#------------------------------------------------------------------------------
#$Date: 2022-09-06 13:12:40 +0300 (Tue, 06 Sep 2022) $
#$Revision: 277672 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/16/7061671.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_7061671
loop_
_publ_author_name
'Zimnitskiy, Nikolay S.'
'Barkov, Alexey Yu.'
'Kochnev, Ivan A.'
'Kutyashev, Igor B.'
'Korotaev, Vladislav Yu.'
'Sosnovskikh, Vyacheslav Ya.'
_publ_section_title
;
 Highly diastereoselective annulation of 2-substituted
 3-nitro-2H-chromenes with hemicurcuminoids and curcuminoids via a double
 and triple Michael reaction cascade
;
_journal_issue                   33
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16047
_journal_page_last               16057
_journal_paper_doi               10.1039/D2NJ02019J
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C33 H22 Cl2 F3 N3 O3'
_chemical_formula_sum            'C33 H22 Cl2 F3 N3 O3'
_chemical_formula_weight         636.43
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-02-24 deposited with the CCDC.	2022-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                79.867(8)
_cell_angle_beta                 78.202(7)
_cell_angle_gamma                85.035(7)
_cell_formula_units_Z            2
_cell_length_a                   8.4663(7)
_cell_length_b                   12.6932(12)
_cell_length_c                   13.8600(13)
_cell_measurement_reflns_used    1972
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.9310
_cell_measurement_theta_min      3.5780
_cell_volume                     1433.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     51.00  77.00   1.00   30.00    --   22.52-138.00   1.00   26
  2  ω     18.00  43.00   1.00   30.00    --   22.52-132.00 177.00   25
  3  ω    -86.00 -20.00   1.00   30.00    --  -23.92 132.00-113.00   66
  4  ω    -89.00 -58.00   1.00   30.00    --  -23.92 138.00  63.00   31
  5  ω     -3.00  92.00   1.00   30.00    --   22.52  38.00-180.00   95
  6  ω      1.00  91.00   1.00   30.00    --   22.52  57.00 -90.00   90
  7  ω    -46.00  48.00   1.00   30.00    --   22.52 -38.00   0.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0282104000
_diffrn_orient_matrix_UB_12      -0.0354731000
_diffrn_orient_matrix_UB_13      0.0446660000
_diffrn_orient_matrix_UB_21      0.0144006000
_diffrn_orient_matrix_UB_22      0.0381890000
_diffrn_orient_matrix_UB_23      0.0284953000
_diffrn_orient_matrix_UB_31      -0.0796386000
_diffrn_orient_matrix_UB_32      0.0226825000
_diffrn_orient_matrix_UB_33      0.0003330000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0961
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13615
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.915
_diffrn_reflns_theta_min         3.479
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       prism
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0046(15)
_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   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         7704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0604
_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)+(0.0581P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3497
_reflns_number_total             7704
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02019j2.cif
_cod_data_source_block           exp_1002
_cod_depositor_comments
'Adding full bibliography for 7061667--7061671.cif.'
_cod_database_code               7061671
_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   0.942
_shelx_estimated_absorpt_t_min   0.882
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
 C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
;
_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 1.191
_oxdiff_exptl_absorpt_empirical_full_min 0.850
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
Cl1 Cl -0.05658(11) 0.99621(9) 0.29727(7) 0.0757(3) Uani 1 1 d . . . . .
Cl2 Cl 0.45335(13) 0.97779(9) 0.85392(7) 0.0766(3) Uani 1 1 d . . . . .
F1 F 0.3021(2) 0.50403(19) 0.05723(15) 0.0737(6) Uani 1 1 d . . . . .
F2 F 0.1977(2) 0.54072(18) 0.20165(14) 0.0708(6) Uani 1 1 d . . . . .
F3 F 0.4009(3) 0.42808(19) 0.18358(18) 0.0839(7) Uani 1 1 d . . . . .
O1 O 0.3796(2) 0.70241(19) 0.07199(14) 0.0495(6) Uani 1 1 d . . . . .
O2 O 0.7071(3) 0.4899(2) 0.20433(19) 0.0721(7) Uani 1 1 d . . . . .
O3 O 0.5443(3) 0.4957(2) 0.34411(18) 0.0742(8) Uani 1 1 d . . . . .
N1 N 0.5095(3) 0.7750(2) 0.49471(17) 0.0469(7) Uani 1 1 d . . . . .
N2 N 0.6498(3) 0.7834(2) 0.42501(18) 0.0537(7) Uani 1 1 d . . . . .
N3 N 0.5962(3) 0.5325(2) 0.2576(2) 0.0505(7) Uani 1 1 d . . . . .
C1 C 0.3377(4) 0.5202(3) 0.1424(2) 0.0534(8) Uani 1 1 d . . . . .
C2 C 0.4541(3) 0.6107(3) 0.1213(2) 0.0451(7) Uani 1 1 d . . . . .
C3 C 0.5183(3) 0.6367(2) 0.2098(2) 0.0398(7) Uani 1 1 d . . . . .
C4 C 0.6498(3) 0.7233(3) 0.1713(2) 0.0457(7) Uani 1 1 d . . . . .
C5 C 0.7370(4) 0.7358(4) 0.2549(3) 0.0557(9) Uani 1 1 d . . . . .
C6 C 0.6166(3) 0.7473(3) 0.3473(2) 0.0475(8) Uani 1 1 d . . . . .
C7 C 0.4552(3) 0.7193(3) 0.3645(2) 0.0417(7) Uani 1 1 d . . . . .
C8 C 0.3819(3) 0.6787(3) 0.2876(2) 0.0389(7) Uani 1 1 d . . . . .
C9 C 0.2768(3) 0.7622(3) 0.2323(2) 0.0390(7) Uani 1 1 d . . . . .
C10 C 0.1707(3) 0.8344(3) 0.2823(2) 0.0437(7) Uani 1 1 d . . . . .
C11 C 0.0760(3) 0.9095(3) 0.2323(2) 0.0502(8) Uani 1 1 d . . . . .
C12 C 0.0843(4) 0.9164(3) 0.1308(3) 0.0581(9) Uani 1 1 d . . . . .
C13 C 0.1849(4) 0.8450(3) 0.0804(2) 0.0537(9) Uani 1 1 d . . . . .
C14 C 0.2798(3) 0.7688(3) 0.1312(2) 0.0431(7) Uani 1 1 d . . . . .
C15 C 0.3884(3) 0.7361(3) 0.4602(2) 0.0415(7) Uani 1 1 d . . . . .
C16 C 0.2250(3) 0.7165(3) 0.5180(2) 0.0449(7) Uani 1 1 d . . . . .
C17 C 0.1683(4) 0.6144(3) 0.5351(2) 0.0591(9) Uani 1 1 d . . . . .
H17 H 0.236049 0.558222 0.513046 0.071 Uiso 1 1 calc R U . . .
C18 C 0.0119(5) 0.5953(4) 0.5846(3) 0.0802(13) Uani 1 1 d . . . . .
H18 H -0.024737 0.526328 0.597319 0.096 Uiso 1 1 calc R U . . .
C19 C -0.0905(5) 0.6798(5) 0.6153(3) 0.0872(15) Uani 1 1 d . . . . .
H19 H -0.196824 0.667548 0.646943 0.105 Uiso 1 1 calc R U . . .
C20 C -0.0359(4) 0.7805(4) 0.5993(3) 0.0765(13) Uani 1 1 d . . . . .
H20 H -0.104487 0.836414 0.621110 0.092 Uiso 1 1 calc R U . . .
C21 C 0.1202(4) 0.7998(3) 0.5511(2) 0.0570(9) Uani 1 1 d . . . . .
H21 H 0.156459 0.868784 0.540435 0.068 Uiso 1 1 calc R U . . .
C22 C 0.5006(3) 0.8187(3) 0.5837(2) 0.0433(7) Uani 1 1 d . . . . .
C23 C 0.4156(4) 0.7716(3) 0.6747(2) 0.0520(8) Uani 1 1 d . . . . .
H23 H 0.367230 0.707270 0.679841 0.062 Uiso 1 1 calc R U . . .
C24 C 0.4022(4) 0.8197(3) 0.7577(2) 0.0530(8) Uani 1 1 d . . . . .
H24 H 0.343053 0.788758 0.818747 0.064 Uiso 1 1 calc R U . . .
C25 C 0.4769(4) 0.9140(3) 0.7499(2) 0.0514(8) Uani 1 1 d . . . . .
C26 C 0.5676(4) 0.9595(3) 0.6614(2) 0.0577(9) Uani 1 1 d . . . . .
H26 H 0.619874 1.022007 0.657487 0.069 Uiso 1 1 calc R U . . .
C27 C 0.5809(4) 0.9112(3) 0.5775(2) 0.0537(8) Uani 1 1 d . . . . .
H27 H 0.643525 0.940772 0.517094 0.064 Uiso 1 1 calc R U . . .
C28 C 0.7622(3) 0.7173(3) 0.0712(2) 0.0468(8) Uani 1 1 d . . . . .
C29 C 0.7259(4) 0.7838(3) -0.0131(2) 0.0624(10) Uani 1 1 d . . . . .
H29 H 0.633365 0.829131 -0.006895 0.075 Uiso 1 1 calc R U . . .
C30 C 0.8243(4) 0.7841(4) -0.1062(3) 0.0752(12) Uani 1 1 d . . . . .
H30 H 0.797682 0.828932 -0.161909 0.090 Uiso 1 1 calc R U . . .
C31 C 0.9618(4) 0.7176(4) -0.1156(3) 0.0714(12) Uani 1 1 d . . . . .
H31 H 1.028259 0.716961 -0.177882 0.086 Uiso 1 1 calc R U . . .
C32 C 1.0006(4) 0.6524(4) -0.0335(3) 0.0651(11) Uani 1 1 d . . . . .
H32 H 1.093256 0.607210 -0.040180 0.078 Uiso 1 1 calc R U . . .
C33 C 0.9036(3) 0.6531(3) 0.0591(2) 0.0560(9) Uani 1 1 d . . . . .
H33 H 0.933378 0.609696 0.114557 0.067 Uiso 1 1 calc R U . . .
H2 H 0.544(3) 0.589(3) 0.074(2) 0.053(9) Uiso 1 1 d . . . . .
H4 H 0.578(3) 0.788(2) 0.1585(18) 0.036(7) Uiso 1 1 d . . . . .
H8 H 0.316(3) 0.621(2) 0.3193(19) 0.038(8) Uiso 1 1 d . . . . .
H10 H 0.166(3) 0.831(2) 0.351(2) 0.040(8) Uiso 1 1 d . . . . .
H13 H 0.186(3) 0.846(3) 0.010(2) 0.060(9) Uiso 1 1 d . . . . .
H5A H 0.811(4) 0.674(3) 0.263(2) 0.072(11) Uiso 1 1 d . . . . .
H12 H 0.020(3) 0.965(3) 0.095(2) 0.055(9) Uiso 1 1 d . . . . .
H5B H 0.805(4) 0.797(3) 0.232(2) 0.061(10) Uiso 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'
F F 0.0171 0.0103 '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
C14 O1 C2 117.4(2) . . ?
N2 N1 C15 112.1(2) . . ?
N2 N1 C22 118.2(2) . . ?
C15 N1 C22 129.1(2) . . ?
C6 N2 N1 104.6(2) . . ?
O2 N3 C3 116.8(3) . . ?
O3 N3 O2 123.6(3) . . ?
O3 N3 C3 119.6(2) . . ?
F1 C1 F2 106.4(2) . . ?
F1 C1 C2 109.7(3) . . ?
F2 C1 C2 113.7(3) . . ?
F3 C1 F1 107.0(3) . . ?
F3 C1 F2 107.4(3) . . ?
F3 C1 C2 112.3(3) . . ?
O1 C2 C1 107.7(2) . . ?
O1 C2 C3 111.2(2) . . ?
O1 C2 H2 106.4(18) . . ?
C1 C2 C3 117.5(3) . . ?
C1 C2 H2 105.2(19) . . ?
C3 C2 H2 108.2(16) . . ?
N3 C3 C2 106.9(2) . . ?
N3 C3 C4 109.5(2) . . ?
N3 C3 C8 109.6(2) . . ?
C2 C3 C4 109.8(2) . . ?
C2 C3 C8 111.7(2) . . ?
C8 C3 C4 109.3(2) . . ?
C3 C4 H4 99.4(15) . . ?
C5 C4 C3 110.7(3) . . ?
C5 C4 H4 108.8(15) . . ?
C28 C4 C3 117.7(2) . . ?
C28 C4 C5 113.9(2) . . ?
C28 C4 H4 104.8(15) . . ?
C4 C5 H5A 107(2) . . ?
C4 C5 H5B 108.4(19) . . ?
C6 C5 C4 109.7(2) . . ?
C6 C5 H5A 113(2) . . ?
C6 C5 H5B 112.7(19) . . ?
H5A C5 H5B 105(3) . . ?
N2 C6 C5 124.0(3) . . ?
N2 C6 C7 111.6(2) . . ?
C7 C6 C5 124.4(3) . . ?
C6 C7 C8 123.3(2) . . ?
C15 C7 C6 106.0(2) . . ?
C15 C7 C8 130.7(2) . . ?
C3 C8 H8 107.8(16) . . ?
C7 C8 C3 109.2(2) . . ?
C7 C8 C9 114.6(3) . . ?
C7 C8 H8 109.6(16) . . ?
C9 C8 C3 108.2(2) . . ?
C9 C8 H8 107.3(15) . . ?
C10 C9 C8 121.2(2) . . ?
C14 C9 C8 121.8(3) . . ?
C14 C9 C10 116.9(3) . . ?
C9 C10 H10 118.6(17) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 120.2(17) . . ?
C10 C11 Cl1 119.8(2) . . ?
C10 C11 C12 120.9(3) . . ?
C12 C11 Cl1 119.3(3) . . ?
C11 C12 H12 122.8(19) . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 118.0(19) . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.0(19) . . ?
C14 C13 H13 120.0(19) . . ?
C9 C14 O1 123.2(3) . . ?
C9 C14 C13 122.0(3) . . ?
C13 C14 O1 114.8(3) . . ?
N1 C15 C7 105.6(2) . . ?
N1 C15 C16 125.0(2) . . ?
C7 C15 C16 129.4(2) . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 C21 118.6(3) . . ?
C21 C16 C15 121.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(4) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.7(4) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.3(4) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.3(4) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.5(4) . . ?
C20 C21 H21 119.7 . . ?
C23 C22 N1 121.9(3) . . ?
C23 C22 C27 119.7(3) . . ?
C27 C22 N1 118.3(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.6(3) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 Cl2 119.7(3) . . ?
C26 C25 Cl2 119.2(3) . . ?
C26 C25 C24 121.1(3) . . ?
C25 C26 H26 120.4 . . ?
C25 C26 C27 119.3(3) . . ?
C27 C26 H26 120.4 . . ?
C22 C27 C26 120.0(3) . . ?
C22 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C4 118.4(3) . . ?
C33 C28 C4 124.3(3) . . ?
C33 C28 C29 117.3(3) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 C28 121.6(3) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 H30 120.3 . . ?
C31 C30 C29 119.4(4) . . ?
C31 C30 H30 120.3 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0(3) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C33 120.5(3) . . ?
C33 C32 H32 119.8 . . ?
C28 C33 H33 119.4 . . ?
C32 C33 C28 121.2(3) . . ?
C32 C33 H33 119.4 . . ?
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 C11 1.733(3) . ?
Cl2 C25 1.743(3) . ?
F1 C1 1.329(3) . ?
F2 C1 1.331(3) . ?
F3 C1 1.327(4) . ?
O1 C2 1.411(4) . ?
O1 C14 1.391(3) . ?
O2 N3 1.220(3) . ?
O3 N3 1.213(3) . ?
N1 N2 1.368(3) . ?
N1 C15 1.377(3) . ?
N1 C22 1.424(3) . ?
N2 C6 1.330(3) . ?
N3 C3 1.530(4) . ?
C1 C2 1.528(5) . ?
C2 C3 1.535(4) . ?
C2 H2 0.95(3) . ?
C3 C4 1.580(4) . ?
C3 C8 1.538(4) . ?
C4 C5 1.532(4) . ?
C4 C28 1.523(4) . ?
C4 H4 1.00(3) . ?
C5 C6 1.485(4) . ?
C5 H5A 0.96(4) . ?
C5 H5B 0.97(4) . ?
C6 C7 1.404(4) . ?
C7 C8 1.519(4) . ?
C7 C15 1.377(4) . ?
C8 C9 1.527(4) . ?
C8 H8 0.95(3) . ?
C9 C10 1.397(4) . ?
C9 C14 1.385(4) . ?
C10 C11 1.376(4) . ?
C10 H10 0.94(3) . ?
C11 C12 1.383(4) . ?
C12 C13 1.371(5) . ?
C12 H12 0.93(3) . ?
C13 C14 1.391(4) . ?
C13 H13 0.98(3) . ?
C15 C16 1.467(4) . ?
C16 C17 1.385(5) . ?
C16 C21 1.399(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.363(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(4) . ?
C22 C27 1.388(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.375(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(5) . ?
C25 C26 1.367(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.389(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.388(4) . ?
C28 C33 1.386(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.386(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.375(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.364(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.376(4) . ?
C33 H33 0.9300 . ?
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 C11 C12 C13 -177.6(3) . . . . ?
Cl2 C25 C26 C27 -177.3(2) . . . . ?
F1 C1 C2 O1 57.4(3) . . . . ?
F1 C1 C2 C3 -176.2(3) . . . . ?
F2 C1 C2 O1 -61.5(3) . . . . ?
F2 C1 C2 C3 64.9(4) . . . . ?
F3 C1 C2 O1 176.3(2) . . . . ?
F3 C1 C2 C3 -57.3(3) . . . . ?
O1 C2 C3 N3 -180.0(2) . . . . ?
O1 C2 C3 C4 -61.2(3) . . . . ?
O1 C2 C3 C8 60.2(3) . . . . ?
O2 N3 C3 C2 58.9(3) . . . . ?
O2 N3 C3 C4 -60.1(3) . . . . ?
O2 N3 C3 C8 -179.9(2) . . . . ?
O3 N3 C3 C2 -119.7(3) . . . . ?
O3 N3 C3 C4 121.4(3) . . . . ?
O3 N3 C3 C8 1.5(4) . . . . ?
N1 N2 C6 C5 -176.6(3) . . . . ?
N1 N2 C6 C7 2.1(4) . . . . ?
N1 C15 C16 C17 -121.0(4) . . . . ?
N1 C15 C16 C21 63.3(4) . . . . ?
N1 C22 C23 C24 -176.2(3) . . . . ?
N1 C22 C27 C26 176.4(3) . . . . ?
N2 N1 C15 C7 0.0(4) . . . . ?
N2 N1 C15 C16 178.9(3) . . . . ?
N2 N1 C22 C23 -145.2(3) . . . . ?
N2 N1 C22 C27 34.6(4) . . . . ?
N2 C6 C7 C8 178.2(3) . . . . ?
N2 C6 C7 C15 -2.2(4) . . . . ?
N3 C3 C4 C5 -52.7(3) . . . . ?
N3 C3 C4 C28 80.7(3) . . . . ?
N3 C3 C8 C7 70.5(3) . . . . ?
N3 C3 C8 C9 -164.1(2) . . . . ?
C1 C2 C3 N3 55.4(3) . . . . ?
C1 C2 C3 C4 174.1(3) . . . . ?
C1 C2 C3 C8 -64.5(3) . . . . ?
C2 O1 C14 C9 14.0(4) . . . . ?
C2 O1 C14 C13 -167.7(3) . . . . ?
C2 C3 C4 C5 -169.9(3) . . . . ?
C2 C3 C4 C28 -36.5(4) . . . . ?
C2 C3 C8 C7 -171.2(3) . . . . ?
C2 C3 C8 C9 -45.8(3) . . . . ?
C3 C4 C5 C6 -48.0(4) . . . . ?
C3 C4 C28 C29 98.1(4) . . . . ?
C3 C4 C28 C33 -85.0(4) . . . . ?
C3 C8 C9 C10 -162.9(3) . . . . ?
C3 C8 C9 C14 18.4(4) . . . . ?
C4 C3 C8 C7 -49.5(3) . . . . ?
C4 C3 C8 C9 75.9(3) . . . . ?
C4 C5 C6 N2 -164.0(3) . . . . ?
C4 C5 C6 C7 17.5(5) . . . . ?
C4 C28 C29 C30 178.8(3) . . . . ?
C4 C28 C33 C32 -179.3(3) . . . . ?
C5 C4 C28 C29 -130.0(4) . . . . ?
C5 C4 C28 C33 46.9(5) . . . . ?
C5 C6 C7 C8 -3.2(6) . . . . ?
C5 C6 C7 C15 176.5(3) . . . . ?
C6 C7 C8 C3 19.8(4) . . . . ?
C6 C7 C8 C9 -101.7(3) . . . . ?
C6 C7 C15 N1 1.3(3) . . . . ?
C6 C7 C15 C16 -177.6(3) . . . . ?
C7 C8 C9 C10 -40.8(4) . . . . ?
C7 C8 C9 C14 140.4(3) . . . . ?
C7 C15 C16 C17 57.6(5) . . . . ?
C7 C15 C16 C21 -118.1(4) . . . . ?
C8 C3 C4 C5 67.3(3) . . . . ?
C8 C3 C4 C28 -159.3(3) . . . . ?
C8 C7 C15 N1 -179.1(3) . . . . ?
C8 C7 C15 C16 2.0(6) . . . . ?
C8 C9 C10 C11 -179.9(3) . . . . ?
C8 C9 C14 O1 -1.4(4) . . . . ?
C8 C9 C14 C13 -179.7(3) . . . . ?
C9 C10 C11 Cl1 179.0(2) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C10 C9 C14 O1 179.8(3) . . . . ?
C10 C9 C14 C13 1.6(4) . . . . ?
C10 C11 C12 C13 2.0(5) . . . . ?
C11 C12 C13 C14 -1.6(6) . . . . ?
C12 C13 C14 O1 -178.6(3) . . . . ?
C12 C13 C14 C9 -0.2(5) . . . . ?
C14 O1 C2 C1 87.6(3) . . . . ?
C14 O1 C2 C3 -42.5(3) . . . . ?
C14 C9 C10 C11 -1.2(4) . . . . ?
C15 N1 N2 C6 -1.3(4) . . . . ?
C15 N1 C22 C23 44.3(5) . . . . ?
C15 N1 C22 C27 -135.9(3) . . . . ?
C15 C7 C8 C3 -159.7(3) . . . . ?
C15 C7 C8 C9 78.7(4) . . . . ?
C15 C16 C17 C18 -176.4(3) . . . . ?
C15 C16 C21 C20 175.6(3) . . . . ?
C16 C17 C18 C19 1.6(5) . . . . ?
C17 C16 C21 C20 -0.2(5) . . . . ?
C17 C18 C19 C20 -1.9(6) . . . . ?
C18 C19 C20 C21 1.1(6) . . . . ?
C19 C20 C21 C16 -0.1(5) . . . . ?
C21 C16 C17 C18 -0.6(5) . . . . ?
C22 N1 N2 C6 -173.3(3) . . . . ?
C22 N1 C15 C7 170.9(3) . . . . ?
C22 N1 C15 C16 -10.2(5) . . . . ?
C22 C23 C24 C25 -1.3(5) . . . . ?
C23 C22 C27 C26 -3.8(5) . . . . ?
C23 C24 C25 Cl2 177.5(2) . . . . ?
C23 C24 C25 C26 -1.6(5) . . . . ?
C24 C25 C26 C27 1.8(5) . . . . ?
C25 C26 C27 C22 0.9(5) . . . . ?
C27 C22 C23 C24 4.0(5) . . . . ?
C28 C4 C5 C6 176.7(3) . . . . ?
C28 C29 C30 C31 -0.3(6) . . . . ?
C29 C28 C33 C32 -2.4(5) . . . . ?
C29 C30 C31 C32 -0.3(6) . . . . ?
C30 C31 C32 C33 -0.4(6) . . . . ?
C31 C32 C33 C28 1.8(6) . . . . ?
C33 C28 C29 C30 1.7(5) . . . . ?
