 
data_f 
  
_audit_creation_method           SHELXL-2014/7 
_shelx_SHELXL_version_number     2014/7 
_chemical_name_systematic        ? 
_chemical_name_common            ? 
_chemical_formula_moiety         'C17 H15 N3 O' 
_chemical_formula_sum            'C17 H15 N3 O' 
_chemical_melting_point          ? 
  
_exptl_crystal_description       parallelepiped 
_exptl_crystal_colour            orange 
_diffrn_ambient_temperature      296(2) 
_chemical_formula_weight         277.32 
  
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      monoclinic 
_space_group_IT_number           14 
_space_group_name_H-M_alt        'P 21/c' 
_space_group_name_Hall           '-P 2ybc' 
  
_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+1/2, -z+1/2' 
'-x, -y, -z' 
'x, -y-1/2, z-1/2' 
  
_cell_length_a                   8.3881(7) 
_cell_length_b                   21.067(2) 
_cell_length_c                   8.2714(7) 
_cell_angle_alpha                90 
_cell_angle_beta                 99.418(3) 
_cell_angle_gamma                90 
_cell_volume                     1442.0(2) 
_cell_formula_units_Z            4 
_cell_measurement_temperature    296(2) 
_cell_measurement_reflns_used    7909 
_cell_measurement_theta_min      3.130 
_cell_measurement_theta_max      26.199 
_exptl_crystal_density_meas      ? 
_exptl_crystal_density_method    ? 
_exptl_crystal_density_diffrn    1.277 
_exptl_crystal_F_000             584 
_exptl_transmission_factor_min   ? 
_exptl_transmission_factor_max   ? 
_exptl_crystal_size_max          0.520 
_exptl_crystal_size_mid          0.480 
_exptl_crystal_size_min          0.270 
_exptl_absorpt_coefficient_mu    0.082 
_shelx_estimated_absorpt_T_min   0.959 
_shelx_estimated_absorpt_T_max   0.978 
_exptl_absorpt_correction_type   multi-scan 
_exptl_absorpt_correction_T_min  0.8598 
_exptl_absorpt_correction_T_max  0.9281 
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)' 
_exptl_absorpt_special_details   ? 
_diffrn_radiation_probe          x-ray 
_diffrn_radiation_type           MoK\a 
_diffrn_radiation_wavelength     0.71073 
_diffrn_source                   ? 
_diffrn_measurement_device_type  'Bruker APEX-II CCD' 
_diffrn_measurement_method       'φ and ω scans' 
_diffrn_detector_area_resol_mean ? 
_diffrn_reflns_number            26980 
_diffrn_reflns_av_unetI/netI     0.0210 
_diffrn_reflns_av_R_equivalents  0.0439 
_diffrn_reflns_limit_h_min       -10 
_diffrn_reflns_limit_h_max       10 
_diffrn_reflns_limit_k_min       -26 
_diffrn_reflns_limit_k_max       26 
_diffrn_reflns_limit_l_min       -10 
_diffrn_reflns_limit_l_max       10 
_diffrn_reflns_theta_min         3.131 
_diffrn_reflns_theta_max         26.432 
_diffrn_reflns_theta_full        25.242 
_diffrn_measured_fraction_theta_max 0.997 
_diffrn_measured_fraction_theta_full 0.998 
_diffrn_reflns_Laue_measured_fraction_max 0.997 
_diffrn_reflns_Laue_measured_fraction_full 0.998 
_diffrn_reflns_point_group_measured_fraction_max 0.997 
_diffrn_reflns_point_group_measured_fraction_full 0.998 
_reflns_number_total             2972 
_reflns_number_gt                2165 
_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       'APEX2 (Bruker AXS, 2010)' 
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)' 
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)' 
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics    'Bruker SHELXTL' 
_computing_publication_material  'Bruker SHELXTL' 
_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)+(0.0868P)²+0.6433P] 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         2972 
_refine_ls_number_parameters     190 
_refine_ls_number_restraints     0 
_refine_ls_R_factor_all          0.0770 
_refine_ls_R_factor_gt           0.0531 
_refine_ls_wR_factor_ref         0.1673 
_refine_ls_wR_factor_gt          0.1461 
_refine_ls_goodness_of_fit_ref   1.008 
_refine_ls_restrained_S_all      1.008 
_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 
O O 0.1175(2) 0.42480(8) 0.10020(18) 0.0656(5) Uani 1 1 d . . . . . 
N1 N 0.2963(2) 0.40435(8) 0.3370(2) 0.0431(4) Uani 1 1 d . . . . . 
N2 N 0.26117(19) 0.49003(7) 0.48994(19) 0.0409(4) Uani 1 1 d . . . . . 
N3 N -0.1283(3) 0.69962(9) 0.3362(2) 0.0585(5) Uani 1 1 d . . . . . 
C1 C 0.1593(2) 0.49592(9) 0.3383(2) 0.0377(4) Uani 1 1 d . . . . . 
C2 C 0.1814(3) 0.43951(9) 0.2373(2) 0.0440(5) Uani 1 1 d . . . . . 
C3 C 0.3368(2) 0.43662(9) 0.4836(2) 0.0391(4) Uani 1 1 d . . . . . 
C4 C 0.0573(2) 0.54312(9) 0.2834(2) 0.0402(5) Uani 1 1 d . . . . . 
H4A H 0.0001 0.5375 0.1782 0.048 Uiso 1 1 calc R U . . . 
C5 C 0.0230(2) 0.60151(9) 0.3638(2) 0.0373(4) Uani 1 1 d . . . . . 
C6 C 0.0897(3) 0.61824(10) 0.5234(3) 0.0459(5) Uani 1 1 d . . . . . 
H6A H 0.1620 0.5913 0.5872 0.055 Uiso 1 1 calc R U . . . 
C7 C 0.0470(3) 0.67500(11) 0.5849(3) 0.0545(6) Uani 1 1 d . . . . . 
H7A H 0.0906 0.6872 0.6910 0.065 Uiso 1 1 calc R U . . . 
C8 C -0.0610(3) 0.71388(11) 0.4880(3) 0.0564(6) Uani 1 1 d . . . . . 
H8A H -0.0883 0.7523 0.5316 0.068 Uiso 1 1 calc R U . . . 
C9 C -0.0857(3) 0.64426(10) 0.2778(3) 0.0484(5) Uani 1 1 d . . . . . 
H9A H -0.1321 0.6334 0.1715 0.058 Uiso 1 1 calc R U . . . 
C10 C 0.3543(3) 0.34380(9) 0.2874(3) 0.0500(5) Uani 1 1 d . . . . . 
H10A H 0.2633 0.3199 0.2305 0.060 Uiso 1 1 calc R U . . . 
H10B H 0.3991 0.3201 0.3848 0.060 Uiso 1 1 calc R U . . . 
C11 C 0.4812(2) 0.34879(10) 0.1775(2) 0.0430(5) Uani 1 1 d . . . . . 
C12 C 0.5621(3) 0.40374(11) 0.1537(3) 0.0570(6) Uani 1 1 d . . . . . 
H12A H 0.5372 0.4410 0.2044 0.068 Uiso 1 1 calc R U . . . 
C13 C 0.6806(3) 0.40419(16) 0.0547(3) 0.0743(8) Uani 1 1 d . . . . . 
H13A H 0.7350 0.4416 0.0392 0.089 Uiso 1 1 calc R U . . . 
C14 C 0.7173(4) 0.34946(19) -0.0200(4) 0.0814(9) Uani 1 1 d . . . . . 
H14A H 0.7969 0.3496 -0.0861 0.098 Uiso 1 1 calc R U . . . 
C15 C 0.6376(4) 0.29488(18) 0.0023(4) 0.0867(10) Uani 1 1 d . . . . . 
H15A H 0.6624 0.2578 -0.0491 0.104 Uiso 1 1 calc R U . . . 
C16 C 0.5202(3) 0.29424(13) 0.1007(3) 0.0667(7) Uani 1 1 d . . . . . 
H16A H 0.4666 0.2566 0.1155 0.080 Uiso 1 1 calc R U . . . 
C17 C 0.4571(3) 0.41046(11) 0.6189(3) 0.0556(6) Uani 1 1 d . . . . . 
H17A H 0.4965 0.3705 0.5857 0.083 Uiso 1 1 calc R U . . . 
H17B H 0.5456 0.4396 0.6443 0.083 Uiso 1 1 calc R U . . . 
H17C H 0.4070 0.4043 0.7141 0.083 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 
O C2 1.212(2) . ? 
N1 C2 1.378(3) . ? 
N1 C3 1.383(2) . ? 
N1 C10 1.448(2) . ? 
N2 C3 1.297(2) . ? 
N2 C1 1.403(2) . ? 
N3 C8 1.324(3) . ? 
N3 C9 1.333(3) . ? 
C1 C4 1.342(3) . ? 
C1 C2 1.482(3) . ? 
C3 C17 1.485(3) . ? 
C4 C5 1.449(3) . ? 
C4 H4A 0.9300 . ? 
C5 C9 1.391(3) . ? 
C5 C6 1.392(3) . ? 
C6 C7 1.370(3) . ? 
C6 H6A 0.9300 . ? 
C7 C8 1.378(3) . ? 
C7 H7A 0.9300 . ? 
C8 H8A 0.9300 . ? 
C9 H9A 0.9300 . ? 
C10 C11 1.512(3) . ? 
C10 H10A 0.9700 . ? 
C10 H10B 0.9700 . ? 
C11 C12 1.373(3) . ? 
C11 C16 1.378(3) . ? 
C12 C13 1.388(4) . ? 
C12 H12A 0.9300 . ? 
C13 C14 1.367(4) . ? 
C13 H13A 0.9300 . ? 
C14 C15 1.358(5) . ? 
C14 H14A 0.9300 . ? 
C15 C16 1.376(4) . ? 
C15 H15A 0.9300 . ? 
C16 H16A 0.9300 . ? 
C17 H17A 0.9600 . ? 
C17 H17B 0.9600 . ? 
C17 H17C 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 
C2 N1 C3 107.94(16) . . ? 
C2 N1 C10 122.56(17) . . ? 
C3 N1 C10 129.48(17) . . ? 
C3 N2 C1 105.73(16) . . ? 
C8 N3 C9 116.35(19) . . ? 
C4 C1 N2 129.03(17) . . ? 
C4 C1 C2 122.33(18) . . ? 
N2 C1 C2 108.63(16) . . ? 
O C2 N1 125.54(19) . . ? 
O C2 C1 130.99(19) . . ? 
N1 C2 C1 103.47(16) . . ? 
N2 C3 N1 114.23(17) . . ? 
N2 C3 C17 124.64(18) . . ? 
N1 C3 C17 121.14(18) . . ? 
C1 C4 C5 129.58(18) . . ? 
C1 C4 H4A 115.2 . . ? 
C5 C4 H4A 115.2 . . ? 
C9 C5 C6 116.65(18) . . ? 
C9 C5 C4 118.54(18) . . ? 
C6 C5 C4 124.80(18) . . ? 
C7 C6 C5 119.0(2) . . ? 
C7 C6 H6A 120.5 . . ? 
C5 C6 H6A 120.5 . . ? 
C6 C7 C8 119.3(2) . . ? 
C6 C7 H7A 120.3 . . ? 
C8 C7 H7A 120.3 . . ? 
N3 C8 C7 123.7(2) . . ? 
N3 C8 H8A 118.2 . . ? 
C7 C8 H8A 118.2 . . ? 
N3 C9 C5 125.0(2) . . ? 
N3 C9 H9A 117.5 . . ? 
C5 C9 H9A 117.5 . . ? 
N1 C10 C11 114.28(17) . . ? 
N1 C10 H10A 108.7 . . ? 
C11 C10 H10A 108.7 . . ? 
N1 C10 H10B 108.7 . . ? 
C11 C10 H10B 108.7 . . ? 
H10A C10 H10B 107.6 . . ? 
C12 C11 C16 118.5(2) . . ? 
C12 C11 C10 123.92(19) . . ? 
C16 C11 C10 117.6(2) . . ? 
C11 C12 C13 120.6(2) . . ? 
C11 C12 H12A 119.7 . . ? 
C13 C12 H12A 119.7 . . ? 
C14 C13 C12 119.8(3) . . ? 
C14 C13 H13A 120.1 . . ? 
C12 C13 H13A 120.1 . . ? 
C15 C14 C13 120.0(3) . . ? 
C15 C14 H14A 120.0 . . ? 
C13 C14 H14A 120.0 . . ? 
C14 C15 C16 120.3(3) . . ? 
C14 C15 H15A 119.8 . . ? 
C16 C15 H15A 119.8 . . ? 
C11 C16 C15 120.8(3) . . ? 
C11 C16 H16A 119.6 . . ? 
C15 C16 H16A 119.6 . . ? 
C3 C17 H17A 109.5 . . ? 
C3 C17 H17B 109.5 . . ? 
H17A C17 H17B 109.5 . . ? 
C3 C17 H17C 109.5 . . ? 
H17A C17 H17C 109.5 . . ? 
H17B C17 H17C 109.5 . . ? 
  
_refine_diff_density_max         0.383 
_refine_diff_density_min         -0.292 
_refine_diff_density_rms         0.043 
  
  
_symmetry_cell_setting           Monoclinic 
_symmetry_space_group_name_h-m   P2(1)/c 
_symmetry_int_tables_number      ? 
_chemical_absolute_configuration ? 
  


