# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_1M1
_audit_block_doi                 10.5517/cc13d1g0
_database_code_depnum_ccdc_archive 'CCDC 1024471'
_audit_update_record             
;
2016-02-09 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 Cu N5 O'
_chemical_formula_sum            'C16 H19 Cu N5 O'
_chemical_formula_weight         360.90

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   8.3103(3)
_cell_length_b                   9.0566(5)
_cell_length_c                   20.1313(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1515.14(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1949
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       plate
_exptl_crystal_colour            dark-green
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    1.454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6378
_exptl_absorpt_correction_T_max  0.8926
_exptl_absorpt_process_details   'SADABS (Bruker-AXS, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7573
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         28.58
_reflns_number_total             3626
_reflns_number_gt                3097
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.8944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.085(17)
_refine_ls_number_reflns         3626
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.07465(4) 0.02997(4) 0.993271(18) 0.01371(11) Uani 1 1 d . . .
O1 O 0.1062(2) 0.0119(3) 0.93552(10) 0.0164(5) Uani 1 1 d . . .
N2 N -0.2526(3) 0.0003(3) 1.06315(13) 0.0151(7) Uani 1 1 d . . .
N4 N 0.1914(3) 0.1822(3) 1.05266(13) 0.0146(6) Uani 1 1 d . . .
N3 N 0.0631(3) 0.1244(4) 1.06208(13) 0.0194(6) Uani 1 1 d . . .
N5 N 0.3157(3) 0.2397(4) 1.04728(16) 0.0222(7) Uani 1 1 d . . .
C16 C -0.1579(4) -0.1737(4) 0.88418(17) 0.0160(8) Uani 1 1 d . . .
C9 C 0.1092(3) -0.0439(4) 0.87603(15) 0.0142(7) Uani 1 1 d . . .
C1 C 0.3909(4) 0.0470(4) 0.86895(15) 0.0156(7) Uani 1 1 d . . .
H1 H 0.3805 0.0866 0.9124 0.019 Uiso 1 1 calc R . .
N1 N -0.1995(3) -0.1116(3) 0.93961(14) 0.0158(6) Uani 1 1 d . . .
C10 C 0.2595(4) -0.0246(4) 0.83930(15) 0.0149(7) Uani 1 1 d . . .
C5 C 0.2755(4) -0.0832(4) 0.77412(16) 0.0157(7) Uani 1 1 d . . .
C3 C 0.5525(4) 0.0032(4) 0.77155(15) 0.0195(8) Uani 1 1 d . . .
H3 H 0.6524 0.0129 0.7490 0.023 Uiso 1 1 calc R . .
C4 C 0.4258(4) -0.0670(4) 0.74116(15) 0.0186(8) Uani 1 1 d . . .
H4 H 0.4387 -0.1053 0.6975 0.022 Uiso 1 1 calc R . .
C2 C 0.5347(4) 0.0605(4) 0.83567(16) 0.0179(8) Uani 1 1 d . . .
H2 H 0.6227 0.1091 0.8564 0.022 Uiso 1 1 calc R . .
C7 C 0.0057(4) -0.1786(4) 0.77967(17) 0.0192(8) Uani 1 1 d . . .
H7 H -0.0810 -0.2291 0.7589 0.023 Uiso 1 1 calc R . .
C14 C -0.2949(4) 0.1297(4) 1.10432(18) 0.0195(8) Uani 1 1 d . . .
H14A H -0.2010 0.1599 1.1305 0.029 Uiso 1 1 calc R . .
H14B H -0.3834 0.1037 1.1343 0.029 Uiso 1 1 calc R . .
H14C H -0.3283 0.2113 1.0755 0.029 Uiso 1 1 calc R . .
C8 C -0.0148(4) -0.1284(4) 0.84713(17) 0.0159(8) Uani 1 1 d . . .
C6 C 0.1416(4) -0.1574(4) 0.74464(18) 0.0194(8) Uani 1 1 d . . .
H6 H 0.1486 -0.1919 0.7002 0.023 Uiso 1 1 calc R . .
C11 C -0.2534(4) -0.3014(4) 0.85699(18) 0.0212(8) Uani 1 1 d . . .
H11A H -0.3021 -0.3564 0.8938 0.032 Uiso 1 1 calc R . .
H11B H -0.1821 -0.3668 0.8318 0.032 Uiso 1 1 calc R . .
H11C H -0.3384 -0.2640 0.8277 0.032 Uiso 1 1 calc R . .
C13 C -0.3943(3) -0.0449(4) 1.02391(15) 0.0177(7) Uani 1 1 d . . .
H13A H -0.4393 0.0420 1.0006 0.021 Uiso 1 1 calc R . .
H13B H -0.4782 -0.0845 1.0539 0.021 Uiso 1 1 calc R . .
C12 C -0.3477(4) -0.1617(4) 0.97364(18) 0.0204(8) Uani 1 1 d . . .
H12A H -0.3281 -0.2571 0.9963 0.025 Uiso 1 1 calc R . .
H12B H -0.4354 -0.1756 0.9410 0.025 Uiso 1 1 calc R . .
C15 C -0.1996(4) -0.1189(4) 1.10728(18) 0.0185(8) Uani 1 1 d . . .
H15A H -0.1052 -0.0863 1.1325 0.028 Uiso 1 1 calc R . .
H15B H -0.1714 -0.2059 1.0807 0.028 Uiso 1 1 calc R . .
H15C H -0.2866 -0.1442 1.1381 0.028 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.907(2) . ?
Cu1 N1 1.972(3) . ?
Cu1 N3 1.990(3) . ?
Cu1 N2 2.059(3) . ?
Cu1 N5 2.418(3) 3_457 ?
O1 C9 1.300(4) . ?
N2 C15 1.466(4) . ?
N2 C13 1.476(4) . ?
N2 C14 1.478(4) . ?
N4 N5 1.163(4) . ?
N4 N3 1.203(4) . ?
N5 Cu1 2.418(3) 3_557 ?
C16 N1 1.297(4) . ?
C16 C8 1.462(5) . ?
C16 C11 1.506(5) . ?
C9 C8 1.409(5) . ?
C9 C10 1.462(4) . ?
C1 C2 1.375(4) . ?
C1 C10 1.404(5) . ?
C1 H1 0.9500 . ?
N1 C12 1.480(4) . ?
C10 C5 1.421(5) . ?
C5 C4 1.422(5) . ?
C5 C6 1.429(5) . ?
C3 C4 1.374(5) . ?
C3 C2 1.399(5) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C2 H2 0.9500 . ?
C7 C6 1.345(5) . ?
C7 C8 1.442(5) . ?
C7 H7 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C6 H6 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C12 1.514(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 91.44(11) . . ?
O1 Cu1 N3 90.45(10) . . ?
N1 Cu1 N3 164.48(12) . . ?
O1 Cu1 N2 166.27(11) . . ?
N1 Cu1 N2 84.91(11) . . ?
N3 Cu1 N2 89.64(11) . . ?
O1 Cu1 N5 99.50(10) . 3_457 ?
N1 Cu1 N5 100.23(12) . 3_457 ?
N3 Cu1 N5 94.65(12) . 3_457 ?
N2 Cu1 N5 94.17(11) . 3_457 ?
C9 O1 Cu1 127.57(19) . . ?
C15 N2 C13 111.1(3) . . ?
C15 N2 C14 108.4(3) . . ?
C13 N2 C14 109.3(3) . . ?
C15 N2 Cu1 107.11(19) . . ?
C13 N2 Cu1 104.09(18) . . ?
C14 N2 Cu1 116.8(2) . . ?
N5 N4 N3 176.2(3) . . ?
N4 N3 Cu1 126.0(2) . . ?
N4 N5 Cu1 138.8(3) . 3_557 ?
N1 C16 C8 122.3(3) . . ?
N1 C16 C11 120.3(3) . . ?
C8 C16 C11 117.3(3) . . ?
O1 C9 C8 125.3(3) . . ?
O1 C9 C10 115.8(3) . . ?
C8 C9 C10 118.7(3) . . ?
C2 C1 C10 120.7(3) . . ?
C2 C1 H1 119.7 . . ?
C10 C1 H1 119.7 . . ?
C16 N1 C12 119.2(3) . . ?
C16 N1 Cu1 127.8(2) . . ?
C12 N1 Cu1 112.6(2) . . ?
C1 C10 C5 119.5(3) . . ?
C1 C10 C9 120.3(3) . . ?
C5 C10 C9 120.1(3) . . ?
C10 C5 C4 118.3(3) . . ?
C10 C5 C6 119.1(3) . . ?
C4 C5 C6 122.6(3) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C6 C7 C8 123.2(3) . . ?
C6 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C8 C7 118.3(3) . . ?
C9 C8 C16 122.4(3) . . ?
C7 C8 C16 119.2(3) . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C16 C11 H11A 109.5 . . ?
C16 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C16 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C13 C12 110.3(3) . . ?
N2 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
N2 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N1 C12 C13 107.9(3) . . ?
N1 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
N1 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        28.58
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.094
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2M1
_audit_block_doi                 10.5517/cc13d1j2
_database_code_depnum_ccdc_archive 'CCDC 1024473'
_audit_update_record             
;
2016-02-09 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 Cu N3 O2'
_chemical_formula_sum            'C16 H17 Cu N3 O2'
_chemical_formula_weight         346.87

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   6.9439(2)
_cell_length_b                   7.7514(2)
_cell_length_c                   27.5560(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1483.20(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3418
_cell_measurement_theta_min      2.7220
_cell_measurement_theta_max      30.2410

_exptl_crystal_description       block
_exptl_crystal_colour            dark-blue
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    1.483
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.0107
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4428
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2606
_reflns_number_gt                2512
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    
;
SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0279P)²+0.1334P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(12)
_refine_ls_number_reflns         2606
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0592
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.56138(4) -0.71156(4) -0.670508(10) 0.02099(10) Uani 1 1 d . . .
O1 O -0.3529(2) -0.5704(2) -0.64706(7) 0.0271(4) Uani 1 1 d . . .
N2 N -0.7922(3) -0.8662(3) -0.68887(7) 0.0211(5) Uani 1 1 d . . .
N1 N -0.7221(3) -0.6376(3) -0.61690(7) 0.0197(5) Uani 1 1 d . . .
N3 N -0.3999(3) -0.8135(4) -0.71920(9) 0.0394(7) Uani 1 1 d . . .
C10 C -0.5320(4) -0.3898(3) -0.59247(8) 0.0198(5) Uani 1 1 d . . .
C4 C -0.3743(4) -0.1143(4) -0.56881(9) 0.0248(6) Uani 1 1 d . . .
C9 C -0.5358(4) -0.2288(3) -0.56532(8) 0.0217(5) Uani 1 1 d . . .
C11 C -0.6981(4) -0.5004(3) -0.59081(9) 0.0207(6) Uani 1 1 d . . .
H11 H -0.7980 -0.4705 -0.5688 0.025 Uiso 1 1 calc R . .
C1 C -0.3701(4) -0.4329(3) -0.62081(9) 0.0224(6) Uani 1 1 d . . .
C12 C -0.9024(3) -0.7348(3) -0.61297(9) 0.0228(6) Uani 1 1 d . . .
H12A H -1.0040 -0.6618 -0.5984 0.027 Uiso 1 1 calc R . .
H12B H -0.8839 -0.8376 -0.5922 0.027 Uiso 1 1 calc R . .
C13 C -0.9599(3) -0.7889(3) -0.66381(8) 0.0231(5) Uani 1 1 d . . .
H13A H -1.0661 -0.8739 -0.6621 0.028 Uiso 1 1 calc R . .
H13B H -1.0061 -0.6873 -0.6822 0.028 Uiso 1 1 calc R . .
C7 C -0.6884(4) -0.0176(4) -0.51187(10) 0.0312(7) Uani 1 1 d . . .
H7 H -0.7936 0.0136 -0.4916 0.037 Uiso 1 1 calc R . .
C2 C -0.2082(4) -0.3170(3) -0.62088(9) 0.0271(6) Uani 1 1 d . . .
H2 H -0.0956 -0.3474 -0.6385 0.032 Uiso 1 1 calc R . .
C3 C -0.2128(4) -0.1665(4) -0.59651(10) 0.0293(7) Uani 1 1 d . . .
H3 H -0.1037 -0.0927 -0.5980 0.035 Uiso 1 1 calc R . .
C6 C -0.5343(5) 0.0953(4) -0.51755(10) 0.0358(7) Uani 1 1 d . . .
H6 H -0.5362 0.2052 -0.5023 0.043 Uiso 1 1 calc R . .
C5 C -0.3802(4) 0.0470(4) -0.54527(10) 0.0332(7) Uani 1 1 d . . .
H5 H -0.2747 0.1240 -0.5488 0.040 Uiso 1 1 calc R . .
C8 C -0.6894(4) -0.1745(3) -0.53548(9) 0.0263(6) Uani 1 1 d . . .
H8 H -0.7972 -0.2485 -0.5315 0.032 Uiso 1 1 calc R . .
C15 C -0.8322(4) -0.8749(4) -0.74159(9) 0.0303(7) Uani 1 1 d . . .
H15A H -0.8453 -0.7578 -0.7546 0.045 Uiso 1 1 calc R . .
H15B H -0.9520 -0.9388 -0.7471 0.045 Uiso 1 1 calc R . .
H15C H -0.7258 -0.9339 -0.7580 0.045 Uiso 1 1 calc R . .
O2 O -0.2838(3) -0.9674(3) -0.78738(7) 0.0364(5) Uani 1 1 d . . .
C16 C -0.3462(4) -0.8902(3) -0.75277(10) 0.0247(6) Uani 1 1 d . . .
C14 C -0.7525(4) -1.0436(3) -0.67088(12) 0.0336(7) Uani 1 1 d . . .
H14A H -0.6398 -1.0905 -0.6877 0.050 Uiso 1 1 calc R . .
H14B H -0.8644 -1.1173 -0.6771 0.050 Uiso 1 1 calc R . .
H14C H -0.7271 -1.0398 -0.6359 0.050 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N3 1.919(2) . ?
Cu1 O1 1.9264(17) . ?
Cu1 N1 1.938(2) . ?
Cu1 N2 2.065(2) . ?
O1 C1 1.293(3) . ?
N2 C15 1.481(3) . ?
N2 C13 1.481(3) . ?
N2 C14 1.487(3) . ?
N1 C11 1.294(3) . ?
N1 C12 1.465(3) . ?
N3 C16 1.161(3) . ?
C10 C1 1.409(3) . ?
C10 C11 1.438(3) . ?
C10 C9 1.455(3) . ?
C4 C5 1.409(4) . ?
C4 C3 1.415(4) . ?
C4 C9 1.434(4) . ?
C9 C8 1.411(4) . ?
C11 H11 0.9500 . ?
C1 C2 1.439(3) . ?
C12 C13 1.516(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C7 C8 1.379(4) . ?
C7 C6 1.391(4) . ?
C7 H7 0.9500 . ?
C2 C3 1.347(4) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C6 C5 1.367(4) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C8 H8 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 C16 1.207(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 O1 91.69(9) . . ?
N3 Cu1 N1 172.42(11) . . ?
O1 Cu1 N1 90.51(8) . . ?
N3 Cu1 N2 92.47(10) . . ?
O1 Cu1 N2 174.58(8) . . ?
N1 Cu1 N2 84.93(9) . . ?
C1 O1 Cu1 125.91(16) . . ?
C15 N2 C13 109.18(19) . . ?
C15 N2 C14 108.7(2) . . ?
C13 N2 C14 111.4(2) . . ?
C15 N2 Cu1 114.37(17) . . ?
C13 N2 Cu1 105.14(15) . . ?
C14 N2 Cu1 108.12(16) . . ?
C11 N1 C12 119.4(2) . . ?
C11 N1 Cu1 126.33(18) . . ?
C12 N1 Cu1 113.35(16) . . ?
C16 N3 Cu1 162.9(2) . . ?
C1 C10 C11 121.1(2) . . ?
C1 C10 C9 120.2(2) . . ?
C11 C10 C9 118.7(2) . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 C9 119.7(3) . . ?
C3 C4 C9 118.6(2) . . ?
C8 C9 C4 116.4(2) . . ?
C8 C9 C10 124.7(2) . . ?
C4 C9 C10 118.9(2) . . ?
N1 C11 C10 125.1(2) . . ?
N1 C11 H11 117.4 . . ?
C10 C11 H11 117.4 . . ?
O1 C1 C10 125.3(2) . . ?
O1 C1 C2 116.2(2) . . ?
C10 C1 C2 118.5(2) . . ?
N1 C12 C13 107.42(19) . . ?
N1 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
N1 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
N2 C13 C12 109.62(19) . . ?
N2 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
N2 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 122.4(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C8 C9 122.3(3) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 O2 177.7(3) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 Cu1 O1 C1 161.3(2) . . . . ?
N1 Cu1 O1 C1 -26.0(2) . . . . ?
N3 Cu1 N2 C15 -47.7(2) . . . . ?
N1 Cu1 N2 C15 139.49(19) . . . . ?
N3 Cu1 N2 C13 -167.41(16) . . . . ?
N1 Cu1 N2 C13 19.73(15) . . . . ?
N3 Cu1 N2 C14 73.52(19) . . . . ?
N1 Cu1 N2 C14 -99.34(18) . . . . ?
O1 Cu1 N1 C11 20.4(2) . . . . ?
N2 Cu1 N1 C11 -162.5(2) . . . . ?
O1 Cu1 N1 C12 -170.66(17) . . . . ?
N2 Cu1 N1 C12 6.41(17) . . . . ?
O1 Cu1 N3 C16 -168.6(9) . . . . ?
N2 Cu1 N3 C16 14.9(9) . . . . ?
C5 C4 C9 C8 -3.5(4) . . . . ?
C3 C4 C9 C8 177.1(2) . . . . ?
C5 C4 C9 C10 176.0(2) . . . . ?
C3 C4 C9 C10 -3.4(3) . . . . ?
C1 C10 C9 C8 -179.2(2) . . . . ?
C11 C10 C9 C8 2.5(4) . . . . ?
C1 C10 C9 C4 1.3(3) . . . . ?
C11 C10 C9 C4 -177.0(2) . . . . ?
C12 N1 C11 C10 -177.5(2) . . . . ?
Cu1 N1 C11 C10 -9.1(4) . . . . ?
C1 C10 C11 N1 -5.7(4) . . . . ?
C9 C10 C11 N1 172.6(2) . . . . ?
Cu1 O1 C1 C10 20.6(4) . . . . ?
Cu1 O1 C1 C2 -159.88(18) . . . . ?
C11 C10 C1 O1 -0.3(4) . . . . ?
C9 C10 C1 O1 -178.6(2) . . . . ?
C11 C10 C1 C2 -179.9(2) . . . . ?
C9 C10 C1 C2 1.9(4) . . . . ?
C11 N1 C12 C13 139.0(2) . . . . ?
Cu1 N1 C12 C13 -30.7(2) . . . . ?
C15 N2 C13 C12 -164.8(2) . . . . ?
C14 N2 C13 C12 75.2(3) . . . . ?
Cu1 N2 C13 C12 -41.6(2) . . . . ?
N1 C12 C13 N2 48.2(3) . . . . ?
O1 C1 C2 C3 177.2(3) . . . . ?
C10 C1 C2 C3 -3.2(4) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C5 C4 C3 C2 -177.1(3) . . . . ?
C9 C4 C3 C2 2.2(4) . . . . ?
C8 C7 C6 C5 -2.4(4) . . . . ?
C7 C6 C5 C4 0.7(4) . . . . ?
C3 C4 C5 C6 -178.3(3) . . . . ?
C9 C4 C5 C6 2.3(4) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C4 C9 C8 C7 1.8(4) . . . . ?
C10 C9 C8 C7 -177.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.045
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1M2
_database_code_depnum_ccdc_archive 'CCDC 1053243'
_audit_update_record             
;
2016-02-09 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 Cu N5 O'
_chemical_formula_weight         360.90

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   8.385(2)
_cell_length_b                   9.168(3)
_cell_length_c                   20.215(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1554.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1947
_cell_measurement_theta_min      2.03
_cell_measurement_theta_max      23.93

_exptl_crystal_description       plate
_exptl_crystal_colour            dark-green
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    1.417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_T_max  0.842
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12855
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         23.51
_reflns_number_total             2296
_reflns_number_gt                2148
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0347P)²+0.1202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.021(17)
_refine_ls_number_reflns         2296
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.07588(4) 0.52779(4) 0.992647(18) 0.02848(14) Uani 1 1 d . . .
O1 O 0.1017(3) 0.5140(3) 0.93442(10) 0.0345(6) Uani 1 1 d . . .
N3 N 0.0611(4) 0.6203(4) 1.06090(14) 0.0414(8) Uani 1 1 d . . .
N1 N -0.2000(3) 0.3886(3) 0.93919(14) 0.0311(7) Uani 1 1 d . . .
N2 N -0.2532(3) 0.4984(3) 1.06180(12) 0.0290(7) Uani 1 1 d . . .
C14 C -0.2000(4) 0.3805(4) 1.10617(18) 0.0388(9) Uani 1 1 d . . .
H14A H -0.1081 0.4122 1.1306 0.058 Uiso 1 1 calc R . .
H14B H -0.1729 0.2960 1.0804 0.058 Uiso 1 1 calc R . .
H14C H -0.2843 0.3564 1.1364 0.058 Uiso 1 1 calc R . .
N4 N 0.1871(4) 0.6783(3) 1.05252(13) 0.0319(7) Uani 1 1 d . . .
N5 N 0.3089(4) 0.7363(4) 1.04777(18) 0.0474(9) Uani 1 1 d . . .
C16 C -0.1584(4) 0.3281(4) 0.88349(18) 0.0328(9) Uani 1 1 d . . .
C8 C -0.0171(4) 0.3732(4) 0.84658(17) 0.0302(8) Uani 1 1 d . . .
C7 C 0.0048(5) 0.3226(5) 0.77963(18) 0.0421(10) Uani 1 1 d . . .
H7 H -0.0782 0.2724 0.7593 0.051 Uiso 1 1 calc R . .
C6 C 0.1407(5) 0.3449(5) 0.74515(18) 0.0426(11) Uani 1 1 d . . .
H6 H 0.1479 0.3120 0.7017 0.051 Uiso 1 1 calc R . .
C5 C 0.2732(4) 0.4183(4) 0.77445(17) 0.0324(9) Uani 1 1 d . . .
C10 C 0.2555(4) 0.4765(4) 0.83918(14) 0.0269(7) Uani 1 1 d . . .
C1 C 0.3847(4) 0.5482(4) 0.86843(16) 0.0334(8) Uani 1 1 d . . .
H1 H 0.3737 0.5864 0.9108 0.040 Uiso 1 1 calc R . .
C2 C 0.5282(4) 0.5632(4) 0.83569(17) 0.0372(10) Uani 1 1 d . . .
H2 H 0.6130 0.6109 0.8559 0.045 Uiso 1 1 calc R . .
C3 C 0.5452(4) 0.5063(4) 0.77208(17) 0.0415(10) Uani 1 1 d . . .
H3 H 0.6419 0.5165 0.7500 0.050 Uiso 1 1 calc R . .
C4 C 0.4220(5) 0.4360(4) 0.74190(16) 0.0405(9) Uani 1 1 d . . .
H4 H 0.4354 0.3991 0.6994 0.049 Uiso 1 1 calc R . .
C9 C 0.1061(4) 0.4571(4) 0.87534(15) 0.0283(8) Uani 1 1 d . . .
C11 C -0.2553(5) 0.2031(4) 0.8558(2) 0.0469(10) Uani 1 1 d . . .
H11A H -0.3441 0.1837 0.8845 0.070 Uiso 1 1 calc R . .
H11B H -0.1895 0.1177 0.8527 0.070 Uiso 1 1 calc R . .
H11C H -0.2939 0.2286 0.8126 0.070 Uiso 1 1 calc R . .
C12 C -0.3466(4) 0.3407(4) 0.97251(18) 0.0400(10) Uani 1 1 d . . .
H12A H -0.3288 0.2477 0.9941 0.048 Uiso 1 1 calc R . .
H12B H -0.4314 0.3287 0.9403 0.048 Uiso 1 1 calc R . .
C13 C -0.3935(4) 0.4534(4) 1.02291(17) 0.0369(8) Uani 1 1 d . . .
H13A H -0.4387 0.5377 1.0007 0.044 Uiso 1 1 calc R . .
H13B H -0.4741 0.4134 1.0522 0.044 Uiso 1 1 calc R . .
C15 C -0.2959(4) 0.6266(4) 1.10303(19) 0.0409(10) Uani 1 1 d . . .
H15A H -0.2048 0.6565 1.1284 0.061 Uiso 1 1 calc R . .
H15B H -0.3814 0.6009 1.1324 0.061 Uiso 1 1 calc R . .
H15C H -0.3293 0.7053 1.0749 0.061 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.902(2) . ?
Cu1 N1 1.970(3) . ?
Cu1 N3 1.986(3) . ?
Cu1 N2 2.058(3) . ?
O1 C9 1.304(4) . ?
N3 N4 1.194(4) . ?
N1 C16 1.303(4) . ?
N1 C12 1.468(4) . ?
N2 C14 1.474(4) . ?
N2 C13 1.474(4) . ?
N2 C15 1.485(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N4 N5 1.155(4) . ?
C16 C8 1.460(5) . ?
C16 C11 1.513(5) . ?
C8 C9 1.413(5) . ?
C8 C7 1.443(5) . ?
C7 C6 1.351(5) . ?
C7 H7 0.9300 . ?
C6 C5 1.428(5) . ?
C6 H6 0.9300 . ?
C5 C4 1.420(5) . ?
C5 C10 1.421(5) . ?
C10 C1 1.398(5) . ?
C10 C9 1.462(4) . ?
C1 C2 1.380(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.504(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 91.78(11) . . ?
O1 Cu1 N3 90.32(11) . . ?
N1 Cu1 N3 164.52(13) . . ?
O1 Cu1 N2 167.64(11) . . ?
N1 Cu1 N2 84.61(11) . . ?
N3 Cu1 N2 90.11(11) . . ?
C9 O1 Cu1 128.0(2) . . ?
N4 N3 Cu1 127.1(2) . . ?
C16 N1 C12 119.6(3) . . ?
C16 N1 Cu1 127.5(2) . . ?
C12 N1 Cu1 112.6(2) . . ?
C14 N2 C13 111.2(3) . . ?
C14 N2 C15 108.2(3) . . ?
C13 N2 C15 109.1(3) . . ?
C14 N2 Cu1 106.9(2) . . ?
C13 N2 Cu1 104.53(19) . . ?
C15 N2 Cu1 116.9(2) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 N4 N3 176.5(4) . . ?
N1 C16 C8 122.6(3) . . ?
N1 C16 C11 119.9(3) . . ?
C8 C16 C11 117.5(3) . . ?
C9 C8 C7 117.9(3) . . ?
C9 C8 C16 122.5(3) . . ?
C7 C8 C16 119.4(3) . . ?
C6 C7 C8 122.9(4) . . ?
C6 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C4 C5 C10 118.4(3) . . ?
C4 C5 C6 123.0(3) . . ?
C10 C5 C6 118.5(3) . . ?
C1 C10 C5 119.0(3) . . ?
C1 C10 C9 120.7(3) . . ?
C5 C10 C9 120.3(3) . . ?
C2 C1 C10 121.3(3) . . ?
C2 C1 H1 119.4 . . ?
C10 C1 H1 119.4 . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
O1 C9 C8 125.0(3) . . ?
O1 C9 C10 115.7(3) . . ?
C8 C9 C10 119.2(3) . . ?
C16 C11 H11A 109.5 . . ?
C16 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C16 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 108.9(3) . . ?
N1 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
N1 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
N2 C13 C12 110.2(3) . . ?
N2 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
N2 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        23.51
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1M3
_database_code_depnum_ccdc_archive 'CCDC 1053244'
_audit_update_record             
;
2016-02-09 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 Cu N5 O'
_chemical_formula_weight         360.90

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   8.3537(3)
_cell_length_b                   9.1463(4)
_cell_length_c                   20.1898(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1542.61(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1941
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      28.57

_exptl_crystal_description       plate
_exptl_crystal_colour            dark-green
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13408
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         28.76
_reflns_number_total             3895
_reflns_number_gt                3349
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0349P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.004(13)
_refine_ls_number_reflns         3895
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.07596(3) 0.02764(3) 1.007366(14) 0.02687(9) Uani 1 1 d . . .
O1 O -0.10137(19) 0.0139(2) 1.06581(9) 0.0340(4) Uani 1 1 d . . .
N2 N 0.2532(2) -0.0016(2) 0.93793(10) 0.0288(5) Uani 1 1 d . . .
N4 N -0.1870(3) 0.1782(3) 0.94755(10) 0.0292(5) Uani 1 1 d . . .
N1 N 0.1999(2) -0.1111(3) 1.06112(12) 0.0307(5) Uani 1 1 d . . .
N5 N -0.3083(3) 0.2365(3) 0.95220(15) 0.0471(7) Uani 1 1 d . . .
C10 C -0.2555(3) -0.0240(3) 1.16093(11) 0.0258(5) Uani 1 1 d . . .
C9 C -0.1061(3) -0.0429(3) 1.12447(12) 0.0258(5) Uani 1 1 d . . .
N3 N -0.0609(3) 0.1207(3) 0.93914(11) 0.0387(6) Uani 1 1 d . . .
C13 C 0.3932(3) -0.0461(3) 0.97697(14) 0.0356(6) Uani 1 1 d . . .
H13A H 0.4378 0.0385 0.9993 0.043 Uiso 1 1 calc R . .
H13B H 0.4746 -0.0856 0.9477 0.043 Uiso 1 1 calc R . .
C1 C -0.3841(3) 0.0489(3) 1.13138(13) 0.0308(6) Uani 1 1 d . . .
H1 H -0.3725 0.0883 1.0892 0.037 Uiso 1 1 calc R . .
C8 C 0.0171(3) -0.1266(3) 1.15338(13) 0.0297(6) Uani 1 1 d . . .
C5 C -0.2725(3) -0.0817(3) 1.22569(13) 0.0308(6) Uani 1 1 d . . .
C11 C 0.2551(3) -0.2973(4) 1.14428(16) 0.0464(8) Uani 1 1 d . . .
H11A H 0.3444 -0.3165 1.1156 0.070 Uiso 1 1 calc R . .
H11B H 0.1888 -0.3828 1.1470 0.070 Uiso 1 1 calc R . .
H11C H 0.2935 -0.2725 1.1877 0.070 Uiso 1 1 calc R . .
C16 C 0.1582(3) -0.1711(3) 1.11675(14) 0.0313(6) Uani 1 1 d . . .
C7 C -0.0053(4) -0.1773(4) 1.22033(14) 0.0401(7) Uani 1 1 d . . .
H7 H 0.0782 -0.2275 1.2406 0.048 Uiso 1 1 calc R . .
C4 C -0.4216(3) -0.0642(3) 1.25811(13) 0.0386(7) Uani 1 1 d . . .
H4 H -0.4351 -0.1013 1.3006 0.046 Uiso 1 1 calc R . .
C12 C 0.3470(3) -0.1594(3) 1.02733(15) 0.0386(7) Uani 1 1 d . . .
H12A H 0.3288 -0.2526 1.0057 0.046 Uiso 1 1 calc R . .
H12B H 0.4326 -0.1717 1.0593 0.046 Uiso 1 1 calc R . .
C6 C -0.1402(3) -0.1559(4) 1.25482(14) 0.0413(8) Uani 1 1 d . . .
H6 H -0.1476 -0.1898 1.2981 0.050 Uiso 1 1 calc R . .
C3 C -0.5451(3) 0.0062(3) 1.22803(14) 0.0412(7) Uani 1 1 d . . .
H3 H -0.6420 0.0166 1.2502 0.049 Uiso 1 1 calc R . .
C14 C 0.2958(3) 0.1264(3) 0.89695(15) 0.0382(7) Uani 1 1 d . . .
H14A H 0.2045 0.1561 0.8714 0.057 Uiso 1 1 calc R . .
H14B H 0.3819 0.1009 0.8677 0.057 Uiso 1 1 calc R . .
H14C H 0.3288 0.2054 0.9252 0.057 Uiso 1 1 calc R . .
C15 C 0.2009(3) -0.1195(3) 0.89411(15) 0.0361(7) Uani 1 1 d . . .
H15A H 0.1090 -0.0881 0.8694 0.054 Uiso 1 1 calc R . .
H15B H 0.1734 -0.2038 0.9201 0.054 Uiso 1 1 calc R . .
H15C H 0.2859 -0.1441 0.8641 0.054 Uiso 1 1 calc R . .
C2 C -0.5282(3) 0.0629(3) 1.16427(14) 0.0361(7) Uani 1 1 d . . .
H2 H -0.6138 0.1100 1.1440 0.043 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.8981(16) . ?
Cu1 N1 1.965(2) . ?
Cu1 N3 1.982(2) . ?
Cu1 N2 2.056(2) . ?
O1 C9 1.294(3) . ?
N2 C15 1.461(3) . ?
N2 C13 1.468(3) . ?
N2 C14 1.477(3) . ?
N4 N5 1.149(3) . ?
N4 N3 1.189(3) . ?
N1 C16 1.298(3) . ?
N1 C12 1.473(3) . ?
C10 C1 1.398(3) . ?
C10 C5 1.417(4) . ?
C10 C9 1.459(3) . ?
C9 C8 1.410(3) . ?
C13 C12 1.502(4) . ?
C1 C2 1.381(3) . ?
C8 C7 1.441(4) . ?
C8 C16 1.450(4) . ?
C5 C4 1.416(4) . ?
C5 C6 1.424(4) . ?
C11 C16 1.515(4) . ?
C7 C6 1.340(4) . ?
C4 C3 1.359(4) . ?
C3 C2 1.395(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
O1 Cu1 N1 91.44(9) . . ?
O1 Cu1 N3 90.58(8) . . ?
N1 Cu1 N3 164.83(10) . . ?
O1 Cu1 N2 167.70(9) . . ?
N1 Cu1 N2 85.01(9) . . ?
N3 Cu1 N2 89.85(8) . . ?
C9 O1 Cu1 128.29(15) . . ?
C15 N2 C13 111.0(2) . . ?
C15 N2 C14 108.5(2) . . ?
C13 N2 C14 109.14(19) . . ?
C15 N2 Cu1 107.08(15) . . ?
C13 N2 Cu1 104.10(15) . . ?
C14 N2 Cu1 116.89(16) . . ?
N5 N4 N3 176.3(3) . . ?
C16 N1 C12 119.9(2) . . ?
C16 N1 Cu1 127.57(18) . . ?
C12 N1 Cu1 112.18(18) . . ?
C1 C10 C5 119.6(2) . . ?
C1 C10 C9 119.9(2) . . ?
C5 C10 C9 120.5(2) . . ?
O1 C9 C8 125.1(2) . . ?
O1 C9 C10 116.1(2) . . ?
C8 C9 C10 118.7(2) . . ?
N4 N3 Cu1 126.98(19) . . ?
N2 C13 C12 110.5(2) . . ?
C2 C1 C10 120.6(2) . . ?
C9 C8 C7 117.9(2) . . ?
C9 C8 C16 122.4(2) . . ?
C7 C8 C16 119.6(2) . . ?
C4 C5 C10 118.2(2) . . ?
C4 C5 C6 123.1(3) . . ?
C10 C5 C6 118.7(2) . . ?
N1 C16 C8 122.7(2) . . ?
N1 C16 C11 119.8(2) . . ?
C8 C16 C11 117.5(2) . . ?
C6 C7 C8 123.3(3) . . ?
C3 C4 C5 121.0(2) . . ?
N1 C12 C13 108.7(2) . . ?
C7 C6 C5 120.6(3) . . ?
C4 C3 C2 120.8(2) . . ?
C1 C2 C3 119.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.76
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.064
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1P1
_database_code_depnum_ccdc_archive 'CCDC 1053245'
_audit_update_record             
;
2016-02-09 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 Cu N5 O'
_chemical_formula_weight         360.90

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   8.3629(15)
_cell_length_b                   9.1293(17)
_cell_length_c                   20.174(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1540.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1943
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      26.73

_exptl_crystal_description       plate
_exptl_crystal_colour            dark-green
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    1.430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10013
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         26.22
_reflns_number_total             3081
_reflns_number_gt                2845
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0361P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(13)
_refine_ls_number_reflns         3081
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.07563(3) 0.97188(3) 0.507242(14) 0.02467(9) Uani 1 1 d . . .
O1 O -0.10231(18) 0.9864(2) 0.56562(8) 0.0308(4) Uani 1 1 d . . .
N2 N 0.2530(2) 1.0011(2) 0.43783(10) 0.0266(5) Uani 1 1 d . . .
N4 N -0.1879(2) 0.8209(3) 0.44742(10) 0.0270(5) Uani 1 1 d . . .
N5 N -0.3096(3) 0.7631(3) 0.45235(14) 0.0431(7) Uani 1 1 d . . .
N1 N 0.1996(2) 1.1113(3) 0.56102(11) 0.0278(5) Uani 1 1 d . . .
C10 C -0.2561(3) 1.0237(3) 0.66111(11) 0.0242(5) Uani 1 1 d . . .
N3 N -0.0615(2) 0.8787(3) 0.43894(11) 0.0354(5) Uani 1 1 d . . .
C5 C -0.2732(3) 1.0823(3) 0.72548(13) 0.0297(6) Uani 1 1 d . . .
C9 C -0.1067(3) 1.0427(3) 0.62426(12) 0.0250(5) Uani 1 1 d . . .
C1 C -0.3855(3) 0.9515(3) 0.63138(13) 0.0282(6) Uani 1 1 d . . .
H1 H -0.3742 0.9127 0.5890 0.034 Uiso 1 1 calc R . .
C8 C 0.0168(3) 1.1266(3) 0.65345(13) 0.0274(6) Uani 1 1 d . . .
C7 C -0.0049(3) 1.1779(3) 0.72021(14) 0.0374(7) Uani 1 1 d . . .
H7 H 0.0785 1.2284 0.7404 0.045 Uiso 1 1 calc R . .
C11 C 0.2550(3) 1.2982(3) 0.64392(15) 0.0417(7) Uani 1 1 d . . .
H11A H 0.3442 1.3173 0.6152 0.063 Uiso 1 1 calc R . .
H11B H 0.2935 1.2736 0.6874 0.063 Uiso 1 1 calc R . .
H11C H 0.1888 1.3839 0.6466 0.063 Uiso 1 1 calc R . .
C12 C 0.3472(3) 1.1599(3) 0.52723(14) 0.0350(7) Uani 1 1 d . . .
H12A H 0.4325 1.1722 0.5593 0.042 Uiso 1 1 calc R . .
H12B H 0.3290 1.2532 0.5055 0.042 Uiso 1 1 calc R . .
C16 C 0.1583(3) 1.1717(3) 0.61656(14) 0.0284(6) Uani 1 1 d . . .
C13 C 0.3934(2) 1.0462(3) 0.47690(13) 0.0326(6) Uani 1 1 d . . .
H13A H 0.4745 1.0857 0.4476 0.039 Uiso 1 1 calc R . .
H13B H 0.4382 0.9616 0.4993 0.039 Uiso 1 1 calc R . .
C4 C -0.4220(3) 1.0642(3) 0.75828(13) 0.0367(7) Uani 1 1 d . . .
H4 H -0.4351 1.1006 0.8010 0.044 Uiso 1 1 calc R . .
C6 C -0.1406(3) 1.1562(4) 0.75485(14) 0.0390(7) Uani 1 1 d . . .
H6 H -0.1480 1.1897 0.7983 0.047 Uiso 1 1 calc R . .
C3 C -0.5462(3) 0.9943(3) 0.72799(13) 0.0369(7) Uani 1 1 d . . .
H3 H -0.6432 0.9846 0.7501 0.044 Uiso 1 1 calc R . .
C2 C -0.5297(3) 0.9372(3) 0.66425(14) 0.0335(7) Uani 1 1 d . . .
H2 H -0.6151 0.8898 0.6440 0.040 Uiso 1 1 calc R . .
C15 C 0.2953(3) 0.8732(3) 0.39676(14) 0.0351(7) Uani 1 1 d . . .
H15A H 0.2039 0.8434 0.3714 0.053 Uiso 1 1 calc R . .
H15B H 0.3286 0.7941 0.4249 0.053 Uiso 1 1 calc R . .
H15C H 0.3810 0.8989 0.3673 0.053 Uiso 1 1 calc R . .
C14 C 0.2004(3) 1.1192(3) 0.39348(14) 0.0339(6) Uani 1 1 d . . .
H14A H 0.1086 1.0874 0.3688 0.051 Uiso 1 1 calc R . .
H14B H 0.2853 1.1434 0.3634 0.051 Uiso 1 1 calc R . .
H14C H 0.1731 1.2040 0.4193 0.051 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9023(16) . ?
Cu1 N1 1.968(2) . ?
Cu1 N3 1.984(2) . ?
Cu1 N2 2.0574(19) . ?
O1 C9 1.290(3) . ?
N2 C14 1.468(3) . ?
N2 C13 1.473(3) . ?
N2 C15 1.475(3) . ?
N4 N5 1.151(3) . ?
N4 N3 1.194(3) . ?
N1 C16 1.296(3) . ?
N1 C12 1.478(3) . ?
C10 C1 1.402(3) . ?
C10 C5 1.411(4) . ?
C10 C9 1.464(3) . ?
C5 C4 1.419(4) . ?
C5 C6 1.427(4) . ?
C9 C8 1.414(3) . ?
C1 C2 1.382(3) . ?
C8 C7 1.437(4) . ?
C8 C16 1.458(4) . ?
C7 C6 1.348(4) . ?
C11 C16 1.514(4) . ?
C12 C13 1.503(4) . ?
C4 C3 1.364(4) . ?
C3 C2 1.394(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
O1 Cu1 N1 91.47(8) . . ?
O1 Cu1 N3 90.45(8) . . ?
N1 Cu1 N3 164.72(10) . . ?
O1 Cu1 N2 167.51(9) . . ?
N1 Cu1 N2 84.91(9) . . ?
N3 Cu1 N2 89.98(8) . . ?
C9 O1 Cu1 128.15(15) . . ?
C14 N2 C13 111.1(2) . . ?
C14 N2 C15 108.1(2) . . ?
C13 N2 C15 109.30(19) . . ?
C14 N2 Cu1 107.10(15) . . ?
C13 N2 Cu1 104.29(15) . . ?
C15 N2 Cu1 116.91(16) . . ?
N5 N4 N3 176.6(3) . . ?
C16 N1 C12 119.6(2) . . ?
C16 N1 Cu1 127.69(17) . . ?
C12 N1 Cu1 112.31(17) . . ?
C1 C10 C5 119.6(2) . . ?
C1 C10 C9 119.8(2) . . ?
C5 C10 C9 120.6(2) . . ?
N4 N3 Cu1 127.00(18) . . ?
C10 C5 C4 118.3(2) . . ?
C10 C5 C6 118.9(2) . . ?
C4 C5 C6 122.9(2) . . ?
O1 C9 C8 125.2(2) . . ?
O1 C9 C10 116.3(2) . . ?
C8 C9 C10 118.4(2) . . ?
C2 C1 C10 120.8(2) . . ?
C9 C8 C7 118.3(2) . . ?
C9 C8 C16 122.2(2) . . ?
C7 C8 C16 119.2(2) . . ?
C6 C7 C8 123.0(3) . . ?
N1 C12 C13 108.6(2) . . ?
N1 C16 C8 122.5(2) . . ?
N1 C16 C11 119.8(2) . . ?
C8 C16 C11 117.6(2) . . ?
N2 C13 C12 110.45(19) . . ?
C3 C4 C5 120.9(2) . . ?
C7 C6 C5 120.6(3) . . ?
C4 C3 C2 120.8(2) . . ?
C1 C2 C3 119.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.22
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2M2
_database_code_depnum_ccdc_archive 'CCDC 1053247'
_audit_update_record             
;
2016-02-09 deposited with the CCDC.
2016-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 Cu N3 O2'
_chemical_formula_weight         346.87

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   7.032(12)
_cell_length_b                   7.827(14)
_cell_length_c                   27.76(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1528(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3418
_cell_measurement_theta_min      2.7220
_cell_measurement_theta_max      30.2410

_exptl_crystal_description       block
_exptl_crystal_colour            dark-blue
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    1.439
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_T_max  0.789
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9390
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.52
_reflns_number_total             2860
_reflns_number_gt                2582
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0803P)²+0.4153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(16)
_refine_ls_number_reflns         2860
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_restrained_S_all      0.856
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.005

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.43801(5) 1.20595(5) 0.170640(13) 0.03564(13) Uani 1 1 d . . .
O1 O 0.6430(3) 1.0638(3) 0.14744(9) 0.0453(6) Uani 1 1 d . . .
O2 O 0.7171(4) 1.4602(4) 0.28564(11) 0.0646(8) Uani 1 1 d . . .
N2 N 0.2090(4) 1.3598(3) 0.18878(10) 0.0357(6) Uani 1 1 d . . .
C15 C 0.1717(5) 1.3686(6) 0.24191(13) 0.0537(10) Uani 1 1 d . . .
H15A H 0.1462 1.2536 0.2542 0.081 Uiso 1 1 calc R . .
H15B H 0.0612 1.4419 0.2479 0.081 Uiso 1 1 calc R . .
H15C H 0.2833 1.4161 0.2583 0.081 Uiso 1 1 calc R . .
N1 N 0.2772(4) 1.1313(3) 0.11737(9) 0.0340(6) Uani 1 1 d . . .
N3 N 0.6008(4) 1.3086(5) 0.21839(13) 0.0646(10) Uani 1 1 d . . .
C16 C 0.6559(5) 1.3849(5) 0.25152(14) 0.0445(8) Uani 1 1 d . . .
C14 C 0.2471(6) 1.5347(4) 0.17028(17) 0.0570(10) Uani 1 1 d . . .
H14A H 0.3582 1.5824 0.1868 0.085 Uiso 1 1 calc R . .
H14B H 0.1362 1.6075 0.1763 0.085 Uiso 1 1 calc R . .
H14C H 0.2719 1.5295 0.1356 0.085 Uiso 1 1 calc R . .
C13 C 0.0429(4) 1.2839(4) 0.16405(11) 0.0399(7) Uani 1 1 d . . .
H13A H -0.0612 1.3688 0.1622 0.048 Uiso 1 1 calc R . .
H13B H -0.0036 1.1841 0.1825 0.048 Uiso 1 1 calc R . .
C12 C 0.0985(4) 1.2283(5) 0.11375(12) 0.0407(7) Uani 1 1 d . . .
H12A H -0.0025 1.1559 0.0996 0.049 Uiso 1 1 calc R . .
H12B H 0.1164 1.3295 0.0928 0.049 Uiso 1 1 calc R . .
C11 C 0.3009(4) 0.9961(4) 0.09147(11) 0.0352(7) Uani 1 1 d . . .
H11 H 0.2020 0.9669 0.0696 0.042 Uiso 1 1 calc R . .
C10 C 0.4647(5) 0.8855(4) 0.09288(10) 0.0338(7) Uani 1 1 d . . .
C1 C 0.6263(4) 0.9282(4) 0.12115(12) 0.0365(7) Uani 1 1 d . . .
C2 C 0.7857(5) 0.8116(5) 0.12115(13) 0.0470(8) Uani 1 1 d . . .
H2 H 0.8969 0.8410 0.1387 0.056 Uiso 1 1 calc R . .
C3 C 0.7810(5) 0.6616(5) 0.09689(14) 0.0506(9) Uani 1 1 d . . .
H3 H 0.8880 0.5877 0.0983 0.061 Uiso 1 1 calc R . .
C4 C 0.6188(5) 0.6118(5) 0.06909(12) 0.0435(8) Uani 1 1 d . . .
C5 C 0.6148(6) 0.4521(5) 0.04524(14) 0.0570(10) Uani 1 1 d . . .
H5 H 0.7194 0.3762 0.0485 0.068 Uiso 1 1 calc R . .
C6 C 0.4619(7) 0.4052(5) 0.01744(14) 0.0613(11) Uani 1 1 d . . .
H6 H 0.4597 0.2968 0.0020 0.074 Uiso 1 1 calc R . .
C7 C 0.3104(6) 0.5180(5) 0.01211(14) 0.0542(10) Uani 1 1 d . . .
H7 H 0.2067 0.4877 -0.0081 0.065 Uiso 1 1 calc R . .
C8 C 0.3084(5) 0.6728(4) 0.03562(13) 0.0449(8) Uani 1 1 d . . .
H8 H 0.2018 0.7461 0.0318 0.054 Uiso 1 1 calc R . .
C9 C 0.4623(5) 0.7263(4) 0.06562(10) 0.0364(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.927(4) . ?
Cu1 O1 1.931(3) . ?
Cu1 N1 1.951(3) . ?
Cu1 N2 2.073(4) . ?
O1 C1 1.294(4) . ?
O2 C16 1.196(5) . ?
N2 C14 1.486(5) . ?
N2 C13 1.480(4) . ?
N2 C15 1.500(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 C11 1.290(4) . ?
N1 C12 1.471(4) . ?
N3 C16 1.163(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 C12 1.514(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C11 C10 1.441(5) . ?
C11 H11 0.9500 . ?
C10 C1 1.421(5) . ?
C10 C9 1.458(5) . ?
C1 C2 1.445(5) . ?
C2 C3 1.354(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.431(5) . ?
C3 H3 0.9500 . ?
C4 C9 1.423(5) . ?
C4 C5 1.414(6) . ?
C5 C6 1.373(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.428(5) . ?
C8 H8 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
N3 Cu1 O1 91.51(16) . . ?
N3 Cu1 N1 172.12(16) . . ?
O1 Cu1 N1 90.42(15) . . ?
N3 Cu1 N2 92.98(16) . . ?
O1 Cu1 N2 174.51(11) . . ?
N1 Cu1 N2 84.71(14) . . ?
C1 O1 Cu1 126.4(2) . . ?
C14 N2 C13 110.6(3) . . ?
C14 N2 C15 109.2(3) . . ?
C13 N2 C15 109.7(3) . . ?
C14 N2 Cu1 108.1(2) . . ?
C13 N2 Cu1 105.5(2) . . ?
C15 N2 Cu1 113.7(2) . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 N1 C12 119.7(3) . . ?
C11 N1 Cu1 126.4(2) . . ?
C12 N1 Cu1 113.1(2) . . ?
C16 N3 Cu1 163.0(3) . . ?
N3 C16 O2 178.1(4) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C13 C12 109.8(3) . . ?
N2 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
N2 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N1 C12 C13 107.8(3) . . ?
N1 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
N1 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.5 . . ?
N1 C11 C10 125.5(3) . . ?
N1 C11 H11 117.3 . . ?
C10 C11 H11 117.3 . . ?
C1 C10 C11 120.9(3) . . ?
C1 C10 C9 119.8(3) . . ?
C11 C10 C9 119.3(3) . . ?
O1 C1 C10 125.3(3) . . ?
O1 C1 C2 116.6(3) . . ?
C10 C1 C2 118.1(3) . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C9 C4 C5 120.6(4) . . ?
C9 C4 C3 118.7(3) . . ?
C5 C4 C3 120.6(3) . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.3(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 121.1(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.8(4) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C4 C9 C8 116.2(3) . . ?
C4 C9 C10 119.6(3) . . ?
C8 C9 C10 124.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.52
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.127
