# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_xb7149_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cu F N3 O3'
_chemical_formula_weight         290.74

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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                   7.6404(15)
_cell_length_b                   6.3146(12)
_cell_length_c                   24.268(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.497(4)
_cell_angle_gamma                90.00
_cell_volume                     1168.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    667
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      19.38

_exptl_crystal_description       strip
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    1.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_T_max  0.740
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6021
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_sigmaI/netI    0.0922
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.19
_reflns_number_total             2331
_reflns_number_gt                1299
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0637P)²+0.0000P] 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         2331
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

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
O2 O 0.8901(5) 0.7353(7) 0.31776(17) 0.0432(11) Uani 1 1 d . . .
Cu1 Cu 0.75533(10) 1.16269(11) 0.24801(3) 0.0356(3) Uani 1 1 d . . .
O1 O 0.9079(5) 1.0885(7) 0.31246(18) 0.0434(11) Uani 1 1 d . . .
F1 F 1.3328(6) 0.9359(9) 0.53687(18) 0.0903(16) Uani 1 1 d . . .
C2 C 1.0444(8) 0.9191(10) 0.3893(2) 0.0360(14) Uani 1 1 d . . .
C1 C 0.9375(8) 0.9125(11) 0.3354(3) 0.0366(15) Uani 1 1 d . . .
C7 C 1.1342(9) 1.0994(11) 0.4062(3) 0.0543(19) Uani 1 1 d . . .
H7 H 1.1277 1.2193 0.3839 0.065 Uiso 1 1 calc R . .
C5 C 1.2365(10) 0.9310(15) 0.4876(3) 0.062(2) Uani 1 1 d . . .
C3 C 1.0542(8) 0.7408(12) 0.4237(3) 0.0477(17) Uani 1 1 d . . .
H10 H 0.9967 0.6164 0.4129 0.057 Uiso 1 1 calc R . .
C6 C 1.2337(11) 1.1046(13) 0.4555(3) 0.066(2) Uani 1 1 d . . .
H8 H 1.2972 1.2250 0.4663 0.080 Uiso 1 1 calc R . .
C4 C 1.1490(10) 0.7505(15) 0.4735(3) 0.061(2) Uani 1 1 d . . .
H9 H 1.1533 0.6347 0.4972 0.073 Uiso 1 1 calc R . .
O3 O 0.9284(5) 0.9138(7) 0.19852(18) 0.0444(11) Uani 1 1 d D . .
C8 C 0.9159(11) 0.8875(12) 0.1400(3) 0.065(2) Uani 1 1 d . . .
H2 H 0.7942 0.8644 0.1277 0.078 Uiso 1 1 calc R . .
H3 H 0.9816 0.7626 0.1305 0.078 Uiso 1 1 calc R . .
C9 C 0.9841(12) 1.0745(15) 0.1101(3) 0.092(3) Uani 1 1 d . . .
H4 H 0.9252 1.2003 0.1213 0.137 Uiso 1 1 calc R . .
H5 H 0.9630 1.0547 0.0710 0.137 Uiso 1 1 calc R . .
H6 H 1.1078 1.0885 0.1188 0.137 Uiso 1 1 calc R . .
N1 N 0.5987(6) 0.9192(8) 0.2616(2) 0.0371(12) Uani 1 1 d . . .
N2 N 0.4448(8) 0.9228(8) 0.2469(2) 0.0475(14) Uani 1 1 d . . .
N3 N 0.3012(8) 0.9246(11) 0.2325(4) 0.092(3) Uani 1 1 d . . .
H1 H 1.0205 0.9040 0.2115 0.110 Uiso 1 1 d RD . .

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
O2 0.054(3) 0.028(3) 0.047(3) -0.004(2) -0.009(2) 0.000(2)
Cu1 0.0363(4) 0.0252(4) 0.0441(5) 0.0006(4) -0.0081(3) -0.0026(4)
O1 0.047(3) 0.032(3) 0.050(3) 0.001(2) -0.014(2) -0.005(2)
F1 0.095(4) 0.121(4) 0.050(3) 0.003(3) -0.030(2) 0.000(3)
C2 0.032(3) 0.042(4) 0.033(4) -0.003(3) -0.005(3) 0.004(3)
C1 0.036(3) 0.038(4) 0.036(4) 0.004(3) 0.003(3) 0.000(3)
C7 0.061(5) 0.048(5) 0.052(5) 0.006(4) -0.016(4) -0.002(4)
C5 0.063(5) 0.082(6) 0.038(4) 0.002(5) -0.017(4) 0.010(5)
C3 0.051(4) 0.048(4) 0.043(4) 0.008(4) -0.005(3) -0.003(4)
C6 0.075(6) 0.060(6) 0.060(5) -0.007(4) -0.019(4) -0.016(4)
C4 0.066(5) 0.074(6) 0.042(4) 0.016(4) -0.007(4) 0.007(5)
O3 0.039(3) 0.046(3) 0.047(3) 0.002(2) -0.004(2) 0.001(2)
C8 0.075(6) 0.068(6) 0.051(5) -0.010(4) 0.003(4) 0.002(4)
C9 0.096(7) 0.106(8) 0.075(7) 0.025(6) 0.027(5) 0.002(6)
N1 0.030(3) 0.036(3) 0.045(3) -0.003(3) -0.005(2) 0.001(2)
N2 0.046(4) 0.023(3) 0.073(4) 0.000(3) 0.002(3) 0.000(3)
N3 0.035(4) 0.068(5) 0.168(8) 0.004(5) -0.019(4) 0.007(3)

_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
O2 C1 1.244(8) . ?
O2 Cu1 1.943(4) 2_645 ?
Cu1 O2 1.943(4) 2_655 ?
Cu1 O1 1.950(4) . ?
Cu1 N1 1.988(5) . ?
Cu1 N1 1.989(5) 2_655 ?
Cu1 O3 2.419(4) . ?
O1 C1 1.258(7) . ?
F1 C5 1.365(7) . ?
C2 C7 1.379(9) . ?
C2 C3 1.401(8) . ?
C2 C1 1.500(8) . ?
C7 C6 1.379(9) . ?
C7 H7 0.9300 . ?
C5 C6 1.345(10) . ?
C5 C4 1.355(11) . ?
C3 C4 1.371(8) . ?
C3 H10 0.9300 . ?
C6 H8 0.9300 . ?
C4 H9 0.9300 . ?
O3 C8 1.428(8) . ?
O3 H1 0.7560 . ?
C8 C9 1.496(10) . ?
C8 H2 0.9700 . ?
C8 H3 0.9700 . ?
C9 H4 0.9600 . ?
C9 H5 0.9600 . ?
C9 H6 0.9600 . ?
N1 N2 1.208(7) . ?
N1 Cu1 1.989(5) 2_645 ?
N2 N3 1.131(7) . ?

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
C1 O2 Cu1 129.4(4) . 2_645 ?
O2 Cu1 O1 178.07(18) 2_655 . ?
O2 Cu1 N1 89.95(19) 2_655 . ?
O1 Cu1 N1 91.00(19) . . ?
O2 Cu1 N1 90.45(19) 2_655 2_655 ?
O1 Cu1 N1 88.73(19) . 2_655 ?
N1 Cu1 N1 175.56(16) . 2_655 ?
O2 Cu1 O3 92.73(17) 2_655 . ?
O1 Cu1 O3 85.65(17) . . ?
N1 Cu1 O3 86.15(17) . . ?
N1 Cu1 O3 98.24(18) 2_655 . ?
C1 O1 Cu1 130.5(4) . . ?
C7 C2 C3 118.6(6) . . ?
C7 C2 C1 121.1(6) . . ?
C3 C2 C1 120.3(6) . . ?
O2 C1 O1 127.0(6) . . ?
O2 C1 C2 117.2(6) . . ?
O1 C1 C2 115.8(6) . . ?
C2 C7 C6 121.1(7) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C6 C5 C4 123.3(7) . . ?
C6 C5 F1 118.6(8) . . ?
C4 C5 F1 118.2(8) . . ?
C4 C3 C2 119.7(7) . . ?
C4 C3 H10 120.2 . . ?
C2 C3 H10 120.2 . . ?
C5 C6 C7 118.2(7) . . ?
C5 C6 H8 120.9 . . ?
C7 C6 H8 120.9 . . ?
C5 C4 C3 119.1(8) . . ?
C5 C4 H9 120.4 . . ?
C3 C4 H9 120.4 . . ?
C8 O3 Cu1 124.4(4) . . ?
C8 O3 H1 114.1 . . ?
Cu1 O3 H1 111.7 . . ?
O3 C8 C9 112.7(7) . . ?
O3 C8 H2 109.0 . . ?
C9 C8 H2 109.0 . . ?
O3 C8 H3 109.0 . . ?
C9 C8 H3 109.0 . . ?
H2 C8 H3 107.8 . . ?
C8 C9 H4 109.5 . . ?
C8 C9 H5 109.5 . . ?
H4 C9 H5 109.5 . . ?
C8 C9 H6 109.5 . . ?
H4 C9 H6 109.5 . . ?
H5 C9 H6 109.5 . . ?
N2 N1 Cu1 121.4(4) . . ?
N2 N1 Cu1 121.6(4) . 2_645 ?
Cu1 N1 Cu1 105.2(2) . 2_645 ?
N3 N2 N1 179.1(8) . . ?

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
O2 Cu1 O1 C1 -92(6) 2_655 . . . ?
N1 Cu1 O1 C1 27.4(6) . . . . ?
N1 Cu1 O1 C1 -157.0(6) 2_655 . . . ?
O3 Cu1 O1 C1 -58.7(5) . . . . ?
Cu1 O2 C1 O1 -3.8(10) 2_645 . . . ?
Cu1 O2 C1 C2 177.3(4) 2_645 . . . ?
Cu1 O1 C1 O2 9.4(10) . . . . ?
Cu1 O1 C1 C2 -171.7(4) . . . . ?
C7 C2 C1 O2 165.7(6) . . . . ?
C3 C2 C1 O2 -14.4(9) . . . . ?
C7 C2 C1 O1 -13.2(9) . . . . ?
C3 C2 C1 O1 166.6(6) . . . . ?
C3 C2 C7 C6 0.8(11) . . . . ?
C1 C2 C7 C6 -179.4(6) . . . . ?
C7 C2 C3 C4 1.4(10) . . . . ?
C1 C2 C3 C4 -178.5(6) . . . . ?
C4 C5 C6 C7 1.2(13) . . . . ?
F1 C5 C6 C7 -179.1(7) . . . . ?
C2 C7 C6 C5 -2.0(12) . . . . ?
C6 C5 C4 C3 0.9(13) . . . . ?
F1 C5 C4 C3 -178.8(6) . . . . ?
C2 C3 C4 C5 -2.2(11) . . . . ?
O2 Cu1 O3 C8 7.8(5) 2_655 . . . ?
O1 Cu1 O3 C8 -171.1(5) . . . . ?
N1 Cu1 O3 C8 97.6(5) . . . . ?
N1 Cu1 O3 C8 -83.0(5) 2_655 . . . ?
Cu1 O3 C8 C9 69.0(8) . . . . ?
O2 Cu1 N1 N2 -29.3(5) 2_655 . . . ?
O1 Cu1 N1 N2 152.4(5) . . . . ?
N1 Cu1 N1 N2 66.0(12) 2_655 . . . ?
O3 Cu1 N1 N2 -122.0(5) . . . . ?
O2 Cu1 N1 Cu1 114.0(2) 2_655 . . 2_645 ?
O1 Cu1 N1 Cu1 -64.3(2) . . . 2_645 ?
N1 Cu1 N1 Cu1 -150.8(13) 2_655 . . 2_645 ?
O3 Cu1 N1 Cu1 21.3(2) . . . 2_645 ?
Cu1 N1 N2 N3 104(62) . . . . ?
Cu1 N1 N2 N3 -34(62) 2_645 . . . ?

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
O3 H1 N3 0.76 2.18 2.918(7) 166.2 1_655

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.19
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 980967'
