data_cu_xsj_1124_0m_a
_audit_creation_date               2022-11-24
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.11.02 svn.ra8b101fa for OlexSys, GUI svn.r6635)
;
_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           'C19 H19 N O2'
_chemical_formula_sum              'C19 H19 N O2'
_chemical_formula_weight           293.35
_chemical_absolute_configuration   ad
_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' 0.0181 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'

_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        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                     9.1997(4)
_cell_length_b                     10.9159(5)
_cell_length_c                     16.2574(8)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1632.62(13)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9986
_cell_measurement_temperature      220.00
_cell_measurement_theta_max        66.65
_cell_measurement_theta_min        4.88
_shelx_estimated_absorpt_T_max     0.964
_shelx_estimated_absorpt_T_min     0.953
_exptl_absorpt_coefficient_mu      0.613
_exptl_absorpt_correction_T_max    ?
_exptl_absorpt_correction_T_min    ?
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.193
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               624
_exptl_crystal_size_max            0.08
_exptl_crystal_size_mid            0.08
_exptl_crystal_size_min            0.06
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0843
_diffrn_reflns_av_unetI/netI       0.0584
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         18
_diffrn_reflns_limit_l_min         -19
_diffrn_reflns_number              15298
_diffrn_reflns_point_group_measured_fraction_full  0.991
_diffrn_reflns_point_group_measured_fraction_max  0.991
_diffrn_reflns_theta_full          66.845
_diffrn_reflns_theta_max           66.845
_diffrn_reflns_theta_min           4.880
_diffrn_ambient_temperature        220.00
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_source_current             1.1
_diffrn_source_power               0.05500000000000001
_diffrn_source_voltage             50.0
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.718
_reflns_Friedel_fraction_full      0.984
_reflns_Friedel_fraction_max       0.984
_reflns_number_gt                  2749
_reflns_number_total               2863
_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 V8.38A (Bruker, 2018)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics      'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max           0.198
_refine_diff_density_min           -0.221
_refine_diff_density_rms           0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1103 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.06(14)
_refine_ls_extinction_coef         0.0137(19)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.086
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       202
_refine_ls_number_reflns           2863
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0471
_refine_ls_R_factor_gt             0.0458
_refine_ls_restrained_S_all        1.086
_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)+(0.0684P)²+0.1310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1172
_refine_ls_wR_factor_ref           0.1188
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C18(H18)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C)
;
_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
 C1 C 0.8104(2) 0.6089(2) 0.37894(14) 0.0372(5) Uani 1 1 d . . . . .
 C2 C 0.4461(4) 0.6392(3) 0.3506(3) 0.0839(12) Uani 1 1 d . . . . .
 H2 H 0.503126 0.575292 0.372070 0.101 Uiso 1 1 calc R U . . .
 C3 C 0.2760(3) 0.8218(3) 0.28652(19) 0.0597(7) Uani 1 1 d . . . . .
 H3 H 0.218558 0.884857 0.264286 0.072 Uiso 1 1 calc R U . . .
 C4 C 0.8723(2) 0.5136(2) 0.43051(14) 0.0370(5) Uani 1 1 d . . . . .
 C5 C 0.4227(3) 0.8428(3) 0.30274(17) 0.0495(6) Uani 1 1 d . . . . .
 H5 H 0.464057 0.919375 0.290401 0.059 Uiso 1 1 calc R U . . .
 C6 C 0.7584(2) 0.7284(2) 0.27811(14) 0.0399(5) Uani 1 1 d . . . . .
 C7 C 0.8730(4) 0.9167(3) 0.3939(3) 0.0727(10) Uani 1 1 d . . . . .
 H7A H 0.903803 0.861668 0.438254 0.087 Uiso 1 1 calc R U . . .
 H7B H 0.926343 0.893827 0.344051 0.087 Uiso 1 1 calc R U . . .
 C8 C 0.8259(3) 0.5009(2) 0.51209(15) 0.0429(5) Uani 1 1 d . . . . .
 H8 H 0.755223 0.554182 0.533639 0.052 Uiso 1 1 calc R U . . .
 C9 C 0.2999(4) 0.6189(4) 0.3332(4) 0.1037(16) Uani 1 1 d . . . . .
 H9 H 0.259123 0.541139 0.342485 0.124 Uiso 1 1 calc R U . . .
 C10 C 0.9770(3) 0.4346(2) 0.39995(14) 0.0412(5) Uani 1 1 d . . . . .
 H10 H 1.007138 0.441660 0.344901 0.049 Uiso 1 1 calc R U . . .
 C11 C 0.7113(3) 0.9006(2) 0.37905(19) 0.0527(7) Uani 1 1 d . . . . .
 H11A H 0.680420 0.958511 0.336462 0.063 Uiso 1 1 calc R U . . .
 H11B H 0.658904 0.921047 0.429696 0.063 Uiso 1 1 calc R U . . .
 C12 C 0.5074(3) 0.7518(2) 0.33682(15) 0.0435(6) Uani 1 1 d . . . . .
 C13 C 1.0582(4) 0.2374(3) 0.5863(2) 0.0628(7) Uani 1 1 d . . . . .
 H13A H 0.983990 0.179790 0.603568 0.094 Uiso 1 1 calc R U . . .
 H13B H 1.099673 0.277089 0.634225 0.094 Uiso 1 1 calc R U . . .
 H13C H 1.133966 0.194112 0.556685 0.094 Uiso 1 1 calc R U . . .
 C14 C 1.0375(3) 0.3457(2) 0.44964(16) 0.0450(6) Uani 1 1 d . . . . .
 H14 H 1.110006 0.293854 0.428479 0.054 Uiso 1 1 calc R U . . .
 C15 C 0.2155(3) 0.7109(4) 0.3026(3) 0.0767(10) Uani 1 1 d . . . . .
 H15 H 0.116040 0.697612 0.292787 0.092 Uiso 1 1 calc R U . . .
 C16 C 0.9918(3) 0.3319(2) 0.53128(15) 0.0452(6) Uani 1 1 d . . . . .
 C17 C 0.9107(5) 1.0472(3) 0.4169(4) 0.0980(16) Uani 1 1 d . . . . .
 H17A H 0.878815 1.102091 0.373593 0.147 Uiso 1 1 calc R U . . .
 H17B H 1.015057 1.054509 0.423878 0.147 Uiso 1 1 calc R U . . .
 H17C H 0.862406 1.068617 0.467942 0.147 Uiso 1 1 calc R U . . .
 C18 C 0.8846(3) 0.4099(2) 0.56065(15) 0.0472(6) Uani 1 1 d . . . . .
 H18 H 0.851178 0.400476 0.614922 0.057 Uiso 1 1 calc R U . . .
 C19 C 0.6689(3) 0.7716(2) 0.35256(14) 0.0398(5) Uani 1 1 d . . . . .
 N1 N 0.8385(2) 0.62548(18) 0.30102(12) 0.0402(5) Uani 1 1 d . . . . .
 O1 O 0.71680(18) 0.68558(15) 0.41493(10) 0.0430(4) Uani 1 1 d . . . . .
 O2 O 0.7589(2) 0.77777(18) 0.21145(11) 0.0537(5) 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
 C1 C4 1.453(3) . ?
 C1 N1 1.305(3) . ?
 C1 O1 1.335(3) . ?
 C2 H2 0.9400 . ?
 C2 C9 1.392(5) . ?
 C2 C12 1.370(4) . ?
 C3 H3 0.9400 . ?
 C3 C5 1.394(4) . ?
 C3 C15 1.358(5) . ?
 C4 C8 1.400(3) . ?
 C4 C10 1.385(3) . ?
 C5 H5 0.9400 . ?
 C5 C12 1.379(4) . ?
 C6 C19 1.538(3) . ?
 C6 N1 1.394(3) . ?
 C6 O2 1.211(3) . ?
 C7 H7A 0.9800 . ?
 C7 H7B 0.9800 . ?
 C7 C11 1.517(4) . ?
 C7 C17 1.513(5) . ?
 C8 H8 0.9400 . ?
 C8 C18 1.379(4) . ?
 C9 H9 0.9400 . ?
 C9 C15 1.363(6) . ?
 C10 H10 0.9400 . ?
 C10 C14 1.380(4) . ?
 C11 H11A 0.9800 . ?
 C11 H11B 0.9800 . ?
 C11 C19 1.523(3) . ?
 C12 C19 1.523(3) . ?
 C13 H13A 0.9700 . ?
 C13 H13B 0.9700 . ?
 C13 H13C 0.9700 . ?
 C13 C16 1.495(4) . ?
 C14 H14 0.9400 . ?
 C14 C16 1.400(4) . ?
 C15 H15 0.9400 . ?
 C16 C18 1.388(4) . ?
 C17 H17A 0.9700 . ?
 C17 H17B 0.9700 . ?
 C17 H17C 0.9700 . ?
 C18 H18 0.9400 . ?
 C19 O1 1.451(3) . ?

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
 N1 C1 C4 125.6(2) . . ?
 N1 C1 O1 117.8(2) . . ?
 O1 C1 C4 116.7(2) . . ?
 C9 C2 H2 119.8 . . ?
 C12 C2 H2 119.8 . . ?
 C12 C2 C9 120.5(3) . . ?
 C5 C3 H3 119.8 . . ?
 C15 C3 H3 119.8 . . ?
 C15 C3 C5 120.5(3) . . ?
 C8 C4 C1 119.9(2) . . ?
 C10 C4 C1 120.8(2) . . ?
 C10 C4 C8 119.4(2) . . ?
 C3 C5 H5 119.9 . . ?
 C12 C5 C3 120.3(3) . . ?
 C12 C5 H5 119.9 . . ?
 N1 C6 C19 108.68(18) . . ?
 O2 C6 C19 124.7(2) . . ?
 O2 C6 N1 126.6(2) . . ?
 H7A C7 H7B 107.9 . . ?
 C11 C7 H7A 109.2 . . ?
 C11 C7 H7B 109.2 . . ?
 C17 C7 H7A 109.2 . . ?
 C17 C7 H7B 109.2 . . ?
 C17 C7 C11 111.9(3) . . ?
 C4 C8 H8 120.2 . . ?
 C18 C8 C4 119.6(2) . . ?
 C18 C8 H8 120.2 . . ?
 C2 C9 H9 119.8 . . ?
 C15 C9 C2 120.5(3) . . ?
 C15 C9 H9 119.8 . . ?
 C4 C10 H10 119.7 . . ?
 C14 C10 C4 120.5(2) . . ?
 C14 C10 H10 119.7 . . ?
 C7 C11 H11A 108.8 . . ?
 C7 C11 H11B 108.8 . . ?
 C7 C11 C19 113.8(2) . . ?
 H11A C11 H11B 107.7 . . ?
 C19 C11 H11A 108.8 . . ?
 C19 C11 H11B 108.8 . . ?
 C2 C12 C5 118.7(3) . . ?
 C2 C12 C19 120.1(2) . . ?
 C5 C12 C19 121.0(2) . . ?
 H13A C13 H13B 109.5 . . ?
 H13A C13 H13C 109.5 . . ?
 H13B C13 H13C 109.5 . . ?
 C16 C13 H13A 109.5 . . ?
 C16 C13 H13B 109.5 . . ?
 C16 C13 H13C 109.5 . . ?
 C10 C14 H14 119.7 . . ?
 C10 C14 C16 120.6(2) . . ?
 C16 C14 H14 119.7 . . ?
 C3 C15 C9 119.6(3) . . ?
 C3 C15 H15 120.2 . . ?
 C9 C15 H15 120.2 . . ?
 C14 C16 C13 121.2(2) . . ?
 C18 C16 C13 120.5(2) . . ?
 C18 C16 C14 118.3(2) . . ?
 C7 C17 H17A 109.5 . . ?
 C7 C17 H17B 109.5 . . ?
 C7 C17 H17C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 109.5 . . ?
 C8 C18 C16 121.6(2) . . ?
 C8 C18 H18 119.2 . . ?
 C16 C18 H18 119.2 . . ?
 C11 C19 C6 111.7(2) . . ?
 C11 C19 C12 115.4(2) . . ?
 C12 C19 C6 110.25(19) . . ?
 O1 C19 C6 100.85(17) . . ?
 O1 C19 C11 108.83(19) . . ?
 O1 C19 C12 108.76(19) . . ?
 C1 N1 C6 105.43(19) . . ?
 C1 O1 C19 107.19(17) . . ?

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
 C1 C4 C8 C18 179.7(2) . . . . ?
 C1 C4 C10 C14 178.8(2) . . . . ?
 C2 C9 C15 C3 2.3(8) . . . . ?
 C2 C12 C19 C6 82.9(4) . . . . ?
 C2 C12 C19 C11 -149.4(3) . . . . ?
 C2 C12 C19 O1 -26.8(4) . . . . ?
 C3 C5 C12 C2 3.0(4) . . . . ?
 C3 C5 C12 C19 178.1(2) . . . . ?
 C4 C1 N1 C6 -178.5(2) . . . . ?
 C4 C1 O1 C19 -179.71(18) . . . . ?
 C4 C8 C18 C16 1.7(4) . . . . ?
 C4 C10 C14 C16 1.4(4) . . . . ?
 C5 C3 C15 C9 -1.5(6) . . . . ?
 C5 C12 C19 C6 -92.1(3) . . . . ?
 C5 C12 C19 C11 35.6(3) . . . . ?
 C5 C12 C19 O1 158.2(2) . . . . ?
 C6 C19 O1 C1 -1.7(2) . . . . ?
 C7 C11 C19 C6 -52.9(3) . . . . ?
 C7 C11 C19 C12 -179.9(3) . . . . ?
 C7 C11 C19 O1 57.6(3) . . . . ?
 C8 C4 C10 C14 -1.3(3) . . . . ?
 C9 C2 C12 C5 -2.2(7) . . . . ?
 C9 C2 C12 C19 -177.3(4) . . . . ?
 C10 C4 C8 C18 -0.3(3) . . . . ?
 C10 C14 C16 C13 -178.9(2) . . . . ?
 C10 C14 C16 C18 0.0(4) . . . . ?
 C11 C19 O1 C1 -119.3(2) . . . . ?
 C12 C2 C9 C15 -0.5(9) . . . . ?
 C12 C19 O1 C1 114.20(19) . . . . ?
 C13 C16 C18 C8 177.4(2) . . . . ?
 C14 C16 C18 C8 -1.5(4) . . . . ?
 C15 C3 C5 C12 -1.2(4) . . . . ?
 C17 C7 C11 C19 177.8(3) . . . . ?
 C19 C6 N1 C1 -2.6(2) . . . . ?
 N1 C1 C4 C8 -175.9(2) . . . . ?
 N1 C1 C4 C10 4.1(3) . . . . ?
 N1 C1 O1 C19 0.2(3) . . . . ?
 N1 C6 C19 C11 118.1(2) . . . . ?
 N1 C6 C19 C12 -112.1(2) . . . . ?
 N1 C6 C19 O1 2.7(2) . . . . ?
 O1 C1 C4 C8 4.0(3) . . . . ?
 O1 C1 C4 C10 -176.0(2) . . . . ?
 O1 C1 N1 C6 1.6(3) . . . . ?
 O2 C6 C19 C11 -61.0(3) . . . . ?
 O2 C6 C19 C12 68.7(3) . . . . ?
 O2 C6 C19 O1 -176.5(2) . . . . ?
 O2 C6 N1 C1 176.5(2) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
