# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_12am0511
_database_code_depnum_ccdc_archive 'CCDC 960834'
#Added by publCIF
_audit_update_record             
;
2014-06-24 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;
#Added by publCIF


_audit_creation_date             2014-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.23 svn.r2948 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3

_chemical_name_common            ?
_chemical_formula_moiety         'C32 H36 Cu N5 O10 P2, N O3'
_chemical_formula_sum            'C32 H36 Cu N6 O13 P2'
_chemical_formula_weight         838.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   18.6371(6)
_cell_length_b                   7.9394(2)
_cell_length_c                   23.7780(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.779(2)
_cell_angle_gamma                90
_cell_volume                     3514.23(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    115
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1732
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether / DCM'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            152871
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_min         2.705
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6676
_reflns_number_total             8162
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     490
_refine_ls_number_reflns         8162
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+5.8343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1055
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid bond restraints
 P2, O6A, O6B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(O6A) = Uanis(O6B) = Uanis(C25B) = Uanis(C25A) = Uanis(C26A) = Uanis(C26B)
4. Same fragment restrains
{O6A, C25A, C26A}
as
{O6B, C25B, C26B}
5. Others
 Fixed Sof: O6A(0.83583) C25A(0.83583) H25A(0.83583) H25B(0.83583)
 C26A(0.83583) H26A(0.83583) H26B(0.83583) H26C(0.83583) C28A(0.5) H28A(0.5)
 H28B(0.5) H28C(0.5) O6B(0.16417) C25B(0.16417) H25C(0.16417) H25D(0.16417)
 C26B(0.16417) H26D(0.16417) H26E(0.16417) H26F(0.16417) C28B(0.5) H28D(0.5)
 H28E(0.5) H28F(0.5) H27A(0.5) H27B(0.5) H27C(0.5) H27D(0.5)
6.a Rotating group:
 O13(H13A,H13B)
6.b Secondary CH2 refined with riding coordinates:
 C25A(H25A,H25B), C25B(H25C,H25D), C27(H27A,H27B), C27(H27C,H27D), C29(H29A,
 H29B), C31(H31A,H31B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C22(H22)
6.d Idealised Me refined as rotating group:
 C26A(H26A,H26B,H26C), C28A(H28A,H28B,H28C), C26B(H26D,H26E,H26F), C28B(H28D,
 H28E,H28F), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.49408(13) 0.5636(3) 0.61994(11) 0.0185(5) Uani 1 1 d . . . . .
H1 H 0.5019 0.5127 0.6559 0.022 Uiso 1 1 calc R . . . .
C2 C 0.42574(13) 0.5488(3) 0.59198(11) 0.0206(5) Uani 1 1 d . . . . .
H2 H 0.3881 0.4908 0.6093 0.025 Uiso 1 1 calc R . . . .
C3 C 0.41423(12) 0.6184(3) 0.53990(11) 0.0184(5) Uani 1 1 d . . . . .
H3 H 0.3685 0.6090 0.5207 0.022 Uiso 1 1 calc R . . . .
C4 C 0.47063(12) 0.7045(3) 0.51475(10) 0.0148(4) Uani 1 1 d . . . . .
C5 C 0.46449(13) 0.7781(3) 0.45971(10) 0.0175(5) Uani 1 1 d . . . . .
H5 H 0.4202 0.7713 0.4383 0.021 Uiso 1 1 calc R . . . .
C6 C 0.52115(13) 0.8573(3) 0.43789(10) 0.0173(5) Uani 1 1 d . . . . .
H6 H 0.5162 0.9027 0.4009 0.021 Uiso 1 1 calc R . . . .
C7 C 0.58863(12) 0.8744(3) 0.46938(10) 0.0133(4) Uani 1 1 d . . . . .
C8 C 0.64817(12) 0.9591(3) 0.44921(10) 0.0147(4) Uani 1 1 d . . . . .
H8 H 0.6457 1.0077 0.4127 0.018 Uiso 1 1 calc R . . . .
C9 C 0.71036(12) 0.9712(3) 0.48289(10) 0.0130(4) Uani 1 1 d . . . . .
C10 C 0.71242(12) 0.8985(3) 0.53719(9) 0.0129(4) Uani 1 1 d . . . . .
H10 H 0.7550 0.9093 0.5605 0.016 Uiso 1 1 calc R . . . .
C11 C 0.59584(11) 0.8040(3) 0.52342(9) 0.0112(4) Uani 1 1 d . . . . .
C12 C 0.53656(12) 0.7158(3) 0.54609(9) 0.0121(4) Uani 1 1 d . . . . .
C13 C 0.55826(13) 0.9676(3) 0.70046(10) 0.0172(5) Uani 1 1 d . . . . .
H13 H 0.5155 0.9255 0.6822 0.021 Uiso 1 1 calc R . . . .
C14 C 0.55295(13) 1.1045(3) 0.73715(11) 0.0199(5) Uani 1 1 d . . . . .
H14 H 0.5077 1.1555 0.7427 0.024 Uiso 1 1 calc R . . . .
C15 C 0.61389(14) 1.1640(3) 0.76495(10) 0.0195(5) Uani 1 1 d . . . . .
H15 H 0.6113 1.2567 0.7900 0.023 Uiso 1 1 calc R . . . .
C16 C 0.68041(13) 1.0864(3) 0.75601(10) 0.0170(5) Uani 1 1 d . . . . .
C17 C 0.74665(14) 1.1390(3) 0.78391(11) 0.0216(5) Uani 1 1 d . . . . .
H17 H 0.7466 1.2292 0.8101 0.026 Uiso 1 1 calc R . . . .
C18 C 0.80919(14) 1.0612(3) 0.77327(11) 0.0220(5) Uani 1 1 d . . . . .
H18 H 0.8524 1.0970 0.7924 0.026 Uiso 1 1 calc R . . . .
C19 C 0.81116(13) 0.9257(3) 0.73349(10) 0.0171(5) Uani 1 1 d . . . . .
C20 C 0.87490(13) 0.8412(3) 0.72106(10) 0.0186(5) Uani 1 1 d . . . . .
H20 H 0.9192 0.8724 0.7397 0.022 Uiso 1 1 calc R . . . .
C21 C 0.87306(12) 0.7131(3) 0.68180(10) 0.0168(5) Uani 1 1 d . . . . .
C22 C 0.80661(12) 0.6700(3) 0.65488(10) 0.0157(5) Uani 1 1 d . . . . .
H22 H 0.8054 0.5822 0.6277 0.019 Uiso 1 1 calc R . . . .
C23 C 0.74710(12) 0.8726(3) 0.70494(9) 0.0143(4) Uani 1 1 d . . . . .
C24 C 0.68050(12) 0.9532(3) 0.71731(9) 0.0141(4) Uani 1 1 d . . . . .
O6A O 0.93112(14) 0.4397(3) 0.63447(10) 0.0261(4) Uani 0.8358 1 d . U P A 1
C25A C 0.92211(19) 0.2834(4) 0.66583(14) 0.0261(4) Uani 0.8358 1 d . . P A 1
H25A H 0.8715 0.2700 0.6760 0.031 Uiso 0.8358 1 calc R . P A 1
H25B H 0.9532 0.2837 0.7008 0.031 Uiso 0.8358 1 calc R . P A 1
C26A C 0.9435(2) 0.1422(4) 0.62729(16) 0.0261(4) Uani 0.8358 1 d . . P A 1
H26A H 0.9111 0.1411 0.5935 0.039 Uiso 0.8358 1 calc GR . P A 1
H26B H 0.9401 0.0343 0.6470 0.039 Uiso 0.8358 1 calc GR . P A 1
H26C H 0.9930 0.1598 0.6164 0.039 Uiso 0.8358 1 calc GR . P A 1
C28A C 0.9863(4) 0.7237(11) 0.5101(3) 0.0327(18) Uiso 0.5 1 d . . P B 1
H28A H 0.9561 0.7349 0.4754 0.049 Uiso 0.5 1 calc GR . P B 1
H28B H 1.0124 0.6166 0.5096 0.049 Uiso 0.5 1 calc GR . P B 1
H28C H 1.0207 0.8170 0.5128 0.049 Uiso 0.5 1 calc GR . P B 1
O6B O 0.9207(8) 0.4247(16) 0.6537(6) 0.0261(4) Uani 0.1642 1 d . U P A 2
C25B C 0.9705(9) 0.2817(18) 0.6523(7) 0.0261(4) Uani 0.1642 1 d . . P A 2
H25C H 0.9824 0.2364 0.6904 0.031 Uiso 0.1642 1 calc R . P A 2
H25D H 1.0153 0.3114 0.6339 0.031 Uiso 0.1642 1 calc R . P A 2
C26B C 0.9226(10) 0.156(2) 0.6156(8) 0.0261(4) Uani 0.1642 1 d . . P A 2
H26D H 0.8888 0.2200 0.5909 0.039 Uiso 0.1642 1 calc GR . P A 2
H26E H 0.8957 0.0831 0.6403 0.039 Uiso 0.1642 1 calc GR . P A 2
H26F H 0.9533 0.0868 0.5926 0.039 Uiso 0.1642 1 calc GR . P A 2
C28B C 0.9877(4) 0.7742(10) 0.5153(3) 0.0279(16) Uiso 0.5 1 d . . P B 2
H28D H 1.0206 0.6807 0.5087 0.042 Uiso 0.5 1 calc GR . P B 2
H28E H 1.0156 0.8742 0.5268 0.042 Uiso 0.5 1 calc GR . P B 2
H28F H 0.9591 0.7987 0.4806 0.042 Uiso 0.5 1 calc GR . P B 2
C27 C 0.93972(14) 0.7278(4) 0.56004(12) 0.0282(6) Uani 1 1 d . . . . .
H27A H 0.9139 0.8366 0.5609 0.034 Uiso 0.5 1 calc R . P B 1
H27B H 0.9036 0.6364 0.5567 0.034 Uiso 0.5 1 calc R . P B 1
H27C H 0.9035 0.8172 0.5647 0.034 Uiso 0.5 1 calc R . P B 2
H27D H 0.9143 0.6215 0.5502 0.034 Uiso 0.5 1 calc R . P B 2
C29 C 0.81965(15) 1.3948(3) 0.45987(14) 0.0302(6) Uani 1 1 d . . . . .
H29A H 0.8501 1.3794 0.4273 0.036 Uiso 1 1 calc R . . . .
H29B H 0.8507 1.3887 0.4948 0.036 Uiso 1 1 calc R . . . .
C30 C 0.78270(16) 1.5605(3) 0.45614(14) 0.0319(7) Uani 1 1 d . . . . .
H30A H 0.7554 1.5690 0.4200 0.048 Uiso 1 1 calc GR . . . .
H30B H 0.8185 1.6510 0.4590 0.048 Uiso 1 1 calc GR . . . .
H30C H 0.7499 1.5709 0.4870 0.048 Uiso 1 1 calc GR . . . .
Cu1 Cu 0.64686(2) 0.68897(4) 0.63197(2) 0.01275(8) Uani 1 1 d . . . . .
C31 C 0.83995(14) 0.9233(3) 0.36857(11) 0.0227(5) Uani 1 1 d . . . . .
H31A H 0.8141 0.8231 0.3534 0.027 Uiso 1 1 calc R . . . .
H31B H 0.8764 0.8854 0.3975 0.027 Uiso 1 1 calc R . . . .
C32 C 0.87581(15) 1.0132(4) 0.32225(12) 0.0276(6) Uani 1 1 d . . . . .
H32A H 0.8395 1.0482 0.2934 0.041 Uiso 1 1 calc GR . . . .
H32B H 0.9104 0.9376 0.3055 0.041 Uiso 1 1 calc GR . . . .
H32C H 0.9010 1.1127 0.3376 0.041 Uiso 1 1 calc GR . . . .
N1 N 0.54777(10) 0.6460(2) 0.59772(8) 0.0145(4) Uani 1 1 d . . . . .
N2 N 0.65706(10) 0.8155(2) 0.55692(8) 0.0119(4) Uani 1 1 d . . . . .
N3 N 0.61995(10) 0.8935(2) 0.68988(8) 0.0144(4) Uani 1 1 d . . . . .
N4 N 0.74545(10) 0.7473(2) 0.66596(8) 0.0134(4) Uani 1 1 d . . . . .
O1 O 0.76482(9) 1.2643(2) 0.46014(8) 0.0213(4) Uani 1 1 d . . . . .
O2 O 0.85453(9) 1.0263(2) 0.49115(8) 0.0216(4) Uani 1 1 d . . . . .
O3 O 0.78950(9) 1.0390(2) 0.39355(8) 0.0240(4) Uani 1 1 d . . . . .
O4 O 0.98382(9) 0.7066(2) 0.61227(8) 0.0248(4) Uani 1 1 d . . . . .
O5 O 1.00835(10) 0.6028(3) 0.71123(8) 0.0276(4) Uani 1 1 d . . . . .
O13 O 0.63050(9) 0.5018(2) 0.68653(8) 0.0232(4) Uani 1 1 d . . . . .
H13A H 0.6510 0.4132 0.6714 0.035 Uiso 1 1 d GR . . . .
H13B H 0.6592 0.5388 0.7145 0.035 Uiso 1 1 d GR . . . .
P1 P 0.78899(3) 1.07459(8) 0.45875(3) 0.01548(13) Uani 1 1 d . . . . .
P2 P 0.95491(3) 0.60939(8) 0.66389(3) 0.01981(14) Uani 1 1 d . U . . .
N5 N 0.33968(12) 0.1426(3) 0.68562(9) 0.0236(5) Uani 1 1 d . . . . .
O10 O 0.32294(13) 0.2656(3) 0.65579(9) 0.0384(5) Uani 1 1 d . . . . .
O11 O 0.39722(11) 0.0638(3) 0.68142(9) 0.0395(6) Uani 1 1 d . . . . .
O12 O 0.29595(10) 0.0896(3) 0.72034(8) 0.0270(4) Uani 1 1 d . . . . .
N6 N 0.72024(12) 0.3065(3) 0.59887(9) 0.0252(5) Uani 1 1 d . . . . .
O7 O 0.70060(11) 0.4477(2) 0.57803(8) 0.0278(4) Uani 1 1 d . . . . .
O8 O 0.67976(12) 0.2320(3) 0.63073(9) 0.0328(5) Uani 1 1 d . . . . .
O9 O 0.77808(12) 0.2426(3) 0.58736(11) 0.0452(6) 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 H1 0.9500 . ?
C1 C2 1.413(3) . ?
C1 N1 1.327(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.364(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.411(3) . ?
C4 C5 1.433(3) . ?
C4 C12 1.409(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.354(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.439(3) . ?
C7 C8 1.402(3) . ?
C7 C11 1.402(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(3) . ?
C9 C10 1.413(3) . ?
C9 P1 1.798(2) . ?
C10 H10 0.9500 . ?
C10 N2 1.329(3) . ?
C11 C12 1.435(3) . ?
C11 N2 1.362(3) . ?
C12 N1 1.354(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.401(4) . ?
C13 N3 1.326(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.370(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.409(3) . ?
C16 C17 1.435(3) . ?
C16 C24 1.402(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.354(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.434(3) . ?
C19 C20 1.408(3) . ?
C19 C23 1.409(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(3) . ?
C21 C22 1.409(3) . ?
C21 P2 1.803(2) . ?
C22 H22 0.9500 . ?
C22 N4 1.332(3) . ?
C23 C24 1.440(3) . ?
C23 N4 1.358(3) . ?
C24 N3 1.361(3) . ?
O6A C25A 1.462(4) . ?
O6A P2 1.572(3) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C25A C26A 1.513(5) . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
C28A H28A 0.9800 . ?
C28A H28B 0.9800 . ?
C28A H28C 0.9800 . ?
C28A C27 1.505(8) . ?
O6B C25B 1.468(15) . ?
O6B P2 1.613(14) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C25B C26B 1.575(16) . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 0.9800 . ?
C28B H28D 0.9800 . ?
C28B H28E 0.9800 . ?
C28B H28F 0.9800 . ?
C28B C27 1.470(7) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 H27C 0.9900 . ?
C27 H27D 0.9900 . ?
C27 O4 1.465(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.486(4) . ?
C29 O1 1.455(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
Cu1 N1 2.0110(19) . ?
Cu1 N2 2.0647(19) . ?
Cu1 N3 2.203(2) . ?
Cu1 N4 2.0248(19) . ?
Cu1 O13 2.0057(18) . ?
Cu1 O7 2.538(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.497(4) . ?
C31 O3 1.461(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O1 P1 1.5731(18) . ?
O2 P1 1.4632(18) . ?
O3 P1 1.5763(19) . ?
O4 P2 1.567(2) . ?
O5 P2 1.4675(18) . ?
O13 H13A 0.8853 . ?
O13 H13B 0.8837 . ?
N5 O10 1.237(3) . ?
N5 O11 1.250(3) . ?
N5 O12 1.260(3) . ?
N6 O7 1.272(3) . ?
N6 O8 1.244(3) . ?
N6 O9 1.234(3) . ?

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
C2 C1 H1 118.9 . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.3(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 123.8(2) . . ?
C12 C4 C3 117.1(2) . . ?
C12 C4 C5 119.1(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.5(2) . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 123.6(2) . . ?
C11 C7 C6 118.8(2) . . ?
C11 C7 C8 117.6(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 P1 121.42(18) . . ?
C10 C9 P1 119.46(17) . . ?
C9 C10 H10 118.7 . . ?
N2 C10 C9 122.5(2) . . ?
N2 C10 H10 118.7 . . ?
C7 C11 C12 119.8(2) . . ?
N2 C11 C7 123.3(2) . . ?
N2 C11 C12 116.8(2) . . ?
C4 C12 C11 120.0(2) . . ?
N1 C12 C4 123.1(2) . . ?
N1 C12 C11 116.90(19) . . ?
C14 C13 H13 118.3 . . ?
N3 C13 H13 118.3 . . ?
N3 C13 C14 123.4(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 123.1(2) . . ?
C24 C16 C15 117.2(2) . . ?
C24 C16 C17 119.6(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 123.0(2) . . ?
C20 C19 C23 117.4(2) . . ?
C23 C19 C18 119.6(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 118.6(2) . . ?
C20 C21 P2 120.21(18) . . ?
C22 C21 P2 121.12(18) . . ?
C21 C22 H22 118.7 . . ?
N4 C22 C21 122.7(2) . . ?
N4 C22 H22 118.7 . . ?
C19 C23 C24 119.2(2) . . ?
N4 C23 C19 122.6(2) . . ?
N4 C23 C24 118.3(2) . . ?
C16 C24 C23 119.9(2) . . ?
N3 C24 C16 123.4(2) . . ?
N3 C24 C23 116.8(2) . . ?
C25A O6A P2 122.5(2) . . ?
O6A C25A H25A 110.5 . . ?
O6A C25A H25B 110.5 . . ?
O6A C25A C26A 106.3(3) . . ?
H25A C25A H25B 108.7 . . ?
C26A C25A H25A 110.5 . . ?
C26A C25A H25B 110.5 . . ?
C25A C26A H26A 109.5 . . ?
C25A C26A H26B 109.5 . . ?
C25A C26A H26C 109.5 . . ?
H26A C26A H26B 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
H28A C28A H28B 109.5 . . ?
H28A C28A H28C 109.5 . . ?
H28B C28A H28C 109.5 . . ?
C27 C28A H28A 109.5 . . ?
C27 C28A H28B 109.5 . . ?
C27 C28A H28C 109.5 . . ?
C25B O6B P2 117.4(11) . . ?
O6B C25B H25C 111.9 . . ?
O6B C25B H25D 111.9 . . ?
O6B C25B C26B 99.2(12) . . ?
H25C C25B H25D 109.6 . . ?
C26B C25B H25C 111.9 . . ?
C26B C25B H25D 111.9 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26E 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
H28D C28B H28E 109.5 . . ?
H28D C28B H28F 109.5 . . ?
H28E C28B H28F 109.5 . . ?
C27 C28B H28D 109.5 . . ?
C27 C28B H28E 109.5 . . ?
C27 C28B H28F 109.5 . . ?
C28A C27 H27A 109.6 . . ?
C28A C27 H27B 109.6 . . ?
C28B C27 H27C 110.1 . . ?
C28B C27 H27D 110.1 . . ?
H27A C27 H27B 108.1 . . ?
H27C C27 H27D 108.5 . . ?
O4 C27 C28A 110.2(3) . . ?
O4 C27 C28B 107.8(3) . . ?
O4 C27 H27A 109.6 . . ?
O4 C27 H27B 109.6 . . ?
O4 C27 H27C 110.1 . . ?
O4 C27 H27D 110.1 . . ?
H29A C29 H29B 108.4 . . ?
C30 C29 H29A 110.1 . . ?
C30 C29 H29B 110.1 . . ?
O1 C29 H29A 110.1 . . ?
O1 C29 H29B 110.1 . . ?
O1 C29 C30 107.9(2) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N1 Cu1 N2 81.58(8) . . ?
N1 Cu1 N3 98.38(8) . . ?
N1 Cu1 N4 176.53(8) . . ?
N1 Cu1 O7 92.54(7) . . ?
N2 Cu1 N3 102.41(7) . . ?
N2 Cu1 O7 82.84(7) . . ?
N3 Cu1 O7 168.44(7) . . ?
N4 Cu1 N2 96.54(8) . . ?
N4 Cu1 N3 79.13(8) . . ?
N4 Cu1 O7 90.11(7) . . ?
O13 Cu1 N1 88.33(8) . . ?
O13 Cu1 N2 160.52(8) . . ?
O13 Cu1 N3 95.49(7) . . ?
O13 Cu1 N4 94.30(7) . . ?
O13 Cu1 O7 81.00(7) . . ?
H31A C31 H31B 108.4 . . ?
C32 C31 H31A 110.0 . . ?
C32 C31 H31B 110.0 . . ?
O3 C31 H31A 110.0 . . ?
O3 C31 H31B 110.0 . . ?
O3 C31 C32 108.6(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C1 N1 C12 118.5(2) . . ?
C1 N1 Cu1 128.17(17) . . ?
C12 N1 Cu1 113.34(15) . . ?
C10 N2 C11 118.00(19) . . ?
C10 N2 Cu1 130.69(15) . . ?
C11 N2 Cu1 111.29(15) . . ?
C13 N3 C24 117.5(2) . . ?
C13 N3 Cu1 132.15(16) . . ?
C24 N3 Cu1 110.34(15) . . ?
C22 N4 C23 118.7(2) . . ?
C22 N4 Cu1 125.74(16) . . ?
C23 N4 Cu1 115.46(15) . . ?
C29 O1 P1 118.67(16) . . ?
C31 O3 P1 123.19(16) . . ?
C27 O4 P2 121.35(17) . . ?
Cu1 O13 H13A 104.1 . . ?
Cu1 O13 H13B 97.7 . . ?
H13A O13 H13B 108.3 . . ?
O1 P1 C9 101.05(10) . . ?
O1 P1 O3 102.00(10) . . ?
O2 P1 C9 112.63(11) . . ?
O2 P1 O1 118.19(11) . . ?
O2 P1 O3 115.22(10) . . ?
O3 P1 C9 106.02(10) . . ?
O6A P2 C21 105.85(13) . . ?
O6B P2 C21 96.8(5) . . ?
O4 P2 C21 106.69(11) . . ?
O4 P2 O6A 99.99(12) . . ?
O4 P2 O6B 118.6(5) . . ?
O5 P2 C21 112.69(12) . . ?
O5 P2 O6A 118.49(13) . . ?
O5 P2 O6B 109.4(5) . . ?
O5 P2 O4 111.84(11) . . ?
O10 N5 O11 122.9(2) . . ?
O10 N5 O12 119.1(2) . . ?
O11 N5 O12 118.0(2) . . ?
O8 N6 O7 119.0(2) . . ?
O9 N6 O7 120.9(3) . . ?
O9 N6 O8 120.1(2) . . ?
N6 O7 Cu1 125.54(16) . . ?

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
O13 H13A O8 0.89 1.83 2.704(3) 169.7 .
O13 H13B O12 0.88 1.77 2.641(3) 167.7 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
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C1 N1 C12 -1.0(4) . . . . ?
C2 C1 N1 Cu1 177.23(18) . . . . ?
C2 C3 C4 C5 178.3(2) . . . . ?
C2 C3 C4 C12 -1.0(3) . . . . ?
C3 C4 C5 C6 -179.2(2) . . . . ?
C3 C4 C12 C11 -179.0(2) . . . . ?
C3 C4 C12 N1 1.3(3) . . . . ?
C4 C5 C6 C7 -1.6(4) . . . . ?
C4 C12 N1 C1 -0.3(3) . . . . ?
C4 C12 N1 Cu1 -178.74(17) . . . . ?
C5 C4 C12 C11 1.6(3) . . . . ?
C5 C4 C12 N1 -178.1(2) . . . . ?
C5 C6 C7 C8 -178.2(2) . . . . ?
C5 C6 C7 C11 1.3(3) . . . . ?
C6 C7 C8 C9 179.0(2) . . . . ?
C6 C7 C11 C12 0.5(3) . . . . ?
C6 C7 C11 N2 -179.0(2) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 P1 178.72(17) . . . . ?
C7 C11 C12 C4 -1.9(3) . . . . ?
C7 C11 C12 N1 177.9(2) . . . . ?
C7 C11 N2 C10 0.3(3) . . . . ?
C7 C11 N2 Cu1 -178.16(17) . . . . ?
C8 C7 C11 C12 -180.0(2) . . . . ?
C8 C7 C11 N2 0.6(3) . . . . ?
C8 C9 C10 N2 1.3(3) . . . . ?
C8 C9 P1 O1 72.3(2) . . . . ?
C8 C9 P1 O2 -160.59(18) . . . . ?
C8 C9 P1 O3 -33.7(2) . . . . ?
C9 C10 N2 C11 -1.3(3) . . . . ?
C9 C10 N2 Cu1 176.83(16) . . . . ?
C10 C9 P1 O1 -108.63(19) . . . . ?
C10 C9 P1 O2 18.4(2) . . . . ?
C10 C9 P1 O3 145.32(18) . . . . ?
C11 C7 C8 C9 -0.6(3) . . . . ?
C11 C12 N1 C1 180.0(2) . . . . ?
C11 C12 N1 Cu1 1.5(2) . . . . ?
C12 C4 C5 C6 0.1(3) . . . . ?
C12 C11 N2 C10 -179.11(19) . . . . ?
C12 C11 N2 Cu1 2.4(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C13 N3 C24 1.4(3) . . . . ?
C14 C13 N3 Cu1 -176.09(17) . . . . ?
C14 C15 C16 C17 -179.1(2) . . . . ?
C14 C15 C16 C24 1.6(3) . . . . ?
C15 C16 C17 C18 -179.2(2) . . . . ?
C15 C16 C24 C23 177.9(2) . . . . ?
C15 C16 C24 N3 -2.0(3) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C16 C24 N3 C13 0.5(3) . . . . ?
C16 C24 N3 Cu1 178.54(18) . . . . ?
C17 C16 C24 C23 -1.3(3) . . . . ?
C17 C16 C24 N3 178.7(2) . . . . ?
C17 C18 C19 C20 180.0(3) . . . . ?
C17 C18 C19 C23 0.1(4) . . . . ?
C18 C19 C20 C21 -179.2(2) . . . . ?
C18 C19 C23 C24 -1.4(3) . . . . ?
C18 C19 C23 N4 178.7(2) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C19 C20 C21 P2 177.84(19) . . . . ?
C19 C23 C24 C16 2.0(3) . . . . ?
C19 C23 C24 N3 -178.0(2) . . . . ?
C19 C23 N4 C22 1.0(3) . . . . ?
C19 C23 N4 Cu1 178.53(18) . . . . ?
C20 C19 C23 C24 178.7(2) . . . . ?
C20 C19 C23 N4 -1.2(3) . . . . ?
C20 C21 C22 N4 -0.3(4) . . . . ?
C20 C21 P2 O6A 162.4(2) . . . . ?
C20 C21 P2 O6B 145.7(5) . . . . ?
C20 C21 P2 O4 -91.7(2) . . . . ?
C20 C21 P2 O5 31.4(2) . . . . ?
C21 C22 N4 C23 -0.2(3) . . . . ?
C21 C22 N4 Cu1 -177.45(17) . . . . ?
C22 C21 P2 O6A -19.8(2) . . . . ?
C22 C21 P2 O6B -36.5(5) . . . . ?
C22 C21 P2 O4 86.0(2) . . . . ?
C22 C21 P2 O5 -150.8(2) . . . . ?
C23 C19 C20 C21 0.7(4) . . . . ?
C23 C24 N3 C13 -179.4(2) . . . . ?
C23 C24 N3 Cu1 -1.4(2) . . . . ?
C24 C16 C17 C18 0.0(4) . . . . ?
C24 C23 N4 C22 -178.9(2) . . . . ?
C24 C23 N4 Cu1 -1.4(3) . . . . ?
C25A O6A P2 C21 -90.1(3) . . . . ?
C25A O6A P2 O6B -27.3(16) . . . . ?
C25A O6A P2 O4 159.2(2) . . . . ?
C25A O6A P2 O5 37.5(3) . . . . ?
C28A C27 O4 P2 -145.6(4) . . . . ?
C25B O6B P2 C21 -164.1(11) . . . . ?
C25B O6B P2 O6A 75.4(18) . . . . ?
C25B O6B P2 O4 82.7(12) . . . . ?
C25B O6B P2 O5 -47.1(12) . . . . ?
C28B C27 O4 P2 -162.5(4) . . . . ?
C27 O4 P2 C21 -56.8(2) . . . . ?
C27 O4 P2 O6A 53.2(2) . . . . ?
C27 O4 P2 O6B 50.9(6) . . . . ?
C27 O4 P2 O5 179.55(19) . . . . ?
C29 O1 P1 C9 161.7(2) . . . . ?
C29 O1 P1 O2 38.4(2) . . . . ?
C29 O1 P1 O3 -89.1(2) . . . . ?
C30 C29 O1 P1 175.0(2) . . . . ?
C31 O3 P1 C9 -107.6(2) . . . . ?
C31 O3 P1 O1 147.07(19) . . . . ?
C31 O3 P1 O2 17.7(2) . . . . ?
C32 C31 O3 P1 -127.9(2) . . . . ?
N1 C1 C2 C3 1.2(4) . . . . ?
N2 C11 C12 C4 177.5(2) . . . . ?
N2 C11 C12 N1 -2.7(3) . . . . ?
N3 C13 C14 C15 -1.7(4) . . . . ?
N4 C23 C24 C16 -178.0(2) . . . . ?
N4 C23 C24 N3 1.9(3) . . . . ?
P1 C9 C10 N2 -177.74(17) . . . . ?
P2 C21 C22 N4 -178.07(18) . . . . ?
P2 O6A C25A C26A -146.8(2) . . . . ?
P2 O6B C25B C26B -155.2(12) . . . . ?
O8 N6 O7 Cu1 45.8(3) . . . . ?
O9 N6 O7 Cu1 -135.0(2) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_13ma2105
_database_code_depnum_ccdc_archive 'CCDC 960835'
#Added by publCIF



_audit_update_record             
;
2014-06-24 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;
#Added by publCIF




_refine_ls_number_constraints    4
# publcif _publ_body_element loop end
_audit_creation_date             2014-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.23 svn.r2948 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 Cu N4 O9 P'
_chemical_formula_sum            'C16 H17 Cu N4 O9 P'
_chemical_formula_weight         503.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   15.6819(7)
_cell_length_b                   10.5814(5)
_cell_length_c                   25.5715(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4243.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    115
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.845
_shelx_estimated_absorpt_T_min   0.722
_exptl_absorpt_coefficient_mu    1.161
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2056
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether / DCM'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20472
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         2.816
_diffrn_ambient_temperature      115.0
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3724
_reflns_number_total             4863
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
'SHELXS-97, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122'
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4863
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+4.6609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C16-C15 \\sim C16A-C15A \\sim C14-C13
 with sigma of 0.01
 O9-C15 \\sim O9-C15A \\sim O8-C13
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C15A) = Uanis(C16A) = Uanis(C15) = Uanis(C16)
4. Others
 Fixed Sof: C15(0.75) H15A(0.75) H15B(0.75) C16(0.75) H16A(0.75) H16B(0.75)
 H16C(0.75) C15A(0.25) H15C(0.25) H15D(0.25) C16A(0.25) H16D(0.25) H16E(0.25)
 H16F(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C15A(H15C,H15D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.01396(2) 0.58403(3) 0.14934(2) 0.01714(9) Uani 1 1 d . . . . .
P1 P -0.09101(4) 0.29132(6) 0.14704(2) 0.01744(13) Uani 1 1 d . . . . .
O1 O -0.03330(11) 0.59952(17) 0.07781(7) 0.0280(4) Uani 1 1 d . . . . .
O2 O 0.08095(13) 0.7067(2) 0.05765(8) 0.0421(5) Uani 1 1 d . . . A 1
O4 O -0.08451(10) 0.67855(15) 0.17667(7) 0.0224(4) Uani 1 1 d . . . . .
O5 O -0.00729(12) 0.83984(19) 0.15383(9) 0.0389(5) Uani 1 1 d . . . . .
O7 O -0.06046(11) 0.41449(15) 0.16571(7) 0.0231(4) Uani 1 1 d . . . . .
O8 O -0.01769(10) 0.22322(15) 0.11679(7) 0.0229(4) Uani 1 1 d . . . . .
O9 O -0.17233(11) 0.29082(18) 0.11199(7) 0.0293(4) Uani 1 1 d . . . . .
O3 O -0.02520(18) 0.7007(2) 0.00498(9) 0.0656(8) Uani 1 1 d . . . A 1
N1 N 0.08256(11) 0.60965(17) 0.21587(7) 0.0159(4) Uani 1 1 d . . . . .
N2 N 0.11673(12) 0.48549(19) 0.12871(8) 0.0218(4) Uani 1 1 d . . . . .
N3 N 0.00903(16) 0.6712(2) 0.04588(8) 0.0325(5) Uani 1 1 d . . . A 1
C1 C 0.06403(14) 0.6729(2) 0.25875(9) 0.0166(5) Uani 1 1 d . . . . .
H1 H 0.0082 0.7067 0.2625 0.020 Uiso 1 1 calc R . . . .
C2 C 0.12337(14) 0.6928(2) 0.29936(9) 0.0167(5) Uani 1 1 d . . . . .
C3 C 0.20402(14) 0.6423(2) 0.29484(9) 0.0185(5) Uani 1 1 d . . . . .
H3 H 0.2451 0.6553 0.3216 0.022 Uiso 1 1 calc R . . . .
C4 C 0.22478(14) 0.5713(2) 0.25028(9) 0.0188(5) Uani 1 1 d . . . . .
C5 C 0.30577(15) 0.5092(3) 0.24245(11) 0.0278(6) Uani 1 1 d . . . . .
H5 H 0.3491 0.5169 0.2682 0.033 Uiso 1 1 calc R . . . .
C6 C 0.32066(16) 0.4405(3) 0.19910(11) 0.0315(6) Uani 1 1 d . . . . .
H6 H 0.3743 0.3999 0.1951 0.038 Uiso 1 1 calc R . . . .
C7 C 0.25818(16) 0.4272(2) 0.15913(10) 0.0260(6) Uani 1 1 d . . . . .
C8 C 0.26910(18) 0.3573(3) 0.11273(12) 0.0366(7) Uani 1 1 d . . . . .
H8 H 0.3208 0.3129 0.1067 0.044 Uiso 1 1 calc R . . . .
C9 C 0.20536(18) 0.3533(3) 0.07637(12) 0.0381(7) Uani 1 1 d . . . . .
H9 H 0.2125 0.3059 0.0451 0.046 Uiso 1 1 calc R . . . .
C10 C 0.12949(17) 0.4191(3) 0.08541(11) 0.0318(6) Uani 1 1 d . . . . .
H10 H 0.0857 0.4163 0.0597 0.038 Uiso 1 1 calc R . . . .
C11 C 0.17936(14) 0.4882(2) 0.16531(9) 0.0193(5) Uani 1 1 d . . . . .
C12 C 0.16225(14) 0.5583(2) 0.21171(9) 0.0157(5) Uani 1 1 d . . . . .
N4 N -0.07530(14) 0.8000(2) 0.17236(9) 0.0269(5) Uani 1 1 d . . . . .
O6 O -0.13355(14) 0.8673(2) 0.18638(11) 0.0516(6) Uani 1 1 d . . . B 1
C13 C -0.03250(18) 0.1048(2) 0.08828(11) 0.0318(6) Uani 1 1 d . . . . .
H13A H -0.0685 0.1207 0.0572 0.038 Uiso 1 1 calc R . . . .
H13B H -0.0622 0.0432 0.1111 0.038 Uiso 1 1 calc R . . . .
C14 C 0.0521(2) 0.0537(3) 0.07194(14) 0.0454(8) Uani 1 1 d . . . . .
H14A H 0.0787 0.1118 0.0470 0.068 Uiso 1 1 calc GR . . . .
H14B H 0.0443 -0.0291 0.0554 0.068 Uiso 1 1 calc GR . . . .
H14C H 0.0889 0.0447 0.1027 0.068 Uiso 1 1 calc GR . . . .
C15 C -0.1813(3) 0.3683(5) 0.06454(17) 0.0465(8) Uani 0.75 1 d . . P C 1
H15A H -0.1538 0.3266 0.0343 0.056 Uiso 0.75 1 calc R . P C 1
H15B H -0.1550 0.4525 0.0696 0.056 Uiso 0.75 1 calc R . P C 1
C16 C -0.2747(3) 0.3801(5) 0.05612(19) 0.0465(8) Uani 0.75 1 d . . P C 1
H16A H -0.2854 0.4240 0.0230 0.070 Uiso 0.75 1 calc GR . P C 1
H16B H -0.3000 0.4284 0.0849 0.070 Uiso 0.75 1 calc GR . P C 1
H16C H -0.3004 0.2957 0.0549 0.070 Uiso 0.75 1 calc GR . P C 1
C15A C -0.2015(8) 0.4107(9) 0.0891(5) 0.0465(8) Uani 0.25 1 d . . P C 2
H15C H -0.2289 0.4588 0.1177 0.056 Uiso 0.25 1 calc R . P C 2
H15D H -0.1495 0.4583 0.0793 0.056 Uiso 0.25 1 calc R . P C 2
C16A C -0.2589(8) 0.4183(16) 0.0443(5) 0.0465(8) Uani 0.25 1 d . . P C 2
H16D H -0.2360 0.3677 0.0155 0.070 Uiso 0.25 1 calc GR . P C 2
H16E H -0.2643 0.5065 0.0332 0.070 Uiso 0.25 1 calc GR . P C 2
H16F H -0.3152 0.3857 0.0543 0.070 Uiso 0.25 1 calc GR . P C 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 O1 1.9803(18) . ?
Cu1 O4 1.9681(16) . ?
Cu1 O7 2.1807(16) . ?
Cu1 N1 2.0310(19) . ?
Cu1 N2 1.991(2) . ?
P1 O7 1.4684(17) . ?
P1 O8 1.5621(17) . ?
P1 O9 1.5587(18) . ?
P1 C2 1.795(2) 3_545 ?
O1 N3 1.297(3) . ?
O2 N3 1.226(3) . ?
O4 N4 1.298(3) . ?
O5 N4 1.241(3) . ?
O8 C13 1.468(3) . ?
O9 C15 1.471(4) . ?
O9 C15A 1.470(7) . ?
O3 N3 1.216(3) . ?
N1 C1 1.317(3) . ?
N1 C12 1.367(3) . ?
N2 C10 1.326(3) . ?
N2 C11 1.357(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.410(3) . ?
C2 P1 1.795(2) 3 ?
C2 C3 1.378(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.403(3) . ?
C4 C5 1.444(3) . ?
C4 C12 1.398(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.346(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.423(4) . ?
C7 C8 1.409(4) . ?
C7 C11 1.403(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.366(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.398(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.425(3) . ?
N4 O6 1.213(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.493(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.486(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C16A 1.459(8) . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?

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 O7 92.58(7) . . ?
O1 Cu1 N1 163.91(7) . . ?
O1 Cu1 N2 95.83(8) . . ?
O4 Cu1 O1 89.55(8) . . ?
O4 Cu1 O7 85.98(6) . . ?
O4 Cu1 N1 92.88(7) . . ?
O4 Cu1 N2 174.57(8) . . ?
N1 Cu1 O7 103.45(7) . . ?
N2 Cu1 O7 93.05(7) . . ?
N2 Cu1 N1 82.13(8) . . ?
O7 P1 O8 109.28(10) . . ?
O7 P1 O9 117.19(10) . . ?
O7 P1 C2 111.06(10) . 3_545 ?
O8 P1 C2 108.57(10) . 3_545 ?
O9 P1 O8 108.41(10) . . ?
O9 P1 C2 101.88(10) . 3_545 ?
N3 O1 Cu1 115.99(14) . . ?
N4 O4 Cu1 112.69(15) . . ?
P1 O7 Cu1 147.39(11) . . ?
C13 O8 P1 121.54(16) . . ?
C15 O9 P1 123.4(2) . . ?
C15A O9 P1 118.7(5) . . ?
C1 N1 Cu1 130.41(15) . . ?
C1 N1 C12 117.94(19) . . ?
C12 N1 Cu1 111.47(15) . . ?
C10 N2 Cu1 128.37(18) . . ?
C10 N2 C11 118.5(2) . . ?
C11 N2 Cu1 113.09(15) . . ?
O2 N3 O1 119.7(2) . . ?
O3 N3 O1 117.7(2) . . ?
O3 N3 O2 122.6(2) . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 122.9(2) . . ?
C2 C1 H1 118.5 . . ?
C1 C2 P1 117.54(17) . 3 ?
C3 C2 P1 123.30(18) . 3 ?
C3 C2 C1 119.1(2) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.3(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 124.1(2) . . ?
C12 C4 C3 117.6(2) . . ?
C12 C4 C5 118.3(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.7(2) . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 125.0(2) . . ?
C11 C7 C6 118.7(2) . . ?
C11 C7 C8 116.3(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.7(3) . . ?
C10 C9 H9 120.2 . . ?
N2 C10 C9 122.0(3) . . ?
N2 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
N2 C11 C7 123.4(2) . . ?
N2 C11 C12 116.7(2) . . ?
C7 C11 C12 120.0(2) . . ?
N1 C12 C4 123.2(2) . . ?
N1 C12 C11 116.4(2) . . ?
C4 C12 C11 120.4(2) . . ?
O5 N4 O4 117.7(2) . . ?
O6 N4 O4 118.2(2) . . ?
O6 N4 O5 124.1(2) . . ?
O8 C13 H13A 110.1 . . ?
O8 C13 H13B 110.1 . . ?
O8 C13 C14 107.9(2) . . ?
H13A C13 H13B 108.4 . . ?
C14 C13 H13A 110.1 . . ?
C14 C13 H13B 110.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 H15A 110.7 . . ?
O9 C15 H15B 110.7 . . ?
O9 C15 C16 105.1(3) . . ?
H15A C15 H15B 108.8 . . ?
C16 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O9 C15A H15C 106.5 . . ?
O9 C15A H15D 106.5 . . ?
H15C C15A H15D 106.5 . . ?
C16A C15A O9 123.5(10) . . ?
C16A C15A H15C 106.5 . . ?
C16A C15A H15D 106.5 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 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
Cu1 O1 N3 O2 12.4(3) . . . . ?
Cu1 O1 N3 O3 -167.5(2) . . . . ?
Cu1 O4 N4 O5 -2.1(3) . . . . ?
Cu1 O4 N4 O6 177.5(2) . . . . ?
Cu1 N1 C1 C2 -172.72(17) . . . . ?
Cu1 N1 C12 C4 174.77(17) . . . . ?
Cu1 N1 C12 C11 -5.7(2) . . . . ?
Cu1 N2 C10 C9 -179.4(2) . . . . ?
Cu1 N2 C11 C7 -179.03(19) . . . . ?
Cu1 N2 C11 C12 0.4(3) . . . . ?
P1 O8 C13 C14 -170.29(19) . . . . ?
P1 O9 C15 C16 -157.8(3) . . . . ?
P1 O9 C15A C16A 160.9(11) . . . . ?
P1 C2 C3 C4 -176.95(18) 3 . . . ?
O7 P1 O8 C13 -172.67(18) . . . . ?
O7 P1 O9 C15 53.0(3) . . . . ?
O7 P1 O9 C15A 14.7(7) . . . . ?
O8 P1 O7 Cu1 40.3(2) . . . . ?
O8 P1 O9 C15 -71.2(3) . . . . ?
O8 P1 O9 C15A -109.5(7) . . . . ?
O9 P1 O7 Cu1 -83.5(2) . . . . ?
O9 P1 O8 C13 -43.9(2) . . . . ?
N1 C1 C2 P1 175.28(18) . . . 3 ?
N1 C1 C2 C3 -1.2(4) . . . . ?
N2 C11 C12 N1 3.6(3) . . . . ?
N2 C11 C12 C4 -176.8(2) . . . . ?
C1 N1 C12 C4 -0.9(3) . . . . ?
C1 N1 C12 C11 178.7(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 P1 O7 Cu1 160.07(18) 3_545 . . . ?
C2 P1 O8 C13 66.1(2) 3_545 . . . ?
C2 P1 O9 C15 174.4(3) 3_545 . . . ?
C2 P1 O9 C15A 136.1(7) 3_545 . . . ?
C2 C3 C4 C5 -177.1(2) . . . . ?
C2 C3 C4 C12 1.6(3) . . . . ?
C3 C4 C5 C6 178.7(3) . . . . ?
C3 C4 C12 N1 -0.9(3) . . . . ?
C3 C4 C12 C11 179.6(2) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C5 C4 C12 N1 177.9(2) . . . . ?
C5 C4 C12 C11 -1.6(3) . . . . ?
C5 C6 C7 C8 179.9(3) . . . . ?
C5 C6 C7 C11 0.3(4) . . . . ?
C6 C7 C8 C9 -178.5(3) . . . . ?
C6 C7 C11 N2 177.4(2) . . . . ?
C6 C7 C11 C12 -2.0(4) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C7 C11 C12 N1 -176.9(2) . . . . ?
C7 C11 C12 C4 2.7(3) . . . . ?
C8 C7 C11 N2 -2.1(4) . . . . ?
C8 C7 C11 C12 178.4(2) . . . . ?
C8 C9 C10 N2 -0.5(5) . . . . ?
C10 N2 C11 C7 1.9(4) . . . . ?
C10 N2 C11 C12 -178.7(2) . . . . ?
C11 N2 C10 C9 -0.5(4) . . . . ?
C11 C7 C8 C9 1.0(4) . . . . ?
C12 N1 C1 C2 2.0(3) . . . . ?
C12 C4 C5 C6 0.0(4) . . . . ?
C15 O9 C15A C16A 52.9(12) . . . . ?
C15A O9 C15 C16 -65.5(10) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_13al0205
_database_code_depnum_ccdc_archive 'CCDC 1009948'
#Added by publCIF



_audit_update_record             
;
2014-06-24 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;


_refine_ls_number_constraints    0
# publcif _publ_body_element loop end
_audit_creation_date             2014-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.23 svn.r2948 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H52 Cu2 N8 O24 P4'
_chemical_formula_sum            'C40 H52 Cu2 N8 O24 P4'
_chemical_formula_weight         1279.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.7003(6)
_cell_length_b                   9.8407(8)
_cell_length_c                   17.8602(16)
_cell_angle_alpha                105.813(2)
_cell_angle_beta                 92.591(3)
_cell_angle_gamma                90.967(2)
_cell_volume                     1300.23(19)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    115
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             658
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM / diethyl ether'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            50096
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.843
_diffrn_reflns_theta_min         2.727
_diffrn_ambient_temperature      115.0
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4983
_reflns_number_total             6099
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6099
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.6505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0867
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C17(H17A,H17B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C11(H11), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2578(3) 0.1703(2) -0.28668(12) 0.0203(5) Uani 1 1 d . . . . .
H1A H -0.2263 0.1359 -0.3416 0.024 Uiso 1 1 calc R . . . .
H1B H -0.2902 0.2704 -0.2767 0.024 Uiso 1 1 calc R . . . .
C2 C -0.4080(3) 0.0837(3) -0.27222(16) 0.0331(6) Uani 1 1 d . . . . .
H2A H -0.5023 0.0801 -0.3115 0.050 Uiso 1 1 calc GR . . . .
H2B H -0.4493 0.1266 -0.2202 0.050 Uiso 1 1 calc GR . . . .
H2C H -0.3705 -0.0124 -0.2755 0.050 Uiso 1 1 calc GR . . . .
C3 C 0.2698(3) 0.3667(2) -0.23183(12) 0.0221(5) Uani 1 1 d . . . . .
H3A H 0.3976 0.3618 -0.2247 0.027 Uiso 1 1 calc R . . . .
H3B H 0.2372 0.4659 -0.2093 0.027 Uiso 1 1 calc R . . . .
C4 C 0.2173(4) 0.3215(3) -0.31730(13) 0.0323(6) Uani 1 1 d . . . . .
H4A H 0.2849 0.3769 -0.3445 0.049 Uiso 1 1 calc GR . . . .
H4B H 0.0931 0.3373 -0.3246 0.049 Uiso 1 1 calc GR . . . .
H4C H 0.2398 0.2209 -0.3385 0.049 Uiso 1 1 calc GR . . . .
C5 C -0.0261(3) 0.2468(2) -0.08400(11) 0.0122(4) Uani 1 1 d . . . . .
C6 C 0.0868(3) 0.3202(2) -0.02054(11) 0.0121(4) Uani 1 1 d . . . . .
H6 H 0.1705 0.3865 -0.0282 0.015 Uiso 1 1 calc R . . . .
C7 C -0.1435(3) 0.1470(2) -0.07388(11) 0.0131(4) Uani 1 1 d . . . . .
H7 H -0.2168 0.0946 -0.1165 0.016 Uiso 1 1 calc R . . . .
C8 C -0.1543(3) 0.1228(2) -0.00006(11) 0.0124(4) Uani 1 1 d . . . . .
C9 C -0.0415(2) 0.2039(2) 0.05984(11) 0.0111(4) Uani 1 1 d . . . . .
C10 C -0.2716(3) 0.0211(2) 0.01645(11) 0.0135(4) Uani 1 1 d . . . . .
H10 H -0.3444 -0.0372 -0.0246 0.016 Uiso 1 1 calc R . . . .
C11 C -0.2803(3) 0.0070(2) 0.08932(11) 0.0139(4) Uani 1 1 d . . . . .
H11 H -0.3592 -0.0610 0.0988 0.017 Uiso 1 1 calc R . . . .
C12 C -0.1722(3) 0.0930(2) 0.15267(11) 0.0124(4) Uani 1 1 d . . . . .
C13 C -0.0515(3) 0.1886(2) 0.13698(11) 0.0117(4) Uani 1 1 d . . . . .
C14 C 0.0537(3) 0.2648(2) 0.26516(11) 0.0139(4) Uani 1 1 d . . . . .
H14 H 0.1316 0.3229 0.3040 0.017 Uiso 1 1 calc R . . . .
C15 C -0.0658(3) 0.1741(2) 0.28689(11) 0.0141(4) Uani 1 1 d . . . . .
C16 C -0.1775(3) 0.0879(2) 0.23059(11) 0.0140(4) Uani 1 1 d . . . . .
H16 H -0.2576 0.0253 0.2443 0.017 Uiso 1 1 calc R . . . .
C17 C -0.2266(3) 0.3918(3) 0.47158(13) 0.0261(5) Uani 1 1 d . . . . .
H17A H -0.3302 0.3384 0.4427 0.031 Uiso 1 1 calc R . . . .
H17B H -0.2307 0.4896 0.4669 0.031 Uiso 1 1 calc R . . . .
C18 C -0.2288(3) 0.3936(3) 0.55554(13) 0.0318(6) Uani 1 1 d . . . . .
H18A H -0.2340 0.2964 0.5597 0.048 Uiso 1 1 calc GR . . . .
H18B H -0.3310 0.4435 0.5785 0.048 Uiso 1 1 calc GR . . . .
H18C H -0.1230 0.4421 0.5834 0.048 Uiso 1 1 calc GR . . . .
C19 C 0.1903(3) 0.1195(3) 0.47626(13) 0.0297(6) Uani 1 1 d . . . . .
H19A H 0.1788 0.0207 0.4792 0.036 Uiso 1 1 calc R . . . .
H19B H 0.1221 0.1799 0.5176 0.036 Uiso 1 1 calc R . . . .
C20 C 0.3766(3) 0.1673(3) 0.48754(16) 0.0418(7) Uani 1 1 d . . . . .
H20A H 0.4423 0.1090 0.4454 0.063 Uiso 1 1 calc GR . . . .
H20B H 0.4239 0.1578 0.5377 0.063 Uiso 1 1 calc GR . . . .
H20C H 0.3863 0.2664 0.4870 0.063 Uiso 1 1 calc GR . . . .
N1 N 0.0786(2) 0.29870(17) 0.04938(9) 0.0118(3) Uani 1 1 d . . . . .
N2 N 0.0611(2) 0.27191(17) 0.19219(9) 0.0118(3) Uani 1 1 d . . . . .
N3 N 0.4677(3) 0.3402(2) 0.25306(11) 0.0261(4) Uani 1 1 d . . . . .
N4 N 0.5206(2) 0.38733(18) 0.05730(10) 0.0163(4) Uani 1 1 d . . . . .
O1 O -0.11032(19) 0.15853(15) -0.23481(8) 0.0166(3) Uani 1 1 d . . . . .
O2 O -0.08433(19) 0.42484(15) -0.17714(8) 0.0172(3) Uani 1 1 d . . . . .
O3 O 0.18391(18) 0.27502(15) -0.19057(8) 0.0160(3) Uani 1 1 d . . . . .
O4 O -0.2062(2) 0.07531(17) 0.40058(9) 0.0226(3) Uani 1 1 d . . . . .
O5 O -0.0696(2) 0.32614(16) 0.43795(8) 0.0225(3) Uani 1 1 d . . . . .
O6 O 0.1251(2) 0.12919(17) 0.39993(8) 0.0223(3) Uani 1 1 d . . . . .
O7 O 0.36812(19) 0.44188(16) 0.24788(8) 0.0183(3) Uani 1 1 d . . . . .
O8 O 0.4619(2) 0.2310(2) 0.19792(11) 0.0372(4) Uani 1 1 d . . . . .
O9 O 0.5626(3) 0.3569(3) 0.31220(11) 0.0501(6) Uani 1 1 d . . . . .
O10 O 0.41384(19) 0.47121(15) 0.10112(8) 0.0182(3) Uani 1 1 d . . . . .
O11 O 0.4705(2) 0.26569(16) 0.02216(10) 0.0277(4) Uani 1 1 d . . . . .
O12 O 0.6671(2) 0.43417(17) 0.05168(9) 0.0247(4) Uani 1 1 d . . . . .
P1 P -0.01389(7) 0.28794(5) -0.17545(3) 0.01149(11) Uani 1 1 d . . . . .
P2 P -0.06842(7) 0.16822(6) 0.38642(3) 0.01585(12) Uani 1 1 d . . . . .
Cu1 Cu 0.22951(3) 0.38383(2) 0.14663(2) 0.01113(8) 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 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.498(3) . ?
C1 O1 1.459(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.503(3) . ?
C3 O3 1.477(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.416(3) . ?
C5 C7 1.377(3) . ?
C5 P1 1.792(2) . ?
C6 H6 0.9500 . ?
C6 N1 1.326(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.408(3) . ?
C8 C9 1.401(3) . ?
C8 C10 1.435(3) . ?
C9 C13 1.432(3) . ?
C9 N1 1.357(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.351(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.435(3) . ?
C12 C13 1.402(3) . ?
C12 C16 1.409(3) . ?
C13 N2 1.362(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.410(3) . ?
C14 N2 1.328(2) . ?
C15 C16 1.379(3) . ?
C15 P2 1.795(2) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.496(3) . ?
C17 O5 1.456(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.490(4) . ?
C19 O6 1.459(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 Cu1 2.0152(16) . ?
N2 Cu1 2.0229(16) . ?
N3 O7 1.292(3) . ?
N3 O8 1.242(3) . ?
N3 O9 1.228(3) . ?
N4 O10 1.303(2) . ?
N4 O11 1.236(2) . ?
N4 O12 1.230(2) . ?
O1 P1 1.5679(14) . ?
O2 P1 1.4681(15) . ?
O2 Cu1 2.1584(14) 2_565 ?
O3 P1 1.5602(15) . ?
O4 P2 1.4638(15) . ?
O5 P2 1.5760(16) . ?
O6 P2 1.5699(16) . ?
O7 Cu1 1.9944(14) . ?
O10 Cu1 1.9643(14) . ?
Cu1 O2 2.1584(14) 2_565 ?

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
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
O1 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
O1 C1 C2 108.73(18) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
O3 C3 C4 110.73(18) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 P1 118.96(15) . . ?
C7 C5 C6 119.40(17) . . ?
C7 C5 P1 121.64(14) . . ?
C5 C6 H6 119.2 . . ?
N1 C6 C5 121.67(17) . . ?
N1 C6 H6 119.2 . . ?
C5 C7 H7 120.1 . . ?
C5 C7 C8 119.74(17) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C10 124.04(17) . . ?
C9 C8 C7 116.73(18) . . ?
C9 C8 C10 119.23(17) . . ?
C8 C9 C13 119.36(17) . . ?
N1 C9 C8 123.64(17) . . ?
N1 C9 C13 117.00(16) . . ?
C8 C10 H10 119.5 . . ?
C11 C10 C8 121.09(18) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.03(18) . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 118.65(17) . . ?
C13 C12 C16 116.89(17) . . ?
C16 C12 C11 124.46(18) . . ?
C12 C13 C9 120.54(17) . . ?
N2 C13 C9 115.95(17) . . ?
N2 C13 C12 123.51(17) . . ?
C15 C14 H14 118.9 . . ?
N2 C14 H14 118.9 . . ?
N2 C14 C15 122.22(18) . . ?
C14 C15 P2 120.17(15) . . ?
C16 C15 C14 119.27(18) . . ?
C16 C15 P2 120.54(15) . . ?
C12 C16 H16 120.2 . . ?
C15 C16 C12 119.70(18) . . ?
C15 C16 H16 120.2 . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
O5 C17 H17A 109.6 . . ?
O5 C17 H17B 109.6 . . ?
O5 C17 C18 110.13(19) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
O6 C19 H19A 110.0 . . ?
O6 C19 H19B 110.0 . . ?
O6 C19 C20 108.4(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 N1 C9 118.74(16) . . ?
C6 N1 Cu1 128.90(13) . . ?
C9 N1 Cu1 112.32(12) . . ?
C13 N2 Cu1 112.43(13) . . ?
C14 N2 C13 118.38(17) . . ?
C14 N2 Cu1 129.09(13) . . ?
O8 N3 O7 118.09(18) . . ?
O9 N3 O7 118.1(2) . . ?
O9 N3 O8 123.8(2) . . ?
O11 N4 O10 119.22(17) . . ?
O12 N4 O10 118.06(17) . . ?
O12 N4 O11 122.71(18) . . ?
C1 O1 P1 124.05(13) . . ?
P1 O2 Cu1 161.01(9) . 2_565 ?
C3 O3 P1 120.50(13) . . ?
C17 O5 P2 122.50(14) . . ?
C19 O6 P2 120.72(14) . . ?
N3 O7 Cu1 108.95(12) . . ?
N4 O10 Cu1 117.50(12) . . ?
O1 P1 C5 103.44(9) . . ?
O2 P1 C5 114.91(9) . . ?
O2 P1 O1 113.66(8) . . ?
O2 P1 O3 113.99(8) . . ?
O3 P1 C5 102.58(9) . . ?
O3 P1 O1 107.07(8) . . ?
O4 P2 C15 113.68(9) . . ?
O4 P2 O5 115.26(9) . . ?
O4 P2 O6 117.80(9) . . ?
O5 P2 C15 106.64(9) . . ?
O6 P2 C15 100.06(9) . . ?
O6 P2 O5 101.53(9) . . ?
N1 Cu1 N2 81.79(6) . . ?
N1 Cu1 O2 93.25(6) . 2_565 ?
N2 Cu1 O2 94.48(6) . 2_565 ?
O7 Cu1 N1 171.19(6) . . ?
O7 Cu1 N2 90.38(6) . . ?
O7 Cu1 O2 91.37(6) . 2_565 ?
O10 Cu1 N1 99.17(6) . . ?
O10 Cu1 N2 172.33(6) . . ?
O10 Cu1 O2 93.06(6) . 2_565 ?
O10 Cu1 O7 88.05(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
C1 O1 P1 C5 124.51(16) . . . . ?
C1 O1 P1 O2 -0.77(18) . . . . ?
C1 O1 P1 O3 -127.57(16) . . . . ?
C2 C1 O1 P1 -123.21(18) . . . . ?
C3 O3 P1 C5 -147.01(14) . . . . ?
C3 O3 P1 O1 104.46(15) . . . . ?
C3 O3 P1 O2 -22.14(17) . . . . ?
C4 C3 O3 P1 -73.3(2) . . . . ?
C5 C6 N1 C9 -0.1(3) . . . . ?
C5 C6 N1 Cu1 177.42(14) . . . . ?
C5 C7 C8 C9 -0.2(3) . . . . ?
C5 C7 C8 C10 -179.80(19) . . . . ?
C6 C5 C7 C8 2.3(3) . . . . ?
C6 C5 P1 O1 163.05(15) . . . . ?
C6 C5 P1 O2 -72.47(18) . . . . ?
C6 C5 P1 O3 51.79(17) . . . . ?
C7 C5 C6 N1 -2.3(3) . . . . ?
C7 C5 P1 O1 -17.65(19) . . . . ?
C7 C5 P1 O2 106.83(17) . . . . ?
C7 C5 P1 O3 -128.91(17) . . . . ?
C7 C8 C9 C13 177.35(18) . . . . ?
C7 C8 C9 N1 -2.3(3) . . . . ?
C7 C8 C10 C11 -177.41(19) . . . . ?
C8 C9 C13 C12 0.3(3) . . . . ?
C8 C9 C13 N2 -179.37(17) . . . . ?
C8 C9 N1 C6 2.4(3) . . . . ?
C8 C9 N1 Cu1 -175.46(15) . . . . ?
C8 C10 C11 C12 -0.1(3) . . . . ?
C9 C8 C10 C11 3.0(3) . . . . ?
C9 C13 N2 C14 178.03(17) . . . . ?
C9 C13 N2 Cu1 -5.3(2) . . . . ?
C10 C8 C9 C13 -3.0(3) . . . . ?
C10 C8 C9 N1 177.35(18) . . . . ?
C10 C11 C12 C13 -2.6(3) . . . . ?
C10 C11 C12 C16 177.84(19) . . . . ?
C11 C12 C13 C9 2.5(3) . . . . ?
C11 C12 C13 N2 -177.85(18) . . . . ?
C11 C12 C16 C15 179.10(19) . . . . ?
C12 C13 N2 C14 -1.6(3) . . . . ?
C12 C13 N2 Cu1 175.05(15) . . . . ?
C13 C9 N1 C6 -177.22(17) . . . . ?
C13 C9 N1 Cu1 4.9(2) . . . . ?
C13 C12 C16 C15 -0.4(3) . . . . ?
C14 C15 C16 C12 -0.8(3) . . . . ?
C14 C15 P2 O4 176.60(16) . . . . ?
C14 C15 P2 O5 48.47(19) . . . . ?
C14 C15 P2 O6 -56.89(18) . . . . ?
C15 C14 N2 C13 0.2(3) . . . . ?
C15 C14 N2 Cu1 -175.82(15) . . . . ?
C16 C12 C13 C9 -177.90(18) . . . . ?
C16 C12 C13 N2 1.7(3) . . . . ?
C16 C15 P2 O4 -4.9(2) . . . . ?
C16 C15 P2 O5 -133.02(17) . . . . ?
C16 C15 P2 O6 121.62(18) . . . . ?
C17 O5 P2 C15 102.20(17) . . . . ?
C17 O5 P2 O4 -24.99(19) . . . . ?
C17 O5 P2 O6 -153.50(16) . . . . ?
C18 C17 O5 P2 100.3(2) . . . . ?
C19 O6 P2 C15 176.69(18) . . . . ?
C19 O6 P2 O4 -59.6(2) . . . . ?
C19 O6 P2 O5 67.24(18) . . . . ?
C20 C19 O6 P2 -146.35(19) . . . . ?
N1 C9 C13 C12 179.94(18) . . . . ?
N1 C9 C13 N2 0.3(3) . . . . ?
N2 C14 C15 C16 1.0(3) . . . . ?
N2 C14 C15 P2 179.52(15) . . . . ?
O8 N3 O7 Cu1 0.3(2) . . . . ?
O9 N3 O7 Cu1 -179.63(18) . . . . ?
O11 N4 O10 Cu1 27.2(2) . . . . ?
O12 N4 O10 Cu1 -154.03(14) . . . . ?
P1 C5 C6 N1 177.02(15) . . . . ?
P1 C5 C7 C8 -176.95(15) . . . . ?
P2 C15 C16 C12 -179.35(15) . . . . ?
Cu1 O2 P1 C5 -19.6(3) 2_565 . . . ?
Cu1 O2 P1 O1 99.3(3) 2_565 . . . ?
Cu1 O2 P1 O3 -137.6(3) 2_565 . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_13al2406
_database_code_depnum_ccdc_archive 'CCDC 1009991'
#Added by publCIF



_audit_update_record             
;
2014-06-24 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;


_refine_ls_number_constraints    0
# publcif _publ_body_element loop end
_audit_creation_date             2014-06-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.23 svn.r2948 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C40 H52 Cu2 N8 O24 P4'
_chemical_formula_sum            'C40 H52 Cu2 N8 O24 P4'
_chemical_formula_weight         1279.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.6399(12)
_cell_length_b                   12.1111(14)
_cell_length_c                   12.1162(16)
_cell_angle_alpha                77.046(6)
_cell_angle_beta                 88.932(6)
_cell_angle_gamma                77.832(6)
_cell_volume                     1347.0(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    115
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.789
_shelx_estimated_absorpt_T_min   0.722
_exptl_absorpt_coefficient_mu    0.997
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             658
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether / DCM'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34624
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.657
_diffrn_reflns_theta_min         2.726
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5073
_reflns_number_total             6260
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.8394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C15(H15A,H15B), C13(H13A,H13B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C7(H7), C1(H1), C12(H12), C2(H2)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.26999(3) 0.19553(2) 0.49278(2) 0.01233(7) Uani 1 1 d . . . . .
P2 P 0.08925(5) -0.29601(4) 0.47149(4) 0.01206(11) Uani 1 1 d . . . . .
P1 P -0.05640(7) 0.26938(5) -0.00291(5) 0.02199(14) Uani 1 1 d . . . . .
O12 O 0.14323(16) -0.37566(12) 0.58917(12) 0.0175(3) Uani 1 1 d . . . . .
O2 O 0.36362(15) 0.32893(12) 0.45277(13) 0.0181(3) Uani 1 1 d . . . . .
O10 O -0.06304(14) -0.28000(12) 0.44473(12) 0.0161(3) Uani 1 1 d . . . . .
N7 N 0.17526(17) 0.22999(14) 0.33807(14) 0.0128(3) Uani 1 1 d . . . . .
O1 O 0.47626(16) 0.22327(14) 0.34151(13) 0.0237(3) Uani 1 1 d . . . . .
O5 O 0.33265(15) 0.15659(13) 0.65325(12) 0.0187(3) Uani 1 1 d . . . . .
O9 O -0.19803(17) 0.22462(14) 0.02424(14) 0.0272(4) Uani 1 1 d . . . . .
O11 O 0.17611(15) -0.34314(12) 0.37571(13) 0.0177(3) Uani 1 1 d . . . . .
O7 O -0.0711(2) 0.38880(14) -0.06790(14) 0.0331(4) Uani 1 1 d . . . . .
O8 O 0.02561(17) 0.16977(13) -0.05766(13) 0.0235(3) Uani 1 1 d . . . . .
O3 O 0.53328(18) 0.38490(14) 0.35014(17) 0.0378(5) Uani 1 1 d . . . . .
N17 N 0.46070(18) 0.31203(15) 0.37872(15) 0.0190(4) Uani 1 1 d . . . . .
N16 N 0.21922(17) 0.04129(14) 0.50122(14) 0.0114(3) Uani 1 1 d . . . . .
C5 C 0.1295(2) 0.13815(16) 0.31585(17) 0.0119(4) Uani 1 1 d . . . . .
C3 C 0.0337(2) 0.24904(17) 0.13235(17) 0.0166(4) Uani 1 1 d . . . . .
C4 C 0.0598(2) 0.14148(17) 0.21425(17) 0.0140(4) Uani 1 1 d . . . . .
C9 C 0.1135(2) -0.06507(16) 0.38959(16) 0.0110(4) Uani 1 1 d . . . . .
O6 O 0.5157(2) 0.0869(2) 0.76737(16) 0.0582(7) Uani 1 1 d . . . . .
C11 C 0.2080(2) -0.15594(17) 0.57851(17) 0.0135(4) Uani 1 1 d . . . . .
H11 H 0.2284 -0.2212 0.6406 0.016 Uiso 1 1 calc R . . . .
C10 C 0.1415(2) -0.16384(16) 0.48205(17) 0.0114(4) Uani 1 1 d . . . . .
N18 N 0.46769(19) 0.11260(17) 0.67051(16) 0.0224(4) Uani 1 1 d . . . . .
O4 O 0.53921(18) 0.09922(17) 0.58862(15) 0.0391(5) Uani 1 1 d . . . . .
C6 C 0.15550(19) 0.03472(16) 0.40436(16) 0.0111(4) Uani 1 1 d . . . . .
C8 C 0.0468(2) -0.06076(17) 0.28341(17) 0.0151(4) Uani 1 1 d . . . . .
H8 H 0.0201 -0.1283 0.2712 0.018 Uiso 1 1 calc R . . . .
C7 C 0.0208(2) 0.03721(17) 0.20000(18) 0.0163(4) Uani 1 1 d . . . . .
H7 H -0.0240 0.0369 0.1309 0.020 Uiso 1 1 calc R . . . .
C1 C 0.1499(2) 0.32904(17) 0.26041(18) 0.0170(4) Uani 1 1 d . . . . .
H1 H 0.1809 0.3937 0.2756 0.020 Uiso 1 1 calc R . . . .
C12 C 0.2459(2) -0.05196(16) 0.58568(17) 0.0128(4) Uani 1 1 d . . . . .
H12 H 0.2920 -0.0483 0.6530 0.015 Uiso 1 1 calc R . . . .
C2 C 0.0792(2) 0.34169(18) 0.15721(18) 0.0190(4) Uani 1 1 d . . . . .
H2 H 0.0624 0.4142 0.1040 0.023 Uiso 1 1 calc R . . . .
C17 C 0.3311(2) -0.3577(2) 0.3700(2) 0.0234(5) Uani 1 1 d . . . . .
H17A H 0.3785 -0.4370 0.4099 0.028 Uiso 1 1 calc R . . . .
H17B H 0.3638 -0.3014 0.4056 0.028 Uiso 1 1 calc R . . . .
C15 C 0.1748(3) 0.1678(2) -0.0886(2) 0.0313(6) Uani 1 1 d . . . . .
H15A H 0.2020 0.2386 -0.0760 0.038 Uiso 1 1 calc R . . . .
H15B H 0.1851 0.1675 -0.1700 0.038 Uiso 1 1 calc R . . . .
C13 C -0.3205(3) 0.2979(3) 0.0630(3) 0.0431(7) Uani 1 1 d . . . . .
H13A H -0.3406 0.3760 0.0119 0.052 Uiso 1 1 calc R . . . .
H13B H -0.3009 0.3061 0.1403 0.052 Uiso 1 1 calc R . . . .
C19 C 0.1534(4) -0.5004(2) 0.6119(2) 0.0461(8) Uani 1 1 d . . . . .
H19A H 0.0574 -0.5168 0.6078 0.055 Uiso 1 1 calc R . . . .
H19B H 0.2116 -0.5330 0.5540 0.055 Uiso 1 1 calc R . . . .
C16 C 0.2713(3) 0.0630(3) -0.0193(3) 0.0437(7) Uani 1 1 d . . . . .
H16A H 0.3677 0.0578 -0.0479 0.066 Uiso 1 1 calc GR . . . .
H16B H 0.2376 -0.0066 -0.0247 0.066 Uiso 1 1 calc GR . . . .
H16C H 0.2719 0.0690 0.0600 0.066 Uiso 1 1 calc GR . . . .
C18 C 0.3648(3) -0.3371(3) 0.2474(2) 0.0488(8) Uani 1 1 d . . . . .
H18A H 0.3186 -0.2580 0.2093 0.073 Uiso 1 1 calc GR . . . .
H18B H 0.3301 -0.3925 0.2130 0.073 Uiso 1 1 calc GR . . . .
H18C H 0.4678 -0.3475 0.2394 0.073 Uiso 1 1 calc GR . . . .
C20 C 0.2176(3) -0.5547(2) 0.7238(3) 0.0492(8) Uani 1 1 d . . . . .
H20A H 0.3066 -0.5296 0.7312 0.074 Uiso 1 1 calc GR . . . .
H20B H 0.2372 -0.6392 0.7341 0.074 Uiso 1 1 calc GR . . . .
H20C H 0.1523 -0.5318 0.7817 0.074 Uiso 1 1 calc GR . . . .
C14 C -0.4464(3) 0.2421(3) 0.0631(3) 0.0567(9) Uani 1 1 d . . . . .
H14A H -0.4607 0.2290 -0.0124 0.085 Uiso 1 1 calc GR . . . .
H14B H -0.5314 0.2933 0.0832 0.085 Uiso 1 1 calc GR . . . .
H14C H -0.4288 0.1678 0.1187 0.085 Uiso 1 1 calc GR . . . .


_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 1.9766(14) . ?
Cu1 O10 2.2428(14) 2_556 ?
Cu1 N7 2.0185(17) . ?
Cu1 O5 1.9698(15) . ?
Cu1 N16 2.0094(16) . ?
P2 O12 1.5601(15) . ?
P2 O10 1.4723(14) . ?
P2 O11 1.5597(15) . ?
P2 C10 1.8073(19) . ?
P1 O9 1.5752(17) . ?
P1 O7 1.4626(16) . ?
P1 O8 1.5677(17) . ?
P1 C3 1.812(2) . ?
O12 C19 1.456(3) . ?
O2 N17 1.301(2) . ?
O10 Cu1 2.2428(14) 2_556 ?
N7 C5 1.360(2) . ?
N7 C1 1.328(3) . ?
O1 N17 1.236(2) . ?
O5 N18 1.300(2) . ?
O9 C13 1.458(3) . ?
O11 C17 1.470(2) . ?
O8 C15 1.477(3) . ?
O3 N17 1.226(2) . ?
N16 C6 1.360(2) . ?
N16 C12 1.326(2) . ?
C5 C4 1.402(3) . ?
C5 C6 1.434(3) . ?
C3 C4 1.427(3) . ?
C3 C2 1.381(3) . ?
C4 C7 1.438(3) . ?
C9 C10 1.426(3) . ?
C9 C6 1.401(3) . ?
C9 C8 1.435(3) . ?
O6 N18 1.218(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.375(3) . ?
C11 C12 1.404(3) . ?
N18 O4 1.219(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.356(3) . ?
C7 H7 0.9500 . ?
C1 H1 0.9500 . ?
C1 C2 1.398(3) . ?
C12 H12 0.9500 . ?
C2 H2 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.490(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.495(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.508(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.454(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 O10 100.47(6) . 2_556 ?
O2 Cu1 N7 93.17(6) . . ?
O2 Cu1 N16 162.37(6) . . ?
N7 Cu1 O10 88.04(6) . 2_556 ?
O5 Cu1 O2 93.84(6) . . ?
O5 Cu1 O10 84.61(6) . 2_556 ?
O5 Cu1 N7 170.65(6) . . ?
O5 Cu1 N16 93.57(6) . . ?
N16 Cu1 O10 96.13(6) . 2_556 ?
N16 Cu1 N7 81.46(7) . . ?
O12 P2 C10 100.80(9) . . ?
O10 P2 O12 115.90(8) . . ?
O10 P2 O11 108.67(8) . . ?
O10 P2 C10 113.53(8) . . ?
O11 P2 O12 109.73(8) . . ?
O11 P2 C10 107.77(8) . . ?
O9 P1 C3 106.17(9) . . ?
O7 P1 O9 116.50(10) . . ?
O7 P1 O8 117.80(10) . . ?
O7 P1 C3 110.78(10) . . ?
O8 P1 O9 98.70(9) . . ?
O8 P1 C3 105.49(9) . . ?
C19 O12 P2 121.25(15) . . ?
N17 O2 Cu1 110.54(11) . . ?
P2 O10 Cu1 137.47(9) . 2_556 ?
C5 N7 Cu1 113.19(13) . . ?
C1 N7 Cu1 128.49(14) . . ?
C1 N7 C5 118.28(18) . . ?
N18 O5 Cu1 114.01(12) . . ?
C13 O9 P1 120.17(17) . . ?
C17 O11 P2 122.86(14) . . ?
C15 O8 P1 119.11(14) . . ?
O1 N17 O2 118.72(16) . . ?
O3 N17 O2 118.02(18) . . ?
O3 N17 O1 123.25(19) . . ?
C6 N16 Cu1 113.24(12) . . ?
C12 N16 Cu1 128.01(14) . . ?
C12 N16 C6 118.68(16) . . ?
N7 C5 C4 123.58(18) . . ?
N7 C5 C6 115.81(17) . . ?
C4 C5 C6 120.61(17) . . ?
C4 C3 P1 122.91(15) . . ?
C2 C3 P1 118.53(16) . . ?
C2 C3 C4 118.56(19) . . ?
C5 C4 C3 116.95(17) . . ?
C5 C4 C7 118.04(18) . . ?
C3 C4 C7 125.01(19) . . ?
C10 C9 C8 125.01(17) . . ?
C6 C9 C10 116.93(18) . . ?
C6 C9 C8 118.06(17) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.32(18) . . ?
C12 C11 H11 119.8 . . ?
C9 C10 P2 120.12(15) . . ?
C11 C10 P2 121.18(15) . . ?
C11 C10 C9 118.70(17) . . ?
O6 N18 O5 118.34(19) . . ?
O6 N18 O4 123.7(2) . . ?
O4 N18 O5 118.00(18) . . ?
N16 C6 C5 116.24(17) . . ?
N16 C6 C9 123.44(18) . . ?
C9 C6 C5 120.31(18) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 C9 121.75(18) . . ?
C7 C8 H8 119.1 . . ?
C4 C7 H7 119.4 . . ?
C8 C7 C4 121.17(19) . . ?
C8 C7 H7 119.4 . . ?
N7 C1 H1 118.8 . . ?
N7 C1 C2 122.47(18) . . ?
C2 C1 H1 118.8 . . ?
N16 C12 C11 121.91(18) . . ?
N16 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C3 C2 C1 120.14(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
O11 C17 H17A 110.4 . . ?
O11 C17 H17B 110.4 . . ?
O11 C17 C18 106.56(19) . . ?
H17A C17 H17B 108.6 . . ?
C18 C17 H17A 110.4 . . ?
C18 C17 H17B 110.4 . . ?
O8 C15 H15A 109.5 . . ?
O8 C15 H15B 109.5 . . ?
O8 C15 C16 110.75(19) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
O9 C13 H13A 110.0 . . ?
O9 C13 H13B 110.0 . . ?
O9 C13 C14 108.4(2) . . ?
H13A C13 H13B 108.4 . . ?
C14 C13 H13A 110.0 . . ?
C14 C13 H13B 110.0 . . ?
O12 C19 H19A 109.7 . . ?
O12 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 O12 109.9(2) . . ?
C20 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Cu1 O2 N17 O1 3.1(2) . . . . ?
Cu1 O2 N17 O3 -176.19(15) . . . . ?
Cu1 N7 C5 C4 179.60(15) . . . . ?
Cu1 N7 C5 C6 0.1(2) . . . . ?
Cu1 N7 C1 C2 -178.15(15) . . . . ?
Cu1 O5 N18 O6 179.42(18) . . . . ?
Cu1 O5 N18 O4 -0.7(2) . . . . ?
Cu1 N16 C6 C5 -2.7(2) . . . . ?
Cu1 N16 C6 C9 178.55(15) . . . . ?
Cu1 N16 C12 C11 -177.88(14) . . . . ?
P2 O12 C19 C20 175.2(2) . . . . ?
P2 O11 C17 C18 -148.30(19) . . . . ?
P1 O9 C13 C14 170.56(19) . . . . ?
P1 O8 C15 C16 115.4(2) . . . . ?
P1 C3 C4 C5 -179.43(15) . . . . ?
P1 C3 C4 C7 0.8(3) . . . . ?
P1 C3 C2 C1 -179.58(16) . . . . ?
O12 P2 O10 Cu1 67.43(14) . . . 2_556 ?
O12 P2 O11 C17 -58.66(17) . . . . ?
O12 P2 C10 C9 179.20(15) . . . . ?
O12 P2 C10 C11 -1.02(18) . . . . ?
O10 P2 O12 C19 70.7(2) . . . . ?
O10 P2 O11 C17 173.67(15) . . . . ?
O10 P2 C10 C9 -56.18(18) . . . . ?
O10 P2 C10 C11 123.59(16) . . . . ?
N7 C5 C4 C3 -1.7(3) . . . . ?
N7 C5 C4 C7 178.08(18) . . . . ?
N7 C5 C6 N16 1.8(2) . . . . ?
N7 C5 C6 C9 -179.47(17) . . . . ?
N7 C1 C2 C3 -0.5(3) . . . . ?
O9 P1 O8 C15 -174.34(16) . . . . ?
O9 P1 C3 C4 51.3(2) . . . . ?
O9 P1 C3 C2 -128.84(18) . . . . ?
O11 P2 O12 C19 -52.9(2) . . . . ?
O11 P2 O10 Cu1 -168.49(11) . . . 2_556 ?
O11 P2 C10 C9 64.24(17) . . . . ?
O11 P2 C10 C11 -115.99(16) . . . . ?
O7 P1 O9 C13 -44.1(2) . . . . ?
O7 P1 O8 C15 59.43(19) . . . . ?
O7 P1 C3 C4 178.62(18) . . . . ?
O7 P1 C3 C2 -1.5(2) . . . . ?
O8 P1 O9 C13 -171.27(18) . . . . ?
O8 P1 C3 C4 -52.9(2) . . . . ?
O8 P1 C3 C2 127.05(17) . . . . ?
C5 N7 C1 C2 -0.5(3) . . . . ?
C5 C4 C7 C8 1.8(3) . . . . ?
C3 P1 O9 C13 79.72(19) . . . . ?
C3 P1 O8 C15 -64.78(17) . . . . ?
C3 C4 C7 C8 -178.4(2) . . . . ?
C4 C5 C6 N16 -177.75(17) . . . . ?
C4 C5 C6 C9 1.0(3) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
C9 C8 C7 C4 0.3(3) . . . . ?
C10 P2 O12 C19 -166.3(2) . . . . ?
C10 P2 O10 Cu1 -48.58(15) . . . 2_556 ?
C10 P2 O11 C17 50.24(17) . . . . ?
C10 C9 C6 N16 -0.5(3) . . . . ?
C10 C9 C6 C5 -179.19(17) . . . . ?
C10 C9 C8 C7 178.55(19) . . . . ?
C10 C11 C12 N16 0.1(3) . . . . ?
C6 N16 C12 C11 -1.2(3) . . . . ?
C6 C5 C4 C3 177.80(18) . . . . ?
C6 C5 C4 C7 -2.5(3) . . . . ?
C6 C9 C10 P2 179.27(14) . . . . ?
C6 C9 C10 C11 -0.5(3) . . . . ?
C6 C9 C8 C7 -1.7(3) . . . . ?
C8 C9 C10 P2 -1.0(3) . . . . ?
C8 C9 C10 C11 179.19(18) . . . . ?
C8 C9 C6 N16 179.76(17) . . . . ?
C8 C9 C6 C5 1.1(3) . . . . ?
C1 N7 C5 C4 1.6(3) . . . . ?
C1 N7 C5 C6 -177.92(17) . . . . ?
C12 N16 C6 C5 -179.92(17) . . . . ?
C12 N16 C6 C9 1.4(3) . . . . ?
C12 C11 C10 P2 -179.08(15) . . . . ?
C12 C11 C10 C9 0.7(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C2 C3 C4 C7 -179.1(2) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop oil'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_15ami230_0ma
_database_code_depnum_ccdc_archive 'CCDC 1049575'
#Added by publCIF



_audit_update_record             
;
2015-02-16 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;


_refine_ls_number_constraints    22


_audit_creation_date             2015-02-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 Cu N4 O12 P2'
_chemical_formula_sum            'C20 H26 Cu N4 O12 P2'
_chemical_formula_weight         639.93
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   16.2508(6)
_cell_length_b                   9.2040(4)
_cell_length_c                   34.9028(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5220.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.377
_cell_measurement_theta_min      3.716
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.971
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0828 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.8522.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2632
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: heptane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            26677
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.463
_diffrn_reflns_theta_min         3.716
_diffrn_ambient_temperature      100
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'QUAZAR MX multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'high brilliance microfocus sealed tube, Cu'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4457
_reflns_number_total             4744
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.141
_refine_diff_density_min         -1.458
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4744
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0994
_refine_ls_restrained_S_all      1.186
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0740P)²+64.6063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2459
_refine_ls_wR_factor_ref         0.2480
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O5-C17A \\sim O5-C19 \\sim O6-C17 \\sim O6-C19A \\sim O1-C1 \\sim O1A-C1 \\sim
O3A-C3A \\sim O3-C3
 with sigma of 0.02
 C2-C1 \\sim C4A-C3A \\sim C4-C3 \\sim C20-C19 \\sim C18A-C17A \\sim C20A-C19A
\\sim C18-C17
 with sigma of 0.02
 P2-O4 \\sim P1A-O2A \\sim P1-O2
 with sigma of 0.02
 P1-O1 \\sim P1A-O1A \\sim P1A-O3A \\sim P1-O3 \\sim P2-O5 \\sim P2-O6
 with sigma of 0.02
 P1A-C5 \\sim P1-C5 \\sim P2-C12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C3A) = Uanis(C4) = Uanis(C4A) = Uanis(O3A) = Uanis(O3) =
Uanis(O2) = Uanis(O2A) = Uanis(P1) = Uanis(O1A) = Uanis(O1) = Uanis(C1) =
Uanis(C2) = Uanis(P1A)
Uanis(C17A) = Uanis(C19) = Uanis(C20) = Uanis(C18A) = Uanis(C19A) = Uanis(C17)
= Uanis(C18) = Uanis(C20A)
4. Others
 Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=
 Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19)=
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
 Sof(H1BC)=Sof(H1BD)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=
 Sof(H4AC)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(P1A)=1-FVAR(2)
 Sof(H1AB)=Sof(H1AA)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=
 Sof(H4C)=Sof(O1)=Sof(O2)=Sof(O3)=Sof(P1)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AB,H1AA), C1(H1BC,H1BD), C3(H3A,H3B), C3A(H3AA,H3AB), C17(H17A,H17B),
 C17A(H17C,H17D), C19(H19A,H19B), C19A(H19C,H19D)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C11(H11), C13(H13), C16(H16)
5.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), C4A(H4AA,H4AB,H4AC), C18(H18A,H18B,H18C),
 C18A(H18D,H18E,H18F), C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8489(6) -0.0785(13) 0.5353(3) 0.0654(10) Uani 1 1 d D . . . .
H1AB H 0.8510 -0.1587 0.5541 0.078 Uiso 0.470(7) 1 calc R . P A 1
H1AA H 0.8827 0.0020 0.5456 0.078 Uiso 0.470(7) 1 calc R . P A 1
H1BC H 0.8927 -0.0669 0.5547 0.078 Uiso 0.530(7) 1 calc R . P A 2
H1BD H 0.8259 0.0193 0.5303 0.078 Uiso 0.530(7) 1 calc R . P A 2
C2 C 0.8870(7) -0.1286(14) 0.5004(3) 0.0654(10) Uani 1 1 d D . . . .
H2A H 0.8470 -0.1842 0.4854 0.098 Uiso 1 1 calc GR . . . .
H2B H 0.9341 -0.1907 0.5067 0.098 Uiso 1 1 calc GR . . . .
H2C H 0.9059 -0.0449 0.4855 0.098 Uiso 1 1 calc GR . . . .
C3 C 0.5874(14) -0.122(3) 0.5028(5) 0.0654(10) Uani 0.470(7) 1 d D . P A 1
H3A H 0.5267 -0.1118 0.5031 0.078 Uiso 0.470(7) 1 calc R . P A 1
H3B H 0.6007 -0.2274 0.5033 0.078 Uiso 0.470(7) 1 calc R . P A 1
C3A C 0.6178(11) -0.117(3) 0.5004(5) 0.0654(10) Uani 0.530(7) 1 d D . P A 2
H3AA H 0.5676 -0.0655 0.4919 0.078 Uiso 0.530(7) 1 calc R . P A 2
H3AB H 0.6010 -0.2138 0.5101 0.078 Uiso 0.530(7) 1 calc R . P A 2
C4 C 0.6209(14) -0.056(3) 0.4680(6) 0.0654(10) Uani 0.470(7) 1 d D . P A 1
H4A H 0.6399 -0.1327 0.4506 0.098 Uiso 0.470(7) 1 calc GR . P A 1
H4B H 0.6672 0.0069 0.4748 0.098 Uiso 0.470(7) 1 calc GR . P A 1
H4C H 0.5780 0.0014 0.4554 0.098 Uiso 0.470(7) 1 calc GR . P A 1
C4A C 0.6729(12) -0.136(3) 0.4679(5) 0.0654(10) Uani 0.530(7) 1 d D . P A 2
H4AA H 0.6405 -0.1588 0.4449 0.098 Uiso 0.530(7) 1 calc GR . P A 2
H4AB H 0.7111 -0.2161 0.4731 0.098 Uiso 0.530(7) 1 calc GR . P A 2
H4AC H 0.7040 -0.0464 0.4636 0.098 Uiso 0.530(7) 1 calc GR . P A 2
C5 C 0.6956(5) -0.0060(10) 0.6029(2) 0.042(2) Uani 1 1 d D . . . .
C6 C 0.7643(4) 0.0037(10) 0.6256(2) 0.0371(18) Uani 1 1 d . . . . .
H6 H 0.8149 -0.0378 0.6175 0.045 Uiso 1 1 calc R . . . .
C7 C 0.7590(4) 0.0764(9) 0.6612(2) 0.0299(16) Uani 1 1 d . . . . .
C8 C 0.8264(4) 0.0948(9) 0.6875(2) 0.0315(16) Uani 1 1 d . . . . .
H8 H 0.8798 0.0624 0.6803 0.038 Uiso 1 1 calc R . . . .
C9 C 0.8156(4) 0.1567(8) 0.7219(2) 0.0267(15) Uani 1 1 d . . . . .
H9 H 0.8609 0.1642 0.7390 0.032 Uiso 1 1 calc R . . . .
C10 C 0.7361(4) 0.2123(8) 0.73357(19) 0.0227(14) Uani 1 1 d . . . . .
C11 C 0.7205(4) 0.2741(8) 0.7691(2) 0.0242(14) Uani 1 1 d . . . . .
H11 H 0.7631 0.2819 0.7876 0.029 Uiso 1 1 calc R . . . .
C12 C 0.6421(4) 0.3243(7) 0.77721(19) 0.0217(14) Uani 1 1 d D . . . .
C13 C 0.5798(4) 0.3045(7) 0.75000(19) 0.0210(13) Uani 1 1 d . . . . .
H13 H 0.5257 0.3356 0.7562 0.025 Uiso 1 1 calc R . . . .
C14 C 0.6702(4) 0.1991(7) 0.70785(19) 0.0200(13) Uani 1 1 d . . . . .
C15 C 0.6817(4) 0.1329(7) 0.67160(19) 0.0227(14) Uani 1 1 d . . . . .
C16 C 0.6220(5) 0.0589(9) 0.6146(2) 0.0332(17) Uani 1 1 d . . . . .
H16 H 0.5756 0.0553 0.5980 0.040 Uiso 1 1 calc R . . . .
C17 C 0.5287(9) 0.255(2) 0.8664(4) 0.0405(16) Uani 0.542(17) 1 d D . P B 1
H17A H 0.5194 0.1556 0.8562 0.049 Uiso 0.542(17) 1 calc R . P B 1
H17B H 0.4861 0.3193 0.8553 0.049 Uiso 0.542(17) 1 calc R . P B 1
C17A C 0.717(2) 0.559(3) 0.8661(6) 0.0405(16) Uani 0.458(17) 1 d D . P B 2
H17C H 0.6653 0.5608 0.8810 0.049 Uiso 0.458(17) 1 calc R . P B 2
H17D H 0.7352 0.6613 0.8627 0.049 Uiso 0.458(17) 1 calc R . P B 2
C18 C 0.5202(11) 0.253(2) 0.9086(4) 0.0405(16) Uani 0.542(17) 1 d D . P B 1
H18A H 0.4702 0.1993 0.9157 0.061 Uiso 0.542(17) 1 calc GR . P B 1
H18B H 0.5166 0.3524 0.9182 0.061 Uiso 0.542(17) 1 calc GR . P B 1
H18C H 0.5682 0.2045 0.9199 0.061 Uiso 0.542(17) 1 calc GR . P B 1
C18A C 0.7799(15) 0.482(3) 0.8885(6) 0.0405(16) Uani 0.458(17) 1 d D . P B 2
H18D H 0.8234 0.4471 0.8713 0.061 Uiso 0.458(17) 1 calc GR . P B 2
H18E H 0.7545 0.3985 0.9015 0.061 Uiso 0.458(17) 1 calc GR . P B 2
H18F H 0.8036 0.5475 0.9076 0.061 Uiso 0.458(17) 1 calc GR . P B 2
C19 C 0.7215(17) 0.575(3) 0.8632(5) 0.0405(16) Uani 0.542(17) 1 d D . P B 1
H19A H 0.6751 0.5713 0.8816 0.049 Uiso 0.542(17) 1 calc R . P B 1
H19B H 0.7338 0.6777 0.8574 0.049 Uiso 0.542(17) 1 calc R . P B 1
C19A C 0.5413(11) 0.254(3) 0.8756(5) 0.0405(16) Uani 0.458(17) 1 d D . P B 2
H19C H 0.5400 0.1469 0.8761 0.049 Uiso 0.458(17) 1 calc R . P B 2
H19D H 0.4893 0.2906 0.8643 0.049 Uiso 0.458(17) 1 calc R . P B 2
C20 C 0.7945(13) 0.503(2) 0.8799(5) 0.0405(16) Uani 0.542(17) 1 d D . P B 1
H20A H 0.8373 0.4941 0.8602 0.061 Uiso 0.542(17) 1 calc GR . P B 1
H20B H 0.7794 0.4066 0.8892 0.061 Uiso 0.542(17) 1 calc GR . P B 1
H20C H 0.8155 0.5619 0.9012 0.061 Uiso 0.542(17) 1 calc GR . P B 1
C20A C 0.5535(13) 0.313(2) 0.9143(5) 0.0405(16) Uani 0.458(17) 1 d D . P B 2
H20D H 0.5597 0.4191 0.9129 0.061 Uiso 0.458(17) 1 calc GR . P B 2
H20E H 0.6031 0.2707 0.9256 0.061 Uiso 0.458(17) 1 calc GR . P B 2
H20F H 0.5057 0.2894 0.9303 0.061 Uiso 0.458(17) 1 calc GR . P B 2
N1 N 0.6152(3) 0.1256(6) 0.64829(16) 0.0241(12) Uani 1 1 d . . . . .
N2 N 0.5926(3) 0.2453(6) 0.71651(16) 0.0213(12) Uani 1 1 d . . . . .
N3 N 0.4224(3) 0.4362(6) 0.70985(16) 0.0234(12) Uani 1 1 d . . . . .
N4 N 0.4863(4) 0.3380(8) 0.60186(17) 0.0314(14) Uani 1 1 d . . . . .
O1 O 0.7677(7) -0.0304(18) 0.5329(4) 0.0654(10) Uani 0.470(7) 1 d D . P A 1
O1A O 0.7849(7) -0.1652(15) 0.5519(4) 0.0654(10) Uani 0.530(7) 1 d D . P A 2
O2 O 0.7073(10) -0.2579(16) 0.5655(4) 0.0654(10) Uani 0.470(7) 1 d D . P A 1
O2A O 0.6486(9) -0.2640(15) 0.5717(4) 0.0654(10) Uani 0.530(7) 1 d D . P A 2
O3 O 0.6226(9) -0.051(2) 0.5358(4) 0.0654(10) Uani 0.470(7) 1 d D . P A 1
O3A O 0.6561(9) -0.0358(17) 0.5312(4) 0.0654(10) Uani 0.530(7) 1 d D . P A 2
O4 O 0.5420(3) 0.5057(6) 0.81624(14) 0.0276(11) Uani 1 1 d D . . . .
O5 O 0.7001(3) 0.4978(6) 0.82843(15) 0.0344(12) Uani 1 1 d D . . . .
O6 O 0.6110(3) 0.3061(6) 0.85439(14) 0.0367(13) Uani 1 1 d D . . . .
O7 O 0.4781(3) 0.5150(6) 0.69782(16) 0.0332(12) Uani 1 1 d . . . . .
O8 O 0.4195(3) 0.3021(5) 0.69864(14) 0.0256(10) Uani 1 1 d . . . . .
O9 O 0.3706(3) 0.4775(6) 0.73290(16) 0.0348(13) Uani 1 1 d . . . . .
O10 O 0.5400(3) 0.4142(6) 0.61708(16) 0.0373(13) Uani 1 1 d . . . . .
O11 O 0.4582(3) 0.2280(6) 0.62125(14) 0.0275(11) Uani 1 1 d . . . . .
O12 O 0.4575(4) 0.3618(8) 0.57047(16) 0.0530(17) Uani 1 1 d . . . . .
P1 P 0.7000(8) -0.1033(11) 0.5582(3) 0.0654(10) Uani 0.470(7) 1 d D . P A 1
P1A P 0.6953(7) -0.1284(10) 0.5629(2) 0.0654(10) Uani 0.530(7) 1 d D . P A 2
P2 P 0.61721(10) 0.4174(2) 0.82085(5) 0.0233(4) Uani 1 1 d D . . . .
Cu1 Cu 0.51464(5) 0.21813(12) 0.67181(3) 0.0217(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
C1 H1AB 0.9900 . ?
C1 H1AA 0.9900 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 C2 1.441(11) . ?
C1 O1 1.394(12) . ?
C1 O1A 1.434(13) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.463(16) . ?
C3 O3 1.444(14) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.457(15) . ?
C3A O3A 1.450(14) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C5 C6 1.371(11) . ?
C5 C16 1.398(11) . ?
C5 P1 1.800(12) . ?
C5 P1A 1.794(11) . ?
C6 H6 0.9500 . ?
C6 C7 1.414(11) . ?
C7 C8 1.440(10) . ?
C7 C15 1.407(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.340(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.449(9) . ?
C10 C11 1.388(10) . ?
C10 C14 1.403(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(9) . ?
C12 C13 1.400(9) . ?
C12 P2 1.794(7) . ?
C13 H13 0.9500 . ?
C13 N2 1.306(9) . ?
C14 C15 1.417(9) . ?
C14 N2 1.364(8) . ?
C15 N1 1.354(9) . ?
C16 H16 0.9500 . ?
C16 N1 1.332(9) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.481(14) . ?
C17 O6 1.480(12) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C17A C18A 1.471(14) . ?
C17A O5 1.458(13) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.475(14) . ?
C19 O5 1.448(12) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A C20A 1.468(15) . ?
C19A O6 1.435(13) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
N1 Cu1 2.018(6) . ?
N2 Cu1 2.025(5) . ?
N3 O7 1.235(7) . ?
N3 O8 1.295(7) . ?
N3 O9 1.225(7) . ?
N4 O10 1.240(8) . ?
N4 O11 1.300(8) . ?
N4 O12 1.211(8) . ?
O1 P1 1.562(13) . ?
O1A P1A 1.544(12) . ?
O2 P1 1.450(14) . ?
O2A P1A 1.493(13) . ?
O3 P1 1.557(13) . ?
O3A P1A 1.536(12) . ?
O4 P2 1.476(5) . ?
O4 Cu1 2.201(5) 3_656 ?
O5 P2 1.560(5) . ?
O6 P2 1.558(5) . ?
O8 Cu1 1.966(5) . ?
O11 Cu1 1.991(5) . ?
Cu1 O4 2.201(5) 3_646 ?

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
H1AB C1 H1AA 107.2 . . ?
H1BC C1 H1BD 107.1 . . ?
C2 C1 H1AB 108.0 . . ?
C2 C1 H1AA 108.0 . . ?
C2 C1 H1BC 107.7 . . ?
C2 C1 H1BD 107.7 . . ?
O1 C1 H1AB 108.0 . . ?
O1 C1 H1AA 108.0 . . ?
O1 C1 C2 117.4(10) . . ?
O1A C1 H1BC 107.7 . . ?
O1A C1 H1BD 107.7 . . ?
O1A C1 C2 118.5(11) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
O3 C3 H3A 109.9 . . ?
O3 C3 H3B 109.9 . . ?
O3 C3 C4 109.0(18) . . ?
H3AA C3A H3AB 107.9 . . ?
C4A C3A H3AA 109.2 . . ?
C4A C3A H3AB 109.2 . . ?
O3A C3A H3AA 109.2 . . ?
O3A C3A H3AB 109.2 . . ?
O3A C3A C4A 112.1(16) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3A C4A H4AA 109.5 . . ?
C3A C4A H4AB 109.5 . . ?
C3A C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C6 C5 C16 120.1(7) . . ?
C6 C5 P1 120.0(7) . . ?
C6 C5 P1A 119.5(7) . . ?
C16 C5 P1 119.9(7) . . ?
C16 C5 P1A 119.5(7) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.2(7) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C8 124.7(7) . . ?
C15 C7 C6 117.1(6) . . ?
C15 C7 C8 118.1(7) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(7) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.3(6) . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 124.0(6) . . ?
C11 C10 C14 117.9(6) . . ?
C14 C10 C9 118.1(6) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.2(6) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 118.9(6) . . ?
C11 C12 P2 122.7(5) . . ?
C13 C12 P2 118.4(5) . . ?
C12 C13 H13 118.5 . . ?
N2 C13 C12 123.1(6) . . ?
N2 C13 H13 118.5 . . ?
C10 C14 C15 120.5(6) . . ?
N2 C14 C10 122.4(6) . . ?
N2 C14 C15 117.0(6) . . ?
C7 C15 C14 120.5(6) . . ?
N1 C15 C7 122.6(6) . . ?
N1 C15 C14 116.9(6) . . ?
C5 C16 H16 119.2 . . ?
N1 C16 C5 121.7(7) . . ?
N1 C16 H16 119.2 . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
O6 C17 H17A 109.3 . . ?
O6 C17 H17B 109.3 . . ?
O6 C17 C18 111.7(12) . . ?
H17C C17A H17D 107.5 . . ?
C18A C17A H17C 108.5 . . ?
C18A C17A H17D 108.5 . . ?
O5 C17A H17C 108.5 . . ?
O5 C17A H17D 108.5 . . ?
O5 C17A C18A 114.9(19) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.1 . . ?
C20 C19 H19B 110.1 . . ?
O5 C19 H19A 110.1 . . ?
O5 C19 H19B 110.1 . . ?
O5 C19 C20 107.8(16) . . ?
H19C C19A H19D 108.9 . . ?
C20A C19A H19C 110.9 . . ?
C20A C19A H19D 110.9 . . ?
O6 C19A H19C 110.9 . . ?
O6 C19A H19D 110.9 . . ?
O6 C19A C20A 104.3(13) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C15 N1 Cu1 112.4(4) . . ?
C16 N1 C15 119.2(6) . . ?
C16 N1 Cu1 128.4(5) . . ?
C13 N2 C14 118.4(6) . . ?
C13 N2 Cu1 129.9(5) . . ?
C14 N2 Cu1 111.6(4) . . ?
O7 N3 O8 118.9(5) . . ?
O9 N3 O7 123.0(6) . . ?
O9 N3 O8 118.0(6) . . ?
O10 N4 O11 117.7(6) . . ?
O12 N4 O10 123.9(7) . . ?
O12 N4 O11 118.4(7) . . ?
C1 O1 P1 119.8(13) . . ?
C1 O1A P1A 131.5(11) . . ?
C3 O3 P1 125.7(15) . . ?
C3A O3A P1A 115.2(15) . . ?
P2 O4 Cu1 144.6(3) . 3_656 ?
C17A O5 P2 120.1(15) . . ?
C19 O5 P2 125.5(13) . . ?
C17 O6 P2 118.8(8) . . ?
C19A O6 P2 131.1(11) . . ?
N3 O8 Cu1 119.3(4) . . ?
N4 O11 Cu1 109.6(4) . . ?
O1 P1 C5 107.7(9) . . ?
O2 P1 C5 109.8(9) . . ?
O2 P1 O1 117.6(12) . . ?
O2 P1 O3 117.1(13) . . ?
O3 P1 C5 104.5(9) . . ?
O3 P1 O1 98.8(10) . . ?
O1A P1A C5 109.2(8) . . ?
O2A P1A C5 111.4(8) . . ?
O2A P1A O1A 110.3(10) . . ?
O2A P1A O3A 113.7(12) . . ?
O3A P1A C5 102.4(8) . . ?
O3A P1A O1A 109.6(10) . . ?
O4 P2 C12 110.9(3) . . ?
O4 P2 O5 118.2(3) . . ?
O4 P2 O6 112.9(3) . . ?
O5 P2 C12 100.1(3) . . ?
O6 P2 C12 109.8(3) . . ?
O6 P2 O5 103.9(3) . . ?
N1 Cu1 N2 81.9(2) . . ?
N1 Cu1 O4 92.4(2) . 3_646 ?
N2 Cu1 O4 103.0(2) . 3_646 ?
O8 Cu1 N1 175.5(2) . . ?
O8 Cu1 N2 94.4(2) . . ?
O8 Cu1 O4 86.0(2) . 3_646 ?
O8 Cu1 O11 92.4(2) . . ?
O11 Cu1 N1 91.8(2) . . ?
O11 Cu1 N2 164.9(2) . . ?
O11 Cu1 O4 90.9(2) . 3_646 ?

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
C1 O1 P1 C5 89.6(14) . . . . ?
C1 O1 P1 O2 -35.1(18) . . . . ?
C1 O1 P1 O3 -162.0(13) . . . . ?
C1 O1A P1A C5 -69.0(15) . . . . ?
C1 O1A P1A O2A 168.2(13) . . . . ?
C1 O1A P1A O3A 42.3(17) . . . . ?
C2 C1 O1 P1 122.5(13) . . . . ?
C2 C1 O1A P1A -124.2(13) . . . . ?
C3 O3 P1 C5 -163.8(17) . . . . ?
C3 O3 P1 O1 85(2) . . . . ?
C3 O3 P1 O2 -42(2) . . . . ?
C3A O3A P1A C5 -156.6(11) . . . . ?
C3A O3A P1A O1A 87.7(15) . . . . ?
C3A O3A P1A O2A -36.3(16) . . . . ?
C4 C3 O3 P1 -94(2) . . . . ?
C4A C3A O3A P1A -96(2) . . . . ?
C5 C6 C7 C8 -179.7(8) . . . . ?
C5 C6 C7 C15 1.1(12) . . . . ?
C5 C16 N1 C15 1.1(12) . . . . ?
C5 C16 N1 Cu1 -177.0(6) . . . . ?
C6 C5 C16 N1 -3.0(14) . . . . ?
C6 C5 P1 O1 -58.8(12) . . . . ?
C6 C5 P1 O2 70.5(13) . . . . ?
C6 C5 P1 O3 -163.2(11) . . . . ?
C6 C5 P1A O1A -20.0(12) . . . . ?
C6 C5 P1A O2A 102.1(11) . . . . ?
C6 C5 P1A O3A -136.1(11) . . . . ?
C6 C7 C8 C9 -175.6(8) . . . . ?
C6 C7 C15 C14 176.0(7) . . . . ?
C6 C7 C15 N1 -3.1(11) . . . . ?
C7 C8 C9 C10 -2.2(12) . . . . ?
C7 C15 N1 C16 2.0(11) . . . . ?
C7 C15 N1 Cu1 -179.6(5) . . . . ?
C8 C7 C15 C14 -3.2(11) . . . . ?
C8 C7 C15 N1 177.6(7) . . . . ?
C8 C9 C10 C11 178.3(7) . . . . ?
C8 C9 C10 C14 0.3(11) . . . . ?
C9 C10 C11 C12 179.8(7) . . . . ?
C9 C10 C14 C15 0.1(10) . . . . ?
C9 C10 C14 N2 178.6(6) . . . . ?
C10 C11 C12 C13 3.2(10) . . . . ?
C10 C11 C12 P2 -175.5(5) . . . . ?
C10 C14 C15 C7 1.5(10) . . . . ?
C10 C14 C15 N1 -179.3(6) . . . . ?
C10 C14 N2 C13 0.2(9) . . . . ?
C10 C14 N2 Cu1 177.2(5) . . . . ?
C11 C10 C14 C15 -178.1(6) . . . . ?
C11 C10 C14 N2 0.5(10) . . . . ?
C11 C12 C13 N2 -2.6(10) . . . . ?
C11 C12 P2 O4 158.3(6) . . . . ?
C11 C12 P2 O5 32.8(6) . . . . ?
C11 C12 P2 O6 -76.1(6) . . . . ?
C12 C13 N2 C14 0.9(10) . . . . ?
C12 C13 N2 Cu1 -175.5(5) . . . . ?
C13 C12 P2 O4 -20.4(6) . . . . ?
C13 C12 P2 O5 -146.0(5) . . . . ?
C13 C12 P2 O6 105.1(6) . . . . ?
C14 C10 C11 C12 -2.2(10) . . . . ?
C14 C15 N1 C16 -177.1(7) . . . . ?
C14 C15 N1 Cu1 1.2(8) . . . . ?
C15 C7 C8 C9 3.6(12) . . . . ?
C15 C14 N2 C13 178.8(6) . . . . ?
C15 C14 N2 Cu1 -4.2(7) . . . . ?
C16 C5 C6 C7 1.8(14) . . . . ?
C16 C5 P1 O1 121.5(11) . . . . ?
C16 C5 P1 O2 -109.2(12) . . . . ?
C16 C5 P1 O3 17.1(14) . . . . ?
C16 C5 P1A O1A 171.0(9) . . . . ?
C16 C5 P1A O2A -66.9(12) . . . . ?
C16 C5 P1A O3A 54.9(12) . . . . ?
C17 O6 P2 C12 -99.0(10) . . . . ?
C17 O6 P2 O4 25.4(10) . . . . ?
C17 O6 P2 O5 154.7(9) . . . . ?
C17A O5 P2 C12 -164.4(14) . . . . ?
C17A O5 P2 O4 75.1(14) . . . . ?
C17A O5 P2 O6 -50.9(14) . . . . ?
C18 C17 O6 P2 -135.9(13) . . . . ?
C18A C17A O5 P2 108(2) . . . . ?
C19 O5 P2 C12 -170.2(13) . . . . ?
C19 O5 P2 O4 69.3(14) . . . . ?
C19 O5 P2 O6 -56.7(13) . . . . ?
C19A O6 P2 C12 -109.4(12) . . . . ?
C19A O6 P2 O4 15.0(13) . . . . ?
C19A O6 P2 O5 144.2(12) . . . . ?
C20 C19 O5 P2 118.7(16) . . . . ?
C20A C19A O6 P2 -112.3(15) . . . . ?
N2 C14 C15 C7 -177.1(6) . . . . ?
N2 C14 C15 N1 2.1(9) . . . . ?
O7 N3 O8 Cu1 12.4(7) . . . . ?
O9 N3 O8 Cu1 -165.5(5) . . . . ?
O10 N4 O11 Cu1 -0.2(7) . . . . ?
O12 N4 O11 Cu1 -178.7(6) . . . . ?
P1 C5 C6 C7 -177.9(8) . . . . ?
P1 C5 C16 N1 176.7(7) . . . . ?
P1A C5 C6 C7 -167.1(7) . . . . ?
P1A C5 C16 N1 165.9(7) . . . . ?
P2 C12 C13 N2 176.2(5) . . . . ?
Cu1 O4 P2 C12 -135.8(5) 3_656 . . . ?
Cu1 O4 P2 O5 -21.1(7) 3_656 . . . ?
Cu1 O4 P2 O6 100.4(5) 3_656 . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
