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

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

data_NCU_2
_database_code_depnum_ccdc_archive 'CCDC 1051117'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 N5 O13 P3 Zn3'
_chemical_formula_weight         807.44

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.2153(4)
_cell_length_b                   11.1328(6)
_cell_length_c                   15.2684(9)
_cell_angle_alpha                70.278(3)
_cell_angle_beta                 83.973(3)
_cell_angle_gamma                71.336(3)
_cell_volume                     1396.98(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       yellow
_exptl_crystal_colour            thin-plate
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    2.799
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'SADABS program'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46514
_diffrn_reflns_av_R_equivalents  0.1370
_diffrn_reflns_av_sigmaI/netI    0.0749
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         27.53
_reflns_number_total             6418
_reflns_number_gt                4199
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker X8 Apex'
_computing_cell_refinement       'Bruker X8 Apex'
_computing_data_reduction        'Bruker X8 Apex'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1237P)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     SHELXL
_refine_ls_extinction_coef       0.0107(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6418
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1987
_refine_ls_wR_factor_gt          0.1777
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn -1.31194(7) 1.74919(7) 0.74625(5) 0.0369(2) Uani 1 1 d . . .
Zn2 Zn -1.50991(8) 1.47112(7) 0.64980(5) 0.0406(2) Uani 1 1 d . . .
Zn3 Zn -1.85513(7) 1.81390(6) 0.51218(5) 0.0329(2) Uani 1 1 d . . .
P1 P -1.60176(17) 1.76324(16) 0.65559(11) 0.0351(4) Uani 1 1 d . . .
H1 H -1.6905 1.8201 0.7258 0.050 Uiso 1 1 d . . .
P2 P -1.75360(17) 1.51760(15) 0.50222(10) 0.0321(4) Uani 1 1 d . . .
H2 H -1.8555 1.4515 0.5091 0.050 Uiso 1 1 d . . .
P3 P -2.08044(16) 1.91720(16) 0.65906(10) 0.0343(4) Uani 1 1 d . . .
H3 H -1.9644 1.8905 0.7048 0.050 Uiso 1 1 d . . .
O1 O -1.4452(4) 1.7878(4) 0.6442(3) 0.0400(10) Uani 1 1 d . . .
O2 O -1.5928(5) 1.6172(5) 0.6998(3) 0.0516(12) Uani 1 1 d . . .
O3 O -1.6845(5) 1.8299(5) 0.5654(3) 0.0504(12) Uani 1 1 d . . .
O4 O -1.6598(7) 1.4423(5) 0.5894(4) 0.0714(16) Uani 1 1 d . . .
O5A O -1.6780(14) 1.5551(11) 0.4096(7) 0.061(2) Uani 0.50 1 d P . .
O5B O -1.6592(14) 1.4692(11) 0.4276(7) 0.061(2) Uani 0.50 1 d P . .
O6A O -1.8707(15) 1.6369(11) 0.5229(8) 0.060(2) Uani 0.50 1 d P . .
O6B O -1.8306(15) 1.6637(11) 0.4700(8) 0.060(2) Uani 0.50 1 d P . .
O7 O -2.0323(5) 1.8386(5) 0.5933(3) 0.0539(13) Uani 1 1 d . . .
O8 O -2.2054(5) 1.8789(5) 0.7231(4) 0.0595(13) Uani 1 1 d . . .
O9 O -2.1194(6) 2.0679(5) 0.6133(3) 0.0582(13) Uani 1 1 d . . .
N1 N -1.1701(5) 1.5593(5) 0.7813(3) 0.0380(12) Uani 1 1 d . . .
N2 N -0.5582(6) 0.6876(5) 1.2306(3) 0.0407(12) Uani 1 1 d . . .
N3 N -0.6372(6) 1.1527(5) 0.5430(3) 0.0384(12) Uani 1 1 d . . .
H4 H -0.6399 1.1728 0.4803 0.050 Uiso 1 1 d . . .
N4 N -0.8343(5) 1.1036(5) 0.9641(3) 0.0376(12) Uani 1 1 d . . .
N5 N -0.6546(5) 0.9825(5) 0.8901(3) 0.0338(11) Uani 1 1 d . . .
C1 C -1.0446(7) 1.5259(6) 0.7312(5) 0.0415(14) Uani 1 1 d . . .
H1A H -1.0278 1.5902 0.6771 0.050 Uiso 1 1 calc R . .
C2 C -0.9389(7) 1.3993(6) 0.7569(4) 0.0407(15) Uani 1 1 d . . .
H2A H -0.8522 1.3798 0.7209 0.049 Uiso 1 1 calc R . .
C3 C -1.1968(7) 1.4639(7) 0.8570(4) 0.0439(15) Uani 1 1 d . . .
H3A H -1.2860 1.4859 0.8905 0.053 Uiso 1 1 calc R . .
C4 C -1.0982(7) 1.3341(6) 0.8879(4) 0.0416(15) Uani 1 1 d . . .
H4A H -1.1203 1.2704 0.9406 0.050 Uiso 1 1 calc R . .
C5 C -0.9635(6) 1.3021(6) 0.8366(4) 0.0354(13) Uani 1 1 d . . .
C6 C -0.6878(7) 0.7888(6) 1.2254(4) 0.0414(15) Uani 1 1 d . . .
H6A H -0.7451 0.7901 1.2792 0.050 Uiso 1 1 calc R . .
C7 C -0.7391(7) 0.8900(6) 1.1442(4) 0.0430(15) Uani 1 1 d . . .
H7A H -0.8290 0.9589 1.1435 0.052 Uiso 1 1 calc R . .
C8 C -0.4737(8) 0.6871(7) 1.1527(4) 0.0476(16) Uani 1 1 d . . .
H8A H -0.3825 0.6184 1.1561 0.057 Uiso 1 1 calc R . .
C9 C -0.5196(7) 0.7874(6) 1.0670(4) 0.0432(15) Uani 1 1 d . . .
H9A H -0.4594 0.7853 1.0144 0.052 Uiso 1 1 calc R . .
C10 C -0.6554(7) 0.8895(6) 1.0615(4) 0.0377(14) Uani 1 1 d . . .
C11 C -0.5237(7) 1.1039(6) 0.6049(4) 0.0421(15) Uani 1 1 d . . .
H11A H -0.4222 1.0836 0.5855 0.050 Uiso 1 1 calc R . .
C12 C -0.5575(6) 1.0842(6) 0.6959(4) 0.0362(13) Uani 1 1 d . . .
H12A H -0.4787 1.0501 0.7393 0.043 Uiso 1 1 calc R . .
C13 C -0.7824(7) 1.1810(6) 0.5678(4) 0.0432(15) Uani 1 1 d . . .
H13A H -0.8580 1.2144 0.5225 0.052 Uiso 1 1 calc R . .
C14 C -0.8239(6) 1.1623(6) 0.6589(4) 0.0363(13) Uani 1 1 d . . .
H14A H -0.9265 1.1811 0.6763 0.044 Uiso 1 1 calc R . .
C15 C -0.7075(6) 1.1140(5) 0.7253(4) 0.0277(11) Uani 1 1 d . . .
C16 C -0.8491(6) 1.1675(5) 0.8723(4) 0.0306(12) Uani 1 1 d . . .
C17 C -0.7134(6) 0.9907(6) 0.9738(4) 0.0347(13) Uani 1 1 d . . .
C18 C -0.7412(6) 1.0922(5) 0.8258(4) 0.0309(12) Uani 1 1 d . . .
OW1 O -1.4477(4) 1.7728(4) 0.8497(3) 0.0389(10) Uani 1 1 d . . .
OW2 O -0.8984(13) 1.2714(12) 1.0794(9) 0.202 Uiso 1 1 d . . .
OW3 O -1.4035(15) 1.4030(13) 1.0612(9) 0.226 Uiso 1 1 d . . .
OW4 O -0.1621(10) 0.4834(9) 1.0724(6) 0.136 Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O8 1.914(5) 1_655 ?
Zn1 O1 1.932(4) . ?
Zn1 OW1 1.945(4) . ?
Zn1 N1 2.019(5) . ?
Zn2 O5A 1.853(11) 2_286 ?
Zn2 O4 1.901(5) . ?
Zn2 O2 1.931(5) . ?
Zn2 O5B 2.004(12) 2_286 ?
Zn2 N2 2.050(5) 2_377 ?
Zn3 O9 1.912(4) 2_196 ?
Zn3 O3 1.925(4) . ?
Zn3 O6B 1.928(12) . ?
Zn3 O7 1.947(4) . ?
Zn3 O6A 1.972(12) . ?
P1 O3 1.483(4) . ?
P1 O2 1.514(5) . ?
P1 O1 1.534(4) . ?
P1 H1 1.4701 . ?
P2 O6B 1.478(11) . ?
P2 O5A 1.496(11) . ?
P2 O4 1.499(5) . ?
P2 O5B 1.500(11) . ?
P2 O6A 1.524(12) . ?
P2 H2 1.3430 . ?
P3 O7 1.491(5) . ?
P3 O8 1.503(5) . ?
P3 O9 1.519(5) . ?
P3 H3 1.2380 . ?
O5A O5B 0.865(14) . ?
O5A Zn2 1.853(11) 2_286 ?
O5B Zn2 2.003(12) 2_286 ?
O6A O6B 0.850(13) . ?
O8 Zn1 1.914(5) 1_455 ?
O9 Zn3 1.912(4) 2_196 ?
N1 C1 1.338(7) . ?
N1 C3 1.344(8) . ?
N2 C6 1.342(7) . ?
N2 C8 1.352(8) . ?
N2 Zn2 2.050(5) 2_377 ?
N3 C13 1.318(8) . ?
N3 C11 1.334(8) . ?
N3 H4 0.9074 . ?
N4 C16 1.339(7) . ?
N4 C17 1.363(7) . ?
N5 C18 1.350(7) . ?
N5 C17 1.355(7) . ?
C1 C2 1.385(8) . ?
C1 H1A 0.9300 . ?
C2 C5 1.383(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.388(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.408(8) . ?
C4 H4A 0.9300 . ?
C5 C16 1.488(7) . ?
C6 C7 1.368(8) . ?
C6 H6A 0.9300 . ?
C7 C10 1.410(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.402(8) . ?
C8 H8A 0.9300 . ?
C9 C10 1.382(8) . ?
C9 H9A 0.9300 . ?
C10 C17 1.447(8) . ?
C11 C12 1.351(8) . ?
C11 H11A 0.9300 . ?
C12 C15 1.377(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.367(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.400(8) . ?
C14 H14A 0.9300 . ?
C15 C18 1.486(7) . ?
C16 C18 1.383(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Zn1 O1 112.1(2) 1_655 . ?
O8 Zn1 OW1 104.89(19) 1_655 . ?
O1 Zn1 OW1 105.35(17) . . ?
O8 Zn1 N1 112.8(2) 1_655 . ?
O1 Zn1 N1 111.5(2) . . ?
OW1 Zn1 N1 109.67(18) . . ?
O5A Zn2 O4 112.7(5) 2_286 . ?
O5A Zn2 O2 121.7(4) 2_286 . ?
O4 Zn2 O2 113.0(2) . . ?
O5A Zn2 O5B 25.5(4) 2_286 2_286 ?
O4 Zn2 O5B 118.0(4) . 2_286 ?
O2 Zn2 O5B 99.2(4) . 2_286 ?
O5A Zn2 N2 96.9(4) 2_286 2_377 ?
O4 Zn2 N2 108.5(2) . 2_377 ?
O2 Zn2 N2 100.93(19) . 2_377 ?
O5B Zn2 N2 115.5(3) 2_286 2_377 ?
O9 Zn3 O3 107.9(2) 2_196 . ?
O9 Zn3 O6B 90.5(4) 2_196 . ?
O3 Zn3 O6B 120.4(4) . . ?
O9 Zn3 O7 116.6(2) 2_196 . ?
O3 Zn3 O7 109.50(19) . . ?
O6B Zn3 O7 111.1(4) . . ?
O9 Zn3 O6A 112.0(4) 2_196 . ?
O3 Zn3 O6A 121.1(4) . . ?
O6B Zn3 O6A 25.2(4) . . ?
O7 Zn3 O6A 89.1(4) . . ?
O3 P1 O2 114.3(3) . . ?
O3 P1 O1 109.2(3) . . ?
O2 P1 O1 113.6(3) . . ?
O3 P1 H1 109.4 . . ?
O2 P1 H1 101.0 . . ?
O1 P1 H1 109.0 . . ?
O6B P2 O5A 80.3(6) . . ?
O6B P2 O4 124.8(6) . . ?
O5A P2 O4 120.7(5) . . ?
O6B P2 O5B 112.6(6) . . ?
O5A P2 O5B 33.5(5) . . ?
O4 P2 O5B 105.4(5) . . ?
O6B P2 O6A 32.9(5) . . ?
O5A P2 O6A 113.2(6) . . ?
O4 P2 O6A 104.8(5) . . ?
O5B P2 O6A 144.8(6) . . ?
O6B P2 H2 110.1 . . ?
O5A P2 H2 116.2 . . ?
O4 P2 H2 104.0 . . ?
O5B P2 H2 95.6 . . ?
O6A P2 H2 94.2 . . ?
O7 P3 O8 111.9(3) . . ?
O7 P3 O9 114.7(3) . . ?
O8 P3 O9 111.9(3) . . ?
O7 P3 H3 105.5 . . ?
O8 P3 H3 109.8 . . ?
O9 P3 H3 102.3 . . ?
P1 O1 Zn1 124.4(2) . . ?
P1 O2 Zn2 129.2(3) . . ?
P1 O3 Zn3 135.3(3) . . ?
P2 O4 Zn2 135.4(3) . . ?
O5B O5A P2 73.5(12) . . ?
O5B O5A Zn2 87.0(13) . 2_286 ?
P2 O5A Zn2 143.2(7) . 2_286 ?
O5A O5B P2 73.0(12) . . ?
O5A O5B Zn2 67.5(12) . 2_286 ?
P2 O5B Zn2 129.8(8) . 2_286 ?
O6B O6A P2 70.6(13) . . ?
O6B O6A Zn3 74.6(14) . . ?
P2 O6A Zn3 130.5(8) . . ?
O6A O6B P2 76.5(13) . . ?
O6A O6B Zn3 80.3(14) . . ?
P2 O6B Zn3 137.6(8) . . ?
P3 O7 Zn3 132.0(3) . . ?
P3 O8 Zn1 136.5(3) . 1_455 ?
P3 O9 Zn3 134.8(3) . 2_196 ?
C1 N1 C3 118.1(5) . . ?
C1 N1 Zn1 121.0(4) . . ?
C3 N1 Zn1 120.9(4) . . ?
C6 N2 C8 118.6(5) . . ?
C6 N2 Zn2 122.5(4) . 2_377 ?
C8 N2 Zn2 118.9(4) . 2_377 ?
C13 N3 C11 122.1(5) . . ?
C13 N3 H4 104.4 . . ?
C11 N3 H4 133.5 . . ?
C16 N4 C17 105.3(5) . . ?
C18 N5 C17 105.8(4) . . ?
N1 C1 C2 122.6(6) . . ?
N1 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C5 C2 C1 119.4(5) . . ?
C5 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
N1 C3 C4 123.4(6) . . ?
N1 C3 H3A 118.3 . . ?
C4 C3 H3A 118.3 . . ?
C3 C4 C5 117.7(6) . . ?
C3 C4 H4A 121.1 . . ?
C5 C4 H4A 121.1 . . ?
C2 C5 C4 118.7(5) . . ?
C2 C5 C16 122.2(5) . . ?
C4 C5 C16 119.0(5) . . ?
N2 C6 C7 122.6(6) . . ?
N2 C6 H6A 118.7 . . ?
C7 C6 H6A 118.7 . . ?
C6 C7 C10 119.8(5) . . ?
C6 C7 H7A 120.1 . . ?
C10 C7 H7A 120.1 . . ?
N2 C8 C9 121.9(6) . . ?
N2 C8 H8A 119.1 . . ?
C9 C8 H8A 119.1 . . ?
C10 C9 C8 119.3(6) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C9 C10 C7 117.7(5) . . ?
C9 C10 C17 121.7(5) . . ?
C7 C10 C17 120.5(5) . . ?
N3 C11 C12 119.4(5) . . ?
N3 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C11 C12 C15 120.8(6) . . ?
C11 C12 H12A 119.6 . . ?
C15 C12 H12A 119.6 . . ?
N3 C13 C14 121.3(5) . . ?
N3 C13 H13A 119.4 . . ?
C14 C13 H13A 119.4 . . ?
C13 C14 C15 118.0(5) . . ?
C13 C14 H14A 121.0 . . ?
C15 C14 H14A 121.0 . . ?
C12 C15 C14 118.5(5) . . ?
C12 C15 C18 119.6(5) . . ?
C14 C15 C18 121.9(5) . . ?
N4 C16 C18 109.4(5) . . ?
N4 C16 C5 119.8(5) . . ?
C18 C16 C5 130.6(5) . . ?
N5 C17 N4 111.4(5) . . ?
N5 C17 C10 123.4(5) . . ?
N4 C17 C10 125.1(5) . . ?
N5 C18 C16 108.0(5) . . ?
N5 C18 C15 119.8(5) . . ?
C16 C18 C15 132.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.895
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.229
####################################################################### 
# 
# 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_NCU_2a
_database_code_depnum_ccdc_archive 'CCDC 1051118'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N5 O10 P3 Zn3'
_chemical_formula_weight         753.39

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.149(3)
_cell_length_b                   11.202(4)
_cell_length_c                   14.628(5)
_cell_angle_alpha                73.526(13)
_cell_angle_beta                 88.045(14)
_cell_angle_gamma                71.284(12)
_cell_volume                     1358.9(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       yellow
_exptl_crystal_colour            thin-plate
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.841
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.863
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   'SADABS program'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48630
_diffrn_reflns_av_R_equivalents  0.1968
_diffrn_reflns_av_sigmaI/netI    0.1688
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6229
_reflns_number_gt                2765
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker X8 Apex'
_computing_cell_refinement       'Bruker X8 Apex'
_computing_data_reduction        'Bruker X8 Apex'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1930P)²+27.8142P] 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         6229
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2472
_refine_ls_R_factor_gt           0.1320
_refine_ls_wR_factor_ref         0.4261
_refine_ls_wR_factor_gt          0.3552
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 1.8496(2) 0.18320(19) -0.01364(15) 0.0500(6) Uani 1 1 d . . .
Zn2 Zn 1.2906(3) 0.2364(2) -0.26010(16) 0.0570(7) Uani 1 1 d . . .
Zn3 Zn 0.5055(3) 1.4873(2) -0.84766(15) 0.0573(7) Uani 1 1 d . . .
P1 P 1.7501(5) 0.4792(4) -0.0030(4) 0.0476(11) Uani 1 1 d . . .
P2 P 2.0658(5) 0.0796(5) -0.1636(4) 0.0503(12) Uani 1 1 d . . .
H2 H 1.9737 0.1228 -0.2387 0.050 Uiso 1 1 d . . .
P3 P 1.5888(5) 0.2275(5) -0.1643(4) 0.0515(12) Uani 1 1 d . . .
H3 H 1.6478 0.1546 -0.2334 0.050 Uiso 1 1 d . . .
O1 O 1.6593(19) 0.5409(16) -0.0944(12) 0.086(5) Uani 1 1 d . . .
O2 O 1.669(2) 0.525(2) 0.0769(13) 0.109(6) Uani 1 1 d . . .
O3A O 1.793(4) 0.330(4) 0.036(3) 0.081(8) Uani 0.50 1 d P . .
O3B O 1.853(4) 0.348(4) -0.004(3) 0.081(8) Uani 0.50 1 d P . .
O4 O 2.0143(15) 0.1678(14) -0.0995(10) 0.063(4) Uani 1 1 d . . .
O5 O 2.1022(19) -0.0667(14) -0.1112(10) 0.080(4) Uani 1 1 d . . .
O6 O 2.1926(17) 0.1062(15) -0.2254(12) 0.079(4) Uani 1 1 d . . .
O7 O 1.6746(16) 0.1599(14) -0.0689(10) 0.066(4) Uani 1 1 d . . .
O8 O 1.4310(14) 0.2075(13) -0.1517(9) 0.061(3) Uani 1 1 d . . .
O9 O 1.5776(18) 0.3691(13) -0.2071(10) 0.071(4) Uani 1 1 d . . .
N1 N 0.6384(19) 0.8361(15) -0.0365(11) 0.055(4) Uani 1 1 d . . .
H4 H 0.6223 0.8178 0.0295 0.050 Uiso 1 1 d . . .
N2 N 1.1464(19) 0.4265(16) -0.2969(12) 0.064(4) Uani 1 1 d . . .
N3 N 0.582(2) 1.3286(16) -0.7289(11) 0.061(4) Uani 1 1 d . . .
N4 N 0.6566(19) 1.0128(14) -0.3901(11) 0.058(4) Uani 1 1 d . . .
N5 N 0.8333(18) 0.8977(14) -0.4679(11) 0.057(4) Uani 1 1 d . . .
C1 C 0.787(2) 0.8026(19) -0.0604(14) 0.054(5) Uani 1 1 d . . .
H1A H 0.8665 0.7668 -0.0128 0.065 Uiso 1 1 calc R . .
C2 C 0.821(2) 0.8207(18) -0.1530(16) 0.058(5) Uani 1 1 d . . .
H2A H 0.9236 0.7976 -0.1687 0.070 Uiso 1 1 calc R . .
C3 C 0.521(2) 0.8903(16) -0.1030(15) 0.057(5) Uani 1 1 d . . .
H3A H 0.4195 0.9167 -0.0849 0.068 Uiso 1 1 calc R . .
C4 C 0.5495(19) 0.9074(16) -0.2005(14) 0.049(4) Uani 1 1 d . . .
H4A H 0.4690 0.9402 -0.2473 0.059 Uiso 1 1 calc R . .
C5 C 0.7042(19) 0.8731(14) -0.2241(13) 0.046(4) Uani 1 1 d . . .
C6 C 1.167(3) 0.517(2) -0.3738(16) 0.085(8) Uani 1 1 d . . .
H6A H 1.2470 0.4910 -0.4122 0.102 Uiso 1 1 calc R . .
C7 C 1.075(2) 0.647(2) -0.3989(17) 0.073(6) Uani 1 1 d . . .
H7A H 1.0977 0.7082 -0.4504 0.088 Uiso 1 1 calc R . .
C8 C 1.030(3) 0.4660(18) -0.2443(15) 0.067(6) Uani 1 1 d . . .
H8A H 1.0189 0.4055 -0.1882 0.081 Uiso 1 1 calc R . .
C9 C 0.925(2) 0.5899(18) -0.2673(15) 0.061(5) Uani 1 1 d . . .
H9A H 0.8396 0.6098 -0.2312 0.073 Uiso 1 1 calc R . .
C10 C 0.947(2) 0.6876(17) -0.3468(15) 0.063(5) Uani 1 1 d . . .
C11 C 0.697(3) 1.2229(17) -0.7264(13) 0.062(6) Uani 1 1 d . . .
H11A H 0.7494 1.2178 -0.7815 0.075 Uiso 1 1 calc R . .
C12 C 0.744(3) 1.1199(19) -0.6461(15) 0.067(6) Uani 1 1 d . . .
H12A H 0.8286 1.0477 -0.6480 0.080 Uiso 1 1 calc R . .
C13 C 0.504(3) 1.331(2) -0.6472(14) 0.073(6) Uani 1 1 d . . .
H13A H 0.4199 1.4051 -0.6474 0.087 Uiso 1 1 calc R . .
C14 C 0.545(2) 1.233(2) -0.5692(14) 0.068(6) Uani 1 1 d . . .
H14A H 0.4876 1.2393 -0.5159 0.081 Uiso 1 1 calc R . .
C15 C 0.672(2) 1.1179(17) -0.5623(13) 0.054(5) Uani 1 1 d . . .
C16 C 0.7371(18) 0.8976(14) -0.3266(12) 0.041(4) Uani 1 1 d . . .
C17 C 0.844(2) 0.8267(18) -0.3756(14) 0.054(5) Uani 1 1 d . . .
C18 C 0.719(2) 1.0087(17) -0.4749(13) 0.051(4) Uani 1 1 d . . .
OW1 O 1.4220(12) 0.2070(11) -0.3602(8) 0.051(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O5 1.888(14) 2_955 ?
Zn1 O3B 1.90(4) . ?
Zn1 O3A 1.90(4) . ?
Zn1 O4 1.925(12) . ?
Zn1 O7 1.940(13) . ?
Zn2 O6 1.892(14) 1_455 ?
Zn2 OW1 1.897(10) . ?
Zn2 O8 1.962(13) . ?
Zn2 N2 2.039(16) . ?
Zn3 O1 1.907(16) 2_774 ?
Zn3 O2 1.919(19) 1_464 ?
Zn3 O9 1.926(13) 2_774 ?
Zn3 N3 2.049(15) . ?
P1 O1 1.462(17) . ?
P1 O3B 1.48(3) . ?
P1 O2 1.490(17) . ?
P1 O3A 1.53(4) . ?
P2 O6 1.500(15) . ?
P2 O4 1.508(13) . ?
P2 O5 1.530(16) . ?
P2 H2 1.2851 . ?
P3 O7 1.493(14) . ?
P3 O9 1.502(14) . ?
P3 O8 1.527(14) . ?
P3 H3 1.4593 . ?
O1 Zn3 1.907(16) 2_774 ?
O2 Zn3 1.919(19) 1_646 ?
O3A O3B 0.82(4) . ?
O5 Zn1 1.888(14) 2_955 ?
O6 Zn2 1.892(14) 1_655 ?
O9 Zn3 1.926(13) 2_774 ?
N1 C3 1.34(2) . ?
N1 C1 1.35(2) . ?
N1 H4 0.9451 . ?
N2 C8 1.33(2) . ?
N2 C6 1.34(3) . ?
N3 C11 1.30(2) . ?
N3 C13 1.37(2) . ?
N4 C16 1.35(2) . ?
N4 C18 1.35(2) . ?
N5 C18 1.32(2) . ?
N5 C17 1.35(2) . ?
C1 C2 1.35(3) . ?
C1 H1A 0.9300 . ?
C2 C5 1.38(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.41(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.40(2) . ?
C4 H4A 0.9300 . ?
C5 C16 1.48(2) . ?
C6 C7 1.38(3) . ?
C6 H6A 0.9300 . ?
C7 C10 1.39(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.37(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.41(3) . ?
C9 H9A 0.9300 . ?
C10 C17 1.49(2) . ?
C11 C12 1.36(3) . ?
C11 H11A 0.9300 . ?
C12 C15 1.37(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.31(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.41(3) . ?
C14 H14A 0.9300 . ?
C15 C18 1.46(2) . ?
C16 C17 1.37(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
O5 Zn1 O3B 105.9(15) 2_955 . ?
O5 Zn1 O3A 90.5(15) 2_955 . ?
O3B Zn1 O3A 25.0(12) . . ?
O5 Zn1 O4 116.3(7) 2_955 . ?
O3B Zn1 O4 93.3(11) . . ?
O3A Zn1 O4 118.1(11) . . ?
O5 Zn1 O7 108.4(7) 2_955 . ?
O3B Zn1 O7 123.6(13) . . ?
O3A Zn1 O7 113.0(13) . . ?
O4 Zn1 O7 109.2(6) . . ?
O6 Zn2 OW1 109.3(6) 1_455 . ?
O6 Zn2 O8 107.4(7) 1_455 . ?
OW1 Zn2 O8 104.7(5) . . ?
O6 Zn2 N2 115.6(7) 1_455 . ?
OW1 Zn2 N2 110.1(6) . . ?
O8 Zn2 N2 109.1(6) . . ?
O1 Zn3 O2 119.7(8) 2_774 1_464 ?
O1 Zn3 O9 109.4(7) 2_774 2_774 ?
O2 Zn3 O9 105.7(7) 1_464 2_774 ?
O1 Zn3 N3 105.0(7) 2_774 . ?
O2 Zn3 N3 113.4(8) 1_464 . ?
O9 Zn3 N3 102.3(6) 2_774 . ?
O1 P1 O3B 108(2) . . ?
O1 P1 O2 113.2(11) . . ?
O3B P1 O2 130.4(19) . . ?
O1 P1 O3A 116.6(19) . . ?
O3B P1 O3A 31.7(15) . . ?
O2 P1 O3A 102.5(17) . . ?
O6 P2 O4 113.4(8) . . ?
O6 P2 O5 112.3(9) . . ?
O4 P2 O5 113.7(8) . . ?
O6 P2 H2 89.3 . . ?
O4 P2 H2 110.6 . . ?
O5 P2 H2 115.3 . . ?
O7 P3 O9 116.2(8) . . ?
O7 P3 O8 105.4(8) . . ?
O9 P3 O8 113.1(8) . . ?
O7 P3 H3 111.9 . . ?
O9 P3 H3 109.6 . . ?
O8 P3 H3 99.5 . . ?
P1 O1 Zn3 134.8(9) . 2_774 ?
P1 O2 Zn3 133.3(13) . 1_646 ?
O3B O3A P1 71(4) . . ?
O3B O3A Zn1 77(4) . . ?
P1 O3A Zn1 137(3) . . ?
O3A O3B P1 78(4) . . ?
O3A O3B Zn1 78(4) . . ?
P1 O3B Zn1 142(2) . . ?
P2 O4 Zn1 130.5(8) . . ?
P2 O5 Zn1 140.0(10) . 2_955 ?
P2 O6 Zn2 137.7(10) . 1_655 ?
P3 O7 Zn1 130.8(8) . . ?
P3 O8 Zn2 122.7(8) . . ?
P3 O9 Zn3 127.9(9) . 2_774 ?
C3 N1 C1 121.6(16) . . ?
C3 N1 H4 122.0 . . ?
C1 N1 H4 116.5 . . ?
C8 N2 C6 117.2(17) . . ?
C8 N2 Zn2 121.2(14) . . ?
C6 N2 Zn2 121.6(13) . . ?
C11 N3 C13 117.4(16) . . ?
C11 N3 Zn3 124.2(13) . . ?
C13 N3 Zn3 118.4(13) . . ?
C16 N4 C18 105.6(15) . . ?
C18 N5 C17 105.4(15) . . ?
N1 C1 C2 120.6(17) . . ?
N1 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C1 C2 C5 120.3(18) . . ?
C1 C2 H2A 119.9 . . ?
C5 C2 H2A 119.9 . . ?
N1 C3 C4 120.1(17) . . ?
N1 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 117.5(18) . . ?
C5 C4 H4A 121.2 . . ?
C3 C4 H4A 121.2 . . ?
C2 C5 C4 119.9(17) . . ?
C2 C5 C16 121.8(16) . . ?
C4 C5 C16 118.3(16) . . ?
N2 C6 C7 123(2) . . ?
N2 C6 H6A 118.4 . . ?
C7 C6 H6A 118.4 . . ?
C6 C7 C10 120(2) . . ?
C6 C7 H7A 120.1 . . ?
C10 C7 H7A 120.1 . . ?
N2 C8 C9 124.1(19) . . ?
N2 C8 H8A 118.0 . . ?
C9 C8 H8A 118.0 . . ?
C8 C9 C10 119.2(17) . . ?
C8 C9 H9A 120.4 . . ?
C10 C9 H9A 120.4 . . ?
C7 C10 C9 116.3(16) . . ?
C7 C10 C17 120.2(17) . . ?
C9 C10 C17 123.5(17) . . ?
N3 C11 C12 122.3(18) . . ?
N3 C11 H11A 118.8 . . ?
C12 C11 H11A 118.8 . . ?
C11 C12 C15 122.8(18) . . ?
C11 C12 H12A 118.6 . . ?
C15 C12 H12A 118.6 . . ?
C14 C13 N3 121.8(17) . . ?
C14 C13 H13A 119.1 . . ?
N3 C13 H13A 119.1 . . ?
C13 C14 C15 122.8(18) . . ?
C13 C14 H14A 118.6 . . ?
C15 C14 H14A 118.6 . . ?
C12 C15 C14 112.9(17) . . ?
C12 C15 C18 124.1(17) . . ?
C14 C15 C18 123.1(17) . . ?
N4 C16 C17 107.3(16) . . ?
N4 C16 C5 119.7(14) . . ?
C17 C16 C5 132.9(15) . . ?
N5 C17 C16 109.5(15) . . ?
N5 C17 C10 118.7(16) . . ?
C16 C17 C10 131.3(18) . . ?
N5 C18 N4 112.2(15) . . ?
N5 C18 C15 124.1(17) . . ?
N4 C18 C15 123.6(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.253
_refine_diff_density_min         -1.413
_refine_diff_density_rms         0.254
####################################################################### 
# 
# 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_NCU_2b
_database_code_depnum_ccdc_archive 'CCDC 1051119'
_audit_update_record             
;
2015-02-25 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N5 O9 P3 Zn3'
_chemical_formula_weight         735.38

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.578(3)
_cell_length_b                   11.517(4)
_cell_length_c                   13.244(5)
_cell_angle_alpha                76.705(12)
_cell_angle_beta                 88.391(13)
_cell_angle_gamma                69.043(11)
_cell_volume                     1325.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       yellow
_exptl_crystal_colour            thin-plate
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    2.930
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.730
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   'SADABS program'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47444
_diffrn_reflns_av_R_equivalents  0.2094
_diffrn_reflns_av_sigmaI/netI    0.1791
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.98
_reflns_number_total             6201
_reflns_number_gt                2702
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker X8 Apex'
_computing_cell_refinement       'Bruker X8 Apex'
_computing_data_reduction        'Bruker X8 Apex'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1530P)²+4.1322P] 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     SHELXL
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6201
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2144
_refine_ls_R_factor_gt           0.0955
_refine_ls_wR_factor_ref         0.3260
_refine_ls_wR_factor_gt          0.2475
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 1.28966(16) -0.25167(13) 0.80176(13) 0.0550(5) Uani 1 1 d . . .
Zn2 Zn 1.81430(15) -0.32249(13) 0.96733(13) 0.0543(5) Uani 1 1 d . . .
Zn3 Zn 1.50665(16) 0.01797(13) 0.82485(12) 0.0535(5) Uani 1 1 d . . .
P1 P 1.1018(4) -0.4282(3) 0.8399(3) 0.0529(9) Uani 1 1 d . . .
H1 H 1.0514 -0.4994 0.7872 0.050 Uiso 1 1 d . . .
P2 P 1.6047(4) -0.2422(3) 0.7611(3) 0.0537(9) Uani 1 1 d . . .
H2 H 1.7127 -0.2848 0.6841 0.050 Uiso 1 1 d . . .
P3 P 1.2622(4) 0.0444(3) 0.9866(3) 0.0514(9) Uani 1 1 d . . .
H3 H 1.1695 -0.0120 0.9642 0.050 Uiso 1 1 d . . .
O1 O 1.1901(12) -0.5415(10) 0.9217(10) 0.103(4) Uani 1 1 d . . .
O2 O 0.9827(10) -0.3286(8) 0.8816(8) 0.071(3) Uani 1 1 d . . .
O3 O 1.2043(9) -0.3696(8) 0.7749(7) 0.057(2) Uani 1 1 d . . .
O4 O 1.4754(9) -0.2779(8) 0.7313(7) 0.061(2) Uani 1 1 d . . .
O5 O 1.5681(12) -0.1002(8) 0.7361(8) 0.080(3) Uani 1 1 d . . .
O6 O 1.6574(11) -0.3047(10) 0.8684(9) 0.079(3) Uani 1 1 d . . .
O7 O 1.3444(10) -0.0093(9) 0.9001(8) 0.068(3) Uani 1 1 d . . .
O8 O 1.3373(11) -0.0221(9) 1.0913(8) 0.073(3) Uani 1 1 d . . .
O9 O 1.2190(12) 0.1870(9) 0.9634(9) 0.082(3) Uani 1 1 d . . .
N1 N 1.1346(11) -0.0718(8) 0.7358(9) 0.059(3) Uani 1 1 d . . .
N2 N 0.6960(11) 0.2853(9) 1.0399(9) 0.054(3) Uani 1 1 d . . .
N3 N 0.5517(12) 0.8198(9) 0.2929(9) 0.055(3) Uani 1 1 d . . .
N4 N 0.8020(13) 0.3840(9) 0.5466(9) 0.061(3) Uani 1 1 d . . .
N5 N 0.6393(11) 0.4944(9) 0.6472(8) 0.054(3) Uani 1 1 d . . .
H4 H 0.5429 0.5481 0.6564 0.050 Uiso 1 1 d . . .
C1 C 1.1727(15) 0.0227(13) 0.6772(12) 0.070(4) Uani 1 1 d . . .
H1A H 1.2711 0.0028 0.6581 0.084 Uiso 1 1 calc R . .
C2 C 1.0775(15) 0.1449(11) 0.6442(12) 0.064(4) Uani 1 1 d . . .
H2A H 1.1094 0.2058 0.6017 0.076 Uiso 1 1 calc R . .
C3 C 0.9967(15) -0.0402(12) 0.7618(11) 0.066(4) Uani 1 1 d . . .
H3A H 0.9676 -0.1046 0.8015 0.079 Uiso 1 1 calc R . .
C4 C 0.8907(13) 0.0807(11) 0.7353(11) 0.056(3) Uani 1 1 d . . .
H4A H 0.7941 0.0966 0.7576 0.067 Uiso 1 1 calc R . .
C5 C 0.9288(14) 0.1788(11) 0.6752(11) 0.056(3) Uani 1 1 d . . .
C6 C 0.8274(13) 0.2466(11) 0.9931(11) 0.053(3) Uani 1 1 d . . .
H6A H 0.9148 0.1989 1.0348 0.063 Uiso 1 1 calc R . .
C7 C 0.8370(14) 0.2744(11) 0.8880(11) 0.054(3) Uani 1 1 d . . .
H7A H 0.9299 0.2450 0.8603 0.065 Uiso 1 1 calc R . .
C8 C 0.5742(14) 0.3542(11) 0.9737(11) 0.052(3) Uani 1 1 d . . .
H8A H 0.4821 0.3824 1.0028 0.063 Uiso 1 1 calc R . .
C9 C 0.5749(14) 0.3857(11) 0.8683(11) 0.054(3) Uani 1 1 d . . .
H9A H 0.4863 0.4332 0.8279 0.065 Uiso 1 1 calc R . .
C10 C 0.7111(14) 0.3455(11) 0.8215(10) 0.051(3) Uani 1 1 d . . .
C11 C 0.4909(16) 0.8250(12) 0.3851(13) 0.070(4) Uani 1 1 d . . .
H11A H 0.4196 0.9023 0.3917 0.084 Uiso 1 1 calc R . .
C12 C 0.5272(17) 0.7241(14) 0.4694(11) 0.072(4) Uani 1 1 d . . .
H12A H 0.4792 0.7322 0.5309 0.086 Uiso 1 1 calc R . .
C13 C 0.6566(16) 0.7084(13) 0.2834(11) 0.068(4) Uani 1 1 d . . .
H13A H 0.7022 0.7023 0.2209 0.081 Uiso 1 1 calc R . .
C14 C 0.6972(17) 0.6004(12) 0.3689(11) 0.066(4) Uani 1 1 d . . .
H14A H 0.7659 0.5225 0.3610 0.080 Uiso 1 1 calc R . .
C15 C 0.6368(15) 0.6093(10) 0.4622(10) 0.050(3) Uani 1 1 d . . .
C16 C 0.8210(14) 0.3118(11) 0.6465(11) 0.057(3) Uani 1 1 d . . .
C17 C 0.7228(12) 0.3759(10) 0.7106(11) 0.054(3) Uani 1 1 d . . .
C18 C 0.6905(17) 0.4942(12) 0.5493(11) 0.064(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.916(9) . ?
Zn1 O4 1.944(8) . ?
Zn1 N2 2.042(12) 2_757 ?
Zn1 N1 2.073(10) . ?
Zn2 O1 1.897(10) 2_847 ?
Zn2 O9 1.914(10) 2_857 ?
Zn2 O2 1.936(9) 1_655 ?
Zn2 O6 1.945(11) . ?
Zn3 O7 1.904(9) . ?
Zn3 O8 1.907(10) 2_857 ?
Zn3 O5 1.924(9) . ?
Zn3 N3 2.048(10) 2_766 ?
P1 O1 1.485(10) . ?
P1 O2 1.497(9) . ?
P1 O3 1.523(9) . ?
P1 H1 1.3996 . ?
P2 O6 1.450(11) . ?
P2 O5 1.502(9) . ?
P2 O4 1.524(10) . ?
P2 H2 1.4687 . ?
P3 O8 1.483(10) . ?
P3 O7 1.497(9) . ?
P3 O9 1.501(10) . ?
P3 H3 1.3470 . ?
O1 Zn2 1.897(10) 2_847 ?
O2 Zn2 1.936(9) 1_455 ?
O8 Zn3 1.907(10) 2_857 ?
O9 Zn2 1.914(10) 2_857 ?
N1 C3 1.298(15) . ?
N1 C1 1.342(16) . ?
N2 C8 1.355(16) . ?
N2 C6 1.360(15) . ?
N2 Zn1 2.042(12) 2_757 ?
N3 C11 1.342(17) . ?
N3 C13 1.348(16) . ?
N3 Zn3 2.048(10) 2_766 ?
N4 C18 1.342(16) . ?
N4 C16 1.369(16) . ?
N5 C18 1.373(17) . ?
N5 C17 1.391(14) . ?
N5 H4 0.9332 . ?
C1 C2 1.350(17) . ?
C1 H1A 0.9300 . ?
C2 C5 1.411(17) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(16) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(17) . ?
C4 H4A 0.9300 . ?
C5 C16 1.477(15) . ?
C6 C7 1.363(18) . ?
C6 H6A 0.9300 . ?
C7 C10 1.386(17) . ?
C7 H7A 0.9300 . ?
C8 C9 1.360(17) . ?
C8 H8A 0.9300 . ?
C9 C10 1.397(17) . ?
C9 H9A 0.9300 . ?
C10 C17 1.440(18) . ?
C11 C12 1.362(19) . ?
C11 H11A 0.9300 . ?
C12 C15 1.385(17) . ?
C12 H12A 0.9300 . ?
C13 C14 1.418(19) . ?
C13 H13A 0.9300 . ?
C14 C15 1.360(18) . ?
C14 H14A 0.9300 . ?
C15 C18 1.481(18) . ?
C16 C17 1.378(17) . ?

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 O4 108.3(4) . . ?
O3 Zn1 N2 104.2(4) . 2_757 ?
O4 Zn1 N2 117.2(4) . 2_757 ?
O3 Zn1 N1 105.1(4) . . ?
O4 Zn1 N1 109.8(4) . . ?
N2 Zn1 N1 111.4(4) 2_757 . ?
O1 Zn2 O9 101.8(5) 2_847 2_857 ?
O1 Zn2 O2 124.4(4) 2_847 1_655 ?
O9 Zn2 O2 107.7(4) 2_857 1_655 ?
O1 Zn2 O6 103.5(5) 2_847 . ?
O9 Zn2 O6 117.5(5) 2_857 . ?
O2 Zn2 O6 102.9(5) 1_655 . ?
O7 Zn3 O8 114.4(4) . 2_857 ?
O7 Zn3 O5 107.9(4) . . ?
O8 Zn3 O5 115.8(5) 2_857 . ?
O7 Zn3 N3 115.1(4) . 2_766 ?
O8 Zn3 N3 106.5(4) 2_857 2_766 ?
O5 Zn3 N3 95.8(4) . 2_766 ?
O1 P1 O2 113.5(7) . . ?
O1 P1 O3 110.8(6) . . ?
O2 P1 O3 110.3(5) . . ?
O1 P1 H1 93.9 . . ?
O2 P1 H1 115.8 . . ?
O3 P1 H1 111.6 . . ?
O6 P2 O5 113.5(6) . . ?
O6 P2 O4 110.3(5) . . ?
O5 P2 O4 112.7(6) . . ?
O6 P2 H2 114.8 . . ?
O5 P2 H2 103.3 . . ?
O4 P2 H2 101.5 . . ?
O8 P3 O7 114.2(6) . . ?
O8 P3 O9 113.6(6) . . ?
O7 P3 O9 111.4(6) . . ?
O8 P3 H3 109.7 . . ?
O7 P3 H3 81.7 . . ?
O9 P3 H3 122.6 . . ?
P1 O1 Zn2 146.5(7) . 2_847 ?
P1 O2 Zn2 136.5(6) . 1_455 ?
P1 O3 Zn1 129.7(5) . . ?
P2 O4 Zn1 125.3(6) . . ?
P2 O5 Zn3 130.1(7) . . ?
P2 O6 Zn2 139.3(6) . . ?
P3 O7 Zn3 131.9(6) . . ?
P3 O8 Zn3 137.4(6) . 2_857 ?
P3 O9 Zn2 140.7(7) . 2_857 ?
C3 N1 C1 116.0(11) . . ?
C3 N1 Zn1 120.2(9) . . ?
C1 N1 Zn1 123.1(9) . . ?
C8 N2 C6 114.7(12) . . ?
C8 N2 Zn1 128.4(9) . 2_757 ?
C6 N2 Zn1 116.5(9) . 2_757 ?
C11 N3 C13 118.1(11) . . ?
C11 N3 Zn3 119.6(8) . 2_766 ?
C13 N3 Zn3 122.2(9) . 2_766 ?
C18 N4 C16 104.6(11) . . ?
C18 N5 C17 106.6(10) . . ?
C18 N5 H4 120.6 . . ?
C17 N5 H4 127.5 . . ?
N1 C1 C2 124.3(12) . . ?
N1 C1 H1A 117.8 . . ?
C2 C1 H1A 117.8 . . ?
C1 C2 C5 119.0(12) . . ?
C1 C2 H2A 120.5 . . ?
C5 C2 H2A 120.5 . . ?
N1 C3 C4 125.1(13) . . ?
N1 C3 H3A 117.4 . . ?
C4 C3 H3A 117.4 . . ?
C3 C4 C5 119.3(12) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C2 116.2(11) . . ?
C4 C5 C16 121.9(11) . . ?
C2 C5 C16 121.9(11) . . ?
N2 C6 C7 123.0(12) . . ?
N2 C6 H6A 118.5 . . ?
C7 C6 H6A 118.5 . . ?
C6 C7 C10 121.4(12) . . ?
C6 C7 H7A 119.3 . . ?
C10 C7 H7A 119.3 . . ?
N2 C8 C9 125.6(12) . . ?
N2 C8 H8A 117.2 . . ?
C9 C8 H8A 117.2 . . ?
C8 C9 C10 119.0(12) . . ?
C8 C9 H9A 120.5 . . ?
C10 C9 H9A 120.5 . . ?
C7 C10 C9 116.3(12) . . ?
C7 C10 C17 120.9(11) . . ?
C9 C10 C17 122.8(11) . . ?
N3 C11 C12 124.1(12) . . ?
N3 C11 H11A 118.0 . . ?
C12 C11 H11A 118.0 . . ?
C11 C12 C15 118.9(13) . . ?
C11 C12 H12A 120.6 . . ?
C15 C12 H12A 120.6 . . ?
N3 C13 C14 119.8(13) . . ?
N3 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
C15 C14 C13 120.8(12) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C12 118.2(12) . . ?
C14 C15 C18 117.6(11) . . ?
C12 C15 C18 124.2(12) . . ?
N4 C16 C17 111.7(11) . . ?
N4 C16 C5 121.6(11) . . ?
C17 C16 C5 126.5(12) . . ?
C16 C17 N5 105.2(11) . . ?
C16 C17 C10 131.8(11) . . ?
N5 C17 C10 122.6(11) . . ?
N4 C18 N5 111.9(12) . . ?
N4 C18 C15 125.7(12) . . ?
N5 C18 C15 122.1(12) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        27.98
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         1.629
_refine_diff_density_min         -1.220
_refine_diff_density_rms         0.191
