#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:43:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178403 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/24/4022458.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_4022458
loop_
_publ_author_name
'Christopher A. Burnett'
'Dariusz Witt'
'James C. Fettinger'
'Lyle Isaacs'
_publ_contact_author
;
Lyle Isaacs
University of Maryland
Department of Chemistry and Biochemistry
College Park, MD 20742
;
_publ_contact_author_email       LI8@umail.umd.edu
_publ_section_title
;
 Acyclic Congener of Cucurbituril: Synthesis and Recognition Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6184
_journal_page_last               6191
_journal_paper_doi               10.1021/jo034399w
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C57.56 H63 Cl0.67 N8 O16.22'
_chemical_formula_weight         1150.02
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   47.427(5)
_cell_length_b                   47.427(5)
_cell_length_c                   12.6667(18)
_cell_measurement_temperature    153(2)
_cell_volume                     24674(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            55632
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.49
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   'Empirical, SADABS'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             10898
_exptl_crystal_size_max          0.545
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.182
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.00002(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     779
_refine_ls_number_reflns         9642
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1011P)²+19.4131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.1739
_reflns_number_gt                7164
_reflns_number_total             9642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo034399wsi20030327_111424.cif
_cod_data_source_block           Compound3C
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Rhombohedral' changed to 'rhombohedral'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4022458
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.42477(6) 0.43267(8) -0.0814(2) 0.0474(7) Uani 1 1 d . . .
C1B C 0.41313(10) 0.39574(12) -0.2251(3) 0.0850(12) Uani 1 1 d . . .
H1B1 H 0.4092 0.4095 -0.2736 0.128 Uiso 1 1 calc R . .
H1B2 H 0.3985 0.3728 -0.2427 0.128 Uiso 1 1 calc R . .
H1B3 H 0.4358 0.4008 -0.2314 0.128 Uiso 1 1 calc R . .
O1 O 0.40710(5) 0.40162(6) -0.12043(16) 0.0638(6) Uani 1 1 d . . .
C2 C 0.44739(7) 0.45928(9) -0.1377(2) 0.0545(8) Uani 1 1 d . . .
H2 H 0.4521 0.4566 -0.2086 0.065 Uiso 1 1 calc R . .
C3 C 0.46326(7) 0.48968(8) -0.0925(2) 0.0500(7) Uani 1 1 d . . .
H3 H 0.4793 0.5076 -0.1318 0.060 Uiso 1 1 calc R . .
C4 C 0.45613(6) 0.49452(7) 0.0099(2) 0.0437(6) Uani 1 1 d . . .
C4A C 0.43383(6) 0.46769(7) 0.0702(2) 0.0394(6) Uani 1 1 d . . .
C4B C 0.49539(7) 0.55157(8) 0.0033(3) 0.0595(8) Uani 1 1 d . . .
H4B1 H 0.5130 0.5470 -0.0119 0.089 Uiso 1 1 calc R . .
H4B2 H 0.5038 0.5711 0.0474 0.089 Uiso 1 1 calc R . .
H4B3 H 0.4870 0.5551 -0.0631 0.089 Uiso 1 1 calc R . .
O4 O 0.46956(5) 0.52434(5) 0.05826(16) 0.0538(5) Uani 1 1 d . . .
C5 C 0.42594(6) 0.47286(6) 0.1828(2) 0.0370(6) Uani 1 1 d . . .
H5A H 0.4380 0.4965 0.1985 0.044 Uiso 1 1 calc R . .
H5B H 0.4024 0.4655 0.1872 0.044 Uiso 1 1 calc R . .
C5B C 0.41476(5) 0.42098(6) 0.27745(19) 0.0327(5) Uani 1 1 d . . .
C5C C 0.38142(5) 0.41099(6) 0.3276(2) 0.0347(5) Uani 1 1 d . . .
C5D C 0.35566(6) 0.41909(7) 0.4741(2) 0.0460(7) Uani 1 1 d . . .
H5D1 H 0.3411 0.3952 0.4798 0.055 Uiso 1 1 calc R . .
H5D2 H 0.3439 0.4283 0.4359 0.055 Uiso 1 1 calc R . .
C5E C 0.36528(8) 0.43380(8) 0.5807(2) 0.0557(8) Uani 1 1 d . . .
H5E1 H 0.3779 0.4253 0.6162 0.084 Uiso 1 1 calc R . .
H5E2 H 0.3457 0.4283 0.6220 0.084 Uiso 1 1 calc R . .
H5E3 H 0.3786 0.4575 0.5741 0.084 Uiso 1 1 calc R . .
N5 N 0.43382(4) 0.45592(5) 0.26319(16) 0.0338(5) Uani 1 1 d . . .
O5C O 0.35580(4) 0.39210(5) 0.28925(16) 0.0508(5) Uani 1 1 d . . .
O5D O 0.38566(4) 0.42651(4) 0.41754(14) 0.0421(4) Uani 1 1 d . . .
C6 C 0.46315(5) 0.46986(6) 0.31538(18) 0.0309(5) Uani 1 1 d . . .
C6B C 0.43816(5) 0.41410(6) 0.34872(19) 0.0331(5) Uani 1 1 d . . .
C6C C 0.42219(6) 0.39284(6) 0.4477(2) 0.0373(6) Uani 1 1 d . . .
C6D C 0.38259(7) 0.33945(7) 0.5021(2) 0.0519(7) Uani 1 1 d . . .
H6D1 H 0.3978 0.3438 0.5614 0.062 Uiso 1 1 calc R . .
H6D2 H 0.3755 0.3174 0.4746 0.062 Uiso 1 1 calc R . .
C6E C 0.35392(7) 0.34101(7) 0.5403(3) 0.0571(8) Uani 1 1 d . . .
H6E1 H 0.3612 0.3621 0.5740 0.086 Uiso 1 1 calc R . .
H6E2 H 0.3420 0.3236 0.5917 0.086 Uiso 1 1 calc R . .
H6E3 H 0.3397 0.3384 0.4806 0.086 Uiso 1 1 calc R . .
N6 N 0.46382(4) 0.44616(5) 0.37747(15) 0.0322(4) Uani 1 1 d . . .
O6 O 0.48454(4) 0.49827(4) 0.31050(14) 0.0404(4) Uani 1 1 d . . .
O6C O 0.43065(4) 0.40204(5) 0.53541(15) 0.0498(5) Uani 1 1 d . . .
O6D O 0.39922(4) 0.36348(4) 0.41834(15) 0.0465(5) Uani 1 1 d . . .
C7 C 0.49500(5) 0.45155(6) 0.41847(19) 0.0364(5) Uani 1 1 d . . .
H7A H 0.4907 0.4356 0.4754 0.044 Uiso 1 1 calc R . .
H7B H 0.5069 0.4736 0.4502 0.044 Uiso 1 1 calc R . .
C7A C 0.51664(5) 0.44864(6) 0.33659(19) 0.0329(5) Uani 1 1 d . . .
C8 C 0.54717(5) 0.47544(6) 0.31359(19) 0.0327(5) Uani 1 1 d . . .
H8 H 0.5539 0.4955 0.3490 0.039 Uiso 1 1 calc R . .
C8A C 0.56797(5) 0.47354(6) 0.24029(19) 0.0328(5) Uani 1 1 d . . .
C9 C 0.59993(5) 0.50333(6) 0.2131(2) 0.0364(6) Uani 1 1 d . . .
H9A H 0.5996 0.5090 0.1381 0.044 Uiso 1 1 calc R . .
H9B H 0.6027 0.5218 0.2568 0.044 Uiso 1 1 calc R . .
C9B C 0.62425(5) 0.46679(5) 0.24964(18) 0.0300(5) Uani 1 1 d . . .
C9C C 0.60781(5) 0.45177(5) 0.35596(18) 0.0299(5) Uani 1 1 d . . .
C9D C 0.59268(7) 0.46152(6) 0.5234(2) 0.0437(6) Uani 1 1 d . . .
H9D1 H 0.6028 0.4505 0.5610 0.052 Uiso 1 1 calc R . .
H9D2 H 0.5694 0.4455 0.5120 0.052 Uiso 1 1 calc R . .
C9E C 0.59601(8) 0.48930(7) 0.5874(2) 0.0564(8) Uani 1 1 d . . .
H9E1 H 0.6191 0.5056 0.5948 0.085 Uiso 1 1 calc R . .
H9E2 H 0.5865 0.4815 0.6574 0.085 Uiso 1 1 calc R . .
H9E3 H 0.5846 0.4991 0.5521 0.085 Uiso 1 1 calc R . .
N9 N 0.62763(4) 0.49826(5) 0.23051(16) 0.0328(4) Uani 1 1 d . . .
O9C O 0.59649(4) 0.42324(4) 0.37459(14) 0.0404(4) Uani 1 1 d . . .
O9D O 0.60887(4) 0.47397(4) 0.42195(13) 0.0331(4) Uani 1 1 d . . .
C10 C 0.65873(5) 0.52107(5) 0.19935(18) 0.0312(5) Uani 1 1 d . . .
C10B C 0.66055(5) 0.47374(5) 0.24477(18) 0.0305(5) Uani 1 1 d . . .
C10C C 0.67390(5) 0.47165(6) 0.3534(2) 0.0375(6) Uani 1 1 d . A .
C10D C 0.68831(8) 0.44087(9) 0.4664(3) 0.0678(9) Uani 0.72 1 d P A 1
H10A H 0.7027 0.4625 0.4982 0.081 Uiso 0.72 1 calc PR A 1
H10B H 0.7013 0.4300 0.4547 0.081 Uiso 0.72 1 calc PR A 1
C10E C 0.66081(13) 0.42092(14) 0.5394(5) 0.0797(15) Uiso 0.72 1 d P A 1
H10C H 0.6486 0.4322 0.5531 0.119 Uiso 0.72 1 calc PR A 1
H10D H 0.6694 0.4178 0.6060 0.119 Uiso 0.72 1 calc PR A 1
H10E H 0.6464 0.3997 0.5070 0.119 Uiso 0.72 1 calc PR A 1
C10F C 0.68831(8) 0.44087(9) 0.4664(3) 0.0678(9) Uani 0.28 1 d P A 2
H10F H 0.6721 0.4350 0.5236 0.081 Uiso 0.28 1 calc PR A 2
H10G H 0.7085 0.4610 0.4863 0.081 Uiso 0.28 1 calc PR A 2
C10G C 0.6953(4) 0.4116(4) 0.4429(13) 0.087(4) Uiso 0.28 1 d P A 2
H10H H 0.6749 0.3921 0.4229 0.130 Uiso 0.28 1 calc PR A 2
H10I H 0.7042 0.4071 0.5064 0.130 Uiso 0.28 1 calc PR A 2
H10J H 0.7110 0.4179 0.3851 0.130 Uiso 0.28 1 calc PR A 2
N10 N 0.67766(4) 0.50687(4) 0.20796(15) 0.0308(4) Uani 1 1 d . . .
O10 O 0.66738(4) 0.54876(4) 0.17225(14) 0.0375(4) Uani 1 1 d . . .
O10C O 0.68130(5) 0.49263(5) 0.41840(15) 0.0536(5) Uani 1 1 d . . .
O10D O 0.67555(4) 0.44482(5) 0.36530(15) 0.0497(5) Uani 1 1 d . . .
C11 C 0.71169(5) 0.52227(6) 0.17530(19) 0.0341(5) Uani 1 1 d . . .
H11A H 0.7240 0.5178 0.2296 0.041 Uiso 1 1 calc R . .
H11B H 0.7207 0.5461 0.1728 0.041 Uiso 1 1 calc R . .
C11A C 0.71738(5) 0.51120(6) 0.06915(19) 0.0326(5) Uani 1 1 d . . .
C12 C 0.73600(6) 0.53533(6) -0.0054(2) 0.0385(6) Uani 1 1 d . . .
C12B C 0.76150(8) 0.59172(7) -0.0501(3) 0.0609(8) Uani 1 1 d . . .
H12A H 0.7818 0.5932 -0.0747 0.091 Uiso 1 1 calc R . .
H12B H 0.7662 0.6125 -0.0185 0.091 Uiso 1 1 calc R . .
H12C H 0.7466 0.5867 -0.1100 0.091 Uiso 1 1 calc R . .
O12 O 0.74682(4) 0.56677(4) 0.02605(15) 0.0476(5) Uani 1 1 d . . .
C13 C 0.74363(6) 0.52675(7) -0.1008(2) 0.0464(7) Uani 1 1 d . . .
H13 H 0.7558 0.5431 -0.1517 0.056 Uiso 1 1 calc R . .
C14 C 0.73358(7) 0.49447(7) -0.1228(2) 0.0469(7) Uani 1 1 d . . .
H14 H 0.7392 0.4888 -0.1882 0.056 Uiso 1 1 calc R . .
C15 C 0.71531(6) 0.47035(6) -0.0496(2) 0.0382(6) Uani 1 1 d . . .
C15A C 0.70689(5) 0.47853(6) 0.04696(19) 0.0327(5) Uani 1 1 d . . .
C15B C 0.71458(9) 0.42893(8) -0.1587(3) 0.0648(9) Uani 1 1 d . . .
H15A H 0.7054 0.4343 -0.2197 0.097 Uiso 1 1 calc R . .
H15B H 0.7066 0.4055 -0.1579 0.097 Uiso 1 1 calc R . .
H15C H 0.7384 0.4408 -0.1635 0.097 Uiso 1 1 calc R . .
O15 O 0.70484(5) 0.43788(5) -0.06443(15) 0.0491(5) Uani 1 1 d . . .
C16 C 0.68846(6) 0.45191(6) 0.1276(2) 0.0350(5) Uani 1 1 d . . .
H16A H 0.6823 0.4307 0.0946 0.042 Uiso 1 1 calc R . .
H16B H 0.7033 0.4551 0.1871 0.042 Uiso 1 1 calc R . .
N16 N 0.65898(4) 0.45035(4) 0.16993(16) 0.0312(4) Uani 1 1 d . . .
C17 C 0.63042(5) 0.43655(6) 0.11368(19) 0.0331(5) Uani 1 1 d . . .
N17 N 0.60924(4) 0.44371(5) 0.16484(16) 0.0349(5) Uani 1 1 d . . .
O17 O 0.62433(4) 0.42001(4) 0.03463(14) 0.0428(4) Uani 1 1 d . . .
C18 C 0.58029(6) 0.44028(7) 0.1115(2) 0.0394(6) Uani 1 1 d . . .
H18A H 0.5684 0.4187 0.0770 0.047 Uiso 1 1 calc R . .
H18B H 0.5869 0.4572 0.0562 0.047 Uiso 1 1 calc R . .
C18A C 0.55826(5) 0.44370(6) 0.19009(19) 0.0350(5) Uani 1 1 d . . .
C19 C 0.52805(5) 0.41713(6) 0.2126(2) 0.0362(5) Uani 1 1 d . . .
H19 H 0.5216 0.3970 0.1784 0.043 Uiso 1 1 calc R . .
C19A C 0.50700(5) 0.41933(6) 0.2841(2) 0.0348(5) Uani 1 1 d . . .
C20 C 0.47339(5) 0.38997(6) 0.2998(2) 0.0382(6) Uani 1 1 d . . .
H20A H 0.4710 0.3720 0.2539 0.046 Uiso 1 1 calc R . .
H20B H 0.4711 0.3826 0.3740 0.046 Uiso 1 1 calc R . .
N20 N 0.44767(4) 0.39717(5) 0.27565(16) 0.0350(5) Uani 1 1 d . . .
C21 C 0.43460(5) 0.39364(5) 0.1770(2) 0.0347(5) Uani 1 1 d . . .
N21 N 0.41091(5) 0.40253(5) 0.18372(16) 0.0363(5) Uani 1 1 d . . .
O21 O 0.44177(4) 0.38367(4) 0.09910(15) 0.0436(4) Uani 1 1 d . . .
C22 C 0.39617(6) 0.40677(7) 0.0878(2) 0.0444(6) Uani 1 1 d . . .
H22A H 0.3766 0.4080 0.1078 0.053 Uiso 1 1 calc R . .
H22B H 0.3889 0.3873 0.0425 0.053 Uiso 1 1 calc R . .
C22A C 0.41855(6) 0.43661(7) 0.0248(2) 0.0415(6) Uani 1 1 d . . .
C31 C 0.66655(14) 0.50504(18) 0.7633(5) 0.0775(17) Uani 0.67 1 d P B 1
C32 C 0.65303(13) 0.4996(3) 0.8587(5) 0.0738(16) Uani 0.67 1 d P B 1
H32 H 0.6434 0.4778 0.8835 0.089 Uiso 0.67 1 calc PR B 1
C33 C 0.65133(14) 0.5193(3) 0.9197(6) 0.088(2) Uani 0.67 1 d P B 1
H33 H 0.6411 0.5126 0.9868 0.105 Uiso 0.67 1 calc PR B 1
C34 C 0.66469(17) 0.5511(2) 0.8869(7) 0.097(2) Uani 0.67 1 d P B 1
H34 H 0.6639 0.5669 0.9308 0.116 Uiso 0.67 1 calc PR B 1
C35 C 0.68012(11) 0.56003(13) 0.7837(5) 0.0657(14) Uani 0.67 1 d P B 1
H35 H 0.6893 0.5819 0.7603 0.079 Uiso 0.67 1 calc PR B 1
C36 C 0.68181(16) 0.53682(17) 0.7168(7) 0.083(2) Uani 0.67 1 d P B 1
H36 H 0.6919 0.5418 0.6493 0.100 Uiso 0.67 1 calc PR B 1
C37 C 0.6693(2) 0.4827(3) 0.6908(6) 0.126(3) Uani 0.67 1 d P B 1
H37A H 0.6807 0.4944 0.6268 0.189 Uiso 0.67 1 calc PR B 1
H37B H 0.6475 0.4651 0.6721 0.189 Uiso 0.67 1 calc PR B 1
H37C H 0.6815 0.4735 0.7247 0.189 Uiso 0.67 1 calc PR B 1
C41 C 0.66738(17) 0.54156(13) 0.8441(5) 0.067(3) Uiso 0.33 1 d PGD C 2
C42 C 0.65164(18) 0.51163(14) 0.8952(4) 0.24(3) Uiso 0.33 1 d PGD C 2
H42 H 0.6428 0.5100 0.9638 0.293 Uiso 0.33 1 calc PR C 2
C43 C 0.64884(15) 0.48414(12) 0.8461(4) 0.148(12) Uiso 0.33 1 d PG C 2
H43 H 0.6381 0.4637 0.8810 0.178 Uiso 0.33 1 calc PR C 2
C44 C 0.66176(11) 0.48659(9) 0.7458(3) 0.122(8) Uiso 0.33 1 d PG C 2
H44 H 0.6598 0.4678 0.7121 0.146 Uiso 0.33 1 calc PR C 2
C45 C 0.67750(12) 0.51652(8) 0.6947(4) 0.106(5) Uiso 0.33 1 d PG C 2
H45 H 0.6863 0.5182 0.6261 0.127 Uiso 0.33 1 calc PR C 2
C46 C 0.68030(14) 0.54401(10) 0.7438(5) 0.042(3) Uiso 0.33 1 d PGD C 2
H46 H 0.6911 0.5645 0.7089 0.051 Uiso 0.33 1 calc PR C 2
C47 C 0.6671(2) 0.56297(16) 0.9165(6) 0.103(7) Uiso 0.33 1 d PGD C 2
H47A H 0.6447 0.5550 0.9409 0.155 Uiso 0.33 1 calc PR C 2
H47B H 0.6754 0.5844 0.8835 0.155 Uiso 0.33 1 calc PR C 2
H47C H 0.6809 0.5648 0.9768 0.155 Uiso 0.33 1 calc PR C 2
C51 C 0.66667(6) 0.33333(5) 0.5945(3) 0.073(2) Uani 0.56 3 d SPGU . .
H51 H 0.6667 0.3333 0.5156 0.087 Uiso 0.56 3 calc SPR . .
Cl51 Cl 0.69814(5) 0.37088(5) 0.63401(19) 0.1018(7) Uani 0.56 1 d PG . .
C52 C 0.66667(6) 0.33333(5) 0.5945(3) 0.073(2) Uani 0.11 3 d SPGU . 1
H52 H 0.6667 0.3333 0.5156 0.087 Uiso 0.11 3 calc SPR C 1
Cl52 Cl 0.70539(6) 0.35249(5) 0.6467(2) 0.160(7) Uani 0.11 1 d PG . 1
C61 C 0.66110(19) 0.35807(15) 0.3311(3) 0.171(14) Uani 0.33 1 d PG . 2
H61 H 0.6571 0.3757 0.3247 0.257 Uiso 0.33 1 calc PR C 2
O71 O 0.5480(2) 0.5337(2) 0.4043(8) 0.099(4) Uani 0.22 1 d PRD . .
H71A H 0.5477 0.5405 0.4656 0.148 Uiso 0.22 1 d PRD . .
H71B H 0.5292 0.5232 0.3763 0.148 Uiso 0.22 1 d PRD . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 C1 C2 125.1(3) . .
O1 C1 C22A 115.5(2) . .
C2 C1 C22A 119.4(3) . .
O1 C1B H1B1 109.5 . .
O1 C1B H1B2 109.5 . .
H1B1 C1B H1B2 109.5 . .
O1 C1B H1B3 109.5 . .
H1B1 C1B H1B3 109.5 . .
H1B2 C1B H1B3 109.5 . .
C1 O1 C1B 118.3(3) . .
C3 C2 C1 120.9(3) . .
C3 C2 H2 119.6 . .
C1 C2 H2 119.6 . .
C2 C3 C4 120.8(3) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
O4 C4 C3 124.2(2) . .
O4 C4 C4A 116.3(2) . .
C3 C4 C4A 119.6(3) . .
C22A C4A C4 119.3(2) . .
C22A C4A C5 120.9(2) . .
C4 C4A C5 119.8(2) . .
O4 C4B H4B1 109.5 . .
O4 C4B H4B2 109.5 . .
H4B1 C4B H4B2 109.5 . .
O4 C4B H4B3 109.5 . .
H4B1 C4B H4B3 109.5 . .
H4B2 C4B H4B3 109.5 . .
C4 O4 C4B 117.2(2) . .
N5 C5 C4A 114.5(2) . .
N5 C5 H5A 108.6 . .
C4A C5 H5A 108.6 . .
N5 C5 H5B 108.6 . .
C4A C5 H5B 108.6 . .
H5A C5 H5B 107.6 . .
N21 C5B N5 114.31(19) . .
N21 C5B C5C 110.86(18) . .
N5 C5B C5C 111.12(19) . .
N21 C5B C6B 103.59(19) . .
N5 C5B C6B 101.86(17) . .
C5C C5B C6B 114.70(19) . .
O5C C5C O5D 125.8(2) . .
O5C C5C C5B 124.4(2) . .
O5D C5C C5B 109.77(19) . .
O5D C5D C5E 107.3(2) . .
O5D C5D H5D1 110.2 . .
C5E C5D H5D1 110.2 . .
O5D C5D H5D2 110.2 . .
C5E C5D H5D2 110.2 . .
H5D1 C5D H5D2 108.5 . .
C5D C5E H5E1 109.5 . .
C5D C5E H5E2 109.5 . .
H5E1 C5E H5E2 109.5 . .
C5D C5E H5E3 109.5 . .
H5E1 C5E H5E3 109.5 . .
H5E2 C5E H5E3 109.5 . .
C6 N5 C5B 113.14(18) . .
C6 N5 C5 123.22(19) . .
C5B N5 C5 122.19(19) . .
C5C O5D C5D 115.44(19) . .
O6 C6 N5 126.2(2) . .
O6 C6 N6 125.6(2) . .
N5 C6 N6 108.13(19) . .
N20 C6B N6 114.64(18) . .
N20 C6B C6C 110.20(19) . .
N6 C6B C6C 111.3(2) . .
N20 C6B C5B 101.28(19) . .
N6 C6B C5B 103.65(18) . .
C6C C6B C5B 115.45(18) . .
O6C C6C O6D 126.8(2) . .
O6C C6C C6B 123.6(2) . .
O6D C6C C6B 109.6(2) . .
O6D C6D C6E 110.4(2) . .
O6D C6D H6D1 109.6 . .
C6E C6D H6D1 109.6 . .
O6D C6D H6D2 109.6 . .
C6E C6D H6D2 109.6 . .
H6D1 C6D H6D2 108.1 . .
C6D C6E H6E1 109.5 . .
C6D C6E H6E2 109.5 . .
H6E1 C6E H6E2 109.5 . .
C6D C6E H6E3 109.5 . .
H6E1 C6E H6E3 109.5 . .
H6E2 C6E H6E3 109.5 . .
C6 N6 C6B 111.27(18) . .
C6 N6 C7 119.39(18) . .
C6B N6 C7 121.38(19) . .
C6C O6D C6D 117.1(2) . .
N6 C7 C7A 114.38(19) . .
N6 C7 H7A 108.7 . .
C7A C7 H7A 108.7 . .
N6 C7 H7B 108.7 . .
C7A C7 H7B 108.7 . .
H7A C7 H7B 107.6 . .
C19A C7A C8 118.7(2) . .
C19A C7A C7 121.2(2) . .
C8 C7A C7 120.1(2) . .
C8A C8 C7A 121.8(2) . .
C8A C8 H8 119.1 . .
C7A C8 H8 119.1 . .
C8 C8A C18A 118.9(2) . .
C8 C8A C9 120.4(2) . .
C18A C8A C9 120.7(2) . .
N9 C9 C8A 112.07(18) . .
N9 C9 H9A 109.2 . .
C8A C9 H9A 109.2 . .
N9 C9 H9B 109.2 . .
C8A C9 H9B 109.2 . .
H9A C9 H9B 107.9 . .
N9 C9B N17 114.72(19) . .
N9 C9B C9C 113.24(19) . .
N17 C9B C9C 110.89(18) . .
N9 C9B C10B 103.40(16) . .
N17 C9B C10B 101.64(17) . .
C9C C9B C10B 112.12(18) . .
O9C C9C O9D 126.0(2) . .
O9C C9C C9B 122.0(2) . .
O9D C9C C9B 112.00(18) . .
O9D C9D C9E 108.7(2) . .
O9D C9D H9D1 110.0 . .
C9E C9D H9D1 110.0 . .
O9D C9D H9D2 110.0 . .
C9E C9D H9D2 110.0 . .
H9D1 C9D H9D2 108.3 . .
C9D C9E H9E1 109.5 . .
C9D C9E H9E2 109.5 . .
H9E1 C9E H9E2 109.5 . .
C9D C9E H9E3 109.5 . .
H9E1 C9E H9E3 109.5 . .
H9E2 C9E H9E3 109.5 . .
C10 N9 C9B 112.43(18) . .
C10 N9 C9 121.51(19) . .
C9B N9 C9 123.45(17) . .
C9C O9D C9D 115.48(17) . .
O10 C10 N10 127.2(2) . .
O10 C10 N9 125.4(2) . .
N10 C10 N9 107.36(19) . .
N16 C10B N10 114.44(18) . .
N16 C10B C10C 113.93(19) . .
N10 C10B C10C 109.55(19) . .
N16 C10B C9B 103.56(17) . .
N10 C10B C9B 101.59(17) . .
C10C C10B C9B 113.03(18) . .
O10C C10C O10D 125.9(2) . .
O10C C10C C10B 121.2(2) . .
O10D C10C C10B 112.8(2) . .
O10D C10D C10E 109.7(3) . .
O10D C10D H10A 109.7 . .
C10E C10D H10A 109.7 . .
O10D C10D H10B 109.7 . .
C10E C10D H10B 109.7 . .
H10A C10D H10B 108.2 . .
H10H C10G H10I 109.5 . .
H10H C10G H10J 109.5 . .
H10I C10G H10J 109.5 . .
C10 N10 C10B 114.35(17) . .
C10 N10 C11 124.35(19) . .
C10B N10 C11 121.13(18) . .
C10C O10D C10D 116.7(2) . .
N10 C11 C11A 114.96(19) . .
N10 C11 H11A 108.5 . .
C11A C11 H11A 108.5 . .
N10 C11 H11B 108.5 . .
C11A C11 H11B 108.5 . .
H11A C11 H11B 107.5 . .
C15A C11A C12 119.9(2) . .
C15A C11A C11 122.4(2) . .
C12 C11A C11 117.6(2) . .
O12 C12 C13 124.4(2) . .
O12 C12 C11A 115.6(2) . .
C13 C12 C11A 120.0(2) . .
O12 C12B H12A 109.5 . .
O12 C12B H12B 109.5 . .
H12A C12B H12B 109.5 . .
O12 C12B H12C 109.5 . .
H12A C12B H12C 109.5 . .
H12B C12B H12C 109.5 . .
C12 O12 C12B 118.2(2) . .
C12 C13 C14 120.4(2) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C13 C14 C15 120.3(2) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
O15 C15 C14 124.0(2) . .
O15 C15 C15A 115.9(2) . .
C14 C15 C15A 120.1(2) . .
C11A C15A C15 119.3(2) . .
C11A C15A C16 121.7(2) . .
C15 C15A C16 118.9(2) . .
O15 C15B H15A 109.5 . .
O15 C15B H15B 109.5 . .
H15A C15B H15B 109.5 . .
O15 C15B H15C 109.5 . .
H15A C15B H15C 109.5 . .
H15B C15B H15C 109.5 . .
C15 O15 C15B 117.5(2) . .
N16 C16 C15A 115.29(19) . .
N16 C16 H16A 108.5 . .
C15A C16 H16A 108.5 . .
N16 C16 H16B 108.5 . .
C15A C16 H16B 108.5 . .
H16A C16 H16B 107.5 . .
C17 N16 C10B 111.68(18) . .
C17 N16 C16 121.6(2) . .
C10B N16 C16 121.64(18) . .
O17 C17 N16 126.5(2) . .
O17 C17 N17 125.6(2) . .
N16 C17 N17 107.9(2) . .
C17 N17 C9B 113.24(18) . .
C17 N17 C18 121.1(2) . .
C9B N17 C18 120.51(19) . .
N17 C18 C18A 110.2(2) . .
N17 C18 H18A 109.6 . .
C18A C18 H18A 109.6 . .
N17 C18 H18B 109.6 . .
C18A C18 H18B 109.6 . .
H18A C18 H18B 108.1 . .
C19 C18A C8A 119.5(2) . .
C19 C18A C18 119.7(2) . .
C8A C18A C18 120.8(2) . .
C18A C19 C19A 121.4(2) . .
C18A C19 H19 119.3 . .
C19A C19 H19 119.3 . .
C19 C19A C7A 119.7(2) . .
C19 C19A C20 118.8(2) . .
C7A C19A C20 121.5(2) . .
N20 C20 C19A 112.15(19) . .
N20 C20 H20A 109.2 . .
C19A C20 H20A 109.2 . .
N20 C20 H20B 109.2 . .
C19A C20 H20B 109.2 . .
H20A C20 H20B 107.9 . .
C21 N20 C6B 114.01(19) . .
C21 N20 C20 123.1(2) . .
C6B N20 C20 122.0(2) . .
O21 C21 N20 126.3(2) . .
O21 C21 N21 126.6(2) . .
N20 C21 N21 107.1(2) . .
C21 N21 C5B 111.22(19) . .
C21 N21 C22 120.4(2) . .
C5B N21 C22 121.9(2) . .
N21 C22 C22A 114.1(2) . .
N21 C22 H22A 108.7 . .
C22A C22 H22A 108.7 . .
N21 C22 H22B 108.7 . .
C22A C22 H22B 108.7 . .
H22A C22 H22B 107.6 . .
C4A C22A C1 119.9(2) . .
C4A C22A C22 121.5(2) . .
C1 C22A C22 118.5(3) . .
C32 C31 C36 121.2(8) . .
C32 C31 C37 129.8(9) . .
C36 C31 C37 108.9(7) . .
C33 C32 C31 128.5(9) . .
C33 C32 H32 115.7 . .
C31 C32 H32 115.7 . .
C32 C33 C34 117.8(7) . .
C32 C33 H33 121.1 . .
C34 C33 H33 121.1 . .
C33 C34 C35 118.8(8) . .
C33 C34 H34 120.6 . .
C35 C34 H34 120.6 . .
C36 C35 C34 121.6(6) . .
C36 C35 H35 119.2 . .
C34 C35 H35 119.2 . .
C35 C36 C31 112.0(7) . .
C35 C36 H36 124.0 . .
C31 C36 H36 124.0 . .
C31 C37 H37A 109.5 . .
C31 C37 H37B 109.5 . .
H37A C37 H37B 109.5 . .
C31 C37 H37C 109.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
C47 C41 C42 104.2 . .
C47 C41 C46 135.7 . .
C42 C41 C46 120.0 . .
C43 C42 C41 120.0 . .
C43 C42 H42 120.0 . .
C41 C42 H42 120.0 . .
C42 C43 C44 120.0 . .
C42 C43 H43 120.0 . .
C44 C43 H43 120.0 . .
C43 C44 C45 120.0 . .
C43 C44 H44 120.0 . .
C45 C44 H44 120.0 . .
C44 C45 C46 120.0 . .
C44 C45 H45 120.0 . .
C46 C45 H45 120.0 . .
C45 C46 C41 120.0 . .
C45 C46 H46 120.0 . .
C41 C46 H46 120.0 . .
C41 C47 H47A 109.5 . .
C41 C47 H47B 109.5 . .
H47A C47 H47B 109.5 . .
C41 C47 H47C 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
Cl51 C51 Cl51 111.99(16) . 2_655
Cl51 C51 Cl51 111.99(16) . 3_665
Cl51 C51 Cl51 111.99(8) 2_655 3_665
Cl51 C51 H51 106.8 . .
Cl51 C51 H51 106.8 2_655 .
Cl51 C51 H51 106.8 3_665 .
Cl52 Cl51 C51 71.1 . .
Cl52 Cl51 Cl52 114.33(13) . 2_655
C51 Cl51 Cl52 52.06(12) . 2_655
Cl52 C52 Cl52 106.20(10) . 2_655
Cl52 C52 Cl52 106.20(17) . 3_665
Cl52 C52 Cl52 106.20(6) 2_655 3_665
Cl52 C52 H52 112.6 . .
Cl52 C52 H52 112.6 2_655 .
Cl52 C52 H52 112.6 3_665 .
Cl51 Cl52 C52 71.8 . .
Cl51 Cl52 Cl51 123.29(13) . 3_665
C52 Cl52 Cl51 52.37(12) . 3_665
C61 C61 C61 119.8 18_545 17
C61 C61 H61 120.1 18_545 .
C61 C61 H61 120.1 17 .
H71A O71 H71B 113.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.371(4) .
C1 C2 1.377(4) .
C1 C22A 1.410(4) .
C1B O1 1.413(4) .
C1B H1B1 0.9800 .
C1B H1B2 0.9800 .
C1B H1B3 0.9800 .
C2 C3 1.374(5) .
C2 H2 0.9500 .
C3 C4 1.389(4) .
C3 H3 0.9500 .
C4 O4 1.371(3) .
C4 C4A 1.405(4) .
C4A C22A 1.400(4) .
C4A C5 1.525(4) .
C4B O4 1.439(3) .
C4B H4B1 0.9800 .
C4B H4B2 0.9800 .
C4B H4B3 0.9800 .
C5 N5 1.457(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C5B N21 1.431(3) .
C5B N5 1.449(3) .
C5B C5C 1.542(3) .
C5B C6B 1.586(3) .
C5C O5C 1.194(3) .
C5C O5D 1.316(3) .
C5D O5D 1.470(3) .
C5D C5E 1.482(4) .
C5D H5D1 0.9900 .
C5D H5D2 0.9900 .
C5E H5E1 0.9800 .
C5E H5E2 0.9800 .
C5E H5E3 0.9800 .
N5 C6 1.375(3) .
C6 O6 1.217(3) .
C6 N6 1.385(3) .
C6B N20 1.438(3) .
C6B N6 1.440(3) .
C6B C6C 1.548(3) .
C6C O6C 1.188(3) .
C6C O6D 1.321(3) .
C6D O6D 1.465(3) .
C6D C6E 1.480(4) .
C6D H6D1 0.9900 .
C6D H6D2 0.9900 .
C6E H6E1 0.9800 .
C6E H6E2 0.9800 .
C6E H6E3 0.9800 .
N6 C7 1.464(3) .
C7 C7A 1.513(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C7A C19A 1.396(4) .
C7A C8 1.399(3) .
C8 C8A 1.390(3) .
C8 H8 0.9500 .
C8A C18A 1.403(3) .
C8A C9 1.507(3) .
C9 N9 1.465(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9B N9 1.440(3) .
C9B N17 1.442(3) .
C9B C9C 1.541(3) .
C9B C10B 1.584(3) .
C9C O9C 1.203(3) .
C9C O9D 1.325(3) .
C9D O9D 1.462(3) .
C9D C9E 1.486(4) .
C9D H9D1 0.9900 .
C9D H9D2 0.9900 .
C9E H9E1 0.9800 .
C9E H9E2 0.9800 .
C9E H9E3 0.9800 .
N9 C10 1.381(3) .
C10 O10 1.213(3) .
C10 N10 1.370(3) .
C10B N16 1.433(3) .
C10B N10 1.439(3) .
C10B C10C 1.539(3) .
C10C O10C 1.201(3) .
C10C O10D 1.322(3) .
C10D O10D 1.468(3) .
C10D C10E 1.489(6) .
C10D H10A 0.9900 .
C10D H10B 0.9900 .
C10E H10C 0.9800 .
C10E H10D 0.9800 .
C10E H10E 0.9800 .
C10G H10H 0.9800 .
C10G H10I 0.9800 .
C10G H10J 0.9800 .
N10 C11 1.460(3) .
C11 C11A 1.516(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C11A C15A 1.399(3) .
C11A C12 1.404(3) .
C12 O12 1.371(3) .
C12 C13 1.380(4) .
C12B O12 1.411(3) .
C12B H12A 0.9800 .
C12B H12B 0.9800 .
C12B H12C 0.9800 .
C13 C14 1.385(4) .
C13 H13 0.9500 .
C14 C15 1.389(4) .
C14 H14 0.9500 .
C15 O15 1.374(3) .
C15 C15A 1.400(3) .
C15A C16 1.516(3) .
C15B O15 1.419(3) .
C15B H15A 0.9800 .
C15B H15B 0.9800 .
C15B H15C 0.9800 .
C16 N16 1.464(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
N16 C17 1.373(3) .
C17 O17 1.214(3) .
C17 N17 1.373(3) .
N17 C18 1.465(3) .
C18 C18A 1.509(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18A C19 1.384(3) .
C19 C19A 1.390(4) .
C19 H19 0.9500 .
C19A C20 1.517(3) .
C20 N20 1.454(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
N20 C21 1.368(3) .
C21 O21 1.214(3) .
C21 N21 1.386(3) .
N21 C22 1.464(3) .
C22 C22A 1.505(4) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C31 C32 1.331(9) .
C31 C36 1.433(10) .
C31 C37 1.456(11) .
C32 C33 1.247(17) .
C32 H32 0.9500 .
C33 C34 1.375(11) .
C33 H33 0.9500 .
C34 C35 1.454(10) .
C34 H34 0.9500 .
C35 C36 1.422(10) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C37 H37A 0.9800 .
C37 H37B 0.9800 .
C37 H37C 0.9800 .
C41 C47 1.3731 .
C41 C42 1.3900 .
C41 C46 1.3900 .
C42 C43 1.3900 .
C42 H42 0.9500 .
C43 C44 1.3900 .
C43 H43 0.9500 .
C44 C45 1.3900 .
C44 H44 0.9500 .
C45 C46 1.3900 .
C45 H45 0.9500 .
C46 H46 0.9500 .
C47 H47A 0.9800 .
C47 H47B 0.9800 .
C47 H47C 0.9800 .
C51 Cl51 1.7295 .
C51 Cl51 1.729(3) 2_655
C51 Cl51 1.729(4) 3_665
C51 H51 1.0000 .
Cl51 Cl52 1.0971 .
Cl51 Cl52 2.115(3) 2_655
C52 Cl52 1.7222 .
C52 Cl52 1.722(4) 2_655
C52 Cl52 1.722(4) 3_665
C52 H52 1.0000 .
Cl52 Cl51 2.115(5) 3_665
C61 C61 1.326(4) 18_545
C61 C61 1.327(4) 17
C61 H61 0.9500 .
O71 H71A 0.8446 .
O71 H71B 0.8492 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O71 H71B O6 0.85 2.02 2.868(8) 179.8 .
O71 H71A N6 0.84 2.23 3.067(10) 168.4 10_666
O71 H71A O6C 0.84 2.38 2.796(8) 110.7 10_666
