data_hsl-20180905
_audit_creation_date               2018-09-13
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number       '2016/6'
_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           'C23 H24 N6 O2'
_chemical_formula_sum              'C23 H24 N6 O2'
_chemical_formula_weight           416.48
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C1 H1 O1 N1'
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        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     8.2396(2)
_cell_length_b                     11.5901(5)
_cell_length_c                     12.2867(6)
_cell_angle_alpha                  107.523(4)
_cell_angle_beta                   104.775(3)
_cell_angle_gamma                  90.140(3)
_cell_volume                       1077.91(8)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      5031
_cell_measurement_temperature      293(2)
_cell_measurement_theta_max        70.8210
_cell_measurement_theta_min        3.9910
_shelx_estimated_absorpt_T_max     0.973
_shelx_estimated_absorpt_T_min     0.830
_exptl_absorpt_coefficient_mu      0.692
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.81744
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear light colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     light
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.283
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               440
_exptl_crystal_size_max            0.28
_exptl_crystal_size_mid            0.06
_exptl_crystal_size_min            0.04
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0291
_diffrn_reflns_av_unetI/netI       0.0404
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.979
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         14
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         14
_diffrn_reflns_limit_l_min         -14
_diffrn_reflns_number              9969
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.979
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           71.409
_diffrn_reflns_theta_min           3.916
_diffrn_ambient_temperature        293(2)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   8.0528
_diffrn_detector_type              EosS2
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -105.00 -17.00   1.00    3.50    --  -35.62 -38.00  30.00   88
  2  ω    -52.00  32.00   1.00    3.50    --  -35.62  57.00-180.00   84
  3  ω   -105.00 -17.00   1.00    3.50    --  -35.62 -38.00   0.00   88
  4  ω    -89.00  -2.00   1.00    3.50    --  -35.62 125.00-180.00   87
  5  ω   -105.00 -17.00   1.00    3.50    --  -35.62 -38.00 -60.00   88
  6  ω    -36.00  65.00   1.00    3.50    --   35.62 -19.00  60.00  101
  7  ω      1.00  75.00   1.00    3.50    --   35.62 -99.00 -60.00   74
  8  ω     23.00  89.00   1.00    3.50    --   35.62-125.00  90.00   66
  9  ω     23.00  89.00   1.00    3.50    --   35.62-125.00-120.00   66
 10  ω     38.00 124.00   1.00   17.00    --  106.50 -45.00 120.00   86
 11  ω     37.00 109.00   1.00   17.00    --  106.50 -95.00-120.00   72
 12  ω     37.00 109.00   1.00   17.00    --  106.50 -95.00 120.00   72
 13  ω     38.00 124.00   1.00   17.00    --  106.50 -45.00 -30.00   86
 14  ω     85.00 176.00   1.00   17.00    --  106.50  30.00 -60.00   91
 15  ω     38.00 124.00   1.00   17.00    --  106.50 -45.00-150.00   86
 16  ω     37.00 109.00   1.00   17.00    --  106.50 -95.00   0.00   72
 17  ω     68.00 178.00   1.00   17.00    --  106.50  15.00-120.00  110
 18  ω     37.00 112.00   1.00   17.00    --  106.50-111.00  90.00   75
 19  ω     37.00 109.00   1.00   17.00    --  106.50 -95.00 150.00   72
 20  ω     37.00 128.00   1.00   17.00    --  106.50 -30.00  30.00   91
 21  ω     37.00 109.00   1.00   17.00    --  106.50 -95.00 -90.00   72
 22  ω     35.00 145.00   1.00   17.00    --  106.50 -15.00 -90.00  110
 23  ω   -103.00  -9.00   1.00    3.50    --  -35.62 -77.00-150.00   94
 24  ω    -36.00  65.00   1.00    3.50    --   35.62 -19.00 -30.00  101
 25  ω     19.00 103.00   1.00    3.50    --   35.62  57.00 150.00   84
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.0033074000
_diffrn_orient_matrix_UB_12        0.1127466000
_diffrn_orient_matrix_UB_13        0.1065358000
_diffrn_orient_matrix_UB_21        0.0493705000
_diffrn_orient_matrix_UB_22        0.0820842000
_diffrn_orient_matrix_UB_23        -0.0664810000
_diffrn_orient_matrix_UB_31        -0.1876676000
_diffrn_orient_matrix_UB_32        0.0111477000
_diffrn_orient_matrix_UB_33        -0.0534695000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3386
_reflns_number_total               4103
_reflns_odcompleteness_completeness  99.84
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       66.97
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection         'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction          'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max           0.203
_refine_diff_density_min           -0.195
_refine_diff_density_rms           0.042
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.178
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       280
_refine_ls_number_reflns           4103
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0738
_refine_ls_R_factor_gt             0.0549
_refine_ls_restrained_S_all        1.178
_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)+(0.0739P)²+0.3792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1661
_refine_ls_wR_factor_ref           0.1740
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C25(H25A,H25B), C18(H18A,H18B), C8(H8A,H8B), C12(H12A,H12B),
 C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C27(H27), C31(H31), C20(H20), C28(H28), C29(H29), C23(H23),
 C30(H30), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       ?
_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
 O13 O 0.98061(18) 0.88758(14) 0.57609(14) 0.0420(4) Uani 1 1 d . . . . .
 O9 O 0.90496(19) 0.60232(14) 0.41445(15) 0.0454(4) Uani 1 1 d . . . . .
 N1 N 0.4781(2) 0.77416(16) 0.35168(16) 0.0370(4) Uani 1 1 d . . . . .
 N4 N 0.7701(2) 0.86907(16) 0.23521(15) 0.0367(4) Uani 1 1 d . . . . .
 N16 N 0.5429(2) 0.87986(17) 0.53460(18) 0.0443(5) Uani 1 1 d . . . . .
 N6 N 0.9244(3) 0.7245(2) 0.18608(18) 0.0508(5) Uani 1 1 d . . . . .
 N17 N 0.4194(2) 0.81201(19) 0.44755(19) 0.0480(5) Uani 1 1 d . . . . .
 N5 N 0.8784(2) 0.8285(2) 0.17023(18) 0.0505(5) Uani 1 1 d . . . . .
 C3 C 0.7434(2) 0.79057(18) 0.29274(17) 0.0320(4) Uani 1 1 d . . . . .
 C2 C 0.6408(2) 0.81728(17) 0.37669(18) 0.0317(4) Uani 1 1 d . . . . .
 C15 C 0.6792(3) 0.88610(18) 0.49365(19) 0.0349(4) Uani 1 1 d . . . . .
 C26 C 0.5058(3) 0.92701(19) 0.13070(19) 0.0372(5) Uani 1 1 d . . . . .
 C7 C 0.8425(3) 0.6978(2) 0.25984(19) 0.0393(5) Uani 1 1 d . . . . .
 C14 C 0.8408(3) 0.95891(19) 0.57069(19) 0.0388(5) Uani 1 1 d . . . . .
 H14A H 0.861973 1.023900 0.540186 0.047 Uiso 1 1 calc R . . . .
 H14B H 0.829141 0.995615 0.650128 0.047 Uiso 1 1 calc R . . . .
 C25 C 0.6743(3) 0.9714(2) 0.2197(2) 0.0425(5) Uani 1 1 d . . . . .
 H25A H 0.737148 1.022985 0.192821 0.051 Uiso 1 1 calc R . . . .
 H25B H 0.657458 1.019233 0.295113 0.051 Uiso 1 1 calc R . . . .
 C19 C 0.3570(3) 0.5633(2) 0.2385(2) 0.0410(5) Uani 1 1 d . . . . .
 C18 C 0.3697(3) 0.6936(2) 0.2415(2) 0.0462(5) Uani 1 1 d . . . . .
 H18A H 0.412507 0.698371 0.176309 0.055 Uiso 1 1 calc R . . . .
 H18B H 0.257668 0.721806 0.229715 0.055 Uiso 1 1 calc R . . . .
 C8 C 0.8633(3) 0.5826(2) 0.2911(2) 0.0476(6) Uani 1 1 d . . . . .
 H8A H 0.759262 0.530378 0.253813 0.057 Uiso 1 1 calc R . . . .
 H8B H 0.951194 0.540755 0.259605 0.057 Uiso 1 1 calc R . . . .
 C12 C 0.9671(3) 0.7961(2) 0.6298(2) 0.0502(6) Uani 1 1 d . . . . .
 H12A H 0.854200 0.755523 0.599212 0.060 Uiso 1 1 calc R . . . .
 H12B H 0.988852 0.832553 0.714833 0.060 Uiso 1 1 calc R . . . .
 C24 C 0.4498(4) 0.5213(2) 0.3271(2) 0.0547(6) Uani 1 1 d . . . . .
 H24 H 0.526325 0.574662 0.392405 0.066 Uiso 1 1 calc R . . . .
 C27 C 0.4946(3) 0.8419(3) 0.0219(2) 0.0553(6) Uani 1 1 d . . . . .
 H27 H 0.591925 0.813293 0.002115 0.066 Uiso 1 1 calc R . . . .
 C31 C 0.3608(3) 0.9692(3) 0.1580(2) 0.0535(6) Uani 1 1 d . . . . .
 H31 H 0.366977 1.026880 0.230769 0.064 Uiso 1 1 calc R . . . .
 C10 C 1.0745(3) 0.6530(2) 0.4721(3) 0.0542(6) Uani 1 1 d . . . . .
 H10A H 1.101460 0.715678 0.440599 0.065 Uiso 1 1 calc R . . . .
 H10B H 1.151401 0.590325 0.458113 0.065 Uiso 1 1 calc R . . . .
 C11 C 1.0934(4) 0.7059(2) 0.6024(3) 0.0605(7) Uani 1 1 d . . . . .
 H11A H 1.206081 0.745706 0.640871 0.073 Uiso 1 1 calc R . . . .
 H11B H 1.080143 0.640866 0.634757 0.073 Uiso 1 1 calc R . . . .
 C20 C 0.2444(4) 0.4821(3) 0.1414(3) 0.0612(7) Uani 1 1 d . . . . .
 H20 H 0.181345 0.509380 0.081036 0.073 Uiso 1 1 calc R . . . .
 C28 C 0.3392(4) 0.7995(3) -0.0572(3) 0.0735(9) Uani 1 1 d . . . . .
 H28 H 0.332013 0.741851 -0.130094 0.088 Uiso 1 1 calc R . . . .
 C29 C 0.1957(4) 0.8418(4) -0.0290(3) 0.0810(11) Uani 1 1 d . . . . .
 H29 H 0.091249 0.812946 -0.082710 0.097 Uiso 1 1 calc R . . . .
 C23 C 0.4298(5) 0.4000(3) 0.3193(3) 0.0761(10) Uani 1 1 d . . . . .
 H23 H 0.492733 0.371881 0.379072 0.091 Uiso 1 1 calc R . . . .
 C30 C 0.2055(4) 0.9260(4) 0.0775(3) 0.0783(10) Uani 1 1 d . . . . .
 H30 H 0.107612 0.954769 0.096365 0.094 Uiso 1 1 calc R . . . .
 C21 C 0.2250(5) 0.3619(3) 0.1336(3) 0.0852(12) Uani 1 1 d . . . . .
 H21 H 0.149902 0.308110 0.067765 0.102 Uiso 1 1 calc R . . . .
 C22 C 0.3156(6) 0.3211(3) 0.2221(4) 0.0898(13) Uani 1 1 d . . . . .
 H22 H 0.300479 0.239933 0.217103 0.108 Uiso 1 1 calc R . . . .


_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
 O13 C14 1.419(3) . ?
 O13 C12 1.425(3) . ?
 O9 C8 1.412(3) . ?
 O9 C10 1.428(3) . ?
 N1 N17 1.339(3) . ?
 N1 C2 1.355(2) . ?
 N1 C18 1.456(3) . ?
 N4 N5 1.339(3) . ?
 N4 C3 1.357(3) . ?
 N4 C25 1.459(3) . ?
 N16 N17 1.316(3) . ?
 N16 C15 1.352(3) . ?
 N6 N5 1.320(3) . ?
 N6 C7 1.361(3) . ?
 C3 C2 1.458(3) . ?
 C3 C7 1.377(3) . ?
 C2 C15 1.370(3) . ?
 C15 C14 1.501(3) . ?
 C26 C25 1.507(3) . ?
 C26 C27 1.382(3) . ?
 C26 C31 1.373(3) . ?
 C7 C8 1.496(3) . ?
 C14 H14A 0.9700 . ?
 C14 H14B 0.9700 . ?
 C25 H25A 0.9700 . ?
 C25 H25B 0.9700 . ?
 C19 C18 1.502(3) . ?
 C19 C24 1.380(4) . ?
 C19 C20 1.387(3) . ?
 C18 H18A 0.9700 . ?
 C18 H18B 0.9700 . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?
 C12 H12A 0.9700 . ?
 C12 H12B 0.9700 . ?
 C12 C11 1.503(4) . ?
 C24 H24 0.9300 . ?
 C24 C23 1.387(4) . ?
 C27 H27 0.9300 . ?
 C27 C28 1.378(4) . ?
 C31 H31 0.9300 . ?
 C31 C30 1.386(4) . ?
 C10 H10A 0.9700 . ?
 C10 H10B 0.9700 . ?
 C10 C11 1.498(4) . ?
 C11 H11A 0.9700 . ?
 C11 H11B 0.9700 . ?
 C20 H20 0.9300 . ?
 C20 C21 1.374(5) . ?
 C28 H28 0.9300 . ?
 C28 C29 1.367(5) . ?
 C29 H29 0.9300 . ?
 C29 C30 1.359(5) . ?
 C23 H23 0.9300 . ?
 C23 C22 1.383(5) . ?
 C30 H30 0.9300 . ?
 C21 H21 0.9300 . ?
 C21 C22 1.364(6) . ?
 C22 H22 0.9300 . ?

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 O13 C12 112.95(18) . . ?
 C8 O9 C10 112.4(2) . . ?
 N17 N1 C2 110.99(18) . . ?
 N17 N1 C18 119.53(18) . . ?
 C2 N1 C18 129.44(19) . . ?
 N5 N4 C3 111.16(18) . . ?
 N5 N4 C25 119.85(18) . . ?
 C3 N4 C25 127.78(18) . . ?
 N17 N16 C15 108.97(18) . . ?
 N5 N6 C7 108.96(19) . . ?
 N16 N17 N1 107.14(17) . . ?
 N6 N5 N4 107.22(18) . . ?
 N4 C3 C2 122.33(18) . . ?
 N4 C3 C7 104.31(18) . . ?
 C7 C3 C2 133.12(19) . . ?
 N1 C2 C3 124.93(19) . . ?
 N1 C2 C15 104.16(17) . . ?
 C15 C2 C3 130.90(18) . . ?
 N16 C15 C2 108.71(18) . . ?
 N16 C15 C14 122.31(19) . . ?
 C2 C15 C14 128.98(18) . . ?
 C27 C26 C25 120.7(2) . . ?
 C31 C26 C25 120.1(2) . . ?
 C31 C26 C27 119.2(2) . . ?
 N6 C7 C3 108.3(2) . . ?
 N6 C7 C8 121.7(2) . . ?
 C3 C7 C8 130.0(2) . . ?
 O13 C14 C15 112.59(16) . . ?
 O13 C14 H14A 109.1 . . ?
 O13 C14 H14B 109.1 . . ?
 C15 C14 H14A 109.1 . . ?
 C15 C14 H14B 109.1 . . ?
 H14A C14 H14B 107.8 . . ?
 N4 C25 C26 110.53(17) . . ?
 N4 C25 H25A 109.5 . . ?
 N4 C25 H25B 109.5 . . ?
 C26 C25 H25A 109.5 . . ?
 C26 C25 H25B 109.5 . . ?
 H25A C25 H25B 108.1 . . ?
 C24 C19 C18 123.5(2) . . ?
 C24 C19 C20 118.9(2) . . ?
 C20 C19 C18 117.6(2) . . ?
 N1 C18 C19 113.72(18) . . ?
 N1 C18 H18A 108.8 . . ?
 N1 C18 H18B 108.8 . . ?
 C19 C18 H18A 108.8 . . ?
 C19 C18 H18B 108.8 . . ?
 H18A C18 H18B 107.7 . . ?
 O9 C8 C7 112.83(19) . . ?
 O9 C8 H8A 109.0 . . ?
 O9 C8 H8B 109.0 . . ?
 C7 C8 H8A 109.0 . . ?
 C7 C8 H8B 109.0 . . ?
 H8A C8 H8B 107.8 . . ?
 O13 C12 H12A 109.9 . . ?
 O13 C12 H12B 109.9 . . ?
 O13 C12 C11 108.7(2) . . ?
 H12A C12 H12B 108.3 . . ?
 C11 C12 H12A 109.9 . . ?
 C11 C12 H12B 109.9 . . ?
 C19 C24 H24 119.8 . . ?
 C19 C24 C23 120.4(3) . . ?
 C23 C24 H24 119.8 . . ?
 C26 C27 H27 120.0 . . ?
 C28 C27 C26 120.0(3) . . ?
 C28 C27 H27 120.0 . . ?
 C26 C31 H31 119.9 . . ?
 C26 C31 C30 120.2(3) . . ?
 C30 C31 H31 119.9 . . ?
 O9 C10 H10A 109.9 . . ?
 O9 C10 H10B 109.9 . . ?
 O9 C10 C11 109.0(2) . . ?
 H10A C10 H10B 108.3 . . ?
 C11 C10 H10A 109.9 . . ?
 C11 C10 H10B 109.9 . . ?
 C12 C11 H11A 109.1 . . ?
 C12 C11 H11B 109.1 . . ?
 C10 C11 C12 112.6(2) . . ?
 C10 C11 H11A 109.1 . . ?
 C10 C11 H11B 109.1 . . ?
 H11A C11 H11B 107.8 . . ?
 C19 C20 H20 119.7 . . ?
 C21 C20 C19 120.6(3) . . ?
 C21 C20 H20 119.7 . . ?
 C27 C28 H28 119.8 . . ?
 C29 C28 C27 120.3(3) . . ?
 C29 C28 H28 119.8 . . ?
 C28 C29 H29 119.9 . . ?
 C30 C29 C28 120.1(3) . . ?
 C30 C29 H29 119.9 . . ?
 C24 C23 H23 120.2 . . ?
 C22 C23 C24 119.6(3) . . ?
 C22 C23 H23 120.2 . . ?
 C31 C30 H30 119.9 . . ?
 C29 C30 C31 120.2(3) . . ?
 C29 C30 H30 119.9 . . ?
 C20 C21 H21 119.9 . . ?
 C22 C21 C20 120.2(3) . . ?
 C22 C21 H21 119.9 . . ?
 C23 C22 H22 119.9 . . ?
 C21 C22 C23 120.3(3) . . ?
 C21 C22 H22 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
 O13 C12 C11 C10 -55.4(3) . . . . ?
 O9 C10 C11 C12 -54.5(3) . . . . ?
 N1 C2 C15 N16 1.4(2) . . . . ?
 N1 C2 C15 C14 -178.7(2) . . . . ?
 N4 C3 C2 N1 99.6(2) . . . . ?
 N4 C3 C2 C15 -81.2(3) . . . . ?
 N4 C3 C7 N6 0.5(2) . . . . ?
 N4 C3 C7 C8 -177.9(2) . . . . ?
 N16 C15 C14 O13 122.8(2) . . . . ?
 N6 C7 C8 O9 128.6(2) . . . . ?
 N17 N1 C2 C3 178.37(19) . . . . ?
 N17 N1 C2 C15 -1.0(2) . . . . ?
 N17 N1 C18 C19 -78.9(3) . . . . ?
 N17 N16 C15 C2 -1.3(2) . . . . ?
 N17 N16 C15 C14 178.79(19) . . . . ?
 N5 N4 C3 C2 175.20(18) . . . . ?
 N5 N4 C3 C7 0.1(2) . . . . ?
 N5 N4 C25 C26 92.9(2) . . . . ?
 N5 N6 C7 C3 -1.0(3) . . . . ?
 N5 N6 C7 C8 177.6(2) . . . . ?
 C3 N4 N5 N6 -0.8(2) . . . . ?
 C3 N4 C25 C26 -73.3(3) . . . . ?
 C3 C2 C15 N16 -177.9(2) . . . . ?
 C3 C2 C15 C14 2.0(4) . . . . ?
 C3 C7 C8 O9 -53.1(3) . . . . ?
 C2 N1 N17 N16 0.2(2) . . . . ?
 C2 N1 C18 C19 98.6(3) . . . . ?
 C2 C3 C7 N6 -173.7(2) . . . . ?
 C2 C3 C7 C8 7.8(4) . . . . ?
 C2 C15 C14 O13 -57.1(3) . . . . ?
 C15 N16 N17 N1 0.6(2) . . . . ?
 C26 C27 C28 C29 0.4(5) . . . . ?
 C26 C31 C30 C29 -0.1(4) . . . . ?
 C7 N6 N5 N4 1.1(3) . . . . ?
 C7 C3 C2 N1 -86.9(3) . . . . ?
 C7 C3 C2 C15 92.3(3) . . . . ?
 C14 O13 C12 C11 164.95(18) . . . . ?
 C25 N4 N5 N6 -169.14(19) . . . . ?
 C25 N4 C3 C2 -17.6(3) . . . . ?
 C25 N4 C3 C7 167.35(19) . . . . ?
 C25 C26 C27 C28 178.0(2) . . . . ?
 C25 C26 C31 C30 -178.2(2) . . . . ?
 C19 C24 C23 C22 -0.2(4) . . . . ?
 C19 C20 C21 C22 0.6(5) . . . . ?
 C18 N1 N17 N16 178.16(18) . . . . ?
 C18 N1 C2 C3 0.7(3) . . . . ?
 C18 N1 C2 C15 -178.7(2) . . . . ?
 C18 C19 C24 C23 179.0(2) . . . . ?
 C18 C19 C20 C21 -179.2(3) . . . . ?
 C8 O9 C10 C11 162.81(19) . . . . ?
 C12 O13 C14 C15 -64.0(2) . . . . ?
 C24 C19 C18 N1 -5.2(3) . . . . ?
 C24 C19 C20 C21 0.2(4) . . . . ?
 C24 C23 C22 C21 1.0(5) . . . . ?
 C27 C26 C25 N4 -49.4(3) . . . . ?
 C27 C26 C31 C30 0.4(4) . . . . ?
 C27 C28 C29 C30 -0.1(5) . . . . ?
 C31 C26 C25 N4 129.3(2) . . . . ?
 C31 C26 C27 C28 -0.6(4) . . . . ?
 C10 O9 C8 C7 -72.9(2) . . . . ?
 C20 C19 C18 N1 174.2(2) . . . . ?
 C20 C19 C24 C23 -0.4(4) . . . . ?
 C20 C21 C22 C23 -1.2(5) . . . . ?
 C28 C29 C30 C31 -0.1(5) . . . . ?

_olex2_date_sample_data_collection  2018-09-05
_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  2.455
_oxdiff_exptl_absorpt_empirical_full_min  0.288
