#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:57:33 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293259 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159937.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159937
loop_
_publ_author_name
'Chang, Meng-Yang'
'Ho, Chin-Huey'
'Chen, Hsing-Yin'
_publ_section_title
;
 K₂CO₃-mediated annulation of
 1,3-acetonedicarboxylates with 2-fluoro-1-nitroarenes: synthesis of
 indoles.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4108
_journal_page_last               4122
_journal_paper_doi               10.1039/d4ob00488d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H16 Cl2 N2 O6'
_chemical_formula_sum            'C20 H16 Cl2 N2 O6'
_chemical_formula_weight         451.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                95.590(2)
_cell_angle_beta                 98.647(2)
_cell_angle_gamma                114.340(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0746(2)
_cell_length_b                   8.2867(3)
_cell_length_c                   16.9277(3)
_cell_measurement_reflns_used    14652
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8580
_cell_measurement_theta_min      2.4620
_cell_volume                     1004.16(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_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    -17.00 100.00   0.50    3.10    --   10.60  82.00 -30.00  234
  2  ω    -17.00 100.00   0.50    3.10    --   10.60  82.00   0.00  234
  3  ω    -17.00 100.00   0.50    3.10    --   10.60  82.00-150.00  234
  4  ω    -79.00  36.00   0.50    3.10    --   10.60 -77.00 150.00  230
  5  ω    -17.00 100.00   0.50    3.10    --   10.60  82.00-180.00  234
  6  ω    -17.00 100.00   0.50    3.10    --   10.60  82.00-120.00  234
  7  ω   -100.00  17.00   0.50    3.10    --  -10.90 -82.00 -30.00  234
  8  ω    -41.00  79.00   0.50    3.10    --  -10.90  57.00  60.00  240
  9  ω   -100.00  15.00   0.50    3.10    --  -10.90 -77.00  30.00  230
 10  ω    -48.00  79.00   0.50    3.10    --  -10.90  37.00 -90.00  254
 11  ω    -38.00  79.00   0.50    3.10    --  -10.90  82.00  60.00  234
 12  ω    -36.00  79.00   0.50    3.10    --  -10.90  77.00 120.00  230
 13  ω    -38.00   6.00   0.50    3.10    --  -10.90  82.00-150.00   88
 14  ω    -38.00  79.00   0.50    3.10    --  -10.90  82.00 -60.00  234
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0198737000
_diffrn_orient_matrix_UB_12      0.0025064000
_diffrn_orient_matrix_UB_13      0.0424883000
_diffrn_orient_matrix_UB_21      -0.0398742000
_diffrn_orient_matrix_UB_22      0.0609081000
_diffrn_orient_matrix_UB_23      0.0061671000
_diffrn_orient_matrix_UB_31      -0.0879753000
_diffrn_orient_matrix_UB_32      -0.0734491000
_diffrn_orient_matrix_UB_33      -0.0033379000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25407
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.473
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0486P)²+0.8160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3037
_reflns_number_total             3539
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00488d3.cif
_cod_data_source_block           k11111-myc-h(chq3739)_auto
_cod_depositor_comments
'Adding full bibliography for 7159934--7159937.cif.'
_cod_original_cell_volume        1004.16(5)
_cod_database_code               7159937
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.868
_shelx_estimated_absorpt_t_min   0.839
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O2, N2
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C2(H2), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.629
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cl2 Cl 1.07588(9) 1.04983(9) 0.60402(4) 0.04676(19) Uani 1 1 d . . . . .
O4 O 0.3697(2) 0.6245(2) 0.69134(9) 0.0333(4) Uani 1 1 d . . . . .
O6 O 0.6105(2) 0.7560(2) 0.56366(9) 0.0317(4) Uani 1 1 d . . . . .
O5 O 0.6376(3) 1.0062(2) 0.63998(10) 0.0411(4) Uani 1 1 d . . . . .
O3 O 0.4207(2) 0.5404(3) 0.81137(10) 0.0427(4) Uani 1 1 d . . . . .
N2 N 0.7437(3) 0.8956(2) 0.95423(10) 0.0272(4) Uani 1 1 d . U . . .
N1 N 0.8120(2) 0.7181(2) 0.81689(10) 0.0246(4) Uani 1 1 d . . . . .
O2 O 0.8615(3) 1.0103(2) 0.92781(11) 0.0452(4) Uani 1 1 d . U . . .
O1 O 0.6183(3) 0.9075(2) 0.97991(11) 0.0453(4) Uani 1 1 d . . . . .
C15 C 0.7872(3) 0.6378(3) 0.88756(12) 0.0233(4) Uani 1 1 d . . . . .
C20 C 0.7885(3) 0.4715(3) 0.89037(12) 0.0257(4) Uani 1 1 d . . . . .
C16 C 0.7581(3) 0.7212(3) 0.95611(12) 0.0240(4) Uani 1 1 d . . . . .
C9 C 0.6610(3) 0.8720(3) 0.63267(13) 0.0296(5) Uani 1 1 d . . . . .
C17 C 0.7341(3) 0.6464(3) 1.02554(12) 0.0270(5) Uani 1 1 d . . . . .
H17 H 0.712871 0.705736 1.071137 0.032 Uiso 1 1 calc R U . . .
C1 C 0.9828(3) 0.8190(3) 0.80030(13) 0.0264(5) Uani 1 1 d . . . . .
C7 C 0.7565(3) 0.8196(3) 0.70143(12) 0.0265(5) Uani 1 1 d . . . . .
C18 C 0.7418(3) 0.4833(3) 1.02684(13) 0.0284(5) Uani 1 1 d . . . . .
H18 H 0.729858 0.431657 1.074577 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6747(3) 0.7199(3) 0.75674(12) 0.0248(4) Uani 1 1 d . . . . .
C12 C 0.4769(3) 0.6191(3) 0.75781(12) 0.0278(5) Uani 1 1 d . . . . .
C19 C 0.7667(3) 0.3944(3) 0.95960(13) 0.0281(5) Uani 1 1 d . . . . .
H19 H 0.768828 0.280871 0.960696 0.034 Uiso 1 1 calc R U . . .
C6 C 0.9525(3) 0.8821(3) 0.72757(13) 0.0266(5) Uani 1 1 d . . . . .
C2 C 1.1603(3) 0.8604(3) 0.84437(14) 0.0302(5) Uani 1 1 d . . . . .
H2 H 1.177760 0.818791 0.893885 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5183(3) 0.7990(3) 0.49369(13) 0.0342(5) Uani 1 1 d . . . . .
H10A H 0.604102 0.913929 0.480565 0.041 Uiso 1 1 calc R U . . .
H10B H 0.407764 0.811959 0.505757 0.041 Uiso 1 1 calc R U . . .
C5 C 1.1094(3) 0.9831(3) 0.69701(14) 0.0339(5) Uani 1 1 d . . . . .
C3 C 1.3089(3) 0.9645(3) 0.81274(15) 0.0373(5) Uani 1 1 d . . . . .
H3 H 1.431543 0.997522 0.841903 0.045 Uiso 1 1 calc R U . . .
C4 C 1.2844(3) 1.0231(3) 0.73881(15) 0.0395(6) Uani 1 1 d . . . . .
H4 H 1.389510 1.090863 0.717621 0.047 Uiso 1 1 calc R U . . .
C11 C 0.4611(4) 0.6497(3) 0.42335(14) 0.0388(6) Uani 1 1 d . . . . .
H11A H 0.406974 0.680422 0.374632 0.058 Uiso 1 1 calc R U . . .
H11B H 0.368752 0.538400 0.435168 0.058 Uiso 1 1 calc R U . . .
H11C H 0.570134 0.632380 0.414161 0.058 Uiso 1 1 calc R U . . .
C13 C 0.1700(3) 0.5241(4) 0.68469(14) 0.0395(6) Uani 1 1 d . . . . .
H13A H 0.126366 0.584974 0.724303 0.047 Uiso 1 1 calc R U . . .
H13B H 0.139773 0.400814 0.695427 0.047 Uiso 1 1 calc R U . . .
C14 C 0.0794(4) 0.5177(5) 0.59968(17) 0.0594(8) Uani 1 1 d . . . . .
H14A H 0.124963 0.458349 0.561205 0.089 Uiso 1 1 calc R U . . .
H14B H 0.109765 0.640550 0.590118 0.089 Uiso 1 1 calc R U . . .
H14C H -0.055660 0.450192 0.592136 0.089 Uiso 1 1 calc R U . . .
Cl1 Cl 0.80936(9) 0.35350(8) 0.80519(3) 0.03881(17) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C12 O4 C13 115.70(17) . . ?
C9 O6 C10 115.59(16) . . ?
O2 N2 C16 116.76(17) . . ?
O1 N2 O2 126.91(19) . . ?
O1 N2 C16 116.33(18) . . ?
C1 N1 C15 123.89(17) . . ?
C1 N1 C8 108.53(16) . . ?
C8 N1 C15 127.45(17) . . ?
C20 C15 N1 121.17(18) . . ?
C20 C15 C16 117.22(18) . . ?
C16 C15 N1 121.60(18) . . ?
C15 C20 C19 121.14(19) . . ?
C15 C20 Cl1 119.76(16) . . ?
C19 C20 Cl1 119.06(16) . . ?
C15 C16 N2 119.24(17) . . ?
C17 C16 N2 117.95(18) . . ?
C17 C16 C15 122.76(19) . . ?
O6 C9 C7 112.36(18) . . ?
O5 C9 O6 124.8(2) . . ?
O5 C9 C7 122.8(2) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 C16 118.29(19) . . ?
C18 C17 H17 120.9 . . ?
N1 C1 C6 107.76(18) . . ?
N1 C1 C2 129.41(19) . . ?
C2 C1 C6 122.83(19) . . ?
C8 C7 C9 126.5(2) . . ?
C8 C7 C6 106.90(18) . . ?
C6 C7 C9 126.16(19) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.80(19) . . ?
C19 C18 H18 119.6 . . ?
N1 C8 C12 120.60(18) . . ?
C7 C8 N1 109.40(18) . . ?
C7 C8 C12 129.96(19) . . ?
O4 C12 C8 110.90(18) . . ?
O3 C12 O4 124.9(2) . . ?
O3 C12 C8 124.2(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 C20 119.76(19) . . ?
C18 C19 H19 120.1 . . ?
C1 C6 C7 107.39(18) . . ?
C5 C6 C1 117.6(2) . . ?
C5 C6 C7 135.0(2) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.0(2) . . ?
C3 C2 H2 121.5 . . ?
O6 C10 H10A 110.0 . . ?
O6 C10 H10B 110.0 . . ?
O6 C10 C11 108.34(18) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C6 C5 Cl2 118.68(18) . . ?
C4 C5 Cl2 120.90(17) . . ?
C4 C5 C6 120.4(2) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C13 H13A 110.4 . . ?
O4 C13 H13B 110.4 . . ?
O4 C13 C14 106.5(2) . . ?
H13A C13 H13B 108.6 . . ?
C14 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
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 . . ?
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
Cl2 C5 1.738(2) . ?
O4 C12 1.329(3) . ?
O4 C13 1.458(3) . ?
O6 C9 1.330(3) . ?
O6 C10 1.456(2) . ?
O5 C9 1.200(3) . ?
O3 C12 1.204(3) . ?
N2 O2 1.214(2) . ?
N2 O1 1.196(2) . ?
N2 C16 1.500(3) . ?
N1 C15 1.425(2) . ?
N1 C1 1.376(3) . ?
N1 C8 1.394(3) . ?
C15 C20 1.388(3) . ?
C15 C16 1.392(3) . ?
C20 C19 1.388(3) . ?
C20 Cl1 1.731(2) . ?
C16 C17 1.384(3) . ?
C9 C7 1.498(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(3) . ?
C1 C6 1.410(3) . ?
C1 C2 1.397(3) . ?
C7 C8 1.372(3) . ?
C7 C6 1.427(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(3) . ?
C8 C12 1.470(3) . ?
C19 H19 0.9500 . ?
C6 C5 1.407(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.496(3) . ?
C5 C4 1.369(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(3) . ?
C4 H4 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.498(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
Cl2 C5 C4 C3 -178.40(19) . . . . ?
O6 C9 C7 C8 -93.5(3) . . . . ?
O6 C9 C7 C6 94.6(3) . . . . ?
O5 C9 C7 C8 88.0(3) . . . . ?
O5 C9 C7 C6 -83.9(3) . . . . ?
N2 C16 C17 C18 178.17(18) . . . . ?
N1 C15 C20 C19 179.19(19) . . . . ?
N1 C15 C20 Cl1 -3.2(3) . . . . ?
N1 C15 C16 N2 2.9(3) . . . . ?
N1 C15 C16 C17 -179.84(19) . . . . ?
N1 C1 C6 C7 1.5(2) . . . . ?
N1 C1 C6 C5 -177.41(19) . . . . ?
N1 C1 C2 C3 179.5(2) . . . . ?
N1 C8 C12 O4 -173.95(18) . . . . ?
N1 C8 C12 O3 5.0(3) . . . . ?
O2 N2 C16 C15 -47.2(3) . . . . ?
O2 N2 C16 C17 135.4(2) . . . . ?
O1 N2 C16 C15 133.6(2) . . . . ?
O1 N2 C16 C17 -43.8(3) . . . . ?
C15 N1 C1 C6 -177.48(18) . . . . ?
C15 N1 C1 C2 1.7(3) . . . . ?
C15 N1 C8 C7 176.64(19) . . . . ?
C15 N1 C8 C12 -5.4(3) . . . . ?
C15 C20 C19 C18 0.5(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C20 C15 C16 N2 -176.28(18) . . . . ?
C20 C15 C16 C17 1.0(3) . . . . ?
C16 C15 C20 C19 -1.7(3) . . . . ?
C16 C15 C20 Cl1 175.98(16) . . . . ?
C16 C17 C18 C19 -2.1(3) . . . . ?
C9 O6 C10 C11 -176.50(19) . . . . ?
C9 C7 C8 N1 -172.89(19) . . . . ?
C9 C7 C8 C12 9.4(4) . . . . ?
C9 C7 C6 C1 172.1(2) . . . . ?
C9 C7 C6 C5 -9.3(4) . . . . ?
C17 C18 C19 C20 1.5(3) . . . . ?
C1 N1 C15 C20 -84.5(3) . . . . ?
C1 N1 C15 C16 96.4(2) . . . . ?
C1 N1 C8 C7 0.6(2) . . . . ?
C1 N1 C8 C12 178.61(18) . . . . ?
C1 C6 C5 Cl2 175.70(16) . . . . ?
C1 C6 C5 C4 -2.4(3) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C7 C8 C12 O4 3.5(3) . . . . ?
C7 C8 C12 O3 -177.5(2) . . . . ?
C7 C6 C5 Cl2 -2.8(4) . . . . ?
C7 C6 C5 C4 179.1(2) . . . . ?
C8 N1 C15 C20 100.1(3) . . . . ?
C8 N1 C15 C16 -79.1(3) . . . . ?
C8 N1 C1 C6 -1.3(2) . . . . ?
C8 N1 C1 C2 177.9(2) . . . . ?
C8 C7 C6 C1 -1.1(2) . . . . ?
C8 C7 C6 C5 177.5(2) . . . . ?
C12 O4 C13 C14 -169.0(2) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C6 C7 C8 N1 0.3(2) . . . . ?
C6 C7 C8 C12 -177.4(2) . . . . ?
C6 C5 C4 C3 -0.3(4) . . . . ?
C2 C1 C6 C7 -177.8(2) . . . . ?
C2 C1 C6 C5 3.4(3) . . . . ?
C2 C3 C4 C5 2.4(4) . . . . ?
C10 O6 C9 O5 -0.9(3) . . . . ?
C10 O6 C9 C7 -179.37(18) . . . . ?
C13 O4 C12 O3 -0.7(3) . . . . ?
C13 O4 C12 C8 178.24(18) . . . . ?
Cl1 C20 C19 C18 -177.20(16) . . . . ?
