data_qhn-1-789
_audit_creation_date               2019-05-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_author_name                 'Farzaneh Fadaei Tirani'
_audit_contact_author              'Farzaneh Fadaei Tirani'
_audit_contact_author_address 
;
   Dr. Farzaneh Fadaei Tirani
   EPFL SB ISIC-GE 
   BCH 2111 (Batochime UNIL)
   Av. F.-A. Forel 2 
   CH-1015 Lausanne
   Suisse
;
_audit_contact_author_email        farzaneh.fadaeitirani@epfl.ch 
_audit_contact_author_phone        '+41 21 693 9840'
_publ_contact_author_id_orcid      https://orcid.org/0000-0002-7515-7593

_publ_section_references
;
CrysAlisPro Software System, Rigaku Oxford Diffraction, (2015).
Sheldrick, G.M., ShelXT-Integrated space-group and
 crystal-structure determination, Acta Cryst., (2015), A71, 3-8.
Sheldrick, G.M., Crystal structure refinement with ShelXL,
 Acta Cryst., (2015), C71, 3-8.
O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard, H. Puschmann,
 Olex2: A complete structure solution, refinement and analysis program,
 J. Appl. Cryst., (2009), 42, 339-341.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C20 H17 N3 O'
_chemical_formula_sum              'C20 H17 N3 O'
_chemical_formula_weight           315.36
_chemical_absolute_configuration   ?
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C20 H17 N3 O1'
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                     7.41462(9)
_cell_length_b                     10.40955(11)
_cell_length_c                     20.8084(2)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1606.05(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      19117
_cell_measurement_temperature      140.00(10)
_cell_measurement_theta_max        73.4190
_cell_measurement_theta_min        4.2190
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.656
_exptl_absorpt_correction_T_max    1.000
_exptl_absorpt_correction_T_min    0.313
_exptl_absorpt_correction_type     Gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_density_diffrn      1.304
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         irregular
_exptl_crystal_F_000               664
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 0 1 0 0.1867
 0 -1 0 0.1934
 1 0 -1 0.1939
 -1 0 1 0.2878
 -1 1 1 0.2898
 1 0 2 0.1476
 -1 0 -2 0.2159
 0 0 1 0.2176
 0 0 -1 0.2015
 -1 -1 2 0.2354
 0 2 -1 0.1582
 -1 -2 0 0.1338
 0 -1 2 0.2544

_exptl_crystal_size_max            0.551
_exptl_crystal_size_mid            0.38
_exptl_crystal_size_min            0.363
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 0.0001 0.9995 0.0000 -0.1047 0.0961 -0.0410
 -0.0001 -0.9995 -0.0000 0.1047 -0.0961 0.0410
 0.9994 0.0001 -1.0005 -0.0516 0.0340 0.2116
 -0.9994 -0.0001 1.0005 0.0516 -0.0340 -0.2116
 -0.9993 0.9995 1.0005 -0.0531 0.0621 -0.2526
 0.9995 0.0002 1.9984 -0.1736 -0.1331 0.1309
 -0.9995 -0.0002 -1.9984 0.1736 0.1331 -0.1309
 0.0000 0.0000 0.9996 -0.0406 -0.0557 -0.0269
 -0.0000 -0.0000 -0.9996 0.0406 0.0557 0.0269
 -0.9995 -0.9996 2.0001 0.1157 -0.1858 -0.1975
 0.0002 1.9991 -0.9995 -0.1688 0.2480 -0.0551
 -0.9996 -1.9992 0.0008 0.3017 -0.1706 -0.1026
 -0.0001 -0.9995 1.9992 0.0234 -0.2075 -0.0128

_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0197
_diffrn_reflns_av_unetI/netI       0.0079
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.991
_diffrn_reflns_limit_h_max         8
_diffrn_reflns_limit_h_min         -8
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         25
_diffrn_reflns_limit_l_min         -25
_diffrn_reflns_number              27630
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.989
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           73.513
_diffrn_reflns_theta_min           4.249
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        140.00(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   10.2665
_diffrn_detector_type              Atlas
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -114.00 -59.00   1.00    2.50    --  -43.01 -57.00-150.00   55
  2  ω    -69.00  29.00   1.00    2.50    --  -43.01  57.00 120.00   98
  3  ω    -44.00 -15.00   1.00    2.50    --  -43.01 -57.00-150.00   29
  4  ω   -128.00  45.00   1.00    2.50    --  -43.01   0.00   0.00  173
  5  ω    -41.00 -15.00   1.00    2.50    --  -43.01 -57.00  90.00   26
  6  ω    -98.00 -20.00   1.00    2.50    --  -43.01 -37.00 -60.00   78
  7  ω     32.00  98.00   1.00    2.50    --   43.01-125.00 -60.00   66
  8  ω     11.00  36.00   1.00    2.50    --   46.00  84.00 -48.95   25
  9  ω     12.00  42.00   1.00    2.50    --   46.00  81.00 124.08   30
 10  ω     11.00  36.00   1.00    2.50    --   46.00  84.00-163.67   25
 11  ω     12.00  37.00   1.00    2.50    --   46.00  83.00  25.98   25
 12  ω     16.00  41.00   1.00    2.50    --   50.00  81.00 -26.70   25
 13  ω     25.00  55.00   1.00    2.50    --   58.00  77.00-129.20   30
 14  ω     34.00  60.00   1.00    2.50    --   62.00  76.00  12.54   26
 15  ω     29.00  60.00   1.00    2.50    --   62.00  77.00  58.79   31
 16  ω     30.00  59.00   1.00    2.50    --   62.00  77.00 121.80   29
 17  ω     35.00  61.00   1.00    2.50    --   66.00  76.00 -76.30   26
 18  ω    120.00 146.00   1.00    2.50    --   70.00  77.00 -25.32   26
 19  ω     84.00 146.00   1.00    2.50    --   70.00  77.00 159.92   62
 20  ω     37.00  69.00   1.00    2.50    --   70.00  77.00 -25.32   32
 21  ω     37.00  77.00   1.00    2.50    --   70.00  77.00 159.92   40
 22  ω     37.00  67.00   1.00    2.50    --   70.00  77.00  96.71   30
 23  ω     42.00  77.00   1.00    2.50    --   74.00  73.00-116.02   35
 24  ω     45.00  72.00   1.00   10.00    --   78.00  77.00  81.60   27
 25  ω     47.00  86.00   1.00   10.00    --   78.00  76.00 -76.02   39
 26  ω     49.00  74.00   1.00   10.00    --   82.00  77.00-170.74   25
 27  ω     50.00  84.00   1.00   10.00    --   82.00  74.00 129.72   34
 28  ω     73.00 161.00   1.00   10.00    --  105.68  77.00 120.00   88
 29  ω     71.00 118.00   1.00   10.00    --  105.68-125.00 150.00   47
 30  ω     78.00 178.00   1.00   10.00    --  105.68  61.00   0.00  100
 31  ω    120.00 161.00   1.00   10.00    --  105.68 125.00 -30.00   41
 32  ω     73.00 170.00   1.00   10.00    --  105.68  77.00 -90.00   97
 33  ω     79.00 106.00   1.00   10.00    --  105.68  61.00-150.00   27
 34  ω    114.00 176.00   1.00   10.00    --  105.68  77.00-180.00   62
 35  ω     74.00 100.00   1.00   10.00    --  105.68  77.00-180.00   26
 36  ω     74.00 133.00   1.00   10.00    --  105.68  77.00  30.00   59
 37  ω     74.00 170.00   1.00   10.00    --  105.68  77.00 150.00   96
 38  ω    132.00 158.00   1.00   10.00    --  105.68  77.00  90.00   26
 39  ω     33.00 118.00   1.00   10.00    --  105.68-125.00 -60.00   85
 40  ω     74.00 129.00   1.00   10.00    --  105.68  77.00  90.00   55
 41  ω    112.00 138.00   1.00   10.00    --  105.68  77.00 -30.00   26
 42  ω     73.00  99.00   1.00   10.00    --  105.68  77.00 -30.00   26
 43  ω     73.00 178.00   1.00   10.00    --  105.68  77.00 -60.00  105
 44  ω     73.00 173.00   1.00   10.00    --  105.68  77.00-120.00  100
 45  ω     73.00 169.00   1.00   10.00    --  105.68  77.00  60.00   96
 46  ω    141.00 168.00   1.00   10.00    --  105.68 125.00 -90.00   27
 47  ω    107.00 177.00   1.00   10.00    --  105.68 125.00  60.00   70
 48  ω     78.00 103.00   1.00   10.00    --  105.68  61.00  30.00   25
 49  ω     73.00 166.00   1.00   10.00    --  105.68  77.00-150.00   93
 50  ω     73.00  99.00   1.00   10.00    --  105.68  77.00   0.00   26
 51  ω     33.00 134.00   1.00   10.00    --  105.68 -77.00 -30.00  101
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0923620000
_diffrn_orient_matrix_UB_12        -0.1047434000
_diffrn_orient_matrix_UB_13        -0.0406530000
_diffrn_orient_matrix_UB_21        -0.0217833000
_diffrn_orient_matrix_UB_22        0.0961817000
_diffrn_orient_matrix_UB_23        -0.0557324000
_diffrn_orient_matrix_UB_31        0.1847699000
_diffrn_orient_matrix_UB_32        -0.0410567000
_diffrn_orient_matrix_UB_33        -0.0269136000
_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           0.721
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       0.986
_reflns_number_gt                  3186
_reflns_number_total               3192
_reflns_odcompleteness_completeness  99.88
_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 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection         'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction          'CrysAlisPro 1.171.40.20a (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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.174
_refine_diff_density_min           -0.130
_refine_diff_density_rms           0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1325 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.02(3)
_refine_ls_extinction_coef         0.0159(10)
_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     1.094
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       220
_refine_ls_number_reflns           3192
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0272
_refine_ls_R_factor_gt             0.0272
_refine_ls_restrained_S_all        1.094
_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)+(0.0474P)²+0.2136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0781
_refine_ls_wR_factor_ref           0.0782
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     difmap
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 0.44758(18) 0.46285(11) 0.45370(5) 0.0357(3) Uani 1 1 d . . . . .
 N1 N 0.59388(18) 0.33088(12) 0.56864(6) 0.0274(3) Uani 1 1 d . . . . .
 N2 N 0.5587(2) 0.21785(13) 0.59707(7) 0.0331(3) Uani 1 1 d . . . . .
 N3 N 0.4082(2) 0.23153(12) 0.62957(6) 0.0309(3) Uani 1 1 d . . . . .
 C1 C 0.4655(2) 0.41984(14) 0.58238(7) 0.0248(3) Uani 1 1 d . . . . .
 C2 C 0.3463(2) 0.35428(14) 0.62212(7) 0.0255(3) Uani 1 1 d . . . . .
 C3 C 0.4726(2) 0.55179(14) 0.55624(7) 0.0239(3) Uani 1 1 d . . . . .
 C4 C 0.4673(2) 0.57043(14) 0.49034(7) 0.0281(3) Uani 1 1 d . . . . .
 C5 C 0.4788(2) 0.69515(16) 0.46386(8) 0.0361(4) Uani 1 1 d . . . . .
 H5 H 0.477233 0.706543 0.419534 0.043 Uiso 1 1 calc R . . . .
 C6 C 0.4920(3) 0.79825(16) 0.50353(9) 0.0389(4) Uani 1 1 d . . . . .
 H6 H 0.498971 0.879975 0.485646 0.047 Uiso 1 1 calc R . . . .
 C7 C 0.4956(2) 0.78550(15) 0.57072(9) 0.0321(4) Uani 1 1 d . . . . .
 C8 C 0.5121(3) 0.89348(16) 0.61160(10) 0.0422(5) Uani 1 1 d . . . . .
 H8 H 0.519461 0.975287 0.593828 0.051 Uiso 1 1 calc R . . . .
 C9 C 0.5173(3) 0.87923(18) 0.67657(10) 0.0449(5) Uani 1 1 d . . . . .
 H9 H 0.529444 0.950957 0.702857 0.054 Uiso 1 1 calc R . . . .
 C10 C 0.5043(2) 0.75610(18) 0.70398(9) 0.0382(4) Uani 1 1 d . . . . .
 H10 H 0.506081 0.747004 0.748441 0.046 Uiso 1 1 calc R . . . .
 C11 C 0.4891(2) 0.64944(16) 0.66582(8) 0.0293(3) Uani 1 1 d . . . . .
 H11 H 0.480581 0.568689 0.684702 0.035 Uiso 1 1 calc R . . . .
 C12 C 0.4861(2) 0.66047(14) 0.59798(7) 0.0253(3) Uani 1 1 d . . . . .
 C13 C 0.4703(3) 0.4732(2) 0.38555(7) 0.0437(5) Uani 1 1 d . . . . .
 H13A H 0.456736 0.390018 0.366263 0.066 Uiso 1 1 calc GR . . . .
 H13B H 0.588482 0.506093 0.376275 0.066 Uiso 1 1 calc GR . . . .
 H13C H 0.381031 0.530566 0.368417 0.066 Uiso 1 1 calc GR . . . .
 C14 C 0.1797(2) 0.39471(14) 0.65475(7) 0.0253(3) Uani 1 1 d . . . . .
 C15 C 0.0957(2) 0.51185(15) 0.64162(7) 0.0282(3) Uani 1 1 d . . . . .
 H15 H 0.145153 0.566803 0.611097 0.034 Uiso 1 1 calc R . . . .
 C16 C -0.0610(2) 0.54715(16) 0.67373(8) 0.0336(4) Uani 1 1 d . . . . .
 H16 H -0.115862 0.625305 0.664455 0.040 Uiso 1 1 calc R . . . .
 C17 C -0.1356(2) 0.46673(18) 0.71936(8) 0.0368(4) Uani 1 1 d . . . . .
 H17 H -0.240336 0.490690 0.740825 0.044 Uiso 1 1 calc R . . . .
 C18 C -0.0538(2) 0.35043(17) 0.73300(8) 0.0371(4) Uani 1 1 d . . . . .
 H18 H -0.103736 0.296168 0.763734 0.044 Uiso 1 1 calc R . . . .
 C19 C 0.1022(2) 0.31449(16) 0.70101(8) 0.0313(4) Uani 1 1 d . . . . .
 H19 H 0.156008 0.236024 0.710438 0.038 Uiso 1 1 calc R . . . .
 C20 C 0.7592(2) 0.34392(16) 0.53118(9) 0.0345(4) Uani 1 1 d . . . . .
 H20A H 0.819200 0.262340 0.528922 0.052 Uiso 1 1 calc GR . . . .
 H20B H 0.837049 0.405518 0.551398 0.052 Uiso 1 1 calc GR . . . .
 H20C H 0.730012 0.372500 0.488562 0.052 Uiso 1 1 calc GR . . . .


_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 C4 1.3626(18) . ?
 O1 C13 1.4323(18) . ?
 N1 N2 1.3425(18) . ?
 N1 C1 1.3586(19) . ?
 N1 C20 1.459(2) . ?
 N2 N3 1.313(2) . ?
 N3 C2 1.366(2) . ?
 C1 C2 1.389(2) . ?
 C1 C3 1.478(2) . ?
 C2 C14 1.471(2) . ?
 C3 C4 1.386(2) . ?
 C3 C12 1.430(2) . ?
 C4 C5 1.413(2) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.358(3) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.405(2) . ?
 C7 C8 1.415(2) . ?
 C7 C12 1.421(2) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.360(3) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.406(3) . ?
 C10 H10 0.9300 . ?
 C10 C11 1.370(2) . ?
 C11 H11 0.9300 . ?
 C11 C12 1.416(2) . ?
 C13 H13A 0.9600 . ?
 C13 H13B 0.9600 . ?
 C13 H13C 0.9600 . ?
 C14 C15 1.396(2) . ?
 C14 C19 1.398(2) . ?
 C15 H15 0.9300 . ?
 C15 C16 1.390(2) . ?
 C16 H16 0.9300 . ?
 C16 C17 1.381(2) . ?
 C17 H17 0.9300 . ?
 C17 C18 1.383(3) . ?
 C18 H18 0.9300 . ?
 C18 C19 1.386(2) . ?
 C19 H19 0.9300 . ?
 C20 H20A 0.9600 . ?
 C20 H20B 0.9600 . ?
 C20 H20C 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
 C4 O1 C13 118.64(13) . . ?
 N2 N1 C1 111.62(13) . . ?
 N2 N1 C20 118.70(13) . . ?
 C1 N1 C20 129.62(13) . . ?
 N3 N2 N1 107.28(13) . . ?
 N2 N3 C2 109.18(13) . . ?
 N1 C1 C2 103.66(13) . . ?
 N1 C1 C3 122.06(13) . . ?
 C2 C1 C3 134.28(14) . . ?
 N3 C2 C1 108.26(14) . . ?
 N3 C2 C14 119.81(13) . . ?
 C1 C2 C14 131.93(14) . . ?
 C4 C3 C1 119.55(13) . . ?
 C4 C3 C12 119.50(14) . . ?
 C12 C3 C1 120.95(13) . . ?
 O1 C4 C3 116.21(13) . . ?
 O1 C4 C5 122.92(14) . . ?
 C3 C4 C5 120.86(15) . . ?
 C4 C5 H5 120.2 . . ?
 C6 C5 C4 119.58(15) . . ?
 C6 C5 H5 120.2 . . ?
 C5 C6 H6 118.9 . . ?
 C5 C6 C7 122.14(15) . . ?
 C7 C6 H6 118.9 . . ?
 C6 C7 C8 121.67(16) . . ?
 C6 C7 C12 118.86(15) . . ?
 C8 C7 C12 119.46(16) . . ?
 C7 C8 H8 119.6 . . ?
 C9 C8 C7 120.88(17) . . ?
 C9 C8 H8 119.6 . . ?
 C8 C9 H9 120.0 . . ?
 C8 C9 C10 120.04(16) . . ?
 C10 C9 H9 120.0 . . ?
 C9 C10 H10 119.7 . . ?
 C11 C10 C9 120.61(17) . . ?
 C11 C10 H10 119.7 . . ?
 C10 C11 H11 119.6 . . ?
 C10 C11 C12 120.89(16) . . ?
 C12 C11 H11 119.6 . . ?
 C7 C12 C3 119.05(14) . . ?
 C11 C12 C3 122.84(14) . . ?
 C11 C12 C7 118.11(14) . . ?
 O1 C13 H13A 109.5 . . ?
 O1 C13 H13B 109.5 . . ?
 O1 C13 H13C 109.5 . . ?
 H13A C13 H13B 109.5 . . ?
 H13A C13 H13C 109.5 . . ?
 H13B C13 H13C 109.5 . . ?
 C15 C14 C2 122.27(14) . . ?
 C15 C14 C19 118.26(14) . . ?
 C19 C14 C2 119.47(14) . . ?
 C14 C15 H15 119.7 . . ?
 C16 C15 C14 120.63(14) . . ?
 C16 C15 H15 119.7 . . ?
 C15 C16 H16 119.8 . . ?
 C17 C16 C15 120.34(16) . . ?
 C17 C16 H16 119.8 . . ?
 C16 C17 H17 120.1 . . ?
 C16 C17 C18 119.72(17) . . ?
 C18 C17 H17 120.1 . . ?
 C17 C18 H18 119.9 . . ?
 C17 C18 C19 120.22(15) . . ?
 C19 C18 H18 119.9 . . ?
 C14 C19 H19 119.6 . . ?
 C18 C19 C14 120.83(15) . . ?
 C18 C19 H19 119.6 . . ?
 N1 C20 H20A 109.5 . . ?
 N1 C20 H20B 109.5 . . ?
 N1 C20 H20C 109.5 . . ?
 H20A C20 H20B 109.5 . . ?
 H20A C20 H20C 109.5 . . ?
 H20B C20 H20C 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 C4 C5 C6 177.70(16) . . . . ?
 N1 N2 N3 C2 -0.13(17) . . . . ?
 N1 C1 C2 N3 -0.35(16) . . . . ?
 N1 C1 C2 C14 179.01(15) . . . . ?
 N1 C1 C3 C4 61.2(2) . . . . ?
 N1 C1 C3 C12 -118.36(16) . . . . ?
 N2 N1 C1 C2 0.28(17) . . . . ?
 N2 N1 C1 C3 -179.39(13) . . . . ?
 N2 N3 C2 C1 0.31(17) . . . . ?
 N2 N3 C2 C14 -179.14(13) . . . . ?
 N3 C2 C14 C15 -170.35(14) . . . . ?
 N3 C2 C14 C19 10.3(2) . . . . ?
 C1 N1 N2 N3 -0.10(17) . . . . ?
 C1 C2 C14 C15 10.4(3) . . . . ?
 C1 C2 C14 C19 -169.05(16) . . . . ?
 C1 C3 C4 O1 2.8(2) . . . . ?
 C1 C3 C4 C5 -178.30(15) . . . . ?
 C1 C3 C12 C7 178.94(14) . . . . ?
 C1 C3 C12 C11 -1.5(2) . . . . ?
 C2 C1 C3 C4 -118.33(19) . . . . ?
 C2 C1 C3 C12 62.1(2) . . . . ?
 C2 C14 C15 C16 -179.57(14) . . . . ?
 C2 C14 C19 C18 179.40(15) . . . . ?
 C3 C1 C2 N3 179.26(16) . . . . ?
 C3 C1 C2 C14 -1.4(3) . . . . ?
 C3 C4 C5 C6 -1.1(3) . . . . ?
 C4 C3 C12 C7 -0.6(2) . . . . ?
 C4 C3 C12 C11 178.89(14) . . . . ?
 C4 C5 C6 C7 0.3(3) . . . . ?
 C5 C6 C7 C8 179.08(17) . . . . ?
 C5 C6 C7 C12 0.4(3) . . . . ?
 C6 C7 C8 C9 -179.29(17) . . . . ?
 C6 C7 C12 C3 -0.2(2) . . . . ?
 C6 C7 C12 C11 -179.73(15) . . . . ?
 C7 C8 C9 C10 -0.7(3) . . . . ?
 C8 C7 C12 C3 -178.93(15) . . . . ?
 C8 C7 C12 C11 1.5(2) . . . . ?
 C8 C9 C10 C11 1.0(3) . . . . ?
 C9 C10 C11 C12 0.0(3) . . . . ?
 C10 C11 C12 C3 179.21(15) . . . . ?
 C10 C11 C12 C7 -1.2(2) . . . . ?
 C12 C3 C4 O1 -177.60(13) . . . . ?
 C12 C3 C4 C5 1.3(2) . . . . ?
 C12 C7 C8 C9 -0.6(3) . . . . ?
 C13 O1 C4 C3 -170.05(15) . . . . ?
 C13 O1 C4 C5 11.1(2) . . . . ?
 C14 C15 C16 C17 0.2(2) . . . . ?
 C15 C14 C19 C18 0.0(2) . . . . ?
 C15 C16 C17 C18 -0.1(3) . . . . ?
 C16 C17 C18 C19 -0.1(3) . . . . ?
 C17 C18 C19 C14 0.1(3) . . . . ?
 C19 C14 C15 C16 -0.2(2) . . . . ?
 C20 N1 N2 N3 177.56(14) . . . . ?
 C20 N1 C1 C2 -177.06(15) . . . . ?
 C20 N1 C1 C3 3.3(2) . . . . ?


_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max  2.085
_oxdiff_exptl_absorpt_empirical_full_min  0.669
