) . ?

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
N6 Zn2 N5 149.2(3) . . ?
N6 Zn2 N4 75.8(2) . . ?
N5 Zn2 N4 74.4(2) . . ?
N6 Zn2 Br4 98.17(19) . . ?
N5 Zn2 Br4 99.56(18) . . ?
N4 Zn2 Br4 139.61(16) . . ?
N6 Zn2 Br3 98.90(17) . . ?
N5 Zn2 Br3 97.38(16) . . ?
N4 Zn2 Br3 108.04(16) . . ?
Br4 Zn2 Br3 112.35(5) . . ?
N2 Zn1 N3 148.8(3) . . ?
N2 Zn1 N1 76.2(3) . . ?
N3 Zn1 N1 73.6(3) . . ?
N2 Zn1 Br1 99.4(2) . . ?
N3 Zn1 Br1 96.63(19) . . ?
N1 Zn1 Br1 135.57(16) . . ?
N2 Zn1 Br2 97.01(18) . . ?
N3 Zn1 Br2 97.83(19) . . ?
N1 Zn1 Br2 104.19(16) . . ?
Br1 Zn1 Br2 120.16(6) . . ?
N3 C15 C16 122.8(9) . . ?
N3 C15 C14 114.1(7) . . ?
C16 C15 C14 123.1(8) . . ?
C38 N6 C34 118.9(7) . . ?
C38 N6 Zn2 125.3(6) . . ?
C34 N6 Zn2 115.6(6) . . ?
N6 C34 C35 121.4(8) . . ?
N6 C34 C33 115.1(7) . . ?
C35 C34 C33 123.5(8) . . ?
C9 N2 C13 119.1(9) . . ?
C9 N2 Zn1 117.8(7) . . ?
C13 N2 Zn1 123.1(7) . . ?
N5 C28 C29 122.6(8) . . ?
N5 C28 C27 116.5(8) . . ?
C29 C28 C27 120.8(9) . . ?
C14 N1 C5 113.4(7) . . ?
C14 N1 C8 114.1(6) . . ?
C5 N1 C8 111.8(7) . . ?
C14 N1 Zn1 98.8(5) . . ?
C5 N1 Zn1 115.2(5) . . ?
C8 N1 Zn1 102.5(5) . . ?
C28 N5 C32 120.0(8) . . ?
C28 N5 Zn2 116.2(5) . . ?
C32 N5 Zn2 123.4(6) . . ?
C26 C25 C24 120.1(8) . . ?
N5 C32 C31 120.5(9) . . ?
C36 C35 C34 117.8(9) . . ?
C27 N4 C33 112.3(6) . . ?
C27 N4 C24 111.7(6) . . ?
C33 N4 C24 111.6(6) . . ?
C27 N4 Zn2 105.7(5) . . ?
C33 N4 Zn2 100.9(5) . . ?
C24 N4 Zn2 114.2(5) . . ?
C19 N3 C15 117.8(7) . . ?
C19 N3 Zn1 126.2(6) . . ?
C15 N3 Zn1 116.0(6) . . ?
C22 C21 C26 116.9(8) . . ?
C22 C21 C20 121.7(9) . . ?
C26 C21 C20 121.3(8) . . ?
C37 C36 C35 121.3(8) . . ?
N2 C9 C10 121.8(9) . . ?
N2 C9 C8 115.4(9) . . ?
C10 C9 C8 122.5(9) . . ?
N4 C33 C34 111.2(6) . . ?
N6 C38 C37 123.5(8) . . ?
C23 C24 C25 118.3(7) . . ?
C23 C24 N4 123.3(7) . . ?
C25 C24 N4 118.4(7) . . ?
C36 C37 C38 117.0(9) . . ?
C24 C23 C22 120.8(8) . . ?
C32 C31 C30 118.9(9) . . ?
C21 C22 C23 122.3(9) . . ?
C25 C26 C21 121.6(8) . . ?
N4 C27 C28 110.0(7) . . ?
N2 C13 C12 121.2(10) . . ?
C13 C12 C11 119.7(10) . . ?
C6 C5 C4 119.9(8) . . ?
C6 C5 N1 120.0(7) . . ?
C4 C5 N1 120.1(8) . . ?
N3 C19 C18 123.3(9) . . ?
C17 C18 C19 117.1(9) . . ?
N1 C8 C9 112.3(7) . . ?
C18 C17 C16 121.0(9) . . ?
N1 C14 C15 109.6(7) . . ?
C5 C6 C7 120.4(8) . . ?
C15 C16 C17 117.8(9) . . ?
C5 C4 C3 118.5(9) . . ?
C2 C3 C4 122.0(9) . . ?
C28 C29 C30 118.0(10) . . ?
C31 C30 C29 120.0(10) . . ?
C9 C10 C11 119.2(9) . . ?
C12 C11 C10 119.0(10) . . ?
C2 C7 C6 120.3(9) . . ?
C3 C2 C7 118.7(9) . . ?
C3 C2 C1 121.0(9) . . ?
C7 C2 C1 120.0(9) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.134
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 861143'
_audit_update_record             
;
2012-01-05 deposited with the CCDC.
2016-06-30 downloaded from the CCDC.
;
#TrackingRef '6.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H42 Cl4 N6 O Zn2'
_chemical_formula_sum            'C39 H42 Cl4 N6 O Zn2'
_chemical_formula_weight         883.33

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

_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                   8.5800(17)
_cell_length_b                   13.601(3)
_cell_length_c                   16.750(3)
_cell_angle_alpha                84.10(3)
_cell_angle_beta                 84.02(3)
_cell_angle_gamma                89.49(3)
_cell_volume                     1933.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             908
_exptl_absorpt_coefficient_mu    1.557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_T_max  0.830
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11090
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_sigmaI/netI    0.1500
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_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         3.04
_diffrn_reflns_theta_max         25.01
_reflns_number_total             6813
_reflns_number_gt                4506
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0579P)²+0.0000P] 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         6677
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.1876
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.003
_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
Zn2 Zn 0.84129(7) 0.75774(4) 0.52966(4) 0.0293(2) Uani 1 1 d . . .
Cl3 Cl 0.96518(18) 0.87782(11) 0.44340(10) 0.0445(4) Uani 1 1 d . . .
Cl4 Cl 0.8036(2) 0.61650(11) 0.47480(12) 0.0551(5) Uani 1 1 d . . .
N5 N 0.6138(5) 0.8141(3) 0.5300(3) 0.0313(12) Uani 1 1 d . . .
N4 N 0.7953(5) 0.8214(3) 0.6502(3) 0.0295(11) Uani 1 1 d . . .
N6 N 1.0331(5) 0.7123(3) 0.5949(3) 0.0332(12) Uani 1 1 d . . .
C34 C 1.0632(7) 0.7665(4) 0.6535(4) 0.0367(16) Uani 1 1 d . . .
C25 C 0.7158(7) 0.6556(4) 0.7083(4) 0.0342(15) Uani 1 1 d . . .
H25 H 0.7708 0.6299 0.6643 0.041 Uiso 1 1 calc R . .
C27 C 0.7038(7) 0.9104(4) 0.6265(4) 0.0384(16) Uani 1 1 d . . .
H27A H 0.7718 0.9591 0.5941 0.046 Uiso 1 1 calc R . .
H27B H 0.6591 0.9393 0.6743 0.046 Uiso 1 1 calc R . .
C24 C 0.7116(6) 0.7561(4) 0.7121(3) 0.0274(13) Uani 1 1 d . . .
C28 C 0.5753(7) 0.8822(4) 0.5790(4) 0.0312(14) Uani 1 1 d . . .
C21 C 0.5572(8) 0.6279(5) 0.8338(4) 0.0431(17) Uani 1 1 d . . .
C38 C 1.1304(7) 0.6403(4) 0.5765(4) 0.0453(18) Uani 1 1 d . . .
H38 H 1.1078 0.6014 0.5366 0.054 Uiso 1 1 calc R . .
C26 C 0.6396(7) 0.5934(4) 0.7687(4) 0.0380(16) Uani 1 1 d . . .
H26 H 0.6442 0.5256 0.7652 0.046 Uiso 1 1 calc R . .
C22 C 0.5577(10) 0.7265(5) 0.8373(4) 0.068(2) Uani 1 1 d . . .
H22 H 0.5032 0.7520 0.8815 0.082 Uiso 1 1 calc R . .
C29 C 0.4336(7) 0.9266(4) 0.5839(4) 0.0398(17) Uani 1 1 d . . .
H29 H 0.4085 0.9723 0.6208 0.048 Uiso 1 1 calc R . .
C30 C 0.3276(7) 0.9027(5) 0.5329(4) 0.0474(19) Uani 1 1 d . . .
H30 H 0.2304 0.9336 0.5341 0.057 Uiso 1 1 calc R . .
C33 C 0.9510(7) 0.8482(4) 0.6697(4) 0.0415(17) Uani 1 1 d . . .
H33A H 0.9459 0.8600 0.7260 0.050 Uiso 1 1 calc R . .
H33B H 0.9865 0.9085 0.6371 0.050 Uiso 1 1 calc R . .
C31 C 0.3643(7) 0.8344(5) 0.4811(4) 0.0458(18) Uani 1 1 d . . .
H31 H 0.2942 0.8175 0.4460 0.055 Uiso 1 1 calc R . .
C23 C 0.6350(9) 0.7902(5) 0.7787(4) 0.054(2) Uani 1 1 d . . .
H23 H 0.6353 0.8575 0.7843 0.065 Uiso 1 1 calc R . .
C36 C 1.2947(8) 0.6774(6) 0.6714(5) 0.063(2) Uani 1 1 d . . .
H36 H 1.3861 0.6668 0.6964 0.075 Uiso 1 1 calc R . .
C35 C 1.1936(7) 0.7508(5) 0.6934(4) 0.0458(18) Uani 1 1 d . . .
H35 H 1.2133 0.7889 0.7343 0.055 Uiso 1 1 calc R . .
C32 C 0.5090(7) 0.7910(4) 0.4823(4) 0.0412(16) Uani 1 1 d . . .
H32 H 0.5349 0.7427 0.4477 0.049 Uiso 1 1 calc R . .
C37 C 1.2631(8) 0.6208(5) 0.6141(5) 0.057(2) Uani 1 1 d . . .
H37 H 1.3297 0.5696 0.6003 0.069 Uiso 1 1 calc R . .
C20 C 0.4688(9) 0.5604(5) 0.8967(4) 0.070(2) Uani 1 1 d . . .
H20A H 0.4907 0.5761 0.9489 0.105 Uiso 1 1 calc R . .
H20B H 0.4994 0.4934 0.8899 0.105 Uiso 1 1 calc R . .
H20C H 0.3586 0.5677 0.8920 0.105 Uiso 1 1 calc R . .
Zn1 Zn 0.33766(9) 0.81345(5) 0.12888(5) 0.0416(3) Uani 1 1 d . . .
Cl1 Cl 0.3289(3) 0.95677(13) 0.18422(14) 0.0863(8) Uani 1 1 d . . .
Cl2 Cl 0.5568(2) 0.76532(17) 0.06036(13) 0.0752(7) Uani 1 1 d . . .
N2 N 0.2055(7) 0.8569(3) 0.0314(3) 0.0436(14) Uani 1 1 d . . .
N1 N 0.0947(6) 0.7455(3) 0.1682(3) 0.0385(13) Uani 1 1 d . . .
C15 C 0.2297(10) 0.6985(5) 0.2836(4) 0.0490(19) Uani 1 1 d . . .
N3 N 0.3604(7) 0.7168(4) 0.2361(3) 0.0427(14) Uani 1 1 d . . .
C5 C 0.0737(7) 0.6452(4) 0.1496(4) 0.0329(15) Uani 1 1 d . . .
C4 C 0.1674(8) 0.6102(4) 0.0879(4) 0.0455(17) Uani 1 1 d . . .
H4 H 0.2434 0.6507 0.0577 0.055 Uiso 1 1 calc R . .
C9 C 0.0510(8) 0.8480(4) 0.0452(4) 0.0412(17) Uani 1 1 d . . .
C3 C 0.1488(8) 0.5151(4) 0.0706(4) 0.0482(18) Uani 1 1 d . . .
H3 H 0.2134 0.4925 0.0283 0.058 Uiso 1 1 calc R . .
C10 C -0.0426(9) 0.8754(5) -0.0137(5) 0.056(2) Uani 1 1 d . . .
H10 H -0.1509 0.8693 -0.0036 0.067 Uiso 1 1 calc R . .
C14 C 0.0890(7) 0.7515(5) 0.2557(4) 0.0415(16) Uani 1 1 d . . .
H14A H -0.0060 0.7208 0.2833 0.050 Uiso 1 1 calc R . .
H14B H 0.0906 0.8200 0.2670 0.050 Uiso 1 1 calc R . .
C13 C 0.2679(10) 0.8930(5) -0.0416(4) 0.056(2) Uani 1 1 d . . .
H13 H 0.3763 0.8984 -0.0510 0.067 Uiso 1 1 calc R . .
C12 C 0.1815(12) 0.9223(5) -0.1026(5) 0.068(3) Uani 1 1 d . . .
H12 H 0.2286 0.9483 -0.1528 0.081 Uiso 1 1 calc R . .
C16 C 0.2262(10) 0.6385(5) 0.3538(4) 0.064(2) Uani 1 1 d . . .
H16 H 0.1331 0.6267 0.3871 0.076 Uiso 1 1 calc R . .
C8 C -0.0113(7) 0.8148(4) 0.1283(4) 0.0458(18) Uani 1 1 d . . .
H8A H -0.0277 0.8717 0.1586 0.055 Uiso 1 1 calc R . .
H8B H -0.1119 0.7830 0.1279 0.055 Uiso 1 1 calc R . .
C19 C 0.4930(9) 0.6742(4) 0.2563(5) 0.052(2) Uani 1 1 d . . .
H19 H 0.5846 0.6852 0.2217 0.062 Uiso 1 1 calc R . .
C6 C -0.0386(10) 0.5847(6) 0.1905(5) 0.075(2) Uani 1 1 d . . .
H6 H -0.1070 0.6076 0.2313 0.089 Uiso 1 1 calc R . .
C11 C 0.0249(12) 0.9124(5) -0.0884(5) 0.072(3) Uani 1 1 d . . .
H11 H -0.0378 0.9308 -0.1294 0.086 Uiso 1 1 calc R . .
C17 C 0.3645(12) 0.5955(5) 0.3742(5) 0.073(3) Uani 1 1 d . . .
H17 H 0.3651 0.5529 0.4213 0.088 Uiso 1 1 calc R . .
C18 C 0.4972(11) 0.6148(5) 0.3269(5) 0.061(2) Uani 1 1 d . . .
H18 H 0.5915 0.5881 0.3417 0.073 Uiso 1 1 calc R . .
C2 C 0.0412(9) 0.4529(5) 0.1121(4) 0.0460(18) Uani 1 1 d . . .
C1 C 0.0308(11) 0.3460(5) 0.0947(5) 0.078(3) Uani 1 1 d . . .
H1A H 0.0996 0.3063 0.1264 0.117 Uiso 1 1 calc R . .
H1B H 0.0611 0.3413 0.0385 0.117 Uiso 1 1 calc R . .
H1C H -0.0749 0.3229 0.1084 0.117 Uiso 1 1 calc R . .
C7 C -0.0513(11) 0.4886(6) 0.1714(6) 0.080(3) Uani 1 1 d . . .
H7 H -0.1271 0.4475 0.2010 0.096 Uiso 1 1 calc R . .
O1 O 0.1892(8) 0.0488(4) 0.7159(4) 0.0867(19) Uani 1 1 d . . .
H1 H 0.1502 0.0606 0.6733 0.130 Uiso 1 1 calc R . .
C39 C 0.3027(11) 0.1184(7) 0.7207(6) 0.095(3) Uani 1 1 d . . .
H39A H 0.2539 0.1779 0.7370 0.142 Uiso 1 1 calc R . .
H39B H 0.3617 0.1323 0.6689 0.142 Uiso 1 1 calc R . .
H39C H 0.3717 0.0934 0.7596 0.142 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
Zn2 N5 2.090(4) . ?
Zn2 N6 2.121(4) . ?
Zn2 Cl4 2.2527(18) . ?
Zn2 Cl3 2.2607(19) . ?
Zn2 N4 2.274(5) . ?
N5 C28 1.316(7) . ?
N5 C32 1.325(7) . ?
N4 C24 1.431(7) . ?
N4 C33 1.465(7) . ?
N4 C27 1.479(6) . ?
N6 C38 1.321(7) . ?
N6 C34 1.334(8) . ?
C34 C35 1.366(8) . ?
C34 C33 1.491(8) . ?
C25 C26 1.365(8) . ?
C25 C24 1.376(7) . ?
C27 C28 1.500(8) . ?
C24 C23 1.355(8) . ?
C28 C29 1.351(8) . ?
C21 C22 1.348(9) . ?
C21 C26 1.360(9) . ?
C21 C20 1.474(9) . ?
C38 C37 1.369(8) . ?
C22 C23 1.363(10) . ?
C29 C30 1.373(9) . ?
C30 C31 1.347(9) . ?
C31 C32 1.371(8) . ?
C36 C37 1.340(10) . ?
C36 C35 1.370(10) . ?
Zn1 N2 2.116(5) . ?
Zn1 N3 2.139(5) . ?
Zn1 Cl2 2.228(2) . ?
Zn1 Cl1 2.240(2) . ?
Zn1 N1 2.293(6) . ?
N2 C9 1.325(8) . ?
N2 C13 1.329(8) . ?
N1 C5 1.447(7) . ?
N1 C8 1.464(6) . ?
N1 C14 1.472(7) . ?
C15 N3 1.316(9) . ?
C15 C16 1.359(9) . ?
C15 C14 1.493(8) . ?
N3 C19 1.331(7) . ?
C5 C6 1.355(9) . ?
C5 C4 1.365(9) . ?
C4 C3 1.367(8) . ?
C9 C10 1.357(8) . ?
C9 C8 1.465(9) . ?
C3 C2 1.345(9) . ?
C10 C11 1.370(11) . ?
C13 C12 1.350(9) . ?
C12 C11 1.345(12) . ?
C16 C17 1.378(10) . ?
C19 C18 1.366(9) . ?
C6 C7 1.385(11) . ?
C17 C18 1.329(11) . ?
C2 C7 1.334(11) . ?
C2 C1 1.517(9) . ?
O1 C39 1.378(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Zn2 N6 148.8(2) . . ?
N5 Zn2 Cl4 98.60(14) . . ?
N6 Zn2 Cl4 98.76(15) . . ?
N5 Zn2 Cl3 98.16(14) . . ?
N6 Zn2 Cl3 98.05(14) . . ?
Cl4 Zn2 Cl3 114.33(7) . . ?
N5 Zn2 N4 75.64(17) . . ?
N6 Zn2 N4 74.27(17) . . ?
Cl4 Zn2 N4 139.55(13) . . ?
Cl3 Zn2 N4 106.11(13) . . ?
C28 N5 C32 117.6(5) . . ?
C28 N5 Zn2 116.8(4) . . ?
C32 N5 Zn2 125.5(4) . . ?
C24 N4 C33 113.3(4) . . ?
C24 N4 C27 112.6(4) . . ?
C33 N4 C27 111.2(5) . . ?
C24 N4 Zn2 113.9(3) . . ?
C33 N4 Zn2 104.4(4) . . ?
C27 N4 Zn2 100.5(3) . . ?
C38 N6 C34 118.9(5) . . ?
C38 N6 Zn2 124.2(4) . . ?
C34 N6 Zn2 116.7(4) . . ?
N6 C34 C35 121.6(6) . . ?
N6 C34 C33 116.1(5) . . ?
C35 C34 C33 122.2(6) . . ?
C26 C25 C24 120.3(6) . . ?
N4 C27 C28 109.4(4) . . ?
C23 C24 C25 117.9(6) . . ?
C23 C24 N4 121.4(5) . . ?
C25 C24 N4 120.5(5) . . ?
N5 C28 C29 123.0(6) . . ?
N5 C28 C27 114.7(5) . . ?
C29 C28 C27 122.2(5) . . ?
C22 C21 C26 116.9(7) . . ?
C22 C21 C20 121.8(7) . . ?
C26 C21 C20 121.3(6) . . ?
N6 C38 C37 122.3(7) . . ?
C21 C26 C25 121.8(6) . . ?
C21 C22 C23 122.6(7) . . ?
C28 C29 C30 118.4(6) . . ?
C31 C30 C29 120.1(6) . . ?
N4 C33 C34 109.5(5) . . ?
C30 C31 C32 117.4(6) . . ?
C24 C23 C22 120.4(6) . . ?
C37 C36 C35 120.6(6) . . ?
C34 C35 C36 118.2(7) . . ?
N5 C32 C31 123.4(6) . . ?
C36 C37 C38 118.4(7) . . ?
N2 Zn1 N3 147.8(2) . . ?
N2 Zn1 Cl2 99.44(18) . . ?
N3 Zn1 Cl2 95.94(17) . . ?
N2 Zn1 Cl1 98.07(14) . . ?
N3 Zn1 Cl1 98.03(15) . . ?
Cl2 Zn1 Cl1 120.72(10) . . ?
N2 Zn1 N1 75.5(2) . . ?
N3 Zn1 N1 73.68(19) . . ?
Cl2 Zn1 N1 135.30(14) . . ?
Cl1 Zn1 N1 103.88(15) . . ?
C9 N2 C13 118.8(6) . . ?
C9 N2 Zn1 117.2(5) . . ?
C13 N2 Zn1 124.0(5) . . ?
C5 N1 C8 112.1(5) . . ?
C5 N1 C14 111.9(5) . . ?
C8 N1 C14 113.5(5) . . ?
C5 N1 Zn1 115.9(4) . . ?
C8 N1 Zn1 103.5(4) . . ?
C14 N1 Zn1 99.1(4) . . ?
N3 C15 C16 121.9(7) . . ?
N3 C15 C14 114.8(6) . . ?
C16 C15 C14 123.3(8) . . ?
C15 N3 C19 119.4(6) . . ?
C15 N3 Zn1 115.3(4) . . ?
C19 N3 Zn1 125.3(5) . . ?
C6 C5 C4 118.4(6) . . ?
C6 C5 N1 122.1(6) . . ?
C4 C5 N1 119.5(6) . . ?
C5 C4 C3 119.6(7) . . ?
N2 C9 C10 121.0(7) . . ?
N2 C9 C8 116.2(5) . . ?
C10 C9 C8 122.7(7) . . ?
C2 C3 C4 123.0(7) . . ?
C9 C10 C11 119.0(8) . . ?
N1 C14 C15 107.1(5) . . ?
N2 C13 C12 123.2(8) . . ?
C11 C12 C13 117.7(8) . . ?
C15 C16 C17 118.0(8) . . ?
N1 C8 C9 111.9(5) . . ?
N3 C19 C18 121.3(8) . . ?
C5 C6 C7 119.8(8) . . ?
C12 C11 C10 120.4(7) . . ?
C18 C17 C16 120.3(7) . . ?
C17 C18 C19 119.0(8) . . ?
C7 C2 C3 116.8(7) . . ?
C7 C2 C1 121.6(8) . . ?
C3 C2 C1 121.5(7) . . ?
C2 C7 C6 122.4(8) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.613
_refine_diff_density_min         -1.191
_refine_diff_density_rms         0.138
####################################################################### 
# 
# 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_L9
_database_code_depnum_ccdc_archive 'CCDC 861145'
_audit_update_record             
;
2012-01-05 deposited with the CCDC.
2016-06-30 downloaded from the CCDC.
;
#TrackingRef 'L9.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H38 Cl2 N6 O3'
_chemical_formula_sum            'C38 H38 Cl2 N6 O3'
_chemical_formula_weight         697.64

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'

_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                   11.813(2)
_cell_length_b                   12.191(2)
_cell_length_c                   13.301(3)
_cell_angle_alpha                89.36(3)
_cell_angle_beta                 87.62(3)
_cell_angle_gamma                78.82(3)
_cell_volume                     1877.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   ?

_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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10570
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.01
_reflns_number_total             6627
_reflns_number_gt                4501
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0979P)²+0.5054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6476
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.2168
_refine_ls_wR_factor_gt          0.1949
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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
O3 O 0.0113(3) 0.7324(3) 0.9484(3) 0.1047(12) Uani 1 1 d . . .
N6 N 0.1617(3) -0.0833(2) 0.4527(2) 0.0494(8) Uani 1 1 d . . .
N3 N 0.3393(3) 0.5038(2) 0.1485(2) 0.0502(8) Uani 1 1 d . . .
N5 N 0.2122(2) -0.0003(2) 0.2731(2) 0.0477(7) Uani 1 1 d . . .
N2 N 0.5571(3) 0.5498(2) 0.1285(2) 0.0503(8) Uani 1 1 d . . .
C24 C 0.2709(3) 0.1589(3) 0.4712(3) 0.0433(8) Uani 1 1 d . . .
N1 N 0.3764(3) 0.7191(2) 0.2001(2) 0.0521(8) Uani 1 1 d . . .
C28 C 0.3111(3) 0.0348(3) 0.2522(3) 0.0462(9) Uani 1 1 d . . .
N4 N 0.3285(3) 0.0542(2) 0.4368(2) 0.0470(7) Uani 1 1 d . . .
C25 C 0.2285(3) 0.1757(3) 0.5705(3) 0.0532(10) Uani 1 1 d . . .
H25 H 0.2356 0.1146 0.6138 0.064 Uiso 1 1 calc R . .
C5 C 0.3927(3) 0.6979(3) 0.3027(3) 0.0451(9) Uani 1 1 d . . .
C33 C 0.3426(3) -0.0407(3) 0.5053(3) 0.0544(10) Uani 1 1 d . . .
H33A H 0.3715 -0.0190 0.5678 0.065 Uiso 1 1 calc R . .
H33B H 0.4004 -0.1006 0.4762 0.065 Uiso 1 1 calc R . .
C23 C 0.2528(3) 0.2527(3) 0.4085(3) 0.0488(9) Uani 1 1 d . . .
H23 H 0.2764 0.2457 0.3409 0.059 Uiso 1 1 calc R . .
C9 C 0.5748(4) 0.6571(3) 0.1258(3) 0.0509(10) Uani 1 1 d . . .
C19 C 0.3212(4) 0.3987(3) 0.1470(3) 0.0561(10) Uani 1 1 d . . .
H19 H 0.3848 0.3402 0.1438 0.067 Uiso 1 1 calc R . .
C4 C 0.4953(3) 0.7083(3) 0.3459(3) 0.0545(10) Uani 1 1 d . . .
H4 H 0.5529 0.7322 0.3065 0.065 Uiso 1 1 calc R . .
C27 C 0.3882(3) 0.0423(3) 0.3393(3) 0.0521(9) Uani 1 1 d . . .
H27A H 0.4480 -0.0246 0.3399 0.063 Uiso 1 1 calc R . .
H27B H 0.4258 0.1056 0.3280 0.063 Uiso 1 1 calc R . .
C22 C 0.1999(3) 0.3563(3) 0.4465(3) 0.0535(10) Uani 1 1 d . . .
H22 H 0.1895 0.4175 0.4032 0.064 Uiso 1 1 calc R . .
C26 C 0.1768(4) 0.2787(3) 0.6063(3) 0.0576(10) Uani 1 1 d . . .
H26 H 0.1510 0.2858 0.6734 0.069 Uiso 1 1 calc R . .
C15 C 0.2470(3) 0.5873(3) 0.1547(3) 0.0519(10) Uani 1 1 d . . .
C32 C 0.1413(4) -0.0110(3) 0.1996(3) 0.0578(10) Uani 1 1 d . . .
H32 H 0.0723 -0.0343 0.2158 0.069 Uiso 1 1 calc R . .
C29 C 0.3417(4) 0.0576(3) 0.1538(3) 0.0583(10) Uani 1 1 d . . .
H29 H 0.4105 0.0816 0.1385 0.070 Uiso 1 1 calc R . .
C12 C 0.7572(4) 0.4800(4) 0.1042(3) 0.0639(11) Uani 1 1 d . . .
H12 H 0.8186 0.4198 0.0963 0.077 Uiso 1 1 calc R . .
C16 C 0.1365(3) 0.5683(3) 0.1595(3) 0.0610(11) Uani 1 1 d . . .
H16 H 0.0739 0.6277 0.1644 0.073 Uiso 1 1 calc R . .
C7 C 0.3277(4) 0.6404(3) 0.4649(3) 0.0620(11) Uani 1 1 d . . .
H7 H 0.2698 0.6183 0.5051 0.074 Uiso 1 1 calc R . .
C14 C 0.2699(4) 0.7070(3) 0.1570(3) 0.0625(11) Uani 1 1 d . . .
H14A H 0.2693 0.7355 0.0886 0.075 Uiso 1 1 calc R . .
H14B H 0.2066 0.7534 0.1948 0.075 Uiso 1 1 calc R . .
C34 C 0.2331(3) -0.0846(3) 0.5287(3) 0.0486(9) Uani 1 1 d . . .
C3 C 0.5128(4) 0.6838(3) 0.4459(3) 0.0614(11) Uani 1 1 d . . .
H3 H 0.5824 0.6914 0.4726 0.074 Uiso 1 1 calc R . .
C17 C 0.1192(4) 0.4594(4) 0.1568(3) 0.0671(12) Uani 1 1 d . . .
H17 H 0.0448 0.4446 0.1594 0.081 Uiso 1 1 calc R . .
C6 C 0.3078(3) 0.6637(3) 0.3652(3) 0.0578(10) Uani 1 1 d . . .
H6 H 0.2377 0.6568 0.3391 0.069 Uiso 1 1 calc R . .
C21 C 0.1620(3) 0.3726(3) 0.5454(3) 0.0558(10) Uani 1 1 d . . .
C38 C 0.0674(3) -0.1290(3) 0.4664(3) 0.0601(11) Uani 1 1 d . . .
H38 H 0.0183 -0.1281 0.4134 0.072 Uiso 1 1 calc R . .
C13 C 0.6467(4) 0.4631(3) 0.1190(3) 0.0567(10) Uani 1 1 d . . .
H13 H 0.6332 0.3904 0.1226 0.068 Uiso 1 1 calc R . .
C8 C 0.4694(4) 0.7490(3) 0.1382(3) 0.0603(11) Uani 1 1 d . . .
H8A H 0.4921 0.8135 0.1676 0.072 Uiso 1 1 calc R . .
H8B H 0.4408 0.7708 0.0722 0.072 Uiso 1 1 calc R . .
C35 C 0.2101(4) -0.1291(3) 0.6211(3) 0.0611(11) Uani 1 1 d . . .
H35 H 0.2594 -0.1277 0.6737 0.073 Uiso 1 1 calc R . .
C2 C 0.4301(4) 0.6483(3) 0.5079(3) 0.0589(11) Uani 1 1 d . . .
C18 C 0.2127(4) 0.3741(3) 0.1502(3) 0.0613(11) Uani 1 1 d . . .
H18 H 0.2030 0.3003 0.1480 0.074 Uiso 1 1 calc R . .
C11 C 0.7757(4) 0.5879(4) 0.1011(3) 0.0699(12) Uani 1 1 d . . .
H11 H 0.8503 0.6012 0.0914 0.084 Uiso 1 1 calc R . .
C20 C 0.1087(4) 0.4863(4) 0.5881(4) 0.0817(15) Uani 1 1 d . . .
H20A H 0.0916 0.5390 0.5340 0.123 Uiso 1 1 calc R . .
H20B H 0.1619 0.5105 0.6314 0.123 Uiso 1 1 calc R . .
H20C H 0.0387 0.4815 0.6258 0.123 Uiso 1 1 calc R . .
C31 C 0.1670(4) 0.0112(4) 0.1016(4) 0.0683(12) Uani 1 1 d . . .
H31 H 0.1162 0.0040 0.0516 0.082 Uiso 1 1 calc R . .
C30 C 0.2683(4) 0.0441(3) 0.0785(3) 0.0687(12) Uani 1 1 d . . .
H30 H 0.2885 0.0577 0.0119 0.082 Uiso 1 1 calc R . .
C10 C 0.6838(4) 0.6762(4) 0.1124(3) 0.0638(11) Uani 1 1 d . . .
H10 H 0.6966 0.7491 0.1109 0.077 Uiso 1 1 calc R . .
C36 C 0.1129(4) -0.1758(3) 0.6349(4) 0.0711(13) Uani 1 1 d . . .
H36 H 0.0959 -0.2063 0.6969 0.085 Uiso 1 1 calc R . .
C37 C 0.0414(4) -0.1768(3) 0.5557(4) 0.0704(13) Uani 1 1 d . . .
H37 H -0.0235 -0.2093 0.5629 0.084 Uiso 1 1 calc R . .
C1 C 0.4509(5) 0.6202(4) 0.6175(3) 0.0835(14) Uani 1 1 d . . .
H1A H 0.4293 0.6869 0.6571 0.125 Uiso 1 1 calc R . .
H1B H 0.5312 0.5893 0.6253 0.125 Uiso 1 1 calc R . .
H1C H 0.4054 0.5666 0.6396 0.125 Uiso 1 1 calc R . .
Cl1 Cl 0.59313(10) 0.18904(8) 0.12545(10) 0.0753(4) Uani 1 1 d . . .
Cl2 Cl 0.90968(10) 0.84831(10) 0.16104(10) 0.0784(4) Uani 1 1 d . . .
O2 O 0.1389(3) 0.8886(3) 0.8741(3) 0.0861(10) Uani 1 1 d . . .
O1 O 0.6409(2) 0.9431(2) 0.2121(2) 0.0758(9) 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
N6 C34 1.341(5) . ?
N6 C38 1.344(5) . ?
N3 C19 1.339(5) . ?
N3 C15 1.340(5) . ?
N5 C32 1.338(5) . ?
N5 C28 1.338(4) . ?
N2 C13 1.346(5) . ?
N2 C9 1.365(4) . ?
C24 C25 1.396(5) . ?
C24 C23 1.396(5) . ?
C24 N4 1.396(4) . ?
N1 C5 1.401(5) . ?
N1 C14 1.438(5) . ?
N1 C8 1.445(5) . ?
C28 C29 1.383(5) . ?
C28 C27 1.517(5) . ?
N4 C27 1.446(5) . ?
N4 C33 1.453(4) . ?
C25 C26 1.367(5) . ?
C5 C4 1.390(5) . ?
C5 C6 1.398(5) . ?
C33 C34 1.512(5) . ?
C23 C22 1.387(5) . ?
C9 C10 1.358(6) . ?
C9 C8 1.509(5) . ?
C19 C18 1.371(6) . ?
C4 C3 1.375(6) . ?
C22 C21 1.376(6) . ?
C26 C21 1.382(5) . ?
C15 C16 1.369(5) . ?
C15 C14 1.535(5) . ?
C32 C31 1.362(6) . ?
C29 C30 1.383(6) . ?
C12 C13 1.367(6) . ?
C12 C11 1.374(6) . ?
C16 C17 1.383(6) . ?
C7 C6 1.374(6) . ?
C7 C2 1.379(6) . ?
C34 C35 1.376(5) . ?
C3 C2 1.383(6) . ?
C17 C18 1.363(6) . ?
C21 C20 1.513(6) . ?
C38 C37 1.367(6) . ?
C35 C36 1.383(6) . ?
C2 C1 1.512(6) . ?
C11 C10 1.378(6) . ?
C31 C30 1.357(6) . ?
C36 C37 1.379(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
C34 N6 C38 119.3(3) . . ?
C19 N3 C15 118.1(3) . . ?
C32 N5 C28 120.3(3) . . ?
C13 N2 C9 120.6(3) . . ?
C25 C24 C23 116.2(3) . . ?
C25 C24 N4 121.9(3) . . ?
C23 C24 N4 122.0(3) . . ?
C5 N1 C14 119.9(3) . . ?
C5 N1 C8 119.1(3) . . ?
C14 N1 C8 120.9(3) . . ?
N5 C28 C29 120.0(4) . . ?
N5 C28 C27 117.2(3) . . ?
C29 C28 C27 122.8(3) . . ?
C24 N4 C27 120.8(3) . . ?
C24 N4 C33 119.3(3) . . ?
C27 N4 C33 119.2(3) . . ?
C26 C25 C24 122.4(3) . . ?
C4 C5 C6 117.5(4) . . ?
C4 C5 N1 120.9(3) . . ?
C6 C5 N1 121.5(3) . . ?
N4 C33 C34 114.3(3) . . ?
C22 C23 C24 120.3(3) . . ?
C10 C9 N2 119.4(4) . . ?
C10 C9 C8 123.6(3) . . ?
N2 C9 C8 117.0(3) . . ?
N3 C19 C18 122.6(4) . . ?
C3 C4 C5 120.9(4) . . ?
N4 C27 C28 114.4(3) . . ?
C21 C22 C23 123.0(3) . . ?
C25 C26 C21 121.7(4) . . ?
N3 C15 C16 122.2(4) . . ?
N3 C15 C14 117.2(3) . . ?
C16 C15 C14 120.6(3) . . ?
N5 C32 C31 122.0(4) . . ?
C30 C29 C28 118.9(4) . . ?
C13 C12 C11 118.7(4) . . ?
C15 C16 C17 119.0(4) . . ?
C6 C7 C2 122.8(4) . . ?
N1 C14 C15 115.6(3) . . ?
N6 C34 C35 121.3(4) . . ?
N6 C34 C33 116.4(3) . . ?
C35 C34 C33 122.2(4) . . ?
C4 C3 C2 122.1(4) . . ?
C18 C17 C16 119.1(4) . . ?
C7 C6 C5 120.1(4) . . ?
C22 C21 C26 116.4(4) . . ?
C22 C21 C20 123.1(4) . . ?
C26 C21 C20 120.5(4) . . ?
N6 C38 C37 122.1(4) . . ?
N2 C13 C12 121.1(4) . . ?
N1 C8 C9 114.5(3) . . ?
C34 C35 C36 119.2(4) . . ?
C7 C2 C3 116.6(4) . . ?
C7 C2 C1 121.8(4) . . ?
C3 C2 C1 121.6(4) . . ?
C17 C18 C19 119.0(4) . . ?
C12 C11 C10 120.0(4) . . ?
C30 C31 C32 118.5(4) . . ?
C31 C30 C29 120.3(4) . . ?
C9 C10 C11 120.2(4) . . ?
C37 C36 C35 119.2(4) . . ?
C38 C37 C36 118.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.055



