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

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

data_2 #stilbene
_database_code_depnum_ccdc_archive 'CCDC 1418959'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_CHEMW03_2                   
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: A number of alerts are related to the given molecular weight and values calculated from it. 
These have all been changed to better reflect a more chemically sensible formula unit
including disordered solvent. Please see _publ_section_exptl_refinement below.
;
_vrf_PLAT051_2                   
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      15.65 %     
RESPONSE: These have been changed to take into account the solvent modelled using the 
SQUEEZE algorithm (see below).
;


# end Validation Reply Form


_audit_creation_date             2015-08-13
_audit_creation_method           CRYSTALS_ver_14.61_build_5555

_oxford_structure_analysis_title 'ST4020 in Fm-3m'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C199.5 H305.5 N34.5 O66.5 Zr6'

# Given Formula = C210 H330 N38 O70.00 Zr6 
# Dc =      1.26 Fooo =  10624.00 Mu =     25.28 M =   5054.46
# Found Formula = C96 H64 O32.00 Zr6 
# Dc =      0.57 FOOO =   4544.00 Mu =     21.00 M =   2276.86

_chemical_formula_sum            'C199.5 H305.5 N34.5 O66.5 Zr6'
_chemical_compound_source        ?
_chemical_melting_point          ?

_exptl_crystal_description       octahedron
_exptl_crystal_colour            grey

_diffrn_ambient_temperature      100
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.003 -0.006 -0.004 17550 5529 ' '
_platon_squeeze_details          
;
This accounts to 138 DMF molecules, which come from the solvent of crystallisation.
These have been included in the formula, and F(000), density, and mu changed 
accordingly.
;

#end of refcif 
_cell_length_a                   29.8884(3)
_cell_length_b                   29.8884(3)
_cell_length_c                   29.8884(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     26699.9(8)

_symmetry_cell_setting           cubic
_symmetry_space_group_name_H-M   'F m -3 m'
_symmetry_int_tables_number      225

# 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 .
_symmetry_space_group_name_Hall  ?
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
x+1/2,y,z+1/2
-x+1/2,-y,-z+1/2
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
y,z,x
-y,-z,-x
y,z+1/2,x+1/2
-y,-z+1/2,-x+1/2
y+1/2,z,x+1/2
-y+1/2,-z,-x+1/2
y+1/2,z+1/2,x
-y+1/2,-z+1/2,-x
z,x,y
-z,-x,-y
z,x+1/2,y+1/2
-z,-x+1/2,-y+1/2
z+1/2,x,y+1/2
-z+1/2,-x,-y+1/2
z+1/2,x+1/2,y
-z+1/2,-x+1/2,-y
x,y,-z
-x,-y,z
x,y+1/2,-z+1/2
-x,-y+1/2,z+1/2
x+1/2,y,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y+1/2,-z
-x+1/2,-y+1/2,z
y,z,-x
-y,-z,x
y,z+1/2,-x+1/2
-y,-z+1/2,x+1/2
y+1/2,z,-x+1/2
-y+1/2,-z,x+1/2
y+1/2,z+1/2,-x
-y+1/2,-z+1/2,x
z,x,-y
-z,-x,y
z,x+1/2,-y+1/2
-z,-x+1/2,y+1/2
z+1/2,x,-y+1/2
-z+1/2,-x,y+1/2
z+1/2,x+1/2,-y
-z+1/2,-x+1/2,y
y,-z,-x
-y,z,x
y,-z+1/2,-x+1/2
-y,z+1/2,x+1/2
y+1/2,-z,-x+1/2
-y+1/2,z,x+1/2
y+1/2,-z+1/2,-x
-y+1/2,z+1/2,x
z,-x,-y
-z,x,y
z,-x+1/2,-y+1/2
-z,x+1/2,y+1/2
z+1/2,-x,-y+1/2
-z+1/2,x,y+1/2
z+1/2,-x+1/2,-y
-z+1/2,x+1/2,y
-z,x,-y
z,-x,y
-z,x+1/2,-y+1/2
z,-x+1/2,y+1/2
-z+1/2,x,-y+1/2
z+1/2,-x,y+1/2
-z+1/2,x+1/2,-y
z+1/2,-x+1/2,y
-x,y,-z
x,-y,z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
-x+1/2,y,-z+1/2
x+1/2,-y,z+1/2
-x+1/2,y+1/2,-z
x+1/2,-y+1/2,z
-y,z,-x
y,-z,x
-y,z+1/2,-x+1/2
y,-z+1/2,x+1/2
-y+1/2,z,-x+1/2
y+1/2,-z,x+1/2
-y+1/2,z+1/2,-x
y+1/2,-z+1/2,x
x,-y,-z
-x,y,z
x,-y+1/2,-z+1/2
-x,y+1/2,z+1/2
x+1/2,-y,-z+1/2
-x+1/2,y,z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z
y,x,z
-y,-x,-z
y,x+1/2,z+1/2
-y,-x+1/2,-z+1/2
y+1/2,x,z+1/2
-y+1/2,-x,-z+1/2
y+1/2,x+1/2,z
-y+1/2,-x+1/2,-z
z,y,x
-z,-y,-x
z,y+1/2,x+1/2
-z,-y+1/2,-x+1/2
z+1/2,y,x+1/2
-z+1/2,-y,-x+1/2
z+1/2,y+1/2,x
-z+1/2,-y+1/2,-x
x,z,y
-x,-z,-y
x,z+1/2,y+1/2
-x,-z+1/2,-y+1/2
x+1/2,z,y+1/2
-x+1/2,-z,-y+1/2
x+1/2,z+1/2,y
-x+1/2,-z+1/2,-y
y,x,-z
-y,-x,z
y,x+1/2,-z+1/2
-y,-x+1/2,z+1/2
y+1/2,x,-z+1/2
-y+1/2,-x,z+1/2
y+1/2,x+1/2,-z
-y+1/2,-x+1/2,z
z,y,-x
-z,-y,x
z,y+1/2,-x+1/2
-z,-y+1/2,x+1/2
z+1/2,y,-x+1/2
-z+1/2,-y,x+1/2
z+1/2,y+1/2,-x
-z+1/2,-y+1/2,x
x,z,-y
-x,-z,y
x,z+1/2,-y+1/2
-x,-z+1/2,y+1/2
x+1/2,z,-y+1/2
-x+1/2,-z,y+1/2
x+1/2,z+1/2,-y
-x+1/2,-z+1/2,y
-z,y,-x
z,-y,x
-z,y+1/2,-x+1/2
z,-y+1/2,x+1/2
-z+1/2,y,-x+1/2
z+1/2,-y,x+1/2
-z+1/2,y+1/2,-x
z+1/2,-y+1/2,x
-x,z,-y
x,-z,y
-x,z+1/2,-y+1/2
x,-z+1/2,y+1/2
-x+1/2,z,-y+1/2
x+1/2,-z,y+1/2
-x+1/2,z+1/2,-y
x+1/2,-z+1/2,y
x,-z,-y
-x,z,y
x,-z+1/2,-y+1/2
-x,z+1/2,y+1/2
x+1/2,-z,-y+1/2
-x+1/2,z,y+1/2
x+1/2,-z+1/2,-y
-x+1/2,z+1/2,y
y,-x,-z
-y,x,z
y,-x+1/2,-z+1/2
-y,x+1/2,z+1/2
y+1/2,-x,-z+1/2
-y+1/2,x,z+1/2
y+1/2,-x+1/2,-z
-y+1/2,x+1/2,z
z,-y,-x
-z,y,x
z,-y+1/2,-x+1/2
-z,y+1/2,x+1/2
z+1/2,-y,-x+1/2
-z+1/2,y,x+1/2
z+1/2,-y+1/2,-x
-z+1/2,y+1/2,x
-y,x,-z
y,-x,z
-y,x+1/2,-z+1/2
y,-x+1/2,z+1/2
-y+1/2,x,-z+1/2
y+1/2,-x,z+1/2
-y+1/2,x+1/2,-z
y+1/2,-x+1/2,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
Zr -0.1862 2.2449 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'
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'
O 0.0492 0.0322 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'
C 0.0181 0.0091 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'
N 0.0311 0.0180 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'


_cell_formula_units_Z            4
_chemical_formula_weight         4798.60


_cell_measurement_reflns_used    1460
_cell_measurement_theta_min      4
_cell_measurement_theta_max      74
_cell_measurement_temperature    100
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             10064.0
_exptl_absorpt_coefficient_mu    2.49

# Sheldrick geometric approximatio 0.73 0.81 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.81
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_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_reflns_number            95174
_reflns_number_total             1235
_diffrn_reflns_av_R_equivalents  0.068
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1235 
# Theoretical number of reflections is about 1952 


_diffrn_reflns_theta_min         2.957
_diffrn_reflns_theta_max         66.283
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        66.283
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       2
_diffrn_reflns_limit_l_max       35
_reflns_limit_h_min              0
_reflns_limit_h_max              20
_reflns_limit_k_min              0
_reflns_limit_k_max              25
_reflns_limit_l_min              2
_reflns_limit_l_max              35

_oxford_diffrn_Wilson_B_factor   1.43
_oxford_diffrn_Wilson_scale      587.59

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

_refine_diff_density_min         -1.36
_refine_diff_density_max         0.61


# 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>2.0\s(I)
_refine_ls_number_reflns         951
_refine_ls_number_restraints     191
_refine_ls_number_parameters     48
_oxford_refine_ls_R_factor_ref   0.0761
_refine_ls_wR_factor_ref         0.0871
_refine_ls_goodness_of_fit_ref   1.0719
_refine_ls_shift/su_max          0.0025576
_refine_ls_shift/su_mean         0.0002726


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1221
_refine_ls_R_factor_all          0.0902
_refine_ls_wR_factor_all         0.0963

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                951
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_gt          0.0871


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #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: 
 2.25 1.23 1.65 
;

# 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 0.58231(3) 0.5000 0.5000 0.0302 1.0000 Uani S T . . . .
O2 O 0.61834(18) 0.5642(2) 0.5000 0.0851 1.0000 Uani DS TU . . . .
C1 C 0.6051(3) 0.6051(3) 0.5000 0.1195 1.0000 Uani DS TU . . . .
C2 C 0.6399(2) 0.6399(2) 0.5000 0.1052 1.0000 Uani DS TU . . . .
C5 C 0.7057(2) 0.7057(2) 0.5000 0.1070 1.0000 Uani DS TU . . . .
C6 C 0.72845(15) 0.7467(2) 0.5143(4) 0.105(3) 0.2500 Uiso D U . . . .
C30 C 0.6351(3) 0.6774(3) 0.5259(3) 0.105(2) 0.2500 Uiso D U . . . .
C31 C 0.6280(3) 0.6846(3) 0.500000(7) 0.105(3) 0.5000 Uiso DS U . . . .
C40 C 0.6680(3) 0.7096(3) 0.5263(3) 0.105(2) 0.2500 Uiso D U . . . .
C41 C 0.6608(3) 0.7174(4) 0.500000(7) 0.105(3) 0.5000 Uiso DS U . . . .
O10 O 0.5341(3) 0.4659(3) 0.4659(3) 0.0298 0.5000 Uani DS TU . . . .
O11 O 0.5458(2) 0.4542(2) 0.4542(2) 0.0351 0.5000 Uani DS TU . . . .
H111 H 0.5621 0.4379 0.4379 0.0461 0.5000 Uiso D . . . . .
H301 H 0.6090 0.6812 0.5437 0.1265 0.2500 Uiso R . . . . .
H401 H 0.6648 0.7351 0.5450 0.1266 0.2500 Uiso R . . . . .
H311 H 0.5973 0.6928 0.5000 0.1260 0.5000 Uiso RS . . . . .
H411 H 0.6525 0.7481 0.5000 0.1259 0.5000 Uiso RS . . . . .
H61 H 0.7102 0.7707 0.5244 0.1263 0.2500 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.0645(4)
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 . Zr1 18_666 3.4793(12) yes
Zr1 . Zr1 9_555 3.4793(12) yes
Zr1 . Zr1 49_566 3.4793(12) yes
Zr1 . Zr1 41_556 3.4793(12) yes
Zr1 . O2 . 2.199(6) yes
Zr1 . O10 . 2.038(2) yes
Zr1 . O11 . 2.223(5) yes
O2 . C1 . 1.287(7) yes
C1 . C2 . 1.470(9) yes
C2 . C31 97_555 1.381(9) yes
C2 . C30 121_556 1.369(9) yes
C2 . C30 25_556 1.369(9) yes
C2 . C30 97_555 1.369(9) yes
C2 . C30 . 1.369(9) yes
C2 . C31 . 1.381(9) yes
C5 . C6 25_556 1.467(8) yes
C5 . C6 97_555 1.467(8) yes
C5 . C6 121_556 1.467(8) yes
C5 . C41 97_555 1.386(9) yes
C5 . C40 97_555 1.377(9) yes
C5 . C40 121_556 1.377(9) yes
C5 . C40 25_556 1.377(9) yes
C5 . C6 . 1.467(8) yes
C5 . C40 . 1.377(9) yes
C5 . C41 . 1.386(9) yes
C6 . C6 8_666 1.558(15) yes
C6 . C6 104_666 1.353(17) yes
C6 . C6 32_665 1.303(9) yes
C6 . C6 121_556 1.15(2) yes
C6 . C6 128_665 1.048(12) yes
C6 . C6 25_556 0.86(2) yes
C6 . C6 97_555 0.773(13) yes
C6 . H61 . 0.950 no
C30 . C30 25_556 1.548(16) yes
C30 . C30 97_555 1.789(16) yes
C30 . C31 . 0.831(8) yes
C30 . C40 . 1.379(9) yes
C30 . C41 . 1.619(13) yes
C30 . H301 . 0.950 no
C31 . C40 25_556 1.616(13) yes
C31 . C40 . 1.616(13) yes
C31 . C41 . 1.388(9) yes
C31 . H311 . 0.950 no
C40 . C40 25_556 1.571(16) yes
C40 . C40 97_555 1.758(16) yes
C40 . C41 . 0.847(8) yes
C40 . H401 . 0.950 no
C41 . H411 . 0.950 no
O11 . H111 . 0.843 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
Zr1 18_666 Zr1 . Zr1 9_555 60.000 yes
Zr1 18_666 Zr1 . Zr1 49_566 60.000 yes
Zr1 9_555 Zr1 . Zr1 49_566 90.000 yes
Zr1 18_666 Zr1 . Zr1 41_556 90.000 yes
Zr1 9_555 Zr1 . Zr1 41_556 60.000 yes
Zr1 49_566 Zr1 . Zr1 41_556 60.000 yes
Zr1 18_666 Zr1 . O2 . 164.31(16) yes
Zr1 9_555 Zr1 . O2 . 110.25(10) yes
Zr1 49_566 Zr1 . O2 . 110.25(10) yes
Zr1 41_556 Zr1 . O2 . 74.31(16) yes
Zr1 18_666 Zr1 . O10 . 31.39(11) yes
Zr1 9_555 Zr1 . O10 . 81.5(3) yes
Zr1 49_566 Zr1 . O10 . 31.39(11) yes
Zr1 41_556 Zr1 . O10 . 81.5(3) yes
O2 . Zr1 . O10 . 141.45(11) yes
Zr1 18_666 Zr1 . O11 . 38.49(17) yes
Zr1 9_555 Zr1 . O11 . 95.1(2) yes
Zr1 49_566 Zr1 . O11 . 38.49(17) yes
Zr1 41_556 Zr1 . O11 . 95.1(2) yes
O2 . Zr1 . O11 . 141.03(6) yes
O10 . Zr1 . O11 . 15.6(4) yes
Zr1 . O2 . C1 . 132.8(6) yes
O2 97_555 C1 . O2 . 125.7(9) yes
O2 97_555 C1 . C2 . 117.1(5) yes
O2 . C1 . C2 . 117.1(5) yes
C1 . C2 . C31 97_555 120.0(5) yes
C1 . C2 . C30 121_556 120.2(5) yes
C31 97_555 C2 . C30 121_556 35.2(3) yes
C1 . C2 . C30 25_556 120.2(5) yes
C31 97_555 C2 . C30 25_556 108.3(6) yes
C30 121_556 C2 . C30 25_556 81.6(7) yes
C1 . C2 . C30 97_555 120.2(5) yes
C31 97_555 C2 . C30 97_555 35.2(3) yes
C30 121_556 C2 . C30 97_555 68.9(6) yes
C30 25_556 C2 . C30 97_555 119.5(10) yes
C1 . C2 . C30 . 120.2(5) yes
C31 97_555 C2 . C30 . 108.3(6) yes
C30 121_556 C2 . C30 . 119.5(10) yes
C30 25_556 C2 . C30 . 68.9(6) yes
C30 97_555 C2 . C30 . 81.6(7) yes
C1 . C2 . C31 . 120.0(5) yes
C31 97_555 C2 . C31 . 119.9(9) yes
C30 121_556 C2 . C31 . 108.3(6) yes
C30 25_556 C2 . C31 . 35.2(3) yes
C30 97_555 C2 . C31 . 108.3(6) yes
C30 . C2 . C31 . 35.2(3) yes
C6 25_556 C5 . C6 97_555 46.3(8) yes
C6 25_556 C5 . C6 121_556 30.5(5) yes
C6 97_555 C5 . C6 121_556 33.9(9) yes
C6 25_556 C5 . C41 97_555 133.8(6) yes
C6 97_555 C5 . C41 97_555 103.7(5) yes
C6 121_556 C5 . C41 97_555 103.7(5) yes
C6 25_556 C5 . C40 97_555 144.0(6) yes
C6 97_555 C5 . C40 97_555 98.1(6) yes
C6 121_556 C5 . C40 97_555 118.2(4) yes
C41 97_555 C5 . C40 97_555 35.7(3) yes
C6 25_556 C5 . C40 121_556 118.5(6) yes
C6 97_555 C5 . C40 121_556 118.2(4) yes
C6 121_556 C5 . C40 121_556 98.1(6) yes
C41 97_555 C5 . C40 121_556 35.7(3) yes
C40 97_555 C5 . C40 121_556 69.6(7) yes
C6 25_556 C5 . C40 25_556 98.1(6) yes
C6 97_555 C5 . C40 25_556 144.0(6) yes
C6 121_556 C5 . C40 25_556 118.5(6) yes
C41 97_555 C5 . C40 25_556 106.9(6) yes
C40 97_555 C5 . C40 25_556 117.8(9) yes
C6 25_556 C5 . C6 . 33.9(9) yes
C6 97_555 C5 . C6 . 30.5(5) yes
C6 121_556 C5 . C6 . 46.3(8) yes
C41 97_555 C5 . C6 . 133.8(6) yes
C40 97_555 C5 . C6 . 118.5(6) yes
C6 25_556 C5 . C40 . 118.2(4) yes
C6 97_555 C5 . C40 . 118.5(6) yes
C6 121_556 C5 . C40 . 144.0(6) yes
C41 97_555 C5 . C40 . 106.9(6) yes
C40 97_555 C5 . C40 . 79.4(6) yes
C6 25_556 C5 . C41 . 103.7(5) yes
C6 97_555 C5 . C41 . 133.8(6) yes
C6 121_556 C5 . C41 . 133.8(6) yes
C41 97_555 C5 . C41 . 119.3(10) yes
C40 97_555 C5 . C41 . 106.9(6) yes
C40 121_556 C5 . C40 25_556 79.4(6) yes
C40 121_556 C5 . C6 . 144.0(6) yes
C40 25_556 C5 . C6 . 118.2(4) yes
C40 121_556 C5 . C40 . 117.8(9) yes
C40 25_556 C5 . C40 . 69.6(7) yes
C6 . C5 . C40 . 98.1(6) yes
C40 121_556 C5 . C41 . 106.9(6) yes
C40 25_556 C5 . C41 . 35.7(3) yes
C6 . C5 . C41 . 103.7(5) yes
C40 . C5 . C41 . 35.7(3) yes
C6 8_666 C6 . C5 . 109.1(10) yes
C6 8_666 C6 . C6 104_666 29.7(5) yes
C5 . C6 . C6 104_666 121.9(12) yes
C6 8_666 C6 . C6 32_665 33.3(7) yes
C5 . C6 . C6 32_665 125.7(8) yes
C6 104_666 C6 . C6 32_665 51.4(8) yes
C6 8_666 C6 . C6 121_556 42.3(7) yes
C5 . C6 . C6 121_556 66.9(4) yes
C6 104_666 C6 . C6 121_556 62.0(8) yes
C6 32_665 C6 . C6 121_556 66.5(6) yes
C6 8_666 C6 . C6 128_665 47.7(7) yes
C5 . C6 . C6 128_665 156.9(4) yes
C6 104_666 C6 . C6 128_665 39.2(8) yes
C6 32_665 C6 . C6 128_665 36.4(6) yes
C6 121_556 C6 . C6 128_665 90.000 yes
C6 8_666 C6 . C6 25_556 56.7(7) yes
C5 . C6 . C6 25_556 73.1(4) yes
C6 104_666 C6 . C6 25_556 50.8(8) yes
C6 32_665 C6 . C6 25_556 90.000 yes
C6 121_556 C6 . C6 25_556 42.1(8) yes
C6 8_666 C6 . C6 97_555 60.3(5) yes
C5 . C6 . C6 97_555 74.7(2) yes
C6 104_666 C6 . C6 97_555 90.000 yes
C6 32_665 C6 . C6 97_555 53.6(6) yes
C6 121_556 C6 . C6 97_555 47.9(8) yes
C6 8_666 C6 . H61 . 123.8 no
C5 . C6 . H61 . 117.1 no
C6 104_666 C6 . H61 . 95.9 no
C6 32_665 C6 . H61 . 117.1 no
C6 121_556 C6 . H61 . 150.0 no
C6 128_665 C6 . C6 25_556 90.000 yes
C6 128_665 C6 . C6 97_555 90.000 yes
C6 25_556 C6 . C6 97_555 90.000 yes
C6 128_665 C6 . H61 . 82.8 no
C6 25_556 C6 . H61 . 108.5 no
C6 97_555 C6 . H61 . 160.0 no
C30 25_556 C30 . C2 . 55.6(3) yes
C30 25_556 C30 . C30 97_555 90.000 yes
C2 . C30 . C30 97_555 49.2(3) yes
C30 25_556 C30 . C31 . 21.3(8) yes
C2 . C30 . C31 . 73.2(9) yes
C30 97_555 C30 . C31 . 111.3(8) yes
C30 25_556 C30 . C40 . 90.5(4) yes
C2 . C30 . C40 . 120.0(7) yes
C30 97_555 C30 . C40 . 89.4(4) yes
C31 . C30 . C40 . 90.5(11) yes
C30 25_556 C30 . C41 . 61.4(3) yes
C2 . C30 . C41 . 106.5(6) yes
C30 97_555 C30 . C41 . 100.7(4) yes
C31 . C30 . C41 . 59.0(8) yes
C40 . C30 . C41 . 31.5(4) yes
C30 25_556 C30 . H301 . 124.0 no
C2 . C30 . H301 . 120.0 no
C30 97_555 C30 . H301 . 131.6 no
C31 . C30 . H301 . 106.3 no
C40 . C30 . H301 . 120.0 no
C41 . C30 . H301 . 124.7 no
C40 25_556 C31 . C2 . 104.9(6) yes
C40 25_556 C31 . C30 . 112.6(12) yes
C2 . C31 . C30 . 71.6(9) yes
C40 25_556 C31 . C30 25_556 58.5(8) yes
C2 . C31 . C30 25_556 71.6(9) yes
C30 . C31 . C30 25_556 137.5(17) yes
C40 25_556 C31 . C40 . 58.1(7) yes
C2 . C31 . C40 . 104.9(6) yes
C30 . C31 . C40 . 58.5(8) yes
C30 25_556 C31 . C40 . 112.6(12) yes
C40 25_556 C31 . C41 . 31.6(4) yes
C2 . C31 . C41 . 120.0(7) yes
C30 . C31 . C41 . 90.1(10) yes
C30 25_556 C31 . C41 . 90.1(10) yes
C40 . C31 . C41 . 31.6(4) yes
C40 25_556 C31 . H311 . 126.5 no
C2 . C31 . H311 . 120.0 no
C30 . C31 . H311 . 108.2 no
C30 25_556 C31 . H311 . 108.2 no
C40 . C31 . H311 . 126.5 no
C41 . C31 . H311 . 120.0 no
C40 25_556 C40 . C31 . 60.9(3) yes
C40 25_556 C40 . C30 . 89.5(4) yes
C31 . C40 . C30 . 30.9(4) yes
C40 25_556 C40 . C5 . 55.2(3) yes
C31 . C40 . C5 . 106.7(6) yes
C30 . C40 . C5 . 121.3(7) yes
C40 25_556 C40 . C40 97_555 90.000 yes
C31 . C40 . C40 97_555 101.3(4) yes
C30 . C40 . C40 97_555 90.6(4) yes
C5 . C40 . C40 97_555 50.3(3) yes
C40 25_556 C40 . C41 . 22.0(8) yes
C31 . C40 . C41 . 59.2(8) yes
C30 . C40 . C41 . 90.1(11) yes
C5 . C40 . C41 . 72.7(8) yes
C40 97_555 C40 . C41 . 111.9(8) yes
C40 25_556 C40 . H401 . 126.2 no
C31 . C40 . H401 . 125.5 no
C30 . C40 . H401 . 119.4 no
C5 . C40 . H401 . 119.4 no
C40 97_555 C40 . H401 . 129.8 no
C41 . C40 . H401 . 107.6 no
C30 25_556 C41 . C30 . 57.1(7) yes
C30 25_556 C41 . C31 . 30.9(4) yes
C30 . C41 . C31 . 30.9(4) yes
C30 25_556 C41 . C5 . 105.9(7) yes
C30 . C41 . C5 . 105.9(7) yes
C31 . C41 . C5 . 120.4(7) yes
C30 25_556 C41 . C40 . 111.3(12) yes
C30 . C41 . C40 . 58.4(8) yes
C31 . C41 . C40 . 89.3(10) yes
C5 . C41 . C40 . 71.6(8) yes
C30 25_556 C41 . C40 25_556 58.4(8) yes
C30 . C41 . C40 25_556 111.3(12) yes
C31 . C41 . C40 25_556 89.3(10) yes
C5 . C41 . C40 25_556 71.6(8) yes
C40 . C41 . C40 25_556 136.1(16) yes
C30 25_556 C41 . H411 . 126.1 no
C30 . C41 . H411 . 126.1 no
C31 . C41 . H411 . 119.9 no
C5 . C41 . H411 . 119.8 no
C40 . C41 . H411 . 109.3 no
C40 25_556 C41 . H411 . 109.3 no
Zr1 . O10 . Zr1 10_666 117.2(2) yes
Zr1 . O10 . Zr1 18_666 117.2(2) yes
Zr1 10_666 O10 . Zr1 18_666 117.2(2) yes
Zr1 . O11 . Zr1 10_666 103.0(3) yes
Zr1 . O11 . Zr1 18_666 103.0(3) yes
Zr1 10_666 O11 . Zr1 18_666 103.0(3) yes
Zr1 . O11 . H111 . 115.3 no
Zr1 10_666 O11 . H111 . 115.3 no
Zr1 18_666 O11 . H111 . 115.3 no



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 0 10 x .
2 2 8 x .
_refine_special_details          SQUEEZE
####################################################################### 
# 
# 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_etdb_Me2
_database_code_depnum_ccdc_archive 'CCDC 1418960'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;
_audit_creation_date             2015-06-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O4'
_chemical_formula_sum            'C18 H18 O4'
_chemical_formula_weight         298.32
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.7414(4)
_cell_length_b                   6.0450(6)
_cell_length_c                   25.976(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.197(4)
_cell_angle_gamma                90
_cell_volume                     742.53(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7105
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      3.15
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7061
_exptl_absorpt_correction_T_min  0.5560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1500 before and 0.1195 after correction.
The Ratio of minimum to maximum transmission is 0.7874.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       column
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10757
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.392
_diffrn_reflns_theta_min         1.572
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1465
_reflns_number_total             1667
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0727P)²+0.4777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1597
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1151(3) 0.5679(2) 0.33004(5) 0.0210(3) Uani 1 1 d . . . . .
O2 O 0.0683(3) 0.2326(2) 0.29350(5) 0.0259(4) Uani 1 1 d . . . . .
C1 C -0.0905(4) 0.6519(3) 0.29053(7) 0.0222(4) Uani 1 1 d . . . . .
H1A H -0.0349 0.6103 0.2571 0.033 Uiso 1 1 calc GR . . . .
H1B H -0.0991 0.8102 0.2928 0.033 Uiso 1 1 calc GR . . . .
H1C H -0.2732 0.5906 0.2956 0.033 Uiso 1 1 calc GR . . . .
C2 C 0.1760(3) 0.3522(3) 0.32620(6) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.3975(3) 0.2801(3) 0.36641(6) 0.0154(4) Uani 1 1 d . . . . .
C4 C 0.5001(4) 0.4185(3) 0.40634(7) 0.0204(4) Uani 1 1 d . . . . .
H4 H 0.4260 0.5600 0.4092 0.024 Uiso 1 1 calc R . . . .
C5 C 0.7128(4) 0.3454(3) 0.44181(7) 0.0223(4) Uani 1 1 d . . . . .
H5 H 0.7780 0.4385 0.4686 0.027 Uiso 1 1 calc R . . . .
C6 C 0.8306(3) 0.1351(3) 0.43809(7) 0.0192(4) Uani 1 1 d . . . . .
C7 C 0.7252(4) -0.0020(3) 0.39821(7) 0.0207(4) Uani 1 1 d . . . . .
H7 H 0.8005 -0.1430 0.3951 0.025 Uiso 1 1 calc R . . . .
C8 C 0.5094(4) 0.0679(3) 0.36291(7) 0.0190(4) Uani 1 1 d . . . . .
H8 H 0.4394 -0.0271 0.3369 0.023 Uiso 1 1 calc R . . . .
C9 C 1.0598(4) 0.0553(3) 0.47689(7) 0.0235(4) Uani 1 1 d . . . . .
H9A H 1.1762 0.1799 0.4887 0.028 Uiso 1 1 calc R . . . .
H9B H 1.1796 -0.0490 0.4603 0.028 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.454(2) . ?
O1 C2 1.341(2) . ?
O2 C2 1.201(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.491(2) . ?
C3 C4 1.392(2) . ?
C3 C8 1.393(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(3) . ?
C6 C7 1.391(3) . ?
C6 C9 1.506(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(2) . ?
C8 H8 0.9300 . ?
C9 C9 1.520(4) 3_756 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 115.09(14) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 112.14(14) . . ?
O2 C2 O1 123.73(16) . . ?
O2 C2 C3 124.11(16) . . ?
C4 C3 C2 122.40(15) . . ?
C4 C3 C8 119.19(15) . . ?
C8 C3 C2 118.39(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.05(16) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.30(17) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C9 121.24(17) . . ?
C7 C6 C5 118.10(16) . . ?
C7 C6 C9 120.65(17) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.17(17) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 H8 119.9 . . ?
C7 C8 C3 120.18(16) . . ?
C7 C8 H8 119.9 . . ?
C6 C9 C9 112.13(18) . 3_756 ?
C6 C9 H9A 109.2 . . ?
C6 C9 H9B 109.2 . . ?
C9 C9 H9A 109.2 3_756 . ?
C9 C9 H9B 109.2 3_756 . ?
H9A C9 H9B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 7.0(2) . . . . ?
O1 C2 C3 C8 -171.49(15) . . . . ?
O2 C2 C3 C4 -174.38(17) . . . . ?
O2 C2 C3 C8 7.1(3) . . . . ?
C1 O1 C2 O2 -1.3(2) . . . . ?
C1 O1 C2 C3 177.35(14) . . . . ?
C2 C3 C4 C5 -177.96(16) . . . . ?
C2 C3 C8 C7 177.04(15) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C3 C8 C7 -1.5(3) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C4 C5 C6 C9 -179.49(16) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C9 C9 88.3(3) . . . 3_756 ?
C6 C7 C8 C3 1.1(3) . . . . ?
C7 C6 C9 C9 -90.0(3) . . . 3_756 ?
C8 C3 C4 C5 0.5(3) . . . . ?
C9 C6 C7 C8 178.51(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

#### END OF CIF for etdb-Me2

####################################################################### 
# 
# 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_2Br2 #2015ncs0303_x_sq
_database_code_depnum_ccdc_archive 'CCDC 1418961'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;
_audit_creation_date             2015-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;

# SQUEEZE RESULTS (Version =  50315)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.280 -0.006 -0.004 18145 3735 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         ' Zr6 O4 (O H)4 (C16 H10 O4 Br2)6'
_chemical_formula_sum            'C96 H64 Br12 O32 Zr6'
_chemical_formula_weight         3235.71
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      cubic
_space_group_IT_number           225
_space_group_name_H-M_alt        'F m -3 m'
_space_group_name_Hall           '-F 4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'x, -z, y'
'x, -y, -z'
'x, z, -y'
'z, y, -x'
'-x, y, -z'
'-z, y, x'
'z, x, y'
'y, z, x'
'-y, -z, x'
'z, -x, -y'
'-y, z, -x'
'-z, -x, y'
'-z, x, -y'
'y, -z, -x'
'y, x, -z'
'-y, -x, -z'
'-x, z, y'
'-x, -z, -y'
'z, -y, x'
'-z, -y, -x'
'x, y+1/2, z+1/2'
'-y, x+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'y, -x+1/2, z+1/2'
'x, -z+1/2, y+1/2'
'x, -y+1/2, -z+1/2'
'x, z+1/2, -y+1/2'
'z, y+1/2, -x+1/2'
'-x, y+1/2, -z+1/2'
'-z, y+1/2, x+1/2'
'z, x+1/2, y+1/2'
'y, z+1/2, x+1/2'
'-y, -z+1/2, x+1/2'
'z, -x+1/2, -y+1/2'
'-y, z+1/2, -x+1/2'
'-z, -x+1/2, y+1/2'
'-z, x+1/2, -y+1/2'
'y, -z+1/2, -x+1/2'
'y, x+1/2, -z+1/2'
'-y, -x+1/2, -z+1/2'
'-x, z+1/2, y+1/2'
'-x, -z+1/2, -y+1/2'
'z, -y+1/2, x+1/2'
'-z, -y+1/2, -x+1/2'
'x+1/2, y, z+1/2'
'-y+1/2, x, z+1/2'
'-x+1/2, -y, z+1/2'
'y+1/2, -x, z+1/2'
'x+1/2, -z, y+1/2'
'x+1/2, -y, -z+1/2'
'x+1/2, z, -y+1/2'
'z+1/2, y, -x+1/2'
'-x+1/2, y, -z+1/2'
'-z+1/2, y, x+1/2'
'z+1/2, x, y+1/2'
'y+1/2, z, x+1/2'
'-y+1/2, -z, x+1/2'
'z+1/2, -x, -y+1/2'
'-y+1/2, z, -x+1/2'
'-z+1/2, -x, y+1/2'
'-z+1/2, x, -y+1/2'
'y+1/2, -z, -x+1/2'
'y+1/2, x, -z+1/2'
'-y+1/2, -x, -z+1/2'
'-x+1/2, z, y+1/2'
'-x+1/2, -z, -y+1/2'
'z+1/2, -y, x+1/2'
'-z+1/2, -y, -x+1/2'
'x+1/2, y+1/2, z'
'-y+1/2, x+1/2, z'
'-x+1/2, -y+1/2, z'
'y+1/2, -x+1/2, z'
'x+1/2, -z+1/2, y'
'x+1/2, -y+1/2, -z'
'x+1/2, z+1/2, -y'
'z+1/2, y+1/2, -x'
'-x+1/2, y+1/2, -z'
'-z+1/2, y+1/2, x'
'z+1/2, x+1/2, y'
'y+1/2, z+1/2, x'
'-y+1/2, -z+1/2, x'
'z+1/2, -x+1/2, -y'
'-y+1/2, z+1/2, -x'
'-z+1/2, -x+1/2, y'
'-z+1/2, x+1/2, -y'
'y+1/2, -z+1/2, -x'
'y+1/2, x+1/2, -z'
'-y+1/2, -x+1/2, -z'
'-x+1/2, z+1/2, y'
'-x+1/2, -z+1/2, -y'
'z+1/2, -y+1/2, x'
'-z+1/2, -y+1/2, -x'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x, z, -y'
'-x, y, z'
'-x, -z, y'
'-z, -y, x'
'x, -y, z'
'z, -y, -x'
'-z, -x, -y'
'-y, -z, -x'
'y, z, -x'
'-z, x, y'
'y, -z, x'
'z, x, -y'
'z, -x, y'
'-y, z, x'
'-y, -x, z'
'y, x, z'
'x, -z, -y'
'x, z, y'
'-z, y, -x'
'z, y, x'
'-x, -y+1/2, -z+1/2'
'y, -x+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'-y, x+1/2, -z+1/2'
'-x, z+1/2, -y+1/2'
'-x, y+1/2, z+1/2'
'-x, -z+1/2, y+1/2'
'-z, -y+1/2, x+1/2'
'x, -y+1/2, z+1/2'
'z, -y+1/2, -x+1/2'
'-z, -x+1/2, -y+1/2'
'-y, -z+1/2, -x+1/2'
'y, z+1/2, -x+1/2'
'-z, x+1/2, y+1/2'
'y, -z+1/2, x+1/2'
'z, x+1/2, -y+1/2'
'z, -x+1/2, y+1/2'
'-y, z+1/2, x+1/2'
'-y, -x+1/2, z+1/2'
'y, x+1/2, z+1/2'
'x, -z+1/2, -y+1/2'
'x, z+1/2, y+1/2'
'-z, y+1/2, -x+1/2'
'z, y+1/2, x+1/2'
'-x+1/2, -y, -z+1/2'
'y+1/2, -x, -z+1/2'
'x+1/2, y, -z+1/2'
'-y+1/2, x, -z+1/2'
'-x+1/2, z, -y+1/2'
'-x+1/2, y, z+1/2'
'-x+1/2, -z, y+1/2'
'-z+1/2, -y, x+1/2'
'x+1/2, -y, z+1/2'
'z+1/2, -y, -x+1/2'
'-z+1/2, -x, -y+1/2'
'-y+1/2, -z, -x+1/2'
'y+1/2, z, -x+1/2'
'-z+1/2, x, y+1/2'
'y+1/2, -z, x+1/2'
'z+1/2, x, -y+1/2'
'z+1/2, -x, y+1/2'
'-y+1/2, z, x+1/2'
'-y+1/2, -x, z+1/2'
'y+1/2, x, z+1/2'
'x+1/2, -z, -y+1/2'
'x+1/2, z, y+1/2'
'-z+1/2, y, -x+1/2'
'z+1/2, y, x+1/2'
'-x+1/2, -y+1/2, -z'
'y+1/2, -x+1/2, -z'
'x+1/2, y+1/2, -z'
'-y+1/2, x+1/2, -z'
'-x+1/2, z+1/2, -y'
'-x+1/2, y+1/2, z'
'-x+1/2, -z+1/2, y'
'-z+1/2, -y+1/2, x'
'x+1/2, -y+1/2, z'
'z+1/2, -y+1/2, -x'
'-z+1/2, -x+1/2, -y'
'-y+1/2, -z+1/2, -x'
'y+1/2, z+1/2, -x'
'-z+1/2, x+1/2, y'
'y+1/2, -z+1/2, x'
'z+1/2, x+1/2, -y'
'z+1/2, -x+1/2, y'
'-y+1/2, z+1/2, x'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'
'x+1/2, -z+1/2, -y'
'x+1/2, z+1/2, y'
'-z+1/2, y+1/2, -x'
'z+1/2, y+1/2, x'

_cell_length_a                   29.7685(8)
_cell_length_b                   29.7685(8)
_cell_length_c                   29.7685(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     26380(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12321
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.077
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    0.815
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             6224
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            95174
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.987
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_min         2.737
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
scan:
	Number of images: 104
	           Slice: -31.0000 - 73.0000
	     Image width: 1.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 0.0000
	             XTD: 45.0166
	          2theta: -17.2137
scan:
	Number of images: 91
	           Slice: -69.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -120.0000
	             XTD: 45.0166
	          2theta: -17.2137
scan:
	Number of images: 93
	           Slice: -71.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 60.0000
	             XTD: 45.0166
	          2theta: -17.2137
scan:
	Number of images: 84
	           Slice: -59.0000 - 25.0000
	     Image width: 1.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: -150.0000
	             XTD: 45.0166
	          2theta: -17.2137
scan:
	Number of images: 18
	           Slice: -26.0000 - -8.0000
	     Image width: 1.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -180.0000
	             XTD: 45.0166
	          2theta: -17.2137
scan:
	Number of images: 108
	           Slice: -35.0000 - 73.0000
	     Image width: 1.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: 60.0000
	             XTD: 45.0166
	          2theta: -17.2137
scan:
	Number of images: 100
	           Slice: -78.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -60.0000
	             XTD: 45.0166
	          2theta: -17.2137
scan:
	Number of images: 90
	           Slice: -68.0000 - 22.0000
	     Image width: 1.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: 120.0000
	             XTD: 45.0166
	          2theta: -17.2137
scan:
	Number of images: 57
	           Slice: -87.0000 - -30.0000
	     Image width: 1.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: -60.0000
	             XTD: 45.0166
	          2theta: -17.2137
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support MiTeGen
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.011322
_diffrn_orient_matrix_UB_12      0.031481
_diffrn_orient_matrix_UB_13      0.003037
_diffrn_orient_matrix_UB_21      -0.022204
_diffrn_orient_matrix_UB_22      -0.005614
_diffrn_orient_matrix_UB_23      -0.024575
_diffrn_orient_matrix_UB_31      -0.022522
_diffrn_orient_matrix_UB_32      -0.010290
_diffrn_orient_matrix_UB_33      0.022700
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1075
_reflns_number_total             1211
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007)
;
_refine_diff_density_max         1.082
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     35
_refine_ls_number_reflns         1211
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0843
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1770P)²+230.5540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2562
_refine_ls_wR_factor_ref         0.2677
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Br1-C6
 1.9 with sigma of 0.02
 C6-C6_$1
 1.53 with sigma of 0.02
 C6-C5
 1.5 with sigma of 0.02
 C3X-C2 = C4X-C3X = C5-C4X
 1.39 with sigma of 0.02
 Br1-C5 \\sim Br1-C6_$1
 with sigma of 0.02
3. Restrained planarity
 C2, C3X, C4X, C5
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C5 \\sim C6 \\sim C4X \\sim C3X: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C6(0.25) C4X(0.5) H4X(0.5) C3X(0.5) H3X(0.5)
7.a Aromatic/amide H refined with riding coordinates:
 C4X(H4X), C3X(H3X)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zr1 Zr 0.5000 0.08279(3) 0.5000 0.0411(6) Uani 1 8 d S TU P . .
Br1 Br 0.7500 0.2500 0.5791(3) 0.509(7) Uani 1 4 d DS TU P . .
O1 O 0.5643(2) 0.11946(19) 0.5000 0.0921(19) Uani 1 2 d S TU P . .
O2 O 0.5405(2) 0.0405(2) 0.4595(2) 0.076(3) Uani 1 6 d S TU P . .
C1 C 0.6045(4) 0.1045(4) 0.5000 0.106(4) Uiso 1 4 d S TU P . .
C2 C 0.6419(5) 0.1419(5) 0.5000 0.146(7) Uiso 1 4 d DS TU P . .
C5 C 0.7061(7) 0.2061(7) 0.5000 0.34(2) Uiso 1 4 d DS TU P . .
C6 C 0.7472(18) 0.2313(8) 0.5179(5) 0.41(3) Uiso 0.25 1 d D U . A .
C4X C 0.6616(6) 0.2197(9) 0.5148(8) 0.223(12) Uiso 0.5 1 d D U . A -2
H4X H 0.6557 0.2496 0.5245 0.267 Uiso 0.5 1 calc R . . A -2
C3X C 0.6268(7) 0.1864(5) 0.5141(6) 0.141(7) Uiso 0.5 1 d D U . A -2
H3X H 0.5966 0.1927 0.5220 0.169 Uiso 0.5 1 calc R . . A -2


_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 Zr1 3.4853(13) 125_645 ?
Zr1 Zr1 3.4853(13) 29 ?
Zr1 Zr1 3.4853(13) 170_556 ?
Zr1 Zr1 3.4853(13) 74_545 ?
Zr1 O1 2.203(5) . ?
Zr1 O1 2.203(5) 102_655 ?
Zr1 O1 2.203(5) 10_655 ?
Zr1 O1 2.203(5) 8_556 ?
Zr1 O2 2.120(3) . ?
Zr1 O2 2.120(3) 172_546 ?
Zr1 O2 2.120(3) 99_556 ?
Zr1 O2 2.120(3) 74_545 ?
Br1 C6 1.905(18) . ?
Br1 C6 1.905(18) 115_665 ?
Br1 C6 1.905(18) 188_545 ?
Br1 C6 1.905(18) 75_655 ?
O1 C1 1.277(10) . ?
O2 Zr1 2.120(3) 170_556 ?
O2 Zr1 2.120(3) 125_645 ?
C1 O1 1.277(10) 91_546 ?
C1 C2 1.58(3) . ?
C2 C3X 1.459(14) . ?
C5 C6 1.53(2) 188_545 ?
C5 C6 1.53(2) 91_546 ?
C5 C6 1.53(2) . ?
C5 C6 1.53(2) 99_556 ?
C5 C4X 1.454(16) . ?
C6 C6 1.55(2) 169_656 ?
C6 C6 1.07(3) 99_556 ?
C6 C6 1.26(4) 91_546 ?
C6 C6 1.13(4) 75_655 ?
C6 C6 0.67(10) 188_545 ?
C6 C6 1.40(5) 20_666 ?
C6 C6 0.91(6) 115_665 ?
C4X H4X 0.9500 . ?
C4X C3X 1.434(17) . ?
C3X H3X 0.9500 . ?

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
Zr1 Zr1 Zr1 60.0 74_545 125_645 ?
Zr1 Zr1 Zr1 90.0 74_545 170_556 ?
Zr1 Zr1 Zr1 60.0 29 170_556 ?
Zr1 Zr1 Zr1 60.0 74_545 29 ?
Zr1 Zr1 Zr1 90.0 125_645 29 ?
Zr1 Zr1 Zr1 60.0 125_645 170_556 ?
O1 Zr1 Zr1 110.52(12) 102_655 125_645 ?
O1 Zr1 Zr1 110.52(12) . 29 ?
O1 Zr1 Zr1 164.71(18) . 74_545 ?
O1 Zr1 Zr1 74.71(18) . 170_556 ?
O1 Zr1 Zr1 110.52(12) 102_655 29 ?
O1 Zr1 Zr1 74.71(18) 8_556 125_645 ?
O1 Zr1 Zr1 164.71(18) 10_655 125_645 ?
O1 Zr1 Zr1 110.52(12) 10_655 74_545 ?
O1 Zr1 Zr1 164.71(18) 8_556 29 ?
O1 Zr1 Zr1 110.52(12) 8_556 170_556 ?
O1 Zr1 Zr1 110.52(12) . 125_645 ?
O1 Zr1 Zr1 74.71(18) 10_655 29 ?
O1 Zr1 Zr1 110.52(12) 10_655 170_556 ?
O1 Zr1 Zr1 110.52(12) 8_556 74_545 ?
O1 Zr1 Zr1 164.71(18) 102_655 170_556 ?
O1 Zr1 Zr1 74.71(18) 102_655 74_545 ?
O1 Zr1 O1 120.6(4) . 102_655 ?
O1 Zr1 O1 75.78(16) 10_655 102_655 ?
O1 Zr1 O1 75.78(16) 8_556 102_655 ?
O1 Zr1 O1 120.6(4) 10_655 8_556 ?
O1 Zr1 O1 75.78(16) . 10_655 ?
O1 Zr1 O1 75.78(16) . 8_556 ?
O2 Zr1 Zr1 89.0(2) 99_556 74_545 ?
O2 Zr1 Zr1 34.71(13) 99_556 29 ?
O2 Zr1 Zr1 34.71(13) . 125_645 ?
O2 Zr1 Zr1 89.0(2) 74_545 29 ?
O2 Zr1 Zr1 34.72(13) 99_556 170_556 ?
O2 Zr1 Zr1 89.0(2) 172_546 125_645 ?
O2 Zr1 Zr1 34.72(13) 172_546 74_545 ?
O2 Zr1 Zr1 34.71(13) 172_546 29 ?
O2 Zr1 Zr1 89.0(2) 99_556 125_645 ?
O2 Zr1 Zr1 89.0(2) . 29 ?
O2 Zr1 Zr1 89.0(2) . 74_545 ?
O2 Zr1 Zr1 34.72(13) 74_545 74_545 ?
O2 Zr1 Zr1 34.71(13) 74_545 125_645 ?
O2 Zr1 Zr1 89.0(2) 172_546 170_556 ?
O2 Zr1 Zr1 34.71(13) . 170_556 ?
O2 Zr1 Zr1 89.0(2) 74_545 170_556 ?
O2 Zr1 O1 142.04(7) 74_545 . ?
O2 Zr1 O1 78.4(3) . . ?
O2 Zr1 O1 78.4(3) 74_545 102_655 ?
O2 Zr1 O1 142.04(7) . 10_655 ?
O2 Zr1 O1 78.4(3) 74_545 8_556 ?
O2 Zr1 O1 142.04(7) 99_556 8_556 ?
O2 Zr1 O1 142.04(7) 172_546 8_556 ?
O2 Zr1 O1 142.04(7) 99_556 102_655 ?
O2 Zr1 O1 142.04(7) 74_545 10_655 ?
O2 Zr1 O1 142.04(7) 172_546 . ?
O2 Zr1 O1 78.4(3) 99_556 . ?
O2 Zr1 O1 78.4(3) 172_546 10_655 ?
O2 Zr1 O1 142.04(7) . 102_655 ?
O2 Zr1 O1 78.4(3) . 8_556 ?
O2 Zr1 O1 78.4(3) 172_546 102_655 ?
O2 Zr1 O1 78.4(3) 99_556 10_655 ?
O2 Zr1 O2 107.2(6) . 172_546 ?
O2 Zr1 O2 69.4(3) 74_545 172_546 ?
O2 Zr1 O2 69.4(3) . 74_545 ?
O2 Zr1 O2 107.2(6) 74_545 99_556 ?
O2 Zr1 O2 69.4(3) . 99_556 ?
O2 Zr1 O2 69.4(3) 172_546 99_556 ?
C6 Br1 C6 34.3(10) . 75_655 ?
C6 Br1 C6 34.3(10) 188_545 115_665 ?
C6 Br1 C6 20(3) . 188_545 ?
C6 Br1 C6 27.5(19) . 115_665 ?
C6 Br1 C6 20(3) 75_655 115_665 ?
C6 Br1 C6 27.5(19) 188_545 75_655 ?
C1 O1 Zr1 129.8(8) . . ?
Zr1 O2 Zr1 110.6(3) 170_556 125_645 ?
Zr1 O2 Zr1 110.6(3) 125_645 . ?
Zr1 O2 Zr1 110.6(3) 170_556 . ?
O1 C1 O1 130.9(16) 91_546 . ?
O1 C1 C2 114.5(8) . . ?
O1 C1 C2 114.5(8) 91_546 . ?
C3X C2 C1 115.1(12) . . ?
C6 C5 C6 25(4) 188_545 . ?
C6 C5 C6 40.8(14) 188_545 91_546 ?
C6 C5 C6 40.8(14) 99_556 . ?
C6 C5 C6 25(4) 91_546 99_556 ?
C6 C5 C6 48.5(15) 188_545 99_556 ?
C6 C5 C6 48.5(15) 91_546 . ?
C4X C5 C6 119(3) . . ?
C4X C5 C6 134(3) . 99_556 ?
C4X C5 C6 109.2(17) . 91_546 ?
C4X C5 C6 96.8(14) . 188_545 ?
C5 C6 Br1 121(2) . . ?
C5 C6 C6 101(3) . 169_656 ?
C6 C6 Br1 125(2) 20_666 . ?
C6 C6 Br1 116(2) 169_656 . ?
C6 C6 Br1 162.8(5) 99_556 . ?
C6 C6 Br1 136(6) 91_546 . ?
C6 C6 Br1 79.9(15) 188_545 . ?
C6 C6 Br1 76.3(10) 115_665 . ?
C6 C6 Br1 72.8(5) 75_655 . ?
C6 C6 C5 77(2) 188_545 . ?
C6 C6 C5 65.7(7) 91_546 . ?
C6 C6 C5 108.9(18) 20_666 . ?
C6 C6 C5 155.7(8) 115_665 . ?
C6 C6 C5 127(7) 75_655 . ?
C6 C6 C5 69.6(7) 99_556 . ?
C6 C6 C6 58(5) 188_545 91_546 ?
C6 C6 C6 43.5(17) 75_655 169_656 ?
C6 C6 C6 36(3) 91_546 169_656 ?
C6 C6 C6 50(2) 91_546 20_666 ?
C6 C6 C6 64(4) 188_545 169_656 ?
C6 C6 C6 54(3) 115_665 169_656 ?
C6 C6 C6 54(6) 188_545 75_655 ?
C6 C6 C6 40.3(17) 99_556 20_666 ?
C6 C6 C6 46.5(17) 99_556 169_656 ?
C6 C6 C6 26(4) 20_666 169_656 ?
C6 C6 C6 89.999(4) 115_665 99_556 ?
C6 C6 C6 90.01(4) 188_545 115_665 ?
C6 C6 C6 89.990(18) 188_545 99_556 ?
C6 C6 C6 32(5) 99_556 91_546 ?
C6 C6 C6 90.00(3) 115_665 91_546 ?
C6 C6 C6 89.999(10) 99_556 75_655 ?
C6 C6 C6 72(5) 75_655 91_546 ?
C6 C6 C6 90.00(3) 188_545 20_666 ?
C6 C6 C6 49.7(17) 115_665 20_666 ?
C6 C6 C6 36(6) 115_665 75_655 ?
C6 C6 C6 59(4) 75_655 20_666 ?
C5 C4X H4X 121.3 . . ?
C3X C4X C5 117(3) . . ?
C3X C4X H4X 121.3 . . ?
C2 C3X H3X 122.9 . . ?
C4X C3X C2 114(2) . . ?
C4X C3X H3X 122.9 . . ?

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
Zr1 O1 C1 O1 0.0 . . . 91_546 ?
Zr1 O1 C1 C2 180.0 . . . . ?
O1 C1 C2 C3X -161.6(7) 91_546 . . . ?
O1 C1 C2 C3X 18.4(7) . . . . ?
C1 C2 C3X C4X 178.7(10) . . . . ?
C5 C4X C3X C2 2(2) . . . . ?
C6 C5 C6 Br1 164.8(17) 99_556 . . . ?
C6 C5 C6 Br1 70(2) 188_545 . . . ?
C6 C5 C6 Br1 130(7) 91_546 . . . ?
C6 C5 C6 C6 34(5) 99_556 . . 91_546 ?
C6 C5 C6 C6 94.8(6) 99_556 . . 188_545 ?
C6 C5 C6 C6 39.2(8) 91_546 . . 75_655 ?
C6 C5 C6 C6 9.1(12) 99_556 . . 20_666 ?
C6 C5 C6 C6 34(5) 99_556 . . 169_656 ?
C6 C5 C6 C6 -85.6(7) 188_545 . . 20_666 ?
C6 C5 C6 C6 -34(5) 91_546 . . 99_556 ?
C6 C5 C6 C6 34(5) 99_556 . . 115_665 ?
C6 C5 C6 C6 -21(4) 188_545 . . 75_655 ?
C6 C5 C6 C6 -60(4) 188_545 . . 115_665 ?
C6 C5 C6 C6 -0.01(6) 91_546 . . 115_665 ?
C6 C5 C6 C6 -60(4) 188_545 . . 91_546 ?
C6 C5 C6 C6 -60(4) 188_545 . . 169_656 ?
C6 C5 C6 C6 -0.002(4) 91_546 . . 169_656 ?
C6 C5 C6 C6 60(4) 91_546 . . 188_545 ?
C6 C5 C6 C6 -94.8(6) 188_545 . . 99_556 ?
C6 C5 C6 C6 -25(4) 91_546 . . 20_666 ?
C6 C5 C6 C6 74(5) 99_556 . . 75_655 ?
C6 C5 C4X C3X -154.0(16) . . . . ?
C6 C5 C4X C3X 157.9(14) 99_556 . . . ?
C6 C5 C4X C3X 153.5(13) 91_546 . . . ?
C6 C5 C4X C3X -166.5(18) 188_545 . . . ?
C4X C5 C6 Br1 40(3) . . . . ?
C4X C5 C6 C6 -30.3(15) . . . 188_545 ?
C4X C5 C6 C6 -91(4) . . . 115_665 ?
C4X C5 C6 C6 -125(2) . . . 99_556 ?
C4X C5 C6 C6 -91(4) . . . 169_656 ?
C4X C5 C6 C6 -115.9(14) . . . 20_666 ?
C4X C5 C6 C6 -51(3) . . . 75_655 ?
C4X C5 C6 C6 -91(4) . . . 91_546 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
