Supplementary data (ESI) for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350

_publ_section_title              
;Simple and quantitative mechanochemical preparation of
the first zinc and copper complexes of the neuroleptic drug gabapentin
;
_publ_contact_author_name        'Prof. Dario Braga'
_publ_contact_author_email       DARIO.BRAGA@UNIBO.IT
loop_
_publ_author_name
'Dario Braga'
'Roberto Brescello'
'Livius Cotarca'
'Fabrizia Grepioni'
'Lucia Maini'

# Attachment '1-Zn.CIF'

data_1_[ZnCl2(gabapentin)2]
_database_code_depnum_ccdc_archive 'CCDC 667687'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H34 Cl2 N2 O4 Zn'
_chemical_formula_weight         478.74

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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)/a

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

_cell_length_a                   13.175(3)
_cell_length_b                   10.498(2)
_cell_length_c                   16.820(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.91(2)
_cell_angle_gamma                90.00
_cell_volume                     2200.8(9)
_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          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.384
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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            3995
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         24.98
_reflns_number_total             3857
_reflns_number_gt                2668
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0484P)^2^+0.3382P] where P=(Fo^2^+2Fc^2^)/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         3857
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3393(2) 0.7372(3) 0.42323(16) 0.0309(6) Uani 1 1 d . . .
C2 C 0.4432(2) 0.7815(3) 0.48922(18) 0.0413(7) Uani 1 1 d . . .
H2A H 0.4785 0.7083 0.5217 0.050 Uiso 1 1 calc R . .
H2B H 0.4905 0.8157 0.4607 0.050 Uiso 1 1 calc R . .
C3 C 0.4269(3) 0.8820(4) 0.5492(2) 0.0534(9) Uani 1 1 d . . .
H3A H 0.4953 0.9013 0.5913 0.064 Uiso 1 1 calc R . .
H3B H 0.3998 0.9595 0.5182 0.064 Uiso 1 1 calc R . .
C4 C 0.3486(3) 0.8361(4) 0.5921(2) 0.0573(9) Uani 1 1 d . . .
H4A H 0.3362 0.9037 0.6271 0.069 Uiso 1 1 calc R . .
H4B H 0.3795 0.7642 0.6280 0.069 Uiso 1 1 calc R . .
C5 C 0.2427(3) 0.7966(4) 0.52818(19) 0.0475(8) Uani 1 1 d . . .
H5A H 0.1960 0.7625 0.5573 0.057 Uiso 1 1 calc R . .
H5B H 0.2079 0.8707 0.4965 0.057 Uiso 1 1 calc R . .
C6 C 0.2588(2) 0.6971(3) 0.46822(18) 0.0401(7) Uani 1 1 d . . .
H6A H 0.1902 0.6790 0.4261 0.048 Uiso 1 1 calc R . .
H6B H 0.2842 0.6191 0.4992 0.048 Uiso 1 1 calc R . .
C7 C 0.3614(2) 0.6179(3) 0.37716(18) 0.0381(7) Uani 1 1 d . . .
H7A H 0.4005 0.5561 0.4187 0.046 Uiso 1 1 calc R . .
H7B H 0.2934 0.5797 0.3451 0.046 Uiso 1 1 calc R . .
C8 C 0.4250(2) 0.6453(3) 0.31820(19) 0.0406(7) Uani 1 1 d . . .
C9 C 0.2958(2) 0.8474(3) 0.36259(18) 0.0376(7) Uani 1 1 d . . .
H9A H 0.2770 0.9171 0.3930 0.045 Uiso 1 1 calc R . .
H9B H 0.3520 0.8773 0.3415 0.045 Uiso 1 1 calc R . .
C10 C 0.13448(19) 0.7528(3) -0.10413(15) 0.0273(5) Uani 1 1 d . . .
C11 C 0.0660(2) 0.7922(3) -0.19497(18) 0.0388(7) Uani 1 1 d . . .
H11A H 0.0139 0.7257 -0.2188 0.047 Uiso 1 1 calc R . .
H11B H 0.0268 0.8693 -0.1921 0.047 Uiso 1 1 calc R . .
C12 C 0.1313(3) 0.8151(3) -0.25303(19) 0.0533(9) Uani 1 1 d . . .
H12A H 0.0832 0.8319 -0.3093 0.064 Uiso 1 1 calc R . .
H12B H 0.1762 0.8897 -0.2342 0.064 Uiso 1 1 calc R . .
C13 C 0.2014(3) 0.7019(4) -0.2552(2) 0.0574(9) Uani 1 1 d . . .
H13A H 0.2440 0.7206 -0.2911 0.069 Uiso 1 1 calc R . .
H13B H 0.1568 0.6285 -0.2780 0.069 Uiso 1 1 calc R . .
C14 C 0.2746(2) 0.6725(3) -0.16705(19) 0.0456(8) Uani 1 1 d . . .
H14A H 0.3210 0.7449 -0.1452 0.055 Uiso 1 1 calc R . .
H14B H 0.3195 0.5999 -0.1686 0.055 Uiso 1 1 calc R . .
C15 C 0.2091(2) 0.6432(3) -0.10945(17) 0.0293(6) Uani 1 1 d . . .
H15A H 0.2576 0.6249 -0.0535 0.035 Uiso 1 1 calc R . .
H15B H 0.1663 0.5675 -0.1298 0.035 Uiso 1 1 calc R . .
C16 C 0.1964(2) 0.8718(3) -0.05888(18) 0.0336(6) Uani 1 1 d . . .
H16A H 0.2147 0.9232 -0.1002 0.040 Uiso 1 1 calc R . .
H16B H 0.1482 0.9219 -0.0384 0.040 Uiso 1 1 calc R . .
C17 C 0.2976(2) 0.8489(2) 0.01364(16) 0.0278(6) Uani 1 1 d . . .
C18 C 0.0528(2) 0.7082(3) -0.06320(18) 0.0352(7) Uani 1 1 d . . .
H18A H 0.0083 0.7800 -0.0595 0.042 Uiso 1 1 calc R . .
H18B H 0.0066 0.6448 -0.0992 0.042 Uiso 1 1 calc R . .
Cl1 Cl 0.53537(8) 0.92015(8) 0.22298(6) 0.0646(3) Uani 1 1 d . . .
Cl2 Cl 0.52504(6) 0.60959(7) 0.11576(4) 0.03794(18) Uani 1 1 d . . .
N1 N 0.2007(2) 0.8127(4) 0.29046(18) 0.0504(8) Uani 1 1 d . . .
H102 H 0.187(3) 0.870(4) 0.254(3) 0.076 Uiso 1 1 d . . .
H100 H 0.217(3) 0.744(4) 0.269(3) 0.076 Uiso 1 1 d . . .
H101 H 0.145(3) 0.807(4) 0.310(2) 0.076 Uiso 1 1 d . . .
N2 N 0.1012(2) 0.6528(3) 0.02222(16) 0.0337(6) Uani 1 1 d . . .
H200 H 0.162(3) 0.701(3) 0.056(2) 0.051 Uiso 1 1 d . . .
H201 H 0.118(3) 0.572(3) 0.024(2) 0.051 Uiso 1 1 d . . .
H202 H 0.053(3) 0.653(3) 0.044(2) 0.051 Uiso 1 1 d . . .
O1 O 0.36669(17) 0.6819(2) 0.24489(12) 0.0481(6) Uani 1 1 d . . .
O2 O 0.52271(17) 0.6348(3) 0.34203(14) 0.0576(6) Uani 1 1 d . . .
O3 O 0.29169(14) 0.78332(19) 0.07614(12) 0.0354(5) Uani 1 1 d . . .
O4 O 0.38373(14) 0.89446(18) 0.01149(12) 0.0344(4) Uani 1 1 d . . .
Zn1 Zn 0.43148(2) 0.75159(3) 0.164531(18) 0.03313(11) 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
C1 0.0274(13) 0.0361(15) 0.0307(13) 0.0007(13) 0.0116(11) -0.0018(12)
C2 0.0255(15) 0.058(2) 0.0379(16) -0.0015(14) 0.0070(12) -0.0052(13)
C3 0.0387(18) 0.069(2) 0.0451(18) -0.0163(17) 0.0040(15) -0.0096(17)
C4 0.049(2) 0.083(3) 0.0392(18) -0.0126(18) 0.0143(16) -0.0008(19)
C5 0.0398(17) 0.069(2) 0.0381(17) -0.0022(16) 0.0190(15) 0.0037(16)
C6 0.0350(16) 0.0516(18) 0.0358(16) 0.0014(14) 0.0142(14) -0.0084(14)
C7 0.0431(17) 0.0391(17) 0.0369(16) 0.0026(13) 0.0194(14) -0.0005(14)
C8 0.0419(18) 0.0444(18) 0.0389(17) -0.0039(14) 0.0180(15) -0.0015(14)
C9 0.0336(16) 0.0409(17) 0.0362(16) -0.0017(13) 0.0087(13) -0.0040(13)
C10 0.0212(12) 0.0293(13) 0.0284(12) -0.0021(12) 0.0038(10) 0.0025(12)
C11 0.0332(16) 0.0371(15) 0.0355(15) 0.0001(13) -0.0036(13) 0.0020(12)
C12 0.058(2) 0.062(2) 0.0299(16) 0.0138(16) 0.0004(15) -0.0098(18)
C13 0.061(2) 0.079(3) 0.0395(18) -0.0019(18) 0.0265(17) -0.005(2)
C14 0.0386(17) 0.057(2) 0.0481(18) 0.0022(16) 0.0234(15) 0.0061(16)
C15 0.0279(14) 0.0291(14) 0.0311(14) -0.0023(11) 0.0097(12) 0.0001(11)
C16 0.0272(14) 0.0289(15) 0.0392(15) -0.0006(12) 0.0031(12) 0.0016(11)
C17 0.0253(14) 0.0220(13) 0.0337(15) -0.0067(11) 0.0064(12) 0.0019(11)
C18 0.0215(14) 0.0439(16) 0.0393(16) -0.0045(13) 0.0084(12) 0.0012(12)
Cl1 0.0587(5) 0.0388(4) 0.0693(6) -0.0098(4) -0.0166(4) 0.0023(4)
Cl2 0.0382(4) 0.0352(4) 0.0426(4) -0.0017(3) 0.0160(3) -0.0001(3)
N1 0.0335(15) 0.072(2) 0.0403(17) 0.0088(14) 0.0041(13) 0.0005(15)
N2 0.0290(13) 0.0354(13) 0.0426(14) -0.0045(12) 0.0197(12) -0.0027(11)
O1 0.0398(12) 0.0761(16) 0.0320(11) 0.0055(11) 0.0167(10) 0.0033(12)
O2 0.0353(13) 0.0887(19) 0.0507(13) 0.0089(13) 0.0165(11) 0.0100(12)
O3 0.0249(10) 0.0451(12) 0.0327(10) 0.0062(9) 0.0044(8) -0.0036(8)
O4 0.0248(10) 0.0353(11) 0.0438(11) -0.0012(9) 0.0122(9) -0.0009(8)
Zn1 0.02474(17) 0.0440(2) 0.02895(17) -0.00059(16) 0.00633(12) 0.00081(15)

_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
C1 C9 1.526(4) . ?
C1 C2 1.528(4) . ?
C1 C6 1.547(4) . ?
C1 C7 1.550(4) . ?
C2 C3 1.522(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.516(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.518(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.514(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.518(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O2 1.223(4) . ?
C8 O1 1.282(4) . ?
C9 N1 1.480(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C18 1.526(4) . ?
C10 C15 1.534(4) . ?
C10 C16 1.551(4) . ?
C10 C11 1.558(3) . ?
C11 C12 1.515(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.512(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.515(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.523(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.506(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O4 1.243(3) . ?
C17 O3 1.280(3) . ?
C18 N2 1.488(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
Cl1 Zn1 2.2581(10) . ?
Cl2 Zn1 2.2515(8) . ?
N1 H102 0.84(4) . ?
N1 H100 0.87(4) . ?
N1 H101 0.90(4) . ?
N2 H200 0.96(4) . ?
N2 H201 0.88(3) . ?
N2 H202 0.84(3) . ?
O1 Zn1 1.959(2) . ?
O3 Zn1 1.9846(19) . ?

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
C9 C1 C2 108.0(2) . . ?
C9 C1 C6 111.4(2) . . ?
C2 C1 C6 108.8(2) . . ?
C9 C1 C7 111.7(2) . . ?
C2 C1 C7 109.9(2) . . ?
C6 C1 C7 107.1(2) . . ?
C3 C2 C1 114.0(2) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 111.0(3) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 111.2(3) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 111.4(3) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C1 113.9(3) . . ?
C5 C6 H6A 108.8 . . ?
C1 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C1 114.0(2) . . ?
C8 C7 H7A 108.8 . . ?
C1 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
O2 C8 O1 125.5(3) . . ?
O2 C8 C7 120.9(3) . . ?
O1 C8 C7 113.6(3) . . ?
N1 C9 C1 113.3(3) . . ?
N1 C9 H9A 108.9 . . ?
C1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C1 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C18 C10 C15 110.8(2) . . ?
C18 C10 C16 111.2(2) . . ?
C15 C10 C16 112.8(2) . . ?
C18 C10 C11 104.8(2) . . ?
C15 C10 C11 108.7(2) . . ?
C16 C10 C11 108.2(2) . . ?
C12 C11 C10 113.9(2) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 111.7(3) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 109.7(3) . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 C15 110.6(3) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C10 113.0(2) . . ?
C14 C15 H15A 109.0 . . ?
C10 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C10 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C10 117.1(2) . . ?
C17 C16 H16A 108.0 . . ?
C10 C16 H16A 108.0 . . ?
C17 C16 H16B 108.0 . . ?
C10 C16 H16B 108.0 . . ?
H16A C16 H16B 107.3 . . ?
O4 C17 O3 122.0(2) . . ?
O4 C17 C16 119.4(2) . . ?
O3 C17 C16 118.5(2) . . ?
N2 C18 C10 114.3(2) . . ?
N2 C18 H18A 108.7 . . ?
C10 C18 H18A 108.7 . . ?
N2 C18 H18B 108.7 . . ?
C10 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C9 N1 H102 110(3) . . ?
C9 N1 H100 107(3) . . ?
H102 N1 H100 109(4) . . ?
C9 N1 H101 107(3) . . ?
H102 N1 H101 107(4) . . ?
H100 N1 H101 116(4) . . ?
C18 N2 H200 113(2) . . ?
C18 N2 H201 116(2) . . ?
H200 N2 H201 110(3) . . ?
C18 N2 H202 106(2) . . ?
H200 N2 H202 109(3) . . ?
H201 N2 H202 102(3) . . ?
C8 O1 Zn1 121.1(2) . . ?
C17 O3 Zn1 114.63(16) . . ?
O1 Zn1 O3 94.21(9) . . ?
O1 Zn1 Cl2 114.62(7) . . ?
O3 Zn1 Cl2 108.84(6) . . ?
O1 Zn1 Cl1 109.29(8) . . ?
O3 Zn1 Cl1 118.62(6) . . ?
Cl2 Zn1 Cl1 110.57(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.064

# Attachment '2-Cu.CIF'

data_2_[CuCl2(gabapentin)2]
_database_code_depnum_ccdc_archive 'CCDC 667688'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H34 Cl2 Cu N2 O4'
_chemical_formula_weight         476.91

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/a

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

_cell_length_a                   11.865(6)
_cell_length_b                   6.750(4)
_cell_length_c                   15.109(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.87(2)
_cell_angle_gamma                90.00
_cell_volume                     1114.9(11)
_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            blue
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             502
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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            2005
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1929
_reflns_number_gt                1198
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0914P)^2^+5.7322P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1929
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1838
_refine_ls_wR_factor_gt          0.1586
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_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
C1 C 0.5050(6) 0.2752(10) 0.3763(5) 0.0302(15) Uani 1 1 d . . .
C2 C 0.4844(6) 0.4713(10) 0.3255(5) 0.0341(16) Uani 1 1 d . . .
H2A H 0.5448 0.4883 0.2975 0.041 Uiso 1 1 calc R . .
H2B H 0.4963 0.5764 0.3721 0.041 Uiso 1 1 calc R . .
C3 C 0.3554(5) 0.4905(10) 0.2457(4) 0.0276(13) Uani 1 1 d . . .
C4 C 0.3376(7) 0.3474(12) 0.1628(5) 0.0423(18) Uani 1 1 d . . .
H4A H 0.2519 0.3468 0.1199 0.051 Uiso 1 1 calc R . .
H4B H 0.3588 0.2146 0.1884 0.051 Uiso 1 1 calc R . .
C5 C 0.4159(9) 0.4015(15) 0.1044(6) 0.061(3) Uani 1 1 d . . .
H5A H 0.5015 0.3788 0.1439 0.073 Uiso 1 1 calc R . .
H5B H 0.3935 0.3155 0.0487 0.073 Uiso 1 1 calc R . .
C6 C 0.3986(10) 0.6135(17) 0.0717(7) 0.073(3) Uani 1 1 d . . .
H6A H 0.3170 0.6297 0.0227 0.088 Uiso 1 1 calc R . .
H6B H 0.4568 0.6451 0.0431 0.088 Uiso 1 1 calc R . .
C7 C 0.4158(9) 0.7577(13) 0.1532(7) 0.060(2) Uani 1 1 d . . .
H7A H 0.5008 0.7567 0.1976 0.072 Uiso 1 1 calc R . .
H7B H 0.3961 0.8906 0.1274 0.072 Uiso 1 1 calc R . .
C8 C 0.3355(7) 0.7046(11) 0.2068(5) 0.0394(18) Uani 1 1 d . . .
H8A H 0.2504 0.7208 0.1640 0.047 Uiso 1 1 calc R . .
H8B H 0.3522 0.7956 0.2601 0.047 Uiso 1 1 calc R . .
C9 C 0.2562(6) 0.4323(11) 0.2837(5) 0.0356(17) Uani 1 1 d . . .
H9A H 0.1774 0.4766 0.2377 0.043 Uiso 1 1 calc R . .
H9B H 0.2533 0.2889 0.2867 0.043 Uiso 1 1 calc R . .
Cl Cl 0.70770(14) 0.0218(3) 0.57697(13) 0.0382(5) Uani 1 1 d . . .
Cu Cu 0.5000 0.0000 0.5000 0.0230(3) Uani 1 2 d S . .
N1 N 0.2731(5) 0.5121(9) 0.3786(4) 0.0349(13) Uani 1 1 d . . .
H100 H 0.2946 0.6532 0.3813 0.090 Uiso 1 1 d . . .
H101 H 0.3519 0.4717 0.4279 0.090 Uiso 1 1 d . . .
H102 H 0.2016 0.4781 0.3881 0.090 Uiso 1 1 d . . .
O1 O 0.4907(4) 0.2722(6) 0.4566(3) 0.0304(10) Uani 1 1 d . . .
O2 O 0.5330(4) 0.1253(7) 0.3426(4) 0.0416(13) 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
C1 0.016(3) 0.033(4) 0.044(4) 0.001(3) 0.015(3) -0.001(3)
C2 0.020(3) 0.042(4) 0.046(4) 0.006(3) 0.019(3) -0.001(3)
C3 0.022(3) 0.030(3) 0.032(3) 0.006(3) 0.011(3) -0.001(3)
C4 0.038(4) 0.046(4) 0.043(4) -0.002(4) 0.016(4) 0.005(4)
C5 0.069(6) 0.081(6) 0.046(5) -0.004(5) 0.037(5) 0.013(5)
C6 0.089(8) 0.092(8) 0.062(6) 0.022(6) 0.055(6) 0.016(6)
C7 0.068(6) 0.051(5) 0.077(6) 0.025(5) 0.046(5) 0.010(4)
C8 0.038(4) 0.034(4) 0.052(5) 0.011(3) 0.023(4) 0.006(3)
C9 0.018(3) 0.043(4) 0.047(4) 0.008(3) 0.014(3) 0.000(3)
Cl 0.0179(8) 0.0407(10) 0.0568(12) 0.0068(9) 0.0155(8) 0.0016(8)
Cu 0.0157(5) 0.0215(5) 0.0349(6) 0.0037(5) 0.0132(4) 0.0022(5)
N1 0.024(3) 0.037(3) 0.056(4) -0.001(3) 0.030(3) -0.002(3)
O1 0.029(3) 0.024(2) 0.042(3) 0.003(2) 0.019(2) 0.0008(19)
O2 0.030(3) 0.040(3) 0.059(3) -0.003(2) 0.022(3) 0.013(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.235(8) . ?
C1 O1 1.289(8) . ?
C1 C2 1.501(9) . ?
C2 C3 1.543(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.531(9) . ?
C3 C8 1.543(9) . ?
C3 C9 1.548(8) . ?
C4 C5 1.553(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.502(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.520(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.514(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.469(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
Cl Cu 2.285(2) . ?
Cu O1 1.939(4) 3_656 ?
Cu O1 1.939(4) . ?
Cu Cl 2.285(2) 3_656 ?
N1 H100 0.9830 . ?
N1 H101 0.9807 . ?
N1 H102 0.9424 . ?

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
O2 C1 O1 122.0(6) . . ?
O2 C1 C2 121.9(6) . . ?
O1 C1 C2 116.1(6) . . ?
C1 C2 C3 112.9(5) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C8 109.1(6) . . ?
C4 C3 C9 105.1(6) . . ?
C8 C3 C9 110.7(5) . . ?
C4 C3 C2 111.5(6) . . ?
C8 C3 C2 109.6(5) . . ?
C9 C3 C2 110.8(5) . . ?
C3 C4 C5 113.2(7) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 112.1(7) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 112.7(7) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 111.6(8) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C3 113.0(6) . . ?
C7 C8 H8A 109.0 . . ?
C3 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C3 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 C3 115.7(5) . . ?
N1 C9 H9A 108.4 . . ?
C3 C9 H9A 108.4 . . ?
N1 C9 H9B 108.4 . . ?
C3 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
O1 Cu O1 180.0(3) 3_656 . ?
O1 Cu Cl 91.11(14) 3_656 3_656 ?
O1 Cu Cl 88.89(14) . 3_656 ?
O1 Cu Cl 88.89(14) 3_656 . ?
O1 Cu Cl 91.11(14) . . ?
Cl Cu Cl 180.00(4) 3_656 . ?
C9 N1 H100 109.3 . . ?
C9 N1 H101 111.6 . . ?
H100 N1 H101 94.7 . . ?
C9 N1 H102 105.6 . . ?
H100 N1 H102 117.6 . . ?
H101 N1 H102 117.7 . . ?
C1 O1 Cu 108.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.241
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.123