# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Stuart Batten'
'Sze Nee Pek.'
'David Turner'

_publ_contact_author_name        'Stuart Batten'
_publ_contact_author_email       STUART.BATTEN@SCI.MONASH.EDU.AU

_publ_section_title              
;
2C or not 2C: The C2 Difference Between
2,2'-Bipyridine and 1,10-Phenanthroline Changes Bridging Species in
[Cu(cdm)Cl(L)]2 Dimers
;

# Attachment '2C_CIF.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 698651'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
[Cu(2,2'-bipy)(cdm)Cl]2.2MeOH
;
_chemical_name_common            "[Cu(2,2'-bipy)(cdm)Cl]2.2MeOH"
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 Cl2 Cu2 N10 O2, 2(C H4 O)'
_chemical_formula_sum            'C30 H28 Cl2 Cu2 N10 O4'
_chemical_formula_weight         790.60

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'
Cl Cl 0.1484 0.1585 '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                   8.3016(8)
_cell_length_b                   8.8946(9)
_cell_length_c                   11.7703(13)
_cell_angle_alpha                83.191(3)
_cell_angle_beta                 81.216(3)
_cell_angle_gamma                67.746(3)
_cell_volume                     793.19(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    5658
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.50

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_absorpt_coefficient_mu    1.564
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7348
_exptl_absorpt_correction_T_max  0.9259
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
OH and NH protons located from Fourier map
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5658
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3610
_reflns_number_gt                2882
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.2000P)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         3610
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.21607(4) 0.99350(4) -0.00694(3) 0.01436(12) Uani 1 1 d . . .
Cl1 Cl 0.02824(9) 0.80725(8) 0.06880(7) 0.01595(17) Uani 1 1 d . . .
O1 O 0.4090(3) 0.9962(2) 0.3684(2) 0.0197(5) Uani 1 1 d . . .
N1 N 0.2911(4) 1.1877(3) 0.4986(3) 0.0211(6) Uani 1 1 d . . .
C1 C 0.1600(4) 1.2226(4) 0.3244(3) 0.0166(7) Uani 1 1 d . . .
H1N H 0.224(4) 1.279(4) 0.525(3) 0.024(10) Uiso 1 1 d . . .
H1O H 0.385(5) 0.785(5) 0.382(4) 0.043(13) Uiso 1 1 d . . .
O2 O 0.3592(3) 0.6995(3) 0.3935(2) 0.0292(6) Uani 1 1 d . . .
N2 N 0.1818(3) 1.1030(3) 0.1349(3) 0.0184(6) Uani 1 1 d . . .
C2 C 0.1695(4) 1.1589(4) 0.2200(3) 0.0170(7) Uani 1 1 d . . .
H2N H 0.373(5) 1.136(5) 0.542(4) 0.040(12) Uiso 1 1 d . . .
N3 N -0.0761(4) 1.4982(3) 0.3757(3) 0.0275(7) Uani 1 1 d . . .
C3 C 0.0281(4) 1.3750(4) 0.3509(3) 0.0187(7) Uani 1 1 d . . .
N4 N 0.4458(3) 0.8224(3) 0.0328(2) 0.0147(5) Uani 1 1 d . . .
C4 C 0.2939(4) 1.1294(4) 0.3989(3) 0.0173(7) Uani 1 1 d . . .
N5 N 0.2955(3) 0.8843(3) -0.1554(2) 0.0161(6) Uani 1 1 d . . .
C5 C 0.5189(4) 0.8075(4) 0.1295(3) 0.0172(7) Uani 1 1 d . . .
H5 H 0.4640 0.8868 0.1847 0.021 Uiso 1 1 calc R . .
C6 C 0.6731(4) 0.6788(4) 0.1510(3) 0.0205(7) Uani 1 1 d . . .
H6 H 0.7229 0.6698 0.2202 0.025 Uiso 1 1 calc R . .
C7 C 0.7524(4) 0.5645(4) 0.0704(3) 0.0209(7) Uani 1 1 d . . .
H7 H 0.8575 0.4754 0.0837 0.025 Uiso 1 1 calc R . .
C8 C 0.6789(4) 0.5802(4) -0.0292(3) 0.0189(7) Uani 1 1 d . . .
H8 H 0.7325 0.5023 -0.0855 0.023 Uiso 1 1 calc R . .
C9 C 0.5243(4) 0.7119(4) -0.0466(3) 0.0161(7) Uani 1 1 d . . .
C10 C 0.4374(4) 0.7430(4) -0.1513(3) 0.0164(7) Uani 1 1 d . . .
C11 C 0.4900(4) 0.6399(4) -0.2403(3) 0.0203(7) Uani 1 1 d . . .
H11 H 0.5871 0.5399 -0.2352 0.024 Uiso 1 1 calc R . .
C12 C 0.4019(4) 0.6820(4) -0.3359(3) 0.0229(7) Uani 1 1 d . . .
H12 H 0.4362 0.6115 -0.3971 0.028 Uiso 1 1 calc R . .
C13 C 0.2616(4) 0.8297(4) -0.3415(3) 0.0219(7) Uani 1 1 d . . .
H13 H 0.2007 0.8637 -0.4077 0.026 Uiso 1 1 calc R . .
C14 C 0.2128(4) 0.9256(4) -0.2496(3) 0.0189(7) Uani 1 1 d . . .
H14 H 0.1159 1.0258 -0.2533 0.023 Uiso 1 1 calc R . .
C15 C 0.1864(5) 0.7434(5) 0.3669(4) 0.0341(9) Uani 1 1 d . . .
H15A H 0.1479 0.6513 0.3881 0.051 Uiso 1 1 calc R . .
H15B H 0.1830 0.7725 0.2841 0.051 Uiso 1 1 calc R . .
H15C H 0.1082 0.8368 0.4101 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 N2 1.962(3) . ?
Cu1 N5 1.999(3) . ?
Cu1 N4 2.019(2) . ?
Cu1 Cl1 2.2819(8) 2_575 ?
Cu1 Cl1 2.6743(8) . ?
Cl1 Cu1 2.2819(8) 2_575 ?
O1 C4 1.259(4) . ?
N1 C4 1.331(4) . ?
N1 H1N 0.86(4) . ?
N1 H2N 0.87(4) . ?
C1 C2 1.392(5) . ?
C1 C3 1.417(4) . ?
C1 C4 1.455(4) . ?
O2 C15 1.411(4) . ?
O2 H1O 0.86(4) . ?
N2 C2 1.145(4) . ?
N3 C3 1.147(4) . ?
N4 C5 1.340(4) . ?
N4 C9 1.347(4) . ?
N5 C14 1.335(4) . ?
N5 C10 1.360(4) . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.468(5) . ?
C10 C11 1.383(5) . ?
C11 C12 1.373(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N5 169.27(10) . . ?
N2 Cu1 N4 92.25(11) . . ?
N5 Cu1 N4 80.94(11) . . ?
N2 Cu1 Cl1 90.91(7) . 2_575 ?
N5 Cu1 Cl1 95.21(7) . 2_575 ?
N4 Cu1 Cl1 174.19(8) . 2_575 ?
N2 Cu1 Cl1 98.10(8) . . ?
N5 Cu1 Cl1 90.76(7) . . ?
N4 Cu1 Cl1 94.66(7) . . ?
Cl1 Cu1 Cl1 89.71(3) 2_575 . ?
Cu1 Cl1 Cu1 90.29(3) 2_575 . ?
C4 N1 H1N 129(3) . . ?
C4 N1 H2N 120(3) . . ?
H1N N1 H2N 111(4) . . ?
C2 C1 C3 119.5(3) . . ?
C2 C1 C4 117.0(3) . . ?
C3 C1 C4 123.4(3) . . ?
C15 O2 H1O 107(3) . . ?
C2 N2 Cu1 176.0(2) . . ?
N2 C2 C1 178.0(3) . . ?
N3 C3 C1 177.6(4) . . ?
C5 N4 C9 119.5(3) . . ?
C5 N4 Cu1 126.5(2) . . ?
C9 N4 Cu1 113.9(2) . . ?
O1 C4 N1 121.4(3) . . ?
O1 C4 C1 119.7(3) . . ?
N1 C4 C1 118.8(3) . . ?
C14 N5 C10 118.6(3) . . ?
C14 N5 Cu1 126.7(2) . . ?
C10 N5 Cu1 114.1(2) . . ?
N4 C5 C6 121.6(3) . . ?
N4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 119.1(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N4 C9 C8 121.2(3) . . ?
N4 C9 C10 115.2(3) . . ?
C8 C9 C10 123.7(3) . . ?
N5 C10 C11 120.9(3) . . ?
N5 C10 C9 114.6(3) . . ?
C11 C10 C9 124.5(3) . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
N5 C14 C13 122.9(3) . . ?
N5 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N3 0.86(4) 2.25(4) 3.094(4) 169(3) 2_586
O2 H1O O1 0.86(4) 1.95(4) 2.799(3) 172(4) .
C5 H5 O1 0.95 2.39 3.276(4) 156.0 .
N1 H2N O1 0.87(4) 2.11(4) 2.970(4) 174(4) 2_676

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.105

data_2
_database_code_depnum_ccdc_archive 'CCDC 698652'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
[(carbamoyldicyanomethanide)(chloro)(1,10-phenanthroline)copper(II)]
methanol solvate
;
_chemical_name_common            '[Cu(cdm)Cl(1,10-phen)]2.2MeOH'
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 Cl2 Cu2 N10 O2, 2(C H4 O)'
_chemical_formula_sum            'C34 H28 Cl2 Cu2 N10 O4'
_chemical_formula_weight         838.64

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'
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'

_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                   7.4044(7)
_cell_length_b                   9.9340(9)
_cell_length_c                   12.0617(13)
_cell_angle_alpha                108.736(5)
_cell_angle_beta                 91.509(5)
_cell_angle_gamma                99.329(5)
_cell_volume                     826.15(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    4985
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             426
_exptl_absorpt_coefficient_mu    1.507
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7328
_exptl_absorpt_correction_T_max  0.9150
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
OH and NH protons located experimentally
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4985
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2864
_reflns_number_gt                2465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.2000P)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         2864
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.013
_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 0.57927(5) 0.66570(4) 0.80510(3) 0.01211(12) Uani 1 1 d . . .
Cl1 Cl 0.49885(11) 0.87839(7) 0.82208(7) 0.0253(2) Uani 1 1 d . . .
O1 O 0.0664(3) 0.7194(2) 0.40236(18) 0.0215(5) Uani 1 1 d . . .
N1 N 0.2163(4) 0.8313(3) 0.5822(2) 0.0185(6) Uani 1 1 d . . .
C1 C 0.2213(4) 0.5801(3) 0.4834(3) 0.0127(6) Uani 1 1 d . . .
H1N H 0.195(4) 0.913(4) 0.582(3) 0.025(9) Uiso 1 1 d . . .
H1O H -0.134(4) 0.839(3) 0.430(3) 0.010(9) Uiso 1 1 d . . .
O2 O -0.2030(3) 0.8835(2) 0.43693(19) 0.0200(5) Uani 1 1 d . . .
N2 N 0.4120(3) 0.5789(2) 0.6614(2) 0.0167(5) Uani 1 1 d . . .
C2 C 0.3255(4) 0.5733(3) 0.5783(3) 0.0133(6) Uani 1 1 d . . .
H2N H 0.283(5) 0.831(4) 0.639(3) 0.030(10) Uiso 1 1 d . . .
N3 N 0.1481(3) 0.3565(3) 0.2998(2) 0.0177(5) Uani 1 1 d . . .
C3 C 0.1762(4) 0.4572(3) 0.3831(3) 0.0141(6) Uani 1 1 d . . .
N4 N 0.5921(3) 0.4757(2) 0.8280(2) 0.0113(5) Uani 1 1 d . . .
C4 C 0.1630(4) 0.7146(3) 0.4868(3) 0.0152(6) Uani 1 1 d . . .
N5 N 0.7279(3) 0.7435(2) 0.9614(2) 0.0123(5) Uani 1 1 d . . .
C5 C 0.5239(4) 0.3432(3) 0.7574(3) 0.0143(6) Uani 1 1 d . . .
H5 H 0.4584 0.3310 0.6850 0.017 Uiso 1 1 calc R . .
C6 C 0.5453(4) 0.2210(3) 0.7861(3) 0.0155(6) Uani 1 1 d . . .
H6 H 0.4953 0.1272 0.7337 0.019 Uiso 1 1 calc R . .
C7 C 0.6388(4) 0.2372(3) 0.8902(3) 0.0158(6) Uani 1 1 d . . .
H7 H 0.6530 0.1545 0.9106 0.019 Uiso 1 1 calc R . .
C8 C 0.7138(4) 0.3757(3) 0.9668(3) 0.0136(6) Uani 1 1 d . . .
C9 C 0.8152(4) 0.4061(3) 1.0774(3) 0.0152(6) Uani 1 1 d . . .
H9 H 0.8329 0.3283 1.1036 0.018 Uiso 1 1 calc R . .
C10 C 0.8859(4) 0.5422(3) 1.1452(3) 0.0156(6) Uani 1 1 d . . .
H10 H 0.9532 0.5584 1.2178 0.019 Uiso 1 1 calc R . .
C11 C 0.8617(3) 0.6634(3) 1.1098(2) 0.0127(6) Uani 1 1 d . . .
C12 C 0.9346(4) 0.8086(3) 1.1743(3) 0.0159(6) Uani 1 1 d . . .
H12 H 1.0063 0.8323 1.2467 0.019 Uiso 1 1 calc R . .
C13 C 0.9015(4) 0.9153(3) 1.1319(3) 0.0162(6) Uani 1 1 d . . .
H13 H 0.9496 1.0136 1.1750 0.019 Uiso 1 1 calc R . .
C14 C 0.7967(4) 0.8789(3) 1.0252(3) 0.0140(6) Uani 1 1 d . . .
H1 H 0.7738 0.9543 0.9972 0.017 Uiso 1 1 calc R . .
C15 C 0.7609(3) 0.6366(3) 1.0028(2) 0.0117(6) Uani 1 1 d . . .
C16 C 0.6866(3) 0.4919(3) 0.9307(2) 0.0107(6) Uani 1 1 d . . .
C17 C -0.2770(5) 0.8871(4) 0.5453(3) 0.0291(8) Uani 1 1 d . . .
H17A H -0.1766 0.9071 0.6061 0.044 Uiso 1 1 calc R . .
H17B H -0.3541 0.7936 0.5361 0.044 Uiso 1 1 calc R . .
H17C H -0.3514 0.9632 0.5683 0.044 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 N2 1.965(3) . ?
Cu1 N4 2.010(2) . ?
Cu1 N5 2.010(2) . ?
Cu1 Cl1 2.2354(8) . ?
Cu1 N3 2.413(2) 2_666 ?
O1 C4 1.247(3) . ?
N1 C4 1.340(4) . ?
N1 H1N 0.86(3) . ?
N1 H2N 0.83(4) . ?
C1 C2 1.389(4) . ?
C1 C3 1.401(4) . ?
C1 C4 1.459(4) . ?
O2 C17 1.423(4) . ?
O2 H1O 0.72(3) . ?
N2 C2 1.156(4) . ?
N3 C3 1.153(4) . ?
N3 Cu1 2.413(2) 2_666 ?
N4 C5 1.324(4) . ?
N4 C16 1.357(4) . ?
N5 C14 1.324(4) . ?
N5 C15 1.361(3) . ?
C5 C6 1.396(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.368(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(4) . ?
C7 H7 0.9500 . ?
C8 C16 1.398(4) . ?
C8 C9 1.432(4) . ?
C9 C10 1.344(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.435(4) . ?
C10 H10 0.9500 . ?
C11 C15 1.400(4) . ?
C11 C12 1.408(4) . ?
C12 C13 1.367(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(4) . ?
C13 H13 0.9500 . ?
C14 H1 0.9500 . ?
C15 C16 1.429(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
N2 Cu1 N4 94.29(10) . . ?
N2 Cu1 N5 173.30(10) . . ?
N4 Cu1 N5 82.14(9) . . ?
N2 Cu1 Cl1 88.51(7) . . ?
N4 Cu1 Cl1 161.56(7) . . ?
N5 Cu1 Cl1 93.13(7) . . ?
N2 Cu1 N3 93.65(9) . 2_666 ?
N4 Cu1 N3 88.58(8) . 2_666 ?
N5 Cu1 N3 91.93(9) . 2_666 ?
Cl1 Cu1 N3 109.46(6) . 2_666 ?
C4 N1 H1N 119(2) . . ?
C4 N1 H2N 123(2) . . ?
H1N N1 H2N 117(3) . . ?
C2 C1 C3 119.4(2) . . ?
C2 C1 C4 120.5(3) . . ?
C3 C1 C4 120.1(3) . . ?
C17 O2 H1O 106(3) . . ?
C2 N2 Cu1 158.1(2) . . ?
N2 C2 C1 174.7(3) . . ?
C3 N3 Cu1 110.2(2) . 2_666 ?
N3 C3 C1 176.7(3) . . ?
C5 N4 C16 118.5(2) . . ?
C5 N4 Cu1 128.93(19) . . ?
C16 N4 Cu1 112.53(18) . . ?
O1 C4 N1 121.5(3) . . ?
O1 C4 C1 120.2(3) . . ?
N1 C4 C1 118.2(3) . . ?
C14 N5 C15 118.2(2) . . ?
C14 N5 Cu1 129.50(19) . . ?
C15 N5 Cu1 112.33(18) . . ?
N4 C5 C6 122.0(3) . . ?
N4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C16 C8 C7 116.6(3) . . ?
C16 C8 C9 118.3(3) . . ?
C7 C8 C9 125.1(3) . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 121.3(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C15 C11 C12 117.0(3) . . ?
C15 C11 C10 118.3(3) . . ?
C12 C11 C10 124.7(3) . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
N5 C14 C13 122.5(3) . . ?
N5 C14 H1 118.8 . . ?
C13 C14 H1 118.8 . . ?
N5 C15 C11 123.1(3) . . ?
N5 C15 C16 116.5(2) . . ?
C11 C15 C16 120.4(2) . . ?
N4 C16 C8 123.3(3) . . ?
N4 C16 C15 116.5(2) . . ?
C8 C16 C15 120.2(3) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O2 0.86(3) 2.09(4) 2.932(4) 166(3) 2_576
O2 H1O O1 0.72(3) 2.02(3) 2.733(3) 177(3) .
N1 H2N Cl1 0.83(4) 2.56(4) 3.386(3) 170(3) .

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.075

data_3
_database_code_depnum_ccdc_archive 'CCDC 698653'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
[Cu(cdm)(acac)(H2O)]2.4H2O
;
_chemical_name_common            '[Cu(cdm)(acac)(H2O)]2.4H2O'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 Cu2 N6 O8, 4(H2 O)'
_chemical_formula_sum            'C18 H30 Cu2 N6 O12'
_chemical_formula_weight         649.56

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.1154(10)
_cell_length_b                   8.9932(9)
_cell_length_c                   11.1540(11)
_cell_angle_alpha                113.154(6)
_cell_angle_beta                 101.507(6)
_cell_angle_gamma                101.847(6)
_cell_volume                     696.12(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    5208
_cell_measurement_theta_min      2.09
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             334
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7411
_exptl_absorpt_correction_T_max  0.9246
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5208
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3042
_reflns_number_gt                2607
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.2000P)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_extinction_expression ?
_refine_ls_number_reflns         3042
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.26136(5) 0.42103(4) 0.07985(4) 0.01908(13) Uani 1 1 d . . .
O1 O 0.3034(3) -0.1184(3) 0.3562(2) 0.0247(5) Uani 1 1 d . . .
O2 O 0.2454(3) 0.5455(3) -0.0268(2) 0.0212(5) Uani 1 1 d . . .
O3 O 0.4858(3) 0.5778(3) 0.2084(2) 0.0216(5) Uani 1 1 d . . .
O4 O 0.0997(4) 0.5461(3) 0.2113(3) 0.0229(5) Uani 1 1 d . . .
O5 O 0.9276(7) 0.5857(8) 0.5902(5) 0.122(2) Uani 1 1 d . . .
O6 O 0.6014(6) 0.4823(4) 0.4224(4) 0.0791(13) Uani 1 1 d . . .
N1 N 0.4896(4) 0.1386(3) 0.4118(3) 0.0287(6) Uani 1 1 d . . .
H1A H 0.5628 0.1372 0.4808 0.034 Uiso 1 1 calc R . .
H1B H 0.5140 0.2264 0.3941 0.034 Uiso 1 1 calc R . .
N2 N 0.2790(4) 0.2627(3) 0.1617(3) 0.0248(6) Uani 1 1 d . . .
N3 N -0.0513(4) -0.2360(3) 0.0651(3) 0.0227(6) Uani 1 1 d . . .
C1 C 0.2252(4) 0.0158(4) 0.2216(3) 0.0198(6) Uani 1 1 d . . .
C2 C 0.2562(4) 0.1531(4) 0.1906(3) 0.0188(6) Uani 1 1 d . . .
C3 C 0.0728(4) -0.1223(4) 0.1366(3) 0.0188(6) Uani 1 1 d . . .
C4 C 0.3425(4) 0.0085(4) 0.3343(3) 0.0215(6) Uani 1 1 d . . .
C5 C 0.3168(5) 0.7540(4) -0.1006(4) 0.0280(7) Uani 1 1 d . . .
H5A H 0.2065 0.7814 -0.0973 0.042 Uiso 1 1 calc R . .
H5B H 0.3016 0.6698 -0.1938 0.042 Uiso 1 1 calc R . .
H5C H 0.4128 0.8577 -0.0749 0.042 Uiso 1 1 calc R . .
C6 C 0.3623(4) 0.6821(4) -0.0022(3) 0.0205(6) Uani 1 1 d . . .
C7 C 0.5191(4) 0.7629(4) 0.1051(3) 0.0231(7) Uani 1 1 d . . .
H7 H 0.5971 0.8620 0.1111 0.028 Uiso 1 1 calc R . .
C8 C 0.5731(4) 0.7116(4) 0.2057(3) 0.0217(6) Uani 1 1 d . . .
C9 C 0.7434(5) 0.8157(4) 0.3196(3) 0.0293(7) Uani 1 1 d . . .
H9A H 0.8242 0.7476 0.3150 0.044 Uiso 1 1 calc R . .
H9B H 0.7201 0.8507 0.4079 0.044 Uiso 1 1 calc R . .
H9C H 0.7976 0.9170 0.3104 0.044 Uiso 1 1 calc R . .
H1O H 0.008(5) 0.525(5) 0.160(4) 0.023(11) Uiso 1 1 d . . .
H2O H 0.149(5) 0.635(5) 0.246(4) 0.023(11) Uiso 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 O3 1.917(2) . ?
Cu1 O2 1.931(2) . ?
Cu1 N3 1.977(3) 2 ?
Cu1 N2 1.984(3) . ?
Cu1 O4 2.283(2) . ?
O1 C4 1.251(4) . ?
O2 C6 1.279(3) . ?
O3 C8 1.279(4) . ?
O3 O6 2.892(4) . ?
O4 H1O 0.77(4) . ?
O4 H2O 0.71(4) . ?
O5 O6 2.649(7) . ?
O5 O5 2.655(12) 2_766 ?
O5 O4 2.917(5) 2_666 ?
N1 C4 1.327(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C2 1.144(4) . ?
N3 C3 1.145(4) . ?
N3 Cu1 1.977(3) 2 ?
C1 C3 1.395(4) . ?
C1 C2 1.397(4) . ?
C1 C4 1.451(4) . ?
C5 C6 1.501(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.382(5) . ?
C7 C8 1.399(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.494(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
O3 Cu1 O2 93.81(9) . . ?
O3 Cu1 N3 171.07(10) . 2 ?
O2 Cu1 N3 88.25(10) . 2 ?
O3 Cu1 N2 90.35(10) . . ?
O2 Cu1 N2 170.56(10) . . ?
N3 Cu1 N2 86.38(11) 2 . ?
O3 Cu1 O4 94.53(10) . . ?
O2 Cu1 O4 94.89(9) . . ?
N3 Cu1 O4 93.95(11) 2 . ?
N2 Cu1 O4 93.21(10) . . ?
C6 O2 Cu1 125.3(2) . . ?
C8 O3 Cu1 125.8(2) . . ?
C8 O3 O6 123.0(2) . . ?
Cu1 O3 O6 111.09(11) . . ?
Cu1 O4 H1O 106(3) . . ?
Cu1 O4 H2O 105(3) . . ?
H1O O4 H2O 114(4) . . ?
O6 O5 O5 98.3(3) . 2_766 ?
O6 O5 O4 105.91(18) . 2_666 ?
O5 O5 O4 111.8(3) 2_766 2_666 ?
O5 O6 O3 126.80(18) . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C2 N2 Cu1 166.4(3) . . ?
C3 N3 Cu1 171.3(2) . 2 ?
C3 C1 C2 117.1(3) . . ?
C3 C1 C4 119.0(2) . . ?
C2 C1 C4 123.9(3) . . ?
N2 C2 C1 178.2(3) . . ?
N3 C3 C1 178.9(3) . . ?
O1 C4 N1 121.8(3) . . ?
O1 C4 C1 119.8(3) . . ?
N1 C4 C1 118.4(3) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 C7 125.0(3) . . ?
O2 C6 C5 114.6(3) . . ?
C7 C6 C5 120.4(3) . . ?
C6 C7 C8 125.6(3) . . ?
C6 C7 H7 117.2 . . ?
C8 C7 H7 117.2 . . ?
O3 C8 C7 124.4(3) . . ?
O3 C8 C9 115.7(3) . . ?
C7 C8 C9 119.9(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.88 2.01 2.883(3) 171.3 2_656
N1 H1B O6 0.88 2.14 2.985(4) 161.3 .
O4 H1O O2 0.77(4) 2.09(4) 2.860(4) 176(4) 2_565
O4 H2O O1 0.71(4) 2.03(4) 2.738(3) 175(4) 1_565

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.950
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.095

data_4
_database_code_depnum_ccdc_archive 'CCDC 698654'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
[Cu(cdm)2(NH2(CH2)3NH2)2]
;
_chemical_name_common            '[Cu(cdm)2(NH2(CH2)3NH2)2]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H24 Cu1 N10 O2'
_chemical_formula_sum            'C14 H24 Cu1 N10 O2'
_chemical_formula_weight         427.97

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   17.8128(12)
_cell_length_b                   28.8740(30)
_cell_length_c                   7.1606(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3682.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    5531
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1784
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7583
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5531
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2092
_reflns_number_gt                1866
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.2000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(15)
_refine_ls_number_reflns         2092
_refine_ls_number_parameters     123
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0650
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.027
_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 0.0000 0.5000 0.45904(6) 0.01350(11) Uani 1 2 d S . .
O1 O 0.40685(7) 0.49813(7) 0.4554(5) 0.0161(3) Uani 1 1 d . . .
N1 N 0.31100(11) 0.45058(8) 0.5288(3) 0.0183(5) Uani 1 1 d . . .
C1 C 0.28493(13) 0.52981(8) 0.4519(5) 0.0153(5) Uani 1 1 d . . .
N2 N 0.14349(12) 0.51529(7) 0.4821(4) 0.0216(5) Uani 1 1 d . . .
C2 C 0.20648(14) 0.52250(8) 0.4701(4) 0.0161(5) Uani 1 1 d . . .
N3 N 0.33290(13) 0.61013(8) 0.3581(3) 0.0228(5) Uani 1 1 d . . .
C3 C 0.31126(14) 0.57381(10) 0.4000(4) 0.0168(6) Uani 1 1 d . . .
H3N H 0.0488 0.4500 0.7210 0.050 Uiso 1 1 d . . .
H4N H -0.0329 0.4611 0.7661 0.050 Uiso 1 1 d . . .
H6N H 0.0332 0.4652 0.1613 0.050 Uiso 1 1 d . . .
H1N H 0.2665 0.4497 0.5564 0.050 Uiso 1 1 d . . .
H5N H -0.0312 0.4373 0.2161 0.050 Uiso 1 1 d . . .
H2N H 0.3406 0.4270 0.5471 0.050 Uiso 1 1 d . . .
N4 N 0.00410(11) 0.45138(9) 0.6625(4) 0.0116(6) Uani 1 1 d . . .
C4 C 0.33781(13) 0.49256(8) 0.4793(5) 0.0139(6) Uani 1 1 d . . .
N5 N 0.01475(13) 0.45116(8) 0.2601(3) 0.0133(6) Uani 1 1 d . . .
C5 C -0.01265(14) 0.40420(9) 0.5983(4) 0.0157(5) Uani 1 1 d . . .
H5A H -0.0607 0.4044 0.5289 0.019 Uiso 1 1 calc R . .
H5B H -0.0188 0.3837 0.7081 0.019 Uiso 1 1 calc R . .
C6 C 0.04850(14) 0.38481(8) 0.4733(4) 0.0180(5) Uani 1 1 d . . .
H6A H 0.0314 0.3546 0.4238 0.022 Uiso 1 1 calc R . .
H6B H 0.0936 0.3790 0.5505 0.022 Uiso 1 1 calc R . .
C7 C 0.07105(14) 0.41556(9) 0.3086(4) 0.0177(6) Uani 1 1 d . . .
H7A H 0.1191 0.4311 0.3388 0.021 Uiso 1 1 calc R . .
H7B H 0.0797 0.3957 0.1980 0.021 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 2.021(3) 2_565 ?
Cu1 N5 2.021(3) . ?
Cu1 N4 2.025(3) 2_565 ?
Cu1 N4 2.025(3) . ?
Cu1 N2 2.599(2) . ?
Cu1 N2 2.599(2) 2_565 ?
O1 C4 1.252(3) . ?
N1 C4 1.350(3) . ?
N1 H1N 0.8173 . ?
N1 H2N 0.8712 . ?
C1 C3 1.404(4) . ?
C1 C2 1.419(4) . ?
C1 C4 1.443(3) . ?
N2 C2 1.145(3) . ?
N3 C3 1.157(3) . ?
N4 C5 1.469(3) . ?
N4 H3N 0.9005 . ?
N4 H4N 1.0310 . ?
N5 C7 1.477(3) . ?
N5 H6N 0.8794 . ?
N5 H5N 0.9641 . ?
C5 C6 1.517(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.530(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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 N5 90.41(14) 2_565 . ?
N5 Cu1 N4 91.07(7) 2_565 2_565 ?
N5 Cu1 N4 174.54(9) . 2_565 ?
N5 Cu1 N4 174.54(9) 2_565 . ?
N5 Cu1 N4 91.07(7) . . ?
N4 Cu1 N4 87.94(14) 2_565 . ?
N5 Cu1 N2 93.10(9) 2_565 . ?
N5 Cu1 N2 92.03(8) . . ?
N4 Cu1 N2 82.64(8) 2_565 . ?
N4 Cu1 N2 92.09(8) . . ?
N5 Cu1 N2 92.03(8) 2_565 2_565 ?
N5 Cu1 N2 93.10(9) . 2_565 ?
N4 Cu1 N2 92.09(8) 2_565 2_565 ?
N4 Cu1 N2 82.64(8) . 2_565 ?
N2 Cu1 N2 172.71(13) . 2_565 ?
C4 N1 H1N 115.8 . . ?
C4 N1 H2N 121.8 . . ?
H1N N1 H2N 121.7 . . ?
C3 C1 C2 119.2(2) . . ?
C3 C1 C4 119.5(2) . . ?
C2 C1 C4 121.3(2) . . ?
C2 N2 Cu1 172.0(3) . . ?
N2 C2 C1 177.9(3) . . ?
N3 C3 C1 179.7(3) . . ?
C5 N4 Cu1 114.23(19) . . ?
C5 N4 H3N 106.5 . . ?
Cu1 N4 H3N 113.4 . . ?
C5 N4 H4N 110.4 . . ?
Cu1 N4 H4N 107.8 . . ?
H3N N4 H4N 104.1 . . ?
O1 C4 N1 119.9(2) . . ?
O1 C4 C1 121.8(2) . . ?
N1 C4 C1 118.3(2) . . ?
C7 N5 Cu1 114.10(18) . . ?
C7 N5 H6N 104.8 . . ?
Cu1 N5 H6N 107.1 . . ?
C7 N5 H5N 111.4 . . ?
Cu1 N5 H5N 114.2 . . ?
H6N N5 H5N 104.2 . . ?
N4 C5 C6 112.4(2) . . ?
N4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 115.4(2) . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C7 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
N5 C7 C6 114.0(2) . . ?
N5 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N5 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?

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
N4 H3N O1 0.90 2.38 3.007(4) 126.3 10_565
N4 H4N O1 1.03 2.03 3.037(4) 163.8 9_455
N5 H6N O1 0.88 2.11 2.976(4) 170.0 10_564
N5 H5N N3 0.96 2.53 3.335(3) 140.7 7_544
N1 H2N N3 0.87 2.40 3.274(3) 176.9 15_545

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.061

data_5
_database_code_depnum_ccdc_archive 'CCDC 698655'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
MnPhenCl
;
_chemical_name_common            MnPhenCl
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H19 Cl1 Mn1 N7 O1.50, C1 O1 H4'
_chemical_formula_sum            'C29 H23 Cl1 Mn1 N7 O2.50'
_chemical_formula_weight         599.93

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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                   10.5476(7)
_cell_length_b                   11.5860(7)
_cell_length_c                   12.2153(7)
_cell_angle_alpha                88.998(3)
_cell_angle_beta                 67.186(2)
_cell_angle_gamma                84.951(3)
_cell_volume                     1370.42(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    21186
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             614
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8353
_exptl_absorpt_correction_T_max  0.8856
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21186
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.49
_reflns_number_total             6270
_reflns_number_gt                5152
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.2000P)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_extinction_expression ?
_refine_ls_number_reflns         6270
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
Mn1 Mn 0.36462(3) 0.19778(2) 0.26708(3) 0.01762(10) Uani 1 1 d . . .
Cl1 Cl 0.38510(5) -0.00110(4) 0.18791(5) 0.02302(13) Uani 1 1 d . . .
O1 O 0.57829(15) 0.21548(12) 0.19990(13) 0.0238(3) Uani 1 1 d . . .
N5 N 0.35142(19) 0.39488(15) 0.30797(16) 0.0220(4) Uani 1 1 d . . .
C4 C 0.6946(2) 0.16477(17) 0.13984(18) 0.0190(4) Uani 1 1 d . . .
N4 N 0.32251(18) 0.29251(14) 0.12127(15) 0.0205(4) Uani 1 1 d . . .
N1 N 0.7088(2) 0.07879(16) 0.06314(17) 0.0238(4) Uani 1 1 d . . .
C2 C 0.9486(2) 0.15290(17) 0.08914(18) 0.0208(4) Uani 1 1 d . . .
C16 C 0.3255(2) 0.40990(18) 0.12118(19) 0.0217(4) Uani 1 1 d . . .
C1 C 0.8140(2) 0.20330(17) 0.15244(18) 0.0197(4) Uani 1 1 d . . .
C15 C 0.3436(2) 0.46367(18) 0.21883(19) 0.0223(4) Uani 1 1 d . . .
C3 C 0.7929(2) 0.29895(18) 0.22844(19) 0.0231(4) Uani 1 1 d . . .
C14 C 0.3695(3) 0.4445(2) 0.3967(2) 0.0294(5) Uani 1 1 d . . .
H14 H 0.3735 0.3973 0.4598 0.035 Uiso 1 1 calc R . .
C8 C 0.3144(3) 0.4785(2) 0.0289(2) 0.0290(5) Uani 1 1 d . . .
C10 C 0.3428(3) 0.6512(2) 0.1225(2) 0.0368(6) Uani 1 1 d . . .
H10 H 0.3494 0.7325 0.1224 0.044 Uiso 1 1 calc R . .
C5 C 0.3079(2) 0.2429(2) 0.0303(2) 0.0275(5) Uani 1 1 d . . .
H5 H 0.3085 0.1609 0.0285 0.033 Uiso 1 1 calc R . .
C11 C 0.3534(2) 0.58407(19) 0.2182(2) 0.0287(5) Uani 1 1 d . . .
C12 C 0.3760(3) 0.6322(2) 0.3135(2) 0.0370(6) Uani 1 1 d . . .
H12 H 0.3864 0.7126 0.3155 0.044 Uiso 1 1 calc R . .
C9 C 0.3238(3) 0.6009(2) 0.0326(2) 0.0384(6) Uani 1 1 d . . .
H9 H 0.3163 0.6474 -0.0298 0.046 Uiso 1 1 calc R . .
C13 C 0.3830(3) 0.5631(2) 0.4026(2) 0.0388(6) Uani 1 1 d . . .
H13 H 0.3968 0.5949 0.4679 0.047 Uiso 1 1 calc R . .
N6 N 0.37304(18) 0.16318(14) 0.44731(15) 0.0203(4) Uani 1 1 d . . .
N7 N 0.14381(18) 0.18253(15) 0.39633(15) 0.0208(4) Uani 1 1 d . . .
C7 C 0.2961(3) 0.4227(2) -0.0644(2) 0.0355(6) Uani 1 1 d . . .
H7 H 0.2871 0.4663 -0.1279 0.043 Uiso 1 1 calc R . .
C6 C 0.2915(3) 0.3054(2) -0.0630(2) 0.0355(6) Uani 1 1 d . . .
H6 H 0.2773 0.2667 -0.1246 0.043 Uiso 1 1 calc R . .
C28 C 0.2515(2) 0.14001(16) 0.53468(18) 0.0193(4) Uani 1 1 d . . .
C27 C 0.1299(2) 0.15017(17) 0.50797(18) 0.0203(4) Uani 1 1 d . . .
C18 C 0.4841(3) 0.12364(18) 0.5833(2) 0.0267(5) Uani 1 1 d . . .
H18 H 0.5671 0.1186 0.5971 0.032 Uiso 1 1 calc R . .
C17 C 0.4851(2) 0.15627(18) 0.4722(2) 0.0243(5) Uani 1 1 d . . .
H17 H 0.5698 0.1743 0.4119 0.029 Uiso 1 1 calc R . .
C20 C 0.2413(2) 0.10736(17) 0.64940(19) 0.0237(5) Uani 1 1 d . . .
C19 C 0.3627(3) 0.09908(18) 0.6716(2) 0.0271(5) Uani 1 1 d . . .
H19 H 0.3606 0.0766 0.7474 0.033 Uiso 1 1 calc R . .
C26 C 0.0320(2) 0.1926(2) 0.3720(2) 0.0271(5) Uani 1 1 d . . .
H26 H 0.0406 0.2166 0.2949 0.032 Uiso 1 1 calc R . .
C21 C 0.1092(3) 0.0846(2) 0.7372(2) 0.0305(5) Uani 1 1 d . . .
H21 H 0.1019 0.0632 0.8147 0.037 Uiso 1 1 calc R . .
C22 C -0.0043(3) 0.0930(2) 0.7120(2) 0.0319(5) Uani 1 1 d . . .
H22 H -0.0903 0.0766 0.7716 0.038 Uiso 1 1 calc R . .
C23 C 0.0025(2) 0.12643(18) 0.5960(2) 0.0259(5) Uani 1 1 d . . .
C24 C -0.1126(2) 0.1365(2) 0.5655(2) 0.0324(5) Uani 1 1 d . . .
H24 H -0.2004 0.1202 0.6221 0.039 Uiso 1 1 calc R . .
C25 C -0.0984(2) 0.1699(2) 0.4541(2) 0.0329(5) Uani 1 1 d . . .
H25 H -0.1761 0.1777 0.4325 0.040 Uiso 1 1 calc R . .
N2 N 1.05751(19) 0.10881(16) 0.03792(17) 0.0279(4) Uani 1 1 d . . .
N3 N 0.7737(2) 0.37725(18) 0.29152(18) 0.0349(5) Uani 1 1 d . . .
O2 O 0.8264(3) 0.61202(19) 0.3001(3) 0.0820(9) Uani 1 1 d . . .
H2 H 0.7951 0.5469 0.3074 0.098 Uiso 1 1 calc R . .
H2N H 0.787(3) 0.040(2) 0.026(2) 0.031(7) Uiso 1 1 d . . .
H1N H 0.637(3) 0.055(2) 0.062(2) 0.034(7) Uiso 1 1 d . . .
O3 O -0.0151(9) 0.4667(11) 0.5523(7) 0.171(5) Uani 0.50 1 d P A -1
C29 C 0.9590(5) 0.6062(4) 0.2081(5) 0.0971(16) Uani 1 1 d . . .
H29A H 0.9692 0.6774 0.1621 0.146 Uiso 1 1 calc R . .
H29B H 0.9706 0.5394 0.1559 0.146 Uiso 1 1 calc R . .
H29C H 1.0292 0.5978 0.2425 0.146 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
Mn1 O1 2.1062(15) . ?
Mn1 N4 2.2436(18) . ?
Mn1 N6 2.2649(17) . ?
Mn1 N7 2.2715(18) . ?
Mn1 N5 2.3268(17) . ?
Mn1 Cl1 2.4738(6) . ?
O1 C4 1.256(2) . ?
N5 C14 1.320(3) . ?
N5 C15 1.362(3) . ?
C4 N1 1.338(3) . ?
C4 C1 1.436(3) . ?
N4 C5 1.326(3) . ?
N4 C16 1.363(3) . ?
N1 H2N 0.86(3) . ?
N1 H1N 0.84(3) . ?
C2 N2 1.150(3) . ?
C2 C1 1.404(3) . ?
C16 C8 1.405(3) . ?
C16 C15 1.439(3) . ?
C1 C3 1.404(3) . ?
C15 C11 1.407(3) . ?
C3 N3 1.153(3) . ?
C14 C13 1.400(3) . ?
C14 H14 0.9500 . ?
C8 C7 1.403(3) . ?
C8 C9 1.433(3) . ?
C10 C9 1.341(4) . ?
C10 C11 1.428(3) . ?
C10 H10 0.9500 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9500 . ?
C11 C12 1.409(3) . ?
C12 C13 1.361(4) . ?
C12 H12 0.9500 . ?
C9 H9 0.9500 . ?
C13 H13 0.9500 . ?
N6 C17 1.325(3) . ?
N6 C28 1.358(3) . ?
N7 C26 1.319(3) . ?
N7 C27 1.363(3) . ?
C7 C6 1.363(3) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C28 C20 1.411(3) . ?
C28 C27 1.436(3) . ?
C27 C23 1.404(3) . ?
C18 C19 1.366(3) . ?
C18 C17 1.399(3) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?
C20 C19 1.404(3) . ?
C20 C21 1.434(3) . ?
C19 H19 0.9500 . ?
C26 C25 1.397(3) . ?
C26 H26 0.9500 . ?
C21 C22 1.342(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.438(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(3) . ?
C24 C25 1.363(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
O2 C29 1.411(5) . ?
O2 H2 0.8400 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Mn1 N4 96.59(6) . . ?
O1 Mn1 N6 88.29(6) . . ?
N4 Mn1 N6 159.58(6) . . ?
O1 Mn1 N7 161.21(6) . . ?
N4 Mn1 N7 99.23(6) . . ?
N6 Mn1 N7 73.41(6) . . ?
O1 Mn1 N5 82.44(6) . . ?
N4 Mn1 N5 73.02(6) . . ?
N6 Mn1 N5 88.07(6) . . ?
N7 Mn1 N5 92.51(6) . . ?
O1 Mn1 Cl1 95.83(4) . . ?
N4 Mn1 Cl1 97.46(5) . . ?
N6 Mn1 Cl1 101.77(4) . . ?
N7 Mn1 Cl1 92.13(5) . . ?
N5 Mn1 Cl1 169.98(5) . . ?
C4 O1 Mn1 143.46(13) . . ?
C14 N5 C15 117.83(18) . . ?
C14 N5 Mn1 127.87(15) . . ?
C15 N5 Mn1 113.58(13) . . ?
O1 C4 N1 121.37(19) . . ?
O1 C4 C1 118.49(18) . . ?
N1 C4 C1 120.11(19) . . ?
C5 N4 C16 117.88(18) . . ?
C5 N4 Mn1 125.28(15) . . ?
C16 N4 Mn1 116.54(13) . . ?
C4 N1 H2N 121.8(17) . . ?
C4 N1 H1N 117.9(18) . . ?
H2N N1 H1N 119(2) . . ?
N2 C2 C1 178.2(2) . . ?
N4 C16 C8 122.43(19) . . ?
N4 C16 C15 117.95(18) . . ?
C8 C16 C15 119.61(19) . . ?
C3 C1 C2 119.72(18) . . ?
C3 C1 C4 117.22(18) . . ?
C2 C1 C4 123.01(18) . . ?
N5 C15 C11 122.8(2) . . ?
N5 C15 C16 118.09(18) . . ?
C11 C15 C16 119.1(2) . . ?
N3 C3 C1 179.0(3) . . ?
N5 C14 C13 123.4(2) . . ?
N5 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
C7 C8 C16 117.8(2) . . ?
C7 C8 C9 123.0(2) . . ?
C16 C8 C9 119.2(2) . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
N4 C5 C6 123.2(2) . . ?
N4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C15 C11 C12 117.1(2) . . ?
C15 C11 C10 119.9(2) . . ?
C12 C11 C10 123.0(2) . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C12 C13 C14 119.0(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C17 N6 C28 118.29(18) . . ?
C17 N6 Mn1 126.33(15) . . ?
C28 N6 Mn1 115.23(13) . . ?
C26 N7 C27 117.86(19) . . ?
C26 N7 Mn1 127.00(15) . . ?
C27 N7 Mn1 114.91(14) . . ?
C6 C7 C8 119.5(2) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C6 C5 119.2(2) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N6 C28 C20 122.4(2) . . ?
N6 C28 C27 118.04(18) . . ?
C20 C28 C27 119.60(19) . . ?
N7 C27 C23 122.6(2) . . ?
N7 C27 C28 117.86(19) . . ?
C23 C27 C28 119.58(19) . . ?
C19 C18 C17 119.3(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
N6 C17 C18 123.0(2) . . ?
N6 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
C19 C20 C28 117.6(2) . . ?
C19 C20 C21 123.2(2) . . ?
C28 C20 C21 119.2(2) . . ?
C18 C19 C20 119.5(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
N7 C26 C25 123.3(2) . . ?
N7 C26 H26 118.4 . . ?
C25 C26 H26 118.4 . . ?
C22 C21 C20 121.3(2) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 120.9(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C27 117.5(2) . . ?
C24 C23 C22 123.1(2) . . ?
C27 C23 C22 119.4(2) . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 119.0(2) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C29 O2 H2 109.5 . . ?
O2 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N3 0.84 2.02 2.835(3) 163.9 .
N1 H2N N2 0.86(3) 2.20(3) 3.019(3) 159(2) 2_755
N1 H1N Cl1 0.84(3) 2.64(3) 3.363(2) 146(2) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.069


