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

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

data_global
_database_code_depnum_ccdc_archive 'CCDC 1535639'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_audit_creation_date             10-12-14
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title II_Co
_chemical_name_systematic        ?
_chemical_melting_point          ?

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   11.5798(18)
_cell_length_b                   12.053(2)
_cell_length_c                   22.060(5)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     3079.0(8)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
Co 0.3494 0.9721 12.2841 4.2791 7.3409 0.2784 4.0034 13.5359 2.3488 71.1692
1.0118 '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            4

# Given Formula = C30 H30 Co2 N2 O12 
# Dc =      1.57 Fooo =   1508.00 Mu =     11.45 M =    728.44
# Found Formula = C29.50 H40 Co2 N2 O11.50 
# Dc =      1.56 FOOO =   1508.00 Mu =     11.43 M =    724.51

_chemical_formula_sum            'C29.50 H40 Co2 N2 O11.50'
_chemical_formula_moiety         'C29.50 H40 Co2 N2 O11.50'
_chemical_compound_source        ?
_chemical_formula_weight         724.51


_cell_measurement_reflns_used    2483
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29
_cell_measurement_temperature    110

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.034
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_max          0.172

_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1508
_exptl_absorpt_coefficient_mu    1.143

# Sheldrick geometric approximatio 0.88 0.96 
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.96
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# 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        'XRED (Stoe & Cie 1996)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      110
_diffrn_reflns_number            16026
_reflns_number_total             7185
_diffrn_reflns_av_R_equivalents  0.124
# Number of reflections without Friedels Law is 7185 
# Number of reflections with Friedels Law is 4271 
# Theoretical number of reflections is about 3440 


_diffrn_reflns_theta_min         3.380
_diffrn_reflns_theta_max         29.546
_diffrn_measured_fraction_theta_max 0.891

_diffrn_reflns_theta_full        25.114
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              27

_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   difmap

_refine_diff_density_min         -1.04
_refine_diff_density_max         0.73


# 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         3314
_refine_ls_number_restraints     0
_refine_ls_number_parameters     416
_oxford_refine_ls_R_factor_ref   0.0681
_refine_ls_wR_factor_ref         0.0763
_refine_ls_goodness_of_fit_ref   1.1179
_refine_ls_shift/su_max          0.0001120
_refine_ls_shift/su_mean         0.0000059


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7166
_refine_ls_R_factor_all          0.1792
_refine_ls_wR_factor_all         0.2201

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3314
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_gt          0.0763

_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_abs_structure_details 'Flack (1983), 2914 Friedel-pairs'
# 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 ad


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 2.08 -0.306 1.01 
;

# 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
Co1 Co 0.41538(10) 0.23399(12) 0.51941(6) 0.0268 1.0000 Uani . . . . . .
Co2 Co 0.48055(10) 0.23549(11) 0.37912(6) 0.0253 1.0000 Uani . . . . . .
O1 O 0.4013(6) 0.3878(6) 0.5672(3) 0.0324 1.0000 Uani . . . . . .
C2 C 0.3734(10) 0.4772(10) 0.5456(5) 0.0325 1.0000 Uani . . . . . .
C3 C 0.3434(8) 0.5034(8) 0.4839(5) 0.0263 1.0000 Uani . . . . . .
C4 C 0.3108(8) 0.6163(9) 0.4719(6) 0.0369 1.0000 Uani . . . . . .
C5 C 0.2841(10) 0.6519(9) 0.4145(6) 0.0365 1.0000 Uani . . . . . .
C6 C 0.2491(10) 0.7717(11) 0.4027(6) 0.0523 1.0000 Uani . . . . . .
C7 C 0.2855(8) 0.5754(9) 0.3686(5) 0.0345 1.0000 Uani . . . . . .
C8 C 0.3155(8) 0.4635(8) 0.3780(5) 0.0283 1.0000 Uani . . . . . .
C9 C 0.3494(9) 0.4270(9) 0.4356(5) 0.0290 1.0000 Uani . . . . . .
O10 O 0.3801(5) 0.3224(6) 0.4432(3) 0.0283 1.0000 Uani . . . . . .
C11 C 0.3024(8) 0.3827(9) 0.3275(5) 0.0343 1.0000 Uani . . . . . .
N12 N 0.4144(7) 0.3357(6) 0.3069(4) 0.0266 1.0000 Uani . . . . . .
C13 C 0.4894(9) 0.4208(9) 0.2788(4) 0.0297 1.0000 Uani . . . . . .
C14 C 0.5710(9) 0.3506(10) 0.2394(5) 0.0353 1.0000 Uani . . . . . .
C15 C 0.5056(8) 0.2471(9) 0.2233(4) 0.0351 1.0000 Uani . . . . . .
C16 C 0.3896(7) 0.2587(9) 0.2558(4) 0.0307 1.0000 Uani . . . . . .
C17 C 0.3395(10) 0.1504(8) 0.2811(6) 0.0354 1.0000 Uani . . . . . .
O18 O 0.2723(7) 0.0970(6) 0.2471(4) 0.0461 1.0000 Uani . . . . . .
O19 O 0.3691(6) 0.1254(6) 0.3342(4) 0.0343 1.0000 Uani . . . . . .
O21 O 0.6164(6) 0.1388(6) 0.3421(3) 0.0319 1.0000 Uani . . . . . .
C22 C 0.6387(10) 0.0448(10) 0.3590(5) 0.0355 1.0000 Uani . . . . . .
C23 C 0.5877(9) -0.0186(8) 0.4077(4) 0.0289 1.0000 Uani . . . . . .
C24 C 0.6182(8) -0.1322(9) 0.4089(5) 0.0297 1.0000 Uani . . . . . .
C25 C 0.5732(9) -0.2044(8) 0.4503(5) 0.0329 1.0000 Uani . . . . . .
C26 C 0.6026(10) -0.3260(10) 0.4502(6) 0.0434 1.0000 Uani . . . . . .
C27 C 0.4981(8) -0.1586(8) 0.4936(5) 0.0285 1.0000 Uani . . . . . .
C28 C 0.4644(8) -0.0474(9) 0.4936(5) 0.0351 1.0000 Uani . . . . . .
C29 C 0.5099(9) 0.0245(8) 0.4487(4) 0.0238 1.0000 Uani . . . . . .
O30 O 0.4747(5) 0.1287(5) 0.4489(3) 0.0277 1.0000 Uani . . . . . .
C31 C 0.3738(8) -0.0114(9) 0.5353(5) 0.0308 1.0000 Uani . . . . . .
N32 N 0.4041(6) 0.0839(7) 0.5755(4) 0.0257 1.0000 Uani . . . . . .
C33 C 0.5028(7) 0.0591(8) 0.6146(5) 0.0297 1.0000 Uani . . . . . .
C34 C 0.4958(8) 0.1436(11) 0.6650(5) 0.0431 1.0000 Uani . . . . . .
C35 C 0.3661(9) 0.1709(12) 0.6697(5) 0.0462 1.0000 Uani . . . . . .
C36 C 0.3091(8) 0.1033(9) 0.6187(6) 0.0358 1.0000 Uani . . . . . .
C37 C 0.2119(9) 0.1667(8) 0.5868(5) 0.0294 1.0000 Uani . . . . . .
O38 O 0.2406(5) 0.2278(6) 0.5440(3) 0.0279 1.0000 Uani . . . . . .
O39 O 0.1113(5) 0.1547(6) 0.6081(3) 0.0304 1.0000 Uani . . . . . .
C51 C 0.002(2) 0.0469(18) 0.2936(11) 0.0782 0.7000 Uani . . . . . .
O52 O 0.0948(11) -0.0229(11) 0.3046(6) 0.0636 0.7000 Uani . . . . . .
C61 C 0.0804(14) 0.2599(15) 0.1730(7) 0.0580 0.8000 Uani . . . . . .
O62 O 0.1654(8) 0.2000(8) 0.1522(4) 0.0385 0.8000 Uani . . . . . .
O71 O 0.8164(7) 0.5570(8) 0.0913(6) 0.0724 1.0000 Uani . . . . . .
O81 O 0.5855(5) 0.2556(6) 0.5428(3) 0.0310 1.0000 Uani . . . . . .
H21 H 0.3718 0.5394 0.5730 0.0411 1.0000 Uiso . . . . . .
H41 H 0.3078 0.6680 0.5043 0.0471 1.0000 Uiso . . . . . .
H62 H 0.2553 0.7902 0.3598 0.0771 1.0000 Uiso . . . . . .
H61 H 0.2990 0.8235 0.4249 0.0772 1.0000 Uiso . . . . . .
H63 H 0.1707 0.7860 0.4155 0.0770 1.0000 Uiso . . . . . .
H71 H 0.2664 0.5997 0.3278 0.0452 1.0000 Uiso . . . . . .
H111 H 0.2521 0.3211 0.3404 0.0439 1.0000 Uiso . . . . . .
H112 H 0.2643 0.4195 0.2928 0.0441 1.0000 Uiso . . . . . .
H132 H 0.5319 0.4645 0.3100 0.0383 1.0000 Uiso . . . . . .
H131 H 0.4447 0.4755 0.2542 0.0381 1.0000 Uiso . . . . . .
H141 H 0.6391 0.3297 0.2628 0.0421 1.0000 Uiso . . . . . .
H142 H 0.5942 0.3898 0.2026 0.0419 1.0000 Uiso . . . . . .
H152 H 0.5472 0.1815 0.2373 0.0450 1.0000 Uiso . . . . . .
H151 H 0.4953 0.2412 0.1785 0.0450 1.0000 Uiso . . . . . .
H161 H 0.3310 0.2932 0.2278 0.0391 1.0000 Uiso . . . . . .
H221 H 0.6982 0.0075 0.3360 0.0443 1.0000 Uiso . . . . . .
H241 H 0.6717 -0.1613 0.3797 0.0401 1.0000 Uiso . . . . . .
H262 H 0.6050 -0.3558 0.4911 0.0661 1.0000 Uiso . . . . . .
H261 H 0.6776 -0.3377 0.4316 0.0662 1.0000 Uiso . . . . . .
H263 H 0.5467 -0.3680 0.4269 0.0661 1.0000 Uiso . . . . . .
H271 H 0.4685 -0.2050 0.5254 0.0334 1.0000 Uiso . . . . . .
H311 H 0.3524 -0.0742 0.5600 0.0392 1.0000 Uiso . . . . . .
H312 H 0.3073 0.0107 0.5102 0.0392 1.0000 Uiso . . . . . .
H332 H 0.4966 -0.0182 0.6306 0.0372 1.0000 Uiso . . . . . .
H331 H 0.5759 0.0641 0.5922 0.0369 1.0000 Uiso . . . . . .
H341 H 0.5248 0.1136 0.7037 0.0521 1.0000 Uiso . . . . . .
H342 H 0.5406 0.2095 0.6553 0.0521 1.0000 Uiso . . . . . .
H352 H 0.3352 0.1491 0.7103 0.0590 1.0000 Uiso . . . . . .
H351 H 0.3515 0.2513 0.6655 0.0591 1.0000 Uiso . . . . . .
H361 H 0.2808 0.0328 0.6354 0.0462 1.0000 Uiso . . . . . .
H611 H 0.0391 0.2954 0.1411 0.0715 0.8000 Uiso . . . . . .
H612 H 0.1032 0.3135 0.2021 0.0715 0.8000 Uiso . . . . . .
H613 H 0.0226 0.2117 0.1939 0.0715 0.8000 Uiso . . . . . .
H511 H -0.0670 0.0193 0.3102 0.0816 0.7000 Uiso . . . . . .
H512 H 0.0154 0.1208 0.3105 0.0816 0.7000 Uiso . . . . . .
H513 H -0.0095 0.0586 0.2504 0.0816 0.7000 Uiso . . . . . .
H6 H 0.2007 0.1656 0.1841 0.0472 0.8000 Uiso . . . . . .
H521 H 0.1624 0.0075 0.2858 0.0750 0.7000 Uiso . . . . . .
H713 H 0.8326 0.6053 0.1240 0.0862 1.0000 Uiso . . . . . .
H813 H 0.6335 0.2294 0.5104 0.0376 1.0000 Uiso . . . . . .
H812 H 0.6002 0.3320 0.5498 0.0371 1.0000 Uiso . . . . . .
H712 H 0.8823 0.5139 0.0790 0.0846 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4463(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
Co1 . O1 . 2.139(7) yes
Co1 . O10 . 2.032(7) yes
Co1 . O30 . 2.121(7) yes
Co1 . N32 . 2.195(9) yes
Co1 . O38 . 2.097(6) yes
Co1 . O81 . 2.052(6) yes
Co2 . O39 2_556 2.031(6) yes
Co2 . O10 . 2.110(7) yes
Co2 . N12 . 2.141(8) yes
Co2 . O19 . 2.099(7) yes
Co2 . O21 . 2.121(7) yes
Co2 . O30 . 2.007(7) yes
O1 . C2 . 1.222(13) yes
C2 . C3 . 1.439(15) yes
C2 . H21 . 0.964 no
C3 . C4 . 1.437(14) yes
C3 . C9 . 1.410(15) yes
C4 . C5 . 1.372(16) yes
C4 . H41 . 0.948 no
C5 . C6 . 1.522(17) yes
C5 . C7 . 1.370(16) yes
C6 . H62 . 0.977 no
C6 . H61 . 0.982 no
C6 . H63 . 0.965 no
C7 . C8 . 1.409(14) yes
C7 . H71 . 0.971 no
C8 . C9 . 1.401(15) yes
C8 . C11 . 1.488(15) yes
C9 . O10 . 1.320(12) yes
C11 . N12 . 1.486(12) yes
C11 . H111 . 0.985 no
C11 . H112 . 0.989 no
N12 . C13 . 1.480(13) yes
N12 . C16 . 1.487(13) yes
C13 . C14 . 1.537(14) yes
C13 . H132 . 0.996 no
C13 . H131 . 0.999 no
C14 . C15 . 1.502(15) yes
C14 . H141 . 0.976 no
C14 . H142 . 0.978 no
C15 . C16 . 1.530(13) yes
C15 . H152 . 0.976 no
C15 . H151 . 0.996 no
C16 . C17 . 1.533(15) yes
C16 . H161 . 1.007 no
C17 . O18 . 1.258(13) yes
C17 . O19 . 1.258(14) yes
O21 . C22 . 1.221(13) yes
C22 . C23 . 1.445(15) yes
C22 . H221 . 0.966 no
C23 . C24 . 1.415(14) yes
C23 . C29 . 1.379(14) yes
C24 . C25 . 1.365(15) yes
C24 . H241 . 0.960 no
C25 . C26 . 1.505(14) yes
C25 . C27 . 1.404(15) yes
C26 . H262 . 0.971 no
C26 . H261 . 0.971 no
C26 . H263 . 0.969 no
C27 . C28 . 1.395(14) yes
C27 . H271 . 0.961 no
C28 . C29 . 1.417(15) yes
C28 . C31 . 1.462(15) yes
C29 . O30 . 1.321(11) yes
C31 . N32 . 1.492(13) yes
C31 . H311 . 0.965 no
C31 . H312 . 0.985 no
N32 . C33 . 1.464(12) yes
N32 . C36 . 1.474(13) yes
C33 . C34 . 1.510(15) yes
C33 . H332 . 0.999 no
C33 . H331 . 0.982 no
C34 . C35 . 1.541(14) yes
C34 . H341 . 0.986 no
C34 . H342 . 0.974 no
C35 . C36 . 1.538(16) yes
C35 . H352 . 1.001 no
C35 . H351 . 0.988 no
C36 . C37 . 1.531(14) yes
C36 . H361 . 0.983 no
C37 . O38 . 1.244(12) yes
C37 . O39 . 1.264(12) yes
C51 . O52 . 1.38(3) yes
C51 . H511 . 0.941 no
C51 . H512 . 0.978 no
C51 . H513 . 0.972 no
O52 . H521 . 0.959 no
C61 . O62 . 1.304(18) yes
C61 . H611 . 0.952 no
C61 . H612 . 0.948 no
C61 . H613 . 0.998 no
O62 . H6 . 0.915 no
O71 . H713 . 0.945 no
O71 . H712 . 0.963 no
O81 . H813 . 0.958 no
O81 . H812 . 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
O1 . Co1 . O10 . 86.4(3) yes
O1 . Co1 . O30 . 154.7(3) yes
O10 . Co1 . O30 . 76.8(3) yes
O1 . Co1 . N32 . 115.6(3) yes
O10 . Co1 . N32 . 152.4(3) yes
O30 . Co1 . N32 . 86.5(3) yes
O1 . Co1 . O38 . 80.2(3) yes
O10 . Co1 . O38 . 92.2(3) yes
O30 . Co1 . O38 . 118.7(3) yes
N32 . Co1 . O38 . 76.6(3) yes
O1 . Co1 . O81 . 80.8(3) yes
O10 . Co1 . O81 . 109.5(3) yes
O30 . Co1 . O81 . 87.1(3) yes
N32 . Co1 . O81 . 91.2(3) yes
O38 . Co1 . O81 . 150.0(2) yes
O39 2_556 Co2 . O10 . 89.7(3) yes
O39 2_556 Co2 . N12 . 90.2(3) yes
O10 . Co2 . N12 . 91.2(3) yes
O39 2_556 Co2 . O19 . 159.4(3) yes
O10 . Co2 . O19 . 106.9(3) yes
N12 . Co2 . O19 . 77.6(3) yes
O39 2_556 Co2 . O21 . 81.9(3) yes
O10 . Co2 . O21 . 160.0(3) yes
N12 . Co2 . O21 . 106.8(3) yes
O19 . Co2 . O21 . 85.8(3) yes
O39 2_556 Co2 . O30 . 109.7(3) yes
O10 . Co2 . O30 . 77.6(3) yes
N12 . Co2 . O30 . 156.9(3) yes
O19 . Co2 . O30 . 86.3(3) yes
O21 . Co2 . O30 . 88.2(3) yes
Co1 . O1 . C2 . 126.3(7) yes
O1 . C2 . C3 . 128.8(10) yes
O1 . C2 . H21 . 116.5 no
C3 . C2 . H21 . 114.7 no
C2 . C3 . C4 . 116.5(10) yes
C2 . C3 . C9 . 124.0(10) yes
C4 . C3 . C9 . 119.5(10) yes
C3 . C4 . C5 . 121.7(10) yes
C3 . C4 . H41 . 119.6 no
C5 . C4 . H41 . 118.7 no
C4 . C5 . C6 . 121.0(11) yes
C4 . C5 . C7 . 118.0(10) yes
C6 . C5 . C7 . 121.0(11) yes
C5 . C6 . H62 . 111.3 no
C5 . C6 . H61 . 111.2 no
H62 . C6 . H61 . 107.0 no
C5 . C6 . H63 . 111.7 no
H62 . C6 . H63 . 108.2 no
H61 . C6 . H63 . 107.1 no
C5 . C7 . C8 . 122.5(11) yes
C5 . C7 . H71 . 118.7 no
C8 . C7 . H71 . 118.8 no
C7 . C8 . C9 . 120.3(10) yes
C7 . C8 . C11 . 119.4(10) yes
C9 . C8 . C11 . 120.2(9) yes
C3 . C9 . C8 . 117.8(10) yes
C3 . C9 . O10 . 122.8(10) yes
C8 . C9 . O10 . 119.3(10) yes
Co2 . O10 . Co1 . 100.5(3) yes
Co2 . O10 . C9 . 122.5(6) yes
Co1 . O10 . C9 . 131.3(7) yes
C8 . C11 . N12 . 113.0(8) yes
C8 . C11 . H111 . 109.7 no
N12 . C11 . H111 . 108.5 no
C8 . C11 . H112 . 109.3 no
N12 . C11 . H112 . 108.9 no
H111 . C11 . H112 . 107.3 no
Co2 . N12 . C11 . 107.4(6) yes
Co2 . N12 . C13 . 119.5(6) yes
C11 . N12 . C13 . 112.1(8) yes
Co2 . N12 . C16 . 106.3(6) yes
C11 . N12 . C16 . 107.5(8) yes
C13 . N12 . C16 . 103.2(7) yes
N12 . C13 . C14 . 102.5(8) yes
N12 . C13 . H132 . 111.5 no
C14 . C13 . H132 . 112.2 no
N12 . C13 . H131 . 112.4 no
C14 . C13 . H131 . 112.1 no
H132 . C13 . H131 . 106.3 no
C13 . C14 . C15 . 106.3(8) yes
C13 . C14 . H141 . 109.9 no
C15 . C14 . H141 . 108.6 no
C13 . C14 . H142 . 111.8 no
C15 . C14 . H142 . 110.1 no
H141 . C14 . H142 . 110.0 no
C14 . C15 . C16 . 104.8(9) yes
C14 . C15 . H152 . 110.4 no
C16 . C15 . H152 . 111.0 no
C14 . C15 . H151 . 110.7 no
C16 . C15 . H151 . 111.5 no
H152 . C15 . H151 . 108.5 no
C15 . C16 . N12 . 104.1(7) yes
C15 . C16 . C17 . 115.2(9) yes
N12 . C16 . C17 . 109.2(8) yes
C15 . C16 . H161 . 110.0 no
N12 . C16 . H161 . 109.6 no
C17 . C16 . H161 . 108.7 no
C16 . C17 . O18 . 116.9(10) yes
C16 . C17 . O19 . 116.1(9) yes
O18 . C17 . O19 . 126.9(10) yes
Co2 . O19 . C17 . 117.1(7) yes
Co2 . O21 . C22 . 123.3(7) yes
O21 . C22 . C23 . 129.1(10) yes
O21 . C22 . H221 . 115.0 no
C23 . C22 . H221 . 115.8 no
C22 . C23 . C24 . 115.1(10) yes
C22 . C23 . C29 . 123.8(10) yes
C24 . C23 . C29 . 121.0(10) yes
C23 . C24 . C25 . 122.3(10) yes
C23 . C24 . H241 . 120.1 no
C25 . C24 . H241 . 117.6 no
C24 . C25 . C26 . 122.2(11) yes
C24 . C25 . C27 . 116.2(9) yes
C26 . C25 . C27 . 121.6(10) yes
C25 . C26 . H262 . 111.4 no
C25 . C26 . H261 . 110.2 no
H262 . C26 . H261 . 108.1 no
C25 . C26 . H263 . 111.0 no
H262 . C26 . H263 . 108.7 no
H261 . C26 . H263 . 107.3 no
C25 . C27 . C28 . 123.4(10) yes
C25 . C27 . H271 . 119.3 no
C28 . C27 . H271 . 117.4 no
C27 . C28 . C29 . 119.0(10) yes
C27 . C28 . C31 . 119.0(10) yes
C29 . C28 . C31 . 121.6(9) yes
C28 . C29 . C23 . 118.1(9) yes
C28 . C29 . O30 . 117.7(9) yes
C23 . C29 . O30 . 124.2(9) yes
Co1 . O30 . Co2 . 101.0(3) yes
Co1 . O30 . C29 . 132.2(6) yes
Co2 . O30 . C29 . 126.6(6) yes
C28 . C31 . N32 . 115.7(8) yes
C28 . C31 . H311 . 107.9 no
N32 . C31 . H311 . 109.1 no
C28 . C31 . H312 . 106.8 no
N32 . C31 . H312 . 108.0 no
H311 . C31 . H312 . 109.2 no
Co1 . N32 . C31 . 108.3(6) yes
Co1 . N32 . C33 . 117.0(6) yes
C31 . N32 . C33 . 112.1(8) yes
Co1 . N32 . C36 . 106.1(6) yes
C31 . N32 . C36 . 109.3(8) yes
C33 . N32 . C36 . 103.5(8) yes
N32 . C33 . C34 . 104.8(7) yes
N32 . C33 . H332 . 110.0 no
C34 . C33 . H332 . 111.4 no
N32 . C33 . H331 . 111.4 no
C34 . C33 . H331 . 112.0 no
H332 . C33 . H331 . 107.2 no
C33 . C34 . C35 . 104.2(8) yes
C33 . C34 . H341 . 111.9 no
C35 . C34 . H341 . 110.7 no
C33 . C34 . H342 . 111.1 no
C35 . C34 . H342 . 111.1 no
H341 . C34 . H342 . 108.0 no
C34 . C35 . C36 . 104.9(9) yes
C34 . C35 . H352 . 110.5 no
C36 . C35 . H352 . 111.3 no
C34 . C35 . H351 . 111.7 no
C36 . C35 . H351 . 112.3 no
H352 . C35 . H351 . 106.2 no
C35 . C36 . N32 . 103.7(8) yes
C35 . C36 . C37 . 112.8(9) yes
N32 . C36 . C37 . 109.3(9) yes
C35 . C36 . H361 . 109.0 no
N32 . C36 . H361 . 110.8 no
C37 . C36 . H361 . 111.0 no
C36 . C37 . O38 . 116.6(9) yes
C36 . C37 . O39 . 116.8(9) yes
O38 . C37 . O39 . 126.6(9) yes
Co1 . O38 . C37 . 118.4(6) yes
Co2 2_456 O39 . C37 . 131.6(6) yes
O52 . C51 . H511 . 112.0 no
O52 . C51 . H512 . 111.3 no
H511 . C51 . H512 . 107.8 no
O52 . C51 . H513 . 111.6 no
H511 . C51 . H513 . 108.4 no
H512 . C51 . H513 . 105.4 no
C51 . O52 . H521 . 109.0 no
O62 . C61 . H611 . 111.6 no
O62 . C61 . H612 . 114.0 no
H611 . C61 . H612 . 109.4 no
O62 . C61 . H613 . 110.3 no
H611 . C61 . H613 . 105.4 no
H612 . C61 . H613 . 105.6 no
C61 . O62 . H6 . 108.5 no
H713 . O71 . H712 . 113.0 no
Co1 . O81 . H813 . 109.2 no
Co1 . O81 . H812 . 109.6 no
H813 . O81 . H812 . 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
C15 . H152 . O21 . 128.3 0.976 2.500 3.197(16) yes
C31 . H311 . O62 4_555 160.0 0.965 2.545 3.468(16) yes
O62 . H6 . O18 . 179.4 0.915 1.817 2.732(16) yes
O52 . H521 . O18 . 166.2 0.959 1.873 2.814(16) yes
O81 . H813 . O38 2_556 143.3 0.958 1.801 2.632(16) yes
O81 . H812 . O71 4_665 149.1 0.950 1.887 2.746(16) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/07/17 at 12:57:59
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/07/17 at 12:57:59
#
#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
-1 3 6 x .
0 2 8 x .
1 2 9 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1535638'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_audit_creation_date             17-01-18
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title I_Cu
_chemical_name_systematic        ?
_chemical_melting_point          ?

#--------------------------------------------------------------- 
# _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                   7.1420(9)
_cell_length_b                   10.8966(15)
_cell_length_c                   18.928(3)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     1473.1(3)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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            4

# Given Formula = C13 H15 Cu1 N1 O4 
# Dc =      1.41 Fooo =    748.00 Mu =     14.94 M =    312.81
# Found Formula = C14 H19 Cu1 N1 O6 
# Dc =      1.63 FOOO =    748.00 Mu =     15.15 M =    360.85

_chemical_formula_sum            'C14 H19 Cu1 N1 O6'
_chemical_formula_moiety         'C14 H19 Cu1 N1 O6'
_chemical_compound_source        ?
_chemical_formula_weight         360.85


_cell_measurement_reflns_used    4070
_cell_measurement_theta_min      4
_cell_measurement_theta_max      29
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_min          0.085
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_max          0.112

_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    1.515

# Sheldrick geometric approximatio 0.85 0.88 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.88
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# 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    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      293
_diffrn_reflns_number            4075
_reflns_number_total             2098
_diffrn_reflns_av_R_equivalents  0.054
# Number of reflections without Friedels Law is 2098 
# Number of reflections with Friedels Law is 2098 
# Theoretical number of reflections is about 2125 


_diffrn_reflns_theta_min         3.576
_diffrn_reflns_theta_max         29.570
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        25.134
_diffrn_measured_fraction_theta_full 0.989


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.66
_refine_diff_density_max         0.59


# 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         2001
_refine_ls_number_restraints     0
_refine_ls_number_parameters     200
_oxford_refine_ls_R_factor_ref   0.0379
_refine_ls_wR_factor_ref         0.0396
_refine_ls_goodness_of_fit_ref   1.1057
_refine_ls_shift/su_max          0.0008052
_refine_ls_shift/su_mean         0.0000177


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2655
_refine_ls_R_factor_all          0.0583
_refine_ls_wR_factor_all         0.0518

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2050
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_gt          0.0420

_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
# 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 ad


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 91.9 -152. 100. -43.7 12.1 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.2831(5) -0.5465(3) -0.4041(2) 0.0258 1.0000 Uani . . . . . .
C2 C 0.1572(6) -0.5173(4) -0.4444(3) 0.0168 1.0000 Uani . . . . . .
C3 C 0.1098(6) -0.5809(4) -0.5099(3) 0.0135 1.0000 Uani . . . . . .
C4 C 0.1789(6) -0.7002(3) -0.5248(3) 0.0139 1.0000 Uani . . . . . .
C5 C 0.1285(6) -0.7621(4) -0.5854(3) 0.0154 1.0000 Uani . . . . . .
C6 C 0.2039(7) -0.8889(4) -0.6021(3) 0.0222 1.0000 Uani . . . . . .
C7 C 0.0104(6) -0.7010(4) -0.6330(3) 0.0150 1.0000 Uani . . . . . .
C8 C -0.0529(6) -0.5817(4) -0.6222(3) 0.0135 1.0000 Uani . . . . . .
C9 C -0.0081(6) -0.5210(3) -0.5594(3) 0.0127 1.0000 Uani . . . . . .
O10 O -0.0689(4) -0.4081(3) -0.54521(19) 0.0142 1.0000 Uani . . . . . .
C11 C -0.1638(6) -0.5147(4) -0.6780(3) 0.0114 1.0000 Uani . . . . . .
N12 N -0.3465(5) -0.4698(3) -0.6494(2) 0.0118 1.0000 Uani . . . . . .
C13 C -0.4719(6) -0.5741(4) -0.6285(3) 0.0149 1.0000 Uani . . . . . .
C14 C -0.5436(6) -0.6243(4) -0.6976(3) 0.0221 1.0000 Uani . . . . . .
C15 C -0.5572(7) -0.5114(4) -0.7462(3) 0.0187 1.0000 Uani . . . . . .
C16 C -0.4647(6) -0.4080(4) -0.7041(3) 0.0141 1.0000 Uani . . . . . .
C17 C -0.6016(6) -0.3221(4) -0.6653(3) 0.0133 1.0000 Uani . . . . . .
O18 O -0.5429(4) -0.2787(3) -0.60580(19) 0.0156 1.0000 Uani . . . . . .
O19 O -0.7550(4) -0.2970(3) -0.6911(2) 0.0209 1.0000 Uani . . . . . .
O31 O -0.1330(4) -0.2036(3) -0.6529(2) 0.0212 1.0000 Uani . . . . . .
O32 O -0.3196(5) -0.2557(3) -0.4868(2) 0.0322 1.0000 Uani . . . . . .
Cu1 Cu -0.30344(7) -0.34377(5) -0.57533(3) 0.0139 1.0000 Uani . . . . . .
H21 H 0.0853 -0.4472 -0.4317 0.0199 1.0000 Uiso . . . . . .
H41 H 0.2615 -0.7380 -0.4923 0.0181 1.0000 Uiso . . . . . .
H61 H 0.1231 -0.9268 -0.6363 0.0370 1.0000 Uiso . . . . . .
H62 H 0.3288 -0.8826 -0.6206 0.0370 1.0000 Uiso . . . . . .
H63 H 0.2046 -0.9408 -0.5609 0.0371 1.0000 Uiso . . . . . .
H71 H -0.0257 -0.7428 -0.6752 0.0210 1.0000 Uiso . . . . . .
H111 H -0.1849 -0.5691 -0.7193 0.0148 1.0000 Uiso . . . . . .
H112 H -0.0947 -0.4420 -0.6950 0.0152 1.0000 Uiso . . . . . .
H131 H -0.3999 -0.6368 -0.6023 0.0202 1.0000 Uiso . . . . . .
H132 H -0.5743 -0.5448 -0.5981 0.0201 1.0000 Uiso . . . . . .
H141 H -0.4548 -0.6863 -0.7178 0.0267 1.0000 Uiso . . . . . .
H142 H -0.6645 -0.6632 -0.6925 0.0262 1.0000 Uiso . . . . . .
H151 H -0.4917 -0.5258 -0.7905 0.0241 1.0000 Uiso . . . . . .
H152 H -0.6883 -0.4904 -0.7572 0.0242 1.0000 Uiso . . . . . .
H161 H -0.3848 -0.3586 -0.7354 0.0141 1.0000 Uiso . . . . . .
H11 H -0.0200 -0.2314 -0.6641 0.0252 1.0000 Uiso . . . . . .
H232 H -0.1594 -0.1276 -0.6354 0.0252 1.0000 Uiso . . . . . .
H1 H -0.2248 -0.2440 -0.4552 0.0410 1.0000 Uiso . . . . . .
H2 H -0.4051 -0.1987 -0.4755 0.0410 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.724(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
O1 . C2 . 1.220(6) yes
C2 . C3 . 1.462(7) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.416(5) yes
C3 . C9 . 1.418(7) yes
C4 . C5 . 1.378(7) yes
C4 . H41 . 0.947 no
C5 . C6 . 1.513(6) yes
C5 . C7 . 1.402(7) yes
C6 . H61 . 0.961 no
C6 . H62 . 0.959 no
C6 . H63 . 0.964 no
C7 . C8 . 1.389(6) yes
C7 . H71 . 0.957 no
C8 . C9 . 1.399(7) yes
C8 . C11 . 1.508(6) yes
C9 . O10 . 1.329(5) yes
O10 . Cu1 . 1.900(3) yes
C11 . N12 . 1.493(5) yes
C11 . H111 . 0.993 no
C11 . H112 . 0.985 no
N12 . C13 . 1.498(5) yes
N12 . C16 . 1.495(6) yes
N12 . Cu1 . 1.986(4) yes
C13 . C14 . 1.509(8) yes
C13 . H131 . 0.987 no
C13 . H132 . 0.983 no
C14 . C15 . 1.538(7) yes
C14 . H141 . 1.000 no
C14 . H142 . 0.965 no
C15 . C16 . 1.529(6) yes
C15 . H151 . 0.975 no
C15 . H152 . 0.984 no
C16 . C17 . 1.539(6) yes
C16 . H161 . 0.983 no
C17 . O18 . 1.292(6) yes
C17 . O19 . 1.229(5) yes
O18 . Cu1 . 1.936(3) yes
O31 . Cu1 . 2.442(4) yes
O31 . H11 . 0.886 no
O31 . H232 . 0.910 no
O32 . Cu1 . 1.936(4) yes
O32 . H1 . 0.912 no
O32 . H2 . 0.895 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 . C2 . C3 . 125.4(4) yes
O1 . C2 . H21 . 116.5 no
C3 . C2 . H21 . 118.1 no
C2 . C3 . C4 . 121.5(4) yes
C2 . C3 . C9 . 118.8(4) yes
C4 . C3 . C9 . 119.7(4) yes
C3 . C4 . C5 . 121.5(4) yes
C3 . C4 . H41 . 118.9 no
C5 . C4 . H41 . 119.5 no
C4 . C5 . C6 . 121.8(4) yes
C4 . C5 . C7 . 117.5(4) yes
C6 . C5 . C7 . 120.7(5) yes
C5 . C6 . H61 . 108.6 no
C5 . C6 . H62 . 110.0 no
H61 . C6 . H62 . 109.9 no
C5 . C6 . H63 . 111.4 no
H61 . C6 . H63 . 107.4 no
H62 . C6 . H63 . 109.5 no
C5 . C7 . C8 . 122.9(5) yes
C5 . C7 . H71 . 118.4 no
C8 . C7 . H71 . 118.6 no
C7 . C8 . C9 . 119.4(4) yes
C7 . C8 . C11 . 121.2(5) yes
C9 . C8 . C11 . 119.3(4) yes
C3 . C9 . C8 . 118.8(4) yes
C3 . C9 . O10 . 119.0(4) yes
C8 . C9 . O10 . 122.2(4) yes
C9 . O10 . Cu1 . 124.5(3) yes
C8 . C11 . N12 . 111.2(4) yes
C8 . C11 . H111 . 110.2 no
N12 . C11 . H111 . 110.4 no
C8 . C11 . H112 . 110.8 no
N12 . C11 . H112 . 107.1 no
H111 . C11 . H112 . 107.2 no
C11 . N12 . C13 . 111.6(3) yes
C11 . N12 . C16 . 112.8(4) yes
C13 . N12 . C16 . 100.8(3) yes
C11 . N12 . Cu1 . 110.3(3) yes
C13 . N12 . Cu1 . 115.3(3) yes
C16 . N12 . Cu1 . 105.5(3) yes
N12 . C13 . C14 . 104.3(4) yes
N12 . C13 . H131 . 110.3 no
C14 . C13 . H131 . 111.3 no
N12 . C13 . H132 . 110.6 no
C14 . C13 . H132 . 112.0 no
H131 . C13 . H132 . 108.4 no
C13 . C14 . C15 . 104.6(4) yes
C13 . C14 . H141 . 111.2 no
C15 . C14 . H141 . 110.4 no
C13 . C14 . H142 . 111.9 no
C15 . C14 . H142 . 110.7 no
H141 . C14 . H142 . 108.0 no
C14 . C15 . C16 . 104.3(4) yes
C14 . C15 . H151 . 111.0 no
C16 . C15 . H151 . 111.2 no
C14 . C15 . H152 . 111.8 no
C16 . C15 . H152 . 110.4 no
H151 . C15 . H152 . 108.1 no
C15 . C16 . N12 . 106.0(3) yes
C15 . C16 . C17 . 115.0(4) yes
N12 . C16 . C17 . 107.4(4) yes
C15 . C16 . H161 . 109.7 no
N12 . C16 . H161 . 109.7 no
C17 . C16 . H161 . 109.0 no
C16 . C17 . O18 . 115.7(4) yes
C16 . C17 . O19 . 120.5(5) yes
O18 . C17 . O19 . 123.8(4) yes
C17 . O18 . Cu1 . 114.4(3) yes
Cu1 . O31 . H11 . 112.6 no
Cu1 . O31 . H232 . 104.1 no
H11 . O31 . H232 . 125.8 no
Cu1 . O32 . H1 . 126.5 no
Cu1 . O32 . H2 . 126.2 no
H1 . O32 . H2 . 104.5 no
O31 . Cu1 . N12 . 94.89(13) yes
O31 . Cu1 . O32 . 103.89(13) yes
N12 . Cu1 . O32 . 160.95(17) yes
O31 . Cu1 . O18 . 91.78(14) yes
N12 . Cu1 . O18 . 84.52(15) yes
O32 . Cu1 . O18 . 91.47(15) yes
O31 . Cu1 . O10 . 88.44(14) yes
N12 . Cu1 . O10 . 95.44(14) yes
O32 . Cu1 . O10 . 88.49(15) yes
O18 . Cu1 . O10 . 179.78(15) 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
C14 . H141 . O19 3_443 159.4 1.000 2.583 3.536(7) yes
O31 . H11 . O19 1_655 179.6 0.886 2.083 2.974(4) yes
O31 . H232 . O1 2_444 179.3 0.910 2.076 2.987(7) yes
O31 . H232 . C2 2_444 152.3 0.910 2.546 3.378(7) yes
O32 . H1 . C17 2_544 152.0 0.912 2.550 3.382(7) yes
O32 . H1 . O18 2_544 179.8 0.912 1.755 2.667(7) yes
O32 . H2 . C9 2_444 153.4 0.895 2.585 3.416(6) yes
O32 . H2 . O10 2_444 179.2 0.895 1.693 2.588(7) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 18/01/17 at 04:43:05
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 18/01/17 at 04:43:05
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H2LA
_database_code_depnum_ccdc_archive 'CCDC 1535640'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;

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

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

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

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

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

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   5.6286(6)
_cell_length_b                   10.2605(16)
_cell_length_c                   12.8165(18)
_cell_angle_alpha                73.668(13)
_cell_angle_beta                 87.745(10)
_cell_angle_gamma                88.353(11)
_cell_volume                     709.65(16)

_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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Na 0.0362 0.0249 4.7626 3.2850 3.1736 8.8422 1.2674 0.3136 1.1128 129.4240
0.6760 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'


_cell_formula_units_Z            1

# Given Formula = C28 H32 Cl1 N2 Na1 O8 
# Dc =      1.36 Fooo =    298.00 Mu =      2.02 M =    583.01
# Found Formula = C28 H35 Cl1 N2 O8 
# Dc =      1.32 FOOO =    298.00 Mu =      1.86 M =    563.05

_chemical_formula_sum            'C28 H35 Cl1 N2 O8'
_chemical_formula_moiety         'C28 H35 Cl1 N2 O8'
_chemical_compound_source        ?
_chemical_formula_weight         563.05


_cell_measurement_reflns_used    3095
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.103
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_max          0.141

_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             298
_exptl_absorpt_coefficient_mu    0.186

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# 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    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      293
_diffrn_reflns_number            5477
_reflns_number_total             3303
_diffrn_reflns_av_R_equivalents  0.034
# Number of reflections without Friedels Law is 3303 
# Number of reflections with Friedels Law is 3303 
# Theoretical number of reflections is about 3913 


_diffrn_reflns_theta_min         3.314
_diffrn_reflns_theta_max         29.651
_diffrn_measured_fraction_theta_max 0.964

_diffrn_reflns_theta_full        25.204
_diffrn_measured_fraction_theta_full 0.983


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -7
_reflns_limit_h_max              5
_reflns_limit_k_min              -13
_reflns_limit_k_max              14
_reflns_limit_l_min              -17
_reflns_limit_l_max              17

_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   difmap

_refine_diff_density_min         -0.24
_refine_diff_density_max         0.22


# 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         2981
_refine_ls_number_restraints     3
_refine_ls_number_parameters     353
_oxford_refine_ls_R_factor_ref   0.0479
_refine_ls_wR_factor_ref         0.0519
_refine_ls_goodness_of_fit_ref   1.0854
_refine_ls_shift/su_max          0.0038836
_refine_ls_shift/su_mean         0.0003307


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4246
_refine_ls_R_factor_all          0.0739
_refine_ls_wR_factor_all         0.0740

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3271
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_gt          0.0549

_refine_ls_abs_structure_Flack   -0.06(10)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
# 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 ad


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 3.26 0.692 1.46 
;

# 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
O2 O 0.1192(5) 0.7835(4) -0.0423(2) 0.0535 1.0000 Uani . . . . . .
C3 C 0.2897(7) 0.7799(4) -0.1024(3) 0.0365 1.0000 Uani . . . . . .
O4 O 0.2887(6) 0.8147(4) -0.2078(2) 0.0564 1.0000 Uani . . . . . .
C5 C 0.5302(7) 0.7290(4) -0.0595(3) 0.0319 1.0000 Uani . . . . . .
N6 N 0.5318(6) 0.7329(3) 0.0575(2) 0.0316 1.0000 Uani . . . . . .
C7 C 0.6441(7) 0.8560(4) 0.0768(3) 0.0348 1.0000 Uani . . . . . .
C8 C 0.5593(7) 0.9873(4) 0.0041(3) 0.0345 1.0000 Uani . . . . . .
C9 C 0.3603(8) 1.0593(4) 0.0256(3) 0.0391 1.0000 Uani . . . . . .
O10 O 0.2155(6) 1.0164(3) 0.1170(3) 0.0567 1.0000 Uani . . . . . .
C11 C 0.3018(8) 1.1843(4) -0.0454(4) 0.0460 1.0000 Uani . . . . . .
C12 C 0.0892(10) 1.2650(5) -0.0245(5) 0.0607 1.0000 Uani . . . . . .
O13 O 0.0475(8) 1.3791(4) -0.0778(4) 0.0928 1.0000 Uani . . . . . .
C14 C 0.4445(9) 1.2368(4) -0.1383(4) 0.0520 1.0000 Uani . . . . . .
C15 C 0.6399(8) 1.1674(5) -0.1639(4) 0.0498 1.0000 Uani . . . . . .
C16 C 0.6979(8) 1.0439(4) -0.0909(3) 0.0409 1.0000 Uani . . . . . .
C17 C 0.7973(11) 1.2217(6) -0.2662(4) 0.0748 1.0000 Uani . . . . . .
C18 C 0.6491(8) 0.6012(4) 0.1184(3) 0.0442 1.0000 Uani . . . . . .
C19 C 0.5688(11) 0.5018(5) 0.0613(4) 0.0649 1.0000 Uani . . . . . .
C20 C 0.5733(10) 0.5776(5) -0.0558(4) 0.0553 1.0000 Uani . . . . . .
O21 O -0.1161(5) 0.8443(4) 0.7229(2) 0.0577 1.0000 Uani . . . . . .
C22 C -0.1224(7) 0.8580(4) 0.6225(3) 0.0377 1.0000 Uani . . . . . .
O23 O 0.0407(6) 0.8962(4) 0.5546(3) 0.0584 1.0000 Uani . . . . . .
C24 C -0.3541(7) 0.8164(4) 0.5852(3) 0.0333 1.0000 Uani . . . . . .
N25 N -0.3247(5) 0.8381(3) 0.4628(2) 0.0298 1.0000 Uani . . . . . .
C26 C -0.4990(7) 0.9374(4) 0.3970(3) 0.0364 1.0000 Uani . . . . . .
C27 C -0.4475(7) 1.0801(4) 0.3971(3) 0.0368 1.0000 Uani . . . . . .
C28 C -0.5939(8) 1.1511(4) 0.4521(3) 0.0391 1.0000 Uani . . . . . .
C29 C -0.5529(8) 1.2865(4) 0.4484(3) 0.0441 1.0000 Uani . . . . . .
C30 C -0.3546(8) 1.3466(4) 0.3889(3) 0.0435 1.0000 Uani . . . . . .
C31 C -0.2028(8) 1.2775(4) 0.3337(3) 0.0422 1.0000 Uani . . . . . .
C32 C -0.2475(8) 1.1426(4) 0.3381(3) 0.0382 1.0000 Uani . . . . . .
O33 O -0.1102(6) 1.0668(3) 0.2881(2) 0.0534 1.0000 Uani . . . . . .
C34 C 0.0054(9) 1.3456(5) 0.2702(4) 0.0521 1.0000 Uani . . . . . .
O35 O 0.1382(7) 1.2922(4) 0.2160(3) 0.0636 1.0000 Uani . . . . . .
C36 C -0.7228(10) 1.3634(5) 0.5063(4) 0.0598 1.0000 Uani . . . . . .
C37 C -0.3295(8) 0.7009(4) 0.4415(3) 0.0396 1.0000 Uani . . . . . .
C38 C -0.2619(10) 0.6042(4) 0.5496(4) 0.0525 1.0000 Uani . . . . . .
C39 C -0.3984(10) 0.6650(5) 0.6305(4) 0.0542 1.0000 Uani . . . . . .
Cl1 Cl 0.1691(2) 0.71874(13) 0.25319(10) 0.0492 1.0000 Uani . . . . . .
H51 H 0.6545 0.7853 -0.1023 0.0383 1.0000 Uiso R . . . . .
H71 H 0.6071 0.8558 0.1506 0.0411 1.0000 Uiso R . . . . .
H72 H 0.8122 0.8459 0.0651 0.0412 1.0000 Uiso R . . . . .
H121 H -0.0162 1.2237 0.0352 0.0732 1.0000 Uiso R . . . . .
H141 H 0.4047 1.3219 -0.1840 0.0624 1.0000 Uiso R . . . . .
H161 H 0.8317 0.9945 -0.1056 0.0487 1.0000 Uiso R . . . . .
H173 H 0.9511 1.1791 -0.2558 0.1134 1.0000 Uiso R . . . . .
H171 H 0.8100 1.3186 -0.2809 0.1131 1.0000 Uiso R . . . . .
H172 H 0.7247 1.2020 -0.3269 0.1135 1.0000 Uiso R . . . . .
H182 H 0.8213 0.6103 0.1118 0.0539 1.0000 Uiso R . . . . .
H181 H 0.6016 0.5766 0.1953 0.0535 1.0000 Uiso R . . . . .
H191 H 0.6736 0.4213 0.0752 0.0781 1.0000 Uiso R . . . . .
H192 H 0.4058 0.4737 0.0858 0.0786 1.0000 Uiso R . . . . .
H201 H 0.7272 0.5659 -0.0880 0.0663 1.0000 Uiso R . . . . .
H202 H 0.4528 0.5473 -0.0944 0.0664 1.0000 Uiso R . . . . .
H241 H -0.4828 0.8707 0.6009 0.0392 1.0000 Uiso R . . . . .
H261 H -0.6550 0.9113 0.4286 0.0432 1.0000 Uiso R . . . . .
H262 H -0.4904 0.9284 0.3239 0.0432 1.0000 Uiso R . . . . .
H281 H -0.7263 1.1072 0.4918 0.0469 1.0000 Uiso R . . . . .
H301 H -0.3237 1.4361 0.3864 0.0513 1.0000 Uiso R . . . . .
H341 H 0.0342 1.4348 0.2728 0.0621 1.0000 Uiso R . . . . .
H362 H -0.7255 1.4582 0.4681 0.0903 1.0000 Uiso R . . . . .
H361 H -0.6726 1.3527 0.5791 0.0903 1.0000 Uiso R . . . . .
H363 H -0.8809 1.3295 0.5104 0.0899 1.0000 Uiso R . . . . .
H371 H -0.4878 0.6849 0.4226 0.0485 1.0000 Uiso R . . . . .
H372 H -0.2188 0.6951 0.3831 0.0480 1.0000 Uiso R . . . . .
H381 H -0.0902 0.6038 0.5585 0.0628 1.0000 Uiso R . . . . .
H382 H -0.3129 0.5114 0.5565 0.0629 1.0000 Uiso R . . . . .
H391 H -0.3404 0.6309 0.7036 0.0651 1.0000 Uiso R . . . . .
H392 H -0.5669 0.6464 0.6317 0.0650 1.0000 Uiso R . . . . .
H101 H 0.2397 0.9336 0.1428 0.0847 1.0000 Uiso R . . . . .
H61 H 0.3815 0.7338 0.0829 0.0469 0.5000 Uiso R . . . . .
H251 H -0.1822 0.8741 0.4450 0.0450 0.5000 Uiso R . . . . .
H331 H 0.0078 1.1071 0.2575 0.0804 1.0000 Uiso R . . . . .
H41 H 0.1465 0.8486 -0.2443 0.0686 1.0000 Uiso R . . . . .
H212 H -0.2384 0.9001 0.7426 0.0694 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.899(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
O2 . C3 . 1.213(5) yes
C3 . O4 . 1.297(5) yes
C3 . C5 . 1.505(5) yes
O4 . H41 . 0.950 no
C5 . N6 . 1.511(4) yes
C5 . C20 . 1.553(6) yes
C5 . H51 . 0.969 no
N6 . C7 . 1.513(5) yes
N6 . C18 . 1.506(5) yes
N6 . H61 . 0.895 no
C7 . C8 . 1.484(5) yes
C7 . H71 . 0.961 no
C7 . H72 . 0.959 no
C8 . C9 . 1.385(5) yes
C8 . C16 . 1.408(5) yes
C9 . O10 . 1.374(5) yes
C9 . C11 . 1.387(6) yes
O10 . H101 . 0.830 no
C11 . C12 . 1.493(7) yes
C11 . C14 . 1.394(7) yes
C12 . O13 . 1.200(6) yes
C12 . H121 . 0.955 no
C14 . C15 . 1.372(7) yes
C14 . H141 . 0.931 no
C15 . C16 . 1.386(6) yes
C15 . C17 . 1.530(6) yes
C16 . H161 . 0.939 no
C17 . H173 . 0.955 no
C17 . H171 . 0.963 no
C17 . H172 . 0.965 no
C18 . C19 . 1.501(7) yes
C18 . H182 . 0.975 no
C18 . H181 . 0.974 no
C19 . C20 . 1.483(7) yes
C19 . H191 . 0.980 no
C19 . H192 . 0.983 no
C20 . H201 . 0.964 no
C20 . H202 . 0.962 no
O21 . C22 . 1.256(5) yes
O21 . H212 . 0.955 no
C22 . O23 . 1.233(5) yes
C22 . C24 . 1.519(6) yes
C24 . N25 . 1.524(4) yes
C24 . C39 . 1.522(6) yes
C24 . H241 . 0.951 no
N25 . C26 . 1.496(5) yes
N25 . C37 . 1.508(5) yes
N25 . H251 . 0.887 no
C26 . C27 . 1.501(5) yes
C26 . H261 . 0.965 no
C26 . H262 . 0.965 no
C27 . C28 . 1.385(6) yes
C27 . C32 . 1.397(6) yes
C28 . C29 . 1.401(6) yes
C28 . H281 . 0.937 no
C29 . C30 . 1.384(6) yes
C29 . C36 . 1.523(6) yes
C30 . C31 . 1.390(6) yes
C30 . H301 . 0.931 no
C31 . C32 . 1.399(6) yes
C31 . C34 . 1.476(7) yes
C32 . O33 . 1.349(5) yes
O33 . H331 . 0.818 no
C34 . O35 . 1.221(6) yes
C34 . H341 . 0.945 no
C36 . H362 . 0.958 no
C36 . H361 . 0.961 no
C36 . H363 . 0.959 no
C37 . C38 . 1.514(6) yes
C37 . H371 . 0.963 no
C37 . H372 . 0.968 no
C38 . C39 . 1.526(7) yes
C38 . H381 . 0.977 no
C38 . H382 . 0.982 no
C39 . H391 . 0.969 no
C39 . H392 . 0.972 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
O2 . C3 . O4 . 125.7(4) yes
O2 . C3 . C5 . 122.0(3) yes
O4 . C3 . C5 . 112.3(3) yes
C3 . O4 . H41 . 120.0 no
C3 . C5 . N6 . 107.5(3) yes
C3 . C5 . C20 . 111.6(4) yes
N6 . C5 . C20 . 105.5(3) yes
C3 . C5 . H51 . 110.5 no
N6 . C5 . H51 . 110.6 no
C20 . C5 . H51 . 110.9 no
C5 . N6 . C7 . 115.9(3) yes
C5 . N6 . C18 . 105.3(3) yes
C7 . N6 . C18 . 112.9(3) yes
C5 . N6 . H61 . 108.9 no
C7 . N6 . H61 . 105.3 no
C18 . N6 . H61 . 108.3 no
N6 . C7 . C8 . 114.0(3) yes
N6 . C7 . H71 . 108.1 no
C8 . C7 . H71 . 108.1 no
N6 . C7 . H72 . 106.3 no
C8 . C7 . H72 . 109.5 no
H71 . C7 . H72 . 110.9 no
C7 . C8 . C9 . 124.6(3) yes
C7 . C8 . C16 . 117.0(4) yes
C9 . C8 . C16 . 118.4(4) yes
C8 . C9 . O10 . 123.7(4) yes
C8 . C9 . C11 . 120.2(4) yes
O10 . C9 . C11 . 116.1(4) yes
C9 . O10 . H101 . 107.5 no
C9 . C11 . C12 . 121.6(4) yes
C9 . C11 . C14 . 119.5(4) yes
C12 . C11 . C14 . 118.9(4) yes
C11 . C12 . O13 . 123.2(6) yes
C11 . C12 . H121 . 117.9 no
O13 . C12 . H121 . 118.9 no
C11 . C14 . C15 . 122.2(4) yes
C11 . C14 . H141 . 118.3 no
C15 . C14 . H141 . 119.6 no
C14 . C15 . C16 . 117.4(4) yes
C14 . C15 . C17 . 123.2(4) yes
C16 . C15 . C17 . 119.4(4) yes
C8 . C16 . C15 . 122.3(4) yes
C8 . C16 . H161 . 118.2 no
C15 . C16 . H161 . 119.4 no
C15 . C17 . H173 . 109.7 no
C15 . C17 . H171 . 109.1 no
H173 . C17 . H171 . 110.3 no
C15 . C17 . H172 . 109.0 no
H173 . C17 . H172 . 109.7 no
H171 . C17 . H172 . 109.0 no
N6 . C18 . C19 . 103.5(3) yes
N6 . C18 . H182 . 109.6 no
C19 . C18 . H182 . 110.9 no
N6 . C18 . H181 . 111.1 no
C19 . C18 . H181 . 113.1 no
H182 . C18 . H181 . 108.6 no
C18 . C19 . C20 . 105.1(4) yes
C18 . C19 . H191 . 111.4 no
C20 . C19 . H191 . 111.4 no
C18 . C19 . H192 . 109.8 no
C20 . C19 . H192 . 109.9 no
H191 . C19 . H192 . 109.2 no
C5 . C20 . C19 . 105.6(4) yes
C5 . C20 . H201 . 110.1 no
C19 . C20 . H201 . 109.5 no
C5 . C20 . H202 . 110.8 no
C19 . C20 . H202 . 111.8 no
H201 . C20 . H202 . 109.2 no
C22 . O21 . H212 . 108.8 no
O21 . C22 . O23 . 126.7(4) yes
O21 . C22 . C24 . 114.8(3) yes
O23 . C22 . C24 . 118.5(3) yes
C22 . C24 . N25 . 106.7(3) yes
C22 . C24 . C39 . 112.5(3) yes
N25 . C24 . C39 . 104.2(3) yes
C22 . C24 . H241 . 110.4 no
N25 . C24 . H241 . 110.2 no
C39 . C24 . H241 . 112.6 no
C24 . N25 . C26 . 114.3(3) yes
C24 . N25 . C37 . 107.9(3) yes
C26 . N25 . C37 . 112.7(3) yes
C24 . N25 . H251 . 105.0 no
C26 . N25 . H251 . 106.5 no
C37 . N25 . H251 . 110.1 no
N25 . C26 . C27 . 111.4(3) yes
N25 . C26 . H261 . 106.9 no
C27 . C26 . H261 . 110.8 no
N25 . C26 . H262 . 107.8 no
C27 . C26 . H262 . 110.9 no
H261 . C26 . H262 . 108.9 no
C26 . C27 . C28 . 121.9(4) yes
C26 . C27 . C32 . 118.4(4) yes
C28 . C27 . C32 . 119.7(4) yes
C27 . C28 . C29 . 122.2(4) yes
C27 . C28 . H281 . 118.4 no
C29 . C28 . H281 . 119.4 no
C28 . C29 . C30 . 117.1(4) yes
C28 . C29 . C36 . 120.9(4) yes
C30 . C29 . C36 . 122.0(4) yes
C29 . C30 . C31 . 122.0(4) yes
C29 . C30 . H301 . 118.2 no
C31 . C30 . H301 . 119.8 no
C30 . C31 . C32 . 120.0(4) yes
C30 . C31 . C34 . 120.5(4) yes
C32 . C31 . C34 . 119.6(4) yes
C31 . C32 . C27 . 119.0(4) yes
C31 . C32 . O33 . 124.4(4) yes
C27 . C32 . O33 . 116.6(4) yes
C32 . O33 . H331 . 112.4 no
C31 . C34 . O35 . 123.3(4) yes
C31 . C34 . H341 . 116.8 no
O35 . C34 . H341 . 119.8 no
C29 . C36 . H362 . 110.2 no
C29 . C36 . H361 . 110.1 no
H362 . C36 . H361 . 108.7 no
C29 . C36 . H363 . 110.7 no
H362 . C36 . H363 . 108.8 no
H361 . C36 . H363 . 108.3 no
N25 . C37 . C38 . 103.1(3) yes
N25 . C37 . H371 . 109.1 no
C38 . C37 . H371 . 111.6 no
N25 . C37 . H372 . 111.7 no
C38 . C37 . H372 . 112.0 no
H371 . C37 . H372 . 109.2 no
C37 . C38 . C39 . 102.0(4) yes
C37 . C38 . H381 . 110.7 no
C39 . C38 . H381 . 111.8 no
C37 . C38 . H382 . 111.6 no
C39 . C38 . H382 . 111.2 no
H381 . C38 . H382 . 109.4 no
C38 . C39 . C24 . 103.0(3) yes
C38 . C39 . H391 . 112.4 no
C24 . C39 . H391 . 111.0 no
C38 . C39 . H392 . 110.6 no
C24 . C39 . H392 . 110.8 no
H391 . C39 . H392 . 109.0 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
C5 . H51 . O21 1_654 145.32 0.969 2.471 3.314(6) yes
C7 . H72 . O2 1_655 146.84 0.959 2.353 3.199(6) yes
C19 . H192 . O35 1_545 146.51 0.983 2.595 3.457(6) yes
C20 . H201 . O13 1_645 139.18 0.964 2.573 3.362(6) yes
C26 . H261 . O23 1_455 154.76 0.965 2.285 3.185(6) yes
C28 . H281 . O23 1_455 147.69 0.937 2.481 3.311(6) yes
N25 . H251 . O23 . 122.81 0.887 1.983 2.574(6) yes
N25 . H251 . O33 . 122.70 0.887 2.421 2.995(6) yes
O33 . H331 . O35 . 139.42 0.818 1.978 2.653(6) yes
O4 . H41 . O21 1_554 156.38 0.950 1.558 2.458(6) yes
O4 . H41 . C22 1_554 151.71 0.950 2.306 3.174(6) yes
O4 . H41 . O23 1_554 131.20 0.950 2.575 3.280(6) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/07/17 at 11:44:05
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE O   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE O   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 173,X'S) H   ( 172,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 202,X'S) H   ( 201,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE N   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE O   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) H   ( 363,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) H   ( 392,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/07/17 at 11:44:05
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1535641'
_audit_update_record             
;
2017-07-19 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_audit_creation_date             10-12-14
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title III_Cu
_chemical_name_systematic        ?
_chemical_melting_point          ?

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   13.9452(6)
_cell_length_b                   15.3362(5)
_cell_length_c                   21.8663(8)
_cell_angle_alpha                90.0
_cell_angle_beta                 89.343(3)
_cell_angle_gamma                90.0
_cell_volume                     4676.1(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,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'
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'


_cell_formula_units_Z            2

# Given Formula = C82 H60 Cu4 N8 O13 
# Dc =      1.15 Fooo =   2043.00 Mu =      9.53 M =   1619.61
# Found Formula = C88.50 H118.50 Cu4 N8 O25 
# Dc =      1.38 FOOO =   2043.00 Mu =      9.74 M =   1948.64

_chemical_formula_sum            'C88.50 H118.50 Cu4 N8 O25'
_chemical_formula_moiety         'C88.50 H118.50 Cu4 N8 O25'
_chemical_compound_source        ?
_chemical_formula_weight         1948.64


_cell_measurement_reflns_used    42007
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30
_cell_measurement_temperature    110

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_min          0.096
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_max          0.453

_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2043
_exptl_absorpt_coefficient_mu    0.974

# Sheldrick geometric approximatio 0.77 0.91 
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.91
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# 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        'XRED (Stoe & Cie 1996)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      110
_diffrn_reflns_number            82661
_reflns_number_total             23180
_diffrn_reflns_av_R_equivalents  0.049
# Number of reflections without Friedels Law is 23180 
# Number of reflections with Friedels Law is 12522 
# Theoretical number of reflections is about 13247 


_diffrn_reflns_theta_min         3.436
_diffrn_reflns_theta_max         29.678
_diffrn_measured_fraction_theta_max 0.913

_diffrn_reflns_theta_full        25.227
_diffrn_measured_fraction_theta_full 0.982


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              -18
_reflns_limit_h_max              18
_reflns_limit_k_min              -21
_reflns_limit_k_max              21
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_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   difmap

_refine_diff_density_min         -1.00
_refine_diff_density_max         1.13


# 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         19548
_refine_ls_number_restraints     13
_refine_ls_number_parameters     1163
_oxford_refine_ls_R_factor_ref   0.0473
_refine_ls_wR_factor_ref         0.0542
_refine_ls_goodness_of_fit_ref   1.0347
_refine_ls_shift/su_max          0.0319124
_refine_ls_shift/su_mean         0.0006510


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        23154
_refine_ls_R_factor_all          0.0592
_refine_ls_wR_factor_all         0.0681

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                20712
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_gt          0.0565

_refine_ls_abs_structure_Flack   0.045(7)
_refine_ls_abs_structure_details 'Flack (1983), 10658 Friedel-pairs'
# 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 ad


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 15.4 -13.0 11.7 -1.56 
;

# 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
Cu1 Cu 0.24470(3) 0.43706(3) 0.047179(17) 0.0192 1.0000 Uani . . . . . .
Cu2 Cu 0.11544(3) 0.30471(3) -0.046487(17) 0.0185 1.0000 Uani . . . . . .
Cu3 Cu 0.63292(3) 0.89518(3) 0.410180(17) 0.0190 1.0000 Uani . . . . . .
Cu4 Cu 0.76629(3) 1.01873(4) 0.507040(17) 0.0211 1.0000 Uani . . . . . .
O1 O 0.22583(16) 0.22933(15) -0.04091(10) 0.0203 1.0000 Uani . . . . . .
O2 O 0.28163(18) 0.10903(18) 0.00228(13) 0.0307 1.0000 Uani . . . . . .
C3 C 0.2152(2) 0.1584(2) -0.01000(15) 0.0211 1.0000 Uani . . . . . .
C4 C 0.1140(2) 0.1327(2) 0.01000(14) 0.0194 1.0000 Uani . . . . . .
C5 C 0.0803(2) 0.0514(2) -0.02502(16) 0.0242 1.0000 Uani . . . . . .
C6 C -0.0276(2) 0.0652(2) -0.02784(16) 0.0244 1.0000 Uani . . . . . .
C7 C -0.0326(2) 0.1617(2) -0.04269(15) 0.0221 1.0000 Uani . . . . . .
N8 N 0.04109(19) 0.20291(18) -0.00262(12) 0.0195 1.0000 Uani . . . . . .
C9 C -0.0108(2) 0.2368(2) 0.05242(15) 0.0217 1.0000 Uani . . . . . .
C10 C 0.0496(2) 0.2482(2) 0.10814(15) 0.0211 1.0000 Uani . . . . . .
C11 C 0.0229(2) 0.2071(2) 0.16193(15) 0.0232 1.0000 Uani . . . . . .
C12 C 0.0736(3) 0.2165(3) 0.21631(16) 0.0287 1.0000 Uani . . . . . .
C13 C 0.0386(3) 0.1715(3) 0.27327(18) 0.0369 1.0000 Uani . . . . . .
C14 C 0.1555(3) 0.2665(2) 0.21417(15) 0.0269 1.0000 Uani . . . . . .
C15 C 0.1852(2) 0.3112(2) 0.16105(15) 0.0215 1.0000 Uani . . . . . .
C16 C 0.1311(2) 0.3046(2) 0.10668(13) 0.0187 1.0000 Uani . . . . . .
O17 O 0.15184(16) 0.34534(15) 0.05588(10) 0.0201 1.0000 Uani . . . . . .
C18 C 0.2720(2) 0.3597(2) 0.16525(15) 0.0221 1.0000 Uani . . . . . .
N19 N 0.3072(2) 0.41349(18) 0.12462(12) 0.0212 1.0000 Uani . . . . . .
C20 C 0.3946(2) 0.4586(2) 0.13817(14) 0.0198 1.0000 Uani . . . . . .
C21 C 0.4158(2) 0.4846(2) 0.19772(14) 0.0210 1.0000 Uani . . . . . .
C22 C 0.4994(2) 0.5313(2) 0.20865(15) 0.0228 1.0000 Uani . . . . . .
C23 C 0.5609(2) 0.5535(2) 0.16107(16) 0.0234 1.0000 Uani . . . . . .
C24 C 0.5392(2) 0.5266(2) 0.10176(15) 0.0246 1.0000 Uani . . . . . .
C25 C 0.4566(3) 0.4798(2) 0.09081(16) 0.0242 1.0000 Uani . . . . . .
C26 C 0.6524(2) 0.6051(3) 0.17373(17) 0.0272 1.0000 Uani . . . . . .
C27 C 0.6343(2) 0.6831(2) 0.21490(15) 0.0229 1.0000 Uani . . . . . .
C28 C 0.5670(2) 0.7458(2) 0.19985(15) 0.0231 1.0000 Uani . . . . . .
C29 C 0.5549(2) 0.8202(2) 0.23452(15) 0.0226 1.0000 Uani . . . . . .
C30 C 0.6119(2) 0.8332(2) 0.28594(14) 0.0189 1.0000 Uani . . . . . .
C31 C 0.6775(2) 0.7694(2) 0.30259(14) 0.0215 1.0000 Uani . . . . . .
C32 C 0.6879(2) 0.6950(2) 0.26741(15) 0.0213 1.0000 Uani . . . . . .
N33 N 0.60541(19) 0.90877(18) 0.32359(12) 0.0194 1.0000 Uani . . . . . .
C34 C 0.5747(2) 0.9821(2) 0.30218(15) 0.0208 1.0000 Uani . . . . . .
C35 C 0.5692(2) 1.0625(2) 0.33479(16) 0.0236 1.0000 Uani . . . . . .
C36 C 0.5189(3) 1.1309(2) 0.30652(18) 0.0310 1.0000 Uani . . . . . .
C37 C 0.5138(3) 1.2133(3) 0.33083(19) 0.0332 1.0000 Uani . . . . . .
C38 C 0.4534(4) 1.2835(3) 0.3019(3) 0.0555 1.0000 Uani . . . . . .
C39 C 0.5653(3) 1.2285(2) 0.38452(18) 0.0297 1.0000 Uani . . . . . .
C40 C 0.6158(3) 1.1622(2) 0.41442(16) 0.0256 1.0000 Uani . . . . . .
C41 C 0.6146(2) 1.0771(2) 0.39161(16) 0.0218 1.0000 Uani . . . . . .
O42 O 0.65957(18) 1.01607(16) 0.42197(11) 0.0239 1.0000 Uani . . . . . .
C43 C 0.6637(3) 1.1844(2) 0.47424(17) 0.0269 1.0000 Uani . . . . . .
N44 N 0.7626(2) 1.15033(19) 0.48191(13) 0.0241 1.0000 Uani . . . . . .
C45 C 0.8267(3) 1.1598(3) 0.42742(17) 0.0295 1.0000 Uani . . . . . .
C46 C 0.8704(4) 1.2509(3) 0.4296(3) 0.0538 1.0000 Uani . . . . . .
C47 C 0.8478(4) 1.2861(3) 0.4941(3) 0.0495 1.0000 Uani . . . . . .
C48 C 0.8123(3) 1.2041(3) 0.5286(2) 0.0394 1.0000 Uani . . . . . .
C49 C 0.8995(3) 1.0864(3) 0.42630(17) 0.0306 1.0000 Uani . . . . . .
O50 O 0.87721(18) 1.01528(18) 0.45423(11) 0.0272 1.0000 Uani . . . . . .
O51 O 0.9758(2) 1.0964(2) 0.39792(14) 0.0437 1.0000 Uani . . . . . .
O101 O -0.0920(2) 0.4465(2) -0.11702(12) 0.0334 1.0000 Uani . . . . . .
O102 O 0.00274(17) 0.37555(16) -0.05340(11) 0.0234 1.0000 Uani . . . . . .
C103 C -0.0203(2) 0.4027(2) -0.10592(15) 0.0230 1.0000 Uani . . . . . .
C104 C 0.0442(2) 0.3779(2) -0.15977(14) 0.0204 1.0000 Uani . . . . . .
C105 C 0.0678(3) 0.2591(3) -0.23007(16) 0.0284 1.0000 Uani . . . . . .
C106 C 0.1232(2) 0.2404(2) -0.17220(15) 0.0227 1.0000 Uani . . . . . .
C107 C -0.0097(3) 0.3201(3) -0.20585(18) 0.0318 1.0000 Uani . . . . . .
N108 N 0.12963(19) 0.32617(17) -0.13969(12) 0.0173 1.0000 Uani . . . . . .
C109 C 0.2229(2) 0.3678(2) -0.15808(14) 0.0206 1.0000 Uani . . . . . .
C110 C 0.2314(2) 0.4627(2) -0.14194(14) 0.0196 1.0000 Uani . . . . . .
C111 C 0.2377(2) 0.5251(2) -0.18722(14) 0.0234 1.0000 Uani . . . . . .
C112 C 0.2509(3) 0.6136(2) -0.17480(15) 0.0257 1.0000 Uani . . . . . .
C113 C 0.2534(3) 0.6802(3) -0.22511(17) 0.0325 1.0000 Uani . . . . . .
C114 C 0.2615(3) 0.6364(2) -0.11436(15) 0.0235 1.0000 Uani . . . . . .
C115 C 0.2564(2) 0.5753(2) -0.06616(15) 0.0204 1.0000 Uani . . . . . .
C116 C 0.2375(2) 0.4873(2) -0.08005(14) 0.0194 1.0000 Uani . . . . . .
O117 O 0.22498(17) 0.42634(15) -0.03816(9) 0.0198 1.0000 Uani . . . . . .
C118 C 0.2645(2) 0.6093(2) -0.00554(14) 0.0183 1.0000 Uani . . . . . .
N119 N 0.26165(19) 0.56553(17) 0.04495(12) 0.0183 1.0000 Uani . . . . . .
C120 C 0.2603(2) 0.6137(2) 0.10107(14) 0.0183 1.0000 Uani . . . . . .
C121 C 0.1948(2) 0.5896(2) 0.14593(15) 0.0200 1.0000 Uani . . . . . .
C122 C 0.1848(2) 0.6389(2) 0.19884(15) 0.0210 1.0000 Uani . . . . . .
C123 C 0.2421(2) 0.7121(2) 0.20864(14) 0.0210 1.0000 Uani . . . . . .
C124 C 0.3091(2) 0.7348(2) 0.16381(16) 0.0231 1.0000 Uani . . . . . .
C125 C 0.3193(2) 0.6862(2) 0.11034(15) 0.0216 1.0000 Uani . . . . . .
C126 C 0.2275(2) 0.7666(2) 0.26530(15) 0.0248 1.0000 Uani . . . . . .
C127 C 0.3126(2) 0.7709(2) 0.30747(14) 0.0196 1.0000 Uani . . . . . .
C128 C 0.3722(2) 0.6990(2) 0.31785(15) 0.0217 1.0000 Uani . . . . . .
C129 C 0.4492(2) 0.7048(2) 0.35755(15) 0.0215 1.0000 Uani . . . . . .
C130 C 0.4671(2) 0.7829(2) 0.38732(13) 0.0180 1.0000 Uani . . . . . .
C131 C 0.4079(3) 0.8543(2) 0.37851(15) 0.0236 1.0000 Uani . . . . . .
C132 C 0.3305(3) 0.8473(2) 0.33935(16) 0.0253 1.0000 Uani . . . . . .
N133 N 0.5501(2) 0.79374(18) 0.42477(11) 0.0190 1.0000 Uani . . . . . .
C134 C 0.5701(2) 0.7346(2) 0.46448(15) 0.0219 1.0000 Uani . . . . . .
C135 C 0.6488(3) 0.7362(2) 0.50624(15) 0.0243 1.0000 Uani . . . . . .
C136 C 0.6522(3) 0.6659(2) 0.54782(17) 0.0272 1.0000 Uani . . . . . .
C137 C 0.7223(3) 0.6583(2) 0.59118(17) 0.0292 1.0000 Uani . . . . . .
C138 C 0.7242(3) 0.5841(3) 0.6359(2) 0.0441 1.0000 Uani . . . . . .
C139 C 0.7928(3) 0.7236(3) 0.59172(16) 0.0271 1.0000 Uani . . . . . .
C140 C 0.7919(2) 0.7939(2) 0.55296(15) 0.0251 1.0000 Uani . . . . . .
C141 C 0.7180(2) 0.8024(2) 0.50932(14) 0.0218 1.0000 Uani . . . . . .
O142 O 0.71826(17) 0.87290(15) 0.47478(10) 0.0208 1.0000 Uani . . . . . .
C143 C 0.8689(2) 0.8617(2) 0.55734(16) 0.0247 1.0000 Uani . . . . . .
N144 N 0.8332(2) 0.9491(2) 0.57743(13) 0.0246 1.0000 Uani . . . . . .
C145 C 0.9170(3) 1.0034(3) 0.59950(16) 0.0289 1.0000 Uani . . . . . .
C146 C 0.8773(3) 1.0559(3) 0.65211(19) 0.0369 1.0000 Uani . . . . . .
C147 C 0.8131(3) 0.9912(3) 0.68381(16) 0.0343 1.0000 Uani . . . . . .
C148 C 0.7636(3) 0.9445(2) 0.63020(14) 0.0254 1.0000 Uani . . . . . .
C149 C 0.6687(2) 0.9874(2) 0.61459(14) 0.0230 1.0000 Uani . . . . . .
O150 O 0.66020(17) 1.02533(18) 0.56258(10) 0.0257 1.0000 Uani . . . . . .
O151 O 0.60274(19) 0.98385(18) 0.65250(12) 0.0302 1.0000 Uani . . . . . .
O201 O 0.4097(4) 0.2196(4) 0.1317(3) 0.0364 0.5000 Uani . . . . . .
C202 C 0.5103(6) 0.2368(7) 0.1393(5) 0.0455 0.5000 Uani . . . . . .
O203 O 0.3874(3) 0.3023(4) 0.0118(3) 0.0621 0.7500 Uani . . . . . .
C204 C 0.4642(6) 0.2695(6) -0.0184(4) 0.0667 0.7500 Uani . . . . . .
O205 O 0.7177(3) 0.3286(2) 0.0377(2) 0.0650 1.0000 Uani . . . . . .
C206 C 0.7461(4) 0.3759(3) 0.0882(3) 0.0522 1.0000 Uani . . . . . .
C207 C 0.9617(4) 0.4479(3) 0.1868(2) 0.0486 1.0000 Uani . . . . . .
O208 O 0.9456(5) 0.5344(3) 0.1925(2) 0.0921 1.0000 Uani . . . . . .
O209 O 0.7340(3) 0.4455(3) 0.3491(2) 0.0685 1.0000 Uani . U . . . .
C210 C 0.7142(5) 0.3949(5) 0.2973(3) 0.0699 1.0000 Uani . U . . . .
C211 C 0.8616(6) 1.5147(6) 0.4921(4) 0.0358 0.5000 Uani . . . . . .
O212 O 0.9038(4) 1.5979(3) 0.4978(2) 0.0274 0.5000 Uani . . . . . .
C213 C 0.5539(4) 0.4622(3) 0.4656(2) 0.0467 1.0000 Uani . . . . . .
O214 O 0.5674(2) 0.4948(3) 0.40552(16) 0.0501 1.0000 Uani . . . . . .
O215 O 0.4249(3) 0.9398(3) 0.1311(2) 0.0494 0.7500 Uani . U . . . .
C216 C 0.4985(5) 0.9831(6) 0.0981(4) 0.0623 0.7500 Uani . U . . . .
O301 O 0.3418(4) 1.0747(6) 0.2036(2) 0.0839 0.7500 Uani . . . . . .
O302 O 0.26823(19) 0.94848(18) 0.05676(13) 0.0319 1.0000 Uani . . . . . .
O303 O 0.1670(2) 0.9891(2) 0.23187(13) 0.0411 1.0000 Uani . . . . . .
O304 O 0.9360(3) 1.4510(2) 0.65971(19) 0.0640 1.0000 Uani . . . . . .
O305 O 0.9273(5) 1.6819(4) 0.3925(3) 0.0736 0.7500 Uani . . . . . .
O307 O 0.8812(3) 0.5550(2) 0.31066(17) 0.0483 1.0000 Uani . . . . . .
O306 O 0.9010(4) 0.8574(3) 0.3772(2) 0.0907 1.0000 Uani . . . . . .
H41 H 0.1143 0.1209 0.0542 0.0241 1.0000 Uiso . . . . . .
H51 H 0.1077 0.0505 -0.0663 0.0302 1.0000 Uiso . . . . . .
H52 H 0.0980 -0.0038 -0.0049 0.0303 1.0000 Uiso . . . . . .
H61 H -0.0566 0.0267 -0.0582 0.0301 1.0000 Uiso . . . . . .
H62 H -0.0577 0.0532 0.0112 0.0302 1.0000 Uiso . . . . . .
H71 H -0.0149 0.1725 -0.0856 0.0280 1.0000 Uiso . . . . . .
H72 H -0.0950 0.1859 -0.0348 0.0273 1.0000 Uiso . . . . . .
H91 H -0.0400 0.2934 0.0429 0.0261 1.0000 Uiso . . . . . .
H92 H -0.0598 0.1949 0.0633 0.0263 1.0000 Uiso . . . . . .
H111 H -0.0310 0.1708 0.1621 0.0276 1.0000 Uiso . . . . . .
H131 H 0.0924 0.1506 0.2955 0.0584 1.0000 Uiso . . . . . .
H132 H 0.0013 0.2115 0.2983 0.0580 1.0000 Uiso . . . . . .
H133 H -0.0022 0.1225 0.2613 0.0584 1.0000 Uiso . . . . . .
H141 H 0.1921 0.2718 0.2492 0.0329 1.0000 Uiso . . . . . .
H181 H 0.3069 0.3508 0.2013 0.0265 1.0000 Uiso . . . . . .
H211 H 0.3741 0.4712 0.2304 0.0261 1.0000 Uiso . . . . . .
H221 H 0.5138 0.5485 0.2482 0.0274 1.0000 Uiso . . . . . .
H241 H 0.5809 0.5411 0.0700 0.0298 1.0000 Uiso . . . . . .
H251 H 0.4421 0.4637 0.0508 0.0291 1.0000 Uiso . . . . . .
H261 H 0.6806 0.6251 0.1351 0.0341 1.0000 Uiso . . . . . .
H262 H 0.6970 0.5663 0.1942 0.0346 1.0000 Uiso . . . . . .
H281 H 0.5294 0.7382 0.1649 0.0281 1.0000 Uiso . . . . . .
H291 H 0.5084 0.8612 0.2236 0.0289 1.0000 Uiso . . . . . .
H311 H 0.7142 0.7770 0.3376 0.0261 1.0000 Uiso . . . . . .
H321 H 0.7333 0.6515 0.2782 0.0263 1.0000 Uiso . . . . . .
H341 H 0.5553 0.9827 0.2609 0.0258 1.0000 Uiso . . . . . .
H361 H 0.4858 1.1201 0.2696 0.0382 1.0000 Uiso . . . . . .
H383 H 0.4800 1.3403 0.3127 0.0860 1.0000 Uiso . . . . . .
H382 H 0.4552 1.2790 0.2580 0.0864 1.0000 Uiso . . . . . .
H381 H 0.3878 1.2807 0.3167 0.0860 1.0000 Uiso . . . . . .
H391 H 0.5662 1.2858 0.4015 0.0362 1.0000 Uiso . . . . . .
H431 H 0.6644 1.2480 0.4777 0.0327 1.0000 Uiso . . . . . .
H432 H 0.6230 1.1608 0.5067 0.0332 1.0000 Uiso . . . . . .
H451 H 0.7859 1.1546 0.3911 0.0357 1.0000 Uiso . . . . . .
H461 H 0.9386 1.2476 0.4216 0.0674 1.0000 Uiso . . . . . .
H462 H 0.8407 1.2898 0.3990 0.0672 1.0000 Uiso . . . . . .
H471 H 0.9057 1.3088 0.5140 0.0620 1.0000 Uiso . . . . . .
H472 H 0.7988 1.3315 0.4937 0.0618 1.0000 Uiso . . . . . .
H481 H 0.7668 1.2205 0.5614 0.0480 1.0000 Uiso . . . . . .
H482 H 0.8661 1.1723 0.5462 0.0481 1.0000 Uiso . . . . . .
H1041 H 0.0659 0.4315 -0.1804 0.0255 1.0000 Uiso . . . . . .
H1051 H 0.1081 0.2891 -0.2596 0.0355 1.0000 Uiso . . . . . .
H1052 H 0.0397 0.2075 -0.2465 0.0353 1.0000 Uiso . . . . . .
H1061 H 0.1854 0.2169 -0.1803 0.0280 1.0000 Uiso . . . . . .
H1062 H 0.0847 0.1998 -0.1480 0.0280 1.0000 Uiso . . . . . .
H1071 H -0.0380 0.3549 -0.2389 0.0406 1.0000 Uiso . . . . . .
H1072 H -0.0598 0.2865 -0.1849 0.0399 1.0000 Uiso . . . . . .
H1111 H 0.2328 0.5068 -0.2288 0.0277 1.0000 Uiso . . . . . .
H1133 H 0.2811 0.7340 -0.2123 0.0505 1.0000 Uiso . . . . . .
H1132 H 0.2894 0.6597 -0.2597 0.0499 1.0000 Uiso . . . . . .
H1131 H 0.1902 0.6921 -0.2391 0.0501 1.0000 Uiso . . . . . .
H1141 H 0.2727 0.6938 -0.1043 0.0292 1.0000 Uiso . . . . . .
H1181 H 0.2719 0.6696 -0.0024 0.0236 1.0000 Uiso . . . . . .
H1211 H 0.1562 0.5402 0.1395 0.0251 1.0000 Uiso . . . . . .
H1221 H 0.1387 0.6238 0.2281 0.0245 1.0000 Uiso . . . . . .
H1241 H 0.3472 0.7832 0.1688 0.0283 1.0000 Uiso . . . . . .
H1251 H 0.3645 0.7010 0.0802 0.0275 1.0000 Uiso . . . . . .
H1261 H 0.2117 0.8255 0.2527 0.0302 1.0000 Uiso . . . . . .
H1262 H 0.1736 0.7413 0.2876 0.0298 1.0000 Uiso . . . . . .
H1281 H 0.3605 0.6468 0.2976 0.0276 1.0000 Uiso . . . . . .
H1291 H 0.4888 0.6568 0.3653 0.0258 1.0000 Uiso . . . . . .
H1311 H 0.4213 0.9065 0.3988 0.0294 1.0000 Uiso . . . . . .
H1321 H 0.2891 0.8938 0.3338 0.0316 1.0000 Uiso . . . . . .
H1341 H 0.5290 0.6871 0.4657 0.0268 1.0000 Uiso . . . . . .
H1361 H 0.6038 0.6229 0.5466 0.0326 1.0000 Uiso . . . . . .
H1383 H 0.7244 0.6037 0.6773 0.0679 1.0000 Uiso . . . . . .
H1382 H 0.6678 0.5481 0.6303 0.0679 1.0000 Uiso . . . . . .
H1381 H 0.7804 0.5473 0.6289 0.0683 1.0000 Uiso . . . . . .
H1391 H 0.8425 0.7191 0.6197 0.0327 1.0000 Uiso . . . . . .
H1431 H 0.9167 0.8413 0.5854 0.0298 1.0000 Uiso . . . . . .
H1432 H 0.8998 0.8677 0.5178 0.0297 1.0000 Uiso . . . . . .
H1451 H 0.9693 0.9651 0.6136 0.0361 1.0000 Uiso . . . . . .
H1452 H 0.9418 1.0409 0.5669 0.0362 1.0000 Uiso . . . . . .
H1461 H 0.9273 1.0789 0.6781 0.0451 1.0000 Uiso . . . . . .
H1462 H 0.8393 1.1049 0.6369 0.0454 1.0000 Uiso . . . . . .
H1471 H 0.7660 1.0182 0.7100 0.0439 1.0000 Uiso . . . . . .
H1472 H 0.8509 0.9493 0.7082 0.0438 1.0000 Uiso . . . . . .
H1481 H 0.7513 0.8827 0.6402 0.0300 1.0000 Uiso . . . . . .
H3051 H 0.8596 1.6874 0.3832 0.1175 1.0000 Uiso . . . . . .
H2121 H 0.8977 1.6239 0.4614 0.0422 1.0000 Uiso . . . . . .
H2111 H 0.8554 1.4890 0.5316 0.0523 0.5000 Uiso . . . . . .
H2112 H 0.9006 1.4788 0.4669 0.0523 0.5000 Uiso . . . . . .
H2113 H 0.7998 1.5203 0.4746 0.0523 0.5000 Uiso . . . . . .
H2161 H 0.5441 0.9412 0.0830 0.0848 0.7500 Uiso . . . . . .
H2162 H 0.5315 1.0232 0.1239 0.0848 0.7500 Uiso . . . . . .
H2163 H 0.4728 1.0139 0.0644 0.0848 0.7500 Uiso . . . . . .
H2131 H 0.4944 0.4824 0.4821 0.0563 1.0000 Uiso . . . . . .
H2132 H 0.6045 0.4827 0.4912 0.0563 1.0000 Uiso . . . . . .
H2133 H 0.5544 0.4005 0.4654 0.0563 1.0000 Uiso . . . . . .
H2101 H 0.7712 0.3777 0.2763 0.0998 1.0000 Uiso . . . . . .
H2102 H 0.6763 0.4292 0.2688 0.0998 1.0000 Uiso . . . . . .
H2103 H 0.6778 0.3446 0.3077 0.0998 1.0000 Uiso . . . . . .
H2071 H 0.9847 0.4353 0.1464 0.0593 1.0000 Uiso . . . . . .
H2072 H 1.0090 0.4297 0.2153 0.0593 1.0000 Uiso . . . . . .
H2073 H 0.9043 0.4162 0.1941 0.0593 1.0000 Uiso . . . . . .
H2061 H 0.8148 0.3794 0.0888 0.0635 0.7500 Uiso . . . . . .
H2062 H 0.7208 0.4335 0.0869 0.0635 0.7500 Uiso . . . . . .
H2063 H 0.7247 0.3480 0.1248 0.0635 0.7500 Uiso . . . . . .
H2021 H 0.5277 0.2297 0.1808 0.0661 0.5000 Uiso . . . . . .
H2022 H 0.5249 0.2954 0.1269 0.0661 0.5000 Uiso . . . . . .
H2023 H 0.5476 0.1979 0.1145 0.0661 0.5000 Uiso . . . . . .
H2041 H 0.4724 0.2082 -0.0061 0.1072 0.7500 Uiso . . . . . .
H2042 H 0.5216 0.2989 -0.0071 0.1072 0.7500 Uiso . . . . . .
H2043 H 0.4570 0.2706 -0.0609 0.1072 0.7500 Uiso . . . . . .
H1001 H 0.3353 0.2788 -0.0054 0.0776 0.7500 Uiso . . . . . .
H1002 H 0.4026 0.2453 0.0948 0.0441 0.5000 Uiso . . . . . .
H1003 H 0.7226 0.3674 0.0070 0.0772 1.0000 Uiso . . . . . .
H1004 H 0.7818 0.4810 0.3367 0.0841 1.0000 Uiso . . . . . .
H1005 H 0.9245 0.5413 0.2313 0.1115 1.0000 Uiso . . . . . .
H1006 H 0.6227 0.4787 0.3868 0.0611 1.0000 Uiso . . . . . .
H1007 H 0.3736 0.9426 0.1067 0.0598 0.7500 Uiso . . . . . .
H1008 H 0.9029 1.4636 0.6942 0.0771 1.0000 Uiso . . . . . .
H1009 H 0.9881 1.4212 0.6477 0.0771 1.0000 Uiso . . . . . .
H1010 H 0.8937 0.9053 0.4005 0.1057 1.0000 Uiso . . . . . .
H1011 H 0.9097 0.7997 0.3820 0.1057 1.0000 Uiso . . . . . .
H1013 H 0.8963 0.5970 0.3376 0.0591 1.0000 Uiso . . . . . .
H1014 H 0.9288 0.5168 0.3259 0.0591 1.0000 Uiso . . . . . .
H1018 H 0.2112 0.9480 0.0760 0.0388 1.0000 Uiso . . . . . .
H1091 H 0.2303 0.3623 -0.2011 0.0245 1.0000 Uiso . . . . . .
H1092 H 0.2731 0.3373 -0.1383 0.0245 1.0000 Uiso . . . . . .
H3054 H 0.9435 1.6218 0.3954 0.0892 0.5000 Uiso . . . . . .
H3022 H 0.2826 0.9851 0.0224 0.0376 0.7500 Uiso . . . . . .
H3011 H 0.3941 1.0353 0.2124 0.1032 0.7500 Uiso . . . . . .
H3013 H 0.3440 1.0878 0.1612 0.1032 0.7500 Uiso . . . . . .
H3031 H 0.1678 1.0000 0.1892 0.0491 1.0000 Uiso . . . . . .
H3032 H 0.2117 1.0263 0.2514 0.0491 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.1902(19)
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 . O17 . 1.920(2) yes
Cu1 . N19 . 1.947(3) yes
Cu1 . O117 . 1.897(2) yes
Cu1 . N119 . 1.985(3) yes
Cu2 . O1 . 1.930(2) yes
Cu2 . N8 . 2.100(3) yes
Cu2 . O17 . 2.384(2) yes
Cu2 . O102 . 1.918(2) yes
Cu2 . N108 . 2.072(3) yes
Cu2 . O117 . 2.419(2) yes
Cu3 . N33 . 1.947(3) yes
Cu3 . O42 . 1.909(2) yes
Cu3 . N133 . 1.961(3) yes
Cu3 . O142 . 1.889(2) yes
Cu4 . O42 . 2.396(2) yes
Cu4 . N44 . 2.093(3) yes
Cu4 . O50 . 1.920(2) yes
Cu4 . O142 . 2.441(2) yes
Cu4 . N144 . 2.101(3) yes
Cu4 . O150 . 1.906(2) yes
O1 . C3 . 1.288(4) yes
O2 . C3 . 1.228(4) yes
C3 . C4 . 1.525(4) yes
C4 . C5 . 1.540(5) yes
C4 . N8 . 1.508(4) yes
C4 . H41 . 0.983 no
C5 . C6 . 1.520(5) yes
C5 . H51 . 0.977 no
C5 . H52 . 0.986 no
C6 . C7 . 1.517(5) yes
C6 . H61 . 0.980 no
C6 . H62 . 0.966 no
C7 . N8 . 1.497(4) yes
C7 . H71 . 0.982 no
C7 . H72 . 0.960 no
N8 . C9 . 1.491(4) yes
C9 . C10 . 1.499(4) yes
C9 . H91 . 0.982 no
C9 . H92 . 0.966 no
C10 . C11 . 1.382(5) yes
C10 . C16 . 1.429(5) yes
C11 . C12 . 1.398(5) yes
C11 . H111 . 0.935 no
C12 . C13 . 1.500(5) yes
C12 . C14 . 1.376(5) yes
C13 . H131 . 0.954 no
C13 . H132 . 0.969 no
C13 . H133 . 0.980 no
C14 . C15 . 1.407(5) yes
C14 . H141 . 0.929 no
C15 . C16 . 1.419(4) yes
C15 . C18 . 1.424(5) yes
C16 . O17 . 1.304(4) yes
C18 . N19 . 1.304(4) yes
C18 . H181 . 0.942 no
N19 . C20 . 1.436(4) yes
C20 . C21 . 1.396(4) yes
C20 . C25 . 1.380(5) yes
C21 . C22 . 1.392(5) yes
C21 . H211 . 0.938 no
C22 . C23 . 1.384(5) yes
C22 . H221 . 0.928 no
C23 . C24 . 1.397(5) yes
C23 . C26 . 1.529(5) yes
C24 . C25 . 1.381(5) yes
C24 . H241 . 0.926 no
C25 . H251 . 0.934 no
C26 . C27 . 1.516(5) yes
C26 . H261 . 0.977 no
C26 . H262 . 0.974 no
C27 . C28 . 1.385(5) yes
C27 . C32 . 1.389(5) yes
C28 . C29 . 1.379(5) yes
C28 . H281 . 0.940 no
C29 . C30 . 1.398(4) yes
C29 . H291 . 0.936 no
C30 . C31 . 1.391(5) yes
C30 . N33 . 1.424(4) yes
C31 . C32 . 1.384(5) yes
C31 . H311 . 0.934 no
C32 . H321 . 0.951 no
N33 . C34 . 1.294(4) yes
C34 . C35 . 1.425(5) yes
C34 . H341 . 0.945 no
C35 . C36 . 1.409(5) yes
C35 . C41 . 1.419(5) yes
C36 . C37 . 1.373(6) yes
C36 . H361 . 0.949 no
C37 . C38 . 1.510(6) yes
C37 . C39 . 1.403(6) yes
C38 . H383 . 0.977 no
C38 . H382 . 0.963 no
C38 . H381 . 0.968 no
C39 . C40 . 1.403(5) yes
C39 . H391 . 0.953 no
C40 . C41 . 1.398(5) yes
C40 . C43 . 1.514(5) yes
C41 . O42 . 1.311(4) yes
C43 . N44 . 1.486(5) yes
C43 . H431 . 0.978 no
C43 . H432 . 0.973 no
N44 . C45 . 1.488(5) yes
N44 . C48 . 1.489(5) yes
C45 . C46 . 1.526(6) yes
C45 . C49 . 1.516(6) yes
C45 . H451 . 0.986 no
C46 . C47 . 1.539(8) yes
C46 . H461 . 0.966 no
C46 . H462 . 0.990 no
C47 . C48 . 1.545(7) yes
C47 . H471 . 0.985 no
C47 . H472 . 0.976 no
C48 . H481 . 0.986 no
C48 . H482 . 0.978 no
C49 . O50 . 1.286(5) yes
C49 . O51 . 1.235(5) yes
O101 . C103 . 1.231(4) yes
O102 . C103 . 1.266(4) yes
C103 . C104 . 1.522(4) yes
C104 . C107 . 1.544(5) yes
C104 . N108 . 1.501(4) yes
C104 . H1041 . 0.982 no
C105 . C106 . 1.518(5) yes
C105 . C107 . 1.520(5) yes
C105 . H1051 . 0.968 no
C105 . H1052 . 0.955 no
C106 . N108 . 1.498(4) yes
C106 . H1061 . 0.954 no
C106 . H1062 . 0.975 no
C107 . H1071 . 0.985 no
C107 . H1072 . 0.978 no
N108 . C109 . 1.500(4) yes
C109 . C110 . 1.502(5) yes
C109 . H1091 . 0.949 no
C109 . H1092 . 0.950 no
C110 . C111 . 1.380(5) yes
C110 . C116 . 1.408(4) yes
C111 . C112 . 1.396(5) yes
C111 . H1111 . 0.955 no
C112 . C113 . 1.501(5) yes
C112 . C114 . 1.377(5) yes
C113 . H1133 . 0.955 no
C113 . H1132 . 0.956 no
C113 . H1131 . 0.953 no
C114 . C115 . 1.411(5) yes
C114 . H1141 . 0.922 no
C115 . C116 . 1.409(5) yes
C115 . C118 . 1.430(4) yes
C116 . O117 . 1.319(4) yes
C118 . N119 . 1.292(4) yes
C118 . H1181 . 0.934 no
N119 . C120 . 1.432(4) yes
C120 . C121 . 1.383(5) yes
C120 . C125 . 1.398(4) yes
C121 . C122 . 1.388(5) yes
C121 . H1211 . 0.941 no
C122 . C123 . 1.397(5) yes
C122 . H1221 . 0.931 no
C123 . C124 . 1.390(5) yes
C123 . C126 . 1.506(5) yes
C124 . C125 . 1.392(5) yes
C124 . H1241 . 0.921 no
C125 . H1251 . 0.936 no
C126 . C127 . 1.513(4) yes
C126 . H1261 . 0.970 no
C126 . H1262 . 0.971 no
C127 . C128 . 1.402(5) yes
C127 . C132 . 1.388(5) yes
C128 . C129 . 1.391(4) yes
C128 . H1281 . 0.931 no
C129 . C130 . 1.388(4) yes
C129 . H1291 . 0.937 no
C130 . C131 . 1.386(5) yes
C130 . N133 . 1.435(4) yes
C131 . C132 . 1.390(5) yes
C131 . H1311 . 0.935 no
C132 . H1321 . 0.926 no
N133 . C134 . 1.289(4) yes
C134 . C135 . 1.436(4) yes
C134 . H1341 . 0.926 no
C135 . C136 . 1.411(5) yes
C135 . C141 . 1.403(5) yes
C136 . C137 . 1.375(5) yes
C136 . H1361 . 0.945 no
C137 . C138 . 1.501(5) yes
C137 . C139 . 1.403(5) yes
C138 . H1383 . 0.955 no
C138 . H1382 . 0.971 no
C138 . H1381 . 0.977 no
C139 . C140 . 1.371(5) yes
C139 . H1391 . 0.932 no
C140 . C141 . 1.418(4) yes
C140 . C143 . 1.500(5) yes
C141 . O142 . 1.319(4) yes
C143 . N144 . 1.494(5) yes
C143 . H1431 . 0.964 no
C143 . H1432 . 0.966 no
N144 . C145 . 1.518(4) yes
N144 . C148 . 1.501(4) yes
C145 . C146 . 1.505(5) yes
C145 . H1451 . 0.989 no
C145 . H1452 . 0.976 no
C146 . C147 . 1.501(6) yes
C146 . H1461 . 0.971 no
C146 . H1462 . 0.980 no
C147 . C148 . 1.543(5) yes
C147 . H1471 . 0.959 no
C147 . H1472 . 0.990 no
C148 . C149 . 1.521(5) yes
C148 . H1481 . 0.988 no
C149 . O150 . 1.284(4) yes
C149 . O151 . 1.232(4) yes
O201 . C202 . 1.439(11) yes
O201 . H1002 . 0.904 no
C202 . H2021 . 0.948 no
C202 . H2022 . 0.960 no
C202 . H2023 . 0.956 no
O203 . C204 . 1.348(10) yes
O203 . H1001 . 0.898 no
C204 . H2041 . 0.986 no
C204 . H2042 . 0.953 no
C204 . H2043 . 0.937 no
O205 . C206 . 1.383(7) yes
O205 . H1003 . 0.899 no
C206 . H2061 . 0.959 no
C206 . H2062 . 0.951 no
C206 . H2063 . 0.953 no
C207 . O208 . 1.351(7) yes
C207 . H2071 . 0.956 no
C207 . H2072 . 0.954 no
C207 . H2073 . 0.950 no
O208 . H1005 . 0.900 no
O209 . C210 . 1.403(7) yes
O209 . H1004 . 0.900 no
C210 . H2101 . 0.951 no
C210 . H2102 . 0.975 no
C210 . H2103 . 0.949 no
C211 . O212 . 1.411(10) yes
C211 . H2111 . 0.953 no
C211 . H2112 . 0.947 no
C211 . H2113 . 0.951 no
O212 . H2121 . 0.894 no
C213 . O214 . 1.416(6) yes
C213 . H2131 . 0.953 no
C213 . H2132 . 0.959 no
C213 . H2133 . 0.947 no
O214 . H1006 . 0.903 no
O215 . C216 . 1.414(9) yes
O215 . H1007 . 0.899 no
C216 . H2161 . 0.959 no
C216 . H2162 . 0.956 no
C216 . H2163 . 0.949 no
O301 . H3011 . 0.968 no
O301 . H3013 . 0.948 no
O302 . H1018 . 0.896 no
O302 . H3022 . 0.957 no
O303 . H3031 . 0.947 no
O303 . H3032 . 0.950 no
O304 . H1008 . 0.900 no
O304 . H1009 . 0.895 no
O305 . H3051 . 0.972 no
O305 . H3054 . 0.951 no
O307 . H1013 . 0.900 no
O307 . H1014 . 0.949 no
O306 . H1010 . 0.899 no
O306 . H1011 . 0.900 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
O17 . Cu1 . N19 . 94.92(11) yes
O17 . Cu1 . O117 . 85.92(10) yes
N19 . Cu1 . O117 . 155.64(11) yes
O17 . Cu1 . N119 . 144.07(11) yes
N19 . Cu1 . N119 . 98.70(11) yes
O117 . Cu1 . N119 . 94.61(11) yes
O1 . Cu2 . N8 . 85.17(11) yes
O1 . Cu2 . O17 . 85.33(9) yes
N8 . Cu2 . O17 . 82.81(9) yes
O1 . Cu2 . O102 . 177.57(11) yes
N8 . Cu2 . O102 . 93.23(11) yes
O17 . Cu2 . O102 . 96.29(9) yes
O1 . Cu2 . N108 . 95.17(10) yes
N8 . Cu2 . N108 . 127.48(10) yes
O17 . Cu2 . N108 . 149.69(9) yes
O102 . Cu2 . N108 . 84.35(10) yes
O1 . Cu2 . O117 . 87.27(9) yes
N8 . Cu2 . O117 . 147.97(9) yes
O17 . Cu2 . O117 . 65.57(7) yes
O102 . Cu2 . O117 . 95.04(10) yes
N108 . Cu2 . O117 . 84.16(9) yes
N33 . Cu3 . O42 . 93.91(11) yes
N33 . Cu3 . N133 . 96.94(11) yes
O42 . Cu3 . N133 . 149.72(11) yes
N33 . Cu3 . O142 . 151.57(11) yes
O42 . Cu3 . O142 . 87.10(10) yes
N133 . Cu3 . O142 . 96.29(11) yes
O42 . Cu4 . N44 . 78.18(10) yes
O42 . Cu4 . O50 . 92.06(10) yes
N44 . Cu4 . O50 . 83.72(12) yes
O42 . Cu4 . O142 . 65.49(8) yes
N44 . Cu4 . O142 . 143.14(10) yes
O50 . Cu4 . O142 . 91.31(10) yes
O42 . Cu4 . N144 . 147.72(10) yes
N44 . Cu4 . N144 . 134.02(12) yes
O50 . Cu4 . N144 . 93.72(11) yes
O142 . Cu4 . N144 . 82.64(10) yes
O42 . Cu4 . O150 . 90.63(10) yes
N44 . Cu4 . O150 . 95.44(12) yes
O50 . Cu4 . O150 . 176.96(11) yes
O142 . Cu4 . O150 . 91.10(10) yes
N144 . Cu4 . O150 . 84.74(11) yes
Cu2 . O1 . C3 . 116.9(2) yes
O1 . C3 . O2 . 123.6(3) yes
O1 . C3 . C4 . 118.0(3) yes
O2 . C3 . C4 . 118.4(3) yes
C3 . C4 . C5 . 110.7(3) yes
C3 . C4 . N8 . 112.7(3) yes
C5 . C4 . N8 . 106.1(2) yes
C3 . C4 . H41 . 108.3 no
C5 . C4 . H41 . 110.1 no
N8 . C4 . H41 . 108.8 no
C4 . C5 . C6 . 102.4(3) yes
C4 . C5 . H51 . 110.6 no
C6 . C5 . H51 . 110.0 no
C4 . C5 . H52 . 113.2 no
C6 . C5 . H52 . 113.0 no
H51 . C5 . H52 . 107.6 no
C5 . C6 . C7 . 101.1(3) yes
C5 . C6 . H61 . 111.1 no
C7 . C6 . H61 . 115.0 no
C5 . C6 . H62 . 111.0 no
C7 . C6 . H62 . 110.8 no
H61 . C6 . H62 . 107.8 no
C6 . C7 . N8 . 104.7(3) yes
C6 . C7 . H71 . 110.9 no
N8 . C7 . H71 . 108.8 no
C6 . C7 . H72 . 112.5 no
N8 . C7 . H72 . 111.0 no
H71 . C7 . H72 . 108.8 no
C4 . N8 . C7 . 105.9(2) yes
C4 . N8 . Cu2 . 106.50(18) yes
C7 . N8 . Cu2 . 112.64(19) yes
C4 . N8 . C9 . 115.0(2) yes
C7 . N8 . C9 . 106.8(2) yes
Cu2 . N8 . C9 . 110.0(2) yes
N8 . C9 . C10 . 115.1(3) yes
N8 . C9 . H91 . 109.7 no
C10 . C9 . H91 . 107.9 no
N8 . C9 . H92 . 107.6 no
C10 . C9 . H92 . 106.2 no
H91 . C9 . H92 . 110.2 no
C9 . C10 . C11 . 119.4(3) yes
C9 . C10 . C16 . 120.4(3) yes
C11 . C10 . C16 . 120.1(3) yes
C10 . C11 . C12 . 122.9(3) yes
C10 . C11 . H111 . 119.0 no
C12 . C11 . H111 . 118.1 no
C11 . C12 . C13 . 119.7(3) yes
C11 . C12 . C14 . 117.2(3) yes
C13 . C12 . C14 . 123.1(3) yes
C12 . C13 . H131 . 109.1 no
C12 . C13 . H132 . 110.2 no
H131 . C13 . H132 . 110.2 no
C12 . C13 . H133 . 108.3 no
H131 . C13 . H133 . 109.9 no
H132 . C13 . H133 . 109.1 no
C12 . C14 . C15 . 122.4(3) yes
C12 . C14 . H141 . 119.0 no
C15 . C14 . H141 . 118.6 no
C14 . C15 . C16 . 120.2(3) yes
C14 . C15 . C18 . 116.3(3) yes
C16 . C15 . C18 . 123.5(3) yes
C10 . C16 . C15 . 117.0(3) yes
C10 . C16 . O17 . 118.5(3) yes
C15 . C16 . O17 . 124.4(3) yes
Cu2 . O17 . C16 . 128.85(19) yes
Cu2 . O17 . Cu1 . 104.42(10) yes
C16 . O17 . Cu1 . 125.32(19) yes
C15 . C18 . N19 . 126.9(3) yes
C15 . C18 . H181 . 115.2 no
N19 . C18 . H181 . 117.9 no
C18 . N19 . Cu1 . 122.7(2) yes
C18 . N19 . C20 . 118.6(3) yes
Cu1 . N19 . C20 . 118.7(2) yes
N19 . C20 . C21 . 121.2(3) yes
N19 . C20 . C25 . 119.0(3) yes
C21 . C20 . C25 . 119.7(3) yes
C20 . C21 . C22 . 119.6(3) yes
C20 . C21 . H211 . 120.8 no
C22 . C21 . H211 . 119.6 no
C21 . C22 . C23 . 120.7(3) yes
C21 . C22 . H221 . 119.8 no
C23 . C22 . H221 . 119.5 no
C22 . C23 . C24 . 119.1(3) yes
C22 . C23 . C26 . 120.2(3) yes
C24 . C23 . C26 . 120.7(3) yes
C23 . C24 . C25 . 120.3(3) yes
C23 . C24 . H241 . 119.0 no
C25 . C24 . H241 . 120.8 no
C24 . C25 . C20 . 120.6(3) yes
C24 . C25 . H251 . 119.3 no
C20 . C25 . H251 . 120.1 no
C23 . C26 . C27 . 112.5(3) yes
C23 . C26 . H261 . 109.5 no
C27 . C26 . H261 . 109.3 no
C23 . C26 . H262 . 107.7 no
C27 . C26 . H262 . 108.2 no
H261 . C26 . H262 . 109.6 no
C26 . C27 . C28 . 121.0(3) yes
C26 . C27 . C32 . 120.4(3) yes
C28 . C27 . C32 . 118.5(3) yes
C27 . C28 . C29 . 121.5(3) yes
C27 . C28 . H281 . 119.5 no
C29 . C28 . H281 . 119.0 no
C28 . C29 . C30 . 119.5(3) yes
C28 . C29 . H291 . 119.8 no
C30 . C29 . H291 . 120.7 no
C29 . C30 . C31 . 119.5(3) yes
C29 . C30 . N33 . 123.3(3) yes
C31 . C30 . N33 . 117.3(3) yes
C30 . C31 . C32 . 120.0(3) yes
C30 . C31 . H311 . 119.7 no
C32 . C31 . H311 . 120.3 no
C27 . C32 . C31 . 120.9(3) yes
C27 . C32 . H321 . 118.7 no
C31 . C32 . H321 . 120.4 no
C30 . N33 . Cu3 . 117.6(2) yes
C30 . N33 . C34 . 121.2(3) yes
Cu3 . N33 . C34 . 121.0(2) yes
N33 . C34 . C35 . 126.0(3) yes
N33 . C34 . H341 . 117.0 no
C35 . C34 . H341 . 117.1 no
C34 . C35 . C36 . 116.6(3) yes
C34 . C35 . C41 . 123.5(3) yes
C36 . C35 . C41 . 119.8(3) yes
C35 . C36 . C37 . 122.6(4) yes
C35 . C36 . H361 . 119.6 no
C37 . C36 . H361 . 117.8 no
C36 . C37 . C38 . 121.4(4) yes
C36 . C37 . C39 . 116.9(3) yes
C38 . C37 . C39 . 121.7(4) yes
C37 . C38 . H383 . 108.6 no
C37 . C38 . H382 . 111.0 no
H383 . C38 . H382 . 107.4 no
C37 . C38 . H381 . 111.0 no
H383 . C38 . H381 . 108.7 no
H382 . C38 . H381 . 110.1 no
C37 . C39 . C40 . 122.3(3) yes
C37 . C39 . H391 . 119.2 no
C40 . C39 . H391 . 118.5 no
C39 . C40 . C41 . 120.2(3) yes
C39 . C40 . C43 . 118.0(3) yes
C41 . C40 . C43 . 121.7(3) yes
C35 . C41 . C40 . 117.8(3) yes
C35 . C41 . O42 . 123.5(3) yes
C40 . C41 . O42 . 118.6(3) yes
Cu4 . O42 . C41 . 133.3(2) yes
Cu4 . O42 . Cu3 . 104.18(10) yes
C41 . O42 . Cu3 . 122.0(2) yes
C40 . C43 . N44 . 116.0(3) yes
C40 . C43 . H431 . 107.1 no
N44 . C43 . H431 . 109.3 no
C40 . C43 . H432 . 106.7 no
N44 . C43 . H432 . 108.8 no
H431 . C43 . H432 . 108.7 no
C43 . N44 . Cu4 . 113.2(2) yes
C43 . N44 . C45 . 115.2(3) yes
Cu4 . N44 . C45 . 106.7(2) yes
C43 . N44 . C48 . 108.8(3) yes
Cu4 . N44 . C48 . 109.9(2) yes
C45 . N44 . C48 . 102.4(3) yes
N44 . C45 . C46 . 107.5(3) yes
N44 . C45 . C49 . 109.7(3) yes
C46 . C45 . C49 . 114.4(4) yes
N44 . C45 . H451 . 106.8 no
C46 . C45 . H451 . 109.5 no
C49 . C45 . H451 . 108.7 no
C45 . C46 . C47 . 105.8(4) yes
C45 . C46 . H461 . 109.8 no
C47 . C46 . H461 . 112.1 no
C45 . C46 . H462 . 111.1 no
C47 . C46 . H462 . 109.0 no
H461 . C46 . H462 . 109.1 no
C46 . C47 . C48 . 102.9(4) yes
C46 . C47 . H471 . 111.7 no
C48 . C47 . H471 . 109.3 no
C46 . C47 . H472 . 112.2 no
C48 . C47 . H472 . 111.4 no
H471 . C47 . H472 . 109.2 no
C47 . C48 . N44 . 105.4(4) yes
C47 . C48 . H481 . 110.3 no
N44 . C48 . H481 . 109.9 no
C47 . C48 . H482 . 110.8 no
N44 . C48 . H482 . 111.1 no
H481 . C48 . H482 . 109.3 no
C45 . C49 . O50 . 117.6(3) yes
C45 . C49 . O51 . 119.3(4) yes
O50 . C49 . O51 . 123.1(4) yes
C49 . O50 . Cu4 . 116.8(2) yes
Cu2 . O102 . C103 . 118.3(2) yes
O102 . C103 . O101 . 125.0(3) yes
O102 . C103 . C104 . 117.8(3) yes
O101 . C103 . C104 . 117.3(3) yes
C103 . C104 . C107 . 111.1(3) yes
C103 . C104 . N108 . 111.7(3) yes
C107 . C104 . N108 . 106.3(3) yes
C103 . C104 . H1041 . 108.8 no
C107 . C104 . H1041 . 109.3 no
N108 . C104 . H1041 . 109.5 no
C106 . C105 . C107 . 101.1(3) yes
C106 . C105 . H1051 . 110.4 no
C107 . C105 . H1051 . 110.2 no
C106 . C105 . H1052 . 111.9 no
C107 . C105 . H1052 . 110.4 no
H1051 . C105 . H1052 . 112.3 no
C105 . C106 . N108 . 105.3(3) yes
C105 . C106 . H1061 . 112.8 no
N108 . C106 . H1061 . 111.2 no
C105 . C106 . H1062 . 106.9 no
N108 . C106 . H1062 . 109.8 no
H1061 . C106 . H1062 . 110.7 no
C104 . C107 . C105 . 103.4(3) yes
C104 . C107 . H1071 . 111.6 no
C105 . C107 . H1071 . 111.6 no
C104 . C107 . H1072 . 110.3 no
C105 . C107 . H1072 . 109.9 no
H1071 . C107 . H1072 . 109.8 no
C104 . N108 . C106 . 105.9(2) yes
C104 . N108 . Cu2 . 107.73(18) yes
C106 . N108 . Cu2 . 108.77(19) yes
C104 . N108 . C109 . 112.6(2) yes
C106 . N108 . C109 . 107.6(2) yes
Cu2 . N108 . C109 . 113.84(19) yes
N108 . C109 . C110 . 114.8(3) yes
N108 . C109 . H1091 . 108.1 no
C110 . C109 . H1091 . 108.2 no
N108 . C109 . H1092 . 108.1 no
C110 . C109 . H1092 . 108.0 no
H1091 . C109 . H1092 . 109.6 no
C109 . C110 . C111 . 120.5(3) yes
C109 . C110 . C116 . 119.4(3) yes
C111 . C110 . C116 . 120.0(3) yes
C110 . C111 . C112 . 122.8(3) yes
C110 . C111 . H1111 . 118.3 no
C112 . C111 . H1111 . 118.8 no
C111 . C112 . C113 . 121.4(3) yes
C111 . C112 . C114 . 116.7(3) yes
C113 . C112 . C114 . 121.9(3) yes
C112 . C113 . H1133 . 112.3 no
C112 . C113 . H1132 . 111.4 no
H1133 . C113 . H1132 . 107.8 no
C112 . C113 . H1131 . 110.5 no
H1133 . C113 . H1131 . 107.9 no
H1132 . C113 . H1131 . 106.7 no
C112 . C114 . C115 . 122.9(3) yes
C112 . C114 . H1141 . 119.5 no
C115 . C114 . H1141 . 117.6 no
C114 . C115 . C116 . 118.9(3) yes
C114 . C115 . C118 . 116.5(3) yes
C116 . C115 . C118 . 124.5(3) yes
C115 . C116 . C110 . 118.5(3) yes
C115 . C116 . O117 . 123.5(3) yes
C110 . C116 . O117 . 117.9(3) yes
Cu2 . O117 . C116 . 124.96(19) yes
Cu2 . O117 . Cu1 . 103.87(9) yes
C116 . O117 . Cu1 . 127.0(2) yes
C115 . C118 . N119 . 126.9(3) yes
C115 . C118 . H1181 . 116.1 no
N119 . C118 . H1181 . 117.0 no
C118 . N119 . Cu1 . 122.6(2) yes
C118 . N119 . C120 . 117.7(3) yes
Cu1 . N119 . C120 . 119.4(2) yes
N119 . C120 . C121 . 118.1(3) yes
N119 . C120 . C125 . 122.2(3) yes
C121 . C120 . C125 . 119.6(3) yes
C120 . C121 . C122 . 120.3(3) yes
C120 . C121 . H1211 . 118.9 no
C122 . C121 . H1211 . 120.7 no
C121 . C122 . C123 . 120.9(3) yes
C121 . C122 . H1221 . 120.0 no
C123 . C122 . H1221 . 119.0 no
C122 . C123 . C124 . 118.2(3) yes
C122 . C123 . C126 . 120.0(3) yes
C124 . C123 . C126 . 121.7(3) yes
C123 . C124 . C125 . 121.3(3) yes
C123 . C124 . H1241 . 120.1 no
C125 . C124 . H1241 . 118.5 no
C120 . C125 . C124 . 119.5(3) yes
C120 . C125 . H1251 . 119.0 no
C124 . C125 . H1251 . 121.5 no
C123 . C126 . C127 . 115.2(3) yes
C123 . C126 . H1261 . 108.2 no
C127 . C126 . H1261 . 108.3 no
C123 . C126 . H1262 . 106.7 no
C127 . C126 . H1262 . 108.6 no
H1261 . C126 . H1262 . 109.7 no
C126 . C127 . C128 . 122.4(3) yes
C126 . C127 . C132 . 119.4(3) yes
C128 . C127 . C132 . 118.2(3) yes
C127 . C128 . C129 . 121.0(3) yes
C127 . C128 . H1281 . 119.5 no
C129 . C128 . H1281 . 119.6 no
C128 . C129 . C130 . 119.5(3) yes
C128 . C129 . H1291 . 121.5 no
C130 . C129 . H1291 . 119.0 no
C129 . C130 . C131 . 120.4(3) yes
C129 . C130 . N133 . 121.2(3) yes
C131 . C130 . N133 . 118.3(3) yes
C130 . C131 . C132 . 119.5(3) yes
C130 . C131 . H1311 . 119.2 no
C132 . C131 . H1311 . 121.3 no
C131 . C132 . C127 . 121.3(3) yes
C131 . C132 . H1321 . 120.7 no
C127 . C132 . H1321 . 118.0 no
C130 . N133 . Cu3 . 118.4(2) yes
C130 . N133 . C134 . 119.0(3) yes
Cu3 . N133 . C134 . 122.5(2) yes
N133 . C134 . C135 . 126.0(3) yes
N133 . C134 . H1341 . 115.8 no
C135 . C134 . H1341 . 118.2 no
C134 . C135 . C136 . 115.3(3) yes
C134 . C135 . C141 . 125.1(3) yes
C136 . C135 . C141 . 119.5(3) yes
C135 . C136 . C137 . 122.6(3) yes
C135 . C136 . H1361 . 119.1 no
C137 . C136 . H1361 . 118.3 no
C136 . C137 . C138 . 122.1(4) yes
C136 . C137 . C139 . 116.7(3) yes
C138 . C137 . C139 . 121.2(3) yes
C137 . C138 . H1383 . 112.3 no
C137 . C138 . H1382 . 109.2 no
H1383 . C138 . H1382 . 108.0 no
C137 . C138 . H1381 . 110.9 no
H1383 . C138 . H1381 . 108.7 no
H1382 . C138 . H1381 . 107.5 no
C137 . C139 . C140 . 122.9(3) yes
C137 . C139 . H1391 . 118.6 no
C140 . C139 . H1391 . 118.4 no
C139 . C140 . C141 . 120.0(3) yes
C139 . C140 . C143 . 119.6(3) yes
C141 . C140 . C143 . 120.4(3) yes
C140 . C141 . C135 . 118.2(3) yes
C140 . C141 . O142 . 117.6(3) yes
C135 . C141 . O142 . 124.2(3) yes
Cu4 . O142 . C141 . 125.78(19) yes
Cu4 . O142 . Cu3 . 103.16(10) yes
C141 . O142 . Cu3 . 125.4(2) yes
C140 . C143 . N144 . 113.8(3) yes
C140 . C143 . H1431 . 108.4 no
N144 . C143 . H1431 . 109.6 no
C140 . C143 . H1432 . 108.8 no
N144 . C143 . H1432 . 108.7 no
H1431 . C143 . H1432 . 107.2 no
C143 . N144 . Cu4 . 112.9(2) yes
C143 . N144 . C145 . 109.3(3) yes
Cu4 . N144 . C145 . 107.7(2) yes
C143 . N144 . C148 . 113.2(3) yes
Cu4 . N144 . C148 . 107.3(2) yes
C145 . N144 . C148 . 105.9(3) yes
N144 . C145 . C146 . 105.0(3) yes
N144 . C145 . H1451 . 110.3 no
C146 . C145 . H1451 . 110.2 no
N144 . C145 . H1452 . 111.0 no
C146 . C145 . H1452 . 111.6 no
H1451 . C145 . H1452 . 108.7 no
C145 . C146 . C147 . 102.2(3) yes
C145 . C146 . H1461 . 112.4 no
C147 . C146 . H1461 . 113.5 no
C145 . C146 . H1462 . 110.2 no
C147 . C146 . H1462 . 110.0 no
H1461 . C146 . H1462 . 108.3 no
C146 . C147 . C148 . 103.0(3) yes
C146 . C147 . H1471 . 113.0 no
C148 . C147 . H1471 . 110.1 no
C146 . C147 . H1472 . 111.1 no
C148 . C147 . H1472 . 110.6 no
H1471 . C147 . H1472 . 108.9 no
C147 . C148 . N144 . 105.8(3) yes
C147 . C148 . C149 . 111.6(3) yes
N144 . C148 . C149 . 111.4(3) yes
C147 . C148 . H1481 . 110.9 no
N144 . C148 . H1481 . 108.9 no
C149 . C148 . H1481 . 108.3 no
C148 . C149 . O150 . 118.9(3) yes
C148 . C149 . O151 . 118.3(3) yes
O150 . C149 . O151 . 122.7(3) yes
C149 . O150 . Cu4 . 117.5(2) yes
C202 . O201 . H1002 . 98.1 no
O201 . C202 . H2021 . 110.5 no
O201 . C202 . H2022 . 110.1 no
H2021 . C202 . H2022 . 108.8 no
O201 . C202 . H2023 . 110.2 no
H2021 . C202 . H2023 . 109.1 no
H2022 . C202 . H2023 . 108.1 no
C204 . O203 . H1001 . 106.7 no
O203 . C204 . H2041 . 108.4 no
O203 . C204 . H2042 . 111.2 no
H2041 . C204 . H2042 . 106.3 no
O203 . C204 . H2043 . 112.7 no
H2041 . C204 . H2043 . 107.6 no
H2042 . C204 . H2043 . 110.3 no
C206 . O205 . H1003 . 103.2 no
O205 . C206 . H2061 . 109.7 no
O205 . C206 . H2062 . 110.7 no
H2061 . C206 . H2062 . 108.6 no
O205 . C206 . H2063 . 110.2 no
H2061 . C206 . H2063 . 108.5 no
H2062 . C206 . H2063 . 109.1 no
O208 . C207 . H2071 . 109.8 no
O208 . C207 . H2072 . 109.9 no
H2071 . C207 . H2072 . 108.6 no
O208 . C207 . H2073 . 110.4 no
H2071 . C207 . H2073 . 109.0 no
H2072 . C207 . H2073 . 109.1 no
C207 . O208 . H1005 . 104.8 no
C210 . O209 . H1004 . 104.2 no
O209 . C210 . H2101 . 111.7 no
O209 . C210 . H2102 . 109.3 no
H2101 . C210 . H2102 . 107.3 no
O209 . C210 . H2103 . 111.4 no
H2101 . C210 . H2103 . 109.4 no
H2102 . C210 . H2103 . 107.5 no
O212 . C211 . H2111 . 109.1 no
O212 . C211 . H2112 . 109.9 no
H2111 . C211 . H2112 . 109.5 no
O212 . C211 . H2113 . 109.5 no
H2111 . C211 . H2113 . 109.1 no
H2112 . C211 . H2113 . 109.6 no
C211 . O212 . H2121 . 106.3 no
O214 . C213 . H2131 . 110.0 no
O214 . C213 . H2132 . 109.6 no
H2131 . C213 . H2132 . 108.5 no
O214 . C213 . H2133 . 110.2 no
H2131 . C213 . H2133 . 109.5 no
H2132 . C213 . H2133 . 109.0 no
C213 . O214 . H1006 . 115.3 no
C216 . O215 . H1007 . 104.6 no
O215 . C216 . H2161 . 109.6 no
O215 . C216 . H2162 . 110.6 no
H2161 . C216 . H2162 . 108.2 no
O215 . C216 . H2163 . 110.6 no
H2161 . C216 . H2163 . 108.8 no
H2162 . C216 . H2163 . 109.1 no
H3011 . O301 . H3013 . 108.2 no
H1018 . O302 . H3022 . 123.4 no
H3031 . O303 . H3032 . 109.7 no
H1008 . O304 . H1009 . 139.6 no
H3051 . O305 . H3054 . 109.3 no
H1013 . O307 . H1014 . 92.4 no
H1010 . O306 . H1011 . 138.7 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
C9 . H91 . O102 . 121.6 0.982 2.520 3.147(6) yes
C21 . H211 . O151 2_646 130.8 0.938 2.592 3.282(6) yes
C36 . H361 . O301 . 155.7 0.949 2.581 3.468(6) yes
C38 . H383 . O151 2_656 131.1 0.977 2.596 3.321(6) yes
C43 . H432 . O150 . 123.3 0.973 2.469 3.111(6) yes
C114 . H1141 . O205 2_655 158.0 0.922 2.533 3.405(6) yes
C118 . H1181 . O205 2_655 158.0 0.934 2.561 3.445(6) yes
O212 . H2121 . O305 . 160.8 0.894 1.794 2.655(6) yes
C213 . H2131 . O150 2_646 134.3 0.953 2.466 3.205(6) yes
O203 . H1001 . O1 . 179.6 0.898 1.879 2.778(6) yes
O203 . H1001 . C3 . 149.4 0.898 2.495 3.300(6) yes
O201 . H1002 . O203 . 179.6 0.904 2.028 2.931(6) yes
O205 . H1003 . O302 2_645 179.5 0.899 1.872 2.771(6) yes
O209 . H1004 . O307 . 179.8 0.900 1.874 2.774(6) yes
O208 . H1005 . O307 . 179.9 0.900 1.843 2.743(6) yes
O214 . H1006 . O209 . 179.6 0.903 1.823 2.726(6) yes
O215 . H1007 . O302 . 179.9 0.899 1.843 2.741(6) yes
O304 . H1008 . O303 2_656 179.3 0.900 1.919 2.819(6) yes
O304 . H1009 . O306 2_756 179.6 0.895 1.903 2.798(6) yes
O306 . H1010 . O50 . 179.8 0.899 2.067 2.966(6) yes
O306 . H1011 . O305 1_545 179.6 0.900 1.838 2.739(6) yes
O307 . H1013 . O305 1_545 179.7 0.900 1.826 2.726(6) yes
O302 . H1018 . O101 2_555 179.42 0.896 1.879 2.775(6) yes
O302 . H3022 . O2 1_565 138.33 0.957 1.951 2.741(6) yes
O303 . H3031 . O101 2_555 132.7 0.947 2.079 2.809(6) yes
O303 . H3032 . O301 . 121.8 0.950 2.212 2.831(6) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/07/17 at 17:17:43
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/07/17 at 17:17:43
#
#LIST     16                                                                    
U(IJ)'S  0.0, 0.010000 = O(209) TO C(210) 
U(IJ)'S  0.0, 0.010000 = O(215) TO C(216) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
