data_lyw306-1
_audit_creation_date               2024-04-13
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number       '2019/3'
_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           'C25 H26 N2 O4'
_chemical_formula_sum              'C25 H26 N2 O4'
_chemical_formula_weight           418.48
_chemical_absolute_configuration   unk
_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        '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                     10.4089(8)
_cell_length_b                     5.1924(3)
_cell_length_c                     19.6147(15)
_cell_angle_alpha                  90
_cell_angle_beta                   96.064(7)
_cell_angle_gamma                  90
_cell_volume                       1054.19(13)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      3964
_cell_measurement_temperature      100.00(10)
_cell_measurement_theta_max        72.5790
_cell_measurement_theta_min        2.2140
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.726
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.78208
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear dark colourless'
_exptl_crystal_density_diffrn      1.318
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               444
_exptl_crystal_size_max            0.16
_exptl_crystal_size_mid            0.1
_exptl_crystal_size_min            0.08
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0502
_diffrn_reflns_av_unetI/netI       0.0532
_diffrn_reflns_Laue_measured_fraction_full  0.990
_diffrn_reflns_Laue_measured_fraction_max  0.936
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         6
_diffrn_reflns_limit_k_min         -2
_diffrn_reflns_limit_l_max         23
_diffrn_reflns_limit_l_min         -23
_diffrn_reflns_number              6548
_diffrn_reflns_point_group_measured_fraction_full  0.724
_diffrn_reflns_point_group_measured_fraction_max  0.673
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           74.784
_diffrn_reflns_theta_min           2.265
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100.00(10)
_diffrn_detector                   'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean   10.0000
_diffrn_detector_type              HyPix
_diffrn_measured_fraction_theta_full  0.990
_diffrn_measured_fraction_theta_max  0.936
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     86.00 139.00   0.50    1.00    --   99.00  25.00  21.00  106
  2  ω     32.00 121.00   0.50    0.82    --   46.12  25.00  21.00  178
  3  ω    -27.00  28.00   0.50    0.82    --   46.12 -19.00  60.00  110
  4  ω     -8.00  18.00   0.50    0.82    --   46.12 -25.00-142.00   52
  5  ω     30.00  55.00   0.50    1.00    --   99.00 -61.00 -60.00   50
  6  ω     27.00  72.00   0.50    1.00    --   99.00 -61.00 -90.00   90
  7  ω     37.00  64.00   0.50    1.00    --   99.00 -61.00  30.00   54
  8  ω     48.00  73.00   0.50    1.00    --   99.00 -61.00  60.00   50
  9  ω     28.00  53.00   0.50    1.00    --   99.00 -45.00   0.00   50
 10  ω     27.00  52.00   0.50    1.00    --   99.00 -45.00  60.00   50
 11  ω     27.00  52.00   0.50    1.00    --   99.00 -45.00  90.00   50
 12  ω     28.00  63.00   0.50    1.00    --   99.00 -61.00 120.00   70
 13  ω     28.00  71.00   0.50    1.00    --   99.00 -61.00 150.00   86
 14  ω     29.00  71.00   0.50    1.00    --   99.00-125.00 120.00   84
 15  ω   -149.00 -83.00   0.50    1.00    --  -99.00 -25.00-142.00  132
 16  ω   -115.00 -31.00   0.50    0.82    --  -46.12 -25.00-142.00  168
 17  ω     87.00 112.00   0.50    1.00    --   99.00-125.00 120.00   50
 18  ω     63.00 110.00   0.50    1.00    --   99.00-125.00  90.00   94
 19  ω     -3.00  22.00   0.50    0.82    --  -46.12  25.00  21.00   50
 20  ω    -66.00 -36.00   0.50    1.00    --  -99.00  61.00   0.00   60
 21  ω    -60.00 -34.00   0.50    1.00    --  -99.00  61.00 -30.00   52
 22  ω    -57.00 -29.00   0.50    1.00    --  -99.00  61.00 -60.00   56
 23  ω    -99.00 -52.00   0.50    1.00    --  -99.00  77.00-180.00   94
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.0970947000
_diffrn_orient_matrix_UB_12        -0.0483532000
_diffrn_orient_matrix_UB_13        0.0635065000
_diffrn_orient_matrix_UB_21        0.1116817000
_diffrn_orient_matrix_UB_22        0.0828646000
_diffrn_orient_matrix_UB_23        -0.0409060000
_diffrn_orient_matrix_UB_31        -0.0161291000
_diffrn_orient_matrix_UB_32        0.2807390000
_diffrn_orient_matrix_UB_33        0.0230018000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             'Cu K\a'
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'Rotating-anode X-ray tube'
_diffrn_source_type                'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage           0.290
_reflns_Friedel_fraction_full      0.384
_reflns_Friedel_fraction_max       0.341
_reflns_number_gt                  2383
_reflns_number_total               2924
_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 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection        
 'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction          'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics      'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max           0.289
_refine_diff_density_min           -0.313
_refine_diff_density_rms           0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.5(3)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.084
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       286
_refine_ls_number_reflns           2924
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0672
_refine_ls_R_factor_gt             0.0500
_refine_ls_restrained_S_all        1.084
_refine_ls_shift/su_max            0.006
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0615P)²+0.9563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1227
_refine_ls_wR_factor_ref           0.1478
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C17(H17),
 C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C)
;
_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 0.0662(3) 0.9403(7) 0.60838(17) 0.0325(8) Uani 1 1 d . . . . .
 O2 O -0.1021(3) 1.0650(9) 0.66210(19) 0.0423(10) Uani 1 1 d . . . . .
 O3 O 0.7163(3) 0.3388(7) 0.50339(17) 0.0305(8) Uani 1 1 d . . . . .
 O17 O 0.2135(3) 0.3138(6) 0.72422(18) 0.0314(8) Uani 1 1 d . . . . .
 N1 N 0.1834(4) 0.7486(9) 0.7256(2) 0.0270(9) Uani 1 1 d . . . . .
 H1 H 0.216(4) 0.864(10) 0.730(2) 0.006(12) Uiso 1 1 d . . . . .
 N2 N 0.4858(4) 0.3800(8) 0.74854(19) 0.0274(9) Uani 1 1 d . . . . .
 C1 C 0.0268(5) 0.6470(10) 0.8429(2) 0.0292(11) Uani 1 1 d . . . . .
 C2 C -0.0508(5) 0.4393(10) 0.8585(3) 0.0329(11) Uani 1 1 d . . . . .
 H2 H -0.128733 0.404447 0.830300 0.040 Uiso 1 1 calc R U . . .
 C3 C -0.0148(5) 0.2840(10) 0.9150(3) 0.0372(13) Uani 1 1 d . . . . .
 H3 H -0.069888 0.147286 0.925788 0.045 Uiso 1 1 calc R U . . .
 C4 C 0.0996(5) 0.3255(12) 0.9555(3) 0.0410(13) Uani 1 1 d . . . . .
 H4 H 0.124937 0.215364 0.993230 0.049 Uiso 1 1 calc R U . . .
 C5 C 0.1773(5) 0.5300(11) 0.9405(3) 0.0360(12) Uani 1 1 d . . . . .
 H5 H 0.255887 0.562348 0.968431 0.043 Uiso 1 1 calc R U . . .
 C6 C 0.1408(5) 0.6874(10) 0.8848(3) 0.0329(12) Uani 1 1 d . . . . .
 H6 H 0.195188 0.826617 0.875050 0.039 Uiso 1 1 calc R U . . .
 C7 C -0.0135(4) 0.8197(11) 0.7829(2) 0.0309(11) Uani 1 1 d . . . . .
 H7A H 0.012253 0.998448 0.795515 0.037 Uiso 1 1 calc R U . . .
 H7B H -0.108843 0.816095 0.774016 0.037 Uiso 1 1 calc R U . . .
 C8 C 0.0437(4) 0.7489(9) 0.7167(2) 0.0242(10) Uani 1 1 d . . . . .
 H8 H 0.013505 0.571911 0.702748 0.029 Uiso 1 1 calc R U . . .
 C9 C -0.0065(4) 0.9356(9) 0.6605(2) 0.0257(10) Uani 1 1 d . . . . .
 C10 C 0.0330(5) 1.1378(11) 0.5574(3) 0.0348(12) Uani 1 1 d . . . . .
 H10A H 0.088004 1.120084 0.520088 0.052 Uiso 1 1 calc R U . . .
 H10B H 0.046265 1.308020 0.578546 0.052 Uiso 1 1 calc R U . . .
 H10C H -0.057817 1.118935 0.539029 0.052 Uiso 1 1 calc R U . . .
 C11 C 0.2564(5) 0.5355(10) 0.7332(3) 0.0285(10) Uani 1 1 d . . . . .
 C12 C 0.3981(4) 0.5901(9) 0.7551(2) 0.0266(10) Uani 1 1 d . . . . .
 H12A H 0.425209 0.736409 0.727624 0.032 Uiso 1 1 calc R U . . .
 H12B H 0.406685 0.645488 0.803669 0.032 Uiso 1 1 calc R U . . .
 C13 C 0.5448(4) 0.3630(9) 0.6857(2) 0.0255(10) Uani 1 1 d . . . . .
 C14 C 0.5055(5) 0.1780(9) 0.6374(2) 0.0286(11) Uani 1 1 d . . . . .
 H14 H 0.439088 0.060725 0.646117 0.034 Uiso 1 1 calc R U . . .
 C15 C 0.5614(5) 0.1603(9) 0.5760(2) 0.0294(11) Uani 1 1 d . . . . .
 H15 H 0.535233 0.028876 0.543746 0.035 Uiso 1 1 calc R U . . .
 C16 C 0.6560(4) 0.3370(9) 0.5624(2) 0.0248(10) Uani 1 1 d . . . . .
 C17 C 0.6931(4) 0.5287(10) 0.6099(3) 0.0280(10) Uani 1 1 d . . . . .
 H17 H 0.755764 0.652606 0.600038 0.034 Uiso 1 1 calc R U . . .
 C18 C 0.6396(4) 0.5401(10) 0.6712(3) 0.0290(10) Uani 1 1 d . . . . .
 H18 H 0.667317 0.669168 0.703805 0.035 Uiso 1 1 calc R U . . .
 C19 C 0.6846(5) 0.1368(10) 0.4549(2) 0.0315(11) Uani 1 1 d . . . . .
 H19A H 0.734227 0.159004 0.415577 0.047 Uiso 1 1 calc R U . . .
 H19B H 0.592044 0.143040 0.439377 0.047 Uiso 1 1 calc R U . . .
 H19C H 0.705806 -0.029933 0.476676 0.047 Uiso 1 1 calc R U . . .
 C20 C 0.5187(4) 0.2114(9) 0.8023(2) 0.0246(10) Uani 1 1 d . . . . .
 C21 C 0.6302(4) 0.0617(10) 0.8046(2) 0.0259(10) Uani 1 1 d . . . . .
 H21 H 0.685684 0.078153 0.769392 0.031 Uiso 1 1 calc R U . . .
 C22 C 0.6611(5) -0.1102(10) 0.8576(3) 0.0306(11) Uani 1 1 d . . . . .
 H22 H 0.737382 -0.210934 0.857965 0.037 Uiso 1 1 calc R U . . .
 C23 C 0.5823(5) -0.1388(10) 0.9106(2) 0.0328(12) Uani 1 1 d . . . . .
 H23 H 0.602791 -0.260472 0.946279 0.039 Uiso 1 1 calc R U . . .
 C24 C 0.4734(5) 0.0154(10) 0.9096(2) 0.0298(11) Uani 1 1 d . . . . .
 H24 H 0.420651 0.004034 0.946155 0.036 Uiso 1 1 calc R U . . .
 C25 C 0.4400(5) 0.1866(10) 0.8560(2) 0.0280(11) Uani 1 1 d . . . . .
 H25 H 0.363667 0.287199 0.855741 0.034 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 C9 1.334(6) . ?
 O1 C10 1.449(6) . ?
 O2 C9 1.204(6) . ?
 O3 C16 1.373(5) . ?
 O3 C19 1.430(6) . ?
 O17 C11 1.241(6) . ?
 N1 H1 0.69(5) . ?
 N1 C8 1.447(6) . ?
 N1 C11 1.342(6) . ?
 N2 C12 1.437(6) . ?
 N2 C13 1.436(6) . ?
 N2 C20 1.385(6) . ?
 C1 C2 1.401(7) . ?
 C1 C6 1.386(7) . ?
 C1 C7 1.504(7) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.389(7) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.378(8) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.385(8) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.385(7) . ?
 C6 H6 0.9500 . ?
 C7 H7A 0.9900 . ?
 C7 H7B 0.9900 . ?
 C7 C8 1.529(6) . ?
 C8 H8 1.0000 . ?
 C8 C9 1.519(6) . ?
 C10 H10A 0.9800 . ?
 C10 H10B 0.9800 . ?
 C10 H10C 0.9800 . ?
 C11 C12 1.519(7) . ?
 C12 H12A 0.9900 . ?
 C12 H12B 0.9900 . ?
 C13 C14 1.381(7) . ?
 C13 C18 1.400(7) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.396(6) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.392(7) . ?
 C16 C17 1.390(7) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.379(7) . ?
 C18 H18 0.9500 . ?
 C19 H19A 0.9800 . ?
 C19 H19B 0.9800 . ?
 C19 H19C 0.9800 . ?
 C20 C21 1.394(6) . ?
 C20 C25 1.408(6) . ?
 C21 H21 0.9500 . ?
 C21 C22 1.381(7) . ?
 C22 H22 0.9500 . ?
 C22 C23 1.400(7) . ?
 C23 H23 0.9500 . ?
 C23 C24 1.386(7) . ?
 C24 H24 0.9500 . ?
 C24 C25 1.393(7) . ?
 C25 H25 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
 C9 O1 C10 115.4(4) . . ?
 C16 O3 C19 117.4(4) . . ?
 C8 N1 H1 120(4) . . ?
 C11 N1 H1 116(4) . . ?
 C11 N1 C8 124.4(5) . . ?
 C13 N2 C12 117.2(4) . . ?
 C20 N2 C12 121.3(4) . . ?
 C20 N2 C13 121.3(4) . . ?
 C2 C1 C7 120.7(5) . . ?
 C6 C1 C2 117.7(5) . . ?
 C6 C1 C7 121.6(5) . . ?
 C1 C2 H2 119.7 . . ?
 C3 C2 C1 120.6(5) . . ?
 C3 C2 H2 119.7 . . ?
 C2 C3 H3 119.6 . . ?
 C4 C3 C2 120.9(5) . . ?
 C4 C3 H3 119.6 . . ?
 C3 C4 H4 120.5 . . ?
 C3 C4 C5 119.1(5) . . ?
 C5 C4 H4 120.5 . . ?
 C4 C5 H5 119.9 . . ?
 C4 C5 C6 120.1(5) . . ?
 C6 C5 H5 119.9 . . ?
 C1 C6 C5 121.7(5) . . ?
 C1 C6 H6 119.2 . . ?
 C5 C6 H6 119.2 . . ?
 C1 C7 H7A 108.5 . . ?
 C1 C7 H7B 108.5 . . ?
 C1 C7 C8 114.9(4) . . ?
 H7A C7 H7B 107.5 . . ?
 C8 C7 H7A 108.5 . . ?
 C8 C7 H7B 108.5 . . ?
 N1 C8 C7 112.0(4) . . ?
 N1 C8 H8 108.3 . . ?
 N1 C8 C9 110.6(4) . . ?
 C7 C8 H8 108.3 . . ?
 C9 C8 C7 109.2(4) . . ?
 C9 C8 H8 108.3 . . ?
 O1 C9 C8 112.9(4) . . ?
 O2 C9 O1 123.2(4) . . ?
 O2 C9 C8 123.9(4) . . ?
 O1 C10 H10A 109.5 . . ?
 O1 C10 H10B 109.5 . . ?
 O1 C10 H10C 109.5 . . ?
 H10A C10 H10B 109.5 . . ?
 H10A C10 H10C 109.5 . . ?
 H10B C10 H10C 109.5 . . ?
 O17 C11 N1 123.9(5) . . ?
 O17 C11 C12 122.5(4) . . ?
 N1 C11 C12 113.6(5) . . ?
 N2 C12 C11 116.1(4) . . ?
 N2 C12 H12A 108.3 . . ?
 N2 C12 H12B 108.3 . . ?
 C11 C12 H12A 108.3 . . ?
 C11 C12 H12B 108.3 . . ?
 H12A C12 H12B 107.4 . . ?
 C14 C13 N2 120.6(4) . . ?
 C14 C13 C18 118.8(4) . . ?
 C18 C13 N2 120.6(4) . . ?
 C13 C14 H14 119.4 . . ?
 C13 C14 C15 121.2(4) . . ?
 C15 C14 H14 119.4 . . ?
 C14 C15 H15 120.3 . . ?
 C16 C15 C14 119.3(4) . . ?
 C16 C15 H15 120.3 . . ?
 O3 C16 C15 124.2(4) . . ?
 O3 C16 C17 116.1(4) . . ?
 C17 C16 C15 119.7(4) . . ?
 C16 C17 H17 119.8 . . ?
 C18 C17 C16 120.4(5) . . ?
 C18 C17 H17 119.8 . . ?
 C13 C18 H18 119.7 . . ?
 C17 C18 C13 120.5(5) . . ?
 C17 C18 H18 119.7 . . ?
 O3 C19 H19A 109.5 . . ?
 O3 C19 H19B 109.5 . . ?
 O3 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?
 N2 C20 C21 121.0(4) . . ?
 N2 C20 C25 120.7(4) . . ?
 C21 C20 C25 118.2(4) . . ?
 C20 C21 H21 119.6 . . ?
 C22 C21 C20 120.8(4) . . ?
 C22 C21 H21 119.6 . . ?
 C21 C22 H22 119.4 . . ?
 C21 C22 C23 121.3(4) . . ?
 C23 C22 H22 119.4 . . ?
 C22 C23 H23 121.0 . . ?
 C24 C23 C22 118.1(5) . . ?
 C24 C23 H23 121.0 . . ?
 C23 C24 H24 119.4 . . ?
 C23 C24 C25 121.2(4) . . ?
 C25 C24 H24 119.4 . . ?
 C20 C25 H25 119.9 . . ?
 C24 C25 C20 120.3(4) . . ?
 C24 C25 H25 119.9 . . ?

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
 O3 C16 C17 C18 -178.9(4) . . . . ?
 O17 C11 C12 N2 15.1(7) . . . . ?
 N1 C8 C9 O1 37.0(5) . . . . ?
 N1 C8 C9 O2 -143.5(5) . . . . ?
 N1 C11 C12 N2 -165.8(4) . . . . ?
 N2 C13 C14 C15 179.6(4) . . . . ?
 N2 C13 C18 C17 -177.8(4) . . . . ?
 N2 C20 C21 C22 -178.6(4) . . . . ?
 N2 C20 C25 C24 179.6(4) . . . . ?
 C1 C2 C3 C4 -2.1(8) . . . . ?
 C1 C7 C8 N1 -58.0(6) . . . . ?
 C1 C7 C8 C9 179.1(4) . . . . ?
 C2 C1 C6 C5 -0.3(7) . . . . ?
 C2 C1 C7 C8 -95.2(5) . . . . ?
 C2 C3 C4 C5 1.9(8) . . . . ?
 C3 C4 C5 C6 -1.0(8) . . . . ?
 C4 C5 C6 C1 0.2(8) . . . . ?
 C6 C1 C2 C3 1.2(7) . . . . ?
 C6 C1 C7 C8 85.1(6) . . . . ?
 C7 C1 C2 C3 -178.5(5) . . . . ?
 C7 C1 C6 C5 179.4(5) . . . . ?
 C7 C8 C9 O1 160.7(4) . . . . ?
 C7 C8 C9 O2 -19.9(6) . . . . ?
 C8 N1 C11 O17 10.3(8) . . . . ?
 C8 N1 C11 C12 -168.9(4) . . . . ?
 C10 O1 C9 O2 8.1(7) . . . . ?
 C10 O1 C9 C8 -172.4(4) . . . . ?
 C11 N1 C8 C7 101.9(5) . . . . ?
 C11 N1 C8 C9 -136.0(5) . . . . ?
 C12 N2 C13 C14 -106.0(5) . . . . ?
 C12 N2 C13 C18 71.4(6) . . . . ?
 C12 N2 C20 C21 -159.9(4) . . . . ?
 C12 N2 C20 C25 20.2(7) . . . . ?
 C13 N2 C12 C11 92.5(5) . . . . ?
 C13 N2 C20 C21 15.7(7) . . . . ?
 C13 N2 C20 C25 -164.2(4) . . . . ?
 C13 C14 C15 C16 -1.9(7) . . . . ?
 C14 C13 C18 C17 -0.4(7) . . . . ?
 C14 C15 C16 O3 -179.3(4) . . . . ?
 C14 C15 C16 C17 -0.2(7) . . . . ?
 C15 C16 C17 C18 1.9(7) . . . . ?
 C16 C17 C18 C13 -1.6(7) . . . . ?
 C18 C13 C14 C15 2.2(7) . . . . ?
 C19 O3 C16 C15 -3.7(6) . . . . ?
 C19 O3 C16 C17 177.1(4) . . . . ?
 C20 N2 C12 C11 -91.8(5) . . . . ?
 C20 N2 C13 C14 78.2(6) . . . . ?
 C20 N2 C13 C18 -104.4(5) . . . . ?
 C20 C21 C22 C23 -0.4(7) . . . . ?
 C21 C20 C25 C24 -0.3(7) . . . . ?
 C21 C22 C23 C24 -1.6(7) . . . . ?
 C22 C23 C24 C25 2.6(7) . . . . ?
 C23 C24 C25 C20 -1.7(7) . . . . ?
 C25 C20 C21 C22 1.3(7) . . . . ?

_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  1.405
_oxdiff_exptl_absorpt_empirical_full_min  0.627
