# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
# 
#######################################################################

data_exp_3405
_database_code_depnum_ccdc_archive 'CCDC 1016871'
_audit_update_record             
;
2014-07-30 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;
_audit_creation_date             2014-04-22
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_systematic        'Bis(3N-triazolyl)copper(I) tetrafluoroborate'
_chemical_name_common            ?
_chemical_formula_moiety         'C30 H26 Cu N6, B F4'
_chemical_formula_sum            'C30 H26 B Cu F4 N6'
_chemical_formula_weight         620.92
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
_chemical_melting_point          551
_diffrn_ambient_temperature      180.01(10)
_chemical_oxdiff_formula         'C1 H1 N1 Cu1'
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'
Cu Cu 0.3201 1.2651 '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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   24.8641(12)
_cell_length_b                   6.0228(3)
_cell_length_c                   18.6609(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.811(5)
_cell_angle_gamma                90
_cell_volume                     2768.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2239
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      27.4700
_cell_measurement_theta_min      3.9590
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4768
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.308
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9628
_diffrn_measured_fraction_theta_max 0.8042
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00  101.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  178.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega  -76.00    8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.5610  -57.0000 -180.0000 84
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0175645000
_diffrn_orient_matrix_UB_12      -0.0271718000
_diffrn_orient_matrix_UB_13      0.0319897000
_diffrn_orient_matrix_UB_21      0.0227735000
_diffrn_orient_matrix_UB_22      0.0156338000
_diffrn_orient_matrix_UB_23      -0.0185769000
_diffrn_orient_matrix_UB_31      0.0010859000
_diffrn_orient_matrix_UB_32      0.1135780000
_diffrn_orient_matrix_UB_33      0.0101699000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2142
_reflns_number_total             2681
_reflns_odcompleteness_completeness 96.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         1.024
_refine_diff_density_min         -0.950
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+11.3961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1482
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.7500 0.2500 0.7500 0.0319(2) Uani 1 2 d S . P . .
F1 F 0.54479(18) 0.1476(10) 0.7619(2) 0.144(2) Uani 1 1 d . . . . .
F2 F 0.50197(18) -0.0865(7) 0.6892(2) 0.1237(18) Uani 1 1 d . . . . .
N1 N 0.68655(10) 0.4190(5) 0.73843(15) 0.0257(6) Uani 1 1 d . . . . .
N2 N 0.64739(11) 0.3438(5) 0.68871(16) 0.0283(6) Uani 1 1 d . . . . .
N3 N 0.60778(10) 0.4912(5) 0.68576(15) 0.0257(6) Uani 1 1 d . . . . .
B1 B 0.5000 0.0317(12) 0.7500 0.0382(14) Uani 1 2 d S T P . .
C1 C 0.67123(12) 0.6131(5) 0.76694(17) 0.0230(7) Uani 1 1 d . . . . .
C2 C 0.62001(13) 0.6598(6) 0.73236(19) 0.0264(7) Uani 1 1 d . . . . .
H2 H 0.5980 0.7844 0.7398 0.032 Uiso 1 1 calc R U . . .
C3 C 0.70439(12) 0.7403(5) 0.82385(17) 0.0227(7) Uani 1 1 d . . . . .
C4 C 0.68515(13) 0.9448(6) 0.84501(19) 0.0294(8) Uani 1 1 d . . . . .
H4 H 0.6516 1.0011 0.8215 0.035 Uiso 1 1 calc R U . . .
C5 C 0.71453(15) 1.0653(6) 0.8998(2) 0.0342(8) Uani 1 1 d . . . . .
H5 H 0.7006 1.2025 0.9144 0.041 Uiso 1 1 calc R U . . .
C6 C 0.76373(15) 0.9898(7) 0.9336(2) 0.0356(9) Uani 1 1 d . . . . .
H6 H 0.7838 1.0743 0.9711 0.043 Uiso 1 1 calc R U . . .
C7 C 0.78365(14) 0.7888(7) 0.9124(2) 0.0335(8) Uani 1 1 d . . . . .
H7 H 0.8178 0.7360 0.9351 0.040 Uiso 1 1 calc R U . . .
C8 C 0.75424(13) 0.6651(6) 0.85850(19) 0.0293(8) Uani 1 1 d . . . . .
H8 H 0.7681 0.5268 0.8448 0.035 Uiso 1 1 calc R U . . .
C9 C 0.55832(13) 0.4591(6) 0.63349(18) 0.0297(8) Uani 1 1 d . . . . .
H9A H 0.5288 0.5533 0.6474 0.036 Uiso 1 1 calc R U . . .
H9B H 0.5466 0.3023 0.6347 0.036 Uiso 1 1 calc R U . . .
C10 C 0.56817(12) 0.5178(6) 0.55845(18) 0.0265(7) Uani 1 1 d . . . . .
C11 C 0.59015(14) 0.3641(6) 0.5160(2) 0.0346(8) Uani 1 1 d . . . . .
H11 H 0.6000 0.2215 0.5352 0.042 Uiso 1 1 calc R U . . .
C12 C 0.59804(16) 0.4146(8) 0.4460(2) 0.0442(10) Uani 1 1 d . . . . .
H12 H 0.6131 0.3064 0.4175 0.053 Uiso 1 1 calc R U . . .
C13 C 0.58433(15) 0.6201(8) 0.4175(2) 0.0430(10) Uani 1 1 d . . . . .
H13 H 0.5897 0.6543 0.3693 0.052 Uiso 1 1 calc R U . . .
C14 C 0.56285(16) 0.7759(7) 0.4591(2) 0.0421(10) Uani 1 1 d . . . . .
H14 H 0.5536 0.9189 0.4397 0.050 Uiso 1 1 calc R U . . .
C15 C 0.55448(14) 0.7260(6) 0.5293(2) 0.0328(8) Uani 1 1 d . . . . .
H15 H 0.5393 0.8345 0.5576 0.039 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0278(3) 0.0306(4) 0.0349(4) -0.0052(3) -0.0044(2) 0.0096(3)
F1 0.139(3) 0.236(5) 0.057(2) 0.003(3) 0.009(2) -0.145(4)
F2 0.154(4) 0.126(3) 0.076(3) -0.061(2) -0.036(2) 0.079(3)
N1 0.0226(13) 0.0260(14) 0.0275(15) 0.0004(12) 0.0001(11) 0.0006(12)
N2 0.0266(14) 0.0290(15) 0.0282(16) -0.0012(13) 0.0005(11) 0.0017(13)
N3 0.0211(13) 0.0331(16) 0.0223(14) 0.0020(12) 0.0007(10) 0.0010(12)
B1 0.031(3) 0.057(4) 0.027(3) 0.000 0.008(2) 0.000
C1 0.0231(15) 0.0261(17) 0.0208(16) 0.0029(13) 0.0063(12) 0.0017(13)
C2 0.0233(15) 0.0292(17) 0.0271(18) -0.0030(15) 0.0044(13) 0.0011(14)
C3 0.0201(15) 0.0285(17) 0.0203(16) 0.0011(13) 0.0054(12) -0.0027(13)
C4 0.0261(16) 0.0305(18) 0.0312(19) 0.0011(15) 0.0025(13) 0.0018(15)
C5 0.040(2) 0.0315(19) 0.032(2) -0.0068(16) 0.0086(15) -0.0028(16)
C6 0.0344(19) 0.045(2) 0.0271(19) -0.0067(17) 0.0043(15) -0.0105(17)
C7 0.0271(17) 0.047(2) 0.0248(18) 0.0041(16) -0.0018(14) -0.0033(16)
C8 0.0271(17) 0.0335(19) 0.0269(18) -0.0006(15) 0.0024(13) 0.0025(15)
C9 0.0197(15) 0.043(2) 0.0253(18) -0.0034(15) -0.0017(13) -0.0038(15)
C10 0.0178(15) 0.0326(18) 0.0276(18) -0.0047(15) -0.0024(12) -0.0021(13)
C11 0.0350(19) 0.0308(19) 0.038(2) -0.0057(16) 0.0059(15) 0.0040(16)
C12 0.042(2) 0.056(3) 0.037(2) -0.013(2) 0.0125(17) -0.001(2)
C13 0.034(2) 0.064(3) 0.030(2) 0.003(2) 0.0004(16) -0.012(2)
C14 0.042(2) 0.039(2) 0.041(2) 0.0109(18) -0.0102(17) -0.0038(18)
C15 0.0291(18) 0.0275(18) 0.039(2) -0.0036(16) -0.0048(15) 0.0027(15)

_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 N1 1.865(3) . ?
Cu1 N1 1.865(3) 7_656 ?
F1 B1 1.307(5) . ?
F2 B1 1.346(5) . ?
N1 N2 1.330(4) . ?
N1 C1 1.361(4) . ?
N2 N3 1.321(4) . ?
N3 C2 1.345(4) . ?
N3 C9 1.475(4) . ?
B1 F1 1.307(5) 2_656 ?
B1 F2 1.346(5) 2_656 ?
C1 C2 1.376(4) . ?
C1 C3 1.468(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(5) . ?
C3 C8 1.393(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(5) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.496(5) . ?
C10 C11 1.379(5) . ?
C10 C15 1.390(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.372(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.371(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(6) . ?
C15 H15 0.9500 . ?

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
N1 Cu1 N1 180.0 7_656 . ?
N2 N1 Cu1 115.0(2) . . ?
N2 N1 C1 110.4(3) . . ?
C1 N1 Cu1 134.5(2) . . ?
N3 N2 N1 105.8(3) . . ?
N2 N3 C2 112.2(3) . . ?
N2 N3 C9 119.3(3) . . ?
C2 N3 C9 128.4(3) . . ?
F1 B1 F1 115.5(8) . 2_656 ?
F1 B1 F2 105.5(2) . 2_656 ?
F1 B1 F2 107.3(3) 2_656 2_656 ?
F1 B1 F2 105.5(2) 2_656 . ?
F1 B1 F2 107.3(3) . . ?
F2 B1 F2 116.1(7) . 2_656 ?
N1 C1 C2 106.4(3) . . ?
N1 C1 C3 124.9(3) . . ?
C2 C1 C3 128.7(3) . . ?
N3 C2 C1 105.2(3) . . ?
N3 C2 H2 127.4 . . ?
C1 C2 H2 127.4 . . ?
C4 C3 C1 118.9(3) . . ?
C8 C3 C1 122.9(3) . . ?
C8 C3 C4 118.2(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C3 C8 H8 119.6 . . ?
C7 C8 C3 120.9(3) . . ?
C7 C8 H8 119.6 . . ?
N3 C9 H9A 109.4 . . ?
N3 C9 H9B 109.4 . . ?
N3 C9 C10 111.1(3) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 C15 118.4(4) . . ?
C15 C10 C9 121.1(3) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.9(4) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.3(4) . . ?
C14 C15 H15 119.8 . . ?

_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.849
_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           2013-3
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

_exptl_crystal_colour            colorless
