# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_H2L
_database_code_depnum_ccdc_archive 'CCDC 1414834'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 O4'
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.8448(8)
_cell_length_b                   21.9422(18)
_cell_length_c                   22.4274(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4844.7(7)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8868
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      29.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9824
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   SADABS,Sheldrick,2008

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            51444
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         31.61
_reflns_number_total             8055
_reflns_number_gt                5395
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0774P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8055
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.89011(13) 0.36166(6) 0.17988(6) 0.0220(3) Uani 1 1 d . . .
H1 H 0.8798 0.4028 0.1924 0.026 Uiso 1 1 calc R . .
C2 C 0.84629(14) 0.31388(6) 0.21594(6) 0.0275(3) Uani 1 1 d . . .
H2A H 0.8042 0.3226 0.2531 0.033 Uiso 1 1 calc R . .
C3 C 0.86314(14) 0.25369(6) 0.19844(6) 0.0272(3) Uani 1 1 d . . .
H3 H 0.8341 0.2218 0.2241 0.033 Uiso 1 1 calc R . .
C4 C 0.92176(13) 0.23961(5) 0.14404(6) 0.0221(3) Uani 1 1 d . . .
H4 H 0.9339 0.1984 0.1322 0.026 Uiso 1 1 calc R . .
C5 C 1.04991(14) 0.23832(6) 0.00860(6) 0.0248(3) Uani 1 1 d . . .
H5 H 1.0335 0.1974 0.0205 0.030 Uiso 1 1 calc R . .
C6 C 1.10436(16) 0.25136(6) -0.04692(7) 0.0316(3) Uani 1 1 d . . .
H6 H 1.1253 0.2189 -0.0734 0.038 Uiso 1 1 calc R . .
C7 C 1.12870(16) 0.31075(7) -0.06438(7) 0.0319(3) Uani 1 1 d . . .
H7 H 1.1671 0.3186 -0.1025 0.038 Uiso 1 1 calc R . .
C8 C 1.09764(13) 0.35936(6) -0.02678(6) 0.0242(3) Uani 1 1 d . . .
H8 H 1.1144 0.4002 -0.0389 0.029 Uiso 1 1 calc R . .
C9 C 0.99991(11) 0.39138(5) 0.07731(5) 0.0151(2) Uani 1 1 d . . .
C10 C 0.94896(11) 0.34803(5) 0.12542(5) 0.0157(2) Uani 1 1 d . . .
C11 C 0.96270(11) 0.28731(5) 0.10697(5) 0.0162(2) Uani 1 1 d . . .
C12 C 1.01972(11) 0.28668(5) 0.04664(6) 0.0171(2) Uani 1 1 d . . .
C13 C 1.04190(11) 0.34696(5) 0.02854(6) 0.0166(2) Uani 1 1 d . . .
C14 C 0.88721(11) 0.43575(5) 0.05680(6) 0.0174(2) Uani 1 1 d . . .
H14A H 0.8691 0.4653 0.0892 0.021 Uiso 1 1 calc R . .
H14B H 0.9202 0.4589 0.0218 0.021 Uiso 1 1 calc R . .
C15 C 0.75551(12) 0.40406(5) 0.04045(6) 0.0216(3) Uani 1 1 d . . .
H15A H 0.7731 0.3750 0.0076 0.026 Uiso 1 1 calc R . .
H15B H 0.7232 0.3804 0.0752 0.026 Uiso 1 1 calc R . .
C16 C 0.64629(12) 0.44750(5) 0.02165(6) 0.0205(3) Uani 1 1 d . . .
C17 C 1.12086(11) 0.43086(5) 0.09800(6) 0.0194(2) Uani 1 1 d . . .
H17A H 1.1455 0.4593 0.0655 0.023 Uiso 1 1 calc R . .
H17B H 1.0918 0.4556 0.1326 0.023 Uiso 1 1 calc R . .
C18 C 1.24621(12) 0.39441(5) 0.11542(6) 0.0214(3) Uani 1 1 d . . .
H18A H 1.2226 0.3661 0.1482 0.026 Uiso 1 1 calc R . .
H18B H 1.2764 0.3697 0.0809 0.026 Uiso 1 1 calc R . .
C19 C 1.36044(12) 0.43496(6) 0.13512(7) 0.0243(3) Uani 1 1 d . . .
C20 C 1.0000 0.58577(7) 0.2500 0.0162(3) Uani 1 2 d S . .
C21 C 0.93493(12) 0.62977(5) 0.29416(6) 0.0180(2) Uani 1 1 d . . .
C22 C 0.85293(13) 0.61635(6) 0.34239(6) 0.0250(3) Uani 1 1 d . . .
H22 H 0.8360 0.5753 0.3535 0.030 Uiso 1 1 calc R . .
C23 C 0.79543(15) 0.66440(7) 0.37452(7) 0.0320(3) Uani 1 1 d . . .
H23 H 0.7370 0.6559 0.4072 0.038 Uiso 1 1 calc R . .
C24 C 0.82267(16) 0.72427(7) 0.35930(7) 0.0334(3) Uani 1 1 d . . .
H24 H 0.7844 0.7564 0.3823 0.040 Uiso 1 1 calc R . .
C25 C 0.90488(14) 0.73807(6) 0.31108(7) 0.0272(3) Uani 1 1 d . . .
H25 H 0.9240 0.7793 0.3011 0.033 Uiso 1 1 calc R . .
C26 C 0.95917(12) 0.69049(5) 0.27740(6) 0.0190(2) Uani 1 1 d . . .
C27 C 0.89146(12) 0.54436(5) 0.22169(6) 0.0195(3) Uani 1 1 d . . .
H27A H 0.9351 0.5191 0.1906 0.023 Uiso 1 1 calc R . .
H27B H 0.8559 0.5165 0.2527 0.023 Uiso 1 1 calc R . .
C28 C 0.77325(13) 0.57829(6) 0.19399(7) 0.0288(3) Uani 1 1 d . . .
H28A H 0.7410 0.6097 0.2224 0.035 Uiso 1 1 calc R . .
H28B H 0.8052 0.5994 0.1576 0.035 Uiso 1 1 calc R . .
C29 C 0.65711(13) 0.53767(6) 0.17798(6) 0.0245(3) Uani 1 1 d . . .
O1 O 0.65503(9) 0.50247(4) 0.02724(5) 0.0281(2) Uani 1 1 d . . .
O2 O 0.53850(10) 0.41993(4) -0.00055(5) 0.0333(3) Uani 1 1 d . . .
H2 H 0.4790 0.4460 -0.0089 0.050 Uiso 1 1 calc R . .
O3 O 1.35684(10) 0.49032(4) 0.13068(6) 0.0400(3) Uani 1 1 d . . .
O4 O 1.46563(10) 0.40503(4) 0.15647(6) 0.0356(3) Uani 1 1 d . . .
H4A H 1.5255 0.4299 0.1673 0.053 Uiso 1 1 calc R . .
O5 O 0.55169(10) 0.56783(4) 0.15704(6) 0.0367(3) Uani 1 1 d . . .
H5A H 0.4885 0.5433 0.1495 0.055 Uiso 1 1 calc R . .
O6 O 0.66033(9) 0.48258(4) 0.18370(5) 0.0319(2) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.3845(18) . ?
C1 C2 1.3927(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3877(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C11 1.3960(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 C12 1.3934(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3937(19) . ?
C7 H7 0.9500 . ?
C8 C13 1.3837(18) . ?
C8 H8 0.9500 . ?
C9 C13 1.5222(16) . ?
C9 C10 1.5235(16) . ?
C9 C17 1.5438(15) . ?
C9 C14 1.5461(15) . ?
C10 C11 1.4017(15) . ?
C11 C12 1.4650(18) . ?
C12 C13 1.4007(15) . ?
C14 C15 1.5163(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.4975(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O1 1.2157(14) . ?
C16 O2 1.3191(14) . ?
C17 C18 1.5216(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5004(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O3 1.2193(16) . ?
C19 O4 1.3164(15) . ?
C20 C21 1.5242(15) 3_755 ?
C20 C21 1.5243(15) . ?
C20 C27 1.5396(14) 3_755 ?
C20 C27 1.5396(14) . ?
C21 C22 1.3815(18) . ?
C21 C26 1.4047(16) . ?
C22 C23 1.3968(18) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.3951(17) . ?
C25 H25 0.9500 . ?
C26 C26 1.468(3) 3_755 ?
C27 C28 1.5147(17) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.4935(17) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 O6 1.2160(15) . ?
C29 O5 1.3175(15) . ?
O2 H2 0.8400 . ?
O4 H4A 0.8400 . ?
O5 H5A 0.8400 . ?

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
C10 C1 C2 118.65(12) . . ?
C10 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
C3 C2 C1 121.00(13) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C4 C3 C2 120.76(12) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C11 118.54(12) . . ?
C3 C4 H4 120.7 . . ?
C11 C4 H4 120.7 . . ?
C6 C5 C12 118.39(12) . . ?
C6 C5 H5 120.8 . . ?
C12 C5 H5 120.8 . . ?
C7 C6 C5 121.10(13) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.82(13) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C13 C8 C7 118.63(12) . . ?
C13 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C13 C9 C10 101.44(9) . . ?
C13 C9 C17 111.46(9) . . ?
C10 C9 C17 113.04(10) . . ?
C13 C9 C14 112.60(10) . . ?
C10 C9 C14 111.57(9) . . ?
C17 C9 C14 106.84(9) . . ?
C1 C10 C11 120.41(11) . . ?
C1 C10 C9 128.88(10) . . ?
C11 C10 C9 110.65(10) . . ?
C4 C11 C10 120.60(12) . . ?
C4 C11 C12 130.81(11) . . ?
C10 C11 C12 108.58(10) . . ?
C5 C12 C13 120.56(12) . . ?
C5 C12 C11 130.87(11) . . ?
C13 C12 C11 108.57(10) . . ?
C8 C13 C12 120.49(11) . . ?
C8 C13 C9 128.76(10) . . ?
C12 C13 C9 110.74(10) . . ?
C15 C14 C9 113.38(9) . . ?
C15 C14 H14A 108.9 . . ?
C9 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C9 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 112.96(10) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
O1 C16 O2 123.42(11) . . ?
O1 C16 C15 123.48(11) . . ?
O2 C16 C15 113.08(10) . . ?
C18 C17 C9 114.07(9) . . ?
C18 C17 H17A 108.7 . . ?
C9 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C9 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 111.83(10) . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
O3 C19 O4 123.33(11) . . ?
O3 C19 C18 123.02(11) . . ?
O4 C19 C18 113.64(11) . . ?
C21 C20 C21 101.40(13) 3_755 . ?
C21 C20 C27 110.49(6) 3_755 3_755 ?
C21 C20 C27 113.42(7) . 3_755 ?
C21 C20 C27 113.42(7) 3_755 . ?
C21 C20 C27 110.49(6) . . ?
C27 C20 C27 107.66(13) 3_755 . ?
C22 C21 C26 120.73(11) . . ?
C22 C21 C20 128.26(11) . . ?
C26 C21 C20 110.82(11) . . ?
C21 C22 C23 118.67(12) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C24 C23 C22 120.73(14) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.91(13) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C26 118.90(13) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C21 119.98(12) . . ?
C25 C26 C26 131.52(8) . 3_755 ?
C21 C26 C26 108.48(7) . 3_755 ?
C28 C27 C20 114.35(10) . . ?
C28 C27 H27A 108.7 . . ?
C20 C27 H27A 108.7 . . ?
C28 C27 H27B 108.7 . . ?
C20 C27 H27B 108.7 . . ?
H27A C27 H27B 107.6 . . ?
C29 C28 C27 113.17(10) . . ?
C29 C28 H28A 108.9 . . ?
C27 C28 H28A 108.9 . . ?
C29 C28 H28B 108.9 . . ?
C27 C28 H28B 108.9 . . ?
H28A C28 H28B 107.8 . . ?
O6 C29 O5 123.88(11) . . ?
O6 C29 C28 123.22(11) . . ?
O5 C29 C28 112.90(11) . . ?
C16 O2 H2 109.5 . . ?
C19 O4 H4A 109.5 . . ?
C29 O5 H5A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 1.1(2) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C2 C3 C4 C11 -0.4(2) . . . . ?
C12 C5 C6 C7 0.2(2) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C6 C7 C8 C13 0.1(2) . . . . ?
C2 C1 C10 C11 0.59(18) . . . . ?
C2 C1 C10 C9 177.53(11) . . . . ?
C13 C9 C10 C1 -176.13(12) . . . . ?
C17 C9 C10 C1 64.42(15) . . . . ?
C14 C9 C10 C1 -56.02(16) . . . . ?
C13 C9 C10 C11 1.05(11) . . . . ?
C17 C9 C10 C11 -118.40(11) . . . . ?
C14 C9 C10 C11 121.16(10) . . . . ?
C3 C4 C11 C10 2.18(18) . . . . ?
C3 C4 C11 C12 -176.21(12) . . . . ?
C1 C10 C11 C4 -2.28(17) . . . . ?
C9 C10 C11 C4 -179.74(10) . . . . ?
C1 C10 C11 C12 176.43(11) . . . . ?
C9 C10 C11 C12 -1.02(13) . . . . ?
C6 C5 C12 C13 1.09(19) . . . . ?
C6 C5 C12 C11 -179.86(13) . . . . ?
C4 C11 C12 C5 -0.1(2) . . . . ?
C10 C11 C12 C5 -178.60(12) . . . . ?
C4 C11 C12 C13 179.08(12) . . . . ?
C10 C11 C12 C13 0.54(13) . . . . ?
C7 C8 C13 C12 1.19(19) . . . . ?
C7 C8 C13 C9 179.77(12) . . . . ?
C5 C12 C13 C8 -1.78(18) . . . . ?
C11 C12 C13 C8 178.97(11) . . . . ?
C5 C12 C13 C9 179.40(11) . . . . ?
C11 C12 C13 C9 0.15(13) . . . . ?
C10 C9 C13 C8 -179.41(12) . . . . ?
C17 C9 C13 C8 -58.83(16) . . . . ?
C14 C9 C13 C8 61.22(15) . . . . ?
C10 C9 C13 C12 -0.71(11) . . . . ?
C17 C9 C13 C12 119.87(10) . . . . ?
C14 C9 C13 C12 -120.09(10) . . . . ?
C13 C9 C14 C15 62.78(13) . . . . ?
C10 C9 C14 C15 -50.53(14) . . . . ?
C17 C9 C14 C15 -174.54(11) . . . . ?
C9 C14 C15 C16 179.02(11) . . . . ?
C14 C15 C16 O1 -10.3(2) . . . . ?
C14 C15 C16 O2 170.97(12) . . . . ?
C13 C9 C17 C18 -52.15(14) . . . . ?
C10 C9 C17 C18 61.36(14) . . . . ?
C14 C9 C17 C18 -175.54(11) . . . . ?
C9 C17 C18 C19 179.99(11) . . . . ?
C17 C18 C19 O3 -8.0(2) . . . . ?
C17 C18 C19 O4 173.26(12) . . . . ?
C21 C20 C21 C22 175.22(15) 3_755 . . . ?
C27 C20 C21 C22 -66.32(14) 3_755 . . . ?
C27 C20 C21 C22 54.68(15) . . . . ?
C21 C20 C21 C26 0.17(6) 3_755 . . . ?
C27 C20 C21 C26 118.63(11) 3_755 . . . ?
C27 C20 C21 C26 -120.38(11) . . . . ?
C26 C21 C22 C23 -0.53(19) . . . . ?
C20 C21 C22 C23 -175.16(11) . . . . ?
C21 C22 C23 C24 -1.6(2) . . . . ?
C22 C23 C24 C25 1.5(2) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C24 C25 C26 C21 -2.75(19) . . . . ?
C24 C25 C26 C26 175.51(16) . . . 3_755 ?
C22 C21 C26 C25 2.72(18) . . . . ?
C20 C21 C26 C25 178.20(10) . . . . ?
C22 C21 C26 C26 -175.91(12) . . . 3_755 ?
C20 C21 C26 C26 -0.42(15) . . . 3_755 ?
C21 C20 C27 C28 -59.94(14) 3_755 . . . ?
C21 C20 C27 C28 53.13(14) . . . . ?
C27 C20 C27 C28 177.49(14) 3_755 . . . ?
C20 C27 C28 C29 -168.38(11) . . . . ?
C27 C28 C29 O6 -3.7(2) . . . . ?
C27 C28 C29 O5 176.40(13) . . . . ?

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
O5 H5A O3 0.84 1.79 2.6310(13) 177.7 1_455
O4 H4A O6 0.84 1.80 2.6348(13) 174.7 1_655
O2 H2 O1 0.84 1.79 2.6244(12) 176.4 5_665

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        31.61
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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 1414835'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C96 H88 Cu2 N4 O16, 2(H2 O)'
_chemical_formula_sum            'C96 H92 Cu2 N4 O18'
_chemical_formula_weight         1716.84

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'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5945(16)
_cell_length_b                   12.9146(19)
_cell_length_c                   15.642(2)
_cell_angle_alpha                91.073(2)
_cell_angle_beta                 94.126(2)
_cell_angle_gamma                93.942(2)
_cell_volume                     2129.1(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4694
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.54

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             898
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8941
_exptl_absorpt_correction_T_max  0.9450
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19323
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         27.94
_reflns_number_total             10038
_reflns_number_gt                7089
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1050P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10038
_refine_ls_number_parameters     549
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1391
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.41242(3) 0.48079(2) 0.401949(18) 0.03442(12) Uani 1 1 d . . .
C1 C 0.3263(3) 0.2875(3) -0.02625(17) 0.0455(7) Uani 1 1 d . . .
C2 C 0.3931(3) 0.3769(3) -0.0501(2) 0.0628(9) Uani 1 1 d . . .
H2 H 0.3664 0.4419 -0.0365 0.075 Uiso 1 1 calc R . .
C3 C 0.5015(4) 0.3679(4) -0.0950(3) 0.0847(14) Uani 1 1 d . . .
H3 H 0.5468 0.4274 -0.1118 0.102 Uiso 1 1 calc R . .
C4 C 0.5416(4) 0.2720(6) -0.1145(3) 0.0957(17) Uani 1 1 d . . .
H4 H 0.6136 0.2677 -0.1446 0.115 Uiso 1 1 calc R . .
C5 C 0.4774(4) 0.1818(4) -0.0904(2) 0.0792(13) Uani 1 1 d . . .
H5 H 0.5050 0.1171 -0.1042 0.095 Uiso 1 1 calc R . .
C6 C 0.3695(3) 0.1905(3) -0.04472(18) 0.0530(8) Uani 1 1 d . . .
C7 C 0.2903(3) 0.1113(3) -0.00524(18) 0.0526(8) Uani 1 1 d . . .
C8 C 0.1989(3) 0.1592(2) 0.03917(17) 0.0443(7) Uani 1 1 d . . .
C9 C 0.2068(3) 0.2752(2) 0.02253(16) 0.0406(6) Uani 1 1 d . . .
C10 C 0.1148(3) 0.1018(3) 0.0844(2) 0.0604(9) Uani 1 1 d . . .
H10 H 0.0544 0.1341 0.1137 0.072 Uiso 1 1 calc R . .
C11 C 0.1205(5) -0.0059(3) 0.0863(3) 0.0811(12) Uani 1 1 d . . .
H11 H 0.0646 -0.0457 0.1176 0.097 Uiso 1 1 calc R . .
C12 C 0.2087(5) -0.0528(3) 0.0419(3) 0.0898(15) Uani 1 1 d . . .
H12 H 0.2110 -0.1246 0.0429 0.108 Uiso 1 1 calc R . .
C13 C 0.2934(4) 0.0035(3) -0.0037(3) 0.0765(12) Uani 1 1 d . . .
H13 H 0.3525 -0.0296 -0.0336 0.092 Uiso 1 1 calc R . .
C14 C 0.2106(3) 0.3437(2) 0.10324(17) 0.0458(7) Uani 1 1 d . . .
H14A H 0.2155 0.4157 0.0866 0.055 Uiso 1 1 calc R . .
H14B H 0.1315 0.3305 0.1300 0.055 Uiso 1 1 calc R . .
C15 C 0.3185(3) 0.3286(2) 0.16869(18) 0.0505(7) Uani 1 1 d . . .
H15A H 0.3975 0.3387 0.1413 0.061 Uiso 1 1 calc R . .
H15B H 0.3114 0.2574 0.1873 0.061 Uiso 1 1 calc R . .
C16 C 0.3252(3) 0.4004(2) 0.24746(17) 0.0417(6) Uani 1 1 d . . .
C17 C 0.0854(3) 0.2924(2) -0.03675(19) 0.0477(7) Uani 1 1 d . . .
H17A H 0.0802 0.2422 -0.0840 0.057 Uiso 1 1 calc R . .
H17B H 0.0118 0.2778 -0.0043 0.057 Uiso 1 1 calc R . .
C18 C 0.0781(3) 0.3985(3) -0.0730(2) 0.0534(8) Uani 1 1 d . . .
H18A H 0.1465 0.4113 -0.1102 0.064 Uiso 1 1 calc R . .
H18B H 0.0894 0.4498 -0.0266 0.064 Uiso 1 1 calc R . .
C19 C -0.0469(3) 0.4109(3) -0.1232(2) 0.0538(8) Uani 1 1 d . . .
C20 C 0.2445(3) 0.8096(2) 0.73013(19) 0.0428(6) Uani 1 1 d . . .
C21 C 0.1531(3) 0.7374(3) 0.7553(2) 0.0609(9) Uani 1 1 d . . .
H21 H 0.0794 0.7205 0.7204 0.073 Uiso 1 1 calc R . .
C22 C 0.1735(4) 0.6902(3) 0.8341(3) 0.0740(11) Uani 1 1 d . . .
H22 H 0.1124 0.6415 0.8515 0.089 Uiso 1 1 calc R . .
C23 C 0.2792(5) 0.7135(3) 0.8855(3) 0.0754(11) Uani 1 1 d . . .
H23 H 0.2896 0.6809 0.9378 0.090 Uiso 1 1 calc R . .
C24 C 0.3726(4) 0.7849(3) 0.8621(2) 0.0614(9) Uani 1 1 d . . .
H24 H 0.4455 0.8007 0.8979 0.074 Uiso 1 1 calc R . .
C25 C 0.3546(3) 0.8327(2) 0.78329(18) 0.0455(7) Uani 1 1 d . . .
C26 C 0.4357(3) 0.9092(2) 0.74121(19) 0.0453(7) Uani 1 1 d . . .
C27 C 0.3732(3) 0.9334(2) 0.6633(2) 0.0457(7) Uani 1 1 d . . .
C28 C 0.2463(3) 0.8706(2) 0.64787(18) 0.0437(6) Uani 1 1 d . . .
C29 C 0.4325(4) 1.0034(3) 0.6096(3) 0.0654(9) Uani 1 1 d . . .
H29 H 0.3929 1.0199 0.5571 0.079 Uiso 1 1 calc R . .
C30 C 0.5535(4) 1.0482(3) 0.6367(3) 0.0839(14) Uani 1 1 d . . .
H30 H 0.5943 1.0957 0.6021 0.101 Uiso 1 1 calc R . .
C31 C 0.6128(4) 1.0226(4) 0.7142(3) 0.0844(13) Uani 1 1 d . . .
H31 H 0.6932 1.0529 0.7308 0.101 Uiso 1 1 calc R . .
C32 C 0.5563(3) 0.9544(3) 0.7664(3) 0.0657(10) Uani 1 1 d . . .
H32 H 0.5973 0.9378 0.8185 0.079 Uiso 1 1 calc R . .
C33 C 0.2440(3) 0.7977(2) 0.56818(19) 0.0460(7) Uani 1 1 d . . .
H33A H 0.1685 0.7505 0.5668 0.055 Uiso 1 1 calc R . .
H33B H 0.2377 0.8392 0.5172 0.055 Uiso 1 1 calc R . .
C34 C 0.3584(3) 0.7347(2) 0.56521(18) 0.0446(6) Uani 1 1 d . . .
H34A H 0.3736 0.7028 0.6203 0.054 Uiso 1 1 calc R . .
H34B H 0.4320 0.7810 0.5560 0.054 Uiso 1 1 calc R . .
C35 C 0.3444(3) 0.6507(2) 0.49564(16) 0.0409(6) Uani 1 1 d . . .
C36 C 0.1321(3) 0.9375(3) 0.6346(2) 0.0548(8) Uani 1 1 d . . .
H36A H 0.1418 0.9770 0.5831 0.066 Uiso 1 1 calc R . .
H36B H 0.0560 0.8914 0.6247 0.066 Uiso 1 1 calc R . .
C37 C 0.1123(3) 1.0124(3) 0.7070(2) 0.0569(8) Uani 1 1 d . . .
H37A H 0.1880 1.0586 0.7179 0.068 Uiso 1 1 calc R . .
H37B H 0.0996 0.9736 0.7586 0.068 Uiso 1 1 calc R . .
C38 C -0.0003(3) 1.0763(2) 0.6876(2) 0.0483(7) Uani 1 1 d . . .
C39 C 0.2830(4) 0.2797(3) 0.4400(3) 0.0725(11) Uani 1 1 d . . .
H39 H 0.3507 0.2559 0.4124 0.087 Uiso 1 1 calc R . .
C40 C 0.1949(5) 0.2081(4) 0.4675(3) 0.0959(16) Uani 1 1 d . . .
H40 H 0.2022 0.1375 0.4581 0.115 Uiso 1 1 calc R . .
C41 C 0.0966(5) 0.2418(5) 0.5086(3) 0.105(2) Uani 1 1 d . . .
H41 H 0.0356 0.1944 0.5279 0.126 Uiso 1 1 calc R . .
C43 C 0.1806(4) 0.4132(4) 0.4907(3) 0.0815(13) Uani 1 1 d . . .
H43 H 0.1738 0.4841 0.4989 0.098 Uiso 1 1 calc R . .
C44 C 0.6405(3) 0.5262(3) 0.3110(2) 0.0548(8) Uani 1 1 d . . .
H44 H 0.6412 0.4542 0.3122 0.066 Uiso 1 1 calc R . .
C45 C 0.7383(3) 0.5807(3) 0.2754(2) 0.0633(9) Uani 1 1 d . . .
H45 H 0.8049 0.5466 0.2549 0.076 Uiso 1 1 calc R . .
C46 C 0.7364(4) 0.6854(3) 0.2705(2) 0.0710(11) Uani 1 1 d . . .
H46 H 0.8008 0.7241 0.2458 0.085 Uiso 1 1 calc R . .
C47 C 0.6381(4) 0.7329(3) 0.3027(2) 0.0698(11) Uani 1 1 d . . .
H47 H 0.6348 0.8046 0.3000 0.084 Uiso 1 1 calc R . .
C48 C 0.5442(3) 0.6741(2) 0.3389(2) 0.0529(8) Uani 1 1 d . . .
H48 H 0.4779 0.7073 0.3608 0.064 Uiso 1 1 calc R . .
C42 C 0.0878(4) 0.3445(5) 0.5213(3) 0.1014(18) Uani 1 1 d . . .
H42 H 0.0213 0.3690 0.5499 0.122 Uiso 1 1 calc R . .
N1 N 0.2771(2) 0.3825(2) 0.45078(16) 0.0509(6) Uani 1 1 d . . .
N2 N 0.5442(2) 0.57056(19) 0.34408(14) 0.0419(5) Uani 1 1 d . . .
O1 O 0.41103(18) 0.38366(15) 0.30470(11) 0.0431(4) Uani 1 1 d . . .
O2 O 0.2532(2) 0.47044(19) 0.25427(14) 0.0651(7) Uani 1 1 d . . .
O3 O -0.0370(2) 0.4789(2) -0.18318(17) 0.0675(7) Uani 1 1 d . . .
H3A H -0.1080 0.4914 -0.2029 0.101 Uiso 1 1 calc R . .
O4 O -0.1447(3) 0.3674(3) -0.1084(2) 0.0966(11) Uani 1 1 d . . .
O5 O 0.2609(2) 0.6530(2) 0.43606(14) 0.0684(7) Uani 1 1 d . . .
O6 O 0.42123(17) 0.57974(14) 0.50077(11) 0.0366(4) Uani 1 1 d . . .
O7 O -0.0764(3) 1.0591(2) 0.62624(19) 0.0780(8) Uani 1 1 d . . .
O8 O -0.0056(2) 1.15223(19) 0.74322(17) 0.0683(7) Uani 1 1 d . . .
H8 H -0.0744 1.1774 0.7362 0.102 Uiso 1 1 calc R . .
O9 O 0.2026(3) 0.7361(2) 0.2808(2) 0.0811(8) Uani 1 1 d D . .
H9B H 0.190(5) 0.720(4) 0.3312(11) 0.122 Uiso 1 1 d D . .
H9A H 0.194(5) 0.683(2) 0.250(2) 0.122 Uiso 1 1 d D . .


_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 1.9521(18) . ?
Cu1 O6 1.9799(17) . ?
Cu1 N2 2.028(2) . ?
Cu1 N1 2.048(3) . ?
Cu1 O6 2.4251(18) 2_666 ?
C1 C2 1.384(5) . ?
C1 C6 1.395(4) . ?
C1 C9 1.525(4) . ?
C2 C3 1.399(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.453(5) . ?
C7 C13 1.396(5) . ?
C7 C8 1.402(4) . ?
C8 C10 1.365(4) . ?
C8 C9 1.523(4) . ?
C9 C14 1.525(3) . ?
C9 C17 1.562(4) . ?
C10 C11 1.397(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.504(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.523(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O2 1.230(3) . ?
C16 O1 1.262(3) . ?
C17 C18 1.497(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.510(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O4 1.184(4) . ?
C19 O3 1.302(4) . ?
C20 C21 1.382(4) . ?
C20 C25 1.395(4) . ?
C20 C28 1.522(4) . ?
C21 C22 1.394(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.344(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.379(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.396(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.461(4) . ?
C26 C32 1.395(4) . ?
C26 C27 1.395(4) . ?
C27 C29 1.395(4) . ?
C27 C28 1.523(4) . ?
C28 C36 1.538(4) . ?
C28 C33 1.545(4) . ?
C29 C30 1.403(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.381(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.351(6) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.508(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.514(4) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 O5 1.240(3) . ?
C35 O6 1.267(3) . ?
C36 C37 1.511(4) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.513(4) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 O7 1.215(4) . ?
C38 O8 1.306(4) . ?
C39 N1 1.342(5) . ?
C39 C40 1.366(6) . ?
C39 H39 0.9300 . ?
C40 C41 1.355(8) . ?
C40 H40 0.9300 . ?
C41 C42 1.347(8) . ?
C41 H41 0.9300 . ?
C43 N1 1.316(5) . ?
C43 C42 1.396(6) . ?
C43 H43 0.9300 . ?
C44 N2 1.335(4) . ?
C44 C45 1.371(5) . ?
C44 H44 0.9300 . ?
C45 C46 1.357(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.366(6) . ?
C46 H46 0.9300 . ?
C47 C48 1.372(4) . ?
C47 H47 0.9300 . ?
C48 N2 1.341(4) . ?
C48 H48 0.9300 . ?
C42 H42 0.9300 . ?
O3 H3A 0.8200 . ?
O6 Cu1 2.4251(18) 2_666 ?
O8 H8 0.8200 . ?
O9 H9B 0.836(10) . ?
O9 H9A 0.829(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O6 177.74(7) . . ?
O1 Cu1 N2 87.29(9) . . ?
O6 Cu1 N2 91.13(8) . . ?
O1 Cu1 N1 87.82(10) . . ?
O6 Cu1 N1 93.78(9) . . ?
N2 Cu1 N1 175.04(9) . . ?
O1 Cu1 O6 102.21(7) . 2_666 ?
O6 Cu1 O6 76.17(7) . 2_666 ?
N2 Cu1 O6 89.69(8) . 2_666 ?
N1 Cu1 O6 92.17(8) . 2_666 ?
C2 C1 C6 120.0(3) . . ?
C2 C1 C9 129.7(3) . . ?
C6 C1 C9 110.3(3) . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 118.0(4) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 120.9(4) . . ?
C1 C6 C7 108.7(3) . . ?
C5 C6 C7 130.3(4) . . ?
C13 C7 C8 119.1(4) . . ?
C13 C7 C6 131.7(3) . . ?
C8 C7 C6 109.2(3) . . ?
C10 C8 C7 120.9(3) . . ?
C10 C8 C9 129.3(3) . . ?
C7 C8 C9 109.7(3) . . ?
C8 C9 C14 114.2(2) . . ?
C8 C9 C1 101.5(2) . . ?
C14 C9 C1 114.2(2) . . ?
C8 C9 C17 104.8(2) . . ?
C14 C9 C17 110.1(2) . . ?
C1 C9 C17 111.4(2) . . ?
C8 C10 C11 119.3(4) . . ?
C8 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C7 119.4(4) . . ?
C12 C13 H13 120.3 . . ?
C7 C13 H13 120.3 . . ?
C15 C14 C9 115.3(2) . . ?
C15 C14 H14A 108.5 . . ?
C9 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C9 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 C16 115.1(2) . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
O2 C16 O1 122.5(2) . . ?
O2 C16 C15 122.4(2) . . ?
O1 C16 C15 115.1(2) . . ?
C18 C17 C9 115.9(2) . . ?
C18 C17 H17A 108.3 . . ?
C9 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C9 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 C19 112.3(3) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
O4 C19 O3 123.0(3) . . ?
O4 C19 C18 124.6(3) . . ?
O3 C19 C18 112.4(3) . . ?
C21 C20 C25 119.5(3) . . ?
C21 C20 C28 129.0(3) . . ?
C25 C20 C28 111.4(3) . . ?
C20 C21 C22 118.6(4) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 H21 120.7 . . ?
C23 C22 C21 121.7(4) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 121.2(4) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C25 118.3(3) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
C20 C25 C24 120.8(3) . . ?
C20 C25 C26 108.4(3) . . ?
C24 C25 C26 130.8(3) . . ?
C32 C26 C27 121.1(3) . . ?
C32 C26 C25 130.7(3) . . ?
C27 C26 C25 108.3(3) . . ?
C29 C27 C26 119.5(3) . . ?
C29 C27 C28 129.0(3) . . ?
C26 C27 C28 111.4(3) . . ?
C20 C28 C27 100.4(2) . . ?
C20 C28 C36 112.6(2) . . ?
C27 C28 C36 113.8(2) . . ?
C20 C28 C33 111.5(2) . . ?
C27 C28 C33 111.6(2) . . ?
C36 C28 C33 107.0(2) . . ?
C27 C29 C30 118.3(4) . . ?
C27 C29 H29 120.9 . . ?
C30 C29 H29 120.9 . . ?
C31 C30 C29 120.8(4) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C32 C31 C30 121.3(4) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C31 C32 C26 119.1(4) . . ?
C31 C32 H32 120.5 . . ?
C26 C32 H32 120.5 . . ?
C34 C33 C28 114.3(2) . . ?
C34 C33 H33A 108.7 . . ?
C28 C33 H33A 108.7 . . ?
C34 C33 H33B 108.7 . . ?
C28 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
C33 C34 C35 113.5(2) . . ?
C33 C34 H34A 108.9 . . ?
C35 C34 H34A 108.9 . . ?
C33 C34 H34B 108.9 . . ?
C35 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
O5 C35 O6 122.1(3) . . ?
O5 C35 C34 120.4(3) . . ?
O6 C35 C34 117.5(2) . . ?
C37 C36 C28 116.3(3) . . ?
C37 C36 H36A 108.2 . . ?
C28 C36 H36A 108.2 . . ?
C37 C36 H36B 108.2 . . ?
C28 C36 H36B 108.2 . . ?
H36A C36 H36B 107.4 . . ?
C36 C37 C38 112.6(3) . . ?
C36 C37 H37A 109.1 . . ?
C38 C37 H37A 109.1 . . ?
C36 C37 H37B 109.1 . . ?
C38 C37 H37B 109.1 . . ?
H37A C37 H37B 107.8 . . ?
O7 C38 O8 123.9(3) . . ?
O7 C38 C37 123.4(3) . . ?
O8 C38 C37 112.7(3) . . ?
N1 C39 C40 123.4(4) . . ?
N1 C39 H39 118.3 . . ?
C40 C39 H39 118.3 . . ?
C41 C40 C39 118.7(5) . . ?
C41 C40 H40 120.6 . . ?
C39 C40 H40 120.6 . . ?
C42 C41 C40 119.6(4) . . ?
C42 C41 H41 120.2 . . ?
C40 C41 H41 120.2 . . ?
N1 C43 C42 123.1(5) . . ?
N1 C43 H43 118.4 . . ?
C42 C43 H43 118.4 . . ?
N2 C44 C45 123.6(3) . . ?
N2 C44 H44 118.2 . . ?
C45 C44 H44 118.2 . . ?
C46 C45 C44 118.9(3) . . ?
C46 C45 H45 120.6 . . ?
C44 C45 H45 120.6 . . ?
C45 C46 C47 118.8(3) . . ?
C45 C46 H46 120.6 . . ?
C47 C46 H46 120.6 . . ?
C46 C47 C48 119.5(3) . . ?
C46 C47 H47 120.3 . . ?
C48 C47 H47 120.3 . . ?
N2 C48 C47 122.6(3) . . ?
N2 C48 H48 118.7 . . ?
C47 C48 H48 118.7 . . ?
C41 C42 C43 118.5(5) . . ?
C41 C42 H42 120.8 . . ?
C43 C42 H42 120.8 . . ?
C43 N1 C39 116.6(3) . . ?
C43 N1 Cu1 124.3(3) . . ?
C39 N1 Cu1 119.1(3) . . ?
C44 N2 C48 116.6(3) . . ?
C44 N2 Cu1 119.2(2) . . ?
C48 N2 Cu1 124.2(2) . . ?
C16 O1 Cu1 111.68(17) . . ?
C19 O3 H3A 109.5 . . ?
C35 O6 Cu1 116.10(16) . . ?
C35 O6 Cu1 140.07(16) . 2_666 ?
Cu1 O6 Cu1 103.83(7) . 2_666 ?
C38 O8 H8 109.5 . . ?
H9B O9 H9A 109(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.9(4) . . . . ?
C9 C1 C2 C3 179.9(3) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C2 C1 C6 C5 -2.6(4) . . . . ?
C9 C1 C6 C5 179.1(3) . . . . ?
C2 C1 C6 C7 174.1(3) . . . . ?
C9 C1 C6 C7 -4.2(3) . . . . ?
C4 C5 C6 C1 1.8(5) . . . . ?
C4 C5 C6 C7 -174.2(3) . . . . ?
C1 C6 C7 C13 -179.6(3) . . . . ?
C5 C6 C7 C13 -3.3(6) . . . . ?
C1 C6 C7 C8 -1.0(3) . . . . ?
C5 C6 C7 C8 175.3(3) . . . . ?
C13 C7 C8 C10 0.9(4) . . . . ?
C6 C7 C8 C10 -177.9(3) . . . . ?
C13 C7 C8 C9 -175.4(3) . . . . ?
C6 C7 C8 C9 5.8(3) . . . . ?
C10 C8 C9 C14 53.0(4) . . . . ?
C7 C8 C9 C14 -131.1(2) . . . . ?
C10 C8 C9 C1 176.3(3) . . . . ?
C7 C8 C9 C1 -7.7(3) . . . . ?
C10 C8 C9 C17 -67.6(3) . . . . ?
C7 C8 C9 C17 108.3(3) . . . . ?
C2 C1 C9 C8 -170.9(3) . . . . ?
C6 C1 C9 C8 7.2(3) . . . . ?
C2 C1 C9 C14 -47.6(4) . . . . ?
C6 C1 C9 C14 130.5(3) . . . . ?
C2 C1 C9 C17 78.0(4) . . . . ?
C6 C1 C9 C17 -103.9(3) . . . . ?
C7 C8 C10 C11 0.0(5) . . . . ?
C9 C8 C10 C11 175.6(3) . . . . ?
C8 C10 C11 C12 -1.0(6) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C11 C12 C13 C7 0.1(6) . . . . ?
C8 C7 C13 C12 -1.0(5) . . . . ?
C6 C7 C13 C12 177.5(3) . . . . ?
C8 C9 C14 C15 58.2(4) . . . . ?
C1 C9 C14 C15 -58.0(4) . . . . ?
C17 C9 C14 C15 175.8(3) . . . . ?
C9 C14 C15 C16 177.5(3) . . . . ?
C14 C15 C16 O2 -4.9(5) . . . . ?
C14 C15 C16 O1 175.9(3) . . . . ?
C8 C9 C17 C18 -172.0(2) . . . . ?
C14 C9 C17 C18 64.8(3) . . . . ?
C1 C9 C17 C18 -63.0(3) . . . . ?
C9 C17 C18 C19 -175.1(3) . . . . ?
C17 C18 C19 O4 30.8(5) . . . . ?
C17 C18 C19 O3 -152.0(3) . . . . ?
C25 C20 C21 C22 0.6(4) . . . . ?
C28 C20 C21 C22 179.2(3) . . . . ?
C20 C21 C22 C23 0.0(6) . . . . ?
C21 C22 C23 C24 -0.3(6) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
C21 C20 C25 C24 -1.0(4) . . . . ?
C28 C20 C25 C24 -179.8(3) . . . . ?
C21 C20 C25 C26 178.9(3) . . . . ?
C28 C20 C25 C26 0.1(3) . . . . ?
C23 C24 C25 C20 0.7(5) . . . . ?
C23 C24 C25 C26 -179.2(3) . . . . ?
C20 C25 C26 C32 -177.7(3) . . . . ?
C24 C25 C26 C32 2.2(5) . . . . ?
C20 C25 C26 C27 1.0(3) . . . . ?
C24 C25 C26 C27 -179.1(3) . . . . ?
C32 C26 C27 C29 0.4(4) . . . . ?
C25 C26 C27 C29 -178.5(3) . . . . ?
C32 C26 C27 C28 177.1(3) . . . . ?
C25 C26 C27 C28 -1.7(3) . . . . ?
C21 C20 C28 C27 -179.7(3) . . . . ?
C25 C20 C28 C27 -1.0(3) . . . . ?
C21 C20 C28 C36 58.8(4) . . . . ?
C25 C20 C28 C36 -122.5(3) . . . . ?
C21 C20 C28 C33 -61.5(4) . . . . ?
C25 C20 C28 C33 117.2(3) . . . . ?
C29 C27 C28 C20 178.0(3) . . . . ?
C26 C27 C28 C20 1.7(3) . . . . ?
C29 C27 C28 C36 -61.4(4) . . . . ?
C26 C27 C28 C36 122.3(3) . . . . ?
C29 C27 C28 C33 59.8(4) . . . . ?
C26 C27 C28 C33 -116.5(3) . . . . ?
C26 C27 C29 C30 -0.8(4) . . . . ?
C28 C27 C29 C30 -176.8(3) . . . . ?
C27 C29 C30 C31 0.8(6) . . . . ?
C29 C30 C31 C32 -0.4(6) . . . . ?
C30 C31 C32 C26 0.0(6) . . . . ?
C27 C26 C32 C31 0.0(5) . . . . ?
C25 C26 C32 C31 178.6(3) . . . . ?
C20 C28 C33 C34 -63.3(3) . . . . ?
C27 C28 C33 C34 48.1(4) . . . . ?
C36 C28 C33 C34 173.2(3) . . . . ?
C28 C33 C34 C35 169.9(2) . . . . ?
C33 C34 C35 O5 16.5(4) . . . . ?
C33 C34 C35 O6 -164.0(3) . . . . ?
C20 C28 C36 C37 54.8(4) . . . . ?
C27 C28 C36 C37 -58.6(4) . . . . ?
C33 C28 C36 C37 177.7(3) . . . . ?
C28 C36 C37 C38 178.8(3) . . . . ?
C36 C37 C38 O7 9.7(5) . . . . ?
C36 C37 C38 O8 -169.5(3) . . . . ?
N1 C39 C40 C41 -0.7(7) . . . . ?
C39 C40 C41 C42 0.1(7) . . . . ?
N2 C44 C45 C46 -2.2(5) . . . . ?
C44 C45 C46 C47 1.1(6) . . . . ?
C45 C46 C47 C48 0.0(6) . . . . ?
C46 C47 C48 N2 -0.2(6) . . . . ?
C40 C41 C42 C43 0.6(7) . . . . ?
N1 C43 C42 C41 -0.8(7) . . . . ?
C42 C43 N1 C39 0.2(6) . . . . ?
C42 C43 N1 Cu1 178.2(3) . . . . ?
C40 C39 N1 C43 0.5(6) . . . . ?
C40 C39 N1 Cu1 -177.6(3) . . . . ?
O1 Cu1 N1 C43 -141.6(3) . . . . ?
O6 Cu1 N1 C43 40.0(3) . . . . ?
O6 Cu1 N1 C43 116.3(3) 2_666 . . . ?
O1 Cu1 N1 C39 36.4(3) . . . . ?
O6 Cu1 N1 C39 -142.1(3) . . . . ?
O6 Cu1 N1 C39 -65.8(3) 2_666 . . . ?
C45 C44 N2 C48 2.0(5) . . . . ?
C45 C44 N2 Cu1 -175.8(3) . . . . ?
C47 C48 N2 C44 -0.8(5) . . . . ?
C47 C48 N2 Cu1 177.0(3) . . . . ?
O1 Cu1 N2 C44 -45.2(2) . . . . ?
O6 Cu1 N2 C44 133.2(2) . . . . ?
O6 Cu1 N2 C44 57.1(2) 2_666 . . . ?
O1 Cu1 N2 C48 137.2(2) . . . . ?
O6 Cu1 N2 C48 -44.4(2) . . . . ?
O6 Cu1 N2 C48 -120.6(2) 2_666 . . . ?
O2 C16 O1 Cu1 0.2(4) . . . . ?
C15 C16 O1 Cu1 179.4(2) . . . . ?
N2 Cu1 O1 C16 -93.5(2) . . . . ?
N1 Cu1 O1 C16 85.6(2) . . . . ?
O5 C35 O6 Cu1 6.3(4) . . . . ?
C34 C35 O6 Cu1 -173.26(19) . . . . ?
O5 C35 O6 Cu1 -173.5(2) . . . 2_666 ?
C34 C35 O6 Cu1 6.9(4) . . . 2_666 ?
N2 Cu1 O6 C35 90.7(2) . . . . ?
N1 Cu1 O6 C35 -88.6(2) . . . . ?
O6 Cu1 O6 C35 -179.9(2) 2_666 . . . ?
N2 Cu1 O6 Cu1 -89.40(9) . . . 2_666 ?
N1 Cu1 O6 Cu1 91.30(10) . . . 2_666 ?
O6 Cu1 O6 Cu1 0.0 2_666 . . 2_666 ?

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
O9 H9A O4 0.829(10) 2.31(3) 2.992(5) 139(4) 2_565
O9 H9B O5 0.836(10) 2.00(3) 2.722(4) 145(5) .
O8 H8 O9 0.82 1.82 2.626(4) 165.5 2_576
O3 H3A O2 0.82 1.79 2.604(3) 173.0 2_565

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.091
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1414836'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 Cu O6, C2 H6 O, 2(H2 O)'
_chemical_formula_sum            'C21 H30 Cu O9'
_chemical_formula_weight         489.99

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.6479(12)
_cell_length_b                   12.8941(15)
_cell_length_c                   32.484(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4459.9(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9575
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      31.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2056
_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8207
_exptl_absorpt_correction_T_max  0.8207
_exptl_absorpt_process_details   'SADABS, (Sheldrick,2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31287
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4332
_reflns_number_gt                4224
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0283P)²+40.0648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4332
_refine_ls_number_parameters     303
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.1719
_refine_ls_wR_factor_gt          0.1713
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.214
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.38657(7) 0.41679(5) 0.018114(18) 0.0245(2) Uani 1 1 d . . .
C1 C 0.0208(4) 0.1616(3) 0.15096(13) 0.0102(9) Uani 1 1 d . . .
C2 C 0.1273(4) 0.1155(3) 0.17631(13) 0.0106(9) Uani 1 1 d . . .
C3 C 0.2088(4) 0.0353(4) 0.16635(14) 0.0129(9) Uani 1 1 d . . .
H3 H 0.1983 -0.0026 0.1415 0.015 Uiso 1 1 calc R . .
C4 C 0.3063(5) 0.0114(4) 0.19344(14) 0.0147(9) Uani 1 1 d . . .
H4 H 0.3624 -0.0436 0.1871 0.018 Uiso 1 1 calc R . .
C5 C 0.3219(4) 0.0677(4) 0.22976(14) 0.0154(10) Uani 1 1 d . . .
H5 H 0.3900 0.0516 0.2475 0.019 Uiso 1 1 calc R . .
C6 C 0.2400(4) 0.1465(3) 0.24031(13) 0.0124(9) Uani 1 1 d . . .
H6 H 0.2504 0.1840 0.2653 0.015 Uiso 1 1 calc R . .
C7 C 0.1420(4) 0.1697(3) 0.21352(13) 0.0106(9) Uani 1 1 d . . .
C8 C 0.0459(4) 0.2512(4) 0.21558(13) 0.0114(9) Uani 1 1 d . . .
C9 C 0.0182(5) 0.3230(4) 0.24623(14) 0.0147(9) Uani 1 1 d . . .
H9 H 0.0643 0.3239 0.2713 0.018 Uiso 1 1 calc R . .
C10 C -0.0786(5) 0.3935(4) 0.23946(15) 0.0166(10) Uani 1 1 d . . .
H10 H -0.0995 0.4424 0.2602 0.020 Uiso 1 1 calc R . .
C11 C -0.1446(4) 0.3932(4) 0.20283(15) 0.0162(10) Uani 1 1 d . . .
H11 H -0.2089 0.4432 0.1985 0.019 Uiso 1 1 calc R . .
C12 C -0.1184(5) 0.3206(4) 0.17210(14) 0.0158(10) Uani 1 1 d . . .
H12 H -0.1648 0.3199 0.1471 0.019 Uiso 1 1 calc R . .
C13 C -0.0229(4) 0.2493(4) 0.17899(13) 0.0115(9) Uani 1 1 d . . .
C14 C 0.0706(4) 0.2018(4) 0.10920(13) 0.0124(9) Uani 1 1 d . . .
H14A H 0.1028 0.1421 0.0932 0.015 Uiso 1 1 calc R . .
H14B H -0.0003 0.2321 0.0936 0.015 Uiso 1 1 calc R . .
C15 C 0.1740(5) 0.2825(4) 0.11248(14) 0.0158(10) Uani 1 1 d . . .
H15A H 0.1374 0.3479 0.1230 0.019 Uiso 1 1 calc R . .
H15B H 0.2369 0.2584 0.1328 0.019 Uiso 1 1 calc R . .
C16 C 0.2397(5) 0.3044(4) 0.07209(15) 0.0204(11) Uani 1 1 d . . .
C17 C -0.0903(4) 0.0838(4) 0.14502(13) 0.0126(9) Uani 1 1 d . . .
H17A H -0.0994 0.0429 0.1706 0.015 Uiso 1 1 calc R . .
H17B H -0.1685 0.1244 0.1414 0.015 Uiso 1 1 calc R . .
C18 C -0.0793(5) 0.0083(4) 0.10898(13) 0.0146(9) Uani 1 1 d . . .
H18A H 0.0081 -0.0175 0.1075 0.018 Uiso 1 1 calc R . .
H18B H -0.1347 -0.0520 0.1142 0.018 Uiso 1 1 calc R . .
C19 C -0.1139(5) 0.0560(4) 0.06806(14) 0.0159(10) Uani 1 1 d . . .
C20 C 0.0049(8) 0.1178(10) 0.3801(3) 0.083(4) Uani 1 1 d . . .
H20A H -0.0861 0.1025 0.3813 0.099 Uiso 1 1 calc R . .
H20B H 0.0463 0.0590 0.3659 0.099 Uiso 1 1 calc R . .
C21 C 0.0239(9) 0.2126(9) 0.3553(4) 0.087(4) Uani 1 1 d . . .
H21A H 0.0027 0.2737 0.3719 0.131 Uiso 1 1 calc R . .
H21B H -0.0303 0.2103 0.3309 0.131 Uiso 1 1 calc R . .
H21C H 0.1119 0.2169 0.3466 0.131 Uiso 1 1 calc R . .
O1 O 0.3209(4) 0.3765(3) 0.07262(11) 0.0269(9) Uani 1 1 d . . .
O2 O 0.2145(4) 0.2515(3) 0.04080(11) 0.0321(10) Uani 1 1 d . . .
O3 O -0.0489(4) 0.0315(3) 0.03652(10) 0.0218(8) Uani 1 1 d . . .
O4 O -0.2057(4) 0.1158(3) 0.06529(11) 0.0258(9) Uani 1 1 d . . .
O7 O 0.4970(8) 0.2949(5) 0.01605(19) 0.083(2) Uani 1 1 d D . .
H7B H 0.549(9) 0.276(8) -0.001(3) 0.125 Uiso 1 1 d D . .
H7A H 0.492(11) 0.253(7) 0.035(2) 0.125 Uiso 1 1 d D . .
O6 O 0.2550(6) 0.5263(4) 0.01745(14) 0.0500(13) Uani 1 1 d D . .
H6A H 0.237(9) 0.553(5) -0.0048(12) 0.075 Uiso 1 1 d D . .
H6B H 0.273(9) 0.571(4) 0.0344(17) 0.075 Uiso 1 1 d D . .
O5 O 0.0509(6) 0.1235(6) 0.4201(2) 0.091(3) Uani 1 1 d . . .
H5A H 0.1264 0.1206 0.4249 0.136 Uiso 1 1 d R . .
O8 O -0.0035(7) 0.4537(7) 0.0400(2) 0.094(2) Uani 1 1 d D . .
H8A H 0.0732 0.4618 0.0364 0.141 Uiso 1 1 d RD . .
H8B H -0.0296 0.5034 0.0599 0.141 Uiso 1 1 d RD . .
O9 O 0.7827(9) 0.3389(7) 0.0628(4) 0.051(3) Uani 0.61(2) 1 d PD A 1
H9A H 0.7822 0.2812 0.0735 0.077 Uiso 0.61(2) 1 d PRD A 1
H9B H 0.8550 0.3593 0.0594 0.077 Uiso 0.61(2) 1 d PRD A 1
O9' O 0.8069(16) 0.3110(11) 0.0374(6) 0.052(5) Uani 0.39(2) 1 d PD A 2
H9C H 0.7801 0.2930 0.0148 0.078 Uiso 0.39(2) 1 d PRD A 2
H9D H 0.8653 0.3532 0.0345 0.078 Uiso 0.39(2) 1 d PRD A 2


_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 O7 1.964(6) . ?
Cu1 O1 1.973(3) . ?
Cu1 O6 1.989(6) . ?
Cu1 O3 2.016(3) 4 ?
Cu1 O3 2.352(4) 8_665 ?
C1 C2 1.522(6) . ?
C1 C13 1.525(6) . ?
C1 C14 1.546(6) . ?
C1 C17 1.563(6) . ?
C2 C3 1.387(6) . ?
C2 C7 1.405(6) . ?
C3 C4 1.396(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.468(6) . ?
C8 C9 1.391(6) . ?
C8 C13 1.397(6) . ?
C9 C10 1.391(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(7) . ?
C12 H12 0.9500 . ?
C14 C15 1.518(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.514(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O2 1.253(6) . ?
C16 O1 1.270(6) . ?
C17 C18 1.527(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.510(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O4 1.249(6) . ?
C19 O3 1.276(6) . ?
C20 O5 1.391(10) . ?
C20 C21 1.478(15) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O3 Cu1 2.017(3) 4_455 ?
O3 Cu1 2.352(4) 8_655 ?
O7 H7B 0.821(11) . ?
O7 H7A 0.822(11) . ?
O6 H6A 0.823(11) . ?
O6 H6B 0.825(11) . ?
O5 H5A 0.8200 . ?
O8 H8A 0.8318 . ?
O8 H8B 0.9507 . ?
O9 H9A 0.8208 . ?
O9 H9B 0.8215 . ?
O9 H9D 1.2849 . ?
O9' H9A 1.2626 . ?
O9' H9B 1.0785 . ?
O9' H9C 0.8200 . ?
O9' H9D 0.8314 . ?

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
O7 Cu1 O1 91.8(2) . . ?
O7 Cu1 O6 171.6(3) . . ?
O1 Cu1 O6 86.98(19) . . ?
O7 Cu1 O3 91.75(19) . 4 ?
O1 Cu1 O3 175.95(17) . 4 ?
O6 Cu1 O3 89.75(18) . 4 ?
O7 Cu1 O3 94.1(3) . 8_665 ?
O1 Cu1 O3 101.41(13) . 8_665 ?
O6 Cu1 O3 94.23(19) . 8_665 ?
O3 Cu1 O3 76.44(14) 4 8_665 ?
C2 C1 C13 101.2(3) . . ?
C2 C1 C14 110.5(4) . . ?
C13 C1 C14 112.3(4) . . ?
C2 C1 C17 112.4(4) . . ?
C13 C1 C17 108.6(4) . . ?
C14 C1 C17 111.5(3) . . ?
C3 C2 C7 120.1(4) . . ?
C3 C2 C1 129.1(4) . . ?
C7 C2 C1 110.7(4) . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 118.4(4) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C6 C7 C2 121.0(4) . . ?
C6 C7 C8 130.4(4) . . ?
C2 C7 C8 108.6(4) . . ?
C9 C8 C13 120.6(4) . . ?
C9 C8 C7 131.1(4) . . ?
C13 C8 C7 108.3(4) . . ?
C10 C9 C8 118.6(4) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.0(4) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 118.3(4) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C8 120.6(4) . . ?
C12 C13 C1 128.2(4) . . ?
C8 C13 C1 111.2(4) . . ?
C15 C14 C1 114.7(4) . . ?
C15 C14 H14A 108.6 . . ?
C1 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C1 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 113.7(4) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O2 C16 O1 123.7(5) . . ?
O2 C16 C15 120.2(4) . . ?
O1 C16 C15 116.1(4) . . ?
C18 C17 C1 116.4(4) . . ?
C18 C17 H17A 108.2 . . ?
C1 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
C1 C17 H17B 108.2 . . ?
H17A C17 H17B 107.3 . . ?
C19 C18 C17 113.4(4) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
O4 C19 O3 121.3(4) . . ?
O4 C19 C18 120.4(4) . . ?
O3 C19 C18 118.3(4) . . ?
O5 C20 C21 114.6(9) . . ?
O5 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
O5 C20 H20B 108.6 . . ?
C21 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 O1 Cu1 114.9(3) . . ?
C19 O3 Cu1 116.1(3) . 4_455 ?
C19 O3 Cu1 139.3(3) . 8_655 ?
Cu1 O3 Cu1 103.56(14) 4_455 8_655 ?
Cu1 O7 H7B 132(7) . . ?
Cu1 O7 H7A 117(7) . . ?
H7B O7 H7A 111(2) . . ?
Cu1 O6 H6A 118(7) . . ?
Cu1 O6 H6B 109(6) . . ?
H6A O6 H6B 110.1(19) . . ?
C20 O5 H5A 121.5 . . ?
H8A O8 H8B 107.2 . . ?
H9A O9 H9B 110.7 . . ?
H9A O9 H9D 115.9 . . ?
H9A O9' H9B 70.0 . . ?
H9A O9' H9C 132.3 . . ?
H9B O9' H9C 157.2 . . ?
H9A O9' H9D 117.3 . . ?
H9C O9' H9D 110.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C1 C2 C3 -176.7(4) . . . . ?
C14 C1 C2 C3 -57.6(6) . . . . ?
C17 C1 C2 C3 67.6(6) . . . . ?
C13 C1 C2 C7 -0.1(5) . . . . ?
C14 C1 C2 C7 119.1(4) . . . . ?
C17 C1 C2 C7 -115.7(4) . . . . ?
C7 C2 C3 C4 -1.3(7) . . . . ?
C1 C2 C3 C4 175.1(4) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 1.6(7) . . . . ?
C4 C5 C6 C7 -0.8(7) . . . . ?
C5 C6 C7 C2 -0.9(7) . . . . ?
C5 C6 C7 C8 -176.6(4) . . . . ?
C3 C2 C7 C6 2.1(7) . . . . ?
C1 C2 C7 C6 -175.0(4) . . . . ?
C3 C2 C7 C8 178.6(4) . . . . ?
C1 C2 C7 C8 1.6(5) . . . . ?
C6 C7 C8 C9 -6.2(8) . . . . ?
C2 C7 C8 C9 177.7(5) . . . . ?
C6 C7 C8 C13 173.5(5) . . . . ?
C2 C7 C8 C13 -2.6(5) . . . . ?
C13 C8 C9 C10 -0.7(7) . . . . ?
C7 C8 C9 C10 179.0(4) . . . . ?
C8 C9 C10 C11 -0.9(7) . . . . ?
C9 C10 C11 C12 1.7(7) . . . . ?
C10 C11 C12 C13 -0.9(7) . . . . ?
C11 C12 C13 C8 -0.7(7) . . . . ?
C11 C12 C13 C1 178.3(4) . . . . ?
C9 C8 C13 C12 1.5(7) . . . . ?
C7 C8 C13 C12 -178.3(4) . . . . ?
C9 C8 C13 C1 -177.6(4) . . . . ?
C7 C8 C13 C1 2.6(5) . . . . ?
C2 C1 C13 C12 179.3(4) . . . . ?
C14 C1 C13 C12 61.5(6) . . . . ?
C17 C1 C13 C12 -62.3(6) . . . . ?
C2 C1 C13 C8 -1.6(5) . . . . ?
C14 C1 C13 C8 -119.4(4) . . . . ?
C17 C1 C13 C8 116.8(4) . . . . ?
C2 C1 C14 C15 -57.6(5) . . . . ?
C13 C1 C14 C15 54.6(5) . . . . ?
C17 C1 C14 C15 176.7(4) . . . . ?
C1 C14 C15 C16 168.0(4) . . . . ?
C14 C15 C16 O2 -6.0(7) . . . . ?
C14 C15 C16 O1 175.3(5) . . . . ?
C2 C1 C17 C18 -85.8(5) . . . . ?
C13 C1 C17 C18 163.2(4) . . . . ?
C14 C1 C17 C18 38.9(5) . . . . ?
C1 C17 C18 C19 -79.9(5) . . . . ?
C17 C18 C19 O4 -40.8(7) . . . . ?
C17 C18 C19 O3 140.8(5) . . . . ?
O2 C16 O1 Cu1 9.8(8) . . . . ?
C15 C16 O1 Cu1 -171.4(4) . . . . ?
O7 Cu1 O1 C16 -77.8(5) . . . . ?
O6 Cu1 O1 C16 93.9(4) . . . . ?
O4 C19 O3 Cu1 -5.9(7) . . . 4_455 ?
C18 C19 O3 Cu1 172.4(3) . . . 4_455 ?
O4 C19 O3 Cu1 -171.9(4) . . . 8_655 ?
C18 C19 O3 Cu1 6.4(8) . . . 8_655 ?

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
O9' H9D O8 0.83 1.91 2.732(17) 168.2 1_655
O9' H9C O2 0.82 2.02 2.840(18) 179.9 4
O9 H9B O8 0.82 2.04 2.815(13) 157.9 1_655
O9 H9A O4 0.82 2.15 2.880(10) 147.6 1_655
O8 H8B O5 0.95 1.70 2.595(12) 156.3 3
O8 H8A O6 0.83 2.20 2.999(10) 162.3 .
O5 H5A O4 0.82 1.82 2.636(7) 178.7 6_656
O6 H6B O2 0.825(11) 2.33(5) 3.019(7) 141(6) 8_665
O6 H6A O9 0.823(11) 2.35(3) 3.159(11) 166(8) 5_665
O6 H6A O9' 0.823(11) 2.10(4) 2.829(14) 148(7) 5_665
O7 H7A O5 0.822(11) 2.30(4) 3.085(9) 159(10) 6_656
O7 H7B O2 0.821(11) 2.21(3) 3.022(7) 169(13) 4

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.179
_refine_diff_density_min         -1.214
_refine_diff_density_rms         0.121
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1414837'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H31 Cu N3 O4'
_chemical_formula_sum            'C34 H31 Cu N3 O4'
_chemical_formula_weight         609.16

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'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'I 41/a c d'
_symmetry_space_group_name_Hall  '-I 4bd 2c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z'
'x, -y, -z+1/2'
'y+1/4, x+3/4, -z+3/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1'
'y+3/4, x+5/4, -z+5/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z'
'-x, y, z-1/2'
'-y-1/4, -x-3/4, z-3/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'-y+1/4, -x-1/4, z-1/4'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   31.962(2)
_cell_length_b                   31.962(2)
_cell_length_c                   12.6995(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     12973.2(17)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7927
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5072
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9093
_exptl_absorpt_correction_T_max  0.9321
_exptl_absorpt_process_details   'SADABS, (Sheldrick,2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3196
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.27
_diffrn_reflns_theta_max         25.98
_reflns_number_total             3196
_reflns_number_gt                2640
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0486P)²+8.7079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3196
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.2500 0.305322(9) 0.0000 0.01905(11) Uani 1 2 d S . .
C1 C 0.31003(5) 0.33342(5) 0.14686(13) 0.0210(4) Uani 1 1 d . . .
C2 C 0.34347(5) 0.32579(5) 0.23069(13) 0.0198(4) Uani 1 1 d . . .
H2A H 0.3351 0.3015 0.2742 0.024 Uiso 1 1 calc R . .
H2B H 0.3702 0.3187 0.1955 0.024 Uiso 1 1 calc R . .
C3 C 0.35027(5) 0.36332(5) 0.30210(13) 0.0176(3) Uani 1 1 d . . .
H3A H 0.3251 0.3669 0.3465 0.021 Uiso 1 1 calc R . .
H3B H 0.3528 0.3886 0.2575 0.021 Uiso 1 1 calc R . .
C4 C 0.38893(5) 0.36107(5) 0.3750 0.0146(4) Uani 1 2 d S . .
C5 C 0.39170(5) 0.32079(5) 0.43907(12) 0.0155(3) Uani 1 1 d . . .
C6 C 0.36398(5) 0.30574(5) 0.51390(14) 0.0204(4) Uani 1 1 d . . .
H6 H 0.3389 0.3205 0.5289 0.025 Uiso 1 1 calc R . .
C7 C 0.37340(6) 0.26881(6) 0.56674(15) 0.0290(4) Uani 1 1 d . . .
H7 H 0.3544 0.2581 0.6175 0.035 Uiso 1 1 calc R . .
C8 C 0.41037(6) 0.24752(6) 0.54594(16) 0.0309(4) Uani 1 1 d . . .
H8 H 0.4168 0.2228 0.5842 0.037 Uiso 1 1 calc R . .
C9 C 0.43810(6) 0.26197(6) 0.46990(15) 0.0260(4) Uani 1 1 d . . .
H9 H 0.4631 0.2471 0.4550 0.031 Uiso 1 1 calc R . .
C10 C 0.42847(5) 0.29874(5) 0.41597(13) 0.0180(3) Uani 1 1 d . . .
C11 C 0.29609(7) 0.35830(7) -0.15092(17) 0.0403(5) Uani 1 1 d . . .
H11 H 0.2732 0.3767 -0.1390 0.048 Uiso 1 1 calc R . .
C12 C 0.32814(8) 0.37096(9) -0.21798(18) 0.0531(7) Uani 1 1 d . . .
H12 H 0.3268 0.3974 -0.2520 0.064 Uiso 1 1 calc R . .
C13 C 0.36116(8) 0.34544(10) -0.23447(18) 0.0538(7) Uani 1 1 d . . .
H13 H 0.3834 0.3537 -0.2795 0.065 Uiso 1 1 calc R . .
C14 C 0.36190(8) 0.30734(9) -0.1848(2) 0.0560(7) Uani 1 1 d . . .
H14 H 0.3848 0.2888 -0.1949 0.067 Uiso 1 1 calc R . .
C15 C 0.32895(7) 0.29616(7) -0.11976(16) 0.0386(5) Uani 1 1 d . . .
H15 H 0.3297 0.2696 -0.0860 0.046 Uiso 1 1 calc R . .
C16 C 0.25242(5) 0.21298(6) 0.08985(15) 0.0261(4) Uani 1 1 d . . .
H16 H 0.2545 0.2280 0.1542 0.031 Uiso 1 1 calc R . .
C17 C 0.25200(6) 0.16962(6) 0.09380(18) 0.0336(5) Uani 1 1 d . . .
H17 H 0.2530 0.1553 0.1593 0.040 Uiso 1 1 calc R . .
C18 C 0.2500 0.14771(9) 0.0000 0.0404(8) Uani 1 2 d S . .
H18 H 0.2500 0.1180 0.0000 0.048 Uiso 1 2 calc SR . .
N1 N 0.2500 0.23467(6) 0.0000 0.0211(4) Uani 1 2 d S . .
N2 N 0.29641(5) 0.32110(5) -0.10272(11) 0.0263(3) Uani 1 1 d . . .
O1 O 0.29016(4) 0.30099(4) 0.11678(9) 0.0217(3) Uani 1 1 d . . .
O2 O 0.30426(4) 0.36900(4) 0.11151(11) 0.0348(3) Uani 1 1 d . . .


_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 1.9662(11) . ?
Cu1 O1 1.9663(11) 5 ?
Cu1 N2 2.0387(15) 5 ?
Cu1 N2 2.0387(15) . ?
Cu1 N1 2.258(2) . ?
C1 O2 1.237(2) . ?
C1 O1 1.274(2) . ?
C1 C2 1.528(2) . ?
C2 C3 1.519(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.546(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.526(2) . ?
C4 C5 1.526(2) 16 ?
C4 C3 1.546(2) 16 ?
C5 C6 1.385(2) . ?
C5 C10 1.401(2) . ?
C6 C7 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(2) . ?
C9 H9 0.9500 . ?
C10 C10 1.464(3) 16 ?
C11 N2 1.337(3) . ?
C11 C12 1.392(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.350(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 N2 1.328(3) . ?
C15 H15 0.9500 . ?
C16 N1 1.337(2) . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9500 . ?
C18 C17 1.383(3) 5 ?
C18 H18 0.9500 . ?
N1 C16 1.337(2) 5 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 171.93(7) . 5 ?
O1 Cu1 N2 90.56(5) . 5 ?
O1 Cu1 N2 91.44(5) 5 5 ?
O1 Cu1 N2 91.44(5) . . ?
O1 Cu1 N2 90.56(5) 5 . ?
N2 Cu1 N2 151.36(9) 5 . ?
O1 Cu1 N1 85.97(3) . . ?
O1 Cu1 N1 85.97(3) 5 . ?
N2 Cu1 N1 104.32(5) 5 . ?
N2 Cu1 N1 104.32(5) . . ?
O2 C1 O1 124.39(16) . . ?
O2 C1 C2 120.27(15) . . ?
O1 C1 C2 115.33(15) . . ?
C3 C2 C1 112.95(14) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 115.80(13) . . ?
C2 C3 H3A 108.3 . . ?
C4 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C5 C4 C5 100.74(17) . 16 ?
C5 C4 C3 110.97(8) . 16 ?
C5 C4 C3 113.90(8) 16 16 ?
C5 C4 C3 113.90(8) . . ?
C5 C4 C3 110.97(8) 16 . ?
C3 C4 C3 106.54(18) 16 . ?
C6 C5 C10 120.35(15) . . ?
C6 C5 C4 128.43(15) . . ?
C10 C5 C4 111.19(14) . . ?
C5 C6 C7 119.15(16) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.54(16) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.80(17) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 118.71(17) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C5 120.40(15) . . ?
C9 C10 C10 131.18(10) . 16 ?
C5 C10 C10 108.41(9) . 16 ?
N2 C11 C12 122.2(2) . . ?
N2 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 118.6(2) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
N2 C15 C14 122.5(2) . . ?
N2 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
N1 C16 C17 123.24(19) . . ?
N1 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
C18 C17 C16 118.38(19) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C17 C18 C17 119.2(3) . 5 ?
C17 C18 H18 120.4 . . ?
C17 C18 H18 120.4 5 . ?
C16 N1 C16 117.6(2) . 5 ?
C16 N1 Cu1 121.22(12) . . ?
C16 N1 Cu1 121.22(12) 5 . ?
C15 N2 C11 117.71(18) . . ?
C15 N2 Cu1 121.70(14) . . ?
C11 N2 Cu1 120.48(14) . . ?
C1 O1 Cu1 119.63(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 30.6(2) . . . . ?
O1 C1 C2 C3 -150.67(15) . . . . ?
C1 C2 C3 C4 -169.10(12) . . . . ?
C2 C3 C4 C5 -51.18(18) . . . . ?
C2 C3 C4 C5 61.65(17) . . . 16 ?
C2 C3 C4 C3 -173.85(16) . . . 16 ?
C5 C4 C5 C6 179.1(2) 16 . . . ?
C3 C4 C5 C6 58.19(19) 16 . . . ?
C3 C4 C5 C6 -62.0(2) . . . . ?
C5 C4 C5 C10 0.82(8) 16 . . . ?
C3 C4 C5 C10 -120.12(15) 16 . . . ?
C3 C4 C5 C10 119.66(15) . . . . ?
C10 C5 C6 C7 0.9(2) . . . . ?
C4 C5 C6 C7 -177.31(14) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C6 C7 C8 C9 -1.9(3) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C8 C9 C10 C5 0.6(3) . . . . ?
C8 C9 C10 C10 179.3(2) . . . 16 ?
C6 C5 C10 C9 -1.6(2) . . . . ?
C4 C5 C10 C9 176.85(14) . . . . ?
C6 C5 C10 C10 179.43(17) . . . 16 ?
C4 C5 C10 C10 -2.1(2) . . . 16 ?
N2 C11 C12 C13 -1.0(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C13 C14 C15 N2 -0.4(3) . . . . ?
N1 C16 C17 C18 1.6(2) . . . . ?
C16 C17 C18 C17 -0.78(11) . . . 5 ?
C17 C16 N1 C16 -0.84(13) . . . 5 ?
C17 C16 N1 Cu1 179.16(13) . . . . ?
O1 Cu1 N1 C16 36.99(9) . . . . ?
O1 Cu1 N1 C16 -143.01(9) 5 . . . ?
N2 Cu1 N1 C16 -52.56(9) 5 . . . ?
N2 Cu1 N1 C16 127.45(9) . . . . ?
O1 Cu1 N1 C16 -143.01(9) . . . 5 ?
O1 Cu1 N1 C16 36.99(9) 5 . . 5 ?
N2 Cu1 N1 C16 127.44(9) 5 . . 5 ?
N2 Cu1 N1 C16 -52.56(9) . . . 5 ?
C14 C15 N2 C11 0.0(3) . . . . ?
C14 C15 N2 Cu1 -176.37(17) . . . . ?
C12 C11 N2 C15 0.7(3) . . . . ?
C12 C11 N2 Cu1 177.12(16) . . . . ?
O1 Cu1 N2 C15 58.55(15) . . . . ?
O1 Cu1 N2 C15 -113.63(15) 5 . . . ?
N2 Cu1 N2 C15 152.35(15) 5 . . . ?
N1 Cu1 N2 C15 -27.65(15) . . . . ?
O1 Cu1 N2 C11 -117.67(15) . . . . ?
O1 Cu1 N2 C11 70.14(15) 5 . . . ?
N2 Cu1 N2 C11 -23.87(14) 5 . . . ?
N1 Cu1 N2 C11 156.12(14) . . . . ?
O2 C1 O1 Cu1 4.4(2) . . . . ?
C2 C1 O1 Cu1 -174.29(10) . . . . ?
N2 Cu1 O1 C1 -87.69(13) 5 . . . ?
N2 Cu1 O1 C1 63.73(13) . . . . ?
N1 Cu1 O1 C1 167.99(12) . . . . ?

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
C11 H11 O2 0.95 2.51 3.264(3) 136.0 5

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.049


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.000 0.047 457 129 ' '
2 0.250 0.500 0.537 457 129 ' '
3 0.750 0.000 0.452 457 129 ' '
4 0.750 0.500 0.939 457 129 ' '
_platon_squeeze_details          
;
N: Total Potential Solvent Accessible Void Vol ..................  1827.4 Ang^3
N: Electron Count / Cell =    516 - To be included in D(calc), F000 & Mol.Wght.

Due to the seriously disorder of the water molecules clathered in the channel, 
the contribution from these water molecules were taken into account in the final
refinement using the SQUEEZE/PLATON program. According the the analysis, each host
unit was assigned ca. 3.2 water molecules.
;
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1414838'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H21 Cu N O4), C5 H5 N'
_chemical_formula_sum            'C53 H47 Cu2 N3 O8'
_chemical_formula_weight         981.02

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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/m'
_symmetry_space_group_name_Hall  '-C 2y'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.0623(12)
_cell_length_b                   22.070(2)
_cell_length_c                   10.3481(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.293(2)
_cell_angle_gamma                90.00
_cell_volume                     2398.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1449
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      21.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8852
_exptl_absorpt_correction_T_max  0.9115
_exptl_absorpt_process_details   'SADABS, (Sheldrick,2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6941
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2430
_reflns_number_gt                1880
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2430
_refine_ls_number_parameters     159
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.04218(5) 0.5000 0.13363(5) 0.0313(2) Uani 1 2 d S . .
C1 C 0.5000 0.36679(19) 0.0000 0.0383(11) Uani 1 2 d S . .
C2 C 0.5316(3) 0.32274(15) 0.1187(4) 0.0440(9) Uani 1 1 d . . .
C3 C 0.5676(4) 0.33603(18) 0.2555(4) 0.0622(11) Uani 1 1 d . . .
H3 H 0.5757 0.3760 0.2852 0.075 Uiso 1 1 calc R . .
C4 C 0.5917(5) 0.2888(2) 0.3482(5) 0.0869(15) Uani 1 1 d . . .
H4 H 0.6156 0.2970 0.4410 0.104 Uiso 1 1 calc R . .
C5 C 0.5805(5) 0.2300(2) 0.3033(7) 0.0963(17) Uani 1 1 d . . .
H5 H 0.5980 0.1988 0.3669 0.116 Uiso 1 1 calc R . .
C6 C 0.5445(4) 0.21592(18) 0.1687(6) 0.0756(13) Uani 1 1 d . . .
H6 H 0.5364 0.1757 0.1403 0.091 Uiso 1 1 calc R . .
C7 C 0.5202(3) 0.26300(15) 0.0743(4) 0.0507(10) Uani 1 1 d . . .
C8 C 0.6139(3) 0.40802(13) 0.0033(4) 0.0397(8) Uani 1 1 d . . .
H8A H 0.5893 0.4338 -0.0767 0.048 Uiso 1 1 calc R . .
H8B H 0.6319 0.4341 0.0825 0.048 Uiso 1 1 calc R . .
C9 C 0.7353(3) 0.37455(14) 0.0077(4) 0.0458(9) Uani 1 1 d . . .
H9A H 0.7643 0.3504 0.0901 0.055 Uiso 1 1 calc R . .
H9B H 0.7187 0.3475 -0.0698 0.055 Uiso 1 1 calc R . .
C10 C 0.8371(3) 0.41972(14) 0.0047(4) 0.0375(8) Uani 1 1 d . . .
C11 C 1.1348(4) 0.4497(2) 0.4220(4) 0.0706(12) Uani 1 1 d . . .
H11 H 1.1226 0.4131 0.3749 0.085 Uiso 1 1 calc R . .
C12 C 1.1718(5) 0.4477(3) 0.5625(5) 0.1002(19) Uani 1 1 d . . .
H12 H 1.1837 0.4108 0.6081 0.120 Uiso 1 1 calc R . .
C13 C 1.1901(7) 0.5000 0.6317(7) 0.103(3) Uani 1 2 d S . .
H13 H 1.2152 0.5000 0.7263 0.123 Uiso 1 2 calc SR . .
N1 N 1.1159(4) 0.5000 0.3513(4) 0.0460(10) Uani 1 2 d S . .
O1 O 0.9110(2) 0.43723(10) 0.1173(2) 0.0466(6) Uani 1 1 d . . .
O2 O 0.8403(2) 0.43711(10) -0.1084(2) 0.0471(6) Uani 1 1 d . . .
C14 C 0.4291(5) 0.4707(2) 0.3927(5) 0.124(3) Uani 1 1 d DU . .
H14 H 0.3784 0.4505 0.3159 0.149 Uiso 1 1 calc R A 1
C15 C 0.5000 0.4375(4) 0.5000 0.083(9) Uani 0.50 2 d SPDU . 1
H15 H 0.5000 0.3954 0.5000 0.100 Uiso 0.50 2 calc SPR . 1
N2 N 0.5000 0.4375(4) 0.5000 0.171(15) Uani 0.50 2 d SPDU . 2


_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 O2 1.974(2) 5_765 ?
Cu1 O2 1.974(2) 2_755 ?
Cu1 O1 1.975(2) 6_565 ?
Cu1 O1 1.975(2) . ?
Cu1 N1 2.141(4) . ?
Cu1 Cu1 2.6266(11) 5_765 ?
C1 C2 1.519(4) 2_655 ?
C1 C2 1.519(4) . ?
C1 C8 1.546(4) . ?
C1 C8 1.546(4) 2_655 ?
C2 C3 1.377(5) . ?
C2 C7 1.389(5) . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.359(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(5) . ?
C6 H6 0.9300 . ?
C7 C7 1.460(8) 2_655 ?
C8 C9 1.521(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.511(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O2 1.243(4) . ?
C10 O1 1.256(4) . ?
C11 N1 1.311(4) . ?
C11 C12 1.381(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.339(6) . ?
C12 H12 0.9300 . ?
C13 C12 1.339(6) 6_565 ?
C13 H13 0.9300 . ?
N1 C11 1.311(4) 6_565 ?
O2 Cu1 1.974(2) 5_765 ?
C14 C14 1.293(11) 6_565 ?
C14 C15 1.356(5) . ?
C14 H14 0.9300 . ?
C15 C14 1.356(5) 2_656 ?
C15 H15 0.9300 . ?

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 O2 89.36(13) 5_765 2_755 ?
O2 Cu1 O1 89.54(10) 5_765 6_565 ?
O2 Cu1 O1 168.12(9) 2_755 6_565 ?
O2 Cu1 O1 168.12(9) 5_765 . ?
O2 Cu1 O1 89.54(10) 2_755 . ?
O1 Cu1 O1 89.10(13) 6_565 . ?
O2 Cu1 N1 95.16(10) 5_765 . ?
O2 Cu1 N1 95.16(10) 2_755 . ?
O1 Cu1 N1 96.72(10) 6_565 . ?
O1 Cu1 N1 96.72(10) . . ?
O2 Cu1 Cu1 83.79(7) 5_765 5_765 ?
O2 Cu1 Cu1 83.79(7) 2_755 5_765 ?
O1 Cu1 Cu1 84.33(7) 6_565 5_765 ?
O1 Cu1 Cu1 84.33(7) . 5_765 ?
N1 Cu1 Cu1 178.51(11) . 5_765 ?
C2 C1 C2 100.4(4) 2_655 . ?
C2 C1 C8 111.95(17) 2_655 . ?
C2 C1 C8 112.33(18) . . ?
C2 C1 C8 112.33(18) 2_655 2_655 ?
C2 C1 C8 111.95(17) . 2_655 ?
C8 C1 C8 107.9(3) . 2_655 ?
C3 C2 C7 120.6(3) . . ?
C3 C2 C1 127.9(3) . . ?
C7 C2 C1 111.5(3) . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 122.0(5) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 118.6(4) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C2 C7 C6 119.9(4) . . ?
C2 C7 C7 108.3(2) . 2_655 ?
C6 C7 C7 131.8(3) . 2_655 ?
C9 C8 C1 114.9(2) . . ?
C9 C8 H8A 108.5 . . ?
C1 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C1 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 C8 109.6(2) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O2 C10 O1 125.1(3) . . ?
O2 C10 C9 117.7(3) . . ?
O1 C10 C9 117.2(3) . . ?
N1 C11 C12 123.8(5) . . ?
N1 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C13 C12 C11 118.8(6) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C12 118.9(7) . 6_565 ?
C12 C13 H13 120.5 . . ?
C12 C13 H13 120.5 6_565 . ?
C11 N1 C11 115.9(5) . 6_565 ?
C11 N1 Cu1 121.9(2) . . ?
C11 N1 Cu1 121.9(2) 6_565 . ?
C10 O1 Cu1 122.8(2) . . ?
C10 O2 Cu1 123.8(2) . 5_765 ?
C14 C14 C15 122.7(4) 6_565 . ?
C14 C14 H14 118.7 6_565 . ?
C15 C14 H14 118.7 . . ?
C14 C15 C14 114.6(8) . 2_656 ?
C14 C15 H15 122.7 . . ?
C14 C15 H15 122.7 2_656 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C3 -179.8(4) 2_655 . . . ?
C8 C1 C2 C3 61.1(4) . . . . ?
C8 C1 C2 C3 -60.4(4) 2_655 . . . ?
C2 C1 C2 C7 0.20(17) 2_655 . . . ?
C8 C1 C2 C7 -118.9(3) . . . . ?
C8 C1 C2 C7 119.6(3) 2_655 . . . ?
C7 C2 C3 C4 -0.3(6) . . . . ?
C1 C2 C3 C4 179.7(3) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C3 C4 C5 C6 -0.8(9) . . . . ?
C4 C5 C6 C7 0.8(8) . . . . ?
C3 C2 C7 C6 0.4(5) . . . . ?
C1 C2 C7 C6 -179.6(3) . . . . ?
C3 C2 C7 C7 179.5(3) . . . 2_655 ?
C1 C2 C7 C7 -0.5(4) . . . 2_655 ?
C5 C6 C7 C2 -0.7(6) . . . . ?
C5 C6 C7 C7 -179.5(5) . . . 2_655 ?
C2 C1 C8 C9 -56.3(4) 2_655 . . . ?
C2 C1 C8 C9 55.8(4) . . . . ?
C8 C1 C8 C9 179.6(3) 2_655 . . . ?
C1 C8 C9 C10 177.7(3) . . . . ?
C8 C9 C10 O2 -86.7(3) . . . . ?
C8 C9 C10 O1 92.5(3) . . . . ?
N1 C11 C12 C13 -0.2(9) . . . . ?
C11 C12 C13 C12 0.2(12) . . . 6_565 ?
C12 C11 N1 C11 0.3(8) . . . 6_565 ?
C12 C11 N1 Cu1 -174.2(3) . . . . ?
O2 Cu1 N1 C11 -137.8(4) 5_765 . . . ?
O2 Cu1 N1 C11 -48.0(4) 2_755 . . . ?
O1 Cu1 N1 C11 132.0(4) 6_565 . . . ?
O1 Cu1 N1 C11 42.2(4) . . . . ?
O2 Cu1 N1 C11 48.0(4) 5_765 . . 6_565 ?
O2 Cu1 N1 C11 137.8(4) 2_755 . . 6_565 ?
O1 Cu1 N1 C11 -42.2(4) 6_565 . . 6_565 ?
O1 Cu1 N1 C11 -132.0(4) . . . 6_565 ?
O2 C10 O1 Cu1 3.3(4) . . . . ?
C9 C10 O1 Cu1 -175.85(18) . . . . ?
O2 Cu1 O1 C10 -0.5(6) 5_765 . . . ?
O2 Cu1 O1 C10 -85.2(2) 2_755 . . . ?
O1 Cu1 O1 C10 83.0(2) 6_565 . . . ?
N1 Cu1 O1 C10 179.7(2) . . . . ?
O1 C10 O2 Cu1 -3.6(4) . . . 5_765 ?
C9 C10 O2 Cu1 175.56(18) . . . 5_765 ?
C14 C14 C15 C14 -0.001(2) 6_565 . . 2_656 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.070


# start Validation Reply Form
_vrf_PLAT222_2                   
;
PROBLEM: Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        8.3 Ratio 
RESPONSE: This is due to the disorder of the water molecules.
;
_vrf_PLAT417_2                   
;
PROBLEM: Short Inter D-H..H-D       H6A    ..  H9C     ..       2.02 Ang.  
RESPONSE: This is due to the disorder of the water molecules.
;
_vrf_PLAT601_3                   
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        456 Ang3  
RESPONSE: Due to the seriously disorder of the water molecules clathered in the channel, 
the contribution from these water molecules were taken into account in the final
refinement using the SQUEEZE/PLATON program. According the the analysis, each host
unit was assigned ca. 3.2 water molecules.
;
# end Validation Reply Form
