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

 
data_vbchem152_0m_a
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         'vbchem152_0m_a'
_chemical_name_common             'vbchem152_0m_a'
_chemical_melting_point           ?
_chemical_formula_moiety          'C23 H20 N2 O'
_chemical_formula_sum
 'C23 H20 N2 O' 
_chemical_formula_weight          340.41

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                    9.5942(6)
_cell_length_b                    9.7522(7)
_cell_length_c                    10.4775(6)
_cell_angle_alpha                 101.242(3)
_cell_angle_beta                  98.692(3)
_cell_angle_gamma                 100.998(3)
_cell_volume                      925.62(10)
_cell_formula_units_Z             2
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     3230
_cell_measurement_theta_min       2.205
_cell_measurement_theta_max       28.631
 
_exptl_crystal_description        'vbchem152_0m_a'
_exptl_crystal_colour             ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.221          
_exptl_crystal_F_000              348
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_absorpt_coefficient_mu     0.075
_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             28082
_diffrn_reflns_av_unetI/netI      0.0394
_diffrn_reflns_av_R_equivalents   0.0619
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.205
_diffrn_reflns_theta_max          28.631
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.982
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.982
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.982
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              4749
_reflns_number_gt                 3230
_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+0.6685P] 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          4665
_refine_ls_number_parameters      237
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1304
_refine_ls_R_factor_gt            0.0923
_refine_ls_wR_factor_ref          0.2730
_refine_ls_wR_factor_gt           0.2333
_refine_ls_goodness_of_fit_ref    1.240
_refine_ls_restrained_S_all       1.240
_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 0.6690(2) 0.3650(2) 0.57513(18) 0.0511(5) Uani 1 1 d . . . . .
N2 N 0.5503(2) 0.4237(3) 0.2528(2) 0.0461(6) Uani 1 1 d . . . . .
N1 N 0.5549(2) 0.2427(3) 0.3546(2) 0.0460(6) Uani 1 1 d . . . . .
C17 C 0.8264(3) 0.3385(3) 0.7582(2) 0.0386(5) Uani 1 1 d . . . . .
C15 C 0.8062(3) 0.3445(3) 0.6172(2) 0.0398(6) Uani 1 1 d . . . . .
C9 C 0.6911(3) 0.6294(3) 0.4321(3) 0.0427(6) Uani 1 1 d . . . . .
C8 C 0.6239(3) 0.4759(3) 0.3818(2) 0.0406(6) Uani 1 1 d . . . . .
C18 C 0.7392(3) 0.3931(3) 0.8399(3) 0.0442(6) Uani 1 1 d . . . . .
H14 H 0.6662 0.4342 0.8060 0.053 Uiso 1 1 calc R U . . .
C5 C 0.5091(3) 0.2823(3) 0.2388(3) 0.0430(6) Uani 1 1 d . . . . .
C7 C 0.6264(3) 0.3676(3) 0.4455(2) 0.0424(6) Uani 1 1 d . . . . .
C19 C 0.7611(3) 0.3863(3) 0.9722(3) 0.0505(7) Uani 1 1 d . . . . .
H15 H 0.7023 0.4243 1.0258 0.061 Uiso 1 1 calc R U . . .
C20 C 0.8663(3) 0.3256(4) 1.0269(3) 0.0526(7) Uani 1 1 d . . . . .
C22 C 0.9326(3) 0.2784(4) 0.8120(3) 0.0536(7) Uani 1 1 d . . . . .
H17 H 0.9925 0.2417 0.7589 0.064 Uiso 1 1 calc R U . . .
C10 C 0.7483(3) 0.6879(3) 0.5667(3) 0.0536(7) Uani 1 1 d . . . . .
H11 H 0.7425 0.6298 0.6273 0.064 Uiso 1 1 calc R U . . .
C4 C 0.4275(3) 0.1753(4) 0.1278(3) 0.0578(8) Uani 1 1 d . . . . .
C16 C 0.8988(3) 0.3340(4) 0.5389(3) 0.0574(8) Uani 1 1 d . . . . .
H13 H 0.8739 0.3403 0.4512 0.069 Uiso 1 1 calc R U . . .
H12 H 0.9898 0.3203 0.5706 0.069 Uiso 1 1 calc R U . . .
C21 C 0.9522(3) 0.2717(4) 0.9452(3) 0.0599(8) Uani 1 1 d . . . . .
H16 H 1.0246 0.2300 0.9792 0.072 Uiso 1 1 calc R U . . .
C14 C 0.7028(3) 0.7205(4) 0.3455(3) 0.0588(8) Uani 1 1 d . . . . .
H7 H 0.6653 0.6840 0.2554 0.071 Uiso 1 1 calc R U . . .
C1 C 0.5297(4) 0.1040(4) 0.3660(4) 0.0612(8) Uani 1 1 d . . . . .
H1 H 0.5631 0.0810 0.4454 0.073 Uiso 1 1 calc R U . . .
C11 C 0.8135(4) 0.8322(4) 0.6097(4) 0.0664(9) Uani 1 1 d . . . . .
H10 H 0.8510 0.8711 0.6995 0.080 Uiso 1 1 calc R U . . .
C2 C 0.4556(4) 0.0011(4) 0.2599(4) 0.0715(10) Uani 1 1 d . . . . .
H2 H 0.4395 -0.0945 0.2655 0.086 Uiso 1 1 calc R U . . .
C12 C 0.8233(4) 0.9179(4) 0.5219(4) 0.0714(10) Uani 1 1 d . . . . .
H9 H 0.8679 1.0149 0.5519 0.086 Uiso 1 1 calc R U . . .
C13 C 0.7684(4) 0.8628(4) 0.3905(5) 0.0738(10) Uani 1 1 d . . . . .
H8 H 0.7755 0.9220 0.3311 0.089 Uiso 1 1 calc R U . . .
C3 C 0.4021(4) 0.0353(4) 0.1410(4) 0.0737(11) Uani 1 1 d . . . . .
H3 H 0.3485 -0.0377 0.0698 0.088 Uiso 1 1 calc R U . . .
C23 C 0.8841(4) 0.3174(5) 1.1700(3) 0.0740(11) Uani 1 1 d . . . . .
H18 H 0.8302 0.2263 1.1764 0.111 Uiso 1 1 calc R U . . .
H19 H 0.8489 0.3930 1.2190 0.111 Uiso 1 1 calc R U . . .
H20 H 0.9847 0.3279 1.2059 0.111 Uiso 1 1 calc R U . . .
C6 C 0.3745(4) 0.2195(5) 0.0033(4) 0.0827(12) Uani 1 1 d . . . . .
H5 H 0.4555 0.2554 -0.0340 0.124 Uiso 1 1 calc R U . . .
H4 H 0.3225 0.2933 0.0237 0.124 Uiso 1 1 calc R U . . .
H6 H 0.3114 0.1381 -0.0595 0.124 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 C7 1.365(3) . ?
O1 C15 1.387(3) . ?
N2 C5 1.332(4) . ?
N2 C8 1.375(3) . ?
N1 C1 1.360(4) . ?
N1 C7 1.375(4) . ?
N1 C5 1.378(4) . ?
C17 C22 1.372(4) . ?
C17 C18 1.387(3) . ?
C17 C15 1.475(3) . ?
C15 C16 1.303(4) . ?
C9 C14 1.390(4) . ?
C9 C10 1.396(4) . ?
C9 C8 1.469(4) . ?
C8 C7 1.357(4) . ?
C18 C19 1.387(4) . ?
C18 H14 0.9300 . ?
C5 C4 1.413(4) . ?
C19 C20 1.373(4) . ?
C19 H15 0.9300 . ?
C20 C21 1.375(4) . ?
C20 C23 1.502(4) . ?
C22 C21 1.395(4) . ?
C22 H17 0.9300 . ?
C10 C11 1.380(5) . ?
C10 H11 0.9300 . ?
C4 C3 1.378(5) . ?
C4 C6 1.499(5) . ?
C16 H13 0.9300 . ?
C16 H12 0.9300 . ?
C21 H16 0.9300 . ?
C14 C13 1.365(5) . ?
C14 H7 0.9300 . ?
C1 C2 1.343(5) . ?
C1 H1 0.9300 . ?
C11 C12 1.360(6) . ?
C11 H10 0.9300 . ?
C2 C3 1.400(6) . ?
C2 H2 0.9300 . ?
C12 C13 1.358(6) . ?
C12 H9 0.9300 . ?
C13 H8 0.9300 . ?
C3 H3 0.9300 . ?
C23 H18 0.9600 . ?
C23 H19 0.9600 . ?
C23 H20 0.9600 . ?
C6 H5 0.9600 . ?
C6 H4 0.9600 . ?
C6 H6 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
C7 O1 C15 119.15(19) . . ?
C5 N2 C8 105.2(2) . . ?
C1 N1 C7 130.7(3) . . ?
C1 N1 C5 123.0(3) . . ?
C7 N1 C5 106.2(2) . . ?
C22 C17 C18 118.3(2) . . ?
C22 C17 C15 120.6(2) . . ?
C18 C17 C15 121.2(2) . . ?
C16 C15 O1 122.4(2) . . ?
C16 C15 C17 127.7(2) . . ?
O1 C15 C17 109.9(2) . . ?
C14 C9 C10 117.9(3) . . ?
C14 C9 C8 120.5(3) . . ?
C10 C9 C8 121.6(3) . . ?
C7 C8 N2 110.6(2) . . ?
C7 C8 C9 128.6(2) . . ?
N2 C8 C9 120.7(2) . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H14 120.0 . . ?
C17 C18 H14 120.0 . . ?
N2 C5 N1 111.2(2) . . ?
N2 C5 C4 129.8(3) . . ?
N1 C5 C4 119.0(3) . . ?
C8 C7 O1 133.0(3) . . ?
C8 C7 N1 106.7(2) . . ?
O1 C7 N1 119.8(2) . . ?
C20 C19 C18 122.4(3) . . ?
C20 C19 H15 118.8 . . ?
C18 C19 H15 118.8 . . ?
C19 C20 C21 117.3(3) . . ?
C19 C20 C23 120.7(3) . . ?
C21 C20 C23 122.1(3) . . ?
C17 C22 C21 121.0(3) . . ?
C17 C22 H17 119.5 . . ?
C21 C22 H17 119.5 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H11 120.1 . . ?
C9 C10 H11 120.1 . . ?
C3 C4 C5 117.3(3) . . ?
C3 C4 C6 124.0(3) . . ?
C5 C4 C6 118.7(3) . . ?
C15 C16 H13 120.0 . . ?
C15 C16 H12 120.0 . . ?
H13 C16 H12 120.0 . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 H16 119.4 . . ?
C22 C21 H16 119.4 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H7 119.5 . . ?
C9 C14 H7 119.5 . . ?
C2 C1 N1 118.4(3) . . ?
C2 C1 H1 120.8 . . ?
N1 C1 H1 120.8 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H10 119.7 . . ?
C10 C11 H10 119.7 . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H9 119.8 . . ?
C11 C12 H9 119.8 . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H8 119.9 . . ?
C14 C13 H8 119.9 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C20 C23 H18 109.5 . . ?
C20 C23 H19 109.5 . . ?
H18 C23 H19 109.5 . . ?
C20 C23 H20 109.5 . . ?
H18 C23 H20 109.5 . . ?
H19 C23 H20 109.5 . . ?
C4 C6 H5 109.5 . . ?
C4 C6 H4 109.5 . . ?
H5 C6 H4 109.5 . . ?
C4 C6 H6 109.5 . . ?
H5 C6 H6 109.5 . . ?
H4 C6 H6 109.5 . . ?
 
_refine_diff_density_max    0.619
_refine_diff_density_min   -0.301
_refine_diff_density_rms    0.076



