# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_L1
_audit_creation_date             2014-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H9 N3'
_chemical_formula_sum            'C12 H9 N3'
_chemical_formula_weight         195.22
_chemical_absolute_configuration unk
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   5.0020(6)
_cell_length_b                   13.078(2)
_cell_length_c                   14.257(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     932.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2132
_cell_measurement_temperature    120.0(10)
_cell_measurement_theta_max      73.5880
_cell_measurement_theta_min      3.0986
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3567
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.73
_diffrn_reflns_theta_min         4.59
_diffrn_ambient_temperature      120.0(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1794301000
_diffrn_orient_matrix_UB_12      0.0617150000
_diffrn_orient_matrix_UB_13      -0.0671924000
_diffrn_orient_matrix_UB_21      0.1783259000
_diffrn_orient_matrix_UB_22      0.0315707000
_diffrn_orient_matrix_UB_23      0.0830077000
_diffrn_orient_matrix_UB_31      0.1755071000
_diffrn_orient_matrix_UB_32      -0.0952151000
_diffrn_orient_matrix_UB_33      -0.0159120000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_number_gt                1640
_reflns_number_total             1742
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0384P)²+0.3252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0894
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.2602(3) 1.13135(11) 0.92239(10) 0.0224(3) Uani 1 d . . .
C2 C 0.4412(4) 1.20754(14) 0.91882(13) 0.0243(4) Uani 1 d . . .
H2 H 0.4460 1.2548 0.9694 0.029 Uiso 1 calc . . R
C3 C 0.6203(4) 1.22121(14) 0.84617(13) 0.0253(4) Uani 1 d . . .
H3 H 0.7442 1.2763 0.8465 0.030 Uiso 1 calc . . R
C4 C 0.6130(4) 1.15152(14) 0.77258(13) 0.0248(4) Uani 1 d . . .
H4 H 0.7329 1.1586 0.7213 0.030 Uiso 1 calc . . R
C5 C 0.4318(4) 1.07220(14) 0.77402(12) 0.0235(4) Uani 1 d . . .
H5 H 0.4237 1.0238 0.7244 0.028 Uiso 1 calc . . R
C6 C 0.2605(4) 1.06551(12) 0.85120(12) 0.0191(4) Uani 1 d . . .
N7 N 0.0721(3) 0.98589(11) 0.85745(10) 0.0199(3) Uani 1 d . . .
N8 N 0.0524(3) 0.91779(11) 0.78439(10) 0.0236(3) Uani 1 d . . .
C9 C -0.1411(4) 0.85414(14) 0.80719(13) 0.0253(4) Uani 1 d . . .
H9 H -0.1980 0.7989 0.7688 0.030 Uiso 1 calc . . R
C10 C -0.2551(4) 0.87770(13) 0.89601(12) 0.0225(4) Uani 1 d . . .
C11 C -0.4630(4) 0.83688(14) 0.95089(13) 0.0244(4) Uani 1 d . . .
H11 H -0.5615 0.7790 0.9303 0.029 Uiso 1 calc . . R
C12 C -0.5199(4) 0.88309(14) 1.03507(14) 0.0264(4) Uani 1 d . . .
H12 H -0.6606 0.8572 1.0730 0.032 Uiso 1 calc . . R
C13 C -0.3725(4) 0.96830(14) 1.06593(12) 0.0255(4) Uani 1 d . . .
H13 H -0.4169 0.9987 1.1244 0.031 Uiso 1 calc . . R
C14 C -0.1655(4) 1.00921(13) 1.01411(12) 0.0230(4) Uani 1 d . . .
H14 H -0.0646 1.0658 1.0363 0.028 Uiso 1 calc . . R
C15 C -0.1108(4) 0.96367(13) 0.92729(11) 0.0195(4) Uani 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
N1 C2 1.347(2) . ?
N1 C6 1.331(2) . ?
C2 C3 1.381(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.378(3) . ?
C5 C6 1.397(3) . ?
C6 N7 1.407(2) . ?
N7 N8 1.3740(19) . ?
N7 C15 1.383(2) . ?
N8 C9 1.317(2) . ?
C9 C10 1.422(3) . ?
C10 C11 1.407(3) . ?
C10 C15 1.408(2) . ?
C11 C12 1.373(3) . ?
C12 C13 1.407(3) . ?
C13 C14 1.380(3) . ?
C14 C15 1.401(2) . ?

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
C6 N1 C2 116.67(16) . . ?
N1 C2 C3 124.06(17) . . ?
C2 C3 C4 117.64(17) . . ?
C5 C4 C3 119.98(18) . . ?
C4 C5 C6 117.54(17) . . ?
N1 C6 C5 124.10(17) . . ?
N1 C6 N7 115.45(16) . . ?
C5 C6 N7 120.46(15) . . ?
N8 N7 C6 118.67(14) . . ?
N8 N7 C15 111.23(14) . . ?
C15 N7 C6 130.09(15) . . ?
C9 N8 N7 105.98(14) . . ?
N8 C9 C10 112.16(16) . . ?
C11 C10 C9 135.17(18) . . ?
C11 C10 C15 120.37(17) . . ?
C15 C10 C9 104.45(16) . . ?
C12 C11 C10 118.17(17) . . ?
C11 C12 C13 120.89(18) . . ?
C14 C13 C12 122.20(18) . . ?
C13 C14 C15 117.06(17) . . ?
N7 C15 C10 106.18(15) . . ?
N7 C15 C14 132.54(17) . . ?
C14 C15 C10 121.28(17) . . ?

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
N1 C2 C3 C4 -0.3(3) . . . . ?
N1 C6 N7 N8 176.99(15) . . . . ?
N1 C6 N7 C15 -1.6(3) . . . . ?
C2 N1 C6 C5 -1.1(3) . . . . ?
C2 N1 C6 N7 179.08(15) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 N1 0.7(3) . . . . ?
C4 C5 C6 N7 -179.49(16) . . . . ?
C5 C6 N7 N8 -2.8(2) . . . . ?
C5 C6 N7 C15 178.58(18) . . . . ?
C6 N1 C2 C3 0.9(3) . . . . ?
C6 N7 N8 C9 -178.32(15) . . . . ?
C6 N7 C15 C10 178.04(16) . . . . ?
C6 N7 C15 C14 -2.0(3) . . . . ?
N7 N8 C9 C10 -0.2(2) . . . . ?
N8 N7 C15 C10 -0.64(19) . . . . ?
N8 N7 C15 C14 179.33(18) . . . . ?
N8 C9 C10 C11 178.6(2) . . . . ?
N8 C9 C10 C15 -0.2(2) . . . . ?
C9 C10 C11 C12 -178.7(2) . . . . ?
C9 C10 C15 N7 0.48(18) . . . . ?
C9 C10 C15 C14 -179.49(16) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C10 C15 N7 -178.55(16) . . . . ?
C11 C10 C15 C14 1.5(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C13 C14 C15 N7 177.89(18) . . . . ?
C13 C14 C15 C10 -2.1(2) . . . . ?
C15 N7 N8 C9 0.53(19) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1018276'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_L2
_audit_creation_date             2014-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H9 N3'
_chemical_formula_sum            'C12 H9 N3'
_chemical_formula_weight         195.22
_chemical_absolute_configuration unk
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   5.6717(6)
_cell_length_b                   11.2569(11)
_cell_length_c                   14.8452(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     947.80(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1587
_cell_measurement_temperature    120.0(10)
_cell_measurement_theta_max      73.5298
_cell_measurement_theta_min      2.9743
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4592
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.69
_diffrn_reflns_theta_min         4.93
_diffrn_ambient_temperature      120.0(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.7813   57.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega -107.00  -70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.7813 -152.0000  -51.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -68.00  -28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.7813   57.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega   39.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7813  -99.0000  -60.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7813  -99.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega   51.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega   52.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
  8 omega   48.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega  103.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   61.0000   60.0000 75

#__ type_ start__ end____ width___ exp.time_
 11 omega -114.00  -10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.7813  -57.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
 12 omega -114.00  -10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.7813  -57.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
 13 omega -114.00  -10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.7813  -57.0000  -30.0000 104

#__ type_ start__ end____ width___ exp.time_
 14 omega    1.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.7813  -99.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
 15 omega   25.00  151.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -15.0000   30.0000 126
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1202945000
_diffrn_orient_matrix_UB_12      0.1170098000
_diffrn_orient_matrix_UB_13      0.0284377000
_diffrn_orient_matrix_UB_21      -0.1624714000
_diffrn_orient_matrix_UB_22      -0.0699997000
_diffrn_orient_matrix_UB_23      0.0641545000
_diffrn_orient_matrix_UB_31      0.1801568000
_diffrn_orient_matrix_UB_32      0.0151464000
_diffrn_orient_matrix_UB_33      0.0766023000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_number_gt                1505
_reflns_number_total             1734
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1734
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0474P)²+0.1717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1025
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.3189(3) 0.09633(14) -0.06691(11) 0.0249(4) Uani 1 d . . .
C2 C 0.5104(4) 0.08636(18) -0.12002(14) 0.0276(5) Uani 1 d . . .
H2 H 0.5750 0.1570 -0.1448 0.033 Uiso 1 calc . . R
C3 C 0.6191(4) -0.02011(18) -0.14072(14) 0.0281(5) Uani 1 d . . .
H3 H 0.7545 -0.0223 -0.1784 0.034 Uiso 1 calc . . R
C4 C 0.5245(4) -0.12409(18) -0.10486(14) 0.0280(5) Uani 1 d . . .
H4 H 0.5945 -0.1988 -0.1180 0.034 Uiso 1 calc . . R
C5 C 0.3280(4) -0.11754(17) -0.04998(14) 0.0247(5) Uani 1 d . . .
H5 H 0.2592 -0.1868 -0.0246 0.030 Uiso 1 calc . . R
C6 C 0.2352(3) -0.00506(17) -0.03353(13) 0.0220(4) Uani 1 d . . .
N7 N 0.0337(3) 0.00786(14) 0.02329(11) 0.0223(4) Uani 1 d . . .
N8 N -0.0664(3) -0.09067(14) 0.06028(12) 0.0245(4) Uani 1 d . . .
C9 C -0.2480(4) -0.04599(17) 0.10838(14) 0.0236(5) Uani 1 d . . .
C10 C -0.4186(4) -0.11044(19) 0.15812(14) 0.0291(5) Uani 1 d . . .
H10 H -0.4115 -0.1945 0.1626 0.035 Uiso 1 calc . . R
C11 C -0.5935(4) -0.04738(19) 0.19931(14) 0.0307(5) Uani 1 d . . .
H11 H -0.7109 -0.0889 0.2323 0.037 Uiso 1 calc . . R
C12 C -0.6054(4) 0.0792(2) 0.19433(14) 0.0304(5) Uani 1 d . . .
H12 H -0.7291 0.1196 0.2248 0.036 Uiso 1 calc . . R
C13 C -0.4433(4) 0.14381(19) 0.14683(14) 0.0286(5) Uani 1 d . . .
H13 H -0.4529 0.2280 0.1438 0.034 Uiso 1 calc . . R
C14 C -0.2601(4) 0.08106(17) 0.10219(14) 0.0241(5) Uani 1 d . . .
C15 C -0.0741(4) 0.11153(16) 0.04577(13) 0.0234(5) Uani 1 d . . .
H15 H -0.0311 0.1891 0.0268 0.028 Uiso 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 C2 1.347(3) . ?
N1 C6 1.332(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C6 N7 1.428(2) . ?
N7 N8 1.362(2) . ?
N7 C15 1.359(2) . ?
N8 C9 1.351(3) . ?
C9 C10 1.417(3) . ?
C9 C14 1.435(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.364(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.429(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.368(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.420(3) . ?
C14 C15 1.390(3) . ?
C15 H15 0.9500 . ?

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
C6 N1 C2 115.72(17) . . ?
N1 C2 H2 117.9 . . ?
N1 C2 C3 124.19(19) . . ?
C3 C2 H2 117.9 . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.16(19) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.38(19) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.16(18) . . ?
C6 C5 H5 121.4 . . ?
N1 C6 C5 125.39(18) . . ?
N1 C6 N7 114.70(17) . . ?
C5 C6 N7 119.91(17) . . ?
N8 N7 C6 119.27(15) . . ?
C15 N7 C6 126.34(17) . . ?
C15 N7 N8 114.39(16) . . ?
C9 N8 N7 103.17(15) . . ?
N8 C9 C10 127.28(18) . . ?
N8 C9 C14 111.95(18) . . ?
C10 C9 C14 120.7(2) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 C9 117.62(19) . . ?
C11 C10 H10 121.2 . . ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 122.0(2) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.7(2) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 121.1 . . ?
C12 C13 C14 117.9(2) . . ?
C14 C13 H13 121.1 . . ?
C13 C14 C9 120.1(2) . . ?
C15 C14 C9 104.38(18) . . ?
C15 C14 C13 135.52(19) . . ?
N7 C15 C14 106.11(16) . . ?
N7 C15 H15 126.9 . . ?
C14 C15 H15 126.9 . . ?

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
N1 C2 C3 C4 0.3(3) . . . . ?
N1 C6 N7 N8 179.53(17) . . . . ?
N1 C6 N7 C15 -0.6(3) . . . . ?
C2 N1 C6 C5 -0.6(3) . . . . ?
C2 N1 C6 N7 179.39(16) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 N1 0.6(3) . . . . ?
C4 C5 C6 N7 -179.41(17) . . . . ?
C5 C6 N7 N8 -0.4(3) . . . . ?
C5 C6 N7 C15 179.4(2) . . . . ?
C6 N1 C2 C3 0.2(3) . . . . ?
C6 N7 N8 C9 -179.82(16) . . . . ?
C6 N7 C15 C14 -179.73(17) . . . . ?
N7 N8 C9 C10 177.3(2) . . . . ?
N7 N8 C9 C14 -0.6(2) . . . . ?
N8 N7 C15 C14 0.1(2) . . . . ?
N8 C9 C10 C11 -177.6(2) . . . . ?
N8 C9 C14 C13 178.60(18) . . . . ?
N8 C9 C14 C15 0.7(2) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C9 C14 C15 N7 -0.5(2) . . . . ?
C10 C9 C14 C13 0.6(3) . . . . ?
C10 C9 C14 C15 -177.34(19) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C12 C13 C14 C15 176.5(2) . . . . ?
C13 C14 C15 N7 -177.9(2) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C15 N7 N8 C9 0.3(2) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1018277'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_L4
_audit_creation_date             2014-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C8 H6 N2 O2), H2 O'
_chemical_formula_sum            'C16 H14 N4 O5'
_chemical_formula_weight         342.31
_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'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   4.9524(7)
_cell_length_b                   10.9756(9)
_cell_length_c                   14.6313(15)
_cell_angle_alpha                81.698(8)
_cell_angle_beta                 83.854(10)
_cell_angle_gamma                78.805(9)
_cell_volume                     769.43(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1949
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      74.1487
_cell_measurement_theta_min      3.0600
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4768
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.32
_diffrn_reflns_theta_min         3.06
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   36.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6873   37.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -63.00  -10.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6873  -57.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega  -51.00   39.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6873   77.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega -112.00  -75.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6873  -57.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  -33.00   16.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6873   37.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
  6 omega   69.00   96.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       39.6873 -125.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega   23.00   53.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       39.6873  -99.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega   61.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -94.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
  9 omega   32.00  108.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -94.0000   30.0000 76

#__ type_ start__ end____ width___ exp.time_
 10 omega   94.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  125.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
 11 omega   82.00  137.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -61.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 12 omega   68.00   97.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -45.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 13 omega   96.00  127.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  125.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 14 omega   37.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -30.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega   96.00  158.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  125.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 16 omega   95.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491   31.0000 -108.0000 83

#__ type_ start__ end____ width___ exp.time_
 17 omega   34.00   60.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491  -61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   78.00  162.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491   61.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
 19 omega   38.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7491 -125.0000  -60.0000 83
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2631877000
_diffrn_orient_matrix_UB_12      -0.0126124000
_diffrn_orient_matrix_UB_13      -0.0425061000
_diffrn_orient_matrix_UB_21      -0.0979978000
_diffrn_orient_matrix_UB_22      0.1428379000
_diffrn_orient_matrix_UB_23      -0.0066974000
_diffrn_orient_matrix_UB_31      0.1495177000
_diffrn_orient_matrix_UB_32      0.0156710000
_diffrn_orient_matrix_UB_33      -0.0977062000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_number_gt                2479
_reflns_number_total             2964
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.1198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1158
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
 N13-H13
 0.88 with sigma of 0.02
 O11-H11
 0.84 with sigma of 0.02
 O25-H25B
 0.84 with sigma of 0.02
 O25-H25A
 0.84 with sigma of 0.02
 O23-H23
 0.84 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C15(H15), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.2098(3) 0.45224(13) -0.10805(10) 0.0234(3) Uani 1 d . . D
H1 H 0.320(4) 0.4924(19) -0.0850(15) 0.028 Uiso 1 d . . DR
N2 N 0.1232(3) 0.49248(13) -0.19463(9) 0.0251(3) Uani 1 d . . .
C3 C -0.0430(4) 0.41810(16) -0.20935(12) 0.0262(4) Uani 1 d . . .
H3 H -0.1346 0.4255 -0.2642 0.031 Uiso 1 calc . . R
C4 C -0.0661(3) 0.32523(15) -0.13175(12) 0.0246(4) Uani 1 d . . .
C5 C -0.2061(4) 0.22362(16) -0.10882(12) 0.0265(4) Uani 1 d . . .
H5 H -0.3194 0.2042 -0.1511 0.032 Uiso 1 calc . . R
C6 C -0.1747(4) 0.15276(15) -0.02332(13) 0.0282(4) Uani 1 d . . .
H6 H -0.2675 0.0837 -0.0070 0.034 Uiso 1 calc . . R
C7 C -0.0083(4) 0.18081(15) 0.03995(12) 0.0253(3) Uani 1 d . . .
H7 H 0.0081 0.1302 0.0982 0.030 Uiso 1 calc . . R
C8 C 0.1317(3) 0.27954(14) 0.01989(11) 0.0224(3) Uani 1 d . . .
C9 C 0.1001(3) 0.35223(14) -0.06797(11) 0.0221(3) Uani 1 d . . .
C10 C 0.3086(3) 0.31276(15) 0.08382(11) 0.0233(3) Uani 1 d . . .
O11 O 0.3344(3) 0.23624(11) 0.16287(8) 0.0294(3) Uani 1 d . . D
H11 H 0.437(5) 0.264(2) 0.1965(16) 0.044 Uiso 1 d . . DR
O12 O 0.4217(3) 0.40282(11) 0.06479(8) 0.0254(3) Uani 1 d . . .
N13 N -0.1089(3) -0.01446(13) 0.39315(10) 0.0254(3) Uani 1 d . . D
H13 H -0.269(4) 0.019(2) 0.4228(14) 0.030 Uiso 1 d . . DR
N14 N 0.0053(3) 0.06021(13) 0.32279(10) 0.0276(3) Uani 1 d . . .
C15 C 0.2354(4) -0.00844(16) 0.29068(12) 0.0280(4) Uani 1 d . . .
H15 H 0.3575 0.0206 0.2414 0.034 Uiso 1 calc . . R
C16 C 0.2768(4) -0.13147(16) 0.33932(11) 0.0249(3) Uani 1 d . . .
C17 C 0.4757(4) -0.24145(16) 0.33347(12) 0.0268(4) Uani 1 d . . .
H17 H 0.6320 -0.2427 0.2897 0.032 Uiso 1 calc . . R
C18 C 0.4373(4) -0.34715(16) 0.39294(12) 0.0281(4) Uani 1 d . . .
H18 H 0.5674 -0.4226 0.3892 0.034 Uiso 1 calc . . R
C19 C 0.2094(4) -0.34546(15) 0.45908(12) 0.0267(4) Uani 1 d . . .
H19 H 0.1896 -0.4200 0.4991 0.032 Uiso 1 calc . . R
C20 C 0.0119(4) -0.23801(15) 0.46773(11) 0.0241(3) Uani 1 d . . .
C21 C 0.0485(4) -0.13064(15) 0.40511(11) 0.0234(3) Uani 1 d . . .
C22 C -0.2296(4) -0.23151(15) 0.53631(11) 0.0243(3) Uani 1 d . . .
O23 O -0.2396(3) -0.33612(11) 0.59400(9) 0.0308(3) Uani 1 d . . D
H23 H -0.379(4) -0.322(2) 0.6343(16) 0.046 Uiso 1 d . . DR
O24 O -0.4034(3) -0.13712(11) 0.53927(9) 0.0290(3) Uani 1 d . . .
O25 O 0.6609(3) 0.29565(11) 0.27688(8) 0.0271(3) Uani 1 d . . D
H25A H 0.785(5) 0.2292(18) 0.2886(17) 0.041 Uiso 1 d . . DR
H25B H 0.751(5) 0.3556(19) 0.2565(16) 0.041 Uiso 1 d . . DR


_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 H1 0.885(15) . ?
N1 N2 1.3656(19) . ?
N1 C9 1.350(2) . ?
N2 C3 1.319(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.423(2) . ?
C4 C5 1.407(2) . ?
C4 C9 1.405(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.405(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(2) . ?
C8 C9 1.419(2) . ?
C8 C10 1.474(2) . ?
C10 O11 1.330(2) . ?
C10 O12 1.213(2) . ?
O11 H11 0.865(17) . ?
N13 H13 0.899(16) . ?
N13 N14 1.365(2) . ?
N13 C21 1.358(2) . ?
N14 C15 1.319(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.421(2) . ?
C16 C17 1.409(2) . ?
C16 C21 1.404(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.405(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(2) . ?
C20 C21 1.413(2) . ?
C20 C22 1.474(3) . ?
C22 O23 1.329(2) . ?
C22 O24 1.215(2) . ?
O23 H23 0.863(17) . ?
O25 H25A 0.867(17) . ?
O25 H25B 0.865(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 120.1(14) . . ?
C9 N1 H1 128.7(14) . . ?
C9 N1 N2 111.14(14) . . ?
C3 N2 N1 106.78(14) . . ?
N2 C3 H3 124.6 . . ?
N2 C3 C4 110.70(15) . . ?
C4 C3 H3 124.6 . . ?
C5 C4 C3 135.96(16) . . ?
C9 C4 C3 104.28(15) . . ?
C9 C4 C5 119.77(16) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.41(16) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.31(17) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.90(16) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 116.83(15) . . ?
C7 C8 C10 123.95(15) . . ?
C9 C8 C10 119.21(15) . . ?
N1 C9 C4 107.09(14) . . ?
N1 C9 C8 131.11(16) . . ?
C4 C9 C8 121.79(16) . . ?
O11 C10 C8 114.81(14) . . ?
O12 C10 C8 122.00(15) . . ?
O12 C10 O11 123.18(16) . . ?
C10 O11 H11 108.6(18) . . ?
N14 N13 H13 117.6(14) . . ?
C21 N13 H13 131.4(14) . . ?
C21 N13 N14 111.03(14) . . ?
C15 N14 N13 106.50(14) . . ?
N14 C15 H15 124.4 . . ?
N14 C15 C16 111.23(16) . . ?
C16 C15 H15 124.4 . . ?
C17 C16 C15 135.62(17) . . ?
C21 C16 C15 104.10(15) . . ?
C21 C16 C17 120.26(16) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 C16 118.21(17) . . ?
C18 C17 H17 120.9 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.24(16) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.0 . . ?
C20 C19 C18 121.99(16) . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C21 116.57(16) . . ?
C19 C20 C22 123.94(15) . . ?
C21 C20 C22 119.48(15) . . ?
N13 C21 C16 107.12(15) . . ?
N13 C21 C20 131.17(17) . . ?
C16 C21 C20 121.70(15) . . ?
O23 C22 C20 114.72(14) . . ?
O24 C22 C20 121.94(15) . . ?
O24 C22 O23 123.34(17) . . ?
C22 O23 H23 108.1(17) . . ?
H25A O25 H25B 106(2) . . ?

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
N1 H1 O12 0.885(15) 1.947(16) 2.8154(19) 166(2) 2_665
O11 H11 O25 0.865(17) 1.811(17) 2.6688(18) 171(3) .
N13 H13 O24 0.899(16) 1.955(17) 2.825(2) 162(2) 2_456
O23 H23 O25 0.863(17) 1.813(17) 2.6755(19) 177(3) 2_556
O25 H25A N14 0.867(17) 1.986(17) 2.8409(19) 168(2) 1_655
O25 H25B N2 0.865(17) 1.959(17) 2.8073(19) 166(2) 2_665

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
N1 N2 C3 C4 -0.69(18) . . . . ?
N2 N1 C9 C4 0.25(18) . . . . ?
N2 N1 C9 C8 179.59(16) . . . . ?
N2 C3 C4 C5 -179.19(18) . . . . ?
N2 C3 C4 C9 0.83(19) . . . . ?
C3 C4 C5 C6 179.94(18) . . . . ?
C3 C4 C9 N1 -0.63(18) . . . . ?
C3 C4 C9 C8 179.95(15) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C4 C9 N1 179.39(14) . . . . ?
C5 C4 C9 C8 0.0(2) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C6 C7 C8 C10 179.99(15) . . . . ?
C7 C8 C9 N1 -179.22(16) . . . . ?
C7 C8 C9 C4 0.0(2) . . . . ?
C7 C8 C10 O11 2.7(2) . . . . ?
C7 C8 C10 O12 -177.65(16) . . . . ?
C9 N1 N2 C3 0.27(18) . . . . ?
C9 C4 C5 C6 -0.1(2) . . . . ?
C9 C8 C10 O11 -177.39(14) . . . . ?
C9 C8 C10 O12 2.3(2) . . . . ?
C10 C8 C9 N1 0.9(3) . . . . ?
C10 C8 C9 C4 -179.88(14) . . . . ?
N13 N14 C15 C16 0.5(2) . . . . ?
N14 N13 C21 C16 0.10(19) . . . . ?
N14 N13 C21 C20 -179.16(17) . . . . ?
N14 C15 C16 C17 178.06(19) . . . . ?
N14 C15 C16 C21 -0.4(2) . . . . ?
C15 C16 C17 C18 -177.49(19) . . . . ?
C15 C16 C21 N13 0.17(19) . . . . ?
C15 C16 C21 C20 179.51(15) . . . . ?
C16 C17 C18 C19 -1.2(3) . . . . ?
C17 C16 C21 N13 -178.58(15) . . . . ?
C17 C16 C21 C20 0.8(3) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 1.3(3) . . . . ?
C18 C19 C20 C22 -179.65(16) . . . . ?
C19 C20 C21 N13 177.39(16) . . . . ?
C19 C20 C21 C16 -1.8(2) . . . . ?
C19 C20 C22 O23 3.3(2) . . . . ?
C19 C20 C22 O24 -177.03(16) . . . . ?
C21 N13 N14 C15 -0.35(19) . . . . ?
C21 C16 C17 C18 0.8(3) . . . . ?
C21 C20 C22 O23 -177.75(15) . . . . ?
C21 C20 C22 O24 2.0(3) . . . . ?
C22 C20 C21 N13 -1.7(3) . . . . ?
C22 C20 C21 C16 179.16(15) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1018278'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1
_audit_creation_date             2014-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C24 H18 Cu N7 O3), 2(N O3), 3(H2 O)'
_chemical_formula_sum            'C48 H42 Cu2 N16 O15'
_chemical_formula_weight         1210.06
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4CU1
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2872(2)
_cell_length_b                   15.9102(5)
_cell_length_c                   21.2623(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.328(3)
_cell_angle_gamma                90.00
_cell_volume                     2432.58(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2585
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.4065
_cell_measurement_theta_min      2.7750
_exptl_absorpt_coefficient_mu    1.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9042
_diffrn_reflns_theta_full        73.57
_diffrn_reflns_theta_max         73.57
_diffrn_reflns_theta_min         3.49
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9012   37.0000   60.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega  -70.00    4.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9012   77.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.9012   57.0000  150.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega   51.00   77.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -45.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   89.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -45.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00   94.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -45.0000    0.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega   96.00  178.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   30.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
  8 omega   30.00   82.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -30.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
  9 omega  143.00  169.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  125.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   41.00  116.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853 -125.0000    0.0000 75

#__ type_ start__ end____ width___ exp.time_
 11 omega   44.00   83.00   1.0000   82.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -30.0000 -150.0000 39
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2110275000
_diffrn_orient_matrix_UB_12      -0.0126617000
_diffrn_orient_matrix_UB_13      -0.0036039000
_diffrn_orient_matrix_UB_21      0.0308271000
_diffrn_orient_matrix_UB_22      -0.0264668000
_diffrn_orient_matrix_UB_23      0.0707030000
_diffrn_orient_matrix_UB_31      -0.0200874000
_diffrn_orient_matrix_UB_32      0.0922297000
_diffrn_orient_matrix_UB_33      0.0196295000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_number_gt                3688
_reflns_number_total             4759
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XLMP (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.946
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.086
_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     424
_refine_ls_number_reflns         4759
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0747P)²+3.1349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1536
_refine_special_details          
;
'Non-coordinating nitrate anions were modelled disordered over two sites 
at half occupancy with PART 1 and PART 2 commands. N-O bond lengths for 
disordered nitrate anions were restrainted with standard DFIX commands. 
Residual Fourier peaks were assigned as disordered water molecules with 
a total occupancy of 1.5 water molecules split over three positions as 
confirmed by bulk phase analysis methods. Although partial hydrogen 
bonding connectivity to the disordered nitrate anion was expected, full 
hydrogen bonding connectivity could not be established and water molecule 
hydrogen atoms were allowed to freely rotate. PART 1 and PART 2 commands 
were applied.'
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N37-O39 = N37-O36 = N37-O38
 1.25 with sigma of 0.02
 N41-O43 = N41-O40 = N41-O42
 1.25 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N41) \\sim Ueq, Uanis(O39) \\sim Ueq, Uanis(O43) \\sim Ueq, Uanis(O36)
\\sim Ueq, Uanis(O40) \\sim Ueq, Uanis(O38) \\sim Ueq, Uanis(O42) \\sim Ueq,
Uanis(N37) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.002
4. Others
 Fixed Sof: N41(0.5) O40(0.5) O42(0.5) O43(0.5) N37(0.5) O36(0.5) O38(0.5)
 O39(0.5) O44(0.5) H44A(0.5) H44B(0.5) O45(0.5) H45A(0.5) H45B(0.5) O46(0.5)
 H46A(0.5) H46B(0.5)
5.a Free rotating group:
 O44(H44A,H44B), O45(H45A,H45B), O46(H46A,H46B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C27(H27), C28(H28),
  C29(H29), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C3 C 0.3721(5) 0.8422(2) -0.12158(16) 0.0337(7) Uani 1 d . . . .
H3 H 0.3994 0.7898 -0.1395 0.040 Uiso 1 calc . . R .
C4 C 0.3713(5) 0.9138(3) -0.15800(19) 0.0389(8) Uani 1 d . . . .
H4 H 0.3932 0.9105 -0.2008 0.047 Uiso 1 calc . . R .
C5 C 0.3382(5) 0.9906(3) -0.13172(18) 0.0381(8) Uani 1 d . . . .
H5 H 0.3396 1.0408 -0.1559 0.046 Uiso 1 calc . . R .
C6 C 0.3029(5) 0.9935(2) -0.06939(17) 0.0334(8) Uani 1 d . . . .
H6 H 0.2808 1.0455 -0.0500 0.040 Uiso 1 calc . . R .
C7 C 0.3009(4) 0.9186(2) -0.03622(15) 0.0265(7) Uani 1 d . . . .
C10 C 0.2452(5) 0.8420(2) 0.11312(16) 0.0313(7) Uani 1 d . . . .
H10 H 0.2462 0.7969 0.1424 0.038 Uiso 1 calc . . R .
C11 C 0.1996(5) 0.9274(2) 0.12522(17) 0.0324(7) Uani 1 d . . . .
C12 C 0.1541(5) 0.9681(3) 0.17891(19) 0.0389(8) Uani 1 d . . . .
H12 H 0.1438 0.9378 0.2167 0.047 Uiso 1 calc . . R .
C13 C 0.1248(5) 1.0535(3) 0.17524(19) 0.0402(9) Uani 1 d . . . .
H13 H 0.0992 1.0833 0.2116 0.048 Uiso 1 calc . . R .
C14 C 0.1324(5) 1.0972(2) 0.1181(2) 0.0385(8) Uani 1 d . . . .
H14 H 0.1080 1.1559 0.1166 0.046 Uiso 1 calc . . R .
C15 C 0.1741(5) 1.0579(2) 0.06400(18) 0.0334(7) Uani 1 d . . . .
H15 H 0.1774 1.0881 0.0256 0.040 Uiso 1 calc . . R .
C16 C 0.2112(4) 0.9717(2) 0.06859(17) 0.0287(7) Uani 1 d . . . .
C18 C 0.4987(5) 0.6575(2) 0.11756(16) 0.0312(7) Uani 1 d . . . .
H18 H 0.5446 0.7108 0.1330 0.037 Uiso 1 calc . . R .
C19 C 0.5344(5) 0.5883(2) 0.15635(17) 0.0337(8) Uani 1 d . . . .
H19 H 0.6021 0.5939 0.1983 0.040 Uiso 1 calc . . R .
C20 C 0.4706(5) 0.5108(2) 0.13352(18) 0.0336(8) Uani 1 d . . . .
H20 H 0.4946 0.4624 0.1597 0.040 Uiso 1 calc . . R .
C21 C 0.3715(5) 0.5035(2) 0.07253(17) 0.0320(7) Uani 1 d . . . .
H21 H 0.3277 0.4504 0.0559 0.038 Uiso 1 calc . . R .
C22 C 0.3383(4) 0.5762(2) 0.03633(16) 0.0263(7) Uani 1 d . . . .
C25 C 0.1434(5) 0.6417(2) -0.11597(17) 0.0337(8) Uani 1 d . . . .
H25 H 0.1181 0.6844 -0.1474 0.040 Uiso 1 calc . . R .
C26 C 0.0877(5) 0.5557(2) -0.12494(17) 0.0317(7) Uani 1 d . . . .
C27 C -0.0049(5) 0.5103(3) -0.17707(18) 0.0367(8) Uani 1 d . . . .
H27 H -0.0465 0.5371 -0.2167 0.044 Uiso 1 calc . . R .
C28 C -0.0338(5) 0.4257(3) -0.16918(19) 0.0394(9) Uani 1 d . . . .
H28 H -0.0933 0.3931 -0.2041 0.047 Uiso 1 calc . . R .
C29 C 0.0245(5) 0.3872(2) -0.1095(2) 0.0372(8) Uani 1 d . . . .
H29 H 0.0012 0.3289 -0.1052 0.045 Uiso 1 calc . . R .
C30 C 0.1144(5) 0.4308(2) -0.05710(19) 0.0331(7) Uani 1 d . . . .
H30 H 0.1506 0.4041 -0.0170 0.040 Uiso 1 calc . . R .
C31 C 0.1493(4) 0.5161(2) -0.06604(17) 0.0283(7) Uani 1 d . . . .
Cu1 Cu 0.36036(7) 0.74674(3) -0.00236(2) 0.02838(17) Uani 1 d . . . .
N2 N 0.3356(4) 0.84370(19) -0.06137(13) 0.0288(6) Uani 1 d . . . .
N8 N 0.2641(4) 0.91343(18) 0.02676(13) 0.0272(6) Uani 1 d . . . .
N9 N 0.2858(4) 0.83553(18) 0.05515(13) 0.0278(6) Uani 1 d . . . .
N17 N 0.4004(4) 0.65181(18) 0.05827(13) 0.0278(6) Uani 1 d . . . .
N23 N 0.2401(4) 0.57754(18) -0.02639(13) 0.0259(6) Uani 1 d . . . .
N24 N 0.2342(4) 0.65301(18) -0.05811(14) 0.0282(6) Uani 1 d . . . .
N33 N 0.7485(4) 0.75334(19) -0.00508(18) 0.0392(7) Uani 1 d . . . .
O32 O 0.6290(4) 0.70848(19) -0.03973(16) 0.0490(7) Uani 1 d . . . .
O34 O 0.6904(5) 0.79831(19) 0.03580(16) 0.0544(8) Uani 1 d . . . .
O35 O 0.9117(4) 0.7518(2) -0.0111(2) 0.0605(9) Uani 1 d . . . .
N41 N 0.8518(12) 0.8061(5) 0.2392(4) 0.0336(17) Uani 0.50 d A 2 D U
O40 O 0.7104(17) 0.8507(8) 0.2387(6) 0.098(4) Uani 0.50 d A 2 D U
O42 O 0.8437(17) 0.7387(7) 0.2228(6) 0.100(3) Uani 0.50 d A 2 D U
O43 O 0.9911(14) 0.8266(6) 0.2797(4) 0.083(2) Uani 0.50 d A 2 D U
N37 N 0.7527(15) 0.8120(5) 0.2364(4) 0.043(2) Uani 0.50 d B 1 D U
O36 O 0.5889(9) 0.8358(4) 0.2102(3) 0.0478(14) Uani 0.50 d B 1 D U
O38 O 0.7748(11) 0.7379(4) 0.2473(3) 0.0533(16) Uani 0.50 d B 1 D U
O39 O 0.8584(10) 0.8704(4) 0.2568(3) 0.0554(16) Uani 0.50 d B 1 D U
O44 O 1.2025(10) 0.8174(4) 0.3268(3) 0.0532(15) Uani 0.50 d C 1 . .
H44A H 1.1837 0.7907 0.3598 0.080 Uiso 0.50 d C 1 G .
H44B H 1.1204 0.8037 0.2954 0.080 Uiso 0.50 d C 1 G .
O45 O 0.322(2) 0.7353(10) 0.2588(9) 0.096(4) Uani 0.50 d D 1 . .
H45A H 0.3386 0.7052 0.2923 0.144 Uiso 0.50 d D 1 G .
H45B H 0.2160 0.7585 0.2547 0.144 Uiso 0.50 d D 1 G .
O46 O 0.394(2) 0.7330(9) 0.2440(5) 0.076(4) Uani 0.50 d E 2 . .
H46A H 0.4620 0.6919 0.2588 0.113 Uiso 0.50 d E 2 G .
H46B H 0.4621 0.7735 0.2357 0.113 Uiso 0.50 d E 2 G .


_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
C3 H3 0.9500 . ?
C3 C4 1.378(5) . ?
C3 N2 1.349(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(5) . ?
C7 N2 1.347(5) . ?
C7 N8 1.410(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.431(5) . ?
C10 N9 1.317(5) . ?
C11 C12 1.399(5) . ?
C11 C16 1.410(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.376(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.408(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.399(5) . ?
C16 N8 1.382(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.374(5) . ?
C18 N17 1.348(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.389(5) . ?
C22 N17 1.343(4) . ?
C22 N23 1.408(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.432(5) . ?
C25 N24 1.312(4) . ?
C26 C27 1.401(5) . ?
C26 C31 1.409(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.377(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.410(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.384(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.400(5) . ?
C31 N23 1.387(4) . ?
Cu1 N2 1.978(3) . ?
Cu1 N9 2.000(3) . ?
Cu1 N17 1.976(3) . ?
Cu1 N24 2.030(3) . ?
Cu1 O32 2.310(3) . ?
N8 N9 1.376(4) . ?
N23 N24 1.374(4) . ?
N33 O32 1.266(5) . ?
N33 O34 1.252(5) . ?
N33 O35 1.217(5) . ?
N41 O40 1.250(12) . ?
N41 O42 1.126(11) . ?
N41 O43 1.263(11) . ?
O43 H44B 1.0146 . ?
N37 O36 1.289(12) . ?
N37 O38 1.208(10) . ?
N37 O39 1.240(10) . ?
O44 H44A 0.8512 . ?
O44 H44B 0.8498 . ?
O45 H45A 0.8502 . ?
O45 H45B 0.8497 . ?
O45 H46A 1.2300 . ?
O45 H46B 1.3473 . ?
O46 H45A 1.2439 . ?
O46 H45B 1.4115 . ?
O46 H46A 0.8497 . ?
O46 H46B 0.8497 . ?

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
C4 C3 H3 118.8 . . ?
N2 C3 H3 118.8 . . ?
N2 C3 C4 122.3(4) . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.1(4) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 120.8 . . ?
C7 C6 C5 118.4(4) . . ?
C7 C6 H6 120.8 . . ?
C6 C7 N8 123.6(3) . . ?
N2 C7 C6 122.7(3) . . ?
N2 C7 N8 113.7(3) . . ?
C11 C10 H10 125.2 . . ?
N9 C10 H10 125.2 . . ?
N9 C10 C11 109.6(3) . . ?
C12 C11 C10 132.8(4) . . ?
C12 C11 C16 121.3(4) . . ?
C16 C11 C10 105.9(3) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.8(4) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 118.7 . . ?
C15 C14 C13 122.6(4) . . ?
C15 C14 H14 118.7 . . ?
C14 C15 H15 121.6 . . ?
C14 C15 C16 116.8(4) . . ?
C16 C15 H15 121.6 . . ?
C15 C16 C11 120.8(3) . . ?
N8 C16 C11 106.0(3) . . ?
N8 C16 C15 133.1(3) . . ?
C19 C18 H18 119.1 . . ?
N17 C18 H18 119.1 . . ?
N17 C18 C19 121.9(3) . . ?
C18 C19 H19 120.5 . . ?
C18 C19 C20 119.0(3) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 121.1 . . ?
C20 C21 C22 117.8(3) . . ?
C22 C21 H21 121.1 . . ?
C21 C22 N23 123.7(3) . . ?
N17 C22 C21 122.4(3) . . ?
N17 C22 N23 114.0(3) . . ?
C26 C25 H25 124.9 . . ?
N24 C25 H25 124.9 . . ?
N24 C25 C26 110.2(3) . . ?
C27 C26 C25 133.5(4) . . ?
C27 C26 C31 121.1(4) . . ?
C31 C26 C25 105.4(3) . . ?
C26 C27 H27 121.0 . . ?
C28 C27 C26 118.1(4) . . ?
C28 C27 H27 121.0 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.3(3) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 118.6 . . ?
C30 C29 C28 122.7(4) . . ?
C30 C29 H29 118.6 . . ?
C29 C30 H30 121.7 . . ?
C29 C30 C31 116.7(4) . . ?
C31 C30 H30 121.7 . . ?
C30 C31 C26 121.0(3) . . ?
N23 C31 C26 106.1(3) . . ?
N23 C31 C30 132.9(3) . . ?
N2 Cu1 N9 80.27(12) . . ?
N2 Cu1 N24 102.49(12) . . ?
N2 Cu1 O32 89.01(12) . . ?
N9 Cu1 N24 137.19(12) . . ?
N9 Cu1 O32 136.51(11) . . ?
N17 Cu1 N2 176.65(12) . . ?
N17 Cu1 N9 99.62(12) . . ?
N17 Cu1 N24 79.90(12) . . ?
N17 Cu1 O32 88.80(11) . . ?
N24 Cu1 O32 86.23(11) . . ?
C3 N2 Cu1 125.2(3) . . ?
C7 N2 C3 118.1(3) . . ?
C7 N2 Cu1 116.2(2) . . ?
C16 N8 C7 133.5(3) . . ?
N9 N8 C7 116.3(3) . . ?
N9 N8 C16 110.2(3) . . ?
C10 N9 Cu1 138.7(2) . . ?
C10 N9 N8 108.2(3) . . ?
N8 N9 Cu1 113.0(2) . . ?
C18 N17 Cu1 124.0(2) . . ?
C22 N17 C18 118.9(3) . . ?
C22 N17 Cu1 116.9(2) . . ?
C31 N23 C22 133.2(3) . . ?
N24 N23 C22 116.7(3) . . ?
N24 N23 C31 110.1(3) . . ?
C25 N24 Cu1 139.5(3) . . ?
C25 N24 N23 108.1(3) . . ?
N23 N24 Cu1 112.3(2) . . ?
O34 N33 O32 116.6(3) . . ?
O35 N33 O32 121.3(4) . . ?
O35 N33 O34 122.1(4) . . ?
N33 O32 Cu1 101.1(2) . . ?
O40 N41 O43 115.5(9) . . ?
O42 N41 O40 122.4(12) . . ?
O42 N41 O43 116.9(10) . . ?
N41 O43 H44B 137.0 . . ?
O38 N37 O36 117.0(8) . . ?
O38 N37 O39 127.4(10) . . ?
O39 N37 O36 114.3(9) . . ?
H46A O45 H46B 65.0 . . ?
H46A O46 H46B 109.5 . . ?

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
O44 H44A O32 0.85 2.24 3.001(8) 149.7 4_676
O44 H44B N41 0.85 2.12 2.913(11) 154.9 .
O44 H44B O39 0.85 2.22 2.829(10) 128.4 .
O45 H45B O43 0.85 2.10 2.912(18) 158.7 1_455
O46 H46B O40 0.85 2.18 2.99(2) 158.8 .
O46 H46B N37 0.85 2.20 2.929(17) 143.5 .
O46 H46B O36 0.85 1.51 2.353(15) 169.3 .

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
C3 C4 C5 C6 -1.2(5) . . . . ?
C4 C3 N2 C7 -1.3(5) . . . . ?
C4 C3 N2 Cu1 -172.9(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 N2 1.5(5) . . . . ?
C5 C6 C7 N8 -179.0(3) . . . . ?
C6 C7 N2 C3 -0.5(5) . . . . ?
C6 C7 N2 Cu1 171.8(2) . . . . ?
C6 C7 N8 C16 5.3(5) . . . . ?
C6 C7 N8 N9 -173.7(3) . . . . ?
C7 N8 N9 C10 -179.7(3) . . . . ?
C7 N8 N9 Cu1 -1.3(3) . . . . ?
C10 C11 C12 C13 177.2(4) . . . . ?
C10 C11 C16 C15 179.9(3) . . . . ?
C10 C11 C16 N8 -0.8(4) . . . . ?
C11 C10 N9 Cu1 -179.4(3) . . . . ?
C11 C10 N9 N8 -1.6(4) . . . . ?
C11 C12 C13 C14 2.8(5) . . . . ?
C11 C16 N8 C7 -179.1(3) . . . . ?
C11 C16 N8 N9 -0.1(4) . . . . ?
C12 C11 C16 C15 -1.2(5) . . . . ?
C12 C11 C16 N8 178.1(3) . . . . ?
C12 C13 C14 C15 -1.8(6) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C11 2.2(5) . . . . ?
C14 C15 C16 N8 -176.9(3) . . . . ?
C15 C16 N8 C7 0.1(6) . . . . ?
C15 C16 N8 N9 179.1(3) . . . . ?
C16 C11 C12 C13 -1.3(5) . . . . ?
C16 N8 N9 C10 1.1(4) . . . . ?
C16 N8 N9 Cu1 179.5(2) . . . . ?
C18 C19 C20 C21 -0.3(5) . . . . ?
C19 C18 N17 C22 -1.0(5) . . . . ?
C19 C18 N17 Cu1 -175.1(3) . . . . ?
C19 C20 C21 C22 -0.7(5) . . . . ?
C20 C21 C22 N17 0.8(5) . . . . ?
C20 C21 C22 N23 179.8(3) . . . . ?
C21 C22 N17 C18 0.0(5) . . . . ?
C21 C22 N17 Cu1 174.5(2) . . . . ?
C21 C22 N23 C31 3.3(5) . . . . ?
C21 C22 N23 N24 -173.9(3) . . . . ?
C22 N23 N24 C25 177.9(3) . . . . ?
C22 N23 N24 Cu1 -3.3(3) . . . . ?
C25 C26 C27 C28 178.9(4) . . . . ?
C25 C26 C31 C30 178.6(3) . . . . ?
C25 C26 C31 N23 -1.5(4) . . . . ?
C26 C25 N24 Cu1 -179.3(3) . . . . ?
C26 C25 N24 N23 -1.1(4) . . . . ?
C26 C27 C28 C29 1.6(5) . . . . ?
C26 C31 N23 C22 -176.4(3) . . . . ?
C26 C31 N23 N24 0.9(4) . . . . ?
C27 C26 C31 C30 -2.2(5) . . . . ?
C27 C26 C31 N23 177.7(3) . . . . ?
C27 C28 C29 C30 -1.0(6) . . . . ?
C28 C29 C30 C31 -1.2(5) . . . . ?
C29 C30 C31 C26 2.8(5) . . . . ?
C29 C30 C31 N23 -177.1(3) . . . . ?
C30 C31 N23 C22 3.6(6) . . . . ?
C30 C31 N23 N24 -179.2(3) . . . . ?
C31 C26 C27 C28 -0.1(5) . . . . ?
C31 N23 N24 C25 0.1(4) . . . . ?
C31 N23 N24 Cu1 178.9(2) . . . . ?
N2 C3 C4 C5 2.2(6) . . . . ?
N2 C7 N8 C16 -175.2(3) . . . . ?
N2 C7 N8 N9 5.9(4) . . . . ?
N2 Cu1 N9 C10 175.5(4) . . . . ?
N2 Cu1 N9 N8 -2.2(2) . . . . ?
N2 Cu1 N17 C18 41(2) . . . . ?
N2 Cu1 N17 C22 -133(2) . . . . ?
N2 Cu1 N24 C25 -3.5(4) . . . . ?
N2 Cu1 N24 N23 178.3(2) . . . . ?
N2 Cu1 O32 N33 85.1(2) . . . . ?
N8 C7 N2 C3 179.9(3) . . . . ?
N8 C7 N2 Cu1 -7.8(3) . . . . ?
N9 C10 C11 C12 -177.2(4) . . . . ?
N9 C10 C11 C16 1.6(4) . . . . ?
N9 Cu1 N2 C3 177.3(3) . . . . ?
N9 Cu1 N2 C7 5.6(2) . . . . ?
N9 Cu1 N17 C18 -47.1(3) . . . . ?
N9 Cu1 N17 C22 138.6(2) . . . . ?
N9 Cu1 N24 C25 85.6(4) . . . . ?
N9 Cu1 N24 N23 -92.6(2) . . . . ?
N9 Cu1 O32 N33 10.4(3) . . . . ?
N17 C18 C19 C20 1.1(5) . . . . ?
N17 C22 N23 C31 -177.7(3) . . . . ?
N17 C22 N23 N24 5.1(4) . . . . ?
N17 Cu1 N2 C3 89(2) . . . . ?
N17 Cu1 N2 C7 -83(2) . . . . ?
N17 Cu1 N9 C10 -7.9(4) . . . . ?
N17 Cu1 N9 N8 174.4(2) . . . . ?
N17 Cu1 N24 C25 178.9(4) . . . . ?
N17 Cu1 N24 N23 0.7(2) . . . . ?
N17 Cu1 O32 N33 -92.4(2) . . . . ?
N23 C22 N17 C18 -179.0(3) . . . . ?
N23 C22 N17 Cu1 -4.5(4) . . . . ?
N24 C25 C26 C27 -177.5(4) . . . . ?
N24 C25 C26 C31 1.6(4) . . . . ?
N24 Cu1 N2 C3 -46.3(3) . . . . ?
N24 Cu1 N2 C7 142.0(2) . . . . ?
N24 Cu1 N9 C10 77.6(4) . . . . ?
N24 Cu1 N9 N8 -100.1(2) . . . . ?
N24 Cu1 N17 C18 176.4(3) . . . . ?
N24 Cu1 N17 C22 2.1(2) . . . . ?
N24 Cu1 O32 N33 -172.3(2) . . . . ?
O32 Cu1 N2 C3 39.6(3) . . . . ?
O32 Cu1 N2 C7 -132.1(2) . . . . ?
O32 Cu1 N9 C10 -106.4(4) . . . . ?
O32 Cu1 N9 N8 75.9(3) . . . . ?
O32 Cu1 N17 C18 90.0(3) . . . . ?
O32 Cu1 N17 C22 -84.3(2) . . . . ?
O32 Cu1 N24 C25 -91.6(4) . . . . ?
O32 Cu1 N24 N23 90.2(2) . . . . ?
O34 N33 O32 Cu1 1.7(4) . . . . ?
O35 N33 O32 Cu1 -178.9(3) . . . . ?

# start Validation Reply Form
_vrf_PLAT415_1                   
;
PROBLEM: Short Inter D-H..H-X       H13    ..  H45A    ..       2.00 Ang.  
RESPONSE: Hydrogen atoms for disordered water molecules were included in arbitrary
locations. Hydrogen bonding connectivity could not be unequivocally established
due to anion and solvent disorder
;
_database_code_depnum_ccdc_archive 'CCDC 1018279'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2
_audit_creation_date             2014-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H18 Cu N7 O3, N O3'
_chemical_formula_sum            'C24 H18 Cu N8 O6'
_chemical_formula_weight         578.00
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   18.0728(19)
_cell_length_b                   7.5078(6)
_cell_length_c                   18.9452(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.277(13)
_cell_angle_gamma                90.00
_cell_volume                     2324.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3205
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.6314
_cell_measurement_theta_min      2.7016
_exptl_absorpt_coefficient_mu    1.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9123
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.79
_diffrn_reflns_theta_min         2.70
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00   23.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.7813   37.0000   60.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   36.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.7813   37.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   60.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       39.7813  -99.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega   65.00   96.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       39.7813 -125.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  5 omega   94.00  120.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       39.7813  165.0000  105.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   45.00  115.00   1.0000   49.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801 -116.0000   41.0000 70

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00  121.00   1.0000   49.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801 -125.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
  8 omega   42.00   80.00   1.0000   49.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
  9 omega   78.00  150.00   1.0000   49.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   30.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
 10 omega   53.00   96.00   1.0000   49.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
 11 omega   31.00   90.00   1.0000   49.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000    0.0000 59

#__ type_ start__ end____ width___ exp.time_
 12 omega  111.00  177.00   1.0000   49.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  125.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
 13 omega   57.00   90.00   1.0000   49.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000 -120.0000 33
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0928998000
_diffrn_orient_matrix_UB_12      -0.0187597000
_diffrn_orient_matrix_UB_13      -0.0259258000
_diffrn_orient_matrix_UB_21      0.0062053000
_diffrn_orient_matrix_UB_22      -0.2020655000
_diffrn_orient_matrix_UB_23      -0.0106001000
_diffrn_orient_matrix_UB_31      0.0151531000
_diffrn_orient_matrix_UB_32      -0.0306734000
_diffrn_orient_matrix_UB_33      0.0854585000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_number_gt                3732
_reflns_number_total             4575
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XLMP (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         1.054
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4575
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0707P)²+2.5281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1458
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C26(H26), C27(H27), C28(H28),
  C29(H29), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.27454(3) 0.47162(6) 0.47391(3) 0.02264(15) Uani 1 d . . .
N2 N 0.29646(16) 0.6101(4) 0.38127(15) 0.0260(5) Uani 1 d . . .
C3 C 0.2446(2) 0.6337(5) 0.30521(19) 0.0324(7) Uani 1 d . . .
H3 H 0.1956 0.5659 0.2836 0.039 Uiso 1 calc . . R
C4 C 0.2608(2) 0.7532(5) 0.25796(19) 0.0345(8) Uani 1 d . . .
H4 H 0.2233 0.7685 0.2049 0.041 Uiso 1 calc . . R
C5 C 0.3325(2) 0.8496(5) 0.2896(2) 0.0360(8) Uani 1 d . . .
H5 H 0.3443 0.9340 0.2585 0.043 Uiso 1 calc . . R
C6 C 0.3875(2) 0.8236(5) 0.3670(2) 0.0317(7) Uani 1 d . . .
H6 H 0.4381 0.8857 0.3897 0.038 Uiso 1 calc . . R
C7 C 0.36519(19) 0.7032(4) 0.40935(17) 0.0239(6) Uani 1 d . . .
N8 N 0.41644(15) 0.6692(3) 0.48976(14) 0.0209(5) Uani 1 d . . .
N9 N 0.38524(15) 0.5778(4) 0.53298(15) 0.0228(5) Uani 1 d . . .
C10 C 0.44682(18) 0.5682(4) 0.60518(17) 0.0224(6) Uani 1 d . . .
C11 C 0.4472(2) 0.4880(5) 0.67312(19) 0.0279(7) Uani 1 d . . .
H11 H 0.4003 0.4297 0.6726 0.033 Uiso 1 calc . . R
C12 C 0.5186(2) 0.4991(5) 0.73941(19) 0.0307(7) Uani 1 d . . .
H12 H 0.5210 0.4457 0.7858 0.037 Uiso 1 calc . . R
C13 C 0.5893(2) 0.5867(5) 0.74211(19) 0.0311(7) Uani 1 d . . .
H13 H 0.6371 0.5907 0.7901 0.037 Uiso 1 calc . . R
C14 C 0.59053(19) 0.6654(5) 0.67770(19) 0.0291(7) Uani 1 d . . .
H14 H 0.6381 0.7234 0.6798 0.035 Uiso 1 calc . . R
C15 C 0.51742(18) 0.6568(4) 0.60728(18) 0.0235(6) Uani 1 d . . .
C16 C 0.49413(19) 0.7202(4) 0.53162(19) 0.0253(6) Uani 1 d . . .
H16 H 0.5270 0.7868 0.5132 0.030 Uiso 1 calc . . R
N17 N 0.21340(16) 0.6598(4) 0.50502(15) 0.0229(5) Uani 1 d . . .
C18 C 0.2443(2) 0.8049(4) 0.54921(18) 0.0266(6) Uani 1 d . . .
H18 H 0.3018 0.8229 0.5718 0.032 Uiso 1 calc . . R
C19 C 0.1956(2) 0.9295(5) 0.5633(2) 0.0287(7) Uani 1 d . . .
H19 H 0.2190 1.0291 0.5962 0.034 Uiso 1 calc . . R
C20 C 0.1106(2) 0.9041(5) 0.52748(19) 0.0286(7) Uani 1 d . . .
H20 H 0.0755 0.9890 0.5349 0.034 Uiso 1 calc . . R
C21 C 0.07766(19) 0.7558(5) 0.48152(18) 0.0267(6) Uani 1 d . . .
H21 H 0.0203 0.7364 0.4564 0.032 Uiso 1 calc . . R
C22 C 0.13216(18) 0.6374(4) 0.47395(17) 0.0232(6) Uani 1 d . . .
N23 N 0.10606(16) 0.4769(4) 0.43118(15) 0.0227(5) Uani 1 d . . .
N24 N 0.16223(16) 0.3781(4) 0.41843(16) 0.0263(5) Uani 1 d . . .
C25 C 0.12204(19) 0.2323(4) 0.38110(17) 0.0250(6) Uani 1 d . . .
C26 C 0.1510(2) 0.0872(5) 0.3514(2) 0.0320(7) Uani 1 d . . .
H26 H 0.2058 0.0823 0.3571 0.038 Uiso 1 calc . . R
C27 C 0.0960(2) -0.0442(5) 0.3143(2) 0.0359(8) Uani 1 d . . .
H27 H 0.1132 -0.1418 0.2931 0.043 Uiso 1 calc . . R
C28 C 0.0136(2) -0.0418(5) 0.30599(19) 0.0331(7) Uani 1 d . . .
H28 H -0.0217 -0.1388 0.2811 0.040 Uiso 1 calc . . R
C29 C -0.0149(2) 0.0975(5) 0.33314(18) 0.0280(7) Uani 1 d . . .
H29 H -0.0698 0.0999 0.3272 0.034 Uiso 1 calc . . R
C30 C 0.03947(18) 0.2384(5) 0.37041(17) 0.0246(6) Uani 1 d . . .
C31 C 0.03176(18) 0.3988(5) 0.40344(17) 0.0249(6) Uani 1 d . . .
H31 H -0.0161 0.4442 0.4060 0.030 Uiso 1 calc . . R
O32 O 0.32829(14) 0.2466(3) 0.45890(13) 0.0285(5) Uani 1 d . . .
N33 N 0.34862(15) 0.1574(4) 0.52219(16) 0.0255(5) Uani 1 d . . .
O34 O 0.32108(16) 0.2077(4) 0.56897(14) 0.0344(5) Uani 1 d . . .
O35 O 0.39470(17) 0.0284(3) 0.53506(17) 0.0381(6) Uani 1 d . . .
O36 O 0.1173(2) 0.2838(5) 0.1484(2) 0.0581(8) Uani 1 d . . .
N37 N 0.16768(17) 0.1669(4) 0.15079(16) 0.0298(6) Uani 1 d . . .
O38 O 0.24057(18) 0.1890(5) 0.1887(2) 0.0621(10) Uani 1 d . . .
O39 O 0.1408(2) 0.0244(5) 0.11425(19) 0.0515(8) Uani 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 N2 2.216(3) . ?
Cu1 N9 1.994(3) . ?
Cu1 N17 2.030(3) . ?
Cu1 N24 1.974(3) . ?
Cu1 O32 2.029(2) . ?
N2 C3 1.354(4) . ?
N2 C7 1.323(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.378(5) . ?
C7 N8 1.428(4) . ?
N8 N9 1.361(4) . ?
N8 C16 1.340(4) . ?
N9 C10 1.347(4) . ?
C10 C11 1.419(5) . ?
C10 C15 1.425(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.366(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.418(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.365(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.423(4) . ?
C15 C16 1.394(5) . ?
C16 H16 0.9500 . ?
N17 C18 1.342(4) . ?
N17 C22 1.339(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.402(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.381(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.379(4) . ?
C22 N23 1.416(4) . ?
N23 N24 1.359(4) . ?
N23 C31 1.349(4) . ?
N24 C25 1.337(4) . ?
C25 C26 1.424(5) . ?
C25 C30 1.418(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.364(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.428(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.361(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.411(5) . ?
C30 C31 1.392(5) . ?
C31 H31 0.9500 . ?
O32 N33 1.283(4) . ?
N33 O34 1.246(4) . ?
N33 O35 1.232(4) . ?
O36 N37 1.251(4) . ?
N37 O38 1.213(4) . ?
N37 O39 1.254(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N9 Cu1 N2 77.37(10) . . ?
N9 Cu1 N17 95.68(11) . . ?
N9 Cu1 O32 89.19(10) . . ?
N17 Cu1 N2 101.95(10) . . ?
N24 Cu1 N2 103.65(11) . . ?
N24 Cu1 N9 176.37(11) . . ?
N24 Cu1 N17 80.70(11) . . ?
N24 Cu1 O32 94.26(11) . . ?
O32 Cu1 N2 91.24(10) . . ?
O32 Cu1 N17 166.65(10) . . ?
C3 N2 Cu1 128.9(2) . . ?
C7 N2 Cu1 112.6(2) . . ?
C7 N2 C3 117.6(3) . . ?
N2 C3 H3 118.9 . . ?
N2 C3 C4 122.1(3) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 121.6 . . ?
C7 C6 C5 116.8(3) . . ?
C7 C6 H6 121.6 . . ?
N2 C7 C6 124.8(3) . . ?
N2 C7 N8 113.8(3) . . ?
C6 C7 N8 121.4(3) . . ?
N9 N8 C7 119.0(2) . . ?
C16 N8 C7 128.2(3) . . ?
C16 N8 N9 112.7(2) . . ?
N8 N9 Cu1 115.95(19) . . ?
C10 N9 Cu1 138.1(2) . . ?
C10 N9 N8 105.2(2) . . ?
N9 C10 C11 128.7(3) . . ?
N9 C10 C15 110.2(3) . . ?
C11 C10 C15 121.1(3) . . ?
C10 C11 H11 121.8 . . ?
C12 C11 C10 116.4(3) . . ?
C12 C11 H11 121.8 . . ?
C11 C12 H12 118.5 . . ?
C11 C12 C13 123.0(3) . . ?
C13 C12 H12 118.5 . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 121.5 . . ?
C13 C14 C15 117.1(3) . . ?
C15 C14 H14 121.5 . . ?
C14 C15 C10 120.6(3) . . ?
C16 C15 C10 104.9(3) . . ?
C16 C15 C14 134.5(3) . . ?
N8 C16 C15 106.9(3) . . ?
N8 C16 H16 126.5 . . ?
C15 C16 H16 126.5 . . ?
C18 N17 Cu1 127.8(2) . . ?
C22 N17 Cu1 114.6(2) . . ?
C22 N17 C18 117.5(3) . . ?
N17 C18 H18 118.7 . . ?
N17 C18 C19 122.6(3) . . ?
C19 C18 H18 118.7 . . ?
C18 C19 H19 121.0 . . ?
C18 C19 C20 118.0(3) . . ?
C20 C19 H19 121.0 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 121.6 . . ?
C22 C21 C20 116.8(3) . . ?
C22 C21 H21 121.6 . . ?
N17 C22 C21 124.9(3) . . ?
N17 C22 N23 113.1(3) . . ?
C21 C22 N23 122.0(3) . . ?
N24 N23 C22 118.3(3) . . ?
C31 N23 C22 128.7(3) . . ?
C31 N23 N24 112.9(3) . . ?
N23 N24 Cu1 112.8(2) . . ?
C25 N24 Cu1 140.9(2) . . ?
C25 N24 N23 105.2(3) . . ?
N24 C25 C26 128.8(3) . . ?
N24 C25 C30 110.5(3) . . ?
C30 C25 C26 120.7(3) . . ?
C25 C26 H26 121.7 . . ?
C27 C26 C25 116.5(3) . . ?
C27 C26 H26 121.7 . . ?
C26 C27 H27 118.5 . . ?
C26 C27 C28 123.0(3) . . ?
C28 C27 H27 118.5 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 121.0 . . ?
C28 C29 C30 118.0(3) . . ?
C30 C29 H29 121.0 . . ?
C29 C30 C25 120.9(3) . . ?
C31 C30 C25 105.4(3) . . ?
C31 C30 C29 133.8(3) . . ?
N23 C31 C30 106.1(3) . . ?
N23 C31 H31 127.0 . . ?
C30 C31 H31 127.0 . . ?
N33 O32 Cu1 105.48(18) . . ?
O34 N33 O32 117.7(3) . . ?
O35 N33 O32 119.7(3) . . ?
O35 N33 O34 122.6(3) . . ?
O36 N37 O39 118.3(3) . . ?
O38 N37 O36 121.0(4) . . ?
O38 N37 O39 120.7(4) . . ?

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 N2 C3 C4 166.5(3) . . . . ?
Cu1 N2 C7 C6 -169.3(3) . . . . ?
Cu1 N2 C7 N8 10.5(3) . . . . ?
Cu1 N9 C10 C11 -11.1(6) . . . . ?
Cu1 N9 C10 C15 170.0(2) . . . . ?
Cu1 N17 C18 C19 176.6(2) . . . . ?
Cu1 N17 C22 C21 -174.4(2) . . . . ?
Cu1 N17 C22 N23 5.5(3) . . . . ?
Cu1 N24 C25 C26 -16.3(6) . . . . ?
Cu1 N24 C25 C30 165.8(3) . . . . ?
Cu1 O32 N33 O34 11.3(3) . . . . ?
Cu1 O32 N33 O35 -167.9(2) . . . . ?
N2 Cu1 N9 N8 -1.7(2) . . . . ?
N2 Cu1 N9 C10 -170.3(3) . . . . ?
N2 Cu1 N17 C18 -76.4(3) . . . . ?
N2 Cu1 N17 C22 100.2(2) . . . . ?
N2 Cu1 N24 N23 -102.4(2) . . . . ?
N2 Cu1 N24 C25 92.1(4) . . . . ?
N2 Cu1 O32 N33 159.57(19) . . . . ?
N2 C3 C4 C5 0.6(5) . . . . ?
N2 C7 N8 N9 -12.9(4) . . . . ?
N2 C7 N8 C16 169.0(3) . . . . ?
C3 N2 C7 C6 0.6(5) . . . . ?
C3 N2 C7 N8 -179.5(3) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C4 C5 C6 C7 -2.0(5) . . . . ?
C5 C6 C7 N2 1.1(5) . . . . ?
C5 C6 C7 N8 -178.7(3) . . . . ?
C6 C7 N8 N9 167.0(3) . . . . ?
C6 C7 N8 C16 -11.2(5) . . . . ?
C7 N2 C3 C4 -1.5(5) . . . . ?
C7 N8 N9 Cu1 8.3(3) . . . . ?
C7 N8 N9 C10 -179.5(3) . . . . ?
C7 N8 C16 C15 179.4(3) . . . . ?
N8 N9 C10 C11 179.6(3) . . . . ?
N8 N9 C10 C15 0.6(3) . . . . ?
N9 Cu1 N2 C3 -173.6(3) . . . . ?
N9 Cu1 N2 C7 -5.1(2) . . . . ?
N9 Cu1 N17 C18 1.8(3) . . . . ?
N9 Cu1 N17 C22 178.5(2) . . . . ?
N9 Cu1 N24 N23 3.5(19) . . . . ?
N9 Cu1 N24 C25 -162.0(16) . . . . ?
N9 Cu1 O32 N33 82.22(19) . . . . ?
N9 N8 C16 C15 1.1(4) . . . . ?
N9 C10 C11 C12 -179.5(3) . . . . ?
N9 C10 C15 C14 179.7(3) . . . . ?
N9 C10 C15 C16 0.0(3) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C10 C15 C16 N8 -0.7(3) . . . . ?
C11 C10 C15 C14 0.7(5) . . . . ?
C11 C10 C15 C16 -179.0(3) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C10 -0.5(5) . . . . ?
C13 C14 C15 C16 179.1(3) . . . . ?
C14 C15 C16 N8 179.7(3) . . . . ?
C15 C10 C11 C12 -0.7(5) . . . . ?
C16 N8 N9 Cu1 -173.2(2) . . . . ?
C16 N8 N9 C10 -1.1(3) . . . . ?
N17 Cu1 N2 C3 -80.4(3) . . . . ?
N17 Cu1 N2 C7 88.1(2) . . . . ?
N17 Cu1 N9 N8 -102.7(2) . . . . ?
N17 Cu1 N9 C10 88.7(3) . . . . ?
N17 Cu1 N24 N23 -2.3(2) . . . . ?
N17 Cu1 N24 C25 -167.7(4) . . . . ?
N17 Cu1 O32 N33 -29.4(5) . . . . ?
N17 C18 C19 C20 -2.1(5) . . . . ?
N17 C22 N23 N24 -7.8(4) . . . . ?
N17 C22 N23 C31 168.2(3) . . . . ?
C18 N17 C22 C21 2.6(5) . . . . ?
C18 N17 C22 N23 -177.5(3) . . . . ?
C18 C19 C20 C21 1.8(5) . . . . ?
C19 C20 C21 C22 0.5(5) . . . . ?
C20 C21 C22 N17 -2.9(5) . . . . ?
C20 C21 C22 N23 177.2(3) . . . . ?
C21 C22 N23 N24 172.1(3) . . . . ?
C21 C22 N23 C31 -11.9(5) . . . . ?
C22 N17 C18 C19 0.0(5) . . . . ?
C22 N23 N24 Cu1 6.2(3) . . . . ?
C22 N23 N24 C25 176.7(3) . . . . ?
C22 N23 C31 C30 -176.1(3) . . . . ?
N23 N24 C25 C26 177.6(3) . . . . ?
N23 N24 C25 C30 -0.3(3) . . . . ?
N24 Cu1 N2 C3 2.8(3) . . . . ?
N24 Cu1 N2 C7 171.3(2) . . . . ?
N24 Cu1 N9 N8 -108.4(18) . . . . ?
N24 Cu1 N9 C10 83.0(18) . . . . ?
N24 Cu1 N17 C18 -178.6(3) . . . . ?
N24 Cu1 N17 C22 -1.9(2) . . . . ?
N24 Cu1 O32 N33 -96.64(19) . . . . ?
N24 N23 C31 C30 0.1(3) . . . . ?
N24 C25 C26 C27 -179.0(3) . . . . ?
N24 C25 C30 C29 -179.2(3) . . . . ?
N24 C25 C30 C31 0.3(4) . . . . ?
C25 C26 C27 C28 -1.0(6) . . . . ?
C25 C30 C31 N23 -0.2(3) . . . . ?
C26 C25 C30 C29 2.8(5) . . . . ?
C26 C25 C30 C31 -177.7(3) . . . . ?
C26 C27 C28 C29 2.1(6) . . . . ?
C27 C28 C29 C30 -0.6(5) . . . . ?
C28 C29 C30 C25 -1.7(5) . . . . ?
C28 C29 C30 C31 178.9(3) . . . . ?
C29 C30 C31 N23 179.2(3) . . . . ?
C30 C25 C26 C27 -1.3(5) . . . . ?
C31 N23 N24 Cu1 -170.4(2) . . . . ?
C31 N23 N24 C25 0.1(3) . . . . ?
O32 Cu1 N2 C3 97.5(3) . . . . ?
O32 Cu1 N2 C7 -94.0(2) . . . . ?
O32 Cu1 N9 N8 89.7(2) . . . . ?
O32 Cu1 N9 C10 -78.9(3) . . . . ?
O32 Cu1 N17 C18 112.8(5) . . . . ?
O32 Cu1 N17 C22 -70.6(5) . . . . ?
O32 Cu1 N24 N23 165.2(2) . . . . ?
O32 Cu1 N24 C25 -0.2(4) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1018280'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3
_audit_creation_date             2014-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C36 H32 Cu3 N10 O16, 2.25(C6 H6), 2(H2 O)'
_chemical_formula_sum            'C49.50 H49.50 Cu3 N10 O18'
_chemical_formula_weight         1263.11
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.2213(6)
_cell_length_b                   11.4215(5)
_cell_length_c                   14.0872(7)
_cell_angle_alpha                105.934(4)
_cell_angle_beta                 101.559(4)
_cell_angle_gamma                104.354(4)
_cell_volume                     1467.04(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9142
_cell_measurement_temperature    120.0(10)
_cell_measurement_theta_max      73.7592
_cell_measurement_theta_min      3.4044
_exptl_absorpt_coefficient_mu    1.915
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22189
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.92
_diffrn_reflns_theta_min         3.41
_diffrn_ambient_temperature      120.0(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -114.00  -12.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6512  -57.0000   30.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega -104.00  -10.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6512  -57.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   36.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6512   37.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
  4 omega -103.00  -12.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -39.6512  -57.0000  120.0000 91

#__ type_ start__ end____ width___ exp.time_
  5 omega   26.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       39.6512 -128.0000   19.0000 71

#__ type_ start__ end____ width___ exp.time_
  6 omega    4.00   70.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       39.6512  -99.0000   90.0000 66

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       39.6512 -142.0000  -84.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega    7.00   32.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   88.0000  -21.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   13.00   45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   82.0000 -140.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega   12.00   37.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000   33.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   17.00   45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000  -72.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   17.00   42.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000   76.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega  -55.00  -28.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega  -54.00  -28.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -74.0000 -176.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  -54.00  -28.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   33.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000  -25.0000 28

#__ type_ start__ end____ width___ exp.time_
 17 omega   32.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000   84.0000 29

#__ type_ start__ end____ width___ exp.time_
 18 omega  103.00  141.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000   84.0000 38

#__ type_ start__ end____ width___ exp.time_
 19 omega   31.00   59.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000  131.0000 28

#__ type_ start__ end____ width___ exp.time_
 20 omega  109.00  137.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000  -25.0000 28

#__ type_ start__ end____ width___ exp.time_
 21 omega   96.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000  131.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   37.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  171.0000 38

#__ type_ start__ end____ width___ exp.time_
 23 omega  101.00  146.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
 24 omega   35.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 25 omega   34.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  -72.0000 33

#__ type_ start__ end____ width___ exp.time_
 26 omega   82.00  142.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  171.0000 60

#__ type_ start__ end____ width___ exp.time_
 27 omega   39.00   80.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   75.0000  -10.0000 41

#__ type_ start__ end____ width___ exp.time_
 28 omega   88.00  120.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   77.0000 -125.0000 32

#__ type_ start__ end____ width___ exp.time_
 29 omega   42.00   80.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   77.0000 -125.0000 38

#__ type_ start__ end____ width___ exp.time_
 30 omega   30.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -94.0000   30.0000 76

#__ type_ start__ end____ width___ exp.time_
 31 omega   75.00  170.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000  -30.0000 95

#__ type_ start__ end____ width___ exp.time_
 32 omega   75.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000  120.0000 102

#__ type_ start__ end____ width___ exp.time_
 33 omega  128.00  168.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  125.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 34 omega   78.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   61.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 35 omega   74.00  147.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000 -120.0000 73

#__ type_ start__ end____ width___ exp.time_
 36 omega   78.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   61.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 37 omega   32.00  103.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -94.0000  120.0000 71

#__ type_ start__ end____ width___ exp.time_
 38 omega   82.00  109.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   61.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 39 omega   80.00  170.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   61.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 40 omega   74.00  101.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 41 omega   74.00  100.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 42 omega   59.00   98.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853  -45.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
 43 omega   75.00  143.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
 44 omega   33.00  118.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853 -125.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
 45 omega  113.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000  -90.0000 64

#__ type_ start__ end____ width___ exp.time_
 46 omega   76.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 47 omega   74.00  100.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 48 omega   74.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 49 omega   74.00  101.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 50 omega   81.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   61.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 51 omega   74.00  172.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7853   77.0000   60.0000 98
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0945255000
_diffrn_orient_matrix_UB_12      0.0459974000
_diffrn_orient_matrix_UB_13      0.0643834000
_diffrn_orient_matrix_UB_21      -0.1202720000
_diffrn_orient_matrix_UB_22      -0.0389059000
_diffrn_orient_matrix_UB_23      -0.0996133000
_diffrn_orient_matrix_UB_31      -0.0547346000
_diffrn_orient_matrix_UB_32      -0.1353358000
_diffrn_orient_matrix_UB_33      0.0061135000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_number_gt                4919
_reflns_number_total             5737
_reflns_odcompleteness_completeness 98.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.130
_refine_diff_density_min         -0.820
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         5737
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0996P)²+1.8571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1646
_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. 

Coordinating nitrate anions were split over two positions sharing two oxygen
atoms using the PART instruction, with 50% occupancy at each site. Two non-
coordinating water molecules O36 and O37 per ASU were modelled at 50% 
occupancy and PART commands relative to the occupancy of the adjacent nitrate
anions. Lattice benzene molecules were modelled at 75% occupancy and thermal
parameters were restrained with the ISOR restraint.  Due to the low occupancy
of the lattice water molecules, hydrogen bonding connectivity could not be
fully established. Coordinating ethanol molecule was modelled as full occupancy
in a single orientation and was not further split due to lack of viable nearby
Fourier peaks to assign rotational disorder.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H37A,H37B} of O37, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H36A,H36B} of O36, All O(H) groups
2. Restrained distances
 O27-H27
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C40) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C38) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.002
4. Others
 Fixed Sof: N31(0.5) O33(0.5) N34(0.5) O35(0.5) C41(0.75) H41(0.75) C42(0.75)
 H42(0.75) C43(0.75) H43(0.75) C44(0.75) H44(0.75) C45(0.75) H45(0.75)
 C46(0.75) H46(0.75) C38(0.75) H38(0.75) C39(0.75) H39(0.75) C40(0.75)
 H40(0.75) O36(0.5) H36A(0.5) H36B(0.5) O37(0.5) H37A(0.5) H37B(0.5)
5.a Free rotating group:
 O36(H36A,H36B), O37(H37A,H37B)
5.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
5.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C6(H6), C8(H8), C9(H9), C11(H11), N16(H16), C18(H18), C20(H20),
 C21(H21), C23(H23), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46),
  C38(H38), C39(H39), C40(H40)
5.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 1.50978(4) 0.88878(4) 0.44882(3) 0.02661(16) Uani 1 d . . 1 . . .
Cu2 Cu 0.5000 0.5000 0.0000 0.02999(19) Uani 1 d . . 2 S T P
N3 N 0.6597(3) 0.6325(3) 0.1189(2) 0.0317(6) Uani 1 d . . 1 . . .
N4 N 0.7918(3) 0.6235(3) 0.1383(2) 0.0328(6) Uani 1 d . . 1 . . .
H4 H 0.8160 0.5590 0.1045 0.039 Uiso 1 calc . . 1 R . .
C5 C 0.8814(3) 0.7296(3) 0.2184(2) 0.0303(6) Uani 1 d . . 1 . . .
C6 C 1.0268(3) 0.7619(3) 0.2658(2) 0.0326(7) Uani 1 d . . 1 . . .
H6 H 1.0794 0.7071 0.2441 0.039 Uiso 1 calc . . 1 R . .
C7 C 1.0880(3) 0.8778(3) 0.3456(2) 0.0317(7) Uani 1 d . . 1 . . .
C8 C 1.0095(3) 0.9599(3) 0.3778(3) 0.0351(7) Uani 1 d . . 1 . . .
H8 H 1.0567 1.0402 0.4318 0.042 Uiso 1 calc . . 1 R . .
C9 C 0.8675(3) 0.9264(3) 0.3330(3) 0.0352(7) Uani 1 d . . 1 . . .
H9 H 0.8150 0.9806 0.3562 0.042 Uiso 1 calc . . 1 R . .
C10 C 0.8025(3) 0.8081(3) 0.2511(2) 0.0311(7) Uani 1 d . . 1 . . .
C11 C 0.6629(3) 0.7403(3) 0.1857(2) 0.0311(7) Uani 1 d . . 1 . . .
H11 H 0.5835 0.7685 0.1897 0.037 Uiso 1 calc . . 1 R . .
C12 C 1.2415(3) 0.9187(3) 0.4021(2) 0.0314(7) Uani 1 d . . 1 . . .
O13 O 1.3083(2) 0.8409(2) 0.37940(18) 0.0354(5) Uani 1 d . . 1 . . .
O14 O 1.2926(2) 1.0299(2) 0.46960(19) 0.0390(5) Uani 1 d . . 1 . . .
N15 N 1.5316(3) 1.3648(3) 0.0600(2) 0.0323(6) Uani 1 d . . 1 . . .
N16 N 1.5027(3) 1.3646(3) 0.1501(2) 0.0341(6) Uani 1 d . . 1 . . .
H16 H 1.4664 1.4181 0.1850 0.041 Uiso 1 calc . . 1 R . .
C17 C 1.5384(3) 1.2692(3) 0.1780(2) 0.0323(7) Uani 1 d . . 1 . . .
C18 C 1.5256(3) 1.2315(3) 0.2634(3) 0.0336(7) Uani 1 d . . 1 . . .
H18 H 1.4903 1.2755 0.3148 0.040 Uiso 1 calc . . 1 R . .
C19 C 1.5671(3) 1.1269(3) 0.2684(2) 0.0314(7) Uani 1 d . . 1 . . .
C20 C 1.6225(4) 1.0631(3) 0.1930(3) 0.0358(7) Uani 1 d . . 1 . . .
H20 H 1.6495 0.9910 0.1990 0.043 Uiso 1 calc . . 1 R . .
C21 C 1.6382(4) 1.1029(4) 0.1116(3) 0.0396(8) Uani 1 d . . 1 . . .
H21 H 1.6781 1.0612 0.0623 0.048 Uiso 1 calc . . 1 R . .
C22 C 1.5936(3) 1.2075(3) 0.1031(2) 0.0337(7) Uani 1 d . . 1 . . .
C23 C 1.5862(4) 1.2733(3) 0.0313(3) 0.0354(7) Uani 1 d . . 1 . . .
H23 H 1.6165 1.2539 -0.0290 0.042 Uiso 1 calc . . 1 R . .
C24 C 1.5491(3) 1.0785(3) 0.3557(2) 0.0308(7) Uani 1 d . . 1 . . .
O25 O 1.5503(2) 0.9652(2) 0.34406(18) 0.0345(5) Uani 1 d . . 1 . . .
O26 O 1.4675(3) 0.8455(2) 0.56752(18) 0.0379(5) Uani 1 d . . 1 . . .
O27 O 1.5421(3) 0.7080(3) 0.3807(2) 0.0485(6) Uani 1 d . . 1 D . .
H27 H 1.471(4) 0.641(3) 0.356(4) 0.073 Uiso 1 d . . 1 DR . .
C28 C 1.6651(8) 0.6738(7) 0.4212(7) 0.110(3) Uani 1 d . . 1 . . .
H28A H 1.6641 0.5957 0.3682 0.132 Uiso 1 calc . . 1 R . .
H28B H 1.7503 0.7439 0.4287 0.132 Uiso 1 calc . . 1 R . .
C29 C 1.6810(11) 0.6511(11) 0.5139(10) 0.165(5) Uani 1 d . . 1 . . .
H29A H 1.6975 0.7311 0.5698 0.248 Uiso 1 calc . . 1 GR . .
H29B H 1.7615 0.6197 0.5268 0.248 Uiso 1 calc . . 1 GR . .
H29C H 1.5952 0.5863 0.5104 0.248 Uiso 1 calc . . 1 GR . .
O30 O 0.3488(3) 0.5379(3) 0.1044(2) 0.0520(7) Uani 1 d . . 1 . . .
N31 N 0.2311(7) 0.5490(6) 0.1030(6) 0.0397(13) Uani 0.50 d A 2 1 . . .
O32 O 0.1745(5) 0.5471(5) 0.1692(4) 0.0889(12) Uani 1 d . . 1 . . .
O33 O 0.1630(6) 0.5577(7) 0.0263(5) 0.0466(13) Uani 0.50 d A 2 1 . . .
N34 N 0.2833(9) 0.5330(8) 0.1581(7) 0.063(2) Uani 0.50 d A 1 1 . . .
O35 O 0.3399(9) 0.4986(8) 0.2341(6) 0.075(2) Uani 0.50 d A 1 1 . . .
C41 C 0.0641(8) 0.2216(8) 0.0428(6) 0.080(2) Uani 0.75 d . . 1 . . .
H41 H 0.0369 0.2612 -0.0056 0.096 Uiso 0.75 calc . . 1 R . .
C42 C 0.1542(8) 0.1516(8) 0.0304(5) 0.079(2) Uani 0.75 d . . 1 . . .
H42 H 0.1911 0.1428 -0.0270 0.094 Uiso 0.75 calc . . 1 R . .
C43 C 0.1912(8) 0.0944(7) 0.1000(6) 0.078(2) Uani 0.75 d . . 1 . . .
H43 H 0.2524 0.0446 0.0898 0.094 Uiso 0.75 calc . . 1 R . .
C44 C 0.1416(9) 0.1076(9) 0.1844(6) 0.084(2) Uani 0.75 d . . 1 . . .
H44 H 0.1695 0.0681 0.2327 0.101 Uiso 0.75 calc . . 1 R . .
C45 C 0.0531(10) 0.1767(10) 0.1990(7) 0.097(3) Uani 0.75 d . . 1 . . .
H45 H 0.0186 0.1860 0.2575 0.116 Uiso 0.75 calc . . 1 R . .
C46 C 0.0135(8) 0.2332(9) 0.1287(7) 0.091(3) Uani 0.75 d . . 1 . . .
H46 H -0.0496 0.2810 0.1387 0.109 Uiso 0.75 calc . . 1 R . .
C38 C 0.0235(9) 0.5100(8) 0.4062(7) 0.089(2) Uani 0.75 d . . 1 . U .
H38 H 0.0401 0.5185 0.3441 0.106 Uiso 0.75 calc . . 1 R . .
C39 C 0.1045(8) 0.6003(8) 0.5022(8) 0.092(3) Uani 0.75 d . . 1 . U .
H39 H 0.1790 0.6708 0.5044 0.111 Uiso 0.75 calc . . 1 R . .
C40 C 0.0829(8) 0.5932(9) 0.5941(7) 0.091(3) Uani 0.75 d . . 1 . U .
H40 H 0.1403 0.6584 0.6573 0.110 Uiso 0.75 calc . . 1 R . .
O36 O 0.3445(6) 0.4653(6) 0.2974(5) 0.0532(14) Uani 0.50 d B 2 1 . . .
H36A H 0.2642 0.4715 0.2735 0.080 Uiso 0.50 d B 2 1 G . .
H36B H 0.3412 0.4313 0.3438 0.080 Uiso 0.50 d B 2 1 G . .
O37 O 0.1157(6) 0.5753(8) -0.0494(5) 0.0634(17) Uani 0.50 d C 1 1 . . .
H37A H 0.1279 0.5697 0.0105 0.076 Uiso 0.50 d C 1 1 G . .
H37B H 0.0387 0.5903 -0.0670 0.076 Uiso 0.50 d C 1 1 G . .


_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 Cu1 2.6324(9) 2_876 ?
Cu1 O13 1.959(2) . ?
Cu1 O14 1.953(2) 2_876 ?
Cu1 O25 1.971(2) . ?
Cu1 O26 1.966(2) . ?
Cu1 O27 2.161(3) . ?
Cu2 N3 2.012(3) . ?
Cu2 N3 2.012(3) 2_665 ?
Cu2 N15 2.014(3) 2_775 ?
Cu2 N15 2.014(3) 1_445 ?
Cu2 O30 2.373(3) 2_665 ?
Cu2 O30 2.373(3) . ?
N3 N4 1.358(4) . ?
N3 C11 1.317(5) . ?
N4 H4 0.8800 . ?
N4 C5 1.366(4) . ?
C5 C6 1.409(4) . ?
C5 C10 1.395(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.377(5) . ?
C7 C8 1.420(5) . ?
C7 C12 1.498(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.411(5) . ?
C10 C11 1.421(4) . ?
C11 H11 0.9500 . ?
C12 O13 1.261(4) . ?
C12 O14 1.264(4) . ?
O14 Cu1 1.953(2) 2_876 ?
N15 Cu2 2.014(3) 1_665 ?
N15 N16 1.359(4) . ?
N15 C23 1.310(5) . ?
N16 H16 0.8800 . ?
N16 C17 1.360(4) . ?
C17 C18 1.403(4) . ?
C17 C22 1.399(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.377(5) . ?
C19 C20 1.415(5) . ?
C19 C24 1.504(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.368(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.405(5) . ?
C22 C23 1.418(4) . ?
C23 H23 0.9500 . ?
C24 O25 1.263(4) . ?
C24 O26 1.259(4) 2_876 ?
O26 C24 1.259(4) 2_876 ?
O27 H27 0.84(2) . ?
O27 C28 1.462(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.386(12) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
O30 N31 1.238(7) . ?
O30 N34 1.110(9) . ?
N31 O32 1.194(7) . ?
N31 O33 1.205(9) . ?
O32 N34 1.197(9) . ?
O33 H37A 0.4544 . ?
N34 O35 1.316(12) . ?
O35 H36A 1.0727 . ?
C41 H41 0.9500 . ?
C41 C42 1.367(12) . ?
C41 C46 1.395(11) . ?
C42 H42 0.9500 . ?
C42 C43 1.363(12) . ?
C43 H43 0.9500 . ?
C43 C44 1.369(10) . ?
C44 H44 0.9500 . ?
C44 C45 1.350(13) . ?
C45 H45 0.9500 . ?
C45 C46 1.372(12) . ?
C46 H46 0.9500 . ?
C38 H38 0.9500 . ?
C38 C39 1.393(13) . ?
C38 C40 1.390(10) 2_566 ?
C39 H39 0.9500 . ?
C39 C40 1.376(13) . ?
C40 C38 1.390(10) 2_566 ?
C40 H40 0.9500 . ?
O36 H36A 0.8499 . ?
O36 H36B 0.8503 . ?
O37 H37A 0.8506 . ?
O37 H37B 0.8500 . ?

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
O13 Cu1 Cu1 86.25(8) . 2_876 ?
O13 Cu1 O25 88.51(10) . . ?
O13 Cu1 O26 90.93(10) . . ?
O13 Cu1 O27 98.85(11) . . ?
O14 Cu1 Cu1 82.40(8) 2_876 2_876 ?
O14 Cu1 O13 168.59(10) 2_876 . ?
O14 Cu1 O25 89.69(10) 2_876 . ?
O14 Cu1 O26 88.67(11) 2_876 . ?
O14 Cu1 O27 92.55(11) 2_876 . ?
O25 Cu1 Cu1 86.75(7) . 2_876 ?
O25 Cu1 O27 97.26(11) . . ?
O26 Cu1 Cu1 82.12(8) . 2_876 ?
O26 Cu1 O25 168.86(10) . . ?
O26 Cu1 O27 93.82(11) . . ?
O27 Cu1 Cu1 173.56(8) . 2_876 ?
N3 Cu2 N3 180.0 . 2_665 ?
N3 Cu2 N15 88.79(10) . 1_445 ?
N3 Cu2 N15 91.21(10) 2_665 1_445 ?
N3 Cu2 N15 91.21(10) . 2_775 ?
N3 Cu2 N15 88.79(10) 2_665 2_775 ?
N3 Cu2 O30 92.74(11) . 2_665 ?
N3 Cu2 O30 92.74(11) 2_665 . ?
N3 Cu2 O30 87.26(11) . . ?
N3 Cu2 O30 87.26(11) 2_665 2_665 ?
N15 Cu2 N15 180.00(7) 2_775 1_445 ?
N15 Cu2 O30 91.68(11) 2_775 . ?
N15 Cu2 O30 88.32(11) 2_775 2_665 ?
N15 Cu2 O30 88.32(11) 1_445 . ?
N15 Cu2 O30 91.68(11) 1_445 2_665 ?
O30 Cu2 O30 179.999(1) 2_665 . ?
N4 N3 Cu2 121.6(2) . . ?
C11 N3 Cu2 130.1(2) . . ?
C11 N3 N4 108.2(2) . . ?
N3 N4 H4 125.2 . . ?
N3 N4 C5 109.6(3) . . ?
C5 N4 H4 125.2 . . ?
N4 C5 C6 130.0(3) . . ?
N4 C5 C10 107.5(3) . . ?
C10 C5 C6 122.5(3) . . ?
C5 C6 H6 122.0 . . ?
C7 C6 C5 116.0(3) . . ?
C7 C6 H6 122.0 . . ?
C6 C7 C8 122.0(3) . . ?
C6 C7 C12 119.7(3) . . ?
C8 C7 C12 118.3(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 121.4 . . ?
C8 C9 C10 117.3(3) . . ?
C10 C9 H9 121.4 . . ?
C5 C10 C9 120.5(3) . . ?
C5 C10 C11 104.7(3) . . ?
C9 C10 C11 134.8(3) . . ?
N3 C11 C10 109.9(3) . . ?
N3 C11 H11 125.0 . . ?
C10 C11 H11 125.0 . . ?
O13 C12 C7 118.2(3) . . ?
O13 C12 O14 125.6(3) . . ?
O14 C12 C7 116.2(3) . . ?
C12 O13 Cu1 120.5(2) . . ?
C12 O14 Cu1 125.2(2) . 2_876 ?
N16 N15 Cu2 120.2(2) . 1_665 ?
C23 N15 Cu2 131.6(2) . 1_665 ?
C23 N15 N16 108.1(3) . . ?
N15 N16 H16 125.1 . . ?
N15 N16 C17 109.8(3) . . ?
C17 N16 H16 125.1 . . ?
N16 C17 C18 130.1(3) . . ?
N16 C17 C22 107.4(3) . . ?
C22 C17 C18 122.6(3) . . ?
C17 C18 H18 121.9 . . ?
C19 C18 C17 116.2(3) . . ?
C19 C18 H18 121.9 . . ?
C18 C19 C20 121.9(3) . . ?
C18 C19 C24 118.4(3) . . ?
C20 C19 C24 119.8(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 121.0 . . ?
C20 C21 C22 118.0(3) . . ?
C22 C21 H21 121.0 . . ?
C17 C22 C21 119.9(3) . . ?
C17 C22 C23 104.5(3) . . ?
C21 C22 C23 135.6(3) . . ?
N15 C23 C22 110.2(3) . . ?
N15 C23 H23 124.9 . . ?
C22 C23 H23 124.9 . . ?
O25 C24 C19 116.8(3) . . ?
O26 C24 C19 116.7(3) 2_876 . ?
O26 C24 O25 126.5(3) 2_876 . ?
C24 O25 Cu1 119.4(2) . . ?
C24 O26 Cu1 125.1(2) 2_876 . ?
Cu1 O27 H27 118(4) . . ?
C28 O27 Cu1 124.2(4) . . ?
C28 O27 H27 108(4) . . ?
O27 C28 H28A 107.6 . . ?
O27 C28 H28B 107.6 . . ?
H28A C28 H28B 107.0 . . ?
C29 C28 O27 118.9(8) . . ?
C29 C28 H28A 107.6 . . ?
C29 C28 H28B 107.6 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N31 O30 Cu2 143.6(4) . . ?
N34 O30 Cu2 164.5(6) . . ?
N34 O30 N31 46.8(5) . . ?
O32 N31 O30 126.4(7) . . ?
O32 N31 O33 115.6(6) . . ?
O33 N31 O30 117.9(6) . . ?
N31 O32 N34 46.2(5) . . ?
N31 O33 H37A 150.0 . . ?
O30 N34 O32 140.4(11) . . ?
O30 N34 O35 111.8(9) . . ?
O32 N34 O35 107.8(9) . . ?
C42 C41 H41 121.0 . . ?
C42 C41 C46 118.0(9) . . ?
C46 C41 H41 121.0 . . ?
C41 C42 H42 119.9 . . ?
C43 C42 C41 120.3(7) . . ?
C43 C42 H42 119.9 . . ?
C42 C43 H43 119.5 . . ?
C42 C43 C44 121.0(9) . . ?
C44 C43 H43 119.5 . . ?
C43 C44 H44 120.0 . . ?
C45 C44 C43 120.0(9) . . ?
C45 C44 H44 120.0 . . ?
C44 C45 H45 120.2 . . ?
C44 C45 C46 119.5(8) . . ?
C46 C45 H45 120.2 . . ?
C41 C46 H46 119.4 . . ?
C45 C46 C41 121.2(10) . . ?
C45 C46 H46 119.4 . . ?
C39 C38 H38 121.7 . . ?
C40 C38 H38 121.7 2_566 . ?
C40 C38 C39 116.6(8) 2_566 . ?
C38 C39 H39 118.1 . . ?
C40 C39 C38 123.8(7) . . ?
C40 C39 H39 118.1 . . ?
C38 C40 H40 120.2 2_566 . ?
C39 C40 C38 119.6(8) . 2_566 ?
C39 C40 H40 120.2 . . ?
H36A O36 H36B 109.5 . . ?

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
N16 H16 O30 0.88 2.39 2.940(4) 120.5 1_665
N16 H16 O35 0.88 1.90 2.751(9) 163.7 1_665
N16 H16 O36 0.88 2.24 3.033(7) 150.4 1_665
O27 H27 O35 0.84(2) 1.96(3) 2.717(8) 148(5) 1_655
O27 H27 O36 0.84(2) 1.94(2) 2.762(7) 166(5) 1_655
O36 H36A O32 0.85 2.07 2.762(8) 137.8 .
O37 H37A O30 0.85 2.54 3.082(7) 122.5 .
O37 H37A N31 0.85 1.61 2.367(10) 145.9 .

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 Cu1 O13 C12 -0.5(2) 2_876 . . . ?
Cu1 Cu1 O25 C24 -2.2(2) 2_876 . . . ?
Cu1 Cu1 O26 C24 -2.0(2) 2_876 . . 2_876 ?
Cu1 Cu1 O27 C28 -22.0(10) 2_876 . . . ?
Cu1 O27 C28 C29 69.6(9) . . . . ?
Cu2 N3 N4 C5 175.8(2) . . . . ?
Cu2 N3 C11 C10 -175.2(2) . . . . ?
Cu2 N15 N16 C17 -177.0(2) 1_665 . . . ?
Cu2 N15 C23 C22 176.3(2) 1_665 . . . ?
Cu2 O30 N31 O32 166.0(4) . . . . ?
Cu2 O30 N31 O33 -10.9(10) . . . . ?
Cu2 O30 N34 O32 -142.4(15) . . . . ?
Cu2 O30 N34 O35 36(2) . . . . ?
N3 Cu2 N3 N4 -70(27) 2_665 . . . ?
N3 Cu2 N3 C11 106(27) 2_665 . . . ?
N3 Cu2 O30 N31 -39.5(6) 2_665 . . . ?
N3 Cu2 O30 N31 140.5(6) . . . . ?
N3 Cu2 O30 N34 85.1(19) 2_665 . . . ?
N3 Cu2 O30 N34 -94.9(19) . . . . ?
N3 N4 C5 C6 179.4(3) . . . . ?
N3 N4 C5 C10 0.4(4) . . . . ?
N4 N3 C11 C10 1.4(3) . . . . ?
N4 C5 C6 C7 179.7(3) . . . . ?
N4 C5 C10 C9 -179.5(3) . . . . ?
N4 C5 C10 C11 0.5(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C5 C6 C7 C12 178.6(3) . . . . ?
C5 C10 C11 N3 -1.2(4) . . . . ?
C6 C5 C10 C9 1.4(5) . . . . ?
C6 C5 C10 C11 -178.6(3) . . . . ?
C6 C7 C8 C9 1.9(5) . . . . ?
C6 C7 C12 O13 -4.9(4) . . . . ?
C6 C7 C12 O14 175.3(3) . . . . ?
C7 C8 C9 C10 -1.8(5) . . . . ?
C7 C12 O13 Cu1 179.2(2) . . . . ?
C7 C12 O14 Cu1 -177.5(2) . . . 2_876 ?
C8 C7 C12 O13 174.0(3) . . . . ?
C8 C7 C12 O14 -5.8(4) . . . . ?
C8 C9 C10 C5 0.3(5) . . . . ?
C8 C9 C10 C11 -179.7(3) . . . . ?
C9 C10 C11 N3 178.8(3) . . . . ?
C10 C5 C6 C7 -1.4(5) . . . . ?
C11 N3 N4 C5 -1.1(3) . . . . ?
C12 C7 C8 C9 -177.0(3) . . . . ?
O13 Cu1 O25 C24 84.1(2) . . . . ?
O13 Cu1 O26 C24 -88.0(3) . . . 2_876 ?
O13 Cu1 O27 C28 -164.2(5) . . . . ?
O13 C12 O14 Cu1 2.8(5) . . . 2_876 ?
O14 Cu1 O13 C12 -6.3(7) 2_876 . . . ?
O14 Cu1 O25 C24 -84.7(2) 2_876 . . . ?
O14 Cu1 O26 C24 80.5(3) 2_876 . . 2_876 ?
O14 Cu1 O27 C28 16.2(5) 2_876 . . . ?
O14 C12 O13 Cu1 -1.1(4) . . . . ?
N15 Cu2 N3 N4 -121.4(2) 2_775 . . . ?
N15 Cu2 N3 N4 58.6(2) 1_445 . . . ?
N15 Cu2 N3 C11 -125.2(3) 1_445 . . . ?
N15 Cu2 N3 C11 54.8(3) 2_775 . . . ?
N15 Cu2 O30 N31 -130.6(6) 1_445 . . . ?
N15 Cu2 O30 N31 49.4(6) 2_775 . . . ?
N15 Cu2 O30 N34 174.0(19) 2_775 . . . ?
N15 Cu2 O30 N34 -6.0(19) 1_445 . . . ?
N15 N16 C17 C18 -178.8(3) . . . . ?
N15 N16 C17 C22 0.7(3) . . . . ?
N16 N15 C23 C22 0.7(4) . . . . ?
N16 C17 C18 C19 177.7(3) . . . . ?
N16 C17 C22 C21 -179.3(3) . . . . ?
N16 C17 C22 C23 -0.3(3) . . . . ?
C17 C18 C19 C20 1.4(5) . . . . ?
C17 C18 C19 C24 -177.1(3) . . . . ?
C17 C22 C23 N15 -0.2(4) . . . . ?
C18 C17 C22 C21 0.3(5) . . . . ?
C18 C17 C22 C23 179.3(3) . . . . ?
C18 C19 C20 C21 0.4(5) . . . . ?
C18 C19 C24 O25 161.0(3) . . . . ?
C18 C19 C24 O26 -18.1(4) . . . 2_876 ?
C19 C20 C21 C22 -1.8(5) . . . . ?
C19 C24 O25 Cu1 -174.33(18) . . . . ?
C20 C19 C24 O25 -17.6(4) . . . . ?
C20 C19 C24 O26 163.3(3) . . . 2_876 ?
C20 C21 C22 C17 1.5(5) . . . . ?
C20 C21 C22 C23 -177.1(4) . . . . ?
C21 C22 C23 N15 178.5(4) . . . . ?
C22 C17 C18 C19 -1.7(5) . . . . ?
C23 N15 N16 C17 -0.9(3) . . . . ?
C24 C19 C20 C21 178.9(3) . . . . ?
O25 Cu1 O13 C12 -87.3(2) . . . . ?
O25 Cu1 O26 C24 -1.0(7) . . . 2_876 ?
O25 Cu1 O27 C28 106.2(5) . . . . ?
O26 Cu1 O13 C12 81.5(2) . . . . ?
O26 Cu1 O25 C24 -3.2(6) . . . . ?
O26 Cu1 O27 C28 -72.6(5) . . . . ?
O26 C24 O25 Cu1 4.6(4) 2_876 . . . ?
O27 Cu1 O13 C12 175.5(2) . . . . ?
O27 Cu1 O25 C24 -177.2(2) . . . . ?
O27 Cu1 O26 C24 173.0(3) . . . 2_876 ?
O30 Cu2 N3 N4 147.0(2) . . . . ?
O30 Cu2 N3 N4 -33.0(2) 2_665 . . . ?
O30 Cu2 N3 C11 143.2(3) 2_665 . . . ?
O30 Cu2 N3 C11 -36.8(3) . . . . ?
O30 Cu2 O30 N31 -4(17) 2_665 . . . ?
O30 Cu2 O30 N34 121(17) 2_665 . . . ?
O30 N31 O32 N34 -3.4(7) . . . . ?
N31 O30 N34 O32 -4.5(9) . . . . ?
N31 O30 N34 O35 174.0(11) . . . . ?
N31 O32 N34 O30 4.7(10) . . . . ?
N31 O32 N34 O35 -173.8(11) . . . . ?
O33 N31 O32 N34 173.6(11) . . . . ?
N34 O30 N31 O32 3.6(7) . . . . ?
N34 O30 N31 O33 -173.3(11) . . . . ?
C41 C42 C43 C44 -1.2(10) . . . . ?
C42 C41 C46 C45 0.3(11) . . . . ?
C42 C43 C44 C45 0.9(12) . . . . ?
C43 C44 C45 C46 0.0(13) . . . . ?
C44 C45 C46 C41 -0.6(13) . . . . ?
C46 C41 C42 C43 0.6(10) . . . . ?
C38 C39 C40 C38 1.2(17) . . . 2_566 ?
C40 C38 C39 C40 -1.2(16) 2_566 . . . ?

# start Validation Reply Form
_vrf_PLAT420_3                   
;
PROBLEM: D-H Without Acceptor      *O36    -  *H36B   ...     Please Check 
RESPONSE: Hydrogen atom attached to partial occupancy water molecule, hydrogen
bonding connectivity could not be fully established
;
_database_code_depnum_ccdc_archive 'CCDC 1018281'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4
_audit_creation_date             2014-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H10 Cu N4 O4, 0.5(C2 H2 O2), H2 O'
_chemical_formula_sum            'C17 H16 Cu N4 O6'
_chemical_formula_weight         435.88
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.730(2)
_cell_length_b                   4.5836(2)
_cell_length_c                   17.8406(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.140(11)
_cell_angle_gamma                90.00
_cell_volume                     1741.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2520
_cell_measurement_temperature    120.0(10)
_cell_measurement_theta_max      73.6582
_cell_measurement_theta_min      2.9902
_exptl_absorpt_coefficient_mu    2.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5385
_diffrn_reflns_theta_full        73.82
_diffrn_reflns_theta_max         73.82
_diffrn_reflns_theta_min         4.15
_diffrn_ambient_temperature      120.0(10)
_diffrn_detector_area_resol_mean 10.6501
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.6563   37.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega  -79.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.6563    0.0000  120.0000 123

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00    7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -39.6563   37.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega   30.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.6563 -125.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega   30.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       39.6563 -125.0000  -90.0000 67

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00   76.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega   51.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -77.0000    0.0000 60

#__ type_ start__ end____ width___ exp.time_
  8 omega   73.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   95.00  160.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   61.0000  -60.0000 65

#__ type_ start__ end____ width___ exp.time_
 10 omega  126.00  168.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   45.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega   94.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  125.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
 12 omega   55.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -94.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00  119.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801 -125.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
 14 omega   77.00  171.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801   30.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
 15 omega   33.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -45.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 17 omega   31.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -94.0000  120.0000 61

#__ type_ start__ end____ width___ exp.time_
 18 omega   31.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801  -30.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
 19 omega   55.00  120.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      107.7801 -125.0000 -120.0000 65
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0251861000
_diffrn_orient_matrix_UB_12      -0.2079084000
_diffrn_orient_matrix_UB_13      0.0813072000
_diffrn_orient_matrix_UB_21      0.0677229000
_diffrn_orient_matrix_UB_22      0.0901391000
_diffrn_orient_matrix_UB_23      0.0352295000
_diffrn_orient_matrix_UB_31      -0.0035803000
_diffrn_orient_matrix_UB_32      0.2482970000
_diffrn_orient_matrix_UB_33      0.0550589000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_number_gt                1640
_reflns_number_total             1742
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1742
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0560P)²+5.7306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1215
_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. 

 Lattice methanol molecule was modelled as disordered across two equivalent
 positions with carbon atom C16 occupying a crystallographic special positon.
 As such, hydrogen atoms belonging to C16 were not explicitly modelled but 
 were included in the formula to give correct values of density, F000 and
 absorption coefficient.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 H14-O14
 0.85 with sigma of 0.02
 H15-O15
 0.85 with sigma of 0.02
 H3-N3
 0.88 with sigma of 0.02
3. Others
 Fixed Sof: O15(0.5) H15(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.5000 0.0000 0.5000 0.0191(2) Uani 1 d . . 2 S T P
N2 N 0.55386(11) 0.2526(5) 0.60124(14) 0.0215(5) Uani 1 d . . 1 . . .
N3 N 0.56061(11) 0.2731(5) 0.68202(15) 0.0224(5) Uani 1 d . . 1 D . .
C4 C 0.60397(14) 0.4652(6) 0.73685(19) 0.0240(6) Uani 1 d . . 1 . . .
H4 H 0.6159 0.5137 0.7963 0.029 Uiso 1 calc . . 1 R . .
C5 C 0.62912(13) 0.5845(6) 0.69108(18) 0.0227(6) Uani 1 d . . 1 . . .
C6 C 0.67563(13) 0.7922(6) 0.71099(19) 0.0256(6) Uani 1 d . . 1 . . .
H6 H 0.6980 0.8917 0.7674 0.031 Uiso 1 calc . . 1 R . .
C7 C 0.68771(14) 0.8465(6) 0.6464(2) 0.0277(6) Uani 1 d . . 1 . . .
H7 H 0.7191 0.9847 0.6588 0.033 Uiso 1 calc . . 1 R . .
C8 C 0.65423(13) 0.7006(6) 0.56144(19) 0.0257(6) Uani 1 d . . 1 . . .
H8 H 0.6639 0.7445 0.5185 0.031 Uiso 1 calc . . 1 R . .
C9 C 0.60816(13) 0.4975(6) 0.53931(19) 0.0222(6) Uani 1 d . . 1 . . .
C10 C 0.59572(12) 0.4399(6) 0.60592(18) 0.0197(5) Uani 1 d . . 1 . . .
C11 C 0.57412(13) 0.3412(6) 0.45038(18) 0.0234(6) Uani 1 d . . 1 . . .
O12 O 0.53038(9) 0.1626(4) 0.43252(12) 0.0232(4) Uani 1 d . . 1 . . .
O13 O 0.58880(11) 0.3871(6) 0.39608(14) 0.0353(5) Uani 1 d . . 1 . . .
O15 O 0.7022(4) 0.082(2) 0.4300(5) 0.074(2) Uani 0.50 d . . 1 D . .
H15 H 0.669(4) 0.14(3) 0.425(10) 0.112 Uiso 0.50 d . . 1 DR . .
C16 C 0.7500 0.2500 0.5000 0.078(2) Uani 1 d . . 2 S T P
O14 O 0.5000 0.9715(7) 0.7500 0.0270(6) Uani 1 d . . 2 DS T P
H3 H 0.5387(17) 0.153(8) 0.691(3) 0.041 Uiso 1 d . . 1 DR . .
H14 H 0.4698(14) 0.878(8) 0.707(2) 0.041 Uiso 1 d . . 1 DR . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.927(2) 5_656 ?
Cu1 N2 1.927(2) . ?
Cu1 O12 1.9163(18) . ?
Cu1 O12 1.9164(18) 5_656 ?
N2 N3 1.355(3) . ?
N2 C10 1.343(4) . ?
N3 C4 1.324(4) . ?
N3 H3 0.868(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.406(4) . ?
C5 C6 1.410(4) . ?
C5 C10 1.421(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.373(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.422(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(4) . ?
C9 C10 1.418(4) . ?
C9 C11 1.496(4) . ?
C11 O12 1.279(4) . ?
C11 O13 1.239(3) . ?
O15 H15 0.86(2) . ?
O15 C16 1.395(9) . ?
C16 O15 1.395(9) 7_656 ?
O14 H14 0.841(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N2 179.998(1) . 5_656 ?
O12 Cu1 N2 91.30(9) . . ?
O12 Cu1 N2 88.70(9) 5_656 . ?
O12 Cu1 N2 88.70(9) . 5_656 ?
O12 Cu1 N2 91.30(9) 5_656 5_656 ?
O12 Cu1 O12 180.000(1) . 5_656 ?
N3 N2 Cu1 129.36(19) . . ?
C10 N2 Cu1 124.91(18) . . ?
C10 N2 N3 105.7(2) . . ?
N2 N3 H3 117(3) . . ?
C4 N3 N2 112.6(2) . . ?
C4 N3 H3 130(3) . . ?
N3 C4 H4 126.2 . . ?
N3 C4 C5 107.5(2) . . ?
C5 C4 H4 126.2 . . ?
C4 C5 C6 135.9(3) . . ?
C4 C5 C10 103.9(2) . . ?
C6 C5 C10 120.2(3) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 C5 118.1(3) . . ?
C7 C6 H6 121.0 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.5(3) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.1(3) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C10 116.6(3) . . ?
C8 C9 C11 121.6(3) . . ?
C10 C9 C11 121.7(3) . . ?
N2 C10 C5 110.3(2) . . ?
N2 C10 C9 128.1(2) . . ?
C9 C10 C5 121.5(3) . . ?
O12 C11 C9 118.7(2) . . ?
O13 C11 C9 119.6(3) . . ?
O13 C11 O12 121.7(3) . . ?
C11 O12 Cu1 134.81(17) . . ?
C16 O15 H15 103(10) . . ?
O15 C16 O15 180.0(6) . 7_656 ?

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
O15 H15 O13 0.86(2) 2.13(4) 2.975(8) 166(14) .
N3 H3 O14 0.868(19) 1.99(2) 2.817(3) 160(4) 1_545
O14 H14 O13 0.841(19) 2.01(2) 2.834(3) 169(4) 5_666

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 N2 N3 C4 177.69(19) . . . . ?
Cu1 N2 C10 C5 -177.92(18) . . . . ?
Cu1 N2 C10 C9 1.7(4) . . . . ?
N2 Cu1 N2 N3 42(6) 5_656 . . . ?
N2 Cu1 N2 C10 -141(5) 5_656 . . . ?
N2 Cu1 O12 C11 -172.6(3) 5_656 . . . ?
N2 Cu1 O12 C11 7.4(3) . . . . ?
N2 N3 C4 C5 -0.3(3) . . . . ?
N3 N2 C10 C5 -0.7(3) . . . . ?
N3 N2 C10 C9 178.9(3) . . . . ?
N3 C4 C5 C6 -179.6(3) . . . . ?
N3 C4 C5 C10 -0.1(3) . . . . ?
C4 C5 C6 C7 178.7(3) . . . . ?
C4 C5 C10 N2 0.5(3) . . . . ?
C4 C5 C10 C9 -179.1(2) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C6 C5 C10 N2 -179.9(2) . . . . ?
C6 C5 C10 C9 0.4(4) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C7 C8 C9 C11 -178.8(3) . . . . ?
C8 C9 C10 N2 -179.6(3) . . . . ?
C8 C9 C10 C5 0.0(4) . . . . ?
C8 C9 C11 O12 -177.6(3) . . . . ?
C8 C9 C11 O13 2.4(4) . . . . ?
C9 C11 O12 Cu1 -8.2(4) . . . . ?
C10 N2 N3 C4 0.7(3) . . . . ?
C10 C5 C6 C7 -0.6(4) . . . . ?
C10 C9 C11 O12 3.8(4) . . . . ?
C10 C9 C11 O13 -176.2(3) . . . . ?
C11 C9 C10 N2 -1.0(4) . . . . ?
C11 C9 C10 C5 178.6(2) . . . . ?
O12 Cu1 N2 N3 -180.0(2) . . . . ?
O12 Cu1 N2 N3 0.0(2) 5_656 . . . ?
O12 Cu1 N2 C10 -3.5(2) . . . . ?
O12 Cu1 N2 C10 176.5(2) 5_656 . . . ?
O12 Cu1 O12 C11 2(46) 5_656 . . . ?
O13 C11 O12 Cu1 171.8(2) . . . . ?

# start Validation Reply Form
_vrf_PLAT041_4                   
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: Hydrogen atoms attached to lattice methanol could not be modelled
crystallographically but are included in formula for correct calculation of
F000, density and absorption coefficient.
;
# end Validation Reply Form
_database_code_depnum_ccdc_archive 'CCDC 1018282'
