# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_nih09
_database_code_depnum_ccdc_archive 'CCDC 902586'
#TrackingRef 'nih09_final_submitted.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H40 N4 O16 Zr'
_chemical_formula_weight         587.70

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'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 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'

_cell_length_a                   17.8295(12)
_cell_length_b                   14.3111(14)
_cell_length_c                   13.2223(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 129.061(2)
_cell_angle_gamma                90.00
_cell_volume                     2619.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      29.23

_exptl_crystal_description       'irregular plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.097
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_max          0.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.493
##############################################################################
# #
# NOTE on absorbtion correction with SADABS: #
# #
# (Semi)empirical correction methods for absorption correction are more of #
# a problem in that they often specify only a relative correction range #
# [ Tmin(emp) & Tmax(emp)]. #
# #
# Acta Cryst. procedures call in such cases for the multiplication of both #
# empirical values with Tmax(expected). #
# #
# THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George #
# and Ton are agruing this point!) #
# #
##############################################################################
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_absorpt_correction_T_min  0.7656
_exptl_absorpt_correction_T_max  0.9537


_exptl_special_details           
;
Crystal grown by slow evaporation from mixture of dichloromethane/nitrobenzene
(5:1) over several days.
;

_diffrn_ambient_temperature      150(2)
# APEX 2 parameters
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14468
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         29.23
_reflns_number_total             6080
_reflns_number_gt                5535
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction        
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0586P)^2^+1.5547P] where P=(Fo^2^+2Fc^2^)/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   0.59(5)
_refine_ls_number_reflns         6080
_refine_ls_number_parameters     363
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.147
_refine_ls_shift/su_mean         0.004

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
Zr1 Zr 0.99581(7) 0.118456(13) 0.24810(11) 0.01770(6) Uani 1 1 d . . .
C1 C 1.1314(4) 0.3018(4) 0.5963(5) 0.0333(13) Uani 1 1 d . . .
H1A H 1.0812 0.2934 0.6050 0.050 Uiso 1 1 calc R . .
H1B H 1.1409 0.3686 0.5918 0.050 Uiso 1 1 calc R . .
H1C H 1.1920 0.2742 0.6718 0.050 Uiso 1 1 calc R . .
O1 O 1.0571(2) 0.1771(2) 0.4405(3) 0.0288(9) Uani 1 1 d . . .
N2 N 1.1243(3) 0.2864(3) 0.4023(5) 0.0285(10) Uani 1 1 d U . .
C3 C 1.1009(3) 0.2545(3) 0.4739(5) 0.0198(9) Uani 1 1 d . . .
O4 O 1.0956(2) 0.2333(2) 0.2980(4) 0.0300(9) Uani 1 1 d . . .
C4 C 1.1757(4) 0.3743(4) 0.4175(7) 0.0386(18) Uani 1 1 d . . .
H4A H 1.2295 0.3594 0.4177 0.058 Uiso 1 1 calc R . .
H4B H 1.2007 0.4046 0.4998 0.058 Uiso 1 1 calc R . .
H4C H 1.1306 0.4166 0.3449 0.058 Uiso 1 1 calc R . .
C1A C 1.2174(5) -0.1085(4) 0.4405(6) 0.0388(16) Uani 1 1 d . . .
H1AA H 1.2757 -0.0812 0.5200 0.058 Uiso 1 1 calc R . .
H1AB H 1.2350 -0.1446 0.3952 0.058 Uiso 1 1 calc R . .
H1AC H 1.1862 -0.1496 0.4633 0.058 Uiso 1 1 calc R . .
O1A O 1.0975(2) 0.0061(2) 0.3820(3) 0.0234(8) Uani 1 1 d . . .
N2A C 1.1381(3) -0.0014(3) 0.2502(4) 0.0180(9) Uani 1 1 d U . .
C3A N 1.1486(3) -0.0314(3) 0.3526(4) 0.0276(10) Uani 1 1 d . . .
O4A O 1.0735(2) 0.0643(2) 0.1819(3) 0.0231(8) Uani 1 1 d . . .
C4A C 1.1915(3) -0.0346(4) 0.2049(5) 0.0288(12) Uani 1 1 d . . .
H4AA H 1.1472 -0.0381 0.1095 0.043 Uiso 1 1 calc R . .
H4AB H 1.2184 -0.0967 0.2412 0.043 Uiso 1 1 calc R . .
H4AC H 1.2440 0.0090 0.2340 0.043 Uiso 1 1 calc R . .
C1B C 0.7747(4) -0.1082(4) 0.0532(7) 0.0372(17) Uani 1 1 d . . .
H1BA H 0.7240 -0.1176 0.0607 0.056 Uiso 1 1 calc R . .
H1BB H 0.8110 -0.1665 0.0752 0.056 Uiso 1 1 calc R . .
H1BC H 0.7453 -0.0902 -0.0364 0.056 Uiso 1 1 calc R . .
O1B O 0.8960(3) 0.0079(3) 0.1186(4) 0.0266(9) Uani 1 1 d . . .
N2B N 0.8537(3) -0.0036(3) 0.2433(5) 0.0291(10) Uani 1 1 d U . .
C3B C 0.8394(3) -0.0352(4) 0.1415(4) 0.0209(10) Uani 1 1 d U . .
O4B O 0.9201(2) 0.0638(2) 0.3119(4) 0.0234(8) Uani 1 1 d . . .
C4B C 0.8006(4) -0.0336(4) 0.2883(6) 0.0328(14) Uani 1 1 d . . .
H4BA H 0.7764 0.0213 0.3039 0.049 Uiso 1 1 calc R . .
H4BB H 0.8438 -0.0692 0.3694 0.049 Uiso 1 1 calc R . .
H4BC H 0.7461 -0.0732 0.2218 0.049 Uiso 1 1 calc R . .
O1C O 0.9338(2) 0.1763(2) 0.0553(3) 0.0196(8) Uani 1 1 d . . .
C1C C 0.8586(4) 0.3065(4) -0.0944(5) 0.0288(12) Uani 1 1 d . . .
H1CA H 0.7891 0.3195 -0.1527 0.043 Uiso 1 1 calc R . .
H1CB H 0.8740 0.2665 -0.1394 0.043 Uiso 1 1 calc R . .
H1CC H 0.8943 0.3653 -0.0695 0.043 Uiso 1 1 calc R . .
N2C N 0.8863(3) 0.2580(3) 0.0241(5) 0.0306(10) Uani 1 1 d U . .
C3C C 0.8700(3) 0.2885(3) 0.0980(5) 0.0192(9) Uani 1 1 d U . .
O4C O 0.8949(2) 0.2324(2) 0.1967(3) 0.0249(8) Uani 1 1 d U . .
C4C C 0.8216(5) 0.3753(4) 0.0802(7) 0.0336(15) Uani 1 1 d . . .
H4CA H 0.8382 0.4222 0.0431 0.050 Uiso 1 1 calc R . .
H4CB H 0.8423 0.3974 0.1645 0.050 Uiso 1 1 calc R . .
H4CC H 0.7516 0.3654 0.0209 0.050 Uiso 1 1 calc R . .
O1S O 1.12924(14) 0.28699(16) 0.1240(2) 0.0331(11) Uani 1 1 d D . .
H1SA H 1.1202(4) 0.2653(10) 0.1762(6) 0.050 Uiso 1 1 d D . .
H1SB H 1.1114(15) 0.2449(8) 0.0664(13) 0.050 Uiso 1 1 d D . .
O2S O 0.86158(16) 0.28942(18) 0.3697(3) 0.0380(11) Uani 1 1 d D . .
H2SA H 0.8604(5) 0.2390(6) 0.4041(11) 0.057 Uiso 1 1 d D . .
H2SB H 0.8675(7) 0.2738(12) 0.3123(8) 0.057 Uiso 1 1 d D . .
O3S O 1.02810(14) 0.13922(18) -0.0583(3) 0.0426(11) Uani 1 1 d D . .
H3SA H 1.0679(4) 0.0930(4) -0.0234(17) 0.064 Uiso 1 1 d D . .
H3SB H 0.9967(5) 0.1389(18) -0.0288(8) 0.064 Uiso 1 1 d D . .
O4S O 0.96460(15) -0.13848(19) 0.0557(3) 0.0385(10) Uani 1 1 d D . .
H4SA H 0.9564(5) -0.0912(7) 0.0881(10) 0.058 Uiso 1 1 d D . .
H4SB H 0.9723(8) -0.1176(11) 0.0019(9) 0.058 Uiso 1 1 d D . .
O5S O 0.56626(14) -0.03683(17) -0.0050(3) 0.0349(8) Uani 1 1 d D . .
H5SA H 0.5532(5) 0.0127(6) 0.0181(10) 0.052 Uiso 1 1 d D . .
H5SB H 0.5620(8) -0.0231(11) -0.0718(7) 0.052 Uiso 1 1 d D . .
O6S O 0.4294(2) 0.03805(19) -0.0012(4) 0.0740(17) Uani 1 1 d D . .
H6SA H 0.4227(9) 0.0315(10) -0.0712(8) 0.111 Uiso 1 1 d D . .
H6SB H 0.444(2) 0.0954(6) 0.0231(19) 0.111 Uiso 1 1 d D . .
O7S O 1.01959(14) -0.2489(2) 0.2636(3) 0.0617(13) Uani 0.909(8) 1 d PDU . .
H7SA H 0.9637(3) -0.2497(13) 0.2443(10) 0.093 Uiso 0.909(8) 1 d PD . .
H7SB H 1.0177(10) -0.2087(18) 0.214(2) 0.093 Uiso 0.909(8) 1 d PD . .
O8S O 0.52285(17) -0.06472(17) -0.2408(4) 0.0720(15) Uani 0.896(8) 1 d PDU . .
H8SA H 0.4690(5) -0.0419(8) -0.265(2) 0.108 Uiso 0.896(8) 1 d PD . .
H8SB H 0.518(2) -0.12463(19) -0.242(7) 0.108 Uiso 0.896(8) 1 d PD . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zr1 0.02001(10) 0.01425(9) 0.02127(9) 0.0003(2) 0.01417(8) 0.0008(2)
C1 0.040(2) 0.028(2) 0.032(2) -0.0134(18) 0.0230(19) -0.007(2)
O1 0.0377(16) 0.030(2) 0.0237(15) -0.0038(13) 0.0217(13) -0.0049(15)
N2 0.0284(13) 0.0247(15) 0.0340(14) -0.0067(11) 0.0205(10) -0.0032(11)
C3 0.0182(14) 0.0155(15) 0.0274(16) -0.0059(13) 0.0153(12) -0.0020(13)
O4 0.0397(15) 0.0254(15) 0.0361(15) -0.0148(12) 0.0292(13) -0.0089(13)
C4 0.037(3) 0.028(3) 0.044(3) -0.005(2) 0.023(2) -0.0134(19)
C1A 0.060(3) 0.031(3) 0.038(2) 0.0165(19) 0.036(2) 0.022(2)
O1A 0.0270(14) 0.0188(15) 0.0270(15) 0.0084(12) 0.0182(12) 0.0109(12)
N2A 0.0169(12) 0.0175(13) 0.0192(13) -0.0022(11) 0.0112(9) 0.0004(11)
C3A 0.0260(16) 0.0174(15) 0.0323(18) 0.0037(13) 0.0149(14) 0.0040(13)
O4A 0.0287(14) 0.0215(16) 0.0244(14) -0.0005(12) 0.0193(12) 0.0051(13)
C4A 0.0195(18) 0.043(3) 0.024(2) 0.002(2) 0.0138(16) 0.0079(19)
C1B 0.0162(18) 0.038(3) 0.055(3) -0.011(2) 0.021(2) -0.0091(19)
O1B 0.0290(16) 0.0282(19) 0.0327(18) -0.0013(14) 0.0242(14) -0.0015(14)
N2B 0.0280(14) 0.0251(15) 0.0330(15) 0.0031(12) 0.0187(11) -0.0014(12)
C3B 0.0204(14) 0.0228(16) 0.0219(15) 0.0038(13) 0.0143(11) -0.0022(12)
O4B 0.0218(14) 0.0238(17) 0.0274(16) -0.0045(13) 0.0169(12) -0.0031(13)
C4B 0.039(3) 0.027(2) 0.035(3) 0.008(2) 0.024(2) -0.003(2)
O1C 0.0189(13) 0.0099(14) 0.0267(16) -0.0005(12) 0.0128(12) 0.0020(11)
C1C 0.033(2) 0.030(2) 0.027(2) -0.0023(18) 0.0203(19) -0.003(2)
N2C 0.0260(14) 0.0280(16) 0.0294(15) 0.0032(13) 0.0134(11) 0.0003(13)
C3C 0.0200(13) 0.0150(14) 0.0244(14) 0.0060(11) 0.0148(11) 0.0049(11)
O4C 0.0253(12) 0.0259(14) 0.0279(13) 0.0024(11) 0.0189(10) 0.0091(11)
C4C 0.042(3) 0.027(3) 0.053(3) 0.014(2) 0.040(3) 0.0145(19)
O1S 0.0268(15) 0.0233(17) 0.038(2) -0.0032(14) 0.0152(14) -0.0115(14)
O2S 0.051(2) 0.039(2) 0.044(2) 0.0019(17) 0.0394(19) 0.0088(18)
O3S 0.070(2) 0.0243(17) 0.053(2) -0.0179(16) 0.0484(19) -0.0184(17)
O4S 0.052(2) 0.044(2) 0.048(2) -0.0007(18) 0.0449(19) -0.0004(18)
O5S 0.0263(13) 0.0379(19) 0.0435(17) 0.0116(14) 0.0235(12) 0.0121(13)
O6S 0.112(4) 0.048(3) 0.083(3) -0.013(2) 0.071(3) -0.025(3)
O7S 0.074(2) 0.0545(16) 0.0565(16) -0.0022(13) 0.0408(14) 0.0019(13)
O8S 0.085(2) 0.0687(19) 0.0584(16) -0.0008(14) 0.0438(15) -0.0154(13)

_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
Zr1 O4B 2.141(4) . ?
Zr1 O4A 2.194(4) . ?
Zr1 O4 2.196(4) . ?
Zr1 O1B 2.182(4) . ?
Zr1 O4C 2.195(3) . ?
Zr1 O1C 2.203(3) . ?
Zr1 O1 2.206(3) . ?
Zr1 O1A 2.227(3) . ?
C1 C3 1.505(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O1 C3 1.263(5) . ?
N2 C3 1.333(8) . ?
N2 O4 1.361(6) . ?
N2 C4 1.494(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C1A C3A 1.508(7) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
O1A C3A 1.310(7) . ?
N2A O4A 1.309(5) . ?
N2A C3A 1.317(7) . ?
N2A C4A 1.487(8) . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C1B C3B 1.445(7) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
O1B C3B 1.370(7) . ?
N2B C3B 1.283(8) . ?
N2B O4B 1.341(6) . ?
N2B C4B 1.466(8) . ?
C4B H4BA 0.9800 . ?
C4B H4BB 0.9800 . ?
C4B H4BC 0.9800 . ?
O1C N2C 1.347(5) . ?
C1C N2C 1.485(7) . ?
C1C H1CA 0.9800 . ?
C1C H1CB 0.9800 . ?
C1C H1CC 0.9800 . ?
N2C C3C 1.260(8) . ?
C3C O4C 1.347(6) . ?
C3C C4C 1.445(7) . ?
C4C H4CA 0.9800 . ?
C4C H4CB 0.9800 . ?
C4C H4CC 0.9800 . ?
O1S H1SA 0.8600(11) . ?
O1S H1SB 0.8600(10) . ?
O2S H2SA 0.8599(11) . ?
O2S H2SB 0.8600(11) . ?
O3S H3SA 0.8601(11) . ?
O3S H3SB 0.8600(11) . ?
O4S H4SA 0.8601(11) . ?
O4S H4SB 0.8600(11) . ?
O5S H5SA 0.8602(11) . ?
O5S H5SB 0.8601(11) . ?
O6S H6SA 0.8603(11) . ?
O6S H6SB 0.8601(11) . ?
O7S H7SA 0.8602(10) . ?
O7S H7SB 0.8601(11) . ?
O8S H8SA 0.8601(11) . ?
O8S H8SB 0.8601(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4B Zr1 O4A 137.87(7) . . ?
O4B Zr1 O4 138.41(14) . . ?
O4A Zr1 O4 77.81(14) . . ?
O4B Zr1 O1B 68.85(15) . . ?
O4A Zr1 O1B 80.70(14) . . ?
O4 Zr1 O1B 152.15(16) . . ?
O4B Zr1 O4C 78.23(15) . . ?
O4A Zr1 O4C 137.68(14) . . ?
O4 Zr1 O4C 83.55(7) . . ?
O1B Zr1 O4C 101.05(13) . . ?
O4B Zr1 O1C 127.75(13) . . ?
O4A Zr1 O1C 69.72(13) . . ?
O4 Zr1 O1C 77.71(13) . . ?
O1B Zr1 O1C 78.35(13) . . ?
O4C Zr1 O1C 69.33(14) . . ?
O4B Zr1 O1 70.23(14) . . ?
O4A Zr1 O1 128.01(13) . . ?
O4 Zr1 O1 69.51(15) . . ?
O1B Zr1 O1 138.34(14) . . ?
O4C Zr1 O1 77.79(14) . . ?
O1C Zr1 O1 135.59(6) . . ?
O4B Zr1 O1A 79.80(14) . . ?
O4A Zr1 O1A 70.10(14) . . ?
O4 Zr1 O1A 101.64(13) . . ?
O1B Zr1 O1A 87.33(7) . . ?
O4C Zr1 O1A 151.69(15) . . ?
O1C Zr1 O1A 138.96(13) . . ?
O1 Zr1 O1A 78.11(13) . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 O1 Zr1 119.0(3) . . ?
C3 N2 O4 116.3(4) . . ?
C3 N2 C4 129.3(5) . . ?
O4 N2 C4 114.4(6) . . ?
O1 C3 N2 116.9(5) . . ?
O1 C3 C1 119.7(5) . . ?
N2 C3 C1 123.1(4) . . ?
N2 O4 Zr1 116.0(4) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3A C1A H1AA 109.5 . . ?
C3A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
C3A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C3A O1A Zr1 115.5(3) . . ?
O4A N2A C3A 115.9(5) . . ?
O4A N2A C4A 117.4(5) . . ?
C3A N2A C4A 126.7(4) . . ?
O1A C3A N2A 119.8(4) . . ?
O1A C3A C1A 116.8(5) . . ?
N2A C3A C1A 123.4(5) . . ?
N2A O4A Zr1 118.7(4) . . ?
N2A C4A H4AA 109.5 . . ?
N2A C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
N2A C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C3B C1B H1BA 109.5 . . ?
C3B C1B H1BB 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
C3B C1B H1BC 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
C3B O1B Zr1 120.2(3) . . ?
C3B N2B O4B 118.1(5) . . ?
C3B N2B C4B 124.7(5) . . ?
O4B N2B C4B 117.1(5) . . ?
N2B C3B O1B 112.6(5) . . ?
N2B C3B C1B 129.3(5) . . ?
O1B C3B C1B 118.1(5) . . ?
N2B O4B Zr1 120.1(4) . . ?
N2B C4B H4BA 109.5 . . ?
N2B C4B H4BB 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
N2B C4B H4BC 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
N2C O1C Zr1 116.1(3) . . ?
N2C C1C H1CA 109.5 . . ?
N2C C1C H1CB 109.5 . . ?
H1CA C1C H1CB 109.5 . . ?
N2C C1C H1CC 109.5 . . ?
H1CA C1C H1CC 109.5 . . ?
H1CB C1C H1CC 109.5 . . ?
C3C N2C O1C 118.1(5) . . ?
C3C N2C C1C 124.8(5) . . ?
O1C N2C C1C 117.1(5) . . ?
N2C C3C O4C 116.7(4) . . ?
N2C C3C C4C 125.3(5) . . ?
O4C C3C C4C 117.9(5) . . ?
C3C O4C Zr1 116.6(3) . . ?
C3C C4C H4CA 109.5 . . ?
C3C C4C H4CB 109.5 . . ?
H4CA C4C H4CB 109.5 . . ?
C3C C4C H4CC 109.5 . . ?
H4CA C4C H4CC 109.5 . . ?
H4CB C4C H4CC 109.5 . . ?
H1SA O1S H1SB 107.9(3) . . ?
H2SA O2S H2SB 107.8(3) . . ?
H3SA O3S H3SB 107.8(3) . . ?
H4SA O4S H4SB 107.8(3) . . ?
H5SA O5S H5SB 107.9(3) . . ?
H6SA O6S H6SB 107.8(3) . . ?
H7SA O7S H7SB 107.7(3) . . ?
H8SA O8S H8SB 107.8(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
O4B Zr1 O1 C3 -155.7(4) . . . . ?
O4A Zr1 O1 C3 68.3(4) . . . . ?
O4 Zr1 O1 C3 13.6(3) . . . . ?
O1B Zr1 O1 C3 -167.0(3) . . . . ?
O4C Zr1 O1 C3 -74.0(3) . . . . ?
O1C Zr1 O1 C3 -31.5(5) . . . . ?
O1A Zr1 O1 C3 121.0(4) . . . . ?
Zr1 O1 C3 N2 -13.4(5) . . . . ?
Zr1 O1 C3 C1 171.8(3) . . . . ?
O4 N2 C3 O1 2.1(6) . . . . ?
C4 N2 C3 O1 -179.9(5) . . . . ?
O4 N2 C3 C1 176.7(4) . . . . ?
C4 N2 C3 C1 -5.2(8) . . . . ?
C3 N2 O4 Zr1 9.9(5) . . . . ?
C4 N2 O4 Zr1 -168.5(3) . . . . ?
O4B Zr1 O4 N2 3.5(4) . . . . ?
O4A Zr1 O4 N2 -150.6(3) . . . . ?
O1B Zr1 O4 N2 169.1(3) . . . . ?
O4C Zr1 O4 N2 67.6(3) . . . . ?
O1C Zr1 O4 N2 137.8(3) . . . . ?
O1 Zr1 O4 N2 -11.7(3) . . . . ?
O1A Zr1 O4 N2 -84.2(3) . . . . ?
O4B Zr1 O1A C3A 150.4(3) . . . . ?
O4A Zr1 O1A C3A 0.4(3) . . . . ?
O4 Zr1 O1A C3A -72.0(3) . . . . ?
O1B Zr1 O1A C3A 81.4(3) . . . . ?
O4C Zr1 O1A C3A -170.0(3) . . . . ?
O1C Zr1 O1A C3A 12.6(4) . . . . ?
O1 Zr1 O1A C3A -137.8(3) . . . . ?
Zr1 O1A C3A N2A 0.5(5) . . . . ?
Zr1 O1A C3A C1A -179.3(3) . . . . ?
O4A N2A C3A O1A -1.6(6) . . . . ?
C4A N2A C3A O1A 178.6(4) . . . . ?
O4A N2A C3A C1A 178.2(4) . . . . ?
C4A N2A C3A C1A -1.6(7) . . . . ?
C3A N2A O4A Zr1 1.9(5) . . . . ?
C4A N2A O4A Zr1 -178.3(3) . . . . ?
O4B Zr1 O4A N2A -48.3(4) . . . . ?
O4 Zr1 O4A N2A 106.1(3) . . . . ?
O1B Zr1 O4A N2A -91.7(3) . . . . ?
O4C Zr1 O4A N2A 172.0(3) . . . . ?
O1C Zr1 O4A N2A -172.7(3) . . . . ?
O1 Zr1 O4A N2A 54.7(4) . . . . ?
O1A Zr1 O4A N2A -1.2(3) . . . . ?
O4B Zr1 O1B C3B 1.0(3) . . . . ?
O4A Zr1 O1B C3B 151.4(3) . . . . ?
O4 Zr1 O1B C3B -168.7(3) . . . . ?
O4C Zr1 O1B C3B -71.6(3) . . . . ?
O1C Zr1 O1B C3B -137.5(3) . . . . ?
O1 Zr1 O1B C3B 12.4(4) . . . . ?
O1A Zr1 O1B C3B 81.1(3) . . . . ?
O4B N2B C3B O1B -0.7(6) . . . . ?
C4B N2B C3B O1B 177.3(4) . . . . ?
O4B N2B C3B C1B 178.4(5) . . . . ?
C4B N2B C3B C1B -3.6(9) . . . . ?
Zr1 O1B C3B N2B -0.5(6) . . . . ?
Zr1 O1B C3B C1B -179.8(3) . . . . ?
C3B N2B O4B Zr1 1.8(6) . . . . ?
C4B N2B O4B Zr1 -176.4(3) . . . . ?
O4A Zr1 O4B N2B -48.1(4) . . . . ?
O4 Zr1 O4B N2B 171.4(3) . . . . ?
O1B Zr1 O4B N2B -1.4(3) . . . . ?
O4C Zr1 O4B N2B 105.5(3) . . . . ?
O1C Zr1 O4B N2B 53.6(4) . . . . ?
O1 Zr1 O4B N2B -173.4(3) . . . . ?
O1A Zr1 O4B N2B -92.5(3) . . . . ?
O4B Zr1 O1C N2C 68.3(3) . . . . ?
O4A Zr1 O1C N2C -156.2(3) . . . . ?
O4 Zr1 O1C N2C -74.8(3) . . . . ?
O1B Zr1 O1C N2C 119.5(3) . . . . ?
O4C Zr1 O1C N2C 12.9(3) . . . . ?
O1 Zr1 O1C N2C -32.1(4) . . . . ?
O1A Zr1 O1C N2C -168.5(3) . . . . ?
Zr1 O1C N2C C3C -9.1(5) . . . . ?
Zr1 O1C N2C C1C 169.8(3) . . . . ?
O1C N2C C3C O4C -5.2(6) . . . . ?
C1C N2C C3C O4C 176.0(4) . . . . ?
O1C N2C C3C C4C 178.8(5) . . . . ?
C1C N2C C3C C4C 0.0(8) . . . . ?
N2C C3C O4C Zr1 17.2(5) . . . . ?
C4C C3C O4C Zr1 -166.5(4) . . . . ?
O4B Zr1 O4C C3C -154.0(3) . . . . ?
O4A Zr1 O4C C3C -0.3(4) . . . . ?
O4 Zr1 O4C C3C 63.6(3) . . . . ?
O1B Zr1 O4C C3C -88.6(3) . . . . ?
O1C Zr1 O4C C3C -15.6(3) . . . . ?
O1 Zr1 O4C C3C 134.0(3) . . . . ?
O1A Zr1 O4C C3C 166.2(3) . . . . ?

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
O1S H1SA O4 0.8600(11) 1.971(6) 2.825(6) 172.2(14) .
O1S H1SB O3S 0.8600(10) 2.031(8) 2.838(3) 156.1(17) .
O2S H2SA O4S 0.8599(11) 2.201(6) 2.897(4) 137.9(7) 2
O2S H2SB O4C 0.8600(11) 1.966(6) 2.822(5) 173.7(11) .
O3S H3SA O1A 0.8601(11) 2.166(17) 2.778(5) 127.8(17) 2_554
O3S H3SB O4A 0.8600(11) 2.443(13) 2.941(5) 117.5(11) .
O3S H3SB O1C 0.8600(11) 2.086(8) 2.923(5) 164(2) .
O4S H4SA O1B 0.8601(11) 1.971(5) 2.803(5) 162.4(6) .
O4S H4SB O1 0.8600(11) 2.283(12) 2.918(6) 130.8(13) 2_554
O4S H4SB O4B 0.8600(11) 2.196(7) 2.990(5) 153.6(10) 2_554
O5S H5SA O6S 0.8602(11) 2.087(9) 2.694(4) 127.0(9) .
O5S H5SB O8S 0.8601(11) 1.967(11) 2.727(7) 146.7(15) .
O6S H6SA O5S 0.8603(11) 2.334(13) 2.694(4) 105.5(10) .
O6S H6SB O2S 0.8601(11) 2.29(2) 2.805(4) 118.7(19) 4_454
O7S H7SA O3S 0.8602(10) 2.618(16) 2.754(6) 89.9(10) 2
O7S H7SB O4S 0.8601(11) 1.942(9) 2.759(5) 158(2) .
O8S H8SB O7S 0.8601(11) 1.812(4) 2.670(4) 175(2) 4_444

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.148
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.084