data_publication_text
_publ_requested_journal          'Inorganic Chemistry'
_publ_contact_author_name        'Professor William B. Tolman'
_publ_contact_author_address     
;Department of Chemistry and Center for Metals in Biocatalysis
University of Minnesota
207 Pleasant Street SE
Minneapolis, Minnesota 55455 (USA)
;
_publ_contact_author_email       tolman@umn.edu
_publ_contact_author_phone       '(+1) 612-625-4061'
_publ_contact_author_fax         '(+1) 612-624-7029'
loop_
_publ_author_name
_publ_author_address
'Tolman, William B.'
;Department of Chemistry and Center for Metals in Biocatalysis
University of Minnesota
207 Pleasant Street SE
Minneapolis, Minnesota 55455 (USA)
;
'Gupta, Aalo K.'
;Department of Chemistry and Center for Metals in Biocatalysis
University of Minnesota
207 Pleasant Street SE
Minneapolis, Minnesota 55455 (USA)
; 

data_09151m 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             09151 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C11 H22 Cu N5'
_chemical_formula_sum 
 'C11 H22 Cu N5' 
_chemical_formula_weight          287.88 
 
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' 
 
_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                    6.758(2) 
_cell_length_b                    11.412(4) 
_cell_length_c                    18.971(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  96.256(4) 
_cell_angle_gamma                 90.00 
_cell_volume                      1454.4(8) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     4027
_cell_measurement_theta_min       2.16
_cell_measurement_theta_max       27.44 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             orange
_exptl_crystal_size_max           0.5 
_exptl_crystal_size_mid           0.4
_exptl_crystal_size_min           0.2
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.319 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              608 
_exptl_absorpt_coefficient_mu     1.490 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   .494  
_exptl_absorpt_correction_T_max   0.742 
_exptl_absorpt_process_details    'SADABS, R. Blessing, 1995' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'normal-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Siemens SMART Platform CCD' 
_diffrn_measurement_method        'area detector, omega scans per phi' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             16229 
_diffrn_reflns_av_R_equivalents   0.0352 
_diffrn_reflns_av_sigmaI/netI     0.0279 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -24 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          2.09 
_diffrn_reflns_theta_max          27.50 
_reflns_number_total              3318 
_reflns_number_gt                 2775 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'SMART, Bruker' 
_computing_cell_refinement        'SAINT, Bruker' 
_computing_data_reduction         'SAINT, Bruker' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'SHELXTL, Bruker' 
_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)+(0.0220P)²+1.4022P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3318 
_refine_ls_number_parameters      161 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0469 
_refine_ls_R_factor_gt            0.0354 
_refine_ls_wR_factor_ref          0.0777 
_refine_ls_wR_factor_gt           0.0745 
_refine_ls_goodness_of_fit_ref    1.127 
_refine_ls_restrained_S_all       1.127 
_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 0.25814(4) 0.28355(2) 0.291774(14) 0.02469(9) Uani 1 1 d . . . 
N1 N 0.2725(3) 0.22645(16) 0.38798(9) 0.0247(4) Uani 1 1 d . . . 
N2 N 0.2317(3) 0.13168(17) 0.24402(10) 0.0270(4) Uani 1 1 d . . . 
N3 N 0.3058(3) 0.30137(17) 0.45034(9) 0.0272(4) Uani 1 1 d . . . 
N4 N 0.2181(3) 0.11922(18) 0.16680(10) 0.0328(5) Uani 1 1 d . . . 
N5 N 0.2609(3) 0.42961(17) 0.24490(10) 0.0274(4) Uani 1 1 d . . . 
C1 C 0.2603(4) 0.0762(2) 0.48107(12) 0.0347(6) Uani 1 1 d . . . 
H1A H 0.1480 0.1131 0.5011 0.052 Uiso 1 1 calc R . . 
H1B H 0.3852 0.1006 0.5082 0.052 Uiso 1 1 calc R . . 
H1C H 0.2475 -0.0092 0.4835 0.052 Uiso 1 1 calc R . . 
C2 C 0.2606(3) 0.1135(2) 0.40434(12) 0.0241(5) Uani 1 1 d . . . 
C3 C 0.2459(3) 0.0239(2) 0.35302(12) 0.0257(5) Uani 1 1 d . . . 
H3A H 0.2426 -0.0534 0.3715 0.031 Uiso 1 1 calc R . . 
C4 C 0.2351(3) 0.03059(19) 0.27806(12) 0.0249(5) Uani 1 1 d . . . 
C5 C 0.2294(4) -0.0841(2) 0.23855(13) 0.0300(5) Uani 1 1 d . . . 
H5A H 0.1100 -0.0870 0.2043 0.045 Uiso 1 1 calc R . . 
H5B H 0.2264 -0.1490 0.2722 0.045 Uiso 1 1 calc R . . 
H5C H 0.3481 -0.0910 0.2134 0.045 Uiso 1 1 calc R . . 
C6 C 0.1679(5) 0.3996(2) 0.44076(14) 0.0432(7) Uani 1 1 d . . . 
H6A H 0.0308 0.3703 0.4371 0.065 Uiso 1 1 calc R . . 
H6B H 0.1893 0.4420 0.3973 0.065 Uiso 1 1 calc R . . 
H6C H 0.1907 0.4526 0.4815 0.065 Uiso 1 1 calc R . . 
C7 C 0.5102(4) 0.3424(3) 0.45437(14) 0.0406(6) Uani 1 1 d . . . 
H7A H 0.6009 0.2753 0.4603 0.061 Uiso 1 1 calc R . . 
H7B H 0.5369 0.3955 0.4949 0.061 Uiso 1 1 calc R . . 
H7C H 0.5307 0.3841 0.4106 0.061 Uiso 1 1 calc R . . 
C8 C 0.3969(4) 0.1705(3) 0.14317(13) 0.0447(7) Uani 1 1 d . . . 
H8A H 0.5129 0.1231 0.1607 0.067 Uiso 1 1 calc R . . 
H8B H 0.4141 0.2504 0.1617 0.067 Uiso 1 1 calc R . . 
H8C H 0.3841 0.1725 0.0912 0.067 Uiso 1 1 calc R . . 
C9 C 0.0426(4) 0.1838(3) 0.13694(13) 0.0416(7) Uani 1 1 d . . . 
H9A H -0.0764 0.1498 0.1541 0.062 Uiso 1 1 calc R . . 
H9B H 0.0313 0.1790 0.0851 0.062 Uiso 1 1 calc R . . 
H9C H 0.0551 0.2661 0.1516 0.062 Uiso 1 1 calc R . . 
C10 C 0.2551(3) 0.5124(2) 0.21116(12) 0.0265(5) Uani 1 1 d . . . 
C11 C 0.2485(4) 0.6171(2) 0.16742(14) 0.0342(6) Uani 1 1 d . . . 
H11A H 0.3716 0.6620 0.1786 0.051 Uiso 1 1 calc R . . 
H11B H 0.1343 0.6653 0.1769 0.051 Uiso 1 1 calc R . . 
H11C H 0.2352 0.5946 0.1173 0.051 Uiso 1 1 calc R . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Cu1 N5 1.890(2) . ? 
Cu1 N1 1.9305(19) . ? 
Cu1 N2 1.9548(19) . ? 
N1 C2 1.331(3) . ? 
N1 N3 1.457(2) . ? 
N2 C4 1.321(3) . ? 
N2 N4 1.465(3) . ? 
N3 C7 1.452(3) . ? 
N3 C6 1.457(3) . ? 
N4 C8 1.457(3) . ? 
N4 C9 1.457(3) . ? 
N5 C10 1.139(3) . ? 
C1 C2 1.517(3) . ? 
C1 H1A 0.9800 . ? 
C1 H1B 0.9800 . ? 
C1 H1C 0.9800 . ? 
C2 C3 1.408(3) . ? 
C3 C4 1.418(3) . ? 
C3 H3A 0.9500 . ? 
C4 C5 1.507(3) . ? 
C5 H5A 0.9800 . ? 
C5 H5B 0.9800 . ? 
C5 H5C 0.9800 . ? 
C6 H6A 0.9800 . ? 
C6 H6B 0.9800 . ? 
C6 H6C 0.9800 . ? 
C7 H7A 0.9800 . ? 
C7 H7B 0.9800 . ? 
C7 H7C 0.9800 . ? 
C8 H8A 0.9800 . ? 
C8 H8B 0.9800 . ? 
C8 H8C 0.9800 . ? 
C9 H9A 0.9800 . ? 
C9 H9B 0.9800 . ? 
C9 H9C 0.9800 . ? 
C10 C11 1.453(3) . ? 
C11 H11A 0.9800 . ? 
C11 H11B 0.9800 . ? 
C11 H11C 0.9800 . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
N5 Cu1 N1 137.76(8) . . ? 
N5 Cu1 N2 124.67(8) . . ? 
N1 Cu1 N2 97.56(8) . . ? 
C2 N1 N3 112.78(17) . . ? 
C2 N1 Cu1 123.33(15) . . ? 
N3 N1 Cu1 123.85(14) . . ? 
C4 N2 N4 113.58(18) . . ? 
C4 N2 Cu1 123.49(15) . . ? 
N4 N2 Cu1 122.83(14) . . ? 
C7 N3 C6 110.5(2) . . ? 
C7 N3 N1 107.08(17) . . ? 
C6 N3 N1 108.07(18) . . ? 
C8 N4 C9 110.1(2) . . ? 
C8 N4 N2 107.77(19) . . ? 
C9 N4 N2 107.41(18) . . ? 
C10 N5 Cu1 173.7(2) . . ? 
C2 C1 H1A 109.5 . . ? 
C2 C1 H1B 109.5 . . ? 
H1A C1 H1B 109.5 . . ? 
C2 C1 H1C 109.5 . . ? 
H1A C1 H1C 109.5 . . ? 
H1B C1 H1C 109.5 . . ? 
N1 C2 C3 122.9(2) . . ? 
N1 C2 C1 120.1(2) . . ? 
C3 C2 C1 116.9(2) . . ? 
C2 C3 C4 130.3(2) . . ? 
C2 C3 H3A 114.9 . . ? 
C4 C3 H3A 114.9 . . ? 
N2 C4 C3 122.3(2) . . ? 
N2 C4 C5 121.2(2) . . ? 
C3 C4 C5 116.6(2) . . ? 
C4 C5 H5A 109.5 . . ? 
C4 C5 H5B 109.5 . . ? 
H5A C5 H5B 109.5 . . ? 
C4 C5 H5C 109.5 . . ? 
H5A C5 H5C 109.5 . . ? 
H5B C5 H5C 109.5 . . ? 
N3 C6 H6A 109.5 . . ? 
N3 C6 H6B 109.5 . . ? 
H6A C6 H6B 109.5 . . ? 
N3 C6 H6C 109.5 . . ? 
H6A C6 H6C 109.5 . . ? 
H6B C6 H6C 109.5 . . ? 
N3 C7 H7A 109.5 . . ? 
N3 C7 H7B 109.5 . . ? 
H7A C7 H7B 109.5 . . ? 
N3 C7 H7C 109.5 . . ? 
H7A C7 H7C 109.5 . . ? 
H7B C7 H7C 109.5 . . ? 
N4 C8 H8A 109.5 . . ? 
N4 C8 H8B 109.5 . . ? 
H8A C8 H8B 109.5 . . ? 
N4 C8 H8C 109.5 . . ? 
H8A C8 H8C 109.5 . . ? 
H8B C8 H8C 109.5 . . ? 
N4 C9 H9A 109.5 . . ? 
N4 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
N4 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
N5 C10 C11 179.3(3) . . ? 
C10 C11 H11A 109.5 . . ? 
C10 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C10 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
N5 Cu1 N1 C2 177.98(16) . . . . ? 
N2 Cu1 N1 C2 -1.14(19) . . . . ? 
N5 Cu1 N1 N3 -4.7(2) . . . . ? 
N2 Cu1 N1 N3 176.18(16) . . . . ? 
N5 Cu1 N2 C4 178.26(17) . . . . ? 
N1 Cu1 N2 C4 -2.5(2) . . . . ? 
N5 Cu1 N2 N4 2.1(2) . . . . ? 
N1 Cu1 N2 N4 -178.67(17) . . . . ? 
C2 N1 N3 C7 107.7(2) . . . . ? 
Cu1 N1 N3 C7 -69.9(2) . . . . ? 
C2 N1 N3 C6 -133.2(2) . . . . ? 
Cu1 N1 N3 C6 49.2(2) . . . . ? 
C4 N2 N4 C8 -117.9(2) . . . . ? 
Cu1 N2 N4 C8 58.7(2) . . . . ? 
C4 N2 N4 C9 123.5(2) . . . . ? 
Cu1 N2 N4 C9 -60.0(2) . . . . ? 
N1 Cu1 N5 C10 -161.3(17) . . . . ? 
N2 Cu1 N5 C10 17.6(18) . . . . ? 
N3 N1 C2 C3 -174.4(2) . . . . ? 
Cu1 N1 C2 C3 3.1(3) . . . . ? 
N3 N1 C2 C1 6.2(3) . . . . ? 
Cu1 N1 C2 C1 -176.19(16) . . . . ? 
N1 C2 C3 C4 -1.9(4) . . . . ? 
C1 C2 C3 C4 177.4(2) . . . . ? 
N4 N2 C4 C3 -179.4(2) . . . . ? 
Cu1 N2 C4 C3 4.1(3) . . . . ? 
N4 N2 C4 C5 1.2(3) . . . . ? 
Cu1 N2 C4 C5 -175.38(16) . . . . ? 
C2 C3 C4 N2 -2.1(4) . . . . ? 
C2 C3 C4 C5 177.4(2) . . . . ? 
Cu1 N5 C10 C11 -43(24) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.992 
_diffrn_reflns_theta_full              27.50 
_diffrn_measured_fraction_theta_full   0.992 
_refine_diff_density_max    0.583 
_refine_diff_density_min   -0.375 
_refine_diff_density_rms    0.070 

#==== END
 
data_10100m 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C11 H22 Cu N5'  
_chemical_formula_sum 
 'C11 H22 Cu N5' 
_chemical_formula_weight          287.88 
 
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' 
 
_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                    10.4434(18) 
_cell_length_b                    10.0699(18) 
_cell_length_c                    13.658(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  94.526(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1431.9(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     3420
_cell_measurement_theta_min       2.37
_cell_measurement_theta_max       23.89 
 
_exptl_crystal_description        plate 
_exptl_crystal_colour             colorless 
_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     1.335 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              608 
_exptl_absorpt_coefficient_mu     1.514 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.702 
_exptl_absorpt_correction_T_max   0.739 
_exptl_absorpt_process_details    'SADABS, R. Blessing, 1995' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       123(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'normal-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker SMART Platform CCD' 
_diffrn_measurement_method        'area detector, omega scans per phi' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             12501 
_diffrn_reflns_av_R_equivalents   0.0482 
_diffrn_reflns_av_sigmaI/netI     0.0363 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          2.37 
_diffrn_reflns_theta_max          25.02 
_reflns_number_total              2514 
_reflns_number_gt                 2023 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'SMART, Bruker' 
_computing_cell_refinement        'SAINT, Bruker' 
_computing_data_reduction         'SAINT, Bruker' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'SHELXTL, Bruker' 
_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)+(0.0546P)²+3.1553P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     refall 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2514 
_refine_ls_number_parameters      161 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0541 
_refine_ls_R_factor_gt            0.0386 
_refine_ls_wR_factor_ref          0.1080 
_refine_ls_wR_factor_gt           0.0981 
_refine_ls_goodness_of_fit_ref    0.985 
_refine_ls_restrained_S_all       0.985 
_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 0.07004(4) 0.13579(4) 0.63137(3) 0.02031(16) Uani 1 1 d . . . 
N4 N 0.3391(3) 0.0421(3) 0.6897(2) 0.0227(7) Uani 1 1 d . . . 
N2 N 0.2117(3) 0.0744(3) 0.7205(2) 0.0199(6) Uani 1 1 d . . . 
N1 N -0.0560(3) 0.1593(3) 0.7267(2) 0.0225(7) Uani 1 1 d . . . 
N5 N 0.0542(3) 0.1670(3) 0.4949(2) 0.0227(7) Uani 1 1 d . . . 
N3 N -0.1828(3) 0.2156(3) 0.7031(2) 0.0268(7) Uani 1 1 d . . . 
C11 C 0.0332(4) 0.2037(4) 0.3065(2) 0.0259(8) Uani 1 1 d . . . 
H11A H -0.0377(18) 0.2281(7) 0.2893(5) 0.039 Uiso 1 1 calc R . . 
H11B H 0.0475(5) 0.1355(18) 0.2797(8) 0.039 Uiso 1 1 calc R . . 
H11C H 0.0838(13) 0.2585(15) 0.2926(5) 0.039 Uiso 1 1 calc R . . 
C2 C -0.0314(3) 0.1331(3) 0.8220(2) 0.0224(8) Uani 1 1 d . . . 
C1 C -0.1294(4) 0.1650(4) 0.8934(3) 0.0294(9) Uani 1 1 d . . . 
H1A H -0.1863(18) 0.1917(9) 0.8672(8) 0.044 Uiso 1 1 calc R . . 
H1B H -0.1032(8) 0.2132(15) 0.9285(11) 0.044 Uiso 1 1 calc R . . 
H1C H -0.1458(6) 0.1053(18) 0.9188(8) 0.044 Uiso 1 1 calc R . . 
C4 C 0.2004(3) 0.0538(3) 0.8158(2) 0.0209(7) Uani 1 1 d . . . 
C10 C 0.0438(3) 0.1834(4) 0.4121(3) 0.0225(8) Uani 1 1 d . . . 
C3 C 0.0862(4) 0.0796(4) 0.8609(2) 0.0244(8) Uani 1 1 d . . . 
H3A H 0.0892 0.0572 0.9286 0.029 Uiso 1 1 calc R . . 
C5 C 0.3121(3) 0.0024(4) 0.8823(3) 0.0294(9) Uani 1 1 d . . . 
H5A H 0.3713(17) -0.0095(5) 0.8515(8) 0.044 Uiso 1 1 calc R . . 
H5B H 0.2927(6) -0.0646(19) 0.9064(7) 0.044 Uiso 1 1 calc R . . 
H5C H 0.3302(6) 0.0548(14) 0.9236(11) 0.044 Uiso 1 1 calc R . . 
C9 C 0.3629(4) 0.1294(4) 0.6078(3) 0.0297(9) Uani 1 1 d . . . 
H9A H 0.3651(4) 0.220(2) 0.6299(6) 0.045 Uiso 1 1 calc R . . 
H9B H 0.2955(17) 0.1187(5) 0.5565(13) 0.045 Uiso 1 1 calc R . . 
H9C H 0.444(2) 0.1069(7) 0.5833(7) 0.045 Uiso 1 1 calc R . . 
C8 C 0.3362(4) -0.0952(4) 0.6546(3) 0.0315(9) Uani 1 1 d . . . 
H8A H 0.3204(5) -0.1546(15) 0.7086(13) 0.047 Uiso 1 1 calc R . . 
H8B H 0.418(2) -0.1172(7) 0.6296(7) 0.047 Uiso 1 1 calc R . . 
H8C H 0.2680(17) -0.1053(5) 0.6023(13) 0.047 Uiso 1 1 calc R . . 
C7 C -0.2474(4) 0.1303(5) 0.6291(3) 0.0502(13) Uani 1 1 d . . . 
H7A H -0.332(3) 0.1644(11) 0.6112(6) 0.075 Uiso 1 1 calc R . . 
H7B H -0.2538(5) 0.042(3) 0.6551(8) 0.075 Uiso 1 1 calc R . . 
H7C H -0.1989(15) 0.1281(6) 0.5718(17) 0.075 Uiso 1 1 calc R . . 
C6 C -0.1649(4) 0.3476(5) 0.6630(4) 0.0504(13) Uani 1 1 d . . . 
H6A H -0.1251(13) 0.3999(17) 0.7097(14) 0.076 Uiso 1 1 calc R . . 
H6B H -0.242(2) 0.3828(12) 0.6432(7) 0.076 Uiso 1 1 calc R . . 
H6C H -0.1164(15) 0.3420(5) 0.6114(16) 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 N5 1.884(3) . ? 
Cu1 N1 1.937(3) . ? 
Cu1 N2 1.941(3) . ? 
N4 C9 1.458(5) . ? 
N4 C8 1.463(5) . ? 
N4 N2 1.463(4) . ? 
N2 C4 1.333(4) . ? 
N1 C2 1.333(4) . ? 
N1 N3 1.453(4) . ? 
N5 C10 1.140(4) . ? 
N3 C6 1.455(5) . ? 
N3 C7 1.452(5) . ? 
C11 C10 1.452(5) . ? 
C11 H11A 0.7976 . ? 
C11 H11B 0.7976 . ? 
C11 H11C 0.7976 . ? 
C2 C3 1.407(5) . ? 
C2 C1 1.503(5) . ? 
C1 H1A 0.7217 . ? 
C1 H1B 0.7217 . ? 
C1 H1C 0.7217 . ? 
C4 C3 1.408(5) . ? 
C4 C5 1.513(5) . ? 
C3 H3A 0.9500 . ? 
C5 H5A 0.7840 . ? 
C5 H5B 0.7840 . ? 
C5 H5C 0.7840 . ? 
C9 H9A 0.9598 . ? 
C9 H9B 0.9598 . ? 
C9 H9C 0.9598 . ? 
C8 H8A 0.9734 . ? 
C8 H8B 0.9734 . ? 
C8 H8C 0.9734 . ? 
C7 H7A 0.9648 . ? 
C7 H7B 0.9648 . ? 
C7 H7C 0.9648 . ? 
C6 H6A 0.9024 . ? 
C6 H6B 0.9024 . ? 
C6 H6C 0.9024 . ? 
 
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 
N5 Cu1 N1 129.25(12) . . ? 
N5 Cu1 N2 132.55(12) . . ? 
N1 Cu1 N2 98.19(12) . . ? 
C9 N4 C8 108.6(3) . . ? 
C9 N4 N2 107.5(3) . . ? 
C8 N4 N2 107.9(3) . . ? 
C4 N2 N4 113.6(3) . . ? 
C4 N2 Cu1 122.6(2) . . ? 
N4 N2 Cu1 123.8(2) . . ? 
C2 N1 N3 113.3(3) . . ? 
C2 N1 Cu1 122.9(2) . . ? 
N3 N1 Cu1 123.7(2) . . ? 
C10 N5 Cu1 178.7(3) . . ? 
C6 N3 N1 107.3(3) . . ? 
C6 N3 C7 110.2(4) . . ? 
N1 N3 C7 106.8(3) . . ? 
C10 C11 H11A 109.5 . . ? 
C10 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C10 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
N1 C2 C3 122.7(3) . . ? 
N1 C2 C1 120.2(3) . . ? 
C3 C2 C1 117.1(3) . . ? 
C2 C1 H1A 109.5 . . ? 
C2 C1 H1B 109.5 . . ? 
H1A C1 H1B 109.5 . . ? 
C2 C1 H1C 109.5 . . ? 
H1A C1 H1C 109.5 . . ? 
H1B C1 H1C 109.5 . . ? 
N2 C4 C3 122.8(3) . . ? 
N2 C4 C5 121.1(3) . . ? 
C3 C4 C5 116.1(3) . . ? 
N5 C10 C11 178.9(4) . . ? 
C4 C3 C2 130.5(3) . . ? 
C4 C3 H3A 114.7 . . ? 
C2 C3 H3A 114.7 . . ? 
C4 C5 H5A 109.5 . . ? 
C4 C5 H5B 109.5 . . ? 
H5A C5 H5B 109.5 . . ? 
C4 C5 H5C 109.5 . . ? 
H5A C5 H5C 109.5 . . ? 
H5B C5 H5C 109.5 . . ? 
N4 C9 H9A 109.5 . . ? 
N4 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
N4 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
N4 C8 H8A 109.5 . . ? 
N4 C8 H8B 109.5 . . ? 
H8A C8 H8B 109.5 . . ? 
N4 C8 H8C 109.5 . . ? 
H8A C8 H8C 109.5 . . ? 
H8B C8 H8C 109.5 . . ? 
N3 C7 H7A 109.5 . . ? 
N3 C7 H7B 109.5 . . ? 
H7A C7 H7B 109.5 . . ? 
N3 C7 H7C 109.5 . . ? 
H7A C7 H7C 109.5 . . ? 
H7B C7 H7C 109.5 . . ? 
N3 C6 H6A 109.5 . . ? 
N3 C6 H6B 109.5 . . ? 
H6A C6 H6B 109.5 . . ? 
N3 C6 H6C 109.5 . . ? 
H6A C6 H6C 109.5 . . ? 
H6B C6 H6C 109.5 . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C9 N4 N2 C4 -149.8(3) . . . . ? 
C8 N4 N2 C4 93.2(3) . . . . ? 
C9 N4 N2 Cu1 32.1(4) . . . . ? 
C8 N4 N2 Cu1 -84.9(3) . . . . ? 
N5 Cu1 N2 C4 -177.2(2) . . . . ? 
N1 Cu1 N2 C4 3.5(3) . . . . ? 
N5 Cu1 N2 N4 0.8(3) . . . . ? 
N1 Cu1 N2 N4 -178.6(2) . . . . ? 
N5 Cu1 N1 C2 -180.0(3) . . . . ? 
N2 Cu1 N1 C2 -0.7(3) . . . . ? 
N5 Cu1 N1 N3 -4.5(3) . . . . ? 
N2 Cu1 N1 N3 174.9(3) . . . . ? 
N1 Cu1 N5 C10 -91(13) . . . . ? 
N2 Cu1 N5 C10 90(13) . . . . ? 
C2 N1 N3 C6 117.9(4) . . . . ? 
Cu1 N1 N3 C6 -58.0(4) . . . . ? 
C2 N1 N3 C7 -124.0(3) . . . . ? 
Cu1 N1 N3 C7 60.1(4) . . . . ? 
N3 N1 C2 C3 -179.3(3) . . . . ? 
Cu1 N1 C2 C3 -3.3(5) . . . . ? 
N3 N1 C2 C1 -1.4(5) . . . . ? 
Cu1 N1 C2 C1 174.5(2) . . . . ? 
N4 N2 C4 C3 179.4(3) . . . . ? 
Cu1 N2 C4 C3 -2.5(5) . . . . ? 
N4 N2 C4 C5 0.3(5) . . . . ? 
Cu1 N2 C4 C5 178.4(2) . . . . ? 
Cu1 N5 C10 C11 -91(25) . . . . ? 
N2 C4 C3 C2 -2.6(6) . . . . ? 
C5 C4 C3 C2 176.6(4) . . . . ? 
N1 C2 C3 C4 5.9(6) . . . . ? 
C1 C2 C3 C4 -172.0(4) . . . . ? 
 
_diffrn_measured_fraction_theta_max    1.000 
_diffrn_reflns_theta_full              25.02 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.654 
_refine_diff_density_min   -0.517 
_refine_diff_density_rms    0.082 



