#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/47/4314732.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_4314732
loop_
_publ_author_name
'Jean-François Lemonnier'
'Laure Guénée'
'Gérald Bernardinelli'
'Jean-François Vigier'
'Bernard Bocquet'
'Claude Piguet'
_publ_contact_author_address
;Department of inorganic, analytic and applied chemistry 
University of Geneva, Sciences II 
30 quai Ernest-Ansermet 
CH-1211 Genève 4 
;
_publ_contact_author_email       claude.Piguet@unige.ch
_publ_contact_author_fax         '+41 (0)22 379 68 30 '
_publ_contact_author_name        'Claude Piguet'
_publ_contact_author_phone       '+41 (0)22 379 60 34'
_publ_section_title
;
 Planned Failures from the Principle of Maximum Site Occupancy in
 Lanthanide Helicates
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1252
_journal_page_last               1265
_journal_paper_doi               10.1021/ic902314f
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety         'C52 H44 N10, 3(C H Cl3)'
_chemical_formula_sum            'C55 H47 Cl9 N10'
_chemical_formula_weight         1167.08
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 115.699(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.7383(14)
_cell_length_b                   8.4757(5)
_cell_length_c                   25.3816(11)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    150
_cell_measurement_theta_max      23.75
_cell_measurement_theta_min      1.8
_cell_volume                     5377.0(5)
_computing_cell_refinement       'CELL (Stoe & Cie, 1999)'
_computing_data_collection       'EXPOSE (Stoe & Cie, 1999)'
_computing_data_reduction        'XRED (Stoe & Cie, 1999)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  Shelxl_ACTA
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 6
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Stoe Ipds'
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1265
_diffrn_reflns_av_sigmaI/netI    0.2020
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            30174
_diffrn_reflns_theta_full        24.12
_diffrn_reflns_theta_max         24.12
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.518
_exptl_absorpt_correction_T_max  0.9671
_exptl_absorpt_correction_T_min  0.9114
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'XRED; Stoe & Cie, 1999'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.817
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     672
_refine_ls_number_reflns         8473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.817
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.0561
_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)+(0.0250P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                3252
_reflns_number_total             8473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic902314f_si_002_1.cif
_cod_data_source_block           L8
_cod_original_sg_symbol_Hall     '-P 2YBC'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4314732
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.20237(17) 0.3125(5) 0.0277(2) 0.0302(12) Uani 1 1 d . . .
N2 N 0.18389(17) 0.5205(5) 0.0703(2) 0.0313(11) Uani 1 1 d . . .
N3 N 0.26743(16) 0.3958(5) 0.1844(2) 0.0271(11) Uani 1 1 d . . .
N4 N 0.36139(16) 0.3385(5) 0.33822(19) 0.0246(11) Uani 1 1 d . . .
N5 N 0.30058(15) 0.5317(5) 0.30557(19) 0.0245(11) Uani 1 1 d . . .
N6 N 0.65765(16) 0.3239(5) 0.85526(19) 0.0248(11) Uani 1 1 d . . .
N7 N 0.65296(16) 0.5417(5) 0.90374(19) 0.0239(11) Uani 1 1 d . . .
N8 N 0.73457(16) 0.3934(5) 1.01289(19) 0.0231(11) Uani 1 1 d . . .
N9 N 0.83432(17) 0.3304(5) 1.1631(2) 0.0308(12) Uani 1 1 d . . .
N10 N 0.77080(15) 0.5171(5) 1.13479(19) 0.0269(11) Uani 1 1 d . . .
C1 C 0.0812(2) 0.6047(8) -0.0798(3) 0.0474(17) Uani 1 1 d . . .
H1 H 0.0535 0.6716 -0.1029 0.037(2) Uiso 1 1 calc R . .
C2 C 0.0935(2) 0.4758(8) -0.1059(3) 0.0442(17) Uani 1 1 d . . .
H2 H 0.0741 0.4600 -0.1459 0.037(2) Uiso 1 1 calc R . .
C3 C 0.1331(2) 0.3730(7) -0.0746(3) 0.0398(16) Uani 1 1 d . . .
H3 H 0.1410 0.2876 -0.0925 0.037(2) Uiso 1 1 calc R . .
C4 C 0.1618(2) 0.3995(7) -0.0138(3) 0.0304(14) Uani 1 1 d . . .
C5 C 0.21395(19) 0.3874(6) 0.0776(2) 0.0247(13) Uani 1 1 d . . .
C6 C 0.1494(2) 0.5271(7) 0.0107(2) 0.0315(15) Uani 1 1 d . . .
C7 C 0.1089(2) 0.6359(7) -0.0207(3) 0.0445(17) Uani 1 1 d . . .
H7 H 0.1012 0.7225 -0.0031 0.037(2) Uiso 1 1 calc R . .
C8 C 0.1839(2) 0.6371(7) 0.1133(3) 0.0440(17) Uani 1 1 d . . .
H8A H 0.1771 0.7413 0.0957 0.037(2) Uiso 1 1 calc R . .
H8B H 0.2188 0.6387 0.1465 0.037(2) Uiso 1 1 calc R . .
C9 C 0.1415(2) 0.5981(8) 0.1340(3) 0.061(2) Uani 1 1 d . . .
H9A H 0.1411 0.6783 0.1605 0.037(2) Uiso 1 1 calc R . .
H9B H 0.1494 0.4979 0.1536 0.037(2) Uiso 1 1 calc R . .
H9C H 0.1070 0.5934 0.1010 0.037(2) Uiso 1 1 calc R . .
C10 C 0.25483(19) 0.3215(6) 0.1333(2) 0.0262(14) Uani 1 1 d . . .
C11 C 0.2784(2) 0.1799(6) 0.1295(2) 0.0301(14) Uani 1 1 d . . .
H11 H 0.2691 0.1341 0.0931 0.037(2) Uiso 1 1 calc R . .
C12 C 0.3151(2) 0.1071(6) 0.1788(3) 0.0353(15) Uani 1 1 d . . .
H12 H 0.3306 0.0113 0.1768 0.037(2) Uiso 1 1 calc R . .
C13 C 0.3282(2) 0.1824(6) 0.2316(2) 0.0287(14) Uani 1 1 d . . .
H13 H 0.3527 0.1366 0.2661 0.037(2) Uiso 1 1 calc R . .
C14 C 0.3049(2) 0.3257(6) 0.2332(2) 0.0262(13) Uani 1 1 d . . .
C15 C 0.3217(2) 0.4000(6) 0.2917(2) 0.0247(13) Uani 1 1 d . . .
C16 C 0.36610(19) 0.4333(6) 0.3845(2) 0.0220(12) Uani 1 1 d . . .
C17 C 0.40142(19) 0.4196(6) 0.4441(2) 0.0253(14) Uani 1 1 d . . .
H17 H 0.4268 0.3394 0.4571 0.037(2) Uiso 1 1 calc R . .
C18 C 0.3977(2) 0.5270(6) 0.4827(2) 0.0238(13) Uani 1 1 d . . .
C19 C 0.35941(19) 0.6473(6) 0.4617(2) 0.0254(13) Uani 1 1 d . . .
H19 H 0.3572 0.7188 0.4883 0.037(2) Uiso 1 1 calc R . .
C20 C 0.32455(19) 0.6649(6) 0.4027(2) 0.0243(13) Uani 1 1 d . . .
H20 H 0.3001 0.7476 0.3896 0.037(2) Uiso 1 1 calc R . .
C21 C 0.32779(18) 0.5544(6) 0.3644(2) 0.0217(13) Uani 1 1 d . . .
C22 C 0.25635(19) 0.6364(6) 0.2682(2) 0.0286(14) Uani 1 1 d . . .
H22A H 0.2361 0.6683 0.2894 0.037(2) Uiso 1 1 calc R . .
H22B H 0.2325 0.5790 0.2336 0.037(2) Uiso 1 1 calc R . .
C23 C 0.2770(2) 0.7826(6) 0.2497(3) 0.0404(16) Uani 1 1 d . . .
H23A H 0.2479 0.8538 0.2295 0.037(2) Uiso 1 1 calc R . .
H23B H 0.2929 0.7524 0.2243 0.037(2) Uiso 1 1 calc R . .
H23C H 0.3034 0.8339 0.2837 0.037(2) Uiso 1 1 calc R . .
C24 C 0.43437(19) 0.5130(6) 0.5468(2) 0.0234(13) Uani 1 1 d . . .
C25 C 0.48394(19) 0.4445(6) 0.5664(2) 0.0258(13) Uani 1 1 d . . .
H25 H 0.4941 0.3978 0.5396 0.037(2) Uiso 1 1 calc R . .
C26 C 0.51943(19) 0.4431(6) 0.6256(2) 0.0263(13) Uani 1 1 d . . .
H26 H 0.5526 0.3946 0.6373 0.037(2) Uiso 1 1 calc R . .
C27 C 0.50632(19) 0.5136(6) 0.6679(2) 0.0210(12) Uani 1 1 d . . .
C28 C 0.45529(19) 0.5782(6) 0.6477(2) 0.0254(13) Uani 1 1 d . . .
H28 H 0.4448 0.6234 0.6745 0.037(2) Uiso 1 1 calc R . .
C29 C 0.42002(19) 0.5775(6) 0.5896(2) 0.0248(13) Uani 1 1 d . . .
H29 H 0.3860 0.6201 0.5780 0.037(2) Uiso 1 1 calc R . .
C30 C 0.54569(19) 0.5236(6) 0.7303(2) 0.0214(13) Uani 1 1 d . . .
C31 C 0.58376(19) 0.4074(6) 0.7575(2) 0.0251(13) Uani 1 1 d . . .
H31 H 0.5863 0.3204 0.7366 0.037(2) Uiso 1 1 calc R . .
C32 C 0.61806(18) 0.4233(6) 0.8167(2) 0.0214(13) Uani 1 1 d . . .
C33 C 0.67696(19) 0.3982(6) 0.9063(2) 0.0225(13) Uani 1 1 d . . .
C34 C 0.61449(19) 0.5589(6) 0.8467(2) 0.0230(13) Uani 1 1 d . . .
C35 C 0.57821(19) 0.6796(6) 0.8205(2) 0.0260(13) Uani 1 1 d . . .
H35 H 0.5770 0.7692 0.8411 0.037(2) Uiso 1 1 calc R . .
C36 C 0.54367(19) 0.6591(6) 0.7618(2) 0.0254(13) Uani 1 1 d . . .
H36 H 0.5185 0.7368 0.7426 0.037(2) Uiso 1 1 calc R . .
C37 C 0.6578(2) 0.6525(6) 0.9502(2) 0.0282(14) Uani 1 1 d . . .
H37A H 0.6528 0.7596 0.9354 0.037(2) Uiso 1 1 calc R . .
H37B H 0.6933 0.6447 0.9823 0.037(2) Uiso 1 1 calc R . .
C38 C 0.6157(2) 0.6132(6) 0.9717(2) 0.0325(14) Uani 1 1 d . . .
H38A H 0.6206 0.6798 1.0042 0.037(2) Uiso 1 1 calc R . .
H38B H 0.6192 0.5047 0.9837 0.037(2) Uiso 1 1 calc R . .
H38C H 0.5807 0.6303 0.9407 0.037(2) Uiso 1 1 calc R . .
C39 C 0.7188(2) 0.3247(6) 0.9598(2) 0.0256(14) Uani 1 1 d . . .
C40 C 0.7398(2) 0.1827(6) 0.9527(3) 0.0314(14) Uani 1 1 d . . .
H40 H 0.7287 0.1389 0.9157 0.037(2) Uiso 1 1 calc R . .
C41 C 0.7777(2) 0.1063(7) 1.0014(3) 0.0388(16) Uani 1 1 d . . .
H41 H 0.7920 0.0101 0.9976 0.037(2) Uiso 1 1 calc R . .
C42 C 0.7935(2) 0.1753(6) 1.0549(3) 0.0335(15) Uani 1 1 d . . .
H42 H 0.8186 0.1257 1.0882 0.037(2) Uiso 1 1 calc R . .
C43 C 0.77215(19) 0.3185(6) 1.0596(2) 0.0237(13) Uani 1 1 d . . .
C44 C 0.7923(2) 0.3906(6) 1.1190(2) 0.0245(13) Uani 1 1 d . . .
C45 C 0.8417(2) 0.4255(6) 1.2112(2) 0.0294(14) Uani 1 1 d . . .
C46 C 0.8807(2) 0.4180(7) 1.2686(3) 0.0443(17) Uani 1 1 d . . .
H46 H 0.9081 0.3438 1.2803 0.037(2) Uiso 1 1 calc R . .
C47 C 0.8772(2) 0.5240(7) 1.3069(3) 0.0509(18) Uani 1 1 d . . .
H47 H 0.9026 0.5199 1.3456 0.037(2) Uiso 1 1 calc R . .
C48 C 0.8377(3) 0.6374(7) 1.2912(3) 0.0496(18) Uani 1 1 d . . .
H48 H 0.8365 0.7054 1.3194 0.037(2) Uiso 1 1 calc R . .
C49 C 0.8003(2) 0.6499(7) 1.2346(3) 0.0432(17) Uani 1 1 d . . .
H49 H 0.7741 0.7278 1.2230 0.037(2) Uiso 1 1 calc R . .
C50 C 0.8029(2) 0.5423(6) 1.1950(2) 0.0305(14) Uani 1 1 d . . .
C51 C 0.7258(2) 0.6222(6) 1.1018(3) 0.0361(15) Uani 1 1 d . . .
H51A H 0.7059 0.6416 1.1245 0.037(2) Uiso 1 1 calc R . .
H51B H 0.7019 0.5700 1.0659 0.037(2) Uiso 1 1 calc R . .
C52 C 0.7430(2) 0.7778(6) 1.0869(3) 0.0347(15) Uani 1 1 d . . .
H52A H 0.7124 0.8448 1.0680 0.037(2) Uiso 1 1 calc R . .
H52B H 0.7596 0.7604 1.0611 0.037(2) Uiso 1 1 calc R . .
H52C H 0.7682 0.8276 1.1221 0.037(2) Uiso 1 1 calc R . .
C1S C 0.5496(2) 0.9281(6) 0.6195(2) 0.0330(14) Uani 1 1 d . . .
H1S H 0.5710 0.8347 0.6381 0.037(2) Uiso 1 1 calc R . .
Cl1 Cl 0.49653(6) 0.87079(17) 0.55380(7) 0.0438(4) Uani 1 1 d . . .
Cl2 Cl 0.59089(6) 1.06610(17) 0.60621(7) 0.0442(4) Uani 1 1 d . . .
Cl3 Cl 0.52544(6) 1.00981(17) 0.66717(7) 0.0455(4) Uani 1 1 d . . .
C2S C 0.0501(3) 0.2646(8) 0.4948(3) 0.063(2) Uani 1 1 d . . .
H2S H 0.0679 0.1772 0.4850 0.037(2) Uiso 1 1 calc R . .
Cl7 Cl 0.09521(9) 0.4174(3) 0.52172(13) 0.1094(9) Uani 1 1 d . . .
Cl8 Cl 0.03128(11) 0.1989(3) 0.54779(13) 0.1208(10) Uani 1 1 d . . .
Cl9 Cl -0.00600(10) 0.3139(4) 0.43293(12) 0.1237(10) Uani 1 1 d . . .
C3S C 0.0741(3) 0.5714(8) 0.2995(3) 0.072(2) Uani 1 1 d . . .
H3S H 0.0997 0.6571 0.3178 0.037(2) Uiso 1 1 calc R . .
Cl13 Cl 0.05980(10) 0.4808(3) 0.35249(12) 0.1065(8) Uani 1 1 d . . .
Cl14 Cl 0.01666(10) 0.6493(4) 0.24814(16) 0.207(2) Uani 1 1 d . . .
Cl15 Cl 0.10395(15) 0.4306(4) 0.27393(18) 0.1857(17) 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'
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
C5 N1 C4 104.7(4) . . ?
C5 N2 C6 105.7(4) . . ?
C5 N2 C8 130.5(5) . . ?
C6 N2 C8 123.7(5) . . ?
C10 N3 C14 116.7(4) . . ?
C15 N4 C16 105.4(4) . . ?
C21 N5 C15 107.5(4) . . ?
C21 N5 C22 122.0(4) . . ?
C15 N5 C22 130.6(5) . . ?
C33 N6 C32 105.1(4) . . ?
C33 N7 C34 106.3(4) . . ?
C33 N7 C37 130.9(5) . . ?
C34 N7 C37 122.3(4) . . ?
C43 N8 C39 117.7(4) . . ?
C44 N9 C45 104.9(4) . . ?
C44 N10 C50 106.6(4) . . ?
C44 N10 C51 132.9(5) . . ?
C50 N10 C51 120.5(4) . . ?
C7 C1 C2 122.0(6) . . ?
C7 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 121.8(6) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 117.9(6) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C6 C4 N1 111.1(5) . . ?
C6 C4 C3 119.3(5) . . ?
N1 C4 C3 129.6(6) . . ?
N1 C5 N2 112.6(5) . . ?
N1 C5 C10 119.9(5) . . ?
N2 C5 C10 127.5(5) . . ?
C4 C6 N2 105.8(5) . . ?
C4 C6 C7 124.0(5) . . ?
N2 C6 C7 130.2(6) . . ?
C1 C7 C6 114.9(6) . . ?
C1 C7 H7 122.5 . . ?
C6 C7 H7 122.5 . . ?
N2 C8 C9 111.1(5) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C11 122.6(5) . . ?
N3 C10 C5 120.9(5) . . ?
C11 C10 C5 116.5(5) . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 117.1(5) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 H12 121.5 . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
N3 C14 C13 122.5(5) . . ?
N3 C14 C15 120.5(5) . . ?
C13 C14 C15 116.9(5) . . ?
N4 C15 N5 111.9(5) . . ?
N4 C15 C14 120.2(5) . . ?
N5 C15 C14 127.9(5) . . ?
N4 C16 C21 109.8(5) . . ?
N4 C16 C17 129.1(5) . . ?
C21 C16 C17 121.1(5) . . ?
C18 C17 C16 118.7(5) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 119.3(5) . . ?
C17 C18 C24 119.7(5) . . ?
C19 C18 C24 121.0(5) . . ?
C20 C19 C18 123.1(5) . . ?
C20 C19 H19 118.5 . . ?
C18 C19 H19 118.5 . . ?
C21 C20 C19 117.2(5) . . ?
C21 C20 H20 121.4 . . ?
C19 C20 H20 121.4 . . ?
N5 C21 C20 133.8(5) . . ?
N5 C21 C16 105.5(4) . . ?
C20 C21 C16 120.7(5) . . ?
N5 C22 C23 111.6(4) . . ?
N5 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
N5 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 117.1(5) . . ?
C25 C24 C18 121.8(5) . . ?
C29 C24 C18 121.0(5) . . ?
C24 C25 C26 121.5(5) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C27 121.6(5) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
C28 C27 C26 116.3(5) . . ?
C28 C27 C30 122.1(5) . . ?
C26 C27 C30 121.6(5) . . ?
C29 C28 C27 122.1(5) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C28 C29 C24 121.3(5) . . ?
C28 C29 H29 119.4 . . ?
C24 C29 H29 119.4 . . ?
C31 C30 C36 120.1(5) . . ?
C31 C30 C27 122.6(5) . . ?
C36 C30 C27 117.2(4) . . ?
C30 C31 C32 119.0(5) . . ?
C30 C31 H31 120.5 . . ?
C32 C31 H31 120.5 . . ?
N6 C32 C31 131.4(5) . . ?
N6 C32 C34 109.5(4) . . ?
C31 C32 C34 119.2(5) . . ?
N6 C33 N7 113.1(4) . . ?
N6 C33 C39 121.2(4) . . ?
N7 C33 C39 125.6(5) . . ?
N7 C34 C35 130.5(5) . . ?
N7 C34 C32 106.1(4) . . ?
C35 C34 C32 123.4(5) . . ?
C34 C35 C36 116.2(5) . . ?
C34 C35 H35 121.9 . . ?
C36 C35 H35 121.9 . . ?
C35 C36 C30 122.0(5) . . ?
C35 C36 H36 119.0 . . ?
C30 C36 H36 119.0 . . ?
N7 C37 C38 109.3(4) . . ?
N7 C37 H37A 109.8 . . ?
C38 C37 H37A 109.8 . . ?
N7 C37 H37B 109.8 . . ?
C38 C37 H37B 109.8 . . ?
H37A C37 H37B 108.3 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N8 C39 C40 122.1(5) . . ?
N8 C39 C33 121.1(5) . . ?
C40 C39 C33 116.8(5) . . ?
C39 C40 C41 119.3(5) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
C42 C41 C40 118.7(5) . . ?
C42 C41 H41 120.7 . . ?
C40 C41 H41 120.7 . . ?
C41 C42 C43 119.9(5) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
N8 C43 C42 122.4(5) . . ?
N8 C43 C44 120.2(5) . . ?
C42 C43 C44 117.4(5) . . ?
N9 C44 N10 113.1(5) . . ?
N9 C44 C43 120.3(5) . . ?
N10 C44 C43 126.6(5) . . ?
C50 C45 C46 119.7(5) . . ?
C50 C45 N9 110.5(5) . . ?
C46 C45 N9 129.8(5) . . ?
C47 C46 C45 117.0(6) . . ?
C47 C46 H46 121.5 . . ?
C45 C46 H46 121.5 . . ?
C46 C47 C48 123.4(6) . . ?
C46 C47 H47 118.3 . . ?
C48 C47 H47 118.3 . . ?
C49 C48 C47 120.2(6) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C48 C49 C50 117.4(6) . . ?
C48 C49 H49 121.3 . . ?
C50 C49 H49 121.3 . . ?
C49 C50 C45 122.3(5) . . ?
C49 C50 N10 132.8(5) . . ?
C45 C50 N10 104.9(5) . . ?
N10 C51 C52 113.0(4) . . ?
N10 C51 H51A 109.0 . . ?
C52 C51 H51A 109.0 . . ?
N10 C51 H51B 109.0 . . ?
C52 C51 H51B 109.0 . . ?
H51A C51 H51B 107.8 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
Cl1 C1S Cl3 110.6(3) . . ?
Cl1 C1S Cl2 110.4(3) . . ?
Cl3 C1S Cl2 110.0(3) . . ?
Cl1 C1S H1S 108.6 . . ?
Cl3 C1S H1S 108.6 . . ?
Cl2 C1S H1S 108.6 . . ?
Cl9 C2S Cl7 113.2(4) . . ?
Cl9 C2S Cl8 109.3(4) . . ?
Cl7 C2S Cl8 110.2(4) . . ?
Cl9 C2S H2S 108.0 . . ?
Cl7 C2S H2S 108.0 . . ?
Cl8 C2S H2S 108.0 . . ?
Cl14 C3S Cl15 115.0(5) . . ?
Cl14 C3S Cl13 108.3(4) . . ?
Cl15 C3S Cl13 107.0(4) . . ?
Cl14 C3S H3S 108.8 . . ?
Cl15 C3S H3S 108.8 . . ?
Cl13 C3S H3S 108.8 . . ?
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
N1 C5 1.325(6) . ?
N1 C4 1.375(7) . ?
N2 C5 1.367(6) . ?
N2 C6 1.396(6) . ?
N2 C8 1.472(7) . ?
N3 C10 1.345(6) . ?
N3 C14 1.360(6) . ?
N4 C15 1.323(6) . ?
N4 C16 1.382(6) . ?
N5 C21 1.363(6) . ?
N5 C15 1.376(6) . ?
N5 C22 1.478(6) . ?
N6 C33 1.326(6) . ?
N6 C32 1.393(6) . ?
N7 C33 1.375(6) . ?
N7 C34 1.384(6) . ?
N7 C37 1.467(6) . ?
N8 C43 1.350(6) . ?
N8 C39 1.354(6) . ?
N9 C44 1.319(6) . ?
N9 C45 1.403(7) . ?
N10 C44 1.368(6) . ?
N10 C50 1.412(7) . ?
N10 C51 1.466(6) . ?
C1 C7 1.383(8) . ?
C1 C2 1.395(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.413(8) . ?
C3 H3 0.9300 . ?
C4 C6 1.365(7) . ?
C5 C10 1.486(7) . ?
C6 C7 1.404(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.519(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.390(7) . ?
C11 C12 1.371(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.489(7) . ?
C16 C21 1.404(6) . ?
C16 C17 1.405(7) . ?
C17 C18 1.374(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.400(7) . ?
C18 C24 1.505(7) . ?
C19 C20 1.394(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(7) . ?
C20 H20 0.9300 . ?
C22 C23 1.523(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.372(6) . ?
C24 C29 1.417(7) . ?
C25 C26 1.393(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.409(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.392(6) . ?
C27 C30 1.485(7) . ?
C28 C29 1.373(7) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C31 1.389(6) . ?
C30 C36 1.414(7) . ?
C31 C32 1.393(7) . ?
C31 H31 0.9300 . ?
C32 C34 1.406(7) . ?
C33 C39 1.487(7) . ?
C34 C35 1.386(7) . ?
C35 C36 1.390(7) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C38 1.526(7) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.384(7) . ?
C40 C41 1.386(7) . ?
C40 H40 0.9300 . ?
C41 C42 1.366(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.378(7) . ?
C42 H42 0.9300 . ?
C43 C44 1.493(7) . ?
C45 C50 1.387(7) . ?
C45 C46 1.389(8) . ?
C46 C47 1.358(8) . ?
C46 H46 0.9300 . ?
C47 C48 1.380(8) . ?
C47 H47 0.9300 . ?
C48 C49 1.364(8) . ?
C48 H48 0.9300 . ?
C49 C50 1.381(8) . ?
C49 H49 0.9300 . ?
C51 C52 1.506(7) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C1S Cl1 1.748(5) . ?
C1S Cl3 1.759(5) . ?
C1S Cl2 1.769(5) . ?
C1S H1S 0.9800 . ?
C2S Cl9 1.715(7) . ?
C2S Cl7 1.723(7) . ?
C2S Cl8 1.733(7) . ?
C2S H2S 0.9800 . ?
C3S Cl14 1.695(7) . ?
C3S Cl15 1.732(8) . ?
C3S Cl13 1.737(8) . ?
C3S H3S 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 C3 0.7(9) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
C5 N1 C4 C6 0.6(6) . . . . ?
C5 N1 C4 C3 -178.4(5) . . . . ?
C2 C3 C4 C6 -0.7(8) . . . . ?
C2 C3 C4 N1 178.3(5) . . . . ?
C4 N1 C5 N2 -1.5(6) . . . . ?
C4 N1 C5 C10 177.0(4) . . . . ?
C6 N2 C5 N1 1.8(6) . . . . ?
C8 N2 C5 N1 -179.7(5) . . . . ?
C6 N2 C5 C10 -176.5(5) . . . . ?
C8 N2 C5 C10 2.0(9) . . . . ?
N1 C4 C6 N2 0.4(6) . . . . ?
C3 C4 C6 N2 179.6(5) . . . . ?
N1 C4 C6 C7 -178.8(5) . . . . ?
C3 C4 C6 C7 0.4(8) . . . . ?
C5 N2 C6 C4 -1.3(5) . . . . ?
C8 N2 C6 C4 -180.0(5) . . . . ?
C5 N2 C6 C7 177.9(5) . . . . ?
C8 N2 C6 C7 -0.8(9) . . . . ?
C2 C1 C7 C6 -1.0(8) . . . . ?
C4 C6 C7 C1 0.5(8) . . . . ?
N2 C6 C7 C1 -178.5(5) . . . . ?
C5 N2 C8 C9 -94.7(6) . . . . ?
C6 N2 C8 C9 83.6(6) . . . . ?
C14 N3 C10 C11 0.1(7) . . . . ?
C14 N3 C10 C5 179.4(4) . . . . ?
N1 C5 C10 N3 179.6(4) . . . . ?
N2 C5 C10 N3 -2.1(8) . . . . ?
N1 C5 C10 C11 -1.0(7) . . . . ?
N2 C5 C10 C11 177.2(5) . . . . ?
N3 C10 C11 C12 1.7(8) . . . . ?
C5 C10 C11 C12 -177.7(5) . . . . ?
C10 C11 C12 C13 -1.3(8) . . . . ?
C11 C12 C13 C14 -0.6(8) . . . . ?
C10 N3 C14 C13 -2.0(7) . . . . ?
C10 N3 C14 C15 179.5(4) . . . . ?
C12 C13 C14 N3 2.4(8) . . . . ?
C12 C13 C14 C15 -179.1(5) . . . . ?
C16 N4 C15 N5 0.4(5) . . . . ?
C16 N4 C15 C14 -179.3(4) . . . . ?
C21 N5 C15 N4 -0.8(5) . . . . ?
C22 N5 C15 N4 -179.8(4) . . . . ?
C21 N5 C15 C14 178.9(5) . . . . ?
C22 N5 C15 C14 -0.1(8) . . . . ?
N3 C14 C15 N4 -174.2(4) . . . . ?
C13 C14 C15 N4 7.3(7) . . . . ?
N3 C14 C15 N5 6.1(8) . . . . ?
C13 C14 C15 N5 -172.4(5) . . . . ?
C15 N4 C16 C21 0.1(5) . . . . ?
C15 N4 C16 C17 178.8(5) . . . . ?
N4 C16 C17 C18 -178.3(5) . . . . ?
C21 C16 C17 C18 0.3(7) . . . . ?
C16 C17 C18 C19 -0.7(7) . . . . ?
C16 C17 C18 C24 178.9(4) . . . . ?
C17 C18 C19 C20 -0.4(7) . . . . ?
C24 C18 C19 C20 -179.9(5) . . . . ?
C18 C19 C20 C21 1.8(7) . . . . ?
C15 N5 C21 C20 -179.9(5) . . . . ?
C22 N5 C21 C20 -0.9(8) . . . . ?
C15 N5 C21 C16 0.8(5) . . . . ?
C22 N5 C21 C16 179.9(4) . . . . ?
C19 C20 C21 N5 178.7(5) . . . . ?
C19 C20 C21 C16 -2.2(7) . . . . ?
N4 C16 C21 N5 -0.6(5) . . . . ?
C17 C16 C21 N5 -179.5(4) . . . . ?
N4 C16 C21 C20 -180.0(4) . . . . ?
C17 C16 C21 C20 1.2(7) . . . . ?
C21 N5 C22 C23 84.5(6) . . . . ?
C15 N5 C22 C23 -96.7(6) . . . . ?
C17 C18 C24 C25 27.3(7) . . . . ?
C19 C18 C24 C25 -153.2(5) . . . . ?
C17 C18 C24 C29 -155.8(5) . . . . ?
C19 C18 C24 C29 23.7(7) . . . . ?
C29 C24 C25 C26 -2.2(7) . . . . ?
C18 C24 C25 C26 174.8(5) . . . . ?
C24 C25 C26 C27 -0.7(8) . . . . ?
C25 C26 C27 C28 2.7(7) . . . . ?
C25 C26 C27 C30 -175.0(4) . . . . ?
C26 C27 C28 C29 -1.7(7) . . . . ?
C30 C27 C28 C29 176.0(5) . . . . ?
C27 C28 C29 C24 -1.2(8) . . . . ?
C25 C24 C29 C28 3.2(7) . . . . ?
C18 C24 C29 C28 -173.8(4) . . . . ?
C28 C27 C30 C31 148.5(5) . . . . ?
C26 C27 C30 C31 -34.0(7) . . . . ?
C28 C27 C30 C36 -32.2(7) . . . . ?
C26 C27 C30 C36 145.3(5) . . . . ?
C36 C30 C31 C32 2.9(7) . . . . ?
C27 C30 C31 C32 -177.8(4) . . . . ?
C33 N6 C32 C31 -179.2(5) . . . . ?
C33 N6 C32 C34 -0.1(5) . . . . ?
C30 C31 C32 N6 176.8(5) . . . . ?
C30 C31 C32 C34 -2.2(7) . . . . ?
C32 N6 C33 N7 -0.7(6) . . . . ?
C32 N6 C33 C39 177.0(4) . . . . ?
C34 N7 C33 N6 1.3(6) . . . . ?
C37 N7 C33 N6 172.6(5) . . . . ?
C34 N7 C33 C39 -176.3(4) . . . . ?
C37 N7 C33 C39 -5.0(8) . . . . ?
C33 N7 C34 C35 178.7(5) . . . . ?
C37 N7 C34 C35 6.5(8) . . . . ?
C33 N7 C34 C32 -1.3(5) . . . . ?
C37 N7 C34 C32 -173.5(4) . . . . ?
N6 C32 C34 N7 0.9(5) . . . . ?
C31 C32 C34 N7 -179.9(4) . . . . ?
N6 C32 C34 C35 -179.1(4) . . . . ?
C31 C32 C34 C35 0.1(7) . . . . ?
N7 C34 C35 C36 -178.7(5) . . . . ?
C32 C34 C35 C36 1.3(7) . . . . ?
C34 C35 C36 C30 -0.6(7) . . . . ?
C31 C30 C36 C35 -1.5(7) . . . . ?
C27 C30 C36 C35 179.2(4) . . . . ?
C33 N7 C37 C38 -90.4(6) . . . . ?
C34 N7 C37 C38 79.7(6) . . . . ?
C43 N8 C39 C40 0.0(7) . . . . ?
C43 N8 C39 C33 179.0(4) . . . . ?
N6 C33 C39 N8 -173.3(5) . . . . ?
N7 C33 C39 N8 4.1(8) . . . . ?
N6 C33 C39 C40 5.7(7) . . . . ?
N7 C33 C39 C40 -176.9(5) . . . . ?
N8 C39 C40 C41 1.1(8) . . . . ?
C33 C39 C40 C41 -177.9(5) . . . . ?
C39 C40 C41 C42 -0.9(8) . . . . ?
C40 C41 C42 C43 -0.5(8) . . . . ?
C39 N8 C43 C42 -1.5(7) . . . . ?
C39 N8 C43 C44 178.3(4) . . . . ?
C41 C42 C43 N8 1.7(8) . . . . ?
C41 C42 C43 C44 -178.1(5) . . . . ?
C45 N9 C44 N10 -1.0(6) . . . . ?
C45 N9 C44 C43 -179.9(4) . . . . ?
C50 N10 C44 N9 1.0(6) . . . . ?
C51 N10 C44 N9 178.5(5) . . . . ?
C50 N10 C44 C43 179.8(5) . . . . ?
C51 N10 C44 C43 -2.7(9) . . . . ?
N8 C43 C44 N9 -169.8(5) . . . . ?
C42 C43 C44 N9 10.0(7) . . . . ?
N8 C43 C44 N10 11.5(8) . . . . ?
C42 C43 C44 N10 -168.7(5) . . . . ?
C44 N9 C45 C50 0.6(6) . . . . ?
C44 N9 C45 C46 -178.5(6) . . . . ?
C50 C45 C46 C47 2.8(9) . . . . ?
N9 C45 C46 C47 -178.2(6) . . . . ?
C45 C46 C47 C48 -0.9(10) . . . . ?
C46 C47 C48 C49 -1.6(11) . . . . ?
C47 C48 C49 C50 2.1(9) . . . . ?
C48 C49 C50 C45 -0.2(9) . . . . ?
C48 C49 C50 N10 177.8(6) . . . . ?
C46 C45 C50 C49 -2.3(9) . . . . ?
N9 C45 C50 C49 178.5(5) . . . . ?
C46 C45 C50 N10 179.2(5) . . . . ?
N9 C45 C50 N10 0.0(6) . . . . ?
C44 N10 C50 C49 -178.8(6) . . . . ?
C51 N10 C50 C49 3.3(9) . . . . ?
C44 N10 C50 C45 -0.6(6) . . . . ?
C51 N10 C50 C45 -178.5(4) . . . . ?
C44 N10 C51 C52 -100.3(6) . . . . ?
C50 N10 C51 C52 76.9(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660958
