# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_i2a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Cu F N4 O3, B F4'
_chemical_formula_sum            'C18 H18 B Cu F5 N4 O3'
_chemical_formula_weight         507.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 2/a'
_symmetry_space_group_name_Hall  '-I 2ya'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.4006(3)
_cell_length_b                   9.5362(2)
_cell_length_c                   28.090(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.988(6)
_cell_angle_gamma                90.00
_cell_volume                     4124.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    19255
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      68.30

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2056
_exptl_absorpt_coefficient_mu    2.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6951
_exptl_absorpt_correction_T_max  0.9577
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 Crystals were found to undergo a destructive phase change upon cooling below 240 K and therefore data collection was performed at 240 K 
;

_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            56602
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         68.24
_reflns_number_total             3776
_reflns_number_gt                3032
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0952P)²+2.1294P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3776
_refine_ls_number_parameters     339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1636
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.66528(3) 0.14025(5) 0.099240(17) 0.0603(2) Uani 1 1 d . . .
F1 F 0.63205(16) 0.2638(2) 0.04790(8) 0.0784(6) Uani 1 1 d . . .
N1 N 0.69865(19) 0.0085(3) 0.15158(10) 0.0594(7) Uani 1 1 d . . .
N2 N 0.55888(19) 0.1749(3) 0.13938(10) 0.0581(7) Uani 1 1 d . . .
N3 N 0.7851(2) 0.2198(3) 0.11143(10) 0.0608(7) Uani 1 1 d . . .
O2 O 0.7926(3) 0.3604(3) 0.04521(10) 0.0836(9) Uani 1 1 d . . .
N4 N 0.6634(2) -0.0419(3) 0.05754(10) 0.0654(7) Uani 1 1 d . . .
C3 C 0.4980(3) 0.1137(4) 0.21365(15) 0.0752(11) Uani 1 1 d . . .
H3A H 0.4982 0.0575 0.2407 0.090 Uiso 1 1 calc R . .
O1 O 0.5032(3) 0.3583(3) 0.09570(13) 0.0872(9) Uani 1 1 d . . .
C2 C 0.5568(3) 0.0926(4) 0.17831(12) 0.0639(8) Uani 1 1 d . . .
C8 C 0.8205(3) 0.1738(4) 0.15288(14) 0.0662(9) Uani 1 1 d . . .
C6 C 0.5012(3) 0.2795(4) 0.13448(14) 0.0671(9) Uani 1 1 d . . .
O3 O 0.6034(2) 0.0487(4) -0.01106(10) 0.0915(9) Uani 1 1 d . . .
C1 C 0.6200(3) -0.0292(4) 0.17781(14) 0.0702(9) Uani 1 1 d . . .
H1A H 0.6358 -0.0546 0.2102 0.084 Uiso 1 1 calc R . .
H1B H 0.5924 -0.1097 0.1629 0.084 Uiso 1 1 calc R . .
C7 C 0.7617(3) 0.0862(4) 0.18253(14) 0.0716(10) Uani 1 1 d . . .
H7A H 0.7960 0.0201 0.2012 0.086 Uiso 1 1 calc R . .
H7B H 0.7305 0.1459 0.2044 0.086 Uiso 1 1 calc R . .
C5 C 0.4388(3) 0.3045(4) 0.16864(17) 0.0783(11) Uani 1 1 d . . .
H5A H 0.3985 0.3765 0.1647 0.094 Uiso 1 1 calc R . .
C12 C 0.8299(3) 0.3094(4) 0.08444(15) 0.0707(10) Uani 1 1 d . . .
C14 C 0.6921(3) -0.1535(4) 0.08337(15) 0.0691(9) Uani 1 1 d . . .
C11 C 0.9134(3) 0.3489(4) 0.0970(2) 0.0898(14) Uani 1 1 d . . .
H11A H 0.9451 0.4064 0.0769 0.108 Uiso 1 1 calc R . .
C4 C 0.4379(3) 0.2217(5) 0.20789(17) 0.0829(12) Uani 1 1 d . . .
H4A H 0.3968 0.2373 0.2312 0.100 Uiso 1 1 calc R . .
C15 C 0.6828(3) -0.2881(5) 0.06701(17) 0.0872(13) Uani 1 1 d . . .
H15A H 0.7014 -0.3640 0.0853 0.105 Uiso 1 1 calc R . .
C18 C 0.6283(3) -0.0611(5) 0.01473(14) 0.0755(10) Uani 1 1 d . . .
C9 C 0.9023(3) 0.2130(5) 0.1680(2) 0.0884(13) Uani 1 1 d . . .
H9A H 0.9258 0.1805 0.1966 0.106 Uiso 1 1 calc R . .
C17 C 0.6181(4) -0.1963(6) -0.00409(18) 0.0955(15) Uani 1 1 d . . .
H17A H 0.5934 -0.2094 -0.0342 0.115 Uiso 1 1 calc R . .
C10 C 0.9492(3) 0.3035(5) 0.1386(3) 0.1015(17) Uani 1 1 d . . .
H10A H 1.0047 0.3323 0.1478 0.122 Uiso 1 1 calc R . .
C16 C 0.6449(4) -0.3079(6) 0.0224(2) 0.1013(16) Uani 1 1 d . . .
H16A H 0.6379 -0.3982 0.0105 0.122 Uiso 1 1 calc R . .
C13 C 0.7385(3) -0.1167(4) 0.12903(15) 0.0691(9) Uani 1 1 d . . .
H13A H 0.7360 -0.1956 0.1508 0.083 Uiso 1 1 calc R . .
H13B H 0.7991 -0.0976 0.1227 0.083 Uiso 1 1 calc R . .
H1 H 0.548(4) 0.335(6) 0.082(2) 0.098(18) Uiso 1 1 d . . .
H2 H 0.729(5) 0.331(7) 0.047(2) 0.14(2) Uiso 1 1 d . . .
H3 H 0.608(4) 0.130(6) 0.004(2) 0.11(2) Uiso 1 1 d . . .
B1 B 0.6895(3) -0.4915(5) 0.19062(15) 0.0697(11) Uani 1 1 d . . .
F2 F 0.7542(6) -0.4205(11) 0.2208(3) 0.144(3) Uani 0.57 1 d P A 1
F3 F 0.6302(10) -0.3890(16) 0.1872(7) 0.121(5) Uani 0.57 1 d P A 1
F4 F 0.7297(7) -0.5068(9) 0.1494(3) 0.153(4) Uani 0.57 1 d P A 1
F5 F 0.6423(9) -0.5878(16) 0.2193(5) 0.091(3) Uani 0.57 1 d P A 1
F2A F 0.6541(14) -0.3674(18) 0.1963(7) 0.132(8) Uani 0.43 1 d P A 2
F3A F 0.6716(6) -0.5399(10) 0.1430(3) 0.100(3) Uani 0.43 1 d P A 2
F4A F 0.7704(5) -0.5045(12) 0.2004(4) 0.122(3) Uani 0.43 1 d P A 2
F5A F 0.6710(13) -0.609(2) 0.2103(7) 0.101(5) Uani 0.43 1 d P A 2


_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 F1 1.925(2) . ?
Cu1 N1 1.994(3) . ?
Cu1 N3 2.019(3) . ?
Cu1 N2 2.032(3) . ?
Cu1 N4 2.095(3) . ?
N1 C1 1.474(5) . ?
N1 C13 1.489(5) . ?
N1 C7 1.490(5) . ?
N2 C6 1.341(5) . ?
N2 C2 1.347(5) . ?
N3 C12 1.341(5) . ?
N3 C8 1.350(5) . ?
O2 C12 1.326(5) . ?
N4 C18 1.323(5) . ?
N4 C14 1.357(5) . ?
C3 C2 1.370(5) . ?
C3 C4 1.392(7) . ?
O1 C6 1.324(5) . ?
C2 C1 1.516(5) . ?
C8 C9 1.375(6) . ?
C8 C7 1.495(6) . ?
C6 C5 1.391(6) . ?
O3 C18 1.326(6) . ?
C5 C4 1.356(7) . ?
C12 C11 1.380(7) . ?
C14 C15 1.370(6) . ?
C14 C13 1.500(6) . ?
C11 C10 1.356(8) . ?
C15 C16 1.385(7) . ?
C18 C17 1.401(7) . ?
C9 C10 1.402(8) . ?
C17 C16 1.359(8) . ?
B1 F4A 1.277(9) . ?
B1 F5A 1.284(19) . ?
B1 F2A 1.313(16) . ?
B1 F4 1.330(8) . ?
B1 F3 1.339(14) . ?
B1 F5 1.428(15) . ?
B1 F3A 1.438(9) . ?
B1 F2 1.462(8) . ?

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
F1 Cu1 N1 178.70(12) . . ?
F1 Cu1 N3 97.32(11) . . ?
N1 Cu1 N3 83.60(12) . . ?
F1 Cu1 N2 96.30(11) . . ?
N1 Cu1 N2 83.88(12) . . ?
N3 Cu1 N2 126.04(11) . . ?
F1 Cu1 N4 95.03(11) . . ?
N1 Cu1 N4 83.74(12) . . ?
N3 Cu1 N4 114.19(12) . . ?
N2 Cu1 N4 116.21(12) . . ?
C1 N1 C13 111.5(3) . . ?
C1 N1 C7 111.3(3) . . ?
C13 N1 C7 112.2(3) . . ?
C1 N1 Cu1 108.6(2) . . ?
C13 N1 Cu1 107.1(2) . . ?
C7 N1 Cu1 105.9(2) . . ?
C6 N2 C2 119.4(3) . . ?
C6 N2 Cu1 127.1(2) . . ?
C2 N2 Cu1 112.8(2) . . ?
C12 N3 C8 119.4(4) . . ?
C12 N3 Cu1 128.4(3) . . ?
C8 N3 Cu1 112.2(2) . . ?
C18 N4 C14 120.1(3) . . ?
C18 N4 Cu1 128.7(3) . . ?
C14 N4 Cu1 110.5(2) . . ?
C2 C3 C4 118.1(4) . . ?
N2 C2 C3 121.9(4) . . ?
N2 C2 C1 114.5(3) . . ?
C3 C2 C1 123.5(4) . . ?
N3 C8 C9 122.1(4) . . ?
N3 C8 C7 115.0(3) . . ?
C9 C8 C7 122.7(4) . . ?
O1 C6 N2 118.8(3) . . ?
O1 C6 C5 119.7(4) . . ?
N2 C6 C5 121.4(4) . . ?
N1 C1 C2 110.6(3) . . ?
N1 C7 C8 110.3(3) . . ?
C4 C5 C6 118.5(4) . . ?
O2 C12 N3 118.9(4) . . ?
O2 C12 C11 120.0(4) . . ?
N3 C12 C11 121.0(4) . . ?
N4 C14 C15 121.6(4) . . ?
N4 C14 C13 114.8(3) . . ?
C15 C14 C13 123.5(4) . . ?
C10 C11 C12 119.7(5) . . ?
C5 C4 C3 120.6(4) . . ?
C14 C15 C16 118.1(5) . . ?
N4 C18 O3 119.8(4) . . ?
N4 C18 C17 120.8(4) . . ?
O3 C18 C17 119.4(4) . . ?
C8 C9 C10 117.7(5) . . ?
C16 C17 C18 118.9(5) . . ?
C11 C10 C9 119.9(5) . . ?
C17 C16 C15 120.5(5) . . ?
N1 C13 C14 110.9(3) . . ?
F4A B1 F5A 92.6(11) . . ?
F4A B1 F2A 117.8(11) . . ?
F5A B1 F2A 129.7(12) . . ?
F4A B1 F4 73.1(7) . . ?
F5A B1 F4 112.9(8) . . ?
F2A B1 F4 113.9(11) . . ?
F4A B1 F3 138.4(9) . . ?
F5A B1 F3 120.8(12) . . ?
F2A B1 F3 21.3(14) . . ?
F4 B1 F3 110.1(10) . . ?
F4A B1 F5 108.7(9) . . ?
F5A B1 F5 22.6(9) . . ?
F2A B1 F5 107.1(11) . . ?
F4 B1 F5 132.0(8) . . ?
F3 B1 F5 99.0(11) . . ?
F4A B1 F3A 109.9(7) . . ?
F5A B1 F3A 94.6(10) . . ?
F2A B1 F3A 109.2(10) . . ?
F4 B1 F3A 40.5(5) . . ?
F3 B1 F3A 92.7(9) . . ?
F5 B1 F3A 103.1(8) . . ?
F4A B1 F2 42.9(5) . . ?
F5A B1 F2 108.0(11) . . ?
F2A B1 F2 78.1(11) . . ?
F4 B1 F2 103.4(7) . . ?
F3 B1 F2 99.3(8) . . ?
F5 B1 F2 108.6(8) . . ?
F3A B1 F2 143.6(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.065
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/diethyl ether'
_database_code_depnum_ccdc_archive 'CCDC 1021516'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p21n

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Cu F N4 O3'
_chemical_formula_sum            'C18 H18 Cu F N4 O3'
_chemical_formula_weight         420.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7930(2)
_cell_length_b                   14.8014(3)
_cell_length_c                   13.3814(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.525(7)
_cell_angle_gamma                90.00
_cell_volume                     1738.28(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    85(2)
_cell_measurement_reflns_used    41064
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      68.30

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864.00
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      85(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            44126
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.46
_diffrn_reflns_theta_max         68.23
_reflns_number_total             3182
_reflns_number_gt                3116
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0251P)²+8.9647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0064(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3169
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   1.276
_refine_ls_restrained_S_all      1.276
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.95083(6) 0.31465(4) 0.75869(4) 0.0106(2) Uani 1 1 d . . .
F1 F 0.9335(3) 0.14851(15) 0.74641(17) 0.0154(5) Uani 1 1 d . . .
N1 N 0.9641(4) 0.4642(2) 0.7641(2) 0.0114(7) Uani 1 1 d . . .
N2 N 1.1757(4) 0.3227(2) 0.7706(2) 0.0103(7) Uani 1 1 d . . .
N3 N 0.8074(4) 0.3335(2) 0.8669(2) 0.0119(7) Uani 1 1 d . . .
N4 N 0.8462(4) 0.3408(2) 0.6212(2) 0.0112(7) Uani 1 1 d . . .
O1 O 1.2230(4) 0.17312(19) 0.7419(2) 0.0160(6) Uani 1 1 d . . .
O2 O 0.7705(4) 0.1818(2) 0.8961(2) 0.0172(6) Uani 1 1 d . . .
O3 O 0.7590(3) 0.19607(19) 0.5929(2) 0.0157(6) Uani 1 1 d . . .
C1 C 1.1151(5) 0.4774(3) 0.8150(3) 0.0137(8) Uani 1 1 d . . .
H1A H 1.1076 0.4710 0.8867 0.016 Uiso 1 1 calc R . .
H1B H 1.1506 0.5380 0.8020 0.016 Uiso 1 1 calc R . .
C2 C 1.2289(4) 0.4098(3) 0.7798(3) 0.0116(8) Uani 1 1 d . . .
C3 C 1.3770(5) 0.4323(3) 0.7609(3) 0.0148(8) Uani 1 1 d . . .
H3A H 1.4108 0.4917 0.7669 0.018 Uiso 1 1 calc R . .
C4 C 1.4747(5) 0.3636(3) 0.7325(3) 0.0167(9) Uani 1 1 d . . .
H4A H 1.5736 0.3777 0.7171 0.020 Uiso 1 1 calc R . .
C5 C 1.4255(5) 0.2757(3) 0.7272(3) 0.0165(9) Uani 1 1 d . . .
H5A H 1.4909 0.2293 0.7109 0.020 Uiso 1 1 calc R . .
C6 C 1.2730(5) 0.2578(3) 0.7473(3) 0.0126(8) Uani 1 1 d . . .
C7 C 0.8374(5) 0.4941(3) 0.8213(3) 0.0127(8) Uani 1 1 d . . .
H7A H 0.7549 0.5141 0.7751 0.015 Uiso 1 1 calc R . .
H7B H 0.8702 0.5455 0.8621 0.015 Uiso 1 1 calc R . .
C8 C 0.7772(4) 0.4209(3) 0.8893(3) 0.0121(8) Uani 1 1 d . . .
C9 C 0.6851(5) 0.4437(3) 0.9646(3) 0.0161(8) Uani 1 1 d . . .
H9A H 0.6673 0.5041 0.9795 0.019 Uiso 1 1 calc R . .
C10 C 0.6186(5) 0.3749(3) 1.0184(3) 0.0189(9) Uani 1 1 d . . .
H10A H 0.5558 0.3889 1.0697 0.023 Uiso 1 1 calc R . .
C11 C 0.6468(5) 0.2863(3) 0.9950(3) 0.0182(9) Uani 1 1 d . . .
H11A H 0.6025 0.2396 1.0295 0.022 Uiso 1 1 calc R . .
C12 C 0.7430(5) 0.2679(3) 0.9185(3) 0.0138(8) Uani 1 1 d . . .
C13 C 0.9522(5) 0.4902(3) 0.6582(3) 0.0128(8) Uani 1 1 d . . .
H13A H 1.0516 0.4854 0.6310 0.015 Uiso 1 1 calc R . .
H13B H 0.9194 0.5526 0.6523 0.015 Uiso 1 1 calc R . .
C14 C 0.8397(4) 0.4304(3) 0.5983(3) 0.0122(8) Uani 1 1 d . . .
C15 C 0.7390(5) 0.4638(3) 0.5242(3) 0.0152(8) Uani 1 1 d . . .
H15A H 0.7340 0.5253 0.5107 0.018 Uiso 1 1 calc R . .
C16 C 0.6446(5) 0.4030(3) 0.4701(3) 0.0180(9) Uani 1 1 d . . .
H16A H 0.5763 0.4241 0.4196 0.022 Uiso 1 1 calc R . .
C17 C 0.6521(5) 0.3122(3) 0.4912(3) 0.0169(9) Uani 1 1 d . . .
H17A H 0.5910 0.2710 0.4550 0.020 Uiso 1 1 calc R . .
C18 C 0.7551(5) 0.2840(3) 0.5689(3) 0.0125(8) Uani 1 1 d . . .
H1 H 1.133(6) 0.165(3) 0.746(4) 0.011(12) Uiso 1 1 d . . .
H2 H 0.813(6) 0.176(4) 0.854(4) 0.017(15) Uiso 1 1 d . . .
H3 H 0.817(7) 0.185(4) 0.639(5) 0.034(17) Uiso 1 1 d . . .


_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 N2 1.977(3) . ?
Cu1 N3 1.997(3) . ?
Cu1 N4 2.042(3) . ?
Cu1 N1 2.218(3) . ?
N1 C7 1.458(5) . ?
N1 C13 1.466(5) . ?
N1 C1 1.467(5) . ?
N2 C6 1.336(5) . ?
N2 C2 1.374(5) . ?
N3 C12 1.337(5) . ?
N3 C8 1.358(5) . ?
N4 C18 1.330(5) . ?
N4 C14 1.362(5) . ?
O1 C6 1.329(5) . ?
O2 C12 1.335(5) . ?
O3 C18 1.340(5) . ?
C1 C2 1.511(5) . ?
C2 C3 1.382(6) . ?
C3 C4 1.398(6) . ?
C4 C5 1.372(6) . ?
C5 C6 1.409(6) . ?
C7 C8 1.529(5) . ?
C8 C9 1.374(6) . ?
C9 C10 1.397(6) . ?
C10 C11 1.374(6) . ?
C11 C12 1.394(6) . ?
C13 C14 1.519(5) . ?
C14 C15 1.380(6) . ?
C15 C16 1.396(6) . ?
C16 C17 1.373(6) . ?
C17 C18 1.400(6) . ?

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 127.32(13) . . ?
N2 Cu1 N4 117.00(13) . . ?
N3 Cu1 N4 110.90(13) . . ?
N2 Cu1 N1 83.51(13) . . ?
N3 Cu1 N1 82.61(13) . . ?
N4 Cu1 N1 81.98(13) . . ?
C7 N1 C13 114.6(3) . . ?
C7 N1 C1 114.5(3) . . ?
C13 N1 C1 115.0(3) . . ?
C7 N1 Cu1 106.2(2) . . ?
C13 N1 Cu1 103.3(2) . . ?
C1 N1 Cu1 101.1(2) . . ?
C6 N2 C2 118.4(3) . . ?
C6 N2 Cu1 126.2(3) . . ?
C2 N2 Cu1 113.4(3) . . ?
C12 N3 C8 118.9(3) . . ?
C12 N3 Cu1 125.4(3) . . ?
C8 N3 Cu1 115.7(3) . . ?
C18 N4 C14 118.8(3) . . ?
C18 N4 Cu1 125.3(3) . . ?
C14 N4 Cu1 113.4(3) . . ?
N1 C1 C2 111.4(3) . . ?
N2 C2 C3 122.0(4) . . ?
N2 C2 C1 114.9(3) . . ?
C3 C2 C1 123.1(4) . . ?
C2 C3 C4 118.4(4) . . ?
C5 C4 C3 120.4(4) . . ?
C4 C5 C6 118.0(4) . . ?
O1 C6 N2 118.4(4) . . ?
O1 C6 C5 118.8(4) . . ?
N2 C6 C5 122.7(4) . . ?
N1 C7 C8 113.6(3) . . ?
N3 C8 C9 121.9(4) . . ?
N3 C8 C7 117.7(3) . . ?
C9 C8 C7 120.2(4) . . ?
C8 C9 C10 118.9(4) . . ?
C11 C10 C9 119.4(4) . . ?
C10 C11 C12 118.7(4) . . ?
O2 C12 N3 119.2(4) . . ?
O2 C12 C11 118.5(4) . . ?
N3 C12 C11 122.2(4) . . ?
N1 C13 C14 111.3(3) . . ?
N4 C14 C15 121.8(4) . . ?
N4 C14 C13 115.6(3) . . ?
C15 C14 C13 122.7(4) . . ?
C14 C15 C16 118.5(4) . . ?
C17 C16 C15 120.3(4) . . ?
C16 C17 C18 117.7(4) . . ?
N4 C18 O3 118.8(4) . . ?
N4 C18 C17 122.9(4) . . ?
O3 C18 C17 118.3(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        68.23
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.995
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.125
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/diethyl ether'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
_database_code_depnum_ccdc_archive 'CCDC 1021517'
