
 
data_5du
  
_audit_creation_method            'SHELXL-2017/1' 
_shelx_SHELXL_version_number      '2017/1' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C18 H23 N3 O2' 
_chemical_formula_sum 
 'C18 H23 N3 O2' 
_chemical_formula_weight          313.39 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   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                    12.8362(5) 
_cell_length_b                    11.1053(4) 
_cell_length_c                    11.7668(4) 
_cell_angle_alpha                 90 
_cell_angle_beta                  92.584(4) 
_cell_angle_gamma                 90 
_cell_volume                      1675.64(11) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     1827 
_cell_measurement_theta_min       2.6650 
_cell_measurement_theta_max       28.1090 
  
_exptl_crystal_description        'blocky needles' 
_exptl_crystal_colour             Colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.242 
_exptl_crystal_F_000              672 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.688 
_exptl_crystal_size_mid           0.633 
_exptl_crystal_size_min           0.197 
_exptl_absorpt_coefficient_mu     0.082 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.961 
_exptl_absorpt_correction_T_max   0.986 
_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      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'Enhance (Mo) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur 3 E' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  16.0382 
_diffrn_reflns_number             5811 
_diffrn_reflns_av_unetI/netI      0.0342 
_diffrn_reflns_av_R_equivalents   0.0165 
_diffrn_reflns_limit_h_min        -17 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          2.523 
_diffrn_reflns_theta_max          28.328 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.800 
_diffrn_measured_fraction_theta_full  0.984 
_diffrn_reflns_Laue_measured_fraction_max    0.800 
_diffrn_reflns_Laue_measured_fraction_full   0.984 
_diffrn_reflns_point_group_measured_fraction_max   0.800 
_diffrn_reflns_point_group_measured_fraction_full  0.984 
_reflns_number_total              3343 
_reflns_number_gt                 2478 
_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, 2017)' 
_computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_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)+(0.0340P)²+0.4950P] 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-2017/1 (Sheldrick 2017)' 
_refine_ls_extinction_coef        0.0151(10) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3343 
_refine_ls_number_parameters      210 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0659 
_refine_ls_R_factor_gt            0.0431 
_refine_ls_wR_factor_ref          0.0989 
_refine_ls_wR_factor_gt           0.0875 
_refine_ls_goodness_of_fit_ref    1.014 
_refine_ls_restrained_S_all       1.014 
_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 0.44096(9) 0.39785(11) 0.66882(11) 0.0291(3) Uani 1 1 d . . . . . 
N2 N 0.45207(11) 0.51346(12) 0.70373(12) 0.0380(4) Uani 1 1 d . . . . . 
N3 N 0.50749(11) 0.51079(12) 0.80072(12) 0.0376(4) Uani 1 1 d . . . . . 
C4 C 0.53133(11) 0.39407(14) 0.82833(13) 0.0295(4) Uani 1 1 d . . . . . 
C5 C 0.48948(12) 0.32222(14) 0.74463(14) 0.0312(4) Uani 1 1 d . . . . . 
H5A H 0.493394 0.236942 0.740168 0.037 Uiso 1 1 calc R U . . . 
C6 C 0.38086(11) 0.37075(13) 0.56714(13) 0.0275(3) Uani 1 1 d . . . . . 
C7 C 0.35743(12) 0.25182(14) 0.54097(14) 0.0309(4) Uani 1 1 d . . . . . 
H7A H 0.382856 0.188554 0.588969 0.037 Uiso 1 1 calc R U . . . 
C8 C 0.29646(12) 0.22658(14) 0.44391(13) 0.0309(4) Uani 1 1 d . . . . . 
H8A H 0.280423 0.145288 0.425045 0.037 Uiso 1 1 calc R U . . . 
C9 C 0.25841(12) 0.31866(13) 0.37371(13) 0.0287(4) Uani 1 1 d . . . . . 
C10 C 0.28381(13) 0.43699(14) 0.40094(14) 0.0368(4) Uani 1 1 d . . . . . 
H10A H 0.258681 0.500397 0.352938 0.044 Uiso 1 1 calc R U . . . 
C11 C 0.34522(13) 0.46353(14) 0.49703(14) 0.0362(4) Uani 1 1 d . . . . . 
H11A H 0.362840 0.544653 0.514882 0.043 Uiso 1 1 calc R U . . . 
C12 C 0.18943(12) 0.29529(14) 0.27098(13) 0.0311(4) Uani 1 1 d . . . . . 
O12 O 0.15018(10) 0.37329(10) 0.21172(10) 0.0495(4) Uani 1 1 d . . . . . 
O13 O 0.17481(8) 0.17795(9) 0.25176(9) 0.0336(3) Uani 1 1 d . . . . . 
C14 C 0.10694(12) 0.14794(14) 0.15380(13) 0.0331(4) Uani 1 1 d . . . . . 
H14A H 0.140654 0.169522 0.082558 0.040 Uiso 1 1 calc R U . . . 
H14B H 0.040314 0.192504 0.156593 0.040 Uiso 1 1 calc R U . . . 
C15 C 0.08771(15) 0.01529(16) 0.15821(16) 0.0489(5) Uani 1 1 d . . . . . 
H15A H 0.044453 -0.009131 0.091398 0.073 Uiso 1 1 calc R U . . . 
H15B H 0.051604 -0.004365 0.227456 0.073 Uiso 1 1 calc R U . . . 
H15C H 0.154447 -0.027600 0.158654 0.073 Uiso 1 1 calc R U . . . 
C16 C 0.59483(12) 0.36310(15) 0.93374(13) 0.0324(4) Uani 1 1 d . . . . . 
H16A H 0.582225 0.277764 0.953208 0.039 Uiso 1 1 calc R U . . . 
H16B H 0.571280 0.413196 0.997266 0.039 Uiso 1 1 calc R U . . . 
C17 C 0.71235(11) 0.38215(13) 0.92222(12) 0.0275(4) Uani 1 1 d . . . . . 
H17A H 0.722952 0.466069 0.894166 0.033 Uiso 1 1 calc R U . . . 
C18 C 0.77262(13) 0.36931(15) 1.03634(13) 0.0347(4) Uani 1 1 d . . . . . 
H18A H 0.762236 0.287295 1.066796 0.042 Uiso 1 1 calc R U . . . 
H18B H 0.745466 0.427757 1.091225 0.042 Uiso 1 1 calc R U . . . 
C19 C 0.88885(13) 0.39159(16) 1.02338(15) 0.0401(4) Uani 1 1 d . . . . . 
H19A H 0.899577 0.475564 0.998216 0.048 Uiso 1 1 calc R U . . . 
H19B H 0.926504 0.380888 1.097985 0.048 Uiso 1 1 calc R U . . . 
C20 C 0.93308(13) 0.30552(16) 0.93746(15) 0.0409(4) Uani 1 1 d . . . . . 
H20A H 0.929587 0.222130 0.966790 0.049 Uiso 1 1 calc R U . . . 
H20B H 1.007253 0.325310 0.927132 0.049 Uiso 1 1 calc R U . . . 
C21 C 0.87283(12) 0.31342(15) 0.82339(14) 0.0364(4) Uani 1 1 d . . . . . 
H21A H 0.898969 0.251168 0.771612 0.044 Uiso 1 1 calc R U . . . 
H21B H 0.885062 0.393187 0.788874 0.044 Uiso 1 1 calc R U . . . 
C22 C 0.75637(12) 0.29565(14) 0.83575(13) 0.0303(4) Uani 1 1 d . . . . . 
H22A H 0.743373 0.211788 0.859896 0.036 Uiso 1 1 calc R U . . . 
H22B H 0.719559 0.308131 0.760927 0.036 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 
N1 N2 1.3536(17) . ? 
N1 C5 1.3559(19) . ? 
N1 C6 1.4262(19) . ? 
N2 N3 1.3176(18) . ? 
N3 C4 1.368(2) . ? 
C4 C5 1.359(2) . ? 
C4 C16 1.493(2) . ? 
C6 C11 1.385(2) . ? 
C6 C7 1.386(2) . ? 
C7 C8 1.384(2) . ? 
C8 C9 1.389(2) . ? 
C9 C10 1.388(2) . ? 
C9 C12 1.489(2) . ? 
C10 C11 1.381(2) . ? 
C12 O12 1.2078(18) . ? 
C12 O13 1.3344(18) . ? 
O13 C14 1.4520(17) . ? 
C14 C15 1.495(2) . ? 
C16 C17 1.535(2) . ? 
C17 C18 1.526(2) . ? 
C17 C22 1.526(2) . ? 
C18 C19 1.527(2) . ? 
C19 C20 1.520(2) . ? 
C20 C21 1.521(2) . ? 
C21 C22 1.521(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 C5 110.42(12) . . ? 
N2 N1 C6 120.02(12) . . ? 
C5 N1 C6 129.51(13) . . ? 
N3 N2 N1 106.67(12) . . ? 
N2 N3 C4 109.48(13) . . ? 
C5 C4 N3 107.90(14) . . ? 
C5 C4 C16 130.52(14) . . ? 
N3 C4 C16 121.57(14) . . ? 
N1 C5 C4 105.54(13) . . ? 
C11 C6 C7 120.94(14) . . ? 
C11 C6 N1 119.63(13) . . ? 
C7 C6 N1 119.42(13) . . ? 
C8 C7 C6 119.04(14) . . ? 
C7 C8 C9 120.81(14) . . ? 
C10 C9 C8 119.14(14) . . ? 
C10 C9 C12 118.52(14) . . ? 
C8 C9 C12 122.33(14) . . ? 
C11 C10 C9 120.71(15) . . ? 
C10 C11 C6 119.34(15) . . ? 
O12 C12 O13 123.42(14) . . ? 
O12 C12 C9 124.14(14) . . ? 
O13 C12 C9 112.44(13) . . ? 
C12 O13 C14 115.69(12) . . ? 
O13 C14 C15 107.02(13) . . ? 
C4 C16 C17 113.37(13) . . ? 
C18 C17 C22 109.85(12) . . ? 
C18 C17 C16 111.76(13) . . ? 
C22 C17 C16 111.52(12) . . ? 
C17 C18 C19 110.85(13) . . ? 
C20 C19 C18 111.14(14) . . ? 
C19 C20 C21 111.13(14) . . ? 
C20 C21 C22 111.77(14) . . ? 
C21 C22 C17 112.15(13) . . ? 
  
_refine_diff_density_max    0.194 
_refine_diff_density_min   -0.150 
_refine_diff_density_rms    0.035 
  
  
  
#===END

