# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

 
data_vbchem162_0m_a
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             'vbchem162_0m_a'
_chemical_melting_point           ?
_chemical_formula_moiety          'C18 H16 N2 O3'
_chemical_formula_sum
 'C18 H16 N2 O3' 
_chemical_formula_weight          308.33

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                    8.2376(4)
_cell_length_b                    8.7359(4)
_cell_length_c                    11.8649(6)
_cell_angle_alpha                 98.745(2)
_cell_angle_beta                  102.654(2)
_cell_angle_gamma                 102.432(2)
_cell_volume                      795.58(7)
_cell_formula_units_Z             2
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     2996
_cell_measurement_theta_min       2.441
_cell_measurement_theta_max       28.614
 
_exptl_crystal_description        vbchem162_0m_a
_exptl_crystal_colour             ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.287          
_exptl_crystal_F_000              324
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_absorpt_coefficient_mu     0.089
_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_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   char
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             24863
_diffrn_reflns_av_unetI/netI      0.0419
_diffrn_reflns_av_R_equivalents   0.0650
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.441
_diffrn_reflns_theta_max          28.614
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.995
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.995
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.995
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4065
_reflns_number_gt                 2996
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²+0.2595P] 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          4065
_refine_ls_number_parameters      210
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0913
_refine_ls_R_factor_gt            0.0670
_refine_ls_wR_factor_ref          0.2103
_refine_ls_wR_factor_gt           0.1789
_refine_ls_goodness_of_fit_ref    1.158
_refine_ls_restrained_S_all       1.158
_refine_ls_shift/su_max           0.013
_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 0.25832(17) 0.18653(16) 0.29532(12) 0.0471(4) Uani 1 1 d . . . . .
O2 O -0.23908(18) 0.05316(19) 0.06709(13) 0.0535(4) Uani 1 1 d . . . . .
O3 O -0.0130(2) -0.04063(19) 0.13373(17) 0.0652(5) Uani 1 1 d . . . . .
N2 N 0.63043(18) 0.33339(18) 0.54386(13) 0.0368(4) Uani 1 1 d . . . . .
N1 N 0.3694(2) 0.16099(17) 0.48925(15) 0.0394(4) Uani 1 1 d . . . . .
C8 C 0.6375(2) 0.4346(2) 0.36053(15) 0.0352(4) Uani 1 1 d . . . . .
C17 C -0.0792(2) 0.0687(2) 0.13343(17) 0.0427(4) Uani 1 1 d . . . . .
C7 C 0.5495(2) 0.3380(2) 0.42976(15) 0.0347(4) Uani 1 1 d . . . . .
C14 C 0.3884(2) 0.2344(2) 0.39743(16) 0.0387(4) Uani 1 1 d . . . . .
C6 C 0.5217(2) 0.2261(2) 0.57817(16) 0.0374(4) Uani 1 1 d . . . . .
C9 C 0.8059(2) 0.5263(2) 0.40899(18) 0.0453(5) Uani 1 1 d . . . . .
H9 H 0.8604 0.5268 0.4865 0.054 Uiso 1 1 calc R U . . .
C16 C -0.0047(3) 0.2322(3) 0.20236(19) 0.0488(5) Uani 1 1 d . . . . .
H16 H -0.0703 0.3057 0.1918 0.059 Uiso 1 1 calc R U . . .
C15 C 0.1487(2) 0.2840(2) 0.27861(17) 0.0437(4) Uani 1 1 d . . . . .
H15 H 0.1831 0.3889 0.3219 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5389(3) 0.1701(3) 0.68456(19) 0.0479(5) Uani 1 1 d . . . . .
C5 C 0.2367(3) 0.0418(2) 0.4984(2) 0.0516(5) Uani 1 1 d . . . . .
H5 H 0.1370 0.0008 0.4370 0.062 Uiso 1 1 calc R U . . .
C10 C 0.8944(3) 0.6162(3) 0.3455(2) 0.0530(5) Uani 1 1 d . . . . .
H10 H 1.0070 0.6767 0.3803 0.064 Uiso 1 1 calc R U . . .
C13 C 0.5615(3) 0.4367(3) 0.2445(2) 0.0569(6) Uani 1 1 d . . . . .
H13 H 0.4491 0.3762 0.2088 0.068 Uiso 1 1 calc R U . . .
C18 C -0.3230(3) -0.1014(3) -0.0074(2) 0.0629(6) Uani 1 1 d . . . . .
H18A H -0.2603 -0.1236 -0.0647 0.094 Uiso 1 1 calc R U . . .
H18B H -0.4382 -0.1027 -0.0473 0.094 Uiso 1 1 calc R U . . .
H18C H -0.3266 -0.1816 0.0397 0.094 Uiso 1 1 calc R U . . .
C3 C 0.4058(3) 0.0504(3) 0.6918(2) 0.0582(6) Uani 1 1 d . . . . .
H3 H 0.4153 0.0102 0.7605 0.070 Uiso 1 1 calc R U . . .
C4 C 0.2553(3) -0.0138(3) 0.5990(2) 0.0608(6) Uani 1 1 d . . . . .
H4 H 0.1680 -0.0954 0.6072 0.073 Uiso 1 1 calc R U . . .
C11 C 0.8166(3) 0.6169(3) 0.2307(2) 0.0585(6) Uani 1 1 d . . . . .
H11 H 0.8759 0.6772 0.1872 0.070 Uiso 1 1 calc R U . . .
C12 C 0.6508(3) 0.5275(4) 0.1815(2) 0.0707(8) Uani 1 1 d . . . . .
H12 H 0.5973 0.5280 0.1039 0.085 Uiso 1 1 calc R U . . .
C1 C 0.7001(3) 0.2420(4) 0.7814(2) 0.0673(7) Uani 1 1 d . . . . .
H1A H 0.6855 0.2072 0.8523 0.101 Uiso 1 1 calc R U . . .
H1B H 0.7242 0.3568 0.7950 0.101 Uiso 1 1 calc R U . . .
H1C H 0.7942 0.2083 0.7591 0.101 Uiso 1 1 calc R U . . .
 
 
_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 C14 1.369(2) . ?
O1 C15 1.372(2) . ?
O2 C17 1.345(2) . ?
O2 C18 1.432(3) . ?
O3 C17 1.197(3) . ?
N2 C6 1.327(2) . ?
N2 C7 1.383(2) . ?
N1 C14 1.366(2) . ?
N1 C5 1.374(2) . ?
N1 C6 1.393(2) . ?
C8 C13 1.386(3) . ?
C8 C9 1.389(2) . ?
C8 C7 1.456(2) . ?
C17 C16 1.461(3) . ?
C7 C14 1.372(2) . ?
C6 C2 1.412(3) . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C16 C15 1.322(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C2 C3 1.370(3) . ?
C2 C1 1.494(3) . ?
C5 C4 1.346(4) . ?
C5 H5 0.9300 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C13 C12 1.379(3) . ?
C13 H13 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C3 C4 1.407(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C11 C12 1.367(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
 
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
C14 O1 C15 116.03(14) . . ?
C17 O2 C18 115.59(17) . . ?
C6 N2 C7 106.48(15) . . ?
C14 N1 C5 130.49(18) . . ?
C14 N1 C6 106.06(14) . . ?
C5 N1 C6 123.39(18) . . ?
C13 C8 C9 117.17(18) . . ?
C13 C8 C7 122.63(17) . . ?
C9 C8 C7 120.18(16) . . ?
O3 C17 O2 122.53(19) . . ?
O3 C17 C16 126.83(17) . . ?
O2 C17 C16 110.64(17) . . ?
C14 C7 N2 108.93(16) . . ?
C14 C7 C8 129.47(17) . . ?
N2 C7 C8 121.51(15) . . ?
N1 C14 O1 118.11(16) . . ?
N1 C14 C7 107.77(16) . . ?
O1 C14 C7 133.94(18) . . ?
N2 C6 N1 110.73(16) . . ?
N2 C6 C2 130.86(18) . . ?
N1 C6 C2 118.40(17) . . ?
C10 C9 C8 121.83(19) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C15 C16 C17 125.14(18) . . ?
C15 C16 H16 117.4 . . ?
C17 C16 H16 117.4 . . ?
C16 C15 O1 121.53(18) . . ?
C16 C15 H15 119.2 . . ?
O1 C15 H15 119.2 . . ?
C3 C2 C6 117.4(2) . . ?
C3 C2 C1 123.9(2) . . ?
C6 C2 C1 118.7(2) . . ?
C4 C5 N1 118.0(2) . . ?
C4 C5 H5 121.0 . . ?
N1 C5 H5 121.0 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C13 C8 120.7(2) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 C4 122.3(2) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
 
_refine_diff_density_max    0.298
_refine_diff_density_min   -0.433
_refine_diff_density_rms    0.076



