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

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

data_PF150
_database_code_depnum_ccdc_archive 'CCDC 953036'
_audit_update_record             
;
2013-07-29 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 Cl Cu N3 O'
_chemical_formula_weight         411.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   8.06690(10)
_cell_length_b                   10.2015(2)
_cell_length_c                   10.8792(2)
_cell_angle_alpha                90.4250(10)
_cell_angle_beta                 104.9720(10)
_cell_angle_gamma                94.3570(10)
_cell_volume                     862.07(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             418
_exptl_absorpt_coefficient_mu    1.436
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15679
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4147
_reflns_number_gt                3264
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.2721P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4147
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.65841(3) 0.58739(3) 0.69645(3) 0.03321(11) Uani 1 1 d . . .
Cl1 Cl 0.49951(8) 0.39413(6) 0.66015(9) 0.0537(2) Uani 1 1 d . . .
O1 O 0.4841(2) 0.66849(16) 0.75241(18) 0.0374(4) Uani 1 1 d . . .
N1 N 0.7520(2) 0.75353(19) 0.6381(2) 0.0302(4) Uani 1 1 d . . .
N2 N 1.1679(2) 0.5201(2) 0.7594(2) 0.0343(5) Uani 1 1 d . . .
H2 H 1.2676 0.5401 0.7468 0.041 Uiso 1 1 calc R . .
N3 N 0.8877(2) 0.52161(18) 0.74182(19) 0.0290(4) Uani 1 1 d . . .
C1 C 0.8763(3) 0.7513(2) 0.5655(2) 0.0316(5) Uani 1 1 d . . .
C2 C 1.0093(3) 0.6654(2) 0.5980(2) 0.0299(5) Uani 1 1 d . . .
C3 C 1.1323(3) 0.6686(3) 0.5281(3) 0.0361(6) Uani 1 1 d . . .
H3 H 1.2212 0.6132 0.5493 0.043 Uiso 1 1 calc R . .
C4 C 1.1245(4) 0.7523(3) 0.4283(3) 0.0440(7) Uani 1 1 d . . .
H4 H 1.2091 0.7547 0.3840 0.053 Uiso 1 1 calc R . .
C5 C 0.9913(4) 0.8323(3) 0.3943(3) 0.0465(7) Uani 1 1 d . . .
H5 H 0.9842 0.8870 0.3254 0.056 Uiso 1 1 calc R . .
C6 C 0.8672(3) 0.8320(3) 0.4623(3) 0.0410(6) Uani 1 1 d . . .
H6 H 0.7774 0.8863 0.4385 0.049 Uiso 1 1 calc R . .
C7 C 1.0199(3) 0.5724(2) 0.6998(2) 0.0294(5) Uani 1 1 d . . .
C8 C 1.1315(3) 0.4295(2) 0.8436(2) 0.0333(5) Uani 1 1 d . . .
C9 C 0.9540(3) 0.4296(2) 0.8319(2) 0.0307(5) Uani 1 1 d . . .
C10 C 0.8742(3) 0.3449(3) 0.9016(3) 0.0394(6) Uani 1 1 d . . .
H10 H 0.7569 0.3441 0.8952 0.047 Uiso 1 1 calc R . .
C11 C 0.9776(4) 0.2612(3) 0.9816(3) 0.0470(7) Uani 1 1 d . . .
H11 H 0.9276 0.2021 1.0289 0.056 Uiso 1 1 calc R . .
C12 C 1.1537(4) 0.2631(3) 0.9933(3) 0.0482(7) Uani 1 1 d . . .
H12 H 1.2180 0.2052 1.0482 0.058 Uiso 1 1 calc R . .
C13 C 1.2351(3) 0.3478(3) 0.9263(3) 0.0434(6) Uani 1 1 d . . .
H13 H 1.3532 0.3505 0.9356 0.052 Uiso 1 1 calc R . .
C14 C 0.6995(3) 0.8669(2) 0.6576(3) 0.0359(6) Uani 1 1 d . . .
H14 H 0.7501 0.9390 0.6252 0.043 Uiso 1 1 calc R . .
C15 C 0.5730(3) 0.8938(2) 0.7229(2) 0.0339(5) Uani 1 1 d . . .
C16 C 0.4730(3) 0.7947(2) 0.7685(2) 0.0315(5) Uani 1 1 d . . .
C17 C 0.3580(4) 0.8362(3) 0.8360(3) 0.0436(6) Uani 1 1 d . . .
H17 H 0.2925 0.7734 0.8687 0.052 Uiso 1 1 calc R . .
C18 C 0.3402(4) 0.9663(3) 0.8546(3) 0.0496(7) Uani 1 1 d . . .
H18 H 0.2631 0.9902 0.8996 0.059 Uiso 1 1 calc R . .
C19 C 0.4352(4) 1.0639(3) 0.8077(3) 0.0503(7) Uani 1 1 d . . .
H19 H 0.4211 1.1523 0.8197 0.060 Uiso 1 1 calc R . .
C20 C 0.5487(4) 1.0271(3) 0.7438(3) 0.0460(7) Uani 1 1 d . . .
H20 H 0.6130 1.0920 0.7127 0.055 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9093(16) . ?
Cu1 N3 1.9591(18) . ?
Cu1 N1 1.9786(19) . ?
Cu1 Cl1 2.2425(7) . ?
O1 C16 1.311(3) . ?
N1 C14 1.296(3) . ?
N1 C1 1.430(3) . ?
N2 C7 1.354(3) . ?
N2 C8 1.374(3) . ?
N2 H2 0.8600 . ?
N3 C7 1.336(3) . ?
N3 C9 1.395(3) . ?
C1 C6 1.386(4) . ?
C1 C2 1.413(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.454(3) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C13 1.390(4) . ?
C8 C9 1.405(3) . ?
C9 C10 1.384(3) . ?
C10 C11 1.388(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.426(3) . ?
C14 H14 0.9300 . ?
C15 C20 1.414(3) . ?
C15 C16 1.418(3) . ?
C16 C17 1.410(3) . ?
C17 C18 1.365(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.356(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N3 147.55(9) . . ?
O1 Cu1 N1 94.03(7) . . ?
N3 Cu1 N1 90.83(8) . . ?
O1 Cu1 Cl1 91.73(5) . . ?
N3 Cu1 Cl1 98.83(6) . . ?
N1 Cu1 Cl1 152.01(7) . . ?
C16 O1 Cu1 127.14(15) . . ?
C14 N1 C1 117.0(2) . . ?
C14 N1 Cu1 122.72(16) . . ?
C1 N1 Cu1 120.17(15) . . ?
C7 N2 C8 108.25(19) . . ?
C7 N2 H2 125.9 . . ?
C8 N2 H2 125.9 . . ?
C7 N3 C9 106.31(18) . . ?
C7 N3 Cu1 123.86(16) . . ?
C9 N3 Cu1 129.36(15) . . ?
C6 C1 C2 119.4(2) . . ?
C6 C1 N1 120.7(2) . . ?
C2 C1 N1 119.9(2) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 C7 119.2(2) . . ?
C1 C2 C7 122.1(2) . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N3 C7 N2 111.2(2) . . ?
N3 C7 C2 125.8(2) . . ?
N2 C7 C2 122.9(2) . . ?
N2 C8 C13 131.7(2) . . ?
N2 C8 C9 106.0(2) . . ?
C13 C8 C9 122.3(2) . . ?
C10 C9 N3 131.1(2) . . ?
C10 C9 C8 120.6(2) . . ?
N3 C9 C8 108.2(2) . . ?
C9 C10 C11 116.8(2) . . ?
C9 C10 H10 121.6 . . ?
C11 C10 H10 121.6 . . ?
C10 C11 C12 122.0(3) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C8 116.4(2) . . ?
C12 C13 H13 121.8 . . ?
C8 C13 H13 121.8 . . ?
N1 C14 C15 127.5(2) . . ?
N1 C14 H14 116.2 . . ?
C15 C14 H14 116.2 . . ?
C20 C15 C16 118.8(2) . . ?
C20 C15 C14 117.6(2) . . ?
C16 C15 C14 123.6(2) . . ?
O1 C16 C17 119.2(2) . . ?
O1 C16 C15 123.5(2) . . ?
C17 C16 C15 117.3(2) . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 121.3(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 118.4(3) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 C15 122.5(3) . . ?
C19 C20 H20 118.7 . . ?
C15 C20 H20 118.7 . . ?

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
N3 Cu1 O1 C16 84.5(2) . . . . ?
N1 Cu1 O1 C16 -13.4(2) . . . . ?
Cl1 Cu1 O1 C16 -166.0(2) . . . . ?
O1 Cu1 N1 C14 6.4(2) . . . . ?
N3 Cu1 N1 C14 -141.5(2) . . . . ?
Cl1 Cu1 N1 C14 107.8(2) . . . . ?
O1 Cu1 N1 C1 -170.17(18) . . . . ?
N3 Cu1 N1 C1 41.94(18) . . . . ?
Cl1 Cu1 N1 C1 -68.8(2) . . . . ?
O1 Cu1 N3 C7 -115.8(2) . . . . ?
N1 Cu1 N3 C7 -16.9(2) . . . . ?
Cl1 Cu1 N3 C7 136.69(18) . . . . ?
O1 Cu1 N3 C9 55.2(3) . . . . ?
N1 Cu1 N3 C9 154.1(2) . . . . ?
Cl1 Cu1 N3 C9 -52.3(2) . . . . ?
C14 N1 C1 C6 -38.0(3) . . . . ?
Cu1 N1 C1 C6 138.8(2) . . . . ?
C14 N1 C1 C2 142.6(2) . . . . ?
Cu1 N1 C1 C2 -40.6(3) . . . . ?
C6 C1 C2 C3 2.8(4) . . . . ?
N1 C1 C2 C3 -177.8(2) . . . . ?
C6 C1 C2 C7 -176.0(2) . . . . ?
N1 C1 C2 C7 3.4(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C7 C2 C3 C4 178.1(2) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 C6 1.9(4) . . . . ?
C2 C1 C6 C5 -2.5(4) . . . . ?
N1 C1 C6 C5 178.1(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C9 N3 C7 N2 -1.1(3) . . . . ?
Cu1 N3 C7 N2 171.63(16) . . . . ?
C9 N3 C7 C2 175.1(2) . . . . ?
Cu1 N3 C7 C2 -12.1(3) . . . . ?
C8 N2 C7 N3 0.7(3) . . . . ?
C8 N2 C7 C2 -175.7(2) . . . . ?
C3 C2 C7 N3 -153.1(2) . . . . ?
C1 C2 C7 N3 25.7(4) . . . . ?
C3 C2 C7 N2 22.7(4) . . . . ?
C1 C2 C7 N2 -158.5(2) . . . . ?
C7 N2 C8 C13 179.1(3) . . . . ?
C7 N2 C8 C9 0.0(3) . . . . ?
C7 N3 C9 C10 -177.2(3) . . . . ?
Cu1 N3 C9 C10 10.6(4) . . . . ?
C7 N3 C9 C8 1.1(3) . . . . ?
Cu1 N3 C9 C8 -171.13(17) . . . . ?
N2 C8 C9 C10 177.8(2) . . . . ?
C13 C8 C9 C10 -1.4(4) . . . . ?
N2 C8 C9 N3 -0.7(3) . . . . ?
C13 C8 C9 N3 -179.9(2) . . . . ?
N3 C9 C10 C11 177.9(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C11 C12 C13 C8 -1.6(4) . . . . ?
N2 C8 C13 C12 -176.7(3) . . . . ?
C9 C8 C13 C12 2.3(4) . . . . ?
C1 N1 C14 C15 177.7(2) . . . . ?
Cu1 N1 C14 C15 1.0(4) . . . . ?
N1 C14 C15 C20 173.7(3) . . . . ?
N1 C14 C15 C16 -5.5(4) . . . . ?
Cu1 O1 C16 C17 -166.36(19) . . . . ?
Cu1 O1 C16 C15 12.8(4) . . . . ?
C20 C15 C16 O1 179.0(2) . . . . ?
C14 C15 C16 O1 -1.8(4) . . . . ?
C20 C15 C16 C17 -1.8(4) . . . . ?
C14 C15 C16 C17 177.4(3) . . . . ?
O1 C16 C17 C18 -179.4(3) . . . . ?
C15 C16 C17 C18 1.4(4) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C20 -0.9(5) . . . . ?
C18 C19 C20 C15 0.4(5) . . . . ?
C16 C15 C20 C19 1.0(4) . . . . ?
C14 C15 C20 C19 -178.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_ps121_0m
_database_code_depnum_ccdc_archive 'CCDC 953037'
_audit_update_record             
;
2013-07-29 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;



_audit_creation_date             2013-06-13T23:35:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C24 H20 N4 O8'
_chemical_formula_weight         492.44
_chemical_absolute_configuration unk



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

_cell_length_a                   14.7508(11)
_cell_length_b                   9.8446(8)
_cell_length_c                   13.9881(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.028(3)
_cell_angle_gamma                90
_cell_volume                     2031.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)

_exptl_crystal_density_diffrn    1.61
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_special_details           
;
 ?
;
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   none
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_number            5292
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         22.92
_diffrn_reflns_theta_full        22.92
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             2413
_reflns_number_gt                2121
_reflns_threshold_expression     >2sigma(I)
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0837P)²+0.5103P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0003(8)
_refine_ls_number_reflns         2413
_refine_ls_number_parameters     265
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.045
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.033

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0906(2) 0.2989(4) 0.1620(3) 0.0483(9) Uani 1 1 d . . .
C2 C 0.1049(3) 0.3699(4) 0.0784(3) 0.0597(11) Uani 1 1 d . . .
H2 H 0.1523 0.4314 0.0727 0.072 Uiso 1 1 calc R . .
C3 C 0.0447(3) 0.3440(5) 0.0039(3) 0.0656(12) Uani 1 1 d . . .
H3 H 0.0521 0.3879 -0.0543 0.079 Uiso 1 1 calc R . .
C4 C -0.0268(3) 0.2535(5) 0.0143(3) 0.0675(12) Uani 1 1 d . . .
H4 H -0.0672 0.24 -0.0367 0.081 Uiso 1 1 calc R . .
C5 C -0.0392(3) 0.1837(4) 0.0978(3) 0.0615(11) Uani 1 1 d . . .
H5 H -0.0868 0.1225 0.104 0.074 Uiso 1 1 calc R . .
C6 C 0.0207(2) 0.2069(4) 0.1717(3) 0.0514(10) Uani 1 1 d . . .
C7 C 0.0940(2) 0.2033(4) 0.3048(3) 0.0480(9) Uani 1 1 d . . .
C8 C 0.1291(2) 0.1831(4) 0.4030(3) 0.0498(10) Uani 1 1 d . . .
C9 C 0.1013(3) 0.0758(4) 0.4605(4) 0.0730(13) Uani 1 1 d . . .
H9 H 0.0614 0.0107 0.4362 0.088 Uiso 1 1 calc R . .
C10 C 0.1333(3) 0.0663(6) 0.5544(3) 0.0812(15) Uani 1 1 d . . .
H10 H 0.1161 -0.0054 0.5933 0.097 Uiso 1 1 calc R . .
C11 C 0.1905(3) 0.1645(5) 0.5879(3) 0.0728(13) Uani 1 1 d . . .
H11 H 0.2122 0.158 0.6506 0.087 Uiso 1 1 calc R . .
C12 C 0.2175(3) 0.2721(5) 0.5339(3) 0.0602(11) Uani 1 1 d . . .
H12 H 0.2552 0.3384 0.5602 0.072 Uiso 1 1 calc R . .
C13 C 0.1883(2) 0.2814(4) 0.4403(3) 0.0478(10) Uani 1 1 d . . .
C14 C 0.2196(2) 0.3663(4) 0.2788(2) 0.0409(8) Uani 1 1 d . . .
H14 H 0.2211 0.4543 0.2461 0.049 Uiso 1 1 calc R . .
C15 C 0.3044(2) 0.2878(3) 0.2542(2) 0.0387(8) Uani 1 1 d . . .
C16 C 0.3060(3) 0.1548(4) 0.2245(3) 0.0556(11) Uani 1 1 d . . .
H16 H 0.2517 0.1071 0.2181 0.067 Uiso 1 1 calc R . .
C17 C 0.3872(3) 0.0900(4) 0.2039(3) 0.0698(13) Uani 1 1 d . . .
H17 H 0.3869 0.0005 0.1825 0.084 Uiso 1 1 calc R . .
C18 C 0.4680(3) 0.1586(5) 0.2153(3) 0.0651(12) Uani 1 1 d . . .
H18 H 0.5226 0.115 0.2033 0.078 Uiso 1 1 calc R . .
C19 C 0.4675(3) 0.2937(4) 0.2450(3) 0.0570(11) Uani 1 1 d . . .
H19 H 0.5218 0.3411 0.2521 0.068 Uiso 1 1 calc R . .
C20 C 0.3866(2) 0.3570(4) 0.2638(2) 0.0440(9) Uani 1 1 d . . .
C21 C 0.4087(5) 0.8878(6) 0.4399(5) 0.127(2) Uani 1 1 d . . .
H21A H 0.387 0.9514 0.3927 0.19 Uiso 1 1 calc R . .
H21B H 0.4683 0.8577 0.4235 0.19 Uiso 1 1 calc R . .
H21C H 0.411 0.931 0.5014 0.19 Uiso 1 1 calc R . .
C22 C 0.2693(4) 0.7704(6) 0.3788(5) 0.107(2) Uani 1 1 d . . .
H22A H 0.269 0.8517 0.3409 0.161 Uiso 1 1 calc R . .
H22B H 0.2149 0.7664 0.4154 0.161 Uiso 1 1 calc R . .
H22C H 0.2721 0.6926 0.3376 0.161 Uiso 1 1 calc R . .
C23 C 0.3633(3) 0.6686(5) 0.5014(3) 0.0650(12) Uani 1 1 d . . .
H23A H 0.4234 0.6361 0.4861 0.078 Uiso 1 1 calc R . .
H23B H 0.3685 0.7083 0.5647 0.078 Uiso 1 1 calc R . .
N1 N 0.0243(2) 0.1456(3) 0.2633(2) 0.0560(9) Uani 1 1 d . . .
N2 N 0.13650(19) 0.2956(3) 0.2496(2) 0.0504(8) Uani 1 1 d . . .
N3 N 0.21140(19) 0.3901(3) 0.3815(2) 0.0503(8) Uani 1 1 d . . .
H3A H 0.2207 0.4696 0.4052 0.06 Uiso 1 1 calc R . .
N4 N 0.3474(3) 0.7711(4) 0.4429(3) 0.0740(11) Uani 1 1 d . . .
O1 O 0.38112(16) 0.4871(3) 0.29523(19) 0.0583(8) Uani 1 1 d . . .
H1 H 0.4314 0.5225 0.2935 0.087 Uiso 1 1 calc R . .
O2 O 0.31707(19) 0.5668(3) 0.5107(2) 0.0643(8) Uani 1 1 d . . .
H2A H 0.2919 0.5484 0.4596 0.096 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(6) . ?
C1 C6 1.381(5) . ?
C1 N2 1.389(5) . ?
C2 C3 1.381(6) . ?
C2 H2 0.93 . ?
C3 C4 1.390(6) . ?
C3 H3 0.93 . ?
C4 C5 1.371(6) . ?
C4 H4 0.93 . ?
C5 C6 1.367(5) . ?
C5 H5 0.93 . ?
C6 N1 1.416(5) . ?
C7 N1 1.302(5) . ?
C7 N2 1.354(4) . ?
C7 C8 1.473(5) . ?
C8 C13 1.398(5) . ?
C8 C9 1.395(6) . ?
C9 C10 1.390(7) . ?
C9 H9 0.93 . ?
C10 C11 1.361(7) . ?
C10 H10 0.93 . ?
C11 C12 1.364(6) . ?
C11 H11 0.93 . ?
C12 C13 1.375(5) . ?
C12 H12 0.93 . ?
C13 N3 1.395(5) . ?
C14 N2 1.461(4) . ?
C14 N3 1.463(5) . ?
C14 C15 1.515(5) . ?
C14 H14 0.98 . ?
C15 C16 1.374(5) . ?
C15 C20 1.396(5) . ?
C16 C17 1.392(5) . ?
C16 H16 0.93 . ?
C17 C18 1.377(6) . ?
C17 H17 0.93 . ?
C18 C19 1.394(6) . ?
C18 H18 0.93 . ?
C19 C20 1.376(5) . ?
C19 H19 0.93 . ?
C20 O1 1.356(5) . ?
C21 N4 1.463(6) . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
C22 N4 1.447(7) . ?
C22 H22A 0.96 . ?
C22 H22B 0.96 . ?
C22 H22C 0.96 . ?
C23 O2 1.220(5) . ?
C23 N4 1.318(6) . ?
C23 H23A 0.97 . ?
C23 H23B 0.97 . ?
N3 H3A 0.86 . ?
O1 H1 0.82 . ?
O2 H2A 0.82 . ?

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 C6 122.7(4) . . ?
C2 C1 N2 132.8(4) . . ?
C6 C1 N2 104.5(3) . . ?
C1 C2 C3 116.1(4) . . ?
C1 C2 H2 122 . . ?
C3 C2 H2 122 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C6 C5 C4 117.8(4) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C5 C6 C1 120.6(4) . . ?
C5 C6 N1 128.8(4) . . ?
C1 C6 N1 110.6(3) . . ?
N1 C7 N2 114.1(4) . . ?
N1 C7 C8 128.3(3) . . ?
N2 C7 C8 117.6(3) . . ?
C13 C8 C9 119.8(4) . . ?
C13 C8 C7 117.5(3) . . ?
C9 C8 C7 122.5(3) . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 118.5(4) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C12 123.1(5) . . ?
C10 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 N3 122.5(3) . . ?
C12 C13 C8 119.5(3) . . ?
N3 C13 C8 117.9(3) . . ?
N2 C14 N3 105.5(3) . . ?
N2 C14 C15 112.7(3) . . ?
N3 C14 C15 112.8(3) . . ?
N2 C14 H14 108.6 . . ?
N3 C14 H14 108.6 . . ?
C15 C14 H14 108.6 . . ?
C16 C15 C20 118.4(3) . . ?
C16 C15 C14 125.0(3) . . ?
C20 C15 C14 116.7(3) . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 119.6(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
O1 C20 C19 123.1(3) . . ?
O1 C20 C15 115.8(3) . . ?
C19 C20 C15 121.1(3) . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 N4 127.0(4) . . ?
O2 C23 H23A 105.6 . . ?
N4 C23 H23A 105.6 . . ?
O2 C23 H23B 105.6 . . ?
N4 C23 H23B 105.6 . . ?
H23A C23 H23B 106.1 . . ?
C7 N1 C6 103.5(3) . . ?
C7 N2 C1 107.2(3) . . ?
C7 N2 C14 123.8(3) . . ?
C1 N2 C14 128.9(3) . . ?
C13 N3 C14 118.8(3) . . ?
C13 N3 H3A 120.6 . . ?
C14 N3 H3A 120.6 . . ?
C23 N4 C22 120.7(4) . . ?
C23 N4 C21 121.1(5) . . ?
C22 N4 C21 118.2(5) . . ?
C20 O1 H1 109.5 . . ?
C23 O2 H2A 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
C6 C1 C2 C3 0.1(6) . . . . ?
N2 C1 C2 C3 178.7(4) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C2 C3 C4 C5 -1.7(6) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C4 C5 C6 N1 -178.0(4) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
N2 C1 C6 C5 -179.9(3) . . . . ?
C2 C1 C6 N1 177.7(3) . . . . ?
N2 C1 C6 N1 -1.1(4) . . . . ?
N1 C7 C8 C13 -162.8(4) . . . . ?
N2 C7 C8 C13 15.2(5) . . . . ?
N1 C7 C8 C9 13.3(6) . . . . ?
N2 C7 C8 C9 -168.8(4) . . . . ?
C13 C8 C9 C10 -0.7(7) . . . . ?
C7 C8 C9 C10 -176.6(4) . . . . ?
C8 C9 C10 C11 1.0(8) . . . . ?
C9 C10 C11 C12 0.3(8) . . . . ?
C10 C11 C12 C13 -1.9(7) . . . . ?
C11 C12 C13 N3 178.4(4) . . . . ?
C11 C12 C13 C8 2.2(6) . . . . ?
C9 C8 C13 C12 -0.9(6) . . . . ?
C7 C8 C13 C12 175.2(3) . . . . ?
C9 C8 C13 N3 -177.4(3) . . . . ?
C7 C8 C13 N3 -1.2(5) . . . . ?
N2 C14 C15 C16 -11.6(5) . . . . ?
N3 C14 C15 C16 107.7(4) . . . . ?
N2 C14 C15 C20 169.1(3) . . . . ?
N3 C14 C15 C20 -71.6(4) . . . . ?
C20 C15 C16 C17 -0.4(5) . . . . ?
C14 C15 C16 C17 -179.6(4) . . . . ?
C15 C16 C17 C18 1.5(6) . . . . ?
C16 C17 C18 C19 -1.7(6) . . . . ?
C17 C18 C19 C20 0.8(6) . . . . ?
C18 C19 C20 O1 178.3(4) . . . . ?
C18 C19 C20 C15 0.3(6) . . . . ?
C16 C15 C20 O1 -178.7(3) . . . . ?
C14 C15 C20 O1 0.6(4) . . . . ?
C16 C15 C20 C19 -0.5(5) . . . . ?
C14 C15 C20 C19 178.7(3) . . . . ?
N2 C7 N1 C6 -0.2(4) . . . . ?
C8 C7 N1 C6 177.8(4) . . . . ?
C5 C6 N1 C7 179.5(4) . . . . ?
C1 C6 N1 C7 0.9(4) . . . . ?
N1 C7 N2 C1 -0.5(4) . . . . ?
C8 C7 N2 C1 -178.7(3) . . . . ?
N1 C7 N2 C14 -175.8(3) . . . . ?
C8 C7 N2 C14 5.9(5) . . . . ?
C2 C1 N2 C7 -177.8(4) . . . . ?
C6 C1 N2 C7 1.0(4) . . . . ?
C2 C1 N2 C14 -2.7(6) . . . . ?
C6 C1 N2 C14 176.0(3) . . . . ?
N3 C14 N2 C7 -36.0(4) . . . . ?
C15 C14 N2 C7 87.4(4) . . . . ?
N3 C14 N2 C1 149.7(3) . . . . ?
C15 C14 N2 C1 -86.9(4) . . . . ?
C12 C13 N3 C14 149.5(3) . . . . ?
C8 C13 N3 C14 -34.2(5) . . . . ?
N2 C14 N3 C13 50.1(4) . . . . ?
C15 C14 N3 C13 -73.3(4) . . . . ?
O2 C23 N4 C22 -1.4(7) . . . . ?
O2 C23 N4 C21 179.4(5) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
