#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:45:29 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301091 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/05/7160540.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_7160540
loop_
_publ_author_name
'Yue, Xiao-Jing'
'Pei, Li-Ping'
'Wang, Min-Can'
'Jia, Shi-Kun'
'Mei, Guang-Jian'
_publ_section_title
;
 Synthesis of 3-indolyl all-carbon quaternary centers via
 Rh/Brønsted acid co-catalyzed three-component reactions of
 azoalkenes with indoles and diazoacetates.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5323
_journal_page_last               5327
_journal_paper_doi               10.1039/d5ob00567a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C29 H35 N3 O6, 2(C H Cl3)'
_chemical_formula_sum            'C31 H37 Cl6 N3 O6'
_chemical_formula_weight         760.33
_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             2023-11-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-10-28 deposited with the CCDC.	2025-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                113.796(5)
_cell_angle_beta                 90.707(4)
_cell_angle_gamma                110.206(4)
_cell_formula_units_Z            2
_cell_length_a                   12.7618(5)
_cell_length_b                   13.0621(6)
_cell_length_c                   13.4282(7)
_cell_measurement_reflns_used    8617
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2730
_cell_measurement_theta_min      3.9840
_cell_volume                     1891.85(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  16.00   1.00    1.00    --    0.00 -57.00 -90.00   47
  2  ω    -63.00 -36.00   1.00    1.00    --    0.00 -57.00 -90.00   27
  3  ω    -17.00  19.00   1.00    1.00    --    0.00 -77.00-180.00   36
  4  ω   -102.00 -62.00   1.00    2.25    --  -33.50 -57.00  60.00   40
  5  ω    -58.00 -23.00   1.00    2.25    --  -33.50 -57.00  60.00   35
  6  ω    -56.00  36.00   1.00    2.25    --  -33.50  37.00  60.00   92
  7  ω     65.00  99.00   1.00    2.25    --   36.47 178.00  60.00   34
  8  ω     10.00  37.00   1.00    2.25    --   36.47 -99.00 150.00   27
  9  ω     25.00  84.00   1.00    2.25    --   36.47-125.00  46.00   59
 10  ω     -1.00  24.00   1.00    2.25    --   36.47  93.00 -42.33   25
 11  ω     44.00  72.00   1.00    2.25    --   36.47 -99.00 150.00   28
 12  ω     61.00 108.00   1.00    2.25    --   36.47 178.00-180.00   47
 13  ω     61.00 110.00   1.00    2.25    --   36.47 178.00   0.00   49
 14  ω     -1.00  24.00   1.00    2.25    --   36.47  94.00  46.67   25
 15  ω     62.00 103.00   1.00    2.25    --   36.47 178.00 -90.00   41
 16  ω     -1.00  24.00   1.00    2.25    --   36.47  93.00 156.42   25
 17  ω      9.00  34.00   1.00    2.25    --   44.00  89.00-111.83   25
 18  ω      9.00  34.00   1.00    2.25    --   44.00  88.00 120.38   25
 19  ω     16.00  42.00   1.00    2.25    --   48.00  84.00-152.84   26
 20  ω     16.00  41.00   1.00    2.25    --   48.00  83.00 114.50   25
 21  ω     17.00  42.00   1.00    2.25    --   48.00  81.00 -79.73   25
 22  ω     17.00  42.00   1.00    2.25    --   48.00  82.00  41.67   25
 23  ω     16.00  41.00   1.00    2.25    --   48.00  84.00 -32.04   25
 24  ω     17.00  42.00   1.00    2.25    --   48.00  81.00 172.72   25
 25  ω     30.00  58.00   1.00    2.25    --   52.00  73.00  16.35   28
 26  ω     83.00 124.00   1.00    2.25    --   56.00  73.00 -30.24   41
 27  ω     32.00  80.00   1.00    2.25    --   56.00  69.00 104.31   48
 28  ω     68.00  94.00   1.00    2.25    --   56.00  73.00 157.18   26
 29  ω     31.00  64.00   1.00    2.25    --   56.00  71.00 -81.73   33
 30  ω     37.00  63.00   1.00    2.25    --   56.00  69.00  48.34   26
 31  ω     30.00  58.00   1.00    2.25    --   56.00  73.00 157.18   28
 32  ω     96.00 122.00   1.00    2.25    --   56.00  71.00 -81.73   26
 33  ω     30.00  68.00   1.00    2.25    --   56.00  73.00 -30.24   38
 34  ω     93.00 124.00   1.00    2.25    --   56.00  69.00 104.31   31
 35  ω     32.00  88.00   1.00    2.25    --   56.00  72.00-167.50   56
 36  ω     98.00 126.00   1.00    2.25    --   60.00  67.00  72.53   28
 37  ω     39.00  79.00   1.00    2.25    --   60.00  67.00  72.53   40
 38  ω     41.00 120.00   1.00    2.25    --   60.00  55.00 -96.20   79
 39  ω    124.00 158.00   1.00   11.00    --   88.00  39.00  -6.85   34
 40  ω     66.00  92.00   1.00   11.00    --   88.00  39.00  -6.85   26
 41  ω     89.00 115.00   1.00   11.00    --  108.00  61.00   0.00   26
 42  ω     88.00 122.00   1.00   11.00    --  108.00  45.00 150.00   34
 43  ω     41.00  73.00   1.00   11.00    --  108.00 -94.00-120.00   32
 44  ω     78.00 109.00   1.00   11.00    --  108.00-111.00-180.00   31
 45  ω    127.00 176.00   1.00   11.00    --  108.00  61.00  30.00   49
 46  ω     88.00 120.00   1.00   11.00    --  108.00  45.00-150.00   32
 47  ω     89.00 119.00   1.00   11.00    --  108.00  45.00  60.00   30
 48  ω     44.00 109.00   1.00   11.00    --  108.00-111.00   0.00   65
 49  ω     88.00 158.00   1.00   11.00    --  108.00  45.00 -60.00   70
 50  ω     88.00 167.00   1.00   11.00    --  108.00  61.00 150.00   79
 51  ω     88.00 123.00   1.00   11.00    --  108.00  45.00 120.00   35
 52  ω    151.00 176.00   1.00   11.00    --  108.00  61.00-180.00   25
 53  ω     88.00 113.00   1.00   11.00    --  108.00  61.00-180.00   25
 54  ω     88.00 114.00   1.00   11.00    --  108.00  61.00  30.00   26
 55  ω     88.00 174.00   1.00   11.00    --  108.00  61.00 -30.00   86
 56  ω     88.00 114.00   1.00   11.00    --  108.00  45.00   0.00   26
 57  ω    130.00 175.00   1.00   11.00    --  108.00  61.00-150.00   45
 58  ω     88.00 125.00   1.00   11.00    --  108.00  61.00-150.00   37
 59  ω     88.00 120.00   1.00   11.00    --  108.00  61.00 -90.00   32
 60  ω    135.00 174.00   1.00   11.00    --  108.00  61.00 -90.00   39
 61  ω     48.00  93.00   1.00   11.00    --  108.00 -94.00  90.00   45
 62  ω    127.00 172.00   1.00   11.00    --  108.00  61.00   0.00   45
 63  ω     42.00 109.00   1.00   11.00    --  108.00-111.00  90.00   67
 64  ω    130.00 169.00   1.00   11.00    --  108.00  61.00  60.00   39
 65  ω     89.00 126.00   1.00   11.00    --  108.00  61.00  60.00   37
 66  ω     88.00 117.00   1.00   11.00    --  108.00  45.00  30.00   29
 67  ω    133.00 176.00   1.00   11.00    --  108.00  61.00 120.00   43
 68  ω     45.00 109.00   1.00   11.00    --  108.00-111.00 -90.00   64
 69  ω     88.00 129.00   1.00   11.00    --  108.00  61.00 120.00   41
 70  ω    137.00 176.00   1.00   11.00    --  108.00  45.00-180.00   39
 71  ω    134.00 175.00   1.00   11.00    --  108.00  61.00  90.00   41
 72  ω     89.00 118.00   1.00   11.00    --  108.00  45.00 -90.00   29
 73  ω     88.00 118.00   1.00   11.00    --  108.00  61.00  90.00   30
 74  ω     88.00 176.00   1.00   11.00    --  108.00  61.00 -60.00   88
 75  ω     40.00 125.00   1.00   11.00    --  108.00 -61.00  90.00   85
 76  ω     88.00 117.00   1.00   11.00    --  108.00  45.00  90.00   29
 77  ω     88.00 114.00   1.00   11.00    --  108.00  45.00-120.00   26
 78  ω     88.00 114.00   1.00   11.00    --  108.00  45.00-180.00   26
 79  ω    129.00 175.00   1.00   11.00    --  108.00  61.00-120.00   46
 80  ω     88.00 114.00   1.00   11.00    --  108.00  61.00-120.00   26
 81  ω     38.00  48.00   1.00   11.00    --  108.00 -94.00 -60.00   10
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1002218000
_diffrn_orient_matrix_UB_12      0.1020007000
_diffrn_orient_matrix_UB_13      -0.0085075000
_diffrn_orient_matrix_UB_21      -0.0360892000
_diffrn_orient_matrix_UB_22      -0.0619478000
_diffrn_orient_matrix_UB_23      -0.1266882000
_diffrn_orient_matrix_UB_31      -0.0757142000
_diffrn_orient_matrix_UB_32      0.0723095000
_diffrn_orient_matrix_UB_33      0.0102798000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26449
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.655
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.503
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         6667
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0728
_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)+(0.1173P)²+1.1042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2098
_refine_ls_wR_factor_ref         0.2288
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5111
_reflns_number_total             6667
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob00567a2.cif
_cod_data_source_block           202311316
_cod_depositor_comments
'Adding full bibliography for 7160539--7160540.cif.'
_cod_original_cell_volume        1891.85(17)
_cod_database_code               7160540
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4
_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   0.662
_shelx_estimated_absorpt_t_min   0.515
_reflns_odcompleteness_completeness 98.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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. Restrained distances
 Cl1-Cl2
 2.9 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl4) = Uanis(Cl4A)
Uanis(Cl5A) = Uanis(Cl5)
Uanis(Cl6) = Uanis(Cl6A)
Uanis(Cl2A) = Uanis(Cl1A)
Uanis(Cl1) = Uanis(Cl2)
Uanis(Cl3A) = Uanis(Cl3)
4. Others
 Sof(Cl4A)=Sof(Cl5)=Sof(Cl6A)=Sof(H31A)=1-FVAR(1)
 Sof(Cl4)=Sof(Cl5A)=Sof(Cl6)=Sof(H31)=FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(H30A)=1-FVAR(2)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(H30)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C30(H30), C30(H30A), C31(H31A), C31(H31)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
5.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_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 2.600
_oxdiff_exptl_absorpt_empirical_full_min 0.757
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
O1 O 0.0736(2) 0.1803(2) 0.4957(2) 0.0633(6) Uani 1 1 d . . . . .
O2 O 0.0589(2) 0.0725(2) 0.3141(2) 0.0664(6) Uani 1 1 d . . . . .
O3 O 0.0017(2) 0.2673(3) 0.3064(2) 0.0692(7) Uani 1 1 d . . . . .
O4 O 0.0711(2) 0.2849(3) 0.1604(2) 0.0715(7) Uani 1 1 d . . . . .
O5 O 0.5216(2) 0.2857(3) 0.0939(2) 0.0735(7) Uani 1 1 d . . . . .
O6 O 0.5935(2) 0.4834(3) 0.1262(2) 0.0734(7) Uani 1 1 d . . . . .
N1 N 0.4243(2) 0.1269(3) 0.3524(3) 0.0599(7) Uani 1 1 d . . . . .
N2 N 0.35647(19) 0.3323(2) 0.2101(2) 0.0465(6) Uani 1 1 d . . . . .
N3 N 0.4427(2) 0.4188(3) 0.1927(2) 0.0525(6) Uani 1 1 d . . . . .
H3 H 0.448(3) 0.488(4) 0.222(3) 0.060(11) Uiso 1 1 d . . . . .
C1 C 0.3478(3) 0.2680(3) 0.6119(3) 0.0603(8) Uani 1 1 d . . . . .
H1 H 0.2974 0.3057 0.6381 0.072 Uiso 1 1 calc R . . . .
C2 C 0.4155(4) 0.2551(4) 0.6829(4) 0.0743(10) Uani 1 1 d . . . . .
H2 H 0.4099 0.2840 0.7574 0.089 Uiso 1 1 calc R . . . .
C3 C 0.4921(4) 0.1998(4) 0.6459(4) 0.0815(12) Uani 1 1 d . . . . .
H3A H 0.5374 0.1938 0.6963 0.098 Uiso 1 1 calc R . . . .
C4 C 0.5022(3) 0.1541(3) 0.5366(4) 0.0697(10) Uani 1 1 d . . . . .
H4 H 0.5533 0.1169 0.5119 0.084 Uiso 1 1 calc R . . . .
C5 C 0.4330(3) 0.1654(3) 0.4640(3) 0.0563(8) Uani 1 1 d . . . . .
C6 C 0.3559(3) 0.2236(3) 0.4998(3) 0.0511(7) Uani 1 1 d . . . . .
C7 C 0.3020(2) 0.2209(3) 0.4030(3) 0.0465(6) Uani 1 1 d . . . . .
C8 C 0.3459(3) 0.1599(3) 0.3165(3) 0.0535(7) Uani 1 1 d . . . . .
H8 H 0.3253 0.1432 0.2432 0.064 Uiso 1 1 calc R . . . .
C9 C 0.4864(4) 0.0602(4) 0.2809(4) 0.0862(13) Uani 1 1 d . . . . .
H9A H 0.4522 -0.0236 0.2664 0.129 Uiso 1 1 calc GR . . . .
H9B H 0.5638 0.0932 0.3168 0.129 Uiso 1 1 calc GR . . . .
H9C H 0.4839 0.0670 0.2124 0.129 Uiso 1 1 calc GR . . . .
C10 C 0.2087(2) 0.2676(3) 0.3976(2) 0.0446(6) Uani 1 1 d . . . . .
C11 C 0.1904(2) 0.2688(3) 0.2824(2) 0.0449(6) Uani 1 1 d . . . . .
H11 H 0.1891 0.1913 0.2268 0.054 Uiso 1 1 calc R . . . .
C12 C 0.2348(2) 0.3940(3) 0.4917(2) 0.0457(6) Uani 1 1 d . . . . .
C13 C 0.3463(3) 0.4746(3) 0.5360(3) 0.0537(7) Uani 1 1 d . . . . .
H13 H 0.4049 0.4491 0.5124 0.064 Uiso 1 1 calc R . . . .
C14 C 0.3721(3) 0.5919(3) 0.6144(3) 0.0686(9) Uani 1 1 d . . . . .
H14 H 0.4474 0.6446 0.6429 0.082 Uiso 1 1 calc R . . . .
C15 C 0.2856(4) 0.6307(4) 0.6504(3) 0.0764(11) Uani 1 1 d . . . . .
H15 H 0.3026 0.7096 0.7034 0.092 Uiso 1 1 calc R . . . .
C16 C 0.1753(4) 0.5529(4) 0.6079(3) 0.0707(10) Uani 1 1 d . . . . .
H16 H 0.1172 0.5795 0.6315 0.085 Uiso 1 1 calc R . . . .
C17 C 0.1489(3) 0.4344(3) 0.5297(3) 0.0550(7) Uani 1 1 d . . . . .
H17 H 0.0734 0.3818 0.5025 0.066 Uiso 1 1 calc R . . . .
C18 C 0.1042(2) 0.1714(3) 0.4094(3) 0.0503(7) Uani 1 1 d . . . . .
C19 C -0.0365(4) -0.0247(4) 0.3176(4) 0.0902(14) Uani 1 1 d . . . . .
H19A H -0.0588 -0.0939 0.2470 0.135 Uiso 1 1 calc GR . . . .
H19B H -0.0988 0.0009 0.3347 0.135 Uiso 1 1 calc GR . . . .
H19C H -0.0156 -0.0458 0.3734 0.135 Uiso 1 1 calc GR . . . .
C20 C 0.0771(3) 0.2744(3) 0.2552(3) 0.0507(7) Uani 1 1 d . . . . .
C21 C -0.0329(3) 0.2916(5) 0.1235(4) 0.0812(12) Uani 1 1 d . . . . .
H21A H -0.0330 0.3718 0.1662 0.097 Uiso 1 1 calc R . . . .
H21B H -0.0983 0.2329 0.1330 0.097 Uiso 1 1 calc R . . . .
C22 C -0.0377(5) 0.2655(10) 0.0052(6) 0.162(4) Uani 1 1 d . . . . .
H22A H -0.1150 0.2372 -0.0291 0.242 Uiso 1 1 calc GR . . . .
H22B H -0.0077 0.2043 -0.0308 0.242 Uiso 1 1 calc GR . . . .
H22C H 0.0066 0.3379 -0.0013 0.242 Uiso 1 1 calc GR . . . .
C23 C 0.2863(2) 0.3679(3) 0.2672(2) 0.0452(6) Uani 1 1 d . . . . .
C24 C 0.2901(3) 0.4950(3) 0.3130(3) 0.0608(8) Uani 1 1 d . . . . .
H24A H 0.3621 0.5501 0.3599 0.091 Uiso 1 1 calc GR . . . .
H24B H 0.2305 0.5008 0.3551 0.091 Uiso 1 1 calc GR . . . .
H24C H 0.2803 0.5153 0.2533 0.091 Uiso 1 1 calc GR . . . .
C25 C 0.5206(2) 0.3856(3) 0.1332(3) 0.0533(7) Uani 1 1 d . . . . .
C26 C 0.6866(3) 0.4790(5) 0.0642(4) 0.0818(12) Uani 1 1 d . . . . .
C27 C 0.7338(5) 0.6045(7) 0.0696(7) 0.133(2) Uani 1 1 d . . . . .
H27A H 0.6736 0.6213 0.0443 0.199 Uiso 1 1 calc GR . . . .
H27B H 0.7903 0.6093 0.0233 0.199 Uiso 1 1 calc GR . . . .
H27C H 0.7674 0.6629 0.1445 0.199 Uiso 1 1 calc GR . . . .
C28 C 0.6386(6) 0.3883(7) -0.0553(5) 0.127(2) Uani 1 1 d . . . . .
H28A H 0.6122 0.3076 -0.0606 0.190 Uiso 1 1 calc GR . . . .
H28B H 0.6967 0.3980 -0.0993 0.190 Uiso 1 1 calc GR . . . .
H28C H 0.5766 0.4016 -0.0816 0.190 Uiso 1 1 calc GR . . . .
C29 C 0.7681(4) 0.4508(8) 0.1171(7) 0.138(3) Uani 1 1 d . . . . .
H29A H 0.7860 0.5021 0.1951 0.207 Uiso 1 1 calc GR . . . .
H29B H 0.8361 0.4645 0.0860 0.207 Uiso 1 1 calc GR . . . .
H29C H 0.7352 0.3676 0.1045 0.207 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.1585(5) 0.0283(6) 1.0012(6) 0.0955(16) Uani 0.274(7) 1 d D . P A 1
Cl1A Cl 0.1576(2) 0.0524(3) 0.9711(3) 0.1049(6) Uani 0.726(7) 1 d . . P A 2
Cl2 Cl 0.3221(5) -0.0366(6) 0.9964(6) 0.0955(16) Uani 0.274(7) 1 d D . P A 1
Cl2A Cl 0.3374(2) -0.0535(3) 0.9572(3) 0.1049(6) Uani 0.726(7) 1 d . . P A 2
Cl3 Cl 0.2978(8) 0.0339(10) 0.8310(8) 0.1125(9) Uani 0.274(7) 1 d . . P A 1
Cl3A Cl 0.3311(3) 0.0916(4) 0.8435(2) 0.1125(9) Uani 0.726(7) 1 d . . P A 2
C30 C 0.2987(4) 0.0678(5) 0.9638(4) 0.0952(14) Uani 1 1 d . . . . .
H30 H 0.3500 0.1511 1.0121 0.114 Uiso 0.274(7) 1 calc R . P A 1
H30A H 0.3468 0.1412 1.0286 0.114 Uiso 0.726(7) 1 calc R . P A 2
Cl4 Cl 0.8970(4) 0.3328(4) 0.7556(3) 0.1913(14) Uani 0.855(5) 1 d . . P B 1
Cl4A Cl 0.926(2) 0.353(3) 0.7109(18) 0.1913(14) Uani 0.145(5) 1 d . . P B 2
Cl5 Cl 0.8248(15) 0.1105(19) 0.662(3) 0.205(2) Uani 0.145(5) 1 d . . P B 2
Cl5A Cl 0.7800(2) 0.0844(3) 0.5945(5) 0.205(2) Uani 0.855(5) 1 d . . P B 1
Cl6 Cl 0.82793(16) 0.2774(3) 0.5328(2) 0.1133(7) Uani 0.855(5) 1 d . . P B 1
Cl6A Cl 0.8148(11) 0.2097(17) 0.5061(14) 0.1133(7) Uani 0.145(5) 1 d . . P B 2
C31 C 0.8761(4) 0.2228(4) 0.6178(5) 0.0868(13) Uani 1 1 d . . . . .
H31A H 0.9457 0.2123 0.5947 0.104 Uiso 0.145(5) 1 calc R . P B 2
H31 H 0.9486 0.2164 0.6007 0.104 Uiso 0.855(5) 1 calc R . P B 1
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
C18 O2 C19 115.9(3) . . ?
C20 O4 C21 116.3(3) . . ?
C25 O6 C26 122.1(3) . . ?
C5 N1 C8 108.9(3) . . ?
C5 N1 C9 126.6(3) . . ?
C8 N1 C9 124.5(3) . . ?
C23 N2 N3 116.6(3) . . ?
N2 N3 H3 119(3) . . ?
C25 N3 N2 118.9(3) . . ?
C25 N3 H3 122(3) . . ?
C2 C1 H1 120.5 . . ?
C2 C1 C6 119.1(4) . . ?
C6 C1 H1 120.5 . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.6(4) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.4(4) . . ?
C5 C4 H4 121.3 . . ?
N1 C5 C4 129.6(3) . . ?
N1 C5 C6 107.9(3) . . ?
C4 C5 C6 122.4(4) . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 135.3(3) . . ?
C5 C6 C7 106.6(3) . . ?
C6 C7 C10 126.8(3) . . ?
C8 C7 C6 105.8(3) . . ?
C8 C7 C10 127.3(3) . . ?
N1 C8 C7 110.8(3) . . ?
N1 C8 H8 124.6 . . ?
C7 C8 H8 124.6 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C11 109.8(2) . . ?
C7 C10 C12 112.1(2) . . ?
C7 C10 C18 102.2(2) . . ?
C12 C10 C11 110.5(2) . . ?
C12 C10 C18 111.2(2) . . ?
C18 C10 C11 110.7(2) . . ?
C10 C11 H11 106.4 . . ?
C20 C11 C10 113.1(2) . . ?
C20 C11 H11 106.4 . . ?
C20 C11 C23 109.7(2) . . ?
C23 C11 C10 114.2(2) . . ?
C23 C11 H11 106.4 . . ?
C13 C12 C10 120.3(3) . . ?
C13 C12 C17 118.0(3) . . ?
C17 C12 C10 121.6(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
O1 C18 O2 123.9(3) . . ?
O1 C18 C10 124.1(3) . . ?
O2 C18 C10 111.7(2) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 O4 123.2(3) . . ?
O3 C20 C11 126.9(3) . . ?
O4 C20 C11 109.9(2) . . ?
O4 C21 H21A 110.2 . . ?
O4 C21 H21B 110.2 . . ?
O4 C21 C22 107.4(4) . . ?
H21A C21 H21B 108.5 . . ?
C22 C21 H21A 110.2 . . ?
C22 C21 H21B 110.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 C11 115.0(3) . . ?
N2 C23 C24 124.5(3) . . ?
C24 C23 C11 120.5(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C25 O6 127.1(3) . . ?
O5 C25 N3 125.3(3) . . ?
O6 C25 N3 107.7(3) . . ?
O6 C26 C27 101.9(4) . . ?
O6 C26 C28 109.3(4) . . ?
O6 C26 C29 109.8(4) . . ?
C27 C26 C28 108.5(5) . . ?
C29 C26 C27 114.0(5) . . ?
C29 C26 C28 112.8(6) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
Cl1 C30 H30 112.8 . . ?
Cl1A C30 Cl2A 118.2(3) . . ?
Cl1A C30 Cl3A 107.1(3) . . ?
Cl1A C30 H30A 107.7 . . ?
Cl2 C30 Cl1 90.5(5) . . ?
Cl2 C30 H30 112.8 . . ?
Cl2A C30 Cl3A 107.9(3) . . ?
Cl2A C30 H30A 107.7 . . ?
Cl3 C30 Cl1 114.4(5) . . ?
Cl3 C30 Cl2 111.6(4) . . ?
Cl3 C30 H30 112.8 . . ?
Cl3A C30 H30A 107.7 . . ?
Cl4 C31 H31 109.3 . . ?
Cl4A C31 Cl5 115.0(14) . . ?
Cl4A C31 Cl6A 114.7(11) . . ?
Cl4A C31 H31A 100.4 . . ?
Cl5 C31 H31A 100.4 . . ?
Cl5A C31 Cl4 112.9(3) . . ?
Cl5A C31 Cl6 109.9(3) . . ?
Cl5A C31 H31 109.3 . . ?
Cl6 C31 Cl4 106.0(3) . . ?
Cl6 C31 H31 109.3 . . ?
Cl6A C31 Cl5 120.8(10) . . ?
Cl6A C31 H31A 100.4 . . ?
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
O1 C18 1.201(4) . ?
O2 C18 1.331(4) . ?
O2 C19 1.442(4) . ?
O3 C20 1.189(4) . ?
O4 C20 1.337(4) . ?
O4 C21 1.455(4) . ?
O5 C25 1.198(4) . ?
O6 C25 1.336(4) . ?
O6 C26 1.464(4) . ?
N1 C5 1.363(5) . ?
N1 C8 1.368(4) . ?
N1 C9 1.460(5) . ?
N2 N3 1.379(3) . ?
N2 C23 1.273(4) . ?
N3 H3 0.81(4) . ?
N3 C25 1.361(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(5) . ?
C1 C6 1.398(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(6) . ?
C3 H3A 0.9300 . ?
C3 C4 1.369(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(5) . ?
C5 C6 1.418(5) . ?
C6 C7 1.444(4) . ?
C7 C8 1.369(4) . ?
C7 C10 1.528(4) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.567(4) . ?
C10 C12 1.536(4) . ?
C10 C18 1.546(4) . ?
C11 H11 0.9800 . ?
C11 C20 1.521(4) . ?
C11 C23 1.531(4) . ?
C12 C13 1.388(4) . ?
C12 C17 1.391(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.366(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.390(5) . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.480(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.502(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C26 C27 1.510(8) . ?
C26 C28 1.515(8) . ?
C26 C29 1.475(7) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
Cl1 C30 1.820(9) . ?
Cl1A C30 1.750(6) . ?
Cl2 C30 1.703(10) . ?
Cl2A C30 1.787(7) . ?
Cl3 C30 1.653(10) . ?
Cl3A C30 1.791(6) . ?
C30 H30 0.9800 . ?
C30 H30A 0.9800 . ?
Cl4 C31 1.771(6) . ?
Cl4A C31 1.54(3) . ?
Cl5 C31 1.725(19) . ?
Cl5A C31 1.695(5) . ?
Cl6 C31 1.769(5) . ?
Cl6A C31 1.601(15) . ?
C31 H31A 0.9800 . ?
C31 H31 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
N1 C5 C6 C1 178.3(3) . . . . ?
N1 C5 C6 C7 -1.5(3) . . . . ?
N2 N3 C25 O5 -0.4(5) . . . . ?
N2 N3 C25 O6 179.0(3) . . . . ?
N3 N2 C23 C11 178.7(2) . . . . ?
N3 N2 C23 C24 1.7(4) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C1 C6 C7 C8 -178.1(3) . . . . ?
C1 C6 C7 C10 -2.5(5) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
C2 C1 C6 C7 -179.4(3) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 N1 -178.9(3) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C4 C5 C6 C1 -1.8(5) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C5 N1 C8 C7 0.3(4) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
C5 C6 C7 C10 177.3(3) . . . . ?
C6 C1 C2 C3 0.5(6) . . . . ?
C6 C7 C8 N1 -1.2(3) . . . . ?
C6 C7 C10 C11 169.7(3) . . . . ?
C6 C7 C10 C12 46.4(4) . . . . ?
C6 C7 C10 C18 -72.8(3) . . . . ?
C7 C10 C11 C20 161.5(2) . . . . ?
C7 C10 C11 C23 -72.2(3) . . . . ?
C7 C10 C12 C13 29.9(4) . . . . ?
C7 C10 C12 C17 -154.7(3) . . . . ?
C7 C10 C18 O1 93.9(3) . . . . ?
C7 C10 C18 O2 -80.1(3) . . . . ?
C8 N1 C5 C4 -179.1(3) . . . . ?
C8 N1 C5 C6 0.8(3) . . . . ?
C8 C7 C10 C11 -15.6(4) . . . . ?
C8 C7 C10 C12 -138.9(3) . . . . ?
C8 C7 C10 C18 102.0(3) . . . . ?
C9 N1 C5 C4 1.5(6) . . . . ?
C9 N1 C5 C6 -178.6(3) . . . . ?
C9 N1 C8 C7 179.7(3) . . . . ?
C10 C7 C8 N1 -176.8(3) . . . . ?
C10 C11 C20 O3 -7.0(5) . . . . ?
C10 C11 C20 O4 175.0(3) . . . . ?
C10 C11 C23 N2 100.9(3) . . . . ?
C10 C11 C23 C24 -81.9(3) . . . . ?
C10 C12 C13 C14 174.8(3) . . . . ?
C10 C12 C17 C16 -174.2(3) . . . . ?
C11 C10 C12 C13 -93.0(3) . . . . ?
C11 C10 C12 C17 82.4(3) . . . . ?
C11 C10 C18 O1 -149.2(3) . . . . ?
C11 C10 C18 O2 36.8(3) . . . . ?
C12 C10 C11 C20 -74.3(3) . . . . ?
C12 C10 C11 C23 52.1(3) . . . . ?
C12 C10 C18 O1 -25.9(4) . . . . ?
C12 C10 C18 O2 160.1(3) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C12 C17 C16 1.3(5) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C15 C16 C17 C12 -1.4(5) . . . . ?
C17 C12 C13 C14 -0.8(5) . . . . ?
C18 C10 C11 C20 49.4(3) . . . . ?
C18 C10 C11 C23 175.8(2) . . . . ?
C18 C10 C12 C13 143.6(3) . . . . ?
C18 C10 C12 C17 -41.0(4) . . . . ?
C19 O2 C18 O1 3.6(5) . . . . ?
C19 O2 C18 C10 177.7(3) . . . . ?
C20 O4 C21 C22 -163.1(5) . . . . ?
C20 C11 C23 N2 -130.9(3) . . . . ?
C20 C11 C23 C24 46.2(4) . . . . ?
C21 O4 C20 O3 2.0(5) . . . . ?
C21 O4 C20 C11 -179.9(3) . . . . ?
C23 N2 N3 C25 179.3(3) . . . . ?
C23 C11 C20 O3 -135.7(3) . . . . ?
C23 C11 C20 O4 46.3(3) . . . . ?
C25 O6 C26 C27 173.4(4) . . . . ?
C25 O6 C26 C28 58.7(5) . . . . ?
C25 O6 C26 C29 -65.5(6) . . . . ?
C26 O6 C25 O5 1.5(6) . . . . ?
C26 O6 C25 N3 -177.9(3) . . . . ?
