# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2007

data_global
_journal_name_full               Chem.Commun.
_journal_coden_Cambridge         0182
_publ_contact_author_name        'Rico E. Del Sesto'
_publ_contact_author_address     
;Los Alamos National Laboratory
MS J514
Los Alamos, NM 87545
;
_publ_contact_author_email       ricod@lanl.gov
loop_
_publ_author_name
_publ_author_address
'R.E.Del Sesto' 'McCleskey, T. Mark'
A.K.Burrell 'Baker, Gary A.'
J.D.Thompson 'Scott, Brian L.'
J.S.Wilkes 'Williams, Peg'

_publ_section_title              
;
Structure and Magnetic Behavior of Transition Metal Based
Ionic Liquids
;

# Attachment 'C4MIm2MnBr4_CIF.txt'

data_apx260
_database_code_depnum_ccdc_archive 'CCDC 655280'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H30 Br4 Mn N4'
_chemical_formula_weight         653.02

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'
Mn Mn 0.3368 0.7283 '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           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   15.0240(17)
_cell_length_b                   9.4070(11)
_cell_length_c                   18.726(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.4420(10)
_cell_angle_gamma                90.00
_cell_volume                     2446.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    141(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       orange
_exptl_crystal_colour            irregular
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1276
_exptl_absorpt_coefficient_mu    7.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3622
_exptl_absorpt_correction_T_max  0.6760
_exptl_absorpt_process_details   'SADABS 2.03 (Sheldrick, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      141(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  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13380
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         28.93
_reflns_number_total             3019
_reflns_number_gt                2521
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 1.08 (Bruker AXS, 2003)'
_computing_cell_refinement       'SAINT+, v. 7.06 (Bruker AXS, 2001)'
_computing_data_reduction        'SAINT+, v. 7.06 (Bruker AXS, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.10, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.10, (Bruker AXS, 2000)'

_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^)+(0.0000P)^2^+0.0000P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3019
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0704
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_restrained_S_all      1.218
_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
Br1 Br -0.004760(18) 0.71436(3) 0.354482(15) 0.01695(9) Uani 1 1 d . . .
Br2 Br 0.14945(2) 0.40085(3) 0.295327(17) 0.02320(9) Uani 1 1 d . . .
Mn1 Mn 0.0000 0.54885(6) 0.2500 0.01593(14) Uani 1 2 d S . .
N1 N 0.84515(16) 0.5585(2) 0.47556(13) 0.0166(5) Uiso 1 1 d . . .
N2 N 0.72564(15) 0.4896(2) 0.37352(13) 0.0168(5) Uiso 1 1 d . . .
C1 C 0.80330(19) 0.5707(3) 0.39888(16) 0.0201(6) Uiso 1 1 d . . .
H1 H 0.8253 0.6271 0.3682 0.024 Uiso 1 1 calc R . .
C2 C 0.79069(19) 0.4670(3) 0.49973(16) 0.0181(6) Uiso 1 1 d . . .
H2 H 0.8027 0.4403 0.5504 0.022 Uiso 1 1 calc R . .
C3 C 0.7165(2) 0.4236(3) 0.43572(16) 0.0197(6) Uiso 1 1 d . . .
H3 H 0.6681 0.3606 0.4341 0.024 Uiso 1 1 calc R . .
C4 C 0.6591(2) 0.4760(3) 0.29254(17) 0.0266(7) Uiso 1 1 d . . .
H4A H 0.6263 0.5646 0.2752 0.040 Uiso 1 1 calc R . .
H4B H 0.6128 0.4028 0.2883 0.040 Uiso 1 1 calc R . .
H4C H 0.6947 0.4516 0.2612 0.040 Uiso 1 1 calc R . .
C5 C 0.93311(19) 0.6331(3) 0.52645(16) 0.0173(6) Uiso 1 1 d . . .
H5A H 0.9799 0.6333 0.5023 0.021 Uiso 1 1 calc R . .
H5B H 0.9609 0.5821 0.5750 0.021 Uiso 1 1 calc R . .
C6 C 0.9127(2) 0.7848(3) 0.54245(17) 0.0203(6) Uiso 1 1 d . . .
H6A H 0.8604 0.7858 0.5607 0.024 Uiso 1 1 calc R . .
H6B H 0.8927 0.8393 0.4949 0.024 Uiso 1 1 calc R . .
C7 C 1.0020(2) 0.8543(3) 0.60315(17) 0.0224(6) Uiso 1 1 d . . .
H7A H 0.9861 0.9512 0.6115 0.027 Uiso 1 1 calc R . .
H7B H 1.0184 0.8034 0.6516 0.027 Uiso 1 1 calc R . .
C8 C 1.0895(2) 0.8565(3) 0.58115(18) 0.0282(7) Uiso 1 1 d . . .
H8A H 1.1109 0.7610 0.5794 0.042 Uiso 1 1 calc R . .
H8B H 1.1402 0.9100 0.6189 0.042 Uiso 1 1 calc R . .
H8C H 1.0725 0.9000 0.5313 0.042 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
Br1 0.01933(15) 0.01641(15) 0.01559(16) -0.00131(10) 0.00720(11) -0.00207(10)
Br2 0.02183(16) 0.02348(17) 0.02397(17) 0.00181(11) 0.00837(12) 0.00547(11)
Mn1 0.0183(3) 0.0157(3) 0.0136(3) 0.000 0.0058(2) 0.000

_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
Br1 Mn1 2.5227(5) . ?
Br2 Mn1 2.4990(5) . ?
Mn1 Br2 2.4990(5) 2 ?
Mn1 Br1 2.5227(5) 2 ?
N1 C1 1.335(3) . ?
N1 C2 1.377(3) . ?
N1 C5 1.479(3) . ?
N2 C1 1.321(3) . ?
N2 C3 1.372(3) . ?
N2 C4 1.469(3) . ?
C2 C3 1.352(4) . ?
C5 C6 1.513(4) . ?
C6 C7 1.534(4) . ?
C7 C8 1.521(4) . ?

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
Br2 Mn1 Br2 112.29(3) 2 . ?
Br2 Mn1 Br1 108.630(10) 2 . ?
Br2 Mn1 Br1 111.605(10) . . ?
Br2 Mn1 Br1 111.605(10) 2 2 ?
Br2 Mn1 Br1 108.630(10) . 2 ?
Br1 Mn1 Br1 103.78(2) . 2 ?
C1 N1 C2 108.2(2) . . ?
C1 N1 C5 126.2(2) . . ?
C2 N1 C5 125.6(2) . . ?
C1 N2 C3 108.5(2) . . ?
C1 N2 C4 125.5(2) . . ?
C3 N2 C4 126.0(2) . . ?
N2 C1 N1 109.0(2) . . ?
C3 C2 N1 106.8(2) . . ?
C2 C3 N2 107.5(3) . . ?
N1 C5 C6 112.1(2) . . ?
C5 C6 C7 111.3(2) . . ?
C8 C7 C6 114.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.936
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.117