 
data_K259 
  
_audit_creation_method            'SHELXL-2016/6' 
_shelx_SHELXL_version_number      '2016/6' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C21 H19 N3 O2' 
_chemical_formula_weight          345.39 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       orthorhombic 
_space_group_IT_number            41 
_space_group_name_H-M_alt         'A b a 2' 
_space_group_name_Hall            'A 2 -2ac' 
  
_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' 
 'x+1/2, -y+1/2, z' 
 '-x+1/2, y+1/2, z' 
 'x, y+1/2, z+1/2' 
 '-x, -y+1/2, z+1/2' 
 'x+1/2, -y+1, z+1/2' 
 '-x+1/2, y+1, z+1/2' 
  
_cell_length_a                    6.9993(5) 
_cell_length_b                    40.218(3) 
_cell_length_c                    6.3043(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90 
_cell_angle_gamma                 90 
_cell_volume                      1774.7(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     6560 
_cell_measurement_theta_min       2.20 
_cell_measurement_theta_max       79.26 
  
_exptl_crystal_description        Rod 
_exptl_crystal_colour             Yellow 
_exptl_crystal_density_meas       'Not Measured' 
_exptl_crystal_density_method     'Not Measured' 
_exptl_crystal_density_diffrn     1.293 
_exptl_crystal_F_000              728 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.374 
_exptl_crystal_size_mid           0.069 
_exptl_crystal_size_min           0.017 
_exptl_absorpt_coefficient_mu     0.682 
_shelx_estimated_absorpt_T_min    0.784 
_shelx_estimated_absorpt_T_max    0.988 
_exptl_absorpt_correction_type    Multi-scan 
_exptl_absorpt_correction_T_min   0.6703 
_exptl_absorpt_correction_T_max   0.7543 
_exptl_absorpt_process_details    'Sadabs, (Sheldrick 2012)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker D8 Venture' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             6678 
_diffrn_reflns_av_unetI/netI      0.0270 
_diffrn_reflns_av_R_equivalents   0.0270 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -47 
_diffrn_reflns_limit_k_max        47 
_diffrn_reflns_limit_l_min        -7 
_diffrn_reflns_limit_l_max        7 
_diffrn_reflns_theta_min          4.397 
_diffrn_reflns_theta_max          66.595 
_diffrn_reflns_theta_full         66.595 
_diffrn_measured_fraction_theta_max   0.995 
_diffrn_measured_fraction_theta_full  0.995 
_diffrn_reflns_Laue_measured_fraction_max    0.995 
_diffrn_reflns_Laue_measured_fraction_full   0.995 
_diffrn_reflns_point_group_measured_fraction_max   0.978 
_diffrn_reflns_point_group_measured_fraction_full  0.978 
_reflns_number_total              1548 
_reflns_number_gt                 1518 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.775 
_reflns_Friedel_fraction_max      0.956 
_reflns_Friedel_fraction_full     0.958 
  
_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_bruker_data_scaling	  'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement	  'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection	  'APEX3 (Bruker AXS)'
_computing_data_reduction	  'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics	  'Bruker SHELXTL'
_computing_publication_material	  'Bruker SHELXTL'
_computing_structure_refinement	  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution 	  'SHELXT--(Sheldrick 2015)'
_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)+(0.0426P)²+0.3941P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      'Dual-space' 
_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_abs_structure_details 
; 
 Flack x determined using 651 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    0.05(7) 
_chemical_absolute_configuration  ? 
_refine_ls_number_reflns          1548 
_refine_ls_number_parameters      120 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0259 
_refine_ls_R_factor_gt            0.0256 
_refine_ls_wR_factor_ref          0.0695 
_refine_ls_wR_factor_gt           0.0693 
_refine_ls_goodness_of_fit_ref    1.064 
_refine_ls_restrained_S_all       1.063 
_refine_ls_shift/su_max           0.001 
_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 0.48997(12) 0.71163(3) 0.7814(2) 0.0181(3) Uani 1 1 d . . . . . 
N1 N 0.48985(16) 0.58757(3) 0.3907(2) 0.0170(3) Uani 1 1 d . . . . . 
N2 N 0.500000 0.500000 0.4669(3) 0.0189(5) Uani 1 2 d S T P . . 
C1 C 0.5870(2) 0.71776(3) 0.9771(3) 0.0239(4) Uani 1 1 d . . . . . 
H1A H 0.724361 0.714127 0.957871 0.036 Uiso 1 1 calc R U . . . 
H1B H 0.538570 0.702567 1.086132 0.036 Uiso 1 1 calc R U . . . 
H1C H 0.564576 0.740781 1.021548 0.036 Uiso 1 1 calc R U . . . 
C2 C 0.49669(18) 0.68004(4) 0.7008(3) 0.0155(3) Uani 1 1 d . . . . . 
C3 C 0.58435(18) 0.65306(3) 0.8003(3) 0.0167(3) Uani 1 1 d . . . . . 
H3 H 0.646421 0.655859 0.933156 0.020 Uiso 1 1 calc R U . . . 
C4 C 0.57991(19) 0.62199(4) 0.7030(3) 0.0169(3) Uani 1 1 d . . . . . 
H4 H 0.637929 0.603531 0.771442 0.020 Uiso 1 1 calc R U . . . 
C5 C 0.49166(16) 0.61754(4) 0.5066(3) 0.0158(4) Uani 1 1 d . . . . . 
C6 C 0.40907(19) 0.64507(4) 0.4063(3) 0.0166(3) Uani 1 1 d . . . . . 
H6 H 0.352870 0.642580 0.270051 0.020 Uiso 1 1 calc R U . . . 
C7 C 0.40869(18) 0.67582(3) 0.5039(3) 0.0162(3) Uani 1 1 d . . . . . 
H7 H 0.348308 0.694172 0.436799 0.019 Uiso 1 1 calc R U . . . 
C8 C 0.49000(19) 0.55940(4) 0.4824(3) 0.0194(4) Uani 1 1 d . . . . . 
H8 H 0.486511 0.558206 0.632832 0.023 Uiso 1 1 calc R U . . . 
C9 C 0.4956(2) 0.52858(4) 0.3556(3) 0.0172(4) Uani 1 1 d . . . . . 
C10 C 0.4952(2) 0.52952(4) 0.1352(3) 0.0218(4) Uani 1 1 d . . . . . 
H10 H 0.491637 0.550196 0.062458 0.026 Uiso 1 1 calc R U . . . 
C11 C 0.500000 0.500000 0.0234(5) 0.0243(6) Uani 1 2 d S T P . . 
H11 H 0.499997 0.499999 -0.127261 0.029 Uiso 1 2 calc R U P . . 
  
  
_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 C2 1.3691(17) . ? 
O1 C1 1.430(2) . ? 
N1 C8 1.272(2) . ? 
N1 C5 1.409(2) . ? 
N2 C9 1.3470(19) . ? 
N2 C9 1.3471(19) 2_665 ? 
C1 H1A 0.9800 . ? 
C1 H1B 0.9800 . ? 
C1 H1C 0.9800 . ? 
C2 C3 1.396(2) . ? 
C2 C7 1.396(2) . ? 
C3 C4 1.392(2) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.395(2) . ? 
C4 H4 0.9500 . ? 
C5 C6 1.400(2) . ? 
C6 C7 1.382(2) . ? 
C6 H6 0.9500 . ? 
C7 H7 0.9500 . ? 
C8 C9 1.476(2) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.390(3) . ? 
C10 C11 1.381(2) . ? 
C10 H10 0.9500 . ? 
C11 H11 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 
C2 O1 C1 117.63(11) . . ? 
C8 N1 C5 121.74(15) . . ? 
C9 N2 C9 117.20(19) . 2_665 ? 
O1 C1 H1A 109.5 . . ? 
O1 C1 H1B 109.5 . . ? 
H1A C1 H1B 109.5 . . ? 
O1 C1 H1C 109.5 . . ? 
H1A C1 H1C 109.5 . . ? 
H1B C1 H1C 109.5 . . ? 
O1 C2 C3 124.74(14) . . ? 
O1 C2 C7 115.31(13) . . ? 
C3 C2 C7 119.94(13) . . ? 
C4 C3 C2 119.33(15) . . ? 
C4 C3 H3 120.3 . . ? 
C2 C3 H3 120.3 . . ? 
C3 C4 C5 121.09(14) . . ? 
C3 C4 H4 119.5 . . ? 
C5 C4 H4 119.5 . . ? 
C4 C5 C6 118.82(14) . . ? 
C4 C5 N1 125.03(14) . . ? 
C6 C5 N1 115.99(15) . . ? 
C7 C6 C5 120.50(14) . . ? 
C7 C6 H6 119.8 . . ? 
C5 C6 H6 119.8 . . ? 
C6 C7 C2 120.27(13) . . ? 
C6 C7 H7 119.9 . . ? 
C2 C7 H7 119.9 . . ? 
N1 C8 C9 120.16(15) . . ? 
N1 C8 H8 119.9 . . ? 
C9 C8 H8 119.9 . . ? 
N2 C9 C10 122.97(15) . . ? 
N2 C9 C8 115.81(15) . . ? 
C10 C9 C8 121.23(14) . . ? 
C11 C10 C9 119.12(16) . . ? 
C11 C10 H10 120.4 . . ? 
C9 C10 H10 120.4 . . ? 
C10 C11 C10 118.6(2) 2_665 . ? 
C10 C11 H11 120.7 2_665 . ? 
C10 C11 H11 120.7 . . ? 
  
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 
C1 O1 C2 C3 2.91(19) . . . . ? 
C1 O1 C2 C7 -176.63(13) . . . . ? 
O1 C2 C3 C4 179.37(12) . . . . ? 
C7 C2 C3 C4 -1.1(2) . . . . ? 
C2 C3 C4 C5 0.9(2) . . . . ? 
C3 C4 C5 C6 0.9(2) . . . . ? 
C3 C4 C5 N1 176.08(13) . . . . ? 
C8 N1 C5 C4 31.9(2) . . . . ? 
C8 N1 C5 C6 -152.75(13) . . . . ? 
C4 C5 C6 C7 -2.4(2) . . . . ? 
N1 C5 C6 C7 -178.07(12) . . . . ? 
C5 C6 C7 C2 2.2(2) . . . . ? 
O1 C2 C7 C6 179.13(12) . . . . ? 
C3 C2 C7 C6 -0.4(2) . . . . ? 
C5 N1 C8 C9 -177.64(12) . . . . ? 
C9 N2 C9 C10 0.09(11) 2_665 . . . ? 
C9 N2 C9 C8 179.75(14) 2_665 . . . ? 
N1 C8 C9 N2 178.45(11) . . . . ? 
N1 C8 C9 C10 -1.9(2) . . . . ? 
N2 C9 C10 C11 -0.2(2) . . . . ? 
C8 C9 C10 C11 -179.82(11) . . . . ? 
C9 C10 C11 C10 0.08(10) . . . 2_665 ? 
  
_refine_diff_density_max    0.112 
_refine_diff_density_min   -0.155 
_refine_diff_density_rms    0.038 
  
  
  
