#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:20:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180133 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/31/7103129.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_7103129
loop_
_publ_author_name
'Gabutti, Sandro'
'Knutzen, Marco'
'Neuburger, Markus'
'Schull, Guillaume'
'Berndt, Richard'
'Mayor, Marcel'
_publ_section_title
;
 A rigid sublimable naphthalenediimide cyclophane as model compound for
 UHV STM experiments.
;
_journal_issue                   20
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2370
_journal_page_last               2372
_journal_paper_doi               10.1039/b719796a
_journal_year                    2008
_chemical_formula_moiety         'C52 H40 N4 O8, 0.5(C H2 Cl2), 0.5(C H2 Cl2)'
_chemical_formula_sum            'C53 H42 Cl2 N4 O8'
_chemical_formula_weight         933.84
_space_group_IT_number           2
_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
_audit_creation_date             07-02-22
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90.3583(11)
_cell_angle_beta                 110.9346(11)
_cell_angle_gamma                90.1421(12)
_cell_formula_units_Z            2
_cell_length_a                   11.2478(2)
_cell_length_b                   13.9007(2)
_cell_length_c                   14.9298(3)
_cell_measurement_reflns_used    10367
_cell_measurement_temperature    173
_cell_measurement_theta_max      28
_cell_measurement_theta_min      1
_cell_volume                     2180.15(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20283
_diffrn_reflns_theta_full        27.871
_diffrn_reflns_theta_max         27.871
_diffrn_reflns_theta_min         1.967
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       plate
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.43
_refine_diff_density_min         -1.09
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1417
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         6267
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.000203
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
0.967 1.12 0.546
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1089
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0707
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              18
_reflns_limit_k_min              -18
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                6267
_reflns_number_total             10386
_reflns_threshold_expression     I>1.0σ(I)
_cod_data_source_file            b719796a.txt
_cod_data_source_block           sg21
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      'P -1 '
_cod_database_code               7103129
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.5051(2) 0.23320(13) 0.44747(13) 0.0369 1.0000 Uani . . . . . .
O2 O 0.19741(19) -0.15218(15) 0.58165(14) 0.0423 1.0000 Uani . . . . . .
O3 O 0.5518(2) -0.20269(15) 0.84303(15) 0.0441 1.0000 Uani . . . . . .
O4 O 0.84323(18) 0.20202(14) 0.72513(15) 0.0386 1.0000 Uani . . . . . .
O5 O 0.1351(2) 0.09055(15) 0.97238(14) 0.0456 1.0000 Uani . . . . . .
O6 O 0.3823(2) 0.49528(14) 0.81024(15) 0.0416 1.0000 Uani . . . . . .
O7 O 0.2549(2) 0.36131(16) 0.51273(14) 0.0489 1.0000 Uani . . . . . .
O8 O -0.04266(18) -0.01552(13) 0.66622(13) 0.0363 1.0000 Uani . . . . . .
N1 N 0.6694(2) 0.22332(14) 0.59074(15) 0.0285 1.0000 Uani . . . . . .
N2 N 0.3739(2) -0.17628(15) 0.71362(15) 0.0281 1.0000 Uani . . . . . .
N3 N 0.06007(19) 0.03132(14) 0.82061(15) 0.0269 1.0000 Uani . . . . . .
N4 N 0.3242(2) 0.42636(14) 0.66243(15) 0.0297 1.0000 Uani . . . . . .
C1 C 0.8406(3) 0.6211(2) 0.7704(2) 0.0397 1.0000 Uani . . . . . .
C2 C 0.8274(4) 0.6407(3) 0.8678(2) 0.0532 1.0000 Uani . . . . . .
C3 C 0.8131(4) 0.7153(3) 0.7135(3) 0.0634 1.0000 Uani . . . . . .
C4 C 0.9769(4) 0.5901(3) 0.7892(3) 0.0697 1.0000 Uani . . . . . .
C5 C 0.7430(3) 0.54507(18) 0.71295(18) 0.0319 1.0000 Uani . . . . . .
C6 C 0.7771(3) 0.46452(18) 0.67214(19) 0.0320 1.0000 Uani . . . . . .
C7 C 0.6866(3) 0.39891(17) 0.61642(18) 0.0300 1.0000 Uani . . . . . .
C8 C 0.5591(3) 0.41345(17) 0.60252(18) 0.0299 1.0000 Uani . . . . . .
C9 C 0.5234(2) 0.49154(17) 0.64562(17) 0.0280 1.0000 Uani . . . . . .
C10 C 0.6140(3) 0.55654(18) 0.69919(19) 0.0325 1.0000 Uani . . . . . .
C11 C 0.7258(3) 0.31284(18) 0.5707(2) 0.0324 1.0000 Uani . . . . . .
C12 C 0.5518(3) 0.19374(17) 0.52524(18) 0.0285 1.0000 Uani . . . . . .
C13 C 0.4859(2) 0.11404(17) 0.55401(17) 0.0255 1.0000 Uani . . . . . .
C14 C 0.3640(2) 0.08755(18) 0.49786(17) 0.0289 1.0000 Uani . . . . . .
C15 C 0.3039(2) 0.00952(18) 0.52429(18) 0.0288 1.0000 Uani . . . . . .
C16 C 0.3671(2) -0.04231(17) 0.60569(17) 0.0253 1.0000 Uani . . . . . .
C17 C 0.3041(2) -0.12670(18) 0.63031(17) 0.0288 1.0000 Uani . . . . . .
C18 C 0.4984(2) -0.15363(19) 0.77341(18) 0.0299 1.0000 Uani . . . . . .
C19 C 0.5589(2) -0.06882(17) 0.74824(17) 0.0261 1.0000 Uani . . . . . .
C20 C 0.6792(2) -0.04046(19) 0.80597(18) 0.0305 1.0000 Uani . . . . . .
C21 C 0.7362(2) 0.04012(18) 0.78209(18) 0.0294 1.0000 Uani . . . . . .
C22 C 0.6749(2) 0.09031(16) 0.69954(18) 0.0262 1.0000 Uani . . . . . .
C23 C 0.7376(2) 0.17499(17) 0.67513(18) 0.0288 1.0000 Uani . . . . . .
C24 C 0.5507(2) 0.06365(16) 0.63940(17) 0.0241 1.0000 Uani . . . . . .
C25 C 0.4913(2) -0.01597(17) 0.66458(16) 0.0244 1.0000 Uani . . . . . .
C26 C 0.3139(3) -0.25925(17) 0.74145(19) 0.0296 1.0000 Uani . . . . . .
C27 C 0.2602(2) -0.23381(17) 0.81756(18) 0.0278 1.0000 Uani . . . . . .
C28 C 0.2940(2) -0.28714(18) 0.90164(18) 0.0287 1.0000 Uani . . . . . .
C29 C 0.2420(3) -0.26810(18) 0.97164(18) 0.0308 1.0000 Uani . . . . . .
C30 C 0.1570(2) -0.19044(18) 0.95579(18) 0.0295 1.0000 Uani . . . . . .
C31 C 0.1225(2) -0.13705(17) 0.87262(18) 0.0273 1.0000 Uani . . . . . .
C32 C 0.1731(2) -0.15950(18) 0.80288(18) 0.0292 1.0000 Uani . . . . . .
C33 C 0.2777(3) -0.3278(2) 1.0632(2) 0.0388 1.0000 Uani . . . . . .
C34 C 0.3827(4) -0.2736(3) 1.1430(2) 0.0514 1.0000 Uani . . . . . .
C35 C 0.3278(4) -0.4270(2) 1.0492(2) 0.0496 1.0000 Uani . . . . . .
C36 C 0.1614(4) -0.3435(3) 1.0919(2) 0.0527 1.0000 Uani . . . . . .
C37 C 0.0228(2) -0.05902(17) 0.85514(19) 0.0285 1.0000 Uani . . . . . .
C38 C 0.1215(2) 0.10189(18) 0.88856(18) 0.0295 1.0000 Uani . . . . . .
C39 C 0.1702(2) 0.18769(18) 0.85448(18) 0.0295 1.0000 Uani . . . . . .
C40 C 0.2375(3) 0.25796(19) 0.91848(18) 0.0330 1.0000 Uani . . . . . .
C41 C 0.2878(3) 0.33735(19) 0.88622(19) 0.0348 1.0000 Uani . . . . . .
C42 C 0.2747(2) 0.34547(17) 0.79111(18) 0.0287 1.0000 Uani . . . . . .
C43 C 0.3309(2) 0.42866(17) 0.75852(19) 0.0295 1.0000 Uani . . . . . .
C44 C 0.2587(3) 0.3569(2) 0.59505(19) 0.0333 1.0000 Uani . . . . . .
C45 C 0.1953(2) 0.27810(18) 0.62749(18) 0.0294 1.0000 Uani . . . . . .
C46 C 0.1245(3) 0.21039(19) 0.56307(18) 0.0328 1.0000 Uani . . . . . .
C47 C 0.0675(2) 0.13345(19) 0.59371(18) 0.0315 1.0000 Uani . . . . . .
C48 C 0.0825(2) 0.12577(17) 0.68905(17) 0.0266 1.0000 Uani . . . . . .
C49 C 0.0264(2) 0.04275(17) 0.72172(17) 0.0271 1.0000 Uani . . . . . .
C50 C 0.1531(2) 0.19541(16) 0.75645(17) 0.0248 1.0000 Uani . . . . . .
C51 C 0.2078(2) 0.27369(17) 0.72532(17) 0.0262 1.0000 Uani . . . . . .
C52 C 0.3837(3) 0.50708(18) 0.6289(2) 0.0327 1.0000 Uani . . . . . .
C53 C 0.5456(9) 0.0511(7) 0.9969(6) 0.0886 0.5000 Uani D U . . . .
C54 C 0.9867(7) 0.4911(5) 0.5453(5) 0.0635 0.5000 Uani D U . . . .
Cl1 Cl 0.5602(6) -0.0377(4) 1.0833(5) 0.1136 0.5000 Uani D U . . . .
Cl2 Cl 0.4157(4) 0.0318(4) 0.8915(4) 0.0991 0.5000 Uani D U . . . .
Cl3 Cl 0.93191(13) 0.41511(11) 0.45006(13) 0.1136 1.0000 Uani D U . . . .
H21 H 0.8407 0.5821 0.9044 0.0782 1.0000 Uiso R . . . . .
H22 H 0.8909 0.6891 0.9022 0.0780 1.0000 Uiso R . . . . .
H23 H 0.7431 0.6655 0.8573 0.0783 1.0000 Uiso R . . . . .
H31 H 0.8190 0.7053 0.6523 0.0871 1.0000 Uiso R . . . . .
H32 H 0.8762 0.7624 0.7496 0.0869 1.0000 Uiso R . . . . .
H33 H 0.7298 0.7381 0.7076 0.0871 1.0000 Uiso R . . . . .
H41 H 0.9865 0.5795 0.7278 0.1011 1.0000 Uiso R . . . . .
H42 H 1.0350 0.6417 0.8248 0.1010 1.0000 Uiso R . . . . .
H43 H 0.9938 0.5311 0.8252 0.1011 1.0000 Uiso R . . . . .
H61 H 0.8644 0.4553 0.6822 0.0351 1.0000 Uiso R . . . . .
H81 H 0.4959 0.3693 0.5637 0.0351 1.0000 Uiso R . . . . .
H101 H 0.5888 0.6091 0.7267 0.0369 1.0000 Uiso R . . . . .
H111 H 0.8177 0.3059 0.5937 0.0421 1.0000 Uiso R . . . . .
H112 H 0.6938 0.3200 0.5000 0.0420 1.0000 Uiso R . . . . .
H141 H 0.3205 0.1203 0.4411 0.0301 1.0000 Uiso R . . . . .
H151 H 0.2209 -0.0062 0.4862 0.0301 1.0000 Uiso R . . . . .
H201 H 0.7220 -0.0766 0.8607 0.0351 1.0000 Uiso R . . . . .
H211 H 0.8175 0.0617 0.8233 0.0361 1.0000 Uiso R . . . . .
H261 H 0.3763 -0.3108 0.7655 0.0409 1.0000 Uiso R . . . . .
H262 H 0.2442 -0.2828 0.6838 0.0410 1.0000 Uiso R . . . . .
H281 H 0.3510 -0.3388 0.9100 0.0331 1.0000 Uiso R . . . . .
H301 H 0.1240 -0.1730 1.0029 0.0333 1.0000 Uiso R . . . . .
H321 H 0.1490 -0.1238 0.7456 0.0352 1.0000 Uiso R . . . . .
H341 H 0.4064 -0.3074 1.2032 0.0711 1.0000 Uiso R . . . . .
H342 H 0.3524 -0.2102 1.1521 0.0709 1.0000 Uiso R . . . . .
H343 H 0.4578 -0.2645 1.1261 0.0711 1.0000 Uiso R . . . . .
H351 H 0.3457 -0.4647 1.1066 0.0748 1.0000 Uiso R . . . . .
H352 H 0.4033 -0.4222 1.0337 0.0750 1.0000 Uiso R . . . . .
H353 H 0.2636 -0.4590 0.9976 0.0750 1.0000 Uiso R . . . . .
H361 H 0.1826 -0.3879 1.1451 0.0839 1.0000 Uiso R . . . . .
H362 H 0.1329 -0.2845 1.1102 0.0840 1.0000 Uiso R . . . . .
H363 H 0.0931 -0.3721 1.0388 0.0840 1.0000 Uiso R . . . . .
H371 H 0.0120 -0.0444 0.9167 0.0351 1.0000 Uiso R . . . . .
H372 H -0.0572 -0.0819 0.8085 0.0352 1.0000 Uiso R . . . . .
H401 H 0.2489 0.2529 0.9830 0.0392 1.0000 Uiso R . . . . .
H411 H 0.3312 0.3841 0.9300 0.0401 1.0000 Uiso R . . . . .
H461 H 0.1131 0.2135 0.4972 0.0362 1.0000 Uiso R . . . . .
H471 H 0.0199 0.0879 0.5497 0.0351 1.0000 Uiso R . . . . .
H521 H 0.3766 0.5662 0.6637 0.0421 1.0000 Uiso R . . . . .
H522 H 0.3376 0.5152 0.5599 0.0423 1.0000 Uiso R . . . . .
H531 H 0.5316 0.1142 1.0193 0.1140 0.5000 Uiso R . . . . .
H532 H 0.6196 0.0534 0.9780 0.1140 0.5000 Uiso R . . . . .
H541 H 1.0437 0.4577 0.6008 0.0748 0.5000 Uiso R . . . . .
H542 H 0.9150 0.5159 0.5599 0.0748 0.5000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 . N1 . C12 . 118.0(2) yes
C11 . N1 . C23 . 117.2(2) yes
C12 . N1 . C23 . 124.7(2) yes
C17 . N2 . C18 . 125.0(2) yes
C17 . N2 . C26 . 118.4(2) yes
C18 . N2 . C26 . 116.6(2) yes
C37 . N3 . C38 . 117.9(2) yes
C37 . N3 . C49 . 117.9(2) yes
C38 . N3 . C49 . 124.1(2) yes
C43 . N4 . C44 . 124.6(2) yes
C43 . N4 . C52 . 117.7(2) yes
C44 . N4 . C52 . 117.5(2) yes
C2 . C1 . C3 . 107.9(3) yes
C2 . C1 . C4 . 107.9(3) yes
C3 . C1 . C4 . 109.7(3) yes
C2 . C1 . C5 . 110.8(2) yes
C3 . C1 . C5 . 108.2(2) yes
C4 . C1 . C5 . 112.2(3) yes
C1 . C2 . H21 . 110.0 no
C1 . C2 . H22 . 108.4 no
H21 . C2 . H22 . 110.1 no
C1 . C2 . H23 . 109.2 no
H21 . C2 . H23 . 109.9 no
H22 . C2 . H23 . 109.2 no
C1 . C3 . H31 . 110.0 no
C1 . C3 . H32 . 107.6 no
H31 . C3 . H32 . 109.9 no
C1 . C3 . H33 . 109.4 no
H31 . C3 . H33 . 111.0 no
H32 . C3 . H33 . 108.9 no
C1 . C4 . H41 . 108.3 no
C1 . C4 . H42 . 108.8 no
H41 . C4 . H42 . 109.9 no
C1 . C4 . H43 . 109.4 no
H41 . C4 . H43 . 109.6 no
H42 . C4 . H43 . 110.9 no
C1 . C5 . C6 . 122.6(2) yes
C1 . C5 . C10 . 119.8(2) yes
C6 . C5 . C10 . 117.6(2) yes
C5 . C6 . C7 . 121.7(3) yes
C5 . C6 . H61 . 118.3 no
C7 . C6 . H61 . 120.0 no
C6 . C7 . C8 . 119.2(2) yes
C6 . C7 . C11 . 120.8(2) yes
C8 . C7 . C11 . 120.0(2) yes
C7 . C8 . C9 . 120.0(2) yes
C7 . C8 . H81 . 119.9 no
C9 . C8 . H81 . 120.1 no
C8 . C9 . C10 . 119.9(2) yes
C8 . C9 . C52 . 119.4(2) yes
C10 . C9 . C52 . 120.6(2) yes
C5 . C10 . C9 . 121.4(2) yes
C5 . C10 . H101 . 119.4 no
C9 . C10 . H101 . 119.2 no
C7 . C11 . N1 . 110.9(2) yes
C7 . C11 . H111 . 111.5 no
N1 . C11 . H111 . 108.8 no
C7 . C11 . H112 . 109.9 no
N1 . C11 . H112 . 106.7 no
H111 . C11 . H112 . 108.9 no
N1 . C12 . O1 . 120.8(2) yes
N1 . C12 . C13 . 117.4(2) yes
O1 . C12 . C13 . 121.8(2) yes
C12 . C13 . C14 . 120.8(2) yes
C12 . C13 . C24 . 119.2(2) yes
C14 . C13 . C24 . 119.9(2) yes
C13 . C14 . C15 . 120.3(2) yes
C13 . C14 . H141 . 120.6 no
C15 . C14 . H141 . 119.1 no
C14 . C15 . C16 . 120.5(2) yes
C14 . C15 . H151 . 118.9 no
C16 . C15 . H151 . 120.6 no
C15 . C16 . C17 . 119.7(2) yes
C15 . C16 . C25 . 120.1(2) yes
C17 . C16 . C25 . 120.1(2) yes
C16 . C17 . N2 . 116.7(2) yes
C16 . C17 . O2 . 122.5(2) yes
N2 . C17 . O2 . 120.8(2) yes
N2 . C18 . O3 . 119.9(2) yes
N2 . C18 . C19 . 117.4(2) yes
O3 . C18 . C19 . 122.7(2) yes
C18 . C19 . C20 . 120.3(2) yes
C18 . C19 . C25 . 119.5(2) yes
C20 . C19 . C25 . 120.2(2) yes
C19 . C20 . C21 . 120.2(2) yes
C19 . C20 . H201 . 118.6 no
C21 . C20 . H201 . 121.2 no
C20 . C21 . C22 . 120.8(2) yes
C20 . C21 . H211 . 120.4 no
C22 . C21 . H211 . 118.8 no
C21 . C22 . C23 . 120.0(2) yes
C21 . C22 . C24 . 120.2(2) yes
C23 . C22 . C24 . 119.8(2) yes
C22 . C23 . N1 . 117.0(2) yes
C22 . C23 . O4 . 122.5(2) yes
N1 . C23 . O4 . 120.6(2) yes
C13 . C24 . C22 . 121.3(2) yes
C13 . C24 . C25 . 119.6(2) yes
C22 . C24 . C25 . 119.1(2) yes
C19 . C25 . C24 . 119.3(2) yes
C19 . C25 . C16 . 121.2(2) yes
C24 . C25 . C16 . 119.5(2) yes
N2 . C26 . C27 . 112.4(2) yes
N2 . C26 . H261 . 109.8 no
C27 . C26 . H261 . 108.8 no
N2 . C26 . H262 . 108.0 no
C27 . C26 . H262 . 109.0 no
H261 . C26 . H262 . 108.8 no
C26 . C27 . C28 . 120.1(2) yes
C26 . C27 . C32 . 120.3(2) yes
C28 . C27 . C32 . 119.6(2) yes
C27 . C28 . C29 . 121.5(2) yes
C27 . C28 . H281 . 119.0 no
C29 . C28 . H281 . 119.5 no
C28 . C29 . C30 . 117.4(2) yes
C28 . C29 . C33 . 121.4(2) yes
C30 . C29 . C33 . 121.2(2) yes
C29 . C30 . C31 . 121.6(2) yes
C29 . C30 . H301 . 119.9 no
C31 . C30 . H301 . 118.5 no
C30 . C31 . C32 . 119.7(2) yes
C30 . C31 . C37 . 119.8(2) yes
C32 . C31 . C37 . 120.4(2) yes
C27 . C32 . C31 . 120.1(2) yes
C27 . C32 . H321 . 119.9 no
C31 . C32 . H321 . 120.0 no
C29 . C33 . C34 . 108.1(2) yes
C29 . C33 . C35 . 111.3(2) yes
C34 . C33 . C35 . 108.9(3) yes
C29 . C33 . C36 . 110.5(2) yes
C34 . C33 . C36 . 110.4(3) yes
C35 . C33 . C36 . 107.7(3) yes
C33 . C34 . H341 . 111.3 no
C33 . C34 . H342 . 109.7 no
H341 . C34 . H342 . 108.1 no
C33 . C34 . H343 . 111.0 no
H341 . C34 . H343 . 109.1 no
H342 . C34 . H343 . 107.4 no
C33 . C35 . H351 . 110.1 no
C33 . C35 . H352 . 111.8 no
H351 . C35 . H352 . 109.2 no
C33 . C35 . H353 . 108.3 no
H351 . C35 . H353 . 108.8 no
H352 . C35 . H353 . 108.5 no
C33 . C36 . H361 . 109.6 no
C33 . C36 . H362 . 111.5 no
H361 . C36 . H362 . 109.1 no
C33 . C36 . H363 . 109.5 no
H361 . C36 . H363 . 107.6 no
H362 . C36 . H363 . 109.4 no
C31 . C37 . N3 . 112.79(19) yes
C31 . C37 . H371 . 108.2 no
N3 . C37 . H371 . 107.4 no
C31 . C37 . H372 . 109.4 no
N3 . C37 . H372 . 109.2 no
H371 . C37 . H372 . 109.8 no
N3 . C38 . O5 . 120.0(2) yes
N3 . C38 . C39 . 117.4(2) yes
O5 . C38 . C39 . 122.6(2) yes
C38 . C39 . C40 . 120.5(2) yes
C38 . C39 . C50 . 119.6(2) yes
C40 . C39 . C50 . 119.8(2) yes
C39 . C40 . C41 . 120.2(2) yes
C39 . C40 . H401 . 119.9 no
C41 . C40 . H401 . 119.9 no
C40 . C41 . C42 . 121.0(2) yes
C40 . C41 . H411 . 118.9 no
C42 . C41 . H411 . 120.1 no
C41 . C42 . C43 . 120.4(2) yes
C41 . C42 . C51 . 119.3(2) yes
C43 . C42 . C51 . 120.3(2) yes
C42 . C43 . N4 . 116.6(2) yes
C42 . C43 . O6 . 123.2(2) yes
N4 . C43 . O6 . 120.2(2) yes
N4 . C44 . O7 . 120.6(2) yes
N4 . C44 . C45 . 117.7(2) yes
O7 . C44 . C45 . 121.7(2) yes
C44 . C45 . C46 . 120.1(2) yes
C44 . C45 . C51 . 119.4(2) yes
C46 . C45 . C51 . 120.5(2) yes
C45 . C46 . C47 . 120.5(2) yes
C45 . C46 . H461 . 121.5 no
C47 . C46 . H461 . 118.0 no
C46 . C47 . C48 . 119.9(2) yes
C46 . C47 . H471 . 119.9 no
C48 . C47 . H471 . 120.1 no
C47 . C48 . C49 . 119.8(2) yes
C47 . C48 . C50 . 120.6(2) yes
C49 . C48 . C50 . 119.6(2) yes
C48 . C49 . N3 . 117.1(2) yes
C48 . C49 . O8 . 122.4(2) yes
N3 . C49 . O8 . 120.5(2) yes
C48 . C50 . C39 . 121.1(2) yes
C48 . C50 . C51 . 119.4(2) yes
C39 . C50 . C51 . 119.5(2) yes
C45 . C51 . C50 . 118.9(2) yes
C45 . C51 . C42 . 121.0(2) yes
C50 . C51 . C42 . 120.0(2) yes
C9 . C52 . N4 . 113.5(2) yes
C9 . C52 . H521 . 107.9 no
N4 . C52 . H521 . 108.6 no
C9 . C52 . H522 . 108.6 no
N4 . C52 . H522 . 108.3 no
H521 . C52 . H522 . 109.8 no
Cl1 . C53 . Cl2 . 112.8(5) yes
Cl1 . C53 . H531 . 111.7 no
Cl2 . C53 . H531 . 104.8 no
Cl1 . C53 . H532 . 111.8 no
Cl2 . C53 . H532 . 105.8 no
H531 . C53 . H532 . 109.5 no
Cl3 2_766 C54 . Cl3 . 125.2(4) yes
Cl3 2_766 C54 . H541 . 99.6 no
Cl3 . C54 . H541 . 110.4 no
Cl3 2_766 C54 . H542 . 102.3 no
Cl3 . C54 . H542 . 109.0 no
H541 . C54 . H542 . 109.2 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C12 . 1.224(3) yes
O2 . C17 . 1.211(3) yes
O3 . C18 . 1.213(3) yes
O4 . C23 . 1.213(3) yes
O5 . C38 . 1.217(3) yes
O6 . C43 . 1.207(3) yes
O7 . C44 . 1.216(3) yes
O8 . C49 . 1.214(3) yes
N1 . C11 . 1.476(3) yes
N1 . C12 . 1.394(3) yes
N1 . C23 . 1.396(3) yes
N2 . C17 . 1.398(3) yes
N2 . C18 . 1.399(3) yes
N2 . C26 . 1.470(3) yes
N3 . C37 . 1.476(3) yes
N3 . C38 . 1.397(3) yes
N3 . C49 . 1.397(3) yes
N4 . C43 . 1.409(3) yes
N4 . C44 . 1.394(3) yes
N4 . C52 . 1.484(3) yes
C1 . C2 . 1.535(4) yes
C1 . C3 . 1.537(5) yes
C1 . C4 . 1.521(5) yes
C1 . C5 . 1.538(4) yes
C2 . H21 . 0.967 no
C2 . H22 . 0.979 no
C2 . H23 . 0.969 no
C3 . H31 . 0.949 no
C3 . H32 . 0.971 no
C3 . H33 . 0.963 no
C4 . H41 . 0.970 no
C4 . H42 . 0.984 no
C4 . H43 . 0.965 no
C5 . C6 . 1.390(4) yes
C5 . C10 . 1.401(4) yes
C6 . C7 . 1.393(4) yes
C6 . H61 . 0.948 no
C7 . C8 . 1.390(4) yes
C7 . C11 . 1.516(4) yes
C8 . C9 . 1.390(4) yes
C8 . H81 . 0.957 no
C9 . C10 . 1.378(4) yes
C9 . C52 . 1.516(4) yes
C10 . H101 . 0.928 no
C11 . H111 . 0.971 no
C11 . H112 . 0.992 no
C12 . C13 . 1.480(3) yes
C13 . C14 . 1.375(4) yes
C13 . C24 . 1.413(3) yes
C14 . C15 . 1.408(4) yes
C14 . H141 . 0.935 no
C15 . C16 . 1.377(3) yes
C15 . H151 . 0.928 no
C16 . C17 . 1.484(3) yes
C16 . C25 . 1.405(3) yes
C18 . C19 . 1.476(4) yes
C19 . C20 . 1.374(4) yes
C19 . C25 . 1.419(3) yes
C20 . C21 . 1.399(4) yes
C20 . H201 . 0.937 no
C21 . C22 . 1.374(3) yes
C21 . H211 . 0.948 no
C22 . C23 . 1.483(3) yes
C22 . C24 . 1.412(3) yes
C24 . C25 . 1.412(3) yes
C26 . C27 . 1.505(3) yes
C26 . H261 . 0.980 no
C26 . H262 . 0.988 no
C27 . C28 . 1.394(3) yes
C27 . C32 . 1.389(4) yes
C28 . C29 . 1.393(4) yes
C28 . H281 . 0.943 no
C29 . C30 . 1.408(4) yes
C29 . C33 . 1.531(4) yes
C30 . C31 . 1.383(3) yes
C30 . H301 . 0.936 no
C31 . C32 . 1.388(4) yes
C31 . C37 . 1.517(3) yes
C32 . H321 . 0.945 no
C33 . C34 . 1.536(5) yes
C33 . C35 . 1.532(4) yes
C33 . C36 . 1.531(4) yes
C34 . H341 . 0.967 no
C34 . H342 . 0.972 no
C34 . H343 . 0.972 no
C35 . H351 . 0.967 no
C35 . H352 . 0.959 no
C35 . H353 . 0.953 no
C36 . H361 . 0.970 no
C36 . H362 . 0.954 no
C36 . H363 . 0.968 no
C37 . H371 . 0.990 no
C37 . H372 . 0.972 no
C38 . C39 . 1.478(3) yes
C39 . C40 . 1.381(4) yes
C39 . C50 . 1.411(3) yes
C40 . C41 . 1.403(4) yes
C40 . H401 . 0.929 no
C41 . C42 . 1.380(4) yes
C41 . H411 . 0.923 no
C42 . C43 . 1.482(3) yes
C42 . C51 . 1.408(4) yes
C44 . C45 . 1.481(4) yes
C45 . C46 . 1.372(4) yes
C45 . C51 . 1.418(3) yes
C46 . C47 . 1.406(4) yes
C46 . H461 . 0.946 no
C47 . C48 . 1.377(3) yes
C47 . H471 . 0.928 no
C48 . C49 . 1.480(3) yes
C48 . C50 . 1.412(3) yes
C50 . C51 . 1.409(3) yes
C52 . H521 . 0.988 no
C52 . H522 . 0.981 no
C53 . Cl1 . 1.755(8) yes
C53 . Cl2 . 1.742(7) yes
C53 . H531 . 0.970 no
C53 . H532 . 0.970 no
C54 . Cl3 2_766 1.578(8) yes
C54 . Cl3 . 1.694(7) yes
C54 . H541 . 0.970 no
C54 . H542 . 0.970 no
