#------------------------------------------------------------------------------
#$Date: 2021-12-07 05:49:41 +0200 (Tue, 07 Dec 2021) $
#$Revision: 271205 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158356.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_7158356
loop_
_publ_author_name
'Efremova, Mariia M.'
'Makarova, Anastasia A.'
'Novikov, Alexander S.'
'Kryukova, Mariya A.'
'Kuznetsov, Mikhail A.'
'Molchanov, Alexander P.'
_publ_section_title
;
 Regio- and stereoselective (3 + 2)-cycloaddition reactions of nitrones
 with cyclic allenes.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9773
_journal_page_last               9784
_journal_paper_doi               10.1039/d1ob01584b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C22 H25 Cl2 N O6'
_chemical_formula_sum            'C22 H25 Cl2 N O6'
_chemical_formula_weight         470.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-21 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.532(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0854(3)
_cell_length_b                   7.50448(14)
_cell_length_c                   22.3639(5)
_cell_measurement_reflns_used    11447
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.4200
_cell_measurement_theta_min      3.9490
_cell_volume                     2193.97(8)
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  10.00   0.50    0.63    --  -47.20  22.00 -81.00   64
  2  ω    -67.00 -41.00   0.50    2.53    -- -106.00  61.00   0.00   52
  3  ω    -98.00 -43.00   0.50    2.53    -- -106.00  77.00  30.00  110
  4  ω    -71.00 -40.00   0.50    2.53    -- -106.00  61.00  90.00   62
  5  ω    -71.00 -40.00   0.50    2.53    -- -106.00  61.00 120.00   62
  6  ω    -94.00 -60.00   0.50    2.53    -- -106.00  77.00  60.00   68
  7  ω    -99.00 -61.00   0.50    2.53    -- -106.00  77.00  90.00   76
  8  ω    -79.00 -54.00   0.50    0.63    --  -47.20 -22.00 113.00   50
  9  ω    -25.00  19.00   0.50    0.63    --   47.20 -22.00 113.00   88
 10  ω     -7.00  62.00   0.50    0.63    --   47.20 -57.00  90.00  138
 11  ω     36.00  69.00   0.50    2.53    --  107.75 -61.00   0.00   66
 12  ω     65.00  93.00   0.50    2.53    --  107.75 -94.00   0.00   56
 13  ω     83.00 112.00   0.50    2.53    --  107.75-125.00   0.00   58
 14  ω     44.00  70.00   0.50    2.53    --  107.75-125.00 -90.00   52
 15  ω     38.00  85.00   0.50    2.53    --  107.75 -77.00 -90.00   94
 16  ω     37.00  71.00   0.50    2.53    --  107.75 -61.00-150.00   68
 17  ω     37.00  69.00   0.50    2.53    --  107.75 -61.00 -90.00   64
 18  ω     39.00  78.00   0.50    2.53    --  107.75-125.00   0.00   78
 19  ω     38.00 118.00   0.50    0.63    --   47.20  22.00 -81.00  160
 20  ω     96.00 135.00   0.50    2.53    --  107.75  22.00 -81.00   78
 21  ω    124.00 175.00   0.50    2.53    --  107.75  45.00   0.00  102
 22  ω    147.00 178.00   0.50    2.53    --  107.75  77.00 -30.00   62
 23  ω    103.00 172.00   0.50    2.53    --  107.75  45.00 -30.00  138
 24  ω     86.00 135.00   0.50    2.53    --  107.75  77.00 -30.00   98
 25  ω    -26.00  25.00   0.50    0.63    --   47.20 -19.00 -30.00  102
 26  ω    -64.00 -34.00   0.50    2.53    -- -106.00  61.00 -90.00   60
 27  ω    -63.00 -37.00   0.50    2.53    -- -106.00  61.00-120.00   52
 28  ω    -71.00 -36.00   0.50    2.53    -- -106.00  61.00-180.00   70
 29  ω   -171.00 -95.00   0.50    2.53    -- -106.00 -22.00 113.00  152
 30  ω   -176.00 -99.00   0.50    2.53    -- -106.00 -45.00  30.00  154
 31  ω    -24.00   1.00   0.50    0.63    --   47.20 -22.00 113.00   50
 32  ω     26.00  53.00   0.50    0.63    --   47.20  77.00 -30.00   54
 33  ω     73.00 108.00   0.50    0.63    --   47.20  37.00 -30.00   70
 34  ω     74.00  99.00   0.50    0.63    --   47.20 125.00-180.00   50
 35  ω     29.00  57.00   0.50    0.63    --   47.20  77.00  90.00   56
 36  ω     40.00  67.00   0.50    0.63    --   47.20  77.00   0.00   54
 37  ω     38.00  65.00   0.50    0.63    --   47.20  37.00 -30.00   54
 38  ω     25.00  69.00   0.50    0.63    --   47.20  77.00  30.00   88
 39  ω     52.00  93.00   0.50    0.63    --   47.20  37.00  30.00   82
 40  ω   -123.00 -88.00   0.50    2.53    -- -106.00 -66.00 -26.42   70
 41  ω   -115.00-107.50   0.50    2.53    -- -106.00 -63.00 -13.18   15
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319314000
_diffrn_orient_matrix_UB_12      -0.0567065000
_diffrn_orient_matrix_UB_13      0.0643404000
_diffrn_orient_matrix_UB_21      -0.1134349000
_diffrn_orient_matrix_UB_22      -0.0166777000
_diffrn_orient_matrix_UB_23      0.0149239000
_diffrn_orient_matrix_UB_31      0.0003743000
_diffrn_orient_matrix_UB_32      -0.1965924000
_diffrn_orient_matrix_UB_33      -0.0198010000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21013
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_min         3.841
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25659
_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            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0303
_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)+(0.0439P)²+0.7992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3811
_reflns_number_total             4140
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01584b2.cif
_cod_data_source_block           17723_mme-6
_cod_depositor_comments
'Adding full bibliography for 7158355--7158358.cif.'
_cod_database_code               7158356
_shelx_shelxl_version_number     2014/7
_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.
;
_diffrn_oxdiff_digest_frames
;
0127f9cfa3ba027cbfd235253afde23dce000284cef
;
_diffrn_oxdiff_digest_hkl
;
0191ba616bd7e0766f4a7f92dcff203710f93e
;
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.a Ternary CH refined with riding coordinates:
 C8(H8), C6(H6), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C3(H3), C20(H20), C18(H18), C17(H17)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_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 2.239
_oxdiff_exptl_absorpt_empirical_full_min 0.659
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'
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 -0.17361(2) 0.94899(5) 0.35078(2) 0.02373(10) Uani 1 1 d . . . . .
Cl2 Cl -0.13096(3) 0.74583(5) 0.45951(2) 0.02633(10) Uani 1 1 d . . . . .
O4 O 0.27720(8) 0.77002(13) 0.48721(4) 0.0216(2) Uani 1 1 d . . . . .
O6 O 0.48347(7) 0.73741(13) 0.44932(4) 0.0221(2) Uani 1 1 d . . . . .
O1 O 0.32082(7) 0.74537(12) 0.28460(4) 0.0174(2) Uani 1 1 d . . . . .
O2 O 0.73538(7) 0.34709(13) 0.31235(4) 0.0209(2) Uani 1 1 d . . . . .
O5 O 0.46533(8) 0.98756(13) 0.39465(5) 0.0259(2) Uani 1 1 d . . . . .
O3 O 0.25580(9) 0.50854(13) 0.43946(4) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.34634(8) 0.63654(15) 0.33802(5) 0.0157(2) Uani 1 1 d . . . . .
C2 C 0.25507(10) 0.89636(17) 0.36279(6) 0.0156(3) Uani 1 1 d . . . . .
C19 C 0.64222(10) 0.42896(18) 0.31765(6) 0.0174(3) Uani 1 1 d . . . . .
C12 C 0.28454(10) 0.65990(18) 0.44060(6) 0.0163(3) Uani 1 1 d . . . . .
C21 C 0.52381(10) 0.67183(18) 0.30465(6) 0.0178(3) Uani 1 1 d . . . . .
H21 H 0.5091 0.7871 0.2917 0.021 Uiso 1 1 calc R . . . .
C14 C 0.43353(10) 0.84767(18) 0.41136(6) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.33166(10) 0.76228(17) 0.38922(6) 0.0151(3) Uani 1 1 d . . . . .
C16 C 0.44829(10) 0.56988(18) 0.33029(6) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.22448(10) 1.04414(17) 0.38903(6) 0.0171(3) Uani 1 1 d . . . . .
H3 H 0.2527 1.0720 0.4268 0.021 Uiso 1 1 calc R . . . .
C20 C 0.62124(10) 0.60177(18) 0.29840(6) 0.0181(3) Uani 1 1 d . . . . .
H20 H 0.6718 0.6699 0.2815 0.022 Uiso 1 1 calc R . . . .
C18 C 0.56677(11) 0.32654(18) 0.34305(6) 0.0193(3) Uani 1 1 d . . . . .
H18 H 0.5814 0.2112 0.3559 0.023 Uiso 1 1 calc R . . . .
C8 C 0.01883(10) 0.79070(18) 0.37448(6) 0.0178(3) Uani 1 1 d . . . . .
H8 H 0.0474 0.6872 0.3961 0.021 Uiso 1 1 calc R . . . .
C17 C 0.46970(10) 0.39674(18) 0.34911(6) 0.0181(3) Uani 1 1 d . . . . .
H17 H 0.4190 0.3281 0.3657 0.022 Uiso 1 1 calc R . . . .
C6 C 0.02014(10) 0.96217(18) 0.41166(6) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.0493 0.9465 0.4524 0.023 Uiso 1 1 calc R . . . .
C10 C 0.13690(10) 0.70730(18) 0.29162(6) 0.0183(3) Uani 1 1 d . . . . .
H10A H 0.1501 0.6025 0.3162 0.022 Uiso 1 1 calc R . . . .
H10B H 0.1320 0.6686 0.2502 0.022 Uiso 1 1 calc R . . . .
C11 C 0.22825(10) 0.83371(18) 0.29970(6) 0.0163(3) Uani 1 1 d . . . . .
H11 H 0.2173 0.9375 0.2736 0.020 Uiso 1 1 calc R . . . .
C9 C 0.03353(10) 0.78580(18) 0.30764(6) 0.0182(3) Uani 1 1 d . . . . .
H9A H 0.0280 0.9060 0.2919 0.022 Uiso 1 1 calc R . . . .
H9B H -0.0208 0.7154 0.2885 0.022 Uiso 1 1 calc R . . . .
C4 C 0.14661(11) 1.16893(18) 0.36100(6) 0.0196(3) Uani 1 1 d . . . . .
H4A H 0.1424 1.1491 0.3181 0.024 Uiso 1 1 calc R . . . .
H4B H 0.1691 1.2907 0.3679 0.024 Uiso 1 1 calc R . . . .
C5 C 0.03876(11) 1.14501(18) 0.38601(6) 0.0210(3) Uani 1 1 d . . . . .
H5A H 0.0296 1.2333 0.4170 0.025 Uiso 1 1 calc R . . . .
H5B H -0.0122 1.1677 0.3541 0.025 Uiso 1 1 calc R . . . .
C7 C -0.07760(11) 0.86153(19) 0.39976(6) 0.0202(3) Uani 1 1 d . . . . .
C22 C 0.81982(11) 0.46047(19) 0.30077(7) 0.0221(3) Uani 1 1 d . . . . .
H22A H 0.8104 0.5113 0.2615 0.033 Uiso 1 1 calc GR . . . .
H22B H 0.8819 0.3923 0.3030 0.033 Uiso 1 1 calc GR . . . .
H22C H 0.8239 0.5541 0.3300 0.033 Uiso 1 1 calc GR . . . .
C13 C 0.23119(14) 0.6950(2) 0.53901(6) 0.0296(3) Uani 1 1 d . . . . .
H13A H 0.1617 0.6621 0.5288 0.044 Uiso 1 1 calc GR . . . .
H13B H 0.2323 0.7816 0.5706 0.044 Uiso 1 1 calc GR . . . .
H13C H 0.2689 0.5913 0.5521 0.044 Uiso 1 1 calc GR . . . .
C15 C 0.58725(12) 0.7894(2) 0.46679(8) 0.0322(4) Uani 1 1 d . . . . .
H15A H 0.6288 0.7853 0.4325 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.6144 0.7091 0.4969 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.5872 0.9084 0.4826 0.048 Uiso 1 1 calc GR . . . .
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'
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 115.56(11) . . ?
C14 O6 C15 115.50(12) . . ?
C11 O1 N1 103.23(9) . . ?
C19 O2 C22 116.47(11) . . ?
O1 N1 C1 103.75(9) . . ?
C16 N1 O1 105.83(9) . . ?
C16 N1 C1 117.34(10) . . ?
C3 C2 C1 126.04(12) . . ?
C3 C2 C11 127.64(12) . . ?
C11 C2 C1 106.16(11) . . ?
O2 C19 C20 123.64(12) . . ?
O2 C19 C18 115.85(12) . . ?
C20 C19 C18 120.50(12) . . ?
O4 C12 C1 108.63(11) . . ?
O3 C12 O4 124.76(12) . . ?
O3 C12 C1 126.57(12) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C16 120.23(12) . . ?
O6 C14 C1 109.80(11) . . ?
O5 C14 O6 125.15(12) . . ?
O5 C14 C1 124.95(12) . . ?
N1 C1 C2 102.92(10) . . ?
N1 C1 C12 108.99(10) . . ?
N1 C1 C14 111.60(10) . . ?
C2 C1 C12 110.04(11) . . ?
C2 C1 C14 113.30(11) . . ?
C12 C1 C14 109.76(10) . . ?
C21 C16 N1 122.38(12) . . ?
C17 C16 N1 117.57(12) . . ?
C17 C16 C21 120.05(12) . . ?
C2 C3 H3 118.3 . . ?
C2 C3 C4 123.38(12) . . ?
C4 C3 H3 118.3 . . ?
C19 C20 C21 119.38(13) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 119.95(12) . . ?
C17 C18 H18 120.0 . . ?
C6 C8 H8 113.8 . . ?
C9 C8 H8 113.8 . . ?
C9 C8 C6 123.83(12) . . ?
C7 C8 H8 113.8 . . ?
C7 C8 C6 59.20(9) . . ?
C7 C8 C9 121.66(11) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.89(12) . . ?
C18 C17 H17 120.1 . . ?
C8 C6 H6 113.5 . . ?
C5 C6 C8 123.70(11) . . ?
C5 C6 H6 113.5 . . ?
C7 C6 C8 59.43(9) . . ?
C7 C6 H6 113.5 . . ?
C7 C6 C5 122.73(12) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C11 C10 C9 115.28(11) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
O1 C11 C2 101.51(10) . . ?
O1 C11 C10 110.43(10) . . ?
O1 C11 H11 109.3 . . ?
C2 C11 C10 116.77(11) . . ?
C2 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
C8 C9 C10 113.06(11) . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C3 C4 C5 112.89(11) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C6 C5 C4 113.98(11) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
Cl1 C7 Cl2 111.11(8) . . ?
C8 C7 Cl1 119.14(10) . . ?
C8 C7 Cl2 118.57(10) . . ?
C6 C7 Cl1 120.23(10) . . ?
C6 C7 Cl2 118.48(10) . . ?
C6 C7 C8 61.37(9) . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Cl1 C7 1.7571(14) . ?
Cl2 C7 1.7635(14) . ?
O4 C12 1.3369(16) . ?
O4 C13 1.4434(17) . ?
O6 C14 1.3354(17) . ?
O6 C15 1.4500(18) . ?
O1 N1 1.4732(14) . ?
O1 C11 1.4342(16) . ?
O2 C19 1.3749(16) . ?
O2 C22 1.4272(17) . ?
O5 C14 1.1953(17) . ?
O3 C12 1.1964(17) . ?
N1 C1 1.5026(16) . ?
N1 C16 1.4424(17) . ?
C2 C1 1.5211(18) . ?
C2 C3 1.3249(19) . ?
C2 C11 1.5136(18) . ?
C19 C20 1.390(2) . ?
C19 C18 1.392(2) . ?
C12 C1 1.5342(18) . ?
C21 H21 0.9300 . ?
C21 C16 1.3932(19) . ?
C21 C20 1.3918(19) . ?
C14 C1 1.5410(18) . ?
C16 C17 1.3905(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.5006(19) . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.387(2) . ?
C8 H8 0.9800 . ?
C8 C6 1.5317(19) . ?
C8 C9 1.5161(18) . ?
C8 C7 1.5024(19) . ?
C17 H17 0.9300 . ?
C6 H6 0.9800 . ?
C6 C5 1.511(2) . ?
C6 C7 1.4989(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5305(19) . ?
C10 C9 1.5323(19) . ?
C11 H11 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.551(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
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
O4 C12 C1 N1 176.46(10) . . . . ?
O4 C12 C1 C2 -71.38(13) . . . . ?
O4 C12 C1 C14 53.96(14) . . . . ?
O6 C14 C1 N1 -83.11(13) . . . . ?
O6 C14 C1 C2 161.27(11) . . . . ?
O6 C14 C1 C12 37.83(14) . . . . ?
O1 N1 C1 C2 25.18(12) . . . . ?
O1 N1 C1 C12 141.97(10) . . . . ?
O1 N1 C1 C14 -96.64(11) . . . . ?
O1 N1 C16 C21 37.47(15) . . . . ?
O1 N1 C16 C17 -142.07(11) . . . . ?
O2 C19 C20 C21 178.74(12) . . . . ?
O2 C19 C18 C17 -178.72(12) . . . . ?
O5 C14 C1 N1 93.34(15) . . . . ?
O5 C14 C1 C2 -22.27(19) . . . . ?
O5 C14 C1 C12 -145.72(13) . . . . ?
O3 C12 C1 N1 -5.64(18) . . . . ?
O3 C12 C1 C2 106.51(15) . . . . ?
O3 C12 C1 C14 -128.15(14) . . . . ?
N1 O1 C11 C2 45.86(11) . . . . ?
N1 O1 C11 C10 -78.63(11) . . . . ?
N1 C16 C17 C18 -179.59(11) . . . . ?
C2 C3 C4 C5 100.96(15) . . . . ?
C19 C18 C17 C16 -0.6(2) . . . . ?
C21 C16 C17 C18 0.86(19) . . . . ?
C1 N1 C16 C21 -77.67(15) . . . . ?
C1 N1 C16 C17 102.79(13) . . . . ?
C1 C2 C3 C4 -178.52(12) . . . . ?
C1 C2 C11 O1 -29.56(12) . . . . ?
C1 C2 C11 C10 90.55(13) . . . . ?
C16 N1 C1 C2 141.46(11) . . . . ?
C16 N1 C1 C12 -101.75(12) . . . . ?
C16 N1 C1 C14 19.63(15) . . . . ?
C16 C21 C20 C19 0.4(2) . . . . ?
C3 C2 C1 N1 -173.45(12) . . . . ?
C3 C2 C1 C12 70.51(16) . . . . ?
C3 C2 C1 C14 -52.78(18) . . . . ?
C3 C2 C11 O1 146.12(13) . . . . ?
C3 C2 C11 C10 -93.77(16) . . . . ?
C3 C4 C5 C6 -24.58(16) . . . . ?
C20 C19 C18 C17 0.2(2) . . . . ?
C20 C21 C16 N1 179.71(11) . . . . ?
C20 C21 C16 C17 -0.8(2) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C8 C6 C5 C4 -63.81(17) . . . . ?
C8 C6 C7 Cl1 -108.90(12) . . . . ?
C8 C6 C7 Cl2 108.89(12) . . . . ?
C6 C8 C9 C10 108.54(14) . . . . ?
C6 C8 C7 Cl1 110.63(12) . . . . ?
C6 C8 C7 Cl2 -108.75(11) . . . . ?
C11 O1 N1 C1 -45.58(11) . . . . ?
C11 O1 N1 C16 -169.69(10) . . . . ?
C11 C2 C1 N1 2.32(13) . . . . ?
C11 C2 C1 C12 -113.72(11) . . . . ?
C11 C2 C1 C14 122.99(11) . . . . ?
C11 C2 C3 C4 6.6(2) . . . . ?
C11 C10 C9 C8 -78.47(15) . . . . ?
C9 C8 C6 C5 -1.5(2) . . . . ?
C9 C8 C6 C7 109.64(14) . . . . ?
C9 C8 C7 Cl1 -2.56(18) . . . . ?
C9 C8 C7 Cl2 138.06(11) . . . . ?
C9 C8 C7 C6 -113.20(14) . . . . ?
C9 C10 C11 O1 178.84(10) . . . . ?
C9 C10 C11 C2 63.60(15) . . . . ?
C5 C6 C7 Cl1 3.83(18) . . . . ?
C5 C6 C7 Cl2 -138.39(11) . . . . ?
C5 C6 C7 C8 112.73(14) . . . . ?
C7 C8 C6 C5 -111.16(15) . . . . ?
C7 C8 C9 C10 -179.57(12) . . . . ?
C7 C6 C5 C4 -136.47(13) . . . . ?
C22 O2 C19 C20 16.28(18) . . . . ?
C22 O2 C19 C18 -164.83(12) . . . . ?
C13 O4 C12 O3 0.3(2) . . . . ?
C13 O4 C12 C1 178.23(11) . . . . ?
C15 O6 C14 O5 -5.2(2) . . . . ?
C15 O6 C14 C1 171.27(11) . . . . ?
