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

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Lars Ohrstrom'
_publ_contact_author_email       OHRSTROM@CHALMERS.SE

_publ_section_title              
;
Methyl groups control coordination number,
stoichiometry, network and magnetism of a Cu(II)-azide-pyrazine (6,3)
2D net
;
loop_
_publ_author_name
'Lars Ohrstrom'
'Morsy A.M. Abu-Youssef'
'Vratislav Langer'
'Alshimaa A. Massoud'
'Jana Vejpravova'

# Attachment 'CuazShimo.cif'

data_m
_database_code_depnum_ccdc_archive 'CCDC 649681'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H4 Cu N7'
_chemical_formula_sum            'C3 H4 Cu N7'
_chemical_formula_weight         201.67

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   5.8645(4)
_cell_length_b                   7.5587(5)
_cell_length_c                   8.1625(6)
_cell_angle_alpha                77.744(2)
_cell_angle_beta                 76.991(1)
_cell_angle_gamma                83.633(1)
_cell_volume                     343.75(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2399
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.00

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark yellow brown'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.948
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             200
_exptl_absorpt_coefficient_mu    3.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7677
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
;
Data were collected at 173 K using a Siemens SMART CCD
diffractometer equipped with LT-2A cooling device. A full sphere of reciprocal
space was scanned by 0.3° steps in ω with a crystal--to--detector distance
of 3.97 cm, 30 seconds per frame. Preliminary orientation
matrix was obtained from the first 100 frames using SMART (Bruker,
2003a). The collected frames were integrated using the preliminary
orientation matrix which was updated every 100 frames. Final cell parameters
were obtained by refinement on the position of 2399 reflections with
I>10σ(I) after integration of all the frames data using SAINT
(Bruker, 2003b)

;

_diffrn_ambient_temperature      173(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  'Siemens CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3937
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1350
_reflns_number_gt                1090
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        
'SAINT (Bruker, 2003) & SADABS (Sheldrick, 2003)'
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL (Bruker, 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXTL (Bruker, 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)+(0.0329P)²+0.1258P] 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         1350
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.23328(9) 0.47625(7) 0.07418(7) 0.01626(18) Uani 1 1 d . . .
N1 N 0.0025(6) 0.3196(5) 0.0489(4) 0.0182(8) Uani 1 1 d . . .
N2 N -0.0456(6) 0.1752(5) 0.1436(5) 0.0230(9) Uani 1 1 d . . .
N3 N -0.0954(8) 0.0397(6) 0.2286(7) 0.0520(14) Uani 1 1 d . . .
N4 N 0.4819(6) 0.6386(5) 0.0622(5) 0.0284(10) Uani 1 1 d . . .
N5 N 0.4561(6) 0.7715(5) 0.1289(5) 0.0202(8) Uani 1 1 d . . .
N6 N 0.4329(7) 0.8946(6) 0.1919(6) 0.0392(11) Uani 1 1 d . . .
N7 N 0.0912(6) 0.4858(4) 0.3319(4) 0.0148(7) Uani 1 1 d . . .
C1 C 0.3853(8) 0.2473(7) 0.4120(6) 0.0331(13) Uani 1 1 d . . .
H1A H 0.3361 0.1604 0.3552 0.059(18) Uiso 1 1 calc R . .
H1B H 0.4363 0.1821 0.5163 0.050(16) Uiso 1 1 calc R . .
H1C H 0.5155 0.3124 0.3344 0.059(18) Uiso 1 1 calc R . .
C2 C 0.1841(7) 0.3797(6) 0.4579(5) 0.0151(9) Uani 1 1 d . . .
C4 C -0.0894(7) 0.6042(6) 0.3731(5) 0.0181(9) Uani 1 1 d . . .
H4 H -0.1550 0.6796 0.2840 0.019(12) Uiso 1 1 calc R . .

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 0.0127(3) 0.0192(3) 0.0175(3) -0.0099(2) 0.00294(19) -0.00386(19)
N1 0.0196(19) 0.016(2) 0.0189(19) -0.0032(17) -0.0026(15) -0.0051(15)
N2 0.0144(19) 0.023(2) 0.032(2) -0.008(2) -0.0032(16) -0.0007(16)
N3 0.034(3) 0.031(3) 0.078(4) 0.018(3) -0.008(2) -0.009(2)
N4 0.018(2) 0.031(2) 0.040(2) -0.026(2) 0.0068(17) -0.0081(16)
N5 0.0142(18) 0.025(2) 0.023(2) -0.0088(18) -0.0022(15) -0.0034(15)
N6 0.033(2) 0.038(3) 0.056(3) -0.035(2) -0.007(2) 0.0026(19)
N7 0.0173(18) 0.0146(18) 0.0126(18) -0.0053(15) -0.0003(14) -0.0024(14)
C1 0.034(3) 0.038(3) 0.020(3) -0.008(2) -0.001(2) 0.021(2)
C2 0.018(2) 0.018(2) 0.009(2) -0.0034(18) -0.0016(16) 0.0018(17)
C4 0.018(2) 0.019(2) 0.017(2) -0.0061(19) -0.0016(17) 0.0035(17)

_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 N1 1.965(3) . ?
Cu1 N4 1.981(4) . ?
Cu1 N4 2.009(3) 2_665 ?
Cu1 N7 2.095(3) . ?
Cu1 N1 2.190(4) 2_565 ?
N1 N2 1.216(5) . ?
N1 Cu1 2.190(4) 2_565 ?
N2 N3 1.136(5) . ?
N4 N5 1.220(5) . ?
N4 Cu1 2.009(3) 2_665 ?
N5 N6 1.136(5) . ?
N7 C2 1.343(5) . ?
N7 C4 1.339(5) . ?
C1 C2 1.494(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.392(5) 2_566 ?
C4 C2 1.392(5) 2_566 ?
C4 H4 0.9500 . ?

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 Cu1 N4 171.46(15) . . ?
N1 Cu1 N4 97.46(14) . 2_665 ?
N4 Cu1 N4 77.05(16) . 2_665 ?
N1 Cu1 N7 95.96(13) . . ?
N4 Cu1 N7 92.47(14) . . ?
N4 Cu1 N7 137.60(16) 2_665 . ?
N1 Cu1 N1 79.87(15) . 2_565 ?
N4 Cu1 N1 97.35(15) . 2_565 ?
N4 Cu1 N1 121.88(15) 2_665 2_565 ?
N7 Cu1 N1 100.00(13) . 2_565 ?
N2 N1 Cu1 124.3(3) . . ?
N2 N1 Cu1 128.1(3) . 2_565 ?
Cu1 N1 Cu1 100.13(15) . 2_565 ?
N3 N2 N1 177.7(5) . . ?
N5 N4 Cu1 125.5(3) . . ?
N5 N4 Cu1 131.5(3) . 2_665 ?
Cu1 N4 Cu1 102.95(16) . 2_665 ?
N6 N5 N4 179.5(5) . . ?
C2 N7 C4 118.8(3) . . ?
C2 N7 Cu1 121.1(3) . . ?
C4 N7 Cu1 120.0(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N7 C2 C4 119.0(4) . 2_566 ?
N7 C2 C1 118.8(4) . . ?
C4 C2 C1 122.1(4) 2_566 . ?
N7 C4 C2 122.1(4) . 2_566 ?
N7 C4 H4 118.9 . . ?
C2 C4 H4 118.9 2_566 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 Cu1 N1 N2 136.8(10) . . . . ?
N4 Cu1 N1 N2 87.2(3) 2_665 . . . ?
N7 Cu1 N1 N2 -52.4(3) . . . . ?
N1 Cu1 N1 N2 -151.6(4) 2_565 . . . ?
N4 Cu1 N1 Cu1 -71.7(11) . . . 2_565 ?
N4 Cu1 N1 Cu1 -121.18(16) 2_665 . . 2_565 ?
N7 Cu1 N1 Cu1 99.13(14) . . . 2_565 ?
N1 Cu1 N1 Cu1 0.0 2_565 . . 2_565 ?
Cu1 N1 N2 N3 -177(11) . . . . ?
Cu1 N1 N2 N3 40(11) 2_565 . . . ?
N1 Cu1 N4 N5 131.0(9) . . . . ?
N4 Cu1 N4 N5 -178.3(5) 2_665 . . . ?
N7 Cu1 N4 N5 -39.8(4) . . . . ?
N1 Cu1 N4 N5 60.6(4) 2_565 . . . ?
N1 Cu1 N4 Cu1 -50.7(11) . . . 2_665 ?
N4 Cu1 N4 Cu1 -0.001(2) 2_665 . . 2_665 ?
N7 Cu1 N4 Cu1 138.46(18) . . . 2_665 ?
N1 Cu1 N4 Cu1 -121.12(17) 2_565 . . 2_665 ?
Cu1 N4 N5 N6 107(58) . . . . ?
Cu1 N4 N5 N6 -71(59) 2_665 . . . ?
N1 Cu1 N7 C2 99.5(3) . . . . ?
N4 Cu1 N7 C2 -81.8(3) . . . . ?
N4 Cu1 N7 C2 -8.4(4) 2_665 . . . ?
N1 Cu1 N7 C2 -179.7(3) 2_565 . . . ?
N1 Cu1 N7 C4 -83.2(3) . . . . ?
N4 Cu1 N7 C4 95.5(3) . . . . ?
N4 Cu1 N7 C4 168.9(3) 2_665 . . . ?
N1 Cu1 N7 C4 -2.5(3) 2_565 . . . ?
C4 N7 C2 C4 0.2(7) . . . 2_566 ?
Cu1 N7 C2 C4 177.5(3) . . . 2_566 ?
C4 N7 C2 C1 179.9(4) . . . . ?
Cu1 N7 C2 C1 -2.8(5) . . . . ?
C2 N7 C4 C2 -0.2(7) . . . 2_566 ?
Cu1 N7 C4 C2 -177.5(3) . . . 2_566 ?

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
C1 H1A N6 0.98 2.59 3.473(6) 150.6 1_545
C1 H1B N6 0.98 2.60 3.545(7) 163.2 2_666

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.116


