# 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 2017

####################################################################### 
# 
# 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_me995
_database_code_depnum_ccdc_archive 'CCDC 1449773'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H28 Cu2 N8 O6, 2(C H4 O)'
_chemical_formula_sum            'C12 H18 Cu N4 O4'
_chemical_formula_weight         345.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.7557(4)
_cell_length_b                   10.0442(5)
_cell_length_c                   10.1321(5)
_cell_angle_alpha                78.380(4)
_cell_angle_beta                 78.554(5)
_cell_angle_gamma                68.519(5)
_cell_volume                     712.65(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4616
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      28.28

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.554
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.6048
_exptl_absorpt_correction_T_max  0.8718
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'

_exptl_special_details           
;
  ?
;

_diffrn_ambient_temperature      293(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  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4609
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3131
_reflns_number_gt                2585
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2000)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2000)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0619P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3131
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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 0.32677(4) 0.40585(3) 0.02324(3) 0.02737(13) Uani 1 1 d . . .
O1 O 0.4525(3) 0.4141(2) -0.15686(18) 0.0318(4) Uani 1 1 d . . .
C1 C 0.6008(3) 0.3119(3) -0.2078(2) 0.0245(5) Uani 1 1 d . . .
C2 C 0.6621(4) 0.3306(3) -0.3478(3) 0.0318(6) Uani 1 1 d . . .
H2A H 0.5982 0.4141 -0.4016 0.038 Uiso 1 1 calc R . .
C3 C 0.8146(4) 0.2284(3) -0.4078(3) 0.0321(6) Uani 1 1 d . . .
H3A H 0.8510 0.2432 -0.5012 0.039 Uiso 1 1 calc R . .
C4 C 0.9143(4) 0.1036(3) -0.3298(3) 0.0340(6) Uani 1 1 d . . .
H4A H 1.0176 0.0349 -0.3703 0.041 Uiso 1 1 calc R . .
C5 C 0.8592(4) 0.0830(3) -0.1935(3) 0.0289(6) Uani 1 1 d . . .
H5A H 0.9274 -0.0001 -0.1414 0.035 Uiso 1 1 calc R . .
C6 C 0.7012(3) 0.1839(3) -0.1286(2) 0.0238(5) Uani 1 1 d . . .
C7 C 0.6486(3) 0.1466(3) 0.0144(2) 0.0244(5) Uani 1 1 d . . .
H7A H 0.7256 0.0607 0.0574 0.029 Uiso 1 1 calc R . .
N7 N 0.5039(3) 0.2220(2) 0.0883(2) 0.0230(4) Uani 1 1 d . . .
C8 C 0.4679(3) 0.1748(3) 0.2364(2) 0.0242(5) Uani 1 1 d . . .
C9 C 0.5381(4) 0.0120(3) 0.2781(3) 0.0326(6) Uani 1 1 d . . .
H9A H 0.4795 -0.0317 0.2327 0.049 Uiso 1 1 calc R . .
H9B H 0.5080 -0.0098 0.3748 0.049 Uiso 1 1 calc R . .
H9C H 0.6713 -0.0253 0.2532 0.049 Uiso 1 1 calc R . .
C10 C 0.2562(4) 0.2343(3) 0.2729(3) 0.0313(6) Uani 1 1 d . . .
H10A H 0.1985 0.1783 0.2406 0.038 Uiso 1 1 calc R . .
H10B H 0.2228 0.2292 0.3708 0.038 Uiso 1 1 calc R . .
O10 O 0.1926(3) 0.3822(2) 0.20924(18) 0.0343(5) Uani 1 1 d . . .
H10D H 0.0891 0.4250 0.2479 0.041 Uiso 1 1 calc R . .
C11 C 0.5586(4) 0.2482(3) 0.3075(3) 0.0286(6) Uani 1 1 d . . .
H11A H 0.5006 0.3522 0.2877 0.034 Uiso 1 1 calc R . .
H11B H 0.5355 0.2210 0.4050 0.034 Uiso 1 1 calc R . .
O11 O 0.7527(3) 0.2106(2) 0.26640(19) 0.0347(5) Uani 1 1 d . . .
H11C H 0.7729 0.2350 0.1842 0.052 Uiso 1 1 calc R . .
C20 C -0.1808(5) 0.6141(3) 0.3788(3) 0.0466(8) Uani 1 1 d . . .
H20A H -0.0702 0.6403 0.3517 0.056 Uiso 1 1 d R . .
H20B H -0.2878 0.6956 0.3546 0.056 Uiso 1 1 d R . .
H20C H -0.1959 0.5852 0.4754 0.056 Uiso 1 1 d R . .
O20 O -0.1527(3) 0.4961(2) 0.31036(19) 0.0346(4) Uani 1 1 d . . .
H20D H -0.2294 0.5201 0.2572 0.042 Uiso 1 1 calc R . .
N10 N 0.1622(3) 0.6019(2) -0.0304(2) 0.0365(6) Uani 1 1 d . . .
N11 N 0.0113(3) 0.6733(2) 0.0175(2) 0.0284(5) Uani 1 1 d . . .
N12 N -0.1354(4) 0.7468(3) 0.0548(3) 0.0511(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.8920(18) . ?
Cu1 N7 1.934(2) . ?
Cu1 N10 1.951(2) . ?
Cu1 O10 1.9783(18) . ?
O1 C1 1.325(3) . ?
C1 C2 1.401(3) . ?
C1 C6 1.415(3) . ?
C2 C3 1.378(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.359(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.414(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.437(3) . ?
C7 N7 1.291(3) . ?
C7 H7A 0.9300 . ?
N7 C8 1.482(3) . ?
C8 C9 1.520(3) . ?
C8 C10 1.523(4) . ?
C8 C11 1.533(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O10 1.438(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
O10 H10D 0.8200 . ?
C11 O11 1.407(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
O11 H11C 0.8200 . ?
C20 O20 1.420(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9599 . ?
O20 H20D 0.8200 . ?
N10 N11 1.191(3) . ?
N11 N12 1.144(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
O1 Cu1 N7 94.93(8) . . ?
O1 Cu1 N10 86.91(8) . . ?
N7 Cu1 N10 172.99(9) . . ?
O1 Cu1 O10 175.16(8) . . ?
N7 Cu1 O10 82.78(8) . . ?
N10 Cu1 O10 95.87(8) . . ?
C1 O1 Cu1 126.74(16) . . ?
O1 C1 C2 118.6(2) . . ?
O1 C1 C6 123.6(2) . . ?
C2 C1 C6 117.8(2) . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2A 119.1 . . ?
C1 C2 H2A 119.1 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 122.0(2) . . ?
C4 C5 H5A 119.0 . . ?
C6 C5 H5A 119.0 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 117.2(2) . . ?
C1 C6 C7 123.9(2) . . ?
N7 C7 C6 125.7(2) . . ?
N7 C7 H7A 117.2 . . ?
C6 C7 H7A 117.2 . . ?
C7 N7 C8 120.7(2) . . ?
C7 N7 Cu1 124.83(18) . . ?
C8 N7 Cu1 114.37(15) . . ?
N7 C8 C9 114.5(2) . . ?
N7 C8 C10 105.16(19) . . ?
C9 C8 C10 109.7(2) . . ?
N7 C8 C11 106.90(19) . . ?
C9 C8 C11 110.8(2) . . ?
C10 C8 C11 109.5(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O10 C10 C8 107.7(2) . . ?
O10 C10 H10A 110.2 . . ?
C8 C10 H10A 110.2 . . ?
O10 C10 H10B 110.2 . . ?
C8 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 O10 Cu1 111.32(15) . . ?
C10 O10 H10D 109.5 . . ?
Cu1 O10 H10D 134.7 . . ?
O11 C11 C8 112.7(2) . . ?
O11 C11 H11A 109.1 . . ?
C8 C11 H11A 109.1 . . ?
O11 C11 H11B 109.1 . . ?
C8 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 O11 H11C 109.5 . . ?
O20 C20 H20A 106.5 . . ?
O20 C20 H20B 111.9 . . ?
H20A C20 H20B 109.5 . . ?
O20 C20 H20C 110.0 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C20 O20 H20D 109.5 . . ?
N11 N10 Cu1 132.82(19) . . ?
N12 N11 N10 175.3(3) . . ?

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
N7 Cu1 O1 C1 5.4(2) . . . . ?
N10 Cu1 O1 C1 178.7(2) . . . . ?
O10 Cu1 O1 C1 -56.0(10) . . . . ?
Cu1 O1 C1 C2 172.77(18) . . . . ?
Cu1 O1 C1 C6 -7.0(4) . . . . ?
O1 C1 C2 C3 -179.6(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 C1 -1.7(4) . . . . ?
C4 C5 C6 C7 176.1(2) . . . . ?
O1 C1 C6 C5 -179.2(2) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
O1 C1 C6 C7 3.2(4) . . . . ?
C2 C1 C6 C7 -176.5(2) . . . . ?
C5 C6 C7 N7 -176.4(2) . . . . ?
C1 C6 C7 N7 1.2(4) . . . . ?
C6 C7 N7 C8 -177.8(2) . . . . ?
C6 C7 N7 Cu1 -1.4(4) . . . . ?
O1 Cu1 N7 C7 -1.3(2) . . . . ?
N10 Cu1 N7 C7 -106.3(7) . . . . ?
O10 Cu1 N7 C7 174.4(2) . . . . ?
O1 Cu1 N7 C8 175.24(16) . . . . ?
N10 Cu1 N7 C8 70.3(7) . . . . ?
O10 Cu1 N7 C8 -9.04(16) . . . . ?
C7 N7 C8 C9 -30.6(3) . . . . ?
Cu1 N7 C8 C9 152.66(19) . . . . ?
C7 N7 C8 C10 -151.2(2) . . . . ?
Cu1 N7 C8 C10 32.1(2) . . . . ?
C7 N7 C8 C11 92.5(3) . . . . ?
Cu1 N7 C8 C11 -84.2(2) . . . . ?
N7 C8 C10 O10 -45.7(3) . . . . ?
C9 C8 C10 O10 -169.3(2) . . . . ?
C11 C8 C10 O10 68.9(3) . . . . ?
C8 C10 O10 Cu1 40.6(3) . . . . ?
O1 Cu1 O10 C10 43.6(10) . . . . ?
N7 Cu1 O10 C10 -18.35(18) . . . . ?
N10 Cu1 O10 C10 168.57(18) . . . . ?
N7 C8 C11 O11 -59.9(3) . . . . ?
C9 C8 C11 O11 65.5(3) . . . . ?
C10 C8 C11 O11 -173.3(2) . . . . ?
O1 Cu1 N10 N11 161.8(3) . . . . ?
N7 Cu1 N10 N11 -92.8(7) . . . . ?
O10 Cu1 N10 N11 -14.3(3) . . . . ?
Cu1 N10 N11 N12 -153(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.884
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.076


#
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag
#
####################################################################### 
# 
# 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_tri
_database_code_depnum_ccdc_archive 'CCDC 1449774'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
  ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N3 O'
_chemical_formula_sum            'C16 H15 N3 O'
_chemical_formula_weight         265.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.685(3)
_cell_length_b                   5.5450(10)
_cell_length_c                   16.850(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.38(3)
_cell_angle_gamma                90.00
_cell_volume                     1349.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8687
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'

_exptl_special_details           
;
  ?
;

_diffrn_ambient_temperature      293(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  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8243
_diffrn_reflns_av_R_equivalents  0.1386
_diffrn_reflns_av_sigmaI/netI    0.1805
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         28.49
_reflns_number_total             3089
_reflns_number_gt                918
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2000)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2000)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.1560P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3089
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2969
_refine_ls_R_factor_gt           0.0984
_refine_ls_wR_factor_ref         0.3598
_refine_ls_wR_factor_gt          0.2496
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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
N1 N 0.2946(4) 0.9659(9) 0.2936(3) 0.0581(13) Uani 1 1 d . . .
N2 N 0.3007(4) 1.2000(10) 0.2773(3) 0.0760(17) Uani 1 1 d . . .
N3 N 0.2222(4) 1.2625(9) 0.2292(3) 0.0693(16) Uani 1 1 d . . .
C4 C 0.1679(4) 1.0665(10) 0.2163(3) 0.0520(15) Uani 1 1 d . . .
C5 C 0.2143(5) 0.8812(11) 0.2586(4) 0.0610(17) Uani 1 1 d . . .
H5A H 0.1929 0.7243 0.2619 0.073 Uiso 1 1 calc R . .
C11 C 0.3660(4) 0.8395(13) 0.3495(4) 0.0689(18) Uani 1 1 d . . .
H11A H 0.3671 0.6711 0.3320 0.083 Uiso 1 1 calc R . .
C12 C 0.4592(5) 0.9494(13) 0.3469(4) 0.080(2) Uani 1 1 d . . .
H12A H 0.4588 1.1165 0.3639 0.096 Uiso 1 1 calc R . .
H12B H 0.5059 0.8654 0.3850 0.096 Uiso 1 1 calc R . .
O12 O 0.4839(3) 0.9395(9) 0.2690(3) 0.0887(16) Uani 1 1 d . . .
H12C H 0.4940 1.0763 0.2543 0.133 Uiso 1 1 calc R . .
C13 C 0.3468(4) 0.8429(11) 0.4345(4) 0.0596(16) Uani 1 1 d . . .
C14 C 0.3755(4) 0.6561(12) 0.4858(4) 0.0702(19) Uani 1 1 d . . .
H14A H 0.4066 0.5267 0.4677 0.084 Uiso 1 1 calc R . .
C15 C 0.3592(5) 0.6563(15) 0.5642(4) 0.083(2) Uani 1 1 d . . .
H15A H 0.3793 0.5284 0.5986 0.100 Uiso 1 1 calc R . .
C16 C 0.3132(5) 0.8456(16) 0.5906(4) 0.083(2) Uani 1 1 d . . .
H16A H 0.3022 0.8468 0.6432 0.099 Uiso 1 1 calc R . .
C17 C 0.2837(5) 1.0298(13) 0.5411(4) 0.0715(19) Uani 1 1 d . . .
H17A H 0.2519 1.1572 0.5595 0.086 Uiso 1 1 calc R . .
C18 C 0.3002(4) 1.0317(12) 0.4628(4) 0.0672(18) Uani 1 1 d . . .
H18A H 0.2799 1.1609 0.4290 0.081 Uiso 1 1 calc R . .
C41 C 0.0750(4) 1.0688(10) 0.1658(3) 0.0530(15) Uani 1 1 d . . .
C42 C 0.0475(5) 1.2567(12) 0.1145(4) 0.0724(19) Uani 1 1 d . . .
H42A H 0.0881 1.3825 0.1099 0.087 Uiso 1 1 calc R . .
C43 C -0.0420(5) 1.2584(14) 0.0689(4) 0.084(2) Uani 1 1 d . . .
H43A H -0.0616 1.3878 0.0350 0.101 Uiso 1 1 calc R . .
C44 C -0.0990(5) 1.0762(15) 0.0740(5) 0.081(2) Uani 1 1 d . . .
H44A H -0.1574 1.0756 0.0416 0.097 Uiso 1 1 calc R . .
C45 C -0.0739(5) 0.8927(15) 0.1250(5) 0.089(2) Uani 1 1 d . . .
H45A H -0.1158 0.7703 0.1298 0.106 Uiso 1 1 calc R . .
C46 C 0.0151(5) 0.8854(12) 0.1708(4) 0.0740(19) Uani 1 1 d . . .
H46A H 0.0333 0.7552 0.2047 0.089 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
N1 C5 1.308(7) . ?
N1 N2 1.334(6) . ?
N1 C11 1.456(8) . ?
N2 N3 1.330(7) . ?
N3 C4 1.342(7) . ?
C4 C5 1.361(7) . ?
C4 C41 1.472(8) . ?
C5 H5A 0.9300 . ?
C11 C12 1.506(9) . ?
C11 C13 1.510(9) . ?
C11 H11A 0.9800 . ?
C12 O12 1.424(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O12 H12C 0.8200 . ?
C13 C14 1.366(8) . ?
C13 C18 1.381(8) . ?
C14 C15 1.385(10) . ?
C14 H14A 0.9300 . ?
C15 C16 1.365(10) . ?
C15 H15A 0.9300 . ?
C16 C17 1.340(9) . ?
C16 H16A 0.9300 . ?
C17 C18 1.384(9) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C41 C46 1.357(8) . ?
C41 C42 1.368(8) . ?
C42 C43 1.398(9) . ?
C42 H42A 0.9300 . ?
C43 C44 1.325(9) . ?
C43 H43A 0.9300 . ?
C44 C45 1.340(9) . ?
C44 H44A 0.9300 . ?
C45 C46 1.393(9) . ?
C45 H45A 0.9300 . ?
C46 H46A 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
C5 N1 N2 110.2(5) . . ?
C5 N1 C11 127.2(5) . . ?
N2 N1 C11 122.3(6) . . ?
N3 N2 N1 107.2(5) . . ?
N2 N3 C4 108.2(5) . . ?
N3 C4 C5 107.4(5) . . ?
N3 C4 C41 123.3(5) . . ?
C5 C4 C41 129.3(6) . . ?
N1 C5 C4 106.9(5) . . ?
N1 C5 H5A 126.5 . . ?
C4 C5 H5A 126.5 . . ?
N1 C11 C12 109.8(6) . . ?
N1 C11 C13 111.8(5) . . ?
C12 C11 C13 110.4(5) . . ?
N1 C11 H11A 108.2 . . ?
C12 C11 H11A 108.2 . . ?
C13 C11 H11A 108.2 . . ?
O12 C12 C11 113.2(5) . . ?
O12 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
O12 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 O12 H12C 109.5 . . ?
C14 C13 C18 118.2(6) . . ?
C14 C13 C11 120.1(6) . . ?
C18 C13 C11 121.7(6) . . ?
C13 C14 C15 121.0(7) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C16 C15 C14 119.5(7) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
C17 C16 C15 120.5(7) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C16 C17 C18 120.4(7) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C13 C18 C17 120.4(6) . . ?
C13 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C46 C41 C42 119.3(6) . . ?
C46 C41 C4 120.1(5) . . ?
C42 C41 C4 120.6(6) . . ?
C41 C42 C43 119.6(6) . . ?
C41 C42 H42A 120.2 . . ?
C43 C42 H42A 120.2 . . ?
C44 C43 C42 120.1(7) . . ?
C44 C43 H43A 119.9 . . ?
C42 C43 H43A 119.9 . . ?
C43 C44 C45 121.1(7) . . ?
C43 C44 H44A 119.5 . . ?
C45 C44 H44A 119.5 . . ?
C44 C45 C46 120.0(7) . . ?
C44 C45 H45A 120.0 . . ?
C46 C45 H45A 120.0 . . ?
C41 C46 C45 119.8(6) . . ?
C41 C46 H46A 120.1 . . ?
C45 C46 H46A 120.1 . . ?

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
C5 N1 N2 N3 -1.2(7) . . . . ?
C11 N1 N2 N3 -175.6(5) . . . . ?
N1 N2 N3 C4 0.2(7) . . . . ?
N2 N3 C4 C5 0.8(7) . . . . ?
N2 N3 C4 C41 179.8(5) . . . . ?
N2 N1 C5 C4 1.7(7) . . . . ?
C11 N1 C5 C4 175.8(5) . . . . ?
N3 C4 C5 N1 -1.5(7) . . . . ?
C41 C4 C5 N1 179.6(5) . . . . ?
C5 N1 C11 C12 154.8(6) . . . . ?
N2 N1 C11 C12 -31.7(8) . . . . ?
C5 N1 C11 C13 -82.3(8) . . . . ?
N2 N1 C11 C13 91.2(7) . . . . ?
N1 C11 C12 O12 -59.6(7) . . . . ?
C13 C11 C12 O12 176.7(5) . . . . ?
N1 C11 C13 C14 149.5(6) . . . . ?
C12 C11 C13 C14 -88.0(7) . . . . ?
N1 C11 C13 C18 -30.5(9) . . . . ?
C12 C11 C13 C18 92.0(7) . . . . ?
C18 C13 C14 C15 -0.4(9) . . . . ?
C11 C13 C14 C15 179.6(6) . . . . ?
C13 C14 C15 C16 0.3(10) . . . . ?
C14 C15 C16 C17 0.3(11) . . . . ?
C15 C16 C17 C18 -0.6(10) . . . . ?
C14 C13 C18 C17 0.1(9) . . . . ?
C11 C13 C18 C17 -179.9(6) . . . . ?
C16 C17 C18 C13 0.4(10) . . . . ?
N3 C4 C41 C46 -163.7(6) . . . . ?
C5 C4 C41 C46 15.0(9) . . . . ?
N3 C4 C41 C42 15.2(8) . . . . ?
C5 C4 C41 C42 -166.1(6) . . . . ?
C46 C41 C42 C43 0.8(9) . . . . ?
C4 C41 C42 C43 -178.1(6) . . . . ?
C41 C42 C43 C44 -1.7(11) . . . . ?
C42 C43 C44 C45 2.9(12) . . . . ?
C43 C44 C45 C46 -3.3(12) . . . . ?
C42 C41 C46 C45 -1.2(9) . . . . ?
C4 C41 C46 C45 177.7(6) . . . . ?
C44 C45 C46 C41 2.4(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.901
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.071

#
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared) and status flag
#
