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

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#                                CCDC 
# 
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# 
#  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.
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#  fide research purposes only. It may contain copyright material
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data_H2

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_formula_weight         210.23

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.4256(6)
_cell_length_b                   7.6883(10)
_cell_length_c                   17.242(2)
_cell_angle_alpha                77.679(4)
_cell_angle_beta                 84.616(5)
_cell_angle_gamma                74.348(4)
_cell_volume                     551.49(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.082
_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      100(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            19276
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.420
_diffrn_reflns_theta_max         28.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2739
_reflns_number_gt                2266
_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)+(0.0657P)²+0.9035P] 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         2739
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1878
_refine_ls_wR_factor_gt          0.1792
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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_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
O1 O 1.0037(4) 0.2628(2) 0.28341(9) 0.0204(4) Uani 1 1 d . . . . .
N1 N 1.2791(5) -0.1771(3) 0.25115(12) 0.0258(5) Uani 1 1 d . . . . .
N2 N 0.8116(5) -0.1705(3) 0.06423(12) 0.0273(5) Uani 1 1 d . . . . .
C1 C 1.3606(7) 0.1678(4) 0.58603(16) 0.0335(6) Uani 1 1 d . . . . .
H1 H 1.4805 0.1376 0.6322 0.040 Uiso 1 1 calc R U . . .
C2 C 1.2112(6) 0.2054(3) 0.52853(14) 0.0260(5) Uani 1 1 d . . . . .
C3 C 1.0283(6) 0.2563(4) 0.45652(14) 0.0251(5) Uani 1 1 d . . . . .
H10 H 0.8149 0.3307 0.4680 0.030 Uiso 1 1 calc R U . . .
H3 H 1.0071 0.1431 0.4414 0.030 Uiso 1 1 calc R U . . .
C4 C 1.1814(5) 0.3662(3) 0.38694(13) 0.0215(5) Uani 1 1 d . . . . .
H4 H 1.2121 0.4763 0.4030 0.026 Uiso 1 1 calc R U . . .
H9 H 1.3907 0.2895 0.3738 0.026 Uiso 1 1 calc R U . . .
C5 C 0.9861(5) 0.4267(3) 0.31393(13) 0.0197(5) Uani 1 1 d . . . . .
H7 H 0.7656 0.4857 0.3279 0.024 Uiso 1 1 calc R U . . .
H8 H 1.0697 0.5163 0.2736 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8390(5) 0.2805(3) 0.21895(13) 0.0179(4) Uani 1 1 d . . . . .
C7 C 0.8820(5) 0.1205(3) 0.18848(12) 0.0175(4) Uani 1 1 d . . . . .
C8 C 0.7180(5) 0.1251(3) 0.12170(12) 0.0183(4) Uani 1 1 d . . . . .
C9 C 0.5129(6) 0.2865(3) 0.08594(13) 0.0213(5) Uani 1 1 d . . . . .
H2 H 0.3993 0.2892 0.0414 0.026 Uiso 1 1 calc R U . . .
C10 C 0.6376(5) 0.4447(3) 0.18126(13) 0.0206(5) Uani 1 1 d . . . . .
H6 H 0.6120 0.5554 0.2001 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4764(6) 0.4443(3) 0.11652(13) 0.0218(5) Uani 1 1 d . . . . .
H5 H 0.3362 0.5555 0.0921 0.026 Uiso 1 1 calc R U . . .
C12 C 1.1005(5) -0.0450(3) 0.22421(13) 0.0190(5) Uani 1 1 d . . . . .
C13 C 0.7687(5) -0.0398(3) 0.08984(13) 0.0205(5) Uani 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
O1 C6 1.349(3) . ?
O1 C5 1.447(2) . ?
N1 C12 1.143(3) . ?
N2 C13 1.146(3) . ?
C1 C2 1.184(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.470(3) . ?
C3 C4 1.528(3) . ?
C3 H10 0.9900 . ?
C3 H3 0.9900 . ?
C4 C5 1.512(3) . ?
C4 H4 0.9900 . ?
C4 H9 0.9900 . ?
C5 H7 0.9900 . ?
C5 H8 0.9900 . ?
C6 C10 1.400(3) . ?
C6 C7 1.399(3) . ?
C7 C8 1.407(3) . ?
C7 C12 1.431(3) . ?
C8 C9 1.384(3) . ?
C8 C13 1.442(3) . ?
C9 C11 1.388(3) . ?
C9 H2 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H6 0.9500 . ?
C11 H5 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
C6 O1 C5 118.10(16) . . ?
C2 C1 H1 180.0 . . ?
C1 C2 C3 178.6(3) . . ?
C2 C3 C4 112.2(2) . . ?
C2 C3 H10 109.2 . . ?
C4 C3 H10 109.2 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
H10 C3 H3 107.9 . . ?
C5 C4 C3 112.29(19) . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C5 C4 H9 109.1 . . ?
C3 C4 H9 109.1 . . ?
H4 C4 H9 107.9 . . ?
O1 C5 C4 106.82(17) . . ?
O1 C5 H7 110.4 . . ?
C4 C5 H7 110.4 . . ?
O1 C5 H8 110.4 . . ?
C4 C5 H8 110.4 . . ?
H7 C5 H8 108.6 . . ?
O1 C6 C10 124.95(19) . . ?
O1 C6 C7 115.73(18) . . ?
C10 C6 C7 119.3(2) . . ?
C6 C7 C8 119.86(19) . . ?
C6 C7 C12 119.45(19) . . ?
C8 C7 C12 120.66(19) . . ?
C9 C8 C7 120.61(19) . . ?
C9 C8 C13 120.0(2) . . ?
C7 C8 C13 119.40(19) . . ?
C11 C9 C8 118.6(2) . . ?
C11 C9 H2 120.7 . . ?
C8 C9 H2 120.7 . . ?
C11 C10 C6 119.5(2) . . ?
C11 C10 H6 120.3 . . ?
C6 C10 H6 120.3 . . ?
C10 C11 C9 122.1(2) . . ?
C10 C11 H5 119.0 . . ?
C9 C11 H5 119.0 . . ?
N1 C12 C7 178.4(3) . . ?
N2 C13 C8 179.4(3) . . ?

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
C2 C3 C4 C5 -177.26(19) . . . . ?
C6 O1 C5 C4 178.08(18) . . . . ?
C3 C4 C5 O1 -70.6(2) . . . . ?
C5 O1 C6 C10 -3.5(3) . . . . ?
C5 O1 C6 C7 175.55(18) . . . . ?
O1 C6 C7 C8 179.45(19) . . . . ?
C10 C6 C7 C8 -1.4(3) . . . . ?
O1 C6 C7 C12 -2.5(3) . . . . ?
C10 C6 C7 C12 176.6(2) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C12 C7 C8 C9 -178.3(2) . . . . ?
C6 C7 C8 C13 178.8(2) . . . . ?
C12 C7 C8 C13 0.8(3) . . . . ?
C7 C8 C9 C11 1.1(3) . . . . ?
C13 C8 C9 C11 -178.0(2) . . . . ?
O1 C6 C10 C11 -178.6(2) . . . . ?
C7 C6 C10 C11 2.3(3) . . . . ?
C6 C10 C11 C9 -1.6(3) . . . . ?
C8 C9 C11 C10 -0.1(4) . . . . ?

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
C10 H6 N1 0.95 2.46 3.328(3) 151.2 1_465
C5 H8 N1 0.99 2.70 3.549(3) 144.0 1_565
C10 H6 N1 0.95 2.46 3.328(3) 151.2 1_465
C5 H8 N1 0.99 2.70 3.549(3) 144.0 1_565

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 978750'
