# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1560984'
_audit_update_record             
;
2017-07-08 deposited with the CCDC.
2018-10-15 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                   15.3230(7)
_cell_length_b                   14.3515(6)
_cell_length_c                   7.4141(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1630.42(13)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,y+1/2,z+1/2
x+1/2,-y+1/2,z
-x,-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'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'


_cell_formula_units_Z            4

# Given Formula = C21 Cu1 N3 O6 
# Dc =      1.85 Fooo =    856.00 Mu =     13.92 M =    453.79
# Found Formula = C14 H12 Cu1 N3 O8.50 
# Dc =      1.72 FOOO =    856.00 Mu =     13.94 M =    421.81

_chemical_formula_sum            'C14 H12 Cu1 N3 O8.50'
_chemical_formula_moiety         'C14 H12 Cu1 N3 O8.50'
_chemical_compound_source        ?
_chemical_formula_weight         421.81


_cell_measurement_reflns_used    5805
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29
_cell_measurement_temperature    293

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.138
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_max          0.598

_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):          
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    1.394

# Sheldrick geometric approximatio 0.79 0.82 
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.82
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       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            9821
_reflns_number_total             3548
_diffrn_reflns_av_R_equivalents  0.020
# Number of reflections without Friedels Law is 3548 
# Number of reflections with Friedels Law is 2103 
# Theoretical number of reflections is about 2264 


_diffrn_reflns_theta_min         2.839
_diffrn_reflns_theta_max         29.464
_diffrn_measured_fraction_theta_max 0.904

_diffrn_reflns_theta_full        25.044
_diffrn_measured_fraction_theta_full 0.979


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              0
_reflns_limit_h_max              21
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              -9
_reflns_limit_l_max              10

_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         -0.52
_refine_diff_density_max         0.76


# 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         3222
_refine_ls_number_restraints     1
_refine_ls_number_parameters     245
_oxford_refine_ls_R_factor_ref   0.0324
_refine_ls_wR_factor_ref         0.0328
_refine_ls_goodness_of_fit_ref   1.0460
_refine_ls_shift/su_max          0.0067930
_refine_ls_shift/su_mean         0.0002714


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3538
_refine_ls_R_factor_all          0.0361
_refine_ls_wR_factor_all         0.0334

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3338
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_gt          0.0329

_refine_ls_abs_structure_Flack   0.001(13)
_refine_ls_abs_structure_details 'Flack (1983), 1445 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: 
 4.07 -0.968 2.18 
;

# 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 0.48519(16) 0.95864(13) 0.0004(3) 0.0424 1.0000 Uani . . . . . .
C2 C 0.45205(16) 0.90956(16) -0.1208(4) 0.0238 1.0000 Uani . . . . . .
O3 O 0.41728(13) 0.94390(12) -0.2586(3) 0.0312 1.0000 Uani . . . . . .
C4 C 0.44569(17) 0.80489(16) -0.1024(3) 0.0235 1.0000 Uani . . . . . .
C5 C 0.37576(18) 0.76215(17) -0.1870(4) 0.0298 1.0000 Uani . . . . . .
C6 C 0.36340(19) 0.66688(18) -0.1754(4) 0.0320 1.0000 Uani . . . . . .
C7 C 0.42247(18) 0.61280(16) -0.0807(4) 0.0282 1.0000 Uani . . . . . .
C8 C 0.40856(19) 0.50931(18) -0.0741(4) 0.0326 1.0000 Uani . . . . . .
O9 O 0.35366(18) 0.47090(14) -0.1655(4) 0.0548 1.0000 Uani . . . . . .
O10 O 0.46093(16) 0.46599(13) 0.0369(3) 0.0440 1.0000 Uani . . . . . .
C11 C 0.49309(18) 0.65361(16) 0.0053(4) 0.0267 1.0000 Uani . . . . . .
C12 C 0.50553(16) 0.75030(16) -0.0048(3) 0.0227 1.0000 Uani . . . . . .
N13 N 0.57741(14) 0.79342(14) 0.0823(3) 0.0238 1.0000 Uani . . . . . .
C14 C 0.64624(18) 0.74983(17) 0.1291(3) 0.0290 1.0000 Uani . . . . . .
C15 C 0.71371(17) 0.80222(17) 0.2246(3) 0.0275 1.0000 Uani . . . . . .
C16 C 0.7933(2) 0.7647(2) 0.2750(4) 0.0361 1.0000 Uani . . . . . .
C17 C 0.8534(2) 0.8223(2) 0.3578(4) 0.0403 1.0000 Uani . . . . . .
C18 C 0.8333(2) 0.9148(2) 0.3851(5) 0.0425 1.0000 Uani . . . . . .
C19 C 0.7523(2) 0.9472(2) 0.3319(4) 0.0379 1.0000 Uani . . . . . .
N20 N 0.69338(15) 0.89278(15) 0.2556(3) 0.0294 1.0000 Uani . . . . . .
N31 N 0.6296(2) 0.7361(2) 0.6482(5) 0.0579 1.0000 Uani . . . . . .
O32 O 0.56746(17) 0.71231(15) 0.5440(4) 0.0503 1.0000 Uani . . . . . .
O33 O 0.6460(3) 0.8192(2) 0.6589(6) 0.1167 1.0000 Uani . . . . . .
O34 O 0.6697(2) 0.6758(3) 0.7318(4) 0.0848 1.0000 Uani . . . . . .
O41 O 0.4767(2) 0.86285(16) 0.3680(4) 0.0573 1.0000 Uani . . . . . .
O51 O 0.6643(3) 0.9928(3) -0.1424(7) 0.0505 0.5000 Uani . . . . . .
Cu1 Cu 0.574335(18) 0.924491(17) 0.17254(10) 0.0268 1.0000 Uani . . . . . .
H51 H 0.3360 0.7984 -0.2544 0.0350 1.0000 Uiso R . . . . .
H61 H 0.3153 0.6398 -0.2297 0.0383 1.0000 Uiso R . . . . .
H111 H 0.5320 0.6172 0.0699 0.0306 1.0000 Uiso R . . . . .
H141 H 0.6537 0.6875 0.1046 0.0331 1.0000 Uiso R . . . . .
H161 H 0.8049 0.7028 0.2570 0.0419 1.0000 Uiso R . . . . .
H171 H 0.9070 0.8008 0.3931 0.0484 1.0000 Uiso R . . . . .
H181 H 0.8734 0.9558 0.4377 0.0497 1.0000 Uiso R . . . . .
H191 H 0.7386 1.0096 0.3517 0.0453 1.0000 Uiso R . . . . .
H101 H 0.4441 0.4122 0.0444 0.0642 1.0000 Uiso R . . . . .
H511 H 0.5052 0.8156 0.4234 0.0694 1.0000 Uiso . . . . . .
H512 H 0.4891 0.9201 0.4105 0.0694 1.0000 Uiso . . . . . .
H1 H 0.6103 0.9823 -0.0995 0.0603 0.5000 Uiso R . . . . .
H2 H 0.6585 0.9389 -0.2039 0.0603 0.5000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.006(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.249(3) yes
O1 . Cu1 . 1.933(2) yes
C2 . O3 . 1.254(3) yes
C2 . C4 . 1.511(3) yes
O3 . Cu1 4_674 1.9606(18) yes
C4 . C5 . 1.385(4) yes
C4 . C12 . 1.407(3) yes
C5 . C6 . 1.383(3) yes
C5 . H51 . 0.945 no
C6 . C7 . 1.384(4) yes
C6 . H61 . 0.925 no
C7 . C8 . 1.501(3) yes
C7 . C11 . 1.386(4) yes
C8 . O9 . 1.212(4) yes
C8 . O10 . 1.307(4) yes
O10 . H101 . 0.816 no
C11 . C12 . 1.403(3) yes
C11 . H111 . 0.926 no
C12 . N13 . 1.419(3) yes
N13 . C14 . 1.274(3) yes
N13 . Cu1 . 1.997(2) yes
C14 . C15 . 1.461(4) yes
C14 . H141 . 0.920 no
C15 . C16 . 1.384(4) yes
C15 . N20 . 1.356(3) yes
C16 . C17 . 1.383(4) yes
C16 . H161 . 0.915 no
C17 . C18 . 1.377(5) yes
C17 . H171 . 0.915 no
C18 . C19 . 1.382(4) yes
C18 . H181 . 0.936 no
C19 . N20 . 1.322(4) yes
C19 . H191 . 0.931 no
N20 . Cu1 . 1.978(2) yes
N31 . O32 . 1.273(4) yes
N31 . O33 . 1.221(4) yes
N31 . O34 . 1.229(5) yes
O41 . Cu1 . 2.263(3) yes
O41 . H511 . 0.905 no
O41 . H512 . 0.900 no
O51 . H1 . 0.900 no
O51 . H2 . 0.903 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
C2 . O1 . Cu1 . 128.26(17) yes
O1 . C2 . O3 . 122.5(2) yes
O1 . C2 . C4 . 121.4(2) yes
O3 . C2 . C4 . 115.9(2) yes
C2 . O3 . Cu1 4_674 124.27(17) yes
C2 . C4 . C5 . 116.7(2) yes
C2 . C4 . C12 . 123.9(2) yes
C5 . C4 . C12 . 119.4(2) yes
C4 . C5 . C6 . 121.0(2) yes
C4 . C5 . H51 . 119.7 no
C6 . C5 . H51 . 119.3 no
C5 . C6 . C7 . 119.8(2) yes
C5 . C6 . H61 . 119.8 no
C7 . C6 . H61 . 120.4 no
C6 . C7 . C8 . 118.6(2) yes
C6 . C7 . C11 . 120.5(2) yes
C8 . C7 . C11 . 120.9(2) yes
C7 . C8 . O9 . 122.0(3) yes
C7 . C8 . O10 . 113.8(2) yes
O9 . C8 . O10 . 124.2(2) yes
C8 . O10 . H101 . 107.4 no
C7 . C11 . C12 . 120.0(2) yes
C7 . C11 . H111 . 120.2 no
C12 . C11 . H111 . 119.8 no
C4 . C12 . C11 . 119.3(2) yes
C4 . C12 . N13 . 119.8(2) yes
C11 . C12 . N13 . 120.9(2) yes
C12 . N13 . C14 . 123.5(2) yes
C12 . N13 . Cu1 . 123.02(16) yes
C14 . N13 . Cu1 . 112.99(17) yes
N13 . C14 . C15 . 117.7(2) yes
N13 . C14 . H141 . 121.7 no
C15 . C14 . H141 . 120.6 no
C14 . C15 . C16 . 123.6(2) yes
C14 . C15 . N20 . 114.4(2) yes
C16 . C15 . N20 . 122.0(2) yes
C15 . C16 . C17 . 118.3(3) yes
C15 . C16 . H161 . 120.6 no
C17 . C16 . H161 . 121.0 no
C16 . C17 . C18 . 119.5(3) yes
C16 . C17 . H171 . 121.5 no
C18 . C17 . H171 . 119.0 no
C17 . C18 . C19 . 118.9(3) yes
C17 . C18 . H181 . 121.3 no
C19 . C18 . H181 . 119.7 no
C18 . C19 . N20 . 122.4(3) yes
C18 . C19 . H191 . 118.8 no
N20 . C19 . H191 . 118.7 no
C15 . N20 . C19 . 118.8(2) yes
C15 . N20 . Cu1 . 112.29(17) yes
C19 . N20 . Cu1 . 128.9(2) yes
O32 . N31 . O33 . 117.1(4) yes
O32 . N31 . O34 . 119.4(3) yes
O33 . N31 . O34 . 123.5(5) yes
Cu1 . O41 . H511 . 105.3 no
Cu1 . O41 . H512 . 74.2 no
H511 . O41 . H512 . 115.0 no
H1 . O51 . H2 . 86.8 no
O41 . Cu1 . N13 . 82.07(9) yes
O41 . Cu1 . N20 . 108.69(11) yes
N13 . Cu1 . N20 . 82.29(9) yes
O41 . Cu1 . O3 4_675 104.67(8) yes
N13 . Cu1 . O3 4_675 173.21(9) yes
N20 . Cu1 . O3 4_675 94.60(9) yes
O41 . Cu1 . O1 . 93.12(11) yes
N13 . Cu1 . O1 . 91.96(9) yes
N20 . Cu1 . O1 . 156.29(11) yes
O3 4_675 Cu1 . O1 . 88.51(8) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C5 . H51 . O34 3_464 137.61(10) 0.945 2.576 3.335(4) yes
C17 . H171 . O41 3_565 130.99(10) 0.915 2.587 3.261(4) yes
O10 . H101 . N31 4_664 163.41(11) 0.816 2.529 3.319(4) yes
O10 . H101 . O32 4_664 166.52(11) 0.816 1.796 2.596(4) yes
O10 . H101 . O34 4_664 135.98(11) 0.816 2.562 3.200(4) yes
O41 . H511 . O32 . 179.89(18) 0.905 1.977 2.882(4) yes
O41 . H512 . O1 4_675 179.8(2) 0.900 1.905 2.805(4) yes
O51 . H1 . O1 . 179.7(3) 0.900 2.082 2.982(4) yes
O51 . H2 . O33 1_554 179.8(4) 0.903 2.006 2.908(4) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 30/10/12 at 16:12:02
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE O   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,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   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE O   (  41,X'S) H   (   1,X'S) H   (   2,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 30/10/12 at 16:12:02
#
#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 
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data_4844
_database_code_depnum_ccdc_archive 'CCDC 1560985'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT355_4844                
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O3W      - H3WB     .       1.19 Ang.
RESPONSE: This is an estimation of the hydrogen bonding pattern . It is likely to be disordered resulting in longer O-H distances, especially since it  is Xray and not neutron data
;
_vrf_PLAT415_4844                
;
PROBLEM: Short Inter D-H..H-X       H1WA     ..H25              1.96 Ang.
RESPONSE: This is an estimation of the hydrogen bonding pattern . It is likely to be disordered
;
_vrf_PLAT417_4844                
;
PROBLEM: Short Inter D-H..H-D       H1WB     ..H2WB             2.06 Ang.
RESPONSE: This is an estimation of the hydrogen bonding pattern . It is likely to be disordered. Thre H atoms were located in the difference map and restrained to maximise H bonding contacts 
;
_vrf_PLAT420_4844                
;
PROBLEM: D-H Without Acceptor       O1W      --H1WB           Please Check
RESPONSE: This is an estimation of the hydrogen bonding pattern . It is likely to be disordered
;
# Added during the CSD deposition process: Friday 11 May 2018 10:28 AM
# end Validation Reply Form

_audit_creation_date             2018-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'0.25(C56 H32 Cu4 N8 O16), 0.5(H1.08 O), 1.5(H2 O)'
_chemical_formula_sum            'C14 H12 Cu N2 O6'
_chemical_formula_weight         367.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   18.503(3)
_cell_length_b                   17.141(3)
_cell_length_c                   8.8358(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.932(7)
_cell_angle_gamma                90
_cell_volume                     2800.8(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1409
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.308
_cell_measurement_theta_min      2.203
_shelx_estimated_absorpt_T_max   0.808
_shelx_estimated_absorpt_T_min   0.664
_exptl_absorpt_coefficient_mu    1.595
_exptl_absorpt_correction_T_max  0.800
_exptl_absorpt_correction_T_min  0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2008/4 (Bruker,2010) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0713 before and 0.0545 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0928 before and 0.0658 after correction.
 The Ratio of minimum to maximum transmission is 0.75.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 33237 reflections, Rint = 0.0944
 (9403 with I > 3sig(I), Rint = 0.0708)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5505
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.047
_diffrn_reflns_theta_min         1.101
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4161
_reflns_number_total             5505
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         2.521
_refine_diff_density_min         -1.271
_refine_diff_density_rms         0.187
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5505
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0736
_refine_ls_restrained_S_all      5.907
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1224P)²+10.3995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2216
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.703(2)
 0.297(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Restrained distances
 O1W-H1WB = O1W-H1WA = O2W-H2WA = O2W-H2WB = O4W-H4WA = O4W-H4WB
 0.85 with sigma of 0.01
 O3W-H3WB = O3W-H3WA
 0.8 with sigma of 0.001
4. Others
 Sof(H1WA)=Sof(H1WB)=FVAR(1)
5.a Everything fixed:
 O1W, H1WA, H1WB
5.b Free rotating group:
 O2W(H2WA,H2WB), O3W(H3WA,H3WB), O4W(H4WA,H4WB)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C8(H8), C10(H10), C11(H11), C17(H17),
 C18(H18), C21(H21), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.05156(5) 0.37024(5) 0.88924(13) 0.0174(3) Uani 1 1 d . . . . .
Cu2 Cu 0.55588(5) 0.35891(6) 1.13163(14) 0.0212(3) Uani 1 1 d . . . . .
O1 O 0.0109(3) 0.2833(4) 0.7199(9) 0.0313(17) Uani 1 1 d . . . . .
O2 O 0.0515(3) 0.2964(3) 1.0517(8) 0.0253(14) Uani 1 1 d . . . . .
O3 O 0.1523(3) 0.3477(3) 0.8527(7) 0.0194(13) Uani 1 1 d . . . . .
O4 O 0.1820(3) 0.4142(4) 1.0605(8) 0.0277(15) Uani 1 1 d . . . . .
O5 O 0.5009(4) 0.2724(4) 1.2682(10) 0.044(2) Uani 1 1 d . . . . .
O6 O 0.5502(3) 0.2982(4) 0.9502(9) 0.0316(16) Uani 1 1 d . . . . .
O7 O 0.6558(3) 0.3279(4) 1.1685(8) 0.0269(15) Uani 1 1 d . . . . .
O8 O 0.6784(3) 0.4173(4) 0.9907(10) 0.0386(19) Uani 1 1 d . . . . .
N1 N 0.0505(4) 0.4669(4) 0.7618(8) 0.0200(16) Uani 1 1 d . . . . .
N2 N -0.0502(4) 0.4025(4) 0.9259(8) 0.0156(15) Uani 1 1 d . . . . .
N3 N 0.5644(4) 0.4527(5) 1.2657(10) 0.0260(18) Uani 1 1 d . . . . .
N4 N 0.4577(4) 0.4052(4) 1.0851(9) 0.0189(16) Uani 1 1 d . . . . .
C1 C 0.1025(5) 0.4974(6) 0.6836(11) 0.024(2) Uani 1 1 d . . . . .
H1 H 0.1489 0.4736 0.6877 0.029 Uiso 1 1 calc R . . . .
C2 C 0.0913(6) 0.5643(5) 0.5942(11) 0.029(2) Uani 1 1 d . . . . .
H2 H 0.1297 0.5858 0.5389 0.035 Uiso 1 1 calc R . . . .
C3 C 0.0245(6) 0.5980(5) 0.5879(11) 0.029(2) Uani 1 1 d . . . . .
H3 H 0.0154 0.6418 0.5243 0.034 Uiso 1 1 calc R . . . .
C4 C -0.0304(5) 0.5678(5) 0.6752(11) 0.027(2) Uani 1 1 d . . . . .
H4 H -0.0765 0.5922 0.6772 0.032 Uiso 1 1 calc R . . . .
C5 C -0.0154(4) 0.5019(5) 0.7578(10) 0.0184(19) Uani 1 1 d . . . . .
C6 C -0.0685(4) 0.4642(5) 0.8518(11) 0.0204(19) Uani 1 1 d . . . . .
H6 H -0.1159 0.4850 0.8582 0.025 Uiso 1 1 calc R . . . .
C7 C -0.1007(5) 0.3624(5) 1.0150(10) 0.0201(19) Uani 1 1 d . . . . .
C8 C -0.1741(5) 0.3822(5) 1.0082(11) 0.0203(19) Uani 1 1 d . . . . .
H8 H -0.1902 0.4240 0.9450 0.024 Uiso 1 1 calc R . . . .
C9 C -0.2231(5) 0.3421(5) 1.0919(12) 0.024(2) Uani 1 1 d . . . . .
C10 C -0.1993(5) 0.2807(5) 1.1861(12) 0.026(2) Uani 1 1 d . . . . .
H10 H -0.2325 0.2536 1.2468 0.031 Uiso 1 1 calc R . . . .
C11 C -0.1284(4) 0.2605(5) 1.1893(11) 0.023(2) Uani 1 1 d . . . . .
H11 H -0.1130 0.2181 1.2516 0.027 Uiso 1 1 calc R . . . .
C12 C -0.0769(4) 0.2995(4) 1.1050(11) 0.0164(17) Uani 1 1 d . . . . .
C13 C 0.0004(5) 0.2691(4) 1.1257(11) 0.0192(19) Uani 1 1 d . . . . .
C14 C 0.6977(5) 0.3651(5) 1.0809(12) 0.027(2) Uani 1 1 d . . . . .
C15 C 0.1985(5) 0.3721(5) 0.9538(9) 0.0185(19) Uani 1 1 d . . . . .
C16 C 0.2754(4) 0.3492(5) 0.9318(10) 0.0156(17) Uani 1 1 d . . . . .
C17 C 0.2927(4) 0.2870(5) 0.8379(12) 0.024(2) Uani 1 1 d . . . . .
H17 H 0.2556 0.2595 0.7834 0.029 Uiso 1 1 calc R . . . .
C18 C 0.3639(4) 0.2659(5) 0.8251(12) 0.028(2) Uani 1 1 d . . . . .
H18 H 0.3753 0.2236 0.7606 0.033 Uiso 1 1 calc R . . . .
C19 C 0.4200(4) 0.3044(5) 0.9033(10) 0.0180(18) Uani 1 1 d . . . . .
C20 C 0.4025(4) 0.3665(4) 0.9988(9) 0.0135(17) Uani 1 1 d . . . . .
C21 C 0.3308(5) 0.3875(5) 1.0119(10) 0.0179(18) Uani 1 1 d . . . . .
H21 H 0.3191 0.4292 1.0774 0.021 Uiso 1 1 calc R . . . .
C22 C 0.4959(4) 0.2743(5) 0.8730(12) 0.022(2) Uani 1 1 d . . . . .
C23 C 0.4485(4) 0.4705(4) 1.1532(11) 0.0177(18) Uani 1 1 d . . . . .
H23 H 0.4049 0.4991 1.1375 0.021 Uiso 1 1 calc R . . . .
C24 C 0.5054(5) 0.4999(5) 1.2540(11) 0.0204(19) Uani 1 1 d . . . . .
C25 C 0.5004(5) 0.5682(5) 1.3354(12) 0.029(2) Uani 1 1 d . . . . .
H25 H 0.4580 0.5993 1.3281 0.035 Uiso 1 1 calc R . . . .
C26 C 0.5584(6) 0.5903(6) 1.4276(13) 0.035(2) Uani 1 1 d . . . . .
H26 H 0.5568 0.6372 1.4846 0.042 Uiso 1 1 calc R . . . .
C27 C 0.6186(5) 0.5430(7) 1.4355(14) 0.038(3) Uani 1 1 d . . . . .
H27 H 0.6598 0.5585 1.4950 0.046 Uiso 1 1 calc R . . . .
C28 C 0.6193(5) 0.4730(6) 1.3572(13) 0.032(2) Uani 1 1 d . . . . .
H28 H 0.6598 0.4391 1.3693 0.039 Uiso 1 1 calc R . . . .
O1W O 0.3455 0.6573 1.3021 0.051 Uani 1 1 d D . . . .
H1WA H 0.3742 0.6545 1.2374 0.076 Uiso 0.5416 1 d D . P A 1
H1WB H 0.3466 0.6694 1.3713 0.076 Uiso 0.5416 1 d D . P A 1
O2W O 0.2193(5) 0.5758(5) 1.3693(13) 0.063(3) Uani 1 1 d D . . . .
H2WA H 0.2248 0.5320 1.4179 0.094 Uiso 1 1 d DG . . . .
H2WB H 0.2611 0.5929 1.3421 0.094 Uiso 1 1 d DG . . . .
O3W O 0.2370(4) 0.4142(4) 1.3556(9) 0.0380(18) Uani 1 1 d D . . . .
H3WA H 0.2092 0.3837 1.4069 0.057 Uiso 1 1 d DG . . . .
H3WB H 0.2054 0.4246 1.2383 0.057 Uiso 1 1 d DG . . . .
O4W O 0.1616(4) 0.3179(4) 1.5413(9) 0.0356(17) Uani 1 1 d D . . . .
H4WA H 0.1961 0.2848 1.5248 0.053 Uiso 1 1 d DG . . . .
H4WB H 0.1201 0.2940 1.5342 0.053 Uiso 1 1 d DG . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.225(6) . ?
Cu1 O2 1.913(6) . ?
Cu1 O3 1.942(6) . ?
Cu1 N1 2.002(7) . ?
Cu1 N2 1.999(7) . ?
Cu2 O5 2.185(7) . ?
Cu2 O6 1.911(7) . ?
Cu2 O7 1.941(6) . ?
Cu2 N3 2.001(8) . ?
Cu2 N4 2.012(7) . ?
O1 C13 1.235(11) 4_565 ?
O2 C13 1.257(11) . ?
O3 C15 1.285(10) . ?
O4 C15 1.234(11) . ?
O5 C22 1.230(12) 4_566 ?
O6 C22 1.264(11) . ?
O7 C14 1.282(12) . ?
O8 C14 1.242(12) . ?
N1 C1 1.312(12) . ?
N1 C5 1.360(11) . ?
N2 C6 1.283(11) . ?
N2 C7 1.419(11) . ?
N3 C24 1.359(12) . ?
N3 C28 1.324(13) . ?
N4 C20 1.419(11) . ?
N4 C23 1.286(11) . ?
C1 H1 0.9500 . ?
C1 C2 1.405(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.363(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.368(12) . ?
C5 C6 1.459(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(12) . ?
C7 C12 1.402(12) . ?
C8 H8 0.9500 . ?
C8 C9 1.374(13) . ?
C9 C10 1.403(12) . ?
C9 C14 1.518(12) 1_455 ?
C10 H10 0.9500 . ?
C10 C11 1.358(12) . ?
C11 H11 0.9500 . ?
C11 C12 1.398(12) . ?
C12 C13 1.528(11) . ?
C13 O1 1.235(11) 4_566 ?
C14 C9 1.518(12) 1_655 ?
C15 C16 1.495(12) . ?
C16 C17 1.394(12) . ?
C16 C21 1.391(12) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(12) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(13) . ?
C19 C20 1.403(12) . ?
C19 C22 1.528(12) . ?
C20 C21 1.383(12) . ?
C21 H21 0.9500 . ?
C22 O5 1.230(12) 4_565 ?
C23 H23 0.9500 . ?
C23 C24 1.446(13) . ?
C24 C25 1.379(14) . ?
C25 H25 0.9500 . ?
C25 C26 1.377(15) . ?
C26 H26 0.9500 . ?
C26 C27 1.378(15) . ?
C27 H27 0.9500 . ?
C27 C28 1.385(15) . ?
C28 H28 0.9500 . ?
O1W H1WA 0.7959 . ?
O1W H1WB 0.6448 . ?
O2W H2WA 0.8691 . ?
O2W H2WB 0.8688 . ?
O3W H3WA 0.8703 . ?
O3W H3WB 1.1867 . ?
O4W H4WA 0.8698 . ?
O4W H4WB 0.8705 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 93.0(3) . . ?
O2 Cu1 O3 91.1(3) . . ?
O2 Cu1 N1 165.6(3) . . ?
O2 Cu1 N2 92.1(3) . . ?
O3 Cu1 O1 93.4(2) . . ?
O3 Cu1 N1 93.5(3) . . ?
O3 Cu1 N2 175.4(3) . . ?
N1 Cu1 O1 100.3(3) . . ?
N2 Cu1 O1 89.7(3) . . ?
N2 Cu1 N1 82.6(3) . . ?
O6 Cu2 O5 94.6(3) . . ?
O6 Cu2 O7 91.0(3) . . ?
O6 Cu2 N3 159.3(3) . . ?
O6 Cu2 N4 91.1(3) . . ?
O7 Cu2 O5 100.4(3) . . ?
O7 Cu2 N3 93.8(3) . . ?
O7 Cu2 N4 172.2(3) . . ?
N3 Cu2 O5 104.3(3) . . ?
N3 Cu2 N4 81.7(3) . . ?
N4 Cu2 O5 86.9(3) . . ?
C13 O1 Cu1 169.1(6) 4_565 . ?
C13 O2 Cu1 131.0(6) . . ?
C15 O3 Cu1 116.1(6) . . ?
C22 O5 Cu2 154.9(7) 4_566 . ?
C22 O6 Cu2 130.5(6) . . ?
C14 O7 Cu2 110.7(6) . . ?
C1 N1 Cu1 129.2(6) . . ?
C1 N1 C5 118.9(8) . . ?
C5 N1 Cu1 111.8(6) . . ?
C6 N2 Cu1 112.3(6) . . ?
C6 N2 C7 120.9(7) . . ?
C7 N2 Cu1 126.7(5) . . ?
C24 N3 Cu2 112.7(6) . . ?
C28 N3 Cu2 128.0(7) . . ?
C28 N3 C24 119.3(8) . . ?
C20 N4 Cu2 123.7(5) . . ?
C23 N4 Cu2 112.4(6) . . ?
C23 N4 C20 123.6(7) . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.6(9) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(9) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(9) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.5(9) . . ?
C5 C4 H4 121.2 . . ?
N1 C5 C4 123.0(8) . . ?
N1 C5 C6 114.2(7) . . ?
C4 C5 C6 122.8(8) . . ?
N2 C6 C5 119.0(8) . . ?
N2 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 N2 121.0(8) . . ?
C8 C7 C12 119.8(8) . . ?
C12 C7 N2 119.2(7) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.9(9) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 119.6(8) . . ?
C8 C9 C14 119.3(8) . 1_455 ?
C10 C9 C14 121.0(8) . 1_455 ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(8) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 118.6 . . ?
C10 C11 C12 122.8(9) . . ?
C12 C11 H11 118.6 . . ?
C7 C12 C13 127.2(8) . . ?
C11 C12 C7 117.6(8) . . ?
C11 C12 C13 115.2(7) . . ?
O1 C13 O2 121.2(8) 4_566 . ?
O1 C13 C12 117.0(8) 4_566 . ?
O2 C13 C12 121.9(8) . . ?
O7 C14 C9 115.7(9) . 1_655 ?
O8 C14 O7 125.4(8) . . ?
O8 C14 C9 118.9(9) . 1_655 ?
O3 C15 C16 116.0(8) . . ?
O4 C15 O3 123.0(8) . . ?
O4 C15 C16 121.0(8) . . ?
C17 C16 C15 121.1(8) . . ?
C21 C16 C15 119.9(8) . . ?
C21 C16 C17 118.9(8) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.3(8) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 118.8 . . ?
C17 C18 C19 122.3(9) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C20 118.3(8) . . ?
C18 C19 C22 115.3(8) . . ?
C20 C19 C22 126.4(8) . . ?
C19 C20 N4 120.1(7) . . ?
C21 C20 N4 120.6(7) . . ?
C21 C20 C19 119.3(7) . . ?
C16 C21 H21 119.1 . . ?
C20 C21 C16 121.8(8) . . ?
C20 C21 H21 119.1 . . ?
O5 C22 O6 122.6(9) 4_565 . ?
O5 C22 C19 116.4(8) 4_565 . ?
O6 C22 C19 121.0(9) . . ?
N4 C23 H23 120.5 . . ?
N4 C23 C24 119.0(8) . . ?
C24 C23 H23 120.5 . . ?
N3 C24 C23 114.0(8) . . ?
N3 C24 C25 122.2(9) . . ?
C25 C24 C23 123.8(9) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 C24 118.5(9) . . ?
C26 C25 H25 120.7 . . ?
C25 C26 H26 120.6 . . ?
C25 C26 C27 118.7(10) . . ?
C27 C26 H26 120.6 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.4(10) . . ?
C28 C27 H27 119.8 . . ?
N3 C28 C27 120.8(9) . . ?
N3 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
H1WA O1W H1WB 134.5 . . ?
H2WA O2W H2WB 109.7 . . ?
H3WA O3W H3WB 105.2 . . ?
H4WA O4W H4WB 109.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2W 0.95 2.28 3.148(14) 151.9 1_554
C6 H6 O4 0.95 2.25 3.077(10) 145.1 3_567
C23 H23 O8 0.95 2.36 3.259(10) 156.8 3_667
C27 H27 O3W 0.95 2.33 3.280(12) 175.4 3_668
O2W H2WA O3W 0.87 2.11 2.792(12) 135.3 .
O3W H3WA O4W 0.87 1.88 2.742(10) 170.7 .
O4W H4WB O2 0.87 2.01 2.831(9) 156.1 4_566

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.703(2)
2 0.297(2)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol, water'
