# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cpd3
_database_code_depnum_ccdc_archive 'CCDC 1515799'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.5408(3)
_cell_length_b                   11.7049(5)
_cell_length_c                   15.9042(6)
_cell_angle_alpha                90.095(2)
_cell_angle_beta                 102.741(2)
_cell_angle_gamma                106.596(2)
_cell_volume                     1309.03(5)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Zr -2.9673 0.5597 17.8765 1.2762 10.9480 11.9160 5.4173 0.1176 3.6572 87.6627
2.0693 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C16 H32 N4 O20 Zr1 
# Dc =      1.75 Fooo =    712.00 Mu =      5.20 M =    691.66
# Found Formula = C16 H32 N4 O20 Zr1 
# Dc =      1.75 FOOO =    712.00 Mu =      5.20 M =    691.66

_chemical_formula_sum            'C16 H32 N4 O20 Zr1'
_chemical_formula_moiety         'C8 O16 Zr, 2(C4 H12 N2), 4(H2 O) '
_chemical_compound_source        ?
_chemical_formula_weight         691.66


_cell_measurement_reflns_used    9870
_cell_measurement_theta_min      2
_cell_measurement_theta_max      28
_cell_measurement_temperature    100

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.120
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_max          0.280

_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.520

# Sheldrick geometric approximatio 0.92 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            80562
_reflns_number_total             6512
_diffrn_reflns_av_R_equivalents  0.074
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 6512 
# Theoretical number of reflections is about 13092 


_diffrn_reflns_theta_min         1.820
_diffrn_reflns_theta_max         28.357
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        28.357
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -10
_reflns_limit_h_max              9
_reflns_limit_k_min              -15
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.73
_refine_diff_density_max         2.60


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         5875
_refine_ls_number_restraints     0
_refine_ls_number_parameters     370
_oxford_refine_ls_R_factor_ref   0.0322
_refine_ls_wR_factor_ref         0.0351
_refine_ls_goodness_of_fit_ref   1.1011
_refine_ls_shift/su_max          0.0017155
_refine_ls_shift/su_mean         0.0000492


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6490
_refine_ls_R_factor_all          0.0350
_refine_ls_wR_factor_all         0.0383

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6127
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_gt          0.0356

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.210 0.124 0.656E-01 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.5127(2) 0.89345(15) 0.20956(11) 0.0110 1.0000 Uani . . . . . .
C2 C 0.5314(2) 0.84968(15) 0.12073(11) 0.0101 1.0000 Uani . . . . . .
C3 C 1.0751(3) 0.66705(16) 0.16574(12) 0.0138 1.0000 Uani . . . . . .
C4 C 1.1132(3) 0.63142(16) 0.26040(12) 0.0136 1.0000 Uani . . . . . .
C5 C 1.0554(2) 1.04464(15) 0.26144(11) 0.0098 1.0000 Uani . . . . . .
C6 C 1.0799(2) 1.01030(15) 0.35623(11) 0.0100 1.0000 Uani . . . . . .
C7 C 0.6541(2) 0.58684(15) 0.36125(11) 0.0104 1.0000 Uani . . . . . .
C8 C 0.5942(2) 0.52674(15) 0.26861(11) 0.0102 1.0000 Uani . . . . . .
C9 C 0.7533(3) 1.23796(17) 0.33199(12) 0.0143 1.0000 Uani . . . . . .
C11 C 0.8050(3) 1.30030(17) 0.48550(12) 0.0145 1.0000 Uani . . . . . .
C12 C 0.5928(3) 1.25581(17) 0.47910(12) 0.0140 1.0000 Uani . . . . . .
C14 C 0.5413(3) 1.19368(16) 0.32505(12) 0.0130 1.0000 Uani . . . . . .
C15 C 0.6448(3) 0.5850(2) -0.03254(15) 0.0281 1.0000 Uani . . . . . .
C17 C 0.6730(3) 0.4691(2) 0.00579(14) 0.0271 1.0000 Uani . . . . . .
C18 C 0.0151(3) 0.88480(16) -0.02396(12) 0.0139 1.0000 Uani . . . . . .
C20 C -0.1708(3) 0.91489(16) -0.05044(12) 0.0135 1.0000 Uani . . . . . .
N10 N 0.8597(2) 1.23125(14) 0.42172(10) 0.0131 1.0000 Uani . . . . . .
N13 N 0.4859(2) 1.26219(13) 0.38906(10) 0.0116 1.0000 Uani . . . . . .
N16 N 0.4404(3) 0.56528(18) -0.07056(12) 0.0254 1.0000 Uani . . . . . .
N19 N 0.1314(2) 0.95385(14) 0.05804(10) 0.0124 1.0000 Uani . . . . . .
O1 O 0.63092(18) 0.86725(12) 0.27315(8) 0.0118 1.0000 Uani . . . . . .
O2 O 0.64963(17) 0.79082(11) 0.12477(8) 0.0102 1.0000 Uani . . . . . .
O3 O 0.3967(2) 0.94532(13) 0.21438(9) 0.0183 1.0000 Uani . . . . . .
O4 O 0.43562(19) 0.87537(12) 0.05359(8) 0.0149 1.0000 Uani . . . . . .
O5 O 0.96891(18) 0.73777(12) 0.15287(8) 0.0125 1.0000 Uani . . . . . .
O6 O 1.04026(19) 0.68298(12) 0.30884(8) 0.0147 1.0000 Uani . . . . . .
O7 O 1.1391(2) 0.62903(16) 0.11177(10) 0.0274 1.0000 Uani . . . . . .
O8 O 1.2008(2) 0.55838(14) 0.28142(10) 0.0217 1.0000 Uani . . . . . .
O9 O 0.96702(18) 0.95496(11) 0.20641(8) 0.0111 1.0000 Uani . . . . . .
O10 O 1.01341(18) 0.89882(11) 0.36436(8) 0.0109 1.0000 Uani . . . . . .
O11 O 1.11881(19) 1.14869(12) 0.24516(9) 0.0154 1.0000 Uani . . . . . .
O12 O 1.15794(19) 1.08950(11) 0.41471(8) 0.0137 1.0000 Uani . . . . . .
O13 O 0.73875(19) 0.69800(11) 0.36627(8) 0.0120 1.0000 Uani . . . . . .
O14 O 0.65019(18) 0.59900(11) 0.21187(8) 0.0116 1.0000 Uani . . . . . .
O15 O 0.61888(19) 0.52367(12) 0.42101(8) 0.0149 1.0000 Uani . . . . . .
O16 O 0.5069(2) 0.42096(12) 0.25337(9) 0.0150 1.0000 Uani . . . . . .
O170 O 0.6976(2) 0.99338(12) 0.43296(9) 0.0152 1.0000 Uani . . . . . .
O180 O 0.80027(19) 0.61255(12) 0.58810(9) 0.0169 1.0000 Uani . . . . . .
O190 O 1.0472(2) 0.34688(14) 0.16336(11) 0.0265 1.0000 Uani . . . . . .
O200 O 0.3411(2) 0.77112(17) -0.11756(11) 0.0303 1.0000 Uani . . . . . .
H92 H 0.7894 1.3208 0.3169 0.0163 1.0000 Uiso R . . . . .
H91 H 0.7872 1.1896 0.2930 0.0163 1.0000 Uiso R . . . . .
H112 H 0.8399 1.3843 0.4729 0.0166 1.0000 Uiso R . . . . .
H111 H 0.8725 1.2901 0.5431 0.0162 1.0000 Uiso R . . . . .
H122 H 0.5557 1.3038 0.5170 0.0153 1.0000 Uiso R . . . . .
H121 H 0.5580 1.1731 0.4942 0.0149 1.0000 Uiso R . . . . .
H142 H 0.4744 1.2037 0.2674 0.0144 1.0000 Uiso R . . . . .
H141 H 0.5055 1.1105 0.3363 0.0141 1.0000 Uiso R . . . . .
H152 H 0.7147 0.6028 -0.0783 0.0264 1.0000 Uiso R . . . . .
H151 H 0.6881 0.6511 0.0118 0.0259 1.0000 Uiso R . . . . .
H172 H 0.8077 0.4821 0.0330 0.0273 1.0000 Uiso R . . . . .
H171 H 0.6313 0.4064 -0.0398 0.0277 1.0000 Uiso R . . . . .
H182 H 0.0862 0.9044 -0.0680 0.0152 1.0000 Uiso R . . . . .
H181 H -0.0105 0.8005 -0.0151 0.0149 1.0000 Uiso R . . . . .
H202 H -0.2445 0.8916 -0.0077 0.0153 1.0000 Uiso R . . . . .
H201 H -0.2424 0.8735 -0.1051 0.0154 1.0000 Uiso R . . . . .
H132 H 0.5033 1.3369 0.3761 0.0153 1.0000 Uiso R . . . . .
H192 H 0.0698 0.9327 0.0995 0.0170 1.0000 Uiso R . . . . .
H131 H 0.3622 1.2346 0.3864 0.0156 1.0000 Uiso R . . . . .
H191 H 0.2411 0.9359 0.0699 0.0174 1.0000 Uiso R . . . . .
H102 H 0.8357 1.1546 0.4336 0.0172 1.0000 Uiso R . . . . .
H101 H 0.9837 1.2620 0.4239 0.0171 1.0000 Uiso R . . . . .
H162 H 0.4246 0.6362 -0.0909 0.0324 1.0000 Uiso R . . . . .
H161 H 0.3998 0.5068 -0.1155 0.0319 1.0000 Uiso R . . . . .
H1802 H 0.7319 0.5848 0.5413 0.0245 1.0000 Uiso R . . . . .
H1801 H 0.7917 0.5577 0.6206 0.0242 1.0000 Uiso R . . . . .
H1902 H 1.0974 0.2994 0.1873 0.0372 1.0000 Uiso R . . . . .
H2002 H 0.2223 0.7443 -0.1296 0.0411 1.0000 Uiso R . . . . .
H1702 H 0.6817 0.9518 0.3899 0.0215 1.0000 Uiso R . . . . .
H1701 H 0.7542 0.9649 0.4736 0.0214 1.0000 Uiso R . . . . .
H1901 H 1.1027 0.4126 0.1870 0.0373 1.0000 Uiso R . . . . .
Zr1 Zr 0.83767(2) 0.779394(13) 0.252412(10) 0.0060 1.0000 Uani . . . . . .
H2001 H 0.3692 0.8207 -0.0771 0.0419 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.551(2) yes
C1 . O1 . 1.293(2) yes
C1 . O3 . 1.214(2) yes
C2 . O2 . 1.265(2) yes
C2 . O4 . 1.240(2) yes
C3 . C4 . 1.550(3) yes
C3 . O5 . 1.294(2) yes
C3 . O7 . 1.213(2) yes
C4 . O6 . 1.279(2) yes
C4 . O8 . 1.227(2) yes
C5 . C6 . 1.546(2) yes
C5 . O9 . 1.285(2) yes
C5 . O11 . 1.225(2) yes
C6 . O10 . 1.275(2) yes
C6 . O12 . 1.231(2) yes
C7 . C8 . 1.546(2) yes
C7 . O13 . 1.269(2) yes
C7 . O15 . 1.234(2) yes
C8 . O14 . 1.294(2) yes
C8 . O16 . 1.220(2) yes
C9 . C14 . 1.512(2) yes
C9 . N10 . 1.489(2) yes
C9 . H92 . 0.975 no
C9 . H91 . 0.960 no
C11 . C12 . 1.515(3) yes
C11 . N10 . 1.491(2) yes
C11 . H112 . 0.976 no
C11 . H111 . 0.970 no
C12 . N13 . 1.494(2) yes
C12 . H122 . 0.959 no
C12 . H121 . 0.973 no
C14 . N13 . 1.493(2) yes
C14 . H142 . 0.969 no
C14 . H141 . 0.961 no
C15 . C17 . 1.538(4) yes
C15 . N16 . 1.477(3) yes
C15 . H152 . 0.979 no
C15 . H151 . 0.977 no
C17 . N16 2_665 1.465(3) yes
C17 . H172 . 0.980 no
C17 . H171 . 0.964 no
C18 . C20 . 1.513(3) yes
C18 . N19 . 1.487(2) yes
C18 . H182 . 0.961 no
C18 . H181 . 0.966 no
C20 . N19 2_575 1.490(2) yes
C20 . H202 . 0.963 no
C20 . H201 . 0.962 no
N10 . H102 . 0.892 no
N10 . H101 . 0.894 no
N13 . H132 . 0.879 no
N13 . H131 . 0.887 no
N16 . H162 . 0.921 no
N16 . H161 . 0.926 no
N19 . H192 . 0.884 no
N19 . H191 . 0.891 no
O1 . Zr1 . 2.1768(13) yes
O2 . Zr1 . 2.2337(12) yes
O5 . Zr1 . 2.1649(13) yes
O6 . Zr1 . 2.1900(13) yes
O9 . Zr1 . 2.2101(12) yes
O10 . Zr1 . 2.1847(12) yes
O13 . Zr1 . 2.2224(13) yes
O14 . Zr1 . 2.1820(12) yes
O170 . H1702 . 0.806 no
O170 . H1701 . 0.819 no
O180 . H1802 . 0.812 no
O180 . H1801 . 0.822 no
O190 . H1902 . 0.809 no
O190 . H1901 . 0.809 no
O200 . H2002 . 0.838 no
O200 . H2001 . 0.816 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . O1 . 112.18(15) yes
C2 . C1 . O3 . 120.98(16) yes
O1 . C1 . O3 . 126.84(17) yes
C1 . C2 . O2 . 114.73(15) yes
C1 . C2 . O4 . 119.37(16) yes
O2 . C2 . O4 . 125.89(17) yes
C4 . C3 . O5 . 112.59(16) yes
C4 . C3 . O7 . 121.37(17) yes
O5 . C3 . O7 . 126.04(18) yes
C3 . C4 . O6 . 112.78(16) yes
C3 . C4 . O8 . 120.35(17) yes
O6 . C4 . O8 . 126.84(18) yes
C6 . C5 . O9 . 113.18(14) yes
C6 . C5 . O11 . 120.18(15) yes
O9 . C5 . O11 . 126.63(16) yes
C5 . C6 . O10 . 114.04(15) yes
C5 . C6 . O12 . 118.97(15) yes
O10 . C6 . O12 . 126.99(16) yes
C8 . C7 . O13 . 114.28(15) yes
C8 . C7 . O15 . 118.19(15) yes
O13 . C7 . O15 . 127.52(16) yes
C7 . C8 . O14 . 113.13(14) yes
C7 . C8 . O16 . 121.72(16) yes
O14 . C8 . O16 . 125.12(16) yes
C14 . C9 . N10 . 110.62(15) yes
C14 . C9 . H92 . 110.1 no
N10 . C9 . H92 . 108.5 no
C14 . C9 . H91 . 109.4 no
N10 . C9 . H91 . 109.2 no
H92 . C9 . H91 . 109.0 no
C12 . C11 . N10 . 110.56(14) yes
C12 . C11 . H112 . 109.3 no
N10 . C11 . H112 . 108.4 no
C12 . C11 . H111 . 109.4 no
N10 . C11 . H111 . 108.5 no
H112 . C11 . H111 . 110.6 no
C11 . C12 . N13 . 110.33(14) yes
C11 . C12 . H122 . 110.8 no
N13 . C12 . H122 . 107.9 no
C11 . C12 . H121 . 109.7 no
N13 . C12 . H121 . 108.6 no
H122 . C12 . H121 . 109.5 no
C9 . C14 . N13 . 110.58(14) yes
C9 . C14 . H142 . 109.5 no
N13 . C14 . H142 . 108.9 no
C9 . C14 . H141 . 109.6 no
N13 . C14 . H141 . 108.7 no
H142 . C14 . H141 . 109.4 no
C17 . C15 . N16 . 108.79(17) yes
C17 . C15 . H152 . 107.9 no
N16 . C15 . H152 . 109.0 no
C17 . C15 . H151 . 111.3 no
N16 . C15 . H151 . 108.6 no
H152 . C15 . H151 . 111.2 no
C15 . C17 . N16 2_665 109.59(18) yes
C15 . C17 . H172 . 109.4 no
N16 2_665 C17 . H172 . 109.5 no
C15 . C17 . H171 . 109.1 no
N16 2_665 C17 . H171 . 109.1 no
H172 . C17 . H171 . 110.1 no
C20 . C18 . N19 . 110.12(15) yes
C20 . C18 . H182 . 110.3 no
N19 . C18 . H182 . 108.7 no
C20 . C18 . H181 . 109.4 no
N19 . C18 . H181 . 108.7 no
H182 . C18 . H181 . 109.6 no
C18 . C20 . N19 2_575 109.52(14) yes
C18 . C20 . H202 . 110.2 no
N19 2_575 C20 . H202 . 108.7 no
C18 . C20 . H201 . 109.9 no
N19 2_575 C20 . H201 . 109.4 no
H202 . C20 . H201 . 109.1 no
C11 . N10 . C9 . 111.32(14) yes
C11 . N10 . H102 . 110.4 no
C9 . N10 . H102 . 108.6 no
C11 . N10 . H101 . 109.3 no
C9 . N10 . H101 . 107.8 no
H102 . N10 . H101 . 109.4 no
C12 . N13 . C14 . 111.49(14) yes
C12 . N13 . H132 . 110.5 no
C14 . N13 . H132 . 110.6 no
C12 . N13 . H131 . 109.0 no
C14 . N13 . H131 . 110.7 no
H132 . N13 . H131 . 104.3 no
C15 . N16 . C17 2_665 111.42(17) yes
C15 . N16 . H162 . 108.0 no
C17 2_665 N16 . H162 . 107.8 no
C15 . N16 . H161 . 109.5 no
C17 2_665 N16 . H161 . 110.1 no
H162 . N16 . H161 . 110.0 no
C20 2_575 N19 . C18 . 111.89(14) yes
C20 2_575 N19 . H192 . 109.1 no
C18 . N19 . H192 . 108.9 no
C20 2_575 N19 . H191 . 109.2 no
C18 . N19 . H191 . 107.1 no
H192 . N19 . H191 . 110.7 no
C1 . O1 . Zr1 . 121.94(11) yes
C2 . O2 . Zr1 . 119.31(11) yes
C3 . O5 . Zr1 . 121.16(11) yes
C4 . O6 . Zr1 . 120.48(11) yes
C5 . O9 . Zr1 . 119.55(11) yes
C6 . O10 . Zr1 . 120.20(11) yes
C7 . O13 . Zr1 . 118.97(11) yes
C8 . O14 . Zr1 . 120.39(11) yes
H1702 . O170 . H1701 . 107.7 no
H1802 . O180 . H1801 . 107.0 no
H1902 . O190 . H1901 . 108.6 no
H2002 . O200 . H2001 . 106.2 no
O2 . Zr1 . O13 . 125.39(5) yes
O2 . Zr1 . O9 . 73.68(5) yes
O13 . Zr1 . O9 . 141.13(5) yes
O2 . Zr1 . O6 . 139.04(5) yes
O13 . Zr1 . O6 . 74.77(5) yes
O9 . Zr1 . O6 . 114.65(5) yes
O2 . Zr1 . O10 . 138.18(5) yes
O13 . Zr1 . O10 . 74.17(5) yes
O9 . Zr1 . O10 . 71.63(5) yes
O6 . Zr1 . O10 . 77.92(5) yes
O2 . Zr1 . O14 . 73.45(5) yes
O13 . Zr1 . O14 . 71.63(5) yes
O9 . Zr1 . O14 . 144.34(5) yes
O6 . Zr1 . O14 . 82.68(5) yes
O10 . Zr1 . O14 . 144.03(5) yes
O2 . Zr1 . O1 . 71.24(5) yes
O13 . Zr1 . O1 . 75.03(5) yes
O9 . Zr1 . O1 . 82.15(5) yes
O6 . Zr1 . O1 . 147.06(5) yes
O10 . Zr1 . O1 . 81.49(5) yes
O2 . Zr1 . O5 . 72.46(5) yes
O13 . Zr1 . O5 . 139.02(5) yes
O9 . Zr1 . O5 . 75.70(5) yes
O6 . Zr1 . O5 . 71.46(5) yes
O10 . Zr1 . O5 . 119.37(5) yes
O14 . Zr1 . O1 . 99.96(5) yes
O14 . Zr1 . O5 . 81.58(5) yes
O1 . Zr1 . O5 . 141.48(5) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C11 . H111 . O6 2_776 156.0 0.970 2.297 3.207(3) yes
C14 . H141 . O3 . 122.0 0.961 2.560 3.172(3) yes
C14 . H141 . O170 . 129.0 0.961 2.549 3.245(3) yes
C15 . H152 . O190 2_765 166.0 0.979 2.423 3.382(3) yes
C15 . H151 . O2 . 155.0 0.977 2.545 3.458(3) yes
C20 . H202 . O2 1_455 159.0 0.963 2.584 3.502(3) yes
N13 . H132 . O15 1_565 147.0 0.879 2.163 2.941(3) yes
N13 . H132 . O16 1_565 132.0 0.879 2.189 2.852(3) yes
N19 . H192 . O5 1_455 128.0 0.884 2.409 3.038(3) yes
N19 . H192 . O9 1_455 157.0 0.884 2.063 2.899(3) yes
N13 . H131 . O11 1_455 122.0 0.887 2.558 3.124(3) yes
N13 . H131 . O12 1_455 142.0 0.887 2.067 2.822(3) yes
N19 . H191 . O4 . 159.0 0.891 1.866 2.718(3) yes
N10 . H102 . O170 . 159.0 0.892 1.876 2.726(3) yes
N10 . H101 . O180 2_776 153.0 0.894 1.902 2.728(3) yes
N16 . H162 . O200 . 165.0 0.921 1.876 2.777(3) yes
N16 . H161 . C8 2_665 142.0 0.926 2.477 3.258(3) yes
N16 . H161 . O14 2_665 172.0 0.926 1.869 2.788(3) yes
O180 . H1802 . O15 . 168.0 0.812 1.956 2.755(3) yes
O180 . H1801 . O8 2_766 170.0 0.822 2.071 2.885(3) yes
O190 . H1902 . O11 1_545 158.0 0.809 2.022 2.790(3) yes
O200 . H2002 . O190 2_665 169.0 0.838 1.958 2.785(3) yes
O170 . H1702 . O1 . 172.0 0.806 2.009 2.809(3) yes
O170 . H1701 . O12 2_776 164.0 0.819 1.931 2.729(3) yes
O190 . H1901 . O8 . 161.0 0.809 2.120 2.895(3) yes
O200 . H2001 . O4 . 154.0 0.816 2.081 2.836(3) yes

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1515800'
_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.0194(4)
_cell_length_b                   17.8877(10)
_cell_length_c                   13.4593(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.3052(16)
_cell_angle_gamma                90
_cell_volume                     1689.94(10)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 2/n 1 '
_symmetry_space_group_name_Hall  '-P 2yac '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y,-z+1/2
x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Zr -2.9673 0.5597 17.8765 1.2762 10.9480 11.9160 5.4173 0.1176 3.6572 87.6627
2.0693 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C28 H32 N8 O18 Zr1'
_chemical_formula_moiety         'C8 O16 Zr, 4(C5 H7 N2), 2(H2 O)'
_chemical_compound_source        ?
_chemical_formula_weight         859.82


_cell_measurement_reflns_used    9789
_cell_measurement_theta_min      2
_cell_measurement_theta_max      31
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_max          0.150

_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.421

# Sheldrick geometric approximatio 0.94 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            53638
_reflns_number_total             5156
_diffrn_reflns_av_R_equivalents  0.026
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5156 
# Theoretical number of reflections is about 10329 


_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         30.520
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        30.520
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              25
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.34
_refine_diff_density_max         0.48


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         5077
_refine_ls_number_restraints     0
_refine_ls_number_parameters     249
_oxford_refine_ls_R_factor_ref   0.0197
_refine_ls_wR_factor_ref         0.0201
_refine_ls_goodness_of_fit_ref   1.0630
_refine_ls_shift/su_max          0.0019536
_refine_ls_shift/su_mean         0.0000831


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5141
_refine_ls_R_factor_all          0.0200
_refine_ls_wR_factor_all         0.0206

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5095
_refine_ls_R_factor_gt           0.0198
_refine_ls_wR_factor_gt          0.0202

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.118 0.871E-01 0.416E-01 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.94459(7) 0.19118(3) 0.26468(4) 0.0122 1.0000 Uani . . . . . .
O2 O 1.00682(7) 0.32309(3) 0.33009(4) 0.0127 1.0000 Uani . . . . . .
O3 O 1.24369(8) 0.28537(3) 0.43101(4) 0.0152 1.0000 Uani . . . . . .
O4 O 1.16327(8) 0.13929(3) 0.36466(4) 0.0156 1.0000 Uani . . . . . .
O5 O 0.69964(8) 0.23925(3) 0.40266(4) 0.0118 1.0000 Uani . . . . . .
O6 O 0.64339(7) 0.37478(3) 0.34171(4) 0.0116 1.0000 Uani . . . . . .
O7 O 0.63302(8) 0.41805(3) 0.49800(4) 0.0150 1.0000 Uani . . . . . .
O8 O 0.64668(8) 0.27036(3) 0.56153(4) 0.0129 1.0000 Uani . . . . . .
O9 O 0.90579(11) 0.15643(4) 0.62564(6) 0.0315 1.0000 Uani . . . . . .
N1 N 0.60733(10) 0.06644(4) 0.35019(6) 0.0217 1.0000 Uani . . . . . .
N2 N 0.65113(10) -0.15096(4) 0.44429(5) 0.0174 1.0000 Uani . . . . . .
N3 N 0.54731(9) 0.39128(4) 0.69831(5) 0.0155 1.0000 Uani . . . . . .
N4 N 0.32622(10) 0.43547(4) 0.97365(5) 0.0156 1.0000 Uani . . . . . .
C1 C 1.07678(10) 0.19346(4) 0.33176(5) 0.0108 1.0000 Uani . . . . . .
C2 C 1.11769(10) 0.27418(4) 0.36902(5) 0.0108 1.0000 Uani . . . . . .
C3 C 0.66235(9) 0.28536(4) 0.47213(5) 0.0101 1.0000 Uani . . . . . .
C4 C 0.64327(9) 0.36728(4) 0.43658(5) 0.0103 1.0000 Uani . . . . . .
C5 C 0.63702(10) -0.07984(4) 0.41264(5) 0.0127 1.0000 Uani . . . . . .
C6 C 0.52497(11) -0.06074(5) 0.32843(6) 0.0174 1.0000 Uani . . . . . .
C7 C 0.51359(12) 0.01254(5) 0.29992(6) 0.0212 1.0000 Uani . . . . . .
C8 C 0.71864(11) 0.05039(4) 0.42912(7) 0.0187 1.0000 Uani . . . . . .
C9 C 0.73749(10) -0.02177(4) 0.46158(6) 0.0144 1.0000 Uani . . . . . .
C10 C 0.40460(10) 0.42177(4) 0.88514(5) 0.0124 1.0000 Uani . . . . . .
C11 C 0.45130(11) 0.48022(4) 0.81832(6) 0.0159 1.0000 Uani . . . . . .
C12 C 0.51918(11) 0.46287(5) 0.72609(6) 0.0167 1.0000 Uani . . . . . .
C13 C 0.51175(11) 0.33436(4) 0.76144(6) 0.0156 1.0000 Uani . . . . . .
C14 C 0.44216(11) 0.34744(4) 0.85448(5) 0.0139 1.0000 Uani . . . . . .
Zr1 Zr 0.7500 0.285383(5) 0.2500 0.0073 1.0000 Uani S T . . . .
H6 H 0.4599 -0.0979 0.2927 0.0218 1.0000 Uiso R . . . . .
H7 H 0.4420 0.0281 0.2433 0.0266 1.0000 Uiso R . . . . .
H8 H 0.7806 0.0904 0.4610 0.0240 1.0000 Uiso R . . . . .
H9 H 0.8141 -0.0330 0.5178 0.0180 1.0000 Uiso R . . . . .
H11 H 0.4326 0.5305 0.8356 0.0198 1.0000 Uiso R . . . . .
H12 H 0.5459 0.5003 0.6792 0.0212 1.0000 Uiso R . . . . .
H13 H 0.5372 0.2848 0.7375 0.0195 1.0000 Uiso R . . . . .
H14 H 0.4144 0.3069 0.8973 0.0185 1.0000 Uiso R . . . . .
H22 H 0.7000 -0.1590 0.5019 0.0223 1.0000 Uiso R . . . . .
H21 H 0.5696 -0.1834 0.4230 0.0230 1.0000 Uiso R . . . . .
H41 H 0.2912 0.3982 1.0115 0.0206 1.0000 Uiso R . . . . .
H3 H 0.5919 0.3824 0.6388 0.0226 1.0000 Uiso R . . . . .
H42 H 0.2808 0.4791 0.9866 0.0206 1.0000 Uiso R . . . . .
H1 H 0.5989 0.1123 0.3293 0.0287 1.0000 Uiso R . . . . .
H92 H 0.8275 0.1939 0.6024 0.0487 1.0000 Uiso R . . . . .
H91 H 1.0267 0.1656 0.6034 0.0504 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C1 . 1.2919(8) yes
O1 . Zr1 . 2.1775(5) yes
O2 . C2 . 1.2812(8) yes
O2 . Zr1 . 2.2013(5) yes
O3 . C2 . 1.2291(9) yes
O4 . C1 . 1.2251(9) yes
O5 . C3 . 1.2751(8) yes
O5 . Zr1 . 2.2440(5) yes
O6 . C4 . 1.2838(8) yes
O6 . Zr1 . 2.1566(5) yes
O7 . C4 . 1.2304(8) yes
O8 . C3 . 1.2383(8) yes
O9 . H92 . 0.920 no
O9 . H91 . 0.916 no
N1 . C7 . 1.3474(13) yes
N1 . C8 . 1.3463(11) yes
N1 . H1 . 0.869 no
N2 . C5 . 1.3451(9) yes
N2 . H22 . 0.858 no
N2 . H21 . 0.863 no
N3 . C12 . 1.3490(11) yes
N3 . C13 . 1.3502(10) yes
N3 . H3 . 0.876 no
N4 . C10 . 1.3375(9) yes
N4 . H41 . 0.874 no
N4 . H42 . 0.862 no
C1 . C2 . 1.5546(10) yes
C3 . C4 . 1.5472(10) yes
C5 . C6 . 1.4179(10) yes
C5 . C9 . 1.4161(10) yes
C6 . C7 . 1.3681(12) yes
C6 . H6 . 0.937 no
C7 . H7 . 0.952 no
C8 . C9 . 1.3688(10) yes
C8 . H8 . 0.940 no
C9 . H9 . 0.948 no
C10 . C11 . 1.4186(10) yes
C10 . C14 . 1.4173(10) yes
C11 . C12 . 1.3676(11) yes
C11 . H11 . 0.938 no
C12 . H12 . 0.940 no
C13 . C14 . 1.3668(10) yes
C13 . H13 . 0.960 no
C14 . H14 . 0.948 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . O1 . Zr1 . 119.14(4) yes
C2 . O2 . Zr1 . 119.02(4) yes
C3 . O5 . Zr1 . 117.87(4) yes
C4 . O6 . Zr1 . 119.59(4) yes
H92 . O9 . H91 . 108.2 no
C7 . N1 . C8 . 121.56(7) yes
C7 . N1 . H1 . 118.7 no
C8 . N1 . H1 . 119.7 no
C5 . N2 . H22 . 118.2 no
C5 . N2 . H21 . 118.9 no
H22 . N2 . H21 . 116.7 no
C12 . N3 . C13 . 120.91(6) yes
C12 . N3 . H3 . 118.7 no
C13 . N3 . H3 . 120.4 no
C10 . N4 . H41 . 119.8 no
C10 . N4 . H42 . 120.0 no
H41 . N4 . H42 . 117.9 no
O1 . C1 . O4 . 125.47(7) yes
O1 . C1 . C2 . 112.68(6) yes
O4 . C1 . C2 . 121.85(6) yes
C1 . C2 . O2 . 113.05(6) yes
C1 . C2 . O3 . 120.08(6) yes
O2 . C2 . O3 . 126.85(7) yes
O5 . C3 . O8 . 126.30(6) yes
O5 . C3 . C4 . 113.81(6) yes
O8 . C3 . C4 . 119.85(6) yes
C3 . C4 . O6 . 113.95(6) yes
C3 . C4 . O7 . 119.77(6) yes
O6 . C4 . O7 . 126.26(7) yes
N2 . C5 . C6 . 121.37(7) yes
N2 . C5 . C9 . 120.72(7) yes
C6 . C5 . C9 . 117.90(7) yes
C5 . C6 . C7 . 119.10(8) yes
C5 . C6 . H6 . 120.4 no
C7 . C6 . H6 . 120.5 no
C6 . C7 . N1 . 121.14(7) yes
C6 . C7 . H7 . 122.3 no
N1 . C7 . H7 . 116.5 no
N1 . C8 . C9 . 120.51(8) yes
N1 . C8 . H8 . 117.6 no
C9 . C8 . H8 . 121.9 no
C5 . C9 . C8 . 119.74(7) yes
C5 . C9 . H9 . 119.6 no
C8 . C9 . H9 . 120.6 no
N4 . C10 . C11 . 121.82(7) yes
N4 . C10 . C14 . 120.61(7) yes
C11 . C10 . C14 . 117.57(6) yes
C10 . C11 . C12 . 119.41(7) yes
C10 . C11 . H11 . 121.1 no
C12 . C11 . H11 . 119.5 no
C11 . C12 . N3 . 121.28(7) yes
C11 . C12 . H12 . 121.3 no
N3 . C12 . H12 . 117.4 no
N3 . C13 . C14 . 121.04(7) yes
N3 . C13 . H13 . 116.7 no
C14 . C13 . H13 . 122.2 no
C10 . C14 . C13 . 119.69(7) yes
C10 . C14 . H14 . 120.2 no
C13 . C14 . H14 . 120.1 no
O5 . Zr1 . O5 3_655 136.84(3) yes
O5 . Zr1 . O2 3_655 115.37(2) yes
O5 3_655 Zr1 . O2 3_655 78.28(2) yes
O5 . Zr1 . O2 . 78.28(2) yes
O5 3_655 Zr1 . O2 . 115.37(2) yes
O2 3_655 Zr1 . O2 . 144.32(3) yes
O5 . Zr1 . O1 . 74.58(2) yes
O5 3_655 Zr1 . O1 . 72.34(2) yes
O2 3_655 Zr1 . O1 . 142.487(19) yes
O2 . Zr1 . O1 . 71.396(19) yes
O5 . Zr1 . O1 3_655 72.34(2) yes
O5 3_655 Zr1 . O1 3_655 74.58(2) yes
O2 3_655 Zr1 . O1 3_655 71.396(19) yes
O2 . Zr1 . O1 3_655 142.487(19) yes
O1 . Zr1 . O1 3_655 78.60(3) yes
O5 . Zr1 . O6 . 72.048(19) yes
O5 3_655 Zr1 . O6 . 148.611(19) yes
O2 3_655 Zr1 . O6 . 76.55(2) yes
O2 . Zr1 . O6 . 77.19(2) yes
O1 . Zr1 . O6 . 137.843(19) yes
O5 . Zr1 . O6 3_655 148.611(19) yes
O5 3_655 Zr1 . O6 3_655 72.048(19) yes
O2 3_655 Zr1 . O6 3_655 77.19(2) yes
O2 . Zr1 . O6 3_655 76.55(2) yes
O1 . Zr1 . O6 3_655 113.98(2) yes
O1 3_655 Zr1 . O6 . 113.98(2) yes
O1 3_655 Zr1 . O6 3_655 137.843(19) yes
O6 . Zr1 . O6 3_655 84.28(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H6 . O9 4_454 146.0 0.937 2.508 3.3250(10) yes
C7 . H7 . O4 3_655 146.0 0.952 2.569 3.3998(10) yes
C9 . H9 . O4 2_756 135.0 0.948 2.477 3.2181(10) yes
C14 . H14 . O3 3_656 138.0 0.948 2.598 3.3631(10) yes
N2 . H22 . O3 2_756 123.0 0.858 2.466 3.0215(10) yes
N2 . H22 . O4 2_756 160.0 0.858 2.062 2.8840(10) yes
N2 . H21 . O8 2_656 155.0 0.863 2.184 2.9893(10) yes
N4 . H41 . O3 3_656 161.0 0.874 2.176 3.0171(10) yes
N3 . H3 . O7 . 149.0 0.876 2.022 2.8067(10) yes
N3 . H3 . O8 . 129.0 0.876 2.291 2.9271(10) yes
N4 . H42 . O7 4_465 170.0 0.862 2.118 2.9693(10) yes
N1 . H1 . O1 3_655 157.0 0.869 1.918 2.7379(10) yes
N1 . H1 . O5 . 134.0 0.869 2.574 3.2355(10) yes
O9 . H92 . O8 . 175.0 0.920 1.944 2.8616(10) yes
O9 . H91 . N2 2_756 163.0 0.916 2.368 3.2557(10) yes



####################################################################### 
# 
# 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_cpd2
_database_code_depnum_ccdc_archive 'CCDC 1515798'
_audit_update_record             
;
2016-11-15 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   15.078(5)
_cell_length_b                   20.979(5)
_cell_length_c                   8.776(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.917(5)
_cell_angle_gamma                90
_cell_volume                     2742.5(16)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Zr -2.9673 0.5597 17.8765 1.2762 10.9480 11.9160 5.4173 0.1176 3.6572 87.6627
2.0693 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H28 N4 O20 Zr1 
# Dc =      1.78 Fooo =   1504.00 Mu =      5.03 M =    735.68
# Found Formula = C20 H28 N4 O20 Zr1 
# Dc =      1.78 FOOO =   1504.00 Mu =      5.03 M =    735.68

_chemical_formula_sum            'C20 H28 N4 O20 Zr1'
_chemical_formula_moiety         'C8 O16 Zr, 2(C6 H10 N2), 4(H2 O)'
_chemical_compound_source        ?
_chemical_formula_weight         735.68


_cell_measurement_reflns_used    9636
_cell_measurement_theta_min      2
_cell_measurement_theta_max      35
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            'blue violet'
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.503

# Sheldrick geometric approximatio 0.95 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            43277
_reflns_number_total             12503
_diffrn_reflns_av_R_equivalents  0.058
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 12503 
# Theoretical number of reflections is about 25536 


_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         35.800
_diffrn_measured_fraction_theta_max 0.975

_diffrn_reflns_theta_full        25.060
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -24
_reflns_limit_h_max              24
_reflns_limit_k_min              0
_reflns_limit_k_max              33
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.41
_refine_diff_density_max         0.44


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         6566
_refine_ls_number_restraints     0
_refine_ls_number_parameters     406
_oxford_refine_ls_R_factor_ref   0.0352
_refine_ls_wR_factor_ref         0.0295
_refine_ls_goodness_of_fit_ref   1.1223
_refine_ls_shift/su_max          0.0010708
_refine_ls_shift/su_mean         0.0000930


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        12486
_refine_ls_R_factor_all          0.0842
_refine_ls_wR_factor_all         0.0624

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7226
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_gt          0.0315

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.326 0.342 0.288 0.164 0.722E-01 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Zr1 Zr 0.240914(12) 0.499863(11) 0.963301(19) 0.0193 1.0000 Uani . . . . . .
O1 O 0.29175(11) 0.59854(7) 1.01451(16) 0.0290 1.0000 Uani . . . . . .
O2 O 0.28456(10) 0.54212(7) 0.75152(16) 0.0265 1.0000 Uani . . . . . .
O3 O 0.33413(12) 0.62965(8) 0.64531(17) 0.0350 1.0000 Uani . . . . . .
O4 O 0.33902(11) 0.68914(7) 0.92268(18) 0.0320 1.0000 Uani . . . . . .
O5 O 0.12224(10) 0.54858(8) 0.85055(17) 0.0320 1.0000 Uani . . . . . .
O6 O 0.16153(11) 0.52859(7) 1.13958(17) 0.0310 1.0000 Uani . . . . . .
O7 O 0.03310(14) 0.57135(9) 1.1890(2) 0.0488 1.0000 Uani . . . . . .
O8 O -0.00837(12) 0.59503(9) 0.8713(2) 0.0456 1.0000 Uani . . . . . .
O9 O 0.18919(10) 0.43633(7) 0.76985(16) 0.0273 1.0000 Uani . . . . . .
O10 O 0.20343(10) 0.40914(7) 1.05593(16) 0.0270 1.0000 Uani . . . . . .
O11 O 0.14564(12) 0.31172(7) 1.00949(19) 0.0354 1.0000 Uani . . . . . .
O12 O 0.12669(10) 0.34231(8) 0.69664(18) 0.0323 1.0000 Uani . . . . . .
O13 O 0.36468(10) 0.44983(7) 0.93150(16) 0.0284 1.0000 Uani . . . . . .
O14 O 0.33039(9) 0.49544(9) 1.18520(15) 0.0298 1.0000 Uani . . . . . .
O15 O 0.50364(11) 0.42124(8) 1.03135(18) 0.0368 1.0000 Uani . . . . . .
O16 O 0.46399(12) 0.46900(10) 1.3140(2) 0.0480 1.0000 Uani . . . . . .
O17 O 0.35444(13) 0.45442(9) 0.5493(2) 0.0439 1.0000 Uani . . . . . .
O18 O 0.33700(13) 0.61749(10) 1.3517(2) 0.0502 1.0000 Uani . . . . . .
O19 O 0.19928(13) 0.38684(10) 1.3723(2) 0.0514 1.0000 Uani . . . . . .
O20 O 0.11540(14) 0.51156(9) 0.4856(2) 0.0559 1.0000 Uani . . . . . .
N1 N 0.48865(14) 0.38456(10) 0.7325(3) 0.0380 1.0000 Uani . . . . . .
N2 N -0.00359(13) 0.60279(9) 0.5551(2) 0.0366 1.0000 Uani . . . . . .
N3 N -0.07815(15) 0.71221(10) 0.6940(3) 0.0429 1.0000 Uani . . . . . .
N4 N 0.60633(13) 0.27325(10) 0.7841(2) 0.0361 1.0000 Uani . . . . . .
C1 C 0.31493(13) 0.63267(10) 0.9089(2) 0.0243 1.0000 Uani . . . . . .
C2 C 0.31163(13) 0.59942(10) 0.7528(2) 0.0239 1.0000 Uani . . . . . .
C3 C 0.06157(14) 0.56825(10) 0.9272(3) 0.0293 1.0000 Uani . . . . . .
C4 C 0.08442(15) 0.55578(10) 1.1015(3) 0.0300 1.0000 Uani . . . . . .
C5 C 0.16889(13) 0.36409(10) 0.9676(2) 0.0256 1.0000 Uani . . . . . .
C6 C 0.15926(13) 0.38091(9) 0.7952(2) 0.0240 1.0000 Uani . . . . . .
C7 C 0.40902(15) 0.47142(10) 1.1967(2) 0.0285 1.0000 Uani . . . . . .
C8 C 0.42969(14) 0.44464(10) 1.0419(2) 0.0266 1.0000 Uani . . . . . .
C9 C 0.00694(15) 0.71610(11) 0.6344(3) 0.0317 1.0000 Uani . . . . . .
C10 C 0.04299(15) 0.66375(10) 0.5689(3) 0.0303 1.0000 Uani . . . . . .
C11 C 0.12352(16) 0.66957(13) 0.5135(3) 0.0417 1.0000 Uani . . . . . .
C12 C 0.16772(17) 0.72716(13) 0.5233(4) 0.0476 1.0000 Uani . . . . . .
C13 C 0.13263(18) 0.77893(13) 0.5884(4) 0.0470 1.0000 Uani . . . . . .
C14 C 0.05157(17) 0.77374(12) 0.6442(3) 0.0411 1.0000 Uani . . . . . .
C15 C 0.4717(2) 0.20695(14) 0.7611(4) 0.0534 1.0000 Uani . . . . . .
C16 C 0.3793(2) 0.20025(15) 0.7401(5) 0.0691 1.0000 Uani . . . . . .
C17 C 0.3245(2) 0.25236(16) 0.7136(4) 0.0635 1.0000 Uani . . . . . .
C18 C 0.36097(17) 0.31256(14) 0.7088(4) 0.0479 1.0000 Uani . . . . . .
C19 C 0.45321(15) 0.32011(11) 0.7315(3) 0.0335 1.0000 Uani . . . . . .
C20 C 0.50832(16) 0.26686(11) 0.7574(3) 0.0342 1.0000 Uani . . . . . .
H111 H 0.1477 0.6345 0.4689 0.0499 1.0000 Uiso R . . . . .
H121 H 0.2208 0.7306 0.4845 0.0566 1.0000 Uiso R . . . . .
H131 H 0.1633 0.8180 0.5955 0.0567 1.0000 Uiso R . . . . .
H141 H 0.0269 0.8085 0.6861 0.0493 1.0000 Uiso R . . . . .
H151 H 0.5085 0.1711 0.7793 0.0653 1.0000 Uiso R . . . . .
H161 H 0.3540 0.1603 0.7446 0.0826 1.0000 Uiso R . . . . .
H173 H 0.3429 0.4827 0.6075 0.0649 1.0000 Uiso R . . . . .
H201 H 0.1308 0.5119 0.4018 0.0839 1.0000 Uiso R . . . . .
H202 H 0.1491 0.4966 0.5575 0.0843 1.0000 Uiso R . . . . .
H22 H -0.0531 0.6054 0.4887 0.0543 1.0000 Uiso R . . . . .
H21 H -0.0165 0.5923 0.6446 0.0549 1.0000 Uiso R . . . . .
H42 H 0.6309 0.2361 0.7567 0.0543 1.0000 Uiso R . . . . .
H43 H 0.6248 0.3060 0.7266 0.0539 1.0000 Uiso R . . . . .
H31 H -0.1158 0.6842 0.6389 0.0645 1.0000 Uiso R . . . . .
H23 H 0.0327 0.5737 0.5236 0.0553 1.0000 Uiso R . . . . .
H33 H -0.0698 0.6985 0.7902 0.0646 1.0000 Uiso R . . . . .
H13 H 0.4982 0.4008 0.8323 0.0567 1.0000 Uiso R . . . . .
H41 H 0.6256 0.2813 0.8832 0.0541 1.0000 Uiso R . . . . .
H11 H 0.4480 0.4083 0.6699 0.0557 1.0000 Uiso R . . . . .
H12 H 0.5404 0.3850 0.6944 0.0557 1.0000 Uiso R . . . . .
H32 H -0.1036 0.7496 0.6900 0.0657 1.0000 Uiso R . . . . .
H171 H 0.2607 0.2474 0.6991 0.0752 1.0000 Uiso R . . . . .
H192 H 0.1985 0.3955 1.2791 0.0760 1.0000 Uiso R . . . . .
H191 H 0.2413 0.4029 1.4354 0.0759 1.0000 Uiso R . . . . .
H172 H 0.3812 0.4698 0.4818 0.0667 1.0000 Uiso R . . . . .
H181 H 0.3240 0.3481 0.6920 0.0573 1.0000 Uiso R . . . . .
H182 H 0.3315 0.6133 1.4434 0.0746 1.0000 Uiso R . . . . .
H183 H 0.3087 0.5898 1.3009 0.0754 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zr1 . O1 . 2.2289(16) yes
Zr1 . O2 . 2.2478(17) yes
Zr1 . O5 . 2.1626(16) yes
Zr1 . O6 . 2.1825(16) yes
Zr1 . O9 . 2.2038(16) yes
Zr1 . O10 . 2.1783(15) yes
Zr1 . O13 . 2.1962(15) yes
Zr1 . O14 . 2.1924(16) yes
O1 . C1 . 1.263(2) yes
O2 . C2 . 1.269(2) yes
O3 . C2 . 1.227(2) yes
O4 . C1 . 1.240(2) yes
O5 . C3 . 1.285(3) yes
O6 . C4 . 1.292(3) yes
O7 . C4 . 1.216(3) yes
O8 . C3 . 1.228(3) yes
O9 . C6 . 1.279(2) yes
O10 . C5 . 1.281(2) yes
O11 . C5 . 1.227(3) yes
O12 . C6 . 1.230(2) yes
O13 . C8 . 1.272(2) yes
O14 . C7 . 1.278(3) yes
O15 . C8 . 1.235(3) yes
O16 . C7 . 1.218(3) yes
O17 . H173 . 0.819 no
O17 . H172 . 0.832 no
O18 . H182 . 0.827 no
O18 . H183 . 0.811 no
O19 . H192 . 0.836 no
O19 . H191 . 0.844 no
O20 . H201 . 0.804 no
O20 . H202 . 0.809 no
N1 . C19 . 1.453(3) yes
N1 . H13 . 0.930 no
N1 . H11 . 0.906 no
N1 . H12 . 0.895 no
N2 . C10 . 1.455(3) yes
N2 . H22 . 0.875 no
N2 . H21 . 0.867 no
N2 . H23 . 0.891 no
N3 . C9 . 1.461(3) yes
N3 . H31 . 0.904 no
N3 . H33 . 0.882 no
N3 . H32 . 0.872 no
N4 . C20 . 1.466(3) yes
N4 . H42 . 0.910 no
N4 . H43 . 0.921 no
N4 . H41 . 0.889 no
C1 . C2 . 1.531(3) yes
C3 . C4 . 1.538(3) yes
C5 . C6 . 1.538(3) yes
C7 . C8 . 1.546(3) yes
C9 . C10 . 1.389(3) yes
C9 . C14 . 1.380(3) yes
C10 . C11 . 1.382(3) yes
C11 . C12 . 1.376(4) yes
C11 . H111 . 0.933 no
C12 . C13 . 1.371(4) yes
C12 . H121 . 0.921 no
C13 . C14 . 1.390(4) yes
C13 . H131 . 0.938 no
C14 . H141 . 0.921 no
C15 . C16 . 1.383(4) yes
C15 . C20 . 1.375(4) yes
C15 . H151 . 0.935 no
C16 . C17 . 1.368(5) yes
C16 . H161 . 0.923 no
C17 . C18 . 1.381(4) yes
C17 . H171 . 0.956 no
C18 . C19 . 1.383(3) yes
C18 . H181 . 0.929 no
C19 . C20 . 1.390(3) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . Zr1 . O2 . 70.42(5) yes
O1 . Zr1 . O5 . 83.55(6) yes
O2 . Zr1 . O5 . 76.28(6) yes
O1 . Zr1 . O6 . 79.04(6) yes
O2 . Zr1 . O6 . 137.75(6) yes
O5 . Zr1 . O6 . 71.82(6) yes
O1 . Zr1 . O9 . 141.87(5) yes
O2 . Zr1 . O9 . 73.47(6) yes
O5 . Zr1 . O9 . 76.38(6) yes
O6 . Zr1 . O9 . 123.07(6) yes
O1 . Zr1 . O10 . 146.85(6) yes
O2 . Zr1 . O10 . 141.20(5) yes
O5 . Zr1 . O10 . 109.85(6) yes
O6 . Zr1 . O10 . 76.95(6) yes
O9 . Zr1 . O10 . 71.20(7) yes
O1 . Zr1 . O13 . 101.37(6) yes
O2 . Zr1 . O13 . 73.74(6) yes
O5 . Zr1 . O13 . 145.77(6) yes
O6 . Zr1 . O13 . 142.39(6) yes
O9 . Zr1 . O13 . 79.59(6) yes
O1 . Zr1 . O14 . 73.45(7) yes
O2 . Zr1 . O14 . 122.17(6) yes
O5 . Zr1 . O14 . 141.08(6) yes
O6 . Zr1 . O14 . 73.24(7) yes
O9 . Zr1 . O14 . 138.96(6) yes
O10 . Zr1 . O13 . 84.52(6) yes
O10 . Zr1 . O14 . 77.94(7) yes
O13 . Zr1 . O14 . 71.01(5) yes
Zr1 . O1 . C1 . 120.28(13) yes
Zr1 . O2 . C2 . 120.08(12) yes
Zr1 . O5 . C3 . 121.20(14) yes
Zr1 . O6 . C4 . 120.62(14) yes
Zr1 . O9 . C6 . 120.53(13) yes
Zr1 . O10 . C5 . 121.57(13) yes
Zr1 . O13 . C8 . 120.92(13) yes
Zr1 . O14 . C7 . 121.51(13) yes
H173 . O17 . H172 . 109.7 no
H182 . O18 . H183 . 109.5 no
H192 . O19 . H191 . 116.7 no
H201 . O20 . H202 . 118.8 no
C19 . N1 . H13 . 110.4 no
C19 . N1 . H11 . 107.1 no
H13 . N1 . H11 . 111.2 no
C19 . N1 . H12 . 110.4 no
H13 . N1 . H12 . 109.3 no
H11 . N1 . H12 . 108.3 no
C10 . N2 . H22 . 110.6 no
C10 . N2 . H21 . 108.8 no
H22 . N2 . H21 . 109.3 no
C10 . N2 . H23 . 108.4 no
H22 . N2 . H23 . 109.8 no
H21 . N2 . H23 . 109.9 no
C9 . N3 . H31 . 111.0 no
C9 . N3 . H33 . 111.0 no
H31 . N3 . H33 . 106.5 no
C9 . N3 . H32 . 109.9 no
H31 . N3 . H32 . 109.2 no
H33 . N3 . H32 . 109.2 no
C20 . N4 . H42 . 108.7 no
C20 . N4 . H43 . 111.3 no
H42 . N4 . H43 . 108.9 no
C20 . N4 . H41 . 110.0 no
H42 . N4 . H41 . 109.6 no
H43 . N4 . H41 . 108.3 no
O1 . C1 . O4 . 125.48(19) yes
O1 . C1 . C2 . 115.10(18) yes
O4 . C1 . C2 . 119.43(18) yes
C1 . C2 . O2 . 113.91(17) yes
C1 . C2 . O3 . 118.53(18) yes
O2 . C2 . O3 . 127.56(19) yes
O5 . C3 . O8 . 125.1(2) yes
O5 . C3 . C4 . 113.48(19) yes
O8 . C3 . C4 . 121.4(2) yes
C3 . C4 . O6 . 112.72(18) yes
C3 . C4 . O7 . 121.0(2) yes
O6 . C4 . O7 . 126.2(2) yes
O10 . C5 . O11 . 126.0(2) yes
O10 . C5 . C6 . 113.18(18) yes
O11 . C5 . C6 . 120.83(18) yes
C5 . C6 . O9 . 113.42(17) yes
C5 . C6 . O12 . 120.47(19) yes
O9 . C6 . O12 . 126.1(2) yes
O14 . C7 . O16 . 125.8(2) yes
O14 . C7 . C8 . 112.64(17) yes
O16 . C7 . C8 . 121.6(2) yes
C7 . C8 . O13 . 113.70(18) yes
C7 . C8 . O15 . 121.20(19) yes
O13 . C8 . O15 . 125.1(2) yes
N3 . C9 . C10 . 121.7(2) yes
N3 . C9 . C14 . 118.3(2) yes
C10 . C9 . C14 . 120.0(2) yes
N2 . C10 . C9 . 121.0(2) yes
N2 . C10 . C11 . 119.2(2) yes
C9 . C10 . C11 . 119.8(2) yes
C10 . C11 . C12 . 120.0(2) yes
C10 . C11 . H111 . 120.0 no
C12 . C11 . H111 . 120.1 no
C11 . C12 . C13 . 120.5(2) yes
C11 . C12 . H121 . 119.1 no
C13 . C12 . H121 . 120.5 no
C12 . C13 . C14 . 120.2(2) yes
C12 . C13 . H131 . 120.1 no
C14 . C13 . H131 . 119.8 no
C13 . C14 . C9 . 119.6(2) yes
C13 . C14 . H141 . 120.7 no
C9 . C14 . H141 . 119.7 no
C16 . C15 . C20 . 119.3(3) yes
C16 . C15 . H151 . 120.1 no
C20 . C15 . H151 . 120.6 no
C15 . C16 . C17 . 120.7(3) yes
C15 . C16 . H161 . 120.0 no
C17 . C16 . H161 . 119.3 no
C16 . C17 . C18 . 120.2(3) yes
C16 . C17 . H171 . 120.3 no
C18 . C17 . H171 . 119.5 no
C17 . C18 . C19 . 119.8(3) yes
C17 . C18 . H181 . 120.5 no
C19 . C18 . H181 . 119.7 no
N1 . C19 . C18 . 117.9(2) yes
N1 . C19 . C20 . 122.5(2) yes
C18 . C19 . C20 . 119.6(2) yes
N4 . C20 . C19 . 121.0(2) yes
N4 . C20 . C15 . 118.6(2) yes
C19 . C20 . C15 . 120.4(2) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C12 . H121 . O4 4_564 143.0 0.921 2.570 3.353(4) yes
C14 . H141 . O7 4_564 141.0 0.921 2.522 3.291(4) yes
C15 . H151 . O3 3_646 147.0 0.935 2.517 3.337(4) yes
O17 . H173 . O2 . 166.0 0.819 2.066 2.868(4) yes
O20 . H201 . O6 1_554 170.0 0.804 2.442 3.238(4) yes
O20 . H202 . O9 . 156.0 0.809 2.256 3.015(4) yes
N2 . H22 . O12 2_566 146.0 0.875 2.126 2.895(4) yes
N2 . H21 . O8 . 157.0 0.867 1.975 2.792(4) yes
N4 . H42 . O3 3_646 140.0 0.910 2.422 3.177(4) yes
N4 . H42 . O4 3_646 142.0 0.910 1.969 2.747(4) yes
N4 . H43 . O18 2_667 168.0 0.921 1.871 2.778(4) yes
N3 . H31 . O19 2_567 151.0 0.904 1.943 2.768(4) yes
N2 . H23 . O20 . 172.0 0.891 1.870 2.756(4) yes
N3 . H33 . O8 . 124.0 0.882 2.423 3.011(4) yes
N3 . H33 . O11 2_567 140.0 0.882 2.251 2.980(4) yes
N1 . H13 . O15 . 170.0 0.930 1.788 2.709(4) yes
N1 . H13 . C8 . 146.0 0.930 2.427 3.241(4) yes
N4 . H41 . O4 2_667 171.0 0.889 1.814 2.696(4) yes
N1 . H11 . O17 . 174.0 0.906 1.894 2.796(4) yes
N1 . H12 . O18 2_667 170.0 0.895 1.953 2.839(4) yes
N3 . H32 . O11 3_556 130.0 0.872 2.195 2.832(4) yes
N3 . H32 . O12 3_556 150.0 0.872 2.236 3.021(4) yes
C17 . H171 . O11 4_554 135.0 0.956 2.535 3.285(4) yes
O19 . H192 . O10 . 175.0 0.836 1.992 2.826(4) yes
O19 . H191 . O17 1_556 167.0 0.844 2.133 2.961(4) yes
O17 . H172 . O16 1_554 156.0 0.832 2.073 2.854(4) yes
O18 . H182 . O3 1_556 161.0 0.827 1.799 2.596(4) yes
O18 . H183 . O14 . 140.0 0.811 2.272 2.942(4) yes


####################################################################### 
# 
# 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_cpd1
_database_code_depnum_ccdc_archive 'CCDC 1515797'
_audit_update_record             
;
2016-11-09 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.077(9)
_cell_length_b                   10.810(10)
_cell_length_c                   11.116(11)
_cell_angle_alpha                78.14(3)
_cell_angle_beta                 89.23(5)
_cell_angle_gamma                86.71(3)
_cell_volume                     1183.0(12)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Zr -2.9673 0.5597 17.8765 1.2762 10.9480 11.9160 5.4173 0.1176 3.6572 87.6627
2.0693 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Found Formula = C10 H20 N8 O18 S2 Zr1 
# Dc =      1.95 FOOO =    704.00 Mu =      7.44 M =    695.66

_chemical_formula_sum            'C10 H20 N8 O18 S2 Zr1'
_chemical_formula_moiety         'C8 O16 Zr, 2(C H8 N4 S), 2(H2 O)'
_chemical_compound_source        ?
_chemical_formula_weight         695.66


_cell_measurement_reflns_used    8654
_cell_measurement_theta_min      4
_cell_measurement_theta_max      35
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.953
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.744

# Sheldrick geometric approximatio 0.86 0.86 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.86
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            39412
_reflns_number_total             9351
_diffrn_reflns_av_R_equivalents  0.032
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 9351 
# Theoretical number of reflections is about 20378 


_diffrn_reflns_theta_min         1.872
_diffrn_reflns_theta_max         34.703
_diffrn_measured_fraction_theta_max 0.918

_diffrn_reflns_theta_full        25.334
_diffrn_measured_fraction_theta_full 0.982


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              -16
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.29
_refine_diff_density_max         3.16


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         7487
_refine_ls_number_restraints     0
_refine_ls_number_parameters     352
_oxford_refine_ls_R_factor_ref   0.0470
_refine_ls_wR_factor_ref         0.0402
_refine_ls_goodness_of_fit_ref   0.8618
_refine_ls_shift/su_max          0.0013993
_refine_ls_shift/su_mean         0.0000385


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        9333
_refine_ls_R_factor_all          0.0566
_refine_ls_wR_factor_all         0.0469

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                8001
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_gt          0.0409

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.426 0.424 0.226 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 1.00083(17) 0.58266(17) 0.35690(16) 0.0091 1.0000 Uani . . . . . .
C2 C 0.90025(18) 0.48917(17) 0.33263(17) 0.0098 1.0000 Uani . . . . . .
C3 C 0.61916(18) 0.67240(17) 0.54137(16) 0.0096 1.0000 Uani . . . . . .
C4 C 0.50621(18) 0.65795(17) 0.45391(17) 0.0098 1.0000 Uani . . . . . .
C5 C 0.77727(17) 1.02802(16) 0.29152(16) 0.0083 1.0000 Uani . . . . . .
C6 C 0.64640(18) 1.02383(17) 0.22147(17) 0.0103 1.0000 Uani . . . . . .
C7 C 0.70770(17) 0.73016(17) 0.01582(17) 0.0097 1.0000 Uani . . . . . .
C8 C 0.84053(18) 0.79370(18) 0.01930(17) 0.0108 1.0000 Uani . . . . . .
C9 C 0.67200(17) 0.38824(17) 0.00342(17) 0.0094 1.0000 Uani . . . . . .
C10 C 0.17042(17) 1.01916(17) 0.38602(16) 0.0089 1.0000 Uani . . . . . .
N1 N 0.64167(16) 0.36114(15) 0.22051(15) 0.0101 1.0000 Uani . . . . . .
N2 N 0.58452(16) 0.38851(16) 0.10007(15) 0.0107 1.0000 Uani . . . . . .
N3 N 0.60749(17) 0.37336(18) -0.09801(16) 0.0140 1.0000 Uani . . . . . .
N4 N 0.67944(17) 0.37683(18) -0.20869(15) 0.0133 1.0000 Uani . . . . . .
N5 N 0.16627(16) 0.79768(15) 0.45341(16) 0.0116 1.0000 Uani . . . . . .
N6 N 0.09560(15) 0.91722(16) 0.42671(16) 0.0108 1.0000 Uani . . . . . .
N7 N 0.09384(16) 1.12758(16) 0.35054(15) 0.0109 1.0000 Uani . . . . . .
N8 N 0.15446(16) 1.23856(15) 0.28928(15) 0.0114 1.0000 Uani . . . . . .
S1 S 0.83320(5) 0.40984(5) 0.00865(5) 0.0143 1.0000 Uani . . . . . .
S2 S 0.33657(4) 1.01130(5) 0.38950(5) 0.0127 1.0000 Uani . . . . . .
O1 O 0.94851(13) 0.69480(13) 0.35398(13) 0.0101 1.0000 Uani . . . . . .
O2 O 0.78539(13) 0.54288(13) 0.29959(13) 0.0107 1.0000 Uani . . . . . .
O3 O 0.92999(15) 0.37465(13) 0.34440(14) 0.0129 1.0000 Uani . . . . . .
O4 O 1.11915(14) 0.54845(15) 0.37671(14) 0.0138 1.0000 Uani . . . . . .
O5 O 0.72344(14) 0.71594(13) 0.48584(13) 0.0104 1.0000 Uani . . . . . .
O6 O 0.54409(13) 0.67349(14) 0.34018(13) 0.0104 1.0000 Uani . . . . . .
O7 O 0.39311(14) 0.63615(15) 0.49289(14) 0.0143 1.0000 Uani . . . . . .
O8 O 0.60376(15) 0.64467(15) 0.65490(13) 0.0138 1.0000 Uani . . . . . .
O9 O 0.83444(13) 0.91833(12) 0.33049(13) 0.0094 1.0000 Uani . . . . . .
O10 O 0.60977(13) 0.90970(13) 0.22812(14) 0.0112 1.0000 Uani . . . . . .
O11 O 0.58992(16) 1.12118(14) 0.16456(16) 0.0178 1.0000 Uani . . . . . .
O12 O 0.81758(14) 1.13105(13) 0.30311(14) 0.0117 1.0000 Uani . . . . . .
O13 O 0.64968(14) 0.70256(14) 0.12166(12) 0.0106 1.0000 Uani . . . . . .
O14 O 0.87095(14) 0.80778(14) 0.12829(13) 0.0116 1.0000 Uani . . . . . .
O15 O 0.90778(16) 0.82286(18) -0.07366(14) 0.0180 1.0000 Uani . . . . . .
O16 O 0.66663(14) 0.70946(15) -0.08155(13) 0.0128 1.0000 Uani . . . . . .
O170 O 1.14975(15) 0.83006(15) 0.18640(14) 0.0148 1.0000 Uani . . . . . .
O180 O 0.6450(2) 1.0373(3) -0.07107(19) 0.0358 1.0000 Uani . . . . . .
Zr1 Zr 0.744308(17) 0.747159(17) 0.286517(16) 0.0059 1.0000 Uani . . . . . .
H41 H 0.7457 0.3176 -0.1990 0.0205 1.0000 Uiso R . . . . .
H42 H 0.7118 0.4524 -0.2348 0.0205 1.0000 Uiso R . . . . .
H21 H 0.5109 0.3525 0.0947 0.0140 1.0000 Uiso R . . . . .
H12 H 0.6931 0.4228 0.2312 0.0144 1.0000 Uiso R . . . . .
H11 H 0.6908 0.2881 0.2366 0.0156 1.0000 Uiso R . . . . .
H81 H 0.2380 1.2386 0.3128 0.0177 1.0000 Uiso R . . . . .
H52 H 0.2536 0.8089 0.4567 0.0176 1.0000 Uiso R . . . . .
H53 H 0.1388 0.7551 0.5257 0.0175 1.0000 Uiso R . . . . .
H51 H 0.1493 0.7540 0.3962 0.0182 1.0000 Uiso R . . . . .
H82 H 0.1521 1.2433 0.2076 0.0177 1.0000 Uiso R . . . . .
H83 H 0.1092 1.3049 0.3073 0.0184 1.0000 Uiso R . . . . .
H31 H 0.5261 0.3549 -0.0961 0.0182 1.0000 Uiso R . . . . .
H1701 H 1.1895 0.8857 0.1362 0.0225 1.0000 Uiso R . . . . .
H1702 H 1.0754 0.8305 0.1568 0.0222 1.0000 Uiso R . . . . .
H1801 H 0.6069 1.0741 -0.0217 0.0536 1.0000 Uiso R . . . . .
H1802 H 0.5904 1.0301 -0.1211 0.0542 1.0000 Uiso R . . . . .
H61 H 0.0173 0.9182 0.3968 0.0134 1.0000 Uiso . . . . . .
H13 H 0.5762 0.3566 0.2762 0.0163 1.0000 Uiso . . . . . .
H71 H 0.0105 1.1233 0.3391 0.0147 1.0000 Uiso . . . . . .
H43 H 0.6223 0.3650 -0.2677 0.0212 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.536(3) yes
C1 . O1 . 1.288(2) yes
C1 . O4 . 1.237(2) yes
C2 . O2 . 1.288(2) yes
C2 . O3 . 1.237(2) yes
C3 . C4 . 1.542(3) yes
C3 . O5 . 1.275(2) yes
C3 . O8 . 1.245(3) yes
C4 . O6 . 1.296(3) yes
C4 . O7 . 1.232(2) yes
C5 . C6 . 1.548(3) yes
C5 . O9 . 1.282(2) yes
C5 . O12 . 1.239(2) yes
C6 . O10 . 1.295(2) yes
C6 . O11 . 1.224(2) yes
C7 . C8 . 1.544(3) yes
C7 . O13 . 1.293(2) yes
C7 . O16 . 1.231(2) yes
C8 . O14 . 1.295(3) yes
C8 . O15 . 1.224(3) yes
C9 . N2 . 1.381(3) yes
C9 . N3 . 1.351(3) yes
C9 . S1 . 1.658(2) yes
C10 . N6 . 1.367(3) yes
C10 . N7 . 1.356(3) yes
C10 . S2 . 1.672(2) yes
N1 . N2 . 1.432(3) yes
N1 . H12 . 0.895 no
N1 . H11 . 0.894 no
N1 . H13 . 0.896 no
N2 . H21 . 0.865 no
N3 . N4 . 1.415(3) yes
N3 . H31 . 0.854 no
N4 . H41 . 0.890 no
N4 . H42 . 0.888 no
N4 . H43 . 0.911 no
N5 . N6 . 1.417(3) yes
N5 . H52 . 0.898 no
N5 . H53 . 0.889 no
N5 . H51 . 0.890 no
N6 . H61 . 0.859 no
N7 . N8 . 1.419(2) yes
N7 . H71 . 0.857 no
N8 . H81 . 0.885 no
N8 . H82 . 0.899 no
N8 . H83 . 0.884 no
O1 . Zr1 . 2.202(2) yes
O2 . Zr1 . 2.199(2) yes
O5 . Zr1 . 2.181(3) yes
O6 . Zr1 . 2.240(2) yes
O9 . Zr1 . 2.250(2) yes
O10 . Zr1 . 2.151(2) yes
O13 . Zr1 . 2.228(2) yes
O14 . Zr1 . 2.171(2) yes
O170 . H1701 . 0.847 no
O170 . H1702 . 0.821 no
O180 . H1801 . 0.821 no
O180 . H1802 . 0.806 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . O1 . 113.23(17) yes
C2 . C1 . O4 . 120.87(18) yes
O1 . C1 . O4 . 125.91(18) yes
C1 . C2 . O2 . 112.98(17) yes
C1 . C2 . O3 . 121.94(18) yes
O2 . C2 . O3 . 125.08(18) yes
C4 . C3 . O5 . 113.63(17) yes
C4 . C3 . O8 . 120.70(18) yes
O5 . C3 . O8 . 125.66(18) yes
C3 . C4 . O6 . 112.83(17) yes
C3 . C4 . O7 . 121.05(18) yes
O6 . C4 . O7 . 126.11(18) yes
C6 . C5 . O9 . 113.24(15) yes
C6 . C5 . O12 . 119.97(16) yes
O9 . C5 . O12 . 126.78(18) yes
C5 . C6 . O10 . 112.85(16) yes
C5 . C6 . O11 . 120.85(17) yes
O10 . C6 . O11 . 126.26(19) yes
C8 . C7 . O13 . 113.74(16) yes
C8 . C7 . O16 . 120.25(17) yes
O13 . C7 . O16 . 126.01(18) yes
C7 . C8 . O14 . 112.97(17) yes
C7 . C8 . O15 . 121.00(18) yes
O14 . C8 . O15 . 126.01(18) yes
N2 . C9 . N3 . 110.81(18) yes
N2 . C9 . S1 . 124.79(16) yes
N3 . C9 . S1 . 124.34(16) yes
N6 . C10 . N7 . 111.93(17) yes
N6 . C10 . S2 . 123.46(15) yes
N7 . C10 . S2 . 124.47(16) yes
N2 . N1 . H12 . 111.1 no
N2 . N1 . H11 . 113.3 no
H12 . N1 . H11 . 107.9 no
N2 . N1 . H13 . 108.9 no
H12 . N1 . H13 . 107.5 no
H11 . N1 . H13 . 108.1 no
N1 . N2 . C9 . 116.20(16) yes
N1 . N2 . H21 . 114.3 no
C9 . N2 . H21 . 115.4 no
C9 . N3 . N4 . 119.24(17) yes
C9 . N3 . H31 . 122.1 no
N4 . N3 . H31 . 118.4 no
N3 . N4 . H41 . 111.2 no
N3 . N4 . H42 . 110.6 no
H41 . N4 . H42 . 109.4 no
N3 . N4 . H43 . 108.5 no
H41 . N4 . H43 . 110.2 no
H42 . N4 . H43 . 106.8 no
N6 . N5 . H52 . 109.4 no
N6 . N5 . H53 . 108.7 no
H52 . N5 . H53 . 109.7 no
N6 . N5 . H51 . 109.8 no
H52 . N5 . H51 . 110.8 no
H53 . N5 . H51 . 108.5 no
N5 . N6 . C10 . 115.90(16) yes
N5 . N6 . H61 . 116.0 no
C10 . N6 . H61 . 118.3 no
C10 . N7 . N8 . 119.03(17) yes
C10 . N7 . H71 . 119.3 no
N8 . N7 . H71 . 117.4 no
N7 . N8 . H81 . 111.2 no
N7 . N8 . H82 . 109.5 no
H81 . N8 . H82 . 109.3 no
N7 . N8 . H83 . 108.3 no
H81 . N8 . H83 . 109.2 no
H82 . N8 . H83 . 109.3 no
C1 . O1 . Zr1 . 120.75(13) yes
C2 . O2 . Zr1 . 121.38(13) yes
C3 . O5 . Zr1 . 122.23(14) yes
C4 . O6 . Zr1 . 119.52(13) yes
C5 . O9 . Zr1 . 119.15(13) yes
C6 . O10 . Zr1 . 121.68(13) yes
C7 . O13 . Zr1 . 119.69(13) yes
C8 . O14 . Zr1 . 122.14(13) yes
H1701 . O170 . H1702 . 104.7 no
H1801 . O180 . H1802 . 106.8 no
O9 . Zr1 . O6 . 128.37(6) yes
O9 . Zr1 . O13 . 135.15(6) yes
O6 . Zr1 . O13 . 71.34(7) yes
O9 . Zr1 . O1 . 70.82(9) yes
O6 . Zr1 . O1 . 134.83(7) yes
O13 . Zr1 . O1 . 127.86(7) yes
O9 . Zr1 . O2 . 141.50(7) yes
O6 . Zr1 . O2 . 78.86(10) yes
O13 . Zr1 . O2 . 74.38(9) yes
O1 . Zr1 . O2 . 70.86(8) yes
O9 . Zr1 . O5 . 77.50(10) yes
O6 . Zr1 . O5 . 70.91(9) yes
O13 . Zr1 . O5 . 141.24(7) yes
O1 . Zr1 . O5 . 76.32(10) yes
O2 . Zr1 . O5 . 90.06(10) yes
O9 . Zr1 . O14 . 77.40(7) yes
O6 . Zr1 . O14 . 142.42(6) yes
O13 . Zr1 . O14 . 71.46(9) yes
O1 . Zr1 . O14 . 74.94(8) yes
O2 . Zr1 . O14 . 96.13(8) yes
O9 . Zr1 . O10 . 71.17(8) yes
O6 . Zr1 . O10 . 76.37(7) yes
O13 . Zr1 . O10 . 77.70(8) yes
O1 . Zr1 . O10 . 141.44(6) yes
O2 . Zr1 . O10 . 147.32(6) yes
O5 . Zr1 . O14 . 146.67(6) yes
O5 . Zr1 . O10 . 101.49(8) yes
O14 . Zr1 . O10 . 90.75(9) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N4 . H41 . O170 2_765 166.0 0.890 1.843 2.714(3) yes
N4 . H42 . O8 1_554 130.0 0.888 2.395 3.039(3) yes
N2 . H21 . O16 2_665 173.0 0.865 1.964 2.825(3) yes
N1 . H12 . C2 . 149.0 0.895 2.591 3.387(3) yes
N1 . H12 . O2 . 164.0 0.895 1.921 2.793(3) yes
N1 . H11 . O12 1_545 169.0 0.894 2.079 2.961(3) yes
N8 . H81 . C3 2_676 141.0 0.885 2.547 3.284(3) yes
N8 . H81 . O8 2_676 145.0 0.885 2.167 2.938(3) yes
N5 . H53 . O3 2_666 163.0 0.889 1.946 2.809(3) yes
N5 . H51 . C1 1_455 141.0 0.890 2.556 3.294(3) yes
N5 . H51 . O1 1_455 125.0 0.890 2.241 2.850(3) yes
N5 . H51 . O4 1_455 140.0 0.890 2.314 3.052(3) yes
N5 . H51 . O170 1_455 126.0 0.890 2.308 2.922(3) yes
N8 . H82 . O15 2_675 148.0 0.899 1.898 2.706(3) yes
N8 . H82 . O16 2_675 123.0 0.899 2.303 2.893(3) yes
N8 . H83 . O3 1_465 145.0 0.884 1.988 2.758(3) yes
N3 . H31 . O13 2_665 168.0 0.854 1.954 2.795(3) yes
O170 . H1701 . O180 2_775 150.0 0.847 1.969 2.737(3) yes
O170 . H1702 . O14 . 165.0 0.821 2.125 2.925(3) yes
O180 . H1801 . O11 . 151.0 0.821 2.233 2.978(3) yes
O180 . H1802 . O10 2_675 153.0 0.806 2.346 3.083(3) yes
N6 . H61 . O9 1_455 179.0 0.859 1.994 2.852(3) yes
N1 . H13 . O8 2_666 160.0 0.896 1.958 2.816(3) yes
N7 . H71 . O12 1_455 174.0 0.857 1.983 2.837(3) yes
N4 . H43 . C4 2_665 171.0 0.911 2.519 3.422(3) yes
N4 . H43 . O6 2_665 158.0 0.911 1.972 2.839(3) yes
N4 . H43 . O7 2_665 143.0 0.911 2.513 3.285(3) yes


