# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_sa3599
_database_code_depnum_ccdc_archive 'CCDC 1428286'
_audit_update_record             
;
2015-09-29 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;
_audit_creation_date             2014-09-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H14 F2 N2'
_chemical_formula_sum            'C16 H14 F2 N2'
_chemical_formula_weight         272.29
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.633(2)
_cell_length_b                   10.581(4)
_cell_length_c                   11.330(5)
_cell_angle_alpha                97.097(6)
_cell_angle_beta                 103.762(8)
_cell_angle_gamma                92.953(4)
_cell_volume                     648.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2077
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4832
_cell_measurement_theta_min      2.8817
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8212
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.869
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             2973
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.1574
_diffrn_orient_matrix_UB_12      0.0803
_diffrn_orient_matrix_UB_13      -0.0492
_diffrn_orient_matrix_UB_21      -0.0354
_diffrn_orient_matrix_UB_22      -0.0776
_diffrn_orient_matrix_UB_23      -0.0432
_diffrn_orient_matrix_UB_31      -0.0595
_diffrn_orient_matrix_UB_32      -0.0250
_diffrn_orient_matrix_UB_33      0.0652
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2696
_reflns_number_total             2970
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2970
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      1.148
_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)+(0.0561P)²+0.3266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1488
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H15)=Sof(F2A)=1-FVAR(1)
 Sof(F2)=Sof(H13)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F1 F 0.1950(2) 1.16712(11) 1.08268(11) 0.0417(3) Uani 1 1 d . . . . .
F2 F 0.4556(4) 0.42212(19) 0.28885(19) 0.0581(7) Uani 0.696(4) 1 d . . P A 1
N1 N 0.4109(3) 0.94759(15) 0.61408(14) 0.0344(4) Uani 1 1 d . . . . .
N2 N 0.3556(3) 0.85494(17) 0.51199(16) 0.0398(4) Uani 1 1 d . . . . .
C1 C 0.3730(3) 1.04495(16) 0.80574(15) 0.0256(4) Uani 1 1 d . . . . .
C2 C 0.2408(3) 1.06046(16) 0.89559(16) 0.0278(4) Uani 1 1 d . . . . .
H2A H 0.0991 1.0080 0.8886 0.033 Uiso 1 1 calc R . . . .
C3 C 0.3231(3) 1.15446(17) 0.99458(17) 0.0296(4) Uani 1 1 d . . . . .
C4 C 0.5282(3) 1.23682(17) 1.01040(17) 0.0317(4) Uani 1 1 d . . . . .
H4 H 0.5765 1.3004 1.0778 0.038 Uiso 1 1 calc R . . . .
C5 C 0.6605(3) 1.22092(18) 0.92114(17) 0.0326(4) Uani 1 1 d . . . . .
H5 H 0.8006 1.2748 0.9287 0.039 Uiso 1 1 calc R . . . .
C6 C 0.5865(3) 1.12634(17) 0.82172(16) 0.0297(4) Uani 1 1 d . . . . .
H6 H 0.6798 1.1162 0.7641 0.036 Uiso 1 1 calc R . . . .
C7 C 0.2898(3) 0.94578(16) 0.69668(16) 0.0265(4) Uani 1 1 d . . . . .
C8 C 0.0756(3) 0.85079(17) 0.68904(17) 0.0303(4) Uani 1 1 d . . . . .
H8A H -0.0744 0.8939 0.6754 0.036 Uiso 1 1 calc R . . . .
H8B H 0.0963 0.8172 0.7664 0.036 Uiso 1 1 calc R . . . .
C9 C 0.0529(3) 0.74037(17) 0.58556(17) 0.0319(4) Uani 1 1 d . . . . .
H9A H 0.1644 0.6773 0.6136 0.038 Uiso 1 1 calc R . . . .
H9B H -0.1128 0.6995 0.5633 0.038 Uiso 1 1 calc R . . . .
C10 C 0.1123(4) 0.78780(17) 0.47411(17) 0.0330(4) Uani 1 1 d . . . . .
H10 H -0.0071 0.8476 0.4435 0.040 Uiso 1 1 calc R . . . .
C11 C 0.1058(3) 0.67978(16) 0.37198(16) 0.0301(4) Uani 1 1 d . . . . .
C12 C -0.0946(4) 0.65627(17) 0.27216(18) 0.0352(4) Uani 1 1 d . . . . .
H12 H -0.2233 0.7086 0.2664 0.042 Uiso 1 1 calc R . . . .
C13 C -0.1045(4) 0.55514(19) 0.18078(19) 0.0411(5) Uani 1 1 d . . . . .
H13 H -0.2410 0.5405 0.1144 0.049 Uiso 0.696(4) 1 calc R . P A 1
C14 C 0.0816(4) 0.47578(18) 0.18538(19) 0.0400(5) Uani 1 1 d . . . . .
H14 H 0.0737 0.4081 0.1235 0.048 Uiso 1 1 calc R . . . .
C15 C 0.2795(4) 0.50010(19) 0.2846(2) 0.0401(5) Uani 1 1 d . . . . .
H15 H 0.4075 0.4473 0.2893 0.048 Uiso 0.304(4) 1 calc R . P A 2
C16 C 0.2968(4) 0.59987(19) 0.37815(18) 0.0356(4) Uani 1 1 d . . . . .
H16 H 0.4339 0.6136 0.4443 0.043 Uiso 1 1 calc R . . . .
F2A F -0.2758(9) 0.5287(4) 0.0866(4) 0.0537(15) Uani 0.304(4) 1 d . . P A 2
H2 H 0.403(5) 0.886(2) 0.454(2) 0.051(7) 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
F1 C3 1.362(2) . ?
F2 C15 1.319(3) . ?
N1 N2 1.383(2) . ?
N1 C7 1.284(2) . ?
N2 C10 1.453(3) . ?
C1 C2 1.397(2) . ?
C1 C6 1.404(2) . ?
C1 C7 1.483(2) . ?
C2 C3 1.375(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.391(3) . ?
C5 C6 1.378(3) . ?
C7 C8 1.509(2) . ?
C8 C9 1.527(2) . ?
C9 C10 1.516(3) . ?
C10 C11 1.515(2) . ?
C11 C12 1.382(3) . ?
C11 C16 1.396(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.372(3) . ?
C13 F2A 1.248(4) . ?
C14 C15 1.370(3) . ?
C15 C16 1.382(3) . ?

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
C7 N1 N2 120.22(15) . . ?
N1 N2 C10 119.08(16) . . ?
C2 C1 C6 117.92(16) . . ?
C2 C1 C7 120.94(15) . . ?
C6 C1 C7 121.13(15) . . ?
C3 C2 C1 119.04(16) . . ?
F1 C3 C2 118.48(16) . . ?
F1 C3 C4 117.65(16) . . ?
C4 C3 C2 123.87(16) . . ?
C3 C4 C5 117.03(17) . . ?
C6 C5 C4 120.85(17) . . ?
C5 C6 C1 121.25(17) . . ?
N1 C7 C1 115.88(15) . . ?
N1 C7 C8 124.43(16) . . ?
C1 C7 C8 119.69(15) . . ?
C7 C8 C9 111.74(14) . . ?
C10 C9 C8 110.75(15) . . ?
N2 C10 C9 108.18(16) . . ?
N2 C10 C11 109.46(15) . . ?
C11 C10 C9 112.27(15) . . ?
C12 C11 C10 120.15(17) . . ?
C12 C11 C16 118.70(17) . . ?
C16 C11 C10 121.13(17) . . ?
C11 C12 C13 120.24(19) . . ?
C14 C13 C12 121.8(2) . . ?
F2A C13 C12 124.4(3) . . ?
F2A C13 C14 113.8(3) . . ?
C15 C14 C13 117.45(18) . . ?
F2 C15 C14 116.88(19) . . ?
F2 C15 C16 120.4(2) . . ?
C14 C15 C16 122.69(19) . . ?
C15 C16 C11 119.12(18) . . ?

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
N2 H2 N1 0.85(3) 2.31(3) 3.080(2) 150(2) 2_676

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
F1 C3 C4 C5 178.57(16) . . . . ?
F2 C15 C16 C11 -179.1(2) . . . . ?
N1 N2 C10 C9 -49.8(2) . . . . ?
N1 N2 C10 C11 -172.39(16) . . . . ?
N1 C7 C8 C9 12.0(3) . . . . ?
N2 N1 C7 C1 176.61(16) . . . . ?
N2 N1 C7 C8 -3.0(3) . . . . ?
N2 C10 C11 C12 -138.07(18) . . . . ?
N2 C10 C11 C16 43.9(2) . . . . ?
C1 C2 C3 F1 -178.83(15) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C7 C8 C9 -167.62(15) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C7 N1 173.55(16) . . . . ?
C2 C1 C7 C8 -6.8(2) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C6 C1 C7 N1 -6.2(2) . . . . ?
C6 C1 C7 C8 173.42(16) . . . . ?
C7 N1 N2 C10 23.4(3) . . . . ?
C7 C1 C2 C3 -179.33(15) . . . . ?
C7 C1 C6 C5 178.12(16) . . . . ?
C7 C8 C9 C10 -38.4(2) . . . . ?
C8 C9 C10 N2 55.9(2) . . . . ?
C8 C9 C10 C11 176.75(15) . . . . ?
C9 C10 C11 C12 101.8(2) . . . . ?
C9 C10 C11 C16 -76.2(2) . . . . ?
C10 C11 C12 C13 -177.89(17) . . . . ?
C10 C11 C16 C15 178.01(17) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C11 C12 C13 F2A -178.5(3) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 F2 179.1(2) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
F2A C13 C14 C15 178.6(3) . . . . ?

