data_psu-1432(467b_1)
_audit_creation_date               2022-08-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C14 H15 N O'
_chemical_formula_sum              'C14 H15 N O'
_chemical_formula_weight           213.27
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C H N O'
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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
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                     12.073(3)
_cell_length_b                     5.7407(16)
_cell_length_c                     16.957(4)
_cell_angle_alpha                  90
_cell_angle_beta                   93.28(2)
_cell_angle_gamma                  90
_cell_volume                       1173.3(5)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      1368
_cell_measurement_temperature      295(2)
_cell_measurement_theta_max        26.0790
_cell_measurement_theta_min        2.7840
_shelx_estimated_absorpt_T_max     0.991
_shelx_estimated_absorpt_T_min     0.956
_exptl_absorpt_coefficient_mu      0.076
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.51726
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.207
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         prism
_exptl_crystal_F_000               456
_exptl_crystal_size_max            0.6
_exptl_crystal_size_mid            0.4
_exptl_crystal_size_min            0.12
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0426
_diffrn_reflns_av_unetI/netI       0.0574
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.851
_diffrn_reflns_limit_h_max         15
_diffrn_reflns_limit_h_min         -13
_diffrn_reflns_limit_k_max         6
_diffrn_reflns_limit_k_min         -7
_diffrn_reflns_limit_l_max         23
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              5659
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.851
_diffrn_reflns_theta_full          26.000
_diffrn_reflns_theta_max           29.521
_diffrn_reflns_theta_min           2.406
_diffrn_ambient_temperature        295(2)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   10.4752
_diffrn_detector_type              Ruby
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.851
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   79.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509   57.0000  120.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega  -60.00   26.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509  -77.0000    0.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00    9.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978  -99.0000  -90.0000 25
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'New Xcalibur, Ruby'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_UB_11        0.0571412000
_diffrn_orient_matrix_UB_12        -0.0134698000
_diffrn_orient_matrix_UB_13        -0.0070301000
_diffrn_orient_matrix_UB_21        -0.0127066000
_diffrn_orient_matrix_UB_22        0.0072333000
_diffrn_orient_matrix_UB_23        -0.0411843000
_diffrn_orient_matrix_UB_31        0.0071762000
_diffrn_orient_matrix_UB_32        0.1225460000
_diffrn_orient_matrix_UB_33        0.0019317000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             'Mo K\a'
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1712
_reflns_number_total               2777
_reflns_odcompleteness_completeness  99.85
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       26.32
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics      'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max           0.175
_refine_diff_density_min           -0.283
_refine_diff_density_rms           0.049
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       150
_refine_ls_number_reflns           2777
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0978
_refine_ls_R_factor_gt             0.0587
_refine_ls_restrained_S_all        1.034
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0864P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1430
_refine_ls_wR_factor_ref           0.1794
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     ?
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 0.23748(10) 0.2140(2) 0.39688(7) 0.0469(4) Uani 1 1 d . . . . .
 C1 C 0.13240(15) 0.2667(3) 0.36431(10) 0.0455(5) Uani 1 1 d . . . . .
 N1 N 0.43515(14) 0.6733(3) 0.29072(9) 0.0523(5) Uani 1 1 d . . . . .
 H1 H 0.4716(19) 0.798(4) 0.2765(13) 0.079(7) Uiso 1 1 d . . . . .
 C2 C 0.13893(15) 0.4569(3) 0.31800(10) 0.0455(5) Uani 1 1 d . . . . .
 H2 H 0.080319 0.528803 0.289554 0.055 Uiso 1 1 calc R U . . .
 C3 C 0.25404(14) 0.5280(3) 0.32084(9) 0.0394(4) Uani 1 1 d . . . . .
 C4 C 0.30996(15) 0.3782(3) 0.36894(9) 0.0428(5) Uani 1 1 d . . . . .
 C5 C 0.42882(16) 0.3799(4) 0.39476(11) 0.0545(5) Uani 1 1 d . . . . .
 H5A H 0.467652 0.255886 0.368983 0.065 Uiso 1 1 calc R U . . .
 H5B H 0.438089 0.357639 0.451465 0.065 Uiso 1 1 calc R U . . .
 C6 C 0.47426(17) 0.6163(4) 0.37177(11) 0.0592(6) Uani 1 1 d . . . . .
 H6A H 0.449690 0.734865 0.407606 0.071 Uiso 1 1 calc R U . . .
 H6B H 0.554713 0.612762 0.375730 0.071 Uiso 1 1 calc R U . . .
 C7 C 0.31389(15) 0.7269(3) 0.28390(10) 0.0442(5) Uani 1 1 d . . . . .
 H7 H 0.300811 0.868767 0.314113 0.053 Uiso 1 1 calc R U . . .
 C8 C 0.27674(15) 0.7698(3) 0.19859(10) 0.0413(4) Uani 1 1 d . . . . .
 C9 C 0.22351(17) 0.9742(3) 0.17562(12) 0.0568(6) Uani 1 1 d . . . . .
 H9 H 0.209052 1.085899 0.213411 0.068 Uiso 1 1 calc R U . . .
 C10 C 0.1917(2) 1.0146(4) 0.09774(13) 0.0698(7) Uani 1 1 d . . . . .
 H10 H 0.155393 1.152141 0.083151 0.084 Uiso 1 1 calc R U . . .
 C11 C 0.2135(2) 0.8522(4) 0.04167(12) 0.0668(6) Uani 1 1 d . . . . .
 H11 H 0.192622 0.879862 -0.011136 0.080 Uiso 1 1 calc R U . . .
 C12 C 0.26658(17) 0.6471(4) 0.06352(11) 0.0609(6) Uani 1 1 d . . . . .
 H12 H 0.281680 0.536868 0.025412 0.073 Uiso 1 1 calc R U . . .
 C13 C 0.29707(16) 0.6060(3) 0.14158(10) 0.0491(5) Uani 1 1 d . . . . .
 H13 H 0.331713 0.466572 0.156150 0.059 Uiso 1 1 calc R U . . .
 C14 C 0.04253(18) 0.1059(4) 0.38545(13) 0.0672(6) Uani 1 1 d . . . . .
 H14A H 0.061156 -0.050232 0.370866 0.101 Uiso 1 1 calc R U . . .
 H14B H -0.025733 0.151027 0.357817 0.101 Uiso 1 1 calc R U . . .
 H14C H 0.034030 0.112921 0.441346 0.101 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 C1 1.388(2) . ?
 O1 C4 1.388(2) . ?
 C1 C2 1.350(2) . ?
 C1 C14 1.484(3) . ?
 N1 H1 0.88(2) . ?
 N1 C6 1.465(2) . ?
 N1 C7 1.494(2) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.447(2) . ?
 C3 C4 1.341(2) . ?
 C3 C7 1.506(2) . ?
 C4 C5 1.476(2) . ?
 C5 H5A 0.9700 . ?
 C5 H5B 0.9700 . ?
 C5 C6 1.523(3) . ?
 C6 H6A 0.9700 . ?
 C6 H6B 0.9700 . ?
 C7 H7 0.9800 . ?
 C7 C8 1.510(2) . ?
 C8 C9 1.383(3) . ?
 C8 C13 1.381(2) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.374(3) . ?
 C10 H10 0.9300 . ?
 C10 C11 1.368(3) . ?
 C11 H11 0.9300 . ?
 C11 C12 1.381(3) . ?
 C12 H12 0.9300 . ?
 C12 C13 1.374(2) . ?
 C13 H13 0.9300 . ?
 C14 H14A 0.9600 . ?
 C14 H14B 0.9600 . ?
 C14 H14C 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
 C1 O1 C4 107.20(13) . . ?
 O1 C1 C14 115.62(16) . . ?
 C2 C1 O1 109.00(16) . . ?
 C2 C1 C14 135.36(18) . . ?
 C6 N1 H1 107.4(14) . . ?
 C6 N1 C7 112.37(15) . . ?
 C7 N1 H1 108.4(15) . . ?
 C1 C2 H2 126.4 . . ?
 C1 C2 C3 107.28(16) . . ?
 C3 C2 H2 126.4 . . ?
 C2 C3 C7 133.07(15) . . ?
 C4 C3 C2 106.75(15) . . ?
 C4 C3 C7 120.16(16) . . ?
 O1 C4 C5 121.63(15) . . ?
 C3 C4 O1 109.77(15) . . ?
 C3 C4 C5 128.54(16) . . ?
 C4 C5 H5A 110.4 . . ?
 C4 C5 H5B 110.4 . . ?
 C4 C5 C6 106.75(15) . . ?
 H5A C5 H5B 108.6 . . ?
 C6 C5 H5A 110.4 . . ?
 C6 C5 H5B 110.4 . . ?
 N1 C6 C5 109.74(15) . . ?
 N1 C6 H6A 109.7 . . ?
 N1 C6 H6B 109.7 . . ?
 C5 C6 H6A 109.7 . . ?
 C5 C6 H6B 109.7 . . ?
 H6A C6 H6B 108.2 . . ?
 N1 C7 C3 107.65(14) . . ?
 N1 C7 H7 108.5 . . ?
 N1 C7 C8 110.11(14) . . ?
 C3 C7 H7 108.5 . . ?
 C3 C7 C8 113.51(14) . . ?
 C8 C7 H7 108.5 . . ?
 C9 C8 C7 121.08(16) . . ?
 C13 C8 C7 120.29(16) . . ?
 C13 C8 C9 118.62(17) . . ?
 C8 C9 H9 119.6 . . ?
 C10 C9 C8 120.90(19) . . ?
 C10 C9 H9 119.6 . . ?
 C9 C10 H10 120.0 . . ?
 C11 C10 C9 119.94(19) . . ?
 C11 C10 H10 120.0 . . ?
 C10 C11 H11 120.0 . . ?
 C10 C11 C12 119.96(19) . . ?
 C12 C11 H11 120.0 . . ?
 C11 C12 H12 120.0 . . ?
 C13 C12 C11 119.98(19) . . ?
 C13 C12 H12 120.0 . . ?
 C8 C13 H13 119.7 . . ?
 C12 C13 C8 120.60(18) . . ?
 C12 C13 H13 119.7 . . ?
 C1 C14 H14A 109.5 . . ?
 C1 C14 H14B 109.5 . . ?
 C1 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?

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
 O1 C1 C2 C3 0.35(19) . . . . ?
 O1 C4 C5 C6 -164.29(15) . . . . ?
 C1 O1 C4 C3 -0.10(18) . . . . ?
 C1 O1 C4 C5 177.30(15) . . . . ?
 C1 C2 C3 C4 -0.41(18) . . . . ?
 C1 C2 C3 C7 -178.60(17) . . . . ?
 N1 C7 C8 C9 -124.57(18) . . . . ?
 N1 C7 C8 C13 54.4(2) . . . . ?
 C2 C3 C4 O1 0.31(18) . . . . ?
 C2 C3 C4 C5 -176.86(16) . . . . ?
 C2 C3 C7 N1 -165.10(16) . . . . ?
 C2 C3 C7 C8 -43.0(2) . . . . ?
 C3 C4 C5 C6 12.6(3) . . . . ?
 C3 C7 C8 C9 114.7(2) . . . . ?
 C3 C7 C8 C13 -66.4(2) . . . . ?
 C4 O1 C1 C2 -0.17(18) . . . . ?
 C4 O1 C1 C14 178.41(14) . . . . ?
 C4 C3 C7 N1 16.9(2) . . . . ?
 C4 C3 C7 C8 139.04(17) . . . . ?
 C4 C5 C6 N1 -45.7(2) . . . . ?
 C6 N1 C7 C3 -52.34(18) . . . . ?
 C6 N1 C7 C8 -176.56(15) . . . . ?
 C7 N1 C6 C5 70.5(2) . . . . ?
 C7 C3 C4 O1 178.78(13) . . . . ?
 C7 C3 C4 C5 1.6(3) . . . . ?
 C7 C8 C9 C10 178.76(17) . . . . ?
 C7 C8 C13 C12 -177.97(17) . . . . ?
 C8 C9 C10 C11 -0.6(3) . . . . ?
 C9 C8 C13 C12 1.0(3) . . . . ?
 C9 C10 C11 C12 0.6(3) . . . . ?
 C10 C11 C12 C13 0.2(3) . . . . ?
 C11 C12 C13 C8 -1.0(3) . . . . ?
 C13 C8 C9 C10 -0.2(3) . . . . ?
 C14 C1 C2 C3 -177.8(2) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
