#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/89/2218934.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2218934
loop_
_publ_author_name
'Lee, Hon Man'
'Lu, Chi-Ying'
'Cheng, Pi-Yun'
_publ_section_title
;
 3,3'-Bis(4-fluorobenzyl)-1,1'-ethylenediimidazolium
 tribromidocuprate(I)
;
_journal_coeditor_code           CF2209
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1028
_journal_paper_doi               10.1107/S1600536808021521
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '(C22 H22 F2 N4) [Cu Br3]'
_chemical_formula_moiety         'C22 H22 F2 N4 2+, Br3 Cu 2-'
_chemical_formula_sum            'C22 H22 Br3 Cu F2 N4'
_chemical_formula_weight         683.71
_chemical_name_systematic
;
3,3'-Bis(4-fluorobenzyl)-1,1'-ethylenediimidazolium tribromidocuprate(I)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.582(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4994(11)
_cell_length_b                   11.0825(8)
_cell_length_c                   15.4464(12)
_cell_measurement_reflns_used    3837
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.4
_cell_volume                     2351.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11647
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    6.060
_exptl_absorpt_correction_T_max  0.3177
_exptl_absorpt_correction_T_min  0.2135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.508
_refine_diff_density_min         -0.735
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0522P)²+7.4402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0913
_reflns_number_gt                2242
_reflns_number_total             2686
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf2209.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2218934
_cod_database_fobs_code          2218934
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cu Cu1 0.5000 0.18316(6) 0.2500 0.03387(17) Uani d S 1
Br Br1 0.48562(2) 0.06476(3) 0.11487(2) 0.02810(12) Uani d . 1
Br Br2 0.5000 0.39352(5) 0.2500 0.03037(14) Uani d S 1
F F1 0.8176(2) 0.0493(2) 0.03890(16) 0.0474(6) Uani d . 1
N N1 0.71155(19) 0.6850(2) 0.08805(18) 0.0213(6) Uani d . 1
N N2 0.7085(2) 0.5320(2) 0.17325(18) 0.0213(5) Uani d . 1
C C1 0.7483(2) 0.7770(3) 0.0448(2) 0.0224(6) Uani d . 1
H H1A 0.8143 0.8030 0.0933 0.027 Uiso calc R 1
H H1B 0.7050 0.8484 0.0254 0.027 Uiso calc R 1
C C2 0.7660(2) 0.6007(3) 0.1510(2) 0.0241(7) Uani d . 1
H H2A 0.8343 0.5911 0.1759 0.029 Uiso calc R 1
C C3 0.6162(2) 0.6686(3) 0.0690(3) 0.0286(7) Uani d . 1
H H3A 0.5618 0.7158 0.0264 0.034 Uiso calc R 1
C C4 0.6148(3) 0.5730(3) 0.1223(3) 0.0287(7) Uani d . 1
H H4A 0.5591 0.5401 0.1241 0.034 Uiso calc R 1
C C5 0.7439(3) 0.4259(3) 0.2389(2) 0.0254(7) Uani d . 1
H H5A 0.6941 0.4014 0.2586 0.030 Uiso calc R 1
H H5B 0.8039 0.4478 0.2986 0.030 Uiso calc R 1
C C6 0.7651(2) 0.3216(3) 0.1889(2) 0.0229(7) Uani d . 1
C C7 0.6915(3) 0.2417(3) 0.1315(2) 0.0290(7) Uani d . 1
H H7A 0.6286 0.2509 0.1268 0.035 Uiso calc R 1
C C8 0.7084(3) 0.1489(3) 0.0809(3) 0.0355(9) Uani d . 1
H H8A 0.6581 0.0945 0.0416 0.043 Uiso calc R 1
C C9 0.8001(3) 0.1388(3) 0.0898(2) 0.0325(8) Uani d . 1
C C10 0.8756(3) 0.2142(3) 0.1463(3) 0.0324(8) Uani d . 1
H H10A 0.9386 0.2033 0.1513 0.039 Uiso calc R 1
C C11 0.8573(2) 0.3071(3) 0.1961(2) 0.0268(7) Uani d . 1
H H11A 0.9082 0.3610 0.2352 0.032 Uiso calc R 1
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br2 Cu1 Br1 . . 123.349(16) yes
Br2 Cu1 Br1 . 2_655 123.349(16) ?
Br1 Cu1 Br1 . 2_655 113.30(3) yes
C2 N1 C3 . . 108.6(3) ?
C2 N1 C1 . . 124.8(3) ?
C3 N1 C1 . . 126.6(3) ?
C2 N2 C4 . . 108.7(3) ?
C2 N2 C5 . . 123.3(3) ?
C4 N2 C5 . . 127.9(3) ?
N1 C1 C1 . 7_665 108.8(3) ?
N1 C1 H1A . . 109.9 ?
C1 C1 H1A 7_665 . 109.9 ?
N1 C1 H1B . . 109.9 ?
C1 C1 H1B 7_665 . 109.9 ?
H1A C1 H1B . . 108.3 ?
N1 C2 N2 . . 108.4(3) ?
N1 C2 H2A . . 125.8 ?
N2 C2 H2A . . 125.8 ?
C4 C3 N1 . . 107.0(3) ?
C4 C3 H3A . . 126.5 ?
N1 C3 H3A . . 126.5 ?
C3 C4 N2 . . 107.4(3) ?
C3 C4 H4A . . 126.3 ?
N2 C4 H4A . . 126.3 ?
N2 C5 C6 . . 110.9(3) ?
N2 C5 H5A . . 109.5 ?
C6 C5 H5A . . 109.5 ?
N2 C5 H5B . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.0 ?
C7 C6 C11 . . 119.1(3) ?
C7 C6 C5 . . 120.4(3) ?
C11 C6 C5 . . 120.5(3) ?
C8 C7 C6 . . 121.2(3) ?
C8 C7 H7A . . 119.4 ?
C6 C7 H7A . . 119.4 ?
C9 C8 C7 . . 117.5(3) ?
C9 C8 H8A . . 121.2 ?
C7 C8 H8A . . 121.2 ?
F1 C9 C8 . . 118.3(3) ?
F1 C9 C10 . . 118.0(4) ?
C8 C9 C10 . . 123.6(4) ?
C9 C10 C11 . . 118.0(4) ?
C9 C10 H10A . . 121.0 ?
C11 C10 H10A . . 121.0 ?
C10 C11 C6 . . 120.5(3) ?
C10 C11 H11A . . 119.8 ?
C6 C11 H11A . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 Br2 . 2.3314(9) yes
Cu1 Br1 . 2.3869(5) yes
Cu1 Br1 2_655 2.3869(5) ?
F1 C9 . 1.368(4) ?
N1 C2 . 1.331(4) ?
N1 C3 . 1.379(4) ?
N1 C1 . 1.470(4) ?
N2 C2 . 1.333(4) ?
N2 C4 . 1.370(4) ?
N2 C5 . 1.482(4) ?
C1 C1 7_665 1.532(6) ?
C1 H1A . 0.990 ?
C1 H1B . 0.990 ?
C2 H2A . 0.950 ?
C3 C4 . 1.349(5) ?
C3 H3A . 0.950 ?
C4 H4A . 0.950 ?
C5 C6 . 1.508(5) ?
C5 H5A . 0.990 ?
C5 H5B . 0.990 ?
C6 C7 . 1.390(5) ?
C6 C11 . 1.391(5) ?
C7 C8 . 1.388(6) ?
C7 H7A . 0.950 ?
C8 C9 . 1.369(6) ?
C8 H8A . 0.950 ?
C9 C10 . 1.373(5) ?
C10 C11 . 1.390(5) ?
C10 H10A . 0.950 ?
C11 H11A . 0.950 ?
