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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 999066'
_audit_update_record             
;
2014-06-14 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 Cu N5 O'
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           ?
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.011(5)
_cell_length_b                   6.852(5)
_cell_length_c                   14.033(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 103.777(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     748.1(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.469
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            2717
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0868
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.68
_reflns_number_total             1548
_reflns_number_gt                1487
_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)+(0.1254P)²+1.6164P] 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   0.06(6)
_refine_ls_number_reflns         1487
_refine_ls_number_parameters     157
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.2097
_refine_ls_wR_factor_gt          0.1880
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.07718(18) 0.7436(3) 0.34759(11) 0.0445(6) Uani 1 1 d . . .
O1 O -0.0810(11) 0.9560(14) 0.3021(9) 0.052(3) Uani 1 1 d . . .
N2 N -0.0334(15) 0.5857(18) 0.2363(10) 0.0519(17) Uani 1 1 d . . .
C6 C -0.2973(18) 0.770(3) 0.1904(10) 0.049(4) Uani 1 1 d . . .
N1 N 0.2499(16) 0.5220(18) 0.3808(10) 0.0519(17) Uani 1 1 d . . .
C3 C 0.154(2) 0.351(2) 0.3282(12) 0.055(2) Uani 1 1 d . . .
H3A H 0.0730 0.3032 0.3643 0.066 Uiso 1 1 calc R . .
H3B H 0.2340 0.2464 0.3247 0.066 Uiso 1 1 calc R . .
C7 C -0.478(2) 0.774(2) 0.1334(10) 0.052(5) Uani 1 1 d . . .
C4 C 0.058(2) 0.409(2) 0.2253(11) 0.055(2) Uani 1 1 d . . .
H4A H 0.1377 0.4318 0.1842 0.066 Uiso 1 1 calc R . .
H4B H -0.0217 0.3071 0.1956 0.066 Uiso 1 1 calc R . .
C8 C -0.550(2) 0.613(2) 0.0727(11) 0.062(5) Uani 1 1 d . . .
H8 H -0.4826 0.5066 0.0643 0.074 Uiso 1 1 calc R . .
C10 C -0.828(2) 0.779(3) 0.0345(12) 0.068(6) Uani 1 1 d . . .
H10 H -0.9431 0.7793 0.0006 0.081 Uiso 1 1 calc R . .
C1 C 0.3956(19) 0.575(2) 0.3381(11) 0.055(2) Uani 1 1 d . . .
H1A H 0.3538 0.6019 0.2694 0.082 Uiso 1 1 calc R . .
H1B H 0.4761 0.4692 0.3467 0.082 Uiso 1 1 calc R . .
H1C H 0.4516 0.6893 0.3705 0.082 Uiso 1 1 calc R . .
C14 C -0.348(2) 1.097(2) 0.2500(11) 0.058(5) Uani 1 1 d . . .
H14 H -0.3054 1.2053 0.2882 0.070 Uiso 1 1 calc R . .
C12 C -0.5869(19) 0.936(2) 0.1414(11) 0.051(5) Uani 1 1 d . . .
C9 C -0.726(2) 0.622(3) 0.0263(12) 0.072(6) Uani 1 1 d . . .
H9 H -0.7751 0.5166 -0.0120 0.086 Uiso 1 1 calc R . .
C11 C -0.762(2) 0.934(3) 0.0926(12) 0.072(6) Uani 1 1 d . . .
H11 H -0.8324 1.0380 0.0997 0.086 Uiso 1 1 calc R . .
C13 C -0.515(2) 1.099(3) 0.1975(11) 0.060(5) Uani 1 1 d . . .
H13 H -0.5817 1.2098 0.1987 0.072 Uiso 1 1 calc R . .
C5 C -0.1894(19) 0.608(2) 0.1834(10) 0.051(4) Uani 1 1 d . . .
H5 H -0.2335 0.5115 0.1378 0.061 Uiso 1 1 calc R . .
C15 C -0.2384(19) 0.938(2) 0.2485(11) 0.047(4) Uani 1 1 d . . .
C2 C 0.311(2) 0.483(2) 0.4851(12) 0.055(2) Uani 1 1 d . . .
H2A H 0.2152 0.4489 0.5120 0.082 Uiso 1 1 calc R . .
H2B H 0.3665 0.5968 0.5175 0.082 Uiso 1 1 calc R . .
H2C H 0.3910 0.3762 0.4945 0.082 Uiso 1 1 calc R . .
N4 N 0.1606(16) 0.9959(19) 0.5036(11) 0.0519(17) Uani 1 1 d . . .
N3 N 0.2192(15) 0.9040(19) 0.4498(10) 0.0519(17) Uani 1 1 d . . .
N5 N 0.1173(15) 1.0891(18) 0.5593(10) 0.0519(17) 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 N2 1.932(12) . ?
Cu1 O1 1.935(9) . ?
Cu1 N3 1.945(12) . ?
Cu1 N1 2.032(13) . ?
O1 C15 1.311(15) . ?
N2 C5 1.302(17) . ?
N2 C4 1.443(19) . ?
C6 C5 1.42(2) . ?
C6 C15 1.43(2) . ?
C6 C7 1.48(2) . ?
N1 C2 1.45(2) . ?
N1 C1 1.48(2) . ?
N1 C3 1.497(17) . ?
C3 C4 1.519(19) . ?
C7 C8 1.43(2) . ?
C7 C12 1.43(2) . ?
C8 C9 1.41(2) . ?
C10 C11 1.37(2) . ?
C10 C9 1.37(2) . ?
C14 C13 1.36(2) . ?
C14 C15 1.40(2) . ?
C12 C11 1.41(2) . ?
C12 C13 1.41(2) . ?
N4 N5 1.126(17) . ?
N4 N3 1.164(18) . ?

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 O1 90.9(5) . . ?
N2 Cu1 N3 170.9(6) . . ?
O1 Cu1 N3 92.3(5) . . ?
N2 Cu1 N1 85.6(5) . . ?
O1 Cu1 N1 173.7(6) . . ?
N3 Cu1 N1 90.4(5) . . ?
C15 O1 Cu1 125.8(9) . . ?
C5 N2 C4 118.7(12) . . ?
C5 N2 Cu1 126.0(11) . . ?
C4 N2 Cu1 114.2(9) . . ?
C5 C6 C15 123.1(12) . . ?
C5 C6 C7 120.8(14) . . ?
C15 C6 C7 116.0(16) . . ?
C2 N1 C1 110.2(12) . . ?
C2 N1 C3 111.1(12) . . ?
C1 N1 C3 110.9(13) . . ?
C2 N1 Cu1 114.6(11) . . ?
C1 N1 Cu1 106.4(9) . . ?
C3 N1 Cu1 103.4(8) . . ?
N1 C3 C4 110.3(12) . . ?
C8 C7 C12 118.8(13) . . ?
C8 C7 C6 120.5(16) . . ?
C12 C7 C6 120.7(14) . . ?
N2 C4 C3 105.8(13) . . ?
C9 C8 C7 117.2(17) . . ?
C11 C10 C9 120.2(13) . . ?
C13 C14 C15 122.5(14) . . ?
C11 C12 C13 120.6(16) . . ?
C11 C12 C7 120.5(14) . . ?
C13 C12 C7 118.8(12) . . ?
C10 C9 C8 123.3(15) . . ?
C10 C11 C12 120.0(17) . . ?
C14 C13 C12 120.8(15) . . ?
N2 C5 C6 124.7(13) . . ?
O1 C15 C14 116.1(13) . . ?
O1 C15 C6 122.9(14) . . ?
C14 C15 C6 120.9(13) . . ?
N5 N4 N3 174.3(15) . . ?
N4 N3 Cu1 121.9(10) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.196
_refine_diff_density_min         -0.855
_refine_diff_density_rms         0.135
####################################################################### 
# 
# 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_P
_database_code_depnum_ccdc_archive 'CCDC 1039159'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.0058(3)
_cell_length_b                   6.8434(2)
_cell_length_c                   14.0474(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.658(2)
_cell_angle_gamma                90.00
_cell_volume                     747.85(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_T_max  0.710
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            10888
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.69
_reflns_number_total             2842
_reflns_number_gt                2552
_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)+(0.0293P)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    riding
_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   0.033(14)
_refine_ls_number_reflns         2842
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.57708(4) 0.74228(6) 0.84759(2) 0.03647(11) Uani 1 1 d . . .
O1 O 0.4208(3) 0.5318(3) 0.80274(17) 0.0462(6) Uani 1 1 d . . .
N1 N 0.7525(3) 0.9638(3) 0.87789(18) 0.0353(6) Uani 1 1 d . . .
N2 N 0.4654(3) 0.9011(3) 0.73641(17) 0.0340(6) Uani 1 1 d . . .
C12 C -0.0818(4) 0.5523(5) 0.6397(2) 0.0441(8) Uani 1 1 d . . .
N4 N 0.6632(4) 0.4883(4) 1.0046(2) 0.0425(6) Uani 1 1 d . . .
N5 N 0.6165(5) 0.3957(6) 1.0607(3) 0.0816(11) Uani 1 1 d . . .
C1 C 0.8998(4) 0.9132(5) 0.8371(3) 0.0510(9) Uani 1 1 d . . .
H1A H 0.9566 0.8001 0.8701 0.076 Uiso 1 1 calc R . .
H1B H 0.9788 1.0209 0.8460 0.076 Uiso 1 1 calc R . .
H1C H 0.8602 0.8856 0.7684 0.076 Uiso 1 1 calc R . .
C2 C 0.8150(5) 1.0057(5) 0.9840(2) 0.0521(9) Uani 1 1 d . . .
H2A H 0.7192 1.0384 1.0112 0.078 Uiso 1 1 calc R . .
H2B H 0.8939 1.1134 0.9928 0.078 Uiso 1 1 calc R . .
H2C H 0.8722 0.8924 1.0166 0.078 Uiso 1 1 calc R . .
C3 C 0.6595(4) 1.1371(4) 0.8282(2) 0.0404(7) Uani 1 1 d . . .
H3A H 0.7409 1.2396 0.8238 0.049 Uiso 1 1 calc R . .
H3B H 0.5814 1.1864 0.8659 0.049 Uiso 1 1 calc R . .
C4 C 0.5587(4) 1.0807(4) 0.7259(2) 0.0406(7) Uani 1 1 d . . .
H4A H 0.4789 1.1838 0.6981 0.049 Uiso 1 1 calc R . .
H4B H 0.6362 1.0588 0.6833 0.049 Uiso 1 1 calc R . .
C5 C 0.3108(4) 0.8757(4) 0.6841(2) 0.0382(7) Uani 1 1 d . . .
H5 H 0.2656 0.9730 0.6392 0.046 Uiso 1 1 calc R . .
C6 C 0.2037(4) 0.7113(5) 0.68924(19) 0.0334(8) Uani 1 1 d . . .
C15 C 0.2672(4) 0.5483(4) 0.7480(2) 0.0373(7) Uani 1 1 d . . .
C14 C 0.1545(4) 0.3850(5) 0.7485(2) 0.0464(8) Uani 1 1 d . . .
H14 H 0.1965 0.2745 0.7848 0.056 Uiso 1 1 calc R . .
C13 C -0.0096(5) 0.3885(5) 0.6978(3) 0.0524(9) Uani 1 1 d . . .
H13 H -0.0789 0.2805 0.7005 0.063 Uiso 1 1 calc R . .
C11 C -0.2569(5) 0.5565(6) 0.5914(3) 0.0586(10) Uani 1 1 d . . .
H11 H -0.3264 0.4504 0.5972 0.070 Uiso 1 1 calc R . .
C10 C -0.3263(5) 0.7123(7) 0.5363(2) 0.0637(11) Uani 1 1 d . . .
H10 H -0.4431 0.7149 0.5064 0.076 Uiso 1 1 calc R . .
C9 C -0.2213(5) 0.8675(6) 0.5253(3) 0.0563(9) Uani 1 1 d . . .
H9 H -0.2674 0.9716 0.4851 0.068 Uiso 1 1 calc R . .
C8 C -0.0502(4) 0.8702(5) 0.5726(2) 0.0480(8) Uani 1 1 d . . .
H8 H 0.0169 0.9772 0.5650 0.058 Uiso 1 1 calc R . .
C7 C 0.0253(4) 0.7130(5) 0.63281(19) 0.0368(7) Uani 1 1 d . . .
N3 N 0.7213(4) 0.5770(4) 0.9485(2) 0.0536(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.914(2) . ?
Cu1 N2 1.939(2) . ?
Cu1 N3 1.962(3) . ?
Cu1 N1 2.042(2) . ?
Cu1 N5 2.472(3) 2_657 ?
O1 C15 1.292(4) . ?
N1 C1 1.469(4) . ?
N1 C3 1.484(4) . ?
N1 C2 1.484(4) . ?
N2 C5 1.293(4) . ?
N2 C4 1.464(3) . ?
C12 C11 1.406(5) . ?
C12 C7 1.412(5) . ?
C12 C13 1.426(5) . ?
N4 N5 1.140(4) . ?
N4 N3 1.175(4) . ?
N5 Cu1 2.472(3) 2_647 ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.522(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.427(4) . ?
C5 H5 0.9300 . ?
C6 C15 1.410(4) . ?
C6 C7 1.460(4) . ?
C15 C14 1.438(4) . ?
C14 C13 1.339(5) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C11 C10 1.357(5) . ?
C11 H11 0.9300 . ?
C10 C9 1.386(5) . ?
C10 H10 0.9300 . ?
C9 C8 1.374(5) . ?
C9 H9 0.9300 . ?
C8 C7 1.412(4) . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N2 90.87(10) . . ?
O1 Cu1 N3 91.80(11) . . ?
N2 Cu1 N3 170.34(12) . . ?
O1 Cu1 N1 172.35(10) . . ?
N2 Cu1 N1 85.16(10) . . ?
N3 Cu1 N1 91.09(11) . . ?
O1 Cu1 N5 92.84(11) . 2_657 ?
N2 Cu1 N5 87.43(12) . 2_657 ?
N3 Cu1 N5 101.71(14) . 2_657 ?
N1 Cu1 N5 93.51(10) . 2_657 ?
C15 O1 Cu1 125.90(18) . . ?
C1 N1 C3 111.4(2) . . ?
C1 N1 C2 109.0(3) . . ?
C3 N1 C2 109.3(2) . . ?
C1 N1 Cu1 108.65(19) . . ?
C3 N1 Cu1 104.54(17) . . ?
C2 N1 Cu1 113.9(2) . . ?
C5 N2 C4 119.9(3) . . ?
C5 N2 Cu1 125.5(2) . . ?
C4 N2 Cu1 113.72(19) . . ?
C11 C12 C7 120.2(3) . . ?
C11 C12 C13 121.0(3) . . ?
C7 C12 C13 118.8(3) . . ?
N5 N4 N3 175.6(4) . . ?
N4 N5 Cu1 160.8(3) . 2_647 ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 109.7(2) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N2 C4 C3 106.7(2) . . ?
N2 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
N2 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N2 C5 C6 125.7(3) . . ?
N2 C5 H5 117.2 . . ?
C6 C5 H5 117.2 . . ?
C15 C6 C5 121.0(3) . . ?
C15 C6 C7 119.7(3) . . ?
C5 C6 C7 119.3(3) . . ?
O1 C15 C6 125.4(3) . . ?
O1 C15 C14 116.1(3) . . ?
C6 C15 C14 118.5(3) . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C13 C12 122.2(3) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C10 C9 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C12 C7 C8 117.0(3) . . ?
C12 C7 C6 119.2(3) . . ?
C8 C7 C6 123.8(3) . . ?
N4 N3 Cu1 121.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.69
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_M-2
_database_code_depnum_ccdc_archive 'CCDC 1046260'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.0039(4)
_cell_length_b                   6.8403(3)
_cell_length_c                   14.0443(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.686(2)
_cell_angle_gamma                90.00
_cell_volume                     747.08(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6085
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.66
_reflns_number_total             2608
_reflns_number_gt                2276
_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)+(0.0323P)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    riding
_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   0.006(16)
_refine_ls_number_reflns         2608
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.57718(5) 0.75955(8) 0.84761(3) 0.03651(14) Uani 1 1 d . . .
N3 N 0.7210(5) 0.9242(5) 0.9485(3) 0.0527(9) Uani 1 1 d . . .
N2 N 0.4650(4) 0.6007(4) 0.7365(2) 0.0332(7) Uani 1 1 d . . .
C5 C 0.3112(5) 0.6271(5) 0.6843(3) 0.0379(9) Uani 1 1 d . . .
H5 H 0.2663 0.5302 0.6390 0.045 Uiso 1 1 calc R . .
O1 O 0.4213(4) 0.9697(3) 0.8028(2) 0.0454(7) Uani 1 1 d . . .
N1 N 0.7521(4) 0.5383(4) 0.8779(2) 0.0338(7) Uani 1 1 d . . .
N4 N 0.6629(4) 1.0139(5) 1.0047(2) 0.0413(8) Uani 1 1 d . . .
C6 C 0.2036(5) 0.7900(6) 0.6893(2) 0.0329(9) Uani 1 1 d . . .
C7 C 0.0252(5) 0.7894(6) 0.6331(2) 0.0361(9) Uani 1 1 d . . .
C12 C -0.0812(5) 0.9498(6) 0.6400(3) 0.0418(10) Uani 1 1 d . . .
C13 C -0.0098(6) 1.1131(6) 0.6977(3) 0.0500(11) Uani 1 1 d . . .
H13 H -0.0792 1.2210 0.7005 0.060 Uiso 1 1 calc R . .
C14 C 0.1541(5) 1.1164(6) 0.7481(3) 0.0455(10) Uani 1 1 d . . .
H14 H 0.1960 1.2273 0.7842 0.055 Uiso 1 1 calc R . .
C15 C 0.2676(5) 0.9534(5) 0.7481(3) 0.0368(9) Uani 1 1 d . . .
C11 C -0.2569(6) 0.9453(7) 0.5918(3) 0.0583(12) Uani 1 1 d . . .
H11 H -0.3267 1.0508 0.5982 0.070 Uiso 1 1 calc R . .
C10 C -0.3264(6) 0.7893(9) 0.5359(3) 0.0629(14) Uani 1 1 d . . .
H10 H -0.4429 0.7868 0.5054 0.075 Uiso 1 1 calc R . .
C9 C -0.2206(6) 0.6345(7) 0.5253(3) 0.0548(11) Uani 1 1 d . . .
H9 H -0.2662 0.5301 0.4850 0.066 Uiso 1 1 calc R . .
C8 C -0.0513(5) 0.6322(6) 0.5726(3) 0.0493(10) Uani 1 1 d . . .
H8 H 0.0157 0.5248 0.5651 0.059 Uiso 1 1 calc R . .
C4 C 0.5581(5) 0.4209(5) 0.7256(3) 0.0403(9) Uani 1 1 d . . .
H4A H 0.6352 0.4426 0.6828 0.048 Uiso 1 1 calc R . .
H4B H 0.4782 0.3176 0.6980 0.048 Uiso 1 1 calc R . .
C3 C 0.6595(5) 0.3653(5) 0.8283(3) 0.0407(9) Uani 1 1 d . . .
H3A H 0.5816 0.3158 0.8661 0.049 Uiso 1 1 calc R . .
H3B H 0.7412 0.2629 0.8240 0.049 Uiso 1 1 calc R . .
C1 C 0.8155(6) 0.4960(6) 0.9834(3) 0.0497(11) Uani 1 1 d . . .
H1A H 0.8748 0.6084 1.0159 0.075 Uiso 1 1 calc R . .
H1B H 0.8929 0.3867 0.9918 0.075 Uiso 1 1 calc R . .
H1C H 0.7201 0.4654 1.0112 0.075 Uiso 1 1 calc R . .
C2 C 0.9003(5) 0.5893(6) 0.8366(3) 0.0510(11) Uani 1 1 d . . .
H2A H 0.9571 0.7026 0.8695 0.076 Uiso 1 1 calc R . .
H2B H 0.8604 0.6168 0.7679 0.076 Uiso 1 1 calc R . .
H2C H 0.9794 0.4817 0.8455 0.076 Uiso 1 1 calc R . .
N5 N 0.6164(6) 1.1068(7) 1.0609(3) 0.0837(14) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.910(3) . ?
Cu1 N2 1.938(3) . ?
Cu1 N3 1.957(4) . ?
Cu1 N1 2.037(3) . ?
Cu1 N5 2.467(4) 2_647 ?
N3 N4 1.179(4) . ?
N2 C5 1.288(4) . ?
N2 C4 1.465(4) . ?
C5 C6 1.420(5) . ?
C5 H5 0.9300 . ?
O1 C15 1.291(4) . ?
N1 C3 1.480(4) . ?
N1 C1 1.478(5) . ?
N1 C2 1.480(5) . ?
N4 N5 1.142(5) . ?
C6 C15 1.412(5) . ?
C6 C7 1.459(5) . ?
C7 C12 1.407(5) . ?
C7 C8 1.417(5) . ?
C12 C11 1.409(5) . ?
C12 C13 1.418(6) . ?
C13 C14 1.335(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.439(5) . ?
C14 H14 0.9300 . ?
C11 C10 1.363(6) . ?
C11 H11 0.9300 . ?
C10 C9 1.386(6) . ?
C10 H10 0.9300 . ?
C9 C8 1.361(6) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C4 C3 1.526(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
N5 Cu1 2.467(4) 2_657 ?

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 N2 90.83(12) . . ?
O1 Cu1 N3 91.84(13) . . ?
N2 Cu1 N3 170.54(15) . . ?
O1 Cu1 N1 172.34(12) . . ?
N2 Cu1 N1 85.18(12) . . ?
N3 Cu1 N1 91.09(13) . . ?
O1 Cu1 N5 92.78(13) . 2_647 ?
N2 Cu1 N5 87.33(15) . 2_647 ?
N3 Cu1 N5 101.61(15) . 2_647 ?
N1 Cu1 N5 93.57(12) . 2_647 ?
N4 N3 Cu1 121.8(3) . . ?
C5 N2 C4 120.0(3) . . ?
C5 N2 Cu1 125.3(3) . . ?
C4 N2 Cu1 113.9(2) . . ?
N2 C5 C6 126.3(4) . . ?
N2 C5 H5 116.9 . . ?
C6 C5 H5 116.9 . . ?
C15 O1 Cu1 126.0(2) . . ?
C3 N1 C1 109.3(3) . . ?
C3 N1 C2 111.3(3) . . ?
C1 N1 C2 108.8(3) . . ?
C3 N1 Cu1 104.6(2) . . ?
C1 N1 Cu1 114.2(2) . . ?
C2 N1 Cu1 108.6(2) . . ?
N5 N4 N3 175.7(4) . . ?
C15 C6 C5 120.6(3) . . ?
C15 C6 C7 119.5(4) . . ?
C5 C6 C7 119.9(4) . . ?
C12 C7 C8 116.8(4) . . ?
C12 C7 C6 119.4(4) . . ?
C8 C7 C6 123.8(4) . . ?
C7 C12 C11 120.1(4) . . ?
C7 C12 C13 119.0(4) . . ?
C11 C12 C13 120.9(4) . . ?
C14 C13 C12 121.9(4) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 121.9(4) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
O1 C15 C6 125.4(3) . . ?
O1 C15 C14 116.5(3) . . ?
C6 C15 C14 118.1(4) . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C8 C9 C10 121.3(5) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C8 C7 121.6(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
N2 C4 C3 106.3(3) . . ?
N2 C4 H4A 110.5 . . ?
C3 C4 H4A 110.5 . . ?
N2 C4 H4B 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
N1 C3 C4 109.9(3) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N4 N5 Cu1 160.6(3) . 2_657 ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.66
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_M-3
_database_code_depnum_ccdc_archive 'CCDC 1046261'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.0022(3)
_cell_length_b                   6.8450(2)
_cell_length_c                   14.0354(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.724(2)
_cell_angle_gamma                90.00
_cell_volume                     746.84(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3758
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6174
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.73
_reflns_number_total             2630
_reflns_number_gt                2433
_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)+(0.0412P)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    riding
_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   0.133(16)
_refine_ls_number_reflns         2630
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.42274(4) 0.24079(7) 0.15241(2) 0.03548(13) Uani 1 1 d . . .
N3 N 0.2783(4) 0.4048(5) 0.0518(3) 0.0519(8) Uani 1 1 d . . .
N1 N 0.2480(3) 0.0197(4) 0.1226(2) 0.0349(7) Uani 1 1 d . . .
O1 O 0.5783(3) 0.4514(4) 0.19719(19) 0.0459(6) Uani 1 1 d . . .
N4 N 0.3365(4) 0.4939(5) -0.0045(2) 0.0414(7) Uani 1 1 d . . .
N5 N 0.3833(5) 0.5866(7) -0.0607(3) 0.0834(13) Uani 1 1 d . . .
C1 C 0.0995(4) 0.0694(6) 0.1629(3) 0.0501(10) Uani 1 1 d . . .
H1A H 0.0431 0.1830 0.1300 0.075 Uiso 1 1 calc R . .
H1B H 0.1383 0.0960 0.2317 0.075 Uiso 1 1 calc R . .
H1C H 0.0204 -0.0382 0.1531 0.075 Uiso 1 1 calc R . .
C2 C 0.1859(5) -0.0222(7) 0.0164(3) 0.0521(10) Uani 1 1 d . . .
H2A H 0.1274 0.0904 -0.0162 0.078 Uiso 1 1 calc R . .
H2B H 0.1081 -0.1311 0.0075 0.078 Uiso 1 1 calc R . .
H2C H 0.2820 -0.0531 -0.0108 0.078 Uiso 1 1 calc R . .
C3 C 0.3399(5) -0.1544(5) 0.1721(2) 0.0399(8) Uani 1 1 d . . .
H3A H 0.4172 -0.2048 0.1343 0.048 Uiso 1 1 calc R . .
H3B H 0.2577 -0.2560 0.1768 0.048 Uiso 1 1 calc R . .
C4 C 0.4418(4) -0.0976(5) 0.2745(2) 0.0400(8) Uani 1 1 d . . .
H4A H 0.3649 -0.0759 0.3175 0.048 Uiso 1 1 calc R . .
H4B H 0.5221 -0.2004 0.3023 0.048 Uiso 1 1 calc R . .
N2 N 0.5343(3) 0.0818(4) 0.26369(19) 0.0338(6) Uani 1 1 d . . .
C5 C 0.6899(4) 0.1078(5) 0.3157(2) 0.0376(8) Uani 1 1 d . . .
H5 H 0.7362 0.0098 0.3600 0.045 Uiso 1 1 calc R . .
C6 C 0.7960(4) 0.2721(6) 0.3110(2) 0.0337(9) Uani 1 1 d . . .
C15 C 0.7331(4) 0.4351(5) 0.2519(2) 0.0374(8) Uani 1 1 d . . .
C14 C 0.8448(5) 0.5975(6) 0.2511(3) 0.0455(9) Uani 1 1 d . . .
H14 H 0.8025 0.7076 0.2144 0.055 Uiso 1 1 calc R . .
C12 C 1.0810(4) 0.4302(6) 0.3603(2) 0.0440(10) Uani 1 1 d . . .
C11 C 1.2580(5) 0.4258(7) 0.4086(3) 0.0588(12) Uani 1 1 d . . .
H11 H 1.3284 0.5306 0.4021 0.071 Uiso 1 1 calc R . .
C10 C 1.3254(5) 0.2702(9) 0.4642(3) 0.0634(14) Uani 1 1 d . . .
H10 H 1.4417 0.2684 0.4953 0.076 Uiso 1 1 calc R . .
C9 C 1.2221(5) 0.1146(7) 0.4746(3) 0.0550(11) Uani 1 1 d . . .
H9 H 1.2689 0.0094 0.5139 0.066 Uiso 1 1 calc R . .
C8 C 1.0499(5) 0.1132(7) 0.4274(2) 0.0474(9) Uani 1 1 d . . .
H8 H 0.9820 0.0070 0.4353 0.057 Uiso 1 1 calc R . .
C7 C 0.9756(4) 0.2706(6) 0.3673(2) 0.0363(9) Uani 1 1 d . . .
C13 C 1.0106(5) 0.5947(6) 0.3025(3) 0.0501(10) Uani 1 1 d . . .
H13 H 1.0801 0.7026 0.3001 0.060 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 1.911(2) . ?
Cu1 N2 1.939(3) . ?
Cu1 N3 1.954(3) . ?
Cu1 N1 2.036(3) . ?
Cu1 N5 2.475(4) 2_645 ?
N3 N4 1.178(4) . ?
N1 C1 1.471(4) . ?
N1 C2 1.483(4) . ?
N1 C3 1.483(4) . ?
O1 C15 1.298(4) . ?
N4 N5 1.142(5) . ?
N5 Cu1 2.475(4) 2_655 ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.525(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.460(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
N2 C5 1.298(4) . ?
C5 C6 1.420(5) . ?
C5 H5 0.9300 . ?
C6 C15 1.410(5) . ?
C6 C7 1.466(4) . ?
C15 C14 1.428(5) . ?
C14 C13 1.352(5) . ?
C14 H14 0.9300 . ?
C12 C7 1.398(5) . ?
C12 C11 1.418(5) . ?
C12 C13 1.423(6) . ?
C11 C10 1.354(7) . ?
C11 H11 0.9300 . ?
C10 C9 1.377(6) . ?
C10 H10 0.9300 . ?
C9 C8 1.380(5) . ?
C9 H9 0.9300 . ?
C8 C7 1.410(5) . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N2 91.10(11) . . ?
O1 Cu1 N3 91.81(13) . . ?
N2 Cu1 N3 170.17(13) . . ?
O1 Cu1 N1 172.16(12) . . ?
N2 Cu1 N1 84.87(11) . . ?
N3 Cu1 N1 91.09(13) . . ?
O1 Cu1 N5 93.03(12) . 2_645 ?
N2 Cu1 N5 87.36(14) . 2_645 ?
N3 Cu1 N5 101.85(15) . 2_645 ?
N1 Cu1 N5 93.50(12) . 2_645 ?
N4 N3 Cu1 121.5(3) . . ?
C1 N1 C2 108.8(3) . . ?
C1 N1 C3 111.2(3) . . ?
C2 N1 C3 109.0(3) . . ?
C1 N1 Cu1 109.1(2) . . ?
C2 N1 Cu1 113.6(2) . . ?
C3 N1 Cu1 105.12(18) . . ?
C15 O1 Cu1 125.9(2) . . ?
N5 N4 N3 175.7(4) . . ?
N4 N5 Cu1 160.8(3) . 2_655 ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 109.4(3) . . ?
N1 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
N2 C4 C3 106.7(3) . . ?
N2 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
N2 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C5 N2 C4 119.9(3) . . ?
C5 N2 Cu1 125.0(2) . . ?
C4 N2 Cu1 114.1(2) . . ?
N2 C5 C6 126.0(3) . . ?
N2 C5 H5 117.0 . . ?
C6 C5 H5 117.0 . . ?
C15 C6 C5 121.3(3) . . ?
C15 C6 C7 119.3(3) . . ?
C5 C6 C7 119.3(3) . . ?
O1 C15 C6 125.0(3) . . ?
O1 C15 C14 116.1(3) . . ?
C6 C15 C14 118.9(3) . . ?
C13 C14 C15 121.5(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C7 C12 C11 120.0(4) . . ?
C7 C12 C13 119.6(3) . . ?
C11 C12 C13 120.3(4) . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C8 C7 120.9(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C12 C7 C8 117.6(3) . . ?
C12 C7 C6 119.1(3) . . ?
C8 C7 C6 123.2(3) . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.73
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_M-4
_database_code_depnum_ccdc_archive 'CCDC 1046262'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.0030(2)
_cell_length_b                   6.8474(2)
_cell_length_c                   14.0460(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.701(2)
_cell_angle_gamma                90.00
_cell_volume                     747.81(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6228
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6202
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.70
_reflns_number_total             2620
_reflns_number_gt                2365
_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)+(0.0295P)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    riding
_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   0.035(15)
_refine_ls_number_reflns         2620
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.42280(4) 0.24336(7) 0.15237(2) 0.03588(12) Uani 1 1 d . . .
O1 O 0.5784(3) 0.4547(4) 0.19711(18) 0.0453(6) Uani 1 1 d . . .
N5 N 0.3839(4) 0.5897(7) -0.0609(3) 0.0817(13) Uani 1 1 d . . .
N3 N 0.2785(4) 0.4086(5) 0.0512(2) 0.0521(8) Uani 1 1 d . . .
N4 N 0.3366(3) 0.4975(5) -0.0047(2) 0.0411(7) Uani 1 1 d . . .
N2 N 0.5344(3) 0.0845(4) 0.26357(18) 0.0337(6) Uani 1 1 d . . .
N1 N 0.2477(3) 0.0226(4) 0.12225(19) 0.0343(7) Uani 1 1 d . . .
C5 C 0.6901(4) 0.1105(5) 0.3161(2) 0.0360(8) Uani 1 1 d . . .
H5 H 0.7358 0.0133 0.3610 0.043 Uiso 1 1 calc R . .
C6 C 0.7963(4) 0.2747(6) 0.3109(2) 0.0321(9) Uani 1 1 d . . .
C15 C 0.7335(4) 0.4363(5) 0.2524(2) 0.0372(8) Uani 1 1 d . . .
C14 C 0.8446(4) 0.6010(6) 0.2510(2) 0.0454(9) Uani 1 1 d . . .
H14 H 0.8020 0.7108 0.2142 0.055 Uiso 1 1 calc R . .
C13 C 1.0101(4) 0.5979(6) 0.3027(3) 0.0515(10) Uani 1 1 d . . .
H13 H 1.0796 0.7060 0.3007 0.062 Uiso 1 1 calc R . .
C12 C 1.0802(4) 0.4342(6) 0.3599(2) 0.0444(10) Uani 1 1 d . . .
C11 C 1.2576(5) 0.4300(7) 0.4085(3) 0.0568(11) Uani 1 1 d . . .
H11 H 1.3277 0.5354 0.4027 0.068 Uiso 1 1 calc R . .
C10 C 1.3259(4) 0.2722(9) 0.4639(2) 0.0627(13) Uani 1 1 d . . .
H10 H 1.4425 0.2693 0.4942 0.075 Uiso 1 1 calc R . .
C9 C 1.2220(4) 0.1177(7) 0.4748(3) 0.0539(10) Uani 1 1 d . . .
H9 H 1.2687 0.0132 0.5146 0.065 Uiso 1 1 calc R . .
C8 C 1.0497(4) 0.1150(6) 0.4276(2) 0.0469(9) Uani 1 1 d . . .
H8 H 0.9820 0.0087 0.4356 0.056 Uiso 1 1 calc R . .
C7 C 0.9754(4) 0.2726(6) 0.3672(2) 0.0355(9) Uani 1 1 d . . .
C4 C 0.4420(4) -0.0943(5) 0.2744(2) 0.0409(8) Uani 1 1 d . . .
H4A H 0.3653 -0.0725 0.3175 0.049 Uiso 1 1 calc R . .
H4B H 0.5223 -0.1972 0.3021 0.049 Uiso 1 1 calc R . .
C3 C 0.3395(4) -0.1513(5) 0.1721(2) 0.0409(8) Uani 1 1 d . . .
H3A H 0.4166 -0.2022 0.1343 0.049 Uiso 1 1 calc R . .
H3B H 0.2572 -0.2525 0.1770 0.049 Uiso 1 1 calc R . .
C2 C 0.1849(5) -0.0200(6) 0.0162(3) 0.0508(10) Uani 1 1 d . . .
H2A H 0.1266 0.0926 -0.0165 0.076 Uiso 1 1 calc R . .
H2B H 0.1067 -0.1285 0.0077 0.076 Uiso 1 1 calc R . .
H2C H 0.2806 -0.0518 -0.0111 0.076 Uiso 1 1 calc R . .
C1 C 0.0996(4) 0.0725(6) 0.1635(3) 0.0506(10) Uani 1 1 d . . .
H1A H 0.0427 0.1859 0.1309 0.076 Uiso 1 1 calc R . .
H1B H 0.1394 0.0992 0.2323 0.076 Uiso 1 1 calc R . .
H1C H 0.0205 -0.0351 0.1543 0.076 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 1.916(2) . ?
Cu1 N2 1.939(3) . ?
Cu1 N3 1.963(3) . ?
Cu1 N1 2.037(3) . ?
Cu1 N5 2.468(4) 2_645 ?
O1 C15 1.304(3) . ?
N5 N4 1.142(4) . ?
N5 Cu1 2.468(4) 2_655 ?
N3 N4 1.174(4) . ?
N2 C5 1.301(4) . ?
N2 C4 1.457(4) . ?
N1 C1 1.478(4) . ?
N1 C2 1.484(4) . ?
N1 C3 1.484(4) . ?
C5 C6 1.422(5) . ?
C5 H5 0.9300 . ?
C6 C15 1.399(5) . ?
C6 C7 1.464(4) . ?
C15 C14 1.439(5) . ?
C14 C13 1.352(5) . ?
C14 H14 0.9300 . ?
C13 C12 1.415(5) . ?
C13 H13 0.9300 . ?
C12 C7 1.407(5) . ?
C12 C11 1.422(4) . ?
C11 C10 1.367(6) . ?
C11 H11 0.9300 . ?
C10 C9 1.376(6) . ?
C10 H10 0.9300 . ?
C9 C8 1.382(5) . ?
C9 H9 0.9300 . ?
C8 C7 1.414(5) . ?
C8 H8 0.9300 . ?
C4 C3 1.527(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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 N2 91.13(11) . . ?
O1 Cu1 N3 91.56(12) . . ?
N2 Cu1 N3 170.37(12) . . ?
O1 Cu1 N1 172.25(11) . . ?
N2 Cu1 N1 85.06(11) . . ?
N3 Cu1 N1 91.14(12) . . ?
O1 Cu1 N5 93.08(11) . 2_645 ?
N2 Cu1 N5 87.38(13) . 2_645 ?
N3 Cu1 N5 101.70(14) . 2_645 ?
N1 Cu1 N5 93.49(12) . 2_645 ?
C15 O1 Cu1 125.1(2) . . ?
N4 N5 Cu1 161.1(3) . 2_655 ?
N4 N3 Cu1 121.7(2) . . ?
N5 N4 N3 175.9(4) . . ?
C5 N2 C4 119.8(3) . . ?
C5 N2 Cu1 125.2(2) . . ?
C4 N2 Cu1 114.05(19) . . ?
C1 N1 C2 109.1(3) . . ?
C1 N1 C3 110.7(3) . . ?
C2 N1 C3 109.1(3) . . ?
C1 N1 Cu1 108.8(2) . . ?
C2 N1 Cu1 114.0(2) . . ?
C3 N1 Cu1 104.95(17) . . ?
N2 C5 C6 125.6(3) . . ?
N2 C5 H5 117.2 . . ?
C6 C5 H5 117.2 . . ?
C15 C6 C5 121.3(3) . . ?
C15 C6 C7 119.6(3) . . ?
C5 C6 C7 119.0(3) . . ?
O1 C15 C6 125.8(3) . . ?
O1 C15 C14 114.9(3) . . ?
C6 C15 C14 119.4(3) . . ?
C13 C14 C15 120.7(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C13 C12 121.6(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C7 C12 C13 120.1(3) . . ?
C7 C12 C11 119.6(4) . . ?
C13 C12 C11 120.3(4) . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C9 C8 121.1(4) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C12 C7 C8 118.1(3) . . ?
C12 C7 C6 118.5(3) . . ?
C8 C7 C6 123.4(4) . . ?
N2 C4 C3 106.8(3) . . ?
N2 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
N2 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N1 C3 C4 109.6(3) . . ?
N1 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.70
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_M-5
_database_code_depnum_ccdc_archive 'CCDC 1046263'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.0019(2)
_cell_length_b                   6.8447(2)
_cell_length_c                   14.0472(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.7180(10)
_cell_angle_gamma                90.00
_cell_volume                     747.43(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.470
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12095
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.71
_reflns_number_total             2849
_reflns_number_gt                2641
_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)+(0.0344P)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    riding
_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(12)
_refine_ls_number_reflns         2849
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0602
_refine_ls_wR_factor_gt          0.0592
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.57712(3) 0.74730(5) 0.847635(18) 0.03586(10) Uani 1 1 d . . .
O1 O 0.4212(2) 0.9581(2) 0.80277(15) 0.0463(5) Uani 1 1 d . . .
N1 N 0.7523(3) 0.5257(3) 0.87806(16) 0.0356(5) Uani 1 1 d . . .
N2 N 0.4654(3) 0.5883(3) 0.73642(14) 0.0334(4) Uani 1 1 d . . .
C10 C -0.3258(4) 0.7764(6) 0.5363(2) 0.0631(9) Uani 1 1 d . . .
H10 H -0.4425 0.7733 0.5061 0.076 Uiso 1 1 calc R . .
N4 N 0.6636(3) 1.0013(3) 1.00500(17) 0.0415(5) Uani 1 1 d . . .
C3 C 0.6603(3) 0.3521(3) 0.8281(2) 0.0404(6) Uani 1 1 d . . .
H3A H 0.5830 0.3014 0.8658 0.048 Uiso 1 1 calc R . .
H3B H 0.7426 0.2506 0.8234 0.048 Uiso 1 1 calc R . .
C4 C 0.5583(3) 0.4084(4) 0.72579(19) 0.0414(6) Uani 1 1 d . . .
H4A H 0.6351 0.4298 0.6828 0.050 Uiso 1 1 calc R . .
H4B H 0.4780 0.3054 0.6982 0.050 Uiso 1 1 calc R . .
C5 C 0.3105(3) 0.6138(4) 0.68411(18) 0.0372(6) Uani 1 1 d . . .
H5 H 0.2646 0.5163 0.6394 0.045 Uiso 1 1 calc R . .
C6 C 0.2044(3) 0.7787(4) 0.68928(17) 0.0343(6) Uani 1 1 d . . .
C15 C 0.2667(3) 0.9413(3) 0.74802(19) 0.0376(6) Uani 1 1 d . . .
C14 C 0.1549(3) 1.1041(4) 0.7486(2) 0.0462(6) Uani 1 1 d . . .
H14 H 0.1973 1.2141 0.7853 0.055 Uiso 1 1 calc R . .
C13 C -0.0097(4) 1.1020(4) 0.6975(2) 0.0517(7) Uani 1 1 d . . .
H13 H -0.0787 1.2105 0.6995 0.062 Uiso 1 1 calc R . .
C12 C -0.0808(3) 0.9371(4) 0.64003(19) 0.0456(7) Uani 1 1 d . . .
C11 C -0.2579(4) 0.9336(5) 0.5912(2) 0.0576(8) Uani 1 1 d . . .
H11 H -0.3279 1.0394 0.5969 0.069 Uiso 1 1 calc R . .
C8 C -0.0500(3) 0.6186(5) 0.57209(19) 0.0475(7) Uani 1 1 d . . .
H8 H 0.0176 0.5123 0.5638 0.057 Uiso 1 1 calc R . .
C7 C 0.0248(3) 0.7766(4) 0.63293(16) 0.0370(6) Uani 1 1 d . . .
C2 C 0.9006(3) 0.5769(5) 0.8370(2) 0.0516(7) Uani 1 1 d . . .
H2A H 0.8607 0.6053 0.7684 0.077 Uiso 1 1 calc R . .
H2B H 0.9794 0.4690 0.8455 0.077 Uiso 1 1 calc R . .
H2C H 0.9578 0.6895 0.8704 0.077 Uiso 1 1 calc R . .
N3 N 0.7209(3) 0.9127(4) 0.9488(2) 0.0538(6) Uani 1 1 d . . .
N5 N 0.6163(4) 1.0940(5) 1.0606(2) 0.0837(10) Uani 1 1 d . . .
C9 C -0.2216(4) 0.6215(5) 0.5253(2) 0.0564(8) Uani 1 1 d . . .
H9 H -0.2684 0.5170 0.4855 0.068 Uiso 1 1 calc R . .
C1 C 0.8149(4) 0.4830(5) 0.9838(2) 0.0518(7) Uani 1 1 d . . .
H1A H 0.7191 0.4507 1.0110 0.078 Uiso 1 1 calc R . .
H1B H 0.8727 0.5958 1.0166 0.078 Uiso 1 1 calc R . .
H1C H 0.8934 0.3749 0.9923 0.078 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 1.9141(18) . ?
Cu1 N2 1.9396(19) . ?
Cu1 N3 1.962(3) . ?
Cu1 N1 2.041(2) . ?
Cu1 N5 2.471(3) 2_647 ?
O1 C15 1.297(3) . ?
N1 C2 1.479(3) . ?
N1 C1 1.479(3) . ?
N1 C3 1.484(3) . ?
N2 C5 1.294(3) . ?
N2 C4 1.464(3) . ?
C10 C11 1.360(5) . ?
C10 C9 1.380(5) . ?
C10 H10 0.9300 . ?
N4 N5 1.139(3) . ?
N4 N3 1.172(3) . ?
C3 C4 1.524(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.424(3) . ?
C5 H5 0.9300 . ?
C6 C15 1.405(4) . ?
C6 C7 1.467(3) . ?
C15 C14 1.430(3) . ?
C14 C13 1.343(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.425(4) . ?
C13 H13 0.9300 . ?
C12 C7 1.404(4) . ?
C12 C11 1.421(4) . ?
C11 H11 0.9300 . ?
C8 C9 1.375(4) . ?
C8 C7 1.420(4) . ?
C8 H8 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
N5 Cu1 2.471(3) 2_657 ?
C9 H9 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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 N2 91.03(8) . . ?
O1 Cu1 N3 91.59(9) . . ?
N2 Cu1 N3 170.50(10) . . ?
O1 Cu1 N1 172.37(9) . . ?
N2 Cu1 N1 85.07(8) . . ?
N3 Cu1 N1 91.24(9) . . ?
O1 Cu1 N5 92.97(9) . 2_647 ?
N2 Cu1 N5 87.45(11) . 2_647 ?
N3 Cu1 N5 101.52(12) . 2_647 ?
N1 Cu1 N5 93.40(9) . 2_647 ?
C15 O1 Cu1 125.71(15) . . ?
C2 N1 C1 109.1(2) . . ?
C2 N1 C3 111.0(2) . . ?
C1 N1 C3 109.2(2) . . ?
C2 N1 Cu1 108.49(17) . . ?
C1 N1 Cu1 114.14(17) . . ?
C3 N1 Cu1 104.89(14) . . ?
C5 N2 C4 119.8(2) . . ?
C5 N2 Cu1 125.33(17) . . ?
C4 N2 Cu1 113.96(16) . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
N5 N4 N3 176.0(3) . . ?
N1 C3 C4 109.8(2) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N2 C4 C3 106.7(2) . . ?
N2 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
N2 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N2 C5 C6 125.4(2) . . ?
N2 C5 H5 117.3 . . ?
C6 C5 H5 117.3 . . ?
C15 C6 C5 121.7(2) . . ?
C15 C6 C7 119.4(2) . . ?
C5 C6 C7 119.0(2) . . ?
O1 C15 C6 125.1(2) . . ?
O1 C15 C14 115.9(2) . . ?
C6 C15 C14 119.0(2) . . ?
C13 C14 C15 121.6(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C7 C12 C11 120.1(3) . . ?
C7 C12 C13 119.6(2) . . ?
C11 C12 C13 120.4(3) . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C12 C7 C8 117.6(2) . . ?
C12 C7 C6 118.9(2) . . ?
C8 C7 C6 123.4(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N4 N3 Cu1 122.1(2) . . ?
N4 N5 Cu1 161.0(2) . 2_657 ?
C8 C9 C10 121.3(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.71
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_M-6
_database_code_depnum_ccdc_archive 'CCDC 1046264'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   7.9979(2)
_cell_length_b                   6.8447(2)
_cell_length_c                   14.0483(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.673(2)
_cell_angle_gamma                90.00
_cell_volume                     747.25(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      1.542
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.470
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.765
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11461
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.84
_reflns_number_total             2875
_reflns_number_gt                2543
_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)+(0.0498P)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    riding
_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   0.120(5)
_refine_ls_number_reflns         2875
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.42281(4) 0.24941(7) 0.15246(3) 0.03655(14) Uani 1 1 d . . .
N2 N 0.5346(4) 0.0898(4) 0.2637(2) 0.0341(7) Uani 1 1 d . . .
N1 N 0.2484(4) 0.0285(4) 0.1220(2) 0.0365(7) Uani 1 1 d . . .
O1 O 0.5791(3) 0.4600(4) 0.1973(2) 0.0473(7) Uani 1 1 d . . .
N3 N 0.2789(4) 0.4130(6) 0.0514(3) 0.0536(9) Uani 1 1 d . . .
N4 N 0.3364(4) 0.5025(5) -0.0049(2) 0.0428(8) Uani 1 1 d . . .
N5 N 0.3833(5) 0.5945(7) -0.0608(3) 0.0837(14) Uani 1 1 d . . .
C3 C 0.3419(5) -0.1456(5) 0.1720(3) 0.0440(9) Uani 1 1 d . . .
H3A H 0.4204 -0.1944 0.1344 0.053 Uiso 1 1 calc R . .
H3B H 0.2604 -0.2483 0.1760 0.053 Uiso 1 1 calc R . .
C4 C 0.4421(5) -0.0901(6) 0.2745(3) 0.0434(9) Uani 1 1 d . . .
H4A H 0.3644 -0.0688 0.3171 0.052 Uiso 1 1 calc R . .
H4B H 0.5224 -0.1929 0.3023 0.052 Uiso 1 1 calc R . .
C5 C 0.6903(5) 0.1162(6) 0.3161(3) 0.0390(8) Uani 1 1 d . . .
H5 H 0.7367 0.0193 0.3610 0.047 Uiso 1 1 calc R . .
C6 C 0.7954(4) 0.2810(6) 0.3104(2) 0.0351(9) Uani 1 1 d . . .
C7 C 0.9760(4) 0.2788(7) 0.3671(2) 0.0376(9) Uani 1 1 d . . .
C8 C 1.0487(5) 0.1205(7) 0.4275(3) 0.0482(10) Uani 1 1 d . . .
H8 H 0.9804 0.0145 0.4353 0.058 Uiso 1 1 calc R . .
C9 C 1.2219(5) 0.1228(8) 0.4752(3) 0.0582(11) Uani 1 1 d . . .
H9 H 1.2687 0.0187 0.5152 0.070 Uiso 1 1 calc R . .
C10 C 1.3254(5) 0.2789(10) 0.4636(3) 0.0640(14) Uani 1 1 d . . .
H10 H 1.4421 0.2764 0.4939 0.077 Uiso 1 1 calc R . .
C11 C 1.2582(5) 0.4355(8) 0.4083(3) 0.0596(12) Uani 1 1 d . . .
H11 H 1.3285 0.5406 0.4022 0.071 Uiso 1 1 calc R . .
C12 C 1.0810(4) 0.4396(7) 0.3598(3) 0.0450(10) Uani 1 1 d . . .
C13 C 1.0105(5) 0.6041(6) 0.3025(3) 0.0518(10) Uani 1 1 d . . .
H13 H 1.0795 0.7126 0.3004 0.062 Uiso 1 1 calc R . .
C14 C 0.8456(5) 0.6052(6) 0.2515(3) 0.0489(10) Uani 1 1 d . . .
H14 H 0.8030 0.7148 0.2145 0.059 Uiso 1 1 calc R . .
C15 C 0.7345(5) 0.4435(5) 0.2524(3) 0.0377(8) Uani 1 1 d . . .
C2 C 0.1863(6) -0.0144(7) 0.0169(3) 0.0535(11) Uani 1 1 d . . .
H2A H 0.2822 -0.0472 -0.0102 0.080 Uiso 1 1 calc R . .
H2B H 0.1288 0.0984 -0.0160 0.080 Uiso 1 1 calc R . .
H2C H 0.1075 -0.1223 0.0085 0.080 Uiso 1 1 calc R . .
C1 C 0.0994(5) 0.0786(7) 0.1634(3) 0.0512(11) Uani 1 1 d . . .
H1A H 0.1392 0.1068 0.2320 0.077 Uiso 1 1 calc R . .
H1B H 0.0209 -0.0296 0.1548 0.077 Uiso 1 1 calc R . .
H1C H 0.0417 0.1912 0.1303 0.077 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 1.915(3) . ?
Cu1 N2 1.943(3) . ?
Cu1 N3 1.955(4) . ?
Cu1 N1 2.033(3) . ?
Cu1 N5 2.477(4) 2_645 ?
N2 C5 1.301(4) . ?
N2 C4 1.462(4) . ?
N1 C2 1.472(5) . ?
N1 C1 1.484(5) . ?
N1 C3 1.491(5) . ?
O1 C15 1.304(4) . ?
N3 N4 1.176(5) . ?
N4 N5 1.137(5) . ?
N5 Cu1 2.477(4) 2_655 ?
C3 C4 1.522(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.420(5) . ?
C5 H5 0.9300 . ?
C6 C15 1.396(5) . ?
C6 C7 1.476(5) . ?
C7 C12 1.402(6) . ?
C7 C8 1.413(6) . ?
C8 C9 1.389(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.358(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.420(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.421(6) . ?
C13 C14 1.344(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.421(5) . ?
C14 H14 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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 N2 91.04(12) . . ?
O1 Cu1 N3 91.96(14) . . ?
N2 Cu1 N3 170.49(14) . . ?
O1 Cu1 N1 172.47(13) . . ?
N2 Cu1 N1 85.01(12) . . ?
N3 Cu1 N1 90.95(14) . . ?
O1 Cu1 N5 93.05(13) . 2_645 ?
N2 Cu1 N5 87.26(15) . 2_645 ?
N3 Cu1 N5 101.59(17) . 2_645 ?
N1 Cu1 N5 93.17(13) . 2_645 ?
C5 N2 C4 119.9(3) . . ?
C5 N2 Cu1 125.0(3) . . ?
C4 N2 Cu1 114.2(2) . . ?
C2 N1 C1 109.1(3) . . ?
C2 N1 C3 109.0(3) . . ?
C1 N1 C3 111.1(3) . . ?
C2 N1 Cu1 114.3(2) . . ?
C1 N1 Cu1 108.7(2) . . ?
C3 N1 Cu1 104.6(2) . . ?
C15 O1 Cu1 125.9(2) . . ?
N4 N3 Cu1 122.0(3) . . ?
N5 N4 N3 176.1(4) . . ?
N4 N5 Cu1 161.0(3) . 2_655 ?
N1 C3 C4 109.9(3) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N2 C4 C3 106.1(3) . . ?
N2 C4 H4A 110.5 . . ?
C3 C4 H4A 110.5 . . ?
N2 C4 H4B 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
N2 C5 C6 125.4(3) . . ?
N2 C5 H5 117.3 . . ?
C6 C5 H5 117.3 . . ?
C15 C6 C5 122.4(3) . . ?
C15 C6 C7 119.0(4) . . ?
C5 C6 C7 118.6(4) . . ?
C12 C7 C8 118.5(3) . . ?
C12 C7 C6 118.6(4) . . ?
C8 C7 C6 122.9(4) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.5(5) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 119.7(4) . . ?
C7 C12 C13 119.9(3) . . ?
C11 C12 C13 120.3(4) . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.8(4) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
O1 C15 C6 124.5(3) . . ?
O1 C15 C14 115.9(3) . . ?
C6 C15 C14 119.6(3) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.84
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_P-2
_database_code_depnum_ccdc_archive 'CCDC 1046265'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.0004(2)
_cell_length_b                   6.8446(2)
_cell_length_c                   14.0490(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.671(2)
_cell_angle_gamma                90.00
_cell_volume                     747.52(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6184
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.70
_reflns_number_total             2529
_reflns_number_gt                2321
_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)+(0.0282P)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    riding
_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   0.024(13)
_refine_ls_number_reflns         2529
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0589
_refine_ls_wR_factor_gt          0.0574
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.42284(4) 0.23969(6) 0.15237(2) 0.03601(10) Uani 1 1 d . . .
O1 O 0.5784(3) 0.0292(3) 0.19738(16) 0.0461(5) Uani 1 1 d . . .
N2 N 0.5343(3) 0.3984(3) 0.26367(16) 0.0339(5) Uani 1 1 d . . .
C5 C 0.6892(4) 0.3735(4) 0.3162(2) 0.0372(6) Uani 1 1 d . . .
H5 H 0.7345 0.4708 0.3611 0.045 Uiso 1 1 calc R . .
C12 C 1.0813(4) 0.0499(5) 0.3602(2) 0.0434(8) Uani 1 1 d . . .
N3 N 0.2783(3) 0.0753(4) 0.0514(2) 0.0545(7) Uani 1 1 d . . .
N4 N 0.3368(3) -0.0142(4) -0.0048(2) 0.0427(6) Uani 1 1 d . . .
C6 C 0.7960(3) 0.2091(5) 0.31082(18) 0.0351(7) Uani 1 1 d . . .
C15 C 0.7327(4) 0.0457(4) 0.2519(2) 0.0369(7) Uani 1 1 d . . .
C14 C 0.8445(4) -0.1175(5) 0.2512(2) 0.0465(8) Uani 1 1 d . . .
H14 H 0.8022 -0.2277 0.2147 0.056 Uiso 1 1 calc R . .
C13 C 1.0101(4) -0.1144(5) 0.3026(2) 0.0506(8) Uani 1 1 d . . .
H13 H 1.0795 -0.2225 0.3002 0.061 Uiso 1 1 calc R . .
C7 C 0.9755(3) 0.2093(5) 0.36729(18) 0.0362(7) Uani 1 1 d . . .
C8 C 1.0503(4) 0.3677(5) 0.4279(2) 0.0479(8) Uani 1 1 d . . .
H8 H 0.9826 0.4740 0.4359 0.057 Uiso 1 1 calc R . .
C9 C 1.2215(4) 0.3655(6) 0.4749(2) 0.0562(9) Uani 1 1 d . . .
H9 H 1.2680 0.4703 0.5145 0.067 Uiso 1 1 calc R . .
C10 C 1.3262(4) 0.2099(7) 0.4642(2) 0.0636(11) Uani 1 1 d . . .
H10 H 1.4427 0.2122 0.4949 0.076 Uiso 1 1 calc R . .
C11 C 1.2576(4) 0.0531(6) 0.4084(2) 0.0574(10) Uani 1 1 d . . .
H11 H 1.3274 -0.0525 0.4021 0.069 Uiso 1 1 calc R . .
C4 C 0.4422(4) 0.5784(4) 0.2744(2) 0.0405(7) Uani 1 1 d . . .
H4A H 0.5228 0.6810 0.3019 0.049 Uiso 1 1 calc R . .
H4B H 0.3654 0.5573 0.3174 0.049 Uiso 1 1 calc R . .
C3 C 0.3401(4) 0.6353(4) 0.1721(2) 0.0408(7) Uani 1 1 d . . .
H3A H 0.2580 0.7369 0.1769 0.049 Uiso 1 1 calc R . .
H3B H 0.4174 0.6858 0.1342 0.049 Uiso 1 1 calc R . .
N1 N 0.2477(3) 0.4612(3) 0.12228(17) 0.0340(6) Uani 1 1 d . . .
C2 C 0.1004(4) 0.4101(5) 0.1631(2) 0.0501(8) Uani 1 1 d . . .
H2A H 0.1400 0.3832 0.2318 0.075 Uiso 1 1 calc R . .
H2B H 0.0441 0.2965 0.1303 0.075 Uiso 1 1 calc R . .
H2C H 0.0207 0.5173 0.1538 0.075 Uiso 1 1 calc R . .
C1 C 0.1850(4) 0.5034(5) 0.0162(2) 0.0505(8) Uani 1 1 d . . .
H1A H 0.2809 0.5346 -0.0112 0.076 Uiso 1 1 calc R . .
H1B H 0.1071 0.6122 0.0075 0.076 Uiso 1 1 calc R . .
H1C H 0.1264 0.3908 -0.0164 0.076 Uiso 1 1 calc R . .
N5 N 0.3839(4) -0.1070(6) -0.0606(2) 0.0838(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.911(2) . ?
Cu1 N2 1.939(2) . ?
Cu1 N3 1.960(3) . ?
Cu1 N1 2.039(2) . ?
Cu1 N5 2.469(3) 2_655 ?
O1 C15 1.295(3) . ?
N2 C5 1.295(3) . ?
N2 C4 1.462(3) . ?
C5 C6 1.425(4) . ?
C5 H5 0.9300 . ?
C12 C7 1.399(4) . ?
C12 C11 1.413(4) . ?
C12 C13 1.424(5) . ?
N3 N4 1.180(4) . ?
N4 N5 1.140(4) . ?
C6 C15 1.413(4) . ?
C6 C7 1.467(3) . ?
C15 C14 1.432(4) . ?
C14 C13 1.351(4) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C7 C8 1.421(4) . ?
C8 C9 1.372(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C4 C3 1.527(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 N1 1.487(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N1 C2 1.470(4) . ?
N1 C1 1.485(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N5 Cu1 2.469(3) 2_645 ?

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 N2 90.92(9) . . ?
O1 Cu1 N3 91.91(10) . . ?
N2 Cu1 N3 170.23(12) . . ?
O1 Cu1 N1 172.15(10) . . ?
N2 Cu1 N1 85.03(9) . . ?
N3 Cu1 N1 91.02(10) . . ?
O1 Cu1 N5 93.09(10) . 2_655 ?
N2 Cu1 N5 87.57(12) . 2_655 ?
N3 Cu1 N5 101.61(13) . 2_655 ?
N1 Cu1 N5 93.45(10) . 2_655 ?
C15 O1 Cu1 125.82(18) . . ?
C5 N2 C4 119.3(2) . . ?
C5 N2 Cu1 125.6(2) . . ?
C4 N2 Cu1 114.08(17) . . ?
N2 C5 C6 125.3(3) . . ?
N2 C5 H5 117.3 . . ?
C6 C5 H5 117.3 . . ?
C7 C12 C11 120.4(3) . . ?
C7 C12 C13 119.3(3) . . ?
C11 C12 C13 120.3(3) . . ?
N4 N3 Cu1 121.5(2) . . ?
N5 N4 N3 175.7(3) . . ?
C15 C6 C5 121.3(2) . . ?
C15 C6 C7 119.2(3) . . ?
C5 C6 C7 119.5(3) . . ?
O1 C15 C6 125.1(3) . . ?
O1 C15 C14 116.0(3) . . ?
C6 C15 C14 118.9(3) . . ?
C13 C14 C15 121.3(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C13 C12 121.7(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C12 C7 C8 117.5(3) . . ?
C12 C7 C6 119.5(3) . . ?
C8 C7 C6 123.0(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
N2 C4 C3 106.8(2) . . ?
N2 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
N2 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N1 C3 C4 109.5(2) . . ?
N1 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C2 N1 C1 109.0(2) . . ?
C2 N1 C3 111.2(2) . . ?
C1 N1 C3 109.2(2) . . ?
C2 N1 Cu1 108.50(19) . . ?
C1 N1 Cu1 113.9(2) . . ?
C3 N1 Cu1 104.94(15) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N4 N5 Cu1 161.0(3) . 2_645 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.70
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_P-3
_database_code_depnum_ccdc_archive 'CCDC 1046266'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.0008(4)
_cell_length_b                   6.8493(3)
_cell_length_c                   14.0439(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.685(4)
_cell_angle_gamma                90.00
_cell_volume                     747.76(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10823
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.84
_reflns_number_total             2839
_reflns_number_gt                2489
_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)+(0.0577P)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    riding
_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   -0.01(2)
_refine_ls_number_reflns         2839
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.42291(5) 0.24553(9) 0.15233(3) 0.03586(16) Uani 1 1 d . . .
O1 O 0.5787(4) 0.0336(5) 0.1972(2) 0.0466(8) Uani 1 1 d . . .
N2 N 0.5346(4) 0.4032(5) 0.2637(2) 0.0348(8) Uani 1 1 d . . .
N1 N 0.2477(4) 0.4671(6) 0.1224(2) 0.0360(8) Uani 1 1 d . . .
C2 C 0.1004(6) 0.4151(8) 0.1636(4) 0.0498(12) Uani 1 1 d . . .
H2A H 0.0443 0.3016 0.1306 0.075 Uiso 1 1 calc R . .
H2B H 0.0206 0.5220 0.1546 0.075 Uiso 1 1 calc R . .
H2C H 0.1405 0.3879 0.2322 0.075 Uiso 1 1 calc R . .
C14 C 0.8454(6) -0.1100(8) 0.2510(3) 0.0474(11) Uani 1 1 d . . .
H14 H 0.8035 -0.2198 0.2141 0.057 Uiso 1 1 calc R . .
N4 N 0.3370(5) -0.0078(6) -0.0050(3) 0.0414(9) Uani 1 1 d . . .
C4 C 0.4426(5) 0.5850(7) 0.2745(3) 0.0401(9) Uani 1 1 d . . .
H4A H 0.5236 0.6877 0.3013 0.048 Uiso 1 1 calc R . .
H4B H 0.3665 0.5649 0.3181 0.048 Uiso 1 1 calc R . .
C3 C 0.3392(5) 0.6404(6) 0.1721(3) 0.0411(10) Uani 1 1 d . . .
H3A H 0.2566 0.7414 0.1770 0.049 Uiso 1 1 calc R . .
H3B H 0.4159 0.6916 0.1341 0.049 Uiso 1 1 calc R . .
C1 C 0.1856(6) 0.5082(8) 0.0163(3) 0.0495(12) Uani 1 1 d . . .
H1A H 0.1275 0.3952 -0.0161 0.074 Uiso 1 1 calc R . .
H1B H 0.2816 0.5393 -0.0109 0.074 Uiso 1 1 calc R . .
H1C H 0.1074 0.6166 0.0073 0.074 Uiso 1 1 calc R . .
C5 C 0.6899(5) 0.3779(7) 0.3156(3) 0.0377(9) Uani 1 1 d . . .
H5 H 0.7360 0.4758 0.3600 0.045 Uiso 1 1 calc R . .
C6 C 0.7960(5) 0.2140(7) 0.3107(3) 0.0324(11) Uani 1 1 d . . .
C15 C 0.7338(5) 0.0513(6) 0.2521(3) 0.0373(10) Uani 1 1 d . . .
C13 C 1.0105(6) -0.1071(8) 0.3024(4) 0.0513(12) Uani 1 1 d . . .
H13 H 1.0801 -0.2147 0.2995 0.062 Uiso 1 1 calc R . .
C12 C 1.0807(5) 0.0541(8) 0.3603(3) 0.0438(12) Uani 1 1 d . . .
C11 C 1.2572(6) 0.0594(9) 0.4092(4) 0.0591(15) Uani 1 1 d . . .
H11 H 1.3271 -0.0466 0.4039 0.071 Uiso 1 1 calc R . .
C10 C 1.3267(6) 0.2172(12) 0.4639(3) 0.0671(19) Uani 1 1 d . . .
H10 H 1.4437 0.2213 0.4932 0.081 Uiso 1 1 calc R . .
C9 C 1.2219(6) 0.3692(9) 0.4750(3) 0.0574(13) Uani 1 1 d . . .
H9 H 1.2680 0.4724 0.5159 0.069 Uiso 1 1 calc R . .
C8 C 1.0499(6) 0.3740(8) 0.4274(3) 0.0477(11) Uani 1 1 d . . .
H8 H 0.9828 0.4813 0.4347 0.057 Uiso 1 1 calc R . .
C7 C 0.9755(5) 0.2152(7) 0.3673(3) 0.0355(10) Uani 1 1 d . . .
N5 N 0.3849(6) -0.0990(10) -0.0604(4) 0.0861(18) Uani 1 1 d . . .
N3 N 0.2788(5) 0.0795(7) 0.0516(3) 0.0523(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.920(3) . ?
Cu1 N2 1.936(3) . ?
Cu1 N3 1.963(4) . ?
Cu1 N1 2.041(4) . ?
Cu1 N5 2.471(5) 2_655 ?
O1 C15 1.302(5) . ?
N2 C5 1.295(5) . ?
N2 C4 1.473(5) . ?
N1 C2 1.474(5) . ?
N1 C3 1.480(5) . ?
N1 C1 1.481(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C14 C13 1.347(6) . ?
C14 C15 1.423(6) . ?
C14 H14 0.9300 . ?
N4 N5 1.133(6) . ?
N4 N3 1.175(5) . ?
C4 C3 1.527(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C5 C6 1.419(6) . ?
C5 H5 0.9300 . ?
C6 C15 1.405(6) . ?
C6 C7 1.468(5) . ?
C13 C12 1.407(7) . ?
C13 H13 0.9300 . ?
C12 C7 1.405(7) . ?
C12 C11 1.417(6) . ?
C11 C10 1.366(9) . ?
C11 H11 0.9300 . ?
C10 C9 1.368(9) . ?
C10 H10 0.9300 . ?
C9 C8 1.381(6) . ?
C9 H9 0.9300 . ?
C8 C7 1.419(6) . ?
C8 H8 0.9300 . ?
N5 Cu1 2.471(5) 2_645 ?

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 N2 90.94(13) . . ?
O1 Cu1 N3 91.36(16) . . ?
N2 Cu1 N3 170.22(16) . . ?
O1 Cu1 N1 172.17(14) . . ?
N2 Cu1 N1 85.15(13) . . ?
N3 Cu1 N1 91.40(16) . . ?
O1 Cu1 N5 93.51(15) . 2_655 ?
N2 Cu1 N5 87.50(18) . 2_655 ?
N3 Cu1 N5 101.84(19) . 2_655 ?
N1 Cu1 N5 93.08(16) . 2_655 ?
C15 O1 Cu1 125.3(3) . . ?
C5 N2 C4 119.4(3) . . ?
C5 N2 Cu1 125.3(3) . . ?
C4 N2 Cu1 114.1(2) . . ?
C2 N1 C3 111.1(3) . . ?
C2 N1 C1 109.4(3) . . ?
C3 N1 C1 109.5(4) . . ?
C2 N1 Cu1 108.3(3) . . ?
C3 N1 Cu1 105.1(2) . . ?
C1 N1 Cu1 113.5(3) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C13 C14 C15 121.4(5) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
N5 N4 N3 176.0(5) . . ?
N2 C4 C3 106.6(3) . . ?
N2 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
N2 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N1 C3 C4 110.1(3) . . ?
N1 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C5 C6 125.7(4) . . ?
N2 C5 H5 117.1 . . ?
C6 C5 H5 117.1 . . ?
C15 C6 C5 121.5(3) . . ?
C15 C6 C7 119.2(4) . . ?
C5 C6 C7 119.3(4) . . ?
O1 C15 C6 125.2(4) . . ?
O1 C15 C14 115.8(4) . . ?
C6 C15 C14 119.1(4) . . ?
C14 C13 C12 121.9(4) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C7 C12 C13 119.5(4) . . ?
C7 C12 C11 119.4(5) . . ?
C13 C12 C11 121.0(5) . . ?
C10 C11 C12 121.2(5) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C9 C8 122.0(5) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C8 C7 120.0(5) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C12 C7 C8 118.0(4) . . ?
C12 C7 C6 118.9(4) . . ?
C8 C7 C6 123.1(4) . . ?
N4 N5 Cu1 161.8(4) . 2_645 ?
N4 N3 Cu1 121.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.84
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_P-4
_database_code_depnum_ccdc_archive 'CCDC 1046267'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.0013(2)
_cell_length_b                   6.8445(2)
_cell_length_c                   14.0404(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.717(2)
_cell_angle_gamma                90.00
_cell_volume                     746.99(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11314
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.70
_reflns_number_total             2842
_reflns_number_gt                2634
_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)+(0.0335P)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    riding
_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   0.013(12)
_refine_ls_number_reflns         2842
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.42280(3) 0.24166(5) 0.152377(19) 0.03561(10) Uani 1 1 d . . .
O1 O 0.5786(2) 0.0305(3) 0.19729(15) 0.0456(5) Uani 1 1 d . . .
N2 N 0.5349(3) 0.4004(3) 0.26377(15) 0.0341(5) Uani 1 1 d . . .
N1 N 0.2477(3) 0.4633(3) 0.12208(16) 0.0340(5) Uani 1 1 d . . .
C9 C 1.2215(4) 0.3662(6) 0.4748(2) 0.0564(8) Uani 1 1 d . . .
H9 H 1.2679 0.4703 0.5150 0.068 Uiso 1 1 calc R . .
N3 N 0.2781(3) 0.0761(4) 0.0512(2) 0.0525(6) Uani 1 1 d . . .
N4 N 0.3367(3) -0.0128(4) -0.00492(18) 0.0413(5) Uani 1 1 d . . .
C4 C 0.4419(3) 0.5807(4) 0.27430(19) 0.0409(6) Uani 1 1 d . . .
H4A H 0.5222 0.6837 0.3017 0.049 Uiso 1 1 calc R . .
H4B H 0.3652 0.5594 0.3174 0.049 Uiso 1 1 calc R . .
C3 C 0.3395(3) 0.6369(4) 0.1719(2) 0.0396(6) Uani 1 1 d . . .
H3A H 0.2572 0.7383 0.1767 0.048 Uiso 1 1 calc R . .
H3B H 0.4167 0.6877 0.1341 0.048 Uiso 1 1 calc R . .
C1 C 0.0998(3) 0.4125(5) 0.1630(2) 0.0507(7) Uani 1 1 d . . .
H1A H 0.1394 0.3854 0.2317 0.076 Uiso 1 1 calc R . .
H1B H 0.0432 0.2992 0.1301 0.076 Uiso 1 1 calc R . .
H1C H 0.0204 0.5200 0.1538 0.076 Uiso 1 1 calc R . .
C2 C 0.1844(4) 0.5049(5) 0.0163(2) 0.0514(8) Uani 1 1 d . . .
H2A H 0.1260 0.3919 -0.0161 0.077 Uiso 1 1 calc R . .
H2B H 0.2799 0.5363 -0.0114 0.077 Uiso 1 1 calc R . .
H2C H 0.1061 0.6133 0.0076 0.077 Uiso 1 1 calc R . .
C5 C 0.6898(3) 0.3748(4) 0.31627(19) 0.0363(6) Uani 1 1 d . . .
H5 H 0.7354 0.4719 0.3613 0.044 Uiso 1 1 calc R . .
C6 C 0.7959(3) 0.2107(4) 0.31080(17) 0.0340(7) Uani 1 1 d . . .
C15 C 0.7333(3) 0.0478(4) 0.25199(19) 0.0374(6) Uani 1 1 d . . .
C14 C 0.8452(4) -0.1155(4) 0.2512(2) 0.0467(7) Uani 1 1 d . . .
H14 H 0.8028 -0.2254 0.2144 0.056 Uiso 1 1 calc R . .
C13 C 1.0103(4) -0.1133(5) 0.3025(2) 0.0508(7) Uani 1 1 d . . .
H13 H 1.0796 -0.2216 0.3004 0.061 Uiso 1 1 calc R . .
C12 C 1.0811(3) 0.0516(5) 0.3600(2) 0.0443(7) Uani 1 1 d . . .
C11 C 1.2577(4) 0.0555(6) 0.4087(2) 0.0573(9) Uani 1 1 d . . .
H11 H 1.3276 -0.0503 0.4029 0.069 Uiso 1 1 calc R . .
C10 C 1.3262(4) 0.2120(7) 0.4639(2) 0.0629(10) Uani 1 1 d . . .
H10 H 1.4430 0.2151 0.4941 0.076 Uiso 1 1 calc R . .
C8 C 1.0501(4) 0.3697(5) 0.4275(2) 0.0472(7) Uani 1 1 d . . .
H8 H 0.9827 0.4765 0.4353 0.057 Uiso 1 1 calc R . .
C7 C 0.9752(3) 0.2121(5) 0.36705(17) 0.0360(6) Uani 1 1 d . . .
N5 N 0.3839(4) -0.1048(6) -0.0606(2) 0.0842(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9152(18) . ?
Cu1 N2 1.940(2) . ?
Cu1 N3 1.965(3) . ?
Cu1 N1 2.041(2) . ?
Cu1 N5 2.470(3) 2_655 ?
O1 C15 1.298(3) . ?
N2 C5 1.295(3) . ?
N2 C4 1.466(3) . ?
N1 C1 1.474(3) . ?
N1 C2 1.479(3) . ?
N1 C3 1.482(3) . ?
C9 C8 1.375(4) . ?
C9 C10 1.378(5) . ?
C9 H9 0.9300 . ?
N3 N4 1.177(3) . ?
N4 N5 1.136(4) . ?
C4 C3 1.525(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C5 C6 1.421(4) . ?
C5 H5 0.9300 . ?
C6 C15 1.407(4) . ?
C6 C7 1.465(3) . ?
C15 C14 1.434(4) . ?
C14 C13 1.347(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.424(4) . ?
C13 H13 0.9300 . ?
C12 C7 1.405(4) . ?
C12 C11 1.417(4) . ?
C11 C10 1.359(5) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C8 C7 1.414(4) . ?
C8 H8 0.9300 . ?
N5 Cu1 2.470(3) 2_645 ?

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 N2 90.95(8) . . ?
O1 Cu1 N3 91.66(10) . . ?
N2 Cu1 N3 170.34(10) . . ?
O1 Cu1 N1 172.30(9) . . ?
N2 Cu1 N1 85.13(8) . . ?
N3 Cu1 N1 91.16(10) . . ?
O1 Cu1 N5 93.06(10) . 2_655 ?
N2 Cu1 N5 87.45(11) . 2_655 ?
N3 Cu1 N5 101.70(12) . 2_655 ?
N1 Cu1 N5 93.38(9) . 2_655 ?
C15 O1 Cu1 125.53(17) . . ?
C5 N2 C4 119.8(2) . . ?
C5 N2 Cu1 125.46(18) . . ?
C4 N2 Cu1 113.82(16) . . ?
C1 N1 C2 108.7(2) . . ?
C1 N1 C3 111.0(2) . . ?
C2 N1 C3 109.5(2) . . ?
C1 N1 Cu1 108.58(18) . . ?
C2 N1 Cu1 114.01(18) . . ?
C3 N1 Cu1 104.98(14) . . ?
C8 C9 C10 121.5(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
N4 N3 Cu1 121.4(2) . . ?
N5 N4 N3 175.7(3) . . ?
N2 C4 C3 106.8(2) . . ?
N2 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
N2 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N1 C3 C4 109.8(2) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C5 C6 125.4(2) . . ?
N2 C5 H5 117.3 . . ?
C6 C5 H5 117.3 . . ?
C15 C6 C5 121.6(2) . . ?
C15 C6 C7 119.3(3) . . ?
C5 C6 C7 119.1(3) . . ?
O1 C15 C6 125.2(2) . . ?
O1 C15 C14 115.7(2) . . ?
C6 C15 C14 119.1(2) . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C7 C12 C11 120.0(3) . . ?
C7 C12 C13 119.6(2) . . ?
C11 C12 C13 120.4(3) . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C12 C7 C8 117.5(2) . . ?
C12 C7 C6 119.1(3) . . ?
C8 C7 C6 123.4(3) . . ?
N4 N5 Cu1 161.1(2) . 2_645 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.70
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_P-5
_database_code_depnum_ccdc_archive 'CCDC 1046268'
_audit_update_record             
;
2015-01-29 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cu N5 O'
_chemical_formula_weight         346.89

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           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.0045(2)
_cell_length_b                   6.8435(2)
_cell_length_c                   14.0451(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.689(2)
_cell_angle_gamma                90.00
_cell_volume                     747.52(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    1.470
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11181
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         25.70
_reflns_number_total             2852
_reflns_number_gt                2626
_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)+(0.0363P)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   0.036(13)
_refine_ls_number_reflns         2831
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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 0.57718(3) 0.74495(5) 0.847624(19) 0.03565(10) Uani 1 1 d . . .
O1 O 0.4212(3) 0.5337(3) 0.80277(15) 0.0451(5) Uani 1 1 d . . .
N2 N 0.4653(3) 0.9031(3) 0.73650(15) 0.0342(5) Uani 1 1 d . . .
C1 C 0.9000(4) 0.9149(5) 0.8367(2) 0.0529(8) Uani 1 1 d . . .
H1A H 0.9565 0.8017 0.8698 0.079 Uiso 1 1 calc R . .
H1B H 0.9794 1.0222 0.8455 0.079 Uiso 1 1 calc R . .
H1C H 0.8603 0.8871 0.7680 0.079 Uiso 1 1 calc R . .
N5 N 0.6153(4) 0.3983(5) 1.0602(2) 0.0851(11) Uani 1 1 d . . .
N3 N 0.7212(3) 0.5791(4) 0.9482(2) 0.0526(6) Uani 1 1 d . . .
N4 N 0.6636(3) 0.4908(3) 1.00496(17) 0.0411(5) Uani 1 1 d . . .
C4 C 0.5581(4) 1.0838(4) 0.7257(2) 0.0417(6) Uani 1 1 d . . .
H4A H 0.4777 1.1866 0.6982 0.050 Uiso 1 1 calc R . .
H4B H 0.6347 1.0625 0.6825 0.050 Uiso 1 1 calc R . .
C3 C 0.6603(4) 1.1405(4) 0.8278(2) 0.0408(6) Uani 1 1 d . . .
H3A H 0.7426 1.2419 0.8229 0.049 Uiso 1 1 calc R . .
H3B H 0.5832 1.1914 0.8657 0.049 Uiso 1 1 calc R . .
N1 N 0.7524(3) 0.9664(3) 0.87766(16) 0.0350(5) Uani 1 1 d . . .
C2 C 0.8147(4) 1.0085(5) 0.9834(2) 0.0509(8) Uani 1 1 d . . .
H2A H 0.8732 0.8959 1.0161 0.076 Uiso 1 1 calc R . .
H2B H 0.7189 1.0397 1.0108 0.076 Uiso 1 1 calc R . .
H2C H 0.8926 1.1173 0.9921 0.076 Uiso 1 1 calc R . .
C5 C 0.3102(4) 0.8784(4) 0.68397(19) 0.0370(6) Uani 1 1 d . . .
H5 H 0.2646 0.9760 0.6393 0.044 Uiso 1 1 calc R . .
C6 C 0.2042(3) 0.7139(4) 0.68933(17) 0.0343(6) Uani 1 1 d . . .
C7 C 0.0247(3) 0.7151(4) 0.63294(17) 0.0359(6) Uani 1 1 d . . .
C12 C -0.0812(4) 0.5547(5) 0.6398(2) 0.0449(7) Uani 1 1 d . . .
C11 C -0.2573(4) 0.5585(5) 0.5913(2) 0.0577(9) Uani 1 1 d . . .
H11 H -0.3269 0.4524 0.5969 0.069 Uiso 1 1 calc R . .
C10 C -0.3266(4) 0.7166(7) 0.5360(2) 0.0653(10) Uani 1 1 d . . .
H10 H -0.4434 0.7201 0.5062 0.078 Uiso 1 1 calc R . .
C9 C -0.2218(4) 0.8701(5) 0.5250(2) 0.0561(8) Uani 1 1 d . . .
H9 H -0.2680 0.9742 0.4848 0.067 Uiso 1 1 calc R . .
C8 C -0.0499(4) 0.8734(5) 0.5723(2) 0.0478(7) Uani 1 1 d . . .
H8 H 0.0176 0.9800 0.5645 0.057 Uiso 1 1 calc R . .
C13 C -0.0100(4) 0.3896(4) 0.6975(2) 0.0525(8) Uani 1 1 d . . .
H13 H -0.0788 0.2810 0.6996 0.063 Uiso 1 1 calc R . .
C14 C 0.1548(4) 0.3883(4) 0.7487(2) 0.0464(7) Uani 1 1 d . . .
H14 H 0.1970 0.2785 0.7857 0.056 Uiso 1 1 calc R . .
C15 C 0.2666(4) 0.5501(4) 0.7480(2) 0.0379(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9167(19) . ?
Cu1 N2 1.936(2) . ?
Cu1 N3 1.960(3) . ?
Cu1 N1 2.040(2) . ?
Cu1 N5 2.468(3) 2_657 ?
O1 C15 1.298(3) . ?
N2 C5 1.296(3) . ?
N2 C4 1.469(3) . ?
C1 N1 1.475(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N5 N4 1.138(4) . ?
N5 Cu1 2.468(3) 2_647 ?
N3 N4 1.177(3) . ?
C4 C3 1.524(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 N1 1.486(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N1 C2 1.479(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C5 C6 1.422(4) . ?
C5 H5 0.9300 . ?
C6 C15 1.411(4) . ?
C6 C7 1.467(3) . ?
C7 C12 1.404(4) . ?
C7 C8 1.419(4) . ?
C12 C11 1.413(4) . ?
C12 C13 1.427(4) . ?
C11 C10 1.371(5) . ?
C11 H11 0.9300 . ?
C10 C9 1.375(5) . ?
C10 H10 0.9300 . ?
C9 C8 1.380(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C13 C14 1.345(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.425(4) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N2 90.89(8) . . ?
O1 Cu1 N3 91.51(10) . . ?
N2 Cu1 N3 170.31(11) . . ?
O1 Cu1 N1 172.24(9) . . ?
N2 Cu1 N1 85.16(9) . . ?
N3 Cu1 N1 91.32(10) . . ?
O1 Cu1 N5 93.11(10) . 2_657 ?
N2 Cu1 N5 87.59(11) . 2_657 ?
N3 Cu1 N5 101.64(13) . 2_657 ?
N1 Cu1 N5 93.41(10) . 2_657 ?
C15 O1 Cu1 125.82(16) . . ?
C5 N2 C4 119.4(2) . . ?
C5 N2 Cu1 125.73(18) . . ?
C4 N2 Cu1 113.92(17) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N4 N5 Cu1 161.7(3) . 2_647 ?
N4 N3 Cu1 121.8(2) . . ?
N5 N4 N3 176.2(3) . . ?
N2 C4 C3 106.8(2) . . ?
N2 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
N2 C4 H4B 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N1 C3 C4 109.6(2) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C1 N1 C2 109.1(2) . . ?
C1 N1 C3 111.2(2) . . ?
C2 N1 C3 109.2(2) . . ?
C1 N1 Cu1 108.47(18) . . ?
C2 N1 Cu1 113.86(18) . . ?
C3 N1 Cu1 104.98(15) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C5 C6 125.2(2) . . ?
N2 C5 H5 117.4 . . ?
C6 C5 H5 117.4 . . ?
C15 C6 C5 121.8(2) . . ?
C15 C6 C7 119.0(2) . . ?
C5 C6 C7 119.2(2) . . ?
C12 C7 C8 117.6(2) . . ?
C12 C7 C6 119.3(2) . . ?
C8 C7 C6 123.2(3) . . ?
C7 C12 C11 120.1(3) . . ?
C7 C12 C13 119.4(2) . . ?
C11 C12 C13 120.5(3) . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 121.9(3) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
O1 C15 C6 124.8(2) . . ?
O1 C15 C14 116.2(2) . . ?
C6 C15 C14 119.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.70
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.043
