#------------------------------------------------------------------------------
#$Date: 2025-08-16 01:19:44 +0300 (Sat, 16 Aug 2025) $
#$Revision: 301757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/54/1575476.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_1575476
_journal_paper_doi               10.1039/D5SC03813H
_chemical_formula_moiety         '4(I), 2(C H2 Cl2), 4(C18 H21 N O3)'
_chemical_formula_sum            'C74 H88 Cl4 I4 N4 O12'
_chemical_formula_weight         1874.88
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-11-04
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2024-11-05 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.7932(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.38142(13)
_cell_length_b                   9.39589(8)
_cell_length_c                   27.9600(2)
_cell_measurement_reflns_used    29867
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      78.3610
_cell_measurement_theta_min      3.2390
_cell_volume                     3906.90(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -14.00   0.50    0.16    --  -87.59  57.00 150.00   74
  2  ω    -53.00 -26.00   0.50    0.16    --  -87.59  57.00 120.00   54
  3  ω    -11.00  22.00   0.50    0.16    --  -51.79  29.00  21.00   66
  4  ω    -51.00 -15.00   0.50    0.16    --  -87.59  57.00   0.00   72
  5  ω   -104.00 -78.00   0.50    0.16    --  -87.59 -29.00-138.00   52
  6  ω   -129.00 -35.00   0.50    0.16    --  -51.79 -29.00-138.00  188
  7  ω   -156.00-127.00   0.50    0.16    --  -87.59 -29.00-138.00   58
  8  ω   -113.00 -88.00   0.50    0.16    --  -87.59 -99.00 150.00   50
  9  ω   -153.00-117.00   0.50    0.16    --  -87.59 -99.00 150.00   72
 10  ω    -23.00  28.00   0.50    0.16    --   52.04 -19.00  60.00  102
 11  ω     57.00  82.00   0.50    0.16    --  107.25 -77.00  84.47   50
 12  ω     42.00 100.00   0.50    0.16    --  107.25 -74.00 -21.75  116
 13  ω     49.00  95.00   0.50    0.16    --  107.25 -78.00-149.59   92
 14  ω     46.00  89.00   0.50    0.16    --  107.25 -73.00  29.54   86
 15  ω     40.00  65.00   0.50    0.16    --  107.25 -71.00 114.86   50
 16  ω     51.00  99.00   0.50    0.16    --  107.25 -71.00  52.26   96
 17  ω     46.00  95.00   0.50    0.16    --  107.25 -70.00  -9.76   98
 18  ω     53.00  78.00   0.50    0.16    --  107.25 -71.00 -58.77   50
 19  ω     38.00  90.00   0.50    0.16    --  107.25 -69.00-128.22  104
 20  ω     44.00  82.00   0.50    0.16    --  107.25 -65.00 -50.42   76
 21  ω     35.00  60.00   0.50    0.16    --  107.25 -65.00 -95.19   50
 22  ω     54.00  97.00   0.50    0.16    --  107.25 -67.00  74.59   86
 23  ω     34.00  71.00   0.50    0.16    --  102.09 -57.00 120.00   74
 24  ω     40.00  89.00   0.50    0.16    --  107.25 -63.00 123.97   98
 25  ω     32.00  58.00   0.50    0.16    --  107.25 -49.00  49.09   52
 26  ω     39.00  65.00   0.50    0.16    --  107.25 -56.00 -82.16   52
 27  ω     25.00  50.00   0.50    0.16    --  102.09 -38.00 -90.00   50
 28  ω     25.00  50.00   0.50    0.16    --  102.09 -38.00-180.00   50
 29  ω     26.00  51.00   0.50    0.16    --  102.09 -38.00-120.00   50
 30  ω     25.00  50.00   0.50    0.16    --  102.09 -38.00   0.00   50
 31  ω    -18.00   7.00   0.50    0.16    --   52.04 -29.00-138.00   50
 32  ω     25.00  50.00   0.50    0.16    --  102.09 -38.00  30.00   50
 33  ω     83.00 143.00   0.50    0.16    --  107.25 121.00 -34.94  120
 34  ω    151.00 176.00   0.50    0.16    --  107.25 121.00 -34.94   50
 35  ω     99.00 124.00   0.50    0.16    --  107.25  68.00 102.52   50
 36  ω    134.00 171.00   0.50    0.16    --  107.25  68.00 102.52   74
 37  ω    125.00 175.00   0.50    0.16    --  107.25  57.00  35.78  100
 38  ω    151.00 176.00   0.50    0.16    --  102.09  29.00  21.00   50
 39  ω    149.00 176.00   0.50    0.16    --  107.25  46.00 -41.40   54
 40  ω    106.00 132.00   0.50    0.16    --  107.25  46.00 -41.40   52
 41  ω     88.00 133.00   0.50    0.16    --  102.09  29.00  21.00   90
 42  ω    144.00 170.00   0.50    0.16    --  107.25  16.00  31.43   52
 43  ω     89.00 115.00   0.50    0.16    --   52.04  29.00  21.00   52
 44  ω     39.00  75.00   0.50    0.16    --   52.04  29.00  21.00   72
 45  ω     73.00 124.00   0.50    0.16    --  107.25  16.00  31.43  102
 46  ω    124.00 150.00   0.50    0.16    --  107.25   6.00 -35.08   52
 47  ω     55.00  80.00   0.50    0.16    --  107.25   6.00 -35.08   50
 48  ω     92.00 133.00   0.50    0.16    --  107.25 -81.00-125.48   82
 49  ω    112.00 137.00   0.50    0.16    --  107.25 -86.00 -83.09   50
 50  ω     47.00  73.00   0.50    0.16    --  107.25 -86.00 -83.09   52
 51  ω     45.00  71.00   0.50    0.16    --  107.25 -81.00-125.48   52
 52  ω     37.00  74.00   0.50    0.16    --  102.09 -99.00   0.00   74
 53  ω     78.00 106.00   0.50    0.16    --  102.09 -99.00   0.00   56
 54  ω     51.00 102.00   0.50    0.16    --  107.25 -93.00 143.38  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0077690000
_diffrn_orient_matrix_UB_12      -0.0327648000
_diffrn_orient_matrix_UB_13      -0.0527542000
_diffrn_orient_matrix_UB_21      -0.0969128000
_diffrn_orient_matrix_UB_22      0.0532545000
_diffrn_orient_matrix_UB_23      -0.0212324000
_diffrn_orient_matrix_UB_31      0.0357005000
_diffrn_orient_matrix_UB_32      0.1515577000
_diffrn_orient_matrix_UB_33      -0.0039355000
_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  0.0434
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            55764
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.176
_diffrn_reflns_theta_min         3.004
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    14.273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_description       needle
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.076
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.021
_refine_diff_density_max         1.700
_refine_diff_density_min         -1.153
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         8382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0572P)²+10.1955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1033
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7561
_reflns_number_total             8382
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc03813h2.cif
_cod_data_source_block           3
_cod_database_code               1575476
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C20 H20 N2 I O4 Cl2'
_chemical_oxdiff_usercomment     'DCM-Et2O, RT, gp'
_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   0.754
_shelx_estimated_absorpt_t_min   0.410
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B), C26(H26A,H26B), C30(H30A,H30B), C37(H37A,H37B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C25(H25), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C24(H24A,H24B,
 H24C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 2.956
_oxdiff_exptl_absorpt_empirical_full_min 0.666
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
I1 I 0.53232(2) -0.16754(2) 0.34643(2) 0.02746(8) Uani 1 1 d . . . . .
I2 I 0.02469(2) 0.11490(2) 0.34114(2) 0.02327(7) Uani 1 1 d . . . . .
Cl1 Cl 0.28975(8) 0.47781(12) 0.51389(4) 0.0445(3) Uani 1 1 d . . . . .
Cl2 Cl 0.18241(10) 0.24081(14) 0.46322(5) 0.0571(3) Uani 1 1 d . . . . .
O1 O 0.43889(17) 0.3561(3) 0.23763(9) 0.0258(5) Uani 1 1 d . . . . .
H1 H 0.456(3) 0.407(6) 0.2210(19) 0.040(14) Uiso 1 1 d . . . . .
O2 O 0.43906(17) 0.1667(3) 0.44334(9) 0.0258(5) Uani 1 1 d . . . . .
O3 O 0.52958(19) 0.3686(3) 0.44852(9) 0.0300(6) Uani 1 1 d . . . . .
O4 O 0.56190(17) 0.0712(3) 0.25919(9) 0.0261(5) Uani 1 1 d . . . . .
H4 H 0.542217 0.010080 0.275695 0.039 Uiso 1 1 calc R U . . .
O5 O 0.54145(17) 0.2847(3) 0.05359(8) 0.0265(5) Uani 1 1 d . . . . .
O6 O 0.44468(18) 0.0906(3) 0.04736(9) 0.0300(6) Uani 1 1 d . . . . .
N1 N 0.33011(17) 0.0913(3) 0.31705(10) 0.0170(5) Uani 1 1 d . . . . .
N2 N 0.66447(18) 0.3425(3) 0.17903(10) 0.0176(5) Uani 1 1 d . . . . .
C1 C 0.3726(2) 0.1793(3) 0.29247(12) 0.0185(6) Uani 1 1 d . . . . .
H1A H 0.356073 0.178905 0.257332 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4394(2) 0.2697(3) 0.31708(12) 0.0178(6) Uani 1 1 d . . . . .
C3 C 0.4632(2) 0.2684(3) 0.36852(12) 0.0196(6) Uani 1 1 d . . . . .
C4 C 0.4192(2) 0.1748(3) 0.39331(12) 0.0198(6) Uani 1 1 d . . . . .
C5 C 0.3503(2) 0.0860(4) 0.36694(12) 0.0190(6) Uani 1 1 d . . . . .
C6 C 0.2999(2) -0.0110(4) 0.39264(12) 0.0244(7) Uani 1 1 d . . . . .
H6A H 0.313559 -0.110131 0.386397 0.037 Uiso 1 1 calc R U . . .
H6B H 0.235235 0.005827 0.380088 0.037 Uiso 1 1 calc R U . . .
H6C H 0.317982 0.007645 0.428298 0.037 Uiso 1 1 calc R U . . .
C7 C 0.4852(2) 0.3661(4) 0.28825(12) 0.0208(6) Uani 1 1 d . . . . .
H7A H 0.484058 0.465523 0.299833 0.025 Uiso 1 1 calc R U . . .
H7B H 0.548705 0.337039 0.293010 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5333(3) 0.3662(4) 0.39834(13) 0.0269(7) Uani 1 1 d . . . . .
H8 H 0.574643 0.419375 0.385413 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5243(3) 0.2333(4) 0.46879(13) 0.0296(8) Uani 1 1 d . . . . .
C10 C 0.5194(3) 0.2558(5) 0.52136(14) 0.0405(10) Uani 1 1 d . . . . .
H10A H 0.508021 0.164620 0.535649 0.061 Uiso 1 1 calc R U . . .
H10B H 0.470410 0.322167 0.521832 0.061 Uiso 1 1 calc R U . . .
H10C H 0.576411 0.295449 0.540794 0.061 Uiso 1 1 calc R U . . .
C11 C 0.6003(3) 0.1340(5) 0.46398(16) 0.0367(9) Uani 1 1 d . . . . .
H11A H 0.658187 0.181873 0.476578 0.055 Uiso 1 1 calc R U . . .
H11B H 0.592660 0.109128 0.429116 0.055 Uiso 1 1 calc R U . . .
H11C H 0.598643 0.047167 0.483176 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2583(2) -0.0073(4) 0.28834(12) 0.0240(7) Uani 1 1 d . . . . .
H12A H 0.272913 -0.105634 0.300472 0.029 Uiso 1 1 calc R U . . .
H12B H 0.200259 0.018827 0.295095 0.029 Uiso 1 1 calc R U . . .
C13 C 0.2474(2) -0.0050(4) 0.23355(12) 0.0201(6) Uani 1 1 d . . . . .
C14 C 0.3002(2) -0.0914(4) 0.21186(13) 0.0234(7) Uani 1 1 d . . . . .
H14 H 0.345871 -0.148821 0.232128 0.028 Uiso 1 1 calc R U . . .
C15 C 0.2867(2) -0.0942(4) 0.16072(14) 0.0255(7) Uani 1 1 d . . . . .
H15 H 0.322315 -0.154926 0.146260 0.031 Uiso 1 1 calc R U . . .
C16 C 0.2211(2) -0.0086(4) 0.13068(13) 0.0266(7) Uani 1 1 d . . . . .
H16 H 0.212112 -0.010106 0.095776 0.032 Uiso 1 1 calc R U . . .
C17 C 0.1690(2) 0.0792(4) 0.15225(13) 0.0244(7) Uani 1 1 d . . . . .
H17 H 0.124421 0.138410 0.131992 0.029 Uiso 1 1 calc R U . . .
C18 C 0.1819(2) 0.0808(4) 0.20321(12) 0.0209(6) Uani 1 1 d . . . . .
H18 H 0.145724 0.140799 0.217583 0.025 Uiso 1 1 calc R U . . .
C19 C 0.6253(2) 0.2500(3) 0.20388(11) 0.0182(6) Uani 1 1 d . . . . .
H19 H 0.645822 0.244907 0.238892 0.022 Uiso 1 1 calc R U . . .
C20 C 0.5562(2) 0.1629(3) 0.17964(12) 0.0191(6) Uani 1 1 d . . . . .
C21 C 0.5268(2) 0.1711(3) 0.12834(12) 0.0209(6) Uani 1 1 d . . . . .
C22 C 0.5677(2) 0.2684(4) 0.10367(12) 0.0213(6) Uani 1 1 d . . . . .
C23 C 0.6391(2) 0.3545(4) 0.12908(12) 0.0194(6) Uani 1 1 d . . . . .
C24 C 0.6851(2) 0.4573(4) 0.10313(12) 0.0261(7) Uani 1 1 d . . . . .
H24A H 0.672263 0.554663 0.111842 0.039 Uiso 1 1 calc R U . . .
H24B H 0.663111 0.444093 0.067293 0.039 Uiso 1 1 calc R U . . .
H24C H 0.750114 0.440600 0.113177 0.039 Uiso 1 1 calc R U . . .
C25 C 0.5139(2) 0.0622(4) 0.20919(12) 0.0226(7) Uani 1 1 d . . . . .
H25 H 0.463374 0.002806 0.196238 0.027 Uiso 1 1 calc R U . . .
C26 C 0.4511(3) 0.0795(4) 0.09907(13) 0.0291(8) Uani 1 1 d . . . . .
H26A H 0.462000 -0.020974 0.109613 0.035 Uiso 1 1 calc R U . . .
H26B H 0.393748 0.109944 0.105731 0.035 Uiso 1 1 calc R U . . .
C27 C 0.4509(3) 0.2317(4) 0.03077(13) 0.0299(8) Uani 1 1 d . . . . .
C28 C 0.3832(3) 0.3315(5) 0.04326(16) 0.0387(10) Uani 1 1 d . . . . .
H28A H 0.396128 0.342568 0.079238 0.058 Uiso 1 1 calc R U . . .
H28B H 0.322636 0.292334 0.030665 0.058 Uiso 1 1 calc R U . . .
H28C H 0.386915 0.424416 0.027989 0.058 Uiso 1 1 calc R U . . .
C29 C 0.4450(3) 0.2226(5) -0.02373(14) 0.0386(9) Uani 1 1 d . . . . .
H29A H 0.383176 0.199663 -0.041768 0.058 Uiso 1 1 calc R U . . .
H29B H 0.485651 0.148096 -0.029592 0.058 Uiso 1 1 calc R U . . .
H29C H 0.462331 0.314213 -0.035305 0.058 Uiso 1 1 calc R U . . .
C30 C 0.7374(2) 0.4401(4) 0.20699(12) 0.0243(7) Uani 1 1 d . . . . .
H30A H 0.795218 0.411049 0.200510 0.029 Uiso 1 1 calc R U . . .
H30B H 0.724108 0.538148 0.194284 0.029 Uiso 1 1 calc R U . . .
C31 C 0.7477(2) 0.4405(4) 0.26195(12) 0.0200(6) Uani 1 1 d . . . . .
C32 C 0.6921(2) 0.5258(4) 0.28260(13) 0.0229(7) Uani 1 1 d . . . . .
H32 H 0.646009 0.581078 0.261699 0.027 Uiso 1 1 calc R U . . .
C33 C 0.7041(2) 0.5301(4) 0.33344(13) 0.0251(7) Uani 1 1 d . . . . .
H33 H 0.666375 0.588490 0.347271 0.030 Uiso 1 1 calc R U . . .
C34 C 0.7715(2) 0.4490(4) 0.36429(12) 0.0256(7) Uani 1 1 d . . . . .
H34 H 0.779904 0.452713 0.399134 0.031 Uiso 1 1 calc R U . . .
C35 C 0.8261(2) 0.3630(4) 0.34413(13) 0.0225(7) Uani 1 1 d . . . . .
H35 H 0.871444 0.306706 0.365131 0.027 Uiso 1 1 calc R U . . .
C36 C 0.8146(2) 0.3590(4) 0.29326(12) 0.0205(6) Uani 1 1 d . . . . .
H36 H 0.852474 0.300350 0.279635 0.025 Uiso 1 1 calc R U . . .
C37 C 0.2187(5) 0.3385(8) 0.5183(2) 0.083(2) Uani 1 1 d . . . . .
H37A H 0.165442 0.376983 0.527717 0.100 Uiso 1 1 calc R U . . .
H37B H 0.250235 0.273579 0.545036 0.100 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'
I I -0.3257 6.8362 '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
C7 O1 H1 114(4) . . ?
C4 O2 C9 114.5(3) . . ?
C9 O3 C8 113.9(3) . . ?
C25 O4 H4 109.5 . . ?
C22 O5 C27 114.1(3) . . ?
C27 O6 C26 114.1(3) . . ?
C1 N1 C5 122.4(3) . . ?
C1 N1 C12 119.4(3) . . ?
C5 N1 C12 118.2(3) . . ?
C19 N2 C23 122.4(3) . . ?
C19 N2 C30 119.8(3) . . ?
C23 N2 C30 117.7(3) . . ?
N1 C1 H1A 119.3 . . ?
N1 C1 C2 121.5(3) . . ?
C2 C1 H1A 119.3 . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 C7 119.8(3) . . ?
C3 C2 C7 121.6(3) . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 C8 122.2(3) . . ?
C4 C3 C8 118.8(3) . . ?
O2 C4 C3 122.5(3) . . ?
O2 C4 C5 116.8(3) . . ?
C3 C4 C5 120.7(3) . . ?
N1 C5 C4 117.7(3) . . ?
N1 C5 C6 120.6(3) . . ?
C4 C5 C6 121.7(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C2 108.1(3) . . ?
O1 C7 H7A 110.1 . . ?
O1 C7 H7B 110.1 . . ?
C2 C7 H7A 110.1 . . ?
C2 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O3 C8 C3 110.8(3) . . ?
O3 C8 H8 124.6 . . ?
C3 C8 H8 124.6 . . ?
O2 C9 C10 105.8(3) . . ?
O2 C9 C11 107.8(3) . . ?
O3 C9 O2 109.2(3) . . ?
O3 C9 C10 106.8(3) . . ?
O3 C9 C11 113.2(3) . . ?
C10 C9 C11 113.7(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 108.7 . . ?
N1 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 N1 114.3(3) . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 C18 118.9(3) . . ?
C18 C13 C12 120.3(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
N2 C19 H19 119.3 . . ?
N2 C19 C20 121.4(3) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C21 118.8(3) . . ?
C19 C20 C25 119.4(3) . . ?
C21 C20 C25 121.8(3) . . ?
C20 C21 C26 122.0(3) . . ?
C22 C21 C20 118.7(3) . . ?
C22 C21 C26 119.4(3) . . ?
O5 C22 C21 122.1(3) . . ?
O5 C22 C23 116.3(3) . . ?
C21 C22 C23 121.5(3) . . ?
N2 C23 C22 117.1(3) . . ?
N2 C23 C24 120.5(3) . . ?
C22 C23 C24 122.3(3) . . ?
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 . . ?
O4 C25 C20 108.4(3) . . ?
O4 C25 H25 125.8 . . ?
C20 C25 H25 125.8 . . ?
O6 C26 C21 110.6(3) . . ?
O6 C26 H26A 109.5 . . ?
O6 C26 H26B 109.5 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
O5 C27 C28 108.9(3) . . ?
O5 C27 C29 105.4(3) . . ?
O6 C27 O5 108.2(3) . . ?
O6 C27 C28 113.4(4) . . ?
O6 C27 C29 106.7(3) . . ?
C29 C27 C28 113.8(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N2 C30 H30A 108.8 . . ?
N2 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
C31 C30 N2 113.7(3) . . ?
C31 C30 H30A 108.8 . . ?
C31 C30 H30B 108.8 . . ?
C32 C31 C30 120.4(3) . . ?
C36 C31 C30 120.5(3) . . ?
C36 C31 C32 119.0(3) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.3(3) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.2(3) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 120.0(3) . . ?
C35 C34 H34 120.0 . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C36 120.1(3) . . ?
C36 C35 H35 120.0 . . ?
C31 C36 H36 119.7 . . ?
C35 C36 C31 120.6(3) . . ?
C35 C36 H36 119.7 . . ?
Cl1 C37 Cl2 113.4(3) . . ?
Cl1 C37 H37A 108.9 . . ?
Cl1 C37 H37B 108.9 . . ?
Cl2 C37 H37A 108.9 . . ?
Cl2 C37 H37B 108.9 . . ?
H37A C37 H37B 107.7 . . ?
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 C37 1.730(5) . ?
Cl2 C37 1.758(5) . ?
O1 H1 0.76(5) . ?
O1 C7 1.416(4) . ?
O2 C4 1.356(4) . ?
O2 C9 1.463(4) . ?
O3 C8 1.419(4) . ?
O3 C9 1.403(5) . ?
O4 H4 0.8400 . ?
O4 C25 1.407(4) . ?
O5 C22 1.363(4) . ?
O5 C27 1.463(4) . ?
O6 C26 1.428(4) . ?
O6 C27 1.416(5) . ?
N1 C1 1.346(4) . ?
N1 C5 1.350(4) . ?
N1 C12 1.506(4) . ?
N2 C19 1.347(4) . ?
N2 C23 1.355(4) . ?
N2 C30 1.504(4) . ?
C1 H1A 0.9500 . ?
C1 C2 1.374(4) . ?
C2 C3 1.391(4) . ?
C2 C7 1.503(4) . ?
C3 C4 1.397(5) . ?
C3 C8 1.497(5) . ?
C4 C5 1.401(5) . ?
C5 C6 1.494(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 0.9500 . ?
C9 C10 1.506(5) . ?
C9 C11 1.527(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.498(4) . ?
C13 C14 1.392(5) . ?
C13 C18 1.396(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.375(5) . ?
C20 C21 1.392(5) . ?
C20 C25 1.509(5) . ?
C21 C22 1.388(5) . ?
C21 C26 1.510(5) . ?
C22 C23 1.403(5) . ?
C23 C24 1.491(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.507(6) . ?
C27 C29 1.506(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.504(4) . ?
C31 C32 1.400(5) . ?
C31 C36 1.396(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.386(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.393(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.385(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.388(5) . ?
C36 H36 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
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
O2 C4 C5 N1 -179.3(3) . . . . ?
O2 C4 C5 C6 1.2(5) . . . . ?
O5 C22 C23 N2 178.2(3) . . . . ?
O5 C22 C23 C24 -0.8(5) . . . . ?
N1 C1 C2 C3 0.4(5) . . . . ?
N1 C1 C2 C7 179.9(3) . . . . ?
N1 C12 C13 C14 86.4(4) . . . . ?
N1 C12 C13 C18 -95.7(4) . . . . ?
N2 C19 C20 C21 0.1(5) . . . . ?
N2 C19 C20 C25 -179.3(3) . . . . ?
N2 C30 C31 C32 -83.2(4) . . . . ?
N2 C30 C31 C36 98.7(4) . . . . ?
C1 N1 C5 C4 -1.0(5) . . . . ?
C1 N1 C5 C6 178.6(3) . . . . ?
C1 N1 C12 C13 5.2(4) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C1 C2 C3 C8 -178.2(3) . . . . ?
C1 C2 C7 O1 7.8(4) . . . . ?
C2 C3 C4 O2 179.6(3) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C2 C3 C8 O3 165.7(3) . . . . ?
C3 C2 C7 O1 -172.7(3) . . . . ?
C3 C4 C5 N1 1.9(5) . . . . ?
C3 C4 C5 C6 -177.7(3) . . . . ?
C4 O2 C9 O3 47.2(4) . . . . ?
C4 O2 C9 C10 161.8(3) . . . . ?
C4 O2 C9 C11 -76.1(4) . . . . ?
C4 C3 C8 O3 -13.0(5) . . . . ?
C5 N1 C1 C2 -0.2(5) . . . . ?
C5 N1 C12 C13 -173.8(3) . . . . ?
C7 C2 C3 C4 -179.0(3) . . . . ?
C7 C2 C3 C8 2.3(5) . . . . ?
C8 O3 C9 O2 -65.1(4) . . . . ?
C8 O3 C9 C10 -179.1(3) . . . . ?
C8 O3 C9 C11 55.0(4) . . . . ?
C8 C3 C4 O2 -1.7(5) . . . . ?
C8 C3 C4 C5 177.1(3) . . . . ?
C9 O2 C4 C3 -15.6(5) . . . . ?
C9 O2 C4 C5 165.6(3) . . . . ?
C9 O3 C8 C3 47.0(4) . . . . ?
C12 N1 C1 C2 -179.1(3) . . . . ?
C12 N1 C5 C4 178.0(3) . . . . ?
C12 N1 C5 C6 -2.5(4) . . . . ?
C12 C13 C14 C15 176.7(3) . . . . ?
C12 C13 C18 C17 -177.4(3) . . . . ?
C13 C14 C15 C16 1.2(5) . . . . ?
C14 C13 C18 C17 0.5(5) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C17 C18 C13 0.3(5) . . . . ?
C18 C13 C14 C15 -1.3(5) . . . . ?
C19 N2 C23 C22 1.7(5) . . . . ?
C19 N2 C23 C24 -179.3(3) . . . . ?
C19 N2 C30 C31 -10.2(4) . . . . ?
C19 C20 C21 C22 -0.8(5) . . . . ?
C19 C20 C21 C26 -179.7(3) . . . . ?
C19 C20 C25 O4 -4.7(4) . . . . ?
C20 C21 C22 O5 -178.7(3) . . . . ?
C20 C21 C22 C23 1.9(5) . . . . ?
C20 C21 C26 O6 -170.0(3) . . . . ?
C21 C20 C25 O4 175.9(3) . . . . ?
C21 C22 C23 N2 -2.4(5) . . . . ?
C21 C22 C23 C24 178.7(3) . . . . ?
C22 O5 C27 O6 -51.2(4) . . . . ?
C22 O5 C27 C28 72.5(4) . . . . ?
C22 O5 C27 C29 -165.1(3) . . . . ?
C22 C21 C26 O6 11.1(5) . . . . ?
C23 N2 C19 C20 -0.6(5) . . . . ?
C23 N2 C30 C31 168.1(3) . . . . ?
C25 C20 C21 C22 178.6(3) . . . . ?
C25 C20 C21 C26 -0.3(5) . . . . ?
C26 O6 C27 O5 65.7(4) . . . . ?
C26 O6 C27 C28 -55.2(4) . . . . ?
C26 O6 C27 C29 178.7(3) . . . . ?
C26 C21 C22 O5 0.3(5) . . . . ?
C26 C21 C22 C23 -179.1(3) . . . . ?
C27 O5 C22 C21 20.1(4) . . . . ?
C27 O5 C22 C23 -160.5(3) . . . . ?
C27 O6 C26 C21 -44.7(4) . . . . ?
C30 N2 C19 C20 177.6(3) . . . . ?
C30 N2 C23 C22 -176.6(3) . . . . ?
C30 N2 C23 C24 2.4(5) . . . . ?
C30 C31 C32 C33 -177.5(3) . . . . ?
C30 C31 C36 C35 177.8(3) . . . . ?
C31 C32 C33 C34 -0.2(5) . . . . ?
C32 C31 C36 C35 -0.3(5) . . . . ?
C32 C33 C34 C35 -0.5(5) . . . . ?
C33 C34 C35 C36 0.9(5) . . . . ?
C34 C35 C36 C31 -0.4(5) . . . . ?
C36 C31 C32 C33 0.6(5) . . . . ?
