#------------------------------------------------------------------------------
#$Date: 2020-07-04 04:44:54 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253720 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/77/4517753.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_4517753
loop_
_publ_author_name
'Liu, Xin'
'Carr, Paul'
'Gardiner, Michael G.'
'Banwell, Martin G.'
'Elbanna, Ahmed H.'
'Khalil, Zeinab G.'
'Capon, Robert J.'
_publ_section_title
;
 Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as
 Scaffolds for Drug Discovery and Development.
;
_journal_issue                   23
_journal_name_full               'ACS omega'
_journal_page_first              13926
_journal_page_last               13939
_journal_paper_doi               10.1021/acsomega.0c01331
_journal_volume                  5
_journal_year                    2020
_chemical_formula_sum            'C13 H14 Cl2 N2 O2'
_chemical_formula_weight         301.16
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-08-23
_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_audit_update_record
;
2017-08-24 # Formatted by publCIF

;
_cell_angle_alpha                112.584(3)
_cell_angle_beta                 102.063(3)
_cell_angle_gamma                99.352(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3394(3)
_cell_length_b                   9.2251(3)
_cell_length_c                   10.2483(3)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6000
_cell_measurement_theta_min      4.8850
_cell_volume                     685.68(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics
'SHELXLE (C. B. HÃ¼bschle et al.,2011)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9837
_diffrn_measured_fraction_theta_max 0.7972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     23.00  90.00   1.00    1.00    --   36.95-125.00 -30.00   67
  2  ω     10.00 105.00   1.00    1.00    --   36.95  77.00-150.00   95
  3  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00   0.00   75
  4  ω    -30.00  54.00   1.00    1.00    --   36.95 -57.00 -30.00   84
  5  ω     18.00 106.00   1.00    1.00    --   36.95  38.00 -30.00   88
  6  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00  60.00   75
  7  ω     23.00  90.00   1.00    1.00    --   36.95-125.00 -90.00   67
  8  ω     20.00 104.00   1.00    1.00    --   36.95  57.00  60.00   84
  9  ω    -30.00  54.00   1.00    1.00    --   36.95 -57.00  90.00   84
 10  ω    -30.00  54.00   1.00    1.00    --   36.95 -57.00-180.00   84
 11  ω     43.00 128.00   1.00    1.00    --  111.00 -50.00-180.00   85
 12  ω     57.00 150.00   1.00    1.00    --  111.00 178.00  30.00   93
 13  ω     43.00 138.00   1.00    1.00    --  111.00 -77.00 -30.00   95
 14  ω     43.00 138.00   1.00    1.00    --  111.00 -77.00  90.00   95
 15  ω     41.00 136.00   1.00    1.00    --  111.00 -25.00-180.00   95
 16  ω     42.00 130.00   1.00    1.00    --  111.00 -38.00  60.00   88
 17  ω     92.00 178.00   1.00    1.00    --  111.00  38.00   0.00   86
 18  ω     41.00 157.00   1.00    1.00    --  111.00 -12.00  30.00  116
 19  ω     41.00 116.00   1.00    1.00    --  111.00-111.00 -90.00   75
 20  ω     41.00 136.00   1.00    1.00    --  111.00 -25.00  90.00   95
 21  ω     41.00 116.00   1.00    1.00    --  111.00-111.00-150.00   75
 22  ω     92.00 178.00   1.00    1.00    --  111.00  38.00  30.00   86
 23  ω     42.00 130.00   1.00    1.00    --  111.00 -38.00 -30.00   88
 24  ω     41.00 116.00   1.00    1.00    --  111.00-111.00  60.00   75
 25  ω     92.00 178.00   1.00    1.00    --  111.00  38.00-120.00   86
 26  ω     43.00 138.00   1.00    1.00    --  111.00 -77.00 120.00   95
 27  ω     43.00 128.00   1.00    1.00    --  111.00 -50.00 -30.00   85
 28  ω     41.00 116.00   1.00    1.00    --  111.00-111.00 -30.00   75
 29  ω     43.00 138.00   1.00    1.00    --  111.00 -77.00 -90.00   95
 30  ω     92.00 178.00   1.00    1.00    --  111.00  38.00  60.00   86
 31  ω     44.00 131.00   1.00    1.00    --  111.00 -64.00 -90.00   87
 32  ω     42.00 130.00   1.00    1.00    --  111.00 -38.00-120.00   88
 33  ω     57.00 150.00   1.00    1.00    --  111.00 178.00 -30.00   93
 34  ω     42.00 178.00   1.00    1.00    --  111.00   5.00 165.98  136
 35  ω     42.00 146.00   1.00    1.00    --  111.00 -92.00  90.00  104
 36  ω   -104.00 -20.00   1.00    1.00    --  -36.95 -57.00-150.00   84
 37  ω     10.00 105.00   1.00    1.00    --   36.95  77.00  30.00   95
 38  ω     20.00 104.00   1.00    1.00    --   36.95  57.00  30.00   84
 39  ω     10.00 105.00   1.00    1.00    --   36.95  77.00 -30.00   95
 40  ω     10.00 105.00   1.00    1.00    --   36.95  77.00 150.00   95
 41  ω      8.00 108.00   1.00    1.00    --   36.95  19.00-120.00  100
 42  ω    -32.00  56.00   1.00    1.00    --   36.95 -38.00-120.00   88
 43  ω     20.00 104.00   1.00    1.00    --   36.95  57.00 120.00   84
 44  ω     10.00 105.00   1.00    1.00    --   36.95  77.00 120.00   95
 45  ω     10.00 105.00   1.00    1.00    --   36.95  77.00-120.00   95
 46  ω     92.00 178.00   1.00    1.00    --  111.00  38.00-150.00   86
 47  ω     92.00 178.00   1.00    1.00    --  111.00  38.00 -60.00   86
 48  ω     92.00 178.00   1.00    1.00    --  111.00  38.00-180.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1254854000
_diffrn_orient_matrix_UB_12      0.0331538000
_diffrn_orient_matrix_UB_13      0.1483260000
_diffrn_orient_matrix_UB_21      -0.1476545000
_diffrn_orient_matrix_UB_22      -0.0009817000
_diffrn_orient_matrix_UB_23      0.0685837000
_diffrn_orient_matrix_UB_31      -0.0302793000
_diffrn_orient_matrix_UB_32      -0.1848289000
_diffrn_orient_matrix_UB_33      -0.0488215000
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13949
_diffrn_reflns_theta_full        74.3338
_diffrn_reflns_theta_max         73.7986
_diffrn_reflns_theta_min         4.8960
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.262
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4429
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.1609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0873
_reflns_number_gt                4363
_reflns_number_total             4429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao0c01331_si_010.cif
_cod_data_source_block           ban17_42sn
_cod_depositor_comments
'Adding full bibliography for 4517747--4517755.cif.'
_cod_original_cell_volume        685.67(4)
_cod_database_code               4517753
_publcif_datablock.id            {b49adb2c-5c23-4eaa-9b2e-757b3e6d510b}
loop_
_symmetry_equiv_pos_as_xyz
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5804(3) 0.2841(3) 0.9416(2) 0.0267(5) Uani 1 1 d . . .
H1 H 0.6478 0.2241 0.9844 0.032 Uiso 1 1 calc R . .
C2 C 0.6748(3) 0.3688(3) 0.8716(2) 0.0218(4) Uani 1 1 d . . .
C3 C 0.5906(3) 0.4109(3) 0.7667(2) 0.0205(4) Uani 1 1 d . . .
C4 C 0.3994(3) 0.3639(3) 0.7137(2) 0.0260(4) Uani 1 1 d . . .
H4A H 0.3574 0.2815 0.6091 0.031 Uiso 1 1 calc R . .
H4B H 0.3580 0.4606 0.7209 0.031 Uiso 1 1 calc R . .
C5 C 0.3353(3) 0.2935(3) 0.8127(3) 0.0347(6) Uani 1 1 d . . .
H5 H 0.2100 0.2409 0.7701 0.042 Uiso 1 1 calc R . .
O6 O 0.4232(2) 0.1795(2) 0.83054(18) 0.0345(4) Uani 1 1 d . . .
N9 N 0.8476(2) 0.4234(2) 0.90421(19) 0.0234(4) Uani 1 1 d . . .
H9 H 0.9249 0.4104 0.9686 0.028 Uiso 1 1 calc R . .
O8 O 0.3729(2) 0.4225(3) 0.9584(2) 0.0390(4) Uani 1 1 d . . .
C7 C 0.5122(3) 0.4016(4) 1.0530(3) 0.0346(5) Uani 1 1 d . . .
H7A H 0.4723 0.3539 1.1160 0.042 Uiso 1 1 calc R . .
H7B H 0.5997 0.5063 1.1170 0.042 Uiso 1 1 calc R . .
C10 C 0.8787(3) 0.5020(3) 0.8186(2) 0.0208(4) Uani 1 1 d . . .
C11 C 0.7190(2) 0.4975(3) 0.7312(2) 0.0190(4) Uani 1 1 d . . .
C12 C 1.0291(3) 0.5767(3) 0.8049(2) 0.0249(4) Uani 1 1 d . . .
H12 H 1.1375 0.5811 0.8611 0.030 Uiso 1 1 calc R . .
C13 C 1.0122(3) 0.6443(3) 0.7050(2) 0.0253(4) Uani 1 1 d . . .
H13 H 1.1113 0.6960 0.6912 0.030 Uiso 1 1 calc R . .
C14 C 0.8504(3) 0.6378(3) 0.6233(2) 0.0230(4) Uani 1 1 d . . .
N15 N 0.7048(2) 0.5661(2) 0.63601(18) 0.0196(3) Uani 1 1 d . . .
C16 C 0.8361(3) 0.7144(4) 0.5172(3) 0.0356(6) Uani 1 1 d . . .
H16A H 0.7157 0.6987 0.4697 0.053 Uiso 0.50 1 calc PR . .
H16B H 0.8900 0.6632 0.4416 0.053 Uiso 0.50 1 calc PR . .
H16C H 0.8932 0.8313 0.5713 0.053 Uiso 0.50 1 calc PR . .
H16D H 0.9502 0.7635 0.5187 0.053 Uiso 0.50 1 calc PR . .
H16E H 0.7759 0.7989 0.5468 0.053 Uiso 0.50 1 calc PR . .
H16F H 0.7727 0.6308 0.4171 0.053 Uiso 0.50 1 calc PR . .
C21 C 0.3815(3) 0.8486(3) 0.5334(2) 0.0250(4) Uani 1 1 d . . .
H21 H 0.4352 0.8703 0.6383 0.030 Uiso 1 1 calc R . .
C22 C 0.3240(3) 0.6719(3) 0.4307(2) 0.0214(4) Uani 1 1 d . . .
C23 C 0.1985(3) 0.6145(3) 0.2986(2) 0.0201(4) Uani 1 1 d . . .
C24 C 0.1143(3) 0.7276(3) 0.2542(2) 0.0232(4) Uani 1 1 d . . .
H24A H -0.0076 0.7020 0.2488 0.028 Uiso 1 1 calc R . .
H24B H 0.1225 0.7155 0.1558 0.028 Uiso 1 1 calc R . .
C25 C 0.2057(3) 0.9012(3) 0.3708(2) 0.0249(4) Uani 1 1 d . . .
H25 H 0.1376 0.9774 0.3588 0.030 Uiso 1 1 calc R . .
O26 O 0.2338(2) 0.9111(2) 0.51588(17) 0.0279(3) Uani 1 1 d . . .
C27 C 0.4933(3) 0.9452(3) 0.4775(3) 0.0290(5) Uani 1 1 d . . .
H27A H 0.5539 1.0561 0.5560 0.035 Uiso 1 1 calc R . .
H27B H 0.5776 0.8888 0.4416 0.035 Uiso 1 1 calc R . .
O28 O 0.3718(2) 0.9506(2) 0.35819(19) 0.0288(3) Uani 1 1 d . . .
N29 N 0.3827(2) 0.5472(2) 0.44792(19) 0.0227(4) Uani 1 1 d . . .
H29 H 0.477(4) 0.561(4) 0.516(3) 0.029(7) Uiso 1 1 d . . .
C30 C 0.2947(2) 0.4054(3) 0.3238(2) 0.0201(4) Uani 1 1 d . . .
C31 C 0.1767(2) 0.4434(3) 0.2280(2) 0.0189(4) Uani 1 1 d . . .
C32 C 0.3022(3) 0.2450(3) 0.2821(3) 0.0251(4) Uani 1 1 d . . .
H32 H 0.3778 0.2149 0.3441 0.030 Uiso 1 1 calc R . .
C33 C 0.1937(3) 0.1313(3) 0.1453(3) 0.0278(5) Uani 1 1 d . . .
H33 H 0.1955 0.0204 0.1118 0.033 Uiso 1 1 calc R . .
C34 C 0.0805(3) 0.1766(3) 0.0544(2) 0.0254(4) Uani 1 1 d . . .
N35 N 0.0697(2) 0.3302(2) 0.09513(19) 0.0218(4) Uani 1 1 d . . .
C36 C -0.0320(4) 0.0523(3) -0.0969(3) 0.0410(6) Uani 1 1 d . . .
H36A H -0.1014 0.1052 -0.1438 0.062 Uiso 0.50 1 calc PR . .
H36B H -0.1066 -0.0342 -0.0871 0.062 Uiso 0.50 1 calc PR . .
H36C H 0.0389 0.0052 -0.1580 0.062 Uiso 0.50 1 calc PR . .
H36D H -0.0113 -0.0544 -0.1155 0.062 Uiso 0.50 1 calc PR . .
H36E H -0.0062 0.0850 -0.1722 0.062 Uiso 0.50 1 calc PR . .
H36F H -0.1516 0.0456 -0.1012 0.062 Uiso 0.50 1 calc PR . .
C40 C 0.5330(4) 0.8166(4) 1.0679(3) 0.0415(6) Uani 1 1 d . . .
H40A H 0.4681 0.7026 1.0350 0.050 Uiso 1 1 calc R . .
H40B H 0.5120 0.8850 1.1608 0.050 Uiso 1 1 calc R . .
Cl41 Cl 0.46058(8) 0.88221(9) 0.93205(7) 0.04794(18) Uani 1 1 d . . .
Cl42 Cl 0.75229(9) 0.82855(10) 1.10220(9) 0.0551(2) Uani 1 1 d . . .
C50 C 0.9240(3) 0.2578(4) 0.3903(3) 0.0394(6) Uani 1 1 d . . .
H50A H 0.9789 0.2031 0.3153 0.047 Uiso 1 1 calc R . .
H50B H 0.9932 0.3722 0.4496 0.047 Uiso 1 1 calc R . .
Cl51 Cl 0.71742(10) 0.25428(10) 0.30017(8) 0.0553(2) Uani 1 1 d . . .
Cl52 Cl 0.91874(9) 0.15911(9) 0.50731(7) 0.04814(18) 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 0.0181 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'
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'
Cl Cl 0.3639 0.7018 '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
O6 C1 C2 106.68(17) . . ?
O6 C1 C7 100.1(2) . . ?
C2 C1 C7 110.8(2) . . ?
O6 C1 H1 112.8 . . ?
C2 C1 H1 112.8 . . ?
C7 C1 H1 112.8 . . ?
N9 C2 C3 111.14(19) . . ?
N9 C2 C1 127.51(19) . . ?
C3 C2 C1 121.2(2) . . ?
C2 C3 C11 106.09(18) . . ?
C2 C3 C4 120.58(19) . . ?
C11 C3 C4 133.33(18) . . ?
C3 C4 C5 107.32(18) . . ?
C3 C4 H4A 110.3 . . ?
C5 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
C5 C4 H4B 110.3 . . ?
H4A C4 H4B 108.5 . . ?
O6 C5 O8 105.88(19) . . ?
O6 C5 C4 111.1(2) . . ?
O8 C5 C4 109.0(2) . . ?
O6 C5 H5 110.3 . . ?
O8 C5 H5 110.3 . . ?
C4 C5 H5 110.3 . . ?
C5 O6 C1 102.14(19) . . ?
C2 N9 C10 107.86(17) . . ?
C2 N9 H9 126.1 . . ?
C10 N9 H9 126.1 . . ?
C5 O8 C7 107.12(19) . . ?
O8 C7 C1 102.23(18) . . ?
O8 C7 H7A 111.3 . . ?
C1 C7 H7A 111.3 . . ?
O8 C7 H7B 111.3 . . ?
C1 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
N9 C10 C12 132.08(19) . . ?
N9 C10 C11 108.12(18) . . ?
C12 C10 C11 119.80(19) . . ?
N15 C11 C3 130.08(18) . . ?
N15 C11 C10 123.14(19) . . ?
C3 C11 C10 106.78(17) . . ?
C13 C12 C10 116.33(19) . . ?
C13 C12 H12 121.8 . . ?
C10 C12 H12 121.8 . . ?
C12 C13 C14 121.1(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
N15 C14 C13 122.89(19) . . ?
N15 C14 C16 117.20(19) . . ?
C13 C14 C16 119.9(2) . . ?
C14 N15 C11 116.72(17) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C16 H16D 109.5 . . ?
H16A C16 H16D 141.1 . . ?
H16B C16 H16D 56.3 . . ?
H16C C16 H16D 56.3 . . ?
C14 C16 H16E 109.5 . . ?
H16A C16 H16E 56.3 . . ?
H16B C16 H16E 141.1 . . ?
H16C C16 H16E 56.3 . . ?
H16D C16 H16E 109.5 . . ?
C14 C16 H16F 109.5 . . ?
H16A C16 H16F 56.3 . . ?
H16B C16 H16F 56.3 . . ?
H16C C16 H16F 141.1 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
O26 C21 C22 106.42(17) . . ?
O26 C21 C27 99.51(18) . . ?
C22 C21 C27 111.41(19) . . ?
O26 C21 H21 112.9 . . ?
C22 C21 H21 112.9 . . ?
C27 C21 H21 112.9 . . ?
C23 C22 N29 111.10(19) . . ?
C23 C22 C21 120.75(19) . . ?
N29 C22 C21 128.14(18) . . ?
C22 C23 C31 106.18(18) . . ?
C22 C23 C24 121.14(19) . . ?
C31 C23 C24 132.68(18) . . ?
C23 C24 C25 107.62(17) . . ?
C23 C24 H24A 110.2 . . ?
C25 C24 H24A 110.2 . . ?
C23 C24 H24B 110.2 . . ?
C25 C24 H24B 110.2 . . ?
H24A C24 H24B 108.5 . . ?
O26 C25 O28 105.50(17) . . ?
O26 C25 C24 111.04(18) . . ?
O28 C25 C24 110.35(18) . . ?
O26 C25 H25 110.0 . . ?
O28 C25 H25 110.0 . . ?
C24 C25 H25 110.0 . . ?
C25 O26 C21 102.28(15) . . ?
O28 C27 C21 102.77(17) . . ?
O28 C27 H27A 111.2 . . ?
C21 C27 H27A 111.2 . . ?
O28 C27 H27B 111.2 . . ?
C21 C27 H27B 111.2 . . ?
H27A C27 H27B 109.1 . . ?
C25 O28 C27 107.34(16) . . ?
C30 N29 C22 107.59(17) . . ?
C30 N29 H29 126(2) . . ?
C22 N29 H29 125(2) . . ?
N29 C30 C32 132.25(19) . . ?
N29 C30 C31 108.19(18) . . ?
C32 C30 C31 119.6(2) . . ?
N35 C31 C23 129.81(18) . . ?
N35 C31 C30 123.25(19) . . ?
C23 C31 C30 106.93(18) . . ?
C33 C32 C30 116.4(2) . . ?
C33 C32 H32 121.8 . . ?
C30 C32 H32 121.8 . . ?
C32 C33 C34 121.5(2) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 H33 119.3 . . ?
N35 C34 C33 122.5(2) . . ?
N35 C34 C36 116.7(2) . . ?
C33 C34 C36 120.8(2) . . ?
C34 N35 C31 116.78(18) . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C36 H36D 109.5 . . ?
H36A C36 H36D 141.1 . . ?
H36B C36 H36D 56.3 . . ?
H36C C36 H36D 56.3 . . ?
C34 C36 H36E 109.5 . . ?
H36A C36 H36E 56.3 . . ?
H36B C36 H36E 141.1 . . ?
H36C C36 H36E 56.3 . . ?
H36D C36 H36E 109.5 . . ?
C34 C36 H36F 109.5 . . ?
H36A C36 H36F 56.3 . . ?
H36B C36 H36F 56.3 . . ?
H36C C36 H36F 141.1 . . ?
H36D C36 H36F 109.5 . . ?
H36E C36 H36F 109.5 . . ?
Cl41 C40 Cl42 111.66(17) . . ?
Cl41 C40 H40A 109.3 . . ?
Cl42 C40 H40A 109.3 . . ?
Cl41 C40 H40B 109.3 . . ?
Cl42 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?
Cl52 C50 Cl51 111.53(15) . . ?
Cl52 C50 H50A 109.3 . . ?
Cl51 C50 H50A 109.3 . . ?
Cl52 C50 H50B 109.3 . . ?
Cl51 C50 H50B 109.3 . . ?
H50A C50 H50B 108.0 . . ?
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 O6 1.437(3) . ?
C1 C2 1.487(3) . ?
C1 C7 1.524(3) . ?
C1 H1 1.0000 . ?
C2 N9 1.369(3) . ?
C2 C3 1.375(3) . ?
C3 C11 1.423(3) . ?
C3 C4 1.502(3) . ?
C4 C5 1.535(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O6 1.421(3) . ?
C5 O8 1.436(3) . ?
C5 H5 1.0000 . ?
N9 C10 1.373(3) . ?
N9 H9 0.8800 . ?
O8 C7 1.440(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 C12 1.392(3) . ?
C10 C11 1.425(3) . ?
C11 N15 1.349(3) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.410(3) . ?
C13 H13 0.9500 . ?
C14 N15 1.342(3) . ?
C14 C16 1.503(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 H16F 0.9800 . ?
C21 O26 1.448(3) . ?
C21 C22 1.487(3) . ?
C21 C27 1.528(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.373(3) . ?
C22 N29 1.377(3) . ?
C23 C31 1.422(3) . ?
C23 C24 1.503(3) . ?
C24 C25 1.525(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O26 1.420(3) . ?
C25 O28 1.434(3) . ?
C25 H25 1.0000 . ?
C27 O28 1.439(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
N29 C30 1.374(3) . ?
N29 H29 0.88(3) . ?
C30 C32 1.390(3) . ?
C30 C31 1.424(3) . ?
C31 N35 1.356(3) . ?
C32 C33 1.384(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.412(3) . ?
C33 H33 0.9500 . ?
C34 N35 1.339(3) . ?
C34 C36 1.508(3) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C36 H36D 0.9800 . ?
C36 H36E 0.9800 . ?
C36 H36F 0.9800 . ?
C40 Cl41 1.756(3) . ?
C40 Cl42 1.765(3) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C50 Cl52 1.765(3) . ?
C50 Cl51 1.765(3) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{b49adb2c-5c23-4eaa-9b2e-757b3e6d510b} y y y
loop_
_publcif_info_cif.paper_type
?
