#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/06/2230668.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_2230668
loop_
_publ_author_name
'Liu, Li-Jun'
_publ_section_title
;
 {N,N'-Bis[1-(pyridin-2-yl)ethylidene]propane-1,3-diamine}bromidocopper(II)
 tetrafluoridoborate
;
_journal_coeditor_code           HB5900
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m878
_journal_paper_doi               10.1107/S1600536811022513
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Cu Br (C17 H20 N4)] B F4'
_chemical_formula_moiety         'C17 H20 Br Cu N4 +, B F4 -'
_chemical_formula_sum            'C17 H20 B Br Cu F4 N4'
_chemical_formula_weight         510.63
_chemical_name_systematic
;
{N,N'-Bis[1-(pyridin-2-yl)ethylidene]propane-1,3-
diamine}bromidocopper(II) tetrafluoridoborate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.391(2)
_cell_angle_beta                 94.847(2)
_cell_angle_gamma                96.422(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2508(17)
_cell_length_b                   8.9511(18)
_cell_length_c                   13.158(3)
_cell_measurement_reflns_used    1747
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      2.5
_cell_volume                     960.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5958
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.263
_exptl_absorpt_correction_T_max  0.521
_exptl_absorpt_correction_T_min  0.473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.462
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0353P)²+0.1409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                2723
_reflns_number_total             3683
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5900.cif
_cod_data_source_block           I
_cod_original_cell_volume        960.9(3)
_cod_database_code               2230668
_cod_database_fobs_code          2230668
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.90467(5) 0.78988(5) 0.74936(3) 0.03382(14) Uani d . 1 1 . .
Br Br1 1.14320(5) 0.95979(5) 0.69040(3) 0.04830(14) Uani d . 1 1 . .
F F1 0.5630(4) 0.4076(3) 0.2862(2) 0.0787(8) Uani d . 1 1 . .
F F2 0.4093(3) 0.5940(3) 0.2543(2) 0.0754(8) Uani d . 1 1 . .
F F3 0.6555(3) 0.5941(3) 0.1938(2) 0.0870(9) Uani d . 1 1 . .
F F4 0.4467(4) 0.4290(3) 0.1279(2) 0.0792(8) Uani d . 1 1 . .
N N1 0.9085(3) 0.5870(3) 0.6691(2) 0.0318(7) Uani d . 1 1 . .
N N2 0.7458(4) 0.8146(3) 0.6317(2) 0.0370(7) Uani d . 1 1 . .
N N3 0.7643(3) 0.8783(3) 0.8484(2) 0.0339(7) Uani d . 1 1 . .
N N4 1.0231(3) 0.7455(3) 0.8815(2) 0.0343(7) Uani d . 1 1 . .
B B1 0.5174(6) 0.5077(5) 0.2150(4) 0.0410(11) Uani d . 1 1 . .
C C1 0.8099(4) 0.5758(4) 0.5809(3) 0.0333(8) Uani d . 1 1 . .
C C2 0.7912(5) 0.4481(4) 0.5165(3) 0.0410(10) Uani d . 1 1 . .
H H2 0.7238 0.4432 0.4558 0.049 Uiso calc R 1 1 . .
C C3 0.8740(5) 0.3273(4) 0.5435(3) 0.0490(11) Uani d . 1 1 . .
H H3 0.8628 0.2403 0.5011 0.059 Uiso calc R 1 1 . .
C C4 0.9726(5) 0.3373(4) 0.6333(3) 0.0463(10) Uani d . 1 1 . .
H H4 1.0284 0.2570 0.6530 0.056 Uiso calc R 1 1 . .
C C5 0.9879(5) 0.4694(4) 0.6942(3) 0.0388(9) Uani d . 1 1 . .
H H5 1.0558 0.4764 0.7548 0.047 Uiso calc R 1 1 . .
C C6 0.7252(4) 0.7110(4) 0.5613(3) 0.0338(8) Uani d . 1 1 . .
C C7 0.6216(5) 0.7181(5) 0.4626(3) 0.0549(12) Uani d . 1 1 . .
H H7A 0.5098 0.7227 0.4763 0.082 Uiso calc R 1 1 . .
H H7B 0.6287 0.6299 0.4198 0.082 Uiso calc R 1 1 . .
H H7C 0.6602 0.8062 0.4285 0.082 Uiso calc R 1 1 . .
C C8 0.6550(5) 0.9469(4) 0.6228(3) 0.0506(11) Uani d . 1 1 . .
H H8A 0.5399 0.9130 0.6050 0.061 Uiso calc R 1 1 . .
H H8B 0.6943 1.0060 0.5678 0.061 Uiso calc R 1 1 . .
C C9 0.6728(5) 1.0446(4) 0.7192(3) 0.0496(11) Uani d . 1 1 . .
H H9A 0.6033 1.1245 0.7103 0.060 Uiso calc R 1 1 . .
H H9B 0.7852 1.0911 0.7308 0.060 Uiso calc R 1 1 . .
C C10 0.6290(5) 0.9614(5) 0.8124(3) 0.0478(11) Uani d . 1 1 . .
H H10A 0.6076 1.0324 0.8660 0.057 Uiso calc R 1 1 . .
H H10B 0.5305 0.8919 0.7956 0.057 Uiso calc R 1 1 . .
C C11 0.7903(4) 0.8446(4) 0.9409(3) 0.0339(8) Uani d . 1 1 . .
C C12 0.6860(5) 0.8754(5) 1.0249(3) 0.0546(12) Uani d . 1 1 . .
H H12A 0.7435 0.9522 1.0718 0.082 Uiso calc R 1 1 . .
H H12B 0.6614 0.7850 1.0601 0.082 Uiso calc R 1 1 . .
H H12C 0.5860 0.9089 0.9966 0.082 Uiso calc R 1 1 . .
C C13 0.9414(4) 0.7715(4) 0.9639(3) 0.0316(8) Uani d . 1 1 . .
C C14 0.9996(5) 0.7370(5) 1.0603(3) 0.0447(10) Uani d . 1 1 . .
H H14 0.9410 0.7538 1.1163 0.054 Uiso calc R 1 1 . .
C C15 1.1478(5) 0.6765(5) 1.0722(3) 0.0492(11) Uani d . 1 1 . .
H H15 1.1893 0.6518 1.1364 0.059 Uiso calc R 1 1 . .
C C16 1.2322(5) 0.6535(4) 0.9889(3) 0.0434(10) Uani d . 1 1 . .
H H16 1.3313 0.6130 0.9960 0.052 Uiso calc R 1 1 . .
C C17 1.1684(4) 0.6912(4) 0.8944(3) 0.0403(9) Uani d . 1 1 . .
H H17 1.2275 0.6788 0.8381 0.048 Uiso calc R 1 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'
B B 0.0013 0.0007 '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
N2 Cu1 N4 . . 167.79(12) ?
N2 Cu1 N3 . . 92.15(12) ?
N4 Cu1 N3 . . 79.82(12) ?
N2 Cu1 N1 . . 80.08(12) ?
N4 Cu1 N1 . . 99.56(12) ?
N3 Cu1 N1 . . 137.46(11) ?
N2 Cu1 Br1 . . 96.74(9) ?
N4 Cu1 Br1 . . 95.17(9) ?
N3 Cu1 Br1 . . 118.16(9) ?
N1 Cu1 Br1 . . 104.32(8) ?
C5 N1 C1 . . 118.4(3) ?
C5 N1 Cu1 . . 129.4(2) ?
C1 N1 Cu1 . . 112.2(2) ?
C6 N2 C8 . . 120.0(3) ?
C6 N2 Cu1 . . 117.1(2) ?
C8 N2 Cu1 . . 122.9(3) ?
C11 N3 C10 . . 123.0(3) ?
C11 N3 Cu1 . . 115.8(2) ?
C10 N3 Cu1 . . 120.8(2) ?
C17 N4 C13 . . 119.2(3) ?
C17 N4 Cu1 . . 126.9(2) ?
C13 N4 Cu1 . . 113.8(2) ?
F3 B1 F2 . . 110.9(4) ?
F3 B1 F4 . . 109.5(4) ?
F2 B1 F4 . . 110.2(4) ?
F3 B1 F1 . . 107.5(3) ?
F2 B1 F1 . . 109.3(4) ?
F4 B1 F1 . . 109.3(4) ?
N1 C1 C2 . . 121.8(3) ?
N1 C1 C6 . . 114.1(3) ?
C2 C1 C6 . . 124.1(3) ?
C1 C2 C3 . . 119.1(4) ?
C1 C2 H2 . . 120.4 ?
C3 C2 H2 . . 120.4 ?
C4 C3 C2 . . 119.3(4) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 118.9(4) ?
C3 C4 H4 . . 120.6 ?
C5 C4 H4 . . 120.6 ?
N1 C5 C4 . . 122.5(4) ?
N1 C5 H5 . . 118.8 ?
C4 C5 H5 . . 118.8 ?
N2 C6 C1 . . 116.3(3) ?
N2 C6 C7 . . 124.1(4) ?
C1 C6 C7 . . 119.6(3) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 C9 . . 112.8(3) ?
N2 C8 H8A . . 109.0 ?
C9 C8 H8A . . 109.0 ?
N2 C8 H8B . . 109.0 ?
C9 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C8 C9 C10 . . 113.9(4) ?
C8 C9 H9A . . 108.8 ?
C10 C9 H9A . . 108.8 ?
C8 C9 H9B . . 108.8 ?
C10 C9 H9B . . 108.8 ?
H9A C9 H9B . . 107.7 ?
N3 C10 C9 . . 109.7(3) ?
N3 C10 H10A . . 109.7 ?
C9 C10 H10A . . 109.7 ?
N3 C10 H10B . . 109.7 ?
C9 C10 H10B . . 109.7 ?
H10A C10 H10B . . 108.2 ?
N3 C11 C13 . . 114.8(3) ?
N3 C11 C12 . . 125.8(3) ?
C13 C11 C12 . . 119.4(3) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N4 C13 C14 . . 121.6(3) ?
N4 C13 C11 . . 114.1(3) ?
C14 C13 C11 . . 124.3(3) ?
C13 C14 C15 . . 118.5(4) ?
C13 C14 H14 . . 120.7 ?
C15 C14 H14 . . 120.7 ?
C16 C15 C14 . . 119.7(4) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C17 . . 119.1(4) ?
C15 C16 H16 . . 120.4 ?
C17 C16 H16 . . 120.4 ?
N4 C17 C16 . . 121.7(3) ?
N4 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
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 N2 . 1.978(3) y
Cu1 N4 . 1.998(3) y
Cu1 N3 . 2.010(3) y
Cu1 N1 . 2.067(3) y
Cu1 Br1 . 2.5447(7) y
F1 B1 . 1.381(5) ?
F2 B1 . 1.363(5) ?
F3 B1 . 1.360(5) ?
F4 B1 . 1.370(5) ?
N1 C5 . 1.339(4) ?
N1 C1 . 1.354(4) ?
N2 C6 . 1.270(4) ?
N2 C8 . 1.474(4) ?
N3 C11 . 1.272(4) ?
N3 C10 . 1.467(4) ?
N4 C17 . 1.343(4) ?
N4 C13 . 1.349(4) ?
C1 C2 . 1.381(5) ?
C1 C6 . 1.485(5) ?
C2 C3 . 1.385(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.371(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.388(5) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C6 C7 . 1.501(5) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.498(6) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.511(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C13 . 1.486(5) ?
C11 C12 . 1.492(5) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.378(5) ?
C14 C15 . 1.392(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.367(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.380(5) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 F1 . 0.93 2.49 3.413(5) 173
C12 H12B F3 1_556 0.96 2.50 3.430(5) 162
C15 H15 F2 1_656 0.93 2.40 3.252(5) 152
