# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Euan Brechin'
'Konstantin Kamenev'
'Alistair Lennie'
'Stephen Moggach'
'Mark Murrie'
'Simon Parsons'
'Alessandro Prescimone'
'Javier Sanchez-Benitez'
'John E. Warren'

_publ_contact_author_name        'Euan Brechin'
_publ_contact_author_email       EBRECHIN@STAFFMAIL.ED.AC.UK

_publ_section_title              
;
High pressure studies
of hydroxo-bridged Cu(II) dimers
;
_publ_contact_author_address     
;
Room 85, School of Chemistry,
University of Edinburgh,
West Mains Road
Edinburgh, EH9 3JJ - UK.
;

# Attachment 'cu2003.cif'

data_cu2003
_database_code_depnum_ccdc_archive 'CCDC 746633'

#0.25 GPa data set.

_audit_creation_date             09-07-13
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cu2003 in P2(1)/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;
H atoms placed geometrically after each cycle on carbon.
That attached to O was located in the difference map
and allowed to ride on its parent O-atom.
It wasn't possible to locate H atoms on the water molecule

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.67
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.29 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.74
201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 1
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 712
341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 15
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 11
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 76

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?

H atoms on the water molecules are not present in the refined structure but
they obvioulsy must be counted.

075_ALERT_1_A Occupancy 3.00 greater than 1.0 for ...... O100
244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... >O100
779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 3.40 Deg.
CL1 -O1 -O100 1.555 1.555 1.555

The use of the "ring special shape" in the program CRYSTALS is causing this
alert: it was the best option to model the disordered perchlorate anion

242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1

It is a transition metal surrounded by O and N atoms: this behaviour is not
unexpected.

420_ALERT_2_B D-H Without Acceptor O10 - H101 ... ?

This H atom appeared in the difference map in that position.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.49 Ang.

This data set has been collected using synchrotron radiation at the above
wavelegth.

760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?

No action taken here.
;
#end of refcif
_cell_length_a                   7.7554(3)
_cell_length_b                   15.0450(4)
_cell_length_c                   11.2606(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.887(2)
_cell_angle_gamma                90
_cell_volume                     1257.23(8)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0010 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0020 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0040 0.0030 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'
Cl 0.0780 0.0740 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.2950 0.6400 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C12 H38 Cl2 Cu2 N4 O12
# Dc = 1.66 Fooo = 644.00 Mu = 19.64 M = 314.23
# Found Formula = C12 H34 Cl2 Cu2 N4 O12
# Dc = 1.65 FOOO = 644.00 Mu = 19.64 M = 312.21

_chemical_formula_sum            'C12 H38 Cl2 Cu2 N4 O12.00'
_chemical_formula_moiety         '[Cu2(OH)2(H2O)2(tmen)2][ClO4]2'
_chemical_formula_weight         628.46

_cell_measurement_reflns_used    4553
_cell_measurement_theta_min      2
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.12

_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    1.964

# Sheldrick geometric approximatio 0.82 0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.07
_exptl_absorpt_correction_T_max  0.85
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.48690
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      300
_diffrn_ambient_pressure         250000
_diffrn_reflns_number            11332
_reflns_number_total             1652
_diffrn_reflns_av_R_equivalents  0.074
# Number of reflections with Friedels Law is 1652
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2477

_diffrn_reflns_theta_min         1.592
_diffrn_reflns_theta_max         17.490
_diffrn_measured_fraction_theta_max 0.665

_diffrn_reflns_theta_full        13.292
_diffrn_measured_fraction_theta_full 0.737

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -7
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.72
_refine_diff_density_max         1.09

# 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         1253
_refine_ls_number_restraints     42
_refine_ls_number_parameters     118
_oxford_refine_ls_R_factor_ref   0.0774
_refine_ls_wR_factor_ref         0.1009
_refine_ls_goodness_of_fit_ref   1.3010
_refine_ls_shift/su_max          0.000291

# The values computed from all data
_oxford_reflns_number_all        1646
_refine_ls_R_factor_all          0.1043
_refine_ls_wR_factor_all         0.1096

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                1253
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_gt          0.1009

# 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    noref # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
2.06 1.03 1.24
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 1.00237(17) 0.55890(6) 0.89534(9) 0.0498 1.0000 Uani . . . . . . .
N11 N 1.1687(12) 0.6539(4) 0.8628(6) 0.0502 1.0000 Uani . U . . . . .
N21 N 0.8769(11) 0.5617(4) 0.7098(7) 0.0468 1.0000 Uani . U . . . . .
C11 C 1.075(2) 0.6877(7) 0.7364(9) 0.0699 1.0000 Uani . U . . . . .
C21 C 0.9908(17) 0.6146(7) 0.6541(10) 0.0640 1.0000 Uani . U . . . . .
C31 C 1.1951(18) 0.7293(6) 0.9484(10) 0.0703 1.0000 Uani . U . . . . .
C41 C 1.3429(18) 0.6144(7) 0.8741(12) 0.0699 1.0000 Uani . U . . . . .
C51 C 0.8550(17) 0.4716(6) 0.6525(10) 0.0672 1.0000 Uani . U . . . . .
C61 C 0.6953(16) 0.6018(7) 0.6851(9) 0.0612 1.0000 Uani . U . . . . .
Cl1 Cl 0.6229(4) 0.63095(14) 0.2782(2) 0.0604 1.0000 Uani . . . . . . .
O1 O 0.6586(17) 0.5531(6) 0.3530(10) 0.0999 1.0000 Uani . . . . . . .
O10 O 0.8658(13) 0.4635(5) 0.9352(6) 0.0829 1.0000 Uani . . . . . . .
O11 O 0.825(2) 0.6703(8) 0.9758(13) 0.137(4) 1.0000 Uiso . . . . . . .
O100 O 0.615(2) 0.6590(7) 0.2637(14) 0.128(4) 3.0000 Uiso . . . . . Annulus .
H111 H 1.1597 0.7203 0.7041 0.0861 1.0000 Uiso . . . . . . .
H112 H 0.9801 0.7299 0.7428 0.0863 1.0000 Uiso . . . . . . .
H211 H 1.0877 0.5758 0.6427 0.0801 1.0000 Uiso . . . . . . .
H212 H 0.9212 0.6365 0.5734 0.0799 1.0000 Uiso . . . . . . .
H311 H 1.2478 0.7099 1.0327 0.1039 1.0000 Uiso . . . . . . .
H312 H 1.2768 0.7724 0.9286 0.1041 1.0000 Uiso . . . . . . .
H313 H 1.0833 0.7585 0.9414 0.1040 1.0000 Uiso . . . . . . .
H411 H 1.3999 0.5993 0.9617 0.1130 1.0000 Uiso . . . . . . .
H412 H 1.4211 0.6539 0.8495 0.1130 1.0000 Uiso . . . . . . .
H413 H 1.3309 0.5607 0.8278 0.1133 1.0000 Uiso . . . . . . .
H511 H 0.7627 0.4392 0.6779 0.0971 1.0000 Uiso . . . . . . .
H512 H 0.9643 0.4381 0.6777 0.0970 1.0000 Uiso . . . . . . .
H513 H 0.8151 0.4759 0.5631 0.0969 1.0000 Uiso . . . . . . .
H613 H 0.6223 0.5674 0.7236 0.0940 1.0000 Uiso . . . . . . .
H612 H 0.7033 0.6615 0.7155 0.0941 1.0000 Uiso . . . . . . .
H611 H 0.6371 0.6032 0.5965 0.0940 1.0000 Uiso . . . . . . .
H101 H 0.7586 0.4599 0.8945 0.1160 1.0000 Uiso . . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0577(10) 0.0534(7) 0.0366(6) 0.0122(4) 0.0108(6) -0.0143(4)
N11 0.068(7) 0.046(4) 0.037(4) 0.003(3) 0.016(4) -0.010(3)
N21 0.051(6) 0.050(4) 0.040(4) 0.004(2) 0.012(4) -0.002(3)
C11 0.091(9) 0.076(6) 0.045(5) 0.016(4) 0.025(6) -0.023(5)
C21 0.060(8) 0.086(7) 0.050(6) 0.010(4) 0.024(6) -0.022(5)
C31 0.093(10) 0.046(5) 0.072(7) -0.007(4) 0.024(7) -0.002(5)
C41 0.064(9) 0.071(7) 0.092(9) -0.019(5) 0.050(7) -0.013(5)
C51 0.082(9) 0.058(6) 0.057(6) -0.008(4) 0.011(6) 0.005(5)
C61 0.061(8) 0.075(6) 0.053(6) 0.002(4) 0.024(6) 0.010(5)
Cl1 0.0505(18) 0.0601(14) 0.0646(15) 0.0034(9) 0.0073(13) -0.0048(9)
O1 0.129(10) 0.094(6) 0.086(7) 0.028(4) 0.045(7) 0.018(5)
O10 0.088(7) 0.102(5) 0.045(4) 0.022(3) -0.003(5) -0.051(5)

# special_uiso is a measure of the thickness of the shape
# special_size is the length of the line
# or the radius of the annulus or sphere
# special_declination and azimuth define the direction
# of the line or normal to the annulus
# Because CHECKCIF rejects occupancies greater than unity
# it will generate incorrect formulae, and derived values
loop_
_atom_site_oxford_special_label
_atom_site_oxford_special_uiso
_atom_site_oxford_special_size
_atom_site_oxford_special_declination
_atom_site_oxford_special_azimuth
O100 0.128(4) 1.362(11) 0.6083 -0.7930

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.796(5)
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
Cu1 . Cu1 2_767 2.9578(19) yes
Cu1 . O10 2_767 1.914(6) yes
Cu1 . N11 . 2.029(8) yes
Cu1 . N21 . 2.033(7) yes
Cu1 . O10 . 1.913(7) yes
Cu1 . O11 . 2.501(15) yes
N11 . C11 . 1.487(11) yes
N11 . C31 . 1.464(12) yes
N11 . C41 . 1.448(15) yes
N21 . C21 . 1.460(14) yes
N21 . C51 . 1.490(12) yes
N21 . C61 . 1.482(14) yes
C11 . C21 . 1.464(15) yes
C11 . H111 . 0.973 no
C11 . H112 . 0.988 no
C21 . H211 . 0.989 no
C21 . H212 . 0.969 no
C31 . H311 . 0.963 no
C31 . H312 . 0.977 no
C31 . H313 . 0.954 no
C41 . H411 . 0.983 no
C41 . H412 . 0.947 no
C41 . H413 . 0.951 no
C51 . H511 . 0.975 no
C51 . H512 . 0.956 no
C51 . H513 . 0.965 no
C61 . H613 . 0.959 no
C61 . H612 . 0.957 no
C61 . H611 . 0.968 no
Cl1 . O1 . 1.422(8) yes
O1 . O100 . 1.863(12) yes
O10 . H101 . 0.827 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
Cu1 2_767 Cu1 . O10 2_767 39.4(2) yes
Cu1 2_767 Cu1 . N11 . 136.22(19) yes
O10 2_767 Cu1 . N11 . 96.9(3) yes
Cu1 2_767 Cu1 . N21 . 135.9(2) yes
O10 2_767 Cu1 . N21 . 170.2(4) yes
N11 . Cu1 . N21 . 86.5(3) yes
Cu1 2_767 Cu1 . O10 . 39.41(18) yes
O10 2_767 Cu1 . O10 . 78.8(3) yes
N11 . Cu1 . O10 . 174.5(4) yes
N21 . Cu1 . O10 . 97.2(3) yes
Cu1 2_767 Cu1 . O11 . 88.7(3) yes
O10 2_767 Cu1 . O11 . 87.0(5) yes
N11 . Cu1 . O11 . 92.3(4) yes
N21 . Cu1 . O11 . 102.0(4) yes
O10 . Cu1 . O11 . 91.0(5) yes
Cu1 . N11 . C11 . 104.7(6) yes
Cu1 . N11 . C31 . 113.7(8) yes
C11 . N11 . C31 . 107.5(7) yes
Cu1 . N11 . C41 . 108.7(6) yes
C11 . N11 . C41 . 114.2(11) yes
C31 . N11 . C41 . 108.2(8) yes
Cu1 . N21 . C21 . 106.5(5) yes
Cu1 . N21 . C51 . 112.7(5) yes
C21 . N21 . C51 . 108.5(10) yes
Cu1 . N21 . C61 . 110.3(7) yes
C21 . N21 . C61 . 111.0(8) yes
C51 . N21 . C61 . 107.9(8) yes
N11 . C11 . C21 . 110.7(8) yes
N11 . C11 . H111 . 109.6 no
C21 . C11 . H111 . 111.5 no
N11 . C11 . H112 . 108.5 no
C21 . C11 . H112 . 108.9 no
H111 . C11 . H112 . 107.5 no
C11 . C21 . N21 . 110.5(10) yes
C11 . C21 . H211 . 108.1 no
N21 . C21 . H211 . 108.1 no
C11 . C21 . H212 . 111.3 no
N21 . C21 . H212 . 110.2 no
H211 . C21 . H212 . 108.5 no
N11 . C31 . H311 . 110.6 no
N11 . C31 . H312 . 109.9 no
H311 . C31 . H312 . 108.0 no
N11 . C31 . H313 . 110.6 no
H311 . C31 . H313 . 109.7 no
H312 . C31 . H313 . 108.0 no
N11 . C41 . H411 . 108.7 no
N11 . C41 . H412 . 112.1 no
H411 . C41 . H412 . 107.4 no
N11 . C41 . H413 . 111.1 no
H411 . C41 . H413 . 107.3 no
H412 . C41 . H413 . 110.0 no
N21 . C51 . H511 . 109.2 no
N21 . C51 . H512 . 111.8 no
H511 . C51 . H512 . 108.2 no
N21 . C51 . H513 . 110.6 no
H511 . C51 . H513 . 107.4 no
H512 . C51 . H513 . 109.5 no
N21 . C61 . H613 . 110.5 no
N21 . C61 . H612 . 110.8 no
H613 . C61 . H612 . 109.2 no
N21 . C61 . H611 . 109.6 no
H613 . C61 . H611 . 108.5 no
H612 . C61 . H611 . 108.2 no
Cl1 . O1 . O100 . 3.4(5) yes
Cu1 2_767 O10 . Cu1 . 101.2(3) yes
Cu1 2_767 O10 . H101 . 134.5 no
Cu1 . O10 . H101 . 117.1 no
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
C51 . H513 . O1 . 155 0.97 2.60 3.495(16) yes

# Attachment 'cu2004.cif'

data_cu2004
_database_code_depnum_ccdc_archive 'CCDC 746634'

#0.70 GPa data set.

_audit_creation_date             09-07-13
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cu2004 in P2(1)/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;
H atoms placed geometrically after each cycle on carbon.
That attached to O was located in the difference map
and allowed to ride on its parent O-atom.
It wasn't possible to locate H atoms on the water molecule

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.67
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.46 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.75
201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 1
341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 16
910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) ..... 12
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 680
088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.51
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 101

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?

H atoms on the water molecules are not present in the refined structure but
they obvioulsy must be counted.

075_ALERT_1_A Occupancy 3.00 greater than 1.0 for ...... O100
244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... >O100

The use of the "ring special shape" in the program CRYSTALS is causing this
alert: it was the best option to model the disordered perchlorate anion

242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1

It is a transition metal surrounded by O and N atoms: this behaviour is not
unexpected.

420_ALERT_2_B D-H Without Acceptor O10 - H101 ... ?

This H atom appeared in the difference map in that position.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.49 Ang.

This data set has been collected using synchrotron radiation at the above
wavelegth.

760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N21
250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.11
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 77
213_ALERT_2_C Atom O10 has ADP max/min Ratio ............. 3.10 prola
919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1

No action taken here.

860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 42

Crystals list 16 attached here:

#LIST 16
DIST 0.0, 0.01 = MEAN CL(1) TO O(1), CL(1) TO O(2)
CONT CL(1) TO O(3), CL(1) TO O(4)
DIST 0.0, 0.01 = MEAN O(1) TO O(2) , O(3) TO O(4)
CONT O(2) TO O(4) , O(1) TO O(3)
CONT O(1) TO O(4) , O(2) TO O(3)
U(IJ) .0, 0.04000 = N(11) TO C(11)
U(IJ) .0, 0.08000 = N(11) TO C(31)
U(IJ) .0, 0.08000 = N(11) TO C(41)
U(IJ) .0, 0.04000 = N(21) TO C(21)
U(IJ) .0, 0.08000 = N(21) TO C(51)
U(IJ) .0, 0.08000 = N(21) TO C(61)
U(IJ) .0, 0.04000 = C(11) TO C(21)
U(IJ) .0, 0.08000 = CL(1) TO O(1)
U(IJ) .0, 0.08000 = CL(1) TO O(2)
U(IJ) .0, 0.08000 = CL(1) TO O(3)
U(IJ) .0, 0.08000 = CL(1) TO O(4)
REM THERMSIM END (DO NOT REMOVE THIS LINE)
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END

;
#end of refcif
_cell_length_a                   7.6403(3)
_cell_length_b                   14.7724(4)
_cell_length_c                   11.1904(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.386(3)
_cell_angle_gamma                90
_cell_volume                     1205.31(7)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0010 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0020 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0040 0.0030 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'
Cl 0.0780 0.0740 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.2950 0.6400 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C12 H38 Cl2 Cu2 N4 O12
# Dc = 1.73 Fooo = 644.00 Mu = 20.49 M = 314.23
# Found Formula = C12 H34 Cl2 Cu2 N4 O12
# Dc = 1.72 FOOO = 644.00 Mu = 20.48 M = 312.21

_chemical_formula_sum            'C12 H38 Cl2 Cu2 N4 O12.00'
_chemical_formula_moiety         '[Cu2(OH)2(H2O)2(tmen)2][ClO4]2'
_chemical_formula_weight         628.46

_cell_measurement_reflns_used    3516
_cell_measurement_theta_min      2
_cell_measurement_theta_max      16
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.12

_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.048

# Sheldrick geometric approximatio 0.81 0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_T_max  0.85
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.48690
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      300
_diffrn_ambient_pressure         700000
_diffrn_reflns_number            11243
_reflns_number_total             1646
_diffrn_reflns_av_R_equivalents  0.084
# Number of reflections with Friedels Law is 1646
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2455

_diffrn_reflns_theta_min         2.134
_diffrn_reflns_theta_max         17.716
_diffrn_measured_fraction_theta_max 0.668

_diffrn_reflns_theta_full        13.464
_diffrn_measured_fraction_theta_full 0.751

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -7
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.86
_refine_diff_density_max         1.09

# 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         1122
_refine_ls_number_restraints     42
_refine_ls_number_parameters     118
_oxford_refine_ls_R_factor_ref   0.0829
_refine_ls_wR_factor_ref         0.0985
_refine_ls_goodness_of_fit_ref   1.1092
_refine_ls_shift/su_max          0.000230

# The values computed from all data
_oxford_reflns_number_all        1626
_refine_ls_R_factor_all          0.1139
_refine_ls_wR_factor_all         0.1193

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                1122
_refine_ls_R_factor_gt           0.0829
_refine_ls_wR_factor_gt          0.0985

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.709 0.571 0.270
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 1.0021(2) 0.55965(8) 0.89495(11) 0.0584 1.0000 Uani . . . . . . .
N11 N 1.1722(13) 0.6552(5) 0.8621(7) 0.0546 1.0000 Uani . U . . . . .
N21 N 0.8749(12) 0.5623(5) 0.7064(7) 0.0440 1.0000 Uani . U . . . . .
C11 C 1.0821(18) 0.6900(7) 0.7379(9) 0.0647 1.0000 Uani . U . . . . .
C21 C 0.994(2) 0.6144(8) 0.6517(10) 0.0643 1.0000 Uani . U . . . . .
C31 C 1.2057(19) 0.7328(6) 0.9490(10) 0.0661 1.0000 Uani . U . . . . .
C41 C 1.348(2) 0.6129(7) 0.8732(13) 0.0766 1.0000 Uani . U . . . . .
C51 C 0.8503(19) 0.4699(6) 0.6517(10) 0.0683 1.0000 Uani . U . . . . .
C61 C 0.6941(18) 0.6049(7) 0.6809(11) 0.0692 1.0000 Uani . U . . . . .
Cl1 Cl 0.6256(4) 0.63097(15) 0.2806(3) 0.0600 1.0000 Uani . . . . . . .
O1 O 0.6550(17) 0.5520(6) 0.3562(9) 0.0876 1.0000 Uani . . . . . . .
O10 O 0.8620(17) 0.4643(7) 0.9342(7) 0.1105 1.0000 Uani . . . . . . .
O11 O 0.827(3) 0.6703(11) 0.9792(19) 0.164(6) 1.0000 Uiso . . . . . . .
O100 O 0.619(2) 0.6632(7) 0.2666(13) 0.111(4) 3.0000 Uiso . . . . . Annulus .
H111 H 1.1711 0.7219 0.7062 0.0803 1.0000 Uiso R . . . . . .
H112 H 0.9872 0.7317 0.7437 0.0803 1.0000 Uiso R . . . . . .
H211 H 1.0908 0.5748 0.6423 0.0811 1.0000 Uiso R . . . . . .
H212 H 0.9242 0.6381 0.5706 0.0810 1.0000 Uiso R . . . . . .
H311 H 1.2720 0.7123 1.0316 0.0978 1.0000 Uiso R . . . . . .
H313 H 1.2750 0.7788 0.9225 0.0979 1.0000 Uiso R . . . . . .
H312 H 1.0899 0.7577 0.9504 0.0981 1.0000 Uiso R . . . . . .
H413 H 1.4031 0.5963 0.9593 0.1239 1.0000 Uiso R . . . . . .
H411 H 1.4258 0.6545 0.8477 0.1240 1.0000 Uiso R . . . . . .
H412 H 1.3304 0.5599 0.8215 0.1240 1.0000 Uiso R . . . . . .
H512 H 0.7515 0.4410 0.6736 0.1010 1.0000 Uiso R . . . . . .
H511 H 0.9608 0.4357 0.6854 0.1010 1.0000 Uiso R . . . . . .
H513 H 0.8214 0.4734 0.5623 0.1010 1.0000 Uiso R . . . . . .
H611 H 0.6228 0.5728 0.7242 0.1010 1.0000 Uiso R . . . . . .
H613 H 0.7084 0.6666 0.7088 0.1011 1.0000 Uiso R . . . . . .
H612 H 0.6327 0.6035 0.5922 0.1011 1.0000 Uiso R . . . . . .
H101 H 0.7621 0.4526 0.8837 0.1520 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0749(12) 0.0631(8) 0.0362(7) 0.0084(5) 0.0153(6) -0.0286(6)
N11 0.075(7) 0.045(4) 0.043(4) 0.005(3) 0.016(4) -0.011(3)
N21 0.052(6) 0.054(4) 0.031(4) 0.003(3) 0.019(4) -0.005(3)
C11 0.082(9) 0.070(7) 0.048(5) 0.007(4) 0.027(6) -0.022(5)
C21 0.080(10) 0.083(7) 0.034(5) 0.002(4) 0.024(6) -0.023(5)
C31 0.087(10) 0.049(6) 0.062(6) -0.010(4) 0.021(6) -0.004(5)
C41 0.096(12) 0.064(7) 0.090(9) -0.019(6) 0.059(8) -0.003(6)
C51 0.096(10) 0.050(6) 0.053(6) -0.007(4) 0.012(6) -0.004(5)
C61 0.077(9) 0.062(6) 0.060(6) -0.007(4) 0.009(6) 0.003(5)
Cl1 0.0496(19) 0.0582(15) 0.0660(16) 0.0092(10) 0.0078(14) 0.0008(9)
O1 0.115(9) 0.090(6) 0.069(6) 0.019(4) 0.043(6) 0.016(5)
O10 0.139(10) 0.140(8) 0.040(4) 0.020(4) 0.006(6) -0.099(8)

# special_uiso is a measure of the thickness of the shape
# special_size is the length of the line
# or the radius of the annulus or sphere
# special_declination and azimuth define the direction
# of the line or normal to the annulus
# Because CHECKCIF rejects occupancies greater than unity
# it will generate incorrect formulae, and derived values
loop_
_atom_site_oxford_special_label
_atom_site_oxford_special_uiso
_atom_site_oxford_special_size
_atom_site_oxford_special_declination
_atom_site_oxford_special_azimuth
O100 0.111(4) 1.344(10) 0.6083 -0.7930

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2632(17)
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
Cu1 . Cu1 2_767 2.946(2) yes
Cu1 . O10 2_767 1.916(7) yes
Cu1 . N11 . 2.025(9) yes
Cu1 . N21 . 2.043(7) yes
Cu1 . O10 . 1.899(7) yes
Cu1 . O11 . 2.47(2) yes
N11 . C11 . 1.449(12) yes
N11 . C31 . 1.475(12) yes
N11 . C41 . 1.451(18) yes
N21 . C21 . 1.460(15) yes
N21 . C51 . 1.484(12) yes
N21 . C61 . 1.466(16) yes
C11 . C21 . 1.497(14) yes
C11 . H111 . 0.977 no
C11 . H112 . 0.968 no
C21 . H211 . 0.971 no
C21 . H212 . 0.971 no
C31 . H311 . 0.961 no
C31 . H313 . 0.961 no
C31 . H312 . 0.963 no
C41 . H413 . 0.961 no
C41 . H411 . 0.957 no
C41 . H412 . 0.959 no
C51 . H512 . 0.961 no
C51 . H511 . 0.959 no
C51 . H513 . 0.959 no
C61 . H611 . 0.956 no
C61 . H613 . 0.959 no
C61 . H612 . 0.963 no
Cl1 . O1 . 1.419(8) yes
O10 . H101 . 0.821 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
Cu1 2_767 Cu1 . O10 2_767 39.2(2) yes
Cu1 2_767 Cu1 . N11 . 136.3(2) yes
O10 2_767 Cu1 . N11 . 97.1(3) yes
Cu1 2_767 Cu1 . N21 . 136.1(2) yes
O10 2_767 Cu1 . N21 . 169.4(5) yes
N11 . Cu1 . N21 . 86.1(3) yes
Cu1 2_767 Cu1 . O10 . 39.7(2) yes
O10 2_767 Cu1 . O10 . 78.9(3) yes
N11 . Cu1 . O10 . 174.8(5) yes
N21 . Cu1 . O10 . 97.2(3) yes
Cu1 2_767 Cu1 . O11 . 87.4(5) yes
O10 2_767 Cu1 . O11 . 86.3(6) yes
N11 . Cu1 . O11 . 93.3(5) yes
N21 . Cu1 . O11 . 103.7(5) yes
O10 . Cu1 . O11 . 89.8(7) yes
Cu1 . N11 . C11 . 106.0(6) yes
Cu1 . N11 . C31 . 114.6(8) yes
C11 . N11 . C31 . 107.2(7) yes
Cu1 . N11 . C41 . 108.1(7) yes
C11 . N11 . C41 . 113.4(11) yes
C31 . N11 . C41 . 107.7(9) yes
Cu1 . N21 . C21 . 106.2(5) yes
Cu1 . N21 . C51 . 111.8(5) yes
C21 . N21 . C51 . 109.3(10) yes
Cu1 . N21 . C61 . 109.8(7) yes
C21 . N21 . C61 . 111.2(9) yes
C51 . N21 . C61 . 108.6(8) yes
N11 . C11 . C21 . 110.3(8) yes
N11 . C11 . H111 . 109.7 no
C21 . C11 . H111 . 110.7 no
N11 . C11 . H112 . 108.1 no
C21 . C11 . H112 . 108.5 no
H111 . C11 . H112 . 109.6 no
C11 . C21 . N21 . 109.8(10) yes
C11 . C21 . H211 . 108.0 no
N21 . C21 . H211 . 108.5 no
C11 . C21 . H212 . 110.5 no
N21 . C21 . H212 . 110.1 no
H211 . C21 . H212 . 109.9 no
N11 . C31 . H311 . 109.0 no
N11 . C31 . H313 . 110.4 no
H311 . C31 . H313 . 109.9 no
N11 . C31 . H312 . 109.2 no
H311 . C31 . H312 . 109.1 no
H313 . C31 . H312 . 109.2 no
N11 . C41 . H413 . 108.3 no
N11 . C41 . H411 . 110.0 no
H413 . C41 . H411 . 109.6 no
N11 . C41 . H412 . 110.0 no
H413 . C41 . H412 . 109.6 no
H411 . C41 . H412 . 109.3 no
N21 . C51 . H512 . 108.4 no
N21 . C51 . H511 . 109.5 no
H512 . C51 . H511 . 109.4 no
N21 . C51 . H513 . 110.0 no
H512 . C51 . H513 . 109.7 no
H511 . C51 . H513 . 109.8 no
N21 . C61 . H611 . 109.5 no
N21 . C61 . H613 . 109.6 no
H611 . C61 . H613 . 109.4 no
N21 . C61 . H612 . 109.4 no
H611 . C61 . H612 . 109.6 no
H613 . C61 . H612 . 109.3 no
Cu1 2_767 O10 . Cu1 . 101.1(3) yes
Cu1 2_767 O10 . H101 . 139.7 no
Cu1 . O10 . H101 . 118.0 no
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
C31 . H312 . O11 . 126 0.96 2.49 3.150(17) yes
C51 . H513 . O1 . 150 0.96 2.56 3.417(17) yes

# Attachment 'cu2005.cif'

data_cu2005
_database_code_depnum_ccdc_archive 'CCDC 746635'

#1.20 GPa data set.

_audit_creation_date             09-07-13
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cu2005 in P2(1)/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;
H atoms placed geometrically after each cycle on carbon.
That attached to O was located in the difference map
and allowed to ride on its parent O-atom.
It wasn't possible to locate H atoms on the water molecule

Checkcif output:

027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 15.28 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.72
201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 2
341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 19
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 690
082_ALERT_2_C High R1 Value .................................. 0.12
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 590

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?

H atoms on the water molecules are not present in the refined structure but
they obvioulsy must be counted.

075_ALERT_1_A Occupancy 3.00 greater than 1.0 for ...... O100
244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... >O100

The use of the "ring special shape" in the program CRYSTALS is causing this
alert: it was the best option to model the disordered perchlorate anion

420_ALERT_2_B D-H Without Acceptor O10 - H101 ... ?

This H atom appeared in the difference map in that position.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.49 Ang.

This data set has been collected using synchrotron radiation at the above
wavelegth.

950_ALERT_1_C Reported and Calculated Hmax Values Differ by .. 2

The calculate value is determined assuming an 100% complete data set:
because of the limitations due to the use of the pressure cell this cannot
be achieved therefore platon can be terribly wrong in these calculations

919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N11
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N21
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 11
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?

No action taken here.

860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 42

Crystals list 16 attached here:

#LIST 16
U(IJ) .0, 0.04000 = N(11) TO C(11)
U(IJ) .0, 0.08000 = N(11) TO C(31)
U(IJ) .0, 0.08000 = N(11) TO C(41)
U(IJ) .0, 0.04000 = N(21) TO C(21)
U(IJ) .0, 0.08000 = N(21) TO C(51)
U(IJ) .0, 0.08000 = N(21) TO C(61)
U(IJ) .0, 0.04000 = C(11) TO C(21)
REM THERMSIM END (DO NOT REMOVE THIS LINE)
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END

;
#end of refcif
_cell_length_a                   7.5255(4)
_cell_length_b                   14.4578(5)
_cell_length_c                   11.1416(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.311(2)
_cell_angle_gamma                90
_cell_volume                     1150.85(8)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0010 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0020 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0040 0.0030 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'
Cl 0.0780 0.0740 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.2950 0.6400 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C12 H38 Cl2 Cu2 N4 O12
# Dc = 1.81 Fooo = 644.00 Mu = 21.46 M = 314.23
# Found Formula = C12 H34 Cl2 Cu2 N4 O12
# Dc = 1.80 FOOO = 644.00 Mu = 21.45 M = 312.21

_chemical_formula_sum            'C12 H38 Cl2 Cu2 N4 O12.00'
_chemical_formula_moiety         '[Cu2(OH)2(H2O)2(tmen)2][ClO4]2'
_chemical_formula_weight         628.46

_cell_measurement_reflns_used    3198
_cell_measurement_theta_min      3
_cell_measurement_theta_max      16
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.12

_exptl_crystal_density_diffrn    1.802
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.145

# Sheldrick geometric approximatio 0.81 0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.18
_exptl_absorpt_correction_T_max  0.84
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.48690
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      300
_diffrn_ambient_pressure         1200000
_diffrn_reflns_number            11994
_reflns_number_total             2004
_diffrn_reflns_av_R_equivalents  0.071
# Number of reflections with Friedels Law is 2004
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3511

_diffrn_reflns_theta_min         1.634
_diffrn_reflns_theta_max         20.370
_diffrn_measured_fraction_theta_max 0.570

_diffrn_reflns_theta_full        15.278
_diffrn_measured_fraction_theta_full 0.716

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -7
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -1.10
_refine_diff_density_max         1.86

# 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         1156
_refine_ls_number_restraints     42
_refine_ls_number_parameters     113
_oxford_refine_ls_R_factor_ref   0.1248
_refine_ls_wR_factor_ref         0.1472
_refine_ls_goodness_of_fit_ref   1.1199
_refine_ls_shift/su_max          0.000138

# The values computed from all data
_oxford_reflns_number_all        1971
_refine_ls_R_factor_all          0.1758
_refine_ls_wR_factor_all         0.1804

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                1156
_refine_ls_R_factor_gt           0.1248
_refine_ls_wR_factor_gt          0.1472

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
2.89 0.697 1.11 -0.463 -0.213
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 1.0030(4) 0.56047(14) 0.89463(15) 0.0807 1.0000 Uani . . . . . . .
N11 N 1.1781(16) 0.6558(6) 0.8636(8) 0.0410 1.0000 Uani . U . . . . .
N21 N 0.8708(16) 0.5617(6) 0.7057(9) 0.0385 1.0000 Uani . U . . . . .
C11 C 1.092(2) 0.6906(9) 0.7381(12) 0.0575 1.0000 Uani . U . . . . .
C21 C 1.000(2) 0.6148(9) 0.6510(13) 0.0519 1.0000 Uani . U . . . . .
C31 C 1.208(2) 0.7358(8) 0.9522(12) 0.0548 1.0000 Uani . U . . . . .
C41 C 1.361(3) 0.6113(9) 0.8751(16) 0.0618 1.0000 Uani . U . . . . .
C51 C 0.843(2) 0.4677(8) 0.6505(13) 0.0575 1.0000 Uani . U . . . . .
C61 C 0.693(2) 0.6079(10) 0.6746(16) 0.0587 1.0000 Uani . U . . . . .
Cl1 Cl 0.6300(5) 0.6324(2) 0.2826(3) 0.0560 1.0000 Uani . . . . . . .
O1 O 0.659(2) 0.5526(7) 0.3577(11) 0.0836 1.0000 Uani . . . . . . .
O10 O 0.844(3) 0.4715(9) 0.9350(15) 0.102(4) 1.0000 Uiso . . . . . . .
O11 O 0.824(4) 0.6594(17) 0.996(3) 0.181(9) 1.0000 Uiso . . . . . . .
O100 O 0.632(3) 0.6693(9) 0.2702(16) 0.098(5) 3.0000 Uiso . . . . . Annulus .
H101 H 0.7441 0.4598 0.8845 0.1520 1.0000 Uiso R . . . . . .
H111 H 1.1813 0.7216 0.7086 0.0704 1.0000 Uiso R . . . . . .
H112 H 0.9964 0.7329 0.7407 0.0704 1.0000 Uiso R . . . . . .
H211 H 1.0959 0.5745 0.6434 0.0663 1.0000 Uiso R . . . . . .
H212 H 0.9325 0.6386 0.5701 0.0663 1.0000 Uiso R . . . . . .
H311 H 1.2677 0.7146 1.0359 0.0630 1.0000 Uiso R . . . . . .
H312 H 1.2839 0.7815 0.9310 0.0630 1.0000 Uiso R . . . . . .
H313 H 1.0899 0.7617 0.9468 0.0630 1.0000 Uiso R . . . . . .
H411 H 1.4121 0.5898 0.9596 0.0796 1.0000 Uiso R . . . . . .
H412 H 1.4451 0.6541 0.8571 0.0796 1.0000 Uiso R . . . . . .
H413 H 1.3423 0.5605 0.8185 0.0796 1.0000 Uiso R . . . . . .
H511 H 0.7605 0.4348 0.6846 0.0629 1.0000 Uiso R . . . . . .
H512 H 0.9590 0.4360 0.6704 0.0629 1.0000 Uiso R . . . . . .
H513 H 0.7889 0.4717 0.5612 0.0629 1.0000 Uiso R . . . . . .
H611 H 0.6122 0.5748 0.7094 0.0789 1.0000 Uiso R . . . . . .
H612 H 0.7105 0.6689 0.7081 0.0789 1.0000 Uiso R . . . . . .
H613 H 0.6397 0.6107 0.5852 0.0789 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.112(2) 0.0938(15) 0.0305(8) 0.0046(7) 0.0145(10) -0.0685(14)
N11 0.057(8) 0.045(5) 0.030(4) 0.000(3) 0.027(5) -0.016(4)
N21 0.043(7) 0.052(6) 0.031(5) -0.004(3) 0.027(5) -0.011(4)
C11 0.057(10) 0.072(9) 0.046(7) 0.004(5) 0.020(7) -0.006(6)
C21 0.053(10) 0.070(9) 0.038(6) -0.001(5) 0.021(7) -0.023(6)
C31 0.067(10) 0.039(7) 0.057(7) -0.005(5) 0.017(7) 0.002(5)
C41 0.070(12) 0.053(8) 0.075(10) -0.012(6) 0.041(9) 0.000(7)
C51 0.068(11) 0.042(7) 0.053(7) -0.002(5) 0.005(7) -0.004(5)
C61 0.046(10) 0.063(9) 0.079(10) -0.009(6) 0.036(8) -0.004(6)
Cl1 0.041(2) 0.067(2) 0.061(2) 0.0181(13) 0.0180(17) 0.0104(13)
O1 0.115(12) 0.073(7) 0.060(7) 0.011(5) 0.023(7) 0.021(6)

# special_uiso is a measure of the thickness of the shape
# special_size is the length of the line
# or the radius of the annulus or sphere
# special_declination and azimuth define the direction
# of the line or normal to the annulus
# Because CHECKCIF rejects occupancies greater than unity
# it will generate incorrect formulae, and derived values
loop_
_atom_site_oxford_special_label
_atom_site_oxford_special_uiso
_atom_site_oxford_special_size
_atom_site_oxford_special_declination
_atom_site_oxford_special_azimuth
O100 0.098(5) 1.349(13) 0.6083 -0.7930

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.925(8)
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
Cu1 . Cu1 2_767 2.939(3) yes
Cu1 . O10 2_767 1.941(15) yes
Cu1 . N11 . 2.011(10) yes
Cu1 . N21 . 2.026(9) yes
Cu1 . O10 . 1.905(18) yes
Cu1 . O11 . 2.47(3) yes
N11 . C11 . 1.435(15) yes
N11 . C31 . 1.490(14) yes
N11 . C41 . 1.49(2) yes
N21 . C21 . 1.511(18) yes
N21 . C51 . 1.481(14) yes
N21 . C61 . 1.435(19) yes
C11 . C21 . 1.482(18) yes
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C21 . H211 . 0.950 no
C21 . H212 . 0.950 no
C31 . H311 . 0.950 no
C31 . H312 . 0.950 no
C31 . H313 . 0.950 no
C41 . H411 . 0.950 no
C41 . H412 . 0.950 no
C41 . H413 . 0.950 no
C51 . H511 . 0.950 no
C51 . H512 . 0.950 no
C51 . H513 . 0.950 no
C61 . H611 . 0.950 no
C61 . H612 . 0.950 no
C61 . H613 . 0.950 no
Cl1 . O1 . 1.401(11) yes
O10 . H101 . 0.803 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
Cu1 2_767 Cu1 . O10 2_767 39.7(5) yes
Cu1 2_767 Cu1 . N11 . 136.1(3) yes
O10 2_767 Cu1 . N11 . 96.4(6) yes
Cu1 2_767 Cu1 . N21 . 135.2(3) yes
O10 2_767 Cu1 . N21 . 164.8(6) yes
N11 . Cu1 . N21 . 87.1(4) yes
Cu1 2_767 Cu1 . O10 . 40.6(4) yes
O10 2_767 Cu1 . O10 . 80.3(7) yes
N11 . Cu1 . O10 . 176.5(5) yes
N21 . Cu1 . O10 . 96.4(5) yes
Cu1 2_767 Cu1 . O11 . 80.4(7) yes
O10 2_767 Cu1 . O11 . 86.1(8) yes
N11 . Cu1 . O11 . 99.3(7) yes
N21 . Cu1 . O11 . 108.0(7) yes
O10 . Cu1 . O11 . 79.1(9) yes
Cu1 . N11 . C11 . 106.7(8) yes
Cu1 . N11 . C31 . 112.9(9) yes
C11 . N11 . C31 . 107.6(10) yes
Cu1 . N11 . C41 . 109.1(8) yes
C11 . N11 . C41 . 111.1(13) yes
C31 . N11 . C41 . 109.6(10) yes
Cu1 . N21 . C21 . 104.8(7) yes
Cu1 . N21 . C51 . 112.5(7) yes
C21 . N21 . C51 . 108.9(12) yes
Cu1 . N21 . C61 . 111.8(10) yes
C21 . N21 . C61 . 109.6(11) yes
C51 . N21 . C61 . 109.0(10) yes
N11 . C11 . C21 . 110.7(11) yes
N11 . C11 . H111 . 110.4 no
C21 . C11 . H111 . 110.9 no
N11 . C11 . H112 . 108.1 no
C21 . C11 . H112 . 107.2 no
H111 . C11 . H112 . 109.5 no
N21 . C21 . C11 . 109.7(13) yes
N21 . C21 . H211 . 109.1 no
C11 . C21 . H211 . 107.6 no
N21 . C21 . H212 . 110.2 no
C11 . C21 . H212 . 110.7 no
H211 . C21 . H212 . 109.5 no
N11 . C31 . H311 . 109.1 no
N11 . C31 . H312 . 110.6 no
H311 . C31 . H312 . 109.5 no
N11 . C31 . H313 . 108.7 no
H311 . C31 . H313 . 109.5 no
H312 . C31 . H313 . 109.5 no
N11 . C41 . H411 . 107.6 no
N11 . C41 . H412 . 111.0 no
H411 . C41 . H412 . 109.5 no
N11 . C41 . H413 . 109.7 no
H411 . C41 . H413 . 109.5 no
H412 . C41 . H413 . 109.5 no
N21 . C51 . H511 . 108.6 no
N21 . C51 . H512 . 110.1 no
H511 . C51 . H512 . 109.5 no
N21 . C51 . H513 . 109.7 no
H511 . C51 . H513 . 109.5 no
H512 . C51 . H513 . 109.5 no
N21 . C61 . H611 . 109.6 no
N21 . C61 . H612 . 109.6 no
H611 . C61 . H612 . 109.5 no
N21 . C61 . H613 . 109.2 no
H611 . C61 . H613 . 109.5 no
H612 . C61 . H613 . 109.5 no
Cu1 2_767 O10 . Cu1 . 99.7(7) yes
Cu1 2_767 O10 . H101 . 140.6 no
Cu1 . O10 . H101 . 119.8 no
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
C41 . H413 . O1 2_766 166 0.95 2.55 3.48(2) yes
C51 . H513 . O1 . 155 0.95 2.46 3.35(2) yes
C61 . H612 . O100 4_565 160 0.95 2.56 3.47(2) yes

# Attachment 'cu2006.cif'

data_cu2006
_database_code_depnum_ccdc_archive 'CCDC 746636'

#2.50 GPa data set.

_audit_creation_date             09-07-14
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cu2006 in P-1'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;
H atoms placed geometrically after each cycle on carbon.
It wasn't possible to locate H atoms on the oxygen atoms.

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.42
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 11.93 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.47
088_ALERT_3_A Poor Data / Parameter Ratio .................... 4.83
201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 39
341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 48
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.556 4132
026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc.
082_ALERT_2_C High R1 Value .................................. 0.11
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 5

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

023_ALERT_3_B Resolution (too) Low [sin(theta)/Lambda < 0.6].. 15.69 Deg.

INTENSITY STATISTICS FOR DATASET # 1 cu2006.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) Rsigma

Inf - 2.38 177 346 51.2 4.00 89.7 25.96 0.0519 0.0328
2.38 - 1.87 178 355 50.1 3.37 88.0 24.65 0.0630 0.0362
1.87 - 1.63 179 357 50.1 3.52 54.3 20.43 0.0711 0.0393
1.63 - 1.48 178 365 48.8 3.32 42.5 17.68 0.0838 0.0493
1.48 - 1.36 193 417 46.3 3.33 35.1 15.82 0.0923 0.0535
1.36 - 1.27 189 425 44.5 2.78 34.6 13.96 0.1182 0.0643
1.27 - 1.20 186 423 44.0 2.73 22.4 10.18 0.1357 0.0812
1.20 - 1.14 197 446 44.2 2.21 15.8 7.06 0.1634 0.1260
1.14 - 1.09 184 461 39.9 1.62 15.4 6.19 0.2000 0.1537
1.09 - 1.05 189 425 44.5 1.73 13.8 5.52 0.1661 0.1732
1.05 - 1.01 188 487 38.6 1.34 12.8 4.68 0.2197 0.2044
1.01 - 0.98 187 472 39.6 1.18 18.0 4.65 0.2469 0.1871
0.98 - 0.95 178 450 39.6 1.20 8.8 2.97 0.2730 0.3292
0.95 - 0.92 201 579 34.7 1.00 8.7 2.93 0.2594 0.3372
0.92 - 0.89 231 644 35.9 1.03 8.7 2.88 0.2929 0.3619
0.89 - 0.86 215 702 30.6 0.83 6.6 2.11 0.3569 0.5124
0.86 - 0.84 190 573 33.2 0.83 8.5 2.03 0.5695 0.4927
0.84 - 0.82 179 597 30.0 0.82 3.9 1.22 0.4801 0.8724
0.82 - 0.79 107 482 22.2 0.56 3.2 0.93 0.6104 1.2848
#-----------------------------------------------------------------------------
0.89 - 0.79 766 2586 29.6 0.79 6.1 1.78 0.4469 0.5974
Inf - 0.79 3526 9006 39.2 1.78 25.5 8.97 0.1008 0.1085

Merged [A], lowest resolution = 14.22 Angstroms, 509 outliers downweighted

042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?

H atoms on the water molecules are not present in the refined structure but
they obvioulsy must be counted.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.49 Ang.

This data set has been collected using synchrotron radiation at the above
wavelegth.

951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 2

The calculate value is determined assuming an 100% complete data set:
because of the limitations due to the use of the pressure cell this cannot
be achieved therefore platon can be terribly wrong in these calculations

155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ?

This unit cell has been chosen because it is related to ambient structure
in a more effective way.

241_ALERT_2_B Check High Ueq as Compared to Neighbors for O2
242_ALERT_2_B Check Low Ueq as Compared to Neighbors for O4
430_ALERT_2_B Short Inter D...A Contact O6 .. O34 .. 2.62 Ang.
430_ALERT_2_B Short Inter D...A Contact O6 .. O44 .. 2.64 Ang.
430_ALERT_2_B Short Inter D...A Contact O7 .. O21 .. 2.81 Ang.
913_ALERT_3_B Missing # of Very Strong Reflections in FCF .... 193
919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1
220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.14 Ratio
241_ALERT_2_C Check High Ueq as Compared to Neighbors for Cu3
241_ALERT_2_C Check High Ueq as Compared to Neighbors for Cu4
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Cu1
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O3
412_ALERT_2_C Short Intra XH3 .. XHn H232 .. H433 .. 1.86 Ang.
432_ALERT_2_C Short Inter X...Y Contact O44 .. C11 .. 2.99 Ang.
221_ALERT_4_C Large Solvent/Anion O Ueq(max)/Ueq(min) ... 3.05 Ratio
790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C12 H32 Cu2 N4 O3
790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3
Cl O4
790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 5
Cl O4
790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 6
Cl O4
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 41.70 Deg.
N24 -C54 -CU3 1.555 1.555 1.555
795_ALERT_4_G C-Atom in CIF Coordinate List out of Sequence .. C19
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?

No action taken.

731_ALERT_1_B Bond Calc 1.49(5), Rep 1.497(9) ...... 5.56 su-Ra
N11 -C19 1.555 1.555
731_ALERT_1_B Bond Calc 1.50(5), Rep 1.499(10) ...... 5.00 su-Ra
N12 -C21 1.555 1.555
722_ALERT_1_C Angle Calc 108.00, Rep 109.10 Dev... 1.10 Deg.
H141 -C14 -H143 1.555 1.555 1.555
731_ALERT_1_C Bond Calc 1.42(2), Rep 1.417(7) ...... 2.86 su-Ra
O11 -CL1 1.555 1.555

+ several similar alerts at B and C level.

Platon doesn't use the full matrices of the covariances to calculate esds and
the use of restraints during the refinement process can lead to big differences
in the results of platon calculations.

860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 73

Crystals list 16 is attached:

#LIST 16
DIST 0.0, 0.01 = MEAN O(11) TO O(12) , O(13) TO O(14)
CONT O(12) TO O(14) , O(11) TO O(13)
CONT O(11) TO O(14) , O(12) TO O(13)
DIST 0.0, 0.01 = MEAN CL(1) TO O(11), CL(1) TO O(12)
CONT CL(1) TO O(12), CL(1) TO O(13)
CONT CL(1) TO O(13), CL(1) TO O(14)
DIST 0.0, 0.01 = MEAN O(21) TO O(22) , O(23) TO O(24)
CONT O(22) TO O(24) , O(21) TO O(23)
CONT O(21) TO O(24) , O(22) TO O(23)
DIST 0.0, 0.01 = MEAN CL(2) TO O(21), CL(2) TO O(22)
CONT CL(2) TO O(22), CL(2) TO O(23)
CONT CL(2) TO O(23), CL(2) TO O(24)
DIST 0.0, 0.01 = MEAN O(31) TO O(32) , O(33) TO O(34)
CONT O(32) TO O(34) , O(31) TO O(33)
CONT O(31) TO O(34) , O(32) TO O(33)
DIST 0.0, 0.01 = MEAN CL(3) TO O(31), CL(3) TO O(32)
CONT CL(3) TO O(32), CL(3) TO O(33)
CONT CL(3) TO O(33), CL(3) TO O(34)
DIST 0.0, 0.01 = MEAN O(41) TO O(42) , O(43) TO O(44)
CONT O(42) TO O(44) , O(41) TO O(43)
CONT O(41) TO O(44) , O(42) TO O(43)
DIST 0.0, 0.01 = MEAN CL(4) TO O(41), CL(4) TO O(42)
CONT CL(4) TO O(42), CL(4) TO O(43)
CONT CL(4) TO O(43), CL(4) TO O(44)
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
DISTANCE 1.500000 , 0.010000 = C(19) TO C(31)
DISTANCE 1.500000 , 0.050000 = C(22) TO C(32)
DISTANCE 1.500000 , 0.010000 = C(19) TO N(11)
DISTANCE 1.500000 , 0.030000 = C(11) TO N(11)
DISTANCE 1.500000 , 0.030000 = C(10) TO N(11)
DISTANCE 1.500000 , 0.050000 = C(11) TO N(32)
DISTANCE 1.500000 , 0.050000 = C(41) TO N(21)
DISTANCE 1.500000 , 0.050000 = C(51) TO N(21)
DISTANCE 1.500000 , 0.050000 = C(52) TO N(22)
DISTANCE 1.500000 , 0.010000 = C(42) TO N(22)
DISTANCE 1.500000 , 0.010000 = C(21) TO N(12)
DISTANCE 1.500000 , 0.010000 = C(20) TO N(12)
DISTANCE 1.500000 , 0.010000 = C(14) TO N(14)
DISTANCE 1.500000 , 0.020000 = C(40) TO N(14)
DISTANCE 1.500000 , 0.010000 = C(24) TO N(14)
DISTANCE 1.500000 , 0.050000 = C(24) TO C(34)
DISTANCE 1.500000 , 0.010000 = C(34) TO N(24)
DISTANCE 1.500000 , 0.010000 = C(54) TO N(24)
DISTANCE 1.500000 , 0.050000 = C(44) TO N(24)
DISTANCE 1.500000 , 0.010000 = C(13) TO N(13)
DISTANCE 1.500000 , 0.010000 = C(30) TO N(13)
DISTANCE 1.500000 , 0.050000 = C(23) TO N(13)
DISTANCE 1.500000 , 0.010000 = C(23) TO C(33)
DISTANCE 1.500000 , 0.010000 = C(33) TO N(23)
DISTANCE 1.500000 , 0.030000 = C(53) TO N(23)
DISTANCE 1.500000 , 0.030000 = C(43) TO N(23)
REM THERMSIM START (DO NOT REMOVE THIS LINE)
U(IJ) .0, 0.08000 = O(11) TO CL(1)
U(IJ) .0, 0.08000 = O(12) TO CL(1)
U(IJ) .0, 0.08000 = O(13) TO CL(1)
U(IJ) .0, 0.08000 = O(14) TO CL(1)
U(IJ) .0, 0.08000 = O(21) TO CL(2)
U(IJ) .0, 0.08000 = O(22) TO CL(2)
U(IJ) .0, 0.08000 = O(23) TO CL(2)
U(IJ) .0, 0.08000 = O(24) TO CL(2)
U(IJ) .0, 0.08000 = O(31) TO CL(3)
U(IJ) .0, 0.08000 = O(32) TO CL(3)
U(IJ) .0, 0.08000 = O(33) TO CL(3)
U(IJ) .0, 0.08000 = O(34) TO CL(3)
U(IJ) .0, 0.08000 = O(41) TO CL(4)
U(IJ) .0, 0.08000 = O(42) TO CL(4)
U(IJ) .0, 0.08000 = O(43) TO CL(4)
U(IJ) .0, 0.08000 = O(44) TO CL(4)
U(IJ) .0, 0.08000 = N(11) TO C(10)
U(IJ) .0, 0.08000 = N(11) TO C(11)
U(IJ) .0, 0.04000 = N(11) TO C(21)
U(IJ) .0, 0.08000 = N(12) TO C(20)
U(IJ) .0, 0.04000 = N(12) TO C(21)
U(IJ) .0, 0.04000 = N(12) TO C(22)
U(IJ) .0, 0.08000 = N(13) TO C(13)
U(IJ) .0, 0.04000 = N(13) TO C(23)
U(IJ) .0, 0.04000 = N(13) TO C(30)
U(IJ) .0, 0.08000 = N(14) TO C(14)
U(IJ) .0, 0.04000 = N(14) TO C(24)
U(IJ) .0, 0.08000 = N(14) TO C(40)
U(IJ) .0, 0.04000 = N(21) TO C(31)
U(IJ) .0, 0.08000 = N(21) TO C(41)
U(IJ) .0, 0.08000 = N(21) TO C(51)
U(IJ) .0, 0.04000 = N(22) TO C(32)
U(IJ) .0, 0.08000 = N(22) TO C(42)
U(IJ) .0, 0.08000 = N(22) TO C(52)
U(IJ) .0, 0.08000 = N(23) TO C(43)
U(IJ) .0, 0.08000 = N(23) TO C(53)
U(IJ) .0, 0.04000 = N(23) TO C(33)
U(IJ) .0, 0.04000 = N(24) TO C(34)
U(IJ) .0, 0.08000 = N(24) TO C(44)
U(IJ) .0, 0.08000 = N(24) TO C(54)
U(IJ) .0, 0.04000 = C(21) TO C(31)
U(IJ) .0, 0.04000 = C(22) TO C(32)
U(IJ) .0, 0.04000 = C(23) TO C(33)
U(IJ) .0, 0.04000 = C(24) TO C(34)
REM THERMSIM END (DO NOT REMOVE THIS LINE)
END

;
#end of refcif
_cell_length_a                   11.0214(10)
_cell_length_b                   14.705(3)
_cell_length_c                   16.0463(18)
_cell_angle_alpha                62.486(12)
_cell_angle_beta                 81.394(7)
_cell_angle_gamma                69.543(11)
_cell_volume                     2160.9(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 0.0010 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0020 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0040 0.0030 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'
Cl 0.0780 0.0740 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.2950 0.6400 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C18 H57 Cl3 Cu3 N6 O18
# Dc = 1.45 Fooo = 1264.00 Mu = 17.14 M = 942.68
# Found Formula = C24 H64 Cl4 Cu4 N8 O23
# Dc = 1.89 FOOO = 1264.00 Mu = 22.82 M = 1228.81

_chemical_formula_sum            'C24 H74 Cl4 Cu4 N8 O23'
_chemical_formula_moiety         
'[Cu2(OH)2(H2O)2(tmen)2][Cu2(OH)2(H2O)(tmen)2][ClO4]4'
_chemical_formula_weight         1238.81

_cell_measurement_reflns_used    6228
_cell_measurement_theta_min      2
_cell_measurement_theta_max      18
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.12

_exptl_crystal_density_diffrn    1.888
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    2.282

# Sheldrick geometric approximatio 0.80 0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.01
_exptl_absorpt_correction_T_max  0.83
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.48690
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         2500000
_diffrn_reflns_number            14618
_reflns_number_total             2633
_diffrn_reflns_av_R_equivalents  0.098
# Number of reflections with Friedels Law is 2633
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 6206

_diffrn_reflns_theta_min         0.980
_diffrn_reflns_theta_max         15.694
_diffrn_measured_fraction_theta_max 0.424

_diffrn_reflns_theta_full        11.927
_diffrn_measured_fraction_theta_full 0.470

_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_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              -9
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.51
_refine_diff_density_max         0.64

# 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         1150
_refine_ls_number_restraints     73
_refine_ls_number_parameters     238
_oxford_refine_ls_R_factor_ref   0.1060
_refine_ls_wR_factor_ref         0.0567
_refine_ls_goodness_of_fit_ref   0.9903
_refine_ls_shift/su_max          0.003051

# The values computed from all data
_oxford_reflns_number_all        1929
_refine_ls_R_factor_all          0.1684
_refine_ls_wR_factor_all         0.0630

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                1150
_refine_ls_R_factor_gt           0.1060
_refine_ls_wR_factor_gt          0.0567

# 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    noref # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     
;
Method=
SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6)
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0953(3) 0.2207(5) 0.4434(3) 0.0259 1.0000 Uani . . . . . . .
Cu2 Cu -0.1180(3) 0.2688(5) 0.5636(2) 0.0350 1.0000 Uani . . . . . . .
Cu3 Cu -0.3905(4) 0.1716(8) 0.0891(4) 0.0742 1.0000 Uani . . . . . . .
Cu4 Cu -0.6071(3) 0.3411(6) -0.0226(3) 0.0639 1.0000 Uani . . . . . . .
O1 O 0.0574(14) 0.267(2) 0.5422(11) 0.021(3) 1.0000 Uiso . . . . . . .
O2 O -0.086(2) 0.221(3) 0.4723(15) 0.066(5) 1.0000 Uiso . . . . . . .
O3 O -0.425(2) 0.320(4) 0.0049(19) 0.053(6) 1.0000 Uiso . . . . . . .
O4 O -0.5841(16) 0.220(3) 0.0967(13) 0.032(4) 1.0000 Uiso . . . . . . .
O5 O -0.0409(16) 0.102(3) 0.6810(14) 0.040(4) 1.0000 Uiso . . . . . . .
O6 O -0.008(2) 0.419(4) 0.3427(17) 0.052(5) 1.0000 Uiso . . . . . . .
O7 O -0.5116(19) 0.209(3) -0.0788(15) 0.059(5) 1.0000 Uiso . . . . . . .
O11 O 0.2711(14) -0.2455(11) 0.6709(8) 0.060(5) 1.0000 Uiso D U . . . . .
O12 O 0.3738(12) -0.1241(16) 0.5657(7) 0.048(4) 1.0000 Uiso D U . . . . .
O13 O 0.1809(10) -0.0632(11) 0.6328(9) 0.064(5) 1.0000 Uiso D U . . . . .
O14 O 0.3694(10) -0.1649(14) 0.7233(7) 0.021(3) 1.0000 Uiso D U . . . . .
O21 O 0.2966(13) -0.1035(11) 0.1566(8) 0.068(6) 1.0000 Uiso D U . . . . .
O22 O 0.1974(12) 0.0315(17) 0.2000(9) 0.062(5) 1.0000 Uiso D U . . . . .
O23 O 0.1417(9) 0.0475(15) 0.0614(8) 0.048(4) 1.0000 Uiso D U . . . . .
O24 O 0.3380(12) 0.0574(15) 0.0787(8) 0.045(4) 1.0000 Uiso D U . . . . .
O31 O -0.8346(13) 0.5837(12) 0.0513(8) 0.070(5) 1.0000 Uiso D U . . . . .
O32 O -0.7340(14) 0.5427(17) 0.1817(11) 0.069(5) 1.0000 Uiso D U . . . . .
O33 O -0.6804(12) 0.4241(14) 0.1208(12) 0.126(8) 1.0000 Uiso D U . . . . .
O34 O -0.8724(14) 0.4581(16) 0.1886(8) 0.059(5) 1.0000 Uiso D U . . . . .
O41 O -0.6215(10) 0.2879(14) -0.2728(8) 0.041(4) 1.0000 Uiso D U . . . . .
O42 O -0.8180(14) 0.2987(17) -0.3081(10) 0.104(7) 1.0000 Uiso D U . . . . .
O43 O -0.6683(13) 0.334(2) -0.4218(9) 0.096(6) 1.0000 Uiso D U . . . . .
O44 O -0.7639(14) 0.4505(12) -0.3590(9) 0.079(6) 1.0000 Uiso D U . . . . .
N11 N -0.3190(17) 0.306(2) 0.5590(15) 0.0482(2) 1.0000 Uiso D U . . . . .
N12 N 0.1222(17) 0.170(3) 0.3427(14) 0.0482(2) 1.0000 Uiso D U . . . . .
N13 N -0.6225(18) 0.467(3) -0.1326(18) 0.0482(2) 1.0000 Uiso D U . . . . .
N14 N -0.194(2) 0.136(3) 0.0740(14) 0.0482(2) 1.0000 Uiso D U . . . . .
N21 N -0.158(2) 0.359(3) 0.6411(15) 0.0482(2) 1.0000 Uiso D U . . . . .
N22 N 0.2877(19) 0.196(3) 0.4406(14) 0.0482(2) 1.0000 Uiso D U . . . . .
N23 N -0.8036(19) 0.359(3) -0.0343(15) 0.0482(2) 1.0000 Uiso D U . . . . .
N24 N -0.357(2) 0.014(3) 0.1675(17) 0.0482(2) 1.0000 Uiso D U . . . . .
C10 C -0.343(2) 0.197(3) 0.6039(17) 0.0482(2) 1.0000 Uiso D U . . . . .
C11 C -0.376(2) 0.388(3) 0.4617(17) 0.0482(2) 1.0000 Uiso D U . . . . .
C13 C -0.599(3) 0.547(3) -0.109(2) 0.0482(2) 1.0000 Uiso D U . . . . .
C14 C -0.166(3) 0.184(4) -0.0291(15) 0.0482(2) 1.0000 Uiso D U . . . . .
C20 C 0.0231(19) 0.239(3) 0.2649(15) 0.0482(2) 1.0000 Uiso D U . . . . .
C19 C -0.379(2) 0.364(3) 0.6182(19) 0.0482(2) 1.0000 Uiso D . . . . . .
C21 C 0.135(2) 0.052(3) 0.3936(16) 0.0482(2) 1.0000 Uiso D U . . . . .
C22 C 0.254(3) 0.162(4) 0.311(2) 0.0482(2) 1.0000 Uiso D U . . . . .
C23 C -0.762(2) 0.515(4) -0.1738(17) 0.0482(2) 1.0000 Uiso D U . . . . .
C24 C -0.140(2) 0.015(3) 0.1241(16) 0.0482(2) 1.0000 Uiso D U . . . . .
C30 C -0.528(2) 0.443(4) -0.204(2) 0.0482(2) 1.0000 Uiso D U . . . . .
C31 C -0.299(3) 0.414(4) 0.640(2) 0.0482(2) 1.0000 Uiso D U . . . . .
C32 C 0.349(3) 0.137(4) 0.383(2) 0.0482(2) 1.0000 Uiso D U . . . . .
C33 C -0.849(2) 0.480(3) -0.0911(14) 0.0482(2) 1.0000 Uiso D U . . . . .
C34 C -0.224(2) -0.024(4) 0.2063(18) 0.0482(2) 1.0000 Uiso D U . . . . .
C40 C -0.148(3) 0.193(4) 0.114(2) 0.0482(2) 1.0000 Uiso D U . . . . .
C41 C -0.102(2) 0.450(4) 0.5942(18) 0.0482(2) 1.0000 Uiso D U . . . . .
C42 C 0.348(2) 0.124(3) 0.5366(15) 0.0482(2) 1.0000 Uiso D U . . . . .
C43 C -0.818(3) 0.320(4) -0.102(2) 0.0482(2) 1.0000 Uiso D U . . . . .
C44 C -0.353(3) -0.051(4) 0.115(2) 0.0482(2) 1.0000 Uiso D U . . . . .
C51 C -0.105(2) 0.291(4) 0.7378(18) 0.0482(2) 1.0000 Uiso D U . . . . .
C52 C 0.319(3) 0.300(4) 0.3868(18) 0.0482(2) 1.0000 Uiso D U . . . . .
C53 C -0.861(3) 0.296(4) 0.0542(17) 0.0482(2) 1.0000 Uiso D U . . . . .
C54 C -0.450(3) -0.001(4) 0.246(2) 0.0482(2) 1.0000 Uiso D U . . . . .
Cl1 Cl 0.2984(6) -0.1494(9) 0.6482(5) 0.0327 1.0000 Uani D U . . . . .
Cl2 Cl 0.2434(7) 0.0085(11) 0.1237(5) 0.0482(2) 1.0000 Uiso D U . . . . .
Cl3 Cl -0.7788(7) 0.5023(10) 0.1361(5) 0.0275 1.0000 Uani D U . . . . .
Cl4 Cl -0.7191(7) 0.3425(12) -0.3412(6) 0.0497 1.0000 Uani D U . . . . .
H101 H -0.3018 0.1542 0.6645 0.0579 1.0000 Uiso . . . . . . .
H102 H -0.4331 0.2081 0.6108 0.0579 1.0000 Uiso . . . . . . .
H103 H -0.3078 0.1606 0.5659 0.0579 1.0000 Uiso . . . . . . .
H111 H -0.3535 0.4512 0.4421 0.0579 1.0000 Uiso . . . . . . .
H112 H -0.4675 0.4052 0.4631 0.0579 1.0000 Uiso . . . . . . .
H113 H -0.3422 0.3577 0.4183 0.0579 1.0000 Uiso . . . . . . .
H131 H -0.6064 0.6129 -0.1656 0.0579 1.0000 Uiso . . . . . . .
H132 H -0.6612 0.5617 -0.0659 0.0579 1.0000 Uiso . . . . . . .
H133 H -0.5144 0.5191 -0.0835 0.0579 1.0000 Uiso . . . . . . .
H141 H -0.2037 0.2615 -0.0549 0.0579 1.0000 Uiso . . . . . . .
H142 H -0.2016 0.1582 -0.0599 0.0579 1.0000 Uiso . . . . . . .
H143 H -0.0750 0.1669 -0.0377 0.0579 1.0000 Uiso . . . . . . .
H201 H 0.0236 0.3111 0.2377 0.0579 1.0000 Uiso . . . . . . .
H202 H -0.0599 0.2354 0.2894 0.0579 1.0000 Uiso . . . . . . .
H203 H 0.0436 0.2128 0.2184 0.0579 1.0000 Uiso . . . . . . .
H191 H -0.3998 0.3115 0.6773 0.0579 1.0000 Uiso . . . . . . .
H192 H -0.4562 0.4181 0.5880 0.0579 1.0000 Uiso . . . . . . .
H211 H 0.2004 0.0154 0.4413 0.0579 1.0000 Uiso . . . . . . .
H212 H 0.0550 0.0433 0.4217 0.0579 1.0000 Uiso . . . . . . .
H213 H 0.1585 0.0207 0.3506 0.0579 1.0000 Uiso . . . . . . .
H221 H 0.2550 0.2240 0.2581 0.0579 1.0000 Uiso . . . . . . .
H222 H 0.2848 0.1004 0.2953 0.0579 1.0000 Uiso . . . . . . .
H231 H -0.7876 0.5917 -0.2067 0.0579 1.0000 Uiso . . . . . . .
H232 H -0.7676 0.4872 -0.2163 0.0579 1.0000 Uiso . . . . . . .
H241 H -0.0545 -0.0062 0.1453 0.0579 1.0000 Uiso . . . . . . .
H242 H -0.1401 -0.0152 0.0828 0.0579 1.0000 Uiso . . . . . . .
H301 H -0.5356 0.5071 -0.2601 0.0579 1.0000 Uiso . . . . . . .
H302 H -0.5454 0.3913 -0.2163 0.0579 1.0000 Uiso . . . . . . .
H303 H -0.4420 0.4134 -0.1790 0.0579 1.0000 Uiso . . . . . . .
H311 H -0.3232 0.4128 0.6997 0.0579 1.0000 Uiso . . . . . . .
H312 H -0.3183 0.4871 0.5932 0.0579 1.0000 Uiso . . . . . . .
H321 H 0.4198 0.1605 0.3507 0.0579 1.0000 Uiso . . . . . . .
H322 H 0.3783 0.0620 0.4230 0.0579 1.0000 Uiso . . . . . . .
H331 H -0.9351 0.5024 -0.1135 0.0579 1.0000 Uiso . . . . . . .
H332 H -0.8486 0.5133 -0.0529 0.0579 1.0000 Uiso . . . . . . .
H341 H -0.2245 0.0051 0.2480 0.0579 1.0000 Uiso . . . . . . .
H342 H -0.1944 -0.1009 0.2384 0.0579 1.0000 Uiso . . . . . . .
H401 H -0.1633 0.1666 0.1787 0.0579 1.0000 Uiso . . . . . . .
H402 H -0.1947 0.2692 0.0830 0.0579 1.0000 Uiso . . . . . . .
H403 H -0.0585 0.1828 0.1019 0.0579 1.0000 Uiso . . . . . . .
H411 H -0.0106 0.4202 0.5921 0.0579 1.0000 Uiso . . . . . . .
H412 H -0.1235 0.4904 0.6288 0.0579 1.0000 Uiso . . . . . . .
H413 H -0.1362 0.4944 0.5321 0.0579 1.0000 Uiso . . . . . . .
H421 H 0.3115 0.1584 0.5764 0.0579 1.0000 Uiso . . . . . . .
H422 H 0.4386 0.1114 0.5328 0.0579 1.0000 Uiso . . . . . . .
H423 H 0.3311 0.0572 0.5615 0.0579 1.0000 Uiso . . . . . . .
H431 H -0.7911 0.2432 -0.0729 0.0579 1.0000 Uiso . . . . . . .
H432 H -0.9061 0.3478 -0.1218 0.0579 1.0000 Uiso . . . . . . .
H433 H -0.7659 0.3443 -0.1557 0.0579 1.0000 Uiso . . . . . . .
H441 H -0.4376 -0.0279 0.0893 0.0579 1.0000 Uiso . . . . . . .
H442 H -0.3297 -0.1251 0.1574 0.0579 1.0000 Uiso . . . . . . .
H443 H -0.2931 -0.0379 0.0659 0.0579 1.0000 Uiso . . . . . . .
H511 H -0.0146 0.2571 0.7353 0.0579 1.0000 Uiso . . . . . . .
H512 H -0.1200 0.3348 0.7691 0.0579 1.0000 Uiso . . . . . . .
H513 H -0.1463 0.2373 0.7702 0.0579 1.0000 Uiso . . . . . . .
H521 H 0.2840 0.3445 0.4179 0.0579 1.0000 Uiso . . . . . . .
H522 H 0.4104 0.2844 0.3827 0.0579 1.0000 Uiso . . . . . . .
H523 H 0.2827 0.3365 0.3250 0.0579 1.0000 Uiso . . . . . . .
H531 H -0.8134 0.2212 0.0761 0.0579 1.0000 Uiso . . . . . . .
H532 H -0.9485 0.3079 0.0431 0.0579 1.0000 Uiso . . . . . . .
H533 H -0.8569 0.3183 0.1005 0.0579 1.0000 Uiso . . . . . . .
H541 H -0.5356 0.0245 0.2219 0.0579 1.0000 Uiso . . . . . . .
H542 H -0.4470 0.0411 0.2767 0.0579 1.0000 Uiso . . . . . . .
H543 H -0.4286 -0.0742 0.2895 0.0579 1.0000 Uiso . . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.023(2) 0.036(12) 0.041(4) -0.031(7) 0.008(3) -0.018(5)
Cu2 0.034(3) 0.057(12) 0.034(3) -0.028(6) 0.009(3) -0.029(5)
Cu3 0.043(3) 0.160(18) 0.073(5) -0.084(10) 0.019(4) -0.054(7)
Cu4 0.036(3) 0.117(14) 0.066(4) -0.060(8) 0.011(3) -0.033(6)
Cl1 0.0482(2) 0.0194(2) 0.0360(2) -0.0215(2) -0.0029(2) -0.0025(2)
Cl3 0.0482(2) 0.0093(2) 0.0197(2) 0.0045(2) -0.0080(2) -0.0148(2)
Cl4 0.0482(2) 0.0549(2) 0.0711(2) -0.0428(2) 0.0005(2) -0.0237(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3593(16)
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
Cu1 . O1 . 1.941(11) yes
Cu1 . O2 . 1.979(15) yes
Cu1 . O6 . 2.51(4) yes
Cu1 . N12 . 2.022(17) yes
Cu1 . N22 . 2.019(18) yes
Cu2 . O1 . 1.907(11) yes
Cu2 . O2 . 1.838(17) yes
Cu2 . O5 . 2.24(3) yes
Cu2 . N11 . 2.093(17) yes
Cu2 . N21 . 2.11(2) yes
Cu3 . Cu4 . 2.849(9) yes
Cu3 . O3 . 1.90(4) yes
Cu3 . O4 . 2.004(16) yes
Cu3 . N14 . 2.043(19) yes
Cu3 . N24 . 1.98(4) yes
Cu3 . C54 . 2.82(4) yes
Cu4 . O3 . 2.003(17) yes
Cu4 . O4 . 1.89(3) yes
Cu4 . O7 . 2.36(3) yes
Cu4 . N13 . 1.85(4) yes
Cu4 . N23 . 2.113(17) yes
O11 . Cl1 . 1.417(7) yes
O12 . Cl1 . 1.419(5) yes
O13 . Cl1 . 1.415(6) yes
O14 . Cl1 . 1.422(6) yes
O21 . Cl2 . 1.396(8) yes
O22 . Cl2 . 1.395(6) yes
O23 . Cl2 . 1.393(6) yes
O24 . Cl2 . 1.394(7) yes
O31 . Cl3 . 1.377(7) yes
O32 . Cl3 . 1.358(5) yes
O33 . Cl3 . 1.368(6) yes
O34 . Cl3 . 1.378(7) yes
O41 . Cl4 . 1.393(7) yes
O42 . Cl4 . 1.373(6) yes
O43 . Cl4 . 1.375(5) yes
O44 . Cl4 . 1.387(8) yes
N11 . C10 . 1.51(3) yes
N11 . C11 . 1.52(2) yes
N11 . C19 . 1.497(9) yes
N12 . C20 . 1.498(10) yes
N12 . C21 . 1.499(10) yes
N12 . C22 . 1.45(2) yes
N13 . C13 . 1.503(10) yes
N13 . C23 . 1.56(3) yes
N13 . C30 . 1.507(9) yes
N14 . C14 . 1.501(9) yes
N14 . C24 . 1.497(10) yes
N14 . C40 . 1.510(17) yes
N21 . C31 . 1.48(4) yes
N21 . C41 . 1.49(4) yes
N21 . C51 . 1.48(3) yes
N22 . C32 . 1.48(4) yes
N22 . C42 . 1.497(10) yes
N22 . C52 . 1.51(4) yes
N23 . C33 . 1.501(10) yes
N23 . C43 . 1.50(2) yes
N23 . C53 . 1.48(2) yes
N24 . C34 . 1.489(9) yes
N24 . C44 . 1.53(3) yes
N24 . C54 . 1.484(9) yes
C10 . H101 . 0.955 no
C10 . H102 . 0.952 no
C10 . H103 . 0.949 no
C11 . H111 . 0.951 no
C11 . H112 . 0.947 no
C11 . H113 . 0.954 no
C13 . H131 . 0.955 no
C13 . H132 . 0.945 no
C13 . H133 . 0.951 no
C14 . H141 . 0.958 no
C14 . H142 . 0.945 no
C14 . H143 . 0.947 no
C20 . H201 . 0.945 no
C20 . H202 . 0.948 no
C20 . H203 . 0.954 no
C19 . C31 . 1.495(9) yes
C19 . H191 . 0.962 no
C19 . H192 . 0.939 no
C21 . H211 . 0.952 no
C21 . H212 . 0.949 no
C21 . H213 . 0.952 no
C22 . C32 . 1.50(3) yes
C22 . H221 . 0.922 no
C22 . H222 . 0.979 no
C23 . C33 . 1.507(9) yes
C23 . H231 . 0.956 no
C23 . H232 . 0.955 no
C24 . C34 . 1.49(3) yes
C24 . H241 . 0.948 no
C24 . H242 . 0.950 no
C30 . H301 . 0.948 no
C30 . H302 . 0.955 no
C30 . H303 . 0.950 no
C31 . H311 . 0.951 no
C31 . H312 . 0.951 no
C32 . H321 . 0.951 no
C32 . H322 . 0.946 no
C33 . H331 . 0.952 no
C33 . H332 . 0.947 no
C34 . H341 . 0.944 no
C34 . H342 . 0.954 no
C40 . H401 . 0.942 no
C40 . H402 . 0.962 no
C40 . H403 . 0.947 no
C41 . H411 . 0.953 no
C41 . H412 . 0.946 no
C41 . H413 . 0.949 no
C42 . H421 . 0.954 no
C42 . H422 . 0.951 no
C42 . H423 . 0.945 no
C43 . H431 . 0.946 no
C43 . H432 . 0.950 no
C43 . H433 . 0.954 no
C44 . H441 . 0.959 no
C44 . H442 . 0.941 no
C44 . H443 . 0.943 no
C51 . H511 . 0.952 no
C51 . H512 . 0.948 no
C51 . H513 . 0.946 no
C52 . H521 . 0.945 no
C52 . H522 . 0.950 no
C52 . H523 . 0.953 no
C53 . H531 . 0.948 no
C53 . H532 . 0.949 no
C53 . H533 . 0.953 no
C54 . H541 . 0.956 no
C54 . H542 . 0.959 no
C54 . H543 . 0.938 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
O1 . Cu1 . O2 . 78.8(5) yes
O1 . Cu1 . O6 . 82.0(9) yes
O2 . Cu1 . O6 . 83.8(12) yes
O1 . Cu1 . N12 . 175.7(6) yes
O2 . Cu1 . N12 . 97.0(7) yes
O6 . Cu1 . N12 . 98.3(9) yes
O1 . Cu1 . N22 . 96.2(6) yes
O2 . Cu1 . N22 . 168.4(12) yes
O6 . Cu1 . N22 . 106.0(10) yes
N12 . Cu1 . N22 . 87.8(7) yes
O1 . Cu2 . O2 . 83.3(6) yes
O1 . Cu2 . O5 . 86.6(9) yes
O2 . Cu2 . O5 . 94.1(13) yes
O1 . Cu2 . N11 . 166.4(12) yes
O2 . Cu2 . N11 . 94.6(7) yes
O5 . Cu2 . N11 . 106.9(9) yes
O1 . Cu2 . N21 . 93.6(7) yes
O2 . Cu2 . N21 . 166.5(14) yes
O5 . Cu2 . N21 . 98.9(10) yes
N11 . Cu2 . N21 . 85.3(7) yes
Cu4 . Cu3 . O3 . 44.5(5) yes
Cu4 . Cu3 . O4 . 41.5(8) yes
O3 . Cu3 . O4 . 81.0(11) yes
Cu4 . Cu3 . N14 . 134.1(8) yes
O3 . Cu3 . N14 . 94.1(10) yes
O4 . Cu3 . N14 . 175.1(14) yes
Cu4 . Cu3 . N24 . 132.8(5) yes
O3 . Cu3 . N24 . 174.9(6) yes
O4 . Cu3 . N24 . 98.4(10) yes
N14 . Cu3 . N24 . 86.5(10) yes
Cu4 . Cu3 . C54 . 115.4(7) yes
O3 . Cu3 . C54 . 152.4(10) yes
O4 . Cu3 . C54 . 74.7(12) yes
N14 . Cu3 . C54 . 110.0(11) yes
N24 . Cu3 . C54 . 29.9(9) yes
Cu3 . Cu4 . O3 . 41.6(13) yes
Cu3 . Cu4 . O4 . 44.6(5) yes
O3 . Cu4 . O4 . 81.2(12) yes
Cu3 . Cu4 . O7 . 67.4(6) yes
O3 . Cu4 . O7 . 85.6(10) yes
O4 . Cu4 . O7 . 84.1(10) yes
Cu3 . Cu4 . N13 . 133.1(6) yes
O3 . Cu4 . N13 . 94.5(13) yes
O4 . Cu4 . N13 . 173.1(7) yes
O7 . Cu4 . N13 . 100.9(10) yes
Cu3 . Cu4 . N23 . 135.2(9) yes
O3 . Cu4 . N23 . 173.0(7) yes
O4 . Cu4 . N23 . 93.6(9) yes
O7 . Cu4 . N23 . 98.6(7) yes
N13 . Cu4 . N23 . 90.3(10) yes
Cu1 . O1 . Cu2 . 98.4(4) yes
Cu1 . O2 . Cu2 . 99.5(6) yes
Cu4 . O3 . Cu3 . 93.9(13) yes
Cu3 . O4 . Cu4 . 94.0(7) yes
Cu2 . N11 . C10 . 105.4(16) yes
Cu2 . N11 . C11 . 112.2(13) yes
C10 . N11 . C11 . 118.5(15) yes
Cu2 . N11 . C19 . 108.2(11) yes
C10 . N11 . C19 . 108.9(19) yes
C11 . N11 . C19 . 103.3(18) yes
Cu1 . N12 . C20 . 113.3(14) yes
Cu1 . N12 . C21 . 105.6(14) yes
C20 . N12 . C21 . 116.6(18) yes
Cu1 . N12 . C22 . 106.6(12) yes
C20 . N12 . C22 . 114(2) yes
C21 . N12 . C22 . 100(3) yes
Cu4 . N13 . C13 . 108.1(13) yes
Cu4 . N13 . C23 . 109.8(16) yes
C13 . N13 . C23 . 108.4(20) yes
Cu4 . N13 . C30 . 110(3) yes
C13 . N13 . C30 . 111.8(19) yes
C23 . N13 . C30 . 109.0(16) yes
Cu3 . N14 . C14 . 108.3(14) yes
Cu3 . N14 . C24 . 105.6(15) yes
C14 . N14 . C24 . 115(2) yes
Cu3 . N14 . C40 . 108.6(14) yes
C14 . N14 . C40 . 105.2(16) yes
C24 . N14 . C40 . 114(2) yes
Cu2 . N21 . C31 . 110.0(10) yes
Cu2 . N21 . C41 . 110.6(12) yes
C31 . N21 . C41 . 104(3) yes
Cu2 . N21 . C51 . 112(2) yes
C31 . N21 . C51 . 111.9(17) yes
C41 . N21 . C51 . 108.5(17) yes
Cu1 . N22 . C32 . 108.1(11) yes
Cu1 . N22 . C42 . 111.3(13) yes
C32 . N22 . C42 . 106(2) yes
Cu1 . N22 . C52 . 112.0(20) yes
C32 . N22 . C52 . 102(2) yes
C42 . N22 . C52 . 116.0(16) yes
Cu4 . N23 . C33 . 97.1(15) yes
Cu4 . N23 . C43 . 110.1(13) yes
C33 . N23 . C43 . 103(3) yes
Cu4 . N23 . C53 . 114.7(15) yes
C33 . N23 . C53 . 126(2) yes
C43 . N23 . C53 . 104.7(20) yes
Cu3 . N24 . C34 . 103(2) yes
Cu3 . N24 . C44 . 115.9(19) yes
C34 . N24 . C44 . 106.8(20) yes
Cu3 . N24 . C54 . 108(3) yes
C34 . N24 . C54 . 108.7(17) yes
C44 . N24 . C54 . 113(2) yes
N11 . C10 . H101 . 109.6 no
N11 . C10 . H102 . 109.8 no
H101 . C10 . H102 . 108.9 no
N11 . C10 . H103 . 110.0 no
H101 . C10 . H103 . 109.1 no
H102 . C10 . H103 . 109.4 no
N11 . C11 . H111 . 109.4 no
N11 . C11 . H112 . 109.8 no
H111 . C11 . H112 . 109.7 no
N11 . C11 . H113 . 109.4 no
H111 . C11 . H113 . 109.1 no
H112 . C11 . H113 . 109.4 no
N13 . C13 . H131 . 109.4 no
N13 . C13 . H132 . 109.7 no
H131 . C13 . H132 . 109.5 no
N13 . C13 . H133 . 109.5 no
H131 . C13 . H133 . 109.0 no
H132 . C13 . H133 . 109.8 no
N14 . C14 . H141 . 109.0 no
N14 . C14 . H142 . 109.7 no
H141 . C14 . H142 . 109.2 no
N14 . C14 . H143 . 109.7 no
H141 . C14 . H143 . 109.1 no
H142 . C14 . H143 . 110.1 no
N12 . C20 . H201 . 109.4 no
N12 . C20 . H202 . 109.4 no
H201 . C20 . H202 . 110.0 no
N12 . C20 . H203 . 109.2 no
H201 . C20 . H203 . 109.5 no
H202 . C20 . H203 . 109.3 no
N11 . C19 . C31 . 117.1(17) yes
N11 . C19 . H191 . 106.8 no
C31 . C19 . H191 . 107.0 no
N11 . C19 . H192 . 108.0 no
C31 . C19 . H192 . 108.4 no
H191 . C19 . H192 . 109.4 no
N12 . C21 . H211 . 109.6 no
N12 . C21 . H212 . 109.7 no
H211 . C21 . H212 . 109.3 no
N12 . C21 . H213 . 109.7 no
H211 . C21 . H213 . 109.1 no
H212 . C21 . H213 . 109.4 no
N12 . C22 . C32 . 115.6(15) yes
N12 . C22 . H221 . 109.9 no
C32 . C22 . H221 . 109.5 no
N12 . C22 . H222 . 106.6 no
C32 . C22 . H222 . 105.7 no
H221 . C22 . H222 . 109.4 no
N13 . C23 . C33 . 106.2(19) yes
N13 . C23 . H231 . 110.7 no
C33 . C23 . H231 . 110.3 no
N13 . C23 . H232 . 110.6 no
C33 . C23 . H232 . 110.4 no
H231 . C23 . H232 . 108.6 no
N14 . C24 . C34 . 108(2) yes
N14 . C24 . H241 . 109.9 no
C34 . C24 . H241 . 109.7 no
N14 . C24 . H242 . 109.7 no
C34 . C24 . H242 . 110.0 no
H241 . C24 . H242 . 109.6 no
N13 . C30 . H301 . 109.9 no
N13 . C30 . H302 . 109.3 no
H301 . C30 . H302 . 109.2 no
N13 . C30 . H303 . 109.7 no
H301 . C30 . H303 . 109.7 no
H302 . C30 . H303 . 109.1 no
C19 . C31 . N21 . 114(2) yes
C19 . C31 . H311 . 108.5 no
N21 . C31 . H311 . 108.7 no
C19 . C31 . H312 . 107.7 no
N21 . C31 . H312 . 108.9 no
H311 . C31 . H312 . 109.3 no
C22 . C32 . N22 . 111(3) yes
C22 . C32 . H321 . 108.6 no
N22 . C32 . H321 . 108.5 no
C22 . C32 . H322 . 110.7 no
N22 . C32 . H322 . 108.7 no
H321 . C32 . H322 . 109.7 no
C23 . C33 . N23 . 111(3) yes
C23 . C33 . H331 . 109.1 no
N23 . C33 . H331 . 109.0 no
C23 . C33 . H332 . 109.0 no
N23 . C33 . H332 . 109.4 no
H331 . C33 . H332 . 109.6 no
C24 . C34 . N24 . 106.4(19) yes
C24 . C34 . H341 . 110.6 no
N24 . C34 . H341 . 110.4 no
C24 . C34 . H342 . 110.0 no
N24 . C34 . H342 . 109.7 no
H341 . C34 . H342 . 109.7 no
N14 . C40 . H401 . 110.0 no
N14 . C40 . H402 . 108.7 no
H401 . C40 . H402 . 109.1 no
N14 . C40 . H403 . 109.7 no
H401 . C40 . H403 . 110.5 no
H402 . C40 . H403 . 108.7 no
N21 . C41 . H411 . 109.1 no
N21 . C41 . H412 . 109.5 no
H411 . C41 . H412 . 109.5 no
N21 . C41 . H413 . 109.5 no
H411 . C41 . H413 . 109.3 no
H412 . C41 . H413 . 109.9 no
N22 . C42 . H421 . 109.2 no
N22 . C42 . H422 . 109.4 no
H421 . C42 . H422 . 109.1 no
N22 . C42 . H423 . 109.7 no
H421 . C42 . H423 . 109.6 no
H422 . C42 . H423 . 109.9 no
N23 . C43 . H431 . 109.7 no
N23 . C43 . H432 . 109.4 no
H431 . C43 . H432 . 109.8 no
N23 . C43 . H433 . 109.3 no
H431 . C43 . H433 . 109.5 no
H432 . C43 . H433 . 109.2 no
N24 . C44 . H441 . 108.4 no
N24 . C44 . H442 . 109.4 no
H441 . C44 . H442 . 109.5 no
N24 . C44 . H443 . 109.2 no
H441 . C44 . H443 . 109.3 no
H442 . C44 . H443 . 110.9 no
N21 . C51 . H511 . 109.0 no
N21 . C51 . H512 . 109.3 no
H511 . C51 . H512 . 109.5 no
N21 . C51 . H513 . 109.4 no
H511 . C51 . H513 . 109.6 no
H512 . C51 . H513 . 110.0 no
N22 . C52 . H521 . 109.6 no
N22 . C52 . H522 . 109.4 no
H521 . C52 . H522 . 109.8 no
N22 . C52 . H523 . 109.2 no
H521 . C52 . H523 . 109.6 no
H522 . C52 . H523 . 109.2 no
N23 . C53 . H531 . 109.6 no
N23 . C53 . H532 . 109.5 no
H531 . C53 . H532 . 109.8 no
N23 . C53 . H533 . 109.3 no
H531 . C53 . H533 . 109.4 no
H532 . C53 . H533 . 109.3 no
N24 . C54 . Cu3 . 41.7(19) yes
N24 . C54 . H541 . 109.4 no
Cu3 . C54 . H541 . 90.3 no
N24 . C54 . H542 . 109.1 no
Cu3 . C54 . H542 . 81.2 no
H541 . C54 . H542 . 108.2 no
N24 . C54 . H543 . 110.4 no
Cu3 . C54 . H543 . 151.3 no
H541 . C54 . H543 . 110.0 no
H542 . C54 . H543 . 109.8 no
O14 . Cl1 . O12 . 108.9(5) yes
O14 . Cl1 . O11 . 109.5(7) yes
O12 . Cl1 . O11 . 109.7(6) yes
O14 . Cl1 . O13 . 109.8(6) yes
O12 . Cl1 . O13 . 109.5(7) yes
O11 . Cl1 . O13 . 109.5(6) yes
O21 . Cl2 . O22 . 108.8(7) yes
O21 . Cl2 . O24 . 109.9(7) yes
O22 . Cl2 . O24 . 109.0(6) yes
O21 . Cl2 . O23 . 109.3(6) yes
O22 . Cl2 . O23 . 109.7(6) yes
O24 . Cl2 . O23 . 110.0(7) yes
O34 . Cl3 . O31 . 107.6(6) yes
O34 . Cl3 . O33 . 108.8(7) yes
O31 . Cl3 . O33 . 109.2(6) yes
O34 . Cl3 . O32 . 110.2(6) yes
O31 . Cl3 . O32 . 110.2(7) yes
O33 . Cl3 . O32 . 110.7(7) yes
O41 . Cl4 . O44 . 108.1(6) yes
O41 . Cl4 . O43 . 108.9(7) yes
O44 . Cl4 . O43 . 109.5(7) yes
O41 . Cl4 . O42 . 109.1(7) yes
O44 . Cl4 . O42 . 109.9(7) yes
O43 . Cl4 . O42 . 111.2(6) 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
C10 . H101 . O22 2_556 150 0.96 2.56 3.43(5) yes
C10 . H102 . O43 1_556 151 0.95 2.56 3.42(5) yes
C11 . H111 . O44 2_465 149 0.95 2.13 2.99(5) yes
C11 . H113 . O11 2_556 167 0.95 2.52 3.45(5) yes
C13 . H132 . O31 . 174 0.95 2.52 3.46(5) yes
C13 . H133 . O33 2_465 136 0.95 2.46 3.22(5) yes
C14 . H141 . O31 2_465 138 0.96 2.48 3.26(5) yes
C14 . H141 . O32 2_465 157 0.96 2.55 3.46(5) yes
C14 . H142 . O21 2_555 175 0.95 2.53 3.47(5) yes
C20 . H201 . O34 1_655 155 0.95 2.55 3.43(5) yes
C20 . H202 . O11 2_556 172 0.95 2.29 3.23(5) yes
C20 . H203 . C53 1_655 129 0.95 2.58 3.26(5) yes
C19 . H191 . O41 1_556 126 0.96 2.55 3.21(5) yes
C21 . H211 . O12 . 165 0.95 2.54 3.47(5) yes
C21 . H213 . O22 . 153 0.95 2.33 3.21(5) yes
C23 . H231 . O11 1_464 147 0.96 2.52 3.36(5) yes
C23 . H232 . O44 . 167 0.95 2.58 3.51(5) yes
C24 . H241 . O23 . 132 0.95 2.54 3.25(5) yes
C24 . H242 . O23 2_555 165 0.95 2.57 3.50(5) yes
C30 . H302 . O41 . 169 0.95 2.50 3.44(5) yes
C30 . H303 . O32 2_465 143 0.95 2.24 3.05(5) yes
C31 . H311 . O32 2_466 142 0.95 2.50 3.30(5) yes
C31 . H311 . C30 1_556 139 0.95 2.56 3.34(5) yes
C32 . H321 . O12 2_656 124 0.95 2.58 3.21(5) yes
C32 . H321 . O14 2_656 163 0.95 2.45 3.37(5) yes
C33 . H331 . O34 2_365 169 0.95 2.36 3.29(5) yes
C33 . H332 . O31 . 175 0.95 2.38 3.33(5) yes
C34 . H341 . O13 2_556 170 0.94 2.59 3.52(5) yes
C34 . H341 . O14 2_556 136 0.94 2.54 3.28(5) yes
C34 . H342 . O42 2_455 162 0.95 2.55 3.47(5) yes
C40 . H401 . O14 2_556 133 0.94 2.56 3.28(5) yes
C40 . H402 . O31 2_465 135 0.96 2.32 3.08(5) yes
C41 . H411 . O42 1_656 143 0.95 2.45 3.26(5) yes
C41 . H412 . O6 2_566 129 0.95 2.49 3.17(5) yes
C42 . H422 . O12 2_656 148 0.95 2.41 3.26(5) yes
C42 . H423 . O12 . 150 0.94 2.51 3.36(5) yes
C43 . H433 . O41 . 143 0.95 2.52 3.33(5) yes
C44 . H441 . O24 1_455 154 0.96 2.34 3.23(5) yes
C44 . H442 . O41 2_455 153 0.94 2.44 3.31(5) yes
C44 . H443 . O23 2_555 165 0.94 2.46 3.38(5) yes
C51 . H511 . O42 1_656 141 0.95 2.37 3.17(5) yes
C51 . H512 . O32 2_466 148 0.95 2.32 3.16(5) yes
C52 . H523 . O34 1_655 162 0.95 2.51 3.42(5) yes
C53 . H531 . O22 1_455 145 0.95 2.54 3.36(5) yes
C53 . H531 . O24 1_455 160 0.95 2.39 3.30(5) yes
C53 . H532 . O31 2_365 154 0.95 2.60 3.47(5) yes
C54 . H542 . O14 2_556 147 0.96 2.27 3.12(5) yes

# Attachment 'cubf00.cif'

data_cubf00
_database_code_depnum_ccdc_archive 'CCDC 746637'

# ambient pressure dataset

_audit_creation_date             09-08-03
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cubf00 in C2/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'A. Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry and then were allowed to
ride on their parent atoms

checkcif output:

910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 6
911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 17
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 7
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 93

INTENSITY STATISTICS FOR DATASET # 1 cubf00.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma)

Inf - 1.95 87 87 100.0 7.45 54.8 31.51 0.0562 0.0311
1.95 - 1.55 86 86 100.0 7.71 26.6 28.55 0.0496 0.0279
1.55 - 1.35 89 89 100.0 7.03 18.2 25.70 0.0530 0.0315
1.35 - 1.20 108 108 100.0 6.31 15.0 23.48 0.0546 0.0352
1.20 - 1.10 107 107 100.0 5.64 8.8 18.81 0.0683 0.0412
1.10 - 1.00 145 145 100.0 4.46 6.9 15.70 0.0712 0.0495
1.00 - 0.95 111 111 100.0 3.88 4.9 12.73 0.0910 0.0628
0.95 - 0.90 119 119 100.0 3.50 4.0 11.68 0.0914 0.0712
0.90 - 0.85 157 157 100.0 3.19 3.7 10.67 0.0903 0.0792
0.85 - 0.80 206 206 100.0 3.13 2.7 8.64 0.1195 0.0947
0.80 - 0.75 251 254 98.8 2.77 1.5 6.45 0.1599 0.1308
0.75 - 0.70 241 302 79.8 1.16 1.4 4.05 0.1769 0.2088
#-----------------------------------------------------------------------------
0.80 - 0.70 492 556 88.5 1.90 1.5 5.27 0.1632 0.1671
Inf - 0.70 1707 1771 96.4 3.90 8.9 13.57 0.0608 0.0461

152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?

Volume Reported 1133.6(9) Calculated 1133.7(8)
This alert is caused by a rounding error.

042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.21 Ratio
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
432_ALERT_2_C Short Inter X...Y Contact C4 .. C4 .. 3.17 Ang.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2

No action taken here.

;
#end of refcif
_cell_length_a                   13.312(6)
_cell_length_b                   15.054(7)
_cell_length_c                   6.245(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.06(2)
_cell_angle_gamma                90
_cell_volume                     1133.6(9)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1 '
_symmetry_space_group_name_Hall  '-C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z
x,-y,z
-x+1/2,y+1/2,-z
x+1/2,-y+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
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'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C20 H20 B2 Cu2 F8 N4 O2
# Dc = 1.90 Fooo = 644.00 Mu = 19.71 M = 162.28
# Found Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 1.90 FOOO = 644.00 Mu = 19.71 M = 161.77

_chemical_formula_sum            'C20 H18 B2 Cu2 F8 N4 O2'
_chemical_formula_moiety         '[Cu2(OH)2(bipy)2][BF4]2'
_chemical_formula_weight         647.09

_cell_measurement_reflns_used    3520
_cell_measurement_theta_min      2
_cell_measurement_theta_max      29
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_min          0.15
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_max          0.28

_exptl_crystal_density_diffrn    1.896
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    1.971

# Sheldrick geometric approximatio 0.66 0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.74
_diffrn_measurement_device       'Bruker SMART'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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            13989
_reflns_number_total             1707
_diffrn_reflns_av_R_equivalents  0.061
# Number of reflections with Friedels Law is 1707
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1701

_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         30.313
_diffrn_measured_fraction_theta_max 0.964

_diffrn_reflns_theta_full        27.888
_diffrn_measured_fraction_theta_full 0.999

_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -18
_reflns_limit_h_max              17
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   2.02
_oxford_diffrn_Wilson_scale      129.63

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

_refine_diff_density_min         -0.68
_refine_diff_density_max         0.60

# 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>-10.0\s(I)
_refine_ls_number_reflns         1650
_refine_ls_number_restraints     2
_refine_ls_number_parameters     94
_oxford_refine_ls_R_factor_ref   0.0556
_refine_ls_wR_factor_ref         0.0584
_refine_ls_goodness_of_fit_ref   1.1956
_refine_ls_shift/su_max          0.000084

# The values computed from all data
_oxford_reflns_number_all        1650
_refine_ls_R_factor_all          0.0556
_refine_ls_wR_factor_all         0.0584

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                1467
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_gt          0.0574

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
4.04 3.39 0.409
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1993).
SMART: Area-Detector Software Package; Madison, WI.

Siemens Industrial Automation, Inc (1995).
SAINT: Area-Detector Integration Software.; Madison, WI.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.09520(4) 0.5000 0.0264 1.0000 Uani S T . . . . .
N1 N 0.0545(2) 0.19478(15) 0.7281(4) 0.0244 1.0000 Uani . . . . . . .
C1 C 0.0333(2) 0.27622(19) 0.6301(4) 0.0235 1.0000 Uani . . . . . . .
C2 C 0.1300(2) 0.3448(2) 1.0060(5) 0.0333 1.0000 Uani . . . . . . .
C3 C 0.0708(2) 0.3526(2) 0.7639(5) 0.0301 1.0000 Uani . . . . . . .
C4 C 0.1107(2) 0.1875(2) 0.9633(5) 0.0316 1.0000 Uani . . . . . . .
C5 C 0.1495(2) 0.2618(2) 1.1051(5) 0.0348 1.0000 Uani . . . . . . .
O10 O -0.0484(3) 0.000000(7) 0.2776(5) 0.0301 1.0000 Uani S T . . . . .
B6 B 0.2502(4) 0.0000 0.4305(8) 0.0301 1.0000 Uani S T . . . . .
F1 F 0.20011(13) 0.07592(11) 0.4673(3) 0.0391 1.0000 Uani . . . . . . .
F3 F 0.2416(2) 0.0000 0.1978(4) 0.0364 1.0000 Uani S T . . . . .
F4 F 0.3634(2) 0.0000 0.5854(4) 0.0411 1.0000 Uani S T . . . . .
H21 H 0.1570 0.3947 1.0977 0.0532 1.0000 Uiso R . . . . . .
H31 H 0.0560 0.4086 0.6920 0.0450 1.0000 Uiso R . . . . . .
H41 H 0.1238 0.1307 1.0299 0.0443 1.0000 Uiso R . . . . . .
H51 H 0.1880 0.2552 1.2668 0.0472 1.0000 Uiso R . . . . . .
H10 H -0.1231 0.0000 0.2079 0.0500 1.0000 Uiso RS . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0289(3) 0.0234(3) 0.0239(2) 0.0000 0.0085(2) 0.0000
N1 0.0273(13) 0.0242(13) 0.0220(12) 0.0028(9) 0.0108(10) 0.0022(10)
C1 0.0252(13) 0.0276(14) 0.0187(12) 0.0006(10) 0.0102(10) 0.0007(11)
C2 0.0343(17) 0.0375(17) 0.0259(15) -0.0112(13) 0.0107(13) -0.0058(14)
C3 0.0312(16) 0.0303(16) 0.0277(15) -0.0023(12) 0.0115(13) -0.0001(13)
C4 0.0309(16) 0.0405(18) 0.0227(14) 0.0065(12) 0.0108(12) 0.0071(14)
C5 0.0294(15) 0.051(2) 0.0206(13) -0.0038(13) 0.0075(12) -0.0011(14)
O10 0.0318(17) 0.0239(15) 0.0259(16) 0.0000 0.0040(13) 0.0000
B6 0.029(2) 0.032(3) 0.024(2) 0.0000 0.007(2) 0.0000
F1 0.0436(10) 0.0345(11) 0.0352(9) -0.0036(8) 0.0129(8) 0.0036(8)
F3 0.0427(15) 0.0389(14) 0.0236(12) 0.0000 0.0103(11) 0.0000
F4 0.0308(14) 0.0508(16) 0.0295(13) 0.0000 0.0009(11) 0.0000

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2779(2)
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
Cu1 . N1 5_556 1.982(3) yes
Cu1 . F1 5_556 2.772(2) yes
Cu1 . O10 2_556 1.908(2) yes
Cu1 . N1 . 1.982(3) yes
Cu1 . O10 . 1.908(2) yes
Cu1 . F1 . 2.772(2) yes
N1 . C1 . 1.346(3) yes
N1 . C4 . 1.341(4) yes
C1 . C1 5_556 1.485(5) yes
C1 . C3 . 1.385(4) yes
C2 . C3 . 1.383(4) yes
C2 . C5 . 1.369(4) yes
C2 . H21 . 0.920 no
C3 . H31 . 0.935 no
C4 . C5 . 1.384(4) yes
C4 . H41 . 0.934 no
C5 . H51 . 0.924 no
O10 . H10 . 0.902 no
B6 . F1 6_555 1.391(3) yes
B6 . F1 . 1.391(3) yes
B6 . F3 . 1.408(5) yes
B6 . F4 . 1.404(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
N1 5_556 Cu1 . F1 5_556 93.51(8) yes
N1 5_556 Cu1 . O10 2_556 178.04(14) yes
F1 5_556 Cu1 . O10 2_556 84.62(11) yes
N1 5_556 Cu1 . N1 . 81.68(14) yes
F1 5_556 Cu1 . N1 . 95.57(9) yes
O10 2_556 Cu1 . N1 . 97.89(9) yes
N1 5_556 Cu1 . O10 . 97.89(9) yes
F1 5_556 Cu1 . O10 . 86.36(11) yes
O10 2_556 Cu1 . O10 . 82.60(14) yes
N1 . Cu1 . O10 . 178.04(14) yes
N1 5_556 Cu1 . F1 . 95.57(9) yes
F1 5_556 Cu1 . F1 . 167.98(7) yes
O10 2_556 Cu1 . F1 . 86.36(11) yes
N1 . Cu1 . F1 . 93.51(8) yes
O10 . Cu1 . F1 . 84.62(11) yes
Cu1 . N1 . C1 . 114.84(19) yes
Cu1 . N1 . C4 . 126.2(2) yes
C1 . N1 . C4 . 119.0(3) yes
C1 5_556 C1 . N1 . 114.23(15) yes
C1 5_556 C1 . C3 . 123.76(17) yes
N1 . C1 . C3 . 122.0(2) yes
C3 . C2 . C5 . 118.9(3) yes
C3 . C2 . H21 . 120.1 no
C5 . C2 . H21 . 120.9 no
C1 . C3 . C2 . 118.8(3) yes
C1 . C3 . H31 . 120.6 no
C2 . C3 . H31 . 120.6 no
N1 . C4 . C5 . 121.3(3) yes
N1 . C4 . H41 . 118.3 no
C5 . C4 . H41 . 120.4 no
C4 . C5 . C2 . 120.0(3) yes
C4 . C5 . H51 . 119.8 no
C2 . C5 . H51 . 120.2 no
Cu1 2_556 O10 . Cu1 . 97.40(14) yes
Cu1 2_556 O10 . H10 . 108.3 no
Cu1 . O10 . H10 . 108.3 no
F1 6_555 B6 . F1 . 110.5(4) yes
F1 6_555 B6 . F3 . 109.6(2) yes
F1 . B6 . F3 . 109.6(2) yes
F1 6_555 B6 . F4 . 109.6(2) yes
F1 . B6 . F4 . 109.6(2) yes
F3 . B6 . F4 . 107.8(4) yes
B6 . F1 . Cu1 . 129.9(2) yes

# Attachment 'cubf01.cif'

data_cubf01
_database_code_depnum_ccdc_archive 'CCDC 746638'

#0.30 GPa data set.

_audit_creation_date             09-07-14
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cubf01 in C2/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry.

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.63
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.59 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.68
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 380
088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.10
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 7
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 25
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 47

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 2

Platon calculates this value assuming the dataset is 100% complete: because
of the use of pressure cell this is not the case therefore platon can be wrong.

860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.21 Ratio
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for B6

No action taken here.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength.

;
#end of refcif
_cell_length_a                   13.323(2)
_cell_length_b                   15.038(3)
_cell_length_c                   6.2630(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.043(8)
_cell_angle_gamma                90
_cell_volume                     1136.8(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1 '
_symmetry_space_group_name_Hall  '-C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z
x,-y,z
-x+1/2,y+1/2,-z
x+1/2,-y+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
C 0.0000 0.0000 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0030 0.0030 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'
B 0.0000 0.0000 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0060 0.0040 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'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 1.89 Fooo = 644.00 Mu = 19.65 M = 161.77
# Found Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 1.89 FOOO = 644.00 Mu = 19.65 M = 161.77

_chemical_formula_sum            'C20 H18 B2 Cu2 F8 N4 O2'
_chemical_formula_moiety         '[Cu2(OH)2(bipy)2][BF4]2'
_chemical_formula_weight         647.09

_cell_measurement_reflns_used    1467
_cell_measurement_theta_min      3
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.15

_exptl_crystal_density_diffrn    1.890
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    1.965

# Sheldrick geometric approximatio 0.77 0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.82
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         300000
_diffrn_reflns_number            2969
_reflns_number_total             779
_diffrn_reflns_av_R_equivalents  0.060
# Number of reflections with Friedels Law is 779
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1180

_diffrn_reflns_theta_min         2.951
_diffrn_reflns_theta_max         17.421
_diffrn_measured_fraction_theta_max 0.631

_diffrn_reflns_theta_full        13.589
_diffrn_measured_fraction_theta_full 0.680

_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -15
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.38
_refine_diff_density_max         0.38

# 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         761
_refine_ls_number_restraints     2
_refine_ls_number_parameters     94
_oxford_refine_ls_R_factor_ref   0.0564
_refine_ls_wR_factor_ref         0.0763
_refine_ls_goodness_of_fit_ref   0.9018
_refine_ls_shift/su_max          0.000097

# The values computed from all data
_oxford_reflns_number_all        761
_refine_ls_R_factor_all          0.0564
_refine_ls_wR_factor_all         0.0763

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                595
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_gt          0.0659

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
62.0 62.9 27.4
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.09539(5) 0.5000 0.0328 1.0000 Uani S T . . . . .
N1 N 0.0549(3) 0.1950(2) 0.7273(6) 0.0308 1.0000 Uani . . . . . . .
C1 C 0.0329(3) 0.2766(3) 0.6299(6) 0.0283 1.0000 Uani . . . . . . .
C2 C 0.1306(4) 0.3442(4) 1.0042(7) 0.0452 1.0000 Uani . . . . . . .
C3 C 0.0704(4) 0.3531(3) 0.7633(7) 0.0381 1.0000 Uani . . . . . . .
C4 C 0.1122(4) 0.1881(3) 0.9627(7) 0.0383 1.0000 Uani . . . . . . .
C5 C 0.1504(4) 0.2621(4) 1.1040(7) 0.0411 1.0000 Uani . . . . . . .
O10 O -0.0472(4) 0.000000(7) 0.2779(6) 0.0370 1.0000 Uani S T . . . . .
B6 B 0.2510(6) 0.0000 0.4314(12) 0.0346 1.0000 Uani S T . . . . .
F1 F 0.2000(3) 0.0760(2) 0.4691(5) 0.0564 1.0000 Uani . . . . . . .
F3 F 0.2413(4) 0.0000 0.2023(6) 0.0518 1.0000 Uani S T . . . . .
F4 F 0.3621(3) 0.0000 0.5872(6) 0.0543 1.0000 Uani S T . . . . .
H21 H 0.1576 0.3941 1.0958 0.0532 1.0000 Uiso R . . . . . .
H31 H 0.0557 0.4090 0.6914 0.0450 1.0000 Uiso R . . . . . .
H41 H 0.1253 0.1314 1.0293 0.0443 1.0000 Uiso R . . . . . .
H51 H 0.1889 0.2556 1.2657 0.0472 1.0000 Uiso R . . . . . .
H10 H -0.1219 0.0000 0.2081 0.0500 1.0000 Uiso RS . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0367(5) 0.0242(5) 0.0329(4) 0.0000 0.0105(3) 0.0000
N1 0.035(3) 0.029(3) 0.0287(17) 0.0016(14) 0.0137(17) 0.0024(13)
C1 0.028(3) 0.033(3) 0.0250(18) -0.0028(17) 0.0119(18) 0.0008(15)
C2 0.044(4) 0.050(4) 0.039(2) -0.018(2) 0.014(2) -0.005(2)
C3 0.044(4) 0.033(3) 0.034(2) -0.0016(19) 0.013(2) 0.0008(18)
C4 0.033(3) 0.055(4) 0.0222(19) 0.0067(18) 0.007(2) 0.0076(19)
C5 0.030(3) 0.066(4) 0.0208(19) -0.001(2) 0.004(2) 0.0011(19)
O10 0.043(3) 0.024(3) 0.031(2) 0.0000 0.003(2) 0.0000
B6 0.038(6) 0.027(5) 0.033(3) 0.0000 0.010(4) 0.0000
F1 0.060(3) 0.046(3) 0.0576(16) -0.0065(13) 0.0195(16) 0.0063(13)
F3 0.066(3) 0.047(3) 0.0349(18) 0.0000 0.0140(19) 0.0000
F4 0.041(3) 0.060(4) 0.043(2) 0.0000 -0.0010(19) 0.0000

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.137(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
Cu1 . N1 5_556 1.980(3) yes
Cu1 . F1 5_556 2.768(3) yes
Cu1 . O10 2_556 1.910(2) yes
Cu1 . N1 . 1.980(3) yes
Cu1 . O10 . 1.910(2) yes
Cu1 . F1 . 2.768(3) yes
N1 . C1 . 1.348(5) yes
N1 . C4 . 1.347(5) yes
C1 . C1 5_556 1.486(7) yes
C1 . C3 . 1.384(6) yes
C2 . C3 . 1.383(6) yes
C2 . C5 . 1.358(7) yes
C2 . H21 . 0.920 no
C3 . H31 . 0.935 no
C4 . C5 . 1.378(7) yes
C4 . H41 . 0.934 no
C5 . H51 . 0.926 no
O10 . H10 . 0.902 no
B6 . F1 6_555 1.400(5) yes
B6 . F1 . 1.400(5) yes
B6 . F3 . 1.385(7) yes
B6 . F4 . 1.386(9) 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
N1 5_556 Cu1 . F1 5_556 93.23(12) yes
N1 5_556 Cu1 . O10 2_556 177.40(18) yes
F1 5_556 Cu1 . O10 2_556 84.24(15) yes
N1 5_556 Cu1 . N1 . 81.8(2) yes
F1 5_556 Cu1 . N1 . 95.91(12) yes
O10 2_556 Cu1 . N1 . 97.85(12) yes
N1 5_556 Cu1 . O10 . 97.85(12) yes
F1 5_556 Cu1 . O10 . 86.67(15) yes
O10 2_556 Cu1 . O10 . 82.63(17) yes
N1 . Cu1 . O10 . 177.40(18) yes
N1 5_556 Cu1 . F1 . 95.91(12) yes
F1 5_556 Cu1 . F1 . 167.90(13) yes
O10 2_556 Cu1 . F1 . 86.67(15) yes
N1 . Cu1 . F1 . 93.23(12) yes
O10 . Cu1 . F1 . 84.24(15) yes
Cu1 . N1 . C1 . 114.8(3) yes
Cu1 . N1 . C4 . 126.5(3) yes
C1 . N1 . C4 . 118.6(4) yes
C1 5_556 C1 . N1 . 114.2(2) yes
C1 5_556 C1 . C3 . 123.8(2) yes
N1 . C1 . C3 . 122.0(4) yes
C3 . C2 . C5 . 120.0(5) yes
C3 . C2 . H21 . 119.7 no
C5 . C2 . H21 . 120.3 no
C1 . C3 . C2 . 118.2(4) yes
C1 . C3 . H31 . 120.5 no
C2 . C3 . H31 . 121.3 no
N1 . C4 . C5 . 121.7(4) yes
N1 . C4 . H41 . 118.1 no
C5 . C4 . H41 . 120.2 no
C4 . C5 . C2 . 119.4(4) yes
C4 . C5 . H51 . 119.9 no
C2 . C5 . H51 . 120.6 no
Cu1 2_556 O10 . Cu1 . 97.37(17) yes
Cu1 2_556 O10 . H10 . 107.9 no
Cu1 . O10 . H10 . 107.9 no
F1 6_555 B6 . F1 . 109.5(6) yes
F1 6_555 B6 . F3 . 109.6(4) yes
F1 . B6 . F3 . 109.6(4) yes
F1 6_555 B6 . F4 . 109.3(4) yes
F1 . B6 . F4 . 109.3(4) yes
F3 . B6 . F4 . 109.4(6) yes
B6 . F1 . Cu1 . 130.4(3) yes

# Attachment 'cubf02.cif'

data_cubf02
_database_code_depnum_ccdc_archive 'CCDC 746639'

#0.80 GPa data set.

_audit_creation_date             09-07-14
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cubf02 in C2/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.59
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.89 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.62
088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.21
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 414
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 7
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 30
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 42

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

420_ALERT_2_C D-H Without Acceptor Cu1 - H101 ... ?
432_ALERT_2_C Short Inter X...Y Contact C4 .. C4 .. 3.12 Ang.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.21 Ratio
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?

No action taken here.

152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?

It is just a rounding error.

951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 2

Platon calculates this value assuming the dataset is 100% complete: because
of the use of pressure cell this is not the case therefore platon can be wrong.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength.

;
#end of refcif
_cell_length_a                   13.0669(18)
_cell_length_b                   14.932(2)
_cell_length_c                   6.1859(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.558(7)
_cell_angle_gamma                90
_cell_volume                     1097.8(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1 '
_symmetry_space_group_name_Hall  '-C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z
x,-y,z
-x+1/2,y+1/2,-z
x+1/2,-y+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
C 0.0000 0.0000 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0030 0.0030 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'
B 0.0000 0.0000 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0060 0.0040 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'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 1.96 Fooo = 644.00 Mu = 20.35 M = 161.77
# Found Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 1.96 FOOO = 644.00 Mu = 20.35 M = 161.77

_chemical_formula_sum            'C20 H18 B2 Cu2 F8 N4 O2'
_chemical_formula_moiety         '[Cu2(OH)2(bipy)2][BF4]2'
_chemical_formula_weight         647.09

_cell_measurement_reflns_used    1821
_cell_measurement_theta_min      4
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.15

_exptl_crystal_density_diffrn    1.957
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.035

# Sheldrick geometric approximatio 0.77 0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.82
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         800000
_diffrn_reflns_number            2362
_reflns_number_total             689
_diffrn_reflns_av_R_equivalents  0.046
# Number of reflections with Friedels Law is 689
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1119

_diffrn_reflns_theta_min         1.469
_diffrn_reflns_theta_max         17.317
_diffrn_measured_fraction_theta_max 0.590

_diffrn_reflns_theta_full        14.892
_diffrn_measured_fraction_theta_full 0.621

_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -15
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.31
_refine_diff_density_max         0.33

# 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         678
_refine_ls_number_restraints     2
_refine_ls_number_parameters     94
_oxford_refine_ls_R_factor_ref   0.0489
_refine_ls_wR_factor_ref         0.0616
_refine_ls_goodness_of_fit_ref   1.9123
_refine_ls_shift/su_max          0.000099

# The values computed from all data
_oxford_reflns_number_all        678
_refine_ls_R_factor_all          0.0489
_refine_ls_wR_factor_all         0.0616

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                581
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_gt          0.0601

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
43.5 17.0 9.78
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.09593(4) 0.5000 0.0266 1.0000 Uani S T . . . . .
N1 N 0.0549(3) 0.1963(2) 0.7298(5) 0.0257 1.0000 Uani . . . . . . .
C1 C 0.0331(3) 0.2789(2) 0.6312(5) 0.0214 1.0000 Uani . . . . . . .
C2 C 0.1314(4) 0.3477(3) 1.0078(6) 0.0370 1.0000 Uani . . . . . . .
C3 C 0.0716(3) 0.3556(3) 0.7661(6) 0.0311 1.0000 Uani . . . . . . .
C4 C 0.1119(3) 0.1894(3) 0.9659(6) 0.0335 1.0000 Uani . . . . . . .
C5 C 0.1516(3) 0.2639(3) 1.1103(6) 0.0372 1.0000 Uani . . . . . . .
O10 O -0.0468(3) 0.000000(7) 0.2753(6) 0.0335 1.0000 Uani S T . . . . .
B6 B 0.2510(5) 0.0000 0.4284(9) 0.0298 1.0000 Uani S T . . . . .
F1 F 0.1992(2) 0.07668(15) 0.4667(4) 0.0440 1.0000 Uani . . . . . . .
F3 F 0.2415(3) 0.0000 0.1970(5) 0.0422 1.0000 Uani S T . . . . .
F4 F 0.3642(3) 0.0000 0.5864(5) 0.0437 1.0000 Uani S T . . . . .
H21 H 0.1596 0.3981 1.1018 0.0447 1.0000 Uiso R . . . . . .
H31 H 0.0564 0.4122 0.6945 0.0377 1.0000 Uiso R . . . . . .
H41 H 0.1268 0.1325 1.0316 0.0400 1.0000 Uiso R . . . . . .
H51 H 0.1913 0.2580 1.2724 0.0438 1.0000 Uiso R . . . . . .
H101 H -0.1078 0.0000 0.2855 0.0485 1.0000 Uiso RS . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0304(4) 0.0181(4) 0.0267(3) 0.0000 0.0075(3) 0.0000
N1 0.027(2) 0.026(2) 0.0233(13) 0.0004(11) 0.0104(14) 0.0034(10)
C1 0.020(2) 0.024(2) 0.0214(15) 0.0004(13) 0.0094(15) 0.0026(11)
C2 0.040(3) 0.039(3) 0.0320(17) -0.0151(17) 0.0149(19) -0.0050(16)
C3 0.035(3) 0.024(2) 0.0336(18) -0.0020(15) 0.0134(18) -0.0001(13)
C4 0.036(3) 0.034(3) 0.0289(18) 0.0090(14) 0.0125(19) 0.0081(14)
C5 0.031(3) 0.056(3) 0.0187(16) -0.0032(16) 0.0045(18) 0.0027(16)
O10 0.036(3) 0.025(3) 0.0336(19) 0.0000 0.0088(19) 0.0000
B6 0.037(5) 0.023(4) 0.026(3) 0.0000 0.010(3) 0.0000
F1 0.0482(19) 0.0324(18) 0.0473(12) -0.0045(9) 0.0158(12) 0.0053(9)
F3 0.055(3) 0.039(2) 0.0284(14) 0.0000 0.0129(15) 0.0000
F4 0.034(2) 0.050(3) 0.0351(15) 0.0000 0.0023(15) 0.0000

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.573(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
Cu1 . F1 5_556 2.711(2) yes
Cu1 . N1 5_556 1.984(3) yes
Cu1 . O10 2_556 1.911(2) yes
Cu1 . N1 . 1.984(3) yes
Cu1 . O10 . 1.911(2) yes
Cu1 . F1 . 2.711(2) yes
N1 . C1 . 1.353(4) yes
N1 . C4 . 1.339(4) yes
C1 . C1 5_556 1.489(6) yes
C1 . C3 . 1.382(5) yes
C2 . C3 . 1.374(5) yes
C2 . C5 . 1.379(6) yes
C2 . H21 . 0.928 no
C3 . H31 . 0.936 no
C4 . C5 . 1.385(6) yes
C4 . H41 . 0.927 no
C5 . H51 . 0.922 no
O10 . H101 . 0.825 no
B6 . F1 6_555 1.400(4) yes
B6 . F1 . 1.400(4) yes
B6 . F3 . 1.384(6) yes
B6 . F4 . 1.393(7) 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
F1 5_556 Cu1 . N1 5_556 93.53(10) yes
F1 5_556 Cu1 . O10 2_556 83.82(12) yes
N1 5_556 Cu1 . O10 2_556 177.27(15) yes
F1 5_556 Cu1 . N1 . 95.66(10) yes
N1 5_556 Cu1 . N1 . 81.83(16) yes
O10 2_556 Cu1 . N1 . 97.71(10) yes
F1 5_556 Cu1 . O10 . 87.05(12) yes
N1 5_556 Cu1 . O10 . 97.71(10) yes
O10 2_556 Cu1 . O10 . 82.87(14) yes
N1 . Cu1 . O10 . 177.27(15) yes
F1 5_556 Cu1 . F1 . 167.83(10) yes
N1 5_556 Cu1 . F1 . 95.66(10) yes
O10 2_556 Cu1 . F1 . 87.05(12) yes
N1 . Cu1 . F1 . 93.53(10) yes
O10 . Cu1 . F1 . 83.82(12) yes
Cu1 . N1 . C1 . 114.9(2) yes
Cu1 . N1 . C4 . 126.5(2) yes
C1 . N1 . C4 . 118.6(3) yes
C1 5_556 C1 . N1 . 114.17(18) yes
C1 5_556 C1 . C3 . 123.98(19) yes
N1 . C1 . C3 . 121.8(3) yes
C3 . C2 . C5 . 119.4(4) yes
C3 . C2 . H21 . 120.7 no
C5 . C2 . H21 . 119.8 no
C1 . C3 . C2 . 119.1(4) yes
C1 . C3 . H31 . 120.6 no
C2 . C3 . H31 . 120.3 no
N1 . C4 . C5 . 122.1(3) yes
N1 . C4 . H41 . 118.0 no
C5 . C4 . H41 . 119.9 no
C4 . C5 . C2 . 119.0(3) yes
C4 . C5 . H51 . 121.0 no
C2 . C5 . H51 . 120.0 no
Cu1 2_556 O10 . Cu1 . 97.13(14) yes
Cu1 2_556 O10 . H101 . 88.4 no
Cu1 . O10 . H101 . 88.4 no
F1 6_555 B6 . F1 . 109.8(5) yes
F1 6_555 B6 . F3 . 109.5(3) yes
F1 . B6 . F3 . 109.5(3) yes
F1 6_555 B6 . F4 . 109.1(3) yes
F1 . B6 . F4 . 109.1(3) yes
F3 . B6 . F4 . 109.8(4) yes
B6 . F1 . Cu1 . 130.3(3) yes

# Attachment 'cubf03.cif'

data_cubf03
_database_code_depnum_ccdc_archive 'CCDC 746640'

#1.53 GPa data set.

_audit_creation_date             09-07-30
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cubf03 in C2/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.63
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.14 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.68
088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.53
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 354
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 7
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 30
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 55

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.21 Ratio
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
432_ALERT_2_C Short Inter X...Y Contact C4 .. C4 .. 3.08 Ang.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2

No action taken here.

951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 2

Platon calculates this value assuming the dataset is 100% complete: because
of the use of pressure cell this is not the case therefore platon can be wrong.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength.
;
#end of refcif
_cell_length_a                   12.8135(15)
_cell_length_b                   14.810(2)
_cell_length_c                   6.1079(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.240(7)
_cell_angle_gamma                90
_cell_volume                     1056.9(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1 '
_symmetry_space_group_name_Hall  '-C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z
x,-y,z
-x+1/2,y+1/2,-z
x+1/2,-y+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
C 0.0000 0.0000 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0030 0.0030 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'
B 0.0000 0.0000 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0060 0.0040 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'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.03 Fooo = 644.00 Mu = 21.14 M = 161.77
# Found Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.03 FOOO = 644.00 Mu = 21.14 M = 161.77

_chemical_formula_sum            'C20 H18 B2 Cu2 F8 N4 O2'
_chemical_formula_moiety         '[Cu2(OH)2(bipy)2][BF4]2'
_chemical_formula_weight         647.09

_cell_measurement_reflns_used    1440
_cell_measurement_theta_min      3
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.15

_exptl_crystal_density_diffrn    2.033
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.114

# Sheldrick geometric approximatio 0.76 0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.81
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         1530000
_diffrn_reflns_number            2801
_reflns_number_total             725
_diffrn_reflns_av_R_equivalents  0.042
# Number of reflections with Friedels Law is 725
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1103

_diffrn_reflns_theta_min         3.004
_diffrn_reflns_theta_max         17.453
_diffrn_measured_fraction_theta_max 0.633

_diffrn_reflns_theta_full        14.137
_diffrn_measured_fraction_theta_full 0.675

_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -15
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.25
_refine_diff_density_max         0.37

# 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         708
_refine_ls_number_restraints     2
_refine_ls_number_parameters     94
_oxford_refine_ls_R_factor_ref   0.0380
_refine_ls_wR_factor_ref         0.0638
_refine_ls_goodness_of_fit_ref   0.9134
_refine_ls_shift/su_max          0.000092

# The values computed from all data
_oxford_reflns_number_all        708
_refine_ls_R_factor_all          0.0380
_refine_ls_wR_factor_all         0.0638

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                609
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_gt          0.0588

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
48.9 59.9 29.3 5.86
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.09636(4) 0.5000 0.0242 1.0000 Uani S T . . . . .
N1 N 0.0561(2) 0.19717(18) 0.7315(4) 0.0219 1.0000 Uani . . . . . . .
C1 C 0.0335(3) 0.2804(2) 0.6312(5) 0.0193 1.0000 Uani . . . . . . .
C2 C 0.1332(3) 0.3491(3) 1.0124(5) 0.0319 1.0000 Uani . . . . . . .
C3 C 0.0728(3) 0.3579(2) 0.7673(5) 0.0271 1.0000 Uani . . . . . . .
C4 C 0.1135(3) 0.1902(3) 0.9702(5) 0.0297 1.0000 Uani . . . . . . .
C5 C 0.1529(3) 0.2649(3) 1.1155(5) 0.0305 1.0000 Uani . . . . . . .
O10 O -0.0468(3) 0.000000(7) 0.2730(5) 0.0306 1.0000 Uani S T . . . . .
B6 B 0.2513(5) 0.0000 0.4263(8) 0.0247 1.0000 Uani S T . . . . .
F1 F 0.19910(19) 0.07735(14) 0.4670(3) 0.0369 1.0000 Uani . . . . . . .
F3 F 0.2421(3) 0.0000 0.1930(4) 0.0348 1.0000 Uani S T . . . . .
F4 F 0.3661(3) 0.0000 0.5857(5) 0.0369 1.0000 Uani S T . . . . .
H21 H 0.1615 0.3994 1.1041 0.0389 1.0000 Uiso R . . . . . .
H31 H 0.0587 0.4140 0.6931 0.0333 1.0000 Uiso R . . . . . .
H41 H 0.1263 0.1329 1.0330 0.0350 1.0000 Uiso R . . . . . .
H51 H 0.1917 0.2587 1.2782 0.0360 1.0000 Uiso R . . . . . .
H101 H -0.0968 0.0000 0.1352 0.0446 1.0000 Uiso RS . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0286(4) 0.0170(4) 0.0233(3) 0.0000 0.0066(2) 0.0000
N1 0.0223(18) 0.0238(19) 0.0195(11) 0.0008(9) 0.0083(12) 0.0037(9)
C1 0.016(2) 0.023(2) 0.0182(14) 0.0002(12) 0.0063(13) 0.0005(10)
C2 0.031(3) 0.037(3) 0.0260(15) -0.0135(14) 0.0098(16) -0.0048(13)
C3 0.031(2) 0.022(2) 0.0288(15) -0.0003(12) 0.0125(15) -0.0005(12)
C4 0.023(2) 0.043(2) 0.0205(13) 0.0079(13) 0.0061(14) 0.0065(13)
C5 0.024(2) 0.047(3) 0.0151(13) -0.0027(13) 0.0030(14) 0.0018(13)
O10 0.039(3) 0.018(2) 0.0235(14) 0.0000 0.0011(15) 0.0000
B6 0.024(4) 0.021(4) 0.023(2) 0.0000 0.005(2) 0.0000
F1 0.0383(16) 0.0299(16) 0.0391(10) -0.0035(8) 0.0126(10) 0.0054(8)
F3 0.041(2) 0.036(2) 0.0218(12) 0.0000 0.0063(12) 0.0000
F4 0.027(2) 0.044(2) 0.0301(13) 0.0000 0.0021(13) 0.0000

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.019(7)
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
Cu1 . F1 5_556 2.655(2) yes
Cu1 . N1 5_556 1.978(3) yes
Cu1 . O10 2_556 1.9069(19) yes
Cu1 . N1 . 1.978(3) yes
Cu1 . O10 . 1.9069(19) yes
Cu1 . F1 . 2.655(2) yes
N1 . C1 . 1.354(4) yes
N1 . C4 . 1.340(4) yes
C1 . C1 5_556 1.476(5) yes
C1 . C3 . 1.384(5) yes
C2 . C3 . 1.380(4) yes
C2 . C5 . 1.373(5) yes
C2 . H21 . 0.913 no
C3 . H31 . 0.928 no
C4 . C5 . 1.378(5) yes
C4 . H41 . 0.918 no
C5 . H51 . 0.915 no
O10 . H101 . 0.822 no
B6 . F1 6_555 1.399(4) yes
B6 . F1 . 1.399(4) yes
B6 . F3 . 1.381(5) yes
B6 . F4 . 1.391(6) 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
F1 5_556 Cu1 . N1 5_556 93.20(9) yes
F1 5_556 Cu1 . O10 2_556 83.71(11) yes
N1 5_556 Cu1 . O10 2_556 176.81(13) yes
F1 5_556 Cu1 . N1 . 95.99(9) yes
N1 5_556 Cu1 . N1 . 81.96(14) yes
O10 2_556 Cu1 . N1 . 97.56(9) yes
F1 5_556 Cu1 . O10 . 87.18(12) yes
N1 5_556 Cu1 . O10 . 97.56(9) yes
O10 2_556 Cu1 . O10 . 83.09(13) yes
N1 . Cu1 . O10 . 176.81(13) yes
F1 5_556 Cu1 . F1 . 167.82(10) yes
N1 5_556 Cu1 . F1 . 95.99(9) yes
O10 2_556 Cu1 . F1 . 87.18(12) yes
N1 . Cu1 . F1 . 93.20(9) yes
O10 . Cu1 . F1 . 83.71(11) yes
Cu1 . N1 . C1 . 114.60(18) yes
Cu1 . N1 . C4 . 126.6(2) yes
C1 . N1 . C4 . 118.8(3) yes
C1 5_556 C1 . N1 . 114.37(15) yes
C1 5_556 C1 . C3 . 123.94(18) yes
N1 . C1 . C3 . 121.7(3) yes
C3 . C2 . C5 . 119.9(3) yes
C3 . C2 . H21 . 119.6 no
C5 . C2 . H21 . 120.5 no
C1 . C3 . C2 . 118.5(3) yes
C1 . C3 . H31 . 119.9 no
C2 . C3 . H31 . 121.6 no
N1 . C4 . C5 . 122.1(3) yes
N1 . C4 . H41 . 116.7 no
C5 . C4 . H41 . 121.2 no
C4 . C5 . C2 . 119.0(3) yes
C4 . C5 . H51 . 120.7 no
C2 . C5 . H51 . 120.3 no
Cu1 2_556 O10 . Cu1 . 96.91(13) yes
Cu1 2_556 O10 . H101 . 128.7 no
Cu1 . O10 . H101 . 128.7 no
F1 6_555 B6 . F1 . 110.0(4) yes
F1 6_555 B6 . F3 . 109.8(3) yes
F1 . B6 . F3 . 109.8(3) yes
F1 6_555 B6 . F4 . 108.7(3) yes
F1 . B6 . F4 . 108.7(3) yes
F3 . B6 . F4 . 109.9(4) yes
B6 . F1 . Cu1 . 130.1(2) yes

# Attachment 'cubf04.cif'

data_cubf04
_database_code_depnum_ccdc_archive 'CCDC 746641'

#2.25 GPa data set.

_audit_creation_date             09-07-30
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cubf04 in C2/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.57
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.49 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.63
088_ALERT_3_B Poor Data / Parameter Ratio .................... 6.73
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 385
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 7
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 31
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 58

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 2

Platon calculates these values assuming the dataset is 100% complete: because
of the use of pressure cell this is not the case therefore platon can be wrong.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength.

760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.21 Ratio
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?

No action taken here.

;
#end of refcif
_cell_length_a                   12.628(2)
_cell_length_b                   14.716(3)
_cell_length_c                   6.0524(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.837(9)
_cell_angle_gamma                90
_cell_volume                     1028.8(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1 '
_symmetry_space_group_name_Hall  '-C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z
x,-y,z
-x+1/2,y+1/2,-z
x+1/2,-y+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
C 0.0000 0.0000 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0030 0.0030 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'
B 0.0000 0.0000 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0060 0.0040 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'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.09 Fooo = 644.00 Mu = 21.71 M = 161.77
# Found Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.09 FOOO = 644.00 Mu = 21.71 M = 161.77

_chemical_formula_sum            'C20 H18 B2 Cu2 F8 N4 O2'
_chemical_formula_moiety         '[Cu2(OH)2(bipy)2][BF4]2'
_chemical_formula_weight         647.09

_cell_measurement_reflns_used    1568
_cell_measurement_theta_min      4
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.15

_exptl_crystal_density_diffrn    2.089
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.171

# Sheldrick geometric approximatio 0.75 0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.80
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         2250000
_diffrn_reflns_number            2258
_reflns_number_total             646
_diffrn_reflns_av_R_equivalents  0.039
# Number of reflections with Friedels Law is 646
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1063

_diffrn_reflns_theta_min         3.026
_diffrn_reflns_theta_max         17.462
_diffrn_measured_fraction_theta_max 0.575

_diffrn_reflns_theta_full        14.494
_diffrn_measured_fraction_theta_full 0.631

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -14
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.44
_refine_diff_density_max         0.36

# 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         633
_refine_ls_number_restraints     2
_refine_ls_number_parameters     94
_oxford_refine_ls_R_factor_ref   0.0405
_refine_ls_wR_factor_ref         0.0727
_refine_ls_goodness_of_fit_ref   1.0131
_refine_ls_shift/su_max          0.000071

# The values computed from all data
_oxford_reflns_number_all        633
_refine_ls_R_factor_all          0.0405
_refine_ls_wR_factor_all         0.0727

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                552
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_gt          0.0673

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
45.9 55.0 23.3
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.09658(5) 0.5000 0.0222 1.0000 Uani S T . . . . .
N1 N 0.0562(3) 0.1973(2) 0.7330(5) 0.0208 1.0000 Uani . . . . . . .
C1 C 0.0338(3) 0.2810(3) 0.6315(6) 0.0170 1.0000 Uani . . . . . . .
C2 C 0.1343(4) 0.3507(3) 1.0151(7) 0.0297 1.0000 Uani . . . . . . .
C3 C 0.0734(4) 0.3593(3) 0.7687(7) 0.0243 1.0000 Uani . . . . . . .
C4 C 0.1136(4) 0.1905(3) 0.9722(7) 0.0265 1.0000 Uani . . . . . . .
C5 C 0.1539(4) 0.2662(3) 1.1192(7) 0.0278 1.0000 Uani . . . . . . .
O10 O -0.0467(4) 0.000000(7) 0.2702(6) 0.0289 1.0000 Uani S T . . . . .
B6 B 0.2512(6) 0.0000 0.4263(10) 0.0225 1.0000 Uani S T . . . . .
F1 F 0.1986(2) 0.07799(17) 0.4671(4) 0.0327 1.0000 Uani . . . . . . .
F3 F 0.2419(3) 0.0000 0.1891(5) 0.0311 1.0000 Uani S T . . . . .
F4 F 0.3676(3) 0.0000 0.5849(6) 0.0311 1.0000 Uani S T . . . . .
H21 H 0.1638 0.4010 1.1091 0.0371 1.0000 Uiso R . . . . . .
H31 H 0.0597 0.4157 0.6961 0.0314 1.0000 Uiso R . . . . . .
H41 H 0.1266 0.1340 1.0387 0.0348 1.0000 Uiso R . . . . . .
H51 H 0.1934 0.2601 1.2833 0.0332 1.0000 Uiso R . . . . . .
H101 H -0.0838 0.0000 0.1270 0.0425 1.0000 Uiso RS . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0255(5) 0.0154(5) 0.0216(4) 0.0000 0.0052(3) 0.0000
N1 0.025(2) 0.019(2) 0.0208(15) 0.0019(12) 0.0110(15) 0.0016(11)
C1 0.010(2) 0.022(3) 0.0187(17) -0.0010(14) 0.0055(16) 0.0014(12)
C2 0.025(3) 0.039(3) 0.0252(18) -0.0102(18) 0.0102(19) -0.0042(16)
C3 0.027(3) 0.020(3) 0.0266(18) 0.0019(15) 0.0121(18) 0.0036(14)
C4 0.031(3) 0.028(3) 0.0215(17) 0.0074(16) 0.0115(18) 0.0084(15)
C5 0.020(3) 0.045(3) 0.0141(16) -0.0006(16) 0.0026(17) 0.0016(16)
O10 0.035(3) 0.022(3) 0.0210(18) 0.0000 0.0020(18) 0.0000
B6 0.031(5) 0.016(4) 0.019(3) 0.0000 0.009(3) 0.0000
F1 0.0307(17) 0.0305(19) 0.0326(12) -0.0032(10) 0.0084(11) 0.0049(9)
F3 0.035(2) 0.034(3) 0.0188(14) 0.0000 0.0054(15) 0.0000
F4 0.029(2) 0.030(3) 0.0278(16) 0.0000 0.0044(16) 0.0000

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.985(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
Cu1 . F1 5_556 2.609(3) yes
Cu1 . N1 5_556 1.970(3) yes
Cu1 . O10 2_556 1.908(2) yes
Cu1 . N1 . 1.970(3) yes
Cu1 . O10 . 1.908(2) yes
Cu1 . F1 . 2.609(3) yes
N1 . C1 . 1.353(5) yes
N1 . C4 . 1.335(5) yes
C1 . C1 5_556 1.472(7) yes
C1 . C3 . 1.391(6) yes
C2 . C3 . 1.380(5) yes
C2 . C5 . 1.371(7) yes
C2 . H21 . 0.916 no
C3 . H31 . 0.922 no
C4 . C5 . 1.387(6) yes
C4 . H41 . 0.909 no
C5 . H51 . 0.918 no
O10 . H101 . 0.801 no
B6 . F1 6_555 1.397(4) yes
B6 . F1 . 1.397(4) yes
B6 . F3 . 1.392(6) yes
B6 . F4 . 1.394(8) 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
F1 5_556 Cu1 . N1 5_556 93.12(11) yes
F1 5_556 Cu1 . O10 2_556 83.67(14) yes
N1 5_556 Cu1 . O10 2_556 176.68(15) yes
F1 5_556 Cu1 . N1 . 95.93(11) yes
N1 5_556 Cu1 . N1 . 82.37(18) yes
O10 2_556 Cu1 . N1 . 97.07(12) yes
F1 5_556 Cu1 . O10 . 87.37(14) yes
N1 5_556 Cu1 . O10 . 97.07(12) yes
O10 2_556 Cu1 . O10 . 83.67(16) yes
N1 . Cu1 . O10 . 176.68(15) yes
F1 5_556 Cu1 . F1 . 167.96(12) yes
N1 5_556 Cu1 . F1 . 95.93(11) yes
O10 2_556 Cu1 . F1 . 87.37(14) yes
N1 . Cu1 . F1 . 93.12(11) yes
O10 . Cu1 . F1 . 83.67(13) yes
Cu1 . N1 . C1 . 114.3(2) yes
Cu1 . N1 . C4 . 126.9(3) yes
C1 . N1 . C4 . 118.8(3) yes
C1 5_556 C1 . N1 . 114.5(2) yes
C1 5_556 C1 . C3 . 123.9(2) yes
N1 . C1 . C3 . 121.6(3) yes
C3 . C2 . C5 . 119.9(4) yes
C3 . C2 . H21 . 120.4 no
C5 . C2 . H21 . 119.7 no
C1 . C3 . C2 . 118.5(4) yes
C1 . C3 . H31 . 120.6 no
C2 . C3 . H31 . 120.9 no
N1 . C4 . C5 . 122.2(4) yes
N1 . C4 . H41 . 118.0 no
C5 . C4 . H41 . 119.8 no
C4 . C5 . C2 . 118.8(4) yes
C4 . C5 . H51 . 120.9 no
C2 . C5 . H51 . 120.3 no
Cu1 2_556 O10 . Cu1 . 96.33(16) yes
Cu1 2_556 O10 . H101 . 131.4 no
Cu1 . O10 . H101 . 131.4 no
F1 6_555 B6 . F1 . 110.5(5) yes
F1 6_555 B6 . F3 . 109.5(3) yes
F1 . B6 . F3 . 109.5(3) yes
F1 6_555 B6 . F4 . 108.8(3) yes
F1 . B6 . F4 . 108.8(3) yes
F3 . B6 . F4 . 109.6(5) yes
B6 . F1 . Cu1 . 129.8(3) yes

# Attachment 'cubf05.cif'

data_cubf05
_database_code_depnum_ccdc_archive 'CCDC 746642'

#2.80 GPa data set.

_audit_creation_date             09-07-30
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cubf05 in C2/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.62
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.64 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.66
088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.12
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 344
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 7
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 31
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 52

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 2

Platon calculates these values assuming the dataset is 100% complete: because
of the use of pressure cell this is not the case therefore platon can be wrong.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength.

042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.21 Ratio
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
432_ALERT_2_C Short Inter X...Y Contact C4 .. C4 .. 3.00 Ang.
432_ALERT_2_C Short Inter X...Y Contact C2 .. C4 .. 3.17 Ang.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2

No action taken here.

;
#end of refcif
_cell_length_a                   12.5039(16)
_cell_length_b                   14.673(2)
_cell_length_c                   6.0173(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.653(7)
_cell_angle_gamma                90
_cell_volume                     1011.3(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1 '
_symmetry_space_group_name_Hall  '-C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z
x,-y,z
-x+1/2,y+1/2,-z
x+1/2,-y+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
C 0.0000 0.0000 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0030 0.0030 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'
B 0.0000 0.0000 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0060 0.0040 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'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.12 Fooo = 644.00 Mu = 22.09 M = 161.77
# Found Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.12 FOOO = 644.00 Mu = 22.09 M = 161.77

_chemical_formula_sum            'C20 H18 B2 Cu2 F8 N4 O2'
_chemical_formula_moiety         '[Cu2(OH)2(bipy)2][BF4]2'
_chemical_formula_weight         647.09

_cell_measurement_reflns_used    1430
_cell_measurement_theta_min      3
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.15

_exptl_crystal_density_diffrn    2.125
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.209

# Sheldrick geometric approximatio 0.75 0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.80
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         2800000
_diffrn_reflns_number            2599
_reflns_number_total             679
_diffrn_reflns_av_R_equivalents  0.037
# Number of reflections with Friedels Law is 679
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1050

_diffrn_reflns_theta_min         3.037
_diffrn_reflns_theta_max         17.425
_diffrn_measured_fraction_theta_max 0.620

_diffrn_reflns_theta_full        14.637
_diffrn_measured_fraction_theta_full 0.664

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -14
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.30
_refine_diff_density_max         0.34

# 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         669
_refine_ls_number_restraints     2
_refine_ls_number_parameters     94
_oxford_refine_ls_R_factor_ref   0.0365
_refine_ls_wR_factor_ref         0.0847
_refine_ls_goodness_of_fit_ref   0.7478
_refine_ls_shift/su_max          0.000079

# The values computed from all data
_oxford_reflns_number_all        669
_refine_ls_R_factor_all          0.0365
_refine_ls_wR_factor_all         0.0847

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                569
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_gt          0.0704

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
77.7 112. 59.3 14.9
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.09685(4) 0.5000 0.0213 1.0000 Uani S T . . . . .
N1 N 0.0568(2) 0.1984(2) 0.7338(4) 0.0183 1.0000 Uani . . . . . . .
C1 C 0.0341(3) 0.2818(2) 0.6318(5) 0.0161 1.0000 Uani . . . . . . .
C2 C 0.1353(3) 0.3521(3) 1.0170(6) 0.0265 1.0000 Uani . . . . . . .
C3 C 0.0735(3) 0.3601(3) 0.7692(5) 0.0231 1.0000 Uani . . . . . . .
C4 C 0.1150(3) 0.1914(3) 0.9761(5) 0.0250 1.0000 Uani . . . . . . .
C5 C 0.1541(3) 0.2668(3) 1.1213(5) 0.0248 1.0000 Uani . . . . . . .
O10 O -0.0461(3) 0.000000(7) 0.2693(6) 0.0277 1.0000 Uani S T . . . . .
B6 B 0.2518(5) 0.0000 0.4275(9) 0.0210 1.0000 Uani S T . . . . .
F1 F 0.1981(2) 0.07829(16) 0.4671(4) 0.0303 1.0000 Uani . . . . . . .
F3 F 0.2418(3) 0.0000 0.1870(4) 0.0274 1.0000 Uani S T . . . . .
F4 F 0.3685(3) 0.0000 0.5849(5) 0.0296 1.0000 Uani S T . . . . .
H21 H 0.1645 0.4020 1.1102 0.0337 1.0000 Uiso R . . . . . .
H31 H 0.0609 0.4163 0.6993 0.0280 1.0000 Uiso R . . . . . .
H41 H 0.1284 0.1344 1.0404 0.0313 1.0000 Uiso R . . . . . .
H51 H 0.1938 0.2615 1.2891 0.0314 1.0000 Uiso R . . . . . .
H101 H -0.0861 0.0000 0.1290 0.0410 1.0000 Uiso RS . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0242(5) 0.0149(5) 0.0208(4) 0.0000 0.0047(3) 0.0000
N1 0.0184(18) 0.019(2) 0.0162(12) 0.0025(10) 0.0060(12) 0.0033(9)
C1 0.011(2) 0.023(2) 0.0142(14) -0.0013(11) 0.0049(14) -0.0013(10)
C2 0.030(2) 0.027(3) 0.0238(15) -0.0112(14) 0.0113(17) -0.0045(13)
C3 0.026(2) 0.021(2) 0.0195(14) 0.0008(12) 0.0062(15) 0.0034(12)
C4 0.026(2) 0.028(2) 0.0184(14) 0.0073(13) 0.0066(15) 0.0064(13)
C5 0.019(2) 0.038(3) 0.0137(13) -0.0021(13) 0.0035(14) 0.0019(13)
O10 0.035(3) 0.020(3) 0.0188(14) 0.0000 0.0010(16) 0.0000
B6 0.028(4) 0.016(4) 0.018(2) 0.0000 0.008(2) 0.0000
F1 0.0284(15) 0.0277(16) 0.0312(11) -0.0036(9) 0.0082(11) 0.0052(8)
F3 0.035(2) 0.025(2) 0.0169(12) 0.0000 0.0046(12) 0.0000
F4 0.021(2) 0.036(2) 0.0236(13) 0.0000 0.0000(14) 0.0000

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.966(8)
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
Cu1 . F1 5_556 2.577(2) yes
Cu1 . N1 5_556 1.976(3) yes
Cu1 . O10 2_556 1.907(2) yes
Cu1 . N1 . 1.976(3) yes
Cu1 . O10 . 1.907(2) yes
Cu1 . F1 . 2.577(2) yes
N1 . C1 . 1.347(4) yes
N1 . C4 . 1.347(4) yes
C1 . C1 5_556 1.469(5) yes
C1 . C3 . 1.386(5) yes
C2 . C3 . 1.382(4) yes
C2 . C5 . 1.377(6) yes
C2 . H21 . 0.906 no
C3 . H31 . 0.909 no
C4 . C5 . 1.372(5) yes
C4 . H41 . 0.908 no
C5 . H51 . 0.933 no
O10 . H101 . 0.790 no
B6 . F1 6_555 1.399(4) yes
B6 . F1 . 1.399(4) yes
B6 . F3 . 1.402(5) yes
B6 . F4 . 1.385(7) 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
F1 5_556 Cu1 . N1 5_556 93.01(9) yes
F1 5_556 Cu1 . O10 2_556 83.38(12) yes
N1 5_556 Cu1 . O10 2_556 176.24(12) yes
F1 5_556 Cu1 . N1 . 96.14(9) yes
N1 5_556 Cu1 . N1 . 82.07(15) yes
O10 2_556 Cu1 . N1 . 97.26(11) yes
F1 5_556 Cu1 . O10 . 87.58(12) yes
N1 5_556 Cu1 . O10 . 97.26(11) yes
O10 2_556 Cu1 . O10 . 83.65(14) yes
N1 . Cu1 . O10 . 176.24(12) yes
F1 5_556 Cu1 . F1 . 167.87(11) yes
N1 5_556 Cu1 . F1 . 96.14(9) yes
O10 2_556 Cu1 . F1 . 87.58(12) yes
N1 . Cu1 . F1 . 93.01(9) yes
O10 . Cu1 . F1 . 83.38(12) yes
Cu1 . N1 . C1 . 114.25(19) yes
Cu1 . N1 . C4 . 126.6(3) yes
C1 . N1 . C4 . 119.1(3) yes
C1 5_556 C1 . N1 . 114.65(17) yes
C1 5_556 C1 . C3 . 123.90(18) yes
N1 . C1 . C3 . 121.4(3) yes
C3 . C2 . C5 . 119.2(3) yes
C3 . C2 . H21 . 120.7 no
C5 . C2 . H21 . 120.0 no
C1 . C3 . C2 . 118.9(3) yes
C1 . C3 . H31 . 121.4 no
C2 . C3 . H31 . 119.6 no
N1 . C4 . C5 . 121.8(3) yes
N1 . C4 . H41 . 117.3 no
C5 . C4 . H41 . 120.9 no
C2 . C5 . C4 . 119.4(3) yes
C2 . C5 . H51 . 119.2 no
C4 . C5 . H51 . 121.4 no
Cu1 2_556 O10 . Cu1 . 96.35(14) yes
Cu1 2_556 O10 . H101 . 130.9 no
Cu1 . O10 . H101 . 130.9 no
F1 6_555 B6 . F1 . 110.4(4) yes
F1 6_555 B6 . F3 . 109.0(3) yes
F1 . B6 . F3 . 109.0(3) yes
F1 6_555 B6 . F4 . 109.3(3) yes
F1 . B6 . F4 . 109.3(3) yes
F3 . B6 . F4 . 109.8(4) yes
Cu1 . F1 . B6 . 129.9(2) yes

# Attachment 'cubf06.cif'

data_cubf06
_database_code_depnum_ccdc_archive 'CCDC 746643'

#3.50 GPa data set.

_audit_creation_date             09-07-15
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cubf06 in C2/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.65
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.39 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.70
088_ALERT_3_B Poor Data / Parameter Ratio .................... 7.33
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 302
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 7
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 31
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 49

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 2

Platon calculates these values assuming the dataset is 100% complete: because
of the use of pressure cell this is not the case therefore platon can be wrong.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength.

432_ALERT_2_B Short Inter X...Y Contact C4 .. C4 .. 2.96 Ang.
420_ALERT_2_C D-H Without Acceptor Cu1 - H101 ... ?
432_ALERT_2_C Short Inter X...Y Contact C2 .. C4 .. 3.14 Ang.
432_ALERT_2_C Short Inter X...Y Contact C4 .. C5 .. 3.19 Ang.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?

No action taken here.

;
#end of refcif
_cell_length_a                   12.3731(7)
_cell_length_b                   14.6135(10)
_cell_length_c                   5.9739(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.441(3)
_cell_angle_gamma                90
_cell_volume                     991.02(10)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1 '
_symmetry_space_group_name_Hall  '-C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z
x,-y,z
-x+1/2,y+1/2,-z
x+1/2,-y+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
C 0.0000 0.0000 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'
B 0.0000 0.0000 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0030 0.0030 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'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0060 0.0040 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'

_cell_formula_units_Z            2

# Given Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.17 Fooo = 644.00 Mu = 22.54 M = 161.77
# Found Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.17 FOOO = 644.00 Mu = 22.54 M = 161.77

_chemical_formula_sum            'C20 H18 B2 Cu2 F8 N4 O2'
_chemical_formula_moiety         '[Cu2(OH)2(bipy)2][BF4]2'
_chemical_formula_weight         647.09

_cell_measurement_reflns_used    1607
_cell_measurement_theta_min      3
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.15

_exptl_crystal_density_diffrn    2.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.254

# Sheldrick geometric approximatio 0.75 0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.80
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         3500000
_diffrn_reflns_number            2792
_reflns_number_total             698
_diffrn_reflns_av_R_equivalents  0.033
# Number of reflections with Friedels Law is 698
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1015

_diffrn_reflns_theta_min         1.524
_diffrn_reflns_theta_max         17.341
_diffrn_measured_fraction_theta_max 0.653

_diffrn_reflns_theta_full        14.393
_diffrn_measured_fraction_theta_full 0.702

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -14
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.40
_refine_diff_density_max         0.32

# 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         689
_refine_ls_number_restraints     2
_refine_ls_number_parameters     94
_oxford_refine_ls_R_factor_ref   0.0383
_refine_ls_wR_factor_ref         0.0622
_refine_ls_goodness_of_fit_ref   0.7368
_refine_ls_shift/su_max          0.000081

# The values computed from all data
_oxford_reflns_number_all        689
_refine_ls_R_factor_all          0.0383
_refine_ls_wR_factor_all         0.0622

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                587
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_gt          0.0559

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
66.7 82.8 33.6
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.09694(4) 0.5000 0.0209 1.0000 Uani S T . . . . .
N1 N 0.0567(2) 0.1988(2) 0.7344(4) 0.0182 1.0000 Uani . . . . . . .
C1 C 0.0343(3) 0.2821(2) 0.6337(5) 0.0158 1.0000 Uani . . . . . . .
C2 C 0.1364(3) 0.3527(3) 1.0196(6) 0.0256 1.0000 Uani . . . . . . .
C3 C 0.0738(3) 0.3607(3) 0.7699(5) 0.0228 1.0000 Uani . . . . . . .
C4 C 0.1148(3) 0.1911(3) 0.9770(6) 0.0239 1.0000 Uani . . . . . . .
C5 C 0.1553(3) 0.2678(3) 1.1240(5) 0.0238 1.0000 Uani . . . . . . .
O10 O -0.0449(3) 0.000000(7) 0.2652(6) 0.0268 1.0000 Uani S T . . . . .
B6 B 0.2517(5) 0.0000 0.4250(9) 0.0222 1.0000 Uani S T . . . . .
F1 F 0.19783(19) 0.07882(15) 0.4665(3) 0.0292 1.0000 Uani . . . . . . .
F3 F 0.2422(3) 0.0000 0.1860(4) 0.0267 1.0000 Uani S T . . . . .
F4 F 0.3695(3) 0.0000 0.5847(5) 0.0285 1.0000 Uani S T . . . . .
H21 H 0.1671 0.4044 1.1163 0.0313 1.0000 Uiso R . . . . . .
H31 H 0.0584 0.4177 0.6977 0.0286 1.0000 Uiso R . . . . . .
H41 H 0.1285 0.1315 1.0431 0.0304 1.0000 Uiso R . . . . . .
H51 H 0.1955 0.2621 1.2924 0.0289 1.0000 Uiso R . . . . . .
H101 H -0.1159 0.0000 0.2244 0.0391 1.0000 Uiso RS . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0234(4) 0.0145(4) 0.0202(3) 0.0000 0.0039(3) 0.0000
N1 0.0137(19) 0.026(2) 0.0156(12) 0.0015(11) 0.0062(13) 0.0009(10)
C1 0.010(2) 0.023(2) 0.0147(14) 0.0023(12) 0.0052(14) 0.0010(11)
C2 0.034(3) 0.022(3) 0.0213(15) -0.0100(14) 0.0122(17) -0.0040(14)
C3 0.023(2) 0.024(2) 0.0208(15) -0.0014(13) 0.0077(16) 0.0005(13)
C4 0.026(2) 0.025(2) 0.0203(15) 0.0061(13) 0.0091(16) 0.0056(13)
C5 0.018(2) 0.037(3) 0.0119(13) -0.0007(14) 0.0020(14) 0.0031(13)
O10 0.029(3) 0.017(2) 0.0250(16) 0.0000 0.0017(17) 0.0000
B6 0.032(4) 0.012(4) 0.020(2) 0.0000 0.007(3) 0.0000
F1 0.0273(15) 0.0260(16) 0.0301(10) -0.0027(9) 0.0070(10) 0.0042(8)
F3 0.034(2) 0.024(2) 0.0176(12) 0.0000 0.0052(13) 0.0000
F4 0.019(2) 0.039(2) 0.0208(13) 0.0000 0.0010(13) 0.0000

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.051(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
Cu1 . F1 5_556 2.548(2) yes
Cu1 . N1 5_556 1.972(3) yes
Cu1 . O10 2_556 1.914(2) yes
Cu1 . N1 . 1.972(3) yes
Cu1 . O10 . 1.914(2) yes
Cu1 . F1 . 2.548(2) yes
N1 . C1 . 1.338(4) yes
N1 . C4 . 1.342(4) yes
C1 . C1 5_556 1.481(6) yes
C1 . C3 . 1.379(5) yes
C2 . C3 . 1.385(5) yes
C2 . C5 . 1.367(5) yes
C2 . H21 . 0.935 no
C3 . H31 . 0.923 no
C4 . C5 . 1.388(5) yes
C4 . H41 . 0.943 no
C5 . H51 . 0.932 no
O10 . H101 . 0.812 no
B6 . F1 6_555 1.402(4) yes
B6 . F1 . 1.402(4) yes
B6 . F3 . 1.385(6) yes
B6 . F4 . 1.388(7) 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
F1 5_556 Cu1 . N1 5_556 93.01(9) yes
F1 5_556 Cu1 . O10 2_556 82.74(12) yes
N1 5_556 Cu1 . O10 2_556 175.49(14) yes
F1 5_556 Cu1 . N1 . 95.99(9) yes
N1 5_556 Cu1 . N1 . 81.95(16) yes
O10 2_556 Cu1 . N1 . 96.93(10) yes
F1 5_556 Cu1 . O10 . 88.43(12) yes
N1 5_556 Cu1 . O10 . 96.93(10) yes
O10 2_556 Cu1 . O10 . 84.51(14) yes
N1 . Cu1 . O10 . 175.49(14) yes
F1 5_556 Cu1 . F1 . 168.07(10) yes
N1 5_556 Cu1 . F1 . 95.99(9) yes
O10 2_556 Cu1 . F1 . 88.43(12) yes
N1 . Cu1 . F1 . 93.01(9) yes
O10 . Cu1 . F1 . 82.74(12) yes
Cu1 . N1 . C1 . 114.6(2) yes
Cu1 . N1 . C4 . 126.1(2) yes
C1 . N1 . C4 . 119.2(3) yes
C1 5_556 C1 . N1 . 114.36(17) yes
C1 5_556 C1 . C3 . 123.58(19) yes
N1 . C1 . C3 . 122.1(3) yes
C3 . C2 . C5 . 119.2(3) yes
C3 . C2 . H21 . 120.9 no
C5 . C2 . H21 . 119.9 no
C2 . C3 . C1 . 118.7(3) yes
C2 . C3 . H31 . 120.1 no
C1 . C3 . H31 . 121.1 no
N1 . C4 . C5 . 121.2(3) yes
N1 . C4 . H41 . 117.4 no
C5 . C4 . H41 . 121.4 no
C4 . C5 . C2 . 119.4(3) yes
C4 . C5 . H51 . 121.0 no
C2 . C5 . H51 . 119.6 no
Cu1 . O10 . Cu1 2_556 95.49(14) yes
Cu1 . O10 . H101 . 100.6 no
Cu1 2_556 O10 . H101 . 100.6 no
F1 6_555 B6 . F1 . 110.5(4) yes
F1 6_555 B6 . F3 . 109.3(3) yes
F1 . B6 . F3 . 109.3(3) yes
F1 6_555 B6 . F4 . 108.7(3) yes
F1 . B6 . F4 . 108.7(3) yes
F3 . B6 . F4 . 110.2(4) yes
Cu1 . F1 . B6 . 129.7(2) yes

# Attachment 'cubf07.cif'

data_cubf07
_database_code_depnum_ccdc_archive 'CCDC 746644'

#4.00 GPa data set.

_audit_creation_date             09-07-15
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cubf07 in C2/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.63
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.74 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.68
088_ALERT_3_B Poor Data / Parameter Ratio .................... 6.98
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 325
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 7
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 39
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 48

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

432_ALERT_2_B Short Inter X...Y Contact C4 .. C4 .. 2.93 Ang.
432_ALERT_2_C Short Inter X...Y Contact F3 .. C3 .. 2.96 Ang.
432_ALERT_2_C Short Inter X...Y Contact F3 .. C3 .. 2.96 Ang.
432_ALERT_2_C Short Inter X...Y Contact C1 .. C5 .. 3.19 Ang.
432_ALERT_2_C Short Inter X...Y Contact C2 .. C4 .. 3.13 Ang.
432_ALERT_2_C Short Inter X...Y Contact C4 .. C5 .. 3.17 Ang.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.13 Ratio
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?

No action taken here.

951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 2

Platon calculates these values assuming the dataset is 100% complete: because
of the use of pressure cell this is not the case therefore platon can be wrong.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength.

;
#end of refcif
_cell_length_a                   12.2874(15)
_cell_length_b                   14.573(2)
_cell_length_c                   5.9483(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.258(7)
_cell_angle_gamma                90
_cell_volume                     978.6(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1 '
_symmetry_space_group_name_Hall  '-C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z
x,-y,z
-x+1/2,y+1/2,-z
x+1/2,-y+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
C 0.0000 0.0000 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'
B 0.0000 0.0000 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 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'
F 0.0060 0.0040 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'
O 0.0030 0.0030 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'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.20 Fooo = 644.00 Mu = 22.83 M = 161.77
# Found Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.20 FOOO = 644.00 Mu = 22.83 M = 161.77

_chemical_formula_sum            'C20 H18 B2 Cu2 F8 N4 O2'
_chemical_formula_moiety         '[Cu2(OH)2(bipy)2][BF4]2'
_chemical_formula_weight         647.09

_cell_measurement_reflns_used    1351
_cell_measurement_theta_min      3
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.15

_exptl_crystal_density_diffrn    2.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.283

# Sheldrick geometric approximatio 0.74 0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.80
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         4000000
_diffrn_reflns_number            2579
_reflns_number_total             667
_diffrn_reflns_av_R_equivalents  0.040
# Number of reflections with Friedels Law is 667
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1002

_diffrn_reflns_theta_min         3.062
_diffrn_reflns_theta_max         17.342
_diffrn_measured_fraction_theta_max 0.632

_diffrn_reflns_theta_full        14.741
_diffrn_measured_fraction_theta_full 0.679

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -14
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.42
_refine_diff_density_max         0.43

# 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         656
_refine_ls_number_restraints     2
_refine_ls_number_parameters     94
_oxford_refine_ls_R_factor_ref   0.0426
_refine_ls_wR_factor_ref         0.1190
_refine_ls_goodness_of_fit_ref   0.7457
_refine_ls_shift/su_max          0.000063

# The values computed from all data
_oxford_reflns_number_all        656
_refine_ls_R_factor_all          0.0426
_refine_ls_wR_factor_all         0.1190

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                566
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_gt          0.1004

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
102. 153. 87.7 26.4
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.09714(5) 0.5000 0.0192 1.0000 Uani S T . . . . .
N1 N 0.0576(3) 0.1985(3) 0.7364(5) 0.0163 1.0000 Uani . . . . . . .
C1 C 0.0341(3) 0.2827(3) 0.6323(6) 0.0138 1.0000 Uani . . . . . . .
C2 C 0.1362(4) 0.3532(3) 1.0204(6) 0.0246 1.0000 Uani . . . . . . .
C3 C 0.0740(4) 0.3616(3) 0.7691(6) 0.0195 1.0000 Uani . . . . . . .
C4 C 0.1147(4) 0.1914(3) 0.9778(7) 0.0221 1.0000 Uani . . . . . . .
C5 C 0.1558(4) 0.2681(3) 1.1270(6) 0.0243 1.0000 Uani . . . . . . .
O10 O -0.0456(4) 0.000000(7) 0.2645(7) 0.0269 1.0000 Uani S T . . . . .
B6 B 0.2517(6) 0.0000 0.4239(10) 0.0173 1.0000 Uani S T . . . . .
F1 F 0.1981(2) 0.07899(19) 0.4679(5) 0.0278 1.0000 Uani . . . . . . .
F3 F 0.2423(3) 0.0000 0.1838(5) 0.0265 1.0000 Uani S T . . . . .
F4 F 0.3693(3) 0.0000 0.5844(6) 0.0249 1.0000 Uani S T . . . . .
H21 H 0.1649 0.4058 1.1120 0.0276 1.0000 Uiso R . . . . . .
H31 H 0.0593 0.4182 0.6956 0.0221 1.0000 Uiso R . . . . . .
H41 H 0.1277 0.1330 1.0482 0.0245 1.0000 Uiso R . . . . . .
H51 H 0.1973 0.2624 1.2978 0.0242 1.0000 Uiso R . . . . . .
H101 H -0.1069 0.0000 0.1411 0.0335 1.0000 Uiso RS . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0221(6) 0.0135(6) 0.0172(5) 0.0000 0.0028(4) 0.0000
N1 0.016(2) 0.020(3) 0.0117(14) 0.0012(12) 0.0033(14) 0.0015(12)
C1 0.010(2) 0.018(3) 0.0130(18) -0.0013(13) 0.0042(17) 0.0003(12)
C2 0.023(3) 0.032(3) 0.0168(17) -0.0082(16) 0.0061(18) -0.0022(16)
C3 0.028(2) 0.009(3) 0.0201(18) -0.0006(13) 0.0080(17) 0.0012(13)
C4 0.013(2) 0.032(3) 0.0187(17) 0.0067(17) 0.0045(15) 0.0063(15)
C5 0.022(3) 0.038(3) 0.0093(18) 0.0002(15) 0.0026(18) 0.0028(15)
O10 0.037(3) 0.008(3) 0.0252(19) 0.0000 0.001(2) 0.0000
B6 0.016(4) 0.021(4) 0.011(3) 0.0000 0.000(2) 0.0000
F1 0.0230(18) 0.030(2) 0.0265(13) -0.0038(10) 0.0059(13) 0.0040(10)
F3 0.032(2) 0.027(3) 0.0155(14) 0.0000 0.0035(14) 0.0000
F4 0.024(2) 0.025(3) 0.0188(15) 0.0000 0.0005(15) 0.0000

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.853(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
Cu1 . F1 5_556 2.530(3) yes
Cu1 . Cu1 6_555 2.8313(14) yes
Cu1 . N1 5_556 1.968(4) yes
Cu1 . O10 2_556 1.913(3) yes
Cu1 . N1 . 1.968(4) yes
Cu1 . O10 . 1.913(3) yes
Cu1 . F1 . 2.530(3) yes
N1 . C1 . 1.353(5) yes
N1 . C4 . 1.330(5) yes
C1 . C1 5_556 1.463(7) yes
C1 . C3 . 1.381(6) yes
C2 . C3 . 1.390(5) yes
C2 . C5 . 1.370(7) yes
C2 . H21 . 0.927 no
C3 . H31 . 0.918 no
C4 . C5 . 1.392(7) yes
C4 . H41 . 0.934 no
C5 . H51 . 0.943 no
O10 . H101 . 0.819 no
B6 . F1 6_555 1.401(4) yes
B6 . F1 . 1.401(4) yes
B6 . F3 . 1.387(6) yes
B6 . F4 . 1.382(7) 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
F1 5_556 Cu1 . Cu1 6_555 84.00(7) yes
F1 5_556 Cu1 . N1 5_556 92.71(11) yes
Cu1 6_555 Cu1 . N1 5_556 138.63(10) yes
F1 5_556 Cu1 . O10 2_556 83.08(15) yes
Cu1 6_555 Cu1 . O10 2_556 42.28(9) yes
N1 5_556 Cu1 . O10 2_556 175.62(14) yes
F1 5_556 Cu1 . N1 . 96.29(11) yes
Cu1 6_555 Cu1 . N1 . 138.63(10) yes
N1 5_556 Cu1 . N1 . 82.74(19) yes
O10 2_556 Cu1 . N1 . 96.51(14) yes
F1 5_556 Cu1 . O10 . 88.04(15) yes
Cu1 6_555 Cu1 . O10 . 42.28(9) yes
N1 5_556 Cu1 . O10 . 96.51(14) yes
O10 2_556 Cu1 . O10 . 84.55(18) yes
N1 . Cu1 . O10 . 175.62(14) yes
F1 5_556 Cu1 . F1 . 168.00(13) yes
Cu1 6_555 Cu1 . F1 . 84.00(7) yes
N1 5_556 Cu1 . F1 . 96.29(11) yes
O10 2_556 Cu1 . F1 . 88.04(15) yes
N1 . Cu1 . F1 . 92.71(11) yes
O10 . Cu1 . F1 . 83.08(15) yes
Cu1 . N1 . C1 . 113.7(2) yes
Cu1 . N1 . C4 . 126.9(3) yes
C1 . N1 . C4 . 119.4(4) yes
C1 5_556 C1 . N1 . 114.8(2) yes
C1 5_556 C1 . C3 . 123.6(2) yes
N1 . C1 . C3 . 121.6(3) yes
C3 . C2 . C5 . 119.9(4) yes
C3 . C2 . H21 . 118.6 no
C5 . C2 . H21 . 121.4 no
C2 . C3 . C1 . 118.5(4) yes
C2 . C3 . H31 . 120.9 no
C1 . C3 . H31 . 120.7 no
N1 . C4 . C5 . 122.0(4) yes
N1 . C4 . H41 . 118.6 no
C5 . C4 . H41 . 119.4 no
C4 . C5 . C2 . 118.6(3) yes
C4 . C5 . H51 . 121.5 no
C2 . C5 . H51 . 119.9 no
Cu1 . O10 . Cu1 2_556 95.45(18) yes
Cu1 . O10 . H101 . 123.8 no
Cu1 2_556 O10 . H101 . 123.8 no
F1 6_555 B6 . F1 . 110.5(5) yes
F1 6_555 B6 . F3 . 109.7(3) yes
F1 . B6 . F3 . 109.7(3) yes
F1 6_555 B6 . F4 . 108.2(3) yes
F1 . B6 . F4 . 108.2(3) yes
F3 . B6 . F4 . 110.5(5) yes
Cu1 . F1 . B6 . 129.6(3) yes

# Attachment 'cubf08.cif'

data_cubf08
_database_code_depnum_ccdc_archive 'CCDC 746645'

#4.30 GPa data set.

_audit_creation_date             09-07-15
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cubf06 in C2/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.58
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.71 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.63
088_ALERT_3_B Poor Data / Parameter Ratio .................... 6.63
201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 1
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 362
341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 7
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 34
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 54

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 3

Platon calculates these values assuming the dataset is 100% complete: because
of the use of pressure cell this is not the case therefore platon can be wrong.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength.

432_ALERT_2_B Short Inter X...Y Contact C4 .. C4 .. 2.94 Ang.
420_ALERT_2_C D-H Without Acceptor Cu1 - H101 ... ?
432_ALERT_2_C Short Inter X...Y Contact C2 .. C4 .. 3.14 Ang.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?

No action taken here.
;
#end of refcif
_cell_length_a                   12.3731(7)
_cell_length_b                   14.6135(10)
_cell_length_c                   5.9739(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.441(3)
_cell_angle_gamma                90
_cell_volume                     991.02(10)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1 '
_symmetry_space_group_name_Hall  '-C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z
x,-y,z
-x+1/2,y+1/2,-z
x+1/2,-y+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
C 0.0000 0.0000 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'
B 0.0000 0.0000 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0030 0.0030 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'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0600 0.0040 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'

_cell_formula_units_Z            2

# Given Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.17 Fooo = 644.00 Mu = 22.54 M = 161.77
# Found Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.17 FOOO = 644.00 Mu = 22.54 M = 161.77

_chemical_formula_sum            'C20 H18 B2 Cu2 F8 N4 O2'
_chemical_formula_moiety         '[Cu2(OH)2(bipy)2][BF4]2'
_chemical_formula_weight         647.09

_cell_measurement_reflns_used    1554
_cell_measurement_theta_min      4
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.15

_exptl_crystal_density_diffrn    2.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.254

# Sheldrick geometric approximatio 0.75 0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  0.80
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         4300000
_diffrn_reflns_number            2225
_reflns_number_total             617
_diffrn_reflns_av_R_equivalents  0.041
# Number of reflections with Friedels Law is 617
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1010

_diffrn_reflns_theta_min         3.052
_diffrn_reflns_theta_max         17.311
_diffrn_measured_fraction_theta_max 0.578

_diffrn_reflns_theta_full        14.714
_diffrn_measured_fraction_theta_full 0.626

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -14
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.40
_refine_diff_density_max         0.51

# 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         603
_refine_ls_number_restraints     2
_refine_ls_number_parameters     91
_oxford_refine_ls_R_factor_ref   0.0529
_refine_ls_wR_factor_ref         0.1580
_refine_ls_goodness_of_fit_ref   0.9166
_refine_ls_shift/su_max          0.000036

# The values computed from all data
_oxford_reflns_number_all        603
_refine_ls_R_factor_all          0.0529
_refine_ls_wR_factor_all         0.1580

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                532
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_gt          0.1490

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
147. 220. 132. 46.6
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.09708(6) 0.5000 0.0187 1.0000 Uani S T . . . . .
N1 N 0.0568(4) 0.1992(3) 0.7358(7) 0.0174 1.0000 Uani . . . . . . .
C1 C 0.0339(5) 0.2824(4) 0.6338(7) 0.0161 1.0000 Uani . . . . . . .
C2 C 0.1378(5) 0.3535(4) 1.0228(8) 0.0244 1.0000 Uani . . . . . . .
C3 C 0.0737(5) 0.3618(4) 0.7702(8) 0.0197 1.0000 Uani . . . . . . .
C4 C 0.1144(5) 0.1923(4) 0.9787(7) 0.0190 1.0000 Uani . . . . . . .
C5 C 0.1562(5) 0.2671(4) 1.1272(8) 0.0209 1.0000 Uani . . . . . . .
O10 O -0.0434(6) 0.000000(7) 0.2639(9) 0.0242 1.0000 Uani S T . . . . .
B6 B 0.2536(7) 0.0000 0.4279(13) 0.0162(14) 1.0000 Uiso S . . . . . .
F1 F 0.1974(3) 0.0792(3) 0.4661(6) 0.0276 1.0000 Uani . . . . . . .
F3 F 0.2420(4) 0.0000 0.1835(6) 0.0245 1.0000 Uani S T . . . . .
F4 F 0.3696(4) 0.0000 0.5843(7) 0.0249 1.0000 Uani S T . . . . .
H21 H 0.1671 0.4052 1.1174 0.0277 1.0000 Uiso R . . . . . .
H31 H 0.0588 0.4193 0.6957 0.0234 1.0000 Uiso R . . . . . .
H41 H 0.1267 0.1342 1.0479 0.0263 1.0000 Uiso R . . . . . .
H51 H 0.1958 0.2604 1.2953 0.0278 1.0000 Uiso R . . . . . .
H101 H -0.1146 0.0000 0.2357 0.0332 1.0000 Uiso RS . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0211(9) 0.0124(9) 0.0172(6) 0.0000 0.0020(5) 0.0000
N1 0.026(3) 0.010(4) 0.018(2) -0.0010(15) 0.011(2) 0.0061(16)
C1 0.017(4) 0.020(4) 0.014(3) 0.0026(17) 0.009(3) 0.0035(19)
C2 0.035(4) 0.019(4) 0.022(2) -0.011(2) 0.014(3) -0.002(2)
C3 0.028(4) 0.011(4) 0.021(2) -0.0026(18) 0.010(2) 0.0000(18)
C4 0.021(3) 0.020(4) 0.018(2) 0.0049(18) 0.009(2) 0.0035(19)
C5 0.031(4) 0.019(4) 0.014(2) -0.0019(18) 0.010(2) 0.0023(19)
O10 0.031(4) 0.009(4) 0.025(2) 0.0000 0.004(3) 0.0000
F1 0.029(3) 0.023(3) 0.0274(16) -0.0051(12) 0.0081(16) 0.0040(13)
F3 0.038(3) 0.016(3) 0.0150(16) 0.0000 0.0058(18) 0.0000
F4 0.023(3) 0.026(3) 0.0212(18) 0.0000 0.004(2) 0.0000

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.09(2)
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
Cu1 . F1 5_556 2.543(4) yes
Cu1 . N1 5_556 1.980(5) yes
Cu1 . O10 2_556 1.920(3) yes
Cu1 . N1 . 1.980(5) yes
Cu1 . O10 . 1.920(3) yes
Cu1 . F1 . 2.543(4) yes
N1 . C1 . 1.338(7) yes
N1 . C4 . 1.342(6) yes
C1 . C1 5_556 1.481(9) yes
C1 . C3 . 1.390(8) yes
C2 . C3 . 1.404(6) yes
C2 . C5 . 1.386(8) yes
C2 . H21 . 0.927 no
C3 . H31 . 0.933 no
C4 . C5 . 1.373(8) yes
C4 . H41 . 0.929 no
C5 . H51 . 0.931 no
O10 . H101 . 0.828 no
B6 . F1 6_555 1.414(6) yes
B6 . F1 . 1.414(6) yes
B6 . F3 . 1.409(7) yes
B6 . F4 . 1.365(10) 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
F1 5_556 Cu1 . N1 5_556 93.08(15) yes
F1 5_556 Cu1 . O10 2_556 82.1(2) yes
N1 5_556 Cu1 . O10 2_556 174.91(18) yes
F1 5_556 Cu1 . N1 . 95.84(15) yes
N1 5_556 Cu1 . N1 . 82.1(2) yes
O10 2_556 Cu1 . N1 . 96.79(18) yes
F1 5_556 Cu1 . O10 . 89.2(2) yes
N1 5_556 Cu1 . O10 . 96.79(18) yes
O10 2_556 Cu1 . O10 . 84.7(2) yes
N1 . Cu1 . O10 . 174.91(18) yes
F1 5_556 Cu1 . F1 . 168.18(18) yes
N1 5_556 Cu1 . F1 . 95.84(15) yes
O10 2_556 Cu1 . F1 . 89.2(2) yes
N1 . Cu1 . F1 . 93.08(15) yes
O10 . Cu1 . F1 . 82.1(2) yes
Cu1 . N1 . C1 . 114.2(3) yes
Cu1 . N1 . C4 . 126.7(4) yes
C1 . N1 . C4 . 119.1(5) yes
C1 5_556 C1 . N1 . 114.7(3) yes
C1 5_556 C1 . C3 . 123.3(3) yes
N1 . C1 . C3 . 122.0(4) yes
C3 . C2 . C5 . 119.0(5) yes
C3 . C2 . H21 . 120.1 no
C5 . C2 . H21 . 120.9 no
C2 . C3 . C1 . 118.3(5) yes
C2 . C3 . H31 . 120.7 no
C1 . C3 . H31 . 121.0 no
N1 . C4 . C5 . 122.6(5) yes
N1 . C4 . H41 . 118.2 no
C5 . C4 . H41 . 119.2 no
C2 . C5 . C4 . 118.9(4) yes
C2 . C5 . H51 . 120.2 no
C4 . C5 . H51 . 120.9 no
Cu1 2_556 O10 . Cu1 . 95.3(2) yes
Cu1 2_556 O10 . H101 . 96.5 no
Cu1 . O10 . H101 . 96.5 no
F1 6_555 B6 . F1 . 109.8(6) yes
F1 6_555 B6 . F3 . 108.2(4) yes
F1 . B6 . F3 . 108.2(4) yes
F1 6_555 B6 . F4 . 109.9(4) yes
F1 . B6 . F4 . 109.9(4) yes
F3 . B6 . F4 . 110.8(6) yes
Cu1 . F1 . B6 . 130.3(4) yes

# Attachment 'cubf09.cif'

data_cubf09
_database_code_depnum_ccdc_archive 'CCDC 746646'

#4.70 GPa data set.

_audit_creation_date             09-07-15
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cubf09 in C2/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.56
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 14.87 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.60
088_ALERT_3_A Poor Data / Parameter Ratio .................... 5.85
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 405
341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 6
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 34
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 48

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 2

Platon calculates these values assuming the dataset is 100% complete: because
of the use of pressure cell this is not the case therefore platon can be wrong.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength.

432_ALERT_2_B Short Inter X...Y Contact C4 .. C4 .. 2.91 Ang.
432_ALERT_2_C Short Inter X...Y Contact F3 .. C3 .. 2.91 Ang.
432_ALERT_2_C Short Inter X...Y Contact F3 .. C3 .. 2.91 Ang.
432_ALERT_2_C Short Inter X...Y Contact C1 .. C5 .. 3.15 Ang.
432_ALERT_2_C Short Inter X...Y Contact C2 .. C4 .. 3.10 Ang.
432_ALERT_2_C Short Inter X...Y Contact C4 .. C5 .. 3.15 Ang.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?

No action taken here.

;
#end of refcif
_cell_length_a                   12.1792(16)
_cell_length_b                   14.516(2)
_cell_length_c                   5.8991(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.909(8)
_cell_angle_gamma                90
_cell_volume                     960.7(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/m 1 '
_symmetry_space_group_name_Hall  '-C 2y'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z
x,-y,z
-x+1/2,y+1/2,-z
x+1/2,-y+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
C 0.0000 0.0000 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0030 0.0030 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'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0060 0.0040 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'
B 0.0000 0.0000 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

# Given Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.24 Fooo = 644.00 Mu = 23.25 M = 161.77
# Found Formula = C20 H18 B2 Cu2 F8 N4 O2
# Dc = 2.24 FOOO = 644.00 Mu = 23.25 M = 161.77

_chemical_formula_sum            'C20 H18 B2 Cu2 F8 N4 O2'
_chemical_formula_moiety         '[Cu2(OH)2(bipy)2][BF4]2'
_chemical_formula_weight         647.09

_cell_measurement_reflns_used    1746
_cell_measurement_theta_min      3
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.15

_exptl_crystal_density_diffrn    2.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    2.325

# Sheldrick geometric approximatio 0.74 0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.79
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         4700000
_diffrn_reflns_number            1875
_reflns_number_total             571
_diffrn_reflns_av_R_equivalents  0.056
# Number of reflections with Friedels Law is 571
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 975

_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         17.290
_diffrn_measured_fraction_theta_max 0.559

_diffrn_reflns_theta_full        14.869
_diffrn_measured_fraction_theta_full 0.601

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -14
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.44
_refine_diff_density_max         0.39

# 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         550
_refine_ls_number_restraints     2
_refine_ls_number_parameters     94
_oxford_refine_ls_R_factor_ref   0.0454
_refine_ls_wR_factor_ref         0.0846
_refine_ls_goodness_of_fit_ref   1.2264
_refine_ls_shift/su_max          0.000067

# The values computed from all data
_oxford_reflns_number_all        550
_refine_ls_R_factor_all          0.0454
_refine_ls_wR_factor_all         0.0846

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                481
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_gt          0.0809

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
46.0 56.7 23.8
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.0000 0.09717(6) 0.5000 0.0200 1.0000 Uani S T . . . . .
N1 N 0.0574(4) 0.1989(3) 0.7365(7) 0.0179 1.0000 Uani . . . . . . .
C1 C 0.0350(4) 0.2835(3) 0.6342(8) 0.0148 1.0000 Uani . . . . . . .
C2 C 0.1365(5) 0.3544(4) 1.0219(8) 0.0250 1.0000 Uani . . . . . . .
C3 C 0.0753(5) 0.3629(4) 0.7723(8) 0.0203 1.0000 Uani . . . . . . .
C4 C 0.1151(5) 0.1909(4) 0.9786(9) 0.0224 1.0000 Uani . . . . . . .
C5 C 0.1562(5) 0.2682(4) 1.1294(8) 0.0224 1.0000 Uani . . . . . . .
O10 O -0.0444(5) 0.000000(7) 0.2646(8) 0.0265 1.0000 Uani S T . . . . .
B6 B 0.2520(7) 0.0000 0.4248(13) 0.0188 1.0000 Uani S T . . . . .
F1 F 0.1978(3) 0.0791(2) 0.4676(5) 0.0267 1.0000 Uani . . . . . . .
F3 F 0.2426(4) 0.0000 0.1830(6) 0.0244 1.0000 Uani S T . . . . .
F4 F 0.3708(4) 0.0000 0.5852(7) 0.0255 1.0000 Uani S T . . . . .
H21 H 0.1646 0.4065 1.1189 0.0302 1.0000 Uiso R . . . . . .
H31 H 0.0617 0.4206 0.6975 0.0244 1.0000 Uiso R . . . . . .
H41 H 0.1283 0.1318 1.0459 0.0267 1.0000 Uiso R . . . . . .
H51 H 0.1954 0.2618 1.2976 0.0253 1.0000 Uiso R . . . . . .
H101 H -0.1027 0.0000 0.1344 0.0363 1.0000 Uiso RS . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0246(6) 0.0118(6) 0.0183(5) 0.0000 0.0024(4) 0.0000
N1 0.021(3) 0.016(3) 0.0183(18) 0.0004(15) 0.0091(18) 0.0010(14)
C1 0.011(3) 0.019(3) 0.014(2) 0.0004(17) 0.004(2) -0.0005(15)
C2 0.030(4) 0.027(4) 0.018(2) -0.0057(19) 0.009(2) -0.0017(19)
C3 0.022(4) 0.019(3) 0.020(2) -0.0003(18) 0.008(2) 0.0047(17)
C4 0.021(3) 0.028(3) 0.018(2) 0.0071(19) 0.007(2) 0.0052(18)
C5 0.018(3) 0.035(4) 0.0087(18) 0.0001(18) 0.000(2) 0.0023(19)
O10 0.032(4) 0.019(3) 0.018(2) 0.0000 -0.002(2) 0.0000
B6 0.010(5) 0.026(6) 0.015(3) 0.0000 0.000(3) 0.0000
F1 0.034(2) 0.019(2) 0.0240(14) -0.0032(11) 0.0076(14) 0.0039(11)
F3 0.033(3) 0.023(3) 0.0114(16) 0.0000 0.0016(17) 0.0000
F4 0.022(3) 0.028(3) 0.0199(18) 0.0000 0.0017(19) 0.0000

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.989(11)
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
Cu1 . F1 5_556 2.503(3) yes
Cu1 . N1 5_556 1.964(4) yes
Cu1 . O10 2_556 1.904(3) yes
Cu1 . N1 . 1.964(4) yes
Cu1 . O10 . 1.904(3) yes
Cu1 . F1 . 2.503(3) yes
N1 . C1 . 1.348(6) yes
N1 . C4 . 1.329(6) yes
C1 . C1 5_556 1.477(9) yes
C1 . C3 . 1.386(7) yes
C2 . C3 . 1.372(7) yes
C2 . C5 . 1.380(8) yes
C2 . H21 . 0.930 no
C3 . H31 . 0.932 no
C4 . C5 . 1.399(8) yes
C4 . H41 . 0.931 no
C5 . H51 . 0.923 no
O10 . H101 . 0.818 no
B6 . F1 6_555 1.396(5) yes
B6 . F1 . 1.396(5) yes
B6 . F3 . 1.386(8) yes
B6 . F4 . 1.386(9) 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
F1 5_556 Cu1 . N1 5_556 92.65(14) yes
F1 5_556 Cu1 . O10 2_556 82.83(18) yes
N1 5_556 Cu1 . O10 2_556 175.3(2) yes
F1 5_556 Cu1 . N1 . 96.40(14) yes
N1 5_556 Cu1 . N1 . 82.4(2) yes
O10 2_556 Cu1 . N1 . 96.76(15) yes
F1 5_556 Cu1 . O10 . 88.25(18) yes
N1 5_556 Cu1 . O10 . 96.76(15) yes
O10 2_556 Cu1 . O10 . 84.4(2) yes
N1 . Cu1 . O10 . 175.3(2) yes
F1 5_556 Cu1 . F1 . 167.97(14) yes
N1 5_556 Cu1 . F1 . 96.40(14) yes
O10 2_556 Cu1 . F1 . 88.25(18) yes
N1 . Cu1 . F1 . 92.65(14) yes
O10 . Cu1 . F1 . 82.83(18) yes
Cu1 . N1 . C1 . 114.4(3) yes
Cu1 . N1 . C4 . 126.2(4) yes
C1 . N1 . C4 . 119.5(4) yes
C1 5_556 C1 . N1 . 114.3(3) yes
C1 5_556 C1 . C3 . 123.7(3) yes
N1 . C1 . C3 . 122.0(4) yes
C3 . C2 . C5 . 119.9(5) yes
C3 . C2 . H21 . 120.2 no
C5 . C2 . H21 . 119.9 no
C1 . C3 . C2 . 118.4(5) yes
C1 . C3 . H31 . 120.8 no
C2 . C3 . H31 . 120.7 no
N1 . C4 . C5 . 121.4(5) yes
N1 . C4 . H41 . 118.1 no
C5 . C4 . H41 . 120.5 no
C4 . C5 . C2 . 118.7(4) yes
C4 . C5 . H51 . 120.7 no
C2 . C5 . H51 . 120.6 no
Cu1 . O10 . Cu1 2_556 95.6(2) yes
Cu1 . O10 . H101 . 125.5 no
Cu1 2_556 O10 . H101 . 125.5 no
F1 6_555 B6 . F1 . 110.7(6) yes
F1 6_555 B6 . F3 . 109.3(4) yes
F1 . B6 . F3 . 109.3(4) yes
F1 6_555 B6 . F4 . 108.6(4) yes
F1 . B6 . F4 . 108.6(4) yes
F3 . B6 . F4 . 110.4(6) yes
Cu1 . F1 . B6 . 129.6(3) yes

# Attachment 'cutb00.cif'

data_cutb00
_database_code_depnum_ccdc_archive 'CCDC 746647'

# ambient pressure dataset

_audit_creation_date             09-08-09
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cutb00 in C2/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms on O and N atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry and then let to ride on
their parent atoms.

checkcif output:

911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 203
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 21
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 771
910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) ..... 28

INTENSITY STATISTICS FOR DATASET # 1 cutb00.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma)

Inf - 2.05 448 448 100.0 6.75 513.7 37.86 0.0229 0.0193
2.05 - 1.60 463 463 100.0 7.08 239.3 34.32 0.0264 0.0204
1.60 - 1.40 438 438 100.0 6.65 187.3 31.81 0.0399 0.0225
1.40 - 1.25 528 528 100.0 6.09 145.7 28.12 0.0443 0.0254
1.25 - 1.15 508 508 100.0 5.58 93.9 22.48 0.0524 0.0308
1.15 - 1.05 736 736 100.0 5.20 65.9 18.34 0.0658 0.0384
1.05 - 1.00 473 473 100.0 4.88 60.6 16.14 0.0716 0.0438
1.00 - 0.95 597 597 100.0 4.58 42.2 12.94 0.0872 0.0581
0.95 - 0.90 727 727 100.0 4.35 40.3 11.65 0.0969 0.0672
0.90 - 0.85 899 899 100.0 4.07 29.9 8.86 0.1181 0.0944
0.85 - 0.80 1143 1143 100.0 3.73 22.6 6.28 0.1723 0.1425
0.80 - 0.75 1270 1463 86.8 2.45 16.2 3.58 0.2530 0.2989
0.75 - 0.73 123 528 23.3 0.29 15.3 1.70 0.3279 0.6295
#-----------------------------------------------------------------------------
0.85 - 0.73 2536 3134 80.9 2.56 19.0 4.71 0.2031 0.2280
Inf - 0.73 8353 8951 93.3 4.35 90.3 15.60 0.0459 0.0425

601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 39.00 A**3

No reasonable or relevant peaks were detected in the difference map.

042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
061_ALERT_4_C Tmax/Tmin Range Test RR' too Large ............. 0.83
244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 44.32 Deg.
N13 -C14 -CU1 1.555 1.555 1.555
779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 44.33 Deg.
N16 -C15 -CU1 1.555 1.555 1.555
793_ALERT_4_G The Model has Chirality at N8 (Verify) .... S
793_ALERT_4_G The Model has Chirality at N13 (Verify) .... S
793_ALERT_4_G The Model has Chirality at N16 (Verify) .... S
793_ALERT_4_G The Model has Chirality at N50 (Verify) .... S
795_ALERT_4_G C-Atom in CIF Coordinate List out of Sequence .. C2
796_ALERT_4_G O-Atom in CIF Coordinate List out of Sequence .. O4
797_ALERT_4_G N-Atom in CIF Coordinate List out of Sequence .. N8
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
230_ALERT_2_C Hirshfeld Test Diff for C17 -- C24 .. 6.29 su
232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 -- O2 .. 5.34 su
232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 -- N13 .. 6.91 su
230_ALERT_2_B Hirshfeld Test Diff for C6 -- C7 .. 9.82 su
230_ALERT_2_B Hirshfeld Test Diff for C17 -- C18 .. 11.30 su

No action taken here.
;
#end of refcif
_cell_length_a                   29.8826(6)
_cell_length_b                   11.7561(2)
_cell_length_c                   18.9518(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.6960(10)
_cell_angle_gamma                90
_cell_volume                     6468.5(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1 '
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            8

# Given Formula = C20 H50 Cl2 Cu2 N4 O10
# Dc = 1.45 Fooo = 2960.00 Mu = 15.31 M = 704.64
# Found Formula = C20 H50 Cl2 Cu2 N4 O10
# Dc = 1.45 FOOO = 2960.00 Mu = 15.31 M = 704.64

_chemical_formula_sum            'C20 H50 Cl2 Cu2 N4 O10'
_chemical_formula_moiety         '[Cu2(OH)2(tben)2][ClO4]2'
_chemical_formula_weight         704.64

_cell_measurement_reflns_used    7979
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_max          0.25

_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             2960
_exptl_absorpt_coefficient_mu    1.531

# Sheldrick geometric approximatio 0.73 0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.86
_diffrn_measurement_device       'Bruker SMART'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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            38959
_reflns_number_total             7982
_diffrn_reflns_av_R_equivalents  0.046
# Number of reflections with Friedels Law is 7982
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 8564

_diffrn_reflns_theta_min         1.403
_diffrn_reflns_theta_max         28.956
_diffrn_measured_fraction_theta_max 0.934

_diffrn_reflns_theta_full        27.219
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -40
_reflns_limit_h_max              39
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.72
_refine_diff_density_max         0.94

# 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         7522
_refine_ls_number_restraints     0
_refine_ls_number_parameters     343
_oxford_refine_ls_R_factor_ref   0.0610
_refine_ls_wR_factor_ref         0.0094
_refine_ls_goodness_of_fit_ref   0.9943
_refine_ls_shift/su_max          0.000792

# The values computed from all data
_oxford_reflns_number_all        7522
_refine_ls_R_factor_all          0.0610
_refine_ls_wR_factor_all         0.0094

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                5207
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_gt          0.0090

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.172E-01 -3.59 -2.13
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1993).
SMART: Area-Detector Software Package; Madison, WI.

Siemens Industrial Automation, Inc (1995).
SAINT: Area-Detector Integration Software.; Madison, WI.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.107020(7) 0.21857(2) 0.109874(11) 0.0264 1.0000 Uani . . . . . . .
Cu2 Cu 0.158018(7) -0.00124(2) 0.127261(11) 0.0261 1.0000 Uani . . . . . . .
Cl1 Cl 0.218319(14) 0.46425(4) 0.17527(2) 0.0334 1.0000 Uani . . . . . . .
Cl2 Cl -0.063696(19) 0.23042(6) 0.02075(3) 0.0567 1.0000 Uani . . . . . . .
O1 O 0.16693(4) 0.15729(11) 0.14745(6) 0.0306 1.0000 Uani . . . . . . .
O2 O 0.09778(4) 0.05967(10) 0.08689(6) 0.0318 1.0000 Uani . . . . . . .
O5 O 0.17612(4) 0.48421(15) 0.12249(7) 0.0626 1.0000 Uani . . . . . . .
O8 O -0.03424(6) 0.2956(2) 0.07349(10) 0.0998 1.0000 Uani . . . . . . .
O4 O 0.25196(5) 0.54433(11) 0.16899(10) 0.0696 1.0000 Uani . . . . . . .
O6 O 0.23418(6) 0.35262(14) 0.17068(12) 0.0909 1.0000 Uani . . . . . . .
O10 O -0.07793(9) 0.2971(2) -0.04388(11) 0.1210 1.0000 Uani . . . . . . .
O9 O -0.03862(6) 0.13737(18) -0.00040(10) 0.0885 1.0000 Uani . . . . . . .
O3 O 0.20785(6) 0.4811(2) 0.24399(8) 0.0867 1.0000 Uani . . . . . . .
O7 O -0.10082(7) 0.18840(19) 0.04286(13) 0.1181 1.0000 Uani . . . . . . .
N50 N 0.21915(5) -0.05966(11) 0.11454(7) 0.0275 1.0000 Uani . . . . . . .
N8 N 0.14364(5) -0.15772(14) 0.15651(8) 0.0313 1.0000 Uani . . . . . . .
C6 C 0.21244(7) -0.18542(14) 0.11032(11) 0.0389 1.0000 Uani . . . . . . .
C7 C 0.18783(7) -0.22018(19) 0.16789(10) 0.0437 1.0000 Uani . . . . . . .
C2 C 0.11968(6) -0.16914(16) 0.21937(9) 0.0326 1.0000 Uani . . . . . . .
C25 C 0.07073(6) -0.1275(2) 0.19272(10) 0.0481 1.0000 Uani . . . . . . .
C4 C 0.11960(8) -0.29270(17) 0.24140(11) 0.0516 1.0000 Uani . . . . . . .
C5 C 0.14557(7) -0.09743(19) 0.28202(10) 0.0471 1.0000 Uani . . . . . . .
C9 C 0.23609(5) -0.00980(19) 0.05230(8) 0.0343 1.0000 Uani . . . . . . .
C10 C 0.25343(8) 0.11024(17) 0.07344(13) 0.0561 1.0000 Uani . . . . . . .
C11 C 0.27624(7) -0.07985(18) 0.03758(10) 0.0459 1.0000 Uani . . . . . . .
C12 C 0.19709(7) -0.0056(3) -0.01521(9) 0.0631 1.0000 Uani . . . . . . .
N13 N 0.06261(5) 0.30295(12) 0.03203(8) 0.0294 1.0000 Uani . . . . . . .
N16 N 0.10270(5) 0.34558(12) 0.17904(7) 0.0293 1.0000 Uani . . . . . . .
C14 C 0.06337(7) 0.42105(17) 0.06006(10) 0.0421 1.0000 Uani . . . . . . .
C15 C 0.06328(6) 0.41581(17) 0.13979(10) 0.0392 1.0000 Uani . . . . . . .
C17 C 0.09851(6) 0.30669(16) 0.25408(9) 0.0346 1.0000 Uani . . . . . . .
C18 C 0.14532(7) 0.25971(19) 0.29371(9) 0.0513 1.0000 Uani . . . . . . .
C19 C 0.08606(9) 0.40896(18) 0.29645(12) 0.0572 1.0000 Uani . . . . . . .
C24 C 0.06230(7) 0.2144(2) 0.24489(12) 0.0548 1.0000 Uani . . . . . . .
C20 C 0.07029(6) 0.29588(19) -0.04401(9) 0.0357 1.0000 Uani . . . . . . .
C21 C 0.03791(7) 0.3750(2) -0.09529(11) 0.0469 1.0000 Uani . . . . . . .
C22 C 0.11972(6) 0.32616(18) -0.04112(10) 0.0445 1.0000 Uani . . . . . . .
C23 C 0.06079(7) 0.17368(16) -0.07024(10) 0.0382 1.0000 Uani . . . . . . .
H161 H 0.1292 0.3875 0.1842 0.0483 1.0000 Uiso R . . . . . .
H501 H 0.2417 -0.0403 0.1580 0.0455 1.0000 Uiso R . . . . . .
H21 H 0.0767 0.0129 0.0725 0.0494 1.0000 Uiso R . . . . . .
H81 H 0.1249 -0.1920 0.1167 0.0530 1.0000 Uiso R . . . . . .
H11 H 0.1891 0.2014 0.1706 0.0477 1.0000 Uiso R . . . . . .
H131 H 0.0332 0.2716 0.0260 0.0493 1.0000 Uiso R . . . . . .
H61 H 0.2415 -0.2225 0.1187 0.0523 1.0000 Uiso R . . . . . .
H62 H 0.1945 -0.2056 0.0636 0.0523 1.0000 Uiso R . . . . . .
H251 H 0.0552 -0.1335 0.2309 0.0612 1.0000 Uiso R . . . . . .
H252 H 0.0554 -0.1728 0.1528 0.0612 1.0000 Uiso R . . . . . .
H253 H 0.0708 -0.0504 0.1778 0.0612 1.0000 Uiso R . . . . . .
H41 H 0.1049 -0.3000 0.2805 0.0650 1.0000 Uiso R . . . . . .
H42 H 0.1503 -0.3200 0.2562 0.0650 1.0000 Uiso R . . . . . .
H43 H 0.1033 -0.3359 0.2011 0.0650 1.0000 Uiso R . . . . . .
H51 H 0.1311 -0.1038 0.3214 0.0585 1.0000 Uiso R . . . . . .
H52 H 0.1764 -0.1238 0.2969 0.0585 1.0000 Uiso R . . . . . .
H53 H 0.1455 -0.0201 0.2675 0.0585 1.0000 Uiso R . . . . . .
H101 H 0.2643 0.1436 0.0350 0.0700 1.0000 Uiso R . . . . . .
H102 H 0.2778 0.1074 0.1160 0.0700 1.0000 Uiso R . . . . . .
H103 H 0.2289 0.1546 0.0826 0.0700 1.0000 Uiso R . . . . . .
H111 H 0.2864 -0.0471 -0.0017 0.0567 1.0000 Uiso R . . . . . .
H112 H 0.3009 -0.0801 0.0798 0.0567 1.0000 Uiso R . . . . . .
H113 H 0.2663 -0.1557 0.0256 0.0567 1.0000 Uiso R . . . . . .
H121 H 0.2078 0.0259 -0.0543 0.0751 1.0000 Uiso R . . . . . .
H122 H 0.1861 -0.0806 -0.0274 0.0751 1.0000 Uiso R . . . . . .
H123 H 0.1728 0.0400 -0.0062 0.0751 1.0000 Uiso R . . . . . .
H141 H 0.0905 0.4585 0.0546 0.0470 1.0000 Uiso R . . . . . .
H142 H 0.0371 0.4615 0.0340 0.0470 1.0000 Uiso R . . . . . .
H181 H 0.1438 0.2353 0.3409 0.0616 1.0000 Uiso R . . . . . .
H182 H 0.1680 0.3174 0.2977 0.0616 1.0000 Uiso R . . . . . .
H183 H 0.1532 0.1971 0.2673 0.0616 1.0000 Uiso R . . . . . .
H191 H 0.0836 0.3844 0.3431 0.0765 1.0000 Uiso R . . . . . .
H192 H 0.1094 0.4652 0.3016 0.0765 1.0000 Uiso R . . . . . .
H193 H 0.0575 0.4402 0.2709 0.0765 1.0000 Uiso R . . . . . .
H241 H 0.0594 0.1901 0.2914 0.0717 1.0000 Uiso R . . . . . .
H242 H 0.0336 0.2434 0.2182 0.0717 1.0000 Uiso R . . . . . .
H243 H 0.0711 0.1518 0.2195 0.0717 1.0000 Uiso R . . . . . .
H211 H 0.0431 0.3697 -0.1428 0.0555 1.0000 Uiso R . . . . . .
H212 H 0.0432 0.4510 -0.0782 0.0555 1.0000 Uiso R . . . . . .
H213 H 0.0070 0.3541 -0.0966 0.0555 1.0000 Uiso R . . . . . .
H221 H 0.1250 0.3217 -0.0885 0.0575 1.0000 Uiso R . . . . . .
H222 H 0.1256 0.4014 -0.0231 0.0575 1.0000 Uiso R . . . . . .
H223 H 0.1396 0.2747 -0.0099 0.0575 1.0000 Uiso R . . . . . .
H231 H 0.0655 0.1668 -0.1179 0.0470 1.0000 Uiso R . . . . . .
H232 H 0.0810 0.1235 -0.0385 0.0470 1.0000 Uiso R . . . . . .
H233 H 0.0298 0.1547 -0.0707 0.0470 1.0000 Uiso R . . . . . .
H71 H 0.2070 -0.2021 0.2161 0.0521 1.0000 Uiso R . . . . . .
H72 H 0.1818 -0.3022 0.1645 0.0521 1.0000 Uiso R . . . . . .
H151 H 0.0661 0.4927 0.1604 0.0477 1.0000 Uiso R . . . . . .
H152 H 0.0343 0.3816 0.1450 0.0477 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.02471(11) 0.02798(13) 0.02656(12) -0.00147(12) 0.00629(10) 0.00306(12)
Cu2 0.02556(11) 0.02396(11) 0.02991(11) 0.00099(13) 0.00892(9) -0.00026(13)
Cl1 0.0258(2) 0.0352(3) 0.0390(3) 0.0035(2) 0.0073(2) -0.0010(2)
Cl2 0.0438(3) 0.0894(5) 0.0389(3) -0.0225(4) 0.0139(2) -0.0246(4)
O1 0.0233(7) 0.0263(7) 0.0405(8) -0.0050(6) 0.0043(6) 0.0002(6)
O2 0.0269(7) 0.0322(7) 0.0354(7) -0.0014(6) 0.0055(5) -0.0003(6)
O5 0.0445(7) 0.0717(12) 0.0612(9) 0.0141(10) -0.0081(7) 0.0005(9)
O8 0.0578(11) 0.151(2) 0.0856(12) -0.0639(13) 0.0064(9) -0.0424(13)
O4 0.0368(8) 0.0425(9) 0.1328(14) 0.0113(9) 0.0270(9) -0.0016(8)
O6 0.0415(11) 0.0414(11) 0.1788(19) -0.0268(12) 0.0042(11) 0.0004(8)
O10 0.191(3) 0.0847(15) 0.0701(14) -0.0051(13) -0.0035(15) -0.0241(16)
O9 0.0813(13) 0.1019(15) 0.0854(13) -0.0104(12) 0.0261(11) 0.0048(12)
O3 0.0832(11) 0.1324(17) 0.0492(9) 0.0183(12) 0.0251(7) 0.0153(13)
O7 0.0755(14) 0.161(2) 0.1327(16) -0.0327(15) 0.0534(12) -0.0556(14)
N50 0.0318(8) 0.0203(8) 0.0315(8) 0.0015(6) 0.0098(6) 0.0041(6)
N8 0.0363(9) 0.0286(9) 0.0303(8) 0.0040(7) 0.0108(7) -0.0028(7)
C6 0.0461(12) 0.0230(11) 0.0560(12) -0.0004(9) 0.0287(10) 0.0029(9)
C7 0.0465(11) 0.0265(10) 0.0597(13) 0.0117(12) 0.0158(10) 0.0113(12)
C2 0.0283(10) 0.0413(12) 0.0267(10) 0.0028(9) 0.0036(8) -0.0096(9)
C25 0.0346(12) 0.0704(16) 0.0421(12) 0.0083(11) 0.0143(10) -0.0061(12)
C4 0.0634(15) 0.0489(15) 0.0470(12) 0.0127(12) 0.0223(11) -0.0055(13)
C5 0.0435(12) 0.0627(16) 0.0347(12) -0.0046(11) 0.0086(10) -0.0176(11)
C9 0.0304(9) 0.0420(12) 0.0330(9) 0.0039(11) 0.0123(7) 0.0048(11)
C10 0.0621(14) 0.0391(13) 0.0798(15) 0.0059(12) 0.0422(13) -0.0072(11)
C11 0.0465(13) 0.0463(13) 0.0519(13) 0.0036(11) 0.0255(10) 0.0117(11)
C12 0.0467(11) 0.1070(19) 0.0353(10) 0.0288(16) 0.0095(9) 0.0118(16)
N13 0.0278(8) 0.0292(10) 0.0326(8) -0.0007(7) 0.0102(7) 0.0009(7)
N16 0.0262(8) 0.0338(9) 0.0294(8) -0.0029(7) 0.0096(7) 0.0004(7)
C14 0.0383(11) 0.0347(12) 0.0492(13) 0.0000(11) 0.0019(10) 0.0082(10)
C15 0.0377(11) 0.0329(12) 0.0465(13) -0.0090(10) 0.0090(9) 0.0079(10)
C17 0.0390(11) 0.0371(13) 0.0309(10) -0.0115(9) 0.0149(9) -0.0061(9)
C18 0.0676(15) 0.0594(16) 0.0265(9) -0.0037(11) 0.0105(9) -0.0076(12)
C19 0.0894(17) 0.0471(14) 0.0442(11) -0.0092(12) 0.0340(12) 0.0032(14)
C24 0.0529(13) 0.0574(14) 0.0630(13) -0.0033(14) 0.0312(11) -0.0109(13)
C20 0.0322(10) 0.0474(14) 0.0284(10) 0.0003(10) 0.0089(8) 0.0063(10)
C21 0.0438(13) 0.0553(13) 0.0405(12) 0.0078(11) 0.0077(10) 0.0075(11)
C22 0.0340(11) 0.0641(15) 0.0372(11) 0.0016(11) 0.0120(9) -0.0050(10)
C23 0.0416(12) 0.0428(12) 0.0301(11) 0.0023(9) 0.0080(9) 0.0094(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.130736(14)
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
Cu1 . Cu2 . 2.9784(3) yes
Cu1 . O1 . 1.9045(12) yes
Cu1 . O2 . 1.9231(12) yes
Cu1 . N13 . 1.9986(15) yes
Cu1 . N16 . 2.0112(14) yes
Cu1 . C14 . 2.771(2) yes
Cu1 . C15 . 2.7852(18) yes
Cu2 . O1 . 1.9086(13) yes
Cu2 . O2 . 1.9199(11) yes
Cu2 . N50 . 2.0187(14) yes
Cu2 . N8 . 1.9971(16) yes
Cl1 . O5 . 1.4312(13) yes
Cl1 . O4 . 1.4028(14) yes
Cl1 . O6 . 1.4050(17) yes
Cl1 . O3 . 1.4233(15) yes
Cl2 . O8 . 1.3942(17) yes
Cl2 . O10 . 1.431(2) yes
Cl2 . O9 . 1.4355(19) yes
Cl2 . O7 . 1.3675(18) yes
O1 . H11 . 0.873 no
O2 . H21 . 0.832 no
N50 . C6 . 1.492(2) yes
N50 . C9 . 1.508(2) yes
N50 . H501 . 0.959 no
N8 . C7 . 1.482(2) yes
N8 . C2 . 1.534(2) yes
N8 . H81 . 0.920 no
C6 . C7 . 1.509(3) yes
C6 . H61 . 0.950 no
C6 . H62 . 0.950 no
C7 . H71 . 0.980 no
C7 . H72 . 0.980 no
C2 . C25 . 1.512(3) yes
C2 . C4 . 1.512(2) yes
C2 . C5 . 1.511(2) yes
C25 . H251 . 0.950 no
C25 . H252 . 0.950 no
C25 . H253 . 0.950 no
C4 . H41 . 0.950 no
C4 . H42 . 0.950 no
C4 . H43 . 0.950 no
C5 . H51 . 0.950 no
C5 . H52 . 0.950 no
C5 . H53 . 0.950 no
C9 . C10 . 1.524(3) yes
C9 . C11 . 1.534(2) yes
C9 . C12 . 1.514(2) yes
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C10 . H103 . 0.950 no
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C11 . H113 . 0.950 no
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
N13 . C14 . 1.485(2) yes
N13 . C20 . 1.514(2) yes
N13 . H131 . 0.935 no
N16 . C15 . 1.486(2) yes
N16 . C17 . 1.527(2) yes
N16 . H161 . 0.917 no
C14 . C15 . 1.513(2) yes
C14 . H141 . 0.950 no
C14 . H142 . 0.950 no
C15 . H151 . 0.980 no
C15 . H152 . 0.980 no
C17 . C18 . 1.526(3) yes
C17 . C19 . 1.540(3) yes
C17 . C24 . 1.513(3) yes
C18 . H181 . 0.950 no
C18 . H182 . 0.950 no
C18 . H183 . 0.950 no
C19 . H191 . 0.950 no
C19 . H192 . 0.950 no
C19 . H193 . 0.950 no
C24 . H241 . 0.950 no
C24 . H242 . 0.950 no
C24 . H243 . 0.950 no
C20 . C21 . 1.517(3) yes
C20 . C22 . 1.508(3) yes
C20 . C23 . 1.525(3) yes
C21 . H211 . 0.950 no
C21 . H212 . 0.950 no
C21 . H213 . 0.950 no
C22 . H221 . 0.950 no
C22 . H222 . 0.950 no
C22 . H223 . 0.950 no
C23 . H231 . 0.950 no
C23 . H232 . 0.950 no
C23 . H233 . 0.950 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
Cu2 . Cu1 . O1 . 38.69(4) yes
Cu2 . Cu1 . O2 . 39.15(3) yes
O1 . Cu1 . O2 . 77.83(5) yes
Cu2 . Cu1 . N13 . 138.18(4) yes
O1 . Cu1 . N13 . 149.86(6) yes
O2 . Cu1 . N13 . 106.28(5) yes
Cu2 . Cu1 . N16 . 133.01(4) yes
O1 . Cu1 . N16 . 103.70(6) yes
O2 . Cu1 . N16 . 147.23(5) yes
N13 . Cu1 . N16 . 88.78(6) yes
Cu2 . Cu1 . C14 . 166.03(4) yes
O1 . Cu1 . C14 . 141.02(6) yes
O2 . Cu1 . C14 . 136.61(6) yes
N13 . Cu1 . C14 . 31.27(6) yes
N16 . Cu1 . C14 . 59.10(5) yes
Cu2 . Cu1 . C15 . 162.23(4) yes
O1 . Cu1 . C15 . 133.13(6) yes
O2 . Cu1 . C15 . 143.67(5) yes
N13 . Cu1 . C15 . 58.36(6) yes
N16 . Cu1 . C15 . 31.08(5) yes
C14 . Cu1 . C15 . 31.60(5) yes
Cu1 . Cu2 . O1 . 38.59(4) yes
Cu1 . Cu2 . O2 . 39.23(4) yes
O1 . Cu2 . O2 . 77.81(5) yes
Cu1 . Cu2 . N50 . 137.37(4) yes
O1 . Cu2 . N50 . 105.60(6) yes
O2 . Cu2 . N50 . 150.32(5) yes
Cu1 . Cu2 . N8 . 133.77(4) yes
O1 . Cu2 . N8 . 150.78(5) yes
O2 . Cu2 . N8 . 102.19(6) yes
N50 . Cu2 . N8 . 88.86(6) yes
O5 . Cl1 . O4 . 111.18(10) yes
O5 . Cl1 . O6 . 111.36(10) yes
O4 . Cl1 . O6 . 111.25(10) yes
O5 . Cl1 . O3 . 105.58(10) yes
O4 . Cl1 . O3 . 107.56(12) yes
O6 . Cl1 . O3 . 109.68(13) yes
O8 . Cl2 . O10 . 108.79(13) yes
O8 . Cl2 . O9 . 109.64(12) yes
O10 . Cl2 . O9 . 104.31(13) yes
O8 . Cl2 . O7 . 113.51(13) yes
O10 . Cl2 . O7 . 111.21(16) yes
O9 . Cl2 . O7 . 108.97(14) yes
Cu2 . O1 . Cu1 . 102.72(6) yes
Cu2 . O1 . H11 . 137.2 no
Cu1 . O1 . H11 . 119.9 no
Cu1 . O2 . Cu2 . 101.61(5) yes
Cu1 . O2 . H21 . 140.6 no
Cu2 . O2 . H21 . 116.8 no
Cu2 . N50 . C6 . 103.28(11) yes
Cu2 . N50 . C9 . 116.23(10) yes
C6 . N50 . C9 . 114.16(14) yes
Cu2 . N50 . H501 . 106.7 no
C6 . N50 . H501 . 109.8 no
C9 . N50 . H501 . 106.4 no
Cu2 . N8 . C7 . 104.71(12) yes
Cu2 . N8 . C2 . 117.83(11) yes
C7 . N8 . C2 . 114.04(14) yes
Cu2 . N8 . H81 . 107.8 no
C7 . N8 . H81 . 104.6 no
C2 . N8 . H81 . 107.1 no
N50 . C6 . C7 . 108.18(15) yes
N50 . C6 . H61 . 109.9 no
C7 . C6 . H61 . 109.7 no
N50 . C6 . H62 . 109.7 no
C7 . C6 . H62 . 110.0 no
H61 . C6 . H62 . 109.5 no
C6 . C7 . N8 . 109.31(16) yes
C6 . C7 . H71 . 109.7 no
N8 . C7 . H71 . 109.5 no
C6 . C7 . H72 . 109.4 no
N8 . C7 . H72 . 109.5 no
H71 . C7 . H72 . 109.5 no
N8 . C2 . C25 . 107.75(14) yes
N8 . C2 . C4 . 109.28(16) yes
C25 . C2 . C4 . 109.80(17) yes
N8 . C2 . C5 . 108.37(14) yes
C25 . C2 . C5 . 110.90(17) yes
C4 . C2 . C5 . 110.67(16) yes
C2 . C25 . H251 . 109.3 no
C2 . C25 . H252 . 109.4 no
H251 . C25 . H252 . 109.5 no
C2 . C25 . H253 . 109.7 no
H251 . C25 . H253 . 109.5 no
H252 . C25 . H253 . 109.5 no
C2 . C4 . H41 . 109.4 no
C2 . C4 . H42 . 109.9 no
H41 . C4 . H42 . 109.5 no
C2 . C4 . H43 . 109.0 no
H41 . C4 . H43 . 109.5 no
H42 . C4 . H43 . 109.5 no
C2 . C5 . H51 . 109.2 no
C2 . C5 . H52 . 109.3 no
H51 . C5 . H52 . 109.5 no
C2 . C5 . H53 . 109.9 no
H51 . C5 . H53 . 109.5 no
H52 . C5 . H53 . 109.5 no
N50 . C9 . C10 . 108.10(14) yes
N50 . C9 . C11 . 110.81(15) yes
C10 . C9 . C11 . 108.23(16) yes
N50 . C9 . C12 . 109.88(15) yes
C10 . C9 . C12 . 109.75(19) yes
C11 . C9 . C12 . 110.02(15) yes
C9 . C10 . H101 . 109.7 no
C9 . C10 . H102 . 109.6 no
H101 . C10 . H102 . 109.5 no
C9 . C10 . H103 . 109.1 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no
C9 . C11 . H111 . 109.6 no
C9 . C11 . H112 . 109.4 no
H111 . C11 . H112 . 109.5 no
C9 . C11 . H113 . 109.5 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
C9 . C12 . H121 . 109.7 no
C9 . C12 . H122 . 109.1 no
H121 . C12 . H122 . 109.5 no
C9 . C12 . H123 . 109.6 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no
Cu1 . N13 . C14 . 104.40(11) yes
Cu1 . N13 . C20 . 116.84(10) yes
C14 . N13 . C20 . 113.51(14) yes
Cu1 . N13 . H131 . 109.6 no
C14 . N13 . H131 . 110.2 no
C20 . N13 . H131 . 102.3 no
Cu1 . N16 . C15 . 104.58(11) yes
Cu1 . N16 . C17 . 114.63(11) yes
C15 . N16 . C17 . 113.74(13) yes
Cu1 . N16 . H161 . 106.3 no
C15 . N16 . H161 . 108.4 no
C17 . N16 . H161 . 108.7 no
N13 . C14 . Cu1 . 44.32(8) yes
N13 . C14 . C15 . 108.41(16) yes
Cu1 . C14 . C15 . 74.73(11) yes
N13 . C14 . H141 . 109.6 no
Cu1 . C14 . H141 . 95.1 no
C15 . C14 . H141 . 109.3 no
N13 . C14 . H142 . 110.0 no
Cu1 . C14 . H142 . 150.7 no
C15 . C14 . H142 . 110.1 no
H141 . C14 . H142 . 109.5 no
C14 . C15 . N16 . 109.51(14) yes
C14 . C15 . Cu1 . 73.66(10) yes
N16 . C15 . Cu1 . 44.33(7) yes
C14 . C15 . H151 . 109.8 no
N16 . C15 . H151 . 109.3 no
Cu1 . C15 . H151 . 148.0 no
C14 . C15 . H152 . 109.1 no
N16 . C15 . H152 . 109.6 no
Cu1 . C15 . H152 . 98.5 no
H151 . C15 . H152 . 109.5 no
N16 . C17 . C18 . 107.40(13) yes
N16 . C17 . C19 . 109.59(16) yes
C18 . C17 . C19 . 109.42(17) yes
N16 . C17 . C24 . 108.76(14) yes
C18 . C17 . C24 . 110.13(17) yes
C19 . C17 . C24 . 111.44(16) yes
C17 . C18 . H181 . 109.4 no
C17 . C18 . H182 . 109.6 no
H181 . C18 . H182 . 109.5 no
C17 . C18 . H183 . 109.5 no
H181 . C18 . H183 . 109.5 no
H182 . C18 . H183 . 109.5 no
C17 . C19 . H191 . 109.3 no
C17 . C19 . H192 . 109.5 no
H191 . C19 . H192 . 109.5 no
C17 . C19 . H193 . 109.6 no
H191 . C19 . H193 . 109.5 no
H192 . C19 . H193 . 109.5 no
C17 . C24 . H241 . 109.2 no
C17 . C24 . H242 . 109.6 no
H241 . C24 . H242 . 109.5 no
C17 . C24 . H243 . 109.7 no
H241 . C24 . H243 . 109.5 no
H242 . C24 . H243 . 109.5 no
N13 . C20 . C21 . 111.01(14) yes
N13 . C20 . C22 . 108.69(14) yes
C21 . C20 . C22 . 110.45(17) yes
N13 . C20 . C23 . 107.66(15) yes
C21 . C20 . C23 . 109.13(16) yes
C22 . C20 . C23 . 109.85(17) yes
C20 . C21 . H211 . 110.1 no
C20 . C21 . H212 . 109.2 no
H211 . C21 . H212 . 109.5 no
C20 . C21 . H213 . 109.0 no
H211 . C21 . H213 . 109.5 no
H212 . C21 . H213 . 109.5 no
C20 . C22 . H221 . 109.5 no
C20 . C22 . H222 . 109.3 no
H221 . C22 . H222 . 109.5 no
C20 . C22 . H223 . 109.6 no
H221 . C22 . H223 . 109.5 no
H222 . C22 . H223 . 109.5 no
C20 . C23 . H231 . 109.4 no
C20 . C23 . H232 . 109.7 no
H231 . C23 . H232 . 109.5 no
C20 . C23 . H233 . 109.3 no
H231 . C23 . H233 . 109.5 no
H232 . C23 . H233 . 109.5 no

# Attachment 'cutb01.cif'

data_cutb01
_database_code_depnum_ccdc_archive 'CCDC 746648'

#0.21 GPa data set.

_audit_creation_date             09-07-22
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cutb01 in C2/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.47
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 10.90 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.51
088_ALERT_3_A Poor Data / Parameter Ratio .................... 3.71
341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 32
910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) ..... 29
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.526 1878
913_ALERT_3_B Missing # of Very Strong Reflections in FCF .... 344

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

023_ALERT_3_A Resolution (too) Low [sin(theta)/Lambda < 0.6].. 14.53 Deg.

INTENSITY STATISTICS FOR DATASET # 1 cutb01.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) Rsigma

Inf - 2.34 156 305 51.1 3.96 101.6 16.88 0.0481 0.0579
2.34 - 1.84 158 320 49.4 3.08 81.7 14.23 0.0682 0.0604
1.84 - 1.61 155 294 52.7 3.28 44.2 11.02 0.0864 0.0711
1.61 - 1.45 156 328 47.6 2.93 41.0 10.56 0.1068 0.0741
1.45 - 1.34 157 331 47.4 2.90 33.4 10.37 0.1072 0.0773
1.34 - 1.25 168 349 48.1 2.90 22.2 8.12 0.1859 0.1075
1.25 - 1.18 166 370 44.9 2.55 14.6 6.22 0.1923 0.1377
1.18 - 1.12 166 380 43.7 2.49 11.0 4.98 0.2917 0.1872
1.12 - 1.07 176 390 45.1 2.36 8.1 3.76 0.3195 0.2582
1.07 - 1.03 159 371 42.9 2.17 8.4 3.55 0.3107 0.2593
1.03 - 0.99 167 416 40.1 1.98 5.7 2.35 0.4629 0.4476
0.99 - 0.95 221 520 42.5 2.04 4.4 2.08 0.5086 0.5250
0.95 - 0.92 163 425 38.4 1.69 5.0 2.19 0.4552 0.5338
0.92 - 0.89 209 518 40.3 1.90 3.8 1.67 0.5627 0.6695
0.89 - 0.86 218 552 39.5 1.63 3.3 1.27 0.6807 0.8639
0.86 - 0.84 162 431 37.6 1.59 3.3 1.14 0.7387 0.9731
0.84 - 0.82 175 468 37.4 1.52 2.5 0.96 0.8358 1.1482
0.82 - 0.79 141 396 35.6 1.25 2.3 0.83 0.8389 1.4124
#-----------------------------------------------------------------------------
0.89 - 0.79 760 2034 37.4 1.52 2.9 1.09 0.7449 1.0291
Inf - 0.79 3073 7164 42.9 2.25 20.7 5.41 0.1333 0.1397

601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 49.00 A**3

No chemically significant peaks appeared in the difference map.

414_ALERT_2_A Short Intra D-H..H-X H11 .. H183 .. 1.77 Ang.
220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9
420_ALERT_2_C D-H Without Acceptor Cu2 - H11 ... ?
420_ALERT_2_C D-H Without Acceptor Cu1 - H21 ... ?
960_ALERT_3_G Number of Intensities with I .LT. - 2*sig(I) .. 1
042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
793_ALERT_4_G The Model has Chirality at N5 (Verify) .... S
793_ALERT_4_G The Model has Chirality at N8 (Verify) .... S
793_ALERT_4_G The Model has Chirality at N13 (Verify) .... S
793_ALERT_4_G The Model has Chirality at N16 (Verify) .... S
795_ALERT_4_G C-Atom in CIF Coordinate List out of Sequence .. C2
796_ALERT_4_G O-Atom in CIF Coordinate List out of Sequence .. O4
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?

No action taken here.

731_ALERT_1_C Bond Calc 1.41(2), Rep 1.404(6) ...... 3.33 su-Ra
CL2 -O9 1.555 1.555
731_ALERT_1_C Bond Calc 1.41(2), Rep 1.409(8) ...... 2.50 su-Ra
CL2 -O7 1.555 1.555
732_ALERT_1_C Angle Calc 110.1(15), Rep 110.1(7) ...... 2.14 su-Ra
O8 -CL2 -O9 1.555 1.555 1.555

+ several similar alerts

The use of restraints can lead to significant differences in the esds of bond
distances and angles when platon tries to calculate them using only the diagonal
terms of covariances matrix.

950_ALERT_1_C Reported and Calculated Hmax Values Differ by .. 5
952_ALERT_1_C Reported and Calculated Lmax Values Differ by .. 2

Platon calculates these values assuming an 100% complete dataset: because of the
high pressure cell this is not the case therefore platon's calculation are not
completely reliable.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength

860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 256

Crystals list 16 attached here:

#LIST 16
DIST 0.0, 0.01 = MEAN O(3) TO O(4) , O(3) TO O(5)
CONT O(3) TO O(6) , O(4) TO O(5)
CONT O(4) TO O(6) , O(5) TO O(6)
DIST 0.0, 0.01 = MEAN CL(1) TO O(3), CL(1) TO O(4)
CONT CL(1) TO O(4), CL(1) TO O(5)
CONT CL(1) TO O(5), CL(1) TO O(6)
DIST 0.0, 0.01 = MEAN O(7) TO O(8) , O(7) TO O(9)
CONT O(7) TO O(10) , O(8) TO O(9)
CONT O(8) TO O(10) , O(9) TO O(10)
DIST 0.0, 0.01 = MEAN CL(2) TO O(7), CL(2) TO O(8)
CONT CL(2) TO O(8), CL(2) TO O(9)
CONT CL(2) TO O(9), CL(2) TO O(10)
DIST 1.5,.05 = N(5) TO C(6)
DIST 1.5,.05 = N(5) TO C(9)
DIST 1.5,.05 = N(8) TO C(7)
DIST 1.5,.05 = N(8) TO C(2)
DIST 1.5,.05 = C(6) TO C(7)
DIST 1.5,.05 = C(2) TO C(25)
DIST 1.5,.05 = C(2) TO C(4)
DIST 1.5,.05 = C(2) TO C(5)
DIST 1.5,.05 = C(9) TO C(10)
DIST 1.5,.05 = C(9) TO C(11)
DIST 1.5,.05 = C(9) TO C(12)
DIST 1.5,.05 = N(13) TO C(14)
DIST 1.5,.05 = N(13) TO C(20)
DIST 1.5,.05 = N(16) TO C(15)
DIST 1.5,.05 = N(16) TO C(17)
DIST 1.5,.05 = C(14) TO C(15)
DIST 1.5,.05 = C(17) TO C(18)
DIST 1.5,.05 = C(17) TO C(19)
DIST 1.5,.05 = C(17) TO C(24)
DIST 1.5,.05 = C(20) TO C(21)
DIST 1.5,.05 = C(20) TO C(22)
DIST 1.5,.05 = C(20) TO C(23)
REM SHIFTLIMIT START (DO NOT REMOVE THIS LINE)
REM SHIFTLIMIT END (DO NOT REMOVE THIS LINE)
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
REM DELU START (DO NOT REMOVE THIS LINE)
VIBR .0, 0.00500 = O(2) TO O(1)
VIBR .0, 0.00500 = N(13) TO O(1)
VIBR .0, 0.00500 = N(13) TO O(2)
VIBR .0, 0.00500 = N(16) TO O(1)
VIBR .0, 0.00500 = N(16) TO O(2)
VIBR .0, 0.00500 = N(16) TO N(13)
VIBR .0, 0.00500 = O(2) TO O(1)
VIBR .0, 0.00500 = N(5) TO O(1)
VIBR .0, 0.00500 = N(5) TO O(2)
VIBR .0, 0.00500 = N(8) TO O(1)
VIBR .0, 0.00500 = N(8) TO O(2)
VIBR .0, 0.00500 = N(8) TO N(5)
VIBR .0, 0.00500 = O(4) TO O(5)
VIBR .0, 0.00500 = O(6) TO O(5)
VIBR .0, 0.00500 = O(6) TO O(4)
VIBR .0, 0.00500 = O(3) TO O(5)
VIBR .0, 0.00500 = O(3) TO O(4)
VIBR .0, 0.00500 = O(3) TO O(6)
VIBR .0, 0.00500 = O(10) TO O(8)
VIBR .0, 0.00500 = O(9) TO O(8)
VIBR .0, 0.00500 = O(9) TO O(10)
VIBR .0, 0.00500 = O(7) TO O(8)
VIBR .0, 0.00500 = O(7) TO O(10)
VIBR .0, 0.00500 = O(7) TO O(9)
VIBR .0, 0.00200 = N(5) TO C(6)
VIBR .0, 0.00200 = N(5) TO C(9)
VIBR .0, 0.00500 = C(9) TO C(6)
VIBR .0, 0.00200 = N(8) TO C(7)
VIBR .0, 0.00200 = N(8) TO C(2)
VIBR .0, 0.00500 = C(2) TO C(7)
VIBR .0, 0.00200 = C(6) TO C(7)
VIBR .0, 0.00500 = C(7) TO N(5)
VIBR .0, 0.00500 = C(6) TO N(8)
VIBR .0, 0.00200 = C(2) TO C(25)
VIBR .0, 0.00200 = C(2) TO C(4)
VIBR .0, 0.00200 = C(2) TO C(5)
VIBR .0, 0.00500 = C(25) TO N(8)
VIBR .0, 0.00500 = C(4) TO N(8)
VIBR .0, 0.00500 = C(4) TO C(25)
VIBR .0, 0.00500 = C(5) TO N(8)
VIBR .0, 0.00500 = C(5) TO C(25)
VIBR .0, 0.00500 = C(5) TO C(4)
VIBR .0, 0.00200 = C(9) TO C(10)
VIBR .0, 0.00200 = C(9) TO C(11)
VIBR .0, 0.00200 = C(9) TO C(12)
VIBR .0, 0.00500 = C(10) TO N(5)
VIBR .0, 0.00500 = C(11) TO N(5)
VIBR .0, 0.00500 = C(11) TO C(10)
VIBR .0, 0.00500 = C(12) TO N(5)
VIBR .0, 0.00500 = C(12) TO C(10)
VIBR .0, 0.00500 = C(12) TO C(11)
VIBR .0, 0.00200 = N(13) TO C(14)
VIBR .0, 0.00200 = N(13) TO C(20)
VIBR .0, 0.00500 = C(20) TO C(14)
VIBR .0, 0.00200 = N(16) TO C(15)
VIBR .0, 0.00200 = N(16) TO C(17)
VIBR .0, 0.00500 = C(17) TO C(15)
VIBR .0, 0.00200 = C(14) TO C(15)
VIBR .0, 0.00500 = C(15) TO N(13)
VIBR .0, 0.00500 = C(14) TO N(16)
VIBR .0, 0.00200 = C(17) TO C(18)
VIBR .0, 0.00200 = C(17) TO C(19)
VIBR .0, 0.00200 = C(17) TO C(24)
VIBR .0, 0.00500 = C(18) TO N(16)
VIBR .0, 0.00500 = C(19) TO N(16)
VIBR .0, 0.00500 = C(19) TO C(18)
VIBR .0, 0.00500 = C(24) TO N(16)
VIBR .0, 0.00500 = C(24) TO C(18)
VIBR .0, 0.00500 = C(24) TO C(19)
VIBR .0, 0.00200 = C(20) TO C(21)
VIBR .0, 0.00200 = C(20) TO C(22)
VIBR .0, 0.00200 = C(20) TO C(23)
VIBR .0, 0.00500 = C(21) TO N(13)
VIBR .0, 0.00500 = C(22) TO N(13)
VIBR .0, 0.00500 = C(22) TO C(21)
VIBR .0, 0.00500 = C(23) TO N(13)
VIBR .0, 0.00500 = C(23) TO C(21)
VIBR .0, 0.00500 = C(23) TO C(22)
REM DELU END (DO NOT REMOVE THIS LINE)
REM THERMSIM START (DO NOT REMOVE THIS LINE)
U(IJ) .0, 0.04000 = N(5) TO C(6)
U(IJ) .0, 0.04000 = N(5) TO C(9)
U(IJ) .0, 0.04000 = N(8) TO C(7)
U(IJ) .0, 0.04000 = N(8) TO C(2)
U(IJ) .0, 0.04000 = C(6) TO C(7)
U(IJ) .0, 0.08000 = C(2) TO C(25)
U(IJ) .0, 0.08000 = C(2) TO C(4)
U(IJ) .0, 0.08000 = C(2) TO C(5)
U(IJ) .0, 0.08000 = C(9) TO C(10)
U(IJ) .0, 0.08000 = C(9) TO C(11)
U(IJ) .0, 0.08000 = C(9) TO C(12)
U(IJ) .0, 0.04000 = N(13) TO C(14)
U(IJ) .0, 0.04000 = N(13) TO C(20)
U(IJ) .0, 0.04000 = N(16) TO C(15)
U(IJ) .0, 0.04000 = N(16) TO C(17)
U(IJ) .0, 0.04000 = C(14) TO C(15)
U(IJ) .0, 0.08000 = C(17) TO C(18)
U(IJ) .0, 0.08000 = C(17) TO C(19)
U(IJ) .0, 0.08000 = C(17) TO C(24)
U(IJ) .0, 0.08000 = C(20) TO C(21)
U(IJ) .0, 0.08000 = C(20) TO C(22)
U(IJ) .0, 0.08000 = C(20) TO C(23)
REM THERMSIM END (DO NOT REMOVE THIS LINE)
END

;
#end of refcif
_cell_length_a                   30.038(10)
_cell_length_b                   11.866(2)
_cell_length_c                   18.963(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.837(18)
_cell_angle_gamma                90
_cell_volume                     6533(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1 '
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0000 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0030 0.0030 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'
Cl 0.0750 0.0710 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            8

# Given Formula = C20 H46 Cl2 Cu2 N4 O10
# Dc = 1.42 Fooo = 2960.00 Mu = 15.16 M = 700.60
# Found Formula = C20 H50 Cl2 Cu2 N4 O10
# Dc = 1.43 FOOO = 2960.00 Mu = 15.16 M = 704.64

_chemical_formula_sum            'C20 H50 Cl2 Cu2 N4 O10'
_chemical_formula_moiety         '[Cu2(OH)2(tben)2][ClO4]2'
_chemical_formula_weight         704.64

_cell_measurement_reflns_used    1821
_cell_measurement_theta_min      2
_cell_measurement_theta_max      17
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_min          0.09
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_max          0.12

_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             2960
_exptl_absorpt_coefficient_mu    1.516

# Sheldrick geometric approximatio 0.85 0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_T_max  0.87
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         210000
_diffrn_reflns_number            11282
_reflns_number_total             1864
_diffrn_reflns_av_R_equivalents  0.118
# Number of reflections with Friedels Law is 1864
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 3978

_diffrn_reflns_theta_min         1.243
_diffrn_reflns_theta_max         14.528
_diffrn_measured_fraction_theta_max 0.469

_diffrn_reflns_theta_full        10.896
_diffrn_measured_fraction_theta_full 0.506

_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -18
_reflns_limit_h_max              26
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.51
_refine_diff_density_max         0.56

# 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         1124
_refine_ls_number_restraints     256
_refine_ls_number_parameters     303
_oxford_refine_ls_R_factor_ref   0.0734
_refine_ls_wR_factor_ref         0.0808
_refine_ls_goodness_of_fit_ref   1.0713
_refine_ls_shift/su_max          0.003991

# The values computed from all data
_oxford_reflns_number_all        1838
_refine_ls_R_factor_all          0.1224
_refine_ls_wR_factor_all         0.0997

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                1124
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_gt          0.0808

# 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 # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
2.50 -0.497 1.33
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.10744(10) 0.22082(14) 0.10852(16) 0.0538 1.0000 Uani . . . . . . .
Cu2 Cu 0.15702(10) 0.00250(14) 0.12771(16) 0.0535 1.0000 Uani . . . . . . .
Cl1 Cl 0.2184(2) 0.4678(3) 0.1740(4) 0.0698 1.0000 Uani D . . . . . .
Cl2 Cl -0.0616(3) 0.2303(6) 0.0231(5) 0.1238 1.0000 Uani D . . . . . .
O1 O 0.1662(5) 0.1580(7) 0.1488(8) 0.0597 1.0000 Uani . U . . . . .
O2 O 0.0975(5) 0.0658(7) 0.0868(7) 0.0538 1.0000 Uani . U . . . . .
O5 O 0.1813(5) 0.4908(11) 0.1164(8) 0.132(4) 1.0000 Uiso D U . . . . .
O8 O -0.0358(9) 0.3000(14) 0.0776(11) 0.228(7) 1.0000 Uiso D U . . . . .
O4 O 0.2531(4) 0.5448(11) 0.1757(9) 0.134(4) 1.0000 Uiso D U . . . . .
O6 O 0.2340(6) 0.3604(8) 0.1701(9) 0.136(4) 1.0000 Uiso D U . . . . .
O10 O -0.0781(9) 0.2913(15) -0.0414(9) 0.229(7) 1.0000 Uiso D U . . . . .
O9 O -0.0344(7) 0.1403(18) 0.0100(13) 0.229(7) 1.0000 Uiso D U . . . . .
O3 O 0.2046(5) 0.4791(14) 0.2384(8) 0.141(4) 1.0000 Uiso D U . . . . .
O7 O -0.0993(7) 0.186(2) 0.0453(12) 0.230(7) 1.0000 Uiso D U . . . . .
N5 N 0.2179(7) -0.0583(10) 0.1129(12) 0.0518 1.0000 Uani D U . . . . .
N8 N 0.1420(7) -0.1513(10) 0.1585(11) 0.0516 1.0000 Uani D U . . . . .
C6 C 0.2084(10) -0.1832(12) 0.1077(15) 0.0672 1.0000 Uani D U . . . . .
C7 C 0.1866(9) -0.2167(14) 0.1665(15) 0.0680 1.0000 Uani D U . . . . .
C2 C 0.1172(9) -0.1641(13) 0.2192(13) 0.0595 1.0000 Uani D U . . . . .
C25 C 0.0696(9) -0.1161(17) 0.1976(16) 0.0809 1.0000 Uani D U . . . . .
C4 C 0.1127(12) -0.2871(13) 0.2363(17) 0.0863 1.0000 Uani D U . . . . .
C5 C 0.1456(11) -0.1012(15) 0.2868(14) 0.0792 1.0000 Uani D U . . . . .
C9 C 0.2348(8) -0.0104(14) 0.0542(12) 0.0630 1.0000 Uani D U . . . . .
C10 C 0.2539(11) 0.1082(14) 0.0770(18) 0.0949 1.0000 Uani D U . . . . .
C11 C 0.2732(10) -0.0813(15) 0.0417(14) 0.0737 1.0000 Uani D U . . . . .
C12 C 0.1987(13) -0.001(2) -0.0165(17) 0.1327 1.0000 Uani D U . . . . .
N13 N 0.0651(7) 0.3074(9) 0.0281(10) 0.0510 1.0000 Uani D U . . . . .
N16 N 0.1031(7) 0.3441(10) 0.1778(10) 0.0584 1.0000 Uani D U . . . . .
C14 C 0.0662(8) 0.4245(11) 0.0582(12) 0.0498 1.0000 Uani D U . . . . .
C15 C 0.0646(9) 0.4186(14) 0.1367(12) 0.0635 1.0000 Uani D U . . . . .
C17 C 0.0985(8) 0.3121(13) 0.2505(12) 0.0727 1.0000 Uani D U . . . . .
C18 C 0.1435(9) 0.2594(15) 0.2910(14) 0.0880 1.0000 Uani D U . . . . .
C19 C 0.0909(13) 0.4157(17) 0.2894(17) 0.1122 1.0000 Uani D U . . . . .
C24 C 0.0629(11) 0.2218(17) 0.2390(17) 0.0855 1.0000 Uani D U . . . . .
C20 C 0.0716(8) 0.2984(14) -0.0482(12) 0.0629 1.0000 Uani D U . . . . .
C21 C 0.0394(10) 0.3759(14) -0.1026(14) 0.0727 1.0000 Uani D U . . . . .
C22 C 0.1217(10) 0.3314(19) -0.0485(16) 0.0796 1.0000 Uani D U . . . . .
C23 C 0.0628(9) 0.1824(13) -0.0725(13) 0.0692 1.0000 Uani D U . . . . .
H11 H 0.1759 0.1594 0.1934 0.0781 1.0000 Uiso R . . . . . .
H21 H 0.0719 0.0573 0.0938 0.0691 1.0000 Uiso R . . . . . .
H61 H 0.2368 -0.2253 0.1129 0.0911 1.0000 Uiso R . . . . . .
H62 H 0.1876 -0.1998 0.0606 0.0910 1.0000 Uiso R . . . . . .
H71 H 0.2074 -0.1979 0.2132 0.0891 1.0000 Uiso R . . . . . .
H72 H 0.1805 -0.2970 0.1647 0.0891 1.0000 Uiso R . . . . . .
H253 H 0.0553 -0.1295 0.2367 0.1240 1.0000 Uiso R . . . . . .
H252 H 0.0706 -0.0365 0.1890 0.1240 1.0000 Uiso R . . . . . .
H251 H 0.0521 -0.1525 0.1541 0.1240 1.0000 Uiso R . . . . . .
H41 H 0.0885 -0.2930 0.2608 0.1390 1.0000 Uiso R . . . . . .
H42 H 0.1412 -0.3116 0.2685 0.1390 1.0000 Uiso R . . . . . .
H43 H 0.1054 -0.3337 0.1935 0.1391 1.0000 Uiso R . . . . . .
H53 H 0.1421 -0.1397 0.3295 0.1281 1.0000 Uiso R . . . . . .
H52 H 0.1777 -0.0989 0.2874 0.1281 1.0000 Uiso R . . . . . .
H51 H 0.1342 -0.0256 0.2865 0.1280 1.0000 Uiso R . . . . . .
H101 H 0.2718 0.1314 0.0441 0.1530 1.0000 Uiso R . . . . . .
H102 H 0.2732 0.1072 0.1260 0.1529 1.0000 Uiso R . . . . . .
H103 H 0.2289 0.1600 0.0739 0.1531 1.0000 Uiso R . . . . . .
H113 H 0.2901 -0.0397 0.0137 0.1241 1.0000 Uiso R . . . . . .
H112 H 0.2935 -0.1017 0.0878 0.1240 1.0000 Uiso R . . . . . .
H111 H 0.2607 -0.1482 0.0155 0.1241 1.0000 Uiso R . . . . . .
H121 H 0.2083 0.0461 -0.0511 0.1820 1.0000 Uiso R . . . . . .
H122 H 0.1917 -0.0754 -0.0365 0.1820 1.0000 Uiso R . . . . . .
H123 H 0.1718 0.0306 -0.0057 0.1820 1.0000 Uiso R . . . . . .
H141 H 0.0950 0.4586 0.0553 0.0731 1.0000 Uiso R . . . . . .
H142 H 0.0408 0.4694 0.0304 0.0731 1.0000 Uiso R . . . . . .
H151 H 0.0673 0.4936 0.1576 0.0860 1.0000 Uiso R . . . . . .
H152 H 0.0354 0.3858 0.1390 0.0861 1.0000 Uiso R . . . . . .
H181 H 0.1406 0.2342 0.3379 0.1180 1.0000 Uiso R . . . . . .
H182 H 0.1684 0.3123 0.2976 0.1181 1.0000 Uiso R . . . . . .
H183 H 0.1496 0.1960 0.2636 0.1180 1.0000 Uiso R . . . . . .
H193 H 0.0915 0.3947 0.3385 0.1631 1.0000 Uiso R . . . . . .
H192 H 0.1145 0.4707 0.2900 0.1630 1.0000 Uiso R . . . . . .
H191 H 0.0613 0.4467 0.2661 0.1630 1.0000 Uiso R . . . . . .
H241 H 0.0469 0.2284 0.2773 0.1361 1.0000 Uiso R . . . . . .
H242 H 0.0411 0.2309 0.1918 0.1360 1.0000 Uiso R . . . . . .
H243 H 0.0774 0.1483 0.2417 0.1360 1.0000 Uiso R . . . . . .
H213 H 0.0499 0.3788 -0.1463 0.1021 1.0000 Uiso R . . . . . .
H212 H 0.0399 0.4508 -0.0828 0.1020 1.0000 Uiso R . . . . . .
H211 H 0.0084 0.3471 -0.1139 0.1021 1.0000 Uiso R . . . . . .
H223 H 0.1287 0.3032 -0.0919 0.1371 1.0000 Uiso R . . . . . .
H222 H 0.1249 0.4121 -0.0469 0.1371 1.0000 Uiso R . . . . . .
H221 H 0.1427 0.2991 -0.0065 0.1370 1.0000 Uiso R . . . . . .
H231 H 0.0618 0.1779 -0.1235 0.0960 1.0000 Uiso R . . . . . .
H232 H 0.0865 0.1333 -0.0455 0.0960 1.0000 Uiso R . . . . . .
H233 H 0.0335 0.1600 -0.0654 0.0960 1.0000 Uiso R . . . . . .
H131 H 0.0356 0.2805 0.0252 0.0687 1.0000 Uiso R . . . . . .
H161 H 0.1296 0.3856 0.1855 0.0695 1.0000 Uiso R . . . . . .
H54 H 0.2402 -0.0463 0.1550 0.0640 1.0000 Uiso R . . . . . .
H81 H 0.1222 -0.1808 0.1177 0.0658 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.051(3) 0.0498(10) 0.055(3) -0.0024(11) 0.003(3) 0.0040(11)
Cu2 0.054(3) 0.0433(10) 0.058(3) 0.0023(11) 0.005(3) 0.0017(11)
Cl1 0.063(7) 0.067(3) 0.070(7) 0.002(2) -0.001(7) -0.006(3)
Cl2 0.098(11) 0.158(6) 0.101(9) -0.038(5) -0.002(11) -0.054(5)
O1 0.056(11) 0.041(5) 0.069(13) -0.001(5) -0.008(11) -0.002(4)
O2 0.038(9) 0.059(4) 0.058(12) 0.000(5) 0.001(11) 0.003(5)
N5 0.036(10) 0.053(5) 0.070(13) 0.010(6) 0.019(10) -0.004(6)
N8 0.050(11) 0.053(5) 0.056(14) 0.011(7) 0.020(11) -0.015(5)
C6 0.073(14) 0.049(6) 0.093(19) 0.005(8) 0.045(13) 0.005(8)
C7 0.073(14) 0.049(8) 0.092(18) 0.019(9) 0.037(13) 0.001(8)
C2 0.062(14) 0.068(7) 0.052(14) 0.011(9) 0.022(11) -0.019(9)
C25 0.058(13) 0.113(12) 0.08(2) 0.012(14) 0.037(11) -0.014(11)
C4 0.11(3) 0.070(7) 0.10(2) 0.009(11) 0.074(18) -0.028(10)
C5 0.09(2) 0.099(11) 0.056(14) 0.001(11) 0.024(16) -0.036(13)
C9 0.066(16) 0.066(7) 0.058(14) 0.020(8) 0.018(11) 0.003(7)
C10 0.09(3) 0.067(8) 0.16(3) 0.008(11) 0.087(19) -0.015(9)
C11 0.097(18) 0.080(11) 0.060(18) 0.017(11) 0.049(12) 0.009(11)
C12 0.14(3) 0.180(19) 0.057(15) 0.011(16) -0.005(18) 0.054(19)
N13 0.041(14) 0.060(5) 0.057(9) 0.006(6) 0.022(12) 0.006(7)
N16 0.055(12) 0.055(6) 0.063(9) 0.001(5) 0.011(11) -0.003(6)
C14 0.031(17) 0.059(6) 0.067(10) 0.007(7) 0.026(14) 0.016(8)
C15 0.052(16) 0.081(10) 0.059(10) -0.003(7) 0.016(14) 0.011(8)
C17 0.086(15) 0.074(8) 0.054(10) -0.005(7) 0.010(13) -0.003(7)
C18 0.09(2) 0.094(13) 0.07(2) 0.010(10) 0.00(2) -0.003(10)
C19 0.16(3) 0.096(11) 0.098(16) -0.019(12) 0.061(19) 0.009(13)
C24 0.08(2) 0.124(13) 0.065(19) -0.016(15) 0.050(19) -0.027(13)
C20 0.040(13) 0.099(8) 0.048(10) -0.002(9) 0.008(14) 0.015(9)
C21 0.07(2) 0.094(9) 0.056(13) 0.007(10) 0.015(18) 0.023(12)
C22 0.050(15) 0.130(15) 0.072(19) -0.026(15) 0.039(14) 0.013(12)
C23 0.07(2) 0.095(7) 0.040(14) 0.003(8) 0.009(17) 0.022(9)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2262(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
Cu1 . Cu2 . 2.964(3) yes
Cu1 . O1 . 1.887(12) yes
Cu1 . O2 . 1.891(9) yes
Cu1 . N13 . 2.001(11) yes
Cu1 . N16 . 1.994(18) yes
Cu2 . O1 . 1.893(8) yes
Cu2 . O2 . 1.910(12) yes
Cu2 . N5 . 2.05(3) yes
Cu2 . N8 . 2.003(16) yes
Cl1 . O5 . 1.373(5) yes
Cl1 . O4 . 1.380(6) yes
Cl1 . O6 . 1.367(7) yes
Cl1 . O3 . 1.394(7) yes
Cl2 . O8 . 1.394(6) yes
Cl2 . O10 . 1.399(7) yes
Cl2 . O9 . 1.404(6) yes
Cl2 . O7 . 1.409(8) yes
O1 . H11 . 0.821 no
O2 . H21 . 0.821 no
N5 . C6 . 1.509(18) yes
N5 . C9 . 1.45(3) yes
N5 . H54 . 0.911 no
N8 . C7 . 1.52(3) yes
N8 . C2 . 1.53(3) yes
N8 . H81 . 0.916 no
C6 . C7 . 1.48(3) yes
C6 . H61 . 0.972 no
C6 . H62 . 0.969 no
C7 . H71 . 0.969 no
C7 . H72 . 0.970 no
C2 . C25 . 1.50(3) yes
C2 . C4 . 1.51(2) yes
C2 . C5 . 1.54(2) yes
C25 . H253 . 0.960 no
C25 . H252 . 0.960 no
C25 . H251 . 0.959 no
C4 . H41 . 0.960 no
C4 . H42 . 0.961 no
C4 . H43 . 0.959 no
C5 . H53 . 0.960 no
C5 . H52 . 0.961 no
C5 . H51 . 0.961 no
C9 . C10 . 1.54(2) yes
C9 . C11 . 1.49(3) yes
C9 . C12 . 1.50(2) yes
C10 . H101 . 0.961 no
C10 . H102 . 0.962 no
C10 . H103 . 0.961 no
C11 . H113 . 0.959 no
C11 . H112 . 0.960 no
C11 . H111 . 0.960 no
C12 . H121 . 0.962 no
C12 . H122 . 0.960 no
C12 . H123 . 0.961 no
N13 . C14 . 1.499(18) yes
N13 . C20 . 1.51(3) yes
N13 . H131 . 0.928 no
N16 . C15 . 1.505(19) yes
N16 . C17 . 1.47(3) yes
N16 . H161 . 0.916 no
C14 . C15 . 1.50(3) yes
C14 . H141 . 0.971 no
C14 . H142 . 0.969 no
C15 . H151 . 0.970 no
C15 . H152 . 0.969 no
C17 . C18 . 1.51(2) yes
C17 . C19 . 1.48(3) yes
C17 . C24 . 1.49(3) yes
C18 . H181 . 0.963 no
C18 . H182 . 0.961 no
C18 . H183 . 0.960 no
C19 . H193 . 0.959 no
C19 . H192 . 0.961 no
C19 . H191 . 0.959 no
C24 . H241 . 0.971 no
C24 . H242 . 0.970 no
C24 . H243 . 0.971 no
C20 . C21 . 1.528(19) yes
C20 . C22 . 1.56(3) yes
C20 . C23 . 1.45(2) yes
C21 . H213 . 0.961 no
C21 . H212 . 0.962 no
C21 . H211 . 0.962 no
C22 . H223 . 0.960 no
C22 . H222 . 0.961 no
C22 . H221 . 0.961 no
C23 . H231 . 0.960 no
C23 . H232 . 0.959 no
C23 . H233 . 0.960 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
Cu2 . Cu1 . O1 . 38.4(3) yes
Cu2 . Cu1 . O2 . 39.0(4) yes
O1 . Cu1 . O2 . 77.4(4) yes
Cu2 . Cu1 . N13 . 138.0(5) yes
O1 . Cu1 . N13 . 149.0(9) yes
O2 . Cu1 . N13 . 107.4(4) yes
Cu2 . Cu1 . N16 . 132.6(3) yes
O1 . Cu1 . N16 . 103.7(5) yes
O2 . Cu1 . N16 . 145.5(9) yes
N13 . Cu1 . N16 . 89.4(6) yes
Cu1 . Cu2 . O1 . 38.3(4) yes
Cu1 . Cu2 . O2 . 38.5(3) yes
O1 . Cu2 . O2 . 76.8(4) yes
Cu1 . Cu2 . N5 . 136.7(5) yes
O1 . Cu2 . N5 . 106.5(7) yes
O2 . Cu2 . N5 . 149.0(8) yes
Cu1 . Cu2 . N8 . 133.5(7) yes
O1 . Cu2 . N8 . 149.1(9) yes
O2 . Cu2 . N8 . 102.7(6) yes
N5 . Cu2 . N8 . 89.8(8) yes
O5 . Cl1 . O4 . 110.0(6) yes
O5 . Cl1 . O6 . 111.2(6) yes
O4 . Cl1 . O6 . 110.5(7) yes
O5 . Cl1 . O3 . 108.3(7) yes
O4 . Cl1 . O3 . 107.9(6) yes
O6 . Cl1 . O3 . 108.8(6) yes
O8 . Cl2 . O10 . 110.3(7) yes
O8 . Cl2 . O9 . 110.1(7) yes
O10 . Cl2 . O9 . 109.3(7) yes
O8 . Cl2 . O7 . 109.8(7) yes
O10 . Cl2 . O7 . 109.0(7) yes
O9 . Cl2 . O7 . 108.3(7) yes
Cu2 . O1 . Cu1 . 103.3(5) yes
Cu2 . O1 . H11 . 103.4 no
Cu1 . O1 . H11 . 117.3 no
Cu2 . O2 . Cu1 . 102.4(5) yes
Cu2 . O2 . H21 . 134.8 no
Cu1 . O2 . H21 . 100.8 no
Cu2 . N5 . C6 . 101.1(18) yes
Cu2 . N5 . C9 . 117.8(12) yes
C6 . N5 . C9 . 116(2) yes
Cu2 . N5 . H54 . 107.8 no
C6 . N5 . H54 . 107.1 no
C9 . N5 . H54 . 106.8 no
Cu2 . N8 . C7 . 103.5(15) yes
Cu2 . N8 . C2 . 120.0(13) yes
C7 . N8 . C2 . 117.5(16) yes
Cu2 . N8 . H81 . 104.3 no
C7 . N8 . H81 . 104.6 no
C2 . N8 . H81 . 105.3 no
N5 . C6 . C7 . 109(2) yes
N5 . C6 . H61 . 110.6 no
C7 . C6 . H61 . 109.3 no
N5 . C6 . H62 . 109.1 no
C7 . C6 . H62 . 109.4 no
H61 . C6 . H62 . 109.4 no
N8 . C7 . C6 . 109.6(17) yes
N8 . C7 . H71 . 108.5 no
C6 . C7 . H71 . 108.8 no
N8 . C7 . H72 . 109.9 no
C6 . C7 . H72 . 110.7 no
H71 . C7 . H72 . 109.3 no
N8 . C2 . C25 . 111.7(19) yes
N8 . C2 . C4 . 110(2) yes
C25 . C2 . C4 . 107(2) yes
N8 . C2 . C5 . 108(2) yes
C25 . C2 . C5 . 109(2) yes
C4 . C2 . C5 . 110.6(17) yes
C2 . C25 . H253 . 108.0 no
C2 . C25 . H252 . 110.5 no
H253 . C25 . H252 . 109.5 no
C2 . C25 . H251 . 109.8 no
H253 . C25 . H251 . 109.6 no
H252 . C25 . H251 . 109.4 no
C2 . C4 . H41 . 107.2 no
C2 . C4 . H42 . 108.3 no
H41 . C4 . H42 . 109.4 no
C2 . C4 . H43 . 113.0 no
H41 . C4 . H43 . 109.3 no
H42 . C4 . H43 . 109.6 no
C2 . C5 . H53 . 108.3 no
C2 . C5 . H52 . 111.4 no
H53 . C5 . H52 . 109.4 no
C2 . C5 . H51 . 109.0 no
H53 . C5 . H51 . 109.4 no
H52 . C5 . H51 . 109.3 no
N5 . C9 . C10 . 109(2) yes
N5 . C9 . C11 . 109.7(16) yes
C10 . C9 . C11 . 108(2) yes
N5 . C9 . C12 . 114(3) yes
C10 . C9 . C12 . 108.5(17) yes
C11 . C9 . C12 . 108(2) yes
C9 . C10 . H101 . 108.0 no
C9 . C10 . H102 . 110.4 no
H101 . C10 . H102 . 109.4 no
C9 . C10 . H103 . 109.8 no
H101 . C10 . H103 . 109.6 no
H102 . C10 . H103 . 109.6 no
C9 . C11 . H113 . 109.7 no
C9 . C11 . H112 . 109.5 no
H113 . C11 . H112 . 109.4 no
C9 . C11 . H111 . 109.4 no
H113 . C11 . H111 . 109.3 no
H112 . C11 . H111 . 109.6 no
C9 . C12 . H121 . 112.2 no
C9 . C12 . H122 . 108.8 no
H121 . C12 . H122 . 109.7 no
C9 . C12 . H123 . 107.1 no
H121 . C12 . H123 . 109.3 no
H122 . C12 . H123 . 109.5 no
Cu1 . N13 . C14 . 103.8(9) yes
Cu1 . N13 . C20 . 118.7(13) yes
C14 . N13 . C20 . 115.7(17) yes
Cu1 . N13 . H131 . 106.2 no
C14 . N13 . H131 . 105.6 no
C20 . N13 . H131 . 105.9 no
Cu1 . N16 . C15 . 105.1(11) yes
Cu1 . N16 . C17 . 117.8(10) yes
C15 . N16 . C17 . 113(2) yes
Cu1 . N16 . H161 . 107.3 no
C15 . N16 . H161 . 106.7 no
C17 . N16 . H161 . 106.1 no
N13 . C14 . C15 . 109.3(16) yes
N13 . C14 . H141 . 107.4 no
C15 . C14 . H141 . 109.3 no
N13 . C14 . H142 . 111.4 no
C15 . C14 . H142 . 110.2 no
H141 . C14 . H142 . 109.2 no
N16 . C15 . C14 . 109(2) yes
N16 . C15 . H151 . 110.7 no
C14 . C15 . H151 . 110.0 no
N16 . C15 . H152 . 108.9 no
C14 . C15 . H152 . 108.8 no
H151 . C15 . H152 . 109.3 no
N16 . C17 . C18 . 107(2) yes
N16 . C17 . C19 . 108.4(18) yes
C18 . C17 . C19 . 108.8(16) yes
N16 . C17 . C24 . 106.5(17) yes
C18 . C17 . C24 . 107.0(16) yes
C19 . C17 . C24 . 118(3) yes
C17 . C18 . H181 . 108.6 no
C17 . C18 . H182 . 111.3 no
H181 . C18 . H182 . 109.5 no
C17 . C18 . H183 . 108.6 no
H181 . C18 . H183 . 109.4 no
H182 . C18 . H183 . 109.3 no
C17 . C19 . H193 . 107.6 no
C17 . C19 . H192 . 111.2 no
H193 . C19 . H192 . 109.5 no
C17 . C19 . H191 . 109.3 no
H193 . C19 . H191 . 109.4 no
H192 . C19 . H191 . 109.7 no
C17 . C24 . H241 . 107.8 no
C17 . C24 . H242 . 110.1 no
H241 . C24 . H242 . 109.7 no
C17 . C24 . H243 . 110.0 no
H241 . C24 . H243 . 109.5 no
H242 . C24 . H243 . 109.7 no
N13 . C20 . C21 . 113(2) yes
N13 . C20 . C22 . 110.4(15) yes
C21 . C20 . C22 . 107(2) yes
N13 . C20 . C23 . 108.2(20) yes
C21 . C20 . C23 . 108.9(13) yes
C22 . C20 . C23 . 110(2) yes
C20 . C21 . H213 . 108.2 no
C20 . C21 . H212 . 110.4 no
H213 . C21 . H212 . 109.1 no
C20 . C21 . H211 . 110.2 no
H213 . C21 . H211 . 109.4 no
H212 . C21 . H211 . 109.6 no
C20 . C22 . H223 . 109.8 no
C20 . C22 . H222 . 109.9 no
H223 . C22 . H222 . 109.4 no
C20 . C22 . H221 . 109.0 no
H223 . C22 . H221 . 109.3 no
H222 . C22 . H221 . 109.4 no
C20 . C23 . H231 . 109.2 no
C20 . C23 . H232 . 110.8 no
H231 . C23 . H232 . 109.3 no
C20 . C23 . H233 . 108.4 no
H231 . C23 . H233 . 109.4 no
H232 . C23 . H233 . 109.7 no
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
O1 . H11 . C18 . 130 0.82 2.59 3.18(4) yes
C7 . H71 . O6 7_545 175 0.97 2.55 3.51(4) yes
C25 . H252 . O2 . 128 0.96 2.59 3.27(4) yes
C14 . H141 . O5 . 148 0.97 2.58 3.44(4) yes
C15 . H152 . O8 . 149 0.97 2.39 3.25(4) yes
C18 . H183 . O1 . 139 0.96 2.40 3.18(4) yes
C23 . H232 . O2 . 127 0.96 2.57 3.24(4) yes
N13 . H131 . O8 . 145 0.93 2.59 3.39(4) yes
N16 . H161 . O5 . 142 0.92 2.59 3.36(4) yes
N16 . H161 . O3 . 165 0.92 2.48 3.37(4) yes
N5 . H54 . O3 7_545 178 0.91 2.28 3.19(4) yes
N8 . H81 . O10 2_555 164 0.92 2.14 3.03(4) yes

# Attachment 'cutb02.cif'

data_cutb02
_database_code_depnum_ccdc_archive 'CCDC 746649'

#0.90 GPa data set.

_audit_creation_date             09-07-22
_audit_creation_method           CRYSTALS_ver_12.86

_oxford_structure_analysis_title 'cutb02 in C2/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_chemical_compound_source        'Alessandro Prescimone'

_publ_section_exptl_refinement   
;

The H atoms were all positioned geometrically and then allowed to ride on
their parent atoms.

Checkcif output:

022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.47
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 9.84 Deg.
029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.49
088_ALERT_3_A Poor Data / Parameter Ratio .................... 3.87
201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) ....... 26
341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 69
910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) ..... 26
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.476 1404
913_ALERT_3_B Missing # of Very Strong Reflections in FCF .... 343
020_ALERT_3_C The value of Rint is greater than 0.12 ......... 0.17
082_ALERT_2_C High R1 Value .................................. 0.12

These alerts all derive from shading of reciprocal space by the pressure cell,
and they are unavoidable in high pressure crystal structure determinations.

023_ALERT_3_A Resolution (too) Low [sin(theta)/Lambda < 0.6].. 13.12 Deg.

INTENSITY STATISTICS FOR DATASET # 1 cubt02.hkl

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(sigma)

Inf - 2.95 68 145 46.9 2.94 110.7 11.14 0.0661 0.1001
2.95 - 2.35 67 133 50.4 2.67 56.1 8.98 0.0994 0.1078
2.35 - 2.05 67 140 47.9 1.79 60.6 7.81 0.1077 0.1225
2.05 - 1.85 72 145 49.7 2.13 64.2 8.03 0.0985 0.1087
1.85 - 1.70 74 153 48.4 2.14 43.5 7.07 0.1271 0.1117
1.70 - 1.55 104 221 47.1 2.13 25.5 5.32 0.1989 0.1518
1.55 - 1.45 91 200 45.5 1.95 31.5 5.48 0.1769 0.1580
1.45 - 1.35 118 264 44.7 1.90 29.6 5.59 0.2147 0.1710
1.35 - 1.30 71 159 44.7 1.74 26.9 5.04 0.2382 0.1851
1.30 - 1.25 89 200 44.5 1.73 24.1 4.14 0.3408 0.2211
1.25 - 1.20 95 218 43.6 1.95 11.6 3.67 0.3991 0.2860
1.20 - 1.15 117 257 45.5 1.95 9.4 2.72 0.4290 0.4054
1.15 - 1.10 140 322 43.5 1.92 7.9 2.27 0.5638 0.4594
1.10 - 1.05 155 366 42.3 1.78 7.0 2.07 0.5120 0.5403
#-----------------------------------------------------------------------------
1.15 - 1.05 295 688 42.9 1.85 7.4 2.16 0.5399 0.4995
Inf - 1.05 1328 2923 45.4 2.00 30.6 5.07 0.1754 0.1637

601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 47.00 A**3

No chemically significant peaks appeared in the difference map.

093_ALERT_1_A No su's on H-atoms, but refinement reported as . mixed

H atoms have all been positioned geometrically.

731_ALERT_1_C Bond Calc 1.51(7), Rep 1.50(3) ...... 2.33 su-Ra
N16 -C15 1.555 1.555
731_ALERT_1_C Bond Calc 1.49(7), Rep 1.49(3) ...... 2.33 su-Ra
C20 -C21 1.555 1.555
732_ALERT_1_C Angle Calc 109.4(15), Rep 109.4(7) ...... 2.14 su-Ra
O5 -CL1 -O4 1.555 1.555 1.555
732_ALERT_1_C Angle Calc 108.5(16), Rep 108.5(7) ...... 2.29 su-Ra
O5 -CL1 -O6 1.555 1.555 1.555

+ several similar alerts

The use of restraints can lead to significant differences in the esds of bond
distances and angles when platon tries to calculate them using only the diagonal
terms of covariances matrix.

950_ALERT_1_C Reported and Calculated Hmax Values Differ by .. 5
952_ALERT_1_C Reported and Calculated Lmax Values Differ by .. 2

Platon calculates these values assuming an 100% complete dataset: because of the
high pressure cell this is not the case therefore platon's calculation are not
completely reliable.

092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.48 Ang.

This dataset has been collected using synchrotron radiation at the above
wavelength

242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C2
220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.75 Ratio
222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.24 Ratio
241_ALERT_2_B Check High Ueq as Compared to Neighbors for C15
242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C9
390_ALERT_3_B Deviating Methyl C10 X-C-H Bond Angle ...... 120.00 Deg.
414_ALERT_2_B Short Intra D-H..H-X H10 .. H183 .. 1.84 Ang.
241_ALERT_2_C Check High Ueq as Compared to Neighbors for N5
241_ALERT_2_C Check High Ueq as Compared to Neighbors for N8
241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7
241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O1
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20
360_ALERT_2_C Short C(sp3)-C(sp3) Bond C20 - C23 ... 1.43 Ang.
390_ALERT_3_C Deviating Methyl C10 X-C-H Bond Angle ...... 101.00 Deg.
412_ALERT_2_C Short Intra XH3 .. XHn H141 .. H222 .. 1.88 Ang.
412_ALERT_2_C Short Intra XH3 .. XHn H142 .. H212 .. 1.86 Ang.
420_ALERT_2_C D-H Without Acceptor Cu2 - H10 ... ?
420_ALERT_2_C D-H Without Acceptor Cu1 - H20 ... ?
420_ALERT_2_C D-H Without Acceptor Cu2 - H81 ... ?
343_ALERT_2_G Check sp3 Angle Range in Main Residue for .. C2
042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ?
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 35.10 Deg.
N5 -C9 -CU2 1.555 1.555 1.555
793_ALERT_4_G The Model has Chirality at N5 (Verify) .... S
793_ALERT_4_G The Model has Chirality at N8 (Verify) .... S
793_ALERT_4_G The Model has Chirality at N13 (Verify) .... S
793_ALERT_4_G The Model has Chirality at N16 (Verify) .... S
795_ALERT_4_G C-Atom in CIF Coordinate List out of Sequence .. C2
796_ALERT_4_G O-Atom in CIF Coordinate List out of Sequence .. O4
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?

No action taken here.

860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 54

Crystals list 16 attached here:

#LIST 16
DIST 0.0, 0.01 = MEAN O(3) TO O(4) , O(3) TO O(5)
CONT O(3) TO O(6) , O(4) TO O(5)
CONT O(4) TO O(6) , O(5) TO O(6)
DIST 0.0, 0.01 = MEAN CL(1) TO O(3), CL(1) TO O(4)
CONT CL(1) TO O(4), CL(1) TO O(5)
CONT CL(1) TO O(5), CL(1) TO O(6)
DIST 0.0, 0.01 = MEAN O(7) TO O(8) , O(7) TO O(9)
CONT O(7) TO O(10) , O(8) TO O(9)
CONT O(8) TO O(10) , O(9) TO O(10)
DIST 0.0, 0.01 = MEAN CL(2) TO O(7), CL(2) TO O(8)
CONT CL(2) TO O(8), CL(2) TO O(9)
CONT CL(2) TO O(9), CL(2) TO O(10)
DIST 1.5,.05 = N(5) TO C(6)
DIST 1.5,.05 = N(5) TO C(9)
DIST 1.5,.05 = N(8) TO C(7)
DIST 1.5,.05 = N(8) TO C(2)
DIST 1.5,.05 = C(6) TO C(7)
DIST 1.5,.05 = C(2) TO C(25)
DIST 1.5,.05 = C(2) TO C(4)
DIST 1.5,.05 = C(2) TO C(5)
DIST 1.5,.05 = C(9) TO C(10)
DIST 1.5,.05 = C(9) TO C(11)
DIST 1.5,.05 = C(9) TO C(12)
DIST 1.5,.05 = N(13) TO C(14)
DIST 1.5,.05 = N(13) TO C(20)
DIST 1.5,.05 = N(16) TO C(15)
DIST 1.5,.05 = N(16) TO C(17)
DIST 1.5,.05 = C(14) TO C(15)
DIST 1.5,.05 = C(17) TO C(18)
DIST 1.5,.05 = C(17) TO C(19)
DIST 1.5,.05 = C(17) TO C(24)
DIST 1.5,.05 = C(20) TO C(21)
DIST 1.5,.05 = C(20) TO C(22)
DIST 1.5,.05 = C(20) TO C(23)
REM SHIFTLIMIT START (DO NOT REMOVE THIS LINE)
REM SHIFTLIMIT END (DO NOT REMOVE THIS LINE)
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
REM DELU START (DO NOT REMOVE THIS LINE)
VIBR .0, 0.00200 = CL(1) TO O(5)
VIBR .0, 0.00200 = CL(1) TO O(4)
VIBR .0, 0.00200 = CL(1) TO O(6)
VIBR .0, 0.00200 = CL(1) TO O(3)
VIBR .0, 0.00200 = CL(2) TO O(8)
VIBR .0, 0.00200 = CL(2) TO O(10)
VIBR .0, 0.00200 = CL(2) TO O(9)
VIBR .0, 0.00200 = CL(2) TO O(7)
REM DELU END (DO NOT REMOVE THIS LINE)
REM THERMSIM START (DO NOT REMOVE THIS LINE)
U(IJ) .0, 0.04000 = CL(1) TO O(5)
U(IJ) .0, 0.04000 = CL(1) TO O(4)
U(IJ) .0, 0.04000 = CL(1) TO O(6)
U(IJ) .0, 0.04000 = CL(1) TO O(3)
U(IJ) .0, 0.04000 = CL(2) TO O(8)
U(IJ) .0, 0.04000 = CL(2) TO O(10)
U(IJ) .0, 0.04000 = CL(2) TO O(9)
U(IJ) .0, 0.04000 = CL(2) TO O(7)
REM THERMSIM END (DO NOT REMOVE THIS LINE)
END

;
#end of refcif
_cell_length_a                   29.083(12)
_cell_length_b                   11.634(3)
_cell_length_c                   18.528(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.20(2)
_cell_angle_gamma                90
_cell_volume                     6050(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1 '
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0000 0.0010 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0010 0.0010 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0030 0.0030 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'
Cl 0.0750 0.0710 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.2890 0.6150 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            8

# Given Formula = C20 H50 Cl2 Cu2 N4 O10
# Dc = 1.55 Fooo = 2960.00 Mu = 16.37 M = 704.64
# Found Formula = C20 H50 Cl2 Cu2 N4 O10
# Dc = 1.55 FOOO = 2960.00 Mu = 16.37 M = 704.64

_chemical_formula_sum            'C20 H50 Cl2 Cu2 N4 O10'
_chemical_formula_moiety         '[Cu2(OH)2(tben)2][ClO4]2'
_chemical_formula_weight         704.64

_cell_measurement_reflns_used    1391
_cell_measurement_theta_min      2
_cell_measurement_theta_max      13
_cell_measurement_temperature    300

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_min          0.90
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_max          0.13

_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             2960
_exptl_absorpt_coefficient_mu    1.637

# Sheldrick geometric approximatio 0.84 0.23
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.00
_exptl_absorpt_correction_T_max  0.23
_diffrn_measurement_device       'Bruker SMART APEX-II on Station 9.8, SRS'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.47670
_diffrn_measurement_method       \w

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      300
_diffrn_ambient_pressure         900000
_diffrn_reflns_number            5849
_reflns_number_total             1276
_diffrn_reflns_av_R_equivalents  0.168
# Number of reflections with Friedels Law is 1276
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2734

_diffrn_reflns_theta_min         1.271
_diffrn_reflns_theta_max         13.120
_diffrn_measured_fraction_theta_max 0.466

_diffrn_reflns_theta_full        9.840
_diffrn_measured_fraction_theta_full 0.492

_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -16
_reflns_limit_h_max              23
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     'From ambient pressure structure'
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.51
_refine_diff_density_max         0.51

# 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         670
_refine_ls_number_restraints     54
_refine_ls_number_parameters     173
_oxford_refine_ls_R_factor_ref   0.1229
_refine_ls_wR_factor_ref         0.0854
_refine_ls_goodness_of_fit_ref   1.5891
_refine_ls_shift/su_max          0.004646

# The values computed from all data
_oxford_reflns_number_all        1156
_refine_ls_R_factor_all          0.1948
_refine_ls_wR_factor_all         0.1044

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                670
_refine_ls_R_factor_gt           0.1229
_refine_ls_wR_factor_gt          0.0854

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

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     
;
Method=
SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6)
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.1082(2) 0.2247(3) 0.1058(4) 0.0452 1.0000 Uani . . . . . . .
Cu2 Cu 0.1571(2) 0.0046(4) 0.1283(4) 0.0538 1.0000 Uani . . . . . . .
Cl1 Cl 0.2194(5) 0.4739(9) 0.1681(9) 0.0952 1.0000 Uani D U . . . . .
Cl2 Cl -0.0601(9) 0.2241(12) 0.0230(11) 0.1470 1.0000 Uani D U . . . . .
O1 O 0.1688(11) 0.1697(14) 0.1480(16) 0.033(5) 1.0000 Uiso . . . . . . .
O2 O 0.1007(13) 0.0638(14) 0.0844(17) 0.038(6) 1.0000 Uiso . . . . . . .
O5 O 0.1814(8) 0.5035(14) 0.1074(14) 0.055(4) 1.0000 Uiso D U . . . . .
O8 O -0.0338(14) 0.2957(15) 0.0763(16) 0.101(7) 1.0000 Uiso D U . . . . .
O4 O 0.2556(7) 0.5546(16) 0.1755(13) 0.076(7) 1.0000 Uiso D U . . . . .
O6 O 0.2363(9) 0.3653(14) 0.1545(14) 0.108(9) 1.0000 Uiso D U . . . . .
O10 O -0.0836(15) 0.2872(19) -0.0373(15) 0.141(9) 1.0000 Uiso D U . . . . .
O9 O -0.0308(10) 0.147(3) 0.0018(17) 0.150(18) 1.0000 Uiso D U . . . . .
O3 O 0.2040(9) 0.470(2) 0.2330(14) 0.144(18) 1.0000 Uiso D U . . . . .
O7 O -0.0923(11) 0.166(3) 0.0513(18) 0.20(3) 1.0000 Uiso D U . . . . .
N5 N 0.2148(17) -0.053(3) 0.117(3) 0.079(11) 1.0000 Uiso D . . . . . .
N8 N 0.1459(16) -0.141(3) 0.153(3) 0.089(13) 1.0000 Uiso D . . . . . .
C6 C 0.2073(19) -0.180(3) 0.112(3) 0.065(12) 1.0000 Uiso D . . . . . .
C7 C 0.1857(19) -0.232(4) 0.170(3) 0.101(16) 1.0000 Uiso D . . . . . .
C2 C 0.1204(15) -0.159(3) 0.215(3) 0.040(10) 1.0000 Uiso D . . . . . .
C25 C 0.0721(19) -0.118(4) 0.181(4) 0.15(2) 1.0000 Uiso D . . . . . .
C4 C 0.108(2) -0.271(3) 0.249(3) 0.110(16) 1.0000 Uiso D . . . . . .
C5 C 0.151(2) -0.089(3) 0.281(3) 0.091(14) 1.0000 Uiso D . . . . . .
C9 C 0.2349(16) 0.001(3) 0.059(3) 0.056(11) 1.0000 Uiso D . . . . . .
C10 C 0.254(2) 0.121(3) 0.071(4) 0.125(19) 1.0000 Uiso D . . . . . .
C11 C 0.272(2) -0.077(3) 0.044(3) 0.081(13) 1.0000 Uiso D . . . . . .
C12 C 0.197(2) 0.001(3) -0.013(3) 0.091(14) 1.0000 Uiso D . . . . . .
N13 N 0.0595(14) 0.310(2) 0.031(2) 0.061(9) 1.0000 Uiso D . . . . . .
N16 N 0.1044(16) 0.357(2) 0.172(3) 0.082(11) 1.0000 Uiso D . . . . . .
C14 C 0.068(2) 0.428(3) 0.051(3) 0.075(13) 1.0000 Uiso D . . . . . .
C15 C 0.0644(19) 0.433(3) 0.130(3) 0.110(18) 1.0000 Uiso D . . . . . .
C17 C 0.0994(16) 0.322(4) 0.247(3) 0.106(17) 1.0000 Uiso D . . . . . .
C18 C 0.1494(17) 0.265(2) 0.284(3) 0.064(11) 1.0000 Uiso D . . . . . .
C19 C 0.0851(18) 0.419(3) 0.294(3) 0.079(13) 1.0000 Uiso D . . . . . .
C24 C 0.059(2) 0.238(3) 0.239(4) 0.129(19) 1.0000 Uiso D . . . . . .
C20 C 0.0691(16) 0.301(2) -0.044(2) 0.057(11) 1.0000 Uiso D . . . . . .
C21 C 0.039(3) 0.383(3) -0.098(4) 0.124(19) 1.0000 Uiso D . . . . . .
C22 C 0.1179(18) 0.336(3) -0.048(3) 0.087(14) 1.0000 Uiso D . . . . . .
C23 C 0.0597(17) 0.187(2) -0.073(3) 0.047(9) 1.0000 Uiso D . . . . . .
H61 H 0.2372 -0.2163 0.1176 0.0781 1.0000 Uiso R . . . . . .
H62 H 0.1868 -0.1976 0.0646 0.0781 1.0000 Uiso R . . . . . .
H71 H 0.2056 -0.2290 0.2200 0.1207 1.0000 Uiso R . . . . . .
H72 H 0.1748 -0.3087 0.1591 0.1207 1.0000 Uiso R . . . . . .
H251 H 0.0538 -0.1257 0.2162 0.1844 1.0000 Uiso R . . . . . .
H252 H 0.0732 -0.0388 0.1679 0.1844 1.0000 Uiso R . . . . . .
H253 H 0.0577 -0.1609 0.1373 0.1844 1.0000 Uiso R . . . . . .
H41 H 0.0918 -0.2528 0.2864 0.1306 1.0000 Uiso R . . . . . .
H42 H 0.1358 -0.3130 0.2706 0.1306 1.0000 Uiso R . . . . . .
H43 H 0.0871 -0.3151 0.2108 0.1306 1.0000 Uiso R . . . . . .
H51 H 0.1366 -0.0962 0.3221 0.1107 1.0000 Uiso R . . . . . .
H52 H 0.1823 -0.1180 0.2957 0.1107 1.0000 Uiso R . . . . . .
H53 H 0.1511 -0.0104 0.2679 0.1107 1.0000 Uiso R . . . . . .
H101 H 0.2665 0.1562 0.0345 0.1392 1.0000 Uiso R . . . . . .
H102 H 0.2770 0.1205 0.1179 0.1392 1.0000 Uiso R . . . . . .
H103 H 0.2264 0.1620 0.0755 0.1392 1.0000 Uiso R . . . . . .
H111 H 0.2862 -0.0453 0.0079 0.0974 1.0000 Uiso R . . . . . .
H112 H 0.2957 -0.0897 0.0895 0.0974 1.0000 Uiso R . . . . . .
H113 H 0.2569 -0.1475 0.0262 0.0974 1.0000 Uiso R . . . . . .
H121 H 0.2084 0.0364 -0.0511 0.1053 1.0000 Uiso R . . . . . .
H122 H 0.1889 -0.0767 -0.0261 0.1053 1.0000 Uiso R . . . . . .
H123 H 0.1698 0.0409 -0.0070 0.1053 1.0000 Uiso R . . . . . .
H141 H 0.0981 0.4521 0.0473 0.0893 1.0000 Uiso R . . . . . .
H142 H 0.0438 0.4757 0.0202 0.0893 1.0000 Uiso R . . . . . .
H151 H 0.0686 0.5094 0.1484 0.1349 1.0000 Uiso R . . . . . .
H152 H 0.0346 0.4042 0.1346 0.1349 1.0000 Uiso R . . . . . .
H181 H 0.1498 0.2382 0.3327 0.0768 1.0000 Uiso R . . . . . .
H182 H 0.1739 0.3205 0.2878 0.0768 1.0000 Uiso R . . . . . .
H183 H 0.1544 0.2025 0.2542 0.0768 1.0000 Uiso R . . . . . .
H191 H 0.0822 0.3884 0.3399 0.0941 1.0000 Uiso R . . . . . .
H192 H 0.1090 0.4767 0.3032 0.0941 1.0000 Uiso R . . . . . .
H193 H 0.0555 0.4515 0.2672 0.0941 1.0000 Uiso R . . . . . .
H241 H 0.0566 0.2176 0.2873 0.1534 1.0000 Uiso R . . . . . .
H242 H 0.0301 0.2744 0.2122 0.1534 1.0000 Uiso R . . . . . .
H243 H 0.0641 0.1715 0.2127 0.1534 1.0000 Uiso R . . . . . .
H211 H 0.0452 0.3774 -0.1454 0.1482 1.0000 Uiso R . . . . . .
H212 H 0.0449 0.4593 -0.0794 0.1482 1.0000 Uiso R . . . . . .
H213 H 0.0066 0.3637 -0.1018 0.1482 1.0000 Uiso R . . . . . .
H221 H 0.1203 0.3275 -0.0978 0.1004 1.0000 Uiso R . . . . . .
H222 H 0.1241 0.4135 -0.0325 0.1004 1.0000 Uiso R . . . . . .
H223 H 0.1405 0.2872 -0.0157 0.1004 1.0000 Uiso R . . . . . .
H231 H 0.0661 0.1842 -0.1210 0.0569 1.0000 Uiso R . . . . . .
H232 H 0.0799 0.1340 -0.0406 0.0569 1.0000 Uiso R . . . . . .
H233 H 0.0273 0.1669 -0.0783 0.0569 1.0000 Uiso R . . . . . .
H54 H 0.2364 -0.0400 0.1605 0.0895 1.0000 Uiso R . . . . . .
H81 H 0.1250 -0.1681 0.1122 0.1008 1.0000 Uiso R . . . . . .
H131 H 0.0297 0.2871 0.0295 0.0680 1.0000 Uiso R . . . . . .
H161 H 0.1318 0.3973 0.1793 0.0981 1.0000 Uiso R . . . . . .
H10 H 0.1867 0.1434 0.1892 0.0435 1.0000 Uiso . . . . . . .
H20 H 0.0719 0.0828 0.0647 0.0459 1.0000 Uiso . . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.024(8) 0.071(3) 0.036(8) -0.012(3) -0.002(8) 0.013(4)
Cu2 0.037(9) 0.055(3) 0.058(8) 0.002(3) -0.007(9) -0.006(4)
Cl1 0.044(10) 0.105(9) 0.115(13) 0.002(7) -0.016(7) -0.001(6)
Cl2 0.118(15) 0.146(12) 0.149(15) -0.026(9) -0.015(11) 0.002(14)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1822(17)
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
Cu1 . Cu2 . 2.908(7) yes
Cu1 . O1 . 1.85(3) yes
Cu1 . O2 . 1.915(17) yes
Cu1 . N13 . 1.97(2) yes
Cu1 . N16 . 1.99(4) yes
Cu2 . O1 . 1.968(18) yes
Cu2 . O2 . 1.77(3) yes
Cu2 . N5 . 1.87(6) yes
Cu2 . N8 . 1.81(4) yes
Cu2 . C9 . 2.88(7) yes
Cu2 . H54 . 2.284 no
Cl1 . O5 . 1.398(6) yes
Cl1 . O4 . 1.391(6) yes
Cl1 . O6 . 1.402(8) yes
Cl1 . O3 . 1.390(8) yes
Cl2 . O8 . 1.363(6) yes
Cl2 . O10 . 1.363(8) yes
Cl2 . O9 . 1.363(6) yes
Cl2 . O7 . 1.364(8) yes
O1 . H10 . 0.860 no
O2 . H20 . 0.853 no
N5 . C6 . 1.49(3) yes
N5 . C9 . 1.48(4) yes
N5 . H54 . 0.900 no
N8 . C7 . 1.54(4) yes
N8 . C2 . 1.53(4) yes
N8 . H81 . 0.900 no
C6 . C7 . 1.51(4) yes
C6 . H61 . 0.950 no
C6 . H62 . 0.950 no
C7 . H71 . 0.950 no
C7 . H72 . 0.950 no
C2 . C25 . 1.46(4) yes
C2 . C4 . 1.53(4) yes
C2 . C5 . 1.55(3) yes
C25 . H251 . 0.950 no
C25 . H252 . 0.950 no
C25 . H253 . 0.950 no
C4 . H41 . 0.950 no
C4 . H42 . 0.950 no
C4 . H43 . 0.950 no
C5 . H51 . 0.950 no
C5 . H52 . 0.950 no
C5 . H53 . 0.950 no
C9 . C10 . 1.494(9) yes
C9 . C11 . 1.49(4) yes
C9 . C12 . 1.49(3) yes
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C10 . H103 . 0.950 no
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C11 . H113 . 0.950 no
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
N13 . C14 . 1.44(3) yes
N13 . C20 . 1.48(4) yes
N13 . H131 . 0.900 no
N16 . C15 . 1.50(3) yes
N16 . C17 . 1.50(4) yes
N16 . H161 . 0.900 no
C14 . C15 . 1.49(4) yes
C14 . H141 . 0.950 no
C14 . H142 . 0.950 no
C15 . H151 . 0.950 no
C15 . H152 . 0.950 no
C17 . C18 . 1.58(4) yes
C17 . C19 . 1.55(4) yes
C17 . C24 . 1.50(4) yes
C18 . H181 . 0.950 no
C18 . H182 . 0.950 no
C18 . H183 . 0.950 no
C19 . H191 . 0.950 no
C19 . H192 . 0.950 no
C19 . H193 . 0.950 no
C24 . H241 . 0.950 no
C24 . H242 . 0.950 no
C24 . H243 . 0.950 no
C20 . C21 . 1.49(3) yes
C20 . C22 . 1.50(4) yes
C20 . C23 . 1.44(3) yes
C21 . H211 . 0.950 no
C21 . H212 . 0.950 no
C21 . H213 . 0.950 no
C22 . H221 . 0.950 no
C22 . H222 . 0.950 no
C22 . H223 . 0.950 no
C23 . H231 . 0.950 no
C23 . H232 . 0.950 no
C23 . H233 . 0.950 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
Cu2 . Cu1 . O1 . 41.9(5) yes
Cu2 . Cu1 . O2 . 36.1(8) yes
O1 . Cu1 . O2 . 78.0(9) yes
Cu2 . Cu1 . N13 . 141.0(10) yes
O1 . Cu1 . N13 . 154(2) yes
O2 . Cu1 . N13 . 108.8(8) yes
Cu2 . Cu1 . N16 . 134.3(8) yes
O1 . Cu1 . N16 . 102.0(12) yes
O2 . Cu1 . N16 . 150(2) yes
N13 . Cu1 . N16 . 84.4(14) yes
Cu1 . Cu2 . O1 . 38.8(7) yes
Cu1 . Cu2 . O2 . 39.7(5) yes
O1 . Cu2 . O2 . 78.4(9) yes
Cu1 . Cu2 . N5 . 136.0(14) yes
O1 . Cu2 . N5 . 104.7(16) yes
O2 . Cu2 . N5 . 147(2) yes
Cu1 . Cu2 . N8 . 138.3(17) yes
O1 . Cu2 . N8 . 154(2) yes
O2 . Cu2 . N8 . 105.9(16) yes
N5 . Cu2 . N8 . 86(2) yes
Cu1 . Cu2 . C9 . 111.3(7) yes
O1 . Cu2 . C9 . 88.9(15) yes
O2 . Cu2 . C9 . 122.9(17) yes
N5 . Cu2 . C9 . 27.0(13) yes
N8 . Cu2 . C9 . 108(2) yes
Cu1 . Cu2 . H54 . 131.3 no
O1 . Cu2 . H54 . 93.4 no
O2 . Cu2 . H54 . 163.6 no
N5 . Cu2 . H54 . 22.3 no
N8 . Cu2 . H54 . 87.6 no
C9 . Cu2 . H54 . 41.8 no
O5 . Cl1 . O4 . 109.4(7) yes
O5 . Cl1 . O6 . 108.5(7) yes
O4 . Cl1 . O6 . 109.5(8) yes
O5 . Cl1 . O3 . 109.9(8) yes
O4 . Cl1 . O3 . 110.3(7) yes
O6 . Cl1 . O3 . 109.3(7) yes
O8 . Cl2 . O10 . 109.3(8) yes
O8 . Cl2 . O9 . 109.6(8) yes
O10 . Cl2 . O9 . 109.6(8) yes
O8 . Cl2 . O7 . 109.6(8) yes
O10 . Cl2 . O7 . 109.4(8) yes
O9 . Cl2 . O7 . 109.4(8) yes
Cu2 . O1 . Cu1 . 99.3(10) yes
Cu2 . O1 . H10 . 81.5 no
Cu1 . O1 . H10 . 142.1 no
Cu1 . O2 . Cu2 . 104.2(11) yes
Cu1 . O2 . H20 . 83.1 no
Cu2 . O2 . H20 . 171.5 no
Cu2 . N5 . C6 . 104(4) yes
Cu2 . N5 . C9 . 118(3) yes
C6 . N5 . C9 . 117(5) yes
Cu2 . N5 . H54 . 105.6 no
C6 . N5 . H54 . 105.7 no
C9 . N5 . H54 . 105.5 no
Cu2 . N8 . C7 . 121(4) yes
Cu2 . N8 . C2 . 119(3) yes
C7 . N8 . C2 . 104(4) yes
Cu2 . N8 . H81 . 103.7 no
C7 . N8 . H81 . 103.6 no
C2 . N8 . H81 . 103.4 no
N5 . C6 . C7 . 116(5) yes
N5 . C6 . H61 . 108.5 no
C7 . C6 . H61 . 106.9 no
N5 . C6 . H62 . 108.1 no
C7 . C6 . H62 . 107.4 no
H61 . C6 . H62 . 109.5 no
N8 . C7 . C6 . 90(4) yes
N8 . C7 . H71 . 114.0 no
C6 . C7 . H71 . 114.2 no
N8 . C7 . H72 . 114.3 no
C6 . C7 . H72 . 113.5 no
H71 . C7 . H72 . 109.5 no
N8 . C2 . C25 . 104(4) yes
N8 . C2 . C4 . 130(4) yes
C25 . C2 . C4 . 99(4) yes
N8 . C2 . C5 . 104(4) yes
C25 . C2 . C5 . 117(4) yes
C4 . C2 . C5 . 105(4) yes
C2 . C25 . H251 . 108.6 no
C2 . C25 . H252 . 109.5 no
H251 . C25 . H252 . 109.5 no
C2 . C25 . H253 . 110.3 no
H251 . C25 . H253 . 109.5 no
H252 . C25 . H253 . 109.5 no
C2 . C4 . H41 . 109.6 no
C2 . C4 . H42 . 109.8 no
H41 . C4 . H42 . 109.5 no
C2 . C4 . H43 . 108.9 no
H41 . C4 . H43 . 109.5 no
H42 . C4 . H43 . 109.5 no
C2 . C5 . H51 . 108.4 no
C2 . C5 . H52 . 110.1 no
H51 . C5 . H52 . 109.5 no
C2 . C5 . H53 . 109.9 no
H51 . C5 . H53 . 109.5 no
H52 . C5 . H53 . 109.5 no
N5 . C9 . Cu2 . 35.1(18) yes
N5 . C9 . C10 . 119(5) yes
Cu2 . C9 . C10 . 103(4) yes
N5 . C9 . C11 . 109(3) yes
Cu2 . C9 . C11 . 142(3) yes
C10 . C9 . C11 . 110(4) yes
N5 . C9 . C12 . 108(5) yes
Cu2 . C9 . C12 . 85(4) yes
C10 . C9 . C12 . 107(3) yes
C11 . C9 . C12 . 103(4) yes
C9 . C10 . H101 . 119.9 no
C9 . C10 . H102 . 106.2 no
H101 . C10 . H102 . 109.5 no
C9 . C10 . H103 . 101.8 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no
C9 . C11 . H111 . 111.8 no
C9 . C11 . H112 . 109.0 no
H111 . C11 . H112 . 109.5 no
C9 . C11 . H113 . 107.6 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
C9 . C12 . H121 . 110.6 no
C9 . C12 . H122 . 107.9 no
H121 . C12 . H122 . 109.5 no
C9 . C12 . H123 . 109.9 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no
Cu1 . N13 . C14 . 104.9(19) yes
Cu1 . N13 . C20 . 110(3) yes
C14 . N13 . C20 . 105(4) yes
Cu1 . N13 . H131 . 112.3 no
C14 . N13 . H131 . 112.0 no
C20 . N13 . H131 . 112.1 no
Cu1 . N16 . C15 . 107(3) yes
Cu1 . N16 . C17 . 113(3) yes
C15 . N16 . C17 . 113(4) yes
Cu1 . N16 . H161 . 107.8 no
C15 . N16 . H161 . 108.3 no
C17 . N16 . H161 . 107.3 no
N13 . C14 . C15 . 104(4) yes
N13 . C14 . H141 . 110.6 no
C15 . C14 . H141 . 111.2 no
N13 . C14 . H142 . 110.9 no
C15 . C14 . H142 . 110.5 no
H141 . C14 . H142 . 109.5 no
N16 . C15 . C14 . 104(4) yes
N16 . C15 . H151 . 110.9 no
C14 . C15 . H151 . 110.2 no
N16 . C15 . H152 . 110.8 no
C14 . C15 . H152 . 111.3 no
H151 . C15 . H152 . 109.5 no
N16 . C17 . C18 . 103(4) yes
N16 . C17 . C19 . 115(4) yes
C18 . C17 . C19 . 114(4) yes
N16 . C17 . C24 . 110(4) yes
C18 . C17 . C24 . 112(4) yes
C19 . C17 . C24 . 102(4) yes
C17 . C18 . H181 . 109.4 no
C17 . C18 . H182 . 109.6 no
H181 . C18 . H182 . 109.5 no
C17 . C18 . H183 . 109.3 no
H181 . C18 . H183 . 109.5 no
H182 . C18 . H183 . 109.5 no
C17 . C19 . H191 . 109.3 no
C17 . C19 . H192 . 109.1 no
H191 . C19 . H192 . 109.5 no
C17 . C19 . H193 . 110.0 no
H191 . C19 . H193 . 109.5 no
H192 . C19 . H193 . 109.5 no
C17 . C24 . H241 . 108.4 no
C17 . C24 . H242 . 109.2 no
H241 . C24 . H242 . 109.5 no
C17 . C24 . H243 . 110.8 no
H241 . C24 . H243 . 109.5 no
H242 . C24 . H243 . 109.5 no
N13 . C20 . C21 . 111(5) yes
N13 . C20 . C22 . 116(3) yes
C21 . C20 . C22 . 101(4) yes
N13 . C20 . C23 . 111(4) yes
C21 . C20 . C23 . 108(3) yes
C22 . C20 . C23 . 109(4) yes
C20 . C21 . H211 . 111.0 no
C20 . C21 . H212 . 109.8 no
H211 . C21 . H212 . 109.5 no
C20 . C21 . H213 . 107.6 no
H211 . C21 . H213 . 109.5 no
H212 . C21 . H213 . 109.5 no
C20 . C22 . H221 . 109.5 no
C20 . C22 . H222 . 110.4 no
H221 . C22 . H222 . 109.5 no
C20 . C22 . H223 . 108.5 no
H221 . C22 . H223 . 109.5 no
H222 . C22 . H223 . 109.5 no
C20 . C23 . H231 . 108.7 no
C20 . C23 . H232 . 109.4 no
H231 . C23 . H232 . 109.5 no
C20 . C23 . H233 . 110.4 no
H231 . C23 . H233 . 109.5 no
H232 . C23 . H233 . 109.5 no
N5 . H54 . Cu2 . 52.1 no
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
C7 . H72 . O5 1_545 152 0.95 2.41 3.28(7) yes
C25 . H252 . O2 . 136 0.95 2.26 3.02(7) yes
C25 . H253 . O9 2_555 142 0.95 2.49 3.30(7) yes
C5 . H52 . O6 7_545 163 0.95 2.31 3.24(7) yes
C10 . H103 . O1 . 142 0.95 2.41 3.21(7) yes
C11 . H111 . O5 4_555 167 0.95 2.60 3.53(7) yes
C14 . H141 . O5 . 150 0.95 2.46 3.32(7) yes
C15 . H152 . O8 . 145 0.95 2.36 3.19(7) yes
C18 . H182 . O3 . 148 0.95 2.29 3.14(7) yes
C18 . H183 . O1 . 140 0.95 2.15 2.94(7) yes
C19 . H191 . O8 5_555 152 0.95 2.59 3.46(7) yes
C23 . H232 . O2 . 143 0.95 2.38 3.19(7) yes
C23 . H233 . O9 . 140 0.95 2.54 3.32(7) yes
N5 . H54 . O3 7_545 172 0.90 2.26 3.16(7) yes
N8 . H81 . O10 2_555 159 0.90 2.10 2.96(7) yes
N13 . H131 . O8 . 150 0.90 2.24 3.05(7) yes
N13 . H131 . O9 . 150 0.90 2.35 3.17(7) yes
N16 . H161 . O5 . 141 0.90 2.53 3.28(7) yes
N16 . H161 . O3 . 162 0.90 2.24 3.11(7) yes