# 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_complex_1
_database_code_depnum_ccdc_archive 'CCDC 1042812'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H52 Cu2 N4 O8 P2, 2(N O3), 4(C H4 O)'
_chemical_formula_sum            'C58 H68 Cu2 N6 O18 P2'
_chemical_formula_weight         1324.3

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'
P P 0.1023 0.0942 '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                   11.543(2)
_cell_length_b                   11.603(2)
_cell_length_c                   12.615(2)
_cell_angle_alpha                69.352(10)
_cell_angle_beta                 63.370(10)
_cell_angle_gamma                78.518(12)
_cell_volume                     1411.6(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    132
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             618
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 2 CCD Diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21285
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5469
_reflns_number_gt                3738
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_refine_special_details          
; 

Nitrate molecule was heavily disordered hence, in order to model the electron 
density, the applied constraints are listed herein.

DFIX 1.25 0.01 N3 O5 N3 O6 N3 O7 N3A O5A N3A O6A N3A O7A
DFIX 2.16 0.01 O5 O6 O6 O7 O7 O5
DFIX 2.16 0.01 O5A O6A O6A O7A O7A O5A
FLAT N3 O5 O6 O7
FLAT N3A O5A O6A O7A
SIMU 0.01 0.02 2.90 N3 O5 O6 O7 N3A O5A O6A O7A

 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. 

_platon_squeeze_details 
loop_

# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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  0.000  0.000  0.500        58        26 ' '
   2  0.500  0.500  0.000        97        44 ' '
_platon_squeeze_void_probe_radius                  1.20

_platon_squeeze_details 
loop_                          
The squeeze software (Platon) cannot calculate the absolute value of electrons
that are removed and however 70 elcetrons is very close to four molecules of 
methanol per unit cell (i.e. 72 electrons).Hence, it has been assumed that there
are two molecules of metahnol in an asymmetric unit. Notably, the SQUEEZE treated
structure is very stable with minimal IUCr checkcif problems, improved R factor 
and goodness of fit. Moreover, the TGA results also showed the presence of two methanol
molecules. 

;

_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)+(0.0932P)²+0.5554P] 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         5469
_refine_ls_number_parameters     348
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1574
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_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 0.70069(5) -0.01873(5) 0.30734(5) 0.0322(2) Uani 1 1 d . . .
P1 P 0.45807(10) 0.16510(10) 0.39305(10) 0.0297(3) Uani 1 1 d . . .
O1 O 0.3722(3) 0.0782(3) 0.5120(3) 0.0363(7) Uani 1 1 d . . .
O2 O 0.3707(3) 0.2535(3) 0.3261(3) 0.0384(7) Uani 1 1 d . . .
O3 O 0.5628(3) 0.1054(3) 0.3010(3) 0.0354(7) Uani 1 1 d . . .
O4 O 0.8300(3) 0.1114(3) 0.2944(4) 0.0590(10) Uani 1 1 d . . .
H4A H 0.8272 0.1921 0.2427 0.088 Uiso 1 1 d R . .
H4B H 0.8583 0.1152 0.3525 0.088 Uiso 1 1 d R . .
O5 O 0.1597(10) 0.6527(9) 0.8863(10) 0.081(3) Uiso 0.50 1 d PDU A -1
O6 O 0.0659(14) 0.4767(11) 1.0170(14) 0.164(5) Uiso 0.50 1 d PDU A -1
O7 O -0.0322(12) 0.6155(13) 0.9209(14) 0.167(5) Uiso 0.50 1 d PDU A -1
O5A O 0.1154(13) 0.6689(12) 0.8751(13) 0.117(4) Uiso 0.50 1 d PDU B -2
O6A O 0.2734(16) 0.6271(17) 0.9368(19) 0.223(6) Uiso 0.50 1 d PDU B -2
O7A O 0.127(2) 0.4947(14) 1.0119(18) 0.212(6) Uiso 0.50 1 d PDU B -2
N1 N 0.8375(3) -0.1560(3) 0.2891(4) 0.0383(9) Uani 1 1 d . . .
N2 N 0.7618(3) 0.0024(4) 0.1251(3) 0.0389(9) Uani 1 1 d . . .
N3 N 0.0634(10) 0.5822(10) 0.9409(11) 0.098(4) Uiso 0.50 1 d PDU A -1
N3A N 0.1730(15) 0.6001(14) 0.9367(16) 0.194(6) Uiso 0.50 1 d PDU B -2
C1 C 0.5304(4) 0.2723(4) 0.4168(4) 0.0379(11) Uani 1 1 d . . .
H1A H 0.6087 0.2323 0.4268 0.045 Uiso 1 1 calc R . .
H1B H 0.5568 0.3418 0.3416 0.045 Uiso 1 1 calc R . .
C2 C 0.4488(4) 0.3226(4) 0.5256(4) 0.0345(10) Uani 1 1 d . . .
C3 C 0.4573(4) 0.2637(4) 0.6403(4) 0.0361(10) Uani 1 1 d . . .
C4 C 0.5410(5) 0.1598(4) 0.6640(5) 0.0455(12) Uani 1 1 d . . .
H4 H 0.5937 0.1260 0.5999 0.055 Uiso 1 1 calc R . .
C5 C 0.5475(6) 0.1082(5) 0.7751(6) 0.0580(14) Uani 1 1 d . . .
H5 H 0.6055 0.0415 0.7853 0.070 Uiso 1 1 calc R . .
C6 C 0.4673(6) 0.1540(6) 0.8762(6) 0.0629(16) Uani 1 1 d . . .
H6 H 0.4719 0.1169 0.9527 0.075 Uiso 1 1 calc R . .
C7 C 0.3853(5) 0.2499(5) 0.8620(5) 0.0556(14) Uani 1 1 d . . .
H7 H 0.3311 0.2780 0.9298 0.067 Uiso 1 1 calc R . .
C8 C 0.3785(4) 0.3113(5) 0.7440(5) 0.0430(12) Uani 1 1 d . . .
C9 C 0.2977(5) 0.4168(5) 0.7265(5) 0.0511(14) Uani 1 1 d . . .
H9 H 0.2473 0.4476 0.7932 0.061 Uiso 1 1 calc R . .
C10 C 0.2901(4) 0.4763(4) 0.6145(5) 0.0421(12) Uani 1 1 d . . .
C11 C 0.2098(5) 0.5850(5) 0.5976(6) 0.0568(15) Uani 1 1 d . . .
H11 H 0.1612 0.6164 0.6641 0.068 Uiso 1 1 calc R . .
C12 C 0.2021(5) 0.6434(5) 0.4881(6) 0.0611(16) Uani 1 1 d . . .
H12 H 0.1498 0.7150 0.4789 0.073 Uiso 1 1 calc R . .
C13 C 0.2734(5) 0.5960(5) 0.3877(6) 0.0560(14) Uani 1 1 d . . .
H13 H 0.2664 0.6357 0.3124 0.067 Uiso 1 1 calc R . .
C14 C 0.3522(5) 0.4935(4) 0.3985(5) 0.0456(12) Uani 1 1 d . . .
H14 H 0.3991 0.4648 0.3298 0.055 Uiso 1 1 calc R . .
C15 C 0.3656(4) 0.4287(4) 0.5106(5) 0.0382(11) Uani 1 1 d . . .
C16 C 0.2977(6) 0.2035(5) 0.2882(6) 0.0588(15) Uani 1 1 d . . .
H16B H 0.2573 0.1299 0.3531 0.071 Uiso 1 1 calc R . .
H16A H 0.3553 0.1805 0.2138 0.071 Uiso 1 1 calc R . .
C17 C 0.1970(7) 0.2942(7) 0.2629(8) 0.094(2) Uani 1 1 d . . .
H17C H 0.1376 0.3138 0.3377 0.141 Uiso 1 1 calc R . .
H17B H 0.1508 0.2600 0.2347 0.141 Uiso 1 1 calc R . .
H17A H 0.2369 0.3677 0.2000 0.141 Uiso 1 1 calc R . .
C18 C 0.8742(5) -0.2323(5) 0.3775(5) 0.0498(13) Uani 1 1 d . . .
H18 H 0.8368 -0.2195 0.4551 0.060 Uiso 1 1 calc R . .
C19 C 0.9634(5) -0.3280(5) 0.3601(6) 0.0579(14) Uani 1 1 d . . .
H19 H 0.9847 -0.3803 0.4247 0.069 Uiso 1 1 calc R . .
C20 C 1.0203(5) -0.3451(5) 0.2464(7) 0.0673(18) Uani 1 1 d . . .
H20 H 1.0818 -0.4095 0.2318 0.081 Uiso 1 1 calc R . .
C21 C 0.9860(5) -0.2650(5) 0.1503(6) 0.0594(16) Uani 1 1 d . . .
H21 H 1.0247 -0.2750 0.0714 0.071 Uiso 1 1 calc R . .
C22 C 0.8947(4) -0.1724(4) 0.1755(5) 0.0407(11) Uani 1 1 d . . .
C23 C 0.8514(4) -0.0835(5) 0.0834(4) 0.0403(11) Uani 1 1 d . . .
C24 C 0.8980(5) -0.0824(6) -0.0396(5) 0.0546(14) Uani 1 1 d . . .
H24 H 0.9592 -0.1424 -0.0680 0.066 Uiso 1 1 calc R . .
C25 C 0.8525(5) 0.0087(6) -0.1189(5) 0.0628(16) Uani 1 1 d . . .
H25 H 0.8838 0.0115 -0.2017 0.075 Uiso 1 1 calc R . .
C26 C 0.7603(5) 0.0953(6) -0.0746(5) 0.0562(14) Uani 1 1 d . . .
H26 H 0.7275 0.1567 -0.1264 0.067 Uiso 1 1 calc R . .
C27 C 0.7177(5) 0.0892(5) 0.0481(4) 0.0474(12) Uani 1 1 d . . .
H27 H 0.6558 0.1480 0.0781 0.057 Uiso 1 1 calc R . .


_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 O3 1.932(3) . ?
Cu1 O1 1.944(3) 2_656 ?
Cu1 N1 2.003(4) . ?
Cu1 N2 2.015(4) . ?
Cu1 O4 2.245(3) . ?
P1 O1 1.500(3) . ?
P1 O3 1.505(3) . ?
P1 O2 1.589(3) . ?
P1 C1 1.799(5) . ?
O1 Cu1 1.944(3) 2_656 ?
O2 C16 1.422(6) . ?
O4 H4A 0.9382 . ?
O4 H4B 0.9427 . ?
O5 N3 1.286(8) . ?
O6 N3 1.266(8) . ?
O7 N3 1.201(8) . ?
O5A N3A 1.224(9) . ?
O6A N3A 1.260(9) . ?
O7A N3A 1.290(9) . ?
N1 C18 1.337(6) . ?
N1 C22 1.349(6) . ?
N2 C27 1.329(6) . ?
N2 C23 1.346(6) . ?
C1 C2 1.517(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.404(6) . ?
C2 C15 1.415(6) . ?
C3 C4 1.420(6) . ?
C3 C8 1.444(6) . ?
C4 C5 1.346(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.326(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.436(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(7) . ?
C9 C10 1.370(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.421(7) . ?
C10 C15 1.442(6) . ?
C11 C12 1.342(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.400(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.352(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.410(7) . ?
C14 H14 0.9300 . ?
C16 C17 1.472(8) . ?
C16 H16B 0.9700 . ?
C16 H16A 0.9700 . ?
C17 H17C 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17A 0.9600 . ?
C18 C19 1.362(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.354(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.407(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.362(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.460(7) . ?
C23 C24 1.393(7) . ?
C24 C25 1.377(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.376(7) . ?
C26 H26 0.9300 . ?
C27 H27 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
O3 Cu1 O1 94.24(12) . 2_656 ?
O3 Cu1 N1 168.65(14) . . ?
O1 Cu1 N1 93.35(14) 2_656 . ?
O3 Cu1 N2 90.31(14) . . ?
O1 Cu1 N2 165.64(14) 2_656 . ?
N1 Cu1 N2 80.36(16) . . ?
O3 Cu1 O4 93.97(13) . . ?
O1 Cu1 O4 93.78(14) 2_656 . ?
N1 Cu1 O4 93.94(14) . . ?
N2 Cu1 O4 99.49(14) . . ?
O1 P1 O3 115.56(17) . . ?
O1 P1 O2 108.63(17) . . ?
O3 P1 O2 107.27(17) . . ?
O1 P1 C1 113.3(2) . . ?
O3 P1 C1 108.73(19) . . ?
O2 P1 C1 102.40(19) . . ?
P1 O1 Cu1 149.1(2) . 2_656 ?
C16 O2 P1 120.3(3) . . ?
P1 O3 Cu1 134.80(19) . . ?
Cu1 O4 H4A 115.5 . . ?
Cu1 O4 H4B 131.4 . . ?
H4A O4 H4B 107.1 . . ?
C18 N1 C22 118.2(4) . . ?
C18 N1 Cu1 126.7(3) . . ?
C22 N1 Cu1 115.1(3) . . ?
C27 N2 C23 119.7(4) . . ?
C27 N2 Cu1 125.5(3) . . ?
C23 N2 Cu1 114.7(3) . . ?
O7 N3 O6 118.0(9) . . ?
O7 N3 O5 120.4(9) . . ?
O6 N3 O5 121.6(9) . . ?
O5A N3A O6A 124.3(11) . . ?
O5A N3A O7A 119.6(10) . . ?
O6A N3A O7A 116.0(10) . . ?
C2 C1 P1 117.6(3) . . ?
C2 C1 H1A 107.9 . . ?
P1 C1 H1A 107.9 . . ?
C2 C1 H1B 107.9 . . ?
P1 C1 H1B 107.9 . . ?
H1A C1 H1B 107.2 . . ?
C3 C2 C15 120.6(4) . . ?
C3 C2 C1 119.6(4) . . ?
C15 C2 C1 119.8(4) . . ?
C2 C3 C4 125.1(4) . . ?
C2 C3 C8 119.4(4) . . ?
C4 C3 C8 115.5(4) . . ?
C5 C4 C3 122.9(5) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.0(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 121.3(5) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 121.7(5) . . ?
C9 C8 C3 118.9(5) . . ?
C7 C8 C3 119.5(5) . . ?
C10 C9 C8 122.3(4) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 121.6(5) . . ?
C9 C10 C15 119.7(4) . . ?
C11 C10 C15 118.7(5) . . ?
C12 C11 C10 121.7(5) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 119.7(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 121.0(6) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 122.1(5) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C2 124.1(4) . . ?
C14 C15 C10 116.8(4) . . ?
C2 C15 C10 119.1(4) . . ?
O2 C16 C17 110.6(5) . . ?
O2 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
O2 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
H16B C16 H16A 108.1 . . ?
C16 C17 H17C 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
H17C C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?
N1 C18 C19 123.5(5) . . ?
N1 C18 H18 118.3 . . ?
C19 C18 H18 118.3 . . ?
C20 C19 C18 118.4(6) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 C21 119.7(5) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 118.4(5) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
N1 C22 C21 121.8(5) . . ?
N1 C22 C23 114.8(4) . . ?
C21 C22 C23 123.4(5) . . ?
N2 C23 C24 120.5(5) . . ?
N2 C23 C22 114.9(4) . . ?
C24 C23 C22 124.6(5) . . ?
C25 C24 C23 119.3(5) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 119.5(5) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 118.6(5) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
N2 C27 C26 122.4(5) . . ?
N2 C27 H27 118.8 . . ?
C26 C27 H27 118.8 . . ?

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
O3 P1 O1 Cu1 123.7(3) . . . 2_656 ?
O2 P1 O1 Cu1 -115.8(4) . . . 2_656 ?
C1 P1 O1 Cu1 -2.7(4) . . . 2_656 ?
O1 P1 O2 C16 -61.3(4) . . . . ?
O3 P1 O2 C16 64.2(4) . . . . ?
C1 P1 O2 C16 178.6(4) . . . . ?
O1 P1 O3 Cu1 -54.3(3) . . . . ?
O2 P1 O3 Cu1 -175.6(2) . . . . ?
C1 P1 O3 Cu1 74.4(3) . . . . ?
O1 Cu1 O3 P1 16.2(3) 2_656 . . . ?
N1 Cu1 O3 P1 148.1(6) . . . . ?
N2 Cu1 O3 P1 -177.4(3) . . . . ?
O4 Cu1 O3 P1 -77.9(3) . . . . ?
O3 Cu1 N1 C18 -147.0(6) . . . . ?
O1 Cu1 N1 C18 -15.1(4) 2_656 . . . ?
N2 Cu1 N1 C18 177.9(4) . . . . ?
O4 Cu1 N1 C18 78.9(4) . . . . ?
O3 Cu1 N1 C22 31.4(9) . . . . ?
O1 Cu1 N1 C22 163.4(3) 2_656 . . . ?
N2 Cu1 N1 C22 -3.7(3) . . . . ?
O4 Cu1 N1 C22 -102.6(3) . . . . ?
O3 Cu1 N2 C27 8.0(4) . . . . ?
O1 Cu1 N2 C27 116.6(6) 2_656 . . . ?
N1 Cu1 N2 C27 -178.5(4) . . . . ?
O4 Cu1 N2 C27 -86.1(4) . . . . ?
O3 Cu1 N2 C23 -169.5(3) . . . . ?
O1 Cu1 N2 C23 -60.9(7) 2_656 . . . ?
N1 Cu1 N2 C23 4.0(3) . . . . ?
O4 Cu1 N2 C23 96.4(3) . . . . ?
O1 P1 C1 C2 -37.2(4) . . . . ?
O3 P1 C1 C2 -167.1(3) . . . . ?
O2 P1 C1 C2 79.6(4) . . . . ?
P1 C1 C2 C3 93.3(4) . . . . ?
P1 C1 C2 C15 -87.1(5) . . . . ?
C15 C2 C3 C4 -177.5(4) . . . . ?
C1 C2 C3 C4 2.1(6) . . . . ?
C15 C2 C3 C8 0.9(6) . . . . ?
C1 C2 C3 C8 -179.5(4) . . . . ?
C2 C3 C4 C5 178.6(5) . . . . ?
C8 C3 C4 C5 0.1(7) . . . . ?
C3 C4 C5 C6 1.6(8) . . . . ?
C4 C5 C6 C7 -0.8(8) . . . . ?
C5 C6 C7 C8 -1.8(8) . . . . ?
C6 C7 C8 C9 -176.3(5) . . . . ?
C6 C7 C8 C3 3.5(7) . . . . ?
C2 C3 C8 C9 -1.3(6) . . . . ?
C4 C3 C8 C9 177.3(4) . . . . ?
C2 C3 C8 C7 178.9(4) . . . . ?
C4 C3 C8 C7 -2.5(6) . . . . ?
C7 C8 C9 C10 -179.9(4) . . . . ?
C3 C8 C9 C10 0.3(7) . . . . ?
C8 C9 C10 C11 -178.5(4) . . . . ?
C8 C9 C10 C15 1.1(7) . . . . ?
C9 C10 C11 C12 -180.0(5) . . . . ?
C15 C10 C11 C12 0.4(7) . . . . ?
C10 C11 C12 C13 0.9(8) . . . . ?
C11 C12 C13 C14 -1.5(8) . . . . ?
C12 C13 C14 C15 0.8(8) . . . . ?
C13 C14 C15 C2 -178.6(4) . . . . ?
C13 C14 C15 C10 0.5(7) . . . . ?
C3 C2 C15 C14 179.6(4) . . . . ?
C1 C2 C15 C14 0.0(6) . . . . ?
C3 C2 C15 C10 0.5(6) . . . . ?
C1 C2 C15 C10 -179.1(4) . . . . ?
C9 C10 C15 C14 179.3(4) . . . . ?
C11 C10 C15 C14 -1.0(6) . . . . ?
C9 C10 C15 C2 -1.5(7) . . . . ?
C11 C10 C15 C2 178.1(4) . . . . ?
P1 O2 C16 C17 163.4(4) . . . . ?
C22 N1 C18 C19 -2.0(7) . . . . ?
Cu1 N1 C18 C19 176.4(4) . . . . ?
N1 C18 C19 C20 1.6(8) . . . . ?
C18 C19 C20 C21 -0.3(8) . . . . ?
C19 C20 C21 C22 -0.6(8) . . . . ?
C18 N1 C22 C21 1.1(7) . . . . ?
Cu1 N1 C22 C21 -177.5(4) . . . . ?
C18 N1 C22 C23 -178.7(4) . . . . ?
Cu1 N1 C22 C23 2.8(5) . . . . ?
C20 C21 C22 N1 0.2(8) . . . . ?
C20 C21 C22 C23 179.9(5) . . . . ?
C27 N2 C23 C24 -0.2(7) . . . . ?
Cu1 N2 C23 C24 177.5(4) . . . . ?
C27 N2 C23 C22 178.7(4) . . . . ?
Cu1 N2 C23 C22 -3.7(5) . . . . ?
N1 C22 C23 N2 0.6(6) . . . . ?
C21 C22 C23 N2 -179.1(4) . . . . ?
N1 C22 C23 C24 179.4(4) . . . . ?
C21 C22 C23 C24 -0.3(8) . . . . ?
N2 C23 C24 C25 0.8(7) . . . . ?
C22 C23 C24 C25 -178.0(5) . . . . ?
C23 C24 C25 C26 -1.2(8) . . . . ?
C24 C25 C26 C27 1.0(8) . . . . ?
C23 N2 C27 C26 0.0(7) . . . . ?
Cu1 N2 C27 C26 -177.4(4) . . . . ?
C25 C26 C27 N2 -0.4(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_complex_2
_database_code_depnum_ccdc_archive 'CCDC 1042813'
_audit_update_record             
;
2015-10-27 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H48 Cu2 N6 O12 P2, 2(C H4 O)'
_chemical_formula_sum            'C56 H56 Cu2 N6 O14 P2'
_chemical_formula_weight         1226.11

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'
P P 0.1023 0.0942 '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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.129(3)
_cell_length_b                   14.638(4)
_cell_length_c                   16.334(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.251(10)
_cell_angle_gamma                90.00
_cell_volume                     2660.8(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    142
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.62

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1268
_exptl_absorpt_coefficient_mu    0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41474
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         28.62
_reflns_number_total             6702
_reflns_number_gt                4775
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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)+(0.0369P)²+2.0508P] 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         6702
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 -0.01104(2) 0.371277(17) 0.103270(17) 0.01672(9) Uani 1 1 d . . 1
P1 P 0.17269(5) 0.51824(4) 0.02066(4) 0.01701(14) Uani 1 1 d . A 1
O1 O 0.07622(14) 0.48334(10) 0.07638(10) 0.0192(3) Uani 1 1 d . A 1
O2 O 0.28886(14) 0.54236(10) 0.07317(10) 0.0214(4) Uani 1 1 d . A 1
O3 O 0.14066(14) 0.60205(10) -0.02799(10) 0.0197(3) Uani 1 1 d . . 1
O4 O -0.10448(15) 0.44869(11) 0.20643(11) 0.0269(4) Uani 1 1 d . B 1
O5 O -0.2576(3) 0.48264(16) 0.2758(2) 0.1136(15) Uani 1 1 d . B 1
O6 O -0.22861(17) 0.34272(12) 0.24557(12) 0.0339(4) Uani 1 1 d . B 1
O7 O 0.51958(19) 0.45495(15) 0.34317(14) 0.0480(6) Uani 1 1 d . C 1
H7A H 0.5812 0.4611 0.3164 0.072 Uiso 1 1 calc R C 1
N1 N -0.06960(17) 0.24343(12) 0.11674(11) 0.0179(4) Uani 1 1 d . D 1
N2 N 0.11730(17) 0.32512(13) 0.17755(12) 0.0193(4) Uani 1 1 d . D 1
N3 N -0.1977(2) 0.42311(13) 0.24218(13) 0.0274(5) Uani 1 1 d . B 1
C1 C 0.2295(2) 0.43208(14) -0.04765(14) 0.0198(5) Uani 1 1 d . A 1
H1A H 0.1767 0.4298 -0.0950 0.024 Uiso 1 1 calc R A 1
H1B H 0.3076 0.4522 -0.0668 0.024 Uiso 1 1 calc R A 1
C2 C 0.2434(2) 0.33540(15) -0.01532(14) 0.0193(5) Uani 1 1 d . A 1
C3 C 0.1546(2) 0.26953(14) -0.03381(14) 0.0190(5) Uani 1 1 d . A 1
C4 C 0.0500(2) 0.28744(16) -0.08306(15) 0.0223(5) Uani 1 1 d . A 1
H4 H 0.0352 0.3469 -0.1006 0.027 Uiso 1 1 calc R A 1
C5 C -0.0282(2) 0.21993(16) -0.10491(15) 0.0244(5) Uani 1 1 d . A 1
H5 H -0.0936 0.2335 -0.1384 0.029 Uiso 1 1 calc R A 1
C6 C -0.0106(2) 0.12925(16) -0.07713(16) 0.0259(5) Uani 1 1 d . A 1
H6 H -0.0636 0.0833 -0.0930 0.031 Uiso 1 1 calc R A 1
C7 C 0.0837(2) 0.10955(15) -0.02728(16) 0.0257(6) Uani 1 1 d . A 1
H7 H 0.0926 0.0504 -0.0074 0.031 Uiso 1 1 calc R A 1
C8 C 0.1698(2) 0.17746(15) -0.00457(14) 0.0208(5) Uani 1 1 d . A 1
C9 C 0.2682(2) 0.15559(15) 0.04408(15) 0.0227(5) Uani 1 1 d . A 1
H9 H 0.2756 0.0965 0.0645 0.027 Uiso 1 1 calc R A 1
C10 C 0.3562(2) 0.22000(15) 0.06313(15) 0.0210(5) Uani 1 1 d . A 1
C11 C 0.4565(2) 0.19722(17) 0.11332(15) 0.0267(6) Uani 1 1 d . A 1
H11 H 0.4630 0.1384 0.1343 0.032 Uiso 1 1 calc R A 1
C12 C 0.5427(2) 0.25957(17) 0.13113(16) 0.0276(6) Uani 1 1 d . A 1
H12 H 0.6066 0.2437 0.1652 0.033 Uiso 1 1 calc R A 1
C13 C 0.5357(2) 0.34860(18) 0.09814(17) 0.0299(6) Uani 1 1 d . A 1
H13 H 0.5961 0.3908 0.1095 0.036 Uiso 1 1 calc R A 1
C14 C 0.4410(2) 0.37298(16) 0.04972(16) 0.0249(5) Uani 1 1 d . A 1
H14 H 0.4388 0.4317 0.0279 0.030 Uiso 1 1 calc R A 1
C15 C 0.3454(2) 0.31146(15) 0.03135(14) 0.0199(5) Uani 1 1 d . A 1
C16 C 0.2920(2) 0.62240(17) 0.12479(16) 0.0293(6) Uani 1 1 d . A 1
H16A H 0.2262 0.6209 0.1635 0.035 Uiso 1 1 calc R A 1
H16B H 0.2845 0.6772 0.0918 0.035 Uiso 1 1 calc R A 1
C17 C 0.4099(3) 0.6222(2) 0.1694(2) 0.0515(9) Uani 1 1 d . A 1
H17A H 0.4141 0.5699 0.2047 0.077 Uiso 1 1 calc R A 1
H17B H 0.4170 0.6769 0.2015 0.077 Uiso 1 1 calc R A 1
H17C H 0.4744 0.6197 0.1306 0.077 Uiso 1 1 calc R A 1
C18 C -0.1708(2) 0.20944(15) 0.08500(15) 0.0217(5) Uani 1 1 d . D 1
H18 H -0.2165 0.2457 0.0500 0.026 Uiso 1 1 calc R D 1
C19 C -0.2100(2) 0.12155(15) 0.10269(16) 0.0262(6) Uani 1 1 d . D 1
H19 H -0.2808 0.0990 0.0799 0.031 Uiso 1 1 calc R D 1
C20 C -0.1414(2) 0.06861(15) 0.15487(15) 0.0270(6) Uani 1 1 d . D 1
H20 H -0.1662 0.0098 0.1681 0.032 Uiso 1 1 calc R D 1
C21 C -0.0362(2) 0.10296(16) 0.18736(15) 0.0252(6) Uani 1 1 d . D 1
H21 H 0.0110 0.0674 0.2221 0.030 Uiso 1 1 calc R D 1
C22 C -0.0018(2) 0.19130(15) 0.16752(14) 0.0193(5) Uani 1 1 d . D 1
C23 C 0.1068(2) 0.23670(15) 0.19903(14) 0.0205(5) Uani 1 1 d . D 1
C24 C 0.1929(2) 0.19474(17) 0.24795(15) 0.0266(6) Uani 1 1 d . D 1
H24 H 0.1862 0.1331 0.2609 0.032 Uiso 1 1 calc R D 1
C25 C 0.2883(2) 0.24522(19) 0.27709(15) 0.0288(6) Uani 1 1 d . D 1
H25 H 0.3463 0.2180 0.3103 0.035 Uiso 1 1 calc R D 1
C26 C 0.2974(2) 0.33661(18) 0.25665(15) 0.0270(6) Uani 1 1 d . D 1
H26 H 0.3603 0.3722 0.2765 0.032 Uiso 1 1 calc R D 1
C27 C 0.2110(2) 0.37360(17) 0.20625(15) 0.0232(5) Uani 1 1 d . D 1
H27 H 0.2176 0.4347 0.1914 0.028 Uiso 1 1 calc R D 1
C28 C 0.5424(4) 0.3991(3) 0.4100(2) 0.0821(14) Uani 1 1 d . C 1
H28A H 0.6038 0.4262 0.4436 0.123 Uiso 1 1 calc R C 1
H28B H 0.5689 0.3403 0.3913 0.123 Uiso 1 1 calc R C 1
H28C H 0.4703 0.3921 0.4415 0.123 Uiso 1 1 calc R C 1


_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 O3 1.9312(16) 3_565 ?
Cu1 O1 1.9571(15) . ?
Cu1 N2 1.9882(19) . ?
Cu1 N1 1.9941(18) . ?
Cu1 O4 2.2848(17) . ?
P1 O1 1.5001(17) . ?
P1 O3 1.5037(16) . ?
P1 O2 1.5880(17) . ?
P1 C1 1.801(2) . ?
O2 C16 1.444(3) . ?
O3 Cu1 1.9313(16) 3_565 ?
O4 N3 1.250(3) . ?
O5 N3 1.228(3) . ?
O6 N3 1.227(3) . ?
O7 C28 1.387(4) . ?
O7 H7A 0.8200 . ?
N1 C18 1.334(3) . ?
N1 C22 1.354(3) . ?
N2 C27 1.344(3) . ?
N2 C23 1.346(3) . ?
C1 C2 1.518(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C15 1.408(3) . ?
C2 C3 1.412(3) . ?
C3 C4 1.436(3) . ?
C3 C8 1.440(3) . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.357(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.428(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C9 C10 1.393(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.422(3) . ?
C10 C15 1.441(3) . ?
C11 C12 1.355(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.412(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.425(3) . ?
C14 H14 0.9300 . ?
C16 C17 1.498(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.470(3) . ?
C23 C24 1.388(3) . ?
C24 C25 1.377(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.374(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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
O3 Cu1 O1 93.30(6) 3_565 . ?
O3 Cu1 N2 171.80(7) 3_565 . ?
O1 Cu1 N2 93.78(7) . . ?
O3 Cu1 N1 90.94(7) 3_565 . ?
O1 Cu1 N1 166.91(7) . . ?
N2 Cu1 N1 81.26(8) . . ?
O3 Cu1 O4 91.62(7) 3_565 . ?
O1 Cu1 O4 88.73(6) . . ?
N2 Cu1 O4 92.66(7) . . ?
N1 Cu1 O4 103.53(7) . . ?
O1 P1 O3 115.47(9) . . ?
O1 P1 O2 109.34(9) . . ?
O3 P1 O2 107.14(9) . . ?
O1 P1 C1 113.06(10) . . ?
O3 P1 C1 109.09(10) . . ?
O2 P1 C1 101.71(10) . . ?
P1 O1 Cu1 141.15(10) . . ?
C16 O2 P1 120.90(15) . . ?
P1 O3 Cu1 132.54(9) . 3_565 ?
N3 O4 Cu1 125.26(14) . . ?
C18 N1 C22 119.67(19) . . ?
C18 N1 Cu1 125.66(15) . . ?
C22 N1 Cu1 114.51(15) . . ?
C27 N2 C23 119.0(2) . . ?
C27 N2 Cu1 125.98(16) . . ?
C23 N2 Cu1 115.00(16) . . ?
O6 N3 O5 120.5(2) . . ?
O6 N3 O4 122.8(2) . . ?
O5 N3 O4 116.7(2) . . ?
C2 C1 P1 118.22(17) . . ?
C2 C1 H1A 107.8 . . ?
P1 C1 H1A 107.8 . . ?
C2 C1 H1B 107.8 . . ?
P1 C1 H1B 107.8 . . ?
H1A C1 H1B 107.1 . . ?
C15 C2 C3 120.5(2) . . ?
C15 C2 C1 120.0(2) . . ?
C3 C2 C1 119.5(2) . . ?
C2 C3 C4 124.0(2) . . ?
C2 C3 C8 119.2(2) . . ?
C4 C3 C8 116.8(2) . . ?
C5 C4 C3 121.9(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 121.6(2) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 C3 119.8(2) . . ?
C7 C8 C3 119.2(2) . . ?
C8 C9 C10 121.6(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 C15 119.4(2) . . ?
C11 C10 C15 119.3(2) . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 122.1(2) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C2 C15 C14 123.8(2) . . ?
C2 C15 C10 119.5(2) . . ?
C14 C15 C10 116.8(2) . . ?
O2 C16 C17 107.5(2) . . ?
O2 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
O2 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
N1 C18 C19 122.0(2) . . ?
N1 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C20 C19 C18 118.4(2) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.0(2) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
N1 C22 C21 121.0(2) . . ?
N1 C22 C23 114.49(19) . . ?
C21 C22 C23 124.5(2) . . ?
N2 C23 C24 121.0(2) . . ?
N2 C23 C22 114.6(2) . . ?
C24 C23 C22 124.4(2) . . ?
C25 C24 C23 119.4(2) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 119.5(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 118.3(2) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
N2 C27 C26 122.7(2) . . ?
N2 C27 H27 118.6 . . ?
C26 C27 H27 118.6 . . ?

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
O3 P1 O1 Cu1 128.28(15) . . . . ?
O2 P1 O1 Cu1 -110.86(15) . . . . ?
C1 P1 O1 Cu1 1.7(2) . . . . ?
O3 Cu1 O1 P1 -93.16(16) 3_565 . . . ?
N2 Cu1 O1 P1 82.71(16) . . . . ?
N1 Cu1 O1 P1 15.6(4) . . . . ?
O4 Cu1 O1 P1 175.29(16) . . . . ?
O1 P1 O2 C16 -73.34(19) . . . . ?
O3 P1 O2 C16 52.5(2) . . . . ?
C1 P1 O2 C16 166.88(18) . . . . ?
O1 P1 O3 Cu1 -56.20(16) . . . 3_565 ?
O2 P1 O3 Cu1 -178.24(12) . . . 3_565 ?
C1 P1 O3 Cu1 72.40(16) . . . 3_565 ?
O3 Cu1 O4 N3 70.13(19) 3_565 . . . ?
O1 Cu1 O4 N3 163.40(19) . . . . ?
N2 Cu1 O4 N3 -102.87(19) . . . . ?
N1 Cu1 O4 N3 -21.2(2) . . . . ?
O3 Cu1 N1 C18 -5.59(19) 3_565 . . . ?
O1 Cu1 N1 C18 -114.6(3) . . . . ?
N2 Cu1 N1 C18 177.0(2) . . . . ?
O4 Cu1 N1 C18 86.30(19) . . . . ?
O3 Cu1 N1 C22 179.09(16) 3_565 . . . ?
O1 Cu1 N1 C22 70.1(4) . . . . ?
N2 Cu1 N1 C22 1.63(15) . . . . ?
O4 Cu1 N1 C22 -89.02(16) . . . . ?
O1 Cu1 N2 C27 12.61(19) . . . . ?
N1 Cu1 N2 C27 -179.6(2) . . . . ?
O4 Cu1 N2 C27 -76.29(19) . . . . ?
O1 Cu1 N2 C23 -166.74(16) . . . . ?
N1 Cu1 N2 C23 1.07(16) . . . . ?
O4 Cu1 N2 C23 104.36(16) . . . . ?
Cu1 O4 N3 O6 24.1(3) . . . . ?
Cu1 O4 N3 O5 -157.1(3) . . . . ?
O1 P1 C1 C2 -37.7(2) . . . . ?
O3 P1 C1 C2 -167.59(17) . . . . ?
O2 P1 C1 C2 79.45(19) . . . . ?
P1 C1 C2 C15 -81.4(3) . . . . ?
P1 C1 C2 C3 99.8(2) . . . . ?
C15 C2 C3 C4 -178.0(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C15 C2 C3 C8 -0.2(3) . . . . ?
C1 C2 C3 C8 178.6(2) . . . . ?
C2 C3 C4 C5 174.5(2) . . . . ?
C8 C3 C4 C5 -3.4(3) . . . . ?
C3 C4 C5 C6 2.1(4) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
C5 C6 C7 C8 -2.8(4) . . . . ?
C6 C7 C8 C9 -177.7(2) . . . . ?
C6 C7 C8 C3 1.4(4) . . . . ?
C2 C3 C8 C9 2.8(3) . . . . ?
C4 C3 C8 C9 -179.3(2) . . . . ?
C2 C3 C8 C7 -176.3(2) . . . . ?
C4 C3 C8 C7 1.6(3) . . . . ?
C7 C8 C9 C10 176.6(2) . . . . ?
C3 C8 C9 C10 -2.5(3) . . . . ?
C8 C9 C10 C11 179.7(2) . . . . ?
C8 C9 C10 C15 -0.3(4) . . . . ?
C9 C10 C11 C12 179.3(2) . . . . ?
C15 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 -1.5(4) . . . . ?
C11 C12 C13 C14 1.5(4) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C3 C2 C15 C14 177.4(2) . . . . ?
C1 C2 C15 C14 -1.4(3) . . . . ?
C3 C2 C15 C10 -2.6(3) . . . . ?
C1 C2 C15 C10 178.7(2) . . . . ?
C13 C14 C15 C2 177.0(2) . . . . ?
C13 C14 C15 C10 -3.1(4) . . . . ?
C9 C10 C15 C2 2.9(3) . . . . ?
C11 C10 C15 C2 -177.2(2) . . . . ?
C9 C10 C15 C14 -177.1(2) . . . . ?
C11 C10 C15 C14 2.9(3) . . . . ?
P1 O2 C16 C17 176.53(19) . . . . ?
C22 N1 C18 C19 0.3(3) . . . . ?
Cu1 N1 C18 C19 -174.75(17) . . . . ?
N1 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C18 N1 C22 C21 -0.2(3) . . . . ?
Cu1 N1 C22 C21 175.38(17) . . . . ?
C18 N1 C22 C23 -179.5(2) . . . . ?
Cu1 N1 C22 C23 -3.8(2) . . . . ?
C20 C21 C22 N1 -0.3(3) . . . . ?
C20 C21 C22 C23 178.8(2) . . . . ?
C27 N2 C23 C24 -2.0(3) . . . . ?
Cu1 N2 C23 C24 177.38(17) . . . . ?
C27 N2 C23 C22 177.2(2) . . . . ?
Cu1 N2 C23 C22 -3.4(2) . . . . ?
N1 C22 C23 N2 4.8(3) . . . . ?
C21 C22 C23 N2 -174.4(2) . . . . ?
N1 C22 C23 C24 -176.0(2) . . . . ?
C21 C22 C23 C24 4.8(4) . . . . ?
N2 C23 C24 C25 2.2(4) . . . . ?
C22 C23 C24 C25 -177.0(2) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 C27 -1.2(4) . . . . ?
C23 N2 C27 C26 0.3(3) . . . . ?
Cu1 N2 C27 C26 -179.07(18) . . . . ?
C25 C26 C27 N2 1.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        28.62
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_complex_3
_database_code_depnum_ccdc_archive 'CCDC 1042814'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H32 Cu N4 O3 P, N O3, H2 O, H2 O'
_chemical_formula_sum            'C37 H36 Cu N5 O8 P'
_chemical_formula_weight         773.21

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'
P P 0.1023 0.0942 '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                   11.461(3)
_cell_length_b                   12.537(3)
_cell_length_c                   14.271(3)
_cell_angle_alpha                111.461(11)
_cell_angle_beta                 111.204(12)
_cell_angle_gamma                92.332(13)
_cell_volume                     1743.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    134
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      26.54

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             798.0
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            26914
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         26.54
_reflns_number_total             7155
_reflns_number_gt                4868
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_refine_special_details          
; 
The following constraint was employed to make the thermal ellipsoid in nitrate 
correct

EADP O5 N5

 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)+(0.0464P)²+0.3202P] 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         7155
_refine_ls_number_parameters     472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_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 0.38754(3) 0.65753(3) 0.17961(2) 0.03591(12) Uani 1 1 d . A 4
P1 P 0.28196(7) 0.46309(6) 0.23681(6) 0.03562(18) Uani 1 1 d . A 4
N1 N 0.5150(2) 0.73423(18) 0.14077(17) 0.0336(5) Uani 1 1 d . A 4
N2 N 0.3234(2) 0.55789(18) 0.02016(16) 0.0336(5) Uani 1 1 d . A 4
N3 N 0.2313(2) 0.74150(19) 0.17878(17) 0.0358(5) Uani 1 1 d . A 4
N4 N 0.4504(2) 0.76382(19) 0.33839(17) 0.0348(5) Uani 1 1 d . A 4
N5 N 0.9427(3) 0.8214(3) 0.5971(3) 0.0776(6) Uani 1 1 d . B 4
O1 O 0.16734(19) 0.38661(17) 0.13947(15) 0.0480(5) Uani 1 1 d . A 4
O2 O 0.38472(17) 0.51886(15) 0.21645(14) 0.0379(4) Uani 1 1 d . A 4
O3 O 0.24431(18) 0.56976(16) 0.31699(15) 0.0419(5) Uani 1 1 d . A 4
O4 O 0.9068(3) 0.7654(3) 0.6401(2) 0.0961(9) Uani 1 1 d . B 4
O5 O 1.0399(2) 0.8962(2) 0.6471(2) 0.0776(6) Uani 1 1 d . B 4
O6 O 0.8771(3) 0.7982(2) 0.4973(2) 0.0908(8) Uani 1 1 d . B 4
O7 O 0.1685(3) 0.0046(4) 0.5539(2) 0.0746(8) Uani 1 1 d . C 4
H7W H 0.136(4) 0.065(4) 0.550(3) 0.093(17) Uiso 1 1 d . D 4
H8W H 0.116(4) -0.024(4) 0.565(4) 0.096(19) Uiso 1 1 d . E 4
O8 O 0.9664(3) 0.2603(3) 0.1492(2) 0.1003(10) Uani 1 1 d . F 4
C1 C 0.3568(3) 0.3856(2) 0.3207(2) 0.0414(7) Uani 1 1 d . A 4
H1A H 0.4106 0.4425 0.3944 0.050 Uiso 1 1 calc R A 4
H1B H 0.2906 0.3404 0.3262 0.050 Uiso 1 1 calc R A 4
C2 C 0.4370(3) 0.3039(2) 0.2773(2) 0.0370(6) Uani 1 1 d . A 4
C3 C 0.3811(3) 0.1871(2) 0.2016(2) 0.0386(7) Uani 1 1 d . A 4
C4 C 0.2487(3) 0.1389(3) 0.1602(3) 0.0525(8) Uani 1 1 d . A 4
H4 H 0.1956 0.1851 0.1851 0.063 Uiso 1 1 calc R A 4
C5 C 0.1987(3) 0.0265(3) 0.0848(3) 0.0667(10) Uani 1 1 d . A 4
H5 H 0.1118 -0.0024 0.0586 0.080 Uiso 1 1 calc R A 4
C6 C 0.2753(4) -0.0473(3) 0.0454(3) 0.0640(10) Uani 1 1 d . A 4
H6 H 0.2391 -0.1238 -0.0062 0.077 Uiso 1 1 calc R A 4
C7 C 0.4000(3) -0.0068(3) 0.0824(2) 0.0531(8) Uani 1 1 d . A 4
H7 H 0.4502 -0.0561 0.0565 0.064 Uiso 1 1 calc R A 4
C8 C 0.4581(3) 0.1102(2) 0.1608(2) 0.0395(7) Uani 1 1 d . A 4
C9 C 0.5869(3) 0.1529(3) 0.1965(2) 0.0454(7) Uani 1 1 d . A 4
H9 H 0.6365 0.1031 0.1704 0.054 Uiso 1 1 calc R A 4
C10 C 0.6439(3) 0.2672(3) 0.2698(2) 0.0424(7) Uani 1 1 d . A 4
C11 C 0.7761(3) 0.3099(3) 0.3029(3) 0.0550(8) Uani 1 1 d . A 4
H11 H 0.8248 0.2599 0.2755 0.066 Uiso 1 1 calc R A 4
C12 C 0.8311(3) 0.4215(3) 0.3731(3) 0.0652(10) Uani 1 1 d . A 4
H12 H 0.9173 0.4481 0.3938 0.078 Uiso 1 1 calc R A 4
C13 C 0.7588(3) 0.4983(3) 0.4155(3) 0.0611(10) Uani 1 1 d . A 4
H13 H 0.7981 0.5753 0.4644 0.073 Uiso 1 1 calc R A 4
C14 C 0.6329(3) 0.4619(3) 0.3862(2) 0.0490(8) Uani 1 1 d . A 4
H14 H 0.5873 0.5147 0.4152 0.059 Uiso 1 1 calc R A 4
C15 C 0.5685(3) 0.3448(2) 0.3119(2) 0.0385(7) Uani 1 1 d . A 4
C16 C 0.1292(3) 0.5520(3) 0.3340(3) 0.0510(8) Uani 1 1 d . A 4
H16A H 0.1344 0.4961 0.3669 0.061 Uiso 1 1 calc R A 4
H16B H 0.0558 0.5208 0.2638 0.061 Uiso 1 1 calc R A 4
C17 C 0.1142(3) 0.6655(3) 0.4077(3) 0.0584(9) Uani 1 1 d . A 4
H17A H 0.1885 0.6973 0.4760 0.088 Uiso 1 1 calc R A 4
H17B H 0.0400 0.6532 0.4217 0.088 Uiso 1 1 calc R A 4
H17C H 0.1045 0.7192 0.3729 0.088 Uiso 1 1 calc R A 4
C18 C 0.6117(3) 0.8256(2) 0.2077(2) 0.0409(7) Uani 1 1 d . A 4
H18 H 0.6251 0.8619 0.2815 0.049 Uiso 1 1 calc R A 4
C19 C 0.6927(3) 0.8686(3) 0.1723(2) 0.0442(7) Uani 1 1 d . A 4
H19 H 0.7587 0.9328 0.2212 0.053 Uiso 1 1 calc R A 4
C20 C 0.6744(3) 0.8153(3) 0.0643(2) 0.0441(7) Uani 1 1 d . A 4
H20 H 0.7280 0.8425 0.0388 0.053 Uiso 1 1 calc R A 4
C21 C 0.5759(3) 0.7209(2) -0.0059(2) 0.0409(7) Uani 1 1 d . A 4
H21 H 0.5621 0.6836 -0.0796 0.049 Uiso 1 1 calc R A 4
C22 C 0.4972(2) 0.6820(2) 0.0341(2) 0.0320(6) Uani 1 1 d . A 4
C23 C 0.3878(2) 0.5821(2) -0.0345(2) 0.0311(6) Uani 1 1 d . A 4
C24 C 0.3531(3) 0.5163(2) -0.1454(2) 0.0419(7) Uani 1 1 d . A 4
H24 H 0.3995 0.5329 -0.1817 0.050 Uiso 1 1 calc R A 4
C25 C 0.2492(3) 0.4262(2) -0.2012(2) 0.0451(7) Uani 1 1 d . A 4
H25 H 0.2238 0.3815 -0.2761 0.054 Uiso 1 1 calc R A 4
C26 C 0.1826(3) 0.4023(2) -0.1456(2) 0.0439(7) Uani 1 1 d . A 4
H26 H 0.1113 0.3418 -0.1825 0.053 Uiso 1 1 calc R A 4
C27 C 0.2229(3) 0.4688(2) -0.0350(2) 0.0423(7) Uani 1 1 d . A 4
H27 H 0.1790 0.4515 0.0029 0.051 Uiso 1 1 calc R A 4
C28 C 0.1246(3) 0.7308(3) 0.0939(2) 0.0423(7) Uani 1 1 d . A 4
H28 H 0.1110 0.6758 0.0244 0.051 Uiso 1 1 calc R A 4
C29 C 0.0338(3) 0.7967(3) 0.1039(2) 0.0465(7) Uani 1 1 d . A 4
H29 H -0.0400 0.7855 0.0427 0.056 Uiso 1 1 calc R A 4
C30 C 0.0537(3) 0.8799(3) 0.2062(3) 0.0500(8) Uani 1 1 d . A 4
H30 H -0.0055 0.9270 0.2149 0.060 Uiso 1 1 calc R A 4
C31 C 0.1629(3) 0.8921(3) 0.2953(2) 0.0444(7) Uani 1 1 d . A 4
H31 H 0.1782 0.9475 0.3652 0.053 Uiso 1 1 calc R A 4
C32 C 0.2496(2) 0.8210(2) 0.2797(2) 0.0346(6) Uani 1 1 d . A 4
C33 C 0.3671(3) 0.8245(2) 0.3700(2) 0.0337(6) Uani 1 1 d . A 4
C34 C 0.3905(3) 0.8815(2) 0.4803(2) 0.0432(7) Uani 1 1 d . A 4
H34 H 0.3316 0.9221 0.5013 0.052 Uiso 1 1 calc R A 4
C35 C 0.5015(3) 0.8775(3) 0.5585(2) 0.0490(8) Uani 1 1 d . A 4
H35 H 0.5185 0.9151 0.6329 0.059 Uiso 1 1 calc R A 4
C36 C 0.5874(3) 0.8174(3) 0.5258(2) 0.0475(8) Uani 1 1 d . A 4
H36 H 0.6636 0.8146 0.5776 0.057 Uiso 1 1 calc R A 4
C37 C 0.5587(3) 0.7617(3) 0.4154(2) 0.0436(7) Uani 1 1 d . A 4
H37 H 0.6167 0.7209 0.3933 0.052 Uiso 1 1 calc R A 4


_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 N2 1.979(2) . ?
Cu1 N4 1.990(2) . ?
Cu1 O2 1.9941(18) . ?
Cu1 N1 2.056(2) . ?
Cu1 N3 2.112(2) . ?
P1 O1 1.476(2) . ?
P1 O2 1.5131(18) . ?
P1 O3 1.6027(19) . ?
P1 C1 1.814(3) . ?
N1 C18 1.335(3) . ?
N1 C22 1.350(3) . ?
N2 C27 1.339(3) . ?
N2 C23 1.348(3) . ?
N3 C28 1.333(3) . ?
N3 C32 1.351(3) . ?
N4 C37 1.337(3) . ?
N4 C33 1.346(3) . ?
N5 O5 1.216(4) . ?
N5 O4 1.229(4) . ?
N5 O6 1.259(4) . ?
O3 C16 1.447(3) . ?
O7 H7W 0.86(4) . ?
O7 H8W 0.79(4) . ?
C1 C2 1.517(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.411(4) . ?
C2 C15 1.411(4) . ?
C3 C4 1.425(4) . ?
C3 C8 1.441(4) . ?
C4 C5 1.361(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.333(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.424(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(4) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.427(4) . ?
C10 C15 1.439(4) . ?
C11 C12 1.343(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.408(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.355(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.425(4) . ?
C14 H14 0.9300 . ?
C16 C17 1.489(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.478(4) . ?
C23 C24 1.381(3) . ?
C24 C25 1.368(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.370(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.370(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.377(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.378(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.385(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.476(4) . ?
C33 C34 1.385(3) . ?
C34 C35 1.373(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.374(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.370(4) . ?
C36 H36 0.9300 . ?
C37 H37 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
N2 Cu1 N4 177.47(9) . . ?
N2 Cu1 O2 92.16(8) . . ?
N4 Cu1 O2 90.31(8) . . ?
N2 Cu1 N1 80.21(9) . . ?
N4 Cu1 N1 98.56(9) . . ?
O2 Cu1 N1 131.70(8) . . ?
N2 Cu1 N3 98.78(9) . . ?
N4 Cu1 N3 79.65(9) . . ?
O2 Cu1 N3 114.90(8) . . ?
N1 Cu1 N3 113.39(9) . . ?
O1 P1 O2 117.28(11) . . ?
O1 P1 O3 110.87(12) . . ?
O2 P1 O3 105.32(10) . . ?
O1 P1 C1 110.81(13) . . ?
O2 P1 C1 107.50(12) . . ?
O3 P1 C1 104.13(11) . . ?
C18 N1 C22 117.9(2) . . ?
C18 N1 Cu1 128.06(18) . . ?
C22 N1 Cu1 113.98(17) . . ?
C27 N2 C23 119.0(2) . . ?
C27 N2 Cu1 124.34(17) . . ?
C23 N2 Cu1 116.66(17) . . ?
C28 N3 C32 117.8(2) . . ?
C28 N3 Cu1 129.29(19) . . ?
C32 N3 Cu1 112.78(17) . . ?
C37 N4 C33 119.0(2) . . ?
C37 N4 Cu1 123.45(19) . . ?
C33 N4 Cu1 116.41(17) . . ?
O5 N5 O4 122.3(4) . . ?
O5 N5 O6 119.4(4) . . ?
O4 N5 O6 118.2(3) . . ?
P1 O2 Cu1 128.27(11) . . ?
C16 O3 P1 120.43(17) . . ?
H7W O7 H8W 97(4) . . ?
C2 C1 P1 114.36(17) . . ?
C2 C1 H1A 108.7 . . ?
P1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
P1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C15 119.4(3) . . ?
C3 C2 C1 120.5(3) . . ?
C15 C2 C1 120.1(2) . . ?
C2 C3 C4 123.3(3) . . ?
C2 C3 C8 120.1(3) . . ?
C4 C3 C8 116.6(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 C3 119.2(3) . . ?
C7 C8 C3 119.6(3) . . ?
C10 C9 C8 122.0(3) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 C15 119.6(3) . . ?
C11 C10 C15 119.5(3) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.6(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C2 C15 C14 123.5(3) . . ?
C2 C15 C10 119.8(2) . . ?
C14 C15 C10 116.7(3) . . ?
O3 C16 C17 109.4(2) . . ?
O3 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
O3 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
N1 C18 C19 122.9(3) . . ?
N1 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 119.2(3) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
N1 C22 C21 121.7(2) . . ?
N1 C22 C23 114.5(2) . . ?
C21 C22 C23 123.8(2) . . ?
N2 C23 C24 121.4(2) . . ?
N2 C23 C22 114.6(2) . . ?
C24 C23 C22 124.0(2) . . ?
C25 C24 C23 119.0(3) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 119.5(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 119.0(3) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
N2 C27 C26 122.0(3) . . ?
N2 C27 H27 119.0 . . ?
C26 C27 H27 119.0 . . ?
N3 C28 C29 123.4(3) . . ?
N3 C28 H28 118.3 . . ?
C29 C28 H28 118.3 . . ?
C28 C29 C30 118.9(3) . . ?
C28 C29 H29 120.6 . . ?
C30 C29 H29 120.6 . . ?
C29 C30 C31 118.8(3) . . ?
C29 C30 H30 120.6 . . ?
C31 C30 H30 120.6 . . ?
C30 C31 C32 119.3(3) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 H31 120.4 . . ?
N3 C32 C31 121.7(2) . . ?
N3 C32 C33 114.7(2) . . ?
C31 C32 C33 123.5(2) . . ?
N4 C33 C34 121.1(2) . . ?
N4 C33 C32 115.4(2) . . ?
C34 C33 C32 123.5(3) . . ?
C35 C34 C33 119.2(3) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 119.5(3) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C37 C36 C35 118.8(3) . . ?
C37 C36 H36 120.6 . . ?
C35 C36 H36 120.6 . . ?
N4 C37 C36 122.4(3) . . ?
N4 C37 H37 118.8 . . ?
C36 C37 H37 118.8 . . ?

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
N2 Cu1 N1 C18 179.8(2) . . . . ?
N4 Cu1 N1 C18 2.1(2) . . . . ?
O2 Cu1 N1 C18 -96.0(2) . . . . ?
N3 Cu1 N1 C18 84.5(2) . . . . ?
N2 Cu1 N1 C22 -1.53(17) . . . . ?
N4 Cu1 N1 C22 -179.29(17) . . . . ?
O2 Cu1 N1 C22 82.58(19) . . . . ?
N3 Cu1 N1 C22 -96.93(18) . . . . ?
O2 Cu1 N2 C27 48.3(2) . . . . ?
N1 Cu1 N2 C27 -179.7(2) . . . . ?
N3 Cu1 N2 C27 -67.3(2) . . . . ?
O2 Cu1 N2 C23 -130.78(18) . . . . ?
N1 Cu1 N2 C23 1.21(18) . . . . ?
N3 Cu1 N2 C23 113.61(18) . . . . ?
N2 Cu1 N3 C28 -1.7(2) . . . . ?
N4 Cu1 N3 C28 176.2(2) . . . . ?
O2 Cu1 N3 C28 -98.3(2) . . . . ?
N1 Cu1 N3 C28 81.3(2) . . . . ?
N2 Cu1 N3 C32 -177.89(17) . . . . ?
N4 Cu1 N3 C32 0.09(17) . . . . ?
O2 Cu1 N3 C32 85.58(18) . . . . ?
N1 Cu1 N3 C32 -94.83(18) . . . . ?
O2 Cu1 N4 C37 58.5(2) . . . . ?
N1 Cu1 N4 C37 -73.8(2) . . . . ?
N3 Cu1 N4 C37 173.8(2) . . . . ?
O2 Cu1 N4 C33 -109.08(18) . . . . ?
N1 Cu1 N4 C33 118.58(18) . . . . ?
N3 Cu1 N4 C33 6.21(18) . . . . ?
O1 P1 O2 Cu1 78.30(17) . . . . ?
O3 P1 O2 Cu1 -45.53(16) . . . . ?
C1 P1 O2 Cu1 -156.12(14) . . . . ?
N2 Cu1 O2 P1 -96.72(14) . . . . ?
N4 Cu1 O2 P1 82.72(14) . . . . ?
N1 Cu1 O2 P1 -175.51(11) . . . . ?
N3 Cu1 O2 P1 3.99(16) . . . . ?
O1 P1 O3 C16 38.0(2) . . . . ?
O2 P1 O3 C16 165.8(2) . . . . ?
C1 P1 O3 C16 -81.2(2) . . . . ?
O1 P1 C1 C2 78.7(2) . . . . ?
O2 P1 C1 C2 -50.6(2) . . . . ?
O3 P1 C1 C2 -162.0(2) . . . . ?
P1 C1 C2 C3 -88.3(3) . . . . ?
P1 C1 C2 C15 91.2(3) . . . . ?
C15 C2 C3 C4 -178.6(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C15 C2 C3 C8 0.5(4) . . . . ?
C1 C2 C3 C8 180.0(2) . . . . ?
C2 C3 C4 C5 178.1(3) . . . . ?
C8 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C8 -0.5(5) . . . . ?
C6 C7 C8 C9 -178.0(3) . . . . ?
C6 C7 C8 C3 0.1(5) . . . . ?
C2 C3 C8 C9 -0.4(4) . . . . ?
C4 C3 C8 C9 178.8(3) . . . . ?
C2 C3 C8 C7 -178.5(2) . . . . ?
C4 C3 C8 C7 0.6(4) . . . . ?
C7 C8 C9 C10 177.9(3) . . . . ?
C3 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 -178.2(3) . . . . ?
C8 C9 C10 C15 0.7(4) . . . . ?
C9 C10 C11 C12 179.2(3) . . . . ?
C15 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C3 C2 C15 C14 178.6(2) . . . . ?
C1 C2 C15 C14 -0.9(4) . . . . ?
C3 C2 C15 C10 0.0(4) . . . . ?
C1 C2 C15 C10 -179.5(2) . . . . ?
C13 C14 C15 C2 -178.6(3) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C9 C10 C15 C2 -0.6(4) . . . . ?
C11 C10 C15 C2 178.4(2) . . . . ?
C9 C10 C15 C14 -179.3(2) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
P1 O3 C16 C17 -177.5(2) . . . . ?
C22 N1 C18 C19 0.4(4) . . . . ?
Cu1 N1 C18 C19 179.0(2) . . . . ?
N1 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C18 N1 C22 C21 -0.1(4) . . . . ?
Cu1 N1 C22 C21 -178.9(2) . . . . ?
C18 N1 C22 C23 -179.6(2) . . . . ?
Cu1 N1 C22 C23 1.6(3) . . . . ?
C20 C21 C22 N1 -0.1(4) . . . . ?
C20 C21 C22 C23 179.4(2) . . . . ?
C27 N2 C23 C24 -0.7(4) . . . . ?
Cu1 N2 C23 C24 178.5(2) . . . . ?
C27 N2 C23 C22 -179.9(2) . . . . ?
Cu1 N2 C23 C22 -0.7(3) . . . . ?
N1 C22 C23 N2 -0.6(3) . . . . ?
C21 C22 C23 N2 179.8(2) . . . . ?
N1 C22 C23 C24 -179.8(2) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
N2 C23 C24 C25 1.5(4) . . . . ?
C22 C23 C24 C25 -179.5(3) . . . . ?
C23 C24 C25 C26 -0.7(4) . . . . ?
C24 C25 C26 C27 -0.6(4) . . . . ?
C23 N2 C27 C26 -0.7(4) . . . . ?
Cu1 N2 C27 C26 -179.8(2) . . . . ?
C25 C26 C27 N2 1.4(4) . . . . ?
C32 N3 C28 C29 0.6(4) . . . . ?
Cu1 N3 C28 C29 -175.4(2) . . . . ?
N3 C28 C29 C30 1.1(5) . . . . ?
C28 C29 C30 C31 -1.5(4) . . . . ?
C29 C30 C31 C32 0.3(4) . . . . ?
C28 N3 C32 C31 -1.8(4) . . . . ?
Cu1 N3 C32 C31 174.8(2) . . . . ?
C28 N3 C32 C33 177.6(2) . . . . ?
Cu1 N3 C32 C33 -5.7(3) . . . . ?
C30 C31 C32 N3 1.4(4) . . . . ?
C30 C31 C32 C33 -178.0(3) . . . . ?
C37 N4 C33 C34 -1.7(4) . . . . ?
Cu1 N4 C33 C34 166.4(2) . . . . ?
C37 N4 C33 C32 -179.3(2) . . . . ?
Cu1 N4 C33 C32 -11.2(3) . . . . ?
N3 C32 C33 N4 11.1(3) . . . . ?
C31 C32 C33 N4 -169.4(2) . . . . ?
N3 C32 C33 C34 -166.4(2) . . . . ?
C31 C32 C33 C34 13.1(4) . . . . ?
N4 C33 C34 C35 1.1(4) . . . . ?
C32 C33 C34 C35 178.5(3) . . . . ?
C33 C34 C35 C36 0.2(4) . . . . ?
C34 C35 C36 C37 -0.8(5) . . . . ?
C33 N4 C37 C36 1.1(4) . . . . ?
Cu1 N4 C37 C36 -166.2(2) . . . . ?
C35 C36 C37 N4 0.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_complex_4
_database_code_depnum_ccdc_archive 'CCDC 1042815'
_audit_update_record             
;
2015-11-06 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cu N5 O3, N O3, H2 O'
_chemical_formula_sum            'C20 H16 Cu N6 O7'
_chemical_formula_weight         517.94

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'
P P 0.1023 0.0942 '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                   7.2609(7)
_cell_length_b                   9.9595(10)
_cell_length_c                   15.0827(15)
_cell_angle_alpha                73.778(5)
_cell_angle_beta                 87.900(5)
_cell_angle_gamma                89.707(5)
_cell_volume                     1046.56(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    143
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      28.42

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             526
_exptl_absorpt_coefficient_mu    1.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            16682
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         28.42
_reflns_number_total             5124
_reflns_number_gt                4454
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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)+(0.1000P)²+0.9890P] 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         5124
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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 0.88814(4) 0.68864(3) 0.706197(18) 0.02065(12) Uani 1 1 d . A 4
O1 O 1.1575(3) 0.69516(17) 0.62491(12) 0.0248(4) Uani 1 1 d . A 4
O2 O 1.0559(3) 0.48933(19) 0.62799(14) 0.0321(4) Uani 1 1 d . A 4
O3 O 1.2982(3) 0.5764(2) 0.54202(13) 0.0276(4) Uani 1 1 d . A 4
O4 O 0.6025(4) 0.7675(3) 0.83948(19) 0.0535(7) Uani 1 1 d . B 4
O5 O 0.5876(5) 0.9022(3) 0.92828(19) 0.0638(8) Uani 1 1 d . B 4
O6 O 0.4198(7) 0.9447(4) 0.8137(3) 0.0986(15) Uani 1 1 d . B 4
O7 O 0.8317(4) 0.0278(4) 0.0364(2) 0.0806(11) Uani 1 1 d . C 4
N1 N 0.7802(3) 0.7716(2) 0.58457(13) 0.0201(4) Uani 1 1 d . A 4
N2 N 0.9104(3) 0.8961(2) 0.70195(13) 0.0197(4) Uani 1 1 d . A 4
N3 N 0.7149(3) 0.5243(2) 0.75521(13) 0.0202(4) Uani 1 1 d . A 4
N4 N 1.0231(3) 0.5884(2) 0.81759(14) 0.0215(4) Uani 1 1 d . A 4
N5 N 1.1707(3) 0.5854(2) 0.59739(14) 0.0203(4) Uani 1 1 d . A 4
N6 N 0.5384(4) 0.8717(3) 0.85760(18) 0.0375(6) Uani 1 1 d . B 4
C1 C 0.7313(3) 0.6994(3) 0.52603(16) 0.0232(5) Uani 1 1 d . A 4
H1 H 0.7373 0.6023 0.5449 0.028 Uiso 1 1 calc R A 4
C2 C 0.6723(3) 0.7657(3) 0.43830(17) 0.0248(5) Uani 1 1 d . A 4
H2 H 0.6375 0.7136 0.3992 0.030 Uiso 1 1 calc R A 4
C3 C 0.6659(3) 0.9102(3) 0.40957(16) 0.0237(5) Uani 1 1 d . A 4
H3 H 0.6258 0.9564 0.3511 0.028 Uiso 1 1 calc R A 4
C4 C 0.7200(3) 0.9853(3) 0.46934(16) 0.0218(5) Uani 1 1 d . A 4
H4 H 0.7188 1.0826 0.4510 0.026 Uiso 1 1 calc R A 4
C5 C 0.7760(3) 0.9131(2) 0.55673(15) 0.0185(4) Uani 1 1 d . A 4
C6 C 0.8384(3) 0.9825(2) 0.62560(15) 0.0187(4) Uani 1 1 d . A 4
C7 C 0.8222(3) 1.1253(2) 0.61381(17) 0.0228(5) Uani 1 1 d . A 4
H7 H 0.7715 1.1829 0.5609 0.027 Uiso 1 1 calc R A 4
C8 C 0.8833(4) 1.1804(3) 0.68243(19) 0.0264(5) Uani 1 1 d . A 4
H8 H 0.8746 1.2758 0.6759 0.032 Uiso 1 1 calc R A 4
C9 C 0.9570(4) 1.0922(3) 0.76053(18) 0.0269(5) Uani 1 1 d . A 4
H9 H 0.9992 1.1273 0.8072 0.032 Uiso 1 1 calc R A 4
C10 C 0.9670(3) 0.9505(3) 0.76802(17) 0.0236(5) Uani 1 1 d . A 4
H10 H 1.0148 0.8909 0.8210 0.028 Uiso 1 1 calc R A 4
C11 C 0.5514(3) 0.5042(3) 0.72210(16) 0.0233(5) Uani 1 1 d . A 4
H11 H 0.5067 0.5734 0.6727 0.028 Uiso 1 1 calc R A 4
C12 C 0.4468(4) 0.3843(3) 0.75874(18) 0.0265(5) Uani 1 1 d . A 4
H12 H 0.3344 0.3729 0.7340 0.032 Uiso 1 1 calc R A 4
C13 C 0.5127(4) 0.2814(3) 0.83312(18) 0.0282(5) Uani 1 1 d . A 4
H13 H 0.4467 0.1989 0.8580 0.034 Uiso 1 1 calc R A 4
C14 C 0.6784(4) 0.3036(3) 0.86975(17) 0.0261(5) Uani 1 1 d . A 4
H14 H 0.7232 0.2374 0.9208 0.031 Uiso 1 1 calc R A 4
C15 C 0.7767(3) 0.4261(2) 0.82916(16) 0.0214(4) Uani 1 1 d . A 4
C16 C 0.9543(3) 0.4608(2) 0.86282(15) 0.0207(4) Uani 1 1 d . A 4
C17 C 1.0460(4) 0.3710(3) 0.93525(17) 0.0257(5) Uani 1 1 d . A 4
H17 H 0.9981 0.2827 0.9647 0.031 Uiso 1 1 calc R A 4
C18 C 1.2088(4) 0.4148(3) 0.96262(17) 0.0282(5) Uani 1 1 d . A 4
H18 H 1.2707 0.3573 1.0118 0.034 Uiso 1 1 calc R A 4
C19 C 1.2796(4) 0.5462(3) 0.91563(18) 0.0284(5) Uani 1 1 d . A 4
H19 H 1.3893 0.5777 0.9330 0.034 Uiso 1 1 calc R A 4
C20 C 1.1843(4) 0.6291(3) 0.84268(17) 0.0249(5) Uani 1 1 d . A 4
H20 H 1.2334 0.7156 0.8101 0.030 Uiso 1 1 calc R A 4


_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 N1 1.978(2) . ?
Cu1 N4 1.988(2) . ?
Cu1 N3 2.021(2) . ?
Cu1 N2 2.057(2) . ?
Cu1 O1 2.2611(18) . ?
O1 N5 1.275(3) . ?
O2 N5 1.248(3) . ?
O3 N5 1.244(3) . ?
O4 N6 1.230(4) . ?
O5 N6 1.251(4) . ?
O6 N6 1.215(4) . ?
N1 C1 1.343(3) . ?
N1 C5 1.354(3) . ?
N2 C10 1.337(3) . ?
N2 C6 1.351(3) . ?
N3 C11 1.342(3) . ?
N3 C15 1.351(3) . ?
N4 C20 1.342(3) . ?
N4 C16 1.351(3) . ?
C1 C2 1.386(3) . ?
C2 C3 1.383(4) . ?
C3 C4 1.391(4) . ?
C4 C5 1.388(3) . ?
C5 C6 1.483(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.386(4) . ?
C8 C9 1.382(4) . ?
C9 C10 1.386(3) . ?
C11 C12 1.385(4) . ?
C12 C13 1.389(4) . ?
C13 C14 1.386(4) . ?
C14 C15 1.390(3) . ?
C15 C16 1.480(3) . ?
C16 C17 1.392(3) . ?
C17 C18 1.378(4) . ?
C18 C19 1.393(4) . ?
C19 C20 1.383(4) . ?

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
N1 Cu1 N4 170.67(8) . . ?
N1 Cu1 N3 99.34(8) . . ?
N4 Cu1 N3 81.17(8) . . ?
N1 Cu1 N2 81.40(8) . . ?
N4 Cu1 N2 104.27(8) . . ?
N3 Cu1 N2 140.00(8) . . ?
N1 Cu1 O1 85.32(7) . . ?
N4 Cu1 O1 87.06(8) . . ?
N3 Cu1 O1 127.89(7) . . ?
N2 Cu1 O1 92.11(7) . . ?
N5 O1 Cu1 109.20(14) . . ?
C1 N1 C5 119.4(2) . . ?
C1 N1 Cu1 124.85(16) . . ?
C5 N1 Cu1 115.39(15) . . ?
C10 N2 C6 118.7(2) . . ?
C10 N2 Cu1 128.09(17) . . ?
C6 N2 Cu1 112.79(15) . . ?
C11 N3 C15 118.7(2) . . ?
C11 N3 Cu1 127.23(17) . . ?
C15 N3 Cu1 114.02(16) . . ?
C20 N4 C16 119.2(2) . . ?
C20 N4 Cu1 125.36(17) . . ?
C16 N4 Cu1 114.84(16) . . ?
O3 N5 O2 122.0(2) . . ?
O3 N5 O1 119.4(2) . . ?
O2 N5 O1 118.6(2) . . ?
O6 N6 O4 124.0(3) . . ?
O6 N6 O5 116.3(3) . . ?
O4 N6 O5 119.6(3) . . ?
N1 C1 C2 121.8(2) . . ?
C3 C2 C1 119.3(2) . . ?
C2 C3 C4 119.1(2) . . ?
C5 C4 C3 119.0(2) . . ?
N1 C5 C4 121.5(2) . . ?
N1 C5 C6 114.92(19) . . ?
C4 C5 C6 123.6(2) . . ?
N2 C6 C7 122.0(2) . . ?
N2 C6 C5 115.11(19) . . ?
C7 C6 C5 122.9(2) . . ?
C8 C7 C6 118.7(2) . . ?
C9 C8 C7 119.4(2) . . ?
C8 C9 C10 118.7(2) . . ?
N2 C10 C9 122.5(2) . . ?
N3 C11 C12 122.5(2) . . ?
C11 C12 C13 118.8(2) . . ?
C14 C13 C12 119.0(2) . . ?
C13 C14 C15 119.1(2) . . ?
N3 C15 C14 121.8(2) . . ?
N3 C15 C16 114.6(2) . . ?
C14 C15 C16 123.6(2) . . ?
N4 C16 C17 121.6(2) . . ?
N4 C16 C15 114.8(2) . . ?
C17 C16 C15 123.7(2) . . ?
C18 C17 C16 119.0(2) . . ?
C17 C18 C19 119.2(2) . . ?
C20 C19 C18 119.0(3) . . ?
N4 C20 C19 122.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.42
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.530
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_ligand_L
_database_code_depnum_ccdc_archive 'CCDC 1044127'
_audit_update_record             
;
2015-10-27 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 O3 P'
_chemical_formula_sum            'C17 H17 O3 P'
_chemical_formula_weight         300.28

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'
P P 0.1023 0.0942 '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/c'
_symmetry_space_group_name_Hall  '-C 2yc'


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

_cell_length_a                   31.662(16)
_cell_length_b                   8.649(4)
_cell_length_c                   11.434(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.53(5)
_cell_angle_gamma                90.00
_cell_volume                     3057(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    101
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.00

_exptl_crystal_description       cube
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22464
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2973
_reflns_number_gt                1589
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_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)+(0.0956P)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         2973
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1750
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_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
P1 P 0.04498(3) 0.33278(9) 0.14360(7) 0.0602(3) Uani 1 1 d . . .
O1 O 0.06567(8) 0.2846(3) 0.03881(17) 0.0780(7) Uani 1 1 d . . .
O2 O 0.03091(7) 0.1889(2) 0.20075(18) 0.0686(7) Uani 1 1 d . . .
H2A H 0.0000 0.200(6) 0.2500 0.103 Uiso 1 2 d S . .
O3 O 0.00822(7) 0.4464(3) 0.10171(17) 0.0777(7) Uani 1 1 d . . .
H3A H 0.0000 0.5000 0.0000 0.117 Uiso 1 2 d S . .
C1 C 0.08736(10) 0.4322(3) 0.2435(3) 0.0597(8) Uani 1 1 d . . .
H1A H 0.0966 0.5178 0.2002 0.072 Uiso 1 1 calc R . .
H1B H 0.0754 0.4761 0.3075 0.072 Uiso 1 1 calc R . .
C2 C 0.12699(10) 0.3388(3) 0.2999(3) 0.0531(8) Uani 1 1 d . . .
C3 C 0.12818(10) 0.2600(3) 0.4094(2) 0.0525(8) Uani 1 1 d . . .
C4 C 0.09382(11) 0.2610(3) 0.4687(3) 0.0620(9) Uani 1 1 d . . .
H4 H 0.0687 0.3148 0.4351 0.074 Uiso 1 1 calc R . .
C5 C 0.09627(13) 0.1853(4) 0.5740(3) 0.0773(10) Uani 1 1 d . . .
H5 H 0.0730 0.1887 0.6116 0.093 Uiso 1 1 calc R . .
C6 C 0.13390(15) 0.1012(4) 0.6271(3) 0.0908(12) Uani 1 1 d . . .
H6 H 0.1354 0.0503 0.6995 0.109 Uiso 1 1 calc R . .
C7 C 0.16746(14) 0.0950(4) 0.5731(3) 0.0830(11) Uani 1 1 d . . .
H7 H 0.1919 0.0381 0.6078 0.100 Uiso 1 1 calc R . .
C8 C 0.16616(12) 0.1742(3) 0.4631(3) 0.0631(9) Uani 1 1 d . . .
C9 C 0.20070(12) 0.1689(4) 0.4092(3) 0.0719(10) Uani 1 1 d . . .
H9 H 0.2252 0.1134 0.4458 0.086 Uiso 1 1 calc R . .
C10 C 0.20043(11) 0.2439(3) 0.3011(3) 0.0636(9) Uani 1 1 d . . .
C11 C 0.23585(12) 0.2403(4) 0.2463(4) 0.0809(11) Uani 1 1 d . . .
H11 H 0.2604 0.1853 0.2831 0.097 Uiso 1 1 calc R . .
C12 C 0.23578(14) 0.3127(5) 0.1431(4) 0.0902(12) Uani 1 1 d . . .
H12 H 0.2600 0.3095 0.1093 0.108 Uiso 1 1 calc R . .
C13 C 0.19793(14) 0.3950(4) 0.0856(4) 0.0849(11) Uani 1 1 d . . .
H13 H 0.1973 0.4432 0.0125 0.102 Uiso 1 1 calc R . .
C14 C 0.16343(12) 0.4044(4) 0.1343(3) 0.0693(9) Uani 1 1 d . . .
H14 H 0.1395 0.4606 0.0951 0.083 Uiso 1 1 calc R . .
C15 C 0.16227(10) 0.3305(3) 0.2448(3) 0.0554(8) Uani 1 1 d . . .
C16 C 0.04520(19) 0.1731(5) -0.0526(4) 0.1250(17) Uani 1 1 d . . .
H16A H 0.0410 0.0760 -0.0142 0.150 Uiso 1 1 calc R . .
H16B H 0.0170 0.2116 -0.0925 0.150 Uiso 1 1 calc R . .
C17 C 0.0702(3) 0.1474(5) -0.1378(5) 0.164(3) Uani 1 1 d . . .
H17A H 0.0704 0.2391 -0.1851 0.246 Uiso 1 1 calc R . .
H17B H 0.0582 0.0632 -0.1890 0.246 Uiso 1 1 calc R . .
H17C H 0.0993 0.1224 -0.0978 0.246 Uiso 1 1 calc R . .


_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
P1 O2 1.516(2) . ?
P1 O3 1.519(2) . ?
P1 O1 1.542(2) . ?
P1 C1 1.783(3) . ?
O1 C16 1.465(5) . ?
O2 H2A 1.234(4) . ?
C1 C2 1.514(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C15 1.398(4) . ?
C2 C3 1.419(4) . ?
C3 C4 1.402(4) . ?
C3 C8 1.433(4) . ?
C4 C5 1.358(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.341(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.425(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(5) . ?
C9 C10 1.394(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.399(5) . ?
C10 C15 1.449(4) . ?
C11 C12 1.336(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.426(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.332(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.424(5) . ?
C14 H14 0.9300 . ?
C16 C17 1.401(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 P1 O3 112.95(14) . . ?
O2 P1 O1 109.07(13) . . ?
O3 P1 O1 110.82(12) . . ?
O2 P1 C1 111.73(13) . . ?
O3 P1 C1 107.97(14) . . ?
O1 P1 C1 103.93(15) . . ?
C16 O1 P1 122.4(3) . . ?
P1 O2 H2A 118(2) . . ?
C2 C1 P1 117.00(19) . . ?
C2 C1 H1A 108.0 . . ?
P1 C1 H1A 108.0 . . ?
C2 C1 H1B 108.0 . . ?
P1 C1 H1B 108.0 . . ?
H1A C1 H1B 107.3 . . ?
C15 C2 C3 120.1(3) . . ?
C15 C2 C1 120.3(3) . . ?
C3 C2 C1 119.5(3) . . ?
C4 C3 C2 123.4(3) . . ?
C4 C3 C8 117.5(3) . . ?
C2 C3 C8 119.1(3) . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.9(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 C3 120.2(3) . . ?
C7 C8 C3 119.3(4) . . ?
C8 C9 C10 122.2(3) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C9 C10 C11 122.4(3) . . ?
C9 C10 C15 118.6(3) . . ?
C11 C10 C15 119.0(3) . . ?
C12 C11 C10 122.5(4) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 118.8(4) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 121.7(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C2 C15 C14 123.6(3) . . ?
C2 C15 C10 119.8(3) . . ?
C14 C15 C10 116.5(3) . . ?
C17 C16 O1 111.8(5) . . ?
C17 C16 H16A 109.3 . . ?
O1 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
O1 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O2 P1 O1 C16 48.1(3) . . . . ?
O3 P1 O1 C16 -76.8(3) . . . . ?
C1 P1 O1 C16 167.4(3) . . . . ?
O2 P1 C1 C2 53.2(3) . . . . ?
O3 P1 C1 C2 178.0(2) . . . . ?
O1 P1 C1 C2 -64.3(3) . . . . ?
P1 C1 C2 C15 91.6(3) . . . . ?
P1 C1 C2 C3 -88.7(3) . . . . ?
C15 C2 C3 C4 -178.9(2) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C15 C2 C3 C8 0.8(4) . . . . ?
C1 C2 C3 C8 -178.9(2) . . . . ?
C2 C3 C4 C5 -179.4(3) . . . . ?
C8 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C7 -0.4(6) . . . . ?
C5 C6 C7 C8 1.0(6) . . . . ?
C6 C7 C8 C9 179.2(3) . . . . ?
C6 C7 C8 C3 -0.7(5) . . . . ?
C4 C3 C8 C9 179.9(3) . . . . ?
C2 C3 C8 C9 0.1(4) . . . . ?
C4 C3 C8 C7 -0.2(4) . . . . ?
C2 C3 C8 C7 -180.0(3) . . . . ?
C7 C8 C9 C10 179.4(3) . . . . ?
C3 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C11 179.3(3) . . . . ?
C8 C9 C10 C15 0.2(4) . . . . ?
C9 C10 C11 C12 -179.6(3) . . . . ?
C15 C10 C11 C12 -0.6(5) . . . . ?
C10 C11 C12 C13 -1.0(6) . . . . ?
C11 C12 C13 C14 1.9(6) . . . . ?
C12 C13 C14 C15 -1.2(5) . . . . ?
C3 C2 C15 C14 179.2(3) . . . . ?
C1 C2 C15 C14 -1.1(4) . . . . ?
C3 C2 C15 C10 -1.2(4) . . . . ?
C1 C2 C15 C10 178.5(2) . . . . ?
C13 C14 C15 C2 179.2(3) . . . . ?
C13 C14 C15 C10 -0.4(4) . . . . ?
C9 C10 C15 C2 0.7(4) . . . . ?
C11 C10 C15 C2 -178.4(3) . . . . ?
C9 C10 C15 C14 -179.6(3) . . . . ?
C11 C10 C15 C14 1.2(4) . . . . ?
P1 O1 C16 C17 -179.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.047
