#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:26:59 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268928 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158200.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_7158200
loop_
_publ_author_name
'Ding, Weiwei'
'Zhang, Gang'
_publ_section_title
;
 Access to fused π-extended acridone derivatives through a regioselective
 oxidative demethylation.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6985
_journal_page_last               6989
_journal_paper_doi               10.1039/d1ob01249e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         '2(C H Cl3), C34 H27 N3 O2'
_chemical_formula_sum            'C36 H29 Cl6 N3 O2'
_chemical_formula_weight         748.32
_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             2021-01-16
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-06-11 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                101.203(4)
_cell_angle_beta                 101.376(3)
_cell_angle_gamma                103.039(3)
_cell_formula_units_Z            2
_cell_length_a                   11.5804(4)
_cell_length_b                   12.1813(6)
_cell_length_c                   12.9925(5)
_cell_measurement_reflns_used    5571
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.3910
_cell_measurement_theta_min      3.5610
_cell_volume                     1694.85(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  29.00   1.00    1.00    --  -40.73  57.00  60.00   89
  2  ω     31.00  74.00   1.00    1.00    --   40.73-125.00 -30.00   43
  3  ω     27.00  54.00   1.00    1.00    --   40.73-125.00-120.00   27
  4  ω     28.00  93.00   1.00    1.00    --   40.73-125.00-180.00   65
  5  ω     41.00 130.00   1.00    1.00    --  107.58 -61.00-180.00   89
  6  ω     84.00 116.00   1.00    1.00    --  107.58-125.00 -60.00   32
  7  ω     42.00 138.00   1.00    1.00    --  107.58 -77.00 -60.00   96
  8  ω     83.00 117.00   1.00    1.00    --  107.58  45.00  90.00   34
  9  ω    140.00 172.00   1.00    1.00    --  107.58  45.00  90.00   32
 10  ω     99.00 147.00   1.00    1.00    --  107.58  45.00 150.00   48
 11  ω     60.00 107.00   1.00    1.00    --  107.58 -94.00 150.00   47
 12  ω     69.00 121.00   1.00    1.00    --  107.58-125.00 120.00   52
 13  ω     35.00 132.00   1.00    1.00    --  107.58 -45.00  60.00   97
 14  ω     39.00 136.00   1.00    1.00    --  107.58 -30.00 -90.00   97
 15  ω     39.00 155.00   1.00    1.00    --  107.58 -15.00 120.00  116
 16  ω   -129.00  35.00   1.00    1.00    --  -40.73   0.00-120.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0634279000
_diffrn_orient_matrix_UB_12      -0.0119165000
_diffrn_orient_matrix_UB_13      -0.0936561000
_diffrn_orient_matrix_UB_21      0.0053484000
_diffrn_orient_matrix_UB_22      -0.1228141000
_diffrn_orient_matrix_UB_23      0.0100311000
_diffrn_orient_matrix_UB_31      -0.1259462000
_diffrn_orient_matrix_UB_32      -0.0524479000
_diffrn_orient_matrix_UB_33      -0.0820491000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11542
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.963
_diffrn_reflns_theta_min         3.584
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.935
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0465
_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)+(0.0558P)²+0.9297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5534
_reflns_number_total             6648
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01249e2.cif
_cod_data_source_block           dw218
_cod_depositor_comments
'Adding full bibliography for 7158198--7158200.cif.'
_cod_database_code               7158200
_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.
;
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C35(H35), C36(H36)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C20(H20), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C34(H34A,H34B,H34C)
;
_olex2_date_sample_data_collection 2021-01-16
_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 2.192
_oxdiff_exptl_absorpt_empirical_full_min 0.760
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 0.51119(7) -0.02896(10) 0.28964(6) 0.0699(3) Uani 1 1 d . . . . .
Cl2 Cl 0.76579(8) -0.02442(7) 0.35497(6) 0.0553(2) Uani 1 1 d . . . . .
Cl3 Cl 0.65406(6) 0.08788(6) 0.50798(5) 0.03736(15) Uani 1 1 d . . . . .
C35 C 0.6570(2) 0.0528(2) 0.37051(19) 0.0312(5) Uani 1 1 d . . . . .
H35 H 0.680633 0.125161 0.347976 0.037 Uiso 1 1 calc R U . . .
Cl4 Cl 0.89171(7) 0.93515(6) 0.61948(5) 0.04161(17) Uani 1 1 d . . . . .
Cl5 Cl 1.04011(10) 0.85221(8) 0.77579(8) 0.0820(4) Uani 1 1 d . . . . .
Cl6 Cl 0.78942(12) 0.84803(9) 0.78240(8) 0.0830(4) Uani 1 1 d . . . . .
C36 C 0.8909(3) 0.8345(2) 0.6993(2) 0.0439(7) Uani 1 1 d . . . . .
H36 H 0.861697 0.756155 0.650703 0.053 Uiso 1 1 calc R U . . .
O1 O 0.65293(16) 0.20459(15) 0.20986(13) 0.0343(4) Uani 1 1 d . . . . .
O2 O 0.64646(15) 0.68307(14) 0.52384(14) 0.0321(4) Uani 1 1 d . . . . .
N1 N 0.42731(17) 0.41630(16) 0.18178(15) 0.0236(4) Uani 1 1 d . . . . .
N2 N 0.75897(17) 0.33434(16) 0.41677(15) 0.0241(4) Uani 1 1 d . . . . .
N3 N 0.80084(17) 0.55708(17) 0.55647(15) 0.0251(4) Uani 1 1 d . . . . .
C1 C 0.3623(2) 0.50085(19) 0.15943(17) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.4094(2) 0.5841(2) 0.10876(18) 0.0265(5) Uani 1 1 d . . . . .
H2 H 0.483247 0.586232 0.090158 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3463(2) 0.6649(2) 0.08543(18) 0.0258(5) Uani 1 1 d . . . . .
H3 H 0.378443 0.720140 0.050766 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2361(2) 0.66419(19) 0.11318(17) 0.0231(4) Uani 1 1 d . . . . .
C5 C 0.1915(2) 0.5793(2) 0.16516(19) 0.0278(5) Uani 1 1 d . . . . .
H5 H 0.118175 0.577255 0.184773 0.033 Uiso 1 1 calc R U . . .
C6 C 0.2530(2) 0.4983(2) 0.18838(19) 0.0277(5) Uani 1 1 d . . . . .
H6 H 0.221311 0.442783 0.222983 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1631(2) 0.7508(2) 0.08949(18) 0.0259(5) Uani 1 1 d . . . . .
C8 C 0.0363(2) 0.6830(2) 0.0136(2) 0.0381(6) Uani 1 1 d . . . . .
H8A H 0.046396 0.640105 -0.052712 0.057 Uiso 1 1 calc R U . . .
H8B H -0.009850 0.736738 -0.002018 0.057 Uiso 1 1 calc R U . . .
H8C H -0.006523 0.630124 0.048280 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1464(3) 0.8174(2) 0.1960(2) 0.0414(6) Uani 1 1 d . . . . .
H9A H 0.104689 0.763273 0.230297 0.062 Uiso 1 1 calc R U . . .
H9B H 0.098901 0.870276 0.181128 0.062 Uiso 1 1 calc R U . . .
H9C H 0.225170 0.860307 0.243295 0.062 Uiso 1 1 calc R U . . .
C10 C 0.2270(2) 0.8389(2) 0.0355(2) 0.0326(5) Uani 1 1 d . . . . .
H10A H 0.306505 0.881143 0.081779 0.049 Uiso 1 1 calc R U . . .
H10B H 0.179031 0.892139 0.023540 0.049 Uiso 1 1 calc R U . . .
H10C H 0.235588 0.798748 -0.032612 0.049 Uiso 1 1 calc R U . . .
C11 C 0.3993(2) 0.31125(19) 0.10361(17) 0.0237(4) Uani 1 1 d . . . . .
C12 C 0.4721(2) 0.2350(2) 0.11694(18) 0.0249(5) Uani 1 1 d . . . . .
C13 C 0.4420(2) 0.1283(2) 0.04049(19) 0.0290(5) Uani 1 1 d . . . . .
H13 H 0.490273 0.077648 0.049302 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3428(2) 0.0968(2) -0.04724(19) 0.0319(5) Uani 1 1 d . . . . .
H14 H 0.323683 0.025402 -0.097308 0.038 Uiso 1 1 calc R U . . .
C15 C 0.2707(2) 0.1735(2) -0.06036(19) 0.0320(5) Uani 1 1 d . . . . .
H15 H 0.202897 0.152447 -0.119359 0.038 Uiso 1 1 calc R U . . .
C16 C 0.2988(2) 0.2798(2) 0.01300(19) 0.0294(5) Uani 1 1 d . . . . .
H16 H 0.251171 0.330687 0.002458 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5803(2) 0.26490(19) 0.20937(18) 0.0245(4) Uani 1 1 d . . . . .
C18 C 0.5921(2) 0.36711(19) 0.29447(17) 0.0219(4) Uani 1 1 d . . . . .
C19 C 0.5166(2) 0.44049(19) 0.27668(17) 0.0229(4) Uani 1 1 d . . . . .
C20 C 0.5317(2) 0.5468(2) 0.35510(18) 0.0252(5) Uani 1 1 d . . . . .
H20 H 0.477002 0.591035 0.342687 0.030 Uiso 1 1 calc R U . . .
C21 C 0.6238(2) 0.58389(19) 0.44682(18) 0.0240(4) Uani 1 1 d . . . . .
C22 C 0.7094(2) 0.51545(19) 0.46899(17) 0.0227(4) Uani 1 1 d . . . . .
C23 C 0.68861(19) 0.40358(19) 0.39420(17) 0.0219(4) Uani 1 1 d . . . . .
C24 C 0.8547(2) 0.37611(19) 0.50667(17) 0.0228(4) Uani 1 1 d . . . . .
C25 C 0.8783(2) 0.49001(19) 0.57565(17) 0.0233(4) Uani 1 1 d . . . . .
C26 C 0.9334(2) 0.3069(2) 0.53056(18) 0.0267(5) Uani 1 1 d . . . . .
H26 H 0.918281 0.232980 0.485855 0.032 Uiso 1 1 calc R U . . .
C27 C 1.0338(2) 0.3479(2) 0.62057(18) 0.0257(5) Uani 1 1 d . . . . .
C28 C 1.0578(2) 0.4629(2) 0.68931(18) 0.0259(5) Uani 1 1 d . . . . .
C29 C 0.9799(2) 0.5316(2) 0.66518(18) 0.0269(5) Uani 1 1 d . . . . .
H29 H 0.995738 0.605992 0.709183 0.032 Uiso 1 1 calc R U . . .
C30 C 1.1159(2) 0.2791(2) 0.64634(19) 0.0301(5) Uani 1 1 d . . . . .
H30 H 1.102309 0.205098 0.602378 0.036 Uiso 1 1 calc R U . . .
C31 C 1.2129(2) 0.3212(2) 0.7342(2) 0.0326(5) Uani 1 1 d . . . . .
H31 H 1.265668 0.275862 0.749434 0.039 Uiso 1 1 calc R U . . .
C32 C 1.2351(2) 0.4338(2) 0.80342(19) 0.0321(5) Uani 1 1 d . . . . .
H32 H 1.301154 0.460574 0.864266 0.038 Uiso 1 1 calc R U . . .
C33 C 1.1609(2) 0.5023(2) 0.78141(19) 0.0297(5) Uani 1 1 d . . . . .
H33 H 1.177210 0.576008 0.826941 0.036 Uiso 1 1 calc R U . . .
C34 C 0.5671(2) 0.7564(2) 0.5062(2) 0.0350(6) Uani 1 1 d . . . . .
H34A H 0.574580 0.782827 0.442240 0.052 Uiso 1 1 calc R U . . .
H34B H 0.589821 0.822261 0.567564 0.052 Uiso 1 1 calc R U . . .
H34C H 0.483898 0.713182 0.497058 0.052 Uiso 1 1 calc R U . . .
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
Cl1 C35 Cl3 110.22(14) . . ?
Cl1 C35 H35 108.8 . . ?
Cl2 C35 Cl1 110.75(14) . . ?
Cl2 C35 Cl3 109.57(13) . . ?
Cl2 C35 H35 108.8 . . ?
Cl3 C35 H35 108.8 . . ?
Cl4 C36 Cl5 110.33(17) . . ?
Cl4 C36 Cl6 110.35(17) . . ?
Cl4 C36 H36 108.1 . . ?
Cl5 C36 Cl6 111.70(16) . . ?
Cl5 C36 H36 108.1 . . ?
Cl6 C36 H36 108.1 . . ?
C21 O2 C34 117.08(18) . . ?
C11 N1 C1 118.33(17) . . ?
C19 N1 C1 120.53(18) . . ?
C19 N1 C11 121.12(18) . . ?
C23 N2 C24 117.74(19) . . ?
C22 N3 C25 117.02(19) . . ?
C2 C1 N1 119.80(19) . . ?
C2 C1 C6 120.1(2) . . ?
C6 C1 N1 120.1(2) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 117.3(2) . . ?
C3 C4 C7 123.2(2) . . ?
C5 C4 C7 119.5(2) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C4 C7 C8 108.93(19) . . ?
C4 C7 C9 109.35(19) . . ?
C9 C7 C8 109.2(2) . . ?
C10 C7 C4 112.30(19) . . ?
C10 C7 C8 108.7(2) . . ?
C10 C7 C9 108.4(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 119.2(2) . . ?
N1 C11 C16 121.5(2) . . ?
C12 C11 C16 119.4(2) . . ?
C11 C12 C17 121.6(2) . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 C17 119.2(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.1(2) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
O1 C17 C12 119.7(2) . . ?
O1 C17 C18 125.1(2) . . ?
C18 C17 C12 115.21(19) . . ?
C19 C18 C17 119.85(19) . . ?
C19 C18 C23 117.74(19) . . ?
C23 C18 C17 122.09(19) . . ?
N1 C19 C18 121.8(2) . . ?
N1 C19 C20 116.61(19) . . ?
C18 C19 C20 121.6(2) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.3(2) . . ?
C21 C20 H20 119.3 . . ?
O2 C21 C20 125.6(2) . . ?
O2 C21 C22 113.99(19) . . ?
C20 C21 C22 120.44(19) . . ?
N3 C22 C21 118.53(19) . . ?
N3 C22 C23 123.18(19) . . ?
C23 C22 C21 118.28(19) . . ?
N2 C23 C18 119.83(19) . . ?
N2 C23 C22 119.84(19) . . ?
C22 C23 C18 120.33(19) . . ?
N2 C24 C25 121.34(19) . . ?
N2 C24 C26 119.2(2) . . ?
C26 C24 C25 119.5(2) . . ?
N3 C25 C24 120.57(19) . . ?
N3 C25 C29 119.7(2) . . ?
C29 C25 C24 119.7(2) . . ?
C24 C26 H26 119.6 . . ?
C27 C26 C24 120.7(2) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C28 119.6(2) . . ?
C26 C27 C30 121.8(2) . . ?
C30 C27 C28 118.6(2) . . ?
C29 C28 C27 119.5(2) . . ?
C29 C28 C33 122.1(2) . . ?
C33 C28 C27 118.4(2) . . ?
C25 C29 H29 119.5 . . ?
C28 C29 C25 120.9(2) . . ?
C28 C29 H29 119.5 . . ?
C27 C30 H30 119.7 . . ?
C31 C30 C27 120.5(2) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C32 120.9(2) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 H32 119.7 . . ?
C33 C32 C31 120.5(2) . . ?
C33 C32 H32 119.7 . . ?
C28 C33 H33 119.5 . . ?
C32 C33 C28 121.0(2) . . ?
C32 C33 H33 119.5 . . ?
O2 C34 H34A 109.5 . . ?
O2 C34 H34B 109.5 . . ?
O2 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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 C35 1.755(3) . ?
Cl2 C35 1.754(3) . ?
Cl3 C35 1.763(2) . ?
C35 H35 0.9800 . ?
Cl4 C36 1.752(3) . ?
Cl5 C36 1.759(3) . ?
Cl6 C36 1.759(3) . ?
C36 H36 0.9800 . ?
O1 C17 1.235(3) . ?
O2 C21 1.347(3) . ?
O2 C34 1.436(3) . ?
N1 C1 1.446(3) . ?
N1 C11 1.397(3) . ?
N1 C19 1.377(3) . ?
N2 C23 1.332(3) . ?
N2 C24 1.362(3) . ?
N3 C22 1.315(3) . ?
N3 C25 1.362(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.385(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(3) . ?
C4 C5 1.400(3) . ?
C4 C7 1.532(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.541(3) . ?
C7 C9 1.534(3) . ?
C7 C10 1.526(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.401(3) . ?
C11 C16 1.404(3) . ?
C12 C13 1.398(3) . ?
C12 C17 1.475(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.371(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.456(3) . ?
C18 C19 1.403(3) . ?
C18 C23 1.451(3) . ?
C19 C20 1.435(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.354(3) . ?
C21 C22 1.454(3) . ?
C22 C23 1.451(3) . ?
C24 C25 1.433(3) . ?
C24 C26 1.405(3) . ?
C25 C29 1.399(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.395(3) . ?
C27 C28 1.442(3) . ?
C27 C30 1.435(3) . ?
C28 C29 1.393(3) . ?
C28 C33 1.429(3) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C30 C31 1.354(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.424(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.355(3) . ?
C33 H33 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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
O1 C17 C18 C19 168.7(2) . . . . ?
O1 C17 C18 C23 -4.6(4) . . . . ?
O2 C21 C22 N3 -2.7(3) . . . . ?
O2 C21 C22 C23 176.34(19) . . . . ?
N1 C1 C2 C3 179.0(2) . . . . ?
N1 C1 C6 C5 -179.3(2) . . . . ?
N1 C11 C12 C13 178.1(2) . . . . ?
N1 C11 C12 C17 -2.3(3) . . . . ?
N1 C11 C16 C15 -177.4(2) . . . . ?
N1 C19 C20 C21 -174.1(2) . . . . ?
N2 C24 C25 N3 3.9(3) . . . . ?
N2 C24 C25 C29 -177.8(2) . . . . ?
N2 C24 C26 C27 178.6(2) . . . . ?
N3 C22 C23 N2 4.7(3) . . . . ?
N3 C22 C23 C18 -174.8(2) . . . . ?
N3 C25 C29 C28 177.3(2) . . . . ?
C1 N1 C11 C12 171.48(19) . . . . ?
C1 N1 C11 C16 -9.5(3) . . . . ?
C1 N1 C19 C18 -171.5(2) . . . . ?
C1 N1 C19 C20 6.4(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C7 -180.0(2) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C3 C4 C7 C8 118.8(2) . . . . ?
C3 C4 C7 C9 -122.0(2) . . . . ?
C3 C4 C7 C10 -1.7(3) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C5 C4 C7 C8 -61.2(3) . . . . ?
C5 C4 C7 C9 58.0(3) . . . . ?
C5 C4 C7 C10 178.4(2) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C7 C4 C5 C6 179.7(2) . . . . ?
C11 N1 C1 C2 -90.6(3) . . . . ?
C11 N1 C1 C6 89.2(3) . . . . ?
C11 N1 C19 C18 6.8(3) . . . . ?
C11 N1 C19 C20 -175.31(19) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C11 C12 C17 O1 -168.8(2) . . . . ?
C11 C12 C17 C18 10.9(3) . . . . ?
C12 C11 C16 C15 1.7(3) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C12 C17 C18 C19 -11.0(3) . . . . ?
C12 C17 C18 C23 175.72(19) . . . . ?
C13 C12 C17 O1 10.8(3) . . . . ?
C13 C12 C17 C18 -169.5(2) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C11 -1.4(4) . . . . ?
C16 C11 C12 C13 -1.0(3) . . . . ?
C16 C11 C12 C17 178.6(2) . . . . ?
C17 C12 C13 C14 -179.6(2) . . . . ?
C17 C18 C19 N1 2.7(3) . . . . ?
C17 C18 C19 C20 -175.1(2) . . . . ?
C17 C18 C23 N2 -9.5(3) . . . . ?
C17 C18 C23 C22 170.0(2) . . . . ?
C18 C19 C20 C21 3.8(3) . . . . ?
C19 N1 C1 C2 87.8(3) . . . . ?
C19 N1 C1 C6 -92.4(3) . . . . ?
C19 N1 C11 C12 -6.9(3) . . . . ?
C19 N1 C11 C16 172.2(2) . . . . ?
C19 C18 C23 N2 177.0(2) . . . . ?
C19 C18 C23 C22 -3.4(3) . . . . ?
C19 C20 C21 O2 178.7(2) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 N3 177.0(2) . . . . ?
C20 C21 C22 C23 -3.9(3) . . . . ?
C21 C22 C23 N2 -174.3(2) . . . . ?
C21 C22 C23 C18 6.1(3) . . . . ?
C22 N3 C25 C24 -4.1(3) . . . . ?
C22 N3 C25 C29 177.6(2) . . . . ?
C23 N2 C24 C25 0.8(3) . . . . ?
C23 N2 C24 C26 -177.7(2) . . . . ?
C23 C18 C19 N1 176.3(2) . . . . ?
C23 C18 C19 C20 -1.5(3) . . . . ?
C24 N2 C23 C18 174.71(19) . . . . ?
C24 N2 C23 C22 -4.8(3) . . . . ?
C24 C25 C29 C28 -1.0(3) . . . . ?
C24 C26 C27 C28 -0.6(3) . . . . ?
C24 C26 C27 C30 -179.7(2) . . . . ?
C25 N3 C22 C21 179.06(19) . . . . ?
C25 N3 C22 C23 0.0(3) . . . . ?
C25 C24 C26 C27 0.1(3) . . . . ?
C26 C24 C25 N3 -177.6(2) . . . . ?
C26 C24 C25 C29 0.7(3) . . . . ?
C26 C27 C28 C29 0.3(3) . . . . ?
C26 C27 C28 C33 179.5(2) . . . . ?
C26 C27 C30 C31 179.9(2) . . . . ?
C27 C28 C29 C25 0.5(3) . . . . ?
C27 C28 C33 C32 0.6(3) . . . . ?
C27 C30 C31 C32 0.6(4) . . . . ?
C28 C27 C30 C31 0.8(3) . . . . ?
C29 C28 C33 C32 179.8(2) . . . . ?
C30 C27 C28 C29 179.4(2) . . . . ?
C30 C27 C28 C33 -1.3(3) . . . . ?
C30 C31 C32 C33 -1.4(4) . . . . ?
C31 C32 C33 C28 0.8(4) . . . . ?
C33 C28 C29 C25 -178.7(2) . . . . ?
C34 O2 C21 C20 -1.0(3) . . . . ?
C34 O2 C21 C22 178.7(2) . . . . ?
