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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_xb7306_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 Cl0 Cu N14 O2'
_chemical_formula_weight         371.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   7.1861(14)
_cell_length_b                   7.5759(14)
_cell_length_c                   7.6549(14)
_cell_angle_alpha                89.212(4)
_cell_angle_beta                 63.414(3)
_cell_angle_gamma                64.027(3)
_cell_volume                     326.31(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    333
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      21.99

_exptl_crystal_description       bulk
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             187
_exptl_absorpt_coefficient_mu    1.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_T_max  0.747
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1974
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0774
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         28.47
_reflns_number_total             1449
_reflns_number_gt                1088
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)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_number_reflns         1449
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1641
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 0.5000 0.5000 0.5000 0.0287(3) Uani 1 2 d S . .
O1 O 0.6219(7) 0.2916(6) 0.7366(6) 0.0402(9) Uani 1 1 d . . .
H4 H 0.7047 0.3156 0.7775 0.060 Uiso 1 1 d R . .
N1 N 0.1666(7) 0.5599(6) 0.6911(6) 0.0256(9) Uani 1 1 d . . .
N2 N 0.5009(7) 0.2713(6) 0.3764(6) 0.0270(9) Uani 1 1 d . . .
N5 N 0.3205(8) 0.0973(6) 0.3877(7) 0.0323(10) Uani 1 1 d . . .
N6 N -0.0964(7) 0.4472(6) 0.7846(6) 0.0290(9) Uani 1 1 d . . .
N3 N 0.6512(8) 0.1132(6) 0.2183(6) 0.0339(10) Uani 1 1 d . . .
N4 N 0.5424(8) 0.0098(7) 0.2265(7) 0.0350(10) Uani 1 1 d . . .
N7 N -0.1858(7) 0.6247(6) 0.9127(6) 0.0299(10) Uani 1 1 d . . .
C2 C 0.1144(8) 0.4171(7) 0.6537(7) 0.0246(10) Uani 1 1 d . . .
C1 C 0.3023(8) 0.2569(7) 0.4767(7) 0.0229(10) Uani 1 1 d . . .
C3 C -0.0275(8) 0.6873(7) 0.8548(7) 0.0279(10) Uani 1 1 d . . .
H2 H -0.0492 0.8034 0.9193 0.033 Uiso 1 1 calc R . .
H1 H -0.3134 0.6715 0.9950 0.033 Uiso 1 1 d R . .
H3 H 0.6759 0.1928 0.7069 0.033 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0241(5) 0.0270(5) 0.0290(5) -0.0037(3) -0.0049(4) -0.0158(4)
O1 0.036(2) 0.035(2) 0.050(2) 0.0000(18) -0.0183(19) -0.0208(17)
N1 0.0209(19) 0.023(2) 0.025(2) -0.0013(16) -0.0059(17) -0.0096(16)
N2 0.025(2) 0.024(2) 0.022(2) -0.0047(16) -0.0043(17) -0.0106(17)
N5 0.036(2) 0.027(2) 0.036(2) 0.0023(19) -0.015(2) -0.0190(19)
N6 0.028(2) 0.032(2) 0.026(2) 0.0022(18) -0.0098(18) -0.0176(19)
N3 0.032(2) 0.030(2) 0.027(2) -0.0060(18) -0.0048(19) -0.0150(19)
N4 0.034(2) 0.029(2) 0.035(2) -0.0031(19) -0.011(2) -0.016(2)
N7 0.023(2) 0.033(2) 0.022(2) 0.0001(17) -0.0036(17) -0.0104(18)
C2 0.024(2) 0.025(2) 0.027(2) 0.0047(19) -0.012(2) -0.0134(19)
C1 0.025(2) 0.025(2) 0.020(2) 0.0016(18) -0.0090(19) -0.015(2)
C3 0.026(2) 0.027(3) 0.027(2) 0.003(2) -0.012(2) -0.011(2)

_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 1.981(4) . ?
Cu1 N2 1.981(4) 2_666 ?
Cu1 N1 2.004(4) . ?
Cu1 N1 2.004(4) 2_666 ?
Cu1 O1 2.583(4) . ?
O1 H4 0.8649 . ?
O1 H3 0.6590 . ?
N1 C3 1.318(6) . ?
N1 C2 1.362(6) . ?
N2 C1 1.339(6) . ?
N2 N3 1.343(5) . ?
N5 C1 1.322(6) . ?
N5 N4 1.357(6) . ?
N6 C2 1.302(6) . ?
N6 N7 1.378(6) . ?
N3 N4 1.311(6) . ?
N7 C3 1.315(6) . ?
N7 H1 0.7535 . ?
C2 C1 1.450(6) . ?
C3 H2 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
N2 Cu1 N2 180.0(3) . 2_666 ?
N2 Cu1 N1 81.16(15) . . ?
N2 Cu1 N1 98.84(15) 2_666 . ?
N2 Cu1 N1 98.84(15) . 2_666 ?
N2 Cu1 N1 81.16(15) 2_666 2_666 ?
N1 Cu1 N1 180.000(1) . 2_666 ?
N2 Cu1 O1 90.33(14) . . ?
N2 Cu1 O1 89.67(14) 2_666 . ?
N1 Cu1 O1 86.94(14) . . ?
N1 Cu1 O1 93.06(14) 2_666 . ?
Cu1 O1 H4 118.4 . . ?
Cu1 O1 H3 116.8 . . ?
H4 O1 H3 105.3 . . ?
C3 N1 C2 103.9(4) . . ?
C3 N1 Cu1 142.5(3) . . ?
C2 N1 Cu1 113.5(3) . . ?
C1 N2 N3 106.4(4) . . ?
C1 N2 Cu1 115.1(3) . . ?
N3 N2 Cu1 138.4(3) . . ?
C1 N5 N4 104.1(4) . . ?
C2 N6 N7 102.1(4) . . ?
N4 N3 N2 107.3(4) . . ?
N3 N4 N5 110.9(4) . . ?
C3 N7 N6 110.5(4) . . ?
C3 N7 H1 132.1 . . ?
N6 N7 H1 117.3 . . ?
N6 C2 N1 114.1(4) . . ?
N6 C2 C1 130.9(4) . . ?
N1 C2 C1 115.0(4) . . ?
N5 C1 N2 111.2(4) . . ?
N5 C1 C2 133.7(4) . . ?
N2 C1 C2 115.1(4) . . ?
N7 C3 N1 109.4(4) . . ?
N7 C3 H2 125.3 . . ?
N1 C3 H2 125.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Cu1 N1 C3 178.8(6) . . . . ?
N2 Cu1 N1 C3 -1.2(6) 2_666 . . . ?
N1 Cu1 N1 C3 40(100) 2_666 . . . ?
O1 Cu1 N1 C3 88.0(6) . . . . ?
N2 Cu1 N1 C2 4.3(3) . . . . ?
N2 Cu1 N1 C2 -175.7(3) 2_666 . . . ?
N1 Cu1 N1 C2 -135(100) 2_666 . . . ?
O1 Cu1 N1 C2 -86.6(3) . . . . ?
N2 Cu1 N2 C1 9(100) 2_666 . . . ?
N1 Cu1 N2 C1 -4.0(3) . . . . ?
N1 Cu1 N2 C1 176.0(3) 2_666 . . . ?
O1 Cu1 N2 C1 82.8(3) . . . . ?
N2 Cu1 N2 N3 -168(100) 2_666 . . . ?
N1 Cu1 N2 N3 179.5(5) . . . . ?
N1 Cu1 N2 N3 -0.5(5) 2_666 . . . ?
O1 Cu1 N2 N3 -93.7(5) . . . . ?
C1 N2 N3 N4 0.1(5) . . . . ?
Cu1 N2 N3 N4 176.8(4) . . . . ?
N2 N3 N4 N5 0.3(6) . . . . ?
C1 N5 N4 N3 -0.6(6) . . . . ?
C2 N6 N7 C3 -0.8(5) . . . . ?
N7 N6 C2 N1 1.1(5) . . . . ?
N7 N6 C2 C1 -179.5(5) . . . . ?
C3 N1 C2 N6 -0.9(6) . . . . ?
Cu1 N1 C2 N6 175.7(3) . . . . ?
C3 N1 C2 C1 179.6(4) . . . . ?
Cu1 N1 C2 C1 -3.8(5) . . . . ?
N4 N5 C1 N2 0.6(5) . . . . ?
N4 N5 C1 C2 179.2(5) . . . . ?
N3 N2 C1 N5 -0.5(6) . . . . ?
Cu1 N2 C1 N5 -178.1(3) . . . . ?
N3 N2 C1 C2 -179.3(4) . . . . ?
Cu1 N2 C1 C2 3.1(5) . . . . ?
N6 C2 C1 N5 2.6(9) . . . . ?
N1 C2 C1 N5 -177.9(5) . . . . ?
N6 C2 C1 N2 -178.9(5) . . . . ?
N1 C2 C1 N2 0.5(6) . . . . ?
N6 N7 C3 N1 0.3(6) . . . . ?
C2 N1 C3 N7 0.3(5) . . . . ?
Cu1 N1 C3 N7 -174.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H3 N4 0.66 2.54 2.955(6) 123.6 2_656
O1 H3 N5 0.66 2.31 2.901(6) 150.5 2_656
N7 H1 N4 0.75 2.63 3.016(6) 113.6 1_466
N7 H1 O1 0.75 2.15 2.865(5) 159.4 2_567
O1 H4 N6 0.86 2.09 2.897(5) 155.4 1_655

_diffrn_measured_fraction_theta_max 0.878
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.115
_database_code_depnum_ccdc_archive 'CCDC 1000293'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_xb7515

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H Cu N7 O'
_chemical_formula_weight         214.65

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   7.404(3)
_cell_length_b                   9.672(3)
_cell_length_c                   9.341(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.020(4)
_cell_angle_gamma                90.00
_cell_volume                     615.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    683
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      26.16

_exptl_crystal_description       bulk
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    3.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.436
_exptl_absorpt_correction_T_max  0.514
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3338
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0749
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         26.97
_reflns_number_total             1313
_reflns_number_gt                1001
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0986P)²+14.9244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1313
_refine_ls_number_parameters     109
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0837
_refine_ls_wR_factor_ref         0.2321
_refine_ls_wR_factor_gt          0.2197
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N4 N -0.2227(9) 0.9756(7) 0.3536(7) 0.0189(15) Uani 1 1 d U . .
N3 N 0.1917(9) 0.5972(7) 0.1456(8) 0.0175(14) Uani 1 1 d U . .
N5 N 0.0060(8) 0.6483(6) 0.1077(7) 0.0123(13) Uani 1 1 d U . .
C1 C 0.3111(11) 0.6711(8) 0.2619(9) 0.0161(16) Uani 1 1 d U . .
H1 H 0.4462 0.6582 0.3075 0.019 Uiso 1 1 calc R . .
Cu1 Cu 0.23931(12) 0.91597(9) 0.47028(10) 0.0139(2) Uani 1 1 d U . .
N2 N -0.0598(9) 0.9174(7) 0.3520(8) 0.0173(14) Uani 1 1 d U . .
N1 N 0.2137(9) 0.7680(7) 0.3072(7) 0.0165(14) Uani 1 1 d U . .
N6 N -0.3749(11) 0.9246(9) 0.2359(10) 0.037(2) Uani 1 1 d U . .
N7 N -0.3154(11) 0.8337(9) 0.1545(10) 0.037(2) Uani 1 1 d U . .
C3 C -0.1229(11) 0.8345(9) 0.2296(10) 0.0223(18) Uani 1 1 d U . .
C2 C 0.0283(10) 0.7509(8) 0.2073(8) 0.0152(16) Uani 1 1 d U . .
O1 O 0.679(3) 0.611(2) 0.454(3) 0.194(7) Uani 1 1 d U . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N4 0.015(3) 0.022(3) 0.017(3) -0.005(2) 0.003(2) 0.003(3)
N3 0.016(3) 0.015(3) 0.021(3) -0.003(2) 0.006(2) 0.001(2)
N5 0.008(2) 0.014(3) 0.014(3) -0.005(2) 0.003(2) 0.000(2)
C1 0.010(3) 0.019(3) 0.016(3) -0.006(3) 0.002(2) -0.001(3)
Cu1 0.0102(4) 0.0153(4) 0.0145(4) -0.0023(3) 0.0031(3) 0.0006(4)
N2 0.009(2) 0.017(3) 0.027(3) -0.004(2) 0.009(2) 0.002(2)
N1 0.010(3) 0.019(3) 0.018(3) -0.010(2) 0.004(2) -0.001(2)
N6 0.021(3) 0.041(4) 0.043(4) -0.015(3) 0.007(3) 0.002(3)
N7 0.022(3) 0.045(4) 0.038(4) -0.021(3) 0.007(3) 0.002(3)
C3 0.016(3) 0.019(3) 0.032(4) -0.008(3) 0.010(3) -0.002(3)
C2 0.013(3) 0.017(3) 0.009(3) -0.002(3) -0.002(2) 0.000(3)
O1 0.212(9) 0.192(10) 0.195(9) -0.017(7) 0.096(6) 0.001(7)

_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
N4 N6 1.324(10) . ?
N4 N2 1.336(9) . ?
N4 Cu1 1.995(7) 3_576 ?
N3 C1 1.313(9) . ?
N3 N5 1.371(9) . ?
N3 Cu1 2.222(7) 2_545 ?
N5 C2 1.326(10) . ?
N5 Cu1 1.988(6) 4_575 ?
C1 N1 1.347(10) . ?
C1 H1 0.9300 . ?
Cu1 N5 1.988(6) 4_676 ?
Cu1 N4 1.995(7) 3_576 ?
Cu1 N1 2.044(6) . ?
Cu1 N2 2.053(6) . ?
Cu1 N3 2.222(7) 2 ?
N2 C3 1.323(10) . ?
N1 C2 1.334(9) . ?
N6 N7 1.344(12) . ?
N7 C3 1.320(11) . ?
C3 C2 1.461(11) . ?

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
N6 N4 N2 108.2(7) . . ?
N6 N4 Cu1 125.0(6) . 3_576 ?
N2 N4 Cu1 125.3(5) . 3_576 ?
C1 N3 N5 107.4(6) . . ?
C1 N3 Cu1 128.6(5) . 2_545 ?
N5 N3 Cu1 123.9(4) . 2_545 ?
C2 N5 N3 104.6(6) . . ?
C2 N5 Cu1 120.5(5) . 4_575 ?
N3 N5 Cu1 134.2(5) . 4_575 ?
N3 C1 N1 111.7(6) . . ?
N3 C1 H1 124.2 . . ?
N1 C1 H1 124.2 . . ?
N5 Cu1 N4 89.9(3) 4_676 3_576 ?
N5 Cu1 N1 92.4(2) 4_676 . ?
N4 Cu1 N1 164.8(3) 3_576 . ?
N5 Cu1 N2 160.1(3) 4_676 . ?
N4 Cu1 N2 92.2(3) 3_576 . ?
N1 Cu1 N2 80.6(3) . . ?
N5 Cu1 N3 101.6(2) 4_676 2 ?
N4 Cu1 N3 95.0(3) 3_576 2 ?
N1 Cu1 N3 99.3(3) . 2 ?
N2 Cu1 N3 97.9(3) . 2 ?
C3 N2 N4 104.5(6) . . ?
C3 N2 Cu1 113.8(5) . . ?
N4 N2 Cu1 141.7(5) . . ?
C2 N1 C1 103.0(6) . . ?
C2 N1 Cu1 112.2(5) . . ?
C1 N1 Cu1 144.7(5) . . ?
N4 N6 N7 110.7(7) . . ?
C3 N7 N6 102.7(7) . . ?
N7 C3 N2 113.9(8) . . ?
N7 C3 C2 130.6(8) . . ?
N2 C3 C2 115.3(7) . . ?
N5 C2 N1 113.3(7) . . ?
N5 C2 C3 128.5(7) . . ?
N1 C2 C3 117.9(7) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.560
_refine_diff_density_min         -1.353
_refine_diff_density_rms         0.288
_database_code_depnum_ccdc_archive 'CCDC 1000294'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H2 Cu N7'
_chemical_formula_weight         199.66

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   8.630(3)
_cell_length_b                   9.867(3)
_cell_length_c                   6.736(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.297(6)
_cell_angle_gamma                90.00
_cell_volume                     544.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    986
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.34

_exptl_crystal_description       flake
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    3.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.253
_exptl_absorpt_correction_T_max  0.554
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            986
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.34
_reflns_number_total             986
_reflns_number_gt                695
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+24.0000P] 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_number_reflns         986
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1842
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.5910(2) 0.16584(16) 0.5678(3) 0.0241(5) Uani 1 1 d . . .
N1 N 0.4432(12) 0.3238(10) 0.6052(15) 0.013(2) Uani 1 1 d . . .
N2 N 0.4727(13) 0.4000(11) 0.7745(19) 0.022(3) Uani 1 1 d . . .
N3 N 0.3818(12) 0.5136(11) 0.7267(18) 0.020(2) Uani 1 1 d . . .
N4 N 0.3328(13) 0.3820(11) 0.442(2) 0.027(3) Uani 1 1 d . . .
N5 N 0.1915(12) 0.7274(11) 0.3980(18) 0.019(3) Uani 1 1 d . . .
N6 N 0.0453(12) 0.7699(10) 0.2726(19) 0.021(3) Uani 1 1 d . . .
H6A H 0.0183 0.8529 0.2406 0.025 Uiso 1 1 calc R . .
N7 N 0.0241(14) 0.5505(11) 0.280(2) 0.026(3) Uani 1 1 d . . .
C1 C 0.3002(16) 0.4971(12) 0.523(2) 0.020(3) Uani 1 1 d . . .
C2 C 0.1728(16) 0.5960(13) 0.397(2) 0.019(3) Uani 1 1 d . . .
C3 C -0.0491(16) 0.6649(14) 0.208(2) 0.024(3) Uani 1 1 d . . .
H7A H -0.1562 0.6706 0.1195 0.029 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0238(9) 0.0128(8) 0.0301(9) 0.0005(8) 0.0001(7) -0.0017(7)
N1 0.024(5) 0.004(4) 0.011(5) -0.002(4) 0.005(4) 0.000(4)
N2 0.024(6) 0.010(5) 0.031(7) 0.008(5) 0.007(5) 0.005(5)
N3 0.013(5) 0.017(5) 0.027(6) -0.001(5) 0.002(5) 0.001(5)
N4 0.016(6) 0.011(5) 0.046(8) 0.001(5) 0.000(6) 0.004(5)
N5 0.014(5) 0.016(6) 0.023(7) -0.002(5) 0.002(5) -0.001(4)
N6 0.012(5) 0.009(5) 0.034(7) 0.007(5) -0.004(5) 0.006(4)
N7 0.020(6) 0.021(6) 0.027(7) 0.001(5) -0.005(6) -0.001(5)
C1 0.025(7) 0.006(5) 0.024(7) 0.005(5) 0.001(6) -0.001(5)
C2 0.017(7) 0.022(7) 0.018(7) 0.002(6) 0.007(6) 0.002(6)
C3 0.019(7) 0.015(6) 0.033(8) 0.005(7) -0.001(6) 0.008(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 2.005(11) 2_646 ?
Cu1 N2 2.025(11) 4_565 ?
Cu1 N1 2.079(10) . ?
Cu1 N5 2.101(11) 3_666 ?
N1 N2 1.322(15) . ?
N1 N4 1.338(14) . ?
N2 N3 1.348(15) . ?
N2 Cu1 2.025(11) 4_566 ?
N3 C1 1.340(17) . ?
N3 Cu1 2.005(11) 2_656 ?
N4 C1 1.329(17) . ?
N5 C2 1.306(16) . ?
N5 N6 1.347(14) . ?
N5 Cu1 2.101(11) 3_666 ?
N6 C3 1.306(17) . ?
N6 H6A 0.8600 . ?
N7 C3 1.311(17) . ?
N7 C2 1.354(17) . ?
C1 C2 1.515(17) . ?
C3 H7A 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
N3 Cu1 N2 110.3(4) 2_646 4_565 ?
N3 Cu1 N1 114.9(4) 2_646 . ?
N2 Cu1 N1 102.6(4) 4_565 . ?
N3 Cu1 N5 113.1(4) 2_646 3_666 ?
N2 Cu1 N5 115.3(5) 4_565 3_666 ?
N1 Cu1 N5 99.9(4) . 3_666 ?
N2 N1 N4 111.1(10) . . ?
N2 N1 Cu1 124.9(8) . . ?
N4 N1 Cu1 121.9(8) . . ?
N1 N2 N3 109.1(10) . . ?
N1 N2 Cu1 124.1(8) . 4_566 ?
N3 N2 Cu1 125.3(9) . 4_566 ?
C1 N3 N2 102.9(11) . . ?
C1 N3 Cu1 135.0(9) . 2_656 ?
N2 N3 Cu1 121.6(9) . 2_656 ?
C1 N4 N1 102.4(11) . . ?
C2 N5 N6 102.5(11) . . ?
C2 N5 Cu1 127.1(9) . 3_666 ?
N6 N5 Cu1 122.8(8) . 3_666 ?
C3 N6 N5 109.0(10) . . ?
C3 N6 H6A 125.5 . . ?
N5 N6 H6A 125.5 . . ?
C3 N7 C2 100.9(11) . . ?
N4 C1 N3 114.5(12) . . ?
N4 C1 C2 122.0(12) . . ?
N3 C1 C2 123.4(12) . . ?
N5 C2 N7 115.2(12) . . ?
N5 C2 C1 124.8(12) . . ?
N7 C2 C1 120.0(11) . . ?
N6 C3 N7 112.4(11) . . ?
N6 C3 H7A 123.8 . . ?
N7 C3 H7A 123.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A N7 0.86 1.98 2.831(15) 169.9 2

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.381
_refine_diff_density_min         -1.137
_refine_diff_density_rms         0.250
_database_code_depnum_ccdc_archive 'CCDC 1000295'
