data_mj23707_0m
_audit_creation_date               2023-11-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_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           'C20 H19 N O'
_chemical_formula_sum              'C20 H19 N O'
_chemical_formula_weight           289.36
_chemical_absolute_configuration   rmad
_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' 0.0137 0.0067 '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' 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0389 0.0241 '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             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     4.87580(10)
_cell_length_b                     10.6693(3)
_cell_length_c                     15.5772(4)
_cell_angle_alpha                  90
_cell_angle_beta                   98.1810(10)
_cell_angle_gamma                  90
_cell_volume                       802.10(3)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      9880
_cell_measurement_temperature      169.00
_cell_measurement_theta_max        54.955
_cell_measurement_theta_min        2.494
_shelx_estimated_absorpt_T_max     0.982
_shelx_estimated_absorpt_T_min     0.941
_exptl_absorpt_coefficient_mu      0.363
_exptl_absorpt_correction_T_max    0.7508
_exptl_absorpt_correction_T_min    0.6272
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1095 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.8354.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.198
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               308
_exptl_crystal_size_max            0.17
_exptl_crystal_size_mid            0.17
_exptl_crystal_size_min            0.05
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0420
_diffrn_reflns_av_unetI/netI       0.0351
_diffrn_reflns_Laue_measured_fraction_full  0.991
_diffrn_reflns_Laue_measured_fraction_max  0.990
_diffrn_reflns_limit_h_max         5
_diffrn_reflns_limit_h_min         -5
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         18
_diffrn_reflns_limit_l_min         -18
_diffrn_reflns_number              13354
_diffrn_reflns_point_group_measured_fraction_full  0.989
_diffrn_reflns_point_group_measured_fraction_max  0.988
_diffrn_reflns_theta_full          53.594
_diffrn_reflns_theta_max           54.930
_diffrn_reflns_theta_min           2.493
_diffrn_ambient_temperature        169.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.991
_diffrn_measured_fraction_theta_max  0.990
_diffrn_measurement_device_type    'Bruker D8 Venture'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             GaK\a
_diffrn_radiation_wavelength       1.34139
_diffrn_source                     ?
_diffrn_source_current             2.86
_diffrn_source_power               0.1995708
_diffrn_source_voltage             69.78
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.889
_reflns_Friedel_fraction_full      0.988
_reflns_Friedel_fraction_max       0.985
_reflns_number_gt                  2859
_reflns_number_total               3007
_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         'SAINT V8.40B (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics      'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.147
_refine_diff_density_min           -0.190
_refine_diff_density_rms           0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.09(13)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.055
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       200
_refine_ls_number_reflns           3007
_refine_ls_number_restraints       37
_refine_ls_R_factor_all            0.0419
_refine_ls_R_factor_gt             0.0400
_refine_ls_restrained_S_all        1.185
_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)+(0.0448P)²+0.1073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1021
_refine_ls_wR_factor_ref           0.1040
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
3.a Ternary CH refined with riding coordinates:
 C1(H1A)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
3.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 0.4348(3) 0.6894(2) 0.26699(14) 0.0788(7) Uani 1 1 d . . . . .
 N1 N 0.0217(3) 0.72309(18) 0.31282(12) 0.0506(5) Uani 1 1 d . . . . .
 H1 H -0.157636 0.709241 0.301128 0.061 Uiso 1 1 calc R U . . .
 C1 C 0.0333(4) 0.5988(2) 0.18253(15) 0.0536(6) Uani 1 1 d . . . . .
 H1A H -0.169982 0.603554 0.185403 0.064 Uiso 1 1 calc R U . . .
 C2 C 0.1828(4) 0.6745(2) 0.25796(15) 0.0522(5) Uani 1 1 d . . . . .
 C3 C 0.0852(6) 0.6572(3) 0.09703(18) 0.0665(7) Uani 1 1 d . . . . .
 H3A H 0.287196 0.659621 0.095118 0.080 Uiso 1 1 calc R U . . .
 H3B H -0.000559 0.603776 0.048557 0.080 Uiso 1 1 calc R U . . .
 C4 C -0.0308(7) 0.7889(3) 0.0846(2) 0.0836(9) Uani 1 1 d . . . . .
 H4A H -0.004956 0.819663 0.026977 0.125 Uiso 1 1 calc R U . . .
 H4B H 0.066476 0.844229 0.129062 0.125 Uiso 1 1 calc R U . . .
 H4C H -0.228868 0.787894 0.089588 0.125 Uiso 1 1 calc R U . . .
 C5 C 0.1216(4) 0.4625(2) 0.19514(15) 0.0514(5) Uani 1 1 d . . . . .
 C6 C 0.0198(6) 0.3925(3) 0.26066(19) 0.0695(7) Uani 1 1 d . . . . .
 H6 H -0.103311 0.431378 0.294631 0.083 Uiso 1 1 calc R U . . .
 C7 C 0.0932(6) 0.2710(3) 0.2764(2) 0.0761(8) Uani 1 1 d . . . . .
 H7 H 0.022867 0.227015 0.321634 0.091 Uiso 1 1 calc R U . . .
 C8 C 0.2722(5) 0.2089(3) 0.22682(17) 0.0636(6) Uani 1 1 d . . . . .
 C9 C 0.3542(7) 0.0815(3) 0.2402(2) 0.0840(9) Uani 1 1 d . . . . .
 H9 H 0.292088 0.035367 0.285927 0.101 Uiso 1 1 calc R U . . .
 C10 C 0.5196(8) 0.0251(3) 0.1888(3) 0.0875(9) Uani 1 1 d . . . . .
 H10 H 0.568026 -0.060669 0.197676 0.105 Uiso 1 1 calc R U . . .
 C11 C 0.6188(8) 0.0925(3) 0.1231(2) 0.0844(9) Uani 1 1 d . . . . .
 H11 H 0.737055 0.052596 0.087948 0.101 Uiso 1 1 calc R U . . .
 C12 C 0.5479(6) 0.2147(3) 0.10861(19) 0.0730(8) Uani 1 1 d . . . . .
 H12 H 0.616911 0.259161 0.063358 0.088 Uiso 1 1 calc R U . . .
 C13 C 0.3724(5) 0.2768(2) 0.16019(15) 0.0560(6) Uani 1 1 d . . . . .
 C14 C 0.2960(5) 0.4039(2) 0.14643(15) 0.0538(5) Uani 1 1 d . . . . .
 H14 H 0.367484 0.449794 0.102276 0.065 Uiso 1 1 calc R U . . .
 C15 C 0.1160(5) 0.7948(3) 0.38791(15) 0.0576(6) Uani 1 1 d . U . . .
 C16 C -0.0208(10) 0.9005(4) 0.4047(3) 0.1022(12) Uani 1 1 d . U . A 1
 H16 H -0.178639 0.926812 0.366030 0.123 Uiso 1 1 calc R U . A 1
 C17 C 0.0704(17) 0.9710(6) 0.4790(4) 0.147(2) Uani 1 1 d . U . A 1
 H17 H -0.021779 1.046789 0.489377 0.176 Uiso 1 1 calc R U . A 1
 C18 C 0.2878(16) 0.9324(8) 0.5360(4) 0.160(3) Uani 1 1 d . U . A 1
 H18 H 0.344921 0.979020 0.587376 0.192 Uiso 1 1 calc R U . A 1
 C19 C 0.4226(13) 0.8278(8) 0.5196(3) 0.158(2) Uani 1 1 d . U . A 1
 H19 H 0.577889 0.801328 0.559350 0.190 Uiso 1 1 calc R U . A 1
 C20 C 0.3386(8) 0.7568(5) 0.4451(2) 0.1093(14) Uani 1 1 d . U . A 1
 H20 H 0.435932 0.682570 0.434381 0.131 Uiso 1 1 calc R U . A 1


_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 1.227(3) . ?
 N1 H1 0.8800 . ?
 N1 C2 1.344(3) . ?
 N1 C15 1.418(3) . ?
 C1 H1A 1.0000 . ?
 C1 C2 1.523(3) . ?
 C1 C3 1.524(4) . ?
 C1 C5 1.522(3) . ?
 C3 H3A 0.9900 . ?
 C3 H3B 0.9900 . ?
 C3 C4 1.517(4) . ?
 C4 H4A 0.9800 . ?
 C4 H4B 0.9800 . ?
 C4 H4C 0.9800 . ?
 C5 C6 1.411(4) . ?
 C5 C14 1.368(3) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.358(5) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.410(4) . ?
 C8 C9 1.424(5) . ?
 C8 C13 1.409(4) . ?
 C9 H9 0.9500 . ?
 C9 C10 1.356(5) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.393(5) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.360(5) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.419(4) . ?
 C13 C14 1.415(4) . ?
 C14 H14 0.9500 . ?
 C15 C16 1.355(5) . ?
 C15 C20 1.365(5) . ?
 C16 H16 0.9500 . ?
 C16 C17 1.399(7) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.346(11) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.338(11) . ?
 C19 H19 0.9500 . ?
 C19 C20 1.398(7) . ?
 C20 H20 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 N1 H1 117.2 . . ?
 C2 N1 C15 125.61(19) . . ?
 C15 N1 H1 117.2 . . ?
 C2 C1 H1A 107.9 . . ?
 C2 C1 C3 109.7(2) . . ?
 C3 C1 H1A 107.9 . . ?
 C5 C1 H1A 107.9 . . ?
 C5 C1 C2 108.16(18) . . ?
 C5 C1 C3 115.14(19) . . ?
 O1 C2 N1 122.9(2) . . ?
 O1 C2 C1 121.3(2) . . ?
 N1 C2 C1 115.85(17) . . ?
 C1 C3 H3A 109.1 . . ?
 C1 C3 H3B 109.1 . . ?
 H3A C3 H3B 107.8 . . ?
 C4 C3 C1 112.7(2) . . ?
 C4 C3 H3A 109.1 . . ?
 C4 C3 H3B 109.1 . . ?
 C3 C4 H4A 109.5 . . ?
 C3 C4 H4B 109.5 . . ?
 C3 C4 H4C 109.5 . . ?
 H4A C4 H4B 109.5 . . ?
 H4A C4 H4C 109.5 . . ?
 H4B C4 H4C 109.5 . . ?
 C6 C5 C1 118.5(2) . . ?
 C14 C5 C1 123.5(2) . . ?
 C14 C5 C6 118.1(2) . . ?
 C5 C6 H6 119.2 . . ?
 C7 C6 C5 121.7(3) . . ?
 C7 C6 H6 119.2 . . ?
 C6 C7 H7 119.4 . . ?
 C6 C7 C8 121.1(3) . . ?
 C8 C7 H7 119.4 . . ?
 C7 C8 C9 123.4(3) . . ?
 C13 C8 C7 118.0(3) . . ?
 C13 C8 C9 118.6(3) . . ?
 C8 C9 H9 119.5 . . ?
 C10 C9 C8 121.0(3) . . ?
 C10 C9 H9 119.5 . . ?
 C9 C10 H10 119.9 . . ?
 C9 C10 C11 120.2(3) . . ?
 C11 C10 H10 119.9 . . ?
 C10 C11 H11 119.7 . . ?
 C12 C11 C10 120.7(3) . . ?
 C12 C11 H11 119.7 . . ?
 C11 C12 H12 119.5 . . ?
 C11 C12 C13 120.9(3) . . ?
 C13 C12 H12 119.5 . . ?
 C8 C13 C12 118.5(2) . . ?
 C8 C13 C14 119.5(2) . . ?
 C14 C13 C12 121.9(2) . . ?
 C5 C14 C13 121.6(2) . . ?
 C5 C14 H14 119.2 . . ?
 C13 C14 H14 119.2 . . ?
 C16 C15 N1 119.9(3) . . ?
 C16 C15 C20 119.3(3) . . ?
 C20 C15 N1 120.8(3) . . ?
 C15 C16 H16 120.0 . . ?
 C15 C16 C17 120.0(5) . . ?
 C17 C16 H16 120.0 . . ?
 C16 C17 H17 119.7 . . ?
 C18 C17 C16 120.6(6) . . ?
 C18 C17 H17 119.7 . . ?
 C17 C18 H18 120.3 . . ?
 C19 C18 C17 119.5(5) . . ?
 C19 C18 H18 120.3 . . ?
 C18 C19 H19 119.5 . . ?
 C18 C19 C20 121.1(6) . . ?
 C20 C19 H19 119.5 . . ?
 C15 C20 C19 119.5(5) . . ?
 C15 C20 H20 120.2 . . ?
 C19 C20 H20 120.2 . . ?

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
 N1 C15 C16 C17 179.6(3) . . . . ?
 N1 C15 C20 C19 -178.4(4) . . . . ?
 C1 C5 C6 C7 -179.0(3) . . . . ?
 C1 C5 C14 C13 -179.9(2) . . . . ?
 C2 N1 C15 C16 135.4(3) . . . . ?
 C2 N1 C15 C20 -46.5(4) . . . . ?
 C2 C1 C3 C4 -63.1(3) . . . . ?
 C2 C1 C5 C6 72.8(3) . . . . ?
 C2 C1 C5 C14 -106.9(2) . . . . ?
 C3 C1 C2 O1 -58.9(3) . . . . ?
 C3 C1 C2 N1 120.9(2) . . . . ?
 C3 C1 C5 C6 -164.2(2) . . . . ?
 C3 C1 C5 C14 16.1(3) . . . . ?
 C5 C1 C2 O1 67.4(3) . . . . ?
 C5 C1 C2 N1 -112.8(2) . . . . ?
 C5 C1 C3 C4 174.7(2) . . . . ?
 C5 C6 C7 C8 -0.9(5) . . . . ?
 C6 C5 C14 C13 0.4(3) . . . . ?
 C6 C7 C8 C9 -179.6(3) . . . . ?
 C6 C7 C8 C13 -0.1(4) . . . . ?
 C7 C8 C9 C10 177.8(3) . . . . ?
 C7 C8 C13 C12 -178.7(3) . . . . ?
 C7 C8 C13 C14 1.2(3) . . . . ?
 C8 C9 C10 C11 1.8(5) . . . . ?
 C8 C13 C14 C5 -1.4(3) . . . . ?
 C9 C8 C13 C12 0.8(4) . . . . ?
 C9 C8 C13 C14 -179.3(3) . . . . ?
 C9 C10 C11 C12 -1.1(5) . . . . ?
 C10 C11 C12 C13 0.2(5) . . . . ?
 C11 C12 C13 C8 -0.1(4) . . . . ?
 C11 C12 C13 C14 180.0(3) . . . . ?
 C12 C13 C14 C5 178.5(2) . . . . ?
 C13 C8 C9 C10 -1.7(5) . . . . ?
 C14 C5 C6 C7 0.8(4) . . . . ?
 C15 N1 C2 O1 -1.2(4) . . . . ?
 C15 N1 C2 C1 179.0(2) . . . . ?
 C15 C16 C17 C18 -2.4(7) . . . . ?
 C16 C15 C20 C19 -0.4(6) . . . . ?
 C16 C17 C18 C19 2.2(8) . . . . ?
 C17 C18 C19 C20 -1.1(9) . . . . ?
 C18 C19 C20 C15 0.2(8) . . . . ?
 C20 C15 C16 C17 1.5(6) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
