# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_Yagi13
_database_code_depnum_ccdc_archive 'CCDC 1058367'
_audit_update_record             
;
2015-04-08 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 B2 Cu F8 N4'
_chemical_formula_weight         542.56

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   14.516(7)
_cell_length_b                   9.366(4)
_cell_length_c                   15.706(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.731(7)
_cell_angle_gamma                90
_cell_volume                     2115.9(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            turcoise
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.118
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8041
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.416
_diffrn_reflns_theta_max         22.816
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.750
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.750
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.750
_reflns_number_total             2872
_reflns_number_gt                1880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2872
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   0.886
_refine_ls_restrained_S_all      0.886
_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_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 . . .


_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
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_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
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_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
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) . . . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-4



