data_132-2
_audit_creation_date               2021-12-20
_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. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H19 N O2'
_chemical_formula_sum              'C18 H19 N O2'
_chemical_formula_weight           281.34
_chemical_melting_point            ?
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/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     5.9331(9)
_cell_length_b                     26.240(3)
_cell_length_c                     9.8813(11)
_cell_angle_alpha                  90
_cell_angle_beta                   104.418(13)
_cell_angle_gamma                  90
_cell_volume                       1489.9(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      2100
_cell_measurement_temperature      170.00(10)
_cell_measurement_theta_max        28.6400
_cell_measurement_theta_min        2.6220
_shelx_estimated_absorpt_T_max     0.990
_shelx_estimated_absorpt_T_min     0.988
_exptl_absorpt_coefficient_mu      0.081
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.32711
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.254
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               600
_exptl_crystal_size_max            0.15
_exptl_crystal_size_mid            0.13
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0318
_diffrn_reflns_av_unetI/netI       0.0455
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  1.000
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -5
_diffrn_reflns_limit_k_max         31
_diffrn_reflns_limit_k_min         -29
_diffrn_reflns_limit_l_max         11
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              6245
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  1.000
_diffrn_reflns_theta_full          24.998
_diffrn_reflns_theta_max           24.998
_diffrn_reflns_theta_min           2.265
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        170.00(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   5.2684
_diffrn_detector_type              AtlasS2
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -7.00  23.00   1.00    1.50    --  -11.74 -99.00  60.00   30
  2  ω     41.00  85.00   1.00    1.50    --   12.21-178.00-120.00   44
  3  ω    -25.00  92.00   1.00    1.50    --   12.21  19.00 -60.00  117
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0269821000
_diffrn_orient_matrix_UB_12        0.0254944000
_diffrn_orient_matrix_UB_13        0.0138888000
_diffrn_orient_matrix_UB_21        0.1030809000
_diffrn_orient_matrix_UB_22        0.0084818000
_diffrn_orient_matrix_UB_23        -0.0171103000
_diffrn_orient_matrix_UB_31        -0.0623566000
_diffrn_orient_matrix_UB_32        0.0029639000
_diffrn_orient_matrix_UB_33        -0.0707395000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             'Mo K\a'
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2095
_reflns_number_total               2612
_reflns_odcompleteness_completeness  99.94
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection         'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction          'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max           0.175
_refine_diff_density_min           -0.205
_refine_diff_density_rms           0.044
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.079
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       193
_refine_ls_number_reflns           2612
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0631
_refine_ls_R_factor_gt             0.0473
_refine_ls_restrained_S_all        1.079
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0397P)²+0.4149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0996
_refine_ls_wR_factor_ref           0.1089
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11),
 C12(H12)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_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 0.2207(2) 0.58265(5) 0.57172(13) 0.0370(4) Uani 1 1 d . . . . .
 O2 O 0.4184(2) 0.66151(5) 0.36970(12) 0.0351(4) Uani 1 1 d . . . . .
 N1 N 0.6187(3) 0.64805(5) 0.59579(14) 0.0293(4) Uani 1 1 d . . . . .
 H1 H 0.641630 0.625486 0.660909 0.035 Uiso 1 1 calc R U . . .
 C1 C 0.3042(3) 0.42863(6) 0.07513(17) 0.0231(4) Uani 1 1 d . . . . .
 C2 C 0.0983(3) 0.41584(7) -0.02222(17) 0.0273(4) Uani 1 1 d . . . . .
 H2 H -0.037307 0.433858 -0.023757 0.033 Uiso 1 1 calc R U . . .
 C3 C 0.0937(4) 0.37659(7) -0.11665(18) 0.0314(5) Uani 1 1 d . . . . .
 H3 H -0.044549 0.368302 -0.181069 0.038 Uiso 1 1 calc R U . . .
 C4 C 0.2941(4) 0.34988(7) -0.11492(18) 0.0328(5) Uani 1 1 d . . . . .
 H4 H 0.291034 0.323654 -0.178664 0.039 Uiso 1 1 calc R U . . .
 C5 C 0.4997(4) 0.36180(7) -0.01907(19) 0.0331(5) Uani 1 1 d . . . . .
 H5 H 0.634511 0.343567 -0.018061 0.040 Uiso 1 1 calc R U . . .
 C6 C 0.5045(3) 0.40097(7) 0.07556(18) 0.0275(4) Uani 1 1 d . . . . .
 H6 H 0.643157 0.408876 0.140086 0.033 Uiso 1 1 calc R U . . .
 C7 C 0.3101(3) 0.47047(6) 0.17737(17) 0.0218(4) Uani 1 1 d . . . . .
 C8 C 0.1381(3) 0.47385(7) 0.25110(17) 0.0253(4) Uani 1 1 d . . . . .
 H8 H 0.018280 0.450026 0.234808 0.030 Uiso 1 1 calc R U . . .
 C9 C 0.1435(3) 0.51197(7) 0.34756(17) 0.0253(4) Uani 1 1 d . . . . .
 H9 H 0.028046 0.513545 0.396096 0.030 Uiso 1 1 calc R U . . .
 C10 C 0.3201(3) 0.54808(6) 0.37296(16) 0.0220(4) Uani 1 1 d . . . . .
 C11 C 0.4916(3) 0.54545(7) 0.29934(18) 0.0253(4) Uani 1 1 d . . . . .
 H11 H 0.608964 0.569825 0.314155 0.030 Uiso 1 1 calc R U . . .
 C12 C 0.4874(3) 0.50659(7) 0.20413(17) 0.0254(4) Uani 1 1 d . . . . .
 H12 H 0.604958 0.504578 0.157256 0.030 Uiso 1 1 calc R U . . .
 C13 C 0.3280(3) 0.58710(7) 0.48221(18) 0.0251(4) Uani 1 1 d . . . . .
 C14 C 0.4640(3) 0.63638(7) 0.47744(17) 0.0242(4) Uani 1 1 d . . . . .
 C15 C 0.7555(4) 0.69566(7) 0.62765(18) 0.0301(5) Uani 1 1 d . . . . .
 C16 C 0.9314(5) 0.68672(9) 0.7662(2) 0.0590(8) Uani 1 1 d . . . . .
 H16A H 0.850877 0.679376 0.836989 0.088 Uiso 1 1 calc R U . . .
 H16B H 1.025039 0.716704 0.791705 0.088 Uiso 1 1 calc R U . . .
 H16C H 1.029367 0.658441 0.757346 0.088 Uiso 1 1 calc R U . . .
 C17 C 0.5930(4) 0.73912(8) 0.6386(2) 0.0461(6) Uani 1 1 d . . . . .
 H17A H 0.479063 0.742972 0.551228 0.069 Uiso 1 1 calc R U . . .
 H17B H 0.680770 0.770075 0.660322 0.069 Uiso 1 1 calc R U . . .
 H17C H 0.516054 0.731853 0.711145 0.069 Uiso 1 1 calc R U . . .
 C18 C 0.8842(4) 0.70624(8) 0.5155(2) 0.0394(5) Uani 1 1 d . . . . .
 H18A H 0.973924 0.676840 0.504027 0.059 Uiso 1 1 calc R U . . .
 H18B H 0.986100 0.734874 0.542851 0.059 Uiso 1 1 calc R U . . .
 H18C H 0.773867 0.713701 0.428801 0.059 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 C13 1.217(2) . ?
 O2 C14 1.224(2) . ?
 N1 H1 0.8600 . ?
 N1 C14 1.330(2) . ?
 N1 C15 1.480(2) . ?
 C1 C2 1.395(3) . ?
 C1 C6 1.392(3) . ?
 C1 C7 1.487(2) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.386(3) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.377(3) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.381(3) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.385(2) . ?
 C6 H6 0.9300 . ?
 C7 C8 1.396(2) . ?
 C7 C12 1.391(3) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.377(2) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.388(2) . ?
 C10 C11 1.392(3) . ?
 C10 C13 1.480(2) . ?
 C11 H11 0.9300 . ?
 C11 C12 1.383(2) . ?
 C12 H12 0.9300 . ?
 C13 C14 1.531(3) . ?
 C15 C16 1.518(3) . ?
 C15 C17 1.515(3) . ?
 C15 C18 1.520(3) . ?
 C16 H16A 0.9600 . ?
 C16 H16B 0.9600 . ?
 C16 H16C 0.9600 . ?
 C17 H17A 0.9600 . ?
 C17 H17B 0.9600 . ?
 C17 H17C 0.9600 . ?
 C18 H18A 0.9600 . ?
 C18 H18B 0.9600 . ?
 C18 H18C 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
 C14 N1 H1 116.5 . . ?
 C14 N1 C15 127.08(14) . . ?
 C15 N1 H1 116.5 . . ?
 C2 C1 C7 120.97(16) . . ?
 C6 C1 C2 118.52(16) . . ?
 C6 C1 C7 120.51(16) . . ?
 C1 C2 H2 119.7 . . ?
 C3 C2 C1 120.69(18) . . ?
 C3 C2 H2 119.7 . . ?
 C2 C3 H3 120.1 . . ?
 C4 C3 C2 119.85(18) . . ?
 C4 C3 H3 120.1 . . ?
 C3 C4 H4 119.8 . . ?
 C3 C4 C5 120.39(17) . . ?
 C5 C4 H4 119.8 . . ?
 C4 C5 H5 120.1 . . ?
 C4 C5 C6 119.83(19) . . ?
 C6 C5 H5 120.1 . . ?
 C1 C6 H6 119.6 . . ?
 C5 C6 C1 120.72(17) . . ?
 C5 C6 H6 119.6 . . ?
 C8 C7 C1 120.32(16) . . ?
 C12 C7 C1 121.39(16) . . ?
 C12 C7 C8 118.28(16) . . ?
 C7 C8 H8 119.6 . . ?
 C9 C8 C7 120.87(17) . . ?
 C9 C8 H8 119.6 . . ?
 C8 C9 H9 119.7 . . ?
 C8 C9 C10 120.52(17) . . ?
 C10 C9 H9 119.7 . . ?
 C9 C10 C11 119.24(16) . . ?
 C9 C10 C13 119.31(16) . . ?
 C11 C10 C13 121.39(16) . . ?
 C10 C11 H11 120.0 . . ?
 C12 C11 C10 120.01(17) . . ?
 C12 C11 H11 120.0 . . ?
 C7 C12 H12 119.5 . . ?
 C11 C12 C7 121.06(17) . . ?
 C11 C12 H12 119.5 . . ?
 O1 C13 C10 122.43(17) . . ?
 O1 C13 C14 118.58(15) . . ?
 C10 C13 C14 118.88(15) . . ?
 O2 C14 N1 126.55(17) . . ?
 O2 C14 C13 118.54(15) . . ?
 N1 C14 C13 114.89(15) . . ?
 N1 C15 C16 106.19(14) . . ?
 N1 C15 C17 108.97(17) . . ?
 N1 C15 C18 110.35(15) . . ?
 C16 C15 C18 109.17(19) . . ?
 C17 C15 C16 111.02(18) . . ?
 C17 C15 C18 111.03(16) . . ?
 C15 C16 H16A 109.5 . . ?
 C15 C16 H16B 109.5 . . ?
 C15 C16 H16C 109.5 . . ?
 H16A C16 H16B 109.5 . . ?
 H16A C16 H16C 109.5 . . ?
 H16B C16 H16C 109.5 . . ?
 C15 C17 H17A 109.5 . . ?
 C15 C17 H17B 109.5 . . ?
 C15 C17 H17C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 109.5 . . ?
 C15 C18 H18A 109.5 . . ?
 C15 C18 H18B 109.5 . . ?
 C15 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 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 C13 C14 O2 -122.4(2) . . . . ?
 O1 C13 C14 N1 55.8(2) . . . . ?
 C1 C2 C3 C4 -0.1(3) . . . . ?
 C1 C7 C8 C9 179.02(16) . . . . ?
 C1 C7 C12 C11 179.95(15) . . . . ?
 C2 C1 C6 C5 0.3(3) . . . . ?
 C2 C1 C7 C8 46.1(2) . . . . ?
 C2 C1 C7 C12 -135.02(18) . . . . ?
 C2 C3 C4 C5 0.3(3) . . . . ?
 C3 C4 C5 C6 -0.2(3) . . . . ?
 C4 C5 C6 C1 -0.1(3) . . . . ?
 C6 C1 C2 C3 -0.2(3) . . . . ?
 C6 C1 C7 C8 -133.26(18) . . . . ?
 C6 C1 C7 C12 45.6(2) . . . . ?
 C7 C1 C2 C3 -179.59(16) . . . . ?
 C7 C1 C6 C5 179.70(16) . . . . ?
 C7 C8 C9 C10 0.3(3) . . . . ?
 C8 C7 C12 C11 -1.2(3) . . . . ?
 C8 C9 C10 C11 0.2(3) . . . . ?
 C8 C9 C10 C13 -177.01(16) . . . . ?
 C9 C10 C11 C12 -1.3(2) . . . . ?
 C9 C10 C13 O1 16.9(3) . . . . ?
 C9 C10 C13 C14 -159.28(16) . . . . ?
 C10 C11 C12 C7 1.7(3) . . . . ?
 C10 C13 C14 O2 54.0(2) . . . . ?
 C10 C13 C14 N1 -127.81(17) . . . . ?
 C11 C10 C13 O1 -160.27(18) . . . . ?
 C11 C10 C13 C14 23.5(2) . . . . ?
 C12 C7 C8 C9 0.1(3) . . . . ?
 C13 C10 C11 C12 175.92(16) . . . . ?
 C14 N1 C15 C16 -171.5(2) . . . . ?
 C14 N1 C15 C17 68.9(2) . . . . ?
 C14 N1 C15 C18 -53.3(3) . . . . ?
 C15 N1 C14 O2 5.4(3) . . . . ?
 C15 N1 C14 C13 -172.64(17) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  3.196
_oxdiff_exptl_absorpt_empirical_full_min  0.356
