#------------------------------------------------------------------------------
#$Date: 2015-08-27 16:40:16 +0300 (Thu, 27 Aug 2015) $
#$Revision: 153730 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/76/7117648.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_7117648
loop_
_publ_author_name
'Hiroaki Kotani'
'Tomomi Yagi'
'Tomoya Ishizuka'
'Takahiko Kojima'
_publ_section_title
;
 Enhancement of 4-electron O2 reduction by a Cu(II)-pyridylamine complex
 via protonation of a pendant pyridine in the second coordination sphere
 in water
;
_journal_name_full               Chem.Commun.
_journal_page_first              13385
_journal_paper_doi               10.1039/C5cc03012A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C19 H21 B2 Cu F8 N4'
_chemical_formula_weight         542.56
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-04-08 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.731(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.516(7)
_cell_length_b                   9.366(4)
_cell_length_c                   15.706(7)
_cell_measurement_temperature    120(2)
_cell_volume                     2115.9(17)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.750
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_laue_measured_fraction_full 0.750
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8041
_diffrn_reflns_point_group_measured_fraction_full 0.750
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         22.816
_diffrn_reflns_theta_min         1.416
_exptl_absorpt_coefficient_mu    1.118
_exptl_crystal_colour            turcoise
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1096
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.886
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                1880
_reflns_number_total             2872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc03012a2_3.cif
_cod_data_source_block           Yagi13
_cod_database_code               7117648
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.25558(5) 0.13092(8) 0.83433(5) 0.0224(3) Uani 1 1 d . . . . .
F1 F 0.3802(2) 0.0554(4) 0.7580(2) 0.0295(9) Uani 1 1 d . . . . .
F2 F 0.4096(3) -0.1836(4) 0.7667(3) 0.0433(11) Uani 1 1 d . . . . .
F3 F 0.5069(3) -0.0334(4) 0.7075(3) 0.0401(11) Uani 1 1 d . . . . .
F4 F 0.5024(3) -0.0276(4) 0.8518(2) 0.0436(11) Uani 1 1 d . . . . .
F5 F 0.1211(3) 0.1943(4) 0.9135(3) 0.0404(10) Uani 1 1 d . . . . .
F6 F 0.0512(3) 0.3988(4) 0.8599(3) 0.0503(12) Uani 1 1 d . . . . .
F7 F -0.0168(3) 0.2596(5) 0.9535(3) 0.0666(15) Uani 1 1 d . . . . .
F8 F 0.1127(3) 0.3855(4) 0.9996(3) 0.0531(12) Uani 1 1 d . . . . .
N1 N 0.1576(3) 0.0364(5) 0.7478(3) 0.0243(13) Uani 1 1 d . . . . .
N2 N 0.2565(3) -0.0595(5) 0.8925(3) 0.0198(12) Uani 1 1 d . . . . .
N3 N 0.2288(4) 0.2982(5) 0.7567(3) 0.0254(13) Uani 1 1 d . . . . .
N4 N 0.6522(4) -0.2217(5) 1.0756(3) 0.0232(13) Uani 1 1 d . . . . .
C1 C 0.1114(5) -0.0708(8) 0.7971(5) 0.0361(19) Uani 1 1 d . . . . .
H1 H 0.0794 -0.1427 0.7575 0.043 Uiso 1 1 calc R U . . .
H2 H 0.0644 -0.0235 0.8276 0.043 Uiso 1 1 calc R U . . .
C2 C 0.1828(4) -0.1426(7) 0.8607(4) 0.0270(16) Uani 1 1 d . . . . .
C3 C 0.1770(5) -0.2818(7) 0.8897(5) 0.0362(19) Uani 1 1 d . . . . .
H3 H 0.1260 -0.3404 0.8673 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2456(4) -0.3351(7) 0.9510(4) 0.0305(18) Uani 1 1 d . . . . .
H4 H 0.2408 -0.4299 0.9714 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3206(4) -0.2526(7) 0.9828(4) 0.0253(16) Uani 1 1 d . . . . .
C6 C 0.3221(4) -0.1135(6) 0.9513(4) 0.0227(16) Uani 1 1 d . . . . .
H5 H 0.3728 -0.0538 0.9729 0.027 Uiso 1 1 calc R U . . .
C7 C 0.0953(5) 0.1503(7) 0.7090(4) 0.0324(18) Uani 1 1 d . . . . .
H6 H 0.0472 0.1712 0.7464 0.039 Uiso 1 1 calc R U . . .
H7 H 0.0636 0.1187 0.6524 0.039 Uiso 1 1 calc R U . . .
C8 C 0.1510(4) 0.2818(7) 0.6984(4) 0.0265(16) Uani 1 1 d . . . . .
C9 C 0.1244(5) 0.3849(7) 0.6369(4) 0.0333(18) Uani 1 1 d . . . . .
H8 H 0.0714 0.3702 0.5954 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1762(5) 0.5114(7) 0.6360(5) 0.0370(19) Uani 1 1 d . . . . .
H9 H 0.1577 0.5847 0.5955 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2545(5) 0.5264(7) 0.6953(4) 0.0334(18) Uani 1 1 d . . . . .
H10 H 0.2922 0.6094 0.6956 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2773(5) 0.4186(7) 0.7544(5) 0.0338(18) Uani 1 1 d . . . . .
H11 H 0.3307 0.4310 0.7958 0.041 Uiso 1 1 calc R U . . .
C13 C 0.3963(4) -0.3070(7) 1.0494(4) 0.0271(16) Uani 1 1 d . . . . .
H12 H 0.3853 -0.4098 1.0590 0.032 Uiso 1 1 calc R U . . .
H13 H 0.3920 -0.2566 1.1042 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4942(4) -0.2890(6) 1.0270(4) 0.0223(16) Uani 1 1 d . . . . .
C15 C 0.5170(5) -0.3133(7) 0.9457(4) 0.0299(17) Uani 1 1 d . . . . .
H14 H 0.4708 -0.3440 0.9008 0.036 Uiso 1 1 calc R U . . .
C16 C 0.6080(5) -0.2926(7) 0.9300(4) 0.0298(17) Uani 1 1 d . . . . .
H15 H 0.6247 -0.3099 0.8745 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6733(4) -0.2469(7) 0.9953(4) 0.0232(16) Uani 1 1 d . . . . .
H16 H 0.7354 -0.2325 0.9842 0.028 Uiso 1 1 calc R U . . .
C18 C 0.5638(4) -0.2443(6) 1.0902(4) 0.0183(15) Uani 1 1 d . . . . .
H17 H 0.5487 -0.2289 1.1465 0.022 Uiso 1 1 calc R U . . .
B1 B 0.4513(6) -0.0502(8) 0.7707(5) 0.0277(19) Uani 1 1 d . . . . .
B2 B 0.0643(5) 0.3096(9) 0.9325(6) 0.032(2) Uani 1 1 d . . . . .
C19 C 0.1991(5) -0.0386(8) 0.6771(5) 0.042(2) Uani 1 1 d . . . . .
H18 H 0.2433 -0.1111 0.7021 0.062 Uiso 1 1 calc R U . . .
H19 H 0.2314 0.0310 0.6452 0.062 Uiso 1 1 calc R U . . .
H20 H 0.1495 -0.0845 0.6380 0.062 Uiso 1 1 calc R U . . .
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
N3 Cu1 N4 98.9(2) . 3_657
N3 Cu1 N2 165.6(2) . .
N4 Cu1 N2 95.3(2) 3_657 .
N3 Cu1 N1 82.6(2) . .
N4 Cu1 N1 177.0(2) 3_657 .
N2 Cu1 N1 83.0(2) . .
N3 Cu1 F1 91.36(17) . .
N4 Cu1 F1 90.03(18) 3_657 .
N2 Cu1 F1 90.38(17) . .
N1 Cu1 F1 92.53(17) . .
B1 F1 Cu1 135.5(4) . .
C7 N1 C1 114.3(5) . .
C7 N1 C19 108.5(5) . .
C1 N1 C19 108.8(5) . .
C7 N1 Cu1 107.2(4) . .
C1 N1 Cu1 105.7(4) . .
C19 N1 Cu1 112.5(4) . .
C6 N2 C2 119.3(5) . .
C6 N2 Cu1 127.9(4) . .
C2 N2 Cu1 112.6(4) . .
C12 N3 C8 118.0(6) . .
C12 N3 Cu1 128.5(5) . .
C8 N3 Cu1 113.5(4) . .
C18 N4 C17 118.0(5) . .
C18 N4 Cu1 120.5(4) . 3_657
C17 N4 Cu1 121.1(4) . 3_657
N1 C1 C2 109.4(5) . .
N2 C2 C3 119.8(6) . .
N2 C2 C1 115.2(6) . .
C3 C2 C1 125.0(6) . .
C4 C3 C2 119.9(6) . .
C5 C4 C3 120.8(6) . .
C4 C5 C6 116.5(6) . .
C4 C5 C13 122.2(6) . .
C6 C5 C13 121.3(6) . .
N2 C6 C5 123.8(6) . .
N1 C7 C8 109.3(5) . .
N3 C8 C9 121.2(6) . .
N3 C8 C7 115.5(5) . .
C9 C8 C7 123.3(6) . .
C8 C9 C10 119.8(7) . .
C11 C10 C9 118.3(6) . .
C10 C11 C12 118.7(6) . .
N3 C12 C11 123.9(6) . .
C5 C13 C14 114.9(6) . .
C15 C14 C18 118.2(6) . .
C15 C14 C13 123.0(6) . .
C18 C14 C13 118.9(6) . .
C14 C15 C16 119.5(6) . .
C17 C16 C15 119.3(7) . .
N4 C17 C16 122.0(6) . .
N4 C18 C14 123.0(6) . .
F3 B1 F2 111.5(6) . .
F3 B1 F4 110.5(6) . .
F2 B1 F4 110.6(6) . .
F3 B1 F1 107.7(5) . .
F2 B1 F1 108.4(6) . .
F4 B1 F1 108.0(6) . .
F7 B2 F8 111.2(7) . .
F7 B2 F6 112.1(6) . .
F8 B2 F6 108.2(6) . .
F7 B2 F5 109.8(7) . .
F8 B2 F5 107.6(6) . .
F6 B2 F5 107.6(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N3 1.992(5) .
Cu1 N4 2.001(5) 3_657
Cu1 N2 2.003(5) .
Cu1 N1 2.034(5) .
Cu1 F1 2.407(4) .
F1 B1 1.424(8) .
F2 B1 1.387(9) .
F3 B1 1.371(9) .
F4 B1 1.400(8) .
F5 B2 1.414(9) .
F6 B2 1.406(9) .
F7 B2 1.348(9) .
F8 B2 1.383(9) .
N1 C7 1.476(8) .
N1 C1 1.483(8) .
N1 C19 1.506(9) .
N2 C6 1.334(7) .
N2 C2 1.362(8) .
N3 C12 1.332(8) .
N3 C8 1.364(8) .
N4 C18 1.350(8) .
N4 C17 1.359(8) .
N4 Cu1 2.001(5) 3_657
C1 C2 1.498(9) .
C2 C3 1.387(9) .
C3 C4 1.382(9) .
C4 C5 1.373(9) .
C5 C6 1.395(9) .
C5 C13 1.501(9) .
C7 C8 1.495(9) .
C8 C9 1.383(9) .
C9 C10 1.404(9) .
C10 C11 1.376(10) .
C11 C12 1.380(9) .
C13 C14 1.520(9) .
C14 C15 1.380(9) .
C14 C18 1.382(8) .
C15 C16 1.390(9) .
C16 C17 1.368(9) .
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
C7 N1 C1 C2 -157.3(6) . . . .
C19 N1 C1 C2 81.3(7) . . . .
Cu1 N1 C1 C2 -39.7(6) . . . .
C6 N2 C2 C3 0.0(10) . . . .
Cu1 N2 C2 C3 175.1(5) . . . .
C6 N2 C2 C1 178.2(6) . . . .
Cu1 N2 C2 C1 -6.7(7) . . . .
N1 C1 C2 N2 31.9(8) . . . .
N1 C1 C2 C3 -150.0(7) . . . .
N2 C2 C3 C4 0.5(11) . . . .
C1 C2 C3 C4 -177.6(7) . . . .
C2 C3 C4 C5 -1.1(11) . . . .
C3 C4 C5 C6 1.3(10) . . . .
C3 C4 C5 C13 180.0(7) . . . .
C2 N2 C6 C5 0.2(9) . . . .
Cu1 N2 C6 C5 -174.1(5) . . . .
C4 C5 C6 N2 -0.9(10) . . . .
C13 C5 C6 N2 -179.6(6) . . . .
C1 N1 C7 C8 153.5(6) . . . .
C19 N1 C7 C8 -85.0(7) . . . .
Cu1 N1 C7 C8 36.7(6) . . . .
C12 N3 C8 C9 1.9(10) . . . .
Cu1 N3 C8 C9 -177.0(5) . . . .
C12 N3 C8 C7 -175.0(6) . . . .
Cu1 N3 C8 C7 6.0(7) . . . .
N1 C7 C8 N3 -29.2(8) . . . .
N1 C7 C8 C9 154.0(6) . . . .
N3 C8 C9 C10 -2.4(10) . . . .
C7 C8 C9 C10 174.3(7) . . . .
C8 C9 C10 C11 2.3(11) . . . .
C9 C10 C11 C12 -1.7(11) . . . .
C8 N3 C12 C11 -1.4(10) . . . .
Cu1 N3 C12 C11 177.3(5) . . . .
C10 C11 C12 N3 1.4(11) . . . .
C4 C5 C13 C14 128.2(7) . . . .
C6 C5 C13 C14 -53.2(9) . . . .
C5 C13 C14 C15 -41.1(9) . . . .
C5 C13 C14 C18 138.0(6) . . . .
C18 C14 C15 C16 0.1(9) . . . .
C13 C14 C15 C16 179.1(6) . . . .
C14 C15 C16 C17 -0.7(9) . . . .
C18 N4 C17 C16 0.7(9) . . . .
Cu1 N4 C17 C16 -171.9(5) 3_657 . . .
C15 C16 C17 N4 0.3(9) . . . .
C17 N4 C18 C14 -1.3(8) . . . .
Cu1 N4 C18 C14 171.3(4) 3_657 . . .
C15 C14 C18 N4 0.9(9) . . . .
C13 C14 C18 N4 -178.1(5) . . . .
Cu1 F1 B1 F3 -175.1(3) . . . .
Cu1 F1 B1 F2 64.2(7) . . . .
Cu1 F1 B1 F4 -55.7(8) . . . .
