# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

data_201811442
_audit_creation_date               2018-12-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_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           'C18 H17 Cl N2 O5'
_chemical_formula_sum              'C18 H17 Cl N2 O5'
_chemical_formula_weight           376.78
_chemical_melting_point            ?
_chemical_oxdiff_formula           C15H15O3N2Cl1
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             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     9.7345(3)
_cell_length_b                     14.0642(4)
_cell_length_c                     13.0475(4)
_cell_angle_alpha                  90
_cell_angle_beta                   91.839(3)
_cell_angle_gamma                  90
_cell_volume                       1785.39(10)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      4199
_cell_measurement_temperature      293(2)
_cell_measurement_theta_max        70.7240
_cell_measurement_theta_min        4.5410
_shelx_estimated_absorpt_T_max     0.811
_shelx_estimated_absorpt_T_min     0.682
_exptl_absorpt_coefficient_mu      2.181
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.80793
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.402
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               784
_exptl_crystal_size_max            0.19
_exptl_crystal_size_mid            0.14
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0334
_diffrn_reflns_av_unetI/netI       0.0271
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  1.000
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         16
_diffrn_reflns_limit_k_min         -16
_diffrn_reflns_limit_l_max         15
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              12681
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  1.000
_diffrn_reflns_theta_full          67.065
_diffrn_reflns_theta_max           67.065
_diffrn_reflns_theta_min           4.624
_diffrn_ambient_temperature        293(2)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   16.2312
_diffrn_detector_type              Eos
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  1.000
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000 -150.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega   12.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -65.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  5 omega  -35.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
  8 omega   30.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega  -31.00    2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 10 omega   14.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
 11 omega  -18.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
 12 omega   60.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   70.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 14 omega   -4.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
 15 omega   68.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 16 omega   16.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
 17 omega    2.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -107.0000 -139.0000 31

#__ type_ start__ end____ width___ exp.time_
 19 omega   47.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 44

#__ type_ start__ end____ width___ exp.time_
 20 omega  146.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
 21 omega   96.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 22 omega   51.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 56

#__ type_ start__ end____ width___ exp.time_
 23 omega  137.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega  102.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
 25 omega   38.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
 26 omega   88.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
 27 omega   39.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 76

#__ type_ start__ end____ width___ exp.time_
 28 omega   94.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
 29 omega   57.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
 30 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   42.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
 32 omega   94.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
 33 omega  136.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   38.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 71

#__ type_ start__ end____ width___ exp.time_
 35 omega   46.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 36 omega  115.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  107.0000  -41.0000 55
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'Xcalibur, Eos, Gemini'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_UB_11        0.1008519000
_diffrn_orient_matrix_UB_12        -0.0004208000
_diffrn_orient_matrix_UB_13        -0.0886188000
_diffrn_orient_matrix_UB_21        0.0289946000
_diffrn_orient_matrix_UB_22        -0.1063300000
_diffrn_orient_matrix_UB_23        0.0192004000
_diffrn_orient_matrix_UB_31        -0.1185555000
_diffrn_orient_matrix_UB_32        -0.0264404000
_diffrn_orient_matrix_UB_33        -0.0756813000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2630
_reflns_number_total               3190
_reflns_odcompleteness_completeness  99.94
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max           0.345
_refine_diff_density_min           -0.433
_refine_diff_density_rms           0.049
_refine_ls_extinction_coef         0.0069(6)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref     1.026
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       240
_refine_ls_number_reflns           3190
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0587
_refine_ls_R_factor_gt             0.0484
_refine_ls_restrained_S_all        1.026
_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)+(0.0846P)²+0.6545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1375
_refine_ls_wR_factor_ref           0.1493
_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 Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_atom_sites_solution_hydrogens     geom
_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
 C1 C 0.6278(2) 0.61890(17) 0.64334(17) 0.0450(5) Uani 1 1 d . . . . .
 C2 C 0.8357(2) 0.70975(15) 0.68998(16) 0.0388(5) Uani 1 1 d . . . . .
 C3 C 0.8484(2) 0.53576(15) 0.63419(15) 0.0391(5) Uani 1 1 d . . . . .
 C4 C 0.9181(2) 0.62546(14) 0.66486(16) 0.0378(5) Uani 1 1 d . . . . .
 C5 C 1.0626(2) 0.61881(15) 0.71529(17) 0.0406(5) Uani 1 1 d . . . . .
 C6 C 1.0525(2) 0.64493(15) 0.60548(16) 0.0393(5) Uani 1 1 d . . . . .
 H6 H 1.0759 0.5915 0.5611 0.047 Uiso 1 1 calc R . . . .
 C7 C 1.0759(2) 0.73874(15) 0.55449(16) 0.0396(5) Uani 1 1 d . . . . .
 C8 C 1.1896(3) 0.79507(19) 0.57611(19) 0.0530(6) Uani 1 1 d . . . . .
 H8 H 1.2524 0.7773 0.6278 0.064 Uiso 1 1 calc R . . . .
 C9 C 1.2104(3) 0.87774(19) 0.5213(2) 0.0592(7) Uani 1 1 d . . . . .
 H9 H 1.2864 0.9158 0.5365 0.071 Uiso 1 1 calc R . . . .
 C10 C 1.1181(3) 0.90326(17) 0.44429(18) 0.0515(6) Uani 1 1 d . . . . .
 C11 C 1.0058(3) 0.84844(19) 0.42078(19) 0.0562(6) Uani 1 1 d . . . . .
 H11 H 0.9439 0.8663 0.3685 0.067 Uiso 1 1 calc R . . . .
 C12 C 0.9856(3) 0.76589(17) 0.47596(19) 0.0506(6) Uani 1 1 d . . . . .
 H12 H 0.9097 0.7279 0.4599 0.061 Uiso 1 1 calc R . . . .
 C13 C 1.1119(2) 0.51835(17) 0.7464(2) 0.0507(6) Uani 1 1 d . . . . .
 C14 C 1.2315(3) 0.4788(2) 0.6928(3) 0.0791(10) Uani 1 1 d . . . . .
 H14A H 1.2594 0.4201 0.7247 0.119 Uiso 1 1 calc GR . . . .
 H14B H 1.3063 0.5233 0.6969 0.119 Uiso 1 1 calc GR . . . .
 H14C H 1.2062 0.4674 0.6221 0.119 Uiso 1 1 calc GR . . . .
 C15 C 1.1054(3) 0.68589(17) 0.80281(18) 0.0502(6) Uani 1 1 d . . . . .
 C16 C 1.0233(4) 0.6834(3) 0.8984(2) 0.0784(9) Uani 1 1 d . . . . .
 H16A H 0.9294 0.6682 0.8808 0.118 Uiso 1 1 calc GR . . . .
 H16B H 1.0275 0.7445 0.9313 0.118 Uiso 1 1 calc GR . . . .
 H16C H 1.0607 0.6360 0.9443 0.118 Uiso 1 1 calc GR . . . .
 C17 C 0.6099(3) 0.78537(18) 0.6952(2) 0.0580(7) Uani 1 1 d . . . . .
 H17A H 0.5167 0.7731 0.6727 0.087 Uiso 1 1 calc GR . . . .
 H17B H 0.6445 0.8392 0.6589 0.087 Uiso 1 1 calc GR . . . .
 H17C H 0.6130 0.7984 0.7674 0.087 Uiso 1 1 calc GR . . . .
 C18 C 0.6350(3) 0.44963(18) 0.5993(2) 0.0555(6) Uani 1 1 d . . . . .
 H18A H 0.6195 0.4461 0.5263 0.083 Uiso 1 1 calc GR . . . .
 H18B H 0.5483 0.4482 0.6324 0.083 Uiso 1 1 calc GR . . . .
 H18C H 0.6898 0.3965 0.6219 0.083 Uiso 1 1 calc GR . . . .
 Cl1 Cl 1.14288(10) 1.00852(5) 0.37639(6) 0.0804(3) Uani 1 1 d . . . . .
 N1 N 0.69534(19) 0.70135(13) 0.67445(15) 0.0435(5) Uani 1 1 d . . . . .
 N2 N 0.70750(19) 0.53886(13) 0.62561(14) 0.0423(4) Uani 1 1 d . . . . .
 O1 O 0.50466(18) 0.61685(14) 0.63180(17) 0.0675(6) Uani 1 1 d . . . . .
 O2 O 0.88712(17) 0.78312(11) 0.72115(14) 0.0509(4) Uani 1 1 d . . . . .
 O3 O 0.91160(18) 0.46431(11) 0.61460(14) 0.0536(4) Uani 1 1 d . . . . .
 O4 O 1.0603(2) 0.47938(14) 0.81718(16) 0.0677(6) Uani 1 1 d . . . . .
 O5 O 1.2107(2) 0.72932(14) 0.79854(15) 0.0672(6) 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 N1 1.387(3) . ?
 C1 N2 1.391(3) . ?
 C1 O1 1.204(3) . ?
 C2 C4 1.474(3) . ?
 C2 N1 1.379(3) . ?
 C2 O2 1.212(3) . ?
 C3 C4 1.481(3) . ?
 C3 N2 1.373(3) . ?
 C3 O3 1.210(3) . ?
 C4 C5 1.536(3) . ?
 C4 C6 1.565(3) . ?
 C5 C6 1.479(3) . ?
 C5 C13 1.542(3) . ?
 C5 C15 1.529(3) . ?
 C6 H6 0.9800 . ?
 C6 C7 1.498(3) . ?
 C7 C8 1.382(3) . ?
 C7 C12 1.382(3) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.383(4) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.374(4) . ?
 C10 C11 1.364(4) . ?
 C10 Cl1 1.746(2) . ?
 C11 H11 0.9300 . ?
 C11 C12 1.384(3) . ?
 C12 H12 0.9300 . ?
 C13 C14 1.485(4) . ?
 C13 O4 1.199(3) . ?
 C14 H14A 0.9600 . ?
 C14 H14B 0.9600 . ?
 C14 H14C 0.9600 . ?
 C15 C16 1.503(4) . ?
 C15 O5 1.196(3) . ?
 C16 H16A 0.9600 . ?
 C16 H16B 0.9600 . ?
 C16 H16C 0.9600 . ?
 C17 H17A 0.9600 . ?
 C17 H17B 0.9600 . ?
 C17 H17C 0.9600 . ?
 C17 N1 1.475(3) . ?
 C18 H18A 0.9600 . ?
 C18 H18B 0.9600 . ?
 C18 H18C 0.9600 . ?
 C18 N2 1.475(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 N2 117.61(19) . . ?
 O1 C1 N1 121.2(2) . . ?
 O1 C1 N2 121.2(2) . . ?
 N1 C2 C4 116.23(18) . . ?
 O2 C2 C4 122.5(2) . . ?
 O2 C2 N1 121.3(2) . . ?
 N2 C3 C4 116.26(19) . . ?
 O3 C3 C4 122.2(2) . . ?
 O3 C3 N2 121.50(19) . . ?
 C2 C4 C3 119.80(19) . . ?
 C2 C4 C5 116.82(17) . . ?
 C2 C4 C6 116.03(17) . . ?
 C3 C4 C5 117.96(18) . . ?
 C3 C4 C6 113.45(17) . . ?
 C5 C4 C6 56.96(13) . . ?
 C4 C5 C13 116.21(17) . . ?
 C6 C5 C4 62.52(14) . . ?
 C6 C5 C13 119.5(2) . . ?
 C6 C5 C15 125.33(19) . . ?
 C15 C5 C4 120.42(19) . . ?
 C15 C5 C13 107.08(18) . . ?
 C4 C6 H6 111.8 . . ?
 C5 C6 C4 60.52(14) . . ?
 C5 C6 H6 111.8 . . ?
 C5 C6 C7 129.97(19) . . ?
 C7 C6 C4 121.02(18) . . ?
 C7 C6 H6 111.8 . . ?
 C8 C7 C6 123.1(2) . . ?
 C8 C7 C12 118.6(2) . . ?
 C12 C7 C6 118.0(2) . . ?
 C7 C8 H8 119.8 . . ?
 C7 C8 C9 120.4(2) . . ?
 C9 C8 H8 119.8 . . ?
 C8 C9 H9 120.2 . . ?
 C10 C9 C8 119.6(2) . . ?
 C10 C9 H9 120.2 . . ?
 C9 C10 Cl1 119.66(19) . . ?
 C11 C10 C9 121.1(2) . . ?
 C11 C10 Cl1 119.2(2) . . ?
 C10 C11 H11 120.5 . . ?
 C10 C11 C12 118.9(2) . . ?
 C12 C11 H11 120.5 . . ?
 C7 C12 C11 121.3(2) . . ?
 C7 C12 H12 119.4 . . ?
 C11 C12 H12 119.4 . . ?
 C14 C13 C5 117.5(2) . . ?
 O4 C13 C5 119.1(2) . . ?
 O4 C13 C14 123.1(2) . . ?
 C13 C14 H14A 109.5 . . ?
 C13 C14 H14B 109.5 . . ?
 C13 C14 H14C 109.5 . . ?
 H14A C14 H14B 109.5 . . ?
 H14A C14 H14C 109.5 . . ?
 H14B C14 H14C 109.5 . . ?
 C16 C15 C5 117.8(2) . . ?
 O5 C15 C5 119.6(2) . . ?
 O5 C15 C16 122.0(2) . . ?
 C15 C16 H16A 109.5 . . ?
 C15 C16 H16B 109.5 . . ?
 C15 C16 H16C 109.5 . . ?
 H16A C16 H16B 109.5 . . ?
 H16A C16 H16C 109.5 . . ?
 H16B C16 H16C 109.5 . . ?
 H17A C17 H17B 109.5 . . ?
 H17A C17 H17C 109.5 . . ?
 H17B C17 H17C 109.5 . . ?
 N1 C17 H17A 109.5 . . ?
 N1 C17 H17B 109.5 . . ?
 N1 C17 H17C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 N2 C18 H18A 109.5 . . ?
 N2 C18 H18B 109.5 . . ?
 N2 C18 H18C 109.5 . . ?
 C1 N1 C17 117.30(19) . . ?
 C2 N1 C1 124.92(19) . . ?
 C2 N1 C17 117.76(19) . . ?
 C1 N2 C18 117.5(2) . . ?
 C3 N2 C1 124.98(18) . . ?
 C3 N2 C18 117.47(19) . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
 C6 H6 O3 0.98 2.43 3.285(3) 145.5 3_766

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
 C2 C4 C5 C6 -104.9(2) . . . . ?
 C2 C4 C5 C13 143.8(2) . . . . ?
 C2 C4 C5 C15 11.8(3) . . . . ?
 C2 C4 C6 C5 106.3(2) . . . . ?
 C2 C4 C6 C7 -15.1(3) . . . . ?
 C3 C4 C5 C6 101.1(2) . . . . ?
 C3 C4 C5 C13 -10.2(3) . . . . ?
 C3 C4 C5 C15 -142.2(2) . . . . ?
 C3 C4 C6 C5 -109.1(2) . . . . ?
 C3 C4 C6 C7 129.5(2) . . . . ?
 C4 C2 N1 C1 4.0(3) . . . . ?
 C4 C2 N1 C17 -177.8(2) . . . . ?
 C4 C3 N2 C1 0.0(3) . . . . ?
 C4 C3 N2 C18 -177.59(19) . . . . ?
 C4 C5 C6 C7 107.4(2) . . . . ?
 C4 C5 C13 C14 115.1(3) . . . . ?
 C4 C5 C13 O4 -70.8(3) . . . . ?
 C4 C5 C15 C16 59.9(3) . . . . ?
 C4 C5 C15 O5 -129.1(2) . . . . ?
 C4 C6 C7 C8 123.2(2) . . . . ?
 C4 C6 C7 C12 -62.5(3) . . . . ?
 C5 C4 C6 C7 -121.4(2) . . . . ?
 C5 C6 C7 C8 47.4(3) . . . . ?
 C5 C6 C7 C12 -138.3(2) . . . . ?
 C6 C4 C5 C13 -111.3(2) . . . . ?
 C6 C4 C5 C15 116.8(2) . . . . ?
 C6 C5 C13 C14 43.3(3) . . . . ?
 C6 C5 C13 O4 -142.6(2) . . . . ?
 C6 C5 C15 C16 136.0(3) . . . . ?
 C6 C5 C15 O5 -53.0(3) . . . . ?
 C6 C7 C8 C9 175.4(2) . . . . ?
 C6 C7 C12 C11 -175.6(2) . . . . ?
 C7 C8 C9 C10 -0.7(4) . . . . ?
 C8 C7 C12 C11 -1.2(4) . . . . ?
 C8 C9 C10 C11 0.0(4) . . . . ?
 C8 C9 C10 Cl1 179.0(2) . . . . ?
 C9 C10 C11 C12 0.0(4) . . . . ?
 C10 C11 C12 C7 0.6(4) . . . . ?
 C12 C7 C8 C9 1.2(4) . . . . ?
 C13 C5 C6 C4 106.1(2) . . . . ?
 C13 C5 C6 C7 -146.5(2) . . . . ?
 C13 C5 C15 C16 -75.8(3) . . . . ?
 C13 C5 C15 O5 95.1(3) . . . . ?
 C15 C5 C6 C4 -109.3(2) . . . . ?
 C15 C5 C6 C7 -1.9(4) . . . . ?
 C15 C5 C13 C14 -107.0(3) . . . . ?
 C15 C5 C13 O4 67.1(3) . . . . ?
 Cl1 C10 C11 C12 -179.0(2) . . . . ?
 N1 C1 N2 C3 -1.6(3) . . . . ?
 N1 C1 N2 C18 176.0(2) . . . . ?
 N1 C2 C4 C3 -5.4(3) . . . . ?
 N1 C2 C4 C5 -158.88(18) . . . . ?
 N1 C2 C4 C6 136.77(19) . . . . ?
 N2 C1 N1 C2 -0.6(3) . . . . ?
 N2 C1 N1 C17 -178.8(2) . . . . ?
 N2 C3 C4 C2 3.5(3) . . . . ?
 N2 C3 C4 C5 156.72(19) . . . . ?
 N2 C3 C4 C6 -139.55(19) . . . . ?
 O1 C1 N1 C2 179.7(2) . . . . ?
 O1 C1 N1 C17 1.5(3) . . . . ?
 O1 C1 N2 C3 178.1(2) . . . . ?
 O1 C1 N2 C18 -4.2(3) . . . . ?
 O2 C2 C4 C3 175.6(2) . . . . ?
 O2 C2 C4 C5 22.2(3) . . . . ?
 O2 C2 C4 C6 -42.2(3) . . . . ?
 O2 C2 N1 C1 -177.0(2) . . . . ?
 O2 C2 N1 C17 1.1(3) . . . . ?
 O3 C3 C4 C2 -178.7(2) . . . . ?
 O3 C3 C4 C5 -25.5(3) . . . . ?
 O3 C3 C4 C6 38.2(3) . . . . ?
 O3 C3 N2 C1 -177.7(2) . . . . ?
 O3 C3 N2 C18 4.6(3) . . . . ?


_olex2_submission_special_instructions  'No special instructions were received'
