# 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_1p
_database_code_depnum_ccdc_archive 'CCDC 1418408'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2015-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 N4 O5.50 Zn'
_chemical_formula_weight         433.74

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'

_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                   26.1564(6)
_cell_length_b                   7.8711(2)
_cell_length_c                   21.2024(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.9020(10)
_cell_angle_gamma                90.00
_cell_volume                     3705.80(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4496
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792
_exptl_absorpt_coefficient_mu    1.365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7265
_exptl_absorpt_correction_T_max  0.8214
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
244 frames in 4 sets of ω scans. Rotation/frame = 2.0 °.
Crystal-detector distance = 40 mm. Measuring time  = 40 s/°.
;

_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  
;
Nonius KappaCCD area-detector diffractometer
;
_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            7358
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         27.46
_reflns_number_total             4221
_reflns_number_gt                3552
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.0352P)²+6.0864P] 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         4221
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0807
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.0001

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 0.757420(10) 0.04473(3) 0.779471(12) 0.01710(8) Uani 1 1 d . . .
N1 N 0.85029(8) 0.0832(2) 0.84804(10) 0.0220(4) Uani 1 1 d . . .
N2 N 0.66749(7) 0.0905(2) 0.74273(9) 0.0194(4) Uani 1 1 d . . .
N3 N 0.76632(7) 0.0920(2) 0.88585(9) 0.0175(3) Uani 1 1 d . . .
N4 N 1.11987(8) 0.4506(3) 0.96575(10) 0.0275(4) Uani 1 1 d . . .
O1 O 0.73863(7) -0.45717(18) 0.81854(8) 0.0213(3) Uani 1 1 d . . .
O2 O 0.74993(6) -0.20876(18) 0.78211(7) 0.0212(3) Uani 1 1 d . . .
O3 O 1.16626(8) 0.4233(3) 0.96478(11) 0.0442(5) Uani 1 1 d . . .
O4 O 1.08330(9) 0.5581(3) 0.92198(10) 0.0512(6) Uani 1 1 d . . .
O5 O 1.11153(9) 0.3776(3) 1.01145(11) 0.0477(5) Uani 1 1 d . . .
O6 O 1.0000 0.0761(3) 0.7500 0.0407(6) Uani 1 2 d S . .
C1 C 0.89200(10) 0.0443(3) 0.83093(13) 0.0288(5) Uani 1 1 d . . .
H1 H 0.8797 -0.0117 0.7865 0.035 Uiso 1 1 calc R . .
C2 C 0.95166(11) 0.0847(3) 0.87684(14) 0.0353(6) Uani 1 1 d . . .
H2 H 0.9795 0.0557 0.8640 0.042 Uiso 1 1 calc R . .
C3 C 0.96980(10) 0.1690(3) 0.94244(14) 0.0354(6) Uani 1 1 d . . .
H3 H 1.0099 0.2002 0.9738 0.043 Uiso 1 1 calc R . .
C4 C 0.92769(10) 0.2069(3) 0.96124(12) 0.0291(5) Uani 1 1 d . . .
H4 H 0.9392 0.2613 1.0058 0.035 Uiso 1 1 calc R . .
C5 C 0.86790(9) 0.1620(3) 0.91225(11) 0.0215(4) Uani 1 1 d . . .
C6 C 0.81852(9) 0.2086(3) 0.92631(11) 0.0217(4) Uani 1 1 d . . .
H6A H 0.8341 0.2024 0.9792 0.026 Uiso 1 1 calc R . .
H6B H 0.8055 0.3244 0.9102 0.026 Uiso 1 1 calc R . .
C7 C 0.70986(9) 0.1687(3) 0.87253(11) 0.0197(4) Uani 1 1 d . . .
H7A H 0.7149 0.2909 0.8785 0.024 Uiso 1 1 calc R . .
H7B H 0.7019 0.1266 0.9095 0.024 Uiso 1 1 calc R . .
C8 C 0.65630(9) 0.1295(3) 0.79574(11) 0.0193(4) Uani 1 1 d . . .
C9 C 0.59799(10) 0.1417(3) 0.78006(12) 0.0298(5) Uani 1 1 d . . .
H9 H 0.5908 0.1665 0.8176 0.036 Uiso 1 1 calc R . .
C10 C 0.55042(10) 0.1163(4) 0.70780(13) 0.0358(6) Uani 1 1 d . . .
H10 H 0.5109 0.1247 0.6963 0.043 Uiso 1 1 calc R . .
C11 C 0.56221(10) 0.0784(3) 0.65299(12) 0.0305(5) Uani 1 1 d . . .
H11 H 0.5308 0.0619 0.6041 0.037 Uiso 1 1 calc R . .
C12 C 0.62126(10) 0.0657(3) 0.67196(12) 0.0251(5) Uani 1 1 d . . .
C13 C 0.78060(9) -0.0703(2) 0.92807(11) 0.0199(4) Uani 1 1 d . . .
H13A H 0.7815 -0.0488 0.9737 0.024 Uiso 1 1 calc R . .
H13B H 0.8207 -0.1061 0.9417 0.024 Uiso 1 1 calc R . .
C14 C 0.73691(9) -0.2165(3) 0.88704(11) 0.0202(4) Uani 1 1 d . . .
H14A H 0.7430 -0.3029 0.9230 0.024 Uiso 1 1 calc R . .
H14B H 0.6961 -0.1742 0.8651 0.024 Uiso 1 1 calc R . .
C15 C 0.74253(9) -0.2987(3) 0.82685(10) 0.0186(4) Uani 1 1 d . . .
C16 C 0.90326(13) 0.0622(4) 0.63937(16) 0.0485(7) Uani 1 1 d . . .
H16A H 0.9208 -0.0115 0.6197 0.073 Uiso 1 1 calc R . .
H16B H 0.8718 0.1282 0.5998 0.073 Uiso 1 1 calc R . .
H16C H 0.8869 -0.0048 0.6624 0.073 Uiso 1 1 calc R . .
C17 C 0.95045(13) 0.1780(4) 0.69555(15) 0.0447(7) Uani 1 1 d . . .
H17A H 0.9641 0.2549 0.6717 0.054 Uiso 1 1 calc R . .
H17B H 0.9342 0.2450 0.7193 0.054 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 2.0086(15) . ?
Zn1 N2 2.0815(17) . ?
Zn1 N1 2.0913(18) . ?
Zn1 O1 2.1345(14) 4_656 ?
Zn1 N3 2.1736(16) . ?
Zn1 O2 2.2894(14) 4_656 ?
Zn1 C15 2.570(2) 4_656 ?
N1 C5 1.337(3) . ?
N1 C1 1.354(3) . ?
N2 C8 1.338(3) . ?
N2 C12 1.354(3) . ?
N3 C7 1.478(2) . ?
N3 C6 1.485(3) . ?
N3 C13 1.490(2) . ?
N4 O5 1.241(3) . ?
N4 O3 1.243(2) . ?
N4 O4 1.247(3) . ?
O1 C15 1.257(2) . ?
O1 Zn1 2.1345(14) 4_646 ?
O2 C15 1.278(2) . ?
O2 Zn1 2.2894(14) 4_646 ?
O6 C17 1.440(3) 2_756 ?
O6 C17 1.440(3) . ?
C1 C2 1.371(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.516(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.516(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.382(3) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.529(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.505(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 Zn1 2.570(2) 4_646 ?
C16 C17 1.490(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
O2 Zn1 N2 94.30(6) . . ?
O2 Zn1 N1 102.65(6) . . ?
N2 Zn1 N1 154.53(7) . . ?
O2 Zn1 O1 94.35(5) . 4_656 ?
N2 Zn1 O1 105.27(6) . 4_656 ?
N1 Zn1 O1 92.39(6) . 4_656 ?
O2 Zn1 N3 95.72(6) . . ?
N2 Zn1 N3 80.73(6) . . ?
N1 Zn1 N3 78.80(6) . . ?
O1 Zn1 N3 167.86(6) 4_656 . ?
O2 Zn1 O2 151.38(3) . 4_656 ?
N2 Zn1 O2 84.38(6) . 4_656 ?
N1 Zn1 O2 89.45(6) . 4_656 ?
O1 Zn1 O2 58.89(5) 4_656 4_656 ?
N3 Zn1 O2 112.18(6) . 4_656 ?
O2 Zn1 C15 123.11(6) . 4_656 ?
N2 Zn1 C15 96.48(6) . 4_656 ?
N1 Zn1 C15 90.09(6) . 4_656 ?
O1 Zn1 C15 29.15(6) 4_656 4_656 ?
N3 Zn1 C15 141.14(6) . 4_656 ?
O2 Zn1 C15 29.78(5) 4_656 4_656 ?
C5 N1 C1 119.01(19) . . ?
C5 N1 Zn1 115.06(13) . . ?
C1 N1 Zn1 125.82(15) . . ?
C8 N2 C12 120.00(18) . . ?
C8 N2 Zn1 115.52(13) . . ?
C12 N2 Zn1 124.08(14) . . ?
C7 N3 C6 112.27(16) . . ?
C7 N3 C13 111.89(15) . . ?
C6 N3 C13 108.70(15) . . ?
C7 N3 Zn1 108.87(12) . . ?
C6 N3 Zn1 105.48(12) . . ?
C13 N3 Zn1 109.40(12) . . ?
O5 N4 O3 120.6(2) . . ?
O5 N4 O4 120.9(2) . . ?
O3 N4 O4 118.5(2) . . ?
C15 O1 Zn1 95.02(12) . 4_646 ?
C15 O2 Zn1 128.78(13) . . ?
C15 O2 Zn1 87.36(11) . 4_646 ?
Zn1 O2 Zn1 143.71(6) . 4_646 ?
C17 O6 C17 112.3(3) 2_756 . ?
N1 C1 C2 122.2(2) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.65(19) . . ?
N1 C5 C6 116.20(17) . . ?
C4 C5 C6 122.05(19) . . ?
N3 C6 C5 110.85(16) . . ?
N3 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N3 C7 C8 112.65(16) . . ?
N3 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N3 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N2 C8 C9 121.15(19) . . ?
N2 C8 C7 117.42(17) . . ?
C9 C8 C7 121.35(18) . . ?
C8 C9 C10 119.2(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 118.9(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
N2 C12 C11 121.3(2) . . ?
N3 C13 C14 115.40(16) . . ?
N3 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
N3 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 115.29(17) . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C13 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
O1 C15 O2 118.61(18) . . ?
O1 C15 C14 120.55(18) . . ?
O2 C15 C14 120.82(18) . . ?
O1 C15 Zn1 55.83(10) . 4_646 ?
O2 C15 Zn1 62.86(10) . 4_646 ?
C14 C15 Zn1 174.33(14) . 4_646 ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 C16 108.3(2) . . ?
O6 C17 H17A 110.0 . . ?
C16 C17 H17A 110.0 . . ?
O6 C17 H17B 110.0 . . ?
C16 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Zn1 N1 C5 -111.65(15) . . . . ?
N2 Zn1 N1 C5 18.9(3) . . . . ?
O1 Zn1 N1 C5 153.35(15) 4_656 . . . ?
N3 Zn1 N1 C5 -18.23(15) . . . . ?
O2 Zn1 N1 C5 94.52(15) 4_656 . . . ?
C15 Zn1 N1 C5 124.29(15) 4_656 . . . ?
O2 Zn1 N1 C1 72.26(19) . . . . ?
N2 Zn1 N1 C1 -157.22(17) . . . . ?
O1 Zn1 N1 C1 -22.73(18) 4_656 . . . ?
N3 Zn1 N1 C1 165.68(19) . . . . ?
O2 Zn1 N1 C1 -81.57(18) 4_656 . . . ?
C15 Zn1 N1 C1 -51.80(19) 4_656 . . . ?
O2 Zn1 N2 C8 96.64(15) . . . . ?
N1 Zn1 N2 C8 -35.3(2) . . . . ?
O1 Zn1 N2 C8 -167.66(14) 4_656 . . . ?
N3 Zn1 N2 C8 1.54(14) . . . . ?
O2 Zn1 N2 C8 -112.06(15) 4_656 . . . ?
C15 Zn1 N2 C8 -139.31(15) 4_656 . . . ?
O2 Zn1 N2 C12 -76.15(17) . . . . ?
N1 Zn1 N2 C12 151.91(17) . . . . ?
O1 Zn1 N2 C12 19.55(18) 4_656 . . . ?
N3 Zn1 N2 C12 -171.25(18) . . . . ?
O2 Zn1 N2 C12 75.15(17) 4_656 . . . ?
C15 Zn1 N2 C12 47.90(17) 4_656 . . . ?
O2 Zn1 N3 C7 -107.08(13) . . . . ?
N2 Zn1 N3 C7 -13.64(13) . . . . ?
N1 Zn1 N3 C7 151.12(14) . . . . ?
O1 Zn1 N3 C7 107.1(3) 4_656 . . . ?
O2 Zn1 N3 C7 66.36(13) 4_656 . . . ?
C15 Zn1 N3 C7 75.21(16) 4_656 . . . ?
O2 Zn1 N3 C6 132.25(12) . . . . ?
N2 Zn1 N3 C6 -134.32(13) . . . . ?
N1 Zn1 N3 C6 30.45(12) . . . . ?
O1 Zn1 N3 C6 -13.6(3) 4_656 . . . ?
O2 Zn1 N3 C6 -54.32(13) 4_656 . . . ?
C15 Zn1 N3 C6 -45.47(16) 4_656 . . . ?
O2 Zn1 N3 C13 15.48(13) . . . . ?
N2 Zn1 N3 C13 108.92(13) . . . . ?
N1 Zn1 N3 C13 -86.32(13) . . . . ?
O1 Zn1 N3 C13 -130.4(3) 4_656 . . . ?
O2 Zn1 N3 C13 -171.09(11) 4_656 . . . ?
C15 Zn1 N3 C13 -162.24(12) 4_656 . . . ?
N2 Zn1 O2 C15 -70.64(16) . . . . ?
N1 Zn1 O2 C15 90.22(16) . . . . ?
O1 Zn1 O2 C15 -176.34(16) 4_656 . . . ?
N3 Zn1 O2 C15 10.46(16) . . . . ?
O2 Zn1 O2 C15 -156.77(16) 4_656 . . . ?
C15 Zn1 O2 C15 -171.25(11) 4_656 . . . ?
N2 Zn1 O2 Zn1 103.25(12) . . . 4_646 ?
N1 Zn1 O2 Zn1 -95.89(12) . . . 4_646 ?
O1 Zn1 O2 Zn1 -2.46(12) 4_656 . . 4_646 ?
N3 Zn1 O2 Zn1 -175.66(12) . . . 4_646 ?
O2 Zn1 O2 Zn1 17.11(12) 4_656 . . 4_646 ?
C15 Zn1 O2 Zn1 2.63(15) 4_656 . . 4_646 ?
C5 N1 C1 C2 -0.8(3) . . . . ?
Zn1 N1 C1 C2 175.19(18) . . . . ?
N1 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C1 N1 C5 C4 0.9(3) . . . . ?
Zn1 N1 C5 C4 -175.50(17) . . . . ?
C1 N1 C5 C6 177.43(19) . . . . ?
Zn1 N1 C5 C6 1.1(2) . . . . ?
C3 C4 C5 N1 0.3(3) . . . . ?
C3 C4 C5 C6 -176.1(2) . . . . ?
C7 N3 C6 C5 -156.88(16) . . . . ?
C13 N3 C6 C5 78.78(19) . . . . ?
Zn1 N3 C6 C5 -38.46(18) . . . . ?
N1 C5 C6 N3 26.7(3) . . . . ?
C4 C5 C6 N3 -156.76(19) . . . . ?
C6 N3 C7 C8 139.16(17) . . . . ?
C13 N3 C7 C8 -98.29(19) . . . . ?
Zn1 N3 C7 C8 22.75(19) . . . . ?
C12 N2 C8 C9 1.4(3) . . . . ?
Zn1 N2 C8 C9 -171.73(17) . . . . ?
C12 N2 C8 C7 -175.53(18) . . . . ?
Zn1 N2 C8 C7 11.4(2) . . . . ?
N3 C7 C8 N2 -23.6(3) . . . . ?
N3 C7 C8 C9 159.5(2) . . . . ?
N2 C8 C9 C10 -1.3(4) . . . . ?
C7 C8 C9 C10 175.5(2) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C8 N2 C12 C11 -0.5(3) . . . . ?
Zn1 N2 C12 C11 172.00(17) . . . . ?
C10 C11 C12 N2 -0.4(4) . . . . ?
C7 N3 C13 C14 66.6(2) . . . . ?
C6 N3 C13 C14 -168.80(16) . . . . ?
Zn1 N3 C13 C14 -54.09(19) . . . . ?
N3 C13 C14 C15 74.5(2) . . . . ?
Zn1 O1 C15 O2 -3.55(19) 4_646 . . . ?
Zn1 O1 C15 C14 174.83(16) 4_646 . . . ?
Zn1 O2 C15 O1 179.68(13) . . . . ?
Zn1 O2 C15 O1 3.30(18) 4_646 . . . ?
Zn1 O2 C15 C14 1.3(3) . . . . ?
Zn1 O2 C15 C14 -175.07(17) 4_646 . . . ?
Zn1 O2 C15 Zn1 176.38(15) . . . 4_646 ?
C13 C14 C15 O1 139.39(19) . . . . ?
C13 C14 C15 O2 -42.3(3) . . . . ?
C13 C14 C15 Zn1 -171.6(14) . . . 4_646 ?
C17 O6 C17 C16 176.6(3) 2_756 . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_2p
_database_code_depnum_ccdc_archive 'CCDC 1418409'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2015-11-08 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 H35 N9 O12 Zn2'
_chemical_formula_weight         844.41

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'

_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                   9.5678(2)
_cell_length_b                   23.4648(7)
_cell_length_c                   15.4587(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.616(2)
_cell_angle_gamma                90.00
_cell_volume                     3466.96(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7809
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1736
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7117
_exptl_absorpt_correction_T_max  0.9575
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
320 frames in 4 sets of φ scans + ω scans. Rotation/frame = 1.3 °.
Crystal-detector distance = 40 mm. Measuring time  = 210 s/°.
;

_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  
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15111
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.49
_reflns_number_total             7935
_reflns_number_gt                5754
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.1059P)²+2.4578P] 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         7935
_refine_ls_number_parameters     491
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1954
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.0001

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 0.81663(5) 0.12059(2) 0.40210(3) 0.01804(16) Uani 1 1 d . . .
Zn2 Zn 1.30994(5) 0.21407(2) 0.41870(3) 0.01817(16) Uani 1 1 d . . .
N1 N 0.8782(4) 0.09293(17) 0.2835(2) 0.0220(8) Uani 1 1 d . . .
N2 N 0.8754(4) 0.08072(17) 0.5169(3) 0.0229(8) Uani 1 1 d . . .
N3 N 0.6896(4) 0.04169(17) 0.3895(2) 0.0198(8) Uani 1 1 d . . .
N4 N 1.2965(4) 0.22761(17) 0.2819(2) 0.0218(8) Uani 1 1 d . . .
N5 N 1.2815(4) 0.23363(17) 0.5513(2) 0.0201(8) Uani 1 1 d . . .
N6 N 1.1840(4) 0.29323(17) 0.4075(3) 0.0207(8) Uani 1 1 d . . .
O1 O 0.6161(3) 0.15225(14) 0.3982(2) 0.0246(7) Uani 1 1 d . . .
O2 O 0.3925(3) 0.13310(14) 0.4202(2) 0.0206(7) Uani 1 1 d . . .
O3 O 1.1049(3) 0.17811(14) 0.4142(2) 0.0214(7) Uani 1 1 d . . .
O4 O 0.8784(3) 0.20106(14) 0.4125(2) 0.0235(7) Uani 1 1 d . . .
O5 O 1.5110(4) 0.25545(15) 0.4291(2) 0.0260(8) Uani 1 1 d D . .
C1 C 0.9796(5) 0.1161(2) 0.2376(3) 0.0269(11) Uani 1 1 d . . .
H1 H 1.0331 0.1454 0.2625 0.032 Uiso 1 1 calc R . .
C2 C 1.0077(6) 0.0985(2) 0.1556(3) 0.0323(12) Uani 1 1 d . . .
H2 H 1.0791 0.1154 0.1258 0.039 Uiso 1 1 calc R . .
C3 C 0.9272(5) 0.0548(2) 0.1177(3) 0.0310(12) Uani 1 1 d . . .
H3 H 0.9436 0.0420 0.0621 0.037 Uiso 1 1 calc R . .
C4 C 0.8229(5) 0.0311(2) 0.1645(3) 0.0255(10) Uani 1 1 d . . .
H4 H 0.7680 0.0017 0.1411 0.031 Uiso 1 1 calc R . .
C5 C 0.8005(5) 0.0513(2) 0.2466(3) 0.0214(10) Uani 1 1 d . . .
C6 C 0.6810(5) 0.0267(2) 0.2970(3) 0.0253(10) Uani 1 1 d . . .
H6A H 0.5929 0.0404 0.2715 0.030 Uiso 1 1 calc R . .
H6B H 0.6817 -0.0145 0.2914 0.030 Uiso 1 1 calc R . .
C7 C 0.7671(5) -0.0007(2) 0.4432(3) 0.0246(10) Uani 1 1 d . . .
H7A H 0.8407 -0.0173 0.4102 0.030 Uiso 1 1 calc R . .
H7B H 0.7041 -0.0311 0.4586 0.030 Uiso 1 1 calc R . .
C8 C 0.8307(5) 0.0264(2) 0.5251(3) 0.0225(10) Uani 1 1 d . . .
C9 C 0.8435(5) -0.0027(2) 0.6023(3) 0.0317(12) Uani 1 1 d . . .
H9 H 0.8139 -0.0403 0.6064 0.038 Uiso 1 1 calc R . .
C10 C 0.9014(5) 0.0256(3) 0.6732(3) 0.0365(14) Uani 1 1 d . . .
H10 H 0.9084 0.0072 0.7265 0.044 Uiso 1 1 calc R . .
C11 C 0.9494(6) 0.0808(3) 0.6664(3) 0.0375(14) Uani 1 1 d . . .
H11 H 0.9904 0.0998 0.7138 0.045 Uiso 1 1 calc R . .
C12 C 0.9337(5) 0.1068(2) 0.5856(3) 0.0291(11) Uani 1 1 d . . .
H12 H 0.9654 0.1440 0.5795 0.035 Uiso 1 1 calc R . .
C13 C 0.5506(5) 0.05523(19) 0.4225(3) 0.0197(9) Uani 1 1 d . . .
H13A H 0.5495 0.0450 0.4833 0.024 Uiso 1 1 calc R . .
H13B H 0.4797 0.0328 0.3913 0.024 Uiso 1 1 calc R . .
C14 C 0.5162(4) 0.11783(19) 0.4121(3) 0.0165(9) Uani 1 1 d . . .
C15 C 1.3243(5) 0.1889(2) 0.2205(3) 0.0259(10) Uani 1 1 d . . .
H15 H 1.3615 0.1538 0.2378 0.031 Uiso 1 1 calc R . .
C16 C 1.3001(5) 0.1989(3) 0.1339(3) 0.0321(12) Uani 1 1 d . . .
H16 H 1.3219 0.1716 0.0931 0.039 Uiso 1 1 calc R . .
C17 C 1.2428(6) 0.2505(3) 0.1083(3) 0.0363(13) Uani 1 1 d . . .
H17 H 1.2240 0.2582 0.0499 0.044 Uiso 1 1 calc R . .
C18 C 1.2135(6) 0.2908(2) 0.1705(3) 0.0332(12) Uani 1 1 d . . .
H18 H 1.1741 0.3257 0.1544 0.040 Uiso 1 1 calc R . .
C19 C 1.2440(5) 0.2784(2) 0.2572(3) 0.0231(10) Uani 1 1 d . . .
C20 C 1.2249(5) 0.3218(2) 0.3283(3) 0.0254(10) Uani 1 1 d . . .
H20A H 1.3117 0.3424 0.3397 0.031 Uiso 1 1 calc R . .
H20B H 1.1534 0.3491 0.3098 0.031 Uiso 1 1 calc R . .
C21 C 1.2208(5) 0.3262(2) 0.4873(3) 0.0246(10) Uani 1 1 d . . .
H21A H 1.1504 0.3551 0.4959 0.029 Uiso 1 1 calc R . .
H21B H 1.3101 0.3451 0.4815 0.029 Uiso 1 1 calc R . .
C22 C 1.2297(5) 0.2863(2) 0.5650(3) 0.0212(10) Uani 1 1 d . . .
C23 C 1.1871(6) 0.3028(2) 0.6460(3) 0.0306(11) Uani 1 1 d . . .
H23 H 1.1502 0.3390 0.6544 0.037 Uiso 1 1 calc R . .
C24 C 1.2006(6) 0.2648(3) 0.7135(3) 0.0359(13) Uani 1 1 d . . .
H24 H 1.1732 0.2752 0.7682 0.043 Uiso 1 1 calc R . .
C25 C 1.2547(6) 0.2112(2) 0.7002(3) 0.0323(12) Uani 1 1 d . . .
H25 H 1.2635 0.1850 0.7453 0.039 Uiso 1 1 calc R . .
C26 C 1.2956(5) 0.1973(2) 0.6176(3) 0.0263(11) Uani 1 1 d . . .
H26 H 1.3340 0.1616 0.6083 0.032 Uiso 1 1 calc R . .
C27 C 1.0352(5) 0.2778(2) 0.4041(4) 0.0259(11) Uani 1 1 d . . .
H27A H 0.9923 0.2915 0.3500 0.031 Uiso 1 1 calc R . .
H27B H 0.9903 0.2973 0.4508 0.031 Uiso 1 1 calc R . .
C28 C 1.0071(5) 0.2139(2) 0.4116(3) 0.0205(10) Uani 1 1 d . . .
N7 N 0.5308(5) 0.07671(19) 0.6962(3) 0.0302(10) Uani 1 1 d . . .
N8 N 1.0779(6) 0.1077(2) 0.9092(3) 0.0407(12) Uani 1 1 d . . .
O6 O 0.5333(6) 0.0837(2) 0.6165(3) 0.0565(13) Uani 1 1 d . . .
O7 O 0.6109(4) 0.0431(2) 0.7329(3) 0.0475(11) Uani 1 1 d . . .
O8 O 0.4448(5) 0.10444(18) 0.7394(3) 0.0455(11) Uani 1 1 d . . .
O9 O 0.9740(6) 0.0760(2) 0.9020(4) 0.0723(16) Uani 1 1 d . . .
O10 O 1.0858(5) 0.14617(18) 0.8520(3) 0.0511(12) Uani 1 1 d . . .
O11 O 1.1609(6) 0.1016(4) 0.9674(4) 0.102(3) Uani 1 1 d . . .
C29 C 0.3153(9) -0.0049(3) 0.0708(5) 0.067(2) Uani 1 1 d . . .
H29A H 0.2713 -0.0247 0.1165 0.101 Uiso 1 1 calc R . .
H29B H 0.3709 -0.0311 0.0393 0.101 Uiso 1 1 calc R . .
H29C H 0.2449 0.0116 0.0322 0.101 Uiso 1 1 calc R . .
C30 C 0.4041(7) 0.0399(3) 0.1073(4) 0.0426(14) Uani 1 1 d . . .
N9 N 0.4700(6) 0.0743(2) 0.1362(4) 0.0551(15) Uani 1 1 d . . .
O12 O 1.4366(7) 0.0864(3) 0.9159(4) 0.0768(17) Uani 1 1 d D . .
H1W H 1.530(11) 0.286(3) 0.401(6) 0.115 Uiso 1 1 d D . .
H2W H 1.564(9) 0.232(4) 0.404(6) 0.115 Uiso 1 1 d D . .
H3W H 1.357(6) 0.093(5) 0.937(6) 0.115 Uiso 1 1 d D . .
H4W H 1.434(12) 0.093(5) 0.860(2) 0.115 Uiso 1 1 d D . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O4 1.983(3) . ?
Zn1 O1 2.056(3) . ?
Zn1 N1 2.057(4) . ?
Zn1 N2 2.062(4) . ?
Zn1 N3 2.219(4) . ?
Zn2 O2 2.057(3) 1_655 ?
Zn2 N5 2.130(4) . ?
Zn2 O3 2.134(3) . ?
Zn2 N4 2.136(4) . ?
Zn2 O5 2.154(3) . ?
Zn2 N6 2.217(4) . ?
N1 C5 1.339(6) . ?
N1 C1 1.343(6) . ?
N2 C12 1.326(6) . ?
N2 C8 1.351(6) . ?
N3 C6 1.471(6) . ?
N3 C7 1.475(6) . ?
N3 C13 1.480(6) . ?
N4 C19 1.342(6) . ?
N4 C15 1.350(6) . ?
N5 C26 1.335(6) . ?
N5 C22 1.353(6) . ?
N6 C20 1.465(6) . ?
N6 C27 1.467(6) . ?
N6 C21 1.486(6) . ?
O1 C14 1.277(5) . ?
O2 C14 1.249(5) . ?
O2 Zn2 2.057(3) 1_455 ?
O3 C28 1.257(6) . ?
O4 C28 1.268(6) . ?
O5 H1W 0.86(2) . ?
O5 H2W 0.85(2) . ?
C1 C2 1.372(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.526(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.520(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.376(7) . ?
C9 C10 1.375(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.512(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C16 1.370(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.516(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.522(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.389(7) . ?
C23 C24 1.375(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.391(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.528(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
N7 O7 1.221(6) . ?
N7 O6 1.243(6) . ?
N7 O8 1.264(6) . ?
N8 O11 1.182(7) . ?
N8 O9 1.242(7) . ?
N8 O10 1.267(6) . ?
C29 C30 1.449(9) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 N9 1.106(8) . ?
O12 H3W 0.86(2) . ?
O12 H4W 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Zn1 O1 86.15(14) . . ?
O4 Zn1 N1 106.02(15) . . ?
O1 Zn1 N1 113.14(15) . . ?
O4 Zn1 N2 107.10(15) . . ?
O1 Zn1 N2 114.00(14) . . ?
N1 Zn1 N2 123.11(16) . . ?
O4 Zn1 N3 164.14(14) . . ?
O1 Zn1 N3 77.99(13) . . ?
N1 Zn1 N3 80.58(15) . . ?
N2 Zn1 N3 79.87(15) . . ?
O2 Zn2 N5 104.69(14) 1_655 . ?
O2 Zn2 O3 89.26(12) 1_655 . ?
N5 Zn2 O3 87.62(13) . . ?
O2 Zn2 N4 98.89(14) 1_655 . ?
N5 Zn2 N4 156.33(16) . . ?
O3 Zn2 N4 90.75(14) . . ?
O2 Zn2 O5 94.27(13) 1_655 . ?
N5 Zn2 O5 89.07(14) . . ?
O3 Zn2 O5 175.68(13) . . ?
N4 Zn2 O5 91.16(14) . . ?
O2 Zn2 N6 169.05(14) 1_655 . ?
N5 Zn2 N6 78.58(15) . . ?
O3 Zn2 N6 80.38(13) . . ?
N4 Zn2 N6 77.87(15) . . ?
O5 Zn2 N6 96.24(14) . . ?
C5 N1 C1 118.1(4) . . ?
C5 N1 Zn1 115.7(3) . . ?
C1 N1 Zn1 125.9(3) . . ?
C12 N2 C8 118.9(4) . . ?
C12 N2 Zn1 124.6(4) . . ?
C8 N2 Zn1 115.7(3) . . ?
C6 N3 C7 112.9(4) . . ?
C6 N3 C13 112.1(4) . . ?
C7 N3 C13 112.8(4) . . ?
C6 N3 Zn1 106.9(3) . . ?
C7 N3 Zn1 104.7(3) . . ?
C13 N3 Zn1 106.7(3) . . ?
C19 N4 C15 118.8(4) . . ?
C19 N4 Zn2 114.7(3) . . ?
C15 N4 Zn2 126.2(3) . . ?
C26 N5 C22 119.2(4) . . ?
C26 N5 Zn2 126.1(3) . . ?
C22 N5 Zn2 114.3(3) . . ?
C20 N6 C27 112.3(4) . . ?
C20 N6 C21 113.2(4) . . ?
C27 N6 C21 110.5(4) . . ?
C20 N6 Zn2 106.5(3) . . ?
C27 N6 Zn2 108.6(3) . . ?
C21 N6 Zn2 105.3(3) . . ?
C14 O1 Zn1 118.1(3) . . ?
C14 O2 Zn2 129.0(3) . 1_455 ?
C28 O3 Zn2 114.7(3) . . ?
C28 O4 Zn1 120.8(3) . . ?
Zn2 O5 H1W 123(7) . . ?
Zn2 O5 H2W 103(8) . . ?
H1W O5 H2W 99(9) . . ?
N1 C1 C2 122.9(5) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.8(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 118.4(5) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.4(4) . . ?
N1 C5 C6 118.3(4) . . ?
C4 C5 C6 119.3(4) . . ?
N3 C6 C5 113.3(4) . . ?
N3 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
N3 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N3 C7 C8 111.0(4) . . ?
N3 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C9 122.2(5) . . ?
N2 C8 C7 115.7(4) . . ?
C9 C8 C7 122.1(5) . . ?
C10 C9 C8 118.0(5) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 121.0(5) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 117.2(5) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
N2 C12 C11 122.7(5) . . ?
N2 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
N3 C13 C14 111.5(4) . . ?
N3 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N3 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O2 C14 O1 123.8(4) . . ?
O2 C14 C13 118.1(4) . . ?
O1 C14 C13 118.1(4) . . ?
N4 C15 C16 122.8(5) . . ?
N4 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C17 118.6(5) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C16 C17 C18 119.4(5) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 119.1(5) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
N4 C19 C18 121.3(5) . . ?
N4 C19 C20 116.6(4) . . ?
C18 C19 C20 122.1(5) . . ?
N6 C20 C19 110.1(4) . . ?
N6 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
N6 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.2 . . ?
N6 C21 C22 109.8(4) . . ?
N6 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
N6 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
N5 C22 C23 121.4(5) . . ?
N5 C22 C21 116.4(4) . . ?
C23 C22 C21 122.1(5) . . ?
C24 C23 C22 118.8(5) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 120.2(5) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 118.2(5) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
N5 C26 C25 122.3(5) . . ?
N5 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
N6 C27 C28 114.4(4) . . ?
N6 C27 H27A 108.7 . . ?
C28 C27 H27A 108.7 . . ?
N6 C27 H27B 108.7 . . ?
C28 C27 H27B 108.7 . . ?
H27A C27 H27B 107.6 . . ?
O3 C28 O4 124.2(4) . . ?
O3 C28 C27 121.7(4) . . ?
O4 C28 C27 114.1(4) . . ?
O7 N7 O6 120.4(5) . . ?
O7 N7 O8 119.8(5) . . ?
O6 N7 O8 119.9(5) . . ?
O11 N8 O9 120.1(7) . . ?
O11 N8 O10 123.9(7) . . ?
O9 N8 O10 115.9(6) . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N9 C30 C29 178.8(8) . . ?
H3W O12 H4W 111(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Zn1 N1 C5 -152.3(3) . . . . ?
O1 Zn1 N1 C5 -59.6(4) . . . . ?
N2 Zn1 N1 C5 84.2(4) . . . . ?
N3 Zn1 N1 C5 12.9(3) . . . . ?
O4 Zn1 N1 C1 21.4(4) . . . . ?
O1 Zn1 N1 C1 114.0(4) . . . . ?
N2 Zn1 N1 C1 -102.2(4) . . . . ?
N3 Zn1 N1 C1 -173.4(4) . . . . ?
O4 Zn1 N2 C12 4.7(4) . . . . ?
O1 Zn1 N2 C12 -88.7(4) . . . . ?
N1 Zn1 N2 C12 127.8(4) . . . . ?
N3 Zn1 N2 C12 -160.6(4) . . . . ?
O4 Zn1 N2 C8 174.2(3) . . . . ?
O1 Zn1 N2 C8 80.8(3) . . . . ?
N1 Zn1 N2 C8 -62.7(4) . . . . ?
N3 Zn1 N2 C8 8.9(3) . . . . ?
O4 Zn1 N3 C6 96.5(6) . . . . ?
O1 Zn1 N3 C6 96.7(3) . . . . ?
N1 Zn1 N3 C6 -19.6(3) . . . . ?
N2 Zn1 N3 C6 -145.9(3) . . . . ?
O4 Zn1 N3 C7 -143.4(5) . . . . ?
O1 Zn1 N3 C7 -143.3(3) . . . . ?
N1 Zn1 N3 C7 100.5(3) . . . . ?
N2 Zn1 N3 C7 -25.8(3) . . . . ?
O4 Zn1 N3 C13 -23.7(7) . . . . ?
O1 Zn1 N3 C13 -23.5(3) . . . . ?
N1 Zn1 N3 C13 -139.7(3) . . . . ?
N2 Zn1 N3 C13 94.0(3) . . . . ?
O2 Zn2 N4 C19 179.7(3) 1_655 . . . ?
N5 Zn2 N4 C19 4.5(6) . . . . ?
O3 Zn2 N4 C19 90.3(3) . . . . ?
O5 Zn2 N4 C19 -85.8(3) . . . . ?
N6 Zn2 N4 C19 10.3(3) . . . . ?
O2 Zn2 N4 C15 5.5(4) 1_655 . . . ?
N5 Zn2 N4 C15 -169.7(4) . . . . ?
O3 Zn2 N4 C15 -83.9(4) . . . . ?
O5 Zn2 N4 C15 100.0(4) . . . . ?
N6 Zn2 N4 C15 -163.9(4) . . . . ?
O2 Zn2 N5 C26 -8.8(4) 1_655 . . . ?
O3 Zn2 N5 C26 79.8(4) . . . . ?
N4 Zn2 N5 C26 166.3(4) . . . . ?
O5 Zn2 N5 C26 -103.0(4) . . . . ?
N6 Zn2 N5 C26 160.5(4) . . . . ?
O2 Zn2 N5 C22 178.8(3) 1_655 . . . ?
O3 Zn2 N5 C22 -92.6(3) . . . . ?
N4 Zn2 N5 C22 -6.1(6) . . . . ?
O5 Zn2 N5 C22 84.6(3) . . . . ?
N6 Zn2 N5 C22 -11.9(3) . . . . ?
O2 Zn2 N6 C20 -101.6(7) 1_655 . . . ?
N5 Zn2 N6 C20 149.8(3) . . . . ?
O3 Zn2 N6 C20 -120.7(3) . . . . ?
N4 Zn2 N6 C20 -27.8(3) . . . . ?
O5 Zn2 N6 C20 62.0(3) . . . . ?
O2 Zn2 N6 C27 19.6(9) 1_655 . . . ?
N5 Zn2 N6 C27 -89.0(3) . . . . ?
O3 Zn2 N6 C27 0.5(3) . . . . ?
N4 Zn2 N6 C27 93.4(3) . . . . ?
O5 Zn2 N6 C27 -176.8(3) . . . . ?
O2 Zn2 N6 C21 138.0(7) 1_655 . . . ?
N5 Zn2 N6 C21 29.4(3) . . . . ?
O3 Zn2 N6 C21 118.9(3) . . . . ?
N4 Zn2 N6 C21 -148.2(3) . . . . ?
O5 Zn2 N6 C21 -58.4(3) . . . . ?
O4 Zn1 O1 C14 -163.4(3) . . . . ?
N1 Zn1 O1 C14 90.8(3) . . . . ?
N2 Zn1 O1 C14 -56.4(4) . . . . ?
N3 Zn1 O1 C14 16.7(3) . . . . ?
O2 Zn2 O3 C28 -179.5(3) 1_655 . . . ?
N5 Zn2 O3 C28 75.8(3) . . . . ?
N4 Zn2 O3 C28 -80.6(3) . . . . ?
O5 Zn2 O3 C28 35.7(19) . . . . ?
N6 Zn2 O3 C28 -3.0(3) . . . . ?
O1 Zn1 O4 C28 -174.5(3) . . . . ?
N1 Zn1 O4 C28 -61.5(4) . . . . ?
N2 Zn1 O4 C28 71.5(4) . . . . ?
N3 Zn1 O4 C28 -174.3(4) . . . . ?
C5 N1 C1 C2 -0.9(8) . . . . ?
Zn1 N1 C1 C2 -174.5(4) . . . . ?
N1 C1 C2 C3 0.4(9) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C2 C3 C4 C5 0.5(8) . . . . ?
C1 N1 C5 C4 1.3(7) . . . . ?
Zn1 N1 C5 C4 175.4(4) . . . . ?
C1 N1 C5 C6 -177.3(4) . . . . ?
Zn1 N1 C5 C6 -3.1(6) . . . . ?
C3 C4 C5 N1 -1.1(8) . . . . ?
C3 C4 C5 C6 177.5(5) . . . . ?
C7 N3 C6 C5 -91.3(5) . . . . ?
C13 N3 C6 C5 140.0(4) . . . . ?
Zn1 N3 C6 C5 23.3(5) . . . . ?
N1 C5 C6 N3 -15.1(6) . . . . ?
C4 C5 C6 N3 166.2(4) . . . . ?
C6 N3 C7 C8 154.0(4) . . . . ?
C13 N3 C7 C8 -77.7(5) . . . . ?
Zn1 N3 C7 C8 38.0(4) . . . . ?
C12 N2 C8 C9 0.1(7) . . . . ?
Zn1 N2 C8 C9 -170.1(4) . . . . ?
C12 N2 C8 C7 -179.2(4) . . . . ?
Zn1 N2 C8 C7 10.7(5) . . . . ?
N3 C7 C8 N2 -34.7(5) . . . . ?
N3 C7 C8 C9 146.0(4) . . . . ?
N2 C8 C9 C10 1.3(7) . . . . ?
C7 C8 C9 C10 -179.5(4) . . . . ?
C8 C9 C10 C11 -2.0(7) . . . . ?
C9 C10 C11 C12 1.4(8) . . . . ?
C8 N2 C12 C11 -0.8(7) . . . . ?
Zn1 N2 C12 C11 168.4(4) . . . . ?
C10 C11 C12 N2 0.1(8) . . . . ?
C6 N3 C13 C14 -89.3(5) . . . . ?
C7 N3 C13 C14 141.9(4) . . . . ?
Zn1 N3 C13 C14 27.5(4) . . . . ?
Zn2 O2 C14 O1 -2.2(6) 1_455 . . . ?
Zn2 O2 C14 C13 175.5(3) 1_455 . . . ?
Zn1 O1 C14 O2 172.3(3) . . . . ?
Zn1 O1 C14 C13 -5.3(5) . . . . ?
N3 C13 C14 O2 165.4(4) . . . . ?
N3 C13 C14 O1 -16.8(6) . . . . ?
C19 N4 C15 C16 -0.6(7) . . . . ?
Zn2 N4 C15 C16 173.4(4) . . . . ?
N4 C15 C16 C17 -1.1(8) . . . . ?
C15 C16 C17 C18 1.0(8) . . . . ?
C16 C17 C18 C19 0.6(8) . . . . ?
C15 N4 C19 C18 2.3(7) . . . . ?
Zn2 N4 C19 C18 -172.4(4) . . . . ?
C15 N4 C19 C20 -175.5(4) . . . . ?
Zn2 N4 C19 C20 9.8(5) . . . . ?
C17 C18 C19 N4 -2.3(8) . . . . ?
C17 C18 C19 C20 175.4(5) . . . . ?
C27 N6 C20 C19 -78.5(5) . . . . ?
C21 N6 C20 C19 155.5(4) . . . . ?
Zn2 N6 C20 C19 40.3(4) . . . . ?
N4 C19 C20 N6 -35.2(6) . . . . ?
C18 C19 C20 N6 147.0(5) . . . . ?
C20 N6 C21 C22 -157.7(4) . . . . ?
C27 N6 C21 C22 75.3(5) . . . . ?
Zn2 N6 C21 C22 -41.8(4) . . . . ?
C26 N5 C22 C23 -1.9(7) . . . . ?
Zn2 N5 C22 C23 171.0(4) . . . . ?
C26 N5 C22 C21 178.1(4) . . . . ?
Zn2 N5 C22 C21 -9.0(5) . . . . ?
N6 C21 C22 N5 35.9(6) . . . . ?
N6 C21 C22 C23 -144.1(5) . . . . ?
N5 C22 C23 C24 1.1(8) . . . . ?
C21 C22 C23 C24 -178.9(5) . . . . ?
C22 C23 C24 C25 -0.4(8) . . . . ?
C23 C24 C25 C26 0.5(8) . . . . ?
C22 N5 C26 C25 2.1(7) . . . . ?
Zn2 N5 C26 C25 -170.0(4) . . . . ?
C24 C25 C26 N5 -1.4(8) . . . . ?
C20 N6 C27 C28 119.1(5) . . . . ?
C21 N6 C27 C28 -113.5(4) . . . . ?
Zn2 N6 C27 C28 1.6(5) . . . . ?
Zn2 O3 C28 O4 -176.8(3) . . . . ?
Zn2 O3 C28 C27 5.1(5) . . . . ?
Zn1 O4 C28 O3 -8.5(6) . . . . ?
Zn1 O4 C28 C27 169.8(3) . . . . ?
N6 C27 C28 O3 -4.6(7) . . . . ?
N6 C27 C28 O4 177.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H1W O10 0.86(2) 1.86(3) 2.709(6) 172(10) 4_665
O5 H1W N8 0.86(2) 2.55(6) 3.291(6) 146(9) 4_665
O5 H2W O1 0.85(2) 1.95(7) 2.674(5) 143(10) 1_655
O12 H3W O11 0.86(2) 1.96(3) 2.812(9) 170(11) .
O12 H3W N8 0.86(2) 2.70(6) 3.465(9) 148(9) .
O12 H4W O8 0.87(2) 1.90(2) 2.766(8) 174(11) 1_655

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.253
####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1418410'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2015-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 Br2 N3 O2 Zn'
_chemical_formula_weight         510.53

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                   7.5873(7)
_cell_length_b                   8.5099(8)
_cell_length_c                   17.2513(13)
_cell_angle_alpha                79.837(6)
_cell_angle_beta                 85.822(5)
_cell_angle_gamma                67.110(4)
_cell_volume                     1010.04(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1789
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      26.02

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    5.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3247
_exptl_absorpt_correction_T_max  0.8600
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
83 frames in 2 sets of ω scans. Rotation/frame = 1.9 °.
Crystal-detector distance = 30 mm. Measuring time  = 600 s/°.
;

_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  
;
Nonius KappaCCD area-detector diffractometer
;
_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            4775
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         25.96
_reflns_number_total             3358
_reflns_number_gt                2553
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.0556P)²+1.0925P] 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         3358
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.0001

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 0.95284(8) 0.94229(8) 0.30407(4) 0.0442(2) Uani 1 1 d . . .
Br1 Br 0.79709(9) 0.92126(9) 0.19215(4) 0.0630(2) Uani 1 1 d . . .
Br2 Br 0.74825(10) 1.07406(9) 0.40893(4) 0.0658(2) Uani 1 1 d . . .
N1 N 1.0276(7) 1.1566(6) 0.2539(3) 0.0538(12) Uani 1 1 d . . .
N2 N 1.0266(6) 0.6754(6) 0.3613(3) 0.0497(11) Uani 1 1 d . . .
N3 N 1.2702(6) 0.8383(6) 0.3176(3) 0.0478(11) Uani 1 1 d . . .
O2 O 1.4429(10) 0.8327(7) 0.0425(3) 0.0945(17) Uani 1 1 d . . .
O1 O 1.4952(8) 0.5812(6) 0.1203(3) 0.0823(15) Uani 1 1 d . . .
C1 C 0.9099(10) 1.3011(8) 0.2073(4) 0.0684(17) Uani 1 1 d . . .
H1 H 0.7870 1.3110 0.1972 0.082 Uiso 1 1 calc R . .
C2 C 0.9680(13) 1.4315(10) 0.1750(5) 0.082(2) Uani 1 1 d . . .
H2 H 0.8849 1.5292 0.1437 0.098 Uiso 1 1 calc R . .
C3 C 1.1480(13) 1.4179(11) 0.1888(5) 0.081(2) Uani 1 1 d . . .
H3 H 1.1889 1.5060 0.1669 0.098 Uiso 1 1 calc R . .
C4 C 1.2675(11) 1.2744(11) 0.2349(4) 0.071(2) Uani 1 1 d . . .
H4 H 1.3912 1.2633 0.2444 0.085 Uiso 1 1 calc R . .
C5 C 1.2045(8) 1.1452(8) 0.2678(4) 0.0515(14) Uani 1 1 d . . .
C6 C 1.3258(8) 0.9839(9) 0.3205(4) 0.0594(16) Uani 1 1 d . . .
H6A H 1.4588 0.9533 0.3047 0.071 Uiso 1 1 calc R . .
H6B H 1.3142 1.0063 0.3742 0.071 Uiso 1 1 calc R . .
C7 C 1.3081(8) 0.7173(9) 0.3915(4) 0.0601(16) Uani 1 1 d . . .
H7A H 1.2710 0.7812 0.4353 0.072 Uiso 1 1 calc R . .
H7B H 1.4440 0.6476 0.3957 0.072 Uiso 1 1 calc R . .
C8 C 1.1991(9) 0.6015(8) 0.3957(3) 0.0545(14) Uani 1 1 d . . .
C9 C 1.2653(12) 0.4309(9) 0.4338(4) 0.075(2) Uani 1 1 d . . .
H9 H 1.3866 0.3796 0.4561 0.090 Uiso 1 1 calc R . .
C10 C 1.1508(17) 0.3393(10) 0.4381(5) 0.091(3) Uani 1 1 d . . .
H10 H 1.1912 0.2263 0.4648 0.109 Uiso 1 1 calc R . .
C11 C 0.9758(16) 0.4163(11) 0.4026(5) 0.086(2) Uani 1 1 d . . .
H11 H 0.8956 0.3562 0.4050 0.103 Uiso 1 1 calc R . .
C12 C 0.9187(11) 0.5846(9) 0.3630(4) 0.0683(18) Uani 1 1 d . . .
H12 H 0.8018 0.6348 0.3371 0.082 Uiso 1 1 calc R . .
C13 C 1.3718(8) 0.7416(8) 0.2536(3) 0.0503(13) Uani 1 1 d . . .
H13A H 1.3331 0.6452 0.2547 0.060 Uiso 1 1 calc R . .
H13B H 1.5080 0.6942 0.2641 0.060 Uiso 1 1 calc R . .
C14 C 1.3374(8) 0.8471(8) 0.1712(3) 0.0529(13) Uani 1 1 d . . .
H14A H 1.2011 0.9004 0.1608 0.063 Uiso 1 1 calc R . .
H14B H 1.3854 0.9384 0.1678 0.063 Uiso 1 1 calc R . .
C15 C 1.4360(9) 0.7343(9) 0.1103(4) 0.0561(15) Uani 1 1 d . . .
C16 C 1.5343(19) 0.7415(15) -0.0231(5) 0.128(4) Uani 1 1 d . . .
H16A H 1.6575 0.6552 -0.0070 0.192 Uiso 1 1 calc R . .
H16B H 1.5495 0.8223 -0.0668 0.192 Uiso 1 1 calc R . .
H16C H 1.4558 0.6870 -0.0385 0.192 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 2.139(5) . ?
Zn1 N2 2.179(5) . ?
Zn1 N3 2.233(4) . ?
Zn1 Br1 2.4032(9) . ?
Zn1 Br2 2.4273(9) . ?
N1 C5 1.343(7) . ?
N1 C1 1.363(8) . ?
N2 C12 1.322(8) . ?
N2 C8 1.343(7) . ?
N3 C7 1.459(8) . ?
N3 C6 1.466(7) . ?
N3 C13 1.481(7) . ?
O2 C15 1.324(8) . ?
O2 C16 1.463(10) . ?
O1 C15 1.186(8) . ?
C1 C2 1.365(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.502(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.503(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.391(9) . ?
C9 C10 1.366(13) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(11) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.522(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.505(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 N2 151.98(18) . . ?
N1 Zn1 N3 76.30(18) . . ?
N2 Zn1 N3 75.68(17) . . ?
N1 Zn1 Br1 99.00(13) . . ?
N2 Zn1 Br1 96.32(13) . . ?
N3 Zn1 Br1 123.50(12) . . ?
N1 Zn1 Br2 97.42(14) . . ?
N2 Zn1 Br2 96.33(13) . . ?
N3 Zn1 Br2 119.51(12) . . ?
Br1 Zn1 Br2 116.94(3) . . ?
C5 N1 C1 118.1(5) . . ?
C5 N1 Zn1 117.5(4) . . ?
C1 N1 Zn1 124.4(4) . . ?
C12 N2 C8 119.6(6) . . ?
C12 N2 Zn1 125.6(5) . . ?
C8 N2 Zn1 114.8(4) . . ?
C7 N3 C6 112.3(5) . . ?
C7 N3 C13 108.2(5) . . ?
C6 N3 C13 111.4(5) . . ?
C7 N3 Zn1 104.7(3) . . ?
C6 N3 Zn1 107.9(4) . . ?
C13 N3 Zn1 112.2(3) . . ?
C15 O2 C16 116.0(6) . . ?
N1 C1 C2 121.7(7) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 119.7(7) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 119.4(7) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.8(7) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 121.3(6) . . ?
N1 C5 C6 115.4(5) . . ?
C4 C5 C6 123.3(6) . . ?
N3 C6 C5 112.2(4) . . ?
N3 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N3 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N3 C7 C8 110.8(4) . . ?
N3 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C9 120.9(7) . . ?
N2 C8 C7 115.2(5) . . ?
C9 C8 C7 123.9(6) . . ?
C10 C9 C8 119.5(8) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 118.9(7) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 119.6(8) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
N2 C12 C11 121.5(8) . . ?
N2 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
N3 C13 C14 115.1(5) . . ?
N3 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
N3 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 110.8(5) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O1 C15 O2 124.7(6) . . ?
O1 C15 C14 125.8(6) . . ?
O2 C15 C14 109.5(6) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N2 Zn1 N1 C5 -13.5(7) . . . . ?
N3 Zn1 N1 C5 -13.4(4) . . . . ?
Br1 Zn1 N1 C5 -135.8(4) . . . . ?
Br2 Zn1 N1 C5 105.3(4) . . . . ?
N2 Zn1 N1 C1 164.6(5) . . . . ?
N3 Zn1 N1 C1 164.7(6) . . . . ?
Br1 Zn1 N1 C1 42.2(5) . . . . ?
Br2 Zn1 N1 C1 -76.7(5) . . . . ?
N1 Zn1 N2 C12 -160.4(5) . . . . ?
N3 Zn1 N2 C12 -160.5(5) . . . . ?
Br1 Zn1 N2 C12 -37.5(5) . . . . ?
Br2 Zn1 N2 C12 80.6(5) . . . . ?
N1 Zn1 N2 C8 18.5(6) . . . . ?
N3 Zn1 N2 C8 18.3(4) . . . . ?
Br1 Zn1 N2 C8 141.4(4) . . . . ?
Br2 Zn1 N2 C8 -100.5(4) . . . . ?
N1 Zn1 N3 C7 145.8(4) . . . . ?
N2 Zn1 N3 C7 -34.3(4) . . . . ?
Br1 Zn1 N3 C7 -122.4(3) . . . . ?
Br2 Zn1 N3 C7 55.0(4) . . . . ?
N1 Zn1 N3 C6 26.1(4) . . . . ?
N2 Zn1 N3 C6 -154.0(4) . . . . ?
Br1 Zn1 N3 C6 117.9(3) . . . . ?
Br2 Zn1 N3 C6 -64.8(4) . . . . ?
N1 Zn1 N3 C13 -97.1(4) . . . . ?
N2 Zn1 N3 C13 82.9(4) . . . . ?
Br1 Zn1 N3 C13 -5.2(4) . . . . ?
Br2 Zn1 N3 C13 172.1(3) . . . . ?
C5 N1 C1 C2 0.1(10) . . . . ?
Zn1 N1 C1 C2 -178.0(6) . . . . ?
N1 C1 C2 C3 0.5(12) . . . . ?
C1 C2 C3 C4 -0.2(12) . . . . ?
C2 C3 C4 C5 -0.6(11) . . . . ?
C1 N1 C5 C4 -1.0(8) . . . . ?
Zn1 N1 C5 C4 177.2(5) . . . . ?
C1 N1 C5 C6 179.2(6) . . . . ?
Zn1 N1 C5 C6 -2.6(6) . . . . ?
C3 C4 C5 N1 1.2(10) . . . . ?
C3 C4 C5 C6 -179.0(6) . . . . ?
C7 N3 C6 C5 -150.4(5) . . . . ?
C13 N3 C6 C5 88.0(6) . . . . ?
Zn1 N3 C6 C5 -35.5(6) . . . . ?
N1 C5 C6 N3 26.7(7) . . . . ?
C4 C5 C6 N3 -153.1(6) . . . . ?
C6 N3 C7 C8 163.1(5) . . . . ?
C13 N3 C7 C8 -73.5(6) . . . . ?
Zn1 N3 C7 C8 46.4(5) . . . . ?
C12 N2 C8 C9 -0.5(9) . . . . ?
Zn1 N2 C8 C9 -179.4(5) . . . . ?
C12 N2 C8 C7 -178.9(6) . . . . ?
Zn1 N2 C8 C7 2.2(6) . . . . ?
N3 C7 C8 N2 -34.3(7) . . . . ?
N3 C7 C8 C9 147.3(6) . . . . ?
N2 C8 C9 C10 -2.0(10) . . . . ?
C7 C8 C9 C10 176.3(6) . . . . ?
C8 C9 C10 C11 2.1(11) . . . . ?
C9 C10 C11 C12 0.2(11) . . . . ?
C8 N2 C12 C11 2.8(10) . . . . ?
Zn1 N2 C12 C11 -178.4(5) . . . . ?
C10 C11 C12 N2 -2.7(11) . . . . ?
C7 N3 C13 C14 176.4(5) . . . . ?
C6 N3 C13 C14 -59.7(6) . . . . ?
Zn1 N3 C13 C14 61.4(5) . . . . ?
N3 C13 C14 C15 -176.1(5) . . . . ?
C16 O2 C15 O1 -1.1(12) . . . . ?
C16 O2 C15 C14 -179.7(7) . . . . ?
C13 C14 C15 O1 16.2(9) . . . . ?
C13 C14 C15 O2 -165.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.849
_diffrn_reflns_theta_full        25.96
_diffrn_measured_fraction_theta_full 0.849
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.090
####################################################################### 
# 
# 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_2n
_database_code_depnum_ccdc_archive 'CCDC 1418411'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2015-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N5 O8 Zn'
_chemical_formula_weight         460.71

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'
O O 0.0492 0.0322 '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'

_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                   8.0542(5)
_cell_length_b                   8.5048(6)
_cell_length_c                   16.0539(8)
_cell_angle_alpha                84.712(5)
_cell_angle_beta                 86.468(5)
_cell_angle_gamma                77.287(6)
_cell_volume                     1067.2(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5281
_cell_measurement_theta_min      5.3448
_cell_measurement_theta_max      75.5168

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    2.051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_T_max  0.9044
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9529
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.35
_diffrn_reflns_theta_max         75.70
_reflns_number_total             4345
_reflns_number_gt                3931
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SIR-92 (Giacovazzo,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.1733P)²+0.4338P] 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         4345
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2433
_refine_ls_wR_factor_gt          0.2338
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001

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
Zn01 Zn 0.20768(6) 0.27958(6) 0.83820(3) 0.0444(2) Uani 1 1 d . . .
N1 N 0.3086(4) 0.4632(4) 0.8766(2) 0.0448(7) Uani 1 1 d . . .
N2 N 0.2171(5) 0.0707(4) 0.7809(2) 0.0482(7) Uani 1 1 d . . .
N3 N 0.4802(4) 0.2280(4) 0.7786(2) 0.0437(7) Uani 1 1 d . . .
N4 N -0.0347(5) 0.4842(5) 0.7327(3) 0.0564(8) Uani 1 1 d . . .
N5 N 0.1919(5) 0.1400(5) 0.9950(2) 0.0575(9) Uani 1 1 d . . .
O1 O 0.7765(4) 0.2134(5) 0.6641(2) 0.0691(10) Uani 1 1 d . . .
O2 O 0.6218(5) 0.4060(6) 0.5783(2) 0.0745(10) Uani 1 1 d . . .
O3 O -0.0316(4) 0.4141(4) 0.8069(2) 0.0624(8) Uani 1 1 d . . .
O4 O 0.0961(6) 0.4565(6) 0.6875(3) 0.0841(12) Uani 1 1 d . . .
O5 O -0.1681(5) 0.5728(6) 0.7098(3) 0.0830(12) Uani 1 1 d . . .
O6 O 0.0749(4) 0.2329(5) 0.9527(2) 0.0647(8) Uani 1 1 d . . .
O7 O 0.3345(5) 0.1013(5) 0.9583(2) 0.0667(9) Uani 1 1 d . . .
O8 O 0.1643(7) 0.0929(7) 1.0668(3) 0.1028(17) Uani 1 1 d . . .
C1 C 0.2119(5) 0.5937(5) 0.9099(3) 0.0509(9) Uani 1 1 d . . .
H1 H 0.0946 0.6030 0.9159 0.061 Uiso 1 1 calc R . .
C2 C 0.2830(6) 0.7153(5) 0.9357(3) 0.0537(9) Uani 1 1 d . . .
H2 H 0.2145 0.8047 0.9590 0.064 Uiso 1 1 calc R . .
C3 C 0.4559(6) 0.7010(5) 0.9261(3) 0.0535(9) Uani 1 1 d . . .
H3 H 0.5061 0.7811 0.9427 0.064 Uiso 1 1 calc R . .
C4 C 0.5560(5) 0.5655(5) 0.8914(2) 0.0496(8) Uani 1 1 d . . .
H4 H 0.6733 0.5546 0.8839 0.060 Uiso 1 1 calc R . .
C5 C 0.4786(5) 0.4482(5) 0.8685(2) 0.0424(7) Uani 1 1 d . . .
C6 C 0.5797(5) 0.2917(5) 0.8369(2) 0.0469(8) Uani 1 1 d . . .
H6A H 0.6843 0.3102 0.8084 0.056 Uiso 1 1 calc R . .
H6B H 0.6098 0.2124 0.8840 0.056 Uiso 1 1 calc R . .
C7 C 0.5246(5) 0.0522(5) 0.7765(3) 0.0506(9) Uani 1 1 d . . .
H7A H 0.5650 0.0029 0.8304 0.061 Uiso 1 1 calc R . .
H7B H 0.6157 0.0230 0.7346 0.061 Uiso 1 1 calc R . .
C8 C 0.3701(6) -0.0115(5) 0.7556(2) 0.0479(8) Uani 1 1 d . . .
C9 C 0.3890(7) -0.1533(6) 0.7160(3) 0.0622(11) Uani 1 1 d . . .
H9 H 0.4962 -0.2099 0.6989 0.075 Uiso 1 1 calc R . .
C10 C 0.2425(9) -0.2085(7) 0.7026(4) 0.0733(14) Uani 1 1 d . . .
H10 H 0.2507 -0.3019 0.6752 0.088 Uiso 1 1 calc R . .
C11 C 0.0854(8) -0.1235(7) 0.7301(4) 0.0745(15) Uani 1 1 d . . .
H11 H -0.0129 -0.1604 0.7229 0.089 Uiso 1 1 calc R . .
C12 C 0.0767(6) 0.0154(6) 0.7680(3) 0.0613(11) Uani 1 1 d . . .
H12 H -0.0294 0.0739 0.7855 0.074 Uiso 1 1 calc R . .
C13 C 0.4760(5) 0.3159(5) 0.6956(2) 0.0497(8) Uani 1 1 d . . .
H13A H 0.4289 0.4294 0.7023 0.060 Uiso 1 1 calc R . .
H13B H 0.3982 0.2779 0.6626 0.060 Uiso 1 1 calc R . .
C14 C 0.6447(6) 0.3022(6) 0.6462(3) 0.0547(9) Uani 1 1 d . . .
C15 C 0.7717(10) 0.4088(11) 0.5230(4) 0.097(2) Uani 1 1 d . . .
H15A H 0.8580 0.4385 0.5531 0.145 Uiso 1 1 calc R . .
H15B H 0.7415 0.4862 0.4761 0.145 Uiso 1 1 calc R . .
H15C H 0.8143 0.3034 0.5035 0.145 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Zn01 N2 2.059(4) . ?
Zn01 N1 2.068(3) . ?
Zn01 O3 2.078(3) . ?
Zn01 O6 2.120(3) . ?
Zn01 N3 2.306(3) . ?
Zn01 O7 2.466(4) . ?
N1 C1 1.342(5) . ?
N1 C5 1.346(5) . ?
N2 C8 1.335(6) . ?
N2 C12 1.351(6) . ?
N3 C7 1.462(5) . ?
N3 C13 1.465(5) . ?
N3 C6 1.479(5) . ?
N4 O5 1.224(5) . ?
N4 O4 1.233(6) . ?
N4 O3 1.281(5) . ?
N5 O8 1.209(6) . ?
N5 O7 1.249(6) . ?
N5 O6 1.275(6) . ?
O1 C14 1.194(6) . ?
O2 C14 1.333(6) . ?
O2 C15 1.456(7) . ?
C1 C2 1.393(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.513(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.528(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.390(6) . ?
C9 C10 1.398(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.518(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn01 N1 154.61(15) . . ?
N2 Zn01 O3 101.49(15) . . ?
N1 Zn01 O3 98.74(15) . . ?
N2 Zn01 O6 101.28(16) . . ?
N1 Zn01 O6 96.56(15) . . ?
O3 Zn01 O6 82.05(14) . . ?
N2 Zn01 N3 77.53(13) . . ?
N1 Zn01 N3 77.19(13) . . ?
O3 Zn01 N3 137.75(13) . . ?
O6 Zn01 N3 140.06(13) . . ?
N2 Zn01 O7 86.19(13) . . ?
N1 Zn01 O7 89.35(14) . . ?
O3 Zn01 O7 137.17(13) . . ?
O6 Zn01 O7 55.20(13) . . ?
N3 Zn01 O7 85.08(12) . . ?
C1 N1 C5 119.5(3) . . ?
C1 N1 Zn01 122.6(3) . . ?
C5 N1 Zn01 117.8(3) . . ?
C8 N2 C12 119.6(4) . . ?
C8 N2 Zn01 117.5(3) . . ?
C12 N2 Zn01 122.9(3) . . ?
C7 N3 C13 113.7(3) . . ?
C7 N3 C6 114.3(3) . . ?
C13 N3 C6 112.0(3) . . ?
C7 N3 Zn01 104.2(2) . . ?
C13 N3 Zn01 108.0(2) . . ?
C6 N3 Zn01 103.6(2) . . ?
O5 N4 O4 123.4(5) . . ?
O5 N4 O3 118.4(4) . . ?
O4 N4 O3 118.2(4) . . ?
O8 N5 O7 122.6(5) . . ?
O8 N5 O6 120.9(5) . . ?
O7 N5 O6 116.5(4) . . ?
C14 O2 C15 116.1(5) . . ?
N4 O3 Zn01 113.4(3) . . ?
N5 O6 Zn01 101.9(3) . . ?
N5 O7 Zn01 86.3(3) . . ?
N1 C1 C2 121.5(4) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.7(4) . . ?
N1 C5 C6 116.2(3) . . ?
C4 C5 C6 122.1(4) . . ?
N3 C6 C5 110.9(3) . . ?
N3 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
N3 C7 C8 110.6(3) . . ?
N3 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C9 121.6(4) . . ?
N2 C8 C7 117.0(3) . . ?
C9 C8 C7 121.3(4) . . ?
C8 C9 C10 118.1(5) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C9 119.6(5) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 118.9(5) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
N2 C12 C11 122.1(5) . . ?
N2 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
N3 C13 C14 116.7(3) . . ?
N3 C13 H13A 108.1 . . ?
C14 C13 H13A 108.1 . . ?
N3 C13 H13B 108.1 . . ?
C14 C13 H13B 108.1 . . ?
H13A C13 H13B 107.3 . . ?
O1 C14 O2 125.1(4) . . ?
O1 C14 C13 126.3(4) . . ?
O2 C14 C13 108.6(4) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
N2 Zn01 N1 C1 171.6(3) . . . . ?
O3 Zn01 N1 C1 29.1(3) . . . . ?
O6 Zn01 N1 C1 -53.9(3) . . . . ?
N3 Zn01 N1 C1 166.2(3) . . . . ?
O7 Zn01 N1 C1 -108.7(3) . . . . ?
N2 Zn01 N1 C5 -9.3(5) . . . . ?
O3 Zn01 N1 C5 -151.9(3) . . . . ?
O6 Zn01 N1 C5 125.2(3) . . . . ?
N3 Zn01 N1 C5 -14.7(3) . . . . ?
O7 Zn01 N1 C5 70.4(3) . . . . ?
N1 Zn01 N2 C8 8.8(5) . . . . ?
O3 Zn01 N2 C8 150.9(3) . . . . ?
O6 Zn01 N2 C8 -125.0(3) . . . . ?
N3 Zn01 N2 C8 14.2(3) . . . . ?
O7 Zn01 N2 C8 -71.6(3) . . . . ?
N1 Zn01 N2 C12 -170.9(3) . . . . ?
O3 Zn01 N2 C12 -28.8(4) . . . . ?
O6 Zn01 N2 C12 55.3(4) . . . . ?
N3 Zn01 N2 C12 -165.5(4) . . . . ?
O7 Zn01 N2 C12 108.7(4) . . . . ?
N2 Zn01 N3 C7 -28.5(2) . . . . ?
N1 Zn01 N3 C7 149.1(3) . . . . ?
O3 Zn01 N3 C7 -122.0(3) . . . . ?
O6 Zn01 N3 C7 64.2(3) . . . . ?
O7 Zn01 N3 C7 58.6(3) . . . . ?
N2 Zn01 N3 C13 92.7(3) . . . . ?
N1 Zn01 N3 C13 -89.7(3) . . . . ?
O3 Zn01 N3 C13 -0.8(4) . . . . ?
O6 Zn01 N3 C13 -174.6(3) . . . . ?
O7 Zn01 N3 C13 179.8(3) . . . . ?
N2 Zn01 N3 C6 -148.4(3) . . . . ?
N1 Zn01 N3 C6 29.2(2) . . . . ?
O3 Zn01 N3 C6 118.2(3) . . . . ?
O6 Zn01 N3 C6 -55.6(3) . . . . ?
O7 Zn01 N3 C6 -61.2(2) . . . . ?
O5 N4 O3 Zn01 -176.5(4) . . . . ?
O4 N4 O3 Zn01 4.9(5) . . . . ?
N2 Zn01 O3 N4 -80.2(3) . . . . ?
N1 Zn01 O3 N4 84.3(3) . . . . ?
O6 Zn01 O3 N4 179.8(3) . . . . ?
N3 Zn01 O3 N4 3.8(4) . . . . ?
O7 Zn01 O3 N4 -177.1(3) . . . . ?
O8 N5 O6 Zn01 176.8(5) . . . . ?
O7 N5 O6 Zn01 -3.1(5) . . . . ?
N2 Zn01 O6 N5 79.0(3) . . . . ?
N1 Zn01 O6 N5 -82.9(3) . . . . ?
O3 Zn01 O6 N5 179.2(3) . . . . ?
N3 Zn01 O6 N5 -5.0(4) . . . . ?
O7 Zn01 O6 N5 1.7(3) . . . . ?
O8 N5 O7 Zn01 -177.3(5) . . . . ?
O6 N5 O7 Zn01 2.6(4) . . . . ?
N2 Zn01 O7 N5 -108.3(3) . . . . ?
N1 Zn01 O7 N5 96.7(3) . . . . ?
O3 Zn01 O7 N5 -5.5(4) . . . . ?
O6 Zn01 O7 N5 -1.7(3) . . . . ?
N3 Zn01 O7 N5 173.9(3) . . . . ?
C5 N1 C1 C2 0.6(6) . . . . ?
Zn01 N1 C1 C2 179.7(3) . . . . ?
N1 C1 C2 C3 0.4(7) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C1 N1 C5 C4 -1.8(6) . . . . ?
Zn01 N1 C5 C4 179.1(3) . . . . ?
C1 N1 C5 C6 175.3(4) . . . . ?
Zn01 N1 C5 C6 -3.8(4) . . . . ?
C3 C4 C5 N1 1.8(6) . . . . ?
C3 C4 C5 C6 -175.0(4) . . . . ?
C7 N3 C6 C5 -152.0(3) . . . . ?
C13 N3 C6 C5 76.8(4) . . . . ?
Zn01 N3 C6 C5 -39.4(3) . . . . ?
N1 C5 C6 N3 32.0(4) . . . . ?
C4 C5 C6 N3 -151.0(3) . . . . ?
C13 N3 C7 C8 -79.6(4) . . . . ?
C6 N3 C7 C8 150.1(3) . . . . ?
Zn01 N3 C7 C8 37.7(3) . . . . ?
C12 N2 C8 C9 0.0(6) . . . . ?
Zn01 N2 C8 C9 -179.7(3) . . . . ?
C12 N2 C8 C7 -176.7(4) . . . . ?
Zn01 N2 C8 C7 3.6(5) . . . . ?
N3 C7 C8 N2 -30.8(5) . . . . ?
N3 C7 C8 C9 152.5(4) . . . . ?
N2 C8 C9 C10 0.4(7) . . . . ?
C7 C8 C9 C10 176.9(4) . . . . ?
C8 C9 C10 C11 -1.3(8) . . . . ?
C9 C10 C11 C12 1.7(9) . . . . ?
C8 N2 C12 C11 0.5(7) . . . . ?
Zn01 N2 C12 C11 -179.8(4) . . . . ?
C10 C11 C12 N2 -1.3(8) . . . . ?
C7 N3 C13 C14 -66.6(5) . . . . ?
C6 N3 C13 C14 64.8(5) . . . . ?
Zn01 N3 C13 C14 178.3(3) . . . . ?
C15 O2 C14 O1 -0.1(9) . . . . ?
C15 O2 C14 C13 -179.8(5) . . . . ?
N3 C13 C14 O1 8.8(7) . . . . ?
N3 C13 C14 O2 -171.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        75.70
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         2.228
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.178
####################################################################### 
# 
# 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_3n
_database_code_depnum_ccdc_archive 'CCDC 1418412'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2015-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N5 O8 Zn'
_chemical_formula_weight         560.82

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'

_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                   13.9549(4)
_cell_length_b                   12.2190(4)
_cell_length_c                   14.9510(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.883(2)
_cell_angle_gamma                90.00
_cell_volume                     2365.68(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5568
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7341
_exptl_absorpt_correction_T_max  0.9471
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
200 frames in 5 sets of φ scans + ω scans. Rotation/frame = 2.0 °.
Crystal-detector distance = 31 mm. Measuring time  = 120 s/°.
;

_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  
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9960
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5374
_reflns_number_gt                3115
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO and SCALEPACK'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.0409P)²+4.4986P] 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         5374
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001

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 0.49442(4) 0.75015(4) 0.23447(3) 0.04478(16) Uani 1 1 d . . .
N1 N 0.5529(3) 0.8924(3) 0.3211(2) 0.0495(9) Uani 1 1 d . . .
N2 N 0.4366(2) 0.6533(3) 0.1050(2) 0.0444(8) Uani 1 1 d . . .
N3 N 0.4473(3) 0.8765(3) 0.1237(2) 0.0452(8) Uani 1 1 d . . .
N4 N 0.6882(3) 0.6743(3) 0.2688(3) 0.0564(10) Uani 1 1 d . . .
N5 N 0.3530(4) 0.6959(5) 0.3218(3) 0.0729(12) Uani 1 1 d . . .
O1 O 0.3354(3) 1.0529(3) -0.0049(3) 0.0768(11) Uani 1 1 d . . .
O2 O 0.1896(3) 0.9858(3) 0.0022(2) 0.0706(10) Uani 1 1 d . . .
O3 O 0.6176(2) 0.6495(3) 0.3011(2) 0.0599(8) Uani 1 1 d . . .
O4 O 0.7683(3) 0.6207(3) 0.2946(3) 0.0840(12) Uani 1 1 d . . .
O5 O 0.6705(3) 0.7523(3) 0.2121(2) 0.0714(9) Uani 1 1 d . . .
O6 O 0.3508(5) 0.7629(6) 0.2655(3) 0.159(3) Uani 1 1 d . . .
O7 O 0.2850(3) 0.6792(4) 0.3511(3) 0.1058(15) Uani 1 1 d . . .
O8 O 0.4300(5) 0.6360(6) 0.3492(6) 0.179(3) Uani 1 1 d . . .
C1 C 0.5862(3) 0.9006(4) 0.4206(3) 0.0517(11) Uani 1 1 d . . .
C2 C 0.5982(4) 0.8063(5) 0.4765(3) 0.0621(12) Uani 1 1 d . . .
H2 H 0.5832 0.7380 0.4471 0.074 Uiso 1 1 calc R . .
C3 C 0.6322(4) 0.8149(6) 0.5753(4) 0.0738(16) Uani 1 1 d . . .
H3 H 0.6394 0.7520 0.6122 0.089 Uiso 1 1 calc R . .
C4 C 0.6561(4) 0.9159(6) 0.6208(4) 0.0783(17) Uani 1 1 d . . .
H4 H 0.6787 0.9200 0.6876 0.094 Uiso 1 1 calc R . .
C5 C 0.6468(4) 1.0075(6) 0.5689(4) 0.0739(16) Uani 1 1 d . . .
H5 H 0.6635 1.0746 0.6005 0.089 Uiso 1 1 calc R . .
C6 C 0.6117(3) 1.0042(4) 0.4661(3) 0.0582(13) Uani 1 1 d . . .
C7 C 0.6015(4) 1.0968(4) 0.4088(4) 0.0694(15) Uani 1 1 d . . .
H7 H 0.6160 1.1657 0.4371 0.083 Uiso 1 1 calc R . .
C8 C 0.5708(3) 1.0867(4) 0.3121(4) 0.0614(12) Uani 1 1 d . . .
H8 H 0.5653 1.1481 0.2738 0.074 Uiso 1 1 calc R . .
C9 C 0.5470(3) 0.9822(4) 0.2700(3) 0.0519(11) Uani 1 1 d . . .
C10 C 0.5202(4) 0.9689(4) 0.1632(3) 0.0571(12) Uani 1 1 d . . .
H10A H 0.4892 1.0360 0.1305 0.068 Uiso 1 1 calc R . .
H10B H 0.5828 0.9558 0.1510 0.068 Uiso 1 1 calc R . .
C11 C 0.4552(4) 0.8277(4) 0.0371(3) 0.0524(11) Uani 1 1 d . . .
H11A H 0.5261 0.8320 0.0413 0.063 Uiso 1 1 calc R . .
H11B H 0.4127 0.8689 -0.0192 0.063 Uiso 1 1 calc R . .
C12 C 0.4207(3) 0.7091(4) 0.0252(3) 0.0456(10) Uani 1 1 d . . .
C13 C 0.3794(3) 0.6625(4) -0.0668(3) 0.0530(11) Uani 1 1 d . . .
H13 H 0.3676 0.7057 -0.1211 0.064 Uiso 1 1 calc R . .
C14 C 0.3565(3) 0.5540(4) -0.0766(3) 0.0549(11) Uani 1 1 d . . .
H14 H 0.3289 0.5225 -0.1376 0.066 Uiso 1 1 calc R . .
C15 C 0.3750(3) 0.4896(4) 0.0062(3) 0.0470(10) Uani 1 1 d . . .
C16 C 0.3557(3) 0.3762(4) 0.0026(4) 0.0595(12) Uani 1 1 d . . .
H16 H 0.3305 0.3408 -0.0567 0.071 Uiso 1 1 calc R . .
C17 C 0.3733(4) 0.3185(4) 0.0839(4) 0.0637(13) Uani 1 1 d . . .
H17 H 0.3602 0.2436 0.0802 0.076 Uiso 1 1 calc R . .
C18 C 0.4112(4) 0.3701(4) 0.1740(4) 0.0636(13) Uani 1 1 d . . .
H18 H 0.4225 0.3293 0.2296 0.076 Uiso 1 1 calc R . .
C19 C 0.4320(3) 0.4806(4) 0.1812(3) 0.0537(11) Uani 1 1 d . . .
H19 H 0.4576 0.5143 0.2413 0.064 Uiso 1 1 calc R . .
C20 C 0.4143(3) 0.5422(3) 0.0973(3) 0.0435(9) Uani 1 1 d . . .
C21 C 0.3396(3) 0.9075(4) 0.1061(3) 0.0501(10) Uani 1 1 d . . .
H21A H 0.3371 0.9360 0.1658 0.060 Uiso 1 1 calc R . .
H21B H 0.2977 0.8418 0.0901 0.060 Uiso 1 1 calc R . .
C22 C 0.2908(4) 0.9910(4) 0.0276(3) 0.0550(11) Uani 1 1 d . . .
C23 C 0.1296(5) 1.0681(5) -0.0679(4) 0.098(2) Uani 1 1 d . . .
H23A H 0.1531 1.1400 -0.0436 0.146 Uiso 1 1 calc R . .
H23B H 0.0578 1.0609 -0.0780 0.146 Uiso 1 1 calc R . .
H23C H 0.1386 1.0572 -0.1278 0.146 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O3 2.045(3) . ?
Zn1 N1 2.139(4) . ?
Zn1 N2 2.153(3) . ?
Zn1 N3 2.179(3) . ?
Zn1 O6 2.225(7) . ?
N1 C9 1.322(6) . ?
N1 C1 1.387(5) . ?
N2 C12 1.319(5) . ?
N2 C20 1.388(5) . ?
N3 C11 1.467(5) . ?
N3 C21 1.475(5) . ?
N3 C10 1.486(5) . ?
N4 O4 1.227(5) . ?
N4 O5 1.238(5) . ?
N4 O3 1.285(5) . ?
N5 O6 1.165(7) . ?
N5 O7 1.201(5) . ?
N5 O8 1.238(7) . ?
O1 C22 1.192(6) . ?
O2 C22 1.321(6) . ?
O2 C23 1.469(6) . ?
C1 C2 1.396(7) . ?
C1 C6 1.418(6) . ?
C2 C3 1.377(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.431(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(7) . ?
C7 C8 1.352(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.407(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.507(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.516(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.399(6) . ?
C13 C14 1.359(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.407(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.409(6) . ?
C15 C20 1.418(6) . ?
C16 C17 1.347(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.403(6) . ?
C19 H19 0.9300 . ?
C21 C22 1.512(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
O3 Zn1 N1 97.58(13) . . ?
O3 Zn1 N2 94.15(13) . . ?
N1 Zn1 N2 157.17(14) . . ?
O3 Zn1 N3 139.23(13) . . ?
N1 Zn1 N3 79.83(13) . . ?
N2 Zn1 N3 78.50(13) . . ?
O3 Zn1 O6 126.81(19) . . ?
N1 Zn1 O6 89.26(17) . . ?
N2 Zn1 O6 99.27(15) . . ?
N3 Zn1 O6 93.94(19) . . ?
C9 N1 C1 118.9(4) . . ?
C9 N1 Zn1 113.4(3) . . ?
C1 N1 Zn1 127.5(3) . . ?
C12 N2 C20 118.2(4) . . ?
C12 N2 Zn1 114.2(3) . . ?
C20 N2 Zn1 127.6(3) . . ?
C11 N3 C21 110.7(3) . . ?
C11 N3 C10 113.2(3) . . ?
C21 N3 C10 112.1(3) . . ?
C11 N3 Zn1 106.4(3) . . ?
C21 N3 Zn1 108.5(2) . . ?
C10 N3 Zn1 105.6(2) . . ?
O4 N4 O5 123.5(5) . . ?
O4 N4 O3 119.5(4) . . ?
O5 N4 O3 117.0(4) . . ?
O6 N5 O7 124.8(7) . . ?
O6 N5 O8 116.1(7) . . ?
O7 N5 O8 119.0(7) . . ?
C22 O2 C23 115.9(5) . . ?
N4 O3 Zn1 107.3(3) . . ?
N5 O6 Zn1 108.6(6) . . ?
N1 C1 C2 119.9(4) . . ?
N1 C1 C6 120.2(4) . . ?
C2 C1 C6 119.8(4) . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.2(6) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C1 118.7(4) . . ?
C7 C6 C5 123.6(5) . . ?
C1 C6 C5 117.7(5) . . ?
C8 C7 C6 120.1(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.3(5) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
N1 C9 C8 122.8(4) . . ?
N1 C9 C10 117.4(4) . . ?
C8 C9 C10 119.7(4) . . ?
N3 C10 C9 111.5(4) . . ?
N3 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N3 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
N3 C11 C12 111.5(3) . . ?
N3 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 C13 123.3(4) . . ?
N2 C12 C11 116.7(4) . . ?
C13 C12 C11 120.0(4) . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 123.1(4) . . ?
C14 C15 C20 118.0(4) . . ?
C16 C15 C20 118.9(4) . . ?
C17 C16 C15 120.8(5) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.6(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.6(5) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
N2 C20 C19 119.4(4) . . ?
N2 C20 C15 121.2(4) . . ?
C19 C20 C15 119.4(4) . . ?
N3 C21 C22 116.5(4) . . ?
N3 C21 H21A 108.2 . . ?
C22 C21 H21A 108.2 . . ?
N3 C21 H21B 108.2 . . ?
C22 C21 H21B 108.2 . . ?
H21A C21 H21B 107.3 . . ?
O1 C22 O2 125.3(4) . . ?
O1 C22 C21 126.3(5) . . ?
O2 C22 C21 108.3(4) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
O3 Zn1 N1 C9 130.3(3) . . . . ?
N2 Zn1 N1 C9 10.0(5) . . . . ?
N3 Zn1 N1 C9 -8.5(3) . . . . ?
O6 Zn1 N1 C9 -102.6(3) . . . . ?
O3 Zn1 N1 C1 -55.7(3) . . . . ?
N2 Zn1 N1 C1 -176.0(3) . . . . ?
N3 Zn1 N1 C1 165.5(3) . . . . ?
O6 Zn1 N1 C1 71.4(4) . . . . ?
O3 Zn1 N2 C12 -127.1(3) . . . . ?
N1 Zn1 N2 C12 -6.2(5) . . . . ?
N3 Zn1 N2 C12 12.3(3) . . . . ?
O6 Zn1 N2 C12 104.5(3) . . . . ?
O3 Zn1 N2 C20 53.5(3) . . . . ?
N1 Zn1 N2 C20 174.4(3) . . . . ?
N3 Zn1 N2 C20 -167.1(3) . . . . ?
O6 Zn1 N2 C20 -74.9(4) . . . . ?
O3 Zn1 N3 C11 55.6(3) . . . . ?
N1 Zn1 N3 C11 145.4(3) . . . . ?
N2 Zn1 N3 C11 -27.4(3) . . . . ?
O6 Zn1 N3 C11 -126.0(3) . . . . ?
O3 Zn1 N3 C21 174.7(2) . . . . ?
N1 Zn1 N3 C21 -95.5(3) . . . . ?
N2 Zn1 N3 C21 91.8(3) . . . . ?
O6 Zn1 N3 C21 -6.9(3) . . . . ?
O3 Zn1 N3 C10 -65.0(3) . . . . ?
N1 Zn1 N3 C10 24.9(3) . . . . ?
N2 Zn1 N3 C10 -147.9(3) . . . . ?
O6 Zn1 N3 C10 113.4(3) . . . . ?
O4 N4 O3 Zn1 -176.2(3) . . . . ?
O5 N4 O3 Zn1 3.6(4) . . . . ?
N1 Zn1 O3 N4 -79.3(3) . . . . ?
N2 Zn1 O3 N4 81.1(3) . . . . ?
N3 Zn1 O3 N4 3.9(4) . . . . ?
O6 Zn1 O3 N4 -174.0(3) . . . . ?
O7 N5 O6 Zn1 -177.5(5) . . . . ?
O8 N5 O6 Zn1 -0.5(6) . . . . ?
O3 Zn1 O6 N5 -5.5(5) . . . . ?
N1 Zn1 O6 N5 -104.4(4) . . . . ?
N2 Zn1 O6 N5 96.9(4) . . . . ?
N3 Zn1 O6 N5 175.9(4) . . . . ?
C9 N1 C1 C2 -176.7(4) . . . . ?
Zn1 N1 C1 C2 9.6(6) . . . . ?
C9 N1 C1 C6 1.0(6) . . . . ?
Zn1 N1 C1 C6 -172.7(3) . . . . ?
N1 C1 C2 C3 179.3(4) . . . . ?
C6 C1 C2 C3 1.6(7) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C2 C3 C4 C5 -0.3(8) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
N1 C1 C6 C7 0.7(6) . . . . ?
C2 C1 C6 C7 178.4(4) . . . . ?
N1 C1 C6 C5 -179.2(4) . . . . ?
C2 C1 C6 C5 -1.6(6) . . . . ?
C4 C5 C6 C7 -179.4(5) . . . . ?
C4 C5 C6 C1 0.5(7) . . . . ?
C1 C6 C7 C8 -1.9(7) . . . . ?
C5 C6 C7 C8 178.0(4) . . . . ?
C6 C7 C8 C9 1.4(7) . . . . ?
C1 N1 C9 C8 -1.6(6) . . . . ?
Zn1 N1 C9 C8 173.0(3) . . . . ?
C1 N1 C9 C10 174.5(4) . . . . ?
Zn1 N1 C9 C10 -11.0(5) . . . . ?
C7 C8 C9 N1 0.4(7) . . . . ?
C7 C8 C9 C10 -175.6(4) . . . . ?
C11 N3 C10 C9 -153.3(4) . . . . ?
C21 N3 C10 C9 80.5(4) . . . . ?
Zn1 N3 C10 C9 -37.4(4) . . . . ?
N1 C9 C10 N3 34.2(6) . . . . ?
C8 C9 C10 N3 -149.6(4) . . . . ?
C21 N3 C11 C12 -79.2(4) . . . . ?
C10 N3 C11 C12 153.9(3) . . . . ?
Zn1 N3 C11 C12 38.4(4) . . . . ?
C20 N2 C12 C13 2.2(6) . . . . ?
Zn1 N2 C12 C13 -177.3(3) . . . . ?
C20 N2 C12 C11 -174.5(3) . . . . ?
Zn1 N2 C12 C11 6.0(5) . . . . ?
N3 C11 C12 N2 -31.3(5) . . . . ?
N3 C11 C12 C13 152.0(4) . . . . ?
N2 C12 C13 C14 -2.0(7) . . . . ?
C11 C12 C13 C14 174.6(4) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C16 -178.6(4) . . . . ?
C13 C14 C15 C20 1.9(6) . . . . ?
C14 C15 C16 C17 -179.0(4) . . . . ?
C20 C15 C16 C17 0.5(6) . . . . ?
C15 C16 C17 C18 0.1(7) . . . . ?
C16 C17 C18 C19 -0.6(7) . . . . ?
C17 C18 C19 C20 0.4(7) . . . . ?
C12 N2 C20 C19 179.1(4) . . . . ?
Zn1 N2 C20 C19 -1.5(5) . . . . ?
C12 N2 C20 C15 -0.3(6) . . . . ?
Zn1 N2 C20 C15 179.1(3) . . . . ?
C18 C19 C20 N2 -179.2(4) . . . . ?
C18 C19 C20 C15 0.2(6) . . . . ?
C14 C15 C20 N2 -1.7(6) . . . . ?
C16 C15 C20 N2 178.7(4) . . . . ?
C14 C15 C20 C19 178.9(4) . . . . ?
C16 C15 C20 C19 -0.6(6) . . . . ?
C11 N3 C21 C22 -60.8(5) . . . . ?
C10 N3 C21 C22 66.7(5) . . . . ?
Zn1 N3 C21 C22 -177.2(3) . . . . ?
C23 O2 C22 O1 -3.6(7) . . . . ?
C23 O2 C22 C21 174.9(4) . . . . ?
N3 C21 C22 O1 -19.5(7) . . . . ?
N3 C21 C22 O2 162.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_4n
_database_code_depnum_ccdc_archive 'CCDC 1418413'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2015-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N5 O6 Zn'
_chemical_formula_weight         492.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   7.3797(2)
_cell_length_b                   17.4297(3)
_cell_length_c                   8.7740(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.727(3)
_cell_angle_gamma                90.00
_cell_volume                     1055.52(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3600
_cell_measurement_theta_min      5.9552
_cell_measurement_theta_max      75.6543

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    2.045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7490
_exptl_absorpt_correction_T_max  0.8535
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray source'
_diffrn_measurement_method       'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean \w
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5088
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.96
_diffrn_reflns_theta_max         75.84
_reflns_number_total             3475
_reflns_number_gt                3378
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.1069P)²+0.3207P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_number_reflns         3475
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1482
_refine_ls_wR_factor_gt          0.1449
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001

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 0.57043(7) 0.30014(3) 0.11605(6) 0.03919(18) Uani 1 1 d . . .
N1 N 0.4831(5) 0.1907(2) 0.1562(5) 0.0401(7) Uani 1 1 d . . .
N2 N 0.3681(5) 0.3511(2) -0.0800(5) 0.0399(8) Uani 1 1 d . . .
N3 N 0.6107(5) 0.2335(2) -0.0954(4) 0.0362(7) Uani 1 1 d . . .
N4 N 0.9185(6) 0.3739(2) 0.1727(5) 0.0447(8) Uani 1 1 d . . .
N5 N 0.5669(7) 0.4069(3) 0.3695(6) 0.0495(9) Uani 1 1 d . . .
O1 O 0.8517(5) 0.3230(2) 0.2429(4) 0.0518(8) Uani 1 1 d . . .
O2 O 0.8143(7) 0.3973(3) 0.0372(5) 0.0602(9) Uani 1 1 d . . .
O3 O 1.0835(6) 0.3975(4) 0.2412(5) 0.0717(13) Uani 1 1 d . . .
O4 O 0.5054(6) 0.3402(2) 0.3140(5) 0.0567(9) Uani 1 1 d . . .
O5 O 0.5999(9) 0.4194(3) 0.5134(6) 0.0781(14) Uani 1 1 d . . .
O6 O 0.5878(12) 0.4550(3) 0.2757(8) 0.0923(18) Uani 1 1 d . . .
C1 C 0.4654(7) 0.1680(3) 0.2975(6) 0.0487(10) Uani 1 1 d . . .
H1 H 0.4835 0.2037 0.3803 0.058 Uiso 1 1 calc R . .
C2 C 0.4214(8) 0.0935(4) 0.3221(7) 0.0550(12) Uani 1 1 d . . .
H2 H 0.4093 0.0790 0.4201 0.066 Uiso 1 1 calc R . .
C3 C 0.3954(8) 0.0408(3) 0.1992(8) 0.0547(12) Uani 1 1 d . . .
H3 H 0.3662 -0.0099 0.2138 0.066 Uiso 1 1 calc R . .
C4 C 0.4127(8) 0.0634(3) 0.0549(7) 0.0510(11) Uani 1 1 d . . .
H4 H 0.3941 0.0285 -0.0294 0.061 Uiso 1 1 calc R . .
C5 C 0.4584(6) 0.1394(3) 0.0376(5) 0.0395(9) Uani 1 1 d . . .
C6 C 0.4737(7) 0.1688(3) -0.1203(5) 0.0424(9) Uani 1 1 d . . .
H6A H 0.5154 0.1271 -0.1735 0.051 Uiso 1 1 calc R . .
H6B H 0.3465 0.1851 -0.1922 0.051 Uiso 1 1 calc R . .
C7 C 0.5434(6) 0.2873(3) -0.2331(5) 0.0414(10) Uani 1 1 d . . .
H7A H 0.5034 0.2586 -0.3344 0.050 Uiso 1 1 calc R . .
H7B H 0.6494 0.3207 -0.2309 0.050 Uiso 1 1 calc R . .
C8 C 0.3760(6) 0.3353(3) -0.2272(6) 0.0388(8) Uani 1 1 d . . .
C9 C 0.2427(7) 0.3656(3) -0.3677(6) 0.0451(9) Uani 1 1 d . . .
H9 H 0.2515 0.3550 -0.4688 0.054 Uiso 1 1 calc R . .
C10 C 0.0954(7) 0.4120(3) -0.3556(7) 0.0515(12) Uani 1 1 d . . .
H10 H 0.0026 0.4321 -0.4489 0.062 Uiso 1 1 calc R . .
C11 C 0.0880(7) 0.4281(3) -0.2036(8) 0.0533(12) Uani 1 1 d . . .
H11 H -0.0089 0.4595 -0.1932 0.064 Uiso 1 1 calc R . .
C12 C 0.2267(7) 0.3968(3) -0.0678(7) 0.0463(10) Uani 1 1 d . . .
H12 H 0.2225 0.4076 0.0348 0.056 Uiso 1 1 calc R . .
C13 C 0.8159(6) 0.2086(3) -0.0652(6) 0.0407(9) Uani 1 1 d . . .
H13 H 0.8939 0.2555 -0.0375 0.049 Uiso 1 1 calc R . .
C14 C 0.8930(8) 0.1573(4) 0.0840(6) 0.0528(12) Uani 1 1 d . . .
H14A H 0.8851 0.1839 0.1773 0.079 Uiso 1 1 calc R . .
H14B H 1.0256 0.1444 0.1027 0.079 Uiso 1 1 calc R . .
H14C H 0.8169 0.1113 0.0663 0.079 Uiso 1 1 calc R . .
C15 C 0.8514(7) 0.1749(3) -0.2130(6) 0.0416(9) Uani 1 1 d . . .
C16 C 0.8339(12) 0.0965(3) -0.2478(8) 0.0662(16) Uani 1 1 d . . .
H16 H 0.7920 0.0636 -0.1836 0.079 Uiso 1 1 calc R . .
C17 C 0.8783(16) 0.0675(4) -0.3766(10) 0.084(2) Uani 1 1 d . . .
H17 H 0.8658 0.0152 -0.3983 0.101 Uiso 1 1 calc R . .
C18 C 0.9404(11) 0.1146(4) -0.4732(8) 0.0673(16) Uani 1 1 d . . .
H18 H 0.9723 0.0940 -0.5583 0.081 Uiso 1 1 calc R . .
C19 C 0.9556(8) 0.1926(4) -0.4440(7) 0.0533(11) Uani 1 1 d . . .
H19 H 0.9956 0.2252 -0.5099 0.064 Uiso 1 1 calc R . .
C20 C 0.9099(6) 0.2217(3) -0.3137(6) 0.0453(10) Uani 1 1 d . . .
H20 H 0.9191 0.2743 -0.2943 0.054 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 2.018(4) . ?
Zn1 N2 2.040(4) . ?
Zn1 O4 2.079(4) . ?
Zn1 N1 2.083(4) . ?
Zn1 N3 2.295(3) . ?
N1 C5 1.335(6) . ?
N1 C1 1.351(6) . ?
N2 C8 1.342(6) . ?
N2 C12 1.347(6) . ?
N3 C7 1.469(5) . ?
N3 C6 1.479(6) . ?
N3 C13 1.506(5) . ?
N4 O3 1.223(6) . ?
N4 O2 1.234(6) . ?
N4 O1 1.275(6) . ?
N5 O5 1.217(7) . ?
N5 O6 1.222(7) . ?
N5 O4 1.280(6) . ?
C1 C2 1.373(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.518(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.509(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.381(6) . ?
C9 C10 1.389(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.520(7) . ?
C13 C15 1.528(6) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.380(7) . ?
C15 C16 1.397(8) . ?
C16 C17 1.379(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(7) . ?
C19 H19 0.9300 . ?
C20 H20 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
O1 Zn1 N2 133.02(15) . . ?
O1 Zn1 O4 88.23(16) . . ?
N2 Zn1 O4 103.97(17) . . ?
O1 Zn1 N1 114.03(15) . . ?
N2 Zn1 N1 111.33(15) . . ?
O4 Zn1 N1 89.41(16) . . ?
O1 Zn1 N3 98.26(14) . . ?
N2 Zn1 N3 78.72(14) . . ?
O4 Zn1 N3 168.28(14) . . ?
N1 Zn1 N3 79.04(14) . . ?
C5 N1 C1 119.2(4) . . ?
C5 N1 Zn1 116.6(3) . . ?
C1 N1 Zn1 124.0(3) . . ?
C8 N2 C12 119.8(4) . . ?
C8 N2 Zn1 117.0(3) . . ?
C12 N2 Zn1 123.2(3) . . ?
C7 N3 C6 110.5(3) . . ?
C7 N3 C13 110.8(3) . . ?
C6 N3 C13 113.5(4) . . ?
C7 N3 Zn1 103.9(2) . . ?
C6 N3 Zn1 103.2(3) . . ?
C13 N3 Zn1 114.4(3) . . ?
O3 N4 O2 122.3(5) . . ?
O3 N4 O1 119.0(4) . . ?
O2 N4 O1 118.7(4) . . ?
O5 N5 O6 123.4(6) . . ?
O5 N5 O4 118.1(5) . . ?
O6 N5 O4 118.6(5) . . ?
N4 O1 Zn1 111.7(3) . . ?
N5 O4 Zn1 117.9(3) . . ?
N1 C1 C2 121.8(5) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 118.8(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 118.7(5) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.7(5) . . ?
N1 C5 C6 116.8(4) . . ?
C4 C5 C6 121.4(4) . . ?
N3 C6 C5 113.0(3) . . ?
N3 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
N3 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
N3 C7 C8 111.6(3) . . ?
N3 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C9 121.4(4) . . ?
N2 C8 C7 117.5(4) . . ?
C9 C8 C7 120.9(4) . . ?
C8 C9 C10 118.9(5) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 119.4(5) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 118.9(5) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
N2 C12 C11 121.6(5) . . ?
N2 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
N3 C13 C14 111.6(4) . . ?
N3 C13 C15 115.2(4) . . ?
C14 C13 C15 112.4(4) . . ?
N3 C13 H13 105.6 . . ?
C14 C13 H13 105.6 . . ?
C15 C13 H13 105.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 117.7(5) . . ?
C20 C15 C13 120.2(4) . . ?
C16 C15 C13 122.1(5) . . ?
C17 C16 C15 120.5(6) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 121.1(6) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 119.8(5) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 118.9(5) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C15 C20 C19 122.1(5) . . ?
C15 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?

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
O1 Zn1 N1 C5 -104.9(3) . . . . ?
N2 Zn1 N1 C5 62.5(3) . . . . ?
O4 Zn1 N1 C5 167.3(3) . . . . ?
N3 Zn1 N1 C5 -10.7(3) . . . . ?
O1 Zn1 N1 C1 69.8(4) . . . . ?
N2 Zn1 N1 C1 -122.8(4) . . . . ?
O4 Zn1 N1 C1 -18.0(4) . . . . ?
N3 Zn1 N1 C1 164.0(4) . . . . ?
O1 Zn1 N2 C8 79.0(4) . . . . ?
O4 Zn1 N2 C8 179.9(3) . . . . ?
N1 Zn1 N2 C8 -85.2(3) . . . . ?
N3 Zn1 N2 C8 -11.8(3) . . . . ?
O1 Zn1 N2 C12 -103.3(4) . . . . ?
O4 Zn1 N2 C12 -2.4(4) . . . . ?
N1 Zn1 N2 C12 92.5(4) . . . . ?
N3 Zn1 N2 C12 165.9(4) . . . . ?
O1 Zn1 N3 C7 -106.7(3) . . . . ?
N2 Zn1 N3 C7 25.7(3) . . . . ?
O4 Zn1 N3 C7 130.2(7) . . . . ?
N1 Zn1 N3 C7 140.3(3) . . . . ?
O1 Zn1 N3 C6 138.0(3) . . . . ?
N2 Zn1 N3 C6 -89.7(3) . . . . ?
O4 Zn1 N3 C6 14.8(9) . . . . ?
N1 Zn1 N3 C6 24.9(3) . . . . ?
O1 Zn1 N3 C13 14.2(3) . . . . ?
N2 Zn1 N3 C13 146.6(3) . . . . ?
O4 Zn1 N3 C13 -108.9(8) . . . . ?
N1 Zn1 N3 C13 -98.8(3) . . . . ?
O3 N4 O1 Zn1 175.0(4) . . . . ?
O2 N4 O1 Zn1 -5.4(5) . . . . ?
N2 Zn1 O1 N4 -9.6(4) . . . . ?
O4 Zn1 O1 N4 -117.2(3) . . . . ?
N1 Zn1 O1 N4 154.2(3) . . . . ?
N3 Zn1 O1 N4 72.6(3) . . . . ?
O5 N5 O4 Zn1 -151.5(4) . . . . ?
O6 N5 O4 Zn1 29.2(7) . . . . ?
O1 Zn1 O4 N5 53.0(4) . . . . ?
N2 Zn1 O4 N5 -81.1(4) . . . . ?
N1 Zn1 O4 N5 167.0(4) . . . . ?
N3 Zn1 O4 N5 176.9(6) . . . . ?
C5 N1 C1 C2 -0.5(7) . . . . ?
Zn1 N1 C1 C2 -175.0(4) . . . . ?
N1 C1 C2 C3 0.2(8) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
C2 C3 C4 C5 0.7(8) . . . . ?
C1 N1 C5 C4 0.8(7) . . . . ?
Zn1 N1 C5 C4 175.8(4) . . . . ?
C1 N1 C5 C6 178.1(4) . . . . ?
Zn1 N1 C5 C6 -6.9(5) . . . . ?
C3 C4 C5 N1 -0.9(7) . . . . ?
C3 C4 C5 C6 -178.1(5) . . . . ?
C7 N3 C6 C5 -146.1(4) . . . . ?
C13 N3 C6 C5 88.8(5) . . . . ?
Zn1 N3 C6 C5 -35.6(4) . . . . ?
N1 C5 C6 N3 31.5(6) . . . . ?
C4 C5 C6 N3 -151.2(4) . . . . ?
C6 N3 C7 C8 75.0(4) . . . . ?
C13 N3 C7 C8 -158.4(4) . . . . ?
Zn1 N3 C7 C8 -35.1(4) . . . . ?
C12 N2 C8 C9 0.6(7) . . . . ?
Zn1 N2 C8 C9 178.5(4) . . . . ?
C12 N2 C8 C7 176.8(4) . . . . ?
Zn1 N2 C8 C7 -5.3(5) . . . . ?
N3 C7 C8 N2 30.1(6) . . . . ?
N3 C7 C8 C9 -153.7(4) . . . . ?
N2 C8 C9 C10 -1.4(7) . . . . ?
C7 C8 C9 C10 -177.5(5) . . . . ?
C8 C9 C10 C11 1.3(8) . . . . ?
C9 C10 C11 C12 -0.6(8) . . . . ?
C8 N2 C12 C11 0.1(7) . . . . ?
Zn1 N2 C12 C11 -177.6(4) . . . . ?
C10 C11 C12 N2 -0.1(8) . . . . ?
C7 N3 C13 C14 176.1(4) . . . . ?
C6 N3 C13 C14 -58.9(5) . . . . ?
Zn1 N3 C13 C14 59.1(5) . . . . ?
C7 N3 C13 C15 -54.3(5) . . . . ?
C6 N3 C13 C15 70.7(5) . . . . ?
Zn1 N3 C13 C15 -171.3(3) . . . . ?
N3 C13 C15 C20 91.9(5) . . . . ?
C14 C13 C15 C20 -138.8(5) . . . . ?
N3 C13 C15 C16 -90.6(6) . . . . ?
C14 C13 C15 C16 38.6(7) . . . . ?
C20 C15 C16 C17 1.4(11) . . . . ?
C13 C15 C16 C17 -176.1(7) . . . . ?
C15 C16 C17 C18 0.1(14) . . . . ?
C16 C17 C18 C19 -1.3(14) . . . . ?
C17 C18 C19 C20 1.1(11) . . . . ?
C16 C15 C20 C19 -1.7(8) . . . . ?
C13 C15 C20 C19 175.9(4) . . . . ?
C18 C19 C20 C15 0.4(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        75.84
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_5n
_database_code_depnum_ccdc_archive 'CCDC 1418414'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2015-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H27 N5 O6 Zn'
_chemical_formula_weight         642.96

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   9.8292(5)
_cell_length_b                   11.9795(8)
_cell_length_c                   26.3978(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3108.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2970
_cell_measurement_theta_min      3.5320
_cell_measurement_theta_max      23.4540

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8498
_exptl_absorpt_correction_T_max  0.9206
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11895
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6562
_reflns_number_gt                4386
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SIR-92 (Giacovazzo,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.0935P)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    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   0.02(2)
_refine_ls_number_reflns         6562
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1753
_refine_ls_wR_factor_gt          0.1562
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001

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 0.79427(6) 0.04986(5) 0.36443(2) 0.04861(19) Uani 1 1 d . . .
N1 N 0.9970(4) 0.0518(4) 0.39124(16) 0.0496(10) Uani 1 1 d . . .
N2 N 0.6196(4) 0.1022(4) 0.32328(17) 0.0498(11) Uani 1 1 d . . .
N3 N 0.8423(4) 0.2276(4) 0.35397(17) 0.0504(11) Uani 1 1 d . . .
N4 N 0.6320(5) 0.0151(6) 0.4555(2) 0.0700(16) Uani 1 1 d . . .
N5 N 0.8808(6) -0.0848(6) 0.2878(3) 0.0754(17) Uani 1 1 d . . .
O1 O 0.7185(5) -0.0269(5) 0.4267(2) 0.0928(16) Uani 1 1 d . . .
O2 O 0.5846(6) -0.0251(6) 0.4927(2) 0.114(2) Uani 1 1 d . . .
O3 O 0.5890(7) 0.1124(5) 0.4436(3) 0.1062(19) Uani 1 1 d . . .
O4 O 0.8081(5) -0.1014(4) 0.32561(18) 0.0666(11) Uani 1 1 d . . .
O5 O 0.9165(5) 0.0146(5) 0.2794(2) 0.0843(15) Uani 1 1 d . . .
O6 O 0.9131(6) -0.1608(6) 0.2599(3) 0.116(2) Uani 1 1 d . . .
C1 C 1.0621(6) -0.0292(5) 0.4195(2) 0.0544(14) Uani 1 1 d . . .
C2 C 1.0001(7) -0.1345(6) 0.4262(3) 0.0736(19) Uani 1 1 d . . .
H2 H 0.9162 -0.1489 0.4112 0.088 Uiso 1 1 calc R . .
C3 C 1.0621(8) -0.2154(7) 0.4543(3) 0.090(2) Uani 1 1 d . . .
H3 H 1.0216 -0.2852 0.4576 0.108 Uiso 1 1 calc R . .
C4 C 1.1866(9) -0.1938(9) 0.4784(3) 0.095(3) Uani 1 1 d . . .
H4 H 1.2255 -0.2472 0.4995 0.114 Uiso 1 1 calc R . .
C5 C 1.2492(7) -0.0959(9) 0.4709(3) 0.080(2) Uani 1 1 d . . .
H5 H 1.3341 -0.0839 0.4854 0.096 Uiso 1 1 calc R . .
C6 C 1.1899(6) -0.0107(6) 0.4414(2) 0.0615(16) Uani 1 1 d . . .
C7 C 1.2525(6) 0.0896(7) 0.4317(3) 0.072(2) Uani 1 1 d . . .
H7 H 1.3373 0.1043 0.4459 0.087 Uiso 1 1 calc R . .
C8 C 1.1920(6) 0.1690(6) 0.4013(3) 0.0713(18) Uani 1 1 d . . .
H8 H 1.2367 0.2351 0.3933 0.086 Uiso 1 1 calc R . .
C9 C 1.0618(5) 0.1473(5) 0.3830(2) 0.0527(14) Uani 1 1 d . . .
C10 C 0.9932(6) 0.2325(5) 0.3511(3) 0.0644(17) Uani 1 1 d . . .
H10A H 1.0209 0.2221 0.3161 0.077 Uiso 1 1 calc R . .
H10B H 1.0232 0.3060 0.3616 0.077 Uiso 1 1 calc R . .
C11 C 0.7752(6) 0.2524(5) 0.3045(2) 0.0597(15) Uani 1 1 d . . .
H11A H 0.8313 0.2244 0.2771 0.072 Uiso 1 1 calc R . .
H11B H 0.7667 0.3326 0.3005 0.072 Uiso 1 1 calc R . .
C12 C 0.6367(6) 0.1999(6) 0.3016(2) 0.0589(16) Uani 1 1 d . . .
C13 C 0.5322(8) 0.2529(7) 0.2747(3) 0.076(2) Uani 1 1 d . . .
H13 H 0.5463 0.3233 0.2608 0.092 Uiso 1 1 calc R . .
C14 C 0.4117(8) 0.2017(8) 0.2690(3) 0.083(2) Uani 1 1 d . . .
H14 H 0.3423 0.2367 0.2511 0.099 Uiso 1 1 calc R . .
C15 C 0.3905(6) 0.0964(7) 0.2900(2) 0.0635(18) Uani 1 1 d . . .
C16 C 0.2647(6) 0.0363(9) 0.2867(3) 0.080(2) Uani 1 1 d . . .
H16 H 0.1922 0.0670 0.2688 0.096 Uiso 1 1 calc R . .
C17 C 0.2502(6) -0.0620(9) 0.3086(3) 0.079(2) Uani 1 1 d . . .
H17 H 0.1682 -0.1001 0.3053 0.095 Uiso 1 1 calc R . .
C18 C 0.3548(6) -0.1100(7) 0.3367(3) 0.074(2) Uani 1 1 d . . .
H18 H 0.3420 -0.1788 0.3522 0.089 Uiso 1 1 calc R . .
C19 C 0.4764(5) -0.0556(6) 0.3413(2) 0.0596(15) Uani 1 1 d . . .
H19 H 0.5467 -0.0884 0.3595 0.072 Uiso 1 1 calc R . .
C20 C 0.4964(5) 0.0497(6) 0.31859(19) 0.0516(13) Uani 1 1 d . . .
C21 C 0.7790(7) 0.2932(5) 0.3953(2) 0.0579(14) Uani 1 1 d . . .
H21 H 0.6895 0.2593 0.4010 0.070 Uiso 1 1 calc R . .
C22 C 0.8559(8) 0.2795(6) 0.4449(2) 0.080(2) Uani 1 1 d . . .
H22A H 0.8726 0.2016 0.4509 0.120 Uiso 1 1 calc R . .
H22B H 0.8027 0.3096 0.4721 0.120 Uiso 1 1 calc R . .
H22C H 0.9410 0.3185 0.4428 0.120 Uiso 1 1 calc R . .
C23 C 0.7517(8) 0.4164(6) 0.3850(3) 0.074(2) Uani 1 1 d . . .
C24 C 0.8447(11) 0.4839(6) 0.3596(4) 0.108(3) Uani 1 1 d . . .
H24 H 0.9230 0.4541 0.3452 0.129 Uiso 1 1 calc R . .
C25 C 0.8155(12) 0.6025(7) 0.3564(4) 0.113(3) Uani 1 1 d . . .
H25 H 0.8785 0.6489 0.3407 0.136 Uiso 1 1 calc R . .
C26 C 0.7050(13) 0.6464(7) 0.3746(3) 0.104(3) Uani 1 1 d . . .
H26 H 0.6912 0.7228 0.3712 0.125 Uiso 1 1 calc R . .
C27 C 0.6054(10) 0.5817(6) 0.3995(4) 0.093(3) Uani 1 1 d . . .
C28 C 0.4904(14) 0.6309(9) 0.4205(5) 0.122(4) Uani 1 1 d . . .
H28 H 0.4781 0.7077 0.4182 0.146 Uiso 1 1 calc R . .
C29 C 0.3965(16) 0.5676(11) 0.4442(4) 0.143(5) Uani 1 1 d . . .
H29 H 0.3202 0.6019 0.4580 0.172 Uiso 1 1 calc R . .
C30 C 0.4110(10) 0.4501(10) 0.4487(4) 0.120(3) Uani 1 1 d . . .
H30 H 0.3429 0.4070 0.4634 0.144 Uiso 1 1 calc R . .
C31 C 0.5289(9) 0.4014(7) 0.4306(3) 0.087(2) Uani 1 1 d . . .
H31 H 0.5431 0.3255 0.4359 0.104 Uiso 1 1 calc R . .
C32 C 0.6281(8) 0.4639(6) 0.4045(3) 0.0740(19) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 2.025(5) . ?
Zn1 O4 2.086(4) . ?
Zn1 N1 2.114(4) . ?
Zn1 N2 2.126(4) . ?
Zn1 N3 2.198(4) . ?
N1 C9 1.328(7) . ?
N1 C1 1.382(7) . ?
N2 C12 1.313(7) . ?
N2 C20 1.370(7) . ?
N3 C21 1.482(7) . ?
N3 C10 1.486(7) . ?
N3 C11 1.492(7) . ?
N4 O2 1.187(7) . ?
N4 O1 1.247(8) . ?
N4 O3 1.279(8) . ?
N5 O6 1.214(7) . ?
N5 O4 1.243(8) . ?
N5 O5 1.261(8) . ?
C1 C6 1.400(8) . ?
C1 C2 1.412(9) . ?
C2 C3 1.365(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.339(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(10) . ?
C7 C8 1.379(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.485(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.501(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.402(9) . ?
C13 C14 1.342(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.394(10) . ?
C14 H14 0.9300 . ?
C15 C20 1.403(8) . ?
C15 C16 1.433(10) . ?
C16 C17 1.320(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.410(9) . ?
C19 H19 0.9300 . ?
C21 C22 1.519(9) . ?
C21 C23 1.525(8) . ?
C21 H21 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.391(11) . ?
C23 C32 1.438(10) . ?
C24 C25 1.451(12) . ?
C24 H24 0.9300 . ?
C25 C26 1.298(14) . ?
C25 H25 0.9300 . ?
C26 C27 1.411(13) . ?
C26 H26 0.9300 . ?
C27 C28 1.390(14) . ?
C27 C32 1.435(10) . ?
C28 C29 1.348(16) . ?
C28 H28 0.9300 . ?
C29 C30 1.420(15) . ?
C29 H29 0.9300 . ?
C30 C31 1.382(11) . ?
C30 H30 0.9300 . ?
C31 C32 1.410(11) . ?
C31 H31 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
O1 Zn1 O4 91.6(2) . . ?
O1 Zn1 N1 94.60(19) . . ?
O4 Zn1 N1 96.46(19) . . ?
O1 Zn1 N2 104.56(19) . . ?
O4 Zn1 N2 93.32(18) . . ?
N1 Zn1 N2 158.21(19) . . ?
O1 Zn1 N3 128.4(2) . . ?
O4 Zn1 N3 139.96(18) . . ?
N1 Zn1 N3 80.15(19) . . ?
N2 Zn1 N3 79.84(17) . . ?
C9 N1 C1 118.1(5) . . ?
C9 N1 Zn1 114.0(4) . . ?
C1 N1 Zn1 127.6(4) . . ?
C12 N2 C20 118.9(5) . . ?
C12 N2 Zn1 112.4(4) . . ?
C20 N2 Zn1 128.6(4) . . ?
C21 N3 C10 115.9(5) . . ?
C21 N3 C11 110.6(4) . . ?
C10 N3 C11 112.9(5) . . ?
C21 N3 Zn1 109.3(3) . . ?
C10 N3 Zn1 105.0(4) . . ?
C11 N3 Zn1 102.0(3) . . ?
O2 N4 O1 127.5(7) . . ?
O2 N4 O3 116.3(7) . . ?
O1 N4 O3 116.2(6) . . ?
O6 N5 O4 121.2(7) . . ?
O6 N5 O5 121.8(7) . . ?
O4 N5 O5 117.0(6) . . ?
N4 O1 Zn1 124.3(5) . . ?
N5 O4 Zn1 107.0(4) . . ?
N1 C1 C6 121.9(6) . . ?
N1 C1 C2 119.6(5) . . ?
C6 C1 C2 118.5(6) . . ?
C3 C2 C1 120.6(7) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.3(9) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.7(7) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.7(7) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C1 117.6(6) . . ?
C7 C6 C5 123.4(6) . . ?
C1 C6 C5 119.0(7) . . ?
C6 C7 C8 121.2(6) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 118.0(7) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
N1 C9 C8 123.0(6) . . ?
N1 C9 C10 117.9(5) . . ?
C8 C9 C10 119.1(6) . . ?
C9 C10 N3 113.4(5) . . ?
C9 C10 H10A 108.9 . . ?
N3 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
N3 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N3 C11 C12 111.2(5) . . ?
N3 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 C13 122.0(6) . . ?
N2 C12 C11 117.9(5) . . ?
C13 C12 C11 120.0(6) . . ?
C14 C13 C12 119.7(7) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.1(6) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C20 117.6(6) . . ?
C14 C15 C16 124.1(7) . . ?
C20 C15 C16 118.2(7) . . ?
C17 C16 C15 121.0(6) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 121.5(6) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 119.8(8) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.7(6) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
N2 C20 C15 121.4(6) . . ?
N2 C20 C19 119.8(5) . . ?
C15 C20 C19 118.8(6) . . ?
N3 C21 C22 111.6(5) . . ?
N3 C21 C23 117.1(5) . . ?
C22 C21 C23 110.3(5) . . ?
N3 C21 H21 105.7 . . ?
C22 C21 H21 105.7 . . ?
C23 C21 H21 105.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C32 119.8(7) . . ?
C24 C23 C21 122.3(7) . . ?
C32 C23 C21 117.8(6) . . ?
C23 C24 C25 117.8(10) . . ?
C23 C24 H24 121.1 . . ?
C25 C24 H24 121.1 . . ?
C26 C25 C24 122.7(10) . . ?
C26 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C25 C26 C27 122.0(8) . . ?
C25 C26 H26 119.0 . . ?
C27 C26 H26 119.0 . . ?
C28 C27 C26 121.1(9) . . ?
C28 C27 C32 120.4(10) . . ?
C26 C27 C32 118.4(9) . . ?
C29 C28 C27 120.3(10) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 121.8(10) . . ?
C28 C29 H29 119.1 . . ?
C30 C29 H29 119.1 . . ?
C31 C30 C29 118.3(11) . . ?
C31 C30 H30 120.9 . . ?
C29 C30 H30 120.9 . . ?
C30 C31 C32 121.7(8) . . ?
C30 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C31 C32 C27 117.4(7) . . ?
C31 C32 C23 123.4(7) . . ?
C27 C32 C23 119.1(8) . . ?

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
O1 Zn1 N1 C9 -137.2(4) . . . . ?
O4 Zn1 N1 C9 130.6(4) . . . . ?
N2 Zn1 N1 C9 14.5(7) . . . . ?
N3 Zn1 N1 C9 -9.1(4) . . . . ?
O1 Zn1 N1 C1 36.4(5) . . . . ?
O4 Zn1 N1 C1 -55.8(5) . . . . ?
N2 Zn1 N1 C1 -171.9(4) . . . . ?
N3 Zn1 N1 C1 164.5(5) . . . . ?
O1 Zn1 N2 C12 142.4(4) . . . . ?
O4 Zn1 N2 C12 -125.0(4) . . . . ?
N1 Zn1 N2 C12 -8.4(7) . . . . ?
N3 Zn1 N2 C12 15.2(4) . . . . ?
O1 Zn1 N2 C20 -35.3(5) . . . . ?
O4 Zn1 N2 C20 57.2(5) . . . . ?
N1 Zn1 N2 C20 173.9(5) . . . . ?
N3 Zn1 N2 C20 -162.5(5) . . . . ?
O1 Zn1 N3 C21 -14.4(4) . . . . ?
O4 Zn1 N3 C21 169.2(3) . . . . ?
N1 Zn1 N3 C21 -102.4(4) . . . . ?
N2 Zn1 N3 C21 86.2(4) . . . . ?
O1 Zn1 N3 C10 110.6(4) . . . . ?
O4 Zn1 N3 C10 -65.8(5) . . . . ?
N1 Zn1 N3 C10 22.5(4) . . . . ?
N2 Zn1 N3 C10 -148.8(4) . . . . ?
O1 Zn1 N3 C11 -131.5(4) . . . . ?
O4 Zn1 N3 C11 52.1(4) . . . . ?
N1 Zn1 N3 C11 140.4(4) . . . . ?
N2 Zn1 N3 C11 -30.9(3) . . . . ?
O2 N4 O1 Zn1 -179.4(6) . . . . ?
O3 N4 O1 Zn1 1.0(8) . . . . ?
O4 Zn1 O1 N4 -145.3(5) . . . . ?
N1 Zn1 O1 N4 118.1(5) . . . . ?
N2 Zn1 O1 N4 -51.4(5) . . . . ?
N3 Zn1 O1 N4 37.0(6) . . . . ?
O6 N5 O4 Zn1 175.4(6) . . . . ?
O5 N5 O4 Zn1 -6.2(7) . . . . ?
O1 Zn1 O4 N5 -165.9(4) . . . . ?
N1 Zn1 O4 N5 -71.1(4) . . . . ?
N2 Zn1 O4 N5 89.4(4) . . . . ?
N3 Zn1 O4 N5 11.3(5) . . . . ?
C9 N1 C1 C6 3.2(8) . . . . ?
Zn1 N1 C1 C6 -170.2(4) . . . . ?
C9 N1 C1 C2 -175.7(6) . . . . ?
Zn1 N1 C1 C2 10.9(8) . . . . ?
N1 C1 C2 C3 -179.5(6) . . . . ?
C6 C1 C2 C3 1.6(10) . . . . ?
C1 C2 C3 C4 1.9(12) . . . . ?
C2 C3 C4 C5 -4.5(12) . . . . ?
C3 C4 C5 C6 3.5(12) . . . . ?
N1 C1 C6 C7 -3.2(8) . . . . ?
C2 C1 C6 C7 175.7(6) . . . . ?
N1 C1 C6 C5 178.5(5) . . . . ?
C2 C1 C6 C5 -2.5(9) . . . . ?
C4 C5 C6 C7 -178.2(7) . . . . ?
C4 C5 C6 C1 0.0(10) . . . . ?
C1 C6 C7 C8 -0.3(9) . . . . ?
C5 C6 C7 C8 177.9(6) . . . . ?
C6 C7 C8 C9 3.6(9) . . . . ?
C1 N1 C9 C8 0.3(8) . . . . ?
Zn1 N1 C9 C8 174.6(5) . . . . ?
C1 N1 C9 C10 178.0(5) . . . . ?
Zn1 N1 C9 C10 -7.8(7) . . . . ?
C7 C8 C9 N1 -3.7(9) . . . . ?
C7 C8 C9 C10 178.7(6) . . . . ?
N1 C9 C10 N3 29.4(8) . . . . ?
C8 C9 C10 N3 -152.8(5) . . . . ?
C21 N3 C10 C9 87.5(6) . . . . ?
C11 N3 C10 C9 -143.5(5) . . . . ?
Zn1 N3 C10 C9 -33.2(6) . . . . ?
C21 N3 C11 C12 -73.4(6) . . . . ?
C10 N3 C11 C12 154.9(5) . . . . ?
Zn1 N3 C11 C12 42.7(5) . . . . ?
C20 N2 C12 C13 1.2(9) . . . . ?
Zn1 N2 C12 C13 -176.8(5) . . . . ?
C20 N2 C12 C11 -176.2(5) . . . . ?
Zn1 N2 C12 C11 5.8(7) . . . . ?
N3 C11 C12 N2 -35.5(8) . . . . ?
N3 C11 C12 C13 147.0(6) . . . . ?
N2 C12 C13 C14 -2.3(11) . . . . ?
C11 C12 C13 C14 175.0(6) . . . . ?
C12 C13 C14 C15 0.2(11) . . . . ?
C13 C14 C15 C20 2.9(10) . . . . ?
C13 C14 C15 C16 178.8(7) . . . . ?
C14 C15 C16 C17 -178.0(7) . . . . ?
C20 C15 C16 C17 -2.2(10) . . . . ?
C15 C16 C17 C18 1.5(11) . . . . ?
C16 C17 C18 C19 -0.9(10) . . . . ?
C17 C18 C19 C20 1.1(10) . . . . ?
C12 N2 C20 C15 2.0(8) . . . . ?
Zn1 N2 C20 C15 179.6(4) . . . . ?
C12 N2 C20 C19 179.5(5) . . . . ?
Zn1 N2 C20 C19 -2.9(7) . . . . ?
C14 C15 C20 N2 -4.0(9) . . . . ?
C16 C15 C20 N2 179.8(5) . . . . ?
C14 C15 C20 C19 178.4(6) . . . . ?
C16 C15 C20 C19 2.3(8) . . . . ?
C18 C19 C20 N2 -179.4(5) . . . . ?
C18 C19 C20 C15 -1.8(9) . . . . ?
C10 N3 C21 C22 -43.4(7) . . . . ?
C11 N3 C21 C22 -173.5(5) . . . . ?
Zn1 N3 C21 C22 75.0(6) . . . . ?
C10 N3 C21 C23 85.0(7) . . . . ?
C11 N3 C21 C23 -45.1(7) . . . . ?
Zn1 N3 C21 C23 -156.7(5) . . . . ?
N3 C21 C23 C24 -41.5(10) . . . . ?
C22 C21 C23 C24 87.5(9) . . . . ?
N3 C21 C23 C32 141.6(6) . . . . ?
C22 C21 C23 C32 -89.5(7) . . . . ?
C32 C23 C24 C25 3.3(14) . . . . ?
C21 C23 C24 C25 -173.6(8) . . . . ?
C23 C24 C25 C26 -2.3(17) . . . . ?
C24 C25 C26 C27 0.6(18) . . . . ?
C25 C26 C27 C28 177.4(10) . . . . ?
C25 C26 C27 C32 0.0(15) . . . . ?
C26 C27 C28 C29 -179.8(11) . . . . ?
C32 C27 C28 C29 -2.5(16) . . . . ?
C27 C28 C29 C30 0.0(19) . . . . ?
C28 C29 C30 C31 3.9(18) . . . . ?
C29 C30 C31 C32 -5.4(15) . . . . ?
C30 C31 C32 C27 3.1(12) . . . . ?
C30 C31 C32 C23 -179.7(8) . . . . ?
C28 C27 C32 C31 0.9(12) . . . . ?
C26 C27 C32 C31 178.3(8) . . . . ?
C28 C27 C32 C23 -176.4(8) . . . . ?
C26 C27 C32 C23 1.0(11) . . . . ?
C24 C23 C32 C31 -179.9(8) . . . . ?
C21 C23 C32 C31 -2.9(10) . . . . ?
C24 C23 C32 C27 -2.7(11) . . . . ?
C21 C23 C32 C27 174.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.988
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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_12Zn
_database_code_depnum_ccdc_archive 'CCDC 1418415'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2015-11-08 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 H38 B2 F8 N6 O4 Zn'
_chemical_formula_weight         809.67

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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   19.3596(3)
_cell_length_b                   10.1740(2)
_cell_length_c                   18.4718(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3638.29(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5916
_cell_measurement_theta_min      3.3042
_cell_measurement_theta_max      75.5310

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    1.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7266
_exptl_absorpt_correction_T_max  0.9196
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11828
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.79
_diffrn_reflns_theta_max         75.72
_reflns_number_total             3766
_reflns_number_gt                3242
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.0466P)²+0.7882P] 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         3766
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001

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 0.17972(3) 0.2500 0.04768(11) Uani 1 2 d S . .
N1 N 0.60584(8) 0.22830(15) 0.21347(8) 0.0538(3) Uani 1 1 d . . .
N2 N 0.46213(8) 0.04196(14) 0.17463(8) 0.0538(3) Uani 1 1 d . . .
N3 N 0.48771(7) 0.30796(14) 0.14848(8) 0.0487(3) Uani 1 1 d . . .
O1 O 0.29289(11) 0.4838(3) 0.11922(17) 0.1588(13) Uani 1 1 d . . .
O2 O 0.32553(8) 0.60342(16) 0.02657(10) 0.0797(4) Uani 1 1 d . . .
C1 C 0.66491(11) 0.1714(2) 0.23687(11) 0.0641(5) Uani 1 1 d . . .
H1 H 0.6617 0.0940 0.2635 0.077 Uiso 1 1 calc R . .
C2 C 0.72926(11) 0.2222(3) 0.22334(14) 0.0758(6) Uani 1 1 d . . .
H2 H 0.7687 0.1796 0.2398 0.091 Uiso 1 1 calc R . .
C3 C 0.73412(11) 0.3376(3) 0.18479(15) 0.0791(6) Uani 1 1 d . . .
H3 H 0.7770 0.3755 0.1759 0.095 Uiso 1 1 calc R . .
C4 C 0.67491(10) 0.3961(2) 0.15955(13) 0.0687(5) Uani 1 1 d . . .
H4 H 0.6773 0.4733 0.1327 0.082 Uiso 1 1 calc R . .
C5 C 0.61156(9) 0.33869(18) 0.17460(10) 0.0530(4) Uani 1 1 d . . .
C6 C 0.54544(9) 0.40170(18) 0.14864(10) 0.0550(4) Uani 1 1 d . . .
H6A H 0.5341 0.4752 0.1799 0.066 Uiso 1 1 calc R . .
H6B H 0.5522 0.4354 0.1000 0.066 Uiso 1 1 calc R . .
C7 C 0.49678(10) 0.20943(19) 0.08988(10) 0.0544(4) Uani 1 1 d . . .
H7A H 0.5455 0.1900 0.0842 0.065 Uiso 1 1 calc R . .
H7B H 0.4801 0.2459 0.0446 0.065 Uiso 1 1 calc R . .
C8 C 0.45838(9) 0.08485(17) 0.10612(9) 0.0513(4) Uani 1 1 d . . .
C9 C 0.42349(11) 0.0151(2) 0.05340(11) 0.0640(5) Uani 1 1 d . . .
H9 H 0.4210 0.0466 0.0062 0.077 Uiso 1 1 calc R . .
C10 C 0.39247(13) -0.1020(2) 0.07212(13) 0.0767(6) Uani 1 1 d . . .
H10 H 0.3690 -0.1509 0.0374 0.092 Uiso 1 1 calc R . .
C11 C 0.39644(13) -0.1459(2) 0.14209(13) 0.0727(6) Uani 1 1 d . . .
H11 H 0.3757 -0.2246 0.1555 0.087 Uiso 1 1 calc R . .
C12 C 0.43136(11) -0.07221(19) 0.19187(11) 0.0633(5) Uani 1 1 d . . .
H12 H 0.4339 -0.1021 0.2394 0.076 Uiso 1 1 calc R . .
C13 C 0.42014(9) 0.37514(19) 0.14314(10) 0.0540(4) Uani 1 1 d . . .
H13A H 0.4136 0.4265 0.1868 0.065 Uiso 1 1 calc R . .
H13B H 0.3844 0.3084 0.1423 0.065 Uiso 1 1 calc R . .
C14 C 0.40903(10) 0.4657(2) 0.07825(11) 0.0598(4) Uani 1 1 d . . .
H14A H 0.4411 0.5388 0.0806 0.072 Uiso 1 1 calc R . .
H14B H 0.4177 0.4178 0.0338 0.072 Uiso 1 1 calc R . .
C15 C 0.33636(11) 0.5165(2) 0.07843(13) 0.0712(6) Uani 1 1 d . . .
C16 C 0.25607(14) 0.6546(3) 0.0208(2) 0.1094(11) Uani 1 1 d . . .
H16A H 0.2258 0.5869 0.0033 0.164 Uiso 1 1 calc R . .
H16B H 0.2556 0.7273 -0.0123 0.164 Uiso 1 1 calc R . .
H16C H 0.2407 0.6836 0.0675 0.164 Uiso 1 1 calc R . .
B1 B 0.59455(12) 0.7472(2) 0.11745(12) 0.0600(5) Uani 1 1 d . . .
F4 F 0.59933(9) 0.69778(14) 0.18644(7) 0.0857(4) Uani 1 1 d . . .
F1 F 0.53307(8) 0.70938(17) 0.08611(9) 0.0943(5) Uani 1 1 d . . .
F3 F 0.64688(9) 0.69470(17) 0.07611(9) 0.0977(5) Uani 1 1 d . . .
F2 F 0.60041(9) 0.88212(14) 0.11969(9) 0.0903(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N2 2.1072(14) . ?
Zn1 N2 2.1072(14) 4_655 ?
Zn1 N1 2.2131(15) . ?
Zn1 N1 2.2131(15) 4_655 ?
Zn1 N3 2.2969(15) 4_655 ?
Zn1 N3 2.2969(15) . ?
N1 C5 1.338(2) . ?
N1 C1 1.353(2) . ?
N2 C8 1.341(2) . ?
N2 C12 1.344(2) . ?
N3 C6 1.469(2) . ?
N3 C13 1.479(2) . ?
N3 C7 1.486(2) . ?
O1 C15 1.178(3) . ?
O2 C15 1.320(3) . ?
O2 C16 1.446(3) . ?
C1 C2 1.372(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.510(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.500(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.381(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.527(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.499(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
B1 F4 1.373(3) . ?
B1 F3 1.377(3) . ?
B1 F2 1.378(3) . ?
B1 F1 1.378(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N2 96.61(8) . 4_655 ?
N2 Zn1 N1 105.62(6) . . ?
N2 Zn1 N1 91.59(6) 4_655 . ?
N2 Zn1 N1 91.59(6) . 4_655 ?
N2 Zn1 N1 105.62(6) 4_655 4_655 ?
N1 Zn1 N1 154.19(8) . 4_655 ?
N2 Zn1 N3 162.42(6) . 4_655 ?
N2 Zn1 N3 78.60(5) 4_655 4_655 ?
N1 Zn1 N3 91.50(5) . 4_655 ?
N1 Zn1 N3 73.75(5) 4_655 4_655 ?
N2 Zn1 N3 78.60(5) . . ?
N2 Zn1 N3 162.42(6) 4_655 . ?
N1 Zn1 N3 73.75(5) . . ?
N1 Zn1 N3 91.50(5) 4_655 . ?
N3 Zn1 N3 110.77(7) 4_655 . ?
C5 N1 C1 117.43(17) . . ?
C5 N1 Zn1 115.33(12) . . ?
C1 N1 Zn1 126.15(13) . . ?
C8 N2 C12 118.76(16) . . ?
C8 N2 Zn1 115.21(12) . . ?
C12 N2 Zn1 124.94(13) . . ?
C6 N3 C13 111.90(14) . . ?
C6 N3 C7 110.46(14) . . ?
C13 N3 C7 111.57(14) . . ?
C6 N3 Zn1 106.75(10) . . ?
C13 N3 Zn1 114.11(11) . . ?
C7 N3 Zn1 101.49(10) . . ?
C15 O2 C16 116.3(2) . . ?
N1 C1 C2 123.3(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.31(18) . . ?
N1 C5 C6 117.18(16) . . ?
C4 C5 C6 120.49(17) . . ?
N3 C6 C5 111.71(14) . . ?
N3 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N3 C7 C8 111.47(14) . . ?
N3 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C9 121.65(18) . . ?
N2 C8 C7 115.92(15) . . ?
C9 C8 C7 122.37(17) . . ?
C10 C9 C8 118.7(2) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
N2 C12 C11 122.3(2) . . ?
N2 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N3 C13 C14 117.11(15) . . ?
N3 C13 H13A 108.0 . . ?
C14 C13 H13A 108.0 . . ?
N3 C13 H13B 108.0 . . ?
C14 C13 H13B 108.0 . . ?
H13A C13 H13B 107.3 . . ?
C15 C14 C13 109.79(17) . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O1 C15 O2 122.7(2) . . ?
O1 C15 C14 125.1(2) . . ?
O2 C15 C14 112.23(19) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F4 B1 F3 108.83(19) . . ?
F4 B1 F2 109.36(18) . . ?
F3 B1 F2 110.05(19) . . ?
F4 B1 F1 110.21(19) . . ?
F3 B1 F1 107.10(19) . . ?
F2 B1 F1 111.24(19) . . ?

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
N2 Zn1 N1 C5 97.75(14) . . . . ?
N2 Zn1 N1 C5 -164.93(13) 4_655 . . . ?
N1 Zn1 N1 C5 -32.38(12) 4_655 . . . ?
N3 Zn1 N1 C5 -86.29(13) 4_655 . . . ?
N3 Zn1 N1 C5 24.92(13) . . . . ?
N2 Zn1 N1 C1 -94.57(17) . . . . ?
N2 Zn1 N1 C1 2.75(17) 4_655 . . . ?
N1 Zn1 N1 C1 135.30(17) 4_655 . . . ?
N3 Zn1 N1 C1 81.38(17) 4_655 . . . ?
N3 Zn1 N1 C1 -167.40(18) . . . . ?
N2 Zn1 N2 C8 -154.32(15) 4_655 . . . ?
N1 Zn1 N2 C8 -60.79(14) . . . . ?
N1 Zn1 N2 C8 99.75(13) 4_655 . . . ?
N3 Zn1 N2 C8 132.70(17) 4_655 . . . ?
N3 Zn1 N2 C8 8.55(12) . . . . ?
N2 Zn1 N2 C12 37.81(14) 4_655 . . . ?
N1 Zn1 N2 C12 131.34(16) . . . . ?
N1 Zn1 N2 C12 -68.11(17) 4_655 . . . ?
N3 Zn1 N2 C12 -35.2(3) 4_655 . . . ?
N3 Zn1 N2 C12 -159.32(17) . . . . ?
N2 Zn1 N3 C6 -143.52(12) . . . . ?
N2 Zn1 N3 C6 -67.8(2) 4_655 . . . ?
N1 Zn1 N3 C6 -33.35(11) . . . . ?
N1 Zn1 N3 C6 125.15(11) 4_655 . . . ?
N3 Zn1 N3 C6 51.98(10) 4_655 . . . ?
N2 Zn1 N3 C13 92.33(12) . . . . ?
N2 Zn1 N3 C13 168.01(17) 4_655 . . . ?
N1 Zn1 N3 C13 -157.50(13) . . . . ?
N1 Zn1 N3 C13 1.00(12) 4_655 . . . ?
N3 Zn1 N3 C13 -72.17(11) 4_655 . . . ?
N2 Zn1 N3 C7 -27.81(10) . . . . ?
N2 Zn1 N3 C7 47.9(2) 4_655 . . . ?
N1 Zn1 N3 C7 82.36(11) . . . . ?
N1 Zn1 N3 C7 -119.14(11) 4_655 . . . ?
N3 Zn1 N3 C7 167.69(12) 4_655 . . . ?
C5 N1 C1 C2 0.8(3) . . . . ?
Zn1 N1 C1 C2 -166.69(18) . . . . ?
N1 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C1 N1 C5 C4 -1.4(3) . . . . ?
Zn1 N1 C5 C4 167.37(16) . . . . ?
C1 N1 C5 C6 180.00(17) . . . . ?
Zn1 N1 C5 C6 -11.2(2) . . . . ?
C3 C4 C5 N1 0.5(3) . . . . ?
C3 C4 C5 C6 179.0(2) . . . . ?
C13 N3 C6 C5 164.13(14) . . . . ?
C7 N3 C6 C5 -70.91(18) . . . . ?
Zn1 N3 C6 C5 38.63(16) . . . . ?
N1 C5 C6 N3 -20.1(2) . . . . ?
C4 C5 C6 N3 161.27(18) . . . . ?
C6 N3 C7 C8 156.12(15) . . . . ?
C13 N3 C7 C8 -78.74(18) . . . . ?
Zn1 N3 C7 C8 43.18(16) . . . . ?
C12 N2 C8 C9 0.4(3) . . . . ?
Zn1 N2 C8 C9 -168.27(15) . . . . ?
C12 N2 C8 C7 -177.09(17) . . . . ?
Zn1 N2 C8 C7 14.2(2) . . . . ?
N3 C7 C8 N2 -42.0(2) . . . . ?
N3 C7 C8 C9 140.50(18) . . . . ?
N2 C8 C9 C10 -0.6(3) . . . . ?
C7 C8 C9 C10 176.73(19) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C8 N2 C12 C11 0.0(3) . . . . ?
Zn1 N2 C12 C11 167.42(17) . . . . ?
C10 C11 C12 N2 -0.1(4) . . . . ?
C6 N3 C13 C14 56.7(2) . . . . ?
C7 N3 C13 C14 -67.6(2) . . . . ?
Zn1 N3 C13 C14 178.09(13) . . . . ?
N3 C13 C14 C15 175.51(17) . . . . ?
C16 O2 C15 O1 -1.8(4) . . . . ?
C16 O2 C15 C14 177.9(2) . . . . ?
C13 C14 C15 O1 -5.3(4) . . . . ?
C13 C14 C15 O2 175.09(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        75.72
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_12Co
_database_code_depnum_ccdc_archive 'CCDC 1418416'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2015-11-08 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 H38 B2 Co F8 N6 O4'
_chemical_formula_weight         803.23

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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   19.3097(11)
_cell_length_b                   10.1965(5)
_cell_length_c                   18.4325(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3629.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2306
_cell_measurement_theta_min      3.3120
_cell_measurement_theta_max      73.8610

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1652
_exptl_absorpt_coefficient_mu    4.477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6630
_exptl_absorpt_correction_T_max  0.8071
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9031
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.58
_diffrn_reflns_theta_max         74.03
_reflns_number_total             3604
_reflns_number_gt                2719
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.0522P)²+1.4508P] 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         3604
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0001

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
Co1 Co 0.5000 0.31991(5) 0.2500 0.04380(17) Uani 1 2 d S . .
N1 N 0.39583(11) 0.2718(2) 0.21446(12) 0.0499(5) Uani 1 1 d . . .
N2 N 0.53693(12) 0.4567(2) 0.17378(12) 0.0509(5) Uani 1 1 d . . .
N3 N 0.51354(11) 0.1926(2) 0.14928(12) 0.0456(5) Uani 1 1 d . . .
O1 O 0.70811(16) 0.0143(4) 0.1196(2) 0.1541(18) Uani 1 1 d . . .
O2 O 0.67521(12) -0.1041(2) 0.02700(13) 0.0772(7) Uani 1 1 d . . .
C1 C 0.33653(16) 0.3293(3) 0.23741(17) 0.0621(8) Uani 1 1 d . . .
H1 H 0.3398 0.4062 0.2643 0.075 Uiso 1 1 calc R . .
C2 C 0.27225(16) 0.2801(4) 0.2231(2) 0.0717(9) Uani 1 1 d . . .
H2 H 0.2328 0.3238 0.2391 0.086 Uiso 1 1 calc R . .
C3 C 0.26656(16) 0.1653(4) 0.1849(2) 0.0737(9) Uani 1 1 d . . .
H3 H 0.2234 0.1282 0.1761 0.088 Uiso 1 1 calc R . .
C4 C 0.32624(15) 0.1057(3) 0.15977(18) 0.0663(8) Uani 1 1 d . . .
H4 H 0.3237 0.0289 0.1327 0.080 Uiso 1 1 calc R . .
C5 C 0.38980(14) 0.1616(3) 0.17519(14) 0.0508(6) Uani 1 1 d . . .
C6 C 0.45575(14) 0.0977(3) 0.15003(15) 0.0520(6) Uani 1 1 d . . .
H6A H 0.4671 0.0254 0.1821 0.062 Uiso 1 1 calc R . .
H6B H 0.4492 0.0626 0.1016 0.062 Uiso 1 1 calc R . .
C7 C 0.50367(15) 0.2891(3) 0.08947(14) 0.0519(6) Uani 1 1 d . . .
H7A H 0.4547 0.3071 0.0835 0.062 Uiso 1 1 calc R . .
H7B H 0.5208 0.2521 0.0444 0.062 Uiso 1 1 calc R . .
C8 C 0.54124(14) 0.4142(3) 0.10533(14) 0.0503(6) Uani 1 1 d . . .
C9 C 0.57620(16) 0.4843(3) 0.05299(17) 0.0611(7) Uani 1 1 d . . .
H9 H 0.5789 0.4529 0.0057 0.073 Uiso 1 1 calc R . .
C10 C 0.60702(19) 0.6013(3) 0.07141(19) 0.0729(9) Uani 1 1 d . . .
H10 H 0.6309 0.6497 0.0367 0.087 Uiso 1 1 calc R . .
C11 C 0.60228(18) 0.6460(3) 0.14141(19) 0.0697(8) Uani 1 1 d . . .
H11 H 0.6224 0.7252 0.1548 0.084 Uiso 1 1 calc R . .
C12 C 0.56721(17) 0.5713(3) 0.19126(17) 0.0611(7) Uani 1 1 d . . .
H12 H 0.5642 0.6011 0.2389 0.073 Uiso 1 1 calc R . .
C13 C 0.58138(14) 0.1255(3) 0.14310(15) 0.0511(6) Uani 1 1 d . . .
H13A H 0.5886 0.0751 0.1871 0.061 Uiso 1 1 calc R . .
H13B H 0.6172 0.1922 0.1414 0.061 Uiso 1 1 calc R . .
C14 C 0.59193(15) 0.0341(3) 0.07856(17) 0.0573(7) Uani 1 1 d . . .
H14A H 0.5595 -0.0383 0.0814 0.069 Uiso 1 1 calc R . .
H14B H 0.5833 0.0813 0.0338 0.069 Uiso 1 1 calc R . .
C15 C 0.66433(17) -0.0173(3) 0.07865(19) 0.0676(8) Uani 1 1 d . . .
C16 C 0.7443(2) -0.1569(5) 0.0209(3) 0.1076(16) Uani 1 1 d . . .
H16A H 0.7756 -0.0886 0.0063 0.161 Uiso 1 1 calc R . .
H16B H 0.7448 -0.2258 -0.0146 0.161 Uiso 1 1 calc R . .
H16C H 0.7586 -0.1913 0.0670 0.161 Uiso 1 1 calc R . .
B1 B 0.40507(18) 0.7540(4) 0.11854(19) 0.0576(8) Uani 1 1 d . . .
F1 F 0.39901(12) 0.62028(19) 0.12045(12) 0.0884(6) Uani 1 1 d . . .
F2 F 0.46649(11) 0.7924(2) 0.08672(13) 0.0930(7) Uani 1 1 d . . .
F3 F 0.40065(12) 0.8035(2) 0.18754(10) 0.0843(6) Uani 1 1 d . . .
F4 F 0.35263(12) 0.8077(2) 0.07733(13) 0.0978(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N2 2.104(2) . ?
Co1 N2 2.104(2) 4_655 ?
Co1 N1 2.172(2) . ?
Co1 N1 2.172(2) 4_655 ?
Co1 N3 2.280(2) . ?
Co1 N3 2.280(2) 4_655 ?
N1 C5 1.342(3) . ?
N1 C1 1.354(4) . ?
N2 C8 1.336(3) . ?
N2 C12 1.346(4) . ?
N3 C6 1.477(3) . ?
N3 C13 1.482(3) . ?
N3 C7 1.490(3) . ?
O1 C15 1.178(4) . ?
O2 C15 1.317(4) . ?
O2 C16 1.444(4) . ?
C1 C2 1.364(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.504(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.497(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.377(4) . ?
C9 C10 1.376(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.525(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.493(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
B1 F1 1.369(4) . ?
B1 F3 1.371(4) . ?
B1 F4 1.379(4) . ?
B1 F2 1.380(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Co1 N2 96.98(12) . 4_655 ?
N2 Co1 N1 105.21(9) . . ?
N2 Co1 N1 92.13(8) 4_655 . ?
N2 Co1 N1 92.13(8) . 4_655 ?
N2 Co1 N1 105.21(9) 4_655 4_655 ?
N1 Co1 N1 153.89(12) . 4_655 ?
N2 Co1 N3 78.16(8) . . ?
N2 Co1 N3 163.69(8) 4_655 . ?
N1 Co1 N3 74.46(8) . . ?
N1 Co1 N3 90.62(8) 4_655 . ?
N2 Co1 N3 163.69(8) . 4_655 ?
N2 Co1 N3 78.16(8) 4_655 4_655 ?
N1 Co1 N3 90.61(8) . 4_655 ?
N1 Co1 N3 74.46(8) 4_655 4_655 ?
N3 Co1 N3 110.60(11) . 4_655 ?
C5 N1 C1 117.2(2) . . ?
C5 N1 Co1 115.62(17) . . ?
C1 N1 Co1 126.25(19) . . ?
C8 N2 C12 118.7(2) . . ?
C8 N2 Co1 115.90(17) . . ?
C12 N2 Co1 124.26(19) . . ?
C6 N3 C13 111.5(2) . . ?
C6 N3 C7 110.0(2) . . ?
C13 N3 C7 111.2(2) . . ?
C6 N3 Co1 106.18(15) . . ?
C13 N3 Co1 115.26(16) . . ?
C7 N3 Co1 102.24(15) . . ?
C15 O2 C16 117.0(3) . . ?
N1 C1 C2 123.3(3) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 122.2(3) . . ?
N1 C5 C6 117.1(2) . . ?
C4 C5 C6 120.7(3) . . ?
N3 C6 C5 111.1(2) . . ?
N3 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N3 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N3 C7 C8 110.9(2) . . ?
N3 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C9 121.6(3) . . ?
N2 C8 C7 115.5(2) . . ?
C9 C8 C7 122.9(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
N2 C12 C11 122.4(3) . . ?
N2 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N3 C13 C14 117.4(2) . . ?
N3 C13 H13A 108.0 . . ?
C14 C13 H13A 108.0 . . ?
N3 C13 H13B 108.0 . . ?
C14 C13 H13B 108.0 . . ?
H13A C13 H13B 107.2 . . ?
C15 C14 C13 109.8(2) . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O1 C15 O2 122.2(3) . . ?
O1 C15 C14 125.2(3) . . ?
O2 C15 C14 112.6(3) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F1 B1 F3 109.7(3) . . ?
F1 B1 F4 110.3(3) . . ?
F3 B1 F4 108.6(3) . . ?
F1 B1 F2 111.5(3) . . ?
F3 B1 F2 110.1(3) . . ?
F4 B1 F2 106.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Co1 N1 C5 97.3(2) . . . . ?
N2 Co1 N1 C5 -164.9(2) 4_655 . . . ?
N1 Co1 N1 C5 -32.62(18) 4_655 . . . ?
N3 Co1 N1 C5 24.55(19) . . . . ?
N3 Co1 N1 C5 -86.7(2) 4_655 . . . ?
N2 Co1 N1 C1 -93.9(2) . . . . ?
N2 Co1 N1 C1 3.9(2) 4_655 . . . ?
N1 Co1 N1 C1 136.1(2) 4_655 . . . ?
N3 Co1 N1 C1 -166.7(3) . . . . ?
N3 Co1 N1 C1 82.1(2) 4_655 . . . ?
N2 Co1 N2 C8 -155.6(2) 4_655 . . . ?
N1 Co1 N2 C8 -61.4(2) . . . . ?
N1 Co1 N2 C8 98.8(2) 4_655 . . . ?
N3 Co1 N2 C8 8.64(19) . . . . ?
N3 Co1 N2 C8 133.0(3) 4_655 . . . ?
N2 Co1 N2 C12 36.8(2) 4_655 . . . ?
N1 Co1 N2 C12 131.0(2) . . . . ?
N1 Co1 N2 C12 -68.8(2) 4_655 . . . ?
N3 Co1 N2 C12 -159.0(2) . . . . ?
N3 Co1 N2 C12 -34.6(4) 4_655 . . . ?
N2 Co1 N3 C6 -143.29(17) . . . . ?
N2 Co1 N3 C6 -69.2(3) 4_655 . . . ?
N1 Co1 N3 C6 -33.63(16) . . . . ?
N1 Co1 N3 C6 124.66(16) 4_655 . . . ?
N3 Co1 N3 C6 51.05(14) 4_655 . . . ?
N2 Co1 N3 C13 92.76(18) . . . . ?
N2 Co1 N3 C13 166.8(3) 4_655 . . . ?
N1 Co1 N3 C13 -157.58(19) . . . . ?
N1 Co1 N3 C13 0.71(18) 4_655 . . . ?
N3 Co1 N3 C13 -72.90(17) 4_655 . . . ?
N2 Co1 N3 C7 -27.95(15) . . . . ?
N2 Co1 N3 C7 46.1(4) 4_655 . . . ?
N1 Co1 N3 C7 81.71(16) . . . . ?
N1 Co1 N3 C7 -120.00(16) 4_655 . . . ?
N3 Co1 N3 C7 166.39(17) 4_655 . . . ?
C5 N1 C1 C2 0.6(5) . . . . ?
Co1 N1 C1 C2 -168.0(3) . . . . ?
N1 C1 C2 C3 1.4(5) . . . . ?
C1 C2 C3 C4 -2.4(6) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C1 N1 C5 C4 -1.6(4) . . . . ?
Co1 N1 C5 C4 168.2(2) . . . . ?
C1 N1 C5 C6 -179.8(2) . . . . ?
Co1 N1 C5 C6 -10.0(3) . . . . ?
C3 C4 C5 N1 0.6(5) . . . . ?
C3 C4 C5 C6 178.7(3) . . . . ?
C13 N3 C6 C5 165.4(2) . . . . ?
C7 N3 C6 C5 -70.7(3) . . . . ?
Co1 N3 C6 C5 39.2(2) . . . . ?
N1 C5 C6 N3 -21.5(3) . . . . ?
C4 C5 C6 N3 160.2(3) . . . . ?
C6 N3 C7 C8 155.8(2) . . . . ?
C13 N3 C7 C8 -80.2(3) . . . . ?
Co1 N3 C7 C8 43.3(2) . . . . ?
C12 N2 C8 C9 0.6(4) . . . . ?
Co1 N2 C8 C9 -167.8(2) . . . . ?
C12 N2 C8 C7 -177.4(2) . . . . ?
Co1 N2 C8 C7 14.3(3) . . . . ?
N3 C7 C8 N2 -41.6(3) . . . . ?
N3 C7 C8 C9 140.4(3) . . . . ?
N2 C8 C9 C10 -0.5(5) . . . . ?
C7 C8 C9 C10 177.3(3) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C8 N2 C12 C11 -0.1(4) . . . . ?
Co1 N2 C12 C11 167.2(2) . . . . ?
C10 C11 C12 N2 -0.5(5) . . . . ?
C6 N3 C13 C14 56.1(3) . . . . ?
C7 N3 C13 C14 -67.1(3) . . . . ?
Co1 N3 C13 C14 177.23(19) . . . . ?
N3 C13 C14 C15 176.3(2) . . . . ?
C16 O2 C15 O1 -1.9(6) . . . . ?
C16 O2 C15 C14 178.1(3) . . . . ?
C13 C14 C15 O1 -4.6(6) . . . . ?
C13 C14 C15 O2 175.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        74.03
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_12Ni
_database_code_depnum_ccdc_archive 'CCDC 1418417'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2015-11-08 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 H38 B2 F8 N6 Ni O4'
_chemical_formula_weight         803.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   19.4164(2)
_cell_length_b                   10.34210(10)
_cell_length_c                   17.9742(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3609.33(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7657
_cell_measurement_theta_min      3.3479
_cell_measurement_theta_max      75.6093

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_exptl_absorpt_coefficient_mu    1.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6980
_exptl_absorpt_correction_T_max  0.8008
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11856
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.84
_diffrn_reflns_theta_max         75.80
_reflns_number_total             3712
_reflns_number_gt                3410
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2011)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.0546P)²+0.9493P] 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         3712
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.0001

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 0.5000 0.82008(3) 0.2500 0.04564(14) Uani 1 2 d S . .
N1 N 0.39796(7) 0.78283(14) 0.20991(8) 0.0524(3) Uani 1 1 d . . .
N2 N 0.53687(7) 0.95464(13) 0.17459(7) 0.0521(3) Uani 1 1 d . . .
N3 N 0.51589(7) 0.69430(12) 0.15106(8) 0.0478(3) Uani 1 1 d . . .
O1 O 0.71003(10) 0.5168(3) 0.12676(16) 0.1466(12) Uani 1 1 d . . .
O2 O 0.67713(8) 0.39120(14) 0.03478(10) 0.0791(4) Uani 1 1 d . . .
C1 C 0.33922(10) 0.8432(2) 0.23014(12) 0.0639(5) Uani 1 1 d . . .
H1 H 0.3426 0.9215 0.2553 0.077 Uiso 1 1 calc R . .
C2 C 0.27481(11) 0.7949(2) 0.21540(15) 0.0768(6) Uani 1 1 d . . .
H2 H 0.2356 0.8399 0.2300 0.092 Uiso 1 1 calc R . .
C3 C 0.26924(11) 0.6786(2) 0.17865(15) 0.0798(6) Uani 1 1 d . . .
H3 H 0.2262 0.6425 0.1694 0.096 Uiso 1 1 calc R . .
C4 C 0.32828(10) 0.6165(2) 0.15588(12) 0.0676(5) Uani 1 1 d . . .
H4 H 0.3256 0.5391 0.1297 0.081 Uiso 1 1 calc R . .
C5 C 0.39185(9) 0.67064(16) 0.17244(10) 0.0525(4) Uani 1 1 d . . .
C6 C 0.45750(8) 0.60348(16) 0.15072(10) 0.0531(4) Uani 1 1 d . . .
H6A H 0.4666 0.5335 0.1853 0.064 Uiso 1 1 calc R . .
H6B H 0.4524 0.5666 0.1014 0.064 Uiso 1 1 calc R . .
C7 C 0.50841(10) 0.78653(18) 0.08782(9) 0.0550(4) Uani 1 1 d . . .
H7A H 0.4599 0.8017 0.0783 0.066 Uiso 1 1 calc R . .
H7B H 0.5284 0.7489 0.0434 0.066 Uiso 1 1 calc R . .
C8 C 0.54322(9) 0.91268(16) 0.10434(9) 0.0517(4) Uani 1 1 d . . .
C9 C 0.57732(10) 0.9833(2) 0.05053(11) 0.0628(4) Uani 1 1 d . . .
H9 H 0.5811 0.9521 0.0022 0.075 Uiso 1 1 calc R . .
C10 C 0.60570(12) 1.1010(2) 0.06977(13) 0.0726(5) Uani 1 1 d . . .
H10 H 0.6288 1.1504 0.0344 0.087 Uiso 1 1 calc R . .
C11 C 0.59951(11) 1.14423(19) 0.14159(13) 0.0685(5) Uani 1 1 d . . .
H11 H 0.6183 1.2233 0.1556 0.082 Uiso 1 1 calc R . .
C12 C 0.56516(10) 1.06925(16) 0.19264(11) 0.0607(4) Uani 1 1 d . . .
H12 H 0.5613 1.0987 0.2414 0.073 Uiso 1 1 calc R . .
C13 C 0.58310(8) 0.62628(17) 0.14790(10) 0.0526(4) Uani 1 1 d . . .
H13A H 0.5887 0.5781 0.1938 0.063 Uiso 1 1 calc R . .
H13B H 0.6192 0.6910 0.1464 0.063 Uiso 1 1 calc R . .
C14 C 0.59440(9) 0.53294(18) 0.08285(11) 0.0584(4) Uani 1 1 d . . .
H14A H 0.5620 0.4618 0.0861 0.070 Uiso 1 1 calc R . .
H14B H 0.5867 0.5776 0.0361 0.070 Uiso 1 1 calc R . .
C15 C 0.66673(10) 0.4819(2) 0.08535(13) 0.0681(5) Uani 1 1 d . . .
C16 C 0.74615(14) 0.3381(3) 0.0313(2) 0.1107(10) Uani 1 1 d . . .
H16A H 0.7773 0.4026 0.0128 0.166 Uiso 1 1 calc R . .
H16B H 0.7465 0.2646 -0.0013 0.166 Uiso 1 1 calc R . .
H16C H 0.7604 0.3118 0.0802 0.166 Uiso 1 1 calc R . .
B1 B 0.40530(11) 0.2659(2) 0.12099(12) 0.0601(5) Uani 1 1 d . . .
F1 F 0.39839(8) 0.31498(13) 0.19132(7) 0.0869(4) Uani 1 1 d . . .
F2 F 0.46735(7) 0.30412(15) 0.09008(9) 0.0924(4) Uani 1 1 d . . .
F4 F 0.35390(8) 0.31591(15) 0.07632(9) 0.0961(4) Uani 1 1 d . . .
F3 F 0.40016(8) 0.13373(13) 0.12331(8) 0.0895(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N2 2.0704(14) . ?
Ni1 N2 2.0704(14) 4_655 ?
Ni1 N1 2.1431(14) 4_655 ?
Ni1 N1 2.1431(14) . ?
Ni1 N3 2.2248(14) . ?
Ni1 N3 2.2248(14) 4_655 ?
N1 C5 1.347(2) . ?
N1 C1 1.350(2) . ?
N2 C8 1.341(2) . ?
N2 C12 1.346(2) . ?
N3 C6 1.472(2) . ?
N3 C13 1.483(2) . ?
N3 C7 1.491(2) . ?
O1 C15 1.180(3) . ?
O2 C15 1.321(2) . ?
O2 C16 1.450(3) . ?
C1 C2 1.373(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.503(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.499(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.381(2) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.371(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.532(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.501(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
B1 F1 1.369(3) . ?
B1 F3 1.371(3) . ?
B1 F4 1.381(3) . ?
B1 F2 1.385(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ni1 N2 95.53(8) . 4_655 ?
N2 Ni1 N1 91.22(5) . 4_655 ?
N2 Ni1 N1 102.73(6) 4_655 4_655 ?
N2 Ni1 N1 102.73(6) . . ?
N2 Ni1 N1 91.22(5) 4_655 . ?
N1 Ni1 N1 159.29(8) 4_655 . ?
N2 Ni1 N3 79.73(5) . . ?
N2 Ni1 N3 164.64(5) 4_655 . ?
N1 Ni1 N3 92.03(5) 4_655 . ?
N1 Ni1 N3 75.78(5) . . ?
N2 Ni1 N3 164.64(5) . 4_655 ?
N2 Ni1 N3 79.73(5) 4_655 4_655 ?
N1 Ni1 N3 75.78(5) 4_655 4_655 ?
N1 Ni1 N3 92.03(5) . 4_655 ?
N3 Ni1 N3 108.44(7) . 4_655 ?
C5 N1 C1 117.31(15) . . ?
C5 N1 Ni1 113.85(11) . . ?
C1 N1 Ni1 127.39(12) . . ?
C8 N2 C12 118.33(15) . . ?
C8 N2 Ni1 115.52(11) . . ?
C12 N2 Ni1 125.11(12) . . ?
C6 N3 C13 112.00(12) . . ?
C6 N3 C7 109.26(13) . . ?
C13 N3 C7 111.09(14) . . ?
C6 N3 Ni1 105.64(10) . . ?
C13 N3 Ni1 115.46(10) . . ?
C7 N3 Ni1 102.81(10) . . ?
C15 O2 C16 116.1(2) . . ?
N1 C1 C2 123.30(19) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 118.85(19) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.00(19) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.29(19) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.21(17) . . ?
N1 C5 C6 116.95(14) . . ?
C4 C5 C6 120.81(15) . . ?
N3 C6 C5 110.92(13) . . ?
N3 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
N3 C7 C8 111.22(13) . . ?
N3 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C9 122.17(17) . . ?
N2 C8 C7 115.26(14) . . ?
C9 C8 C7 122.53(16) . . ?
C10 C9 C8 118.84(18) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C10 C9 119.24(19) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 119.15(19) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
N2 C12 C11 122.28(18) . . ?
N2 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
N3 C13 C14 117.00(14) . . ?
N3 C13 H13A 108.0 . . ?
C14 C13 H13A 108.0 . . ?
N3 C13 H13B 108.0 . . ?
C14 C13 H13B 108.0 . . ?
H13A C13 H13B 107.3 . . ?
C15 C14 C13 109.45(16) . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
O1 C15 O2 122.8(2) . . ?
O1 C15 C14 125.31(19) . . ?
O2 C15 C14 111.85(18) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F1 B1 F3 109.55(17) . . ?
F1 B1 F4 109.09(18) . . ?
F3 B1 F4 109.78(18) . . ?
F1 B1 F2 110.49(18) . . ?
F3 B1 F2 111.11(18) . . ?
F4 B1 F2 106.77(18) . . ?

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
N2 Ni1 N1 C5 102.49(13) . . . . ?
N2 Ni1 N1 C5 -161.56(13) 4_655 . . . ?
N1 Ni1 N1 C5 -28.75(12) 4_655 . . . ?
N3 Ni1 N1 C5 26.72(12) . . . . ?
N3 Ni1 N1 C5 -81.80(13) 4_655 . . . ?
N2 Ni1 N1 C1 -91.75(17) . . . . ?
N2 Ni1 N1 C1 4.20(17) 4_655 . . . ?
N1 Ni1 N1 C1 137.01(17) 4_655 . . . ?
N3 Ni1 N1 C1 -167.52(17) . . . . ?
N3 Ni1 N1 C1 83.97(17) 4_655 . . . ?
N2 Ni1 N2 C8 -156.60(15) 4_655 . . . ?
N1 Ni1 N2 C8 100.48(13) 4_655 . . . ?
N1 Ni1 N2 C8 -64.09(13) . . . . ?
N3 Ni1 N2 C8 8.64(12) . . . . ?
N3 Ni1 N2 C8 132.29(19) 4_655 . . . ?
N2 Ni1 N2 C12 35.36(13) 4_655 . . . ?
N1 Ni1 N2 C12 -67.56(15) 4_655 . . . ?
N1 Ni1 N2 C12 127.87(15) . . . . ?
N3 Ni1 N2 C12 -159.40(15) . . . . ?
N3 Ni1 N2 C12 -35.8(3) 4_655 . . . ?
N2 Ni1 N3 C6 -141.38(11) . . . . ?
N2 Ni1 N3 C6 -68.2(2) 4_655 . . . ?
N1 Ni1 N3 C6 127.74(10) 4_655 . . . ?
N1 Ni1 N3 C6 -35.31(10) . . . . ?
N3 Ni1 N3 C6 52.06(9) 4_655 . . . ?
N2 Ni1 N3 C13 94.27(11) . . . . ?
N2 Ni1 N3 C13 167.42(18) 4_655 . . . ?
N1 Ni1 N3 C13 3.40(11) 4_655 . . . ?
N1 Ni1 N3 C13 -159.65(12) . . . . ?
N3 Ni1 N3 C13 -72.29(10) 4_655 . . . ?
N2 Ni1 N3 C7 -26.86(10) . . . . ?
N2 Ni1 N3 C7 46.3(2) 4_655 . . . ?
N1 Ni1 N3 C7 -117.74(10) 4_655 . . . ?
N1 Ni1 N3 C7 79.21(10) . . . . ?
N3 Ni1 N3 C7 166.58(11) 4_655 . . . ?
C5 N1 C1 C2 1.1(3) . . . . ?
Ni1 N1 C1 C2 -164.28(18) . . . . ?
N1 C1 C2 C3 0.5(4) . . . . ?
C1 C2 C3 C4 -2.0(4) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C1 N1 C5 C4 -1.1(3) . . . . ?
Ni1 N1 C5 C4 166.18(15) . . . . ?
C1 N1 C5 C6 -179.48(16) . . . . ?
Ni1 N1 C5 C6 -12.2(2) . . . . ?
C3 C4 C5 N1 -0.3(3) . . . . ?
C3 C4 C5 C6 178.0(2) . . . . ?
C13 N3 C6 C5 166.23(14) . . . . ?
C7 N3 C6 C5 -70.24(17) . . . . ?
Ni1 N3 C6 C5 39.75(15) . . . . ?
N1 C5 C6 N3 -20.2(2) . . . . ?
C4 C5 C6 N3 161.41(17) . . . . ?
C6 N3 C7 C8 152.97(14) . . . . ?
C13 N3 C7 C8 -82.96(17) . . . . ?
Ni1 N3 C7 C8 41.11(15) . . . . ?
C12 N2 C8 C9 -0.3(3) . . . . ?
Ni1 N2 C8 C9 -169.22(14) . . . . ?
C12 N2 C8 C7 -178.04(15) . . . . ?
Ni1 N2 C8 C7 13.06(19) . . . . ?
N3 C7 C8 N2 -38.9(2) . . . . ?
N3 C7 C8 C9 143.41(17) . . . . ?
N2 C8 C9 C10 0.0(3) . . . . ?
C7 C8 C9 C10 177.50(18) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C8 N2 C12 C11 0.5(3) . . . . ?
Ni1 N2 C12 C11 168.27(15) . . . . ?
C10 C11 C12 N2 -0.4(3) . . . . ?
C6 N3 C13 C14 55.7(2) . . . . ?
C7 N3 C13 C14 -66.75(19) . . . . ?
Ni1 N3 C13 C14 176.70(12) . . . . ?
N3 C13 C14 C15 175.42(15) . . . . ?
C16 O2 C15 O1 -1.6(4) . . . . ?
C16 O2 C15 C14 178.3(2) . . . . ?
C13 C14 C15 O1 -6.3(4) . . . . ?
C13 C14 C15 O2 173.78(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        75.80
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.035






