# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_global
_database_code_depnum_ccdc_archive 'CCDC 1429124'
_audit_update_record             
;
2015-10-01 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;
_audit_creation_date             2014-11-25
_audit_creation_method           CRYSTALS_ver_14.61

_oxford_structure_analysis_title 'gdtfa in P 1'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   8.8390(8)
_cell_length_b                   9.3516(6)
_cell_length_c                   13.4022(10)
_cell_angle_alpha                70.942(7)
_cell_angle_beta                 74.685(8)
_cell_angle_gamma                76.421(7)
_cell_volume                     996.41(14)

_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'
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'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Gd -0.1653 3.9035 25.0709 2.2534 19.0798 0.1820 13.8518 12.9331 3.5455 101.3980
2.4196 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            1

# Given Formula = C36 H15 F18 Gd6 O18 
# Dc =      6.74 Fooo =    606.00 Mu =    200.19 M =   2020.97
# Found Formula = C12 H14 F9.00 Gd1 O9 
# Dc =      2.10 FOOO =    606.00 Mu =     34.53 M =    630.47

_chemical_formula_sum            'C24 H28 F18 Gd2 O18'
_chemical_formula_moiety         'C24 H28 F18 Gd2 O18'
_chemical_compound_source        ?
_chemical_formula_weight         1260.96


_cell_measurement_reflns_used    10833
_cell_measurement_theta_min      4.0850
_cell_measurement_theta_max      29.3000
_cell_measurement_temperature    100

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.220
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_max          0.726

_exptl_crystal_density_diffrn    2.101
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             606.000
_exptl_absorpt_coefficient_mu    3.453

# Sheldrick geometric approximatio 0.38 0.47 
_exptl_absorpt_correction_T_min  0.255
_exptl_absorpt_correction_T_max  0.555
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_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            26450
_reflns_number_total             5102
_diffrn_reflns_av_R_equivalents  0.047
# Number of reflections without Friedels Law is 9595 
# Number of reflections with Friedels Law is 5102 
# Theoretical number of reflections is about 5588 


_diffrn_reflns_theta_min         2.896
_diffrn_reflns_theta_max         29.567
_diffrn_measured_fraction_theta_max 0.914

_diffrn_reflns_theta_full        25.132
_diffrn_measured_fraction_theta_full 0.986


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -11
_reflns_limit_h_max              12
_reflns_limit_k_min              -11
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   1.34
_oxford_diffrn_Wilson_scale      0.17

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

_refine_diff_density_min         -2.42
_refine_diff_density_max         3.06


# 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         5083
_refine_ls_number_restraints     42
_refine_ls_number_parameters     308
_oxford_refine_ls_R_factor_ref   0.0399
_refine_ls_wR_factor_ref         0.0909
_refine_ls_goodness_of_fit_ref   0.9897
_refine_ls_shift/su_max          0.0008312
_refine_ls_shift/su_mean         0.0000338


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5091
_refine_ls_R_factor_all          0.0402
_refine_ls_wR_factor_all         0.0920

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4631
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_gt          0.0836

# 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 Fsqd
_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: 
 0.520E+04 0.661E+04 0.611E+04 0.244E+04 0.172E+04 
;

# 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
F1 F 0.8216(5) 0.8767(4) -0.0740(3) 0.0444 1.0000 Uani . . . . . .
F2 F 0.7730(7) 0.9346(5) 0.0731(3) 0.0654 1.0000 Uani . . . . . .
F3 F 0.9647(5) 0.7552(6) 0.0418(4) 0.0698 1.0000 Uani . . . . . .
F4 F 1.0027(4) 0.6286(4) 0.3376(3) 0.0353 1.0000 Uani . . . . . .
F5 F 0.8485(4) 0.8322(3) 0.3656(3) 0.0356 1.0000 Uani . . . . . .
F6 F 0.9837(4) 0.6848(4) 0.4835(3) 0.0337 1.0000 Uani . . . . . .
F7 F 0.8492(10) 0.0233(8) 0.5200(7) 0.0745 0.680(9) Uani . U P 1 2 .
F8 F 0.6252(10) -0.0404(6) 0.5711(7) 0.0623 0.680(9) Uani . U P 1 2 .
F9 F 0.7305(16) -0.0019(8) 0.6830(6) 0.0769 0.680(9) Uani . U P 1 2 .
F10 F 0.8269(18) 0.0378(15) 0.6363(14) 0.0560 0.320(9) Uani . U P 1 1 .
F11 F 0.747(3) -0.0274(15) 0.5287(13) 0.0668 0.320(9) Uani . U P 1 1 .
F12 F 0.606(2) -0.0078(14) 0.6875(14) 0.0727 0.320(9) Uani . U P 1 1 .
C1 C 0.9337(6) 0.3331(8) 0.2594(5) 0.0394 1.0000 Uani . . . . . .
C2 C 0.7559(6) 0.2057(5) 0.2252(4) 0.0261 1.0000 Uani . . . . . .
C3 C 0.6116(5) 0.2454(6) 0.1776(4) 0.0242 1.0000 Uani . . . . . .
C4 C 0.3332(5) 0.3539(5) 0.2164(3) 0.0208 1.0000 Uani . . . . . .
C5 C 0.3132(5) 0.5177(5) 0.1485(3) 0.0207 1.0000 Uani . . . . . .
C6 C 0.3020(6) 0.7690(5) 0.1570(4) 0.0236 1.0000 Uani . . . . . .
C7 C 0.7051(5) 0.6959(5) 0.0840(3) 0.0207 1.0000 Uani . . . . . .
C8 C 0.8162(6) 0.8175(6) 0.0312(4) 0.0307 1.0000 Uani . . . . . .
C9 C 0.7585(5) 0.5995(5) 0.4663(3) 0.0179 1.0000 Uani . . . . . .
C10 C 0.9014(5) 0.6864(5) 0.4127(4) 0.0227 1.0000 Uani . . . . . .
C11 C 0.6328(5) 0.2183(5) 0.5502(3) 0.0189 1.0000 Uani . . . . . .
C12 C 0.7059(9) 0.0479(6) 0.5880(5) 0.0454 1.0000 Uani . U . . . .
O1 O 0.7791(4) 0.3459(4) 0.2382(3) 0.0231 1.0000 Uani . . . . . .
O2 O 0.4849(4) 0.3141(3) 0.2484(2) 0.0182 1.0000 Uani . . . . . .
O3 O 0.3394(4) 0.6080(3) 0.2084(2) 0.0206 1.0000 Uani . . . . . .
O4 O 0.6634(4) 0.6720(4) 0.1846(3) 0.0237 1.0000 Uani . . . . . .
O5 O 0.7136(4) 0.5497(4) 0.4057(3) 0.0260 1.0000 Uani . . . . . .
O6 O 0.6131(4) 0.2627(4) 0.4564(3) 0.0255 1.0000 Uani . . . . . .
O7 O 0.6725(5) 0.6369(5) 0.0248(3) 0.0354 1.0000 Uani . . . . . .
O8 O 0.7029(4) 0.5914(4) 0.5623(3) 0.0238 1.0000 Uani . . . . . .
O9 O 0.6012(4) 0.2901(4) 0.6189(3) 0.0244 1.0000 Uani . . . . . .
Gd1 Gd 0.53781(2) 0.49477(2) 0.326819(15) 0.0158 1.0000 Uani . . . . . .
H233 H 0.3254 0.8265 0.1972 0.0348 1.0000 Uiso R . . . . .
H232 H 0.3629 0.7937 0.0845 0.0351 1.0000 Uiso R . . . . .
H231 H 0.1900 0.7946 0.1546 0.0350 1.0000 Uiso R . . . . .
H212 H 0.3924 0.5295 0.0823 0.0255 1.0000 Uiso R . . . . .
H211 H 0.2071 0.5491 0.1331 0.0250 1.0000 Uiso R . . . . .
H201 H 0.2500 0.3423 0.2808 0.0249 1.0000 Uiso R . . . . .
H202 H 0.3285 0.2866 0.1756 0.0250 1.0000 Uiso R . . . . .
H182 H 0.6301 0.3160 0.1055 0.0291 1.0000 Uiso R . . . . .
H181 H 0.5833 0.1534 0.1743 0.0290 1.0000 Uiso R . . . . .
H172 H 0.8471 0.1666 0.1773 0.0308 1.0000 Uiso R . . . . .
H171 H 0.7400 0.1291 0.2949 0.0307 1.0000 Uiso R . . . . .
H242 H 0.9430 0.4287 0.2673 0.0589 1.0000 Uiso R . . . . .
H241 H 0.9449 0.2531 0.3246 0.0588 1.0000 Uiso R . . . . .
H243 H 1.0143 0.3090 0.2006 0.0587 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.71(9)
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
F1 . C8 . 1.328(6) yes
F2 . C8 . 1.323(6) yes
F3 . C8 . 1.330(7) yes
F4 . C10 . 1.327(5) yes
F5 . C10 . 1.331(5) yes
F6 . C10 . 1.334(5) yes
F7 . C12 . 1.370(10) yes
F8 . C12 . 1.314(9) yes
F9 . C12 . 1.264(8) yes
F10 . C12 . 1.361(15) yes
F11 . C12 . 1.162(13) yes
F12 . C12 . 1.405(16) yes
C1 . O1 . 1.438(6) yes
C1 . H242 . 0.959 no
C1 . H241 . 0.957 no
C1 . H243 . 0.961 no
C2 . C3 . 1.492(7) yes
C2 . O1 . 1.445(5) yes
C2 . H172 . 0.967 no
C2 . H171 . 0.973 no
C3 . O2 . 1.438(5) yes
C3 . H182 . 0.972 no
C3 . H181 . 0.968 no
C4 . C5 . 1.501(6) yes
C4 . O2 . 1.444(5) yes
C4 . H201 . 0.969 no
C4 . H202 . 0.972 no
C5 . O3 . 1.430(5) yes
C5 . H212 . 0.966 no
C5 . H211 . 0.970 no
C6 . O3 . 1.435(5) yes
C6 . H233 . 0.961 no
C6 . H232 . 0.961 no
C6 . H231 . 0.968 no
C7 . C8 . 1.546(6) yes
C7 . O4 . 1.259(5) yes
C7 . O7 . 1.224(5) yes
C9 . C10 . 1.547(6) yes
C9 . O5 . 1.240(5) yes
C9 . O8 . 1.234(5) yes
C11 . C12 . 1.542(7) yes
C11 . O6 . 1.235(5) yes
C11 . O9 . 1.247(5) yes
O1 . Gd1 . 2.499(3) yes
O2 . Gd1 . 2.443(3) yes
O3 . Gd1 . 2.494(3) yes
O4 . Gd1 . 2.301(3) yes
O5 . Gd1 . 2.322(3) yes
O6 . Gd1 . 2.375(3) yes
O8 . Gd1 2_666 2.395(3) yes
O9 . Gd1 2_666 2.326(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 . C1 . H242 . 108.8 no
O1 . C1 . H241 . 109.1 no
H242 . C1 . H241 . 109.8 no
O1 . C1 . H243 . 109.6 no
H242 . C1 . H243 . 110.1 no
H241 . C1 . H243 . 109.5 no
C3 . C2 . O1 . 106.3(4) yes
C3 . C2 . H172 . 110.1 no
O1 . C2 . H172 . 110.4 no
C3 . C2 . H171 . 110.5 no
O1 . C2 . H171 . 110.0 no
H172 . C2 . H171 . 109.5 no
C2 . C3 . O2 . 106.9(3) yes
C2 . C3 . H182 . 110.7 no
O2 . C3 . H182 . 110.8 no
C2 . C3 . H181 . 110.0 no
O2 . C3 . H181 . 108.9 no
H182 . C3 . H181 . 109.5 no
C5 . C4 . O2 . 109.3(3) yes
C5 . C4 . H201 . 109.3 no
O2 . C4 . H201 . 108.5 no
C5 . C4 . H202 . 110.0 no
O2 . C4 . H202 . 109.6 no
H201 . C4 . H202 . 110.2 no
C4 . C5 . O3 . 107.0(3) yes
C4 . C5 . H212 . 110.0 no
O3 . C5 . H212 . 108.2 no
C4 . C5 . H211 . 110.0 no
O3 . C5 . H211 . 110.9 no
H212 . C5 . H211 . 110.6 no
O3 . C6 . H233 . 109.5 no
O3 . C6 . H232 . 109.9 no
H233 . C6 . H232 . 109.9 no
O3 . C6 . H231 . 109.1 no
H233 . C6 . H231 . 109.6 no
H232 . C6 . H231 . 108.8 no
C8 . C7 . O4 . 112.6(4) yes
C8 . C7 . O7 . 117.5(4) yes
O4 . C7 . O7 . 129.9(4) yes
C7 . C8 . F3 . 110.5(4) yes
C7 . C8 . F1 . 112.6(4) yes
F3 . C8 . F1 . 106.1(5) yes
C7 . C8 . F2 . 112.9(4) yes
F3 . C8 . F2 . 108.1(5) yes
F1 . C8 . F2 . 106.3(4) yes
C10 . C9 . O5 . 115.0(4) yes
C10 . C9 . O8 . 116.2(4) yes
O5 . C9 . O8 . 128.8(4) yes
C9 . C10 . F6 . 112.6(4) yes
C9 . C10 . F5 . 109.2(4) yes
F6 . C10 . F5 . 107.6(4) yes
C9 . C10 . F4 . 112.3(4) yes
F6 . C10 . F4 . 107.2(4) yes
F5 . C10 . F4 . 107.7(4) yes
C12 . C11 . O6 . 114.8(4) yes
C12 . C11 . O9 . 115.4(4) yes
O6 . C11 . O9 . 129.8(4) yes
C11 . C12 . F12 . 103.7(7) yes
C11 . C12 . F10 . 108.2(7) yes
F12 . C12 . F10 . 92.1(12) yes
C11 . C12 . F11 . 120.9(8) yes
F12 . C12 . F11 . 118.0(14) yes
F10 . C12 . F11 . 109.8(14) yes
C11 . C12 . F7 . 108.3(6) yes
C11 . C12 . F8 . 111.1(6) yes
F7 . C12 . F8 . 101.4(7) yes
C11 . C12 . F9 . 116.9(5) yes
F7 . C12 . F9 . 107.2(8) yes
F8 . C12 . F9 . 110.6(8) yes
C2 . O1 . C1 . 112.1(4) yes
C2 . O1 . Gd1 . 115.6(2) yes
C1 . O1 . Gd1 . 121.6(3) yes
C4 . O2 . C3 . 114.2(3) yes
C4 . O2 . Gd1 . 114.7(2) yes
C3 . O2 . Gd1 . 119.6(2) yes
C6 . O3 . C5 . 111.5(3) yes
C6 . O3 . Gd1 . 124.1(2) yes
C5 . O3 . Gd1 . 118.6(2) yes
C7 . O4 . Gd1 . 136.5(3) yes
C9 . O5 . Gd1 . 158.2(3) yes
C11 . O6 . Gd1 . 139.3(3) yes
Gd1 2_666 O8 . C9 . 129.0(3) yes
C11 . O9 . Gd1 2_666 147.6(3) yes
O1 . Gd1 . O3 . 111.26(10) yes
O1 . Gd1 . O2 . 64.84(10) yes
O3 . Gd1 . O2 . 66.03(10) yes
O1 . Gd1 . O8 2_666 128.77(11) yes
O3 . Gd1 . O8 2_666 75.88(11) yes
O2 . Gd1 . O8 2_666 74.22(10) yes
O1 . Gd1 . O6 . 71.39(11) yes
O3 . Gd1 . O6 . 139.77(11) yes
O2 . Gd1 . O6 . 81.17(10) yes
O8 2_666 Gd1 . O6 . 73.17(12) yes
O1 . Gd1 . O9 2_666 153.28(11) yes
O3 . Gd1 . O9 2_666 76.20(11) yes
O2 . Gd1 . O9 2_666 137.10(11) yes
O8 2_666 Gd1 . O9 2_666 77.61(11) yes
O6 . Gd1 . O9 2_666 120.34(11) yes
O1 . Gd1 . O5 . 84.86(11) yes
O3 . Gd1 . O5 . 144.70(11) yes
O2 . Gd1 . O5 . 145.96(11) yes
O8 2_666 Gd1 . O5 . 119.18(11) yes
O6 . Gd1 . O5 . 74.39(12) yes
O1 . Gd1 . O4 . 73.92(11) yes
O3 . Gd1 . O4 . 76.64(11) yes
O2 . Gd1 . O4 . 105.79(11) yes
O8 2_666 Gd1 . O4 . 149.62(12) yes
O6 . Gd1 . O4 . 137.21(12) yes
O9 2_666 Gd1 . O5 . 76.59(12) yes
O9 2_666 Gd1 . O4 . 83.52(12) yes
O5 . Gd1 . O4 . 78.32(12) 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 . H233 . O9 2_666 124.29(12) 0.961 2.538 3.180(7) yes
C4 . H202 . O7 2_665 126.38(13) 0.972 2.546 3.219(7) 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_global
_database_code_depnum_ccdc_archive 'CCDC 1429125'
_audit_update_record             
;
2015-10-01 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;
_audit_creation_date             2014-11-25
_audit_creation_method           CRYSTALS_ver_14.61

_oxford_structure_analysis_title 'haya010 in P -1'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   8.8422(7)
_cell_length_b                   9.6242(7)
_cell_length_c                   13.2522(8)
_cell_angle_alpha                69.579(6)
_cell_angle_beta                 74.832(6)
_cell_angle_gamma                72.913(7)
_cell_volume                     994.16(13)

_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'
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'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Tm -0.3139 5.2483 28.1819 2.0286 15.8851 0.2388 15.1542 10.9975 2.9871 102.9610
6.7562 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            1

# Given Formula = C12 H12 F9 O6 Tm1 
# Dc =      1.98 Fooo =    616.00 Mu =     45.67 M =    592.14
# Found Formula = C12 H14 F9 O9 Tm1 
# Dc =      2.15 FOOO =    616.00 Mu =     45.87 M =    642.15

_chemical_formula_sum            'C24 H28 F18 O18 Tm2'
_chemical_formula_moiety         'C24 H28 F18 O18 Tm2'
_chemical_compound_source        ?
_chemical_formula_weight         1284.44


_cell_measurement_reflns_used    13747
_cell_measurement_theta_min      4.4770
_cell_measurement_theta_max      29.5440
_cell_measurement_temperature    160

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.140
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_max          0.359

_exptl_crystal_density_diffrn    2.145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    4.587

# Sheldrick geometric approximatio 0.39 0.52 
_exptl_absorpt_correction_T_min  0.097
_exptl_absorpt_correction_T_max  0.350
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_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      160
_diffrn_reflns_number            26607
_reflns_number_total             5123
_diffrn_reflns_av_R_equivalents  0.078
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5123 
# Theoretical number of reflections is about 11291 


_diffrn_reflns_theta_min         2.806
_diffrn_reflns_theta_max         29.703
_diffrn_measured_fraction_theta_max 0.903

_diffrn_reflns_theta_full        25.247
_diffrn_measured_fraction_theta_full 0.987


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -11
_reflns_limit_h_max              12
_reflns_limit_k_min              -11
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -2.08
_refine_diff_density_max         1.33


# 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>-10.0\s(I)
_refine_ls_number_reflns         5112
_refine_ls_number_restraints     42
_refine_ls_number_parameters     309
_oxford_refine_ls_R_factor_ref   0.0452
_refine_ls_wR_factor_ref         0.0936
_refine_ls_goodness_of_fit_ref   0.9648
_refine_ls_shift/su_max          0.0000928
_refine_ls_shift/su_mean         0.0000094


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5112
_refine_ls_R_factor_all          0.0452
_refine_ls_wR_factor_all         0.0936

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4739
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_gt          0.0875

# 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 Fsqd
_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: 
 0.325E+04 0.483E+04 0.271E+04 913. 
;

# 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
F1 F -0.2349(12) 0.0746(8) 0.9244(6) 0.1081 1.0000 Uani . U . . . .
F2 F -0.2975(10) 0.1262(7) 1.0714(5) 0.0810 1.0000 Uani . U . . . .
F3 F -0.4420(10) 0.2460(11) 0.9540(7) 0.1139 1.0000 Uani . U . . . .
F4 F -0.4887(6) 0.3647(6) 0.6631(4) 0.0539 1.0000 Uani . . . . . .
F5 F -0.3151(7) 0.1709(5) 0.6309(5) 0.0537 1.0000 Uani . . . . . .
F6 F -0.4598(6) 0.3189(6) 0.5130(4) 0.0475 1.0000 Uani . . . . . .
F7 F 0.125(2) -0.0011(12) 0.6982(11) 0.0878 0.585(11) Uani . U P 1 1 .
F8 F 0.259(2) -0.0259(12) 0.5399(11) 0.0816 0.585(11) Uani . U P 1 1 .
F9 F 0.3501(19) 0.0451(12) 0.6439(12) 0.0837 0.585(11) Uani . U P 1 1 .
F10 F 0.234(3) 0.000(2) 0.6959(19) 0.0838 0.415(11) Uani . U P 1 2 .
F11 F 0.125(3) -0.0263(16) 0.5867(17) 0.0842 0.415(11) Uani . U P 1 2 .
F12 F 0.352(3) 0.0199(19) 0.5290(18) 0.0901 0.415(11) Uani . U P 1 2 .
C1 C 0.2096(9) 0.2367(7) 0.8438(5) 0.0303 1.0000 Uani . . . . . .
C2 C 0.1853(9) 0.4869(8) 0.8471(6) 0.0290 1.0000 Uani . . . . . .
C3 C 0.1572(8) 0.6470(8) 0.7765(5) 0.0280 1.0000 Uani . . . . . .
C4 C -0.1265(9) 0.7571(9) 0.8139(6) 0.0339 1.0000 Uani . . . . . .
C5 C -0.2752(9) 0.7918(8) 0.7689(6) 0.0330 1.0000 Uani . . . . . .
C6 C -0.4435(9) 0.6588(11) 0.7439(9) 0.0518 1.0000 Uani . . . . . .
C7 C -0.1939(8) 0.3110(8) 0.9156(5) 0.0283 1.0000 Uani . . . . . .
C8 C -0.2909(12) 0.1869(10) 0.9663(7) 0.0481 1.0000 Uani . . . . . .
C9 C -0.2494(7) 0.4071(7) 0.5357(5) 0.0217 1.0000 Uani . . . . . .
C10 C -0.3818(8) 0.3155(8) 0.5866(5) 0.0284 1.0000 Uani . . . . . .
C11 C 0.1402(8) 0.2243(7) 0.5553(5) 0.0235 1.0000 Uani . . . . . .
C12 C 0.2149(14) 0.0567(10) 0.6009(7) 0.0525 1.0000 Uani . . . . . .
O1 O 0.1624(6) 0.3961(5) 0.7890(4) 0.0259 1.0000 Uani . . . . . .
O2 O 0.0026(6) 0.6867(5) 0.7434(4) 0.0245 1.0000 Uani . . . . . .
O3 O -0.2866(6) 0.6518(5) 0.7576(4) 0.0287 1.0000 Uani . . . . . .
O4 O -0.1495(6) 0.3373(5) 0.8147(3) 0.0291 1.0000 Uani . . . . . .
O5 O -0.2165(6) 0.4587(6) 0.5988(4) 0.0292 1.0000 Uani . . . . . .
O6 O 0.0999(6) 0.2990(5) 0.6217(4) 0.0309 1.0000 Uani . . . . . .
O7 O -0.1715(9) 0.3695(8) 0.9765(5) 0.0529 1.0000 Uani . . . . . .
O8 O -0.1856(6) 0.4140(5) 0.4398(4) 0.0287 1.0000 Uani . . . . . .
O9 O 0.1256(6) 0.2664(6) 0.4585(4) 0.0336 1.0000 Uani . . . . . .
Tm1 Tm -0.04136(3) 0.50868(3) 0.67247(2) 0.0170 1.0000 Uani . . . . . .
H11 H 0.1810 0.1785 0.8080 0.0450 1.0000 Uiso R . . . . .
H13 H 0.1563 0.2161 0.9189 0.0451 1.0000 Uiso R . . . . .
H12 H 0.3240 0.2095 0.8412 0.0450 1.0000 Uiso R . . . . .
H21 H 0.1083 0.4781 0.9154 0.0349 1.0000 Uiso R . . . . .
H22 H 0.2942 0.4541 0.8616 0.0351 1.0000 Uiso R . . . . .
H31 H 0.1567 0.7135 0.8176 0.0340 1.0000 Uiso R . . . . .
H32 H 0.2408 0.6587 0.7126 0.0339 1.0000 Uiso R . . . . .
H63 H -0.4476 0.5627 0.7391 0.0780 1.0000 Uiso R . . . . .
H62 H -0.5221 0.6814 0.8046 0.0780 1.0000 Uiso R . . . . .
H61 H -0.4674 0.7372 0.6772 0.0779 1.0000 Uiso R . . . . .
H52 H -0.3698 0.8281 0.8187 0.0401 1.0000 Uiso R . . . . .
H51 H -0.2665 0.8677 0.6978 0.0402 1.0000 Uiso R . . . . .
H42 H -0.1057 0.8496 0.8162 0.0409 1.0000 Uiso R . . . . .
H41 H -0.1374 0.6867 0.8873 0.0410 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       63(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          5.52(13)
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
F1 . C8 . 1.297(11) yes
F2 . C8 . 1.302(10) yes
F3 . C8 . 1.318(12) yes
F4 . C10 . 1.310(8) yes
F5 . C10 . 1.326(8) yes
F6 . C10 . 1.321(8) yes
F7 . C12 . 1.352(16) yes
F8 . C12 . 1.240(13) yes
F9 . C12 . 1.414(17) yes
F10 . C12 . 1.22(2) yes
F11 . C12 . 1.37(2) yes
F12 . C12 . 1.37(2) yes
C1 . O1 . 1.435(7) yes
C1 . H11 . 0.967 no
C1 . H13 . 0.961 no
C1 . H12 . 0.962 no
C2 . C3 . 1.484(9) yes
C2 . O1 . 1.432(7) yes
C2 . H21 . 0.974 no
C2 . H22 . 0.969 no
C3 . O2 . 1.448(8) yes
C3 . H31 . 0.973 no
C3 . H32 . 0.966 no
C4 . C5 . 1.487(10) yes
C4 . O2 . 1.437(8) yes
C4 . H42 . 0.972 no
C4 . H41 . 0.971 no
C5 . O3 . 1.441(8) yes
C5 . H52 . 0.979 no
C5 . H51 . 0.970 no
C6 . O3 . 1.425(9) yes
C6 . H63 . 0.960 no
C6 . H62 . 0.959 no
C6 . H61 . 0.966 no
C7 . C8 . 1.534(10) yes
C7 . O4 . 1.246(8) yes
C7 . O7 . 1.215(8) yes
C9 . C10 . 1.542(9) yes
C9 . O5 . 1.239(7) yes
C9 . O8 . 1.234(7) yes
C11 . C12 . 1.518(10) yes
C11 . O6 . 1.243(7) yes
C11 . O9 . 1.233(8) yes
O1 . Tm1 . 2.439(5) yes
O2 . Tm1 . 2.383(4) yes
O3 . Tm1 . 2.434(4) yes
O4 . Tm1 . 2.236(4) yes
O5 . Tm1 . 2.267(4) yes
O6 . Tm1 . 2.260(5) yes
O8 . Tm1 2_566 2.310(5) yes
O9 . Tm1 2_566 2.315(5) 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 . C1 . H11 . 109.6 no
O1 . C1 . H13 . 109.2 no
H11 . C1 . H13 . 110.0 no
O1 . C1 . H12 . 109.1 no
H11 . C1 . H12 . 109.6 no
H13 . C1 . H12 . 109.2 no
C3 . C2 . O1 . 107.4(5) yes
C3 . C2 . H21 . 109.7 no
O1 . C2 . H21 . 109.7 no
C3 . C2 . H22 . 109.8 no
O1 . C2 . H22 . 110.0 no
H21 . C2 . H22 . 110.3 no
C2 . C3 . O2 . 108.8(5) yes
C2 . C3 . H31 . 109.4 no
O2 . C3 . H31 . 109.3 no
C2 . C3 . H32 . 110.0 no
O2 . C3 . H32 . 109.7 no
H31 . C3 . H32 . 109.6 no
C5 . C4 . O2 . 106.9(5) yes
C5 . C4 . H42 . 110.6 no
O2 . C4 . H42 . 110.7 no
C5 . C4 . H41 . 110.0 no
O2 . C4 . H41 . 109.4 no
H42 . C4 . H41 . 109.4 no
C4 . C5 . O3 . 106.6(6) yes
C4 . C5 . H52 . 110.7 no
O3 . C5 . H52 . 109.7 no
C4 . C5 . H51 . 109.5 no
O3 . C5 . H51 . 109.9 no
H52 . C5 . H51 . 110.3 no
O3 . C6 . H63 . 109.6 no
O3 . C6 . H62 . 110.4 no
H63 . C6 . H62 . 109.0 no
O3 . C6 . H61 . 109.3 no
H63 . C6 . H61 . 109.2 no
H62 . C6 . H61 . 109.3 no
C8 . C7 . O4 . 113.2(6) yes
C8 . C7 . O7 . 117.6(7) yes
O4 . C7 . O7 . 129.2(7) yes
C7 . C8 . F3 . 109.8(8) yes
C7 . C8 . F2 . 113.9(8) yes
F3 . C8 . F2 . 104.7(8) yes
C7 . C8 . F1 . 113.2(7) yes
F3 . C8 . F1 . 108.9(10) yes
F2 . C8 . F1 . 105.8(8) yes
C10 . C9 . O5 . 114.9(5) yes
C10 . C9 . O8 . 116.6(5) yes
O5 . C9 . O8 . 128.5(6) yes
C9 . C10 . F5 . 109.3(6) yes
C9 . C10 . F6 . 112.2(5) yes
F5 . C10 . F6 . 107.0(6) yes
C9 . C10 . F4 . 112.7(5) yes
F5 . C10 . F4 . 108.0(6) yes
F6 . C10 . F4 . 107.4(6) yes
C12 . C11 . O6 . 115.2(6) yes
C12 . C11 . O9 . 115.6(6) yes
O6 . C11 . O9 . 129.2(6) yes
C11 . C12 . F9 . 108.2(8) yes
C11 . C12 . F7 . 109.2(9) yes
F9 . C12 . F7 . 95.9(11) yes
C11 . C12 . F8 . 119.3(9) yes
F9 . C12 . F8 . 107.0(12) yes
F7 . C12 . F8 . 114.4(13) yes
C11 . C12 . F12 . 107.9(10) yes
C11 . C12 . F11 . 108.3(10) yes
F12 . C12 . F11 . 98.5(14) yes
C11 . C12 . F10 . 122.2(11) yes
F12 . C12 . F10 . 112.3(16) yes
F11 . C12 . F10 . 104.9(16) yes
C1 . O1 . C2 . 111.4(5) yes
C1 . O1 . Tm1 . 124.9(4) yes
C2 . O1 . Tm1 . 117.8(4) yes
C3 . O2 . C4 . 113.4(5) yes
C3 . O2 . Tm1 . 114.9(4) yes
C4 . O2 . Tm1 . 119.7(4) yes
C5 . O3 . C6 . 111.9(6) yes
C5 . O3 . Tm1 . 116.0(4) yes
C6 . O3 . Tm1 . 123.6(4) yes
C7 . O4 . Tm1 . 139.2(4) yes
C9 . O5 . Tm1 . 152.8(4) yes
C11 . O6 . Tm1 . 150.7(5) yes
Tm1 2_566 O8 . C9 . 134.1(4) yes
Tm1 2_566 O9 . C11 . 138.1(4) yes
O1 . Tm1 . O3 . 112.43(16) yes
O1 . Tm1 . O2 . 67.24(15) yes
O3 . Tm1 . O2 . 66.07(16) yes
O1 . Tm1 . O9 2_566 139.33(16) yes
O3 . Tm1 . O9 2_566 71.99(18) yes
O2 . Tm1 . O9 2_566 79.85(16) yes
O1 . Tm1 . O8 2_566 76.26(16) yes
O3 . Tm1 . O8 2_566 130.51(16) yes
O2 . Tm1 . O8 2_566 74.74(16) yes
O9 2_566 Tm1 . O8 2_566 72.41(18) yes
O1 . Tm1 . O5 . 144.74(16) yes
O3 . Tm1 . O5 . 82.61(17) yes
O2 . Tm1 . O5 . 144.56(17) yes
O9 2_566 Tm1 . O5 . 74.82(18) yes
O8 2_566 Tm1 . O5 . 119.11(17) yes
O1 . Tm1 . O6 . 76.50(16) yes
O3 . Tm1 . O6 . 151.27(17) yes
O2 . Tm1 . O6 . 138.44(17) yes
O9 2_566 Tm1 . O6 . 120.01(17) yes
O8 2_566 Tm1 . O6 . 77.59(17) yes
O1 . Tm1 . O4 . 76.11(17) yes
O3 . Tm1 . O4 . 74.03(17) yes
O2 . Tm1 . O4 . 106.92(16) yes
O9 2_566 Tm1 . O4 . 138.66(19) yes
O8 2_566 Tm1 . O4 . 148.92(18) yes
O5 . Tm1 . O6 . 76.59(18) yes
O5 . Tm1 . O4 . 78.12(17) yes
O6 . Tm1 . O4 . 82.38(17) 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
C1 . H11 . O6 . 122.00 0.967 2.529 3.144(11) yes
C3 . H31 . O7 2_567 125.8(2) 0.973 2.588 3.255(11) 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_global
_database_code_depnum_ccdc_archive 'CCDC 1429126'
_audit_update_record             
;
2015-10-01 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;
_audit_creation_date             2014-11-25
_audit_creation_method           CRYSTALS_ver_14.61

_oxford_structure_analysis_title 'hay-a-018 in P -1'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   8.8369(5)
_cell_length_b                   9.6401(6)
_cell_length_c                   13.2137(7)
_cell_angle_alpha                69.577(5)
_cell_angle_beta                 74.812(5)
_cell_angle_gamma                72.774(5)
_cell_volume                     991.63(11)

_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'
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'
Yb -0.3850 5.5486 28.6641 1.9889 15.4345 0.2571 15.3087 10.6647 2.9896 100.4170
7.5667 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Tm -0.3139 5.2483 28.1819 2.0286 15.8851 0.2388 15.1542 10.9975 2.9871 102.9610
6.7562 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Yb -0.3850 5.5486 28.6641 1.9889 15.4345 0.2571 15.3087 10.6647 2.9896 100.4170
7.5667 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            1

# Given Formula = C24 H24 F2 O4 Tm2 Yb4 
# Dc =      4.84 Fooo =    618.00 Mu =    275.76 M =   1444.48
# Found Formula = C12 H14 F9 O9 Yb1 
# Dc =      2.16 FOOO =    618.00 Mu =     48.41 M =    646.26

_chemical_formula_sum            'C24 H28 F18 O18 Yb2'
_chemical_formula_moiety         'C24 H28 F18 O18 Yb2'
_chemical_compound_source        ?
_chemical_formula_weight         1292.54



_cell_measurement_reflns_used    27829
_cell_measurement_theta_min      4.0320
_cell_measurement_theta_max      29.6780
_cell_measurement_temperature    160

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.271
_exptl_crystal_size_mid          0.351
_exptl_crystal_size_max          0.494

_exptl_crystal_density_diffrn    2.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             618
_exptl_absorpt_coefficient_mu    4.841

# Sheldrick geometric approximatio 0.18 0.27 
_exptl_absorpt_correction_T_min  0.071
_exptl_absorpt_correction_T_max  0.186
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_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      160
_diffrn_reflns_number            52157
_reflns_number_total             5185
_diffrn_reflns_av_R_equivalents  0.086
# Number of reflections without Friedels Law is 9787 
# Number of reflections with Friedels Law is 5185 
# Theoretical number of reflections is about 5611 


_diffrn_reflns_theta_min         3.203
_diffrn_reflns_theta_max         29.664
_diffrn_measured_fraction_theta_max 0.920

_diffrn_reflns_theta_full        25.215
_diffrn_measured_fraction_theta_full 0.987


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -11
_reflns_limit_h_max              12
_reflns_limit_k_min              -12
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -1.69
_refine_diff_density_max         1.60


# 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         5172
_refine_ls_number_restraints     42
_refine_ls_number_parameters     309
_oxford_refine_ls_R_factor_ref   0.0426
_refine_ls_wR_factor_ref         0.0925
_refine_ls_goodness_of_fit_ref   0.9918
_refine_ls_shift/su_max          0.0026762
_refine_ls_shift/su_mean         0.0001424


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5176
_refine_ls_R_factor_all          0.0427
_refine_ls_wR_factor_all         0.0928

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4908
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_gt          0.0871

# 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 Fsqd
_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: 
 0.351E+04 0.513E+04 0.315E+04 0.110E+04 
;

# 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
F1 F 0.7586(17) -0.5288(9) 1.0376(7) 0.0812 0.583(9) Uani D U P 1 2 .
F2 F 0.6254(14) -0.5028(10) 1.1968(7) 0.0869 0.583(9) Uani D U P 1 2 .
F3 F 0.8535(12) -0.4509(11) 1.1376(10) 0.0877 0.583(9) Uani D U P 1 2 .
F4 F 0.8569(15) -0.4783(15) 1.0347(10) 0.0916 0.417(9) Uani D U P 1 1 .
F5 F 0.6232(18) -0.5211(13) 1.0925(13) 0.0890 0.417(9) Uani D U P 1 1 .
F6 F 0.745(2) -0.4991(14) 1.2057(8) 0.0906 0.417(9) Uani D U P 1 1 .
F7 F 0.0408(6) -0.1809(6) 1.0123(4) 0.0468 1.0000 Uani . . . . . .
F8 F 0.0112(6) -0.1356(6) 1.1637(4) 0.0515 1.0000 Uani . . . . . .
F9 F 0.1866(7) -0.3290(5) 1.1308(4) 0.0527 1.0000 Uani . . . . . .
F10 F 0.7306(14) 0.4254(9) 0.5758(6) 0.1323 1.0000 Uani . . . . . .
F11 F 0.9406(10) 0.2555(12) 0.5473(8) 0.1311 1.0000 Uani . . . . . .
F12 F 0.7963(8) 0.3738(6) 0.4277(4) 0.0698 1.0000 Uani . . . . . .
C1 C 0.2912(9) 0.2633(7) 0.6553(5) 0.0316 1.0000 Uani . . . . . .
C2 C 0.3143(8) 0.0135(7) 0.6527(5) 0.0286 1.0000 Uani . . . . . .
C3 C 0.3434(8) -0.1476(7) 0.7237(5) 0.0279 1.0000 Uani . . . . . .
C4 C 0.6268(8) -0.2570(8) 0.6866(5) 0.0326 1.0000 Uani . . . . . .
C5 C 0.7767(8) -0.2923(8) 0.7324(6) 0.0326 1.0000 Uani . . . . . .
C6 C 0.9436(8) -0.1573(10) 0.7566(8) 0.0477 1.0000 Uani . . . . . .
C7 C 0.6410(7) -0.2749(6) 1.0550(5) 0.0221 1.0000 Uani . . . . . .
C8 C 0.7183(9) -0.4409(6) 1.1027(5) 0.0484 1.0000 Uani D . . . . .
C9 C 0.2508(6) -0.0928(6) 1.0355(4) 0.0185 1.0000 Uani . . . . . .
C10 C 0.1200(8) -0.1845(8) 1.0859(5) 0.0286 1.0000 Uani . . . . . .
C11 C 0.6928(8) 0.1884(7) 0.5841(5) 0.0266 1.0000 Uani . . . . . .
C12 C 0.7903(12) 0.3127(10) 0.5335(6) 0.0495 1.0000 Uani . . . . . .
O1 O 0.3380(6) 0.1035(5) 0.7114(3) 0.0260 1.0000 Uani . . . . . .
O2 O 0.4983(5) -0.1872(5) 0.7572(3) 0.0231 1.0000 Uani . . . . . .
O3 O 0.7868(5) -0.1515(5) 0.7420(4) 0.0279 1.0000 Uani . . . . . .
O4 O 0.6264(6) -0.2334(5) 0.9586(4) 0.0303 1.0000 Uani . . . . . .
O5 O 0.2844(6) -0.0403(5) 1.0988(4) 0.0306 1.0000 Uani . . . . . .
O6 O 0.6493(6) 0.1615(5) 0.6860(3) 0.0268 1.0000 Uani . . . . . .
O7 O 0.3999(6) 0.2005(5) 0.8784(4) 0.0302 1.0000 Uani . . . . . .
O8 O 0.3147(6) -0.0856(5) 0.9398(3) 0.0286 1.0000 Uani . . . . . .
O9 O 0.6712(8) 0.1300(7) 0.5232(5) 0.0516 1.0000 Uani . . . . . .
Yb1 Yb 0.54166(3) -0.00893(2) 0.827567(17) 0.0168 1.0000 Uani . . . . . .
H263 H 0.9447 -0.0619 0.7647 0.0708 1.0000 Uiso R . . . . .
H262 H 0.9701 -0.2394 0.8214 0.0709 1.0000 Uiso R . . . . .
H261 H 1.0216 -0.1746 0.6931 0.0708 1.0000 Uiso R . . . . .
H242 H 0.7683 -0.3670 0.8047 0.0389 1.0000 Uiso R . . . . .
H241 H 0.8716 -0.3294 0.6837 0.0388 1.0000 Uiso R . . . . .
H231 H 0.6379 -0.1863 0.6137 0.0389 1.0000 Uiso R . . . . .
H232 H 0.6053 -0.3487 0.6844 0.0390 1.0000 Uiso R . . . . .
H212 H 0.2604 -0.1575 0.7883 0.0330 1.0000 Uiso R . . . . .
H211 H 0.3428 -0.2152 0.6834 0.0332 1.0000 Uiso R . . . . .
H202 H 0.2047 0.0470 0.6377 0.0341 1.0000 Uiso R . . . . .
H201 H 0.3898 0.0221 0.5841 0.0339 1.0000 Uiso R . . . . .
H272 H 0.3188 0.3198 0.6925 0.0470 1.0000 Uiso R . . . . .
H271 H 0.1766 0.2915 0.6565 0.0470 1.0000 Uiso R . . . . .
H273 H 0.3485 0.2833 0.5805 0.0471 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       141(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          6.23(18)
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
F1 . C8 . 1.324(5) yes
F2 . C8 . 1.347(5) yes
F3 . C8 . 1.356(5) yes
F4 . C8 . 1.350(5) yes
F5 . C8 . 1.355(5) yes
F6 . C8 . 1.335(5) yes
F7 . C10 . 1.325(8) yes
F8 . C10 . 1.325(7) yes
F9 . C10 . 1.326(8) yes
F10 . C12 . 1.304(11) yes
F11 . C12 . 1.313(12) yes
F12 . C12 . 1.308(9) yes
C1 . O1 . 1.442(7) yes
C1 . H272 . 0.962 no
C1 . H271 . 0.965 no
C1 . H273 . 0.965 no
C2 . C3 . 1.493(9) yes
C2 . O1 . 1.436(7) yes
C2 . H202 . 0.975 no
C2 . H201 . 0.968 no
C3 . O2 . 1.451(7) yes
C3 . H212 . 0.966 no
C3 . H211 . 0.976 no
C4 . C5 . 1.499(10) yes
C4 . O2 . 1.429(7) yes
C4 . H231 . 0.966 no
C4 . H232 . 0.969 no
C5 . O3 . 1.436(8) yes
C5 . H242 . 0.976 no
C5 . H241 . 0.972 no
C6 . O3 . 1.431(8) yes
C6 . H263 . 0.965 no
C6 . H262 . 0.968 no
C6 . H261 . 0.965 no
C7 . O7 2_657 1.241(7) yes
C7 . C8 . 1.517(7) yes
C7 . O4 . 1.224(7) yes
C9 . C10 . 1.534(8) yes
C9 . O5 . 1.248(7) yes
C9 . O8 . 1.230(6) yes
C11 . C12 . 1.541(10) yes
C11 . O6 . 1.254(7) yes
C11 . O9 . 1.209(8) yes
O1 . Yb1 . 2.429(4) yes
O2 . Yb1 . 2.378(4) yes
O3 . Yb1 . 2.429(4) yes
O4 . Yb1 . 2.312(4) yes
O5 . Yb1 2_657 2.252(4) yes
O6 . Yb1 . 2.225(4) yes
O7 . Yb1 . 2.259(4) yes
O8 . Yb1 . 2.307(4) 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 . C1 . H272 . 108.5 no
O1 . C1 . H271 . 109.4 no
H272 . C1 . H271 . 109.8 no
O1 . C1 . H273 . 109.1 no
H272 . C1 . H273 . 109.8 no
H271 . C1 . H273 . 110.2 no
C3 . C2 . O1 . 107.0(5) yes
C3 . C2 . H202 . 110.3 no
O1 . C2 . H202 . 110.2 no
C3 . C2 . H201 . 109.7 no
O1 . C2 . H201 . 110.2 no
H202 . C2 . H201 . 109.4 no
C2 . C3 . O2 . 108.9(5) yes
C2 . C3 . H212 . 109.2 no
O2 . C3 . H212 . 108.9 no
C2 . C3 . H211 . 110.1 no
O2 . C3 . H211 . 109.8 no
H212 . C3 . H211 . 110.0 no
C5 . C4 . O2 . 106.7(5) yes
C5 . C4 . H231 . 109.7 no
O2 . C4 . H231 . 109.2 no
C5 . C4 . H232 . 111.0 no
O2 . C4 . H232 . 110.2 no
H231 . C4 . H232 . 110.0 no
C4 . C5 . O3 . 105.8(5) yes
C4 . C5 . H242 . 110.2 no
O3 . C5 . H242 . 109.6 no
C4 . C5 . H241 . 111.3 no
O3 . C5 . H241 . 109.8 no
H242 . C5 . H241 . 110.1 no
O3 . C6 . H263 . 109.4 no
O3 . C6 . H262 . 109.3 no
H263 . C6 . H262 . 109.9 no
O3 . C6 . H261 . 109.3 no
H263 . C6 . H261 . 109.3 no
H262 . C6 . H261 . 109.6 no
O7 2_657 C7 . C8 . 113.8(5) yes
O7 2_657 C7 . O4 . 129.3(5) yes
C8 . C7 . O4 . 116.9(5) yes
C7 . C8 . F5 . 105.9(7) yes
C7 . C8 . F4 . 108.7(7) yes
F5 . C8 . F4 . 102.9(8) yes
C7 . C8 . F6 . 122.6(7) yes
F5 . C8 . F6 . 106.4(8) yes
F4 . C8 . F6 . 108.5(8) yes
C7 . C8 . F3 . 109.2(6) yes
C7 . C8 . F2 . 110.3(6) yes
F3 . C8 . F2 . 102.2(7) yes
C7 . C8 . F1 . 117.1(6) yes
F3 . C8 . F1 . 107.3(7) yes
F2 . C8 . F1 . 109.7(7) yes
C10 . C9 . O5 . 115.6(5) yes
C10 . C9 . O8 . 116.4(5) yes
O5 . C9 . O8 . 127.9(5) yes
C9 . C10 . F9 . 109.7(5) yes
C9 . C10 . F8 . 112.7(5) yes
F9 . C10 . F8 . 107.4(6) yes
C9 . C10 . F7 . 112.6(5) yes
F9 . C10 . F7 . 107.3(6) yes
F8 . C10 . F7 . 106.8(6) yes
C12 . C11 . O6 . 112.8(6) yes
C12 . C11 . O9 . 117.7(6) yes
O6 . C11 . O9 . 129.4(6) yes
C11 . C12 . F11 . 110.4(7) yes
C11 . C12 . F12 . 113.6(7) yes
F11 . C12 . F12 . 105.7(8) yes
C11 . C12 . F10 . 112.3(7) yes
F11 . C12 . F10 . 108.9(10) yes
F12 . C12 . F10 . 105.6(8) yes
C1 . O1 . C2 . 110.7(5) yes
C1 . O1 . Yb1 . 125.0(4) yes
C2 . O1 . Yb1 . 118.1(3) yes
C3 . O2 . C4 . 113.1(5) yes
C3 . O2 . Yb1 . 114.9(3) yes
C4 . O2 . Yb1 . 119.7(4) yes
C5 . O3 . C6 . 111.9(5) yes
C5 . O3 . Yb1 . 116.1(4) yes
C6 . O3 . Yb1 . 122.9(4) yes
C7 . O4 . Yb1 . 137.9(4) yes
C9 . O5 . Yb1 2_657 153.0(4) yes
C11 . O6 . Yb1 . 139.0(4) yes
C7 2_657 O7 . Yb1 . 150.7(4) yes
C9 . O8 . Yb1 . 134.2(4) yes
O1 . Yb1 . O3 . 112.45(15) yes
O1 . Yb1 . O2 . 67.52(14) yes
O3 . Yb1 . O2 . 66.01(15) yes
O1 . Yb1 . O4 . 139.34(15) yes
O3 . Yb1 . O4 . 72.07(16) yes
O2 . Yb1 . O4 . 79.60(15) yes
O1 . Yb1 . O8 . 76.09(16) yes
O3 . Yb1 . O8 . 130.60(15) yes
O2 . Yb1 . O8 . 74.63(15) yes
O4 . Yb1 . O8 . 72.54(17) yes
O1 . Yb1 . O7 . 76.37(16) yes
O3 . Yb1 . O7 . 151.24(16) yes
O2 . Yb1 . O7 . 138.53(16) yes
O4 . Yb1 . O7 . 120.07(16) yes
O8 . Yb1 . O7 . 77.57(16) yes
O1 . Yb1 . O6 . 76.28(16) yes
O3 . Yb1 . O6 . 74.00(16) yes
O2 . Yb1 . O6 . 107.29(15) yes
O4 . Yb1 . O6 . 138.57(17) yes
O8 . Yb1 . O6 . 148.87(17) yes
O7 . Yb1 . O6 . 82.25(16) 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
C3 . H211 . O9 2_656 124.47(19) 0.976 2.587 3.242(10) yes
C1 . H272 . O7 . 123.00 0.962 2.516 3.142(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_global
_database_code_depnum_ccdc_archive 'CCDC 1429127'
_audit_update_record             
;
2015-11-10 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;
_audit_creation_date             2015-11-10
_audit_creation_method           CRYSTALS_ver_14.61

_oxford_structure_analysis_title 'import in P -1'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   10.769(5)
_cell_length_b                   11.261(5)
_cell_length_c                   12.310(5)
_cell_angle_alpha                76.890(5)
_cell_angle_beta                 77.650(5)
_cell_angle_gamma                74.503(5)
_cell_volume                     1382.3(6)

_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'
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'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Na 0.0362 0.0249 4.7626 3.2850 3.1736 8.8422 1.2674 0.3136 1.1128 129.4240
0.6760 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C14 H14 F12 Na2 O8 
# Dc =      1.40 Fooo =    676.00 Mu =      1.85 M =    584.22
# Found Formula = C14 H14 F12 Na4 O11 
# Dc =      1.63 FOOO =    676.00 Mu =      2.33 M =    678.19

_chemical_formula_sum            'C14 H14 F12 Na4 O11'
_chemical_formula_moiety         'C14 H14 F12 Na4 O11'
_chemical_compound_source        ?
_chemical_formula_weight         678.19


_cell_measurement_reflns_used    2987
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.090
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_max          0.100

_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             676
_exptl_absorpt_coefficient_mu    0.233

# Sheldrick geometric approximatio 0.81 0.98 
_exptl_absorpt_correction_type   none
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_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      150
_diffrn_reflns_number            5486
_reflns_number_total             5486
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 5486 
# Number of reflections with Friedels Law is 0 
# Theoretical number of reflections is about 6557 


_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_max         27.818
_diffrn_measured_fraction_theta_max 0.836

_diffrn_reflns_theta_full        25.036
_diffrn_measured_fraction_theta_full 0.854


_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              -14
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   2.53
_oxford_diffrn_Wilson_scale      0.30

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

_refine_diff_density_min         -0.77
_refine_diff_density_max         0.66


# 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         3555
_refine_ls_number_restraints     79
_refine_ls_number_parameters     424
_oxford_refine_ls_R_factor_ref   0.0583
_refine_ls_wR_factor_ref         0.0678
_refine_ls_goodness_of_fit_ref   1.1388
_refine_ls_shift/su_max          0.0006904
_refine_ls_shift/su_mean         0.0000416


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5467
_refine_ls_R_factor_all          0.0864
_refine_ls_wR_factor_all         0.0874

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3922
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_gt          0.0705

# 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: 
 4.42 0.800E-01 3.16 0.191 
;

# 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
F1 F 1.4526(4) 0.7703(4) -0.2305(3) 0.1093 1.0000 Uani . . . . . .
F2 F 1.3466(5) 0.9058(3) -0.1375(4) 0.0999 1.0000 Uani . . . . . .
F3 F 1.2459(4) 0.8392(5) -0.2300(3) 0.1167 1.0000 Uani D . . . . .
F4 F 1.1910(4) 0.8821(4) 0.2722(4) 0.0982 1.0000 Uani . . . . . .
F5 F 1.0081(6) 1.0047(3) 0.3156(4) 0.1171 1.0000 Uani . . . . . .
F6 F 1.0486(4) 0.8153(3) 0.4022(2) 0.0775 1.0000 Uani . . . . . .
F7 F 0.7881(9) 0.9027(8) -0.1245(14) 0.0914 0.3417 Uani D U . 1 2 .
F8 F 0.6253(11) 0.8377(15) 0.0106(11) 0.0823 0.3417 Uani D U . 1 2 .
F9 F 0.6651(12) 0.7980(10) -0.1514(9) 0.0780 0.3417 Uani D U . 1 2 .
F10 F 0.7158(7) 0.8470(5) -0.1814(3) 0.0753 0.6583 Uani D U . 1 1 .
F11 F 0.7566(5) 0.9066(3) -0.0420(5) 0.0625 0.6583 Uani D U . 1 1 .
F12 F 0.6077(5) 0.8060(7) -0.0123(7) 0.0688 0.6583 Uani D U . 1 1 .
F13 F 1.3456(12) 0.5689(12) 0.4652(6) 0.0849 0.4215 Uani D U . 2 2 .
F14 F 1.4494(10) 0.4302(9) 0.3758(14) 0.1118 0.4215 Uani D U . 2 2 .
F15 F 1.3844(10) 0.6316(9) 0.2948(9) 0.0984 0.4215 Uani D U . 2 2 .
F16 F 1.3354(9) 0.6249(7) 0.4245(8) 0.0903 0.5785 Uani D U . 2 1 .
F17 F 1.4085(6) 0.4264(6) 0.4318(6) 0.0901 0.5785 Uani D U . 2 1 .
F18 F 1.4420(4) 0.5301(8) 0.2744(4) 0.0779 0.5785 Uani D U . 2 1 .
C1 C 0.7571(9) 0.8824(7) 0.5501(6) 0.1086 1.0000 Uani . . . . . .
C2 C 0.6358(6) 0.8549(6) 0.4240(5) 0.0799 1.0000 Uani . . . . . .
C3 C 0.6498(5) 0.8112(5) 0.3166(4) 0.0618 1.0000 Uani . . . . . .
C4 C 0.7163(4) 0.6318(4) 0.2333(3) 0.0441 1.0000 Uani . . . . . .
C5 C 0.7787(4) 0.4961(4) 0.2537(4) 0.0441 1.0000 Uani . . . . . .
C6 C 0.9687(4) 0.3522(3) 0.3101(3) 0.0419 1.0000 Uani . . . . . .
C7 C 0.8252(3) 0.6859(3) -0.0442(3) 0.0241 1.0000 Uani . . . . . .
C8 C 0.7275(3) 0.8100(3) -0.0716(2) 0.0373 1.0000 Uani D . . . . .
C9 C 1.0109(3) 0.8515(3) 0.2107(3) 0.0268 1.0000 Uani . . . . . .
C10 C 1.0647(6) 0.8896(4) 0.3010(4) 0.0539 1.0000 Uani . . . . . .
C11 C 1.3110(3) 0.7029(3) -0.0641(3) 0.0277 1.0000 Uani . . . . . .
C12 C 1.3411(4) 0.8032(4) -0.1663(3) 0.0478 1.0000 Uani D . . . . .
C13 C 1.2209(3) 0.5164(3) 0.3474(3) 0.0272 1.0000 Uani . . . . . .
C14 C 1.3496(3) 0.5319(3) 0.3675(2) 0.0476 1.0000 Uani D . . . . .
O1 O 0.7613(4) 0.8286(3) 0.4560(3) 0.0691 1.0000 Uani . . . . . .
O2 O 0.7023(3) 0.6794(3) 0.3332(2) 0.0451 1.0000 Uani . . . . . .
O3 O 0.9102(3) 0.4808(2) 0.2704(2) 0.0319 1.0000 Uani . . . . . .
O4 O 0.9278(2) 0.6945(2) -0.0197(2) 0.0293 1.0000 Uani . . . . . .
O5 O 1.1963(2) 0.7189(2) -0.0169(2) 0.0338 1.0000 Uani . . . . . .
O6 O 0.9898(3) 0.7445(2) 0.23252(19) 0.0302 1.0000 Uani . . . . . .
O7 O 1.2094(3) 0.4083(2) 0.0501(2) 0.0327 1.0000 Uani . . . . . .
O8 O 0.8676(2) 0.4852(2) 0.56957(19) 0.0322 1.0000 Uani . . . . . .
O9 O 1.2205(2) 0.5054(2) 0.2503(2) 0.0336 1.0000 Uani . . . . . .
O10 O 1.5938(2) 0.3823(2) 0.0408(2) 0.0375 1.0000 Uani . . . . . .
Na1 Na 1.06735(12) 0.58618(11) 0.11908(10) 0.0227 1.0000 Uani . . . . . .
Na2 Na 1.38079(13) 0.45201(13) 0.10516(11) 0.0297 1.0000 Uani . . . . . .
Na3 Na 0.91142(13) 0.62324(12) 0.40224(10) 0.0286 1.0000 Uani . . . . . .
Na4 Na 1.00948(14) 0.86840(11) -0.04401(11) 0.0294 1.0000 Uani . . . . . .
O13 O 1.0012(3) 1.0685(2) -0.1244(2) 0.0350 1.0000 Uani . . . . . .
H11 H 0.8422 0.8628 0.5691 0.1214 1.0000 Uiso R . . . . .
H12 H 0.7270 0.9708 0.5323 0.1214 1.0000 Uiso R . . . . .
H13 H 0.6995 0.8495 0.6125 0.1214 1.0000 Uiso R . . . . .
H21 H 0.5999 0.9427 0.4142 0.0821 1.0000 Uiso R . . . . .
H22 H 0.5800 0.8129 0.4814 0.0821 1.0000 Uiso R . . . . .
H31 H 0.7066 0.8522 0.2594 0.0655 1.0000 Uiso R . . . . .
H32 H 0.5665 0.8296 0.2943 0.0655 1.0000 Uiso R . . . . .
H41 H 0.7695 0.6745 0.1738 0.0523 1.0000 Uiso R . . . . .
H42 H 0.6329 0.6440 0.2131 0.0523 1.0000 Uiso R . . . . .
H51 H 0.7314 0.4549 0.3190 0.0566 1.0000 Uiso R . . . . .
H52 H 0.7794 0.4612 0.1901 0.0566 1.0000 Uiso R . . . . .
H61 H 1.0555 0.3452 0.3204 0.0485 1.0000 Uiso R . . . . .
H62 H 0.9191 0.3232 0.3800 0.0485 1.0000 Uiso R . . . . .
H63 H 0.9701 0.3032 0.2562 0.0485 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.941(6)
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
F1 . C12 . 1.301(5) yes
F2 . C12 . 1.303(6) yes
F3 . C12 . 1.344(2) yes
F4 . C10 . 1.315(7) yes
F5 . C10 . 1.312(6) yes
F6 . C10 . 1.339(5) yes
F7 . C8 . 1.347(2) yes
F7 . Na4 . 2.675(11) yes
F8 . C8 . 1.348(2) yes
F9 . C8 . 1.351(2) yes
F10 . C8 . 1.344(2) yes
F11 . C8 . 1.351(2) yes
F11 . Na4 . 2.637(5) yes
F12 . C8 . 1.346(2) yes
F13 . C14 . 1.348(2) yes
F14 . C14 . 1.346(2) yes
F15 . C14 . 1.352(2) yes
F16 . C14 . 1.348(2) yes
F17 . C14 . 1.351(2) yes
F18 . C14 . 1.348(2) yes
F18 . Na2 . 2.696(6) yes
C1 . O1 . 1.412(7) yes
C1 . H11 . 0.950 no
C1 . H12 . 0.950 no
C1 . H13 . 0.950 no
C2 . C3 . 1.478(9) yes
C2 . O1 . 1.425(8) yes
C2 . H21 . 0.950 no
C2 . H22 . 0.950 no
C3 . O2 . 1.424(6) yes
C3 . H31 . 0.950 no
C3 . H32 . 0.950 no
C4 . C5 . 1.483(7) yes
C4 . O2 . 1.413(5) yes
C4 . H41 . 0.950 no
C4 . H42 . 0.950 no
C5 . O3 . 1.433(5) yes
C5 . H51 . 0.950 no
C5 . H52 . 0.950 no
C6 . O3 . 1.433(5) yes
C6 . H61 . 0.950 no
C6 . H62 . 0.950 no
C6 . H63 . 0.950 no
C7 . O7 2_765 1.235(4) yes
C7 . C8 . 1.525(5) yes
C7 . O4 . 1.238(4) yes
C9 . O13 2_775 1.233(4) yes
C9 . C10 . 1.543(6) yes
C9 . O6 . 1.245(4) yes
C11 . O10 2_865 1.237(4) yes
C11 . C12 . 1.529(5) yes
C11 . O5 . 1.231(4) yes
C13 . O8 2_766 1.240(4) yes
C13 . C14 . 1.519(5) yes
C13 . O9 . 1.230(4) yes
O1 . Na3 . 2.577(4) yes
O2 . Na3 . 2.451(3) yes
O3 . Na1 . 2.543(3) yes
O3 . Na3 . 2.531(3) yes
O4 . Na1 . 2.416(3) yes
O4 . Na4 . 2.289(3) yes
O5 . Na1 . 2.438(3) yes
O5 . Na4 . 2.284(3) yes
O6 . Na1 . 2.379(3) yes
O6 . Na3 . 2.347(3) yes
O7 . Na1 . 2.378(3) yes
O7 . Na2 . 2.298(3) yes
O8 . Na3 2_766 2.425(3) yes
O8 . Na3 . 2.325(3) yes
O9 . Na1 . 2.415(3) yes
O9 . Na2 . 2.269(3) yes
O10 . Na2 2_865 2.308(3) yes
O10 . Na2 . 2.247(3) yes
Na2 . Na2 2_865 3.440(3) yes
Na3 . Na3 2_766 3.639(3) yes
Na4 . O13 2_775 2.311(3) yes
Na4 . Na4 2_775 3.323(3) yes
Na4 . O13 . 2.232(3) yes
Na4 . O13 2_775 2.311(3) yes
Na4 . O13 . 2.232(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
C8 . F7 . Na4 . 109.5(6) yes
C8 . F11 . Na4 . 111.4(3) yes
C14 . F18 . Na2 . 114.0(3) yes
O1 . C1 . H11 . 109.4 no
O1 . C1 . H12 . 109.7 no
H11 . C1 . H12 . 109.5 no
O1 . C1 . H13 . 109.3 no
H11 . C1 . H13 . 109.5 no
H12 . C1 . H13 . 109.5 no
C3 . C2 . O1 . 109.0(4) yes
C3 . C2 . H21 . 109.7 no
O1 . C2 . H21 . 109.2 no
C3 . C2 . H22 . 109.9 no
O1 . C2 . H22 . 109.6 no
H21 . C2 . H22 . 109.5 no
C2 . C3 . O2 . 108.8(4) yes
C2 . C3 . H31 . 109.8 no
O2 . C3 . H31 . 109.7 no
C2 . C3 . H32 . 109.4 no
O2 . C3 . H32 . 109.6 no
H31 . C3 . H32 . 109.5 no
C5 . C4 . O2 . 109.0(3) yes
C5 . C4 . H41 . 109.6 no
O2 . C4 . H41 . 109.5 no
C5 . C4 . H42 . 109.6 no
O2 . C4 . H42 . 109.6 no
H41 . C4 . H42 . 109.5 no
C4 . C5 . O3 . 108.7(3) yes
C4 . C5 . H51 . 109.7 no
O3 . C5 . H51 . 109.7 no
C4 . C5 . H52 . 109.6 no
O3 . C5 . H52 . 109.6 no
H51 . C5 . H52 . 109.5 no
O3 . C6 . H61 . 109.5 no
O3 . C6 . H62 . 109.3 no
H61 . C6 . H62 . 109.5 no
O3 . C6 . H63 . 109.6 no
H61 . C6 . H63 . 109.5 no
H62 . C6 . H63 . 109.5 no
O7 2_765 C7 . C8 . 115.3(3) yes
O7 2_765 C7 . O4 . 129.6(3) yes
C8 . C7 . O4 . 115.1(3) yes
C7 . C8 . F11 . 113.1(3) yes
C7 . C8 . F12 . 111.2(4) yes
F11 . C8 . F12 . 104.1(5) yes
C7 . C8 . F10 . 114.8(3) yes
F11 . C8 . F10 . 105.3(4) yes
F12 . C8 . F10 . 107.7(5) yes
C7 . C8 . F9 . 107.1(5) yes
C7 . C8 . F8 . 116.1(7) yes
F9 . C8 . F8 . 100.3(10) yes
C7 . C8 . F7 . 111.6(5) yes
F9 . C8 . F7 . 102.9(9) yes
F8 . C8 . F7 . 116.7(10) yes
O13 2_775 C9 . C10 . 114.4(3) yes
O13 2_775 C9 . O6 . 129.0(3) yes
C10 . C9 . O6 . 116.6(3) yes
C9 . C10 . F6 . 112.8(4) yes
C9 . C10 . F4 . 110.9(4) yes
F6 . C10 . F4 . 106.1(4) yes
C9 . C10 . F5 . 111.9(4) yes
F6 . C10 . F5 . 107.1(5) yes
F4 . C10 . F5 . 107.8(5) yes
O10 2_865 C11 . C12 . 114.9(3) yes
O10 2_865 C11 . O5 . 129.5(3) yes
C12 . C11 . O5 . 115.6(3) yes
C11 . C12 . F3 . 111.2(3) yes
C11 . C12 . F2 . 112.6(4) yes
F3 . C12 . F2 . 104.6(4) yes
C11 . C12 . F1 . 114.4(3) yes
F3 . C12 . F1 . 108.9(5) yes
F2 . C12 . F1 . 104.6(4) yes
O8 2_766 C13 . C14 . 116.2(3) yes
O8 2_766 C13 . O9 . 129.2(4) yes
C14 . C13 . O9 . 114.6(3) yes
C13 . C14 . F17 . 109.7(4) yes
C13 . C14 . F18 . 112.9(3) yes
F17 . C14 . F18 . 98.0(5) yes
C13 . C14 . F16 . 113.3(5) yes
F17 . C14 . F16 . 105.7(6) yes
F18 . C14 . F16 . 115.7(6) yes
C13 . C14 . F15 . 110.2(5) yes
C13 . C14 . F13 . 115.7(6) yes
F15 . C14 . F13 . 98.5(8) yes
C13 . C14 . F14 . 118.3(7) yes
F15 . C14 . F14 . 112.8(8) yes
F13 . C14 . F14 . 99.4(9) yes
C2 . O1 . C1 . 111.8(5) yes
C2 . O1 . Na3 . 112.9(3) yes
C1 . O1 . Na3 . 128.1(4) yes
C3 . O2 . C4 . 111.4(3) yes
C3 . O2 . Na3 . 111.6(3) yes
C4 . O2 . Na3 . 110.4(2) yes
C5 . O3 . C6 . 111.6(3) yes
C5 . O3 . Na1 . 119.9(2) yes
C6 . O3 . Na1 . 111.7(2) yes
C5 . O3 . Na3 . 109.1(2) yes
C6 . O3 . Na3 . 112.6(2) yes
Na1 . O3 . Na3 . 90.22(9) yes
C7 . O4 . Na1 . 137.0(2) yes
C7 . O4 . Na4 . 129.1(2) yes
Na1 . O4 . Na4 . 90.12(11) yes
C11 . O5 . Na1 . 134.4(2) yes
C11 . O5 . Na4 . 135.0(2) yes
Na1 . O5 . Na4 . 89.69(10) yes
C9 . O6 . Na1 . 127.7(2) yes
C9 . O6 . Na3 . 131.9(2) yes
Na1 . O6 . Na3 . 99.05(10) yes
C7 2_765 O7 . Na1 . 124.5(2) yes
C7 2_765 O7 . Na2 . 137.3(2) yes
Na1 . O7 . Na2 . 89.56(10) yes
Na3 2_766 O8 . C13 2_766 118.3(2) yes
Na3 2_766 O8 . Na3 . 99.96(10) yes
C13 2_766 O8 . Na3 . 136.4(2) yes
C13 . O9 . Na1 . 135.0(2) yes
C13 . O9 . Na2 . 133.5(2) yes
Na1 . O9 . Na2 . 89.34(10) yes
Na2 2_865 O10 . C11 2_865 120.5(2) yes
Na2 2_865 O10 . Na2 . 98.09(11) yes
C11 2_865 O10 . Na2 . 141.1(2) yes
O7 . Na1 . O6 . 157.57(11) yes
O7 . Na1 . O9 . 75.99(10) yes
O6 . Na1 . O9 . 81.86(10) yes
O7 . Na1 . O4 . 107.57(10) yes
O6 . Na1 . O4 . 93.91(10) yes
O9 . Na1 . O4 . 171.39(10) yes
O7 . Na1 . O5 . 89.08(10) yes
O6 . Na1 . O5 . 89.97(9) yes
O9 . Na1 . O5 . 96.54(10) yes
O4 . Na1 . O5 . 75.89(10) yes
O7 . Na1 . O3 . 100.22(10) yes
O6 . Na1 . O3 . 81.47(9) yes
O9 . Na1 . O3 . 85.89(10) yes
O4 . Na1 . O3 . 100.95(10) yes
O5 . Na1 . O3 . 170.70(10) yes
O10 2_865 Na2 . O7 . 96.26(11) yes
O10 2_865 Na2 . O9 . 113.65(11) yes
O7 . Na2 . O9 . 80.48(10) yes
O10 2_865 Na2 . O10 . 81.91(11) yes
O7 . Na2 . O10 . 126.03(12) yes
O9 . Na2 . O10 . 149.08(12) yes
O10 2_865 Na2 . Na2 2_865 40.29(7) yes
O7 . Na2 . Na2 2_865 117.21(10) yes
O9 . Na2 . Na2 2_865 146.03(10) yes
O10 . Na2 . Na2 2_865 41.62(7) yes
O10 2_865 Na2 . F18 . 100.54(18) yes
O7 . Na2 . F18 . 141.74(11) yes
O9 . Na2 . F18 . 61.31(11) yes
O10 . Na2 . F18 . 90.43(14) yes
Na2 2_865 Na2 . F18 . 97.34(11) yes
O8 . Na3 . O6 . 170.99(11) yes
O8 . Na3 . O8 2_766 80.04(10) yes
O6 . Na3 . O8 2_766 91.06(9) yes
O8 . Na3 . O2 . 101.41(10) yes
O6 . Na3 . O2 . 86.50(10) yes
O8 2_766 Na3 . O2 . 160.51(11) yes
O8 . Na3 . O3 . 96.37(10) yes
O6 . Na3 . O3 . 82.34(9) yes
O8 2_766 Na3 . O3 . 91.45(10) yes
O2 . Na3 . O3 . 69.05(10) yes
O8 . Na3 . O1 . 99.83(12) yes
O6 . Na3 . O1 . 87.21(12) yes
O8 2_766 Na3 . O1 . 132.57(13) yes
O2 . Na3 . O1 . 66.68(13) yes
O3 . Na3 . O1 . 134.98(12) yes
O8 . Na3 . Na3 2_766 41.03(7) yes
O6 . Na3 . Na3 2_766 130.05(10) yes
O8 2_766 Na3 . Na3 2_766 39.00(6) yes
O2 . Na3 . Na3 2_766 139.00(10) yes
O3 . Na3 . Na3 2_766 95.04(9) yes
O1 . Na3 . Na3 2_766 124.05(10) yes
O13 2_775 Na4 . O4 . 112.76(11) yes
O13 2_775 Na4 . O5 . 91.72(11) yes
O4 . Na4 . O5 . 81.50(10) yes
O13 2_775 Na4 . Na4 2_775 42.09(7) yes
O4 . Na4 . Na4 2_775 147.11(10) yes
O5 . Na4 . Na4 2_775 114.05(10) yes
O13 2_775 Na4 . F11 . 98.13(15) yes
O4 . Na4 . F11 . 63.18(11) yes
O5 . Na4 . F11 . 144.46(12) yes
Na4 2_775 Na4 . F11 . 95.45(10) yes
O13 2_775 Na4 . O13 . 86.01(11) yes
O4 . Na4 . O13 . 148.14(12) yes
O5 . Na4 . O13 . 125.14(11) yes
Na4 2_775 Na4 . O13 . 43.93(8) yes
F11 . Na4 . O13 . 89.71(13) yes
O13 2_775 Na4 . O4 . 112.76(11) yes
O13 2_775 Na4 . O5 . 91.72(11) yes
O4 . Na4 . O5 . 81.50(10) yes
O13 2_775 Na4 . F7 . 118.8(4) yes
O4 . Na4 . F7 . 63.82(16) yes
O5 . Na4 . F7 . 140.1(3) yes
O13 2_775 Na4 . O13 . 86.01(11) yes
O4 . Na4 . O13 . 148.14(12) yes
O5 . Na4 . O13 . 125.14(11) yes
F7 . Na4 . O13 . 84.74(15) yes
Na4 2_775 O13 . Na4 . 93.99(11) yes
Na4 2_775 O13 . C9 2_775 118.9(2) yes
Na4 . O13 . C9 2_775 146.6(2) yes


