#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:15:31 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178427 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024829.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_4024829
loop_
_publ_author_name
'Na Fu'
'Jeffrey M. Baumes'
'Easwaran Arunkumar'
'Bruce C. Noll'
'Bradley D. Smith'
_publ_section_title
;
Squaraine Rotaxanes with Boat Conformation Macrocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6462
_journal_page_last               6468
_journal_paper_doi               10.1021/jo901298n
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C48 H44 N2 O2, C32 H28 N4 O4, C H Cl3'
_chemical_formula_sum            'C81 H73 Cl3 N6 O6'
_chemical_formula_weight         1332.80
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_space_group_name_Hall           '-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_method           SHELXL-97
_cell_angle_alpha                95.972(2)
_cell_angle_beta                 105.166(2)
_cell_angle_gamma                93.929(2)
_cell_formula_units_Z            2
_cell_length_a                   13.5542(7)
_cell_length_b                   15.7453(8)
_cell_length_c                   16.3164(8)
_cell_measurement_reflns_used    9050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.18
_cell_volume                     3326.0(3)
_computing_cell_refinement       'Bruker SAINT v7.53A'
_computing_data_collection       'Bruker APEX-2, v2008.3'
_computing_data_reduction        'Bruker SAINT v7.53A'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Brucker d8 ApexII CCD diffractometer'
_diffrn_measurement_method       'φ and ω 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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48531
_diffrn_reflns_theta_full        26.60
_diffrn_reflns_theta_max         26.60
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of Göttingen, Germany.'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     865
_refine_ls_number_reflns         13723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0453
_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)+(0.0475P)²+2.5389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                10646
_reflns_number_total             13723
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901298n_si_006.cif
_cod_data_source_block           nf2092009_0m
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024829
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30527(10) 0.85266(8) 0.66670(8) 0.0205(3) Uani 1 1 d . . .
O2 O 0.24050(11) 0.64511(8) 0.82071(8) 0.0235(3) Uani 1 1 d . . .
O3 O 0.88219(12) 0.66173(9) 0.28662(9) 0.0299(3) Uani 1 1 d . . .
O4 O 0.62942(12) 0.42039(9) -0.11266(8) 0.0281(3) Uani 1 1 d . . .
O5 O 0.64871(10) -0.16484(8) 0.20872(8) 0.0217(3) Uani 1 1 d . . .
O6 O 0.90005(10) 0.07553(9) 0.61375(8) 0.0235(3) Uani 1 1 d . . .
N1 N 0.65054(12) -0.02096(10) 0.22188(10) 0.0211(3) Uani 1 1 d . . .
H1A H 0.6766 0.0281 0.2537 0.025 Uiso 1 1 calc R . .
N2 N 0.84554(12) 0.14742(9) 0.50005(9) 0.0178(3) Uani 1 1 d . . .
H2A H 0.8238 0.1429 0.4439 0.021 Uiso 1 1 calc R . .
N3 N 0.86502(12) 0.51751(10) 0.28011(10) 0.0210(3) Uani 1 1 d . . .
H3A H 0.8335 0.4689 0.2504 0.025 Uiso 1 1 calc R . .
N4 N 0.67003(14) 0.34730(10) 0.00155(10) 0.0256(4) Uani 1 1 d . . .
H4A H 0.6902 0.3510 0.0577 0.031 Uiso 1 1 calc R . .
N5 N 0.71559(13) 0.60546(11) 0.72967(10) 0.0244(4) Uani 1 1 d . . .
N6 N -0.15458(12) 0.90276(11) 0.79201(10) 0.0218(3) Uani 1 1 d . . .
C1 C 0.67597(15) 0.50003(12) 0.02707(12) 0.0202(4) Uani 1 1 d . . .
C2 C 0.61156(16) 0.56466(12) 0.00994(12) 0.0230(4) Uani 1 1 d . . .
H2B H 0.5580 0.5587 -0.0418 0.028 Uiso 1 1 calc R . .
C3 C 0.62532(16) 0.63746(13) 0.06796(13) 0.0255(4) Uani 1 1 d . . .
H3B H 0.5814 0.6817 0.0556 0.031 Uiso 1 1 calc R . .
C4 C 0.70223(16) 0.64682(12) 0.14388(12) 0.0233(4) Uani 1 1 d . . .
H4B H 0.7113 0.6974 0.1833 0.028 Uiso 1 1 calc R . .
C5 C 0.76616(15) 0.58236(12) 0.16241(12) 0.0199(4) Uani 1 1 d . . .
C6 C 0.75355(15) 0.51024(12) 0.10285(12) 0.0194(4) Uani 1 1 d . . .
H6A H 0.7990 0.4670 0.1142 0.023 Uiso 1 1 calc R . .
C7 C 0.84402(15) 0.59133(12) 0.24806(12) 0.0208(4) Uani 1 1 d . . .
C8 C 0.93862(16) 0.51554(13) 0.36285(12) 0.0242(4) Uani 1 1 d . . .
H8A H 0.9395 0.5694 0.4004 0.029 Uiso 1 1 calc R . .
H8B H 1.0082 0.5127 0.3546 0.029 Uiso 1 1 calc R . .
C9 C 0.91341(14) 0.44004(12) 0.40637(12) 0.0192(4) Uani 1 1 d . . .
C10 C 0.96066(15) 0.36548(12) 0.40011(12) 0.0201(4) Uani 1 1 d . . .
H10A H 1.0068 0.3606 0.3653 0.024 Uiso 1 1 calc R . .
C11 C 0.94202(14) 0.29783(12) 0.44349(11) 0.0189(4) Uani 1 1 d . . .
H11A H 0.9755 0.2473 0.4378 0.023 Uiso 1 1 calc R . .
C12 C 0.87556(14) 0.30230(11) 0.49491(11) 0.0170(4) Uani 1 1 d . . .
C13 C 0.82617(15) 0.37622(12) 0.49914(12) 0.0223(4) Uani 1 1 d . . .
H13A H 0.7783 0.3804 0.5324 0.027 Uiso 1 1 calc R . .
C14 C 0.84493(15) 0.44408(12) 0.45605(13) 0.0239(4) Uani 1 1 d . . .
H14A H 0.8103 0.4941 0.4606 0.029 Uiso 1 1 calc R . .
C15 C 0.86072(15) 0.23246(12) 0.54850(12) 0.0196(4) Uani 1 1 d . . .
H15A H 0.9217 0.2358 0.5983 0.023 Uiso 1 1 calc R . .
H15B H 0.8003 0.2418 0.5705 0.023 Uiso 1 1 calc R . .
C16 C 0.86306(14) 0.07540(12) 0.53680(12) 0.0181(4) Uani 1 1 d . . .
C17 C 0.83998(14) -0.00620(12) 0.47608(11) 0.0167(4) Uani 1 1 d . . .
C18 C 0.89730(14) -0.07469(12) 0.49640(12) 0.0198(4) Uani 1 1 d . . .
H18A H 0.9479 -0.0708 0.5498 0.024 Uiso 1 1 calc R . .
C19 C 0.88056(15) -0.14838(12) 0.43880(12) 0.0218(4) Uani 1 1 d . . .
H19A H 0.9196 -0.1952 0.4531 0.026 Uiso 1 1 calc R . .
C20 C 0.80815(14) -0.15499(12) 0.36084(12) 0.0194(4) Uani 1 1 d . . .
H20A H 0.7978 -0.2059 0.3217 0.023 Uiso 1 1 calc R . .
C21 C 0.75042(14) -0.08730(11) 0.33956(11) 0.0172(4) Uani 1 1 d . . .
C22 C 0.76537(14) -0.01426(11) 0.39831(11) 0.0165(4) Uani 1 1 d . . .
H22A H 0.7237 0.0312 0.3851 0.020 Uiso 1 1 calc R . .
C23 C 0.67789(14) -0.09476(12) 0.25186(12) 0.0174(4) Uani 1 1 d . . .
C24 C 0.57910(16) -0.02020(13) 0.13838(12) 0.0254(4) Uani 1 1 d . . .
H24A H 0.5086 -0.0192 0.1450 0.031 Uiso 1 1 calc R . .
H24B H 0.5811 -0.0737 0.1014 0.031 Uiso 1 1 calc R . .
C25 C 0.60294(15) 0.05573(12) 0.09517(11) 0.0212(4) Uani 1 1 d . . .
C26 C 0.54069(16) 0.12179(13) 0.08706(12) 0.0242(4) Uani 1 1 d . . .
H26A H 0.4849 0.1208 0.1122 0.029 Uiso 1 1 calc R . .
C27 C 0.55762(16) 0.18937(13) 0.04310(12) 0.0262(4) Uani 1 1 d . . .
H27A H 0.5136 0.2341 0.0387 0.031 Uiso 1 1 calc R . .
C28 C 0.68499(17) 0.06004(13) 0.05967(14) 0.0284(5) Uani 1 1 d . . .
H28A H 0.7301 0.0161 0.0655 0.034 Uiso 1 1 calc R . .
C29 C 0.70197(17) 0.12777(13) 0.01561(14) 0.0297(5) Uani 1 1 d . . .
H29A H 0.7589 0.1296 -0.0081 0.036 Uiso 1 1 calc R . .
C30 C 0.63783(16) 0.19268(12) 0.00542(12) 0.0239(4) Uani 1 1 d . . .
C31 C 0.65188(19) 0.26266(13) -0.04814(13) 0.0298(5) Uani 1 1 d . . .
H31A H 0.7108 0.2527 -0.0719 0.036 Uiso 1 1 calc R . .
H31B H 0.5897 0.2605 -0.0967 0.036 Uiso 1 1 calc R . .
C32 C 0.65735(16) 0.41957(12) -0.03463(12) 0.0224(4) Uani 1 1 d . . .
C33 C 0.28772(14) 0.79687(11) 0.71021(11) 0.0179(4) Uani 1 1 d . . .
C34 C 0.20667(14) 0.77610(12) 0.75054(11) 0.0187(4) Uani 1 1 d . . .
C35 C 0.25949(14) 0.70359(12) 0.78042(11) 0.0189(4) Uani 1 1 d . . .
C36 C 0.34235(15) 0.72635(11) 0.74317(11) 0.0186(4) Uani 1 1 d . . .
C37 C 0.43676(15) 0.69682(12) 0.74161(12) 0.0194(4) Uani 1 1 d . . .
C38 C 0.49654(15) 0.73242(12) 0.69244(12) 0.0220(4) Uani 1 1 d . . .
H38A H 0.4729 0.7782 0.6613 0.026 Uiso 1 1 calc R . .
C39 C 0.58727(15) 0.70286(12) 0.68855(12) 0.0220(4) Uani 1 1 d . . .
H39A H 0.6254 0.7277 0.6542 0.026 Uiso 1 1 calc R . .
C40 C 0.62595(15) 0.63533(12) 0.73521(12) 0.0215(4) Uani 1 1 d . . .
C41 C 0.56748(15) 0.60149(12) 0.78676(12) 0.0215(4) Uani 1 1 d . . .
H41A H 0.5925 0.5577 0.8203 0.026 Uiso 1 1 calc R . .
C42 C 0.47601(15) 0.63076(12) 0.78895(12) 0.0202(4) Uani 1 1 d . . .
H42A H 0.4376 0.6061 0.8232 0.024 Uiso 1 1 calc R . .
C43 C 0.77601(15) 0.64365(14) 0.67867(13) 0.0263(4) Uani 1 1 d . . .
H43A H 0.8453 0.6235 0.6938 0.032 Uiso 1 1 calc R . .
H43B H 0.7842 0.7067 0.6940 0.032 Uiso 1 1 calc R . .
C44 C 0.73029(14) 0.62327(12) 0.58341(12) 0.0207(4) Uani 1 1 d . . .
C45 C 0.76302(15) 0.67482(12) 0.53004(12) 0.0229(4) Uani 1 1 d . . .
H45A H 0.8139 0.7217 0.5541 0.027 Uiso 1 1 calc R . .
C46 C 0.72316(16) 0.65924(13) 0.44287(13) 0.0253(4) Uani 1 1 d . . .
H46A H 0.7474 0.6952 0.4075 0.030 Uiso 1 1 calc R . .
C47 C 0.64801(15) 0.59180(13) 0.40543(13) 0.0244(4) Uani 1 1 d . . .
C48 C 0.61576(15) 0.54013(13) 0.45881(13) 0.0263(4) Uani 1 1 d . . .
H48A H 0.5648 0.4933 0.4347 0.032 Uiso 1 1 calc R . .
C49 C 0.65632(15) 0.55528(13) 0.54654(13) 0.0248(4) Uani 1 1 d . . .
H49A H 0.6332 0.5187 0.5819 0.030 Uiso 1 1 calc R . .
C50 C 0.60637(18) 0.57573(16) 0.31012(14) 0.0362(5) Uani 1 1 d . . .
H50A H 0.5545 0.5261 0.2946 0.054 Uiso 1 1 calc R . .
H50B H 0.6624 0.5642 0.2841 0.054 Uiso 1 1 calc R . .
H50C H 0.5750 0.6264 0.2892 0.054 Uiso 1 1 calc R . .
C51 C 0.76200(16) 0.53781(13) 0.77732(13) 0.0257(4) Uani 1 1 d . . .
H51A H 0.7916 0.4996 0.7400 0.031 Uiso 1 1 calc R . .
H51B H 0.7079 0.5030 0.7933 0.031 Uiso 1 1 calc R . .
C52 C 0.84499(15) 0.57332(13) 0.85720(13) 0.0252(4) Uani 1 1 d . . .
C53 C 0.9440(2) 0.5532(2) 0.87000(17) 0.0612(9) Uani 1 1 d . . .
H53A H 0.9620 0.5170 0.8270 0.073 Uiso 1 1 calc R . .
C54 C 1.0178(2) 0.5849(3) 0.94460(19) 0.0859(14) Uani 1 1 d . . .
H54A H 1.0860 0.5696 0.9521 0.103 Uiso 1 1 calc R . .
C55 C 0.99579(18) 0.6377(2) 1.00805(16) 0.0477(7) Uani 1 1 d . . .
C56 C 0.89690(16) 0.65881(13) 0.99500(14) 0.0295(5) Uani 1 1 d . . .
H56A H 0.8793 0.6957 1.0377 0.035 Uiso 1 1 calc R . .
C57 C 0.82274(16) 0.62721(13) 0.92075(14) 0.0265(4) Uani 1 1 d . . .
H57A H 0.7548 0.6429 0.9131 0.032 Uiso 1 1 calc R . .
C58 C 1.0763(2) 0.6733(3) 1.0898(2) 0.0797(12) Uani 1 1 d . . .
H58A H 1.1422 0.6519 1.0887 0.120 Uiso 1 1 calc R . .
H58B H 1.0555 0.6551 1.1389 0.120 Uiso 1 1 calc R . .
H58C H 1.0836 0.7362 1.0948 0.120 Uiso 1 1 calc R . .
C59 C 0.11670(14) 0.80940(12) 0.75993(11) 0.0190(4) Uani 1 1 d . . .
C60 C 0.08013(15) 0.88232(12) 0.72329(12) 0.0199(4) Uani 1 1 d . . .
H60A H 0.1187 0.9111 0.6916 0.024 Uiso 1 1 calc R . .
C61 C -0.00875(15) 0.91277(12) 0.73193(11) 0.0198(4) Uani 1 1 d . . .
H61A H -0.0317 0.9615 0.7055 0.024 Uiso 1 1 calc R . .
C62 C -0.06739(14) 0.87246(12) 0.77994(11) 0.0194(4) Uani 1 1 d . . .
C63 C -0.03110(15) 0.79850(12) 0.81654(12) 0.0209(4) Uani 1 1 d . . .
H63A H -0.0692 0.7696 0.8484 0.025 Uiso 1 1 calc R . .
C64 C 0.05724(15) 0.76874(12) 0.80648(12) 0.0211(4) Uani 1 1 d . . .
H64A H 0.0796 0.7191 0.8315 0.025 Uiso 1 1 calc R . .
C65 C -0.19677(15) 0.97897(12) 0.75819(12) 0.0219(4) Uani 1 1 d . . .
H65A H -0.1461 1.0097 0.7348 0.026 Uiso 1 1 calc R . .
H65B H -0.2090 1.0181 0.8053 0.026 Uiso 1 1 calc R . .
C66 C -0.29626(14) 0.95602(12) 0.68871(12) 0.0192(4) Uani 1 1 d . . .
C67 C -0.38590(15) 0.98831(13) 0.69688(12) 0.0233(4) Uani 1 1 d . . .
H67A H -0.3848 1.0265 0.7463 0.028 Uiso 1 1 calc R . .
C68 C -0.47730(15) 0.96566(13) 0.63389(13) 0.0245(4) Uani 1 1 d . . .
H68A H -0.5380 0.9890 0.6405 0.029 Uiso 1 1 calc R . .
C69 C -0.48190(15) 0.90965(12) 0.56150(12) 0.0218(4) Uani 1 1 d . . .
C70 C -0.39132(16) 0.87802(13) 0.55322(12) 0.0232(4) Uani 1 1 d . . .
H70A H -0.3923 0.8399 0.5039 0.028 Uiso 1 1 calc R . .
C71 C -0.29969(15) 0.90128(13) 0.61584(12) 0.0221(4) Uani 1 1 d . . .
H71A H -0.2385 0.8794 0.6087 0.026 Uiso 1 1 calc R . .
C72 C -0.58191(16) 0.88287(14) 0.49507(13) 0.0292(5) Uani 1 1 d . . .
H72A H -0.6368 0.9117 0.5119 0.044 Uiso 1 1 calc R . .
H72B H -0.5977 0.8206 0.4901 0.044 Uiso 1 1 calc R . .
H72C H -0.5767 0.8989 0.4398 0.044 Uiso 1 1 calc R . .
C73 C -0.21802(15) 0.85679(13) 0.83617(12) 0.0237(4) Uani 1 1 d . . .
H73A H -0.2231 0.7947 0.8160 0.028 Uiso 1 1 calc R . .
H73B H -0.2882 0.8751 0.8193 0.028 Uiso 1 1 calc R . .
C74 C -0.18057(15) 0.86920(12) 0.93262(12) 0.0206(4) Uani 1 1 d . . .
C75 C -0.08204(16) 0.90207(13) 0.97720(12) 0.0258(4) Uani 1 1 d . . .
H75A H -0.0369 0.9252 0.9476 0.031 Uiso 1 1 calc R . .
C76 C -0.04849(17) 0.90152(14) 1.06492(13) 0.0290(5) Uani 1 1 d . . .
H76A H 0.0199 0.9239 1.0946 0.035 Uiso 1 1 calc R . .
C77 C -0.11254(17) 0.86914(12) 1.11013(13) 0.0259(4) Uani 1 1 d . . .
C78 C -0.21298(16) 0.84013(12) 1.06546(13) 0.0248(4) Uani 1 1 d . . .
H78A H -0.2595 0.8203 1.0955 0.030 Uiso 1 1 calc R . .
C79 C -0.24622(15) 0.83967(12) 0.97817(13) 0.0225(4) Uani 1 1 d . . .
H79A H -0.3152 0.8188 0.9487 0.027 Uiso 1 1 calc R . .
C80 C -0.07329(19) 0.86269(15) 1.20410(13) 0.0356(5) Uani 1 1 d . . .
H80A H -0.0011 0.8862 1.2244 0.053 Uiso 1 1 calc R . .
H80B H -0.0793 0.8023 1.2137 0.053 Uiso 1 1 calc R . .
H80C H -0.1139 0.8953 1.2355 0.053 Uiso 1 1 calc R . .
C83 C 0.36730(18) 0.71328(14) 0.27664(14) 0.0341(5) Uani 1 1 d . . .
H83A H 0.3507 0.6698 0.2245 0.041 Uiso 1 1 calc R . .
Cl1 Cl 0.48078(5) 0.77543(4) 0.28118(4) 0.03845(14) Uani 1 1 d . . .
Cl2 Cl 0.38195(5) 0.65882(4) 0.36725(4) 0.04060(15) Uani 1 1 d . . .
Cl3 Cl 0.26511(5) 0.77768(4) 0.26864(4) 0.04173(15) 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 0.0033 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
_geom_angle_publ_flag
C23 N1 C24 121.68(16) . . ?
C23 N1 H1A 119.2 . . ?
C24 N1 H1A 119.2 . . ?
C16 N2 C15 123.28(15) . . ?
C16 N2 H2A 118.4 . . ?
C15 N2 H2A 118.4 . . ?
C7 N3 C8 121.91(16) . . ?
C7 N3 H3A 119.0 . . ?
C8 N3 H3A 119.0 . . ?
C32 N4 C31 122.75(16) . . ?
C32 N4 H4A 118.6 . . ?
C31 N4 H4A 118.6 . . ?
C40 N5 C43 120.93(16) . . ?
C40 N5 C51 123.71(16) . . ?
C43 N5 C51 115.25(16) . . ?
C62 N6 C73 121.28(16) . . ?
C62 N6 C65 124.25(15) . . ?
C73 N6 C65 114.35(16) . . ?
C6 C1 C2 118.95(18) . . ?
C6 C1 C32 121.47(17) . . ?
C2 C1 C32 119.53(17) . . ?
C3 C2 C1 120.04(18) . . ?
C3 C2 H2B 120.0 . . ?
C1 C2 H2B 120.0 . . ?
C2 C3 C4 120.70(18) . . ?
C2 C3 H3B 119.7 . . ?
C4 C3 H3B 119.7 . . ?
C3 C4 C5 119.93(18) . . ?
C3 C4 H4B 120.0 . . ?
C5 C4 H4B 120.0 . . ?
C4 C5 C6 119.08(18) . . ?
C4 C5 C7 118.78(17) . . ?
C6 C5 C7 122.09(17) . . ?
C1 C6 C5 121.26(18) . . ?
C1 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
O3 C7 N3 123.01(18) . . ?
O3 C7 C5 121.61(17) . . ?
N3 C7 C5 115.32(16) . . ?
N3 C8 C9 112.41(15) . . ?
N3 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N3 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C14 117.74(17) . . ?
C10 C9 C8 120.98(18) . . ?
C14 C9 C8 121.24(18) . . ?
C9 C10 C11 121.28(18) . . ?
C9 C10 H10A 119.4 . . ?
C11 C10 H10A 119.4 . . ?
C12 C11 C10 121.24(18) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C11 C12 C13 117.29(17) . . ?
C11 C12 C15 122.15(17) . . ?
C13 C12 C15 120.47(17) . . ?
C14 C13 C12 121.55(18) . . ?
C14 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?
C13 C14 C9 120.85(18) . . ?
C13 C14 H14A 119.6 . . ?
C9 C14 H14A 119.6 . . ?
N2 C15 C12 112.08(15) . . ?
N2 C15 H15A 109.2 . . ?
C12 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C12 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
O6 C16 N2 123.17(17) . . ?
O6 C16 C17 121.50(17) . . ?
N2 C16 C17 115.23(15) . . ?
C22 C17 C18 118.82(17) . . ?
C22 C17 C16 121.79(16) . . ?
C18 C17 C16 119.34(16) . . ?
C19 C18 C17 119.81(17) . . ?
C19 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
C20 C19 C18 120.97(18) . . ?
C20 C19 H19A 119.5 . . ?
C18 C19 H19A 119.5 . . ?
C19 C20 C21 119.96(18) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?
C20 C21 C22 119.03(17) . . ?
C20 C21 C23 118.17(16) . . ?
C22 C21 C23 122.73(16) . . ?
C21 C22 C17 121.35(17) . . ?
C21 C22 H22A 119.3 . . ?
C17 C22 H22A 119.3 . . ?
O5 C23 N1 122.16(17) . . ?
O5 C23 C21 121.05(16) . . ?
N1 C23 C21 116.72(16) . . ?
N1 C24 C25 112.79(16) . . ?
N1 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
N1 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C26 C25 C28 117.90(18) . . ?
C26 C25 C24 120.61(19) . . ?
C28 C25 C24 121.45(18) . . ?
C25 C26 C27 121.5(2) . . ?
C25 C26 H26A 119.3 . . ?
C27 C26 H26A 119.3 . . ?
C26 C27 C30 120.80(19) . . ?
C26 C27 H27A 119.6 . . ?
C30 C27 H27A 119.6 . . ?
C25 C28 C29 120.63(19) . . ?
C25 C28 H28A 119.7 . . ?
C29 C28 H28A 119.7 . . ?
C30 C29 C28 121.4(2) . . ?
C30 C29 H29A 119.3 . . ?
C28 C29 H29A 119.3 . . ?
C29 C30 C27 117.74(18) . . ?
C29 C30 C31 121.2(2) . . ?
C27 C30 C31 121.00(19) . . ?
N4 C31 C30 111.80(16) . . ?
N4 C31 H31A 109.3 . . ?
C30 C31 H31A 109.3 . . ?
N4 C31 H31B 109.3 . . ?
C30 C31 H31B 109.3 . . ?
H31A C31 H31B 107.9 . . ?
O4 C32 N4 123.02(18) . . ?
O4 C32 C1 122.05(17) . . ?
N4 C32 C1 114.90(16) . . ?
O1 C33 C36 133.70(18) . . ?
O1 C33 C34 135.15(18) . . ?
C36 C33 C34 91.14(15) . . ?
C59 C34 C35 133.72(17) . . ?
C59 C34 C33 137.65(17) . . ?
C35 C34 C33 88.62(15) . . ?
O2 C35 C34 134.13(18) . . ?
O2 C35 C36 134.52(18) . . ?
C34 C35 C36 91.34(15) . . ?
C37 C36 C33 134.53(17) . . ?
C37 C36 C35 136.61(17) . . ?
C33 C36 C35 88.81(15) . . ?
C36 C37 C38 120.88(17) . . ?
C36 C37 C42 121.61(17) . . ?
C38 C37 C42 117.52(17) . . ?
C39 C38 C37 121.54(17) . . ?
C39 C38 H38A 119.2 . . ?
C37 C38 H38A 119.2 . . ?
C38 C39 C40 120.87(17) . . ?
C38 C39 H39A 119.6 . . ?
C40 C39 H39A 119.6 . . ?
N5 C40 C41 122.14(17) . . ?
N5 C40 C39 120.31(17) . . ?
C41 C40 C39 117.54(18) . . ?
C42 C41 C40 120.91(17) . . ?
C42 C41 H41A 119.5 . . ?
C40 C41 H41A 119.5 . . ?
C41 C42 C37 121.57(17) . . ?
C41 C42 H42A 119.2 . . ?
C37 C42 H42A 119.2 . . ?
N5 C43 C44 114.36(17) . . ?
N5 C43 H43A 108.7 . . ?
C44 C43 H43A 108.7 . . ?
N5 C43 H43B 108.7 . . ?
C44 C43 H43B 108.7 . . ?
H43A C43 H43B 107.6 . . ?
C45 C44 C49 118.25(18) . . ?
C45 C44 C43 118.80(17) . . ?
C49 C44 C43 122.95(18) . . ?
C46 C45 C44 120.98(18) . . ?
C46 C45 H45A 119.5 . . ?
C44 C45 H45A 119.5 . . ?
C45 C46 C47 121.13(19) . . ?
C45 C46 H46A 119.4 . . ?
C47 C46 H46A 119.4 . . ?
C48 C47 C46 117.80(19) . . ?
C48 C47 C50 122.09(19) . . ?
C46 C47 C50 120.09(19) . . ?
C49 C48 C47 121.18(19) . . ?
C49 C48 H48A 119.4 . . ?
C47 C48 H48A 119.4 . . ?
C48 C49 C44 120.65(19) . . ?
C48 C49 H49A 119.7 . . ?
C44 C49 H49A 119.7 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
N5 C51 C52 112.35(17) . . ?
N5 C51 H51A 109.1 . . ?
C52 C51 H51A 109.1 . . ?
N5 C51 H51B 109.1 . . ?
C52 C51 H51B 109.1 . . ?
H51A C51 H51B 107.9 . . ?
C53 C52 C57 117.6(2) . . ?
C53 C52 C51 121.9(2) . . ?
C57 C52 C51 120.51(18) . . ?
C52 C53 C54 120.7(2) . . ?
C52 C53 H53A 119.6 . . ?
C54 C53 H53A 119.6 . . ?
C55 C54 C53 121.8(2) . . ?
C55 C54 H54A 119.1 . . ?
C53 C54 H54A 119.1 . . ?
C54 C55 C56 117.6(2) . . ?
C54 C55 C58 122.3(2) . . ?
C56 C55 C58 120.1(3) . . ?
C55 C56 C57 120.8(2) . . ?
C55 C56 H56A 119.6 . . ?
C57 C56 H56A 119.6 . . ?
C56 C57 C52 121.41(19) . . ?
C56 C57 H57A 119.3 . . ?
C52 C57 H57A 119.3 . . ?
C55 C58 H58A 109.5 . . ?
C55 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C55 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C34 C59 C64 119.90(17) . . ?
C34 C59 C60 122.96(17) . . ?
C64 C59 C60 117.13(17) . . ?
C61 C60 C59 121.99(17) . . ?
C61 C60 H60A 119.0 . . ?
C59 C60 H60A 119.0 . . ?
C60 C61 C62 120.65(17) . . ?
C60 C61 H61A 119.7 . . ?
C62 C61 H61A 119.7 . . ?
N6 C62 C61 122.12(17) . . ?
N6 C62 C63 120.36(16) . . ?
C61 C62 C63 117.52(17) . . ?
C64 C63 C62 120.87(17) . . ?
C64 C63 H63A 119.6 . . ?
C62 C63 H63A 119.6 . . ?
C63 C64 C59 121.83(17) . . ?
C63 C64 H64A 119.1 . . ?
C59 C64 H64A 119.1 . . ?
N6 C65 C66 111.68(16) . . ?
N6 C65 H65A 109.3 . . ?
C66 C65 H65A 109.3 . . ?
N6 C65 H65B 109.3 . . ?
C66 C65 H65B 109.3 . . ?
H65A C65 H65B 107.9 . . ?
C67 C66 C71 118.52(18) . . ?
C67 C66 C65 120.92(17) . . ?
C71 C66 C65 120.56(17) . . ?
C66 C67 C68 120.71(18) . . ?
C66 C67 H67A 119.6 . . ?
C68 C67 H67A 119.6 . . ?
C69 C68 C67 121.19(19) . . ?
C69 C68 H68A 119.4 . . ?
C67 C68 H68A 119.4 . . ?
C68 C69 C70 117.85(18) . . ?
C68 C69 C72 120.90(18) . . ?
C70 C69 C72 121.24(18) . . ?
C71 C70 C69 120.97(18) . . ?
C71 C70 H70A 119.5 . . ?
C69 C70 H70A 119.5 . . ?
C66 C71 C70 120.74(18) . . ?
C66 C71 H71A 119.6 . . ?
C70 C71 H71A 119.6 . . ?
C69 C72 H72A 109.5 . . ?
C69 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C69 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
N6 C73 C74 115.70(16) . . ?
N6 C73 H73A 108.4 . . ?
C74 C73 H73A 108.4 . . ?
N6 C73 H73B 108.4 . . ?
C74 C73 H73B 108.4 . . ?
H73A C73 H73B 107.4 . . ?
C75 C74 C79 118.42(18) . . ?
C75 C74 C73 123.31(17) . . ?
C79 C74 C73 118.06(17) . . ?
C74 C75 C76 120.39(18) . . ?
C74 C75 H75A 119.8 . . ?
C76 C75 H75A 119.8 . . ?
C77 C76 C75 121.3(2) . . ?
C77 C76 H76A 119.3 . . ?
C75 C76 H76A 119.3 . . ?
C76 C77 C78 117.89(18) . . ?
C76 C77 C80 121.0(2) . . ?
C78 C77 C80 121.11(19) . . ?
C79 C78 C77 120.89(18) . . ?
C79 C78 H78A 119.6 . . ?
C77 C78 H78A 119.6 . . ?
C78 C79 C74 120.96(19) . . ?
C78 C79 H79A 119.5 . . ?
C74 C79 H79A 119.5 . . ?
C77 C80 H80A 109.5 . . ?
C77 C80 H80B 109.5 . . ?
H80A C80 H80B 109.5 . . ?
C77 C80 H80C 109.5 . . ?
H80A C80 H80C 109.5 . . ?
H80B C80 H80C 109.5 . . ?
Cl1 C83 Cl3 110.55(12) . . ?
Cl1 C83 Cl2 110.78(13) . . ?
Cl3 C83 Cl2 110.01(12) . . ?
Cl1 C83 H83A 108.5 . . ?
Cl3 C83 H83A 108.5 . . ?
Cl2 C83 H83A 108.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C33 1.234(2) . ?
O2 C35 1.236(2) . ?
O3 C7 1.224(2) . ?
O4 C32 1.231(2) . ?
O5 C23 1.226(2) . ?
O6 C16 1.224(2) . ?
N1 C23 1.345(2) . ?
N1 C24 1.452(2) . ?
N1 H1A 0.8800 . ?
N2 C16 1.344(2) . ?
N2 C15 1.455(2) . ?
N2 H2A 0.8800 . ?
N3 C7 1.341(2) . ?
N3 C8 1.458(2) . ?
N3 H3A 0.8800 . ?
N4 C32 1.336(2) . ?
N4 C31 1.456(2) . ?
N4 H4A 0.8800 . ?
N5 C40 1.354(3) . ?
N5 C43 1.455(2) . ?
N5 C51 1.464(2) . ?
N6 C62 1.357(2) . ?
N6 C73 1.459(2) . ?
N6 C65 1.462(2) . ?
C1 C6 1.384(3) . ?
C1 C2 1.389(3) . ?
C1 C32 1.497(3) . ?
C2 C3 1.377(3) . ?
C2 H2B 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3B 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4B 0.9500 . ?
C5 C6 1.386(3) . ?
C5 C7 1.501(3) . ?
C6 H6A 0.9500 . ?
C8 C9 1.510(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.382(3) . ?
C9 C14 1.383(3) . ?
C10 C11 1.383(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.386(3) . ?
C12 C15 1.509(2) . ?
C13 C14 1.383(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.499(3) . ?
C17 C22 1.388(2) . ?
C17 C18 1.390(3) . ?
C18 C19 1.381(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.377(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.386(3) . ?
C21 C23 1.497(3) . ?
C22 H22A 0.9500 . ?
C24 C25 1.507(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.379(3) . ?
C25 C28 1.383(3) . ?
C26 C27 1.382(3) . ?
C26 H26A 0.9500 . ?
C27 C30 1.382(3) . ?
C27 H27A 0.9500 . ?
C28 C29 1.385(3) . ?
C28 H28A 0.9500 . ?
C29 C30 1.382(3) . ?
C29 H29A 0.9500 . ?
C30 C31 1.508(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C33 C36 1.449(3) . ?
C33 C34 1.456(3) . ?
C34 C59 1.398(3) . ?
C34 C35 1.449(3) . ?
C35 C36 1.451(3) . ?
C36 C37 1.397(3) . ?
C37 C38 1.409(3) . ?
C37 C42 1.411(3) . ?
C38 C39 1.359(3) . ?
C38 H38A 0.9500 . ?
C39 C40 1.422(3) . ?
C39 H39A 0.9500 . ?
C40 C41 1.416(3) . ?
C41 C42 1.360(3) . ?
C41 H41A 0.9500 . ?
C42 H42A 0.9500 . ?
C43 C44 1.506(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.383(3) . ?
C44 C49 1.384(3) . ?
C45 C46 1.372(3) . ?
C45 H45A 0.9500 . ?
C46 C47 1.389(3) . ?
C46 H46A 0.9500 . ?
C47 C48 1.382(3) . ?
C47 C50 1.497(3) . ?
C48 C49 1.381(3) . ?
C48 H48A 0.9500 . ?
C49 H49A 0.9500 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 C52 1.507(3) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C53 1.367(3) . ?
C52 C57 1.379(3) . ?
C53 C54 1.379(4) . ?
C53 H53A 0.9500 . ?
C54 C55 1.367(4) . ?
C54 H54A 0.9500 . ?
C55 C56 1.371(3) . ?
C55 C58 1.511(4) . ?
C56 C57 1.376(3) . ?
C56 H56A 0.9500 . ?
C57 H57A 0.9500 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 C64 1.410(3) . ?
C59 C60 1.410(3) . ?
C60 C61 1.362(3) . ?
C60 H60A 0.9500 . ?
C61 C62 1.417(3) . ?
C61 H61A 0.9500 . ?
C62 C63 1.423(3) . ?
C63 C64 1.358(3) . ?
C63 H63A 0.9500 . ?
C64 H64A 0.9500 . ?
C65 C66 1.511(3) . ?
C65 H65A 0.9900 . ?
C65 H65B 0.9900 . ?
C66 C67 1.381(3) . ?
C66 C71 1.382(3) . ?
C67 C68 1.384(3) . ?
C67 H67A 0.9500 . ?
C68 C69 1.383(3) . ?
C68 H68A 0.9500 . ?
C69 C70 1.389(3) . ?
C69 C72 1.499(3) . ?
C70 C71 1.384(3) . ?
C70 H70A 0.9500 . ?
C71 H71A 0.9500 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C73 C74 1.509(3) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C74 C75 1.378(3) . ?
C74 C79 1.386(3) . ?
C75 C76 1.385(3) . ?
C75 H75A 0.9500 . ?
C76 C77 1.382(3) . ?
C76 H76A 0.9500 . ?
C77 C78 1.385(3) . ?
C77 C80 1.502(3) . ?
C78 C79 1.376(3) . ?
C78 H78A 0.9500 . ?
C79 H79A 0.9500 . ?
C80 H80A 0.9800 . ?
C80 H80B 0.9800 . ?
C80 H80C 0.9800 . ?
C83 Cl1 1.746(2) . ?
C83 Cl3 1.758(3) . ?
C83 Cl2 1.759(2) . ?
C83 H83A 1.0000 . ?
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
N1 H1A O1 0.88 2.13 2.983(2) 163.2 2_666
N2 H2A O1 0.88 2.17 2.944(2) 146.4 2_666
N3 H3A O2 0.88 2.07 2.949(2) 179.4 2_666
N4 H4A O2 0.88 1.95 2.822(2) 169.4 2_666
