# 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        'Annie Powell'
_publ_contact_author_email       POWELL@AOC.UNI-KARLSRUHE.DE

_publ_section_title              
;
[Cu(N3)(p-CPA)]n:
a Two Dimensional Network Exhibiting Spin Orientation Behaviour
;
loop_
_publ_author_name
'Annie Powell'
'Ghulam Abbas'
'Christopher E. Anson'
'Gernot Buth'
'George E. Kostakis'
'Yanhua Lan.'
;
K.C.Mondal
;
'Ghenadie Novitchi'

# Attachment 'gek1.cif'

data_gek1
_database_code_depnum_ccdc_archive 'CCDC 724444'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 Cu N4 O3'
_chemical_formula_weight         281.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0043 0.0021 http://skuld.bmsc.washington.edu/scatter/AS_periodic.html
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0082 0.0043 http://skuld.bmsc.washington.edu/scatter/AS_periodic.html
O O 0.0142 0.0079 http://skuld.bmsc.washington.edu/scatter/AS_periodic.html
Cu Cu 0.2705 1.5628 http://skuld.bmsc.washington.edu/scatter/AS_periodic.html

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   11.4821(11)
_cell_length_b                   6.3061(6)
_cell_length_c                   14.7581(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.368(2)
_cell_angle_gamma                90.00
_cell_volume                     1019.87(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3347
_cell_measurement_theta_min      3.99
_cell_measurement_theta_max      32.81

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    2.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   'SADABS (Bruker AXS Inc., 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.80000
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'Bruker SMART Apex'
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4233
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.99
_diffrn_reflns_theta_max         33.12
_reflns_number_total             2361
_reflns_number_gt                2181
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2 (Bruker AXS Inc., 2005)'
_computing_cell_refinement       'Apex2 (Bruker AXS Inc., 2005)'
_computing_data_reduction        'Apex2 (Bruker AXS Inc., 2003)'
_computing_structure_solution    'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_structure_refinement  'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_molecular_graphics    'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_publication_material  'SHELXTL 6.14 (BrukerAXS Inc., 2003)'

_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)+(0.0416P)²+0.2787P] 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         2361
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.236046(19) 0.54388(3) 0.254333(12) 0.02150(9) Uani 1 1 d . . .
O1 O 0.31232(11) 0.46258(17) 0.38685(8) 0.0237(3) Uani 1 1 d . . .
O2 O 0.35504(11) 0.11464(17) 0.37652(7) 0.0248(2) Uani 1 1 d . . .
O3 O 0.41845(11) 0.46442(18) 0.57641(8) 0.0252(3) Uani 1 1 d . . .
C1 C 0.35750(14) 0.2879(2) 0.41979(10) 0.0209(3) Uani 1 1 d . . .
C2 C 0.42538(16) 0.2742(3) 0.52604(11) 0.0250(3) Uani 1 1 d . . .
H2A H 0.3908 0.1561 0.5540 0.030 Uiso 1 1 calc R . .
H2B H 0.5122 0.2411 0.5343 0.030 Uiso 1 1 calc R . .
C3 C 0.31406(16) 0.5071(3) 0.59771(11) 0.0243(3) Uani 1 1 d . . .
C4 C 0.31632(17) 0.6930(3) 0.65037(11) 0.0272(3) Uani 1 1 d . . .
H4A H 0.3871 0.7800 0.6670 0.033 Uiso 1 1 calc R . .
C5 C 0.21587(17) 0.7500(3) 0.67815(11) 0.0281(3) Uani 1 1 d . . .
H5A H 0.2170 0.8772 0.7129 0.034 Uiso 1 1 calc R . .
C6 C 0.11207(16) 0.6190(3) 0.65476(11) 0.0270(3) Uani 1 1 d . . .
C7 C 0.10972(17) 0.4350(3) 0.60110(12) 0.0288(4) Uani 1 1 d . . .
H7A H 0.0390 0.3479 0.5845 0.035 Uiso 1 1 calc R . .
C8 C 0.20915(16) 0.3792(3) 0.57206(11) 0.0275(3) Uani 1 1 d . . .
H8A H 0.2067 0.2552 0.5350 0.033 Uiso 1 1 calc R . .
C9 C 0.01135(17) 0.6664(3) 0.69166(12) 0.0291(4) Uani 1 1 d . . .
N1 N -0.06679(16) 0.6953(3) 0.72376(12) 0.0362(4) Uani 1 1 d . . .
N2 N 0.31816(14) 0.31431(19) 0.20505(9) 0.0233(3) Uani 1 1 d . . .
N3 N 0.33275(14) 0.3438(2) 0.12699(10) 0.0278(3) Uani 1 1 d . . .
N4 N 0.34966(18) 0.3769(3) 0.05597(11) 0.0389(4) 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
Cu1 0.02810(14) 0.01681(12) 0.01850(11) -0.00021(6) 0.00530(8) 0.00255(6)
O1 0.0266(6) 0.0228(5) 0.0201(5) -0.0007(4) 0.0044(5) 0.0028(4)
O2 0.0311(6) 0.0201(5) 0.0203(5) -0.0001(4) 0.0032(4) -0.0012(5)
O3 0.0256(6) 0.0286(6) 0.0214(5) -0.0044(4) 0.0069(5) -0.0030(4)
C1 0.0196(7) 0.0232(7) 0.0199(6) 0.0002(5) 0.0060(6) -0.0026(5)
C2 0.0281(8) 0.0258(7) 0.0196(6) 0.0001(5) 0.0048(6) 0.0018(6)
C3 0.0270(8) 0.0269(7) 0.0185(6) 0.0001(5) 0.0060(6) -0.0027(6)
C4 0.0289(9) 0.0283(8) 0.0247(7) -0.0038(6) 0.0087(7) -0.0073(6)
C5 0.0330(9) 0.0268(7) 0.0251(7) -0.0031(6) 0.0095(7) -0.0032(7)
C6 0.0270(8) 0.0317(8) 0.0229(7) 0.0016(6) 0.0081(6) -0.0007(7)
C7 0.0275(9) 0.0315(8) 0.0259(7) -0.0011(6) 0.0057(7) -0.0071(6)
C8 0.0309(9) 0.0266(8) 0.0240(7) -0.0041(6) 0.0069(6) -0.0062(7)
C9 0.0271(9) 0.0332(8) 0.0259(7) 0.0017(6) 0.0063(7) -0.0006(7)
N1 0.0305(8) 0.0427(9) 0.0348(8) -0.0008(6) 0.0088(7) -0.0050(7)
N2 0.0321(8) 0.0178(5) 0.0224(6) 0.0011(4) 0.0119(6) 0.0000(5)
N3 0.0341(8) 0.0211(6) 0.0288(7) 0.0009(5) 0.0104(6) 0.0040(6)
N4 0.0550(11) 0.0348(8) 0.0335(8) 0.0055(6) 0.0231(8) 0.0097(8)

_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 O2 1.9535(11) 2 ?
Cu1 O1 1.9575(11) . ?
Cu1 N2 1.9692(13) 2 ?
Cu1 N2 1.9806(13) . ?
Cu1 N1 2.5557(17) 3_566 ?
Cu1 N1 2.9400(18) 4_675 ?
O1 C1 1.2525(18) . ?
O2 C1 1.2615(19) . ?
O2 Cu1 1.9535(11) 2_545 ?
O3 C3 1.354(2) . ?
O3 C2 1.4258(19) . ?
C1 C2 1.531(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.403(2) . ?
C3 C8 1.404(2) . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.406(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.400(2) . ?
C6 C9 1.449(3) . ?
C7 C8 1.380(3) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 N1 1.147(3) . ?
N1 Cu1 2.5557(17) 3_566 ?
N2 N3 1.2269(19) . ?
N2 Cu1 1.9692(13) 2_545 ?
N3 N4 1.141(2) . ?

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 Cu1 O1 174.41(5) 2 . ?
O2 Cu1 N2 88.77(5) 2 2 ?
O1 Cu1 N2 90.60(5) . 2 ?
O2 Cu1 N2 88.68(5) 2 . ?
O1 Cu1 N2 93.17(5) . . ?
N2 Cu1 N2 166.68(4) 2 . ?
O2 Cu1 N1 93.26(5) 2 3_566 ?
O1 Cu1 N1 81.34(5) . 3_566 ?
N2 Cu1 N1 98.70(6) 2 3_566 ?
N2 Cu1 N1 94.50(6) . 3_566 ?
O2 Cu1 N1 85.99(5) 2 4_675 ?
O1 Cu1 N1 99.47(5) . 4_675 ?
N2 Cu1 N1 83.69(5) 2 4_675 ?
N2 Cu1 N1 83.10(5) . 4_675 ?
N1 Cu1 N1 177.49(5) 3_566 4_675 ?
C1 O1 Cu1 128.91(10) . . ?
C1 O2 Cu1 128.52(10) . 2_545 ?
C3 O3 C2 118.64(13) . . ?
O1 C1 O2 128.40(14) . . ?
O1 C1 C2 118.19(13) . . ?
O2 C1 C2 113.41(13) . . ?
O3 C2 C1 113.33(13) . . ?
O3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
O3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O3 C3 C4 115.06(15) . . ?
O3 C3 C8 124.82(15) . . ?
C4 C3 C8 120.12(17) . . ?
C5 C4 C3 120.19(16) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 119.71(16) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C7 C6 C5 119.83(17) . . ?
C7 C6 C9 120.05(17) . . ?
C5 C6 C9 119.98(16) . . ?
C8 C7 C6 120.61(16) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C7 C8 C3 119.50(16) . . ?
C7 C8 H8A 120.2 . . ?
C3 C8 H8A 120.2 . . ?
N1 C9 C6 176.57(19) . . ?
C9 N1 Cu1 132.57(14) . 3_566 ?
N3 N2 Cu1 124.15(11) . 2_545 ?
N3 N2 Cu1 116.57(10) . . ?
Cu1 N2 Cu1 107.03(7) 2_545 . ?
N4 N3 N2 177.38(19) . . ?

_diffrn_measured_fraction_theta_max 0.866
_diffrn_reflns_theta_full        28.75
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.063


