#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:12:39 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179681 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/03/7000384.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7000384
loop_
_publ_author_name
'Allen, John J.'
'Barron, Andrew R.'
_publ_section_title
;
 Olefin coordination in copper(I) complexes of bis(2-pyridyl)amine
;
_journal_issue                   5
_journal_name_full               'Dalton Transactions'
_journal_page_first              878
_journal_page_last               890
_journal_paper_doi               10.1039/b814829e
_journal_year                    2009
_chemical_formula_moiety         'C18 H25 Cu N3, B F4'
_chemical_formula_sum            'C18 H25 B Cu F4 N3'
_chemical_formula_weight         433.76
_chemical_melting_point          396
_chemical_name_common
;(2,2'-dipyridylamine)(eta2-1-octene)copper(i)
tetrafluoroborate
;
_chemical_name_systematic
'(2,2'-dipyridylamine)(η2-1-octene)copper(I) tetrafluoroborate'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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                 108.98(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.770(4)
_cell_length_b                   10.399(2)
_cell_length_c                   23.290(5)
_cell_measurement_reflns_used    1049
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14.59
_cell_measurement_theta_min      2.33
_cell_volume                     4069.8(17)
_computing_cell_refinement       'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_collection       'SMART v5.630 (Bruker-AXS 2003)'
_computing_data_reduction        'Bruker SAINT+ v6.45 (Bruker-AXS 2003)'
_computing_molecular_graphics    'SHELXTL v5.1'
_computing_publication_material  'SHELXTL v5.1'
_computing_structure_refinement  'SHELXTL v5.1'
_computing_structure_solution    'SHELXTL v5.1 (Bruker-AXS, 1998)'
_diffrn_ambient_pressure         101.33
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1494
_diffrn_reflns_av_sigmaI/netI    0.1616
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24172
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker SMART CCD'
_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_T_max  0.8595
_exptl_absorpt_correction_T_min  0.5400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker-AXS, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1792
_exptl_crystal_recrystallization_method
'sat. soln in MeOH cooled to -12 deg. C for several days'
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.2500
_refine_ls_R_factor_gt           0.0702
_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)+(0.0671P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.2017
_reflns_number_gt                1475
_reflns_number_total             4921
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b814829e.txt
_cod_data_source_block           dpa1o
_cod_original_cell_volume        4069.5(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7000384
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_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 0.61049(4) 1.16218(7) -0.14515(3) 0.0833(4) Uani 1 1 d . . .
N1 N 0.5232(3) 1.4302(4) -0.1678(2) 0.0811(14) Uani 1 1 d . . .
H1A H 0.4997 1.5026 -0.1678 0.097 Uiso 1 1 calc R . .
N2 N 0.4973(3) 1.2069(5) -0.1788(2) 0.0743(13) Uani 1 1 d . . .
N3 N 0.6521(3) 1.3387(4) -0.13773(19) 0.0729(12) Uani 1 1 d . . .
C1 C 0.4707(4) 1.3290(6) -0.1836(2) 0.0710(15) Uani 1 1 d . . .
C2 C 0.3903(4) 1.3561(6) -0.2044(3) 0.0838(17) Uani 1 1 d . . .
H2A H 0.3730 1.4409 -0.2067 0.101 Uiso 1 1 calc R . .
C3 C 0.3367(4) 1.2590(8) -0.2216(3) 0.095(2) Uani 1 1 d . . .
H3A H 0.2825 1.2772 -0.2362 0.114 Uiso 1 1 calc R . .
C4 C 0.3625(5) 1.1334(7) -0.2175(3) 0.0918(19) Uani 1 1 d . . .
H4A H 0.3267 1.0654 -0.2289 0.110 Uiso 1 1 calc R . .
C5 C 0.4411(5) 1.1132(6) -0.1964(3) 0.0901(19) Uani 1 1 d . . .
H5A H 0.4586 1.0284 -0.1936 0.108 Uiso 1 1 calc R . .
C6 C 0.6059(4) 1.4433(7) -0.1518(2) 0.0739(16) Uani 1 1 d . . .
C7 C 0.6347(4) 1.5656(6) -0.1513(3) 0.0917(19) Uani 1 1 d . . .
H7A H 0.6004 1.6357 -0.1615 0.110 Uiso 1 1 calc R . .
C8 C 0.7150(5) 1.5819(8) -0.1357(3) 0.106(2) Uani 1 1 d . . .
H8A H 0.7362 1.6640 -0.1346 0.127 Uiso 1 1 calc R . .
C9 C 0.7643(4) 1.4775(9) -0.1217(3) 0.106(2) Uani 1 1 d . . .
H9A H 0.8191 1.4876 -0.1110 0.127 Uiso 1 1 calc R . .
C10 C 0.7323(4) 1.3608(8) -0.1235(3) 0.094(2) Uani 1 1 d . . .
H10A H 0.7663 1.2903 -0.1145 0.113 Uiso 1 1 calc R . .
C11 C 0.6281(4) 0.9724(6) -0.1367(3) 0.103(2) Uani 1 1 d . . .
H11A H 0.6071 0.9289 -0.1083 0.123 Uiso 1 1 calc R . .
H11B H 0.6207 0.9247 -0.1739 0.123 Uiso 1 1 calc R . .
C12 C 0.6999(5) 1.0339(6) -0.1123(3) 0.095(2) Uani 1 1 d . . .
H12A H 0.7354 1.0262 -0.1367 0.114 Uiso 1 1 calc R . .
C13 C 0.7426(4) 1.0519(7) -0.0454(3) 0.113(2) Uani 1 1 d . . .
H13A H 0.7121 1.0108 -0.0228 0.135 Uiso 1 1 calc R . .
H13B H 0.7454 1.1431 -0.0361 0.135 Uiso 1 1 calc R . .
C14 C 0.8265(6) 0.9967(11) -0.0247(4) 0.188(5) Uani 1 1 d . . .
H14A H 0.8576 1.0521 -0.0419 0.226 Uiso 1 1 calc R . .
H14B H 0.8470 1.0093 0.0189 0.226 Uiso 1 1 calc R . .
C15 C 0.8455(5) 0.8779(9) -0.0344(4) 0.153(3) Uani 1 1 d . . .
H15A H 0.8244 0.8643 -0.0779 0.183 Uiso 1 1 calc R . .
H15B H 0.8155 0.8220 -0.0164 0.183 Uiso 1 1 calc R . .
C16 C 0.9278(7) 0.8278(11) -0.0146(5) 0.216(6) Uani 1 1 d . . .
H16A H 0.9593 0.8975 -0.0225 0.259 Uiso 1 1 calc R . .
H16B H 0.9426 0.8221 0.0293 0.259 Uiso 1 1 calc R . .
C17 C 0.9555(6) 0.7298(11) -0.0297(4) 0.188(4) Uani 1 1 d . . .
H17A H 0.9365 0.7330 -0.0737 0.225 Uiso 1 1 calc R . .
H17B H 0.9260 0.6606 -0.0190 0.225 Uiso 1 1 calc R . .
C18 C 1.0360(5) 0.6784(9) -0.0150(4) 0.160(4) Uani 1 1 d . . .
H18A H 1.0631 0.7209 -0.0393 0.240 Uiso 1 1 calc R . .
H18B H 1.0335 0.5878 -0.0233 0.240 Uiso 1 1 calc R . .
H18C H 1.0645 0.6927 0.0272 0.240 Uiso 1 1 calc R . .
B1 B 0.3993(7) 1.7416(9) -0.1851(6) 0.112(3) Uani 1 1 d . . .
F1 F 0.4539(3) 1.6740(5) -0.1956(3) 0.215(3) Uani 1 1 d . . .
F2 F 0.4290(4) 1.8269(6) -0.1395(3) 0.215(3) Uani 1 1 d . . .
F3 F 0.3627(3) 1.8178(4) -0.2323(3) 0.1664(19) Uani 1 1 d . . .
F4 F 0.3480(3) 1.6636(4) -0.1720(3) 0.189(2) Uani 1 1 d . . .
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'
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
N2 Cu1 N3 97.0(2) . . ?
N2 Cu1 C11 112.4(3) . . ?
N3 Cu1 C11 150.6(3) . . ?
N2 Cu1 C12 152.1(3) . . ?
N3 Cu1 C12 110.8(3) . . ?
C11 Cu1 C12 39.9(2) . . ?
C1 N1 C6 135.0(5) . . ?
C1 N1 H1A 112.5 . . ?
C6 N1 H1A 112.5 . . ?
C1 N2 C5 116.6(5) . . ?
C1 N2 Cu1 122.8(4) . . ?
C5 N2 Cu1 120.5(5) . . ?
C6 N3 C10 115.4(5) . . ?
C6 N3 Cu1 123.7(4) . . ?
C10 N3 Cu1 120.6(5) . . ?
N2 C1 N1 120.7(6) . . ?
N2 C1 C2 121.1(6) . . ?
N1 C1 C2 118.2(6) . . ?
C3 C2 C1 119.9(6) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 119.9(6) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C5 C4 C3 117.4(6) . . ?
C5 C4 H4A 121.3 . . ?
C3 C4 H4A 121.3 . . ?
C4 C5 N2 125.0(6) . . ?
C4 C5 H5A 117.5 . . ?
N2 C5 H5A 117.5 . . ?
N3 C6 C7 123.8(6) . . ?
N3 C6 N1 119.6(6) . . ?
C7 C6 N1 116.7(6) . . ?
C8 C7 C6 118.2(7) . . ?
C8 C7 H7A 120.9 . . ?
C6 C7 H7A 120.9 . . ?
C7 C8 C9 119.9(7) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C10 C9 C8 118.8(7) . . ?
C10 C9 H9A 120.6 . . ?
C8 C9 H9A 120.6 . . ?
C9 C10 N3 123.9(6) . . ?
C9 C10 H10A 118.1 . . ?
N3 C10 H10A 118.1 . . ?
C12 C11 Cu1 71.1(4) . . ?
C12 C11 H11A 116.5 . . ?
Cu1 C11 H11A 116.5 . . ?
C12 C11 H11B 116.5 . . ?
Cu1 C11 H11B 116.5 . . ?
H11A C11 H11B 113.5 . . ?
C11 C12 C13 125.0(7) . . ?
C11 C12 Cu1 69.0(4) . . ?
C13 C12 Cu1 112.3(4) . . ?
C11 C12 H12A 114.1 . . ?
C13 C12 H12A 114.1 . . ?
Cu1 C12 H12A 114.1 . . ?
C12 C13 C14 113.1(6) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 125.3(9) . . ?
C15 C14 H14A 106.0 . . ?
C13 C14 H14A 106.0 . . ?
C15 C14 H14B 106.0 . . ?
C13 C14 H14B 106.0 . . ?
H14A C14 H14B 106.3 . . ?
C14 C15 C16 123.9(10) . . ?
C14 C15 H15A 106.3 . . ?
C16 C15 H15A 106.3 . . ?
C14 C15 H15B 106.3 . . ?
C16 C15 H15B 106.3 . . ?
H15A C15 H15B 106.4 . . ?
C17 C16 C15 130.5(11) . . ?
C17 C16 H16A 104.6 . . ?
C15 C16 H16A 104.6 . . ?
C17 C16 H16B 104.6 . . ?
C15 C16 H16B 104.6 . . ?
H16A C16 H16B 105.7 . . ?
C16 C17 C18 133.5(12) . . ?
C16 C17 H17A 103.8 . . ?
C18 C17 H17A 103.8 . . ?
C16 C17 H17B 103.8 . . ?
C18 C17 H17B 103.8 . . ?
H17A C17 H17B 105.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F1 B1 F4 109.1(7) . . ?
F1 B1 F3 111.3(10) . . ?
F4 B1 F3 111.3(9) . . ?
F1 B1 F2 112.5(10) . . ?
F4 B1 F2 110.0(10) . . ?
F3 B1 F2 102.6(7) . . ?
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 N2 1.963(5) . ?
Cu1 N3 1.965(5) . ?
Cu1 C11 1.997(6) . ?
Cu1 C12 2.024(6) . ?
N1 C1 1.375(7) . ?
N1 C6 1.401(6) . ?
N1 H1A 0.8600 . ?
N2 C1 1.347(7) . ?
N2 C5 1.360(7) . ?
N3 C6 1.337(7) . ?
N3 C10 1.374(7) . ?
C1 C2 1.380(7) . ?
C2 C3 1.357(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.338(8) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.370(8) . ?
C7 C8 1.364(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.365(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.335(8) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C12 1.374(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.505(8) . ?
C12 H12A 0.9800 . ?
C13 C14 1.523(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.319(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.478(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.233(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.460(11) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
B1 F1 1.284(10) . ?
B1 F4 1.329(10) . ?
B1 F3 1.341(10) . ?
B1 F2 1.353(10) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A F1 0.86 1.98 2.800(7) 159.3 .
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
N3 N2 C11 C12 5.4(5) . . . . ?
N3 Cu1 N2 C1 -7.0(4) . . . . ?
C11 Cu1 N2 C1 174.0(4) . . . . ?
C12 Cu1 N2 C1 167.5(5) . . . . ?
N3 Cu1 N2 C5 175.6(4) . . . . ?
C11 Cu1 N2 C5 -3.4(5) . . . . ?
C12 Cu1 N2 C5 -9.9(7) . . . . ?
N2 Cu1 N3 C6 2.3(5) . . . . ?
C11 Cu1 N3 C6 -179.7(5) . . . . ?
C12 Cu1 N3 C6 -175.0(4) . . . . ?
N2 Cu1 N3 C10 -170.7(4) . . . . ?
C11 Cu1 N3 C10 7.3(7) . . . . ?
C12 Cu1 N3 C10 12.0(5) . . . . ?
C5 N2 C1 N1 -178.9(5) . . . . ?
Cu1 N2 C1 N1 3.6(7) . . . . ?
C5 N2 C1 C2 1.1(8) . . . . ?
Cu1 N2 C1 C2 -176.4(4) . . . . ?
C6 N1 C1 N2 8.3(9) . . . . ?
C6 N1 C1 C2 -171.8(5) . . . . ?
N2 C1 C2 C3 -1.4(9) . . . . ?
N1 C1 C2 C3 178.7(5) . . . . ?
C1 C2 C3 C4 0.8(9) . . . . ?
C2 C3 C4 C5 -0.2(9) . . . . ?
C3 C4 C5 N2 0.0(10) . . . . ?
C1 N2 C5 C4 -0.4(9) . . . . ?
Cu1 N2 C5 C4 177.1(5) . . . . ?
C10 N3 C6 C7 -1.2(8) . . . . ?
Cu1 N3 C6 C7 -174.5(4) . . . . ?
C10 N3 C6 N1 179.1(5) . . . . ?
Cu1 N3 C6 N1 5.7(7) . . . . ?
C1 N1 C6 N3 -13.5(9) . . . . ?
C1 N1 C6 C7 166.7(6) . . . . ?
N3 C6 C7 C8 0.0(9) . . . . ?
N1 C6 C7 C8 179.8(5) . . . . ?
C6 C7 C8 C9 0.7(10) . . . . ?
C7 C8 C9 C10 -0.1(11) . . . . ?
C8 C9 C10 N3 -1.2(11) . . . . ?
C6 N3 C10 C9 1.8(9) . . . . ?
Cu1 N3 C10 C9 175.3(5) . . . . ?
N2 Cu1 C11 C12 -175.2(4) . . . . ?
N3 Cu1 C11 C12 6.9(7) . . . . ?
Cu1 C11 C12 C13 103.1(6) . . . . ?
N2 Cu1 C12 C11 9.4(7) . . . . ?
N3 Cu1 C12 C11 -176.4(4) . . . . ?
N2 Cu1 C12 C13 -111.0(6) . . . . ?
N3 Cu1 C12 C13 63.1(6) . . . . ?
C11 Cu1 C12 C13 -120.5(7) . . . . ?
C11 C12 C13 C14 123.2(8) . . . . ?
Cu1 C12 C13 C14 -157.6(6) . . . . ?
C12 C13 C14 C15 -53.3(13) . . . . ?
C13 C14 C15 C16 178.9(9) . . . . ?
C14 C15 C16 C17 -164.8(14) . . . . ?
C15 C16 C17 C18 175.8(11) . . . . ?
