data_210126c
_audit_creation_date               2021-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number             2013-4
_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. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ?
;
_chemical_formula_moiety           'C19 H15 Cl2 N3 O, C3 H8 O'
_chemical_formula_sum              'C22 H23 Cl2 N3 O2'
_chemical_formula_weight           432.33
_chemical_absolute_configuration   syn
_chemical_melting_point            ?
_chemical_oxdiff_formula           ClC
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'
 'Cl' 'Cl' 0.3639 0.7018 '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                     9.7747(3)
_cell_length_b                     7.5306(3)
_cell_length_c                     14.5872(4)
_cell_angle_alpha                  90
_cell_angle_beta                   104.962(3)
_cell_angle_gamma                  90
_cell_volume                       1037.35(6)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      4463
_cell_measurement_temperature      293(2)
_cell_measurement_theta_max        74.2330
_cell_measurement_theta_min        3.1140
_shelx_estimated_absorpt_T_max     0.864
_shelx_estimated_absorpt_T_min     0.840
_exptl_absorpt_coefficient_mu      3.008
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.50893
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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      1.384
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               452
_exptl_crystal_size_max            0.06
_exptl_crystal_size_mid            0.06
_exptl_crystal_size_min            0.05
_exptl_special_details
;
 ?
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0596
_diffrn_reflns_av_unetI/netI       0.0580
_diffrn_reflns_Laue_measured_fraction_full  0.986
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         8
_diffrn_reflns_limit_k_min         -8
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         -17
_diffrn_reflns_number              10652
_diffrn_reflns_point_group_measured_fraction_full  0.968
_diffrn_reflns_point_group_measured_fraction_max  0.982
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           67.080
_diffrn_reflns_theta_min           3.136
_diffrn_ambient_temperature        293(2)
_diffrn_detector                   'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean   10.0000
_diffrn_detector_type              HyPix
_diffrn_measured_fraction_theta_full  0.986
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     97.00 149.00   1.00    0.31    --  106.49  77.00 -90.00   52
  2  ω    153.00 178.00   1.00    0.31    --  106.49  77.00 -90.00   25
  3  ω     95.00 176.00   1.00    0.31    --  106.49  26.00-121.00   81
  4  ω     56.00  89.00   1.00    0.10    --   48.32  26.00-121.00   33
  5  ω    -25.00  24.00   1.00    0.10    --   48.32 -19.00 -60.00   49
  6  ω     37.00  68.00   1.00    0.31    --  106.49 -77.00-180.00   31
  7  ω     72.00 102.00   1.00    0.31    --  106.49 -77.00-180.00   30
  8  ω     40.00  66.00   1.00    0.31    --  106.49 -57.00 -60.00   26
  9  ω     -5.00  24.00   1.00    0.10    --   48.32 -26.00  75.00   29
 10  ω     34.00  63.00   1.00    0.31    --  106.49 -57.00 150.00   29
 11  ω    129.00 165.00   1.00    0.31    --  106.49 125.00  60.00   36
 12  ω     95.00 127.00   1.00    0.31    --  106.49 125.00  60.00   32
 13  ω     95.00 177.00   1.00    0.31    --  106.49 125.00 -90.00   82
 14  ω     37.00  63.00   1.00    0.31    --  106.49-125.00 -60.00   26
 15  ω     65.00 111.00   1.00    0.31    --  106.49-125.00 -60.00   46
 16  ω    -31.00  26.00   1.00    0.10    --  -48.32  26.00-121.00   57
 17  ω    -65.00 -14.00   1.00    0.31    --  -86.25  57.00 -60.00   51
 18  ω    -66.00 -14.00   1.00    0.31    --  -86.25  57.00  30.00   52
 19  ω    -38.00 -13.00   1.00    0.31    --  -86.25  38.00  60.00   25
 20  ω   -120.00 -37.00   1.00    0.10    --  -48.32 -26.00  75.00   83
 21  ω    -65.00 -26.00   1.00    0.10    --  -48.32 -77.00   0.00   39
 22  ω    -62.00 -28.00   1.00    0.10    --  -48.32 -77.00 -60.00   34
 23  ω   -106.00 -80.00   1.00    0.10    --  -48.32 -77.00   0.00   26
 24  ω   -152.00-127.00   1.00    0.31    --  -86.25 -80.00 -12.87   25
 25  ω   -159.00-120.00   1.00    0.31    --  -86.25 -77.00 -60.00   39
 26  ω   -118.00 -62.00   1.00    0.31    --  -86.25 -80.00 -12.87   56
 27  ω    -88.00 -63.00   1.00    0.31    --  -86.25 -77.00  30.00   25
 28  ω   -130.00 -62.00   1.00    0.31    --  -86.25 -80.00  17.72   68
 29  ω   -148.00-110.00   1.00    0.31    --  -86.25 -77.00  30.00   38
 30  ω   -122.00 -63.00   1.00    0.31    --  -86.25 -77.00   0.00   59
 31  ω   -107.00 -63.00   1.00    0.31    --  -86.25 -77.00 -60.00   44
 32  ω   -107.00 -64.00   1.00    0.31    --  -86.25 -76.00 -39.19   43
 33  ω   -148.00-122.00   1.00    0.31    --  -86.25 -76.00 -39.19   26
 34  ω   -151.00 -67.00   1.00    0.31    --  -86.25 -74.00  47.36   84
 35  ω   -131.00-106.00   1.00    0.31    --  -86.25 -26.00  75.00   25
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method         'ω scans'
_diffrn_measurement_specimen_support  'Mitegen 50um'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.1098427000
_diffrn_orient_matrix_UB_12        0.0637906000
_diffrn_orient_matrix_UB_13        0.0897962000
_diffrn_orient_matrix_UB_21        0.1189726000
_diffrn_orient_matrix_UB_22        -0.0261891000
_diffrn_orient_matrix_UB_23        -0.0504319000
_diffrn_orient_matrix_UB_31        -0.0202497000
_diffrn_orient_matrix_UB_32        0.1925398000
_diffrn_orient_matrix_UB_33        -0.0366470000
_diffrn_oxdiff_digest_frames
;
01e8fa6637855b6523f2b725722352502301506717f
;
_diffrn_oxdiff_digest_hkl
;
0107d27859b773b68d32b93e2e8cc2fec01105
;
_diffrn_radiation_collimation      0.3
_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_current             24.0
_diffrn_source_power               1.2
_diffrn_source_target              Mo
_diffrn_source_type                'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage             50.0
_reflns_Friedel_coverage           0.814
_reflns_Friedel_fraction_full      0.948
_reflns_Friedel_fraction_max       0.962
_reflns_number_gt                  3214
_reflns_number_total               3632
_reflns_odcompleteness_completeness  99.90
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection         'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction          'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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           0.252
_refine_diff_density_min           -0.298
_refine_diff_density_rms           0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack     -0.017(14)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.084
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       274
_refine_ls_number_reflns           3632
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0492
_refine_ls_R_factor_gt             0.0426
_refine_ls_restrained_S_all        1.084
_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)+(0.0640P)²+0.0230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1110
_refine_ls_wR_factor_ref           0.1158
_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, All C(H,H,H,H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H0A(0.6) H0AA(0.4) C1(0.6) H1A(0.6) C1A(0.4) H1AA(0.4) H2AA(0.6)
 H2AB(0.6) H2AC(0.6) H2BD(0.4) H2BE(0.4) H2BF(0.4) H3AA(0.6) H3AB(0.6)
 H3AC(0.6) H3BD(0.4) H3BE(0.4) H3BF(0.4)
3.a Ternary CH refined with riding coordinates:
 C15(H15), C1(H1A), C1A(H1AA)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C4(H4), C6(H6), C9(H9), C19(H19), C20(H20), C22(H22)
3.d Tetrahedral OH refined with riding coordinates:
 O0A(H0A), O0A(H0AA)
3.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C2(H2AA,H2AB,H2AC), C2(H2BD,H2BE,H2BF), C3(H3AA,H3AB,
 H3AC), C3(H3BD,H3BE,H3BF)
;
_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
 Cl1 Cl 0.30605(16) 0.5090(2) 0.02280(7) 0.0766(4) Uani 1 1 d . . . . .
 Cl2 Cl 0.71220(16) 0.5236(2) 0.95785(7) 0.0765(4) Uani 1 1 d . . . . .
 O25 O 0.8741(3) 0.2426(4) 0.50200(17) 0.0420(6) Uani 1 1 d . . . . .
 N1 N 0.4572(3) 0.3666(5) 0.3835(2) 0.0391(7) Uani 1 1 d . . . . .
 H1 H 0.3952 0.2893 0.3893 0.047 Uiso 1 1 calc R . . . .
 N2 N 0.7773(3) 0.5995(4) 0.5829(2) 0.0335(7) Uani 1 1 d . . . . .
 H2 H 0.7886 0.6824 0.6247 0.040 Uiso 1 1 calc R . . . .
 N3 N 0.9473(3) 0.2139(5) 0.6635(2) 0.0444(8) Uani 1 1 d . . . . .
 H3 H 1.0169 0.1421 0.6669 0.053 Uiso 1 1 calc R . . . .
 C4 C 0.5232(5) 0.6474(6) 0.1562(3) 0.0526(11) Uani 1 1 d . . . . .
 H4 H 0.5425 0.7112 0.1064 0.063 Uiso 1 1 calc R . . . .
 C5 C 0.4086(5) 0.5328(7) 0.1393(2) 0.0510(10) Uani 1 1 d . . . . .
 C6 C 0.3733(4) 0.4364(6) 0.2096(3) 0.0466(9) Uani 1 1 d . . . . .
 H6 H 0.2945 0.3624 0.1969 0.056 Uiso 1 1 calc R . . . .
 C7 C 0.4613(4) 0.4546(5) 0.3011(2) 0.0374(8) Uani 1 1 d . . . . .
 C8 C 0.5803(4) 0.5696(5) 0.3212(2) 0.0351(8) Uani 1 1 d . . . . .
 C9 C 0.6090(4) 0.6667(6) 0.2475(3) 0.0450(9) Uani 1 1 d . . . . .
 H9 H 0.6856 0.7444 0.2593 0.054 Uiso 1 1 calc R . . . .
 C10 C 0.6470(3) 0.5482(5) 0.4212(2) 0.0327(7) Uani 1 1 d . . . . .
 C11 C 0.5712(3) 0.4254(5) 0.4552(2) 0.0333(7) Uani 1 1 d . . . . .
 C12 C 0.6052(3) 0.3575(5) 0.5548(2) 0.0364(8) Uani 1 1 d . . . . .
 H12A H 0.5971 0.2291 0.5546 0.044 Uiso 1 1 calc R . . . .
 H12B H 0.5390 0.4061 0.5875 0.044 Uiso 1 1 calc R . . . .
 C13 C 0.7567(3) 0.4128(5) 0.6060(2) 0.0320(7) Uani 1 1 d . . . . .
 C14 C 0.7847(4) 0.8345(5) 0.4702(3) 0.0385(8) Uani 1 1 d . . . . .
 H14A H 0.6995 0.8883 0.4782 0.058 Uiso 1 1 calc GR . . . .
 H14B H 0.7947 0.8603 0.4078 0.058 Uiso 1 1 calc GR . . . .
 H14C H 0.8647 0.8810 0.5167 0.058 Uiso 1 1 calc GR . . . .
 C15 C 0.7771(4) 0.6356(5) 0.4825(2) 0.0323(7) Uani 1 1 d . . . . .
 H15 H 0.8612 0.5809 0.4696 0.039 Uiso 1 1 calc R . . . .
 C16 C 0.8645(4) 0.2805(5) 0.5810(2) 0.0336(8) Uani 1 1 d . . . . .
 C17 C 0.7900(4) 0.3898(5) 0.7126(2) 0.0352(8) Uani 1 1 d . . . . .
 C18 C 0.9050(4) 0.2767(6) 0.7424(3) 0.0410(8) Uani 1 1 d . . . . .
 C19 C 0.9665(5) 0.2445(7) 0.8371(3) 0.0531(11) Uani 1 1 d . . . . .
 H19 H 1.0460 0.1724 0.8561 0.064 Uiso 1 1 calc R . . . .
 C20 C 0.9058(5) 0.3234(7) 0.9032(3) 0.0560(11) Uani 1 1 d . . . . .
 H20 H 0.9440 0.3033 0.9676 0.067 Uiso 1 1 calc R . . . .
 C21 C 0.7892(5) 0.4314(6) 0.8733(3) 0.0508(10) Uani 1 1 d . . . . .
 C22 C 0.7281(4) 0.4657(5) 0.7786(3) 0.0424(9) Uani 1 1 d . . . . .
 H22 H 0.6482 0.5373 0.7598 0.051 Uiso 1 1 calc R . . . .
 O0A O 0.9210(4) 0.3544(5) 0.3275(2) 0.0670(10) Uani 1 1 d . . . . .
 H0A H 0.8888 0.3065 0.3678 0.100 Uiso 0.6 1 calc R . P A 1
 H0AA H 0.9105 0.3302 0.3800 0.100 Uiso 0.4 1 calc R . P B 2
 C1 C 0.8412(8) 0.3029(13) 0.2364(6) 0.0438(18) Uani 0.6 1 d . . P C 1
 H1A H 0.7891 0.4081 0.2067 0.053 Uiso 0.6 1 calc R . P C 1
 C1A C 0.8658(13) 0.211(2) 0.2622(9) 0.052(3) Uani 0.4 1 d . . P C 2
 H1AA H 0.9167 0.1061 0.2930 0.063 Uiso 0.4 1 calc R . P C 2
 C2 C 0.9368(6) 0.2523(8) 0.1786(3) 0.0644(13) Uani 1 1 d . . . . .
 H2AA H 1.0095 0.3406 0.1847 0.097 Uiso 0.6 1 calc GR . P C 1
 H2AB H 0.8844 0.2435 0.1133 0.097 Uiso 0.6 1 calc GR . P C 1
 H2AC H 0.9793 0.1396 0.1997 0.097 Uiso 0.6 1 calc GR . P C 1
 H2BD H 0.8903 0.3521 0.1427 0.097 Uiso 0.4 1 calc GR . P C 2
 H2BE H 0.9280 0.1505 0.1379 0.097 Uiso 0.4 1 calc GR . P C 2
 H2BF H 1.0352 0.2793 0.2045 0.097 Uiso 0.4 1 calc GR . P C 2
 C3 C 0.7320(8) 0.1633(10) 0.2419(5) 0.090(2) Uani 1 1 d . . . . .
 H3AA H 0.7784 0.0515 0.2597 0.135 Uiso 0.6 1 calc GR . P C 1
 H3AB H 0.6653 0.1520 0.1810 0.135 Uiso 0.6 1 calc GR . P C 1
 H3AC H 0.6832 0.1980 0.2883 0.135 Uiso 0.6 1 calc GR . P C 1
 H3BD H 0.7039 0.1457 0.2996 0.135 Uiso 0.4 1 calc GR . P C 2
 H3BE H 0.7198 0.0547 0.2062 0.135 Uiso 0.4 1 calc GR . P C 2
 H3BF H 0.6746 0.2547 0.2049 0.135 Uiso 0.4 1 calc GR . P C 2


_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
 Cl1 C5 1.745(4) . ?
 Cl2 C21 1.747(4) . ?
 O25 C16 1.214(4) . ?
 N1 H1 0.8600 . ?
 N1 C7 1.382(5) . ?
 N1 C11 1.390(4) . ?
 N2 H2 0.8600 . ?
 N2 C13 1.472(5) . ?
 N2 C15 1.489(5) . ?
 N3 H3 0.8600 . ?
 N3 C16 1.361(5) . ?
 N3 C18 1.401(5) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.385(7) . ?
 C4 C9 1.386(6) . ?
 C5 C6 1.371(6) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.395(5) . ?
 C7 C8 1.418(5) . ?
 C8 C9 1.388(5) . ?
 C8 C10 1.445(5) . ?
 C9 H9 0.9300 . ?
 C10 C11 1.357(5) . ?
 C10 C15 1.504(5) . ?
 C11 C12 1.494(5) . ?
 C12 H12A 0.9700 . ?
 C12 H12B 0.9700 . ?
 C12 C13 1.534(5) . ?
 C13 C16 1.560(5) . ?
 C13 C17 1.513(5) . ?
 C14 H14A 0.9600 . ?
 C14 H14B 0.9600 . ?
 C14 H14C 0.9600 . ?
 C14 C15 1.512(5) . ?
 C15 H15 0.9800 . ?
 C17 C18 1.387(5) . ?
 C17 C22 1.386(5) . ?
 C18 C19 1.378(5) . ?
 C19 H19 0.9300 . ?
 C19 C20 1.389(7) . ?
 C20 H20 0.9300 . ?
 C20 C21 1.377(7) . ?
 C21 C22 1.380(6) . ?
 C22 H22 0.9300 . ?
 O0A H0A 0.8200 . ?
 O0A H0AA 0.8200 . ?
 O0A C1 1.410(8) . ?
 O0A C1A 1.448(14) . ?
 C1 H1A 0.9800 . ?
 C1 C2 1.462(10) . ?
 C1 C3 1.514(11) . ?
 C1A H1AA 0.9800 . ?
 C1A C2 1.582(14) . ?
 C1A C3 1.314(14) . ?
 C2 H2AA 0.9600 . ?
 C2 H2AB 0.9600 . ?
 C2 H2AC 0.9600 . ?
 C2 H2BD 0.9600 . ?
 C2 H2BE 0.9600 . ?
 C2 H2BF 0.9600 . ?
 C3 H3AA 0.9600 . ?
 C3 H3AB 0.9600 . ?
 C3 H3AC 0.9600 . ?
 C3 H3BD 0.9600 . ?
 C3 H3BE 0.9600 . ?
 C3 H3BF 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
 C7 N1 H1 126.2 . . ?
 C7 N1 C11 107.7(3) . . ?
 C11 N1 H1 126.2 . . ?
 C13 N2 H2 122.1 . . ?
 C13 N2 C15 115.8(3) . . ?
 C15 N2 H2 122.1 . . ?
 C16 N3 H3 124.2 . . ?
 C16 N3 C18 111.6(3) . . ?
 C18 N3 H3 124.2 . . ?
 C5 C4 H4 120.1 . . ?
 C5 C4 C9 119.9(4) . . ?
 C9 C4 H4 120.1 . . ?
 C4 C5 Cl1 118.2(3) . . ?
 C6 C5 Cl1 118.8(4) . . ?
 C6 C5 C4 123.0(3) . . ?
 C5 C6 H6 121.6 . . ?
 C5 C6 C7 116.8(4) . . ?
 C7 C6 H6 121.6 . . ?
 N1 C7 C6 129.4(4) . . ?
 N1 C7 C8 108.6(3) . . ?
 C6 C7 C8 121.9(3) . . ?
 C7 C8 C10 105.9(3) . . ?
 C9 C8 C7 118.7(3) . . ?
 C9 C8 C10 135.4(3) . . ?
 C4 C9 C8 119.7(4) . . ?
 C4 C9 H9 120.2 . . ?
 C8 C9 H9 120.2 . . ?
 C8 C10 C15 130.0(3) . . ?
 C11 C10 C8 107.3(3) . . ?
 C11 C10 C15 122.6(3) . . ?
 N1 C11 C12 123.8(3) . . ?
 C10 C11 N1 110.5(3) . . ?
 C10 C11 C12 125.7(3) . . ?
 C11 C12 H12A 109.9 . . ?
 C11 C12 H12B 109.9 . . ?
 C11 C12 C13 109.0(3) . . ?
 H12A C12 H12B 108.3 . . ?
 C13 C12 H12A 109.9 . . ?
 C13 C12 H12B 109.9 . . ?
 N2 C13 C12 108.6(3) . . ?
 N2 C13 C16 114.6(3) . . ?
 N2 C13 C17 109.8(3) . . ?
 C12 C13 C16 109.8(3) . . ?
 C17 C13 C12 113.2(3) . . ?
 C17 C13 C16 100.8(3) . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?
 C15 C14 H14A 109.5 . . ?
 C15 C14 H14B 109.5 . . ?
 C15 C14 H14C 109.5 . . ?
 N2 C15 C10 106.9(3) . . ?
 N2 C15 C14 108.1(3) . . ?
 N2 C15 H15 108.9 . . ?
 C10 C15 C14 115.0(3) . . ?
 C10 C15 H15 108.9 . . ?
 C14 C15 H15 108.9 . . ?
 O25 C16 N3 125.4(3) . . ?
 O25 C16 C13 126.4(3) . . ?
 N3 C16 C13 108.2(3) . . ?
 C18 C17 C13 109.5(3) . . ?
 C22 C17 C13 130.5(3) . . ?
 C22 C17 C18 119.9(3) . . ?
 C17 C18 N3 109.7(3) . . ?
 C19 C18 N3 128.2(4) . . ?
 C19 C18 C17 122.0(4) . . ?
 C18 C19 H19 121.1 . . ?
 C18 C19 C20 117.8(4) . . ?
 C20 C19 H19 121.1 . . ?
 C19 C20 H20 120.0 . . ?
 C21 C20 C19 120.0(3) . . ?
 C21 C20 H20 120.0 . . ?
 C20 C21 Cl2 118.9(3) . . ?
 C20 C21 C22 122.5(4) . . ?
 C22 C21 Cl2 118.6(3) . . ?
 C17 C22 H22 121.2 . . ?
 C21 C22 C17 117.7(4) . . ?
 C21 C22 H22 121.2 . . ?
 C1 O0A H0A 109.5 . . ?
 C1A O0A H0AA 109.5 . . ?
 O0A C1 H1A 107.0 . . ?
 O0A C1 C2 109.5(6) . . ?
 O0A C1 C3 111.6(6) . . ?
 C2 C1 H1A 107.0 . . ?
 C2 C1 C3 114.4(7) . . ?
 C3 C1 H1A 107.0 . . ?
 O0A C1A H1AA 103.9 . . ?
 O0A C1A C2 101.4(10) . . ?
 C2 C1A H1AA 103.9 . . ?
 C3 C1A O0A 122.2(10) . . ?
 C3 C1A H1AA 103.9 . . ?
 C3 C1A C2 119.3(9) . . ?
 C1 C2 H2AA 109.5 . . ?
 C1 C2 H2AB 109.5 . . ?
 C1 C2 H2AC 109.5 . . ?
 C1A C2 H2BD 109.5 . . ?
 C1A C2 H2BE 109.5 . . ?
 C1A C2 H2BF 109.5 . . ?
 H2AA C2 H2AB 109.5 . . ?
 H2AA C2 H2AC 109.5 . . ?
 H2AB C2 H2AC 109.5 . . ?
 H2BD C2 H2BE 109.5 . . ?
 H2BD C2 H2BF 109.5 . . ?
 H2BE C2 H2BF 109.5 . . ?
 C1 C3 H3AA 109.5 . . ?
 C1 C3 H3AB 109.5 . . ?
 C1 C3 H3AC 109.5 . . ?
 C1A C3 H3BD 109.5 . . ?
 C1A C3 H3BE 109.5 . . ?
 C1A C3 H3BF 109.5 . . ?
 H3AA C3 H3AB 109.5 . . ?
 H3AA C3 H3AC 109.5 . . ?
 H3AB C3 H3AC 109.5 . . ?
 H3BD C3 H3BE 109.5 . . ?
 H3BD C3 H3BF 109.5 . . ?
 H3BE C3 H3BF 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
 Cl1 C5 C6 C7 177.7(3) . . . . ?
 Cl2 C21 C22 C17 -179.3(3) . . . . ?
 N1 C7 C8 C9 177.4(3) . . . . ?
 N1 C7 C8 C10 -0.8(4) . . . . ?
 N1 C11 C12 C13 164.8(3) . . . . ?
 N2 C13 C16 O25 -66.8(4) . . . . ?
 N2 C13 C16 N3 113.2(3) . . . . ?
 N2 C13 C17 C18 -116.6(3) . . . . ?
 N2 C13 C17 C22 61.1(5) . . . . ?
 N3 C18 C19 C20 179.4(4) . . . . ?
 C4 C5 C6 C7 -1.6(7) . . . . ?
 C5 C4 C9 C8 0.6(6) . . . . ?
 C5 C6 C7 N1 -175.4(4) . . . . ?
 C5 C6 C7 C8 1.1(6) . . . . ?
 C6 C7 C8 C9 0.2(6) . . . . ?
 C6 C7 C8 C10 -178.0(4) . . . . ?
 C7 N1 C11 C10 0.3(4) . . . . ?
 C7 N1 C11 C12 -178.4(3) . . . . ?
 C7 C8 C9 C4 -1.0(6) . . . . ?
 C7 C8 C10 C11 1.0(4) . . . . ?
 C7 C8 C10 C15 179.9(4) . . . . ?
 C8 C10 C11 N1 -0.8(4) . . . . ?
 C8 C10 C11 C12 177.8(3) . . . . ?
 C8 C10 C15 N2 166.3(3) . . . . ?
 C8 C10 C15 C14 46.3(5) . . . . ?
 C9 C4 C5 Cl1 -178.5(3) . . . . ?
 C9 C4 C5 C6 0.7(7) . . . . ?
 C9 C8 C10 C11 -176.7(4) . . . . ?
 C9 C8 C10 C15 2.2(7) . . . . ?
 C10 C8 C9 C4 176.5(4) . . . . ?
 C10 C11 C12 C13 -13.6(5) . . . . ?
 C11 N1 C7 C6 177.3(4) . . . . ?
 C11 N1 C7 C8 0.4(4) . . . . ?
 C11 C10 C15 N2 -15.0(5) . . . . ?
 C11 C10 C15 C14 -134.9(4) . . . . ?
 C11 C12 C13 N2 44.0(4) . . . . ?
 C11 C12 C13 C16 -82.0(4) . . . . ?
 C11 C12 C13 C17 166.3(3) . . . . ?
 C12 C13 C16 O25 55.7(5) . . . . ?
 C12 C13 C16 N3 -124.3(3) . . . . ?
 C12 C13 C17 C18 121.8(3) . . . . ?
 C12 C13 C17 C22 -60.5(5) . . . . ?
 C13 N2 C15 C10 50.1(4) . . . . ?
 C13 N2 C15 C14 174.4(3) . . . . ?
 C13 C17 C18 N3 -3.2(4) . . . . ?
 C13 C17 C18 C19 174.1(4) . . . . ?
 C13 C17 C22 C21 -174.5(4) . . . . ?
 C15 N2 C13 C12 -67.7(3) . . . . ?
 C15 N2 C13 C16 55.4(4) . . . . ?
 C15 N2 C13 C17 168.0(3) . . . . ?
 C15 C10 C11 N1 -179.8(3) . . . . ?
 C15 C10 C11 C12 -1.2(6) . . . . ?
 C16 N3 C18 C17 -0.1(5) . . . . ?
 C16 N3 C18 C19 -177.1(4) . . . . ?
 C16 C13 C17 C18 4.6(4) . . . . ?
 C16 C13 C17 C22 -177.6(4) . . . . ?
 C17 C13 C16 O25 175.4(4) . . . . ?
 C17 C13 C16 N3 -4.6(4) . . . . ?
 C17 C18 C19 C20 2.7(7) . . . . ?
 C18 N3 C16 O25 -176.9(4) . . . . ?
 C18 N3 C16 C13 3.1(4) . . . . ?
 C18 C17 C22 C21 3.1(6) . . . . ?
 C18 C19 C20 C21 -0.8(7) . . . . ?
 C19 C20 C21 Cl2 178.2(4) . . . . ?
 C19 C20 C21 C22 0.1(7) . . . . ?
 C20 C21 C22 C17 -1.2(7) . . . . ?
 C22 C17 C18 N3 178.8(4) . . . . ?
 C22 C17 C18 C19 -4.0(6) . . . . ?
 O0A C1 C2 C1A 73.2(12) . . . . ?
 O0A C1 C3 C1A -59.0(12) . . . . ?
 O0A C1A C2 C1 -63.6(13) . . . . ?
 O0A C1A C3 C1 66.5(16) . . . . ?
 C1 O0A C1A C2 60.3(12) . . . . ?
 C1 O0A C1A C3 -75.4(16) . . . . ?
 C1A O0A C1 C2 -77.9(13) . . . . ?
 C1A O0A C1 C3 49.8(12) . . . . ?
 C2 C1 C3 C1A 66.1(13) . . . . ?
 C2 C1A C3 C1 -61.9(14) . . . . ?
 C3 C1 C2 C1A -53.0(11) . . . . ?
 C3 C1A C2 C1 73.8(15) . . . . ?

_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  3.037
_oxdiff_exptl_absorpt_empirical_full_min  0.446
