# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bar38
_database_code_depnum_ccdc_archive 'CCDC 1480526'
_audit_update_record             
;
2016-11-08 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
[1-methyl-3-carboxymethyl benzimidazolium betaine]2 CuBr2 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Br2 Cu N4 O4'
_chemical_formula_weight         603.76

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'
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'

_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                   7.9693(5)
_cell_length_b                   8.4129(5)
_cell_length_c                   9.1302(5)
_cell_angle_alpha                68.058(5)
_cell_angle_beta                 85.402(5)
_cell_angle_gamma                71.258(6)
_cell_volume                     537.13(5)
_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       parallelpipid
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             299
_exptl_absorpt_coefficient_mu    4.772
_exptl_absorpt_correction_type   analitical
_exptl_absorpt_correction_T_min  1.6115
_exptl_absorpt_correction_T_max  3.2971
_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            4820
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         29.12
_reflns_number_total             2515
_reflns_number_gt                2066
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrysAlis
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEPII,
_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)+(0.0398P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2515
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.0000 1.0000 1.0000 0.02605(11) Uani 1 2 d S . .
Br1 Br 0.26934(3) 0.82068(3) 0.92435(3) 0.04244(11) Uani 1 1 d . . .
N1 N 0.1178(3) 1.6529(2) 0.5392(2) 0.0300(4) Uani 1 1 d . . .
C2 C 0.1170(3) 1.6203(3) 0.6924(3) 0.0292(5) Uani 1 1 d . . .
H2 H 0.0439 1.6976 0.7389 0.035 Uiso 1 1 calc R . .
N3 N 0.2351(3) 1.4616(3) 0.7710(2) 0.0278(4) Uani 1 1 d . . .
C4 C 0.3191(3) 1.3853(3) 0.6624(3) 0.0290(5) Uani 1 1 d . . .
C5 C 0.2434(3) 1.5077(3) 0.5142(3) 0.0302(5) Uani 1 1 d . . .
C6 C 0.2962(4) 1.4728(4) 0.3776(3) 0.0434(7) Uani 1 1 d . . .
H6 H 0.2466 1.5541 0.2784 0.052 Uiso 1 1 calc R . .
C7 C 0.4263(4) 1.3108(4) 0.3973(4) 0.0517(8) Uani 1 1 d . . .
H7 H 0.4641 1.2812 0.3091 0.062 Uiso 1 1 calc R . .
C8 C 0.5027(4) 1.1903(4) 0.5458(4) 0.0499(7) Uani 1 1 d . . .
H8 H 0.5921 1.0840 0.5532 0.060 Uiso 1 1 calc R . .
C9 C 0.4505(3) 1.2232(3) 0.6816(3) 0.0402(6) Uani 1 1 d . . .
H9 H 0.5003 1.1415 0.7806 0.048 Uiso 1 1 calc R . .
C10 C 0.0055(4) 1.8157(3) 0.4165(3) 0.0442(7) Uani 1 1 d . . .
H101 H -0.0697 1.8952 0.4648 0.066 Uiso 1 1 calc R . .
H102 H -0.0664 1.7822 0.3610 0.066 Uiso 1 1 calc R . .
H103 H 0.0791 1.8761 0.3436 0.066 Uiso 1 1 calc R . .
C11 C 0.2585(3) 1.3763(3) 0.9430(3) 0.0326(5) Uani 1 1 d . . .
H111 H 0.2098 1.4682 0.9884 0.039 Uiso 1 1 calc R . .
H112 H 0.3843 1.3235 0.9718 0.039 Uiso 1 1 calc R . .
C12 C 0.1694(3) 1.2299(3) 1.0134(2) 0.0265(5) Uani 1 1 d . . .
O1 O 0.1875(2) 1.1474(2) 1.15725(18) 0.0389(4) Uani 1 1 d . . .
O2 O 0.0837(2) 1.2067(2) 0.91616(17) 0.0335(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 0.0303(2) 0.0260(2) 0.02271(19) -0.00698(15) 0.00056(15) -0.01208(17)
Br1 0.03179(15) 0.04058(17) 0.05567(19) -0.02209(13) 0.00433(12) -0.00770(12)
N1 0.0346(11) 0.0278(10) 0.0260(9) -0.0075(8) -0.0015(8) -0.0100(9)
C2 0.0333(12) 0.0269(12) 0.0280(11) -0.0095(9) 0.0025(9) -0.0111(10)
N3 0.0330(10) 0.0265(10) 0.0247(9) -0.0069(8) 0.0011(8) -0.0133(8)
C4 0.0324(12) 0.0274(12) 0.0323(12) -0.0124(10) 0.0046(10) -0.0150(10)
C5 0.0367(13) 0.0304(12) 0.0282(11) -0.0117(10) 0.0049(10) -0.0165(11)
C6 0.0588(18) 0.0468(16) 0.0347(13) -0.0185(12) 0.0118(12) -0.0281(15)
C7 0.0615(19) 0.061(2) 0.0556(18) -0.0415(16) 0.0259(16) -0.0312(17)
C8 0.0411(15) 0.0419(16) 0.076(2) -0.0355(16) 0.0137(15) -0.0122(13)
C9 0.0356(14) 0.0326(13) 0.0529(16) -0.0162(12) 0.0009(12) -0.0106(12)
C10 0.0549(17) 0.0336(14) 0.0348(13) -0.0044(11) -0.0111(12) -0.0083(13)
C11 0.0410(13) 0.0342(13) 0.0243(11) -0.0080(10) -0.0022(10) -0.0163(11)
C12 0.0269(11) 0.0236(11) 0.0256(11) -0.0084(9) 0.0017(9) -0.0044(9)
O1 0.0431(10) 0.0398(10) 0.0260(8) -0.0032(7) -0.0003(7) -0.0132(9)
O2 0.0430(10) 0.0336(9) 0.0295(8) -0.0101(7) 0.0030(7) -0.0217(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 1.9293(15) 2_577 ?
Cu1 O2 1.9293(15) . ?
Cu1 Br1 2.4125(3) . ?
Cu1 Br1 2.4125(3) 2_577 ?
N1 C2 1.321(3) . ?
N1 C5 1.390(3) . ?
N1 C10 1.469(3) . ?
C2 N3 1.330(3) . ?
C2 H2 0.9300 . ?
N3 C4 1.391(3) . ?
N3 C11 1.461(3) . ?
C4 C9 1.386(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.389(3) . ?
C6 C7 1.380(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.395(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H101 0.9600 . ?
C10 H102 0.9600 . ?
C10 H103 0.9600 . ?
C11 C12 1.527(3) . ?
C11 H111 0.9700 . ?
C11 H112 0.9700 . ?
C12 O1 1.230(3) . ?
C12 O2 1.268(3) . ?

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 O2 180.00(9) 2_577 . ?
O2 Cu1 Br1 90.33(5) 2_577 . ?
O2 Cu1 Br1 89.67(5) . . ?
O2 Cu1 Br1 89.67(5) 2_577 2_577 ?
O2 Cu1 Br1 90.33(5) . 2_577 ?
Br1 Cu1 Br1 180.0 . 2_577 ?
C2 N1 C5 108.41(19) . . ?
C2 N1 C10 125.6(2) . . ?
C5 N1 C10 126.0(2) . . ?
N1 C2 N3 110.5(2) . . ?
N1 C2 H2 124.7 . . ?
N3 C2 H2 124.7 . . ?
C2 N3 C4 108.31(19) . . ?
C2 N3 C11 125.0(2) . . ?
C4 N3 C11 126.41(19) . . ?
C9 C4 N3 131.7(2) . . ?
C9 C4 C5 122.1(2) . . ?
N3 C4 C5 106.2(2) . . ?
C6 C5 N1 132.0(2) . . ?
C6 C5 C4 121.5(2) . . ?
N1 C5 C4 106.5(2) . . ?
C7 C6 C5 116.3(3) . . ?
C7 C6 H6 121.9 . . ?
C5 C6 H6 121.9 . . ?
C6 C7 C8 121.9(3) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 122.2(3) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C4 116.0(3) . . ?
C8 C9 H9 122.0 . . ?
C4 C9 H9 122.0 . . ?
N1 C10 H101 109.5 . . ?
N1 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
N1 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
N3 C11 C12 113.13(19) . . ?
N3 C11 H111 109.0 . . ?
C12 C11 H111 109.0 . . ?
N3 C11 H112 109.0 . . ?
C12 C11 H112 109.0 . . ?
H111 C11 H112 107.8 . . ?
O1 C12 O2 126.8(2) . . ?
O1 C12 C11 117.3(2) . . ?
O2 C12 C11 115.95(18) . . ?
C12 O2 Cu1 115.85(13) . . ?

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
C5 N1 C2 N3 0.1(3) . . . . ?
C10 N1 C2 N3 -179.6(2) . . . . ?
N1 C2 N3 C4 0.1(3) . . . . ?
N1 C2 N3 C11 -174.4(2) . . . . ?
C2 N3 C4 C9 -179.7(3) . . . . ?
C11 N3 C4 C9 -5.3(4) . . . . ?
C2 N3 C4 C5 -0.3(2) . . . . ?
C11 N3 C4 C5 174.2(2) . . . . ?
C2 N1 C5 C6 179.5(3) . . . . ?
C10 N1 C5 C6 -0.8(4) . . . . ?
C2 N1 C5 C4 -0.2(3) . . . . ?
C10 N1 C5 C4 179.4(2) . . . . ?
C9 C4 C5 C6 0.1(4) . . . . ?
N3 C4 C5 C6 -179.5(2) . . . . ?
C9 C4 C5 N1 179.9(2) . . . . ?
N3 C4 C5 N1 0.3(2) . . . . ?
N1 C5 C6 C7 -179.4(2) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C9 1.6(4) . . . . ?
C7 C8 C9 C4 -1.2(4) . . . . ?
N3 C4 C9 C8 179.8(3) . . . . ?
C5 C4 C9 C8 0.4(3) . . . . ?
C2 N3 C11 C12 100.1(3) . . . . ?
C4 N3 C11 C12 -73.5(3) . . . . ?
N3 C11 C12 O1 177.79(19) . . . . ?
N3 C11 C12 O2 -2.4(3) . . . . ?
O1 C12 O2 Cu1 -8.7(3) . . . . ?
C11 C12 O2 Cu1 171.51(15) . . . . ?
O2 Cu1 O2 C12 -118(100) 2_577 . . . ?
Br1 Cu1 O2 C12 -91.70(15) . . . . ?
Br1 Cu1 O2 C12 88.30(15) 2_577 . . . ?

_diffrn_measured_fraction_theta_max 0.874
_diffrn_reflns_theta_full        29.12
_diffrn_measured_fraction_theta_full 0.874
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.073
