
 
data_3dd
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C21 H19 N3 O2' 
_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       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                    12.8553(5) 
_cell_length_b                    5.5968(2) 
_cell_length_c                    24.4632(9) 
_cell_angle_alpha                 90 
_cell_angle_beta                  92.110(3) 
_cell_angle_gamma                 90 
_cell_volume                      1758.90(12) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     2226 
_cell_measurement_theta_min       4.8910 
_cell_measurement_theta_max       73.1880 
  
_exptl_crystal_description        'blocky needles' 
_exptl_crystal_colour             Colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.304 
_exptl_crystal_F_000              728 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.351 
_exptl_crystal_size_mid           0.289 
_exptl_crystal_size_min           0.087 
_exptl_absorpt_coefficient_mu     0.688 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.844 
_exptl_absorpt_correction_T_max   0.945 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    'Enhance Ultra (Cu) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur PX Ultra A' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  10.4115 
_diffrn_reflns_number             5194 
_diffrn_reflns_av_unetI/netI      0.0327 
_diffrn_reflns_av_R_equivalents   0.0265 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -4 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        -30 
_diffrn_reflns_limit_l_max        25 
_diffrn_reflns_theta_min          3.616 
_diffrn_reflns_theta_max          73.722 
_diffrn_reflns_theta_full         67.684 
_diffrn_measured_fraction_theta_max   0.950 
_diffrn_measured_fraction_theta_full  0.983 
_diffrn_reflns_Laue_measured_fraction_max    0.950 
_diffrn_reflns_Laue_measured_fraction_full   0.983 
_diffrn_reflns_point_group_measured_fraction_max   0.950 
_diffrn_reflns_point_group_measured_fraction_full  0.983 
_reflns_number_total              3371 
_reflns_number_gt                 2566 
_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        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2014)' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2014)' 
_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)+(0.0517P)²+0.3626P] 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      'SHELXL-2014/7 (Sheldrick 2014' 
_refine_ls_extinction_coef        0.0058(4) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3371 
_refine_ls_number_parameters      245 
_refine_ls_number_restraints      15 
_refine_ls_R_factor_all           0.0587 
_refine_ls_R_factor_gt            0.0421 
_refine_ls_wR_factor_ref          0.1185 
_refine_ls_wR_factor_gt           0.1036 
_refine_ls_goodness_of_fit_ref    1.037 
_refine_ls_restrained_S_all       1.039 
_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 
N1 N 0.65046(10) 0.3613(2) 0.09857(5) 0.0327(3) Uani 1 1 d . . . . . 
N2 N 0.69806(11) 0.1585(3) 0.08028(6) 0.0372(3) Uani 1 1 d . . . . . 
N3 N 0.79400(11) 0.1599(3) 0.09102(6) 0.0428(4) Uani 1 1 d . . . . . 
C4 C 0.82579(12) 0.3863(3) 0.11779(7) 0.0374(4) Uani 1 1 d . . . . . 
H4A H 0.8698 0.4817 0.0936 0.045 Uiso 1 1 calc R U . . . 
H4B H 0.8654 0.3548 0.1525 0.045 Uiso 1 1 calc R U . . . 
C5 C 0.72353(11) 0.5193(3) 0.12866(6) 0.0303(3) Uani 1 1 d . . . . . 
H5A H 0.7241 0.6805 0.1110 0.036 Uiso 1 1 calc R U . . . 
C6 C 0.54720(11) 0.4072(3) 0.08299(6) 0.0294(3) Uani 1 1 d . . . . . 
C7 C 0.49987(12) 0.6185(3) 0.09921(6) 0.0334(4) Uani 1 1 d . . . . . 
H7A H 0.5380 0.7320 0.1207 0.040 Uiso 1 1 calc R U . . . 
C8 C 0.39701(12) 0.6620(3) 0.08376(6) 0.0344(4) Uani 1 1 d . . . . . 
H8A H 0.3648 0.8054 0.0952 0.041 Uiso 1 1 calc R U . . . 
C9 C 0.34011(11) 0.5001(3) 0.05190(6) 0.0324(4) Uani 1 1 d . . . . . 
C10 C 0.38799(12) 0.2900(3) 0.03561(6) 0.0346(4) Uani 1 1 d . . . . . 
H10A H 0.3499 0.1780 0.0136 0.042 Uiso 1 1 calc R U . . . 
C11 C 0.49031(12) 0.2428(3) 0.05112(6) 0.0330(4) Uani 1 1 d . . . . . 
H11A H 0.5220 0.0982 0.0401 0.040 Uiso 1 1 calc R U . . . 
C12 C 0.22996(13) 0.5424(3) 0.03491(7) 0.0397(4) Uani 1 1 d . . . . . 
O12 O 0.17973(10) 0.4191(3) 0.00325(6) 0.0558(4) Uani 1 1 d . . . . . 
O13 O 0.19116(9) 0.7330(3) 0.06008(5) 0.0530(4) Uani 1 1 d D . . . . 
C14 C 0.0815(2) 0.7805(8) 0.04847(15) 0.0646(10) Uani 0.870(9) 1 d D U P A 1 
H14A H 0.0389 0.6389 0.0570 0.077 Uiso 0.870(9) 1 calc R U P A 1 
H14B H 0.0690 0.8220 0.0094 0.077 Uiso 0.870(9) 1 calc R U P A 1 
C15 C 0.0546(2) 0.9887(8) 0.08473(12) 0.0654(11) Uani 0.870(9) 1 d D U P A 1 
H15A H -0.0190 1.0297 0.0788 0.098 Uiso 0.870(9) 1 calc R U P A 1 
H15B H 0.0677 0.9446 0.1231 0.098 Uiso 0.870(9) 1 calc R U P A 1 
H15C H 0.0977 1.1267 0.0758 0.098 Uiso 0.870(9) 1 calc R U P A 1 
C14' C 0.1012(12) 0.869(3) 0.0364(6) 0.041(4) Uiso 0.130(9) 1 d D U P A 2 
H14C H 0.0679 0.7839 0.0049 0.050 Uiso 0.130(9) 1 calc R U P A 2 
H14D H 0.1219 1.0311 0.0250 0.050 Uiso 0.130(9) 1 calc R U P A 2 
C15' C 0.0312(14) 0.877(5) 0.0844(9) 0.072(6) Uiso 0.130(9) 1 d D U P A 2 
H15D H -0.0327 0.9637 0.0740 0.108 Uiso 0.130(9) 1 calc R U P A 2 
H15E H 0.0136 0.7135 0.0952 0.108 Uiso 0.130(9) 1 calc R U P A 2 
H15F H 0.0671 0.9583 0.1151 0.108 Uiso 0.130(9) 1 calc R U P A 2 
C16 C 0.70077(12) 0.5439(3) 0.18893(6) 0.0327(4) Uani 1 1 d . . . . . 
C17 C 0.62519(14) 0.4118(4) 0.21265(7) 0.0436(4) Uani 1 1 d . . . . . 
H17A H 0.5871 0.2971 0.1914 0.052 Uiso 1 1 calc R U . . . 
C18 C 0.60300(16) 0.4437(4) 0.26839(8) 0.0573(6) Uani 1 1 d . . . . . 
H18A H 0.5501 0.3507 0.2843 0.069 Uiso 1 1 calc R U . . . 
C19 C 0.65689(17) 0.6065(4) 0.29935(8) 0.0595(6) Uani 1 1 d . . . . . 
H19A H 0.6397 0.6301 0.3364 0.071 Uiso 1 1 calc R U . . . 
C20 C 0.73780(15) 0.7408(4) 0.27725(7) 0.0480(5) Uani 1 1 d . . . . . 
C21 C 0.79791(19) 0.9058(5) 0.30921(8) 0.0634(6) Uani 1 1 d . . . . . 
H21A H 0.7814 0.9314 0.3463 0.076 Uiso 1 1 calc R U . . . 
C22 C 0.87826(19) 1.0278(4) 0.28815(9) 0.0641(6) Uani 1 1 d . . . . . 
H22A H 0.9178 1.1356 0.3106 0.077 Uiso 1 1 calc R U . . . 
C23 C 0.90301(16) 0.9949(4) 0.23341(8) 0.0516(5) Uani 1 1 d . . . . . 
H23A H 0.9600 1.0789 0.2189 0.062 Uiso 1 1 calc R U . . . 
C24 C 0.84534(13) 0.8421(3) 0.20080(7) 0.0399(4) Uani 1 1 d . . . . . 
H24A H 0.8620 0.8246 0.1635 0.048 Uiso 1 1 calc R U . . . 
C25 C 0.76162(13) 0.7096(3) 0.22124(6) 0.0351(4) 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 
N1 N2 1.3724(18) . ? 
N1 C6 1.3914(19) . ? 
N1 C5 1.4681(19) . ? 
N2 N3 1.2515(19) . ? 
N3 C4 1.477(2) . ? 
C4 C5 1.542(2) . ? 
C5 C16 1.520(2) . ? 
C6 C7 1.394(2) . ? 
C6 C11 1.396(2) . ? 
C7 C8 1.383(2) . ? 
C8 C9 1.386(2) . ? 
C9 C10 1.393(2) . ? 
C9 C12 1.480(2) . ? 
C10 C11 1.381(2) . ? 
C12 O12 1.207(2) . ? 
C12 O13 1.337(2) . ? 
O13 C14 1.453(2) . ? 
O13 C14' 1.483(13) . ? 
C14 C15 1.512(5) . ? 
C14' C15' 1.505(17) . ? 
C16 C17 1.367(2) . ? 
C16 C25 1.432(2) . ? 
C17 C18 1.415(3) . ? 
C18 C19 1.359(3) . ? 
C19 C20 1.407(3) . ? 
C20 C21 1.420(3) . ? 
C20 C25 1.426(2) . ? 
C21 C22 1.355(3) . ? 
C22 C23 1.400(3) . ? 
C23 C24 1.369(2) . ? 
C24 C25 1.414(2) . ? 
  
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 
N2 N1 C6 119.72(13) . . ? 
N2 N1 C5 112.14(12) . . ? 
C6 N1 C5 127.77(13) . . ? 
N3 N2 N1 111.97(14) . . ? 
N2 N3 C4 110.67(14) . . ? 
N3 C4 C5 105.47(12) . . ? 
N1 C5 C16 113.48(13) . . ? 
N1 C5 C4 99.01(12) . . ? 
C16 C5 C4 113.99(12) . . ? 
N1 C6 C7 120.04(14) . . ? 
N1 C6 C11 120.41(14) . . ? 
C7 C6 C11 119.55(14) . . ? 
C8 C7 C6 119.62(15) . . ? 
C7 C8 C9 121.19(15) . . ? 
C8 C9 C10 118.90(14) . . ? 
C8 C9 C12 122.20(15) . . ? 
C10 C9 C12 118.90(15) . . ? 
C11 C10 C9 120.63(15) . . ? 
C10 C11 C6 120.10(15) . . ? 
O12 C12 O13 123.50(16) . . ? 
O12 C12 C9 124.92(17) . . ? 
O13 C12 C9 111.57(15) . . ? 
C12 O13 C14 115.58(18) . . ? 
C12 O13 C14' 121.8(7) . . ? 
O13 C14 C15 105.5(2) . . ? 
O13 C14' C15' 101.0(12) . . ? 
C17 C16 C25 119.88(15) . . ? 
C17 C16 C5 121.88(15) . . ? 
C25 C16 C5 118.25(14) . . ? 
C16 C17 C18 120.84(18) . . ? 
C19 C18 C17 120.35(19) . . ? 
C18 C19 C20 120.87(18) . . ? 
C19 C20 C21 122.06(18) . . ? 
C19 C20 C25 119.45(18) . . ? 
C21 C20 C25 118.49(19) . . ? 
C22 C21 C20 121.68(19) . . ? 
C21 C22 C23 120.04(19) . . ? 
C24 C23 C22 120.1(2) . . ? 
C23 C24 C25 121.65(17) . . ? 
C24 C25 C20 117.97(16) . . ? 
C24 C25 C16 123.50(15) . . ? 
C20 C25 C16 118.53(16) . . ? 
  
_refine_diff_density_max    0.194 
_refine_diff_density_min   -0.173 
_refine_diff_density_rms    0.038 
  
  
  
#===END
