# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Fabrizia Grepioni'
_publ_contact_author_email       FABRIZIA.GREPIONI@UNIBO.IT

_publ_section_title              
;
Drug-containing coordination
and hydrogen bonding networks obtained mechanochemically
;
loop_
_publ_author_name
'Fabrizia Grepioni'
'Vania Andre'
'Dario Braga'
'Maria Duarte'

# Attachment '1-rev.CIF'

data_1
_database_code_depnum_ccdc_archive 'CCDC 723417'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 Ag N3 O9'
_chemical_formula_weight         474.14

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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pmcn

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

_cell_length_a                   28.665(3)
_cell_length_b                   5.402(7)
_cell_length_c                   10.882(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1685(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    1.253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8944
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5150
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_sigmaI/netI    0.2689
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         27.99
_reflns_number_total             1835
_reflns_number_gt                659
_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)+(0.0284P)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_number_reflns         1835
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2363
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0714
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_restrained_S_all      0.864
_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
Ag1 Ag 0.2500 0.32495(15) 0.26470(11) 0.0481(4) Uani 1 2 d S . .
O1 O 0.13469(13) -0.2171(8) -0.0813(5) 0.0404(16) Uani 1 1 d . . .
H1 H 0.1124 -0.3074 -0.0964 0.061 Uiso 1 1 calc R . .
O2 O 0.05162(16) -0.4054(9) -0.0454(5) 0.0438(18) Uani 1 1 d . . .
O3 O 0.00694(16) -0.2419(9) 0.1037(6) 0.0572(18) Uani 1 1 d . . .
H2 H -0.0087 -0.3675 0.0939 0.086 Uiso 1 1 calc R . .
N1 N 0.18111(16) 0.4712(9) 0.1657(6) 0.033(2) Uani 1 1 d . . .
C1 C 0.08095(14) -0.0682(8) 0.0738(5) 0.027(2) Uani 1 1 d G . .
C2 C 0.12300(16) -0.0564(8) 0.0104(4) 0.023(2) Uani 1 1 d G . .
C3 C 0.15591(12) 0.1220(9) 0.0413(5) 0.031(2) Uani 1 1 d G . .
H3 H 0.1840 0.1299 -0.0011 0.037 Uiso 1 1 calc R . .
C4 C 0.14677(13) 0.2887(8) 0.1356(5) 0.030(2) Uani 1 1 d G . .
C5 C 0.10473(16) 0.2770(9) 0.1990(4) 0.044(3) Uani 1 1 d G . .
H5 H 0.0986 0.3885 0.2620 0.052 Uiso 1 1 calc R . .
C6 C 0.07182(12) 0.0985(9) 0.1680(5) 0.042(3) Uani 1 1 d G . .
H6 H 0.0437 0.0907 0.2104 0.051 Uiso 1 1 calc R . .
C7 C 0.0458(2) -0.2569(15) 0.0363(8) 0.034(2) Uani 1 1 d . . .
N2 N 0.2500 -0.153(2) 0.3864(14) 0.044(4) Uani 1 2 d S . .
O4 O 0.2500 -0.3456(14) 0.4411(8) 0.050(3) Uani 1 2 d S . .
O5 O 0.2500 0.0519(14) 0.4458(9) 0.053(3) Uani 1 2 d S . .
O6 O 0.2500 -0.1363(16) 0.2750(11) 0.063(3) Uani 1 2 d S . .

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
Ag1 0.0498(4) 0.0405(4) 0.0541(10) 0.0063(8) 0.000 0.000
O1 0.035(3) 0.040(3) 0.046(5) -0.008(4) 0.011(3) -0.012(2)
O2 0.045(3) 0.054(4) 0.033(5) -0.025(4) 0.012(3) -0.021(3)
O3 0.049(3) 0.068(4) 0.054(5) -0.021(4) 0.018(3) -0.033(3)
N1 0.028(3) 0.030(3) 0.040(6) 0.005(4) -0.022(3) -0.009(3)
C1 0.026(4) 0.048(5) 0.009(6) 0.009(5) 0.004(4) -0.005(4)
C2 0.030(4) 0.025(4) 0.015(6) -0.003(5) 0.007(4) 0.010(4)
C3 0.024(3) 0.027(4) 0.042(7) 0.005(5) 0.006(4) -0.003(3)
C4 0.032(4) 0.035(4) 0.022(6) 0.003(5) -0.007(4) 0.013(4)
C5 0.043(4) 0.056(5) 0.032(7) -0.031(5) 0.007(4) -0.010(4)
C6 0.036(4) 0.064(6) 0.027(7) -0.011(5) 0.010(4) -0.012(4)
C7 0.034(4) 0.046(5) 0.023(7) 0.006(5) 0.000(5) -0.010(5)
N2 0.019(4) 0.048(8) 0.064(12) 0.048(11) 0.000 0.000
O4 0.057(4) 0.040(5) 0.054(8) 0.035(6) 0.000 0.000
O5 0.064(5) 0.029(5) 0.067(10) -0.012(6) 0.000 0.000
O6 0.097(6) 0.020(4) 0.071(9) 0.018(8) 0.000 0.000

_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
Ag1 N1 2.384(5) . ?
Ag1 N1 2.384(5) 7_655 ?
Ag1 O5 2.462(9) . ?
Ag1 O6 2.494(10) . ?
O1 C2 1.365(6) . ?
O1 H1 0.8200 . ?
O2 C7 1.209(8) . ?
O3 C7 1.337(8) . ?
O3 H2 0.8200 . ?
N1 C4 1.431(6) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.490(8) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N2 O4 1.198(12) . ?
N2 O6 1.215(13) . ?
N2 O5 1.282(14) . ?

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
N1 Ag1 N1 111.8(3) . 7_655 ?
N1 Ag1 O5 124.09(14) . . ?
N1 Ag1 O5 124.09(13) 7_655 . ?
N1 Ag1 O6 110.57(19) . . ?
N1 Ag1 O6 110.57(19) 7_655 . ?
O5 Ag1 O6 50.6(3) . . ?
C2 O1 H1 109.5 . . ?
C7 O3 H2 109.5 . . ?
C4 N1 Ag1 116.4(3) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 C7 118.8(5) . . ?
C6 C1 C7 121.2(5) . . ?
O1 C2 C3 116.8(4) . . ?
O1 C2 C1 123.1(4) . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 N1 121.0(4) . . ?
C3 C4 N1 119.0(4) . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O2 C7 O3 124.0(7) . . ?
O2 C7 C1 124.2(7) . . ?
O3 C7 C1 111.8(7) . . ?
O4 N2 O6 124.1(16) . . ?
O4 N2 O5 119.9(14) . . ?
O6 N2 O5 116.0(14) . . ?
N2 O5 Ag1 96.6(9) . . ?
N2 O6 Ag1 96.9(10) . . ?

_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.110

# Attachment '1H2O-rev.CIF'

data_1_H2O
_database_code_depnum_ccdc_archive 'CCDC 723418'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H28 Ag2 N6 O20'
_chemical_formula_weight         984.30

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'
Ag Ag -0.8971 1.1015 '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                   7.580(5)
_cell_length_b                   7.627(5)
_cell_length_c                   17.111(5)
_cell_angle_alpha                92.062(5)
_cell_angle_beta                 97.578(5)
_cell_angle_gamma                118.434(5)
_cell_volume                     856.7(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    1.240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8673
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5742
_diffrn_reflns_av_R_equivalents  0.1647
_diffrn_reflns_av_sigmaI/netI    0.7254
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2872
_reflns_number_gt                519
_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)+(0.0230P)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_number_reflns         2872
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3692
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   0.633
_refine_ls_restrained_S_all      0.633
_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
Ag1 Ag 0.3508(3) 0.4474(2) 0.39499(7) 0.0759(6) Uani 1 1 d . . .
O1 O 0.3706(19) -0.3510(14) 0.2585(4) 0.070(4) Uani 1 1 d . . .
H1 H 0.3590 -0.4215 0.2187 0.105 Uiso 1 1 calc R . .
O2 O 0.3027(14) -0.4574(14) 0.1046(4) 0.059(3) Uani 1 1 d . . .
O3 O 0.2822(18) -0.2456(16) 0.0248(5) 0.071(4) Uani 1 1 d . . .
H2 H 0.3233 -0.2958 -0.0065 0.107 Uiso 1 1 calc R . .
O4 O -0.1355(14) -0.3709(13) 0.2407(4) 0.072(4) Uani 1 1 d . . .
H7 H -0.1599 -0.4434 0.1997 0.108 Uiso 1 1 calc R . .
O5 O -0.2036(13) -0.4729(13) 0.0877(4) 0.050(3) Uani 1 1 d . . .
O6 O -0.2279(19) -0.2593(15) 0.0072(5) 0.077(4) Uani 1 1 d . . .
H8 H -0.2044 -0.3224 -0.0259 0.116 Uiso 1 1 calc R . .
N1 N 0.5684(15) 0.3329(15) 0.3474(5) 0.049(4) Uani 1 1 d . . .
N2 N 0.0042(15) 0.2945(15) 0.3330(5) 0.047(4) Uani 1 1 d . . .
N3 N 0.171(3) 0.743(3) 0.4737(10) 0.067(6) Uani 1 1 d . . .
O8 O 0.3148(19) 0.720(2) 0.4801(7) 0.084(5) Uani 1 1 d . . .
O9 O 0.1649(18) 0.8745(17) 0.5203(6) 0.087(5) Uani 1 1 d . . .
O10 O 0.0150(19) 0.645(2) 0.4201(7) 0.091(5) Uani 1 1 d . . .
C1 C 0.3633(13) -0.1359(12) 0.1606(4) 0.043(4) Uiso 1 1 d G . .
C2 C 0.3949(14) -0.1746(10) 0.2385(6) 0.061(5) Uiso 1 1 d G . .
C3 C 0.4550(13) -0.0248(14) 0.3007(4) 0.051(4) Uiso 1 1 d G . .
H3 H 0.4762 -0.0507 0.3528 0.062 Uiso 1 1 calc R . .
C4 C 0.4835(13) 0.1636(12) 0.2849(4) 0.051(5) Uiso 1 1 d G . .
C5 C 0.4519(12) 0.2022(10) 0.2070(5) 0.037(4) Uiso 1 1 d G . .
H5 H 0.4709 0.3283 0.1965 0.044 Uiso 1 1 calc R . .
C6 C 0.3918(12) 0.0525(14) 0.1449(3) 0.050(4) Uiso 1 1 d G . .
H6 H 0.3706 0.0783 0.0928 0.060 Uiso 1 1 calc R . .
C7 C 0.317(3) -0.294(3) 0.0985(9) 0.061(6) Uiso 1 1 d . . .
C8 C -0.1387(13) -0.1492(12) 0.1444(4) 0.042(4) Uiso 1 1 d G . .
C9 C -0.1136(14) -0.1902(10) 0.2224(6) 0.060(5) Uiso 1 1 d G . .
C10 C -0.0664(13) -0.0448(14) 0.2847(4) 0.051(4) Uiso 1 1 d G . .
H10 H -0.0496 -0.0723 0.3369 0.061 Uiso 1 1 calc R . .
C11 C -0.0443(13) 0.1415(12) 0.2691(4) 0.043(4) Uiso 1 1 d G . .
C12 C -0.0694(13) 0.1825(10) 0.1912(5) 0.050(4) Uiso 1 1 d G . .
H12 H -0.0546 0.3072 0.1808 0.060 Uiso 1 1 calc R . .
C13 C -0.1166(12) 0.0372(14) 0.1289(3) 0.051(4) Uiso 1 1 d G . .
H13 H -0.1334 0.0646 0.0767 0.062 Uiso 1 1 calc R . .
C14 C -0.189(2) -0.308(2) 0.0795(8) 0.040(5) Uiso 1 1 d . . .
O7 O 0.2947(13) 0.2791(12) 0.5272(4) 0.050(3) Uani 1 1 d . . .

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
Ag1 0.0784(14) 0.0871(13) 0.0528(8) -0.0093(7) -0.0047(7) 0.0376(11)
O1 0.102(11) 0.053(9) 0.051(6) 0.000(6) -0.022(7) 0.044(9)
O2 0.077(10) 0.049(9) 0.051(6) -0.001(5) -0.002(6) 0.035(8)
O3 0.102(12) 0.065(9) 0.054(7) -0.005(6) 0.007(7) 0.049(9)
O4 0.099(12) 0.064(10) 0.047(6) -0.005(6) -0.003(6) 0.039(9)
O5 0.086(10) 0.038(8) 0.034(6) 0.000(5) -0.002(5) 0.039(8)
O6 0.135(13) 0.070(10) 0.044(7) -0.007(6) 0.001(7) 0.068(9)
N1 0.023(10) 0.067(10) 0.044(7) -0.024(6) -0.006(6) 0.016(9)
N2 0.024(10) 0.059(10) 0.043(7) -0.034(6) 0.007(6) 0.011(9)
N3 0.06(2) 0.066(17) 0.082(14) 0.027(11) 0.005(13) 0.036(17)
O8 0.052(13) 0.113(12) 0.101(9) -0.002(7) -0.007(8) 0.056(11)
O9 0.107(13) 0.064(11) 0.107(10) -0.005(7) 0.023(8) 0.056(10)
O10 0.025(11) 0.121(13) 0.127(11) -0.006(9) -0.008(8) 0.043(10)
O7 0.031(9) 0.054(8) 0.056(6) -0.003(5) 0.000(5) 0.016(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
Ag1 N2 2.376(10) . ?
Ag1 N1 2.413(9) . ?
Ag1 O7 2.625(9) . ?
Ag1 O7 2.620(9) 2_666 ?
Ag1 O8 2.635(14) . ?
O1 C2 1.332(8) . ?
O1 H1 0.8200 . ?
O2 C7 1.207(13) . ?
O3 C7 1.354(14) . ?
O3 H2 0.8200 . ?
O4 C9 1.361(8) . ?
O4 H7 0.8200 . ?
O5 C14 1.227(12) . ?
O6 C14 1.339(12) . ?
O6 H8 0.8200 . ?
N1 C4 1.467(10) . ?
N2 C11 1.444(9) . ?
N3 O8 1.172(15) . ?
N3 O9 1.282(16) . ?
N3 O10 1.275(17) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.455(15) . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C8 C14 1.481(13) . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
O7 Ag1 2.620(9) 2_666 ?

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 Ag1 N1 118.6(3) . . ?
N2 Ag1 O7 159.5(2) . 2_666 ?
N1 Ag1 O7 79.9(3) . 2_666 ?
C2 O1 H1 109.5 . . ?
C7 O3 H2 109.5 . . ?
C9 O4 H7 109.5 . . ?
C14 O6 H8 109.5 . . ?
C4 N1 Ag1 120.1(6) . . ?
C11 N2 Ag1 112.3(6) . . ?
O8 N3 O9 121(2) . . ?
O8 N3 O10 124(2) . . ?
O9 N3 O10 115.4(17) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 C7 116.9(10) . . ?
C6 C1 C7 122.9(10) . . ?
O1 C2 C3 116.4(8) . . ?
O1 C2 C1 123.6(8) . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 N1 122.1(7) . . ?
C5 C4 N1 117.6(7) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O2 C7 O3 118.3(14) . . ?
O2 C7 C1 129.0(15) . . ?
O3 C7 C1 112.7(14) . . ?
C9 C8 C13 120.0 . . ?
C9 C8 C14 118.5(9) . . ?
C13 C8 C14 121.5(9) . . ?
O4 C9 C8 122.2(8) . . ?
O4 C9 C10 117.8(8) . . ?
C8 C9 C10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 N2 120.9(8) . . ?
C12 C11 N2 119.1(8) . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
O5 C14 O6 120.4(12) . . ?
O5 C14 C8 125.8(12) . . ?
O6 C14 C8 113.7(12) . . ?

_diffrn_measured_fraction_theta_max 0.898
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.898
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.084

# Attachment '2-rev.CIF'

data_2
_database_code_depnum_ccdc_archive 'CCDC 723419'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H28 Cl2 N4 Ni1 O8'
_chemical_formula_weight         485.97

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'
Cl Cl 0.1484 0.1585 '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'
Ni Ni 0.3393 1.1124 '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)/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                   9.6316(7)
_cell_length_b                   7.3983(5)
_cell_length_c                   15.8730(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.769(6)
_cell_angle_gamma                90.00
_cell_volume                     1035.13(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            light_green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    1.240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9238
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4466
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_sigmaI/netI    0.1864
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1817
_reflns_number_gt                955
_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)+(0.2000P)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_number_reflns         1817
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1543
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.2429
_refine_ls_wR_factor_gt          0.1879
_refine_ls_goodness_of_fit_ref   0.728
_refine_ls_restrained_S_all      0.728
_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
Ni1 Ni 0.0000 0.0000 0.0000 0.0200(5) Uani 1 2 d S . .
O1 O 0.2176(6) 0.0114(9) 0.0979(4) 0.0286(15) Uani 1 1 d . . .
H1 H 0.2330 0.0789 0.1445 0.034 Uiso 1 1 d R . .
H2 H 0.2440 -0.0861 0.1155 0.034 Uiso 1 1 d R . .
O2 O -0.0328(7) -0.1958(9) 0.0844(4) 0.0287(16) Uani 1 1 d . . .
O3 O -0.0542(6) -0.7964(8) 0.0678(4) 0.0260(15) Uani 1 1 d . . .
N1 N -0.1942(9) -0.3940(12) -0.0163(5) 0.044(2) Uani 1 1 d . . .
H10 H -0.2121 -0.3310 -0.0625 0.053 Uiso 1 1 d R . .
H11 H -0.2361 -0.4880 -0.0205 0.053 Uiso 1 1 d R . .
N2 N -0.1897(8) -0.6170(10) 0.1217(5) 0.0262(19) Uani 1 1 d . . .
C1 C -0.1038(9) -0.3407(13) 0.0661(6) 0.024(2) Uani 1 1 d . . .
C2 C -0.0852(10) -0.4663(11) 0.1451(6) 0.024(2) Uani 1 1 d . . .
H2A H 0.0178 -0.5125 0.1704 0.029 Uiso 1 1 d R . .
H2B H -0.0985 -0.3968 0.1931 0.029 Uiso 1 1 d R . .
C3 C -0.1660(10) -0.7744(13) 0.0876(6) 0.025(2) Uani 1 1 d . . .
C4 C -0.2907(10) -0.9014(14) 0.0787(7) 0.030(2) Uani 1 1 d . . .
H4A H -0.2561 -0.9933 0.1263 0.036 Uiso 1 1 d R . .
H4B H -0.3292 -0.9600 0.0190 0.036 Uiso 1 1 d R . .
C5 C -0.4113(12) -0.7850(15) 0.0897(8) 0.046(3) Uani 1 1 d . . .
H5A H -0.4601 -0.8477 0.1241 0.056 Uiso 1 1 d R . .
H5B H -0.4877 -0.7514 0.0300 0.056 Uiso 1 1 d R . .
C6 C -0.3269(12) -0.6208(14) 0.1403(8) 0.047(3) Uani 1 1 d . . .
H6A H -0.3865 -0.5120 0.1174 0.057 Uiso 1 1 d R . .
H6B H -0.3018 -0.6322 0.2057 0.057 Uiso 1 1 d R . .
O4 O -0.3621(7) -0.6858(9) -0.1467(5) 0.0433(19) Uani 1 1 d . . .
H3 H -0.4477 -0.7113 -0.1801 0.052 Uiso 1 1 d R . .
H4 H -0.3437 -0.5973 -0.1771 0.052 Uiso 1 1 d R . .
Cl1 Cl 0.3087(3) -0.6794(4) 0.24174(16) 0.0376(7) Uani 1 1 d . . .

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
Ni1 0.0240(8) 0.0087(9) 0.0273(9) -0.0020(8) 0.0101(6) -0.0012(8)
O1 0.029(3) 0.021(4) 0.030(3) -0.001(3) 0.006(3) 0.003(3)
O2 0.036(4) 0.018(4) 0.031(4) -0.009(3) 0.013(3) -0.013(3)
O3 0.022(3) 0.019(4) 0.035(4) -0.005(3) 0.010(3) -0.009(3)
N1 0.061(6) 0.028(6) 0.026(4) 0.016(4) -0.002(4) -0.011(5)
N2 0.035(4) 0.020(5) 0.038(5) 0.002(4) 0.030(4) 0.000(4)
C1 0.023(4) 0.024(6) 0.031(5) -0.004(5) 0.015(4) 0.007(4)
C2 0.040(5) 0.013(6) 0.023(5) -0.011(4) 0.017(4) -0.010(4)
C3 0.034(5) 0.021(6) 0.019(5) 0.007(4) 0.009(4) -0.005(4)
C4 0.034(5) 0.024(6) 0.039(6) -0.006(5) 0.021(4) -0.006(5)
C5 0.049(7) 0.032(7) 0.073(8) -0.012(6) 0.040(6) -0.013(6)
C6 0.052(6) 0.036(7) 0.072(8) -0.010(7) 0.044(6) -0.005(6)
O4 0.040(4) 0.022(4) 0.050(4) 0.002(4) 0.000(3) -0.001(3)
Cl1 0.0419(14) 0.0319(16) 0.0327(13) -0.0033(12) 0.0083(10) 0.0036(13)

_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
Ni1 O3 2.038(6) 1_565 ?
Ni1 O3 2.038(6) 3_545 ?
Ni1 O1 2.047(5) . ?
Ni1 O1 2.047(5) 3 ?
Ni1 O2 2.082(6) . ?
Ni1 O2 2.082(6) 3 ?
O1 H1 0.8544 . ?
O1 H2 0.7783 . ?
O2 C1 1.242(11) . ?
O3 C3 1.247(10) . ?
O3 Ni1 2.038(6) 1_545 ?
N1 C1 1.305(11) . ?
N1 H10 0.8263 . ?
N1 H11 0.7933 . ?
N2 C3 1.342(12) . ?
N2 C2 1.447(11) . ?
N2 C6 1.466(11) . ?
C1 C2 1.512(12) . ?
C2 H2A 0.9701 . ?
C2 H2B 0.9695 . ?
C3 C4 1.487(12) . ?
C4 C5 1.511(13) . ?
C4 H4A 0.9702 . ?
C4 H4B 0.9696 . ?
C5 C6 1.501(14) . ?
C5 H5A 0.9701 . ?
C5 H5B 0.9691 . ?
C6 H6A 0.9702 . ?
C6 H6B 0.9700 . ?
O4 H3 0.8025 . ?
O4 H4 0.8729 . ?

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 Ni1 O3 180.0(3) 1_565 3_545 ?
O3 Ni1 O1 88.3(2) 1_565 . ?
O3 Ni1 O1 91.7(2) 3_545 . ?
O3 Ni1 O1 91.7(2) 1_565 3 ?
O3 Ni1 O1 88.3(2) 3_545 3 ?
O1 Ni1 O1 180.0(5) . 3 ?
O3 Ni1 O2 92.1(2) 1_565 . ?
O3 Ni1 O2 87.9(2) 3_545 . ?
O1 Ni1 O2 85.1(2) . . ?
O1 Ni1 O2 94.9(2) 3 . ?
O3 Ni1 O2 87.9(2) 1_565 3 ?
O3 Ni1 O2 92.1(2) 3_545 3 ?
O1 Ni1 O2 94.9(2) . 3 ?
O1 Ni1 O2 85.1(2) 3 3 ?
O2 Ni1 O2 180.0(4) . 3 ?
Ni1 O1 H1 116.7 . . ?
Ni1 O1 H2 108.7 . . ?
H1 O1 H2 108.3 . . ?
C1 O2 Ni1 131.5(6) . . ?
C3 O3 Ni1 131.3(6) . 1_545 ?
C1 N1 H10 122.3 . . ?
C1 N1 H11 117.4 . . ?
H10 N1 H11 120.2 . . ?
C3 N2 C2 123.9(7) . . ?
C3 N2 C6 112.2(8) . . ?
C2 N2 C6 123.6(8) . . ?
O2 C1 N1 125.3(9) . . ?
O2 C1 C2 117.8(8) . . ?
N1 C1 C2 117.0(8) . . ?
N2 C2 C1 115.0(7) . . ?
N2 C2 H2A 108.9 . . ?
C1 C2 H2A 108.6 . . ?
N2 C2 H2B 108.2 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.4 . . ?
O3 C3 N2 121.3(8) . . ?
O3 C3 C4 129.8(9) . . ?
N2 C3 C4 108.9(8) . . ?
C3 C4 C5 104.9(8) . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4A 110.4 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 108.9 . . ?
C6 C5 C4 104.3(8) . . ?
C6 C5 H5A 111.5 . . ?
C4 C5 H5A 111.2 . . ?
C6 C5 H5B 110.4 . . ?
C4 C5 H5B 110.4 . . ?
H5A C5 H5B 108.9 . . ?
N2 C6 C5 104.2(8) . . ?
N2 C6 H6A 110.8 . . ?
C5 C6 H6A 111.1 . . ?
N2 C6 H6B 111.1 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 109.1 . . ?
H3 O4 H4 101.2 . . ?

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.090


