# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cpd1

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

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

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

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

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

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.6254(8)
_cell_length_b                   9.6654(10)
_cell_length_c                   10.4451(12)
_cell_angle_alpha                90.651(9)
_cell_angle_beta                 108.055(10)
_cell_angle_gamma                100.708(9)
_cell_volume                     717.21(14)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
Ni 0.3393 1.1124 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421
1.0341 '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'
Fe 0.3463 0.8444 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805
1.0369 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            1


_chemical_formula_sum            'C30 H38 Cu2 N6 O4 '
_chemical_formula_moiety         'C30 H38 Cu2 N6 O4 '
_chemical_compound_source        ?
_chemical_formula_weight         673.76


_cell_measurement_reflns_used    1656
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27
_cell_measurement_temperature    180

_exptl_crystal_description       planar
_exptl_crystal_colour            'pale red'
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             350
_exptl_absorpt_coefficient_mu    1.530

# Sheldrick geometric approximatio 0.86 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            9078
_reflns_number_total             2619
_diffrn_reflns_av_R_equivalents  0.100
# Number of reflections without Friedels Law is 4698 
# Number of reflections with Friedels Law is 2619 
# Theoretical number of reflections is about 2904 


_diffrn_reflns_theta_min         2.867
_diffrn_reflns_theta_max         26.931
_diffrn_measured_fraction_theta_max 0.843

_diffrn_reflns_theta_full        25.045
_diffrn_measured_fraction_theta_full 0.889


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -9
_reflns_limit_h_max              8
_reflns_limit_k_min              -11
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              13

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

_refine_diff_density_min         -0.65
_refine_diff_density_max         0.98


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         1608
_refine_ls_number_restraints     0
_refine_ls_number_parameters     190
_oxford_refine_ls_R_factor_ref   0.0517
_refine_ls_wR_factor_ref         0.0578
_refine_ls_goodness_of_fit_ref   1.0225
_refine_ls_shift/su_max          0.0000638
_refine_ls_shift/su_mean         0.0000084


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2610
_refine_ls_R_factor_all          0.0947
_refine_ls_wR_factor_all         0.0826

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1898
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_gt          0.0644

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


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 15.4 -9.33 12.8 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.4548(7) 0.6870(6) 0.3102(5) 0.0221 1.0000 Uani . . . . . .
C2 C 0.5387(8) 0.8303(6) 0.3165(6) 0.0269 1.0000 Uani . . . . . .
C3 C 0.5648(8) 0.8920(6) 0.2031(6) 0.0295 1.0000 Uani . . . . . .
C4 C 0.5087(8) 0.8155(6) 0.0795(6) 0.0278 1.0000 Uani . . . . . .
C5 C 0.4257(8) 0.6749(6) 0.0700(6) 0.0268 1.0000 Uani . . . . . .
C6 C 0.3943(7) 0.6071(6) 0.1838(5) 0.0235 1.0000 Uani . . . . . .
C7 C 0.3020(7) 0.4607(6) 0.1605(5) 0.0237 1.0000 Uani . . . . . .
C8 C 0.1489(8) 0.2370(6) 0.2160(6) 0.0246 1.0000 Uani . . . . . .
C9 C 0.0419(8) 0.1973(6) 0.0665(6) 0.0283 1.0000 Uani . . . . . .
C10 C 0.3042(8) 0.1528(6) 0.2679(6) 0.0263 1.0000 Uani . . . . . .
C11 C 0.0068(8) 0.2101(6) 0.2949(6) 0.0260 1.0000 Uani . . . . . .
C12 C 0.0257(7) 0.2795(6) 0.5276(5) 0.0218 1.0000 Uani . . . . . .
C13 C -0.1393(8) 0.1675(6) 0.5254(6) 0.0316 1.0000 Uani . . . . . .
C14 C 0.1134(7) 0.3875(6) 0.6356(5) 0.0222 1.0000 Uani . . . . . .
C15 C 0.0828(8) 0.3831(7) 0.7699(6) 0.0294 1.0000 Uani . . . . . .
Cu1 Cu 0.27434(9) 0.45972(7) 0.43219(7) 0.0205 1.0000 Uani . . . . . .
O1 O 0.4372(5) 0.6328(4) 0.4236(4) 0.0237 1.0000 Uani . . . . . .
N1 N 0.2401(6) 0.3883(5) 0.2471(4) 0.0208 1.0000 Uani . . . . . .
N2 N 0.0932(6) 0.2895(5) 0.4263(4) 0.0219 1.0000 Uani . . . . . .
N3 N 0.2296(6) 0.4963(5) 0.6106(4) 0.0206 1.0000 Uani . . . . . .
O2 O 0.3154(5) 0.5980(4) 0.6984(4) 0.0268 1.0000 Uani . . . . . .
H21 H 0.5781 0.8841 0.3982 0.0320 1.0000 Uiso R . . . . .
H31 H 0.6186 0.9875 0.2100 0.0347 1.0000 Uiso R . . . . .
H41 H 0.5269 0.8587 0.0041 0.0332 1.0000 Uiso R . . . . .
H51 H 0.3899 0.6223 -0.0119 0.0321 1.0000 Uiso R . . . . .
H71 H 0.2838 0.4152 0.0773 0.0282 1.0000 Uiso R . . . . .
H93 H -0.0342 0.2651 0.0290 0.0418 1.0000 Uiso R . . . . .
H91 H 0.1297 0.1949 0.0184 0.0420 1.0000 Uiso R . . . . .
H92 H -0.0370 0.1058 0.0547 0.0418 1.0000 Uiso R . . . . .
H101 H 0.3687 0.1789 0.3620 0.0393 1.0000 Uiso R . . . . .
H102 H 0.3926 0.1733 0.2186 0.0388 1.0000 Uiso R . . . . .
H103 H 0.2492 0.0545 0.2541 0.0390 1.0000 Uiso R . . . . .
H111 H -0.1054 0.2433 0.2450 0.0310 1.0000 Uiso R . . . . .
H112 H -0.0252 0.1099 0.3053 0.0309 1.0000 Uiso R . . . . .
H131 H -0.1402 0.0833 0.4767 0.0481 1.0000 Uiso R . . . . .
H133 H -0.2532 0.2002 0.4830 0.0483 1.0000 Uiso R . . . . .
H132 H -0.1348 0.1465 0.6153 0.0483 1.0000 Uiso R . . . . .
H152 H 0.0947 0.4776 0.8063 0.0438 1.0000 Uiso R . . . . .
H151 H -0.0403 0.3306 0.7586 0.0444 1.0000 Uiso R . . . . .
H153 H 0.1746 0.3385 0.8300 0.0438 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.405(8) yes
C1 . C6 . 1.421(8) yes
C1 . O1 . 1.335(7) yes
C2 . C3 . 1.385(8) yes
C2 . H21 . 0.929 no
C3 . C4 . 1.384(9) yes
C3 . H31 . 0.929 no
C4 . C5 . 1.376(8) yes
C4 . H41 . 0.931 no
C5 . C6 . 1.426(8) yes
C5 . H51 . 0.927 no
C6 . C7 . 1.440(8) yes
C7 . N1 . 1.299(7) yes
C7 . H71 . 0.928 no
C8 . C9 . 1.527(8) yes
C8 . C10 . 1.526(8) yes
C8 . C11 . 1.541(8) yes
C8 . N1 . 1.483(7) yes
C9 . H93 . 0.962 no
C9 . H91 . 0.956 no
C9 . H92 . 0.956 no
C10 . H101 . 0.959 no
C10 . H102 . 0.962 no
C10 . H103 . 0.954 no
C11 . N2 . 1.461(7) yes
C11 . H111 . 0.967 no
C11 . H112 . 0.970 no
C12 . C13 . 1.494(7) yes
C12 . C14 . 1.434(8) yes
C12 . N2 . 1.309(7) yes
C13 . H131 . 0.952 no
C13 . H133 . 0.958 no
C13 . H132 . 0.954 no
C14 . C15 . 1.491(8) yes
C14 . N3 . 1.327(7) yes
C15 . H152 . 0.963 no
C15 . H151 . 0.952 no
C15 . H153 . 0.957 no
Cu1 . O1 2_666 2.572(4) yes
Cu1 . O1 . 1.910(4) yes
Cu1 . N1 . 1.968(4) yes
Cu1 . N2 . 1.929(4) yes
Cu1 . N3 . 2.034(4) yes
N3 . O2 . 1.267(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
C2 . C1 . C6 . 118.3(5) yes
C2 . C1 . O1 . 118.2(5) yes
C6 . C1 . O1 . 123.4(5) yes
C1 . C2 . C3 . 121.0(5) yes
C1 . C2 . H21 . 119.4 no
C3 . C2 . H21 . 119.6 no
C2 . C3 . C4 . 121.4(5) yes
C2 . C3 . H31 . 119.1 no
C4 . C3 . H31 . 119.5 no
C3 . C4 . C5 . 118.9(5) yes
C3 . C4 . H41 . 120.3 no
C5 . C4 . H41 . 120.7 no
C4 . C5 . C6 . 121.7(5) yes
C4 . C5 . H51 . 119.6 no
C6 . C5 . H51 . 118.7 no
C5 . C6 . C1 . 118.6(5) yes
C5 . C6 . C7 . 116.5(5) yes
C1 . C6 . C7 . 124.9(5) yes
C6 . C7 . N1 . 124.6(5) yes
C6 . C7 . H71 . 117.7 no
N1 . C7 . H71 . 117.7 no
C9 . C8 . C10 . 111.2(4) yes
C9 . C8 . C11 . 108.3(5) yes
C10 . C8 . C11 . 111.0(5) yes
C9 . C8 . N1 . 113.9(4) yes
C10 . C8 . N1 . 106.7(4) yes
C11 . C8 . N1 . 105.7(4) yes
C8 . C9 . H93 . 110.8 no
C8 . C9 . H91 . 109.4 no
H93 . C9 . H91 . 108.8 no
C8 . C9 . H92 . 110.3 no
H93 . C9 . H92 . 109.2 no
H91 . C9 . H92 . 108.2 no
C8 . C10 . H101 . 109.6 no
C8 . C10 . H102 . 109.3 no
H101 . C10 . H102 . 109.1 no
C8 . C10 . H103 . 108.9 no
H101 . C10 . H103 . 110.5 no
H102 . C10 . H103 . 109.4 no
C8 . C11 . N2 . 108.0(4) yes
C8 . C11 . H111 . 108.7 no
N2 . C11 . H111 . 109.8 no
C8 . C11 . H112 . 109.8 no
N2 . C11 . H112 . 110.9 no
H111 . C11 . H112 . 109.6 no
C13 . C12 . C14 . 122.8(5) yes
C13 . C12 . N2 . 121.6(5) yes
C14 . C12 . N2 . 115.5(5) yes
C12 . C13 . H131 . 110.7 no
C12 . C13 . H133 . 109.4 no
H131 . C13 . H133 . 109.0 no
C12 . C13 . H132 . 110.2 no
H131 . C13 . H132 . 108.8 no
H133 . C13 . H132 . 108.6 no
C12 . C14 . C15 . 124.4(5) yes
C12 . C14 . N3 . 115.7(5) yes
C15 . C14 . N3 . 119.9(5) yes
C14 . C15 . H152 . 109.8 no
C14 . C15 . H151 . 108.6 no
H152 . C15 . H151 . 109.7 no
C14 . C15 . H153 . 109.3 no
H152 . C15 . H153 . 109.5 no
H151 . C15 . H153 . 109.9 no
O1 2_666 Cu1 . O1 . 89.13(15) yes
O1 2_666 Cu1 . N1 . 103.69(15) yes
O1 . Cu1 . N1 . 94.46(17) yes
O1 2_666 Cu1 . N2 . 95.82(15) yes
O1 . Cu1 . N2 . 174.72(18) yes
N1 . Cu1 . N2 . 82.60(19) yes
O1 2_666 Cu1 . N3 . 85.16(14) yes
O1 . Cu1 . N3 . 100.94(17) yes
N1 . Cu1 . N3 . 162.40(17) yes
N2 . Cu1 . N3 . 81.37(19) yes
Cu1 2_666 O1 . C1 . 114.5(3) yes
Cu1 2_666 O1 . Cu1 . 90.87(15) yes
C1 . O1 . Cu1 . 125.2(3) yes
C8 . N1 . C7 . 121.2(4) yes
C8 . N1 . Cu1 . 113.9(3) yes
C7 . N1 . Cu1 . 124.7(4) yes
C11 . N2 . C12 . 125.8(4) yes
C11 . N2 . Cu1 . 115.9(3) yes
C12 . N2 . Cu1 . 115.5(4) yes
C14 . N3 . Cu1 . 111.0(3) yes
C14 . N3 . O2 . 121.5(4) yes
Cu1 . N3 . O2 . 126.9(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C11 . H111 . O2 2_566 135.75(15) 0.967 2.597 3.358(8) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/11/12 at 15:30:31
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  93,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) H   ( 153,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/11/12 at 15:30:31
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
2 0 0 x .
_database_code_depnum_ccdc_archive 'CCDC 996961'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cpd9

_audit_creation_date             2013-07-19T16:43:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H40 Cu2 N9 O14 Tb'
_chemical_formula_sum            'C30 H40 Cu2 N9 O14 Tb'
_chemical_formula_weight         1036.71
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.9478(5)
_cell_length_b                   18.4048(7)
_cell_length_c                   17.5548(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.735(2)
_cell_angle_gamma                90
_cell_volume                     3833.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9791
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      32.5
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2072
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_T_max  0.988

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_number            64206
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             7830
_reflns_number_gt                7080
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0170P)²+3.2529P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7830
_refine_ls_number_parameters     519
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0164
_refine_ls_wR_factor_ref         0.0408
_refine_ls_wR_factor_gt          0.0392
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.80974(16) 0.28543(10) 1.04078(10) 0.0139(4) Uani 1 1 d . . .
C2 C 0.83389(17) 0.35856(10) 1.02544(10) 0.0157(4) Uani 1 1 d . . .
H2 H 0.7735 0.392 1.0149 0.019 Uiso 1 1 calc R . .
C3 C 0.94326(17) 0.38267(11) 1.02539(11) 0.0185(4) Uani 1 1 d . . .
H3 H 0.9569 0.4324 1.0154 0.022 Uiso 1 1 calc R . .
C4 C 1.03409(18) 0.33498(12) 1.03980(11) 0.0210(4) Uani 1 1 d . . .
H4 H 1.1093 0.3518 1.0397 0.025 Uiso 1 1 calc R . .
C5 C 1.01276(18) 0.26353(11) 1.05410(12) 0.0202(4) Uani 1 1 d . . .
H5 H 1.0743 0.2308 1.0637 0.024 Uiso 1 1 calc R . .
C6 C 0.90240(17) 0.23688(10) 1.05511(11) 0.0168(4) Uani 1 1 d . . .
C7 C 0.89188(17) 0.16034(11) 1.07043(11) 0.0181(4) Uani 1 1 d . . .
H7 H 0.9594 0.1326 1.0772 0.022 Uiso 1 1 calc R . .
C8 C 0.79506(18) 0.04648(10) 1.09215(11) 0.0190(4) Uani 1 1 d . . .
C9 C 0.90698(19) 0.01477(12) 1.12756(13) 0.0258(5) Uani 1 1 d . . .
H9A H 0.9615 0.0165 1.09 0.039 Uiso 1 1 calc R . .
H9B H 0.8959 -0.0358 1.1425 0.039 Uiso 1 1 calc R . .
H9C H 0.9356 0.0431 1.1729 0.039 Uiso 1 1 calc R . .
C10 C 0.75439(19) 0.00769(11) 1.01674(11) 0.0219(4) Uani 1 1 d . . .
H10A H 0.6812 0.0275 0.9956 0.033 Uiso 1 1 calc R . .
H10B H 0.7469 -0.0444 1.0264 0.033 Uiso 1 1 calc R . .
H10C H 0.8092 0.0152 0.9801 0.033 Uiso 1 1 calc R . .
C11 C 0.70743(18) 0.03832(10) 1.14929(11) 0.0192(4) Uani 1 1 d . . .
H11A H 0.6802 -0.0125 1.1494 0.023 Uiso 1 1 calc R . .
H11B H 0.7419 0.0507 1.2017 0.023 Uiso 1 1 calc R . .
C12 C 0.52157(18) 0.09227(10) 1.15633(11) 0.0173(4) Uani 1 1 d . . .
C13 C 0.48938(19) 0.04689(11) 1.22086(12) 0.0226(5) Uani 1 1 d . . .
H13A H 0.4186 0.0214 1.2044 0.034 Uiso 1 1 calc R . .
H13B H 0.4795 0.0782 1.2648 0.034 Uiso 1 1 calc R . .
H13C H 0.5489 0.0113 1.2358 0.034 Uiso 1 1 calc R . .
C14 C 0.44474(17) 0.15135(10) 1.12524(11) 0.0166(4) Uani 1 1 d . . .
C15 C 0.32465(17) 0.15435(12) 1.14025(11) 0.0209(4) Uani 1 1 d . . .
H15A H 0.2889 0.1978 1.116 0.031 Uiso 1 1 calc R . .
H15B H 0.321 0.1563 1.1957 0.031 Uiso 1 1 calc R . .
H15C H 0.2851 0.111 1.1189 0.031 Uiso 1 1 calc R . .
C21 C 0.76452(16) 0.36611(10) 0.83071(10) 0.0140(4) Uani 1 1 d . . .
C22 C 0.76321(18) 0.43927(10) 0.85484(11) 0.0181(4) Uani 1 1 d . . .
H22 H 0.6939 0.4606 0.8645 0.022 Uiso 1 1 calc R . .
C23 C 0.86029(18) 0.48041(11) 0.86470(11) 0.0207(4) Uani 1 1 d . . .
H23 H 0.8564 0.5297 0.8801 0.025 Uiso 1 1 calc R . .
C24 C 0.96423(18) 0.45066(11) 0.85233(12) 0.0211(4) Uani 1 1 d . . .
H24 H 1.0309 0.4792 0.8595 0.025 Uiso 1 1 calc R . .
C25 C 0.96815(17) 0.37931(11) 0.82951(11) 0.0183(4) Uani 1 1 d . . .
H25 H 1.0387 0.3587 0.8215 0.022 Uiso 1 1 calc R . .
C26 C 0.87007(17) 0.33581(10) 0.81769(11) 0.0150(4) Uani 1 1 d . . .
C27 C 0.88603(17) 0.26122(10) 0.79544(11) 0.0146(4) Uani 1 1 d . . .
H27 H 0.9607 0.2456 0.7907 0.017 Uiso 1 1 calc R . .
C28 C 0.82870(16) 0.13677(10) 0.76399(11) 0.0145(4) Uani 1 1 d . . .
C29 C 0.82020(17) 0.09399(10) 0.83801(11) 0.0177(4) Uani 1 1 d . . .
H29A H 0.8771 0.1118 0.8785 0.027 Uiso 1 1 calc R . .
H29B H 0.8331 0.0423 0.8289 0.027 Uiso 1 1 calc R . .
H29C H 0.745 0.1006 0.854 0.027 Uiso 1 1 calc R . .
C30 C 0.94151(17) 0.12449(11) 0.73386(11) 0.0178(4) Uani 1 1 d . . .
H30A H 0.9472 0.1563 0.6897 0.027 Uiso 1 1 calc R . .
H30B H 0.9472 0.0737 0.7181 0.027 Uiso 1 1 calc R . .
H30C H 1.0027 0.1356 0.7743 0.027 Uiso 1 1 calc R . .
C31 C 0.73188(16) 0.11421(10) 0.70229(11) 0.0154(4) Uani 1 1 d . . .
H31A H 0.7465 0.1325 0.6513 0.019 Uiso 1 1 calc R . .
H31B H 0.7258 0.0606 0.6997 0.019 Uiso 1 1 calc R . .
C32 C 0.52836(16) 0.13289(10) 0.69124(10) 0.0141(4) Uani 1 1 d . . .
C33 C 0.50190(17) 0.07994(11) 0.62698(11) 0.0179(4) Uani 1 1 d . . .
H33A H 0.5224 0.1011 0.5793 0.027 Uiso 1 1 calc R . .
H33B H 0.4211 0.0689 0.621 0.027 Uiso 1 1 calc R . .
H33C H 0.5449 0.0351 0.6385 0.027 Uiso 1 1 calc R . .
C34 C 0.43866(16) 0.17717(10) 0.72164(10) 0.0147(4) Uani 1 1 d . . .
C35 C 0.31657(17) 0.16051(11) 0.70436(12) 0.0205(4) Uani 1 1 d . . .
H35A H 0.2729 0.195 0.7315 0.031 Uiso 1 1 calc R . .
H35B H 0.3021 0.111 0.7212 0.031 Uiso 1 1 calc R . .
H35C H 0.2942 0.1646 0.649 0.031 Uiso 1 1 calc R . .
N1 N 0.79919(14) 0.12642(8) 1.07566(9) 0.0161(3) Uani 1 1 d . . .
N2 N 0.61361(15) 0.08738(9) 1.12575(9) 0.0173(3) Uani 1 1 d . . .
N3 N 0.49414(14) 0.19855(8) 1.08476(9) 0.0143(3) Uani 1 1 d . . .
N5 N 0.62823(14) 0.14543(8) 0.72374(9) 0.0146(3) Uani 1 1 d . . .
N4 N 0.80623(13) 0.21450(8) 0.78166(9) 0.0129(3) Uani 1 1 d . . .
N6 N 0.48058(14) 0.22982(8) 0.76610(9) 0.0137(3) Uani 1 1 d . . .
N7 N 0.48566(14) 0.12949(9) 0.90648(9) 0.0164(3) Uani 1 1 d . . .
N8 N 0.15644(14) 0.20862(9) 0.91569(9) 0.0177(4) Uani 1 1 d . . .
N9 N 0.28477(14) 0.41657(9) 0.93152(10) 0.0186(4) Uani 1 1 d . . .
O1 O 0.70260(11) 0.26673(7) 1.04270(8) 0.0148(3) Uani 1 1 d . . .
O2 O 0.43618(11) 0.25495(7) 1.05351(7) 0.0156(3) Uani 1 1 d . . .
O3 O 0.66746(11) 0.33019(7) 0.82176(7) 0.0154(3) Uani 1 1 d . . .
O4 O 0.41216(11) 0.27318(7) 0.80030(7) 0.0162(3) Uani 1 1 d . . .
O5 O 0.54939(11) 0.34196(7) 0.94415(8) 0.0152(3) Uani 1 1 d D . .
H5A H 0.5809(16) 0.3435(12) 0.9019(7) 0.018 Uiso 1 1 d D . .
H5B H 0.5990(14) 0.3226(11) 0.9791(8) 0.018 Uiso 1 1 d D . .
O6 O 0.54728(11) 0.18428(7) 0.92648(8) 0.0167(3) Uani 1 1 d . . .
O7 O 0.52563(13) 0.06955(8) 0.89814(9) 0.0288(4) Uani 1 1 d . . .
O8 O 0.38021(11) 0.14062(7) 0.89562(8) 0.0199(3) Uani 1 1 d . . .
O9 O 0.22353(12) 0.20913(8) 0.97731(8) 0.0194(3) Uani 1 1 d . . .
O10 O 0.18598(12) 0.24653(8) 0.86048(8) 0.0219(3) Uani 1 1 d . . .
O11 O 0.06916(12) 0.17348(8) 0.90956(9) 0.0261(3) Uani 1 1 d . . .
O12 O 0.31785(13) 0.39261(8) 0.87009(8) 0.0226(3) Uani 1 1 d . . .
O13 O 0.29519(11) 0.37335(7) 0.98876(8) 0.0178(3) Uani 1 1 d . . .
O14 O 0.24550(14) 0.47745(8) 0.93558(10) 0.0319(4) Uani 1 1 d . . .
Tb1 Tb 0.380063(7) 0.272840(5) 0.925315(5) 0.01175(3) Uani 1 1 d . . .
Cu1 Cu 0.65308(2) 0.173863(12) 1.070756(13) 0.01340(5) Uani 1 1 d . . .
Cu2 Cu 0.647504(19) 0.234949(12) 0.782058(13) 0.01232(5) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.330(2) . ?
C1 C2 1.409(3) . ?
C1 C6 1.422(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.95 . ?
C3 C4 1.396(3) . ?
C3 H3 0.95 . ?
C4 C5 1.368(3) . ?
C4 H4 0.95 . ?
C5 C6 1.409(3) . ?
C5 H5 0.95 . ?
C6 C7 1.442(3) . ?
C7 N1 1.284(3) . ?
C7 H7 0.95 . ?
C8 N1 1.501(2) . ?
C8 C9 1.523(3) . ?
C8 C10 1.532(3) . ?
C8 C11 1.540(3) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 N2 1.461(3) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 N2 1.282(3) . ?
C12 C14 1.485(3) . ?
C12 C13 1.494(3) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 N3 1.306(2) . ?
C14 C15 1.490(3) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C21 O3 1.328(2) . ?
C21 C22 1.412(3) . ?
C21 C26 1.422(3) . ?
C22 C23 1.379(3) . ?
C22 H22 0.95 . ?
C23 C24 1.397(3) . ?
C23 H23 0.95 . ?
C24 C25 1.375(3) . ?
C24 H24 0.95 . ?
C25 C26 1.414(3) . ?
C25 H25 0.95 . ?
C26 C27 1.446(3) . ?
C27 N4 1.286(2) . ?
C27 H27 0.95 . ?
C28 N4 1.495(2) . ?
C28 C30 1.521(3) . ?
C28 C29 1.533(3) . ?
C28 C31 1.546(3) . ?
C29 H29A 0.98 . ?
C29 H29B 0.98 . ?
C29 H29C 0.98 . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 0.98 . ?
C31 N5 1.454(2) . ?
C31 H31A 0.99 . ?
C31 H31B 0.99 . ?
C32 N5 1.282(2) . ?
C32 C34 1.494(3) . ?
C32 C33 1.496(3) . ?
C33 H33A 0.98 . ?
C33 H33B 0.98 . ?
C33 H33C 0.98 . ?
C34 N6 1.307(2) . ?
C34 C35 1.487(3) . ?
C35 H35A 0.98 . ?
C35 H35B 0.98 . ?
C35 H35C 0.98 . ?
N1 Cu1 1.9448(16) . ?
N2 Cu1 1.9481(16) . ?
N3 O2 1.330(2) . ?
N3 Cu1 1.9956(16) . ?
N5 Cu2 1.9392(16) . ?
N4 Cu2 1.9342(16) . ?
N6 O4 1.334(2) . ?
N6 Cu2 1.9834(16) . ?
N7 O7 1.218(2) . ?
N7 O8 1.269(2) . ?
N7 O6 1.273(2) . ?
N7 Tb1 2.9596(16) . ?
N8 O11 1.221(2) . ?
N8 O9 1.269(2) . ?
N8 O10 1.277(2) . ?
N8 Tb1 2.9084(17) . ?
N9 O14 1.220(2) . ?
N9 O12 1.270(2) . ?
N9 O13 1.276(2) . ?
N9 Tb1 2.8870(16) . ?
O1 Cu1 1.8927(13) . ?
O2 Tb1 2.2954(13) . ?
O3 Cu2 1.8911(13) . ?
O4 Tb1 2.2718(13) . ?
O5 Tb1 2.3798(13) . ?
O5 H5A 0.871(9) . ?
O5 H5B 0.876(9) . ?
O6 Tb1 2.5766(13) . ?
O8 Tb1 2.4887(14) . ?
O9 Tb1 2.4711(14) . ?
O10 Tb1 2.5076(14) . ?
O12 Tb1 2.4864(14) . ?
O13 Tb1 2.4405(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 118.12(17) . . ?
O1 C1 C6 124.39(17) . . ?
C2 C1 C6 117.48(18) . . ?
C3 C2 C1 121.49(19) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.93(19) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.68(19) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 122.12(19) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 119.30(18) . . ?
C5 C6 C7 116.40(18) . . ?
C1 C6 C7 124.30(18) . . ?
N1 C7 C6 125.66(18) . . ?
N1 C7 H7 117.2 . . ?
C6 C7 H7 117.2 . . ?
N1 C8 C9 114.01(17) . . ?
N1 C8 C10 107.72(16) . . ?
C9 C8 C10 110.39(17) . . ?
N1 C8 C11 105.16(15) . . ?
C9 C8 C11 109.16(17) . . ?
C10 C8 C11 110.27(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C8 108.26(15) . . ?
N2 C11 H11A 110 . . ?
C8 C11 H11A 110 . . ?
N2 C11 H11B 110 . . ?
C8 C11 H11B 110 . . ?
H11A C11 H11B 108.4 . . ?
N2 C12 C14 114.90(17) . . ?
N2 C12 C13 126.02(19) . . ?
C14 C12 C13 119.02(18) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C12 112.81(18) . . ?
N3 C14 C15 125.27(19) . . ?
C12 C14 C15 121.92(17) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C21 C22 118.03(17) . . ?
O3 C21 C26 124.36(17) . . ?
C22 C21 C26 117.61(18) . . ?
C23 C22 C21 121.49(19) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C22 C23 C24 121.01(19) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 118.73(19) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C26 121.8(2) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 H25 119.1 . . ?
C25 C26 C21 119.32(18) . . ?
C25 C26 C27 116.35(18) . . ?
C21 C26 C27 124.29(18) . . ?
N4 C27 C26 124.57(18) . . ?
N4 C27 H27 117.7 . . ?
C26 C27 H27 117.7 . . ?
N4 C28 C30 113.73(16) . . ?
N4 C28 C29 106.52(15) . . ?
C30 C28 C29 111.58(16) . . ?
N4 C28 C31 105.34(15) . . ?
C30 C28 C31 109.71(15) . . ?
C29 C28 C31 109.72(16) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N5 C31 C28 107.61(15) . . ?
N5 C31 H31A 110.2 . . ?
C28 C31 H31A 110.2 . . ?
N5 C31 H31B 110.2 . . ?
C28 C31 H31B 110.2 . . ?
H31A C31 H31B 108.5 . . ?
N5 C32 C34 114.34(17) . . ?
N5 C32 C33 123.79(18) . . ?
C34 C32 C33 121.85(17) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N6 C34 C35 124.96(18) . . ?
N6 C34 C32 112.16(17) . . ?
C35 C34 C32 122.86(17) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C7 N1 C8 122.58(17) . . ?
C7 N1 Cu1 123.77(14) . . ?
C8 N1 Cu1 113.51(13) . . ?
C12 N2 C11 126.33(17) . . ?
C12 N2 Cu1 114.80(13) . . ?
C11 N2 Cu1 115.02(13) . . ?
C14 N3 O2 119.79(16) . . ?
C14 N3 Cu1 114.37(13) . . ?
O2 N3 Cu1 125.73(12) . . ?
C32 N5 C31 126.18(16) . . ?
C32 N5 Cu2 115.77(13) . . ?
C31 N5 Cu2 114.86(12) . . ?
C27 N4 C28 122.13(16) . . ?
C27 N4 Cu2 125.10(14) . . ?
C28 N4 Cu2 112.77(12) . . ?
C34 N6 O4 120.01(16) . . ?
C34 N6 Cu2 115.36(13) . . ?
O4 N6 Cu2 124.53(12) . . ?
O7 N7 O8 121.66(17) . . ?
O7 N7 O6 121.89(16) . . ?
O8 N7 O6 116.45(15) . . ?
O7 N7 Tb1 177.87(14) . . ?
O8 N7 Tb1 56.22(9) . . ?
O6 N7 Tb1 60.23(9) . . ?
O11 N8 O9 121.78(17) . . ?
O11 N8 O10 122.13(16) . . ?
O9 N8 O10 116.09(16) . . ?
O11 N8 Tb1 171.74(13) . . ?
O9 N8 Tb1 57.53(9) . . ?
O10 N8 Tb1 59.22(9) . . ?
O14 N9 O12 121.90(17) . . ?
O14 N9 O13 121.95(17) . . ?
O12 N9 O13 116.16(15) . . ?
O14 N9 Tb1 178.75(15) . . ?
O12 N9 Tb1 59.11(9) . . ?
O13 N9 Tb1 57.05(9) . . ?
C1 O1 Cu1 124.86(12) . . ?
N3 O2 Tb1 126.47(10) . . ?
C21 O3 Cu2 125.14(12) . . ?
N6 O4 Tb1 127.93(10) . . ?
Tb1 O5 H5A 110.1(14) . . ?
Tb1 O5 H5B 111.9(14) . . ?
H5A O5 H5B 106.6(13) . . ?
N7 O6 Tb1 94.36(10) . . ?
N7 O8 Tb1 98.72(10) . . ?
N8 O9 Tb1 96.80(11) . . ?
N8 O10 Tb1 94.83(10) . . ?
N9 O12 Tb1 94.89(10) . . ?
N9 O13 Tb1 96.92(10) . . ?
O4 Tb1 O2 152.20(5) . . ?
O4 Tb1 O5 84.01(5) . . ?
O2 Tb1 O5 78.15(5) . . ?
O4 Tb1 O13 124.41(5) . . ?
O2 Tb1 O13 75.55(5) . . ?
O5 Tb1 O13 85.61(5) . . ?
O4 Tb1 O9 125.38(5) . . ?
O2 Tb1 O9 73.53(5) . . ?
O5 Tb1 O9 150.48(5) . . ?
O13 Tb1 O9 79.52(5) . . ?
O4 Tb1 O12 72.39(5) . . ?
O2 Tb1 O12 123.30(5) . . ?
O5 Tb1 O12 77.92(5) . . ?
O13 Tb1 O12 52.03(4) . . ?
O9 Tb1 O12 111.11(5) . . ?
O4 Tb1 O8 78.23(5) . . ?
O2 Tb1 O8 93.32(5) . . ?
O5 Tb1 O8 122.03(4) . . ?
O13 Tb1 O8 147.92(5) . . ?
O9 Tb1 O8 68.44(5) . . ?
O12 Tb1 O8 142.44(5) . . ?
O4 Tb1 O10 79.28(5) . . ?
O2 Tb1 O10 124.44(5) . . ?
O5 Tb1 O10 153.14(5) . . ?
O13 Tb1 O10 86.67(5) . . ?
O9 Tb1 O10 51.42(5) . . ?
O12 Tb1 O10 77.06(5) . . ?
O8 Tb1 O10 74.90(5) . . ?
O4 Tb1 O6 77.93(4) . . ?
O2 Tb1 O6 76.37(4) . . ?
O5 Tb1 O6 72.02(4) . . ?
O13 Tb1 O6 147.05(4) . . ?
O9 Tb1 O6 108.46(5) . . ?
O12 Tb1 O6 139.46(5) . . ?
O8 Tb1 O6 50.47(4) . . ?
O10 Tb1 O6 123.80(5) . . ?
O4 Tb1 N9 98.39(5) . . ?
O2 Tb1 N9 99.53(5) . . ?
O5 Tb1 N9 80.65(5) . . ?
O13 Tb1 N9 26.03(5) . . ?
O9 Tb1 N9 95.85(5) . . ?
O12 Tb1 N9 26.00(5) . . ?
O8 Tb1 N9 156.04(5) . . ?
O10 Tb1 N9 81.16(5) . . ?
O6 Tb1 N9 152.65(5) . . ?
O4 Tb1 N8 101.71(5) . . ?
O2 Tb1 N8 99.17(5) . . ?
O5 Tb1 N8 170.24(5) . . ?
O13 Tb1 N8 84.64(5) . . ?
O9 Tb1 N8 25.67(4) . . ?
O12 Tb1 N8 96.15(5) . . ?
O8 Tb1 N8 67.27(5) . . ?
O10 Tb1 N8 25.95(5) . . ?
O6 Tb1 N8 116.71(4) . . ?
N9 Tb1 N8 90.62(5) . . ?
O4 Tb1 N7 76.83(4) . . ?
O2 Tb1 N7 84.40(4) . . ?
O5 Tb1 N7 97.21(5) . . ?
O13 Tb1 N7 158.76(4) . . ?
O9 Tb1 N7 88.24(5) . . ?
O12 Tb1 N7 149.16(4) . . ?
O8 Tb1 N7 25.07(4) . . ?
O10 Tb1 N7 99.25(5) . . ?
O6 Tb1 N7 25.40(4) . . ?
N9 Tb1 N7 174.98(5) . . ?
N8 Tb1 N7 91.83(5) . . ?
O1 Cu1 N1 96.35(6) . . ?
O1 Cu1 N2 165.48(6) . . ?
N1 Cu1 N2 83.07(7) . . ?
O1 Cu1 N3 99.06(6) . . ?
N1 Cu1 N3 163.54(7) . . ?
N2 Cu1 N3 80.55(7) . . ?
O3 Cu2 N4 95.76(6) . . ?
O3 Cu2 N5 169.78(6) . . ?
N4 Cu2 N5 83.60(7) . . ?
O3 Cu2 N6 100.22(6) . . ?
N4 Cu2 N6 163.80(6) . . ?
N5 Cu2 N6 80.20(7) . . ?
_database_code_depnum_ccdc_archive 'CCDC 996962'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cpd13

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

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

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

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

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

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.5144(4)
_cell_length_b                   11.4478(4)
_cell_length_c                   11.5167(4)
_cell_angle_alpha                86.825(2)
_cell_angle_beta                 85.037(2)
_cell_angle_gamma                89.709(2)
_cell_volume                     1378.91(9)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
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'
Ho -0.2175 4.6783 26.9049 2.0705 17.2940 0.1979 14.5583 11.4407 3.6384 92.6566
4.5680 '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'


_cell_formula_units_Z            2

# Given Formula = C18 H29 Cu1 Ho1 N6 O14 
# Dc =      1.88 Fooo =    774.00 Mu =     36.95 M =    781.94
# Found Formula = C18 H29 Cu1 Ho1 N6 O14 
# Dc =      1.88 FOOO =    774.00 Mu =     36.95 M =    781.94

_chemical_formula_sum            'C18 H29 Cu1 Ho1 N6 O14'
_chemical_formula_moiety         'C15 H23 Cu Ho N6 O13, C3 H6 O'
_chemical_compound_source        ?
_chemical_formula_weight         781.94


_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2
_cell_measurement_theta_max      36
_cell_measurement_temperature    100

_exptl_crystal_description       planar
_exptl_crystal_colour            pink
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.883
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             774
_exptl_absorpt_coefficient_mu    3.695

# Sheldrick geometric approximatio 0.57 0.93 
_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  0.93
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

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

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            35046
_reflns_number_total             12207
_diffrn_reflns_av_R_equivalents  0.031
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 12207 
# Theoretical number of reflections is about 27379 


_diffrn_reflns_theta_min         1.782
_diffrn_reflns_theta_max         36.666
_diffrn_measured_fraction_theta_max 0.892

_diffrn_reflns_theta_full        25.300
_diffrn_measured_fraction_theta_full 0.982


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -16
_reflns_limit_h_max              17
_reflns_limit_k_min              -18
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              19

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

_refine_diff_density_min         -0.77
_refine_diff_density_max         0.93


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         9933
_refine_ls_number_restraints     0
_refine_ls_number_parameters     361
_oxford_refine_ls_R_factor_ref   0.0262
_refine_ls_wR_factor_ref         0.0225
_refine_ls_goodness_of_fit_ref   1.1006
_refine_ls_shift/su_max          0.0009846
_refine_ls_shift/su_mean         0.0000274


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        12185
_refine_ls_R_factor_all          0.0387
_refine_ls_wR_factor_all         0.0303

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                10378
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_gt          0.0233

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


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.313 0.291 0.281 0.147 0.872E-01 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C2 C 0.47834(17) 0.72815(16) -0.31926(15) 0.0122 1.0000 Uani . . . . . .
C3 C 0.56188(18) 0.82459(17) -0.32554(16) 0.0146 1.0000 Uani . . . . . .
C4 C 0.59919(19) 0.88384(17) -0.43103(17) 0.0163 1.0000 Uani . . . . . .
C5 C 0.5573(2) 0.84803(18) -0.53506(17) 0.0177 1.0000 Uani . . . . . .
C6 C 0.47709(19) 0.75205(18) -0.53122(17) 0.0166 1.0000 Uani . . . . . .
C7 C 0.43621(17) 0.69070(17) -0.42497(15) 0.0133 1.0000 Uani . . . . . .
C8 C 0.34876(18) 0.59445(17) -0.43229(16) 0.0142 1.0000 Uani . . . . . .
C10 C 0.20104(18) 0.44007(17) -0.35641(17) 0.0151 1.0000 Uani . . . . . .
C11 C 0.2240(2) 0.34057(17) -0.26405(17) 0.0166 1.0000 Uani . . . . . .
C13 C 0.2066(2) 0.39098(19) -0.47779(18) 0.0192 1.0000 Uani . . . . . .
C14 C 0.07157(19) 0.49902(19) -0.32744(19) 0.0188 1.0000 Uani . . . . . .
C15 C 0.25398(18) 0.34550(17) -0.05485(17) 0.0151 1.0000 Uani . . . . . .
C16 C 0.29126(18) 0.42473(16) 0.03497(16) 0.0136 1.0000 Uani . . . . . .
C18 C 0.2245(2) 0.22002(18) -0.0224(2) 0.0222 1.0000 Uani . . . . . .
C19 C 0.2676(2) 0.39824(19) 0.16334(17) 0.0179 1.0000 Uani . . . . . .
C20 C 0.0471(2) 0.90957(19) -0.26014(18) 0.0194 1.0000 Uani . . . . . .
C21 C 0.1785(2) 0.8840(3) -0.3127(2) 0.0325 1.0000 Uani . . . . . .
C22 C -0.0628(3) 0.8852(3) -0.3293(3) 0.0361 1.0000 Uani . . . . . .
O1 O 0.18189(13) 0.71083(13) -0.07223(12) 0.0159 1.0000 Uani . . . . . .
O2 O 0.08028(15) 0.66776(15) 0.09596(13) 0.0207 1.0000 Uani . . . . . .
O3 O -0.00060(16) 0.62018(18) -0.06382(16) 0.0308 1.0000 Uani . . . . . .
O4 O 0.38988(15) 0.94874(14) 0.15154(14) 0.0209 1.0000 Uani . . . . . .
O5 O 0.48781(14) 0.78554(13) 0.18493(13) 0.0177 1.0000 Uani . . . . . .
O6 O 0.59178(15) 0.95058(13) 0.18100(13) 0.0191 1.0000 Uani . . . . . .
O7 O 0.24049(15) 0.67360(14) 0.29673(12) 0.0183 1.0000 Uani . . . . . .
O8 O 0.14978(19) 0.84139(15) 0.27079(14) 0.0281 1.0000 Uani . . . . . .
O9 O 0.11714(18) 0.74422(17) 0.43873(14) 0.0289 1.0000 Uani . . . . . .
O10 O 0.37500(14) 0.60094(12) 0.06424(12) 0.0149 1.0000 Uani . . . . . .
O11 O 0.42031(14) 0.83247(13) -0.05534(12) 0.0169 1.0000 Uani . . . . . .
O12 O 0.15919(15) 0.92955(14) 0.03559(13) 0.0196 1.0000 Uani . . . . . .
O13 O 0.44341(13) 0.67799(13) -0.21463(11) 0.0146 1.0000 Uani . . . . . .
O14 O 0.02893(17) 0.94684(17) -0.16297(14) 0.0272 1.0000 Uani . . . . . .
N1 N 0.08362(16) 0.66403(16) -0.01481(16) 0.0174 1.0000 Uani . . . . . .
N2 N 0.49215(17) 0.89631(15) 0.17325(14) 0.0156 1.0000 Uani . . . . . .
N3 N 0.16718(17) 0.75312(16) 0.33860(15) 0.0183 1.0000 Uani . . . . . .
N4 N 0.30080(15) 0.53030(14) -0.34443(14) 0.0132 1.0000 Uani . . . . . .
N5 N 0.25288(16) 0.39483(14) -0.15771(15) 0.0150 1.0000 Uani . . . . . .
N6 N 0.34104(15) 0.52263(14) -0.00901(14) 0.0125 1.0000 Uani . . . . . .
Cu1 Cu 0.33737(2) 0.54507(2) -0.182311(19) 0.0114 1.0000 Uani . . . . . .
Ho1 Ho 0.280634(9) 0.769967(8) 0.101544(8) 0.0102 1.0000 Uani . . . . . .
H31 H 0.5904 0.8500 -0.2572 0.0182 1.0000 Uiso R . . . . .
H41 H 0.6523 0.9483 -0.4316 0.0199 1.0000 Uiso R . . . . .
H51 H 0.5834 0.8881 -0.6056 0.0207 1.0000 Uiso R . . . . .
H61 H 0.4495 0.7264 -0.6011 0.0201 1.0000 Uiso R . . . . .
H81 H 0.3262 0.5795 -0.5078 0.0166 1.0000 Uiso R . . . . .
H111 H 0.1502 0.2907 -0.2497 0.0197 1.0000 Uiso R . . . . .
H112 H 0.2959 0.2934 -0.2903 0.0199 1.0000 Uiso R . . . . .
H113 H 0.4356 0.7805 -0.1011 0.0265 1.0000 Uiso R . . . . .
H114 H 0.4220 0.8994 -0.0867 0.0262 1.0000 Uiso R . . . . .
H121 H 0.1122 0.9669 0.0797 0.0296 1.0000 Uiso R . . . . .
H122 H 0.1426 0.9345 -0.0321 0.0297 1.0000 Uiso R . . . . .
H131 H 0.1813 0.4495 -0.5340 0.0284 1.0000 Uiso R . . . . .
H132 H 0.2905 0.3649 -0.5016 0.0287 1.0000 Uiso R . . . . .
H133 H 0.1489 0.3263 -0.4755 0.0287 1.0000 Uiso R . . . . .
H141 H 0.0669 0.5285 -0.2506 0.0290 1.0000 Uiso R . . . . .
H142 H 0.0587 0.5618 -0.3843 0.0289 1.0000 Uiso R . . . . .
H143 H 0.0039 0.4427 -0.3297 0.0290 1.0000 Uiso R . . . . .
H181 H 0.2983 0.1822 0.0055 0.0330 1.0000 Uiso R . . . . .
H182 H 0.2006 0.1821 -0.0884 0.0336 1.0000 Uiso R . . . . .
H183 H 0.1566 0.2129 0.0383 0.0332 1.0000 Uiso R . . . . .
H191 H 0.1923 0.4364 0.1933 0.0275 1.0000 Uiso R . . . . .
H192 H 0.2574 0.3165 0.1790 0.0277 1.0000 Uiso R . . . . .
H193 H 0.3377 0.4228 0.2023 0.0278 1.0000 Uiso R . . . . .
H211 H 0.1885 0.8003 -0.3171 0.0498 1.0000 Uiso R . . . . .
H212 H 0.1906 0.9209 -0.3894 0.0493 1.0000 Uiso R . . . . .
H213 H 0.2400 0.9143 -0.2658 0.0492 1.0000 Uiso R . . . . .
H221 H -0.0601 0.8054 -0.3505 0.0546 1.0000 Uiso R . . . . .
H222 H -0.0570 0.9344 -0.3994 0.0544 1.0000 Uiso R . . . . .
H223 H -0.1422 0.9008 -0.2842 0.0541 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C2 . C3 . 1.409(3) yes
C2 . C7 . 1.420(3) yes
C2 . O13 . 1.329(2) yes
C3 . C4 . 1.385(3) yes
C3 . H31 . 0.928 no
C4 . C5 . 1.395(3) yes
C4 . H41 . 0.927 no
C5 . C6 . 1.385(3) yes
C5 . H51 . 0.931 no
C6 . C7 . 1.411(3) yes
C6 . H61 . 0.941 no
C7 . C8 . 1.449(3) yes
C8 . N4 . 1.285(2) yes
C8 . H81 . 0.946 no
C10 . C11 . 1.547(3) yes
C10 . C13 . 1.532(3) yes
C10 . C14 . 1.535(3) yes
C10 . N4 . 1.496(2) yes
C11 . N5 . 1.459(3) yes
C11 . H111 . 0.963 no
C11 . H112 . 0.964 no
C13 . H131 . 0.959 no
C13 . H132 . 0.953 no
C13 . H133 . 0.958 no
C14 . H141 . 0.962 no
C14 . H142 . 0.962 no
C14 . H143 . 0.966 no
C15 . C16 . 1.491(3) yes
C15 . C18 . 1.491(3) yes
C15 . N5 . 1.285(2) yes
C16 . C19 . 1.492(3) yes
C16 . N6 . 1.298(2) yes
C18 . H181 . 0.958 no
C18 . H182 . 0.948 no
C18 . H183 . 0.955 no
C19 . H191 . 0.950 no
C19 . H192 . 0.948 no
C19 . H193 . 0.946 no
C20 . C21 . 1.494(3) yes
C20 . C22 . 1.495(3) yes
C20 . O14 . 1.219(3) yes
C21 . H211 . 0.967 no
C21 . H212 . 0.956 no
C21 . H213 . 0.957 no
C22 . H221 . 0.958 no
C22 . H222 . 0.956 no
C22 . H223 . 0.965 no
O1 . N1 . 1.281(2) yes
O1 . Cu1 . 2.7851(14) yes
O1 . Ho1 . 2.4613(14) yes
O2 . N1 . 1.276(2) yes
O2 . Ho1 . 2.4223(15) yes
O3 . N1 . 1.215(2) yes
O4 . N2 . 1.266(2) yes
O4 . Ho1 . 2.4715(16) yes
O5 . N2 . 1.268(2) yes
O5 . Ho1 . 2.4665(15) yes
O6 . N2 . 1.233(2) yes
O7 . N3 . 1.278(2) yes
O7 . Ho1 . 2.4524(14) yes
O8 . N3 . 1.265(2) yes
O8 . Ho1 . 2.4621(16) yes
O9 . N3 . 1.225(2) yes
O10 . N6 . 1.335(2) yes
O10 . Ho1 . 2.2163(14) yes
O11 . Ho1 . 2.3112(14) yes
O11 . H113 . 0.822 no
O11 . H114 . 0.828 no
O12 . Ho1 . 2.3528(15) yes
O12 . H121 . 0.814 no
O12 . H122 . 0.813 no
O13 . Cu1 . 1.8920(14) yes
N4 . Cu1 . 1.9551(16) yes
N5 . Cu1 . 1.9354(17) yes
N6 . Cu1 . 2.0018(16) 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
C3 . C2 . C7 . 118.07(16) yes
C3 . C2 . O13 . 117.98(16) yes
C7 . C2 . O13 . 123.95(17) yes
C2 . C3 . C4 . 121.32(18) yes
C2 . C3 . H31 . 119.1 no
C4 . C3 . H31 . 119.6 no
C3 . C4 . C5 . 120.84(18) yes
C3 . C4 . H41 . 119.0 no
C5 . C4 . H41 . 120.2 no
C4 . C5 . C6 . 118.81(18) yes
C4 . C5 . H51 . 120.2 no
C6 . C5 . H51 . 120.9 no
C5 . C6 . C7 . 121.68(18) yes
C5 . C6 . H61 . 119.5 no
C7 . C6 . H61 . 118.9 no
C2 . C7 . C6 . 119.24(17) yes
C2 . C7 . C8 . 124.43(16) yes
C6 . C7 . C8 . 116.29(17) yes
C7 . C8 . N4 . 124.65(17) yes
C7 . C8 . H81 . 116.3 no
N4 . C8 . H81 . 119.0 no
C11 . C10 . C13 . 109.79(16) yes
C11 . C10 . C14 . 110.52(16) yes
C13 . C10 . C14 . 110.35(16) yes
C11 . C10 . N4 . 105.80(15) yes
C13 . C10 . N4 . 113.81(16) yes
C14 . C10 . N4 . 106.44(16) yes
C10 . C11 . N5 . 107.54(15) yes
C10 . C11 . H111 . 110.9 no
N5 . C11 . H111 . 111.0 no
C10 . C11 . H112 . 110.5 no
N5 . C11 . H112 . 108.6 no
H111 . C11 . H112 . 108.4 no
C10 . C13 . H131 . 110.4 no
C10 . C13 . H132 . 111.1 no
H131 . C13 . H132 . 108.9 no
C10 . C13 . H133 . 108.9 no
H131 . C13 . H133 . 108.5 no
H132 . C13 . H133 . 109.0 no
C10 . C14 . H141 . 110.7 no
C10 . C14 . H142 . 110.1 no
H141 . C14 . H142 . 109.9 no
C10 . C14 . H143 . 109.6 no
H141 . C14 . H143 . 108.4 no
H142 . C14 . H143 . 108.2 no
C16 . C15 . C18 . 120.28(17) yes
C16 . C15 . N5 . 114.19(17) yes
C18 . C15 . N5 . 125.52(19) yes
C15 . C16 . C19 . 123.86(17) yes
C15 . C16 . N6 . 113.47(16) yes
C19 . C16 . N6 . 122.59(18) yes
C15 . C18 . H181 . 109.5 no
C15 . C18 . H182 . 110.0 no
H181 . C18 . H182 . 109.2 no
C15 . C18 . H183 . 110.8 no
H181 . C18 . H183 . 108.1 no
H182 . C18 . H183 . 109.2 no
C16 . C19 . H191 . 110.5 no
C16 . C19 . H192 . 109.9 no
H191 . C19 . H192 . 108.5 no
C16 . C19 . H193 . 110.4 no
H191 . C19 . H193 . 109.3 no
H192 . C19 . H193 . 108.1 no
C21 . C20 . C22 . 117.9(2) yes
C21 . C20 . O14 . 121.5(2) yes
C22 . C20 . O14 . 120.6(2) yes
C20 . C21 . H211 . 109.0 no
C20 . C21 . H212 . 109.6 no
H211 . C21 . H212 . 109.6 no
C20 . C21 . H213 . 109.5 no
H211 . C21 . H213 . 110.4 no
H212 . C21 . H213 . 108.8 no
C20 . C22 . H221 . 109.9 no
C20 . C22 . H222 . 109.4 no
H221 . C22 . H222 . 108.2 no
C20 . C22 . H223 . 109.9 no
H221 . C22 . H223 . 110.2 no
H222 . C22 . H223 . 109.2 no
N1 . O1 . Cu1 . 111.90(11) yes
N1 . O1 . Ho1 . 94.96(11) yes
Cu1 . O1 . Ho1 . 108.88(5) yes
N1 . O2 . Ho1 . 96.94(11) yes
N2 . O4 . Ho1 . 94.51(11) yes
N2 . O5 . Ho1 . 94.68(11) yes
N3 . O7 . Ho1 . 95.93(11) yes
N3 . O8 . Ho1 . 95.83(12) yes
N6 . O10 . Ho1 . 127.34(11) yes
Ho1 . O11 . H113 . 111.8 no
Ho1 . O11 . H114 . 124.8 no
H113 . O11 . H114 . 114.1 no
Ho1 . O12 . H121 . 122.5 no
Ho1 . O12 . H122 . 119.2 no
H121 . O12 . H122 . 114.7 no
C2 . O13 . Cu1 . 126.53(12) yes
O1 . N1 . O2 . 115.54(16) yes
O1 . N1 . O3 . 121.53(18) yes
O2 . N1 . O3 . 122.93(18) yes
O5 . N2 . O4 . 116.98(17) yes
O5 . N2 . O6 . 121.64(17) yes
O4 . N2 . O6 . 121.37(18) yes
O7 . N3 . O8 . 116.13(16) yes
O7 . N3 . O9 . 121.75(19) yes
O8 . N3 . O9 . 122.12(19) yes
C10 . N4 . C8 . 121.93(16) yes
C10 . N4 . Cu1 . 112.52(12) yes
C8 . N4 . Cu1 . 125.40(13) yes
C11 . N5 . C15 . 127.37(17) yes
C11 . N5 . Cu1 . 114.93(12) yes
C15 . N5 . Cu1 . 115.91(14) yes
O10 . N6 . C16 . 118.19(16) yes
O10 . N6 . Cu1 . 127.27(12) yes
C16 . N6 . Cu1 . 114.07(13) yes
N6 . Cu1 . O1 . 70.12(5) yes
N6 . Cu1 . N4 . 164.00(7) yes
O1 . Cu1 . N4 . 112.09(6) yes
N6 . Cu1 . N5 . 80.68(7) yes
O1 . Cu1 . N5 . 108.10(6) yes
N4 . Cu1 . N5 . 83.68(7) yes
N6 . Cu1 . O13 . 101.07(6) yes
O1 . Cu1 . O13 . 80.90(5) yes
N4 . Cu1 . O13 . 94.91(6) yes
N5 . Cu1 . O13 . 170.77(7) yes
O4 . Ho1 . O5 . 51.89(5) yes
O4 . Ho1 . O8 . 74.97(6) yes
O5 . Ho1 . O8 . 96.20(6) yes
O4 . Ho1 . O1 . 134.24(5) yes
O5 . Ho1 . O1 . 142.74(5) yes
O8 . Ho1 . O1 . 121.05(6) yes
O4 . Ho1 . O7 . 99.85(5) yes
O5 . Ho1 . O7 . 76.79(5) yes
O8 . Ho1 . O7 . 52.09(5) yes
O1 . Ho1 . O7 . 124.25(5) yes
O4 . Ho1 . O2 . 147.27(5) yes
O5 . Ho1 . O2 . 149.05(5) yes
O8 . Ho1 . O2 . 77.03(6) yes
O1 . Ho1 . O2 . 52.57(5) yes
O7 . Ho1 . O2 . 75.37(5) yes
O4 . Ho1 . O12 . 73.36(5) yes
O5 . Ho1 . O12 . 124.97(5) yes
O8 . Ho1 . O12 . 72.00(5) yes
O1 . Ho1 . O12 . 72.73(5) yes
O7 . Ho1 . O12 . 122.82(5) yes
O4 . Ho1 . O11 . 71.19(5) yes
O5 . Ho1 . O11 . 75.76(5) yes
O8 . Ho1 . O11 . 142.23(6) yes
O1 . Ho1 . O11 . 74.77(5) yes
O7 . Ho1 . O11 . 150.42(5) yes
O4 . Ho1 . O10 . 125.39(5) yes
O5 . Ho1 . O10 . 76.49(5) yes
O8 . Ho1 . O10 . 133.80(5) yes
O1 . Ho1 . O10 . 76.82(5) yes
O7 . Ho1 . O10 . 82.15(5) yes
O2 . Ho1 . O12 . 82.16(6) yes
O2 . Ho1 . O11 . 127.34(5) yes
O12 . Ho1 . O11 . 82.57(6) yes
O2 . Ho1 . O10 . 86.54(5) yes
O12 . Ho1 . O10 . 148.24(5) yes
O11 . Ho1 . O10 . 80.96(5) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C5 . H51 . O6 1_554 160.00 0.931 2.515 3.402(3) yes
C6 . H61 . O5 1_554 136.00 0.941 2.518 3.262(3) yes
O11 . H113 . O13 . 169.00 0.822 1.801 2.613(3) yes
O11 . H114 . O6 2_675 171.00 0.828 1.992 2.812(3) yes
O12 . H121 . O14 2_575 168.00 0.814 1.985 2.787(3) yes
O12 . H122 . O14 . 156.00 0.813 2.001 2.763(3) yes
C14 . H141 . O3 . 165.00 0.962 2.492 3.431(3) yes
C19 . H193 . O13 2_665 128.00 0.946 2.581 3.251(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/09/13 at 15:32:25
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  21,X'S) H   ( 212,X'S) H   ( 211,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 222,X'S) H   ( 221,X'S) H   ( 223,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  18,X'S) H   ( 182,X'S) H   ( 181,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 192,X'S) H   ( 191,X'S) H   ( 193,X'S) 
RIDE O  (  11,X'S) H   ( 113,X'S) H   ( 114,X'S) 
RIDE O   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/09/13 at 15:32:25
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;



_database_code_depnum_ccdc_archive 'CCDC 996963'
