# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2011

 
data_1
 
#===============================================================================
 
# 5. CHEMICAL DATA
 
_chemical_name_systematic
;
;
_chemical_name_common                ?
_chemical_melting_point              ?
_chemical_formula_moiety
'C10 H8 Br4 Cu N2'
_chemical_formula_structural         ?
_chemical_formula_sum
'C10 H8 Br4 Cu N2'
_chemical_formula_iupac              ?
_chemical_formula_weight                539.33
_chemical_compound_source           'see text'
 
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
 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'
Br  Br   -0.2901    2.4595
 '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'
 C   C    0.0033    0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
#===============================================================================
 
# 6. CRYSTAL DATA
 
_symmetry_cell_setting                 Monoclinic
_symmetry_space_group_name_Hall      '-P 2ybc'
_symmetry_space_group_name_H-M       'P 21/c'
_symmetry_Int_Tables_number                 14
 
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
   1 x,y,z
   2 -x,1/2+y,1/2-z
   3 -x,-y,-z
   4 x,1/2-y,1/2+z
 
_cell_length_a                         4.01653(10)
_cell_length_b                          13.9440(2)
_cell_length_c                          12.3686(2)
_cell_angle_alpha                               90
_cell_angle_beta                         90.526(1)
_cell_angle_gamma                               90
_cell_volume                             692.69(2)
_cell_formula_units_Z                    2
_cell_measurement_temperature            298

_cell_special_details
;
?
;


 

_exptl_crystal_density_meas          ?
_exptl_crystal_density_diffrn            2.586
_exptl_crystal_density_method       'Not Measured'
_exptl_crystal_F_000                       502


# The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.
_pd_spec_size_axial              12 
# perpendicular to equatorial plane
_pd_spec_size_equat              0.7 
# parallel to scattering vector  in transmission
_pd_spec_size_thick              ? 
# parallel to scattering vector  in reflection

# The next five fields are character fields that describe the specimen.
_pd_spec_mounting                '0.7 mm borosilicate capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_particle_morphology     'visual estimate, prisms'
_pd_char_colour                  green

# The following three fields describe the preparation of the specimen.   
# The cooling rate is in K/min.  The pressure at which the sample was  
# prepared is in kPa.  The temperature of preparation is in K.
_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             298

# The next four fields are normally only needed for transmission experiments.
_exptl_absorpt_coefficient_mu    15.568
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ? # include if applicable
_exptl_absorpt_correction_T_min  ? # include if applicable
_exptl_absorpt_correction_T_max  ? # include if applicable

 
#===============================================================================
 
# 7. EXPERIMENTAL DATA
 
_exptl_special_details
;
;

# This following item is used to identify the equipment used to record the
# powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.
_pd_instr_location               
'Solid-State Research Group, University of Strathclyde, Glasgow, U.K.'

_diffrn_ambient_temperature          298
_diffrn_radiation_probe              'x-ray'
_diffrn_radiation_type               'Cu K\a~1~'

# The following six items are used for angular dispersive measurements only.
_diffrn_radiation_wavelength     1.54056
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Bruker-AXS D8'
_diffrn_source_target            Cu
_diffrn_measurement_device_type  'Bruker AXS D8 Advance'
_diffrn_radiation_monochromator  'primary focussing, Ge 111'
_diffrn_detector                 '1D linear PSD'
_diffrn_detector_type            'Bruker Vantec, microgap linear PSD'
_pd_meas_scan_method             step
_pd_meas_special_details         
;  
Data were collected using a variable count time (VCT) scheme in
which the step time is increased with 2θ (Shankland et al., 
1997; Hill & Madsen,2002). The specific scheme used was:

Data Ranges / ° 2θ	Total Time in Each Range (s)
	 4.0 - 30.0             3058
	30.0 - 50.0		4706
	50.0 - 70.0		9412

;

# The following four items give details of the measured (not processed)
# powder pattern.  Angles are in degrees.
_pd_meas_number_of_points        3883
_pd_meas_2theta_range_min        4.0
_pd_meas_2theta_range_max        70.0
_pd_meas_2theta_range_inc        0.017

_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max      3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max      10
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_number              296
 
# The following fields are used to identify the programs used.
_computing_data_collection       
'DIFFRAC plus XRD Commander (Kienle & Jacob, 2003)'
_computing_data_reduction        'DASH (David et al., 2001)'
_computing_structure_solution    'DASH (David et al., 2001)'
_computing_structure_refinement  'Topas (Coelho, 2003)'
_computing_publication_material 
'enCifer (Cambridge Crystallographic Data Centre, 2004)'


 
#===============================================================================
 
# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.
_pd_proc_ls_special_details      
; 
The structure solution was obtained by global optimisation using the
DASH structure solution program.  The internal coordinate 
description of the molecule was constructed from standard bond
lengths, bond angles and bond torsions where appropriate.
The structure was solved using data to 52.23° 2θ, comprising
213 reflections. The structure was refined against data in the range 
6.0 to 62.1° 2θ (354 reflections).  
;

# The next three items are given as text.
_pd_proc_ls_profile_function     
;   
Fundamental parameters with axial divergence correction
;
_pd_proc_ls_background_function  
;
Chebyshev polynomial
;
_pd_proc_ls_pref_orient_corr     
; 
A spherical harmonics-based preferred orientation correction 
was applied with Topas during the Rietveld refinement.
;

_pd_proc_ls_prof_R_factor        0.03355
_pd_proc_ls_prof_wR_factor       0.04352
_pd_proc_ls_prof_wR_expected     0.02323

_refine_special_details          
; ?
;

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     1/σ(Yobs)²
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     75
_refine_ls_number_restraints     47
_refine_ls_number_constraints    3
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          0.005
_refine_ls_R_I_factor	?

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   1.873

# Give appropriate details in the next two text fields.
_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?
 
#===============================================================================
 
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br Uiso  0.36969(43) 0.46367(12) 0.65119(13) 1.000 0.0174(6) . .
Br3 Br Uiso -0.29861(43) 0.10990(11) 0.59932(13) 1.000 0.0035(6) . .
Cu1 Cu Uiso  0.00000     0.50000     0.50000     1.000 0.032(1) . .
N1  N  Uiso -0.01157(69) 0.36099(22) 0.46145(23) 1.000 0.013(2) . .
C2  C  Uiso -0.13100(10) 0.29468(25) 0.52991(29) 1.000 0.013(2) . .
C3  C  Uiso -0.13870(1)  0.19503(25) 0.50452(28) 1.000 0.013(2) . .
C4  C  Uiso -0.01661(91) 0.16869(22) 0.40319(27) 1.000 0.013(2) . .
C5  C  Uiso  0.10690(11) 0.23695(24) 0.33281(33) 1.000 0.013(2) . .
C6  C  Uiso  0.10700(10) 0.33471(25) 0.36472(29) 1.000 0.013(2) . .
H2  H  Uiso -0.21310(75) 0.31820(17) 0.59980(22) 1.000 0.016(2) . .
H4  H  Uiso -0.01840(70) 0.10170(17) 0.38130(20) 1.000 0.016(2) . .
H5  H  Uiso  0.18870(82) 0.21520(21) 0.26320(21) 1.000 0.016(2) . .
H6  H  Uiso  0.19290(80) 0.38660(18) 0.31640(18) 1.000 0.016(2) . .
 
#===============================================================================
 
# 10. MOLECULAR GEOMETRY
 
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
 
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
 Br1     Cu1          2.4305(16)               .       .                   yes
 Br3     C3           1.792(4)                 .       .                   yes
 Cu1     N1           1.996(3)                 .       .                   yes
 Cu1     N1           1.996(3)                 .     3_566                 yes
 N1      C2           1.345(5)                 .       .                   yes
 N1      C6           1.344(4)                 .       .                   yes
 C2      C3           1.426(6)                 .       .                   no
 C3      C4           1.399(5)                 .       .                   no
 C4      C5           1.385(4)                 .       .                   no
 C5      C6           1.418(5)                 .       .                   no
 C2      H2           0.984(4)                 .       .                   no
 C4      H4           0.973(4)                 .       .                   no
 C5      H5           0.973(4)                 .       .                   no
 C6      H6           1.002(5)                 .       .                   no
 
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
 Br1     Cu1     N1            89.65(8)         .       .       .           yes
 Br1     Cu1     Br1          180.00             .       .     3_566         yes
 Br1     Cu1     N1            90.34             .       .     3_566         yes
 Br1     Cu1     N1            90.34           3_566     .       .           yes
 N1      Cu1     N1           180.00             .       .     3_566         yes
 Br1     Cu1     N1            89.66           3_566     .     3_566         yes
 Cu1     N1      C2           121.7(2)          .       .       .           yes
 Cu1     N1      C6           118.0(2)          .       .       .           yes
 C2      N1      C6           120.3(3)          .       .       .           yes
 N1      C2      C3           122.6(3)          .       .       .           yes
 Br3     C3      C2           120.6(3)          .       .       .           yes
 Br3     C3      C4           122.9(3)          .       .       .           yes
 C2      C3      C4           116.5(3)          .       .       .           no
 C3      C4      C5           120.9(3)          .       .       .           no
 C4      C5      C6           119.0(3)          .       .       .           no
 N1      C6      C5           120.7(3)          .       .       .           yes
 N1      C2      H2           116.6(4)          .       .       .           no
 C3      C2      H2           120.8(4)          .       .       .           no
 C3      C4      H4           120.0(4)          .       .       .           no
 C5      C4      H4           119.2(4)          .       .       .           no
 C4      C5      H5           117.9(3)          .       .       .           no
 C6      C5      H5           123.2(3)          .       .       .           no
 N1      C6      H6           117.5(4)          .       .       .           no
 C5      C6      H6           121.8(4)          .       .       .           no
 
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
 Br1     Cu1     N1      C2            61.6(2)     .     .     .       .   no
 Br1     Cu1     N1      C2          -118.4(2)   3_566   .     .       .   no
 Br1     Cu1     N1      C6          -117.9(2)     .     .     .       .   no
 Br1     Cu1     N1      C6            62.1(2)   3_566   .     .       .   no
 Cu1     N1      C2      C3          -179.39(14)   .     .     .       .   no
 C6      N1      C2      C3             0.00       .     .     .       .   no
 Cu1     N1      C6      C5           179.63(18)   .     .     .       .   no
 C2      N1      C6      C5             0.3(3)     .     .     .       .   no
 N1      C2      C3      Br3          179.63(18)   .     .     .       .   no
 N1      C2      C3      C4            -0.4(3)     .     .     .       .   no
 Br3     C3      C4      C5          -179.5(2)     .     .     .       .   no
 C2      C3      C4      C5             0.5(4)     .     .     .       .   no
 C3      C4      C5      C6            -0.2(4)     .     .     .       .   no
 C4      C5      C6      N1            -0.2(3)     .     .     .       .   no
 
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
 Br1     Cu1          3.2015(16)                .     1_655                 no
 Br1     N1           3.136(3)                  .       .                   no
 Br1     C2           3.434(4)                  .       .                   no
 Br1     C2           3.447(4)                  .     1_655                 no
 Br1     Cu1          3.2015(16)                .     3_666                 no
 Br1     N1           3.155(3)                  .     3_566                 no
 Br1     Br3          3.712(2)                  .     2_556                 no
 Br1     C6           3.517(4)                  .     3_666                 no
 Br1     C6           3.406(4)                  .     3_566                 no
 Br1     C5           3.746(3)                  .     4_555                 no
 Br3     C6           3.732(4)                  .     4_555                 no
 Br3     Br1          3.712(2)                  .     2_546                 no
 Br1     H2           2.710(3)                  .     1_655                 no
 Br1     H2           3.158(3)                  .       .                   no
 Br1     H6           3.105(3)                  .     3_566                 no
 Br1     H6           2.756(3)                  .     3_666                 no
 Br1     H5           2.947(3)                  .     4_555                 no
 Br3     H4           3.222(3)                  .     3_556                 no
 Cu1     Br1          3.2015(16)                .     1_455                 no
 Cu1     Br1          3.2015(16)                .     3_666                 no
 N1      Br1          3.136(3)                  .       .                   no
 N1      Br1          3.155(3)                  .     3_566                 no
 C2      Br1          3.447(4)                  .     1_455                 no
 C5      Br1          3.746(3)                  .     4_554                 no
 C6      Br1          3.517(4)                  .     3_666                 no
 C6      Br3          3.732(4)                  .     4_554                 no
 H2      Br1          2.710(3)                  .     1_455                 no
 H2      Br1          3.158(3)                  .       .                   no
 H4      Br3          3.222(3)                  .     3_556                 no
 H5      Br1          2.947(3)                  .     4_554                 no
 H6      Br1          3.105(3)                  .     3_566                 no
 H6      Br1          2.756(3)                  .     3_666                 no
 

 
 
#===END
