#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/30/1503089.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_1503089
loop_
_publ_author_name
'Fernandes, Carlos'
'Faure, Sophie'
'Pereira, Elisabeth'
'Théry, Vincent'
'Declerck, Valérie'
'Guillot, Régis'
'Aitken, David J.'
_publ_section_title
;
 12-Helix folding of cyclobutane beta-amino acid oligomers.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3606
_journal_page_last               3609
_journal_paper_doi               10.1021/ol101267u
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C46 H68 N8 O11), 3(C H Cl3)'
_chemical_formula_sum            'C95 H139 Cl9 N16 O22'
_chemical_formula_weight         2176.27
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                90.00
_cell_formula_units_Z            2
_cell_length_a                   21.4551(14)
_cell_length_b                   28.4412(19)
_cell_length_c                   8.9866(6)
_cell_measurement_reflns_used    9600
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.35
_cell_volume                     5483.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            70127
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.78
_diffrn_reflns_theta_min         1.43
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2300
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.954
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     662
_refine_ls_number_reflns         14235
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1042P)²+4.3454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1682
_refine_ls_wR_factor_ref         0.1808
_reflns_number_gt                11885
_reflns_number_total             14235
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101267u_si_002.cif
_cod_data_source_block           858GuillotICMMO
_cod_original_formula_sum        'C95 H139 Cl9 N16 O22 '
_cod_database_code               1503089
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -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
C1 C 0.36053(16) 0.20197(12) 0.8503(4) 0.0372(7) Uani 1 1 d .
H1A H 0.3696 0.1691 0.8623 0.056 Uiso 1 1 calc R
H1B H 0.3987 0.2196 0.8510 0.056 Uiso 1 1 calc R
H1C H 0.3395 0.2068 0.7573 0.056 Uiso 1 1 calc R
C2 C 0.34935(15) 0.20772(12) 1.1265(4) 0.0332(6) Uani 1 1 d .
H2A H 0.3209 0.2159 1.2048 0.050 Uiso 1 1 calc R
H2B H 0.3869 0.2257 1.1367 0.050 Uiso 1 1 calc R
H2C H 0.3590 0.1748 1.1325 0.050 Uiso 1 1 calc R
C3 C 0.31940(13) 0.21832(10) 0.9763(4) 0.0271(6) Uani 1 1 d .
C4 C 0.30365(16) 0.27031(11) 0.9616(5) 0.0437(9) Uani 1 1 d .
H4A H 0.2873 0.2763 0.8641 0.066 Uiso 1 1 calc R
H4B H 0.3406 0.2887 0.9767 0.066 Uiso 1 1 calc R
H4C H 0.2731 0.2787 1.0350 0.066 Uiso 1 1 calc R
C5 C 0.24956(13) 0.15000(9) 0.9803(3) 0.0210(5) Uani 1 1 d .
C6 C 0.16786(12) 0.09099(9) 0.9749(3) 0.0218(5) Uani 1 1 d .
H6 H 0.2023 0.0689 0.9597 0.026 Uiso 1 1 calc R
C7 C 0.13301(13) 0.07858(10) 1.1226(3) 0.0270(6) Uani 1 1 d .
H7 H 0.1096 0.1055 1.1615 0.032 Uiso 1 1 calc R
C8 C 0.09134(15) 0.04581(11) 1.0275(5) 0.0392(8) Uani 1 1 d .
H8A H 0.1051 0.0133 1.0260 0.047 Uiso 1 1 calc R
H8B H 0.0473 0.0479 1.0510 0.047 Uiso 1 1 calc R
C9 C 0.11058(15) 0.07413(12) 0.8882(4) 0.0355(7) Uani 1 1 d .
H9A H 0.1204 0.0548 0.8024 0.043 Uiso 1 1 calc R
H9B H 0.0817 0.0990 0.8621 0.043 Uiso 1 1 calc R
C10 C 0.17500(14) 0.05796(10) 1.2369(3) 0.0285(6) Uani 1 1 d .
C11 C 0.23166(16) 0.07069(11) 1.4660(3) 0.0336(7) Uani 1 1 d .
H11 H 0.2320 0.0366 1.4809 0.040 Uiso 1 1 calc R
C12 C 0.2330(2) 0.09570(15) 1.6168(4) 0.0511(11) Uani 1 1 d .
H12A H 0.2148 0.1269 1.6153 0.061 Uiso 1 1 calc R
H12B H 0.2162 0.0771 1.6979 0.061 Uiso 1 1 calc R
C13 C 0.3042(2) 0.09553(14) 1.6090(4) 0.0468(10) Uani 1 1 d .
H13A H 0.3234 0.0693 1.6606 0.056 Uiso 1 1 calc R
H13B H 0.3232 0.1251 1.6378 0.056 Uiso 1 1 calc R
C14 C 0.29901(16) 0.08857(10) 1.4390(3) 0.0296(6) Uani 1 1 d .
H14 H 0.2985 0.1190 1.3878 0.036 Uiso 1 1 calc R
C15 C 0.34342(13) 0.05533(9) 1.3640(3) 0.0215(5) Uani 1 1 d .
C16 C 0.39846(12) 0.03794(9) 1.1325(3) 0.0207(5) Uani 1 1 d .
H16 H 0.4260 0.0179 1.1921 0.025 Uiso 1 1 calc R
C17 C 0.43447(13) 0.05996(9) 1.0029(3) 0.0254(6) Uani 1 1 d .
H17A H 0.4789 0.0627 1.0203 0.031 Uiso 1 1 calc R
H17B H 0.4171 0.0894 0.9679 0.031 Uiso 1 1 calc R
C18 C 0.41587(12) 0.01688(9) 0.9075(3) 0.0219(5) Uani 1 1 d .
H18A H 0.4469 -0.0079 0.9060 0.026 Uiso 1 1 calc R
H18B H 0.4024 0.0248 0.8076 0.026 Uiso 1 1 calc R
C19 C 0.36167(11) 0.00792(8) 1.0178(3) 0.0166(4) Uani 1 1 d .
H19 H 0.3237 0.0241 0.9857 0.020 Uiso 1 1 calc R
C20 C 0.34747(12) -0.04140(8) 1.0684(3) 0.0189(5) Uani 1 1 d .
C21 C 0.26779(13) -0.08767(9) 1.2009(3) 0.0235(5) Uani 1 1 d .
H21 H 0.2904 -0.1156 1.1670 0.028 Uiso 1 1 calc R
C22 C 0.19696(14) -0.09733(11) 1.2038(4) 0.0319(6) Uani 1 1 d .
H22A H 0.1840 -0.1229 1.1395 0.038 Uiso 1 1 calc R
H22B H 0.1716 -0.0696 1.1877 0.038 Uiso 1 1 calc R
C23 C 0.20368(16) -0.11137(12) 1.3695(4) 0.0384(8) Uani 1 1 d .
H23A H 0.1723 -0.0976 1.4337 0.046 Uiso 1 1 calc R
H23B H 0.2068 -0.1450 1.3855 0.046 Uiso 1 1 calc R
C24 C 0.26684(14) -0.08564(10) 1.3740(3) 0.0270(6) Uani 1 1 d .
H24 H 0.2621 -0.0533 1.4096 0.032 Uiso 1 1 calc R
C25 C 0.32121(14) -0.10940(9) 1.4466(3) 0.0257(6) Uani 1 1 d .
C26 C 0.42523(14) -0.10130(9) 1.5435(3) 0.0230(5) Uani 1 1 d .
H26 H 0.4176 -0.1322 1.5883 0.028 Uiso 1 1 calc R
C27 C 0.46889(17) -0.07300(10) 1.6448(3) 0.0334(7) Uani 1 1 d .
H27A H 0.4669 -0.0393 1.6296 0.040 Uiso 1 1 calc R
H27B H 0.4655 -0.0809 1.7495 0.040 Uiso 1 1 calc R
C28 C 0.52339(16) -0.09707(11) 1.5648(4) 0.0327(6) Uani 1 1 d .
H28A H 0.5374 -0.1258 1.6125 0.039 Uiso 1 1 calc R
H28B H 0.5581 -0.0763 1.5437 0.039 Uiso 1 1 calc R
C29 C 0.47989(13) -0.10534(9) 1.4305(3) 0.0229(5) Uani 1 1 d .
H29 H 0.4805 -0.0781 1.3636 0.028 Uiso 1 1 calc R
C30 C 0.48261(12) -0.15040(9) 1.3432(3) 0.0205(5) Uani 1 1 d .
C31 C 0.45369(13) -0.18607(9) 1.1022(3) 0.0200(5) Uani 1 1 d .
H31 H 0.4823 -0.2116 1.1284 0.024 Uiso 1 1 calc R
C32 C 0.45630(16) -0.17644(11) 0.9340(3) 0.0302(6) Uani 1 1 d .
H32A H 0.4951 -0.1858 0.8875 0.036 Uiso 1 1 calc R
H32B H 0.4450 -0.1446 0.9067 0.036 Uiso 1 1 calc R
C33 C 0.40325(17) -0.21228(11) 0.9152(3) 0.0332(7) Uani 1 1 d .
H33A H 0.4174 -0.2438 0.8910 0.040 Uiso 1 1 calc R
H33B H 0.3708 -0.2021 0.8473 0.040 Uiso 1 1 calc R
C34 C 0.38676(13) -0.20545(9) 1.0807(3) 0.0221(5) Uani 1 1 d .
H34 H 0.3559 -0.1803 1.0926 0.026 Uiso 1 1 calc R
C35 C 0.36979(12) -0.24723(9) 1.1750(3) 0.0214(5) Uani 1 1 d .
C36 C 0.32184(12) -0.27061(9) 1.4097(3) 0.0229(5) Uani 1 1 d .
H36 H 0.3243 -0.3027 1.3703 0.028 Uiso 1 1 calc R
C37 C 0.26173(13) -0.26446(11) 1.5018(4) 0.0325(7) Uani 1 1 d .
H37A H 0.2464 -0.2324 1.5045 0.039 Uiso 1 1 calc R
H37B H 0.2288 -0.2863 1.4752 0.039 Uiso 1 1 calc R
C38 C 0.29841(14) -0.27885(11) 1.6416(4) 0.0321(7) Uani 1 1 d .
H38A H 0.2943 -0.3118 1.6671 0.039 Uiso 1 1 calc R
H38B H 0.2905 -0.2590 1.7273 0.039 Uiso 1 1 calc R
C39 C 0.35944(12) -0.26689(10) 1.5586(3) 0.0232(5) Uani 1 1 d .
H39 H 0.3723 -0.2344 1.5780 0.028 Uiso 1 1 calc R
C40 C 0.41385(13) -0.29972(10) 1.5665(3) 0.0243(5) Uani 1 1 d .
C41 C 0.52223(13) -0.30792(10) 1.4821(4) 0.0269(6) Uani 1 1 d .
H41 H 0.5134 -0.3416 1.4925 0.032 Uiso 1 1 calc R
C42 C 0.58612(14) -0.29622(13) 1.5496(4) 0.0349(7) Uani 1 1 d .
H42A H 0.5906 -0.2637 1.5798 0.042 Uiso 1 1 calc R
H42B H 0.5989 -0.3174 1.6284 0.042 Uiso 1 1 calc R
C43 C 0.61512(13) -0.30733(11) 1.3980(3) 0.0284(6) Uani 1 1 d .
H43A H 0.6292 -0.3396 1.3876 0.034 Uiso 1 1 calc R
H43B H 0.6472 -0.2853 1.3673 0.034 Uiso 1 1 calc R
C44 C 0.54992(12) -0.29765(9) 1.3278(3) 0.0234(5) Uani 1 1 d .
H44 H 0.5455 -0.2642 1.3035 0.028 Uiso 1 1 calc R
C45 C 0.53024(14) -0.32718(11) 1.1992(4) 0.0336(7) Uani 1 1 d .
C46 C 0.5140(2) -0.3281(2) 0.9390(5) 0.0618(13) Uani 1 1 d .
H46A H 0.5396 -0.3554 0.9248 0.093 Uiso 1 1 calc R
H46B H 0.5173 -0.3080 0.8537 0.093 Uiso 1 1 calc R
H46C H 0.4714 -0.3377 0.9517 0.093 Uiso 1 1 calc R
C47 C 0.2121(2) 0.93201(15) 0.8276(5) 0.0502(9) Uani 1 1 d .
H47 H 0.2168 0.9383 0.9342 0.060 Uiso 1 1 calc R
C48 C 0.0100(3) 0.03217(13) 0.5204(5) 0.184(13) Uani 0.50 1 d PD
N1 N 0.18997(11) 0.13835(8) 0.9545(3) 0.0232(5) Uani 1 1 d .
H1 H 0.1644 0.1597 0.9250 0.028 Uiso 1 1 calc R
N2 N 0.18415(13) 0.08316(9) 1.3598(3) 0.0339(6) Uani 1 1 d .
H2 H 0.1612 0.1074 1.3761 0.041 Uiso 1 1 calc R
N3 N 0.36237(11) 0.06838(7) 1.2275(3) 0.0218(4) Uani 1 1 d .
H3 H 0.3526 0.0959 1.1956 0.026 Uiso 1 1 calc R
N4 N 0.28923(11) -0.04664(7) 1.1223(3) 0.0202(4) Uani 1 1 d .
H4 H 0.2632 -0.0240 1.1088 0.024 Uiso 1 1 calc R
N5 N 0.36711(12) -0.08170(7) 1.4947(3) 0.0263(5) Uani 1 1 d .
H5 H 0.3618 -0.0517 1.4966 0.032 Uiso 1 1 calc R
N6 N 0.46243(10) -0.14669(7) 1.2014(2) 0.0200(4) Uani 1 1 d .
H6A H 0.4542 -0.1190 1.1680 0.024 Uiso 1 1 calc R
N7 N 0.33544(11) -0.23735(8) 1.2952(3) 0.0229(5) Uani 1 1 d .
H7A H 0.3207 -0.2094 1.3040 0.027 Uiso 1 1 calc R
N8 N 0.46803(11) -0.28064(8) 1.5224(3) 0.0249(5) Uani 1 1 d .
H8 H 0.4706 -0.2505 1.5180 0.030 Uiso 1 1 calc R
O1 O 0.25777(9) 0.19662(7) 0.9630(3) 0.0286(4) Uani 1 1 d .
O2 O 0.29105(9) 0.12204(7) 1.0143(2) 0.0255(4) Uani 1 1 d .
O3 O 0.20371(11) 0.02063(7) 1.2138(3) 0.0351(5) Uani 1 1 d .
O4 O 0.36095(10) 0.01885(6) 1.4259(2) 0.0268(4) Uani 1 1 d .
O5 O 0.38615(9) -0.07317(6) 1.0648(2) 0.0236(4) Uani 1 1 d .
O6 O 0.32398(11) -0.15294(7) 1.4534(2) 0.0306(5) Uani 1 1 d .
O7 O 0.49969(10) -0.18765(7) 1.3985(2) 0.0262(4) Uani 1 1 d .
O8 O 0.38895(9) -0.28715(7) 1.1450(2) 0.0258(4) Uani 1 1 d .
O9 O 0.40826(10) -0.34136(8) 1.6005(3) 0.0349(5) Uani 1 1 d .
O10 O 0.51357(13) -0.36745(9) 1.2094(4) 0.0534(8) Uani 1 1 d .
O11 O 0.53452(11) -0.30314(10) 1.0695(3) 0.0424(6) Uani 1 1 d .
Cl1 Cl 0.24825(9) 0.97779(4) 0.73011(11) 0.0757(4) Uani 1 1 d .
Cl2 Cl 0.25012(6) 0.87935(4) 0.78853(13) 0.0596(3) Uani 1 1 d .
Cl3 Cl 0.13326(6) 0.92722(7) 0.7900(3) 0.1192(9) Uani 1 1 d .
Cl4 Cl 0.0000 0.0000 0.6781(4) 0.201(2) Uani 1 2 d SD
Cl5 Cl 0.0668(2) 0.0083(4) 0.4122(6) 0.356(10) Uani 0.50 1 d PD
Cl6 Cl -0.0580(4) 0.0368(3) 0.4242(5) 0.271(7) Uani 0.50 1 d PD
H48 H 0.0237(12) 0.0644(5) 0.551(3) 0.10(4) Uiso 0.50 1 d PD
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
C3 C1 H1A 109.5 . .
C3 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C3 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 H2A 109.5 . .
C3 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C3 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
O1 C3 C1 109.7(3) . .
O1 C3 C4 101.7(2) . .
C1 C3 C4 111.4(3) . .
O1 C3 C2 111.7(2) . .
C1 C3 C2 110.9(3) . .
C4 C3 C2 111.2(3) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O2 C5 N1 124.9(2) . .
O2 C5 O1 124.7(2) . .
N1 C5 O1 110.4(2) . .
N1 C6 C9 119.5(2) . .
N1 C6 C7 118.5(2) . .
C9 C6 C7 88.7(2) . .
N1 C6 H6 109.5 . .
C9 C6 H6 109.5 . .
C7 C6 H6 109.5 . .
C10 C7 C8 119.6(3) . .
C10 C7 C6 112.7(2) . .
C8 C7 C6 86.8(2) . .
C10 C7 H7 111.8 . .
C8 C7 H7 111.8 . .
C6 C7 H7 111.8 . .
C9 C8 C7 88.8(2) . .
C9 C8 H8A 113.8 . .
C7 C8 H8A 113.8 . .
C9 C8 H8B 113.9 . .
C7 C8 H8B 113.8 . .
H8A C8 H8B 111.1 . .
C6 C9 C8 88.0(2) . .
C6 C9 H9A 114.0 . .
C8 C9 H9A 114.0 . .
C6 C9 H9B 114.0 . .
C8 C9 H9B 114.0 . .
H9A C9 H9B 111.2 . .
O3 C10 N2 121.6(3) . .
O3 C10 C7 121.4(3) . .
N2 C10 C7 116.8(2) . .
N2 C11 C12 119.1(3) . .
N2 C11 C14 118.4(3) . .
C12 C11 C14 88.2(3) . .
N2 C11 H11 109.8 . .
C12 C11 H11 109.8 . .
C14 C11 H11 109.8 . .
C13 C12 C11 88.7(3) . .
C13 C12 H12A 113.9 . .
C11 C12 H12A 113.9 . .
C13 C12 H12B 113.9 . .
C11 C12 H12B 113.9 . .
H12A C12 H12B 111.1 . .
C12 C13 C14 88.5(3) . .
C12 C13 H13A 113.9 . .
C14 C13 H13A 113.9 . .
C12 C13 H13B 113.9 . .
C14 C13 H13B 113.9 . .
H13A C13 H13B 111.1 . .
C15 C14 C13 118.6(3) . .
C15 C14 C11 117.0(2) . .
C13 C14 C11 87.4(3) . .
C15 C14 H14 110.6 . .
C13 C14 H14 110.6 . .
C11 C14 H14 110.6 . .
O4 C15 N3 123.4(2) . .
O4 C15 C14 121.3(3) . .
N3 C15 C14 115.3(2) . .
N3 C16 C17 118.4(2) . .
N3 C16 C19 116.8(2) . .
C17 C16 C19 88.6(2) . .
N3 C16 H16 110.4 . .
C17 C16 H16 110.4 . .
C19 C16 H16 110.4 . .
C16 C17 C18 88.13(19) . .
C16 C17 H17A 114.0 . .
C18 C17 H17A 114.0 . .
C16 C17 H17B 114.0 . .
C18 C17 H17B 114.0 . .
H17A C17 H17B 111.2 . .
C17 C18 C19 88.27(19) . .
C17 C18 H18A 113.9 . .
C19 C18 H18A 113.9 . .
C17 C18 H18B 113.9 . .
C19 C18 H18B 113.9 . .
H18A C18 H18B 111.1 . .
C20 C19 C18 119.9(2) . .
C20 C19 C16 114.5(2) . .
C18 C19 C16 87.29(19) . .
C20 C19 H19 111.0 . .
C18 C19 H19 111.0 . .
C16 C19 H19 111.0 . .
O5 C20 N4 123.7(2) . .
O5 C20 C19 122.8(2) . .
N4 C20 C19 113.5(2) . .
N4 C21 C22 117.8(2) . .
N4 C21 C24 117.7(2) . .
C22 C21 C24 88.7(2) . .
N4 C21 H21 110.3 . .
C22 C21 H21 110.3 . .
C24 C21 H21 110.3 . .
C21 C22 C23 88.3(2) . .
C21 C22 H22A 113.9 . .
C23 C22 H22A 113.9 . .
C21 C22 H22B 113.9 . .
C23 C22 H22B 113.9 . .
H22A C22 H22B 111.1 . .
C24 C23 C22 89.1(2) . .
C24 C23 H23A 113.8 . .
C22 C23 H23A 113.8 . .
C24 C23 H23B 113.8 . .
C22 C23 H23B 113.8 . .
H23A C23 H23B 111.0 . .
C25 C24 C23 118.8(2) . .
C25 C24 C21 114.1(2) . .
C23 C24 C21 88.2(2) . .
C25 C24 H24 111.3 . .
C23 C24 H24 111.3 . .
C21 C24 H24 111.3 . .
O6 C25 N5 122.6(3) . .
O6 C25 C24 120.6(3) . .
N5 C25 C24 116.7(2) . .
N5 C26 C27 120.5(2) . .
N5 C26 C29 119.0(2) . .
C27 C26 C29 88.0(2) . .
N5 C26 H26 109.2 . .
C27 C26 H26 109.2 . .
C29 C26 H26 109.2 . .
C28 C27 C26 87.3(2) . .
C28 C27 H27A 114.1 . .
C26 C27 H27A 114.1 . .
C28 C27 H27B 114.1 . .
C26 C27 H27B 114.1 . .
H27A C27 H27B 111.3 . .
C27 C28 C29 88.5(2) . .
C27 C28 H28A 113.9 . .
C29 C28 H28A 113.9 . .
C27 C28 H28B 113.9 . .
C29 C28 H28B 113.9 . .
H28A C28 H28B 111.1 . .
C30 C29 C28 120.9(2) . .
C30 C29 C26 115.6(2) . .
C28 C29 C26 86.2(2) . .
C30 C29 H29 110.6 . .
C28 C29 H29 110.6 . .
C26 C29 H29 110.6 . .
O7 C30 N6 123.1(2) . .
O7 C30 C29 122.5(2) . .
N6 C30 C29 114.4(2) . .
N6 C31 C32 117.7(2) . .
N6 C31 C34 118.2(2) . .
C32 C31 C34 88.6(2) . .
N6 C31 H31 110.2 . .
C32 C31 H31 110.2 . .
C34 C31 H31 110.2 . .
C31 C32 C33 87.9(2) . .
C31 C32 H32A 114.0 . .
C33 C32 H32A 114.0 . .
C31 C32 H32B 114.0 . .
C33 C32 H32B 114.0 . .
H32A C32 H32B 111.2 . .
C32 C33 C34 88.9(2) . .
C32 C33 H33A 113.8 . .
C34 C33 H33A 113.8 . .
C32 C33 H33B 113.8 . .
C34 C33 H33B 113.8 . .
H33A C33 H33B 111.1 . .
C35 C34 C33 120.0(2) . .
C35 C34 C31 115.8(2) . .
C33 C34 C31 87.3(2) . .
C35 C34 H34 110.6 . .
C33 C34 H34 110.6 . .
C31 C34 H34 110.6 . .
O8 C35 N7 123.5(3) . .
O8 C35 C34 121.5(3) . .
N7 C35 C34 115.0(2) . .
N7 C36 C37 118.8(2) . .
N7 C36 C39 117.8(2) . .
C37 C36 C39 88.0(2) . .
N7 C36 H36 110.2 . .
C37 C36 H36 110.2 . .
C39 C36 H36 110.2 . .
C38 C37 C36 88.9(2) . .
C38 C37 H37A 113.8 . .
C36 C37 H37A 113.8 . .
C38 C37 H37B 113.8 . .
C36 C37 H37B 113.8 . .
H37A C37 H37B 111.1 . .
C37 C38 C39 88.9(2) . .
C37 C38 H38A 113.8 . .
C39 C38 H38A 113.8 . .
C37 C38 H38B 113.8 . .
C39 C38 H38B 113.8 . .
H38A C38 H38B 111.1 . .
C40 C39 C38 120.1(2) . .
C40 C39 C36 113.6(2) . .
C38 C39 C36 87.8(2) . .
C40 C39 H39 111.1 . .
C38 C39 H39 111.1 . .
C36 C39 H39 111.1 . .
O9 C40 N8 123.2(3) . .
O9 C40 C39 122.5(2) . .
N8 C40 C39 114.1(2) . .
N8 C41 C42 120.2(3) . .
N8 C41 C44 115.8(2) . .
C42 C41 C44 88.3(2) . .
N8 C41 H41 110.2 . .
C42 C41 H41 110.2 . .
C44 C41 H41 110.2 . .
C43 C42 C41 88.1(2) . .
C43 C42 H42A 114.0 . .
C41 C42 H42A 114.0 . .
C43 C42 H42B 114.0 . .
C41 C42 H42B 114.0 . .
H42A C42 H42B 111.2 . .
C42 C43 C44 87.7(2) . .
C42 C43 H43A 114.0 . .
C44 C43 H43A 114.0 . .
C42 C43 H43B 114.0 . .
C44 C43 H43B 114.0 . .
H43A C43 H43B 111.2 . .
C45 C44 C41 118.9(2) . .
C45 C44 C43 118.0(2) . .
C41 C44 C43 87.0(2) . .
C45 C44 H44 110.3 . .
C41 C44 H44 110.3 . .
C43 C44 H44 110.3 . .
O10 C45 O11 124.5(3) . .
O10 C45 C44 124.2(3) . .
O11 C45 C44 111.3(3) . .
O11 C46 H46A 109.5 . .
O11 C46 H46B 109.5 . .
H46A C46 H46B 109.5 . .
O11 C46 H46C 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
Cl3 C47 Cl2 110.6(2) . .
Cl3 C47 Cl1 113.2(3) . .
Cl2 C47 Cl1 109.4(2) . .
Cl3 C47 H47 107.8 . .
Cl2 C47 H47 107.9 . .
Cl1 C47 H47 107.9 . .
Cl6 C48 Cl4 110.92(9) . .
Cl6 C48 Cl5 110.82(9) . .
Cl4 C48 Cl5 110.59(9) . .
Cl6 C48 C48 83.09(18) . 2
Cl4 C48 C48 56.46(15) . 2
Cl5 C48 C48 76.98(19) . 2
Cl6 C48 Cl5 35.5(2) . 2
Cl4 C48 Cl5 89.6(3) . 2
Cl5 C48 Cl5 94.3(3) . 2
C48 C48 Cl5 47.92(19) 2 2
Cl6 C48 H48 108.7(13) . .
Cl4 C48 H48 107.4(13) . .
Cl5 C48 H48 108.3(13) . .
C48 C48 H48 163.4(13) 2 .
Cl5 C48 H48 143.9(13) 2 .
C5 N1 C6 121.5(2) . .
C5 N1 H1 119.2 . .
C6 N1 H1 119.2 . .
C10 N2 C11 121.4(2) . .
C10 N2 H2 119.3 . .
C11 N2 H2 119.3 . .
C15 N3 C16 122.5(2) . .
C15 N3 H3 118.8 . .
C16 N3 H3 118.8 . .
C20 N4 C21 124.2(2) . .
C20 N4 H4 117.9 . .
C21 N4 H4 117.9 . .
C25 N5 C26 120.8(2) . .
C25 N5 H5 119.6 . .
C26 N5 H5 119.6 . .
C30 N6 C31 124.3(2) . .
C30 N6 H6A 117.8 . .
C31 N6 H6A 117.8 . .
C35 N7 C36 123.7(2) . .
C35 N7 H7A 118.1 . .
C36 N7 H7A 118.1 . .
C40 N8 C41 123.6(2) . .
C40 N8 H8 118.2 . .
C41 N8 H8 118.2 . .
C5 O1 C3 121.6(2) . .
C45 O11 C46 115.5(3) . .
C48 Cl4 C48 67.1(3) 2 .
Cl6 Cl5 C48 104.0(2) 2 .
Cl6 Cl5 C48 49.3(2) 2 2
C48 Cl5 C48 55.10(15) . 2
Cl5 Cl6 C48 95.2(2) 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.509(5) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.525(4) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 O1 1.464(3) .
C3 C4 1.523(4) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 O2 1.232(3) .
C5 N1 1.341(3) .
C5 O1 1.347(3) .
C6 N1 1.440(3) .
C6 C9 1.532(4) .
C6 C7 1.564(4) .
C6 H6 0.9800 .
C7 C10 1.487(4) .
C7 C8 1.549(5) .
C7 H7 0.9800 .
C8 C9 1.545(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 O3 1.245(3) .
C10 N2 1.331(4) .
C11 N2 1.441(4) .
C11 C12 1.531(5) .
C11 C14 1.551(5) .
C11 H11 0.9800 .
C12 C13 1.529(7) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.544(4) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.502(4) .
C14 H14 0.9800 .
C15 O4 1.236(3) .
C15 N3 1.345(4) .
C16 N3 1.441(3) .
C16 C17 1.532(4) .
C16 C19 1.554(3) .
C16 H16 0.9800 .
C17 C18 1.547(4) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.549(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.506(3) .
C19 H19 0.9800 .
C20 O5 1.227(3) .
C20 N4 1.348(3) .
C21 N4 1.440(3) .
C21 C22 1.544(4) .
C21 C24 1.556(4) .
C21 H21 0.9800 .
C22 C23 1.549(5) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 C24 1.541(5) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C24 C25 1.498(4) .
C24 H24 0.9800 .
C25 O6 1.241(3) .
C25 N5 1.333(4) .
C26 N5 1.434(4) .
C26 C27 1.534(4) .
C26 C29 1.555(4) .
C26 H26 0.9800 .
C27 C28 1.534(5) .
C27 H27A 0.9700 .
C27 H27B 0.9700 .
C28 C29 1.543(4) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C29 C30 1.504(4) .
C29 H29 0.9800 .
C30 O7 1.226(3) .
C30 N6 1.350(4) .
C31 N6 1.444(3) .
C31 C32 1.537(4) .
C31 C34 1.550(4) .
C31 H31 0.9800 .
C32 C33 1.537(5) .
C32 H32A 0.9700 .
C32 H32B 0.9700 .
C33 C34 1.542(4) .
C33 H33A 0.9700 .
C33 H33B 0.9700 .
C34 C35 1.504(4) .
C34 H34 0.9800 .
C35 O8 1.237(3) .
C35 N7 1.338(4) .
C36 N7 1.428(4) .
C36 C37 1.542(4) .
C36 C39 1.566(4) .
C36 H36 0.9800 .
C37 C38 1.538(5) .
C37 H37A 0.9700 .
C37 H37B 0.9700 .
C38 C39 1.545(4) .
C38 H38A 0.9700 .
C38 H38B 0.9700 .
C39 C40 1.497(4) .
C39 H39 0.9800 .
C40 O9 1.229(3) .
C40 N8 1.343(3) .
C41 N8 1.444(4) .
C41 C42 1.535(4) .
C41 C44 1.537(4) .
C41 H41 0.9800 .
C42 C43 1.531(4) .
C42 H42A 0.9700 .
C42 H42B 0.9700 .
C43 C44 1.559(4) .
C43 H43A 0.9700 .
C43 H43B 0.9700 .
C44 C45 1.489(4) .
C44 H44 0.9800 .
C45 O10 1.203(4) .
C45 O11 1.354(5) .
C46 O11 1.440(4) .
C46 H46A 0.9600 .
C46 H46B 0.9600 .
C46 H46C 0.9600 .
C47 Cl3 1.730(4) .
C47 Cl2 1.741(5) .
C47 Cl1 1.750(4) .
C47 H47 0.9800 .
C48 Cl6 1.7006(10) .
C48 Cl4 1.7009(10) .
C48 Cl5 1.7010(10) .
C48 C48 1.880(8) 2
C48 Cl5 2.233(8) 2
C48 H48 1.001(13) .
N1 H1 0.8600 .
N2 H2 0.8600 .
N3 H3 0.8600 .
N4 H4 0.8600 .
N5 H5 0.8600 .
N6 H6A 0.8600 .
N7 H7A 0.8600 .
N8 H8 0.8600 .
Cl4 C48 1.7009(10) 2
Cl5 Cl6 1.301(10) 2
Cl5 C48 2.233(8) 2
Cl6 Cl5 1.301(10) 2
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_4
N1 C6 C7 C10 -95.2(3) . .
C9 C6 C7 C10 141.6(3) . .
N1 C6 C7 C8 144.0(3) . .
C9 C6 C7 C8 20.8(2) . .
C10 C7 C8 C9 -134.9(3) . .
C6 C7 C8 C9 -20.6(2) . .
N1 C6 C9 C8 -143.2(3) . .
C7 C6 C9 C8 -20.8(2) . .
C7 C8 C9 C6 21.0(2) . .
C8 C7 C10 O3 39.0(4) . .
C6 C7 C10 O3 -60.6(4) . .
C8 C7 C10 N2 -146.1(3) . .
C6 C7 C10 N2 114.2(3) . .
N2 C11 C12 C13 -142.0(3) . .
C14 C11 C12 C13 -20.2(3) . .
C11 C12 C13 C14 20.3(3) . .
C12 C13 C14 C15 -139.6(3) . .
C12 C13 C14 C11 -20.1(3) . .
N2 C11 C14 C15 -96.6(3) . .
C12 C11 C14 C15 141.0(3) . .
N2 C11 C14 C13 142.4(3) . .
C12 C11 C14 C13 20.0(2) . .
C13 C14 C15 O4 35.8(5) . .
C11 C14 C15 O4 -66.9(4) . .
C13 C14 C15 N3 -143.8(3) . .
C11 C14 C15 N3 113.5(3) . .
N3 C16 C17 C18 -140.7(2) . .
C19 C16 C17 C18 -20.78(19) . .
C16 C17 C18 C19 20.87(19) . .
C17 C18 C19 C20 -137.4(2) . .
C17 C18 C19 C16 -20.57(19) . .
N3 C16 C19 C20 -96.1(3) . .
C17 C16 C19 C20 142.6(2) . .
N3 C16 C19 C18 142.2(2) . .
C17 C16 C19 C18 20.78(19) . .
C18 C19 C20 O5 22.6(4) . .
C16 C19 C20 O5 -79.0(3) . .
C18 C19 C20 N4 -159.6(2) . .
C16 C19 C20 N4 98.8(3) . .
N4 C21 C22 C23 -138.8(3) . .
C24 C21 C22 C23 -17.9(2) . .
C21 C22 C23 C24 18.1(2) . .
C22 C23 C24 C25 -134.6(3) . .
C22 C23 C24 C21 -18.0(2) . .
N4 C21 C24 C25 -100.0(3) . .
C22 C21 C24 C25 138.9(2) . .
N4 C21 C24 C23 139.0(3) . .
C22 C21 C24 C23 18.0(2) . .
C23 C24 C25 O6 26.4(4) . .
C21 C24 C25 O6 -75.5(3) . .
C23 C24 C25 N5 -157.3(3) . .
C21 C24 C25 N5 100.8(3) . .
N5 C26 C27 C28 -146.4(3) . .
C29 C26 C27 C28 -23.5(2) . .
C26 C27 C28 C29 23.7(2) . .
C27 C28 C29 C30 -141.2(3) . .
C27 C28 C29 C26 -23.4(2) . .
N5 C26 C29 C30 -89.7(3) . .
C27 C26 C29 C30 146.1(2) . .
N5 C26 C29 C28 147.6(2) . .
C27 C26 C29 C28 23.4(2) . .
C28 C29 C30 O7 27.5(4) . .
C26 C29 C30 O7 -74.2(3) . .
C28 C29 C30 N6 -154.9(2) . .
C26 C29 C30 N6 103.4(3) . .
N6 C31 C32 C33 -141.8(3) . .
C34 C31 C32 C33 -20.4(2) . .
C31 C32 C33 C34 20.5(2) . .
C32 C33 C34 C35 -138.7(3) . .
C32 C33 C34 C31 -20.4(2) . .
N6 C31 C34 C35 -96.6(3) . .
C32 C31 C34 C35 142.5(2) . .
N6 C31 C34 C33 141.3(2) . .
C32 C31 C34 C33 20.4(2) . .
C33 C34 C35 O8 26.2(4) . .
C31 C34 C35 O8 -76.3(3) . .
C33 C34 C35 N7 -156.7(3) . .
C31 C34 C35 N7 100.7(3) . .
N7 C36 C37 C38 -139.9(3) . .
C39 C36 C37 C38 -19.1(2) . .
C36 C37 C38 C39 19.3(2) . .
C37 C38 C39 C40 -135.1(3) . .
C37 C38 C39 C36 -19.1(2) . .
N7 C36 C39 C40 -97.2(3) . .
C37 C36 C39 C40 141.0(2) . .
N7 C36 C39 C38 140.8(2) . .
C37 C36 C39 C38 19.0(2) . .
C38 C39 C40 O9 20.4(4) . .
C36 C39 C40 O9 -81.3(3) . .
C38 C39 C40 N8 -164.3(3) . .
C36 C39 C40 N8 94.0(3) . .
N8 C41 C42 C43 -141.8(3) . .
C44 C41 C42 C43 -22.6(2) . .
C41 C42 C43 C44 22.3(2) . .
N8 C41 C44 C45 -94.3(3) . .
C42 C41 C44 C45 142.7(3) . .
N8 C41 C44 C43 145.2(3) . .
C42 C41 C44 C43 22.2(2) . .
C42 C43 C44 C45 -143.6(3) . .
C42 C43 C44 C41 -22.3(2) . .
C41 C44 C45 O10 -28.6(4) . .
C43 C44 C45 O10 74.5(4) . .
C41 C44 C45 O11 152.4(3) . .
C43 C44 C45 O11 -104.5(3) . .
O2 C5 N1 C6 4.5(4) . .
O1 C5 N1 C6 -175.9(2) . .
C9 C6 N1 C5 -155.1(3) . .
C7 C6 N1 C5 98.8(3) . .
O3 C10 N2 C11 5.5(5) . .
C7 C10 N2 C11 -169.3(3) . .
C12 C11 N2 C10 -169.9(3) . .
C14 C11 N2 C10 85.2(4) . .
O4 C15 N3 C16 8.5(4) . .
C14 C15 N3 C16 -171.9(3) . .
C17 C16 N3 C15 -161.5(2) . .
C19 C16 N3 C15 94.4(3) . .
O5 C20 N4 C21 9.1(4) . .
C19 C20 N4 C21 -168.7(2) . .
C22 C21 N4 C20 -157.3(3) . .
C24 C21 N4 C20 98.3(3) . .
O6 C25 N5 C26 6.4(4) . .
C24 C25 N5 C26 -169.8(2) . .
C27 C26 N5 C25 -159.5(3) . .
C29 C26 N5 C25 94.1(3) . .
O7 C30 N6 C31 5.2(4) . .
C29 C30 N6 C31 -172.3(2) . .
C32 C31 N6 C30 -156.1(3) . .
C34 C31 N6 C30 99.5(3) . .
O8 C35 N7 C36 6.1(4) . .
C34 C35 N7 C36 -170.8(2) . .
C37 C36 N7 C35 -153.2(3) . .
C39 C36 N7 C35 102.7(3) . .
O9 C40 N8 C41 12.6(5) . .
C39 C40 N8 C41 -162.6(3) . .
C42 C41 N8 C40 -130.3(3) . .
C44 C41 N8 C40 125.6(3) . .
O2 C5 O1 C3 3.2(4) . .
N1 C5 O1 C3 -176.4(2) . .
C1 C3 O1 C5 66.7(3) . .
C4 C3 O1 C5 -175.3(3) . .
C2 C3 O1 C5 -56.7(4) . .
O10 C45 O11 C46 3.5(5) . .
C44 C45 O11 C46 -177.5(3) . .
Cl6 C48 Cl4 C48 65.9(2) . 2
Cl5 C48 Cl4 C48 -57.5(2) . 2
Cl5 C48 Cl4 C48 36.96(13) 2 2
Cl6 C48 Cl5 Cl6 -84.1(5) . 2
Cl4 C48 Cl5 Cl6 39.3(5) . 2
C48 C48 Cl5 Cl6 -6.8(4) 2 2
Cl5 C48 Cl5 Cl6 -51.8(5) 2 2
Cl6 C48 Cl5 C48 -77.28(17) . 2
Cl4 C48 Cl5 C48 46.16(16) . 2
Cl5 C48 Cl5 C48 -45.0(2) 2 2
Cl4 C48 Cl6 Cl5 -56.6(5) . 2
Cl5 C48 Cl6 Cl5 66.7(5) . 2
C48 C48 Cl6 Cl5 -6.5(3) 2 2
