#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/10/4031090.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_4031090
loop_
_publ_author_name
'Myśliwiec, Damian'
'Lis, Tadeusz'
'Gregoliński, Janusz'
'Stępień, Marcin'
_publ_section_title
;
 Stereoselective Wittig Olefination as a Macrocyclization Tool. Synthesis
 of Large Carbazolophanes.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6300
_journal_page_last               6312
_journal_paper_doi               10.1021/acs.joc.5b00745
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C54 H47 Br6 Cl2 N3, 0.5(C7 H8)'
_chemical_formula_sum            'C57.5 H51 Br6 Cl2 N3'
_chemical_formula_weight         1334.37
_chemical_name_systematic
;
 ?
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.41(3)
_cell_angle_beta                 111.30(3)
_cell_angle_gamma                90.28(3)
_cell_formula_units_Z            2
_cell_length_a                   13.461(4)
_cell_length_b                   14.296(4)
_cell_length_c                   14.910(5)
_cell_measurement_reflns_used    9386
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     2659.0(15)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Kuma KM4 with CCD camera'
_diffrn_measurement_method       ω
_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  0.0532
_diffrn_reflns_av_sigmaI/netI    0.1085
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29656
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    4.672
_exptl_absorpt_correction_T_max  0.589
_exptl_absorpt_correction_T_min  0.287
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5
Analytical numeric absorption correction using a
multifaceted crystal model based on expressions
 derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1322
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.41
_refine_diff_density_min         -0.51
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         13211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.041P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                6730
_reflns_number_total             13211
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00745_si_008.cif
_cod_data_source_block           dste47a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'TRICLINIC' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4031087--4031094.cif.
;
_cod_original_cell_volume        2659.0(14)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C57.50 H51 Br6 Cl2 N3'
_cod_database_code               4031090
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
Cl1 Cl 0.64127(11) 0.37241(10) 0.67351(11) 0.0549(4) Uani 1 1 d . . .
Cl2 Cl 0.16924(11) 0.05200(9) 0.62283(11) 0.0529(4) Uani 1 1 d . . .
Br1 Br 0.45487(4) 0.19333(4) 0.71495(4) 0.03920(14) Uani 1 1 d . . .
Br2 Br 0.08552(4) -0.09436(4) 0.14811(4) 0.04141(14) Uani 1 1 d . . .
Br3 Br 0.38989(4) 0.10952(4) -0.08310(4) 0.04112(14) Uani 1 1 d . . .
Br4 Br 0.22012(4) 0.66946(3) 0.06285(4) 0.03689(14) Uani 1 1 d . . .
Br5 Br -0.23155(4) 0.56872(4) 0.19640(4) 0.04145(14) Uani 1 1 d . . .
Br6 Br -0.09537(4) 0.15043(4) 0.59487(4) 0.04177(15) Uani 1 1 d . . .
N1 N 0.5227(3) 0.0910(3) 0.3422(3) 0.0321(9) Uani 1 1 d . . .
N2 N 0.0824(3) 0.2762(2) 0.0902(3) 0.0251(9) Uani 1 1 d . . .
N3 N 0.1665(3) 0.4171(3) 0.4725(3) 0.0278(9) Uani 1 1 d . B .
C1 C 0.6644(4) 0.2488(4) 0.6778(4) 0.0431(14) Uani 1 1 d . . .
H1A H 0.7354 0.2364 0.6746 0.052 Uiso 1 1 calc R . .
H1B H 0.6643 0.2297 0.7399 0.052 Uiso 1 1 calc R . .
C2 C 0.5805(4) 0.1919(3) 0.5957(3) 0.0329(12) Uani 1 1 d . . .
C3 C 0.4818(4) 0.1624(3) 0.5981(4) 0.0335(12) Uani 1 1 d . . .
C4 C 0.4058(4) 0.1120(3) 0.5228(3) 0.0308(11) Uani 1 1 d . . .
H4 H 0.3410 0.0921 0.5284 0.037 Uiso 1 1 calc R . .
C5 C 0.4236(4) 0.0898(3) 0.4373(3) 0.0293(11) Uani 1 1 d . . .
C6 C 0.3627(4) 0.0417(3) 0.3435(3) 0.0306(11) Uani 1 1 d . . .
C7 C 0.2617(4) -0.0025(3) 0.3020(3) 0.0318(11) Uani 1 1 d . . .
H7 H 0.2176 -0.0067 0.3390 0.038 Uiso 1 1 calc R . .
C8 C 0.2267(4) -0.0396(3) 0.2073(3) 0.0313(11) Uani 1 1 d . . .
C9 C 0.2883(4) -0.0336(3) 0.1490(4) 0.0327(12) Uani 1 1 d . . .
C10 C 0.2504(4) -0.0666(3) 0.0447(4) 0.0368(12) Uani 1 1 d . . .
H10 H 0.2409 -0.1325 0.0262 0.044 Uiso 1 1 calc R . .
C11 C 0.2287(4) -0.0097(3) -0.0244(4) 0.0333(12) Uani 1 1 d . . .
H11 H 0.2145 -0.0364 -0.0888 0.040 Uiso 1 1 calc R . .
C12 C 0.2256(4) 0.0942(3) -0.0062(3) 0.0288(11) Uani 1 1 d . . .
C13 C 0.2876(4) 0.1571(3) -0.0303(3) 0.0287(11) Uani 1 1 d . . .
C14 C 0.2829(3) 0.2533(3) -0.0161(3) 0.0269(10) Uani 1 1 d . . .
H14 H 0.3268 0.2941 -0.0339 0.032 Uiso 1 1 calc R . .
C15 C 0.2115(3) 0.2886(3) 0.0254(3) 0.0241(10) Uani 1 1 d . . .
C16 C 0.1846(3) 0.3830(3) 0.0531(3) 0.0262(10) Uani 1 1 d . . .
C17 C 0.2178(3) 0.4733(3) 0.0459(3) 0.0266(11) Uani 1 1 d . . .
H17 H 0.2707 0.4829 0.0191 0.032 Uiso 1 1 calc R . .
C18 C 0.1727(4) 0.5476(3) 0.0782(3) 0.0297(11) Uani 1 1 d . . .
C19 C 0.0939(3) 0.5386(3) 0.1188(3) 0.0271(11) Uani 1 1 d . . .
C20 C 0.0459(4) 0.6226(3) 0.1497(3) 0.0304(11) Uani 1 1 d . . .
H20 H 0.0471 0.6774 0.1186 0.036 Uiso 1 1 calc R . .
C21 C 0.0011(4) 0.6300(3) 0.2162(3) 0.0335(12) Uani 1 1 d . . .
H21 H -0.0325 0.6874 0.2220 0.040 Uiso 1 1 calc R . .
C22 C -0.0031(4) 0.5610(3) 0.2818(3) 0.0271(11) Uani 1 1 d . . .
C23 C -0.1001(4) 0.5254(3) 0.2822(3) 0.0319(12) Uani 1 1 d . . .
C24 C -0.1073(4) 0.4577(3) 0.3392(3) 0.0311(11) Uani 1 1 d . . .
H24 H -0.1747 0.4347 0.3367 0.037 Uiso 1 1 calc R . .
C25 C -0.0135(3) 0.4239(3) 0.4005(3) 0.0270(11) Uani 1 1 d . . .
C26 C 0.0093(3) 0.3547(3) 0.4680(3) 0.0260(10) Uani 1 1 d . . .
C27 C -0.0554(4) 0.2940(3) 0.4946(3) 0.0268(11) Uani 1 1 d . . .
H27 H -0.1310 0.2943 0.4664 0.032 Uiso 1 1 calc R . .
C28 C -0.0053(4) 0.2338(3) 0.5632(3) 0.0319(11) Uani 1 1 d . . .
C29 C 0.1053(4) 0.2316(3) 0.6066(3) 0.0297(11) Uani 1 1 d . . .
C30 C 0.1576(4) 0.1656(3) 0.6806(4) 0.0387(13) Uani 1 1 d . . .
H30A H 0.1148 0.1589 0.7216 0.046 Uiso 1 1 calc R . .
H30B H 0.2294 0.1916 0.7229 0.046 Uiso 1 1 calc R . .
C31 C 0.1696(4) 0.2913(3) 0.5797(3) 0.0298(11) Uani 1 1 d . . .
H31 H 0.2452 0.2907 0.6080 0.036 Uiso 1 1 calc R . .
C32 C 0.1202(4) 0.3513(3) 0.5106(3) 0.0277(11) Uani 1 1 d . . .
C33 C 0.0855(4) 0.4604(3) 0.4047(3) 0.0265(11) Uani 1 1 d . . .
C34 C 0.0909(4) 0.5282(3) 0.3443(3) 0.0284(11) Uani 1 1 d . . .
H34 H 0.1580 0.5514 0.3463 0.034 Uiso 1 1 calc R . .
C35 C 0.0609(3) 0.4480(3) 0.1245(3) 0.0273(11) Uani 1 1 d . . .
H35 H 0.0070 0.4385 0.1502 0.033 Uiso 1 1 calc R . .
C36 C 0.1066(3) 0.3716(3) 0.0929(3) 0.0232(10) Uani 1 1 d . . .
C37 C 0.1477(3) 0.2261(3) 0.0512(3) 0.0253(10) Uani 1 1 d . . .
C38 C 0.1537(4) 0.1296(3) 0.0359(3) 0.0278(11) Uani 1 1 d . . .
H38 H 0.1100 0.0881 0.0535 0.033 Uiso 1 1 calc R . .
C39 C 0.3893(4) 0.0094(3) 0.1905(3) 0.0320(11) Uani 1 1 d . . .
H39 H 0.4331 0.0141 0.1534 0.038 Uiso 1 1 calc R . .
C40 C 0.4257(4) 0.0456(3) 0.2873(3) 0.0301(11) Uani 1 1 d . . .
C41 C 0.5214(4) 0.1196(3) 0.4328(3) 0.0318(11) Uani 1 1 d . . .
C42 C 0.5988(4) 0.1697(3) 0.5104(4) 0.0344(12) Uani 1 1 d . . .
H42 H 0.6641 0.1891 0.5056 0.041 Uiso 1 1 calc R . .
C1A C 0.6128(4) 0.1018(4) 0.3120(4) 0.0423(13) Uani 1 1 d . . .
H1A1 H 0.6187 0.0428 0.2741 0.051 Uiso 1 1 calc R . .
H1A2 H 0.6788 0.1110 0.3705 0.051 Uiso 1 1 calc R . .
C2A C 0.6064(4) 0.1822(4) 0.2522(4) 0.0564(16) Uani 1 1 d . . .
H2A1 H 0.6038 0.2422 0.2902 0.068 Uiso 1 1 calc R . .
H2A2 H 0.5404 0.1745 0.1937 0.068 Uiso 1 1 calc R . .
C3A C 0.7035(5) 0.1846(5) 0.2227(5) 0.072(2) Uani 1 1 d . . .
H3A1 H 0.7678 0.2008 0.2815 0.086 Uiso 1 1 calc R . .
H3A2 H 0.7118 0.1208 0.1949 0.086 Uiso 1 1 calc R . .
C4A C 0.6986(6) 0.2519(6) 0.1518(5) 0.088(2) Uani 1 1 d . . .
H4A1 H 0.7644 0.2499 0.1378 0.133 Uiso 1 1 calc R . .
H4A2 H 0.6911 0.3155 0.1787 0.133 Uiso 1 1 calc R . .
H4A3 H 0.6373 0.2347 0.0920 0.133 Uiso 1 1 calc R . .
C1B C 0.0105(4) 0.2351(3) 0.1289(3) 0.0298(11) Uani 1 1 d . . .
H1B1 H -0.0296 0.1811 0.0834 0.036 Uiso 1 1 calc R . .
H1B2 H -0.0418 0.2822 0.1330 0.036 Uiso 1 1 calc R . .
C2B C 0.0647(4) 0.2018(3) 0.2277(3) 0.0334(12) Uani 1 1 d . . .
H2B1 H 0.1062 0.2552 0.2733 0.040 Uiso 1 1 calc R . .
H2B2 H 0.1153 0.1531 0.2236 0.040 Uiso 1 1 calc R . .
C3B C -0.0139(4) 0.1614(4) 0.2671(4) 0.0470(14) Uani 1 1 d . . .
H3B1 H -0.0592 0.2123 0.2780 0.056 Uiso 1 1 calc R . .
H3B2 H -0.0611 0.1132 0.2179 0.056 Uiso 1 1 calc R . .
C4B C 0.0380(5) 0.1181(4) 0.3597(4) 0.0511(15) Uani 1 1 d . . .
H4B1 H -0.0171 0.0944 0.3814 0.077 Uiso 1 1 calc R . .
H4B2 H 0.0842 0.1655 0.4093 0.077 Uiso 1 1 calc R . .
H4B3 H 0.0808 0.0660 0.3491 0.077 Uiso 1 1 calc R . .
C1C C 0.2817(4) 0.4347(4) 0.5003(4) 0.0376(12) Uani 1 1 d . . .
H1C1 H 0.3165 0.4313 0.5708 0.045 Uiso 1 1 calc R A 1
H1C2 H 0.2945 0.4994 0.4872 0.045 Uiso 1 1 calc R A 1
C2C C 0.3332(5) 0.3673(4) 0.4487(5) 0.064(2) Uani 0.799(7) 1 d P B 1
H2C1 H 0.4113 0.3734 0.4840 0.076 Uiso 0.799(7) 1 calc PR B 1
H2C2 H 0.3099 0.3026 0.4530 0.076 Uiso 0.799(7) 1 calc PR B 1
C3C C 0.3121(5) 0.3779(4) 0.3491(5) 0.0349(17) Uani 0.799(7) 1 d P B 1
H3C1 H 0.3396 0.4409 0.3444 0.042 Uiso 0.799(7) 1 calc PR B 1
H3C2 H 0.2339 0.3750 0.3137 0.042 Uiso 0.799(7) 1 calc PR B 1
C4C C 0.3624(6) 0.3027(5) 0.2987(5) 0.048(2) Uani 0.799(7) 1 d P B 1
H4C1 H 0.3447 0.3145 0.2311 0.073 Uiso 0.799(7) 1 calc PR B 1
H4C2 H 0.3341 0.2401 0.3012 0.073 Uiso 0.799(7) 1 calc PR B 1
H4C3 H 0.4401 0.3060 0.3321 0.073 Uiso 0.799(7) 1 calc PR B 1
C2D C 0.3332(5) 0.3673(4) 0.4487(5) 0.064(2) Uani 0.20 1 d P B 2
H2D1 H 0.3569 0.3159 0.4908 0.076 Uiso 0.201(7) 1 calc PR B 2
H2D2 H 0.2739 0.3396 0.3902 0.076 Uiso 0.201(7) 1 calc PR B 2
C3D C 0.423(2) 0.3855(19) 0.415(2) 0.048(8) Uiso 0.201(7) 1 d P B 2
H3D1 H 0.4258 0.4549 0.4164 0.058 Uiso 0.201(7) 1 calc PR B 2
H3D2 H 0.4867 0.3710 0.4703 0.058 Uiso 0.201(7) 1 calc PR B 2
C4D C 0.451(3) 0.355(3) 0.333(3) 0.080(11) Uiso 0.201(7) 1 d P B 2
H4D1 H 0.5204 0.3853 0.3416 0.120 Uiso 0.201(7) 1 calc PR B 2
H4D2 H 0.3967 0.3735 0.2742 0.120 Uiso 0.201(7) 1 calc PR B 2
H4D3 H 0.4568 0.2869 0.3282 0.120 Uiso 0.201(7) 1 calc PR B 2
C01 C 0.4919(7) 0.523(2) 0.0882(9) 0.143(5) Uani 1 1 d . . .
H01 H 0.4857 0.5371 0.1472 0.172 Uiso 0.50 1 d PR . .
C02 C 0.4916(6) 0.5888(9) 0.0321(16) 0.123(4) Uani 1 1 d . . .
H02 H 0.4868 0.6522 0.0552 0.148 Uiso 1 1 calc R . .
C03 C 0.5021(8) 0.4290(13) 0.0594(17) 0.146(6) Uani 1 1 d . . .
H03 H 0.5047 0.3804 0.0993 0.176 Uiso 1 1 calc R . .
C04 C 0.4937(13) 0.5229(19) 0.1794(13) 0.158(10) Uani 0.50 1 d P . .
H04A H 0.5663 0.5388 0.2256 0.237 Uiso 0.50 1 d PR . .
H04B H 0.4713 0.4602 0.1882 0.237 Uiso 0.50 1 d PR . .
H04C H 0.4449 0.5692 0.1905 0.237 Uiso 0.50 1 d PR . .
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'
Br Br -0.2901 2.4595 '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
C41 N1 C40 108.2(4) . .
C41 N1 C1A 125.7(4) . .
C40 N1 C1A 126.0(4) . .
C37 N2 C36 107.6(3) . .
C37 N2 C1B 125.1(4) . .
C36 N2 C1B 127.0(4) . .
C33 N3 C32 108.3(4) . .
C33 N3 C1C 127.1(4) . .
C32 N3 C1C 124.6(4) . .
C2 C1 Cl1 111.0(3) . .
C2 C1 H1A 109.4 . .
Cl1 C1 H1A 109.4 . .
C2 C1 H1B 109.4 . .
Cl1 C1 H1B 109.4 . .
H1A C1 H1B 108.0 . .
C42 C2 C3 117.6(4) . .
C42 C2 C1 118.5(4) . .
C3 C2 C1 123.9(5) . .
C4 C3 C2 123.4(5) . .
C4 C3 Br1 118.4(4) . .
C2 C3 Br1 118.2(4) . .
C3 C4 C5 119.2(4) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
C4 C5 C41 118.5(4) . .
C4 C5 C6 135.2(4) . .
C41 C5 C6 106.3(4) . .
C7 C6 C40 118.8(5) . .
C7 C6 C5 134.6(4) . .
C40 C6 C5 106.6(4) . .
C8 C7 C6 119.1(4) . .
C8 C7 H7 120.4 . .
C6 C7 H7 120.4 . .
C7 C8 C9 122.5(4) . .
C7 C8 Br2 119.3(4) . .
C9 C8 Br2 118.0(4) . .
C39 C9 C8 118.3(4) . .
C39 C9 C10 117.5(4) . .
C8 C9 C10 124.2(4) . .
C11 C10 C9 123.7(4) . .
C11 C10 H10 118.2 . .
C9 C10 H10 118.2 . .
C10 C11 C12 123.3(5) . .
C10 C11 H11 118.4 . .
C12 C11 H11 118.4 . .
C13 C12 C38 118.7(4) . .
C13 C12 C11 123.6(4) . .
C38 C12 C11 117.7(4) . .
C14 C13 C12 123.8(4) . .
C14 C13 Br3 117.3(3) . .
C12 C13 Br3 118.9(3) . .
C13 C14 C15 117.7(4) . .
C13 C14 H14 121.1 . .
C15 C14 H14 121.1 . .
C14 C15 C37 119.7(4) . .
C14 C15 C16 134.3(4) . .
C37 C15 C16 106.0(4) . .
C17 C16 C36 119.2(4) . .
C17 C16 C15 134.2(4) . .
C36 C16 C15 106.6(4) . .
C18 C17 C16 118.4(4) . .
C18 C17 H17 120.8 . .
C16 C17 H17 120.8 . .
C17 C18 C19 123.8(4) . .
C17 C18 Br4 115.9(3) . .
C19 C18 Br4 120.3(3) . .
C35 C19 C18 117.0(4) . .
C35 C19 C20 122.1(4) . .
C18 C19 C20 120.9(4) . .
C21 C20 C19 127.3(4) . .
C21 C20 H20 116.4 . .
C19 C20 H20 116.4 . .
C20 C21 C22 128.4(4) . .
C20 C21 H21 115.8 . .
C22 C21 H21 115.8 . .
C34 C22 C23 118.4(4) . .
C34 C22 C21 119.7(4) . .
C23 C22 C21 121.9(4) . .
C24 C23 C22 123.5(4) . .
C24 C23 Br5 116.9(4) . .
C22 C23 Br5 119.6(3) . .
C23 C24 C25 118.0(4) . .
C23 C24 H24 121.0 . .
C25 C24 H24 121.0 . .
C24 C25 C33 120.1(4) . .
C24 C25 C26 133.3(4) . .
C33 C25 C26 106.6(4) . .
C32 C26 C27 119.2(4) . .
C32 C26 C25 107.4(4) . .
C27 C26 C25 133.3(4) . .
C28 C27 C26 117.8(4) . .
C28 C27 H27 121.1 . .
C26 C27 H27 121.1 . .
C27 C28 C29 122.7(4) . .
C27 C28 Br6 116.6(4) . .
C29 C28 Br6 120.7(4) . .
C28 C29 C31 119.5(4) . .
C28 C29 C30 121.7(4) . .
C31 C29 C30 118.8(4) . .
C29 C30 Cl2 110.6(4) . .
C29 C30 H30A 109.5 . .
Cl2 C30 H30A 109.5 . .
C29 C30 H30B 109.5 . .
Cl2 C30 H30B 109.5 . .
H30A C30 H30B 108.1 . .
C32 C31 C29 118.2(4) . .
C32 C31 H31 120.9 . .
C29 C31 H31 120.9 . .
C31 C32 N3 128.9(4) . .
C31 C32 C26 122.5(4) . .
N3 C32 C26 108.6(4) . .
N3 C33 C34 130.1(4) . .
N3 C33 C25 109.0(4) . .
C34 C33 C25 120.8(4) . .
C22 C34 C33 119.0(4) . .
C22 C34 H34 120.5 . .
C33 C34 H34 120.5 . .
C36 C35 C19 120.0(4) . .
C36 C35 H35 120.0 . .
C19 C35 H35 120.0 . .
C35 C36 N2 128.5(4) . .
C35 C36 C16 121.6(4) . .
N2 C36 C16 109.8(4) . .
C38 C37 N2 128.5(4) . .
C38 C37 C15 121.5(4) . .
N2 C37 C15 109.9(4) . .
C37 C38 C12 118.6(4) . .
C37 C38 H38 120.7 . .
C12 C38 H38 120.7 . .
C9 C39 C40 119.1(4) . .
C9 C39 H39 120.4 . .
C40 C39 H39 120.4 . .
N1 C40 C39 128.4(4) . .
N1 C40 C6 109.6(4) . .
C39 C40 C6 122.0(4) . .
C42 C41 N1 128.9(4) . .
C42 C41 C5 121.8(4) . .
N1 C41 C5 109.3(4) . .
C41 C42 C2 119.5(4) . .
C41 C42 H42 120.2 . .
C2 C42 H42 120.2 . .
N1 C1A C2A 114.5(4) . .
N1 C1A H1A1 108.6 . .
C2A C1A H1A1 108.6 . .
N1 C1A H1A2 108.6 . .
C2A C1A H1A2 108.6 . .
H1A1 C1A H1A2 107.6 . .
C1A C2A C3A 109.6(5) . .
C1A C2A H2A1 109.7 . .
C3A C2A H2A1 109.7 . .
C1A C2A H2A2 109.7 . .
C3A C2A H2A2 109.7 . .
H2A1 C2A H2A2 108.2 . .
C4A C3A C2A 114.6(6) . .
C4A C3A H3A1 108.6 . .
C2A C3A H3A1 108.6 . .
C4A C3A H3A2 108.6 . .
C2A C3A H3A2 108.6 . .
H3A1 C3A H3A2 107.6 . .
C3A C4A H4A1 109.5 . .
C3A C4A H4A2 109.5 . .
H4A1 C4A H4A2 109.5 . .
C3A C4A H4A3 109.5 . .
H4A1 C4A H4A3 109.5 . .
H4A2 C4A H4A3 109.5 . .
N2 C1B C2B 114.3(4) . .
N2 C1B H1B1 108.7 . .
C2B C1B H1B1 108.7 . .
N2 C1B H1B2 108.7 . .
C2B C1B H1B2 108.7 . .
H1B1 C1B H1B2 107.6 . .
C1B C2B C3B 112.7(4) . .
C1B C2B H2B1 109.0 . .
C3B C2B H2B1 109.0 . .
C1B C2B H2B2 109.0 . .
C3B C2B H2B2 109.0 . .
H2B1 C2B H2B2 107.8 . .
C4B C3B C2B 113.8(4) . .
C4B C3B H3B1 108.8 . .
C2B C3B H3B1 108.8 . .
C4B C3B H3B2 108.8 . .
C2B C3B H3B2 108.8 . .
H3B1 C3B H3B2 107.7 . .
C3B C4B H4B1 109.5 . .
C3B C4B H4B2 109.5 . .
H4B1 C4B H4B2 109.5 . .
C3B C4B H4B3 109.5 . .
H4B1 C4B H4B3 109.5 . .
H4B2 C4B H4B3 109.5 . .
N3 C1C C2C 114.3(4) . .
N3 C1C H1C1 108.7 . .
C2C C1C H1C1 108.7 . .
N3 C1C H1C2 108.7 . .
C2C C1C H1C2 108.7 . .
H1C1 C1C H1C2 107.6 . .
C3C C2C C1C 116.8(5) . .
C3C C2C H2C1 108.1 . .
C1C C2C H2C1 108.1 . .
C3C C2C H2C2 108.1 . .
C1C C2C H2C2 108.1 . .
H2C1 C2C H2C2 107.3 . .
C2C C3C C4C 114.2(5) . .
C2C C3C H3C1 108.7 . .
C4C C3C H3C1 108.7 . .
C2C C3C H3C2 108.7 . .
C4C C3C H3C2 108.7 . .
H3C1 C3C H3C2 107.6 . .
C3C C4C H4C1 109.5 . .
C3C C4C H4C2 109.5 . .
H4C1 C4C H4C2 109.5 . .
C3C C4C H4C3 109.5 . .
H4C1 C4C H4C3 109.5 . .
H4C2 C4C H4C3 109.5 . .
C4D C3D H3D1 102.8 . .
C4D C3D H3D2 102.8 . .
H3D1 C3D H3D2 105.0 . .
C3D C4D H4D1 109.5 . .
C3D C4D H4D2 109.5 . .
H4D1 C4D H4D2 109.5 . .
C3D C4D H4D3 109.5 . .
H4D1 C4D H4D3 109.5 . .
H4D2 C4D H4D3 109.5 . .
C02 C01 C04 135(3) . .
C02 C01 C03 120.5(14) . .
C04 C01 C03 105(3) . .
C02 C01 H01 121.4 . .
C03 C01 H01 118.1 . .
C01 C02 C03 123.8(14) . 2_665
C01 C02 H02 118.1 . .
C03 C02 H02 118.1 2_665 .
C01 C03 C02 115.6(15) . 2_665
C01 C03 H03 122.2 . .
C02 C03 H03 122.2 2_665 .
C01 C04 H04A 109.5 . .
C01 C04 H04B 109.1 . .
C01 C04 H04C 109.7 . .
H04A C04 H04C 109.5 . .
H04B C04 H04C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.799(5) .
Cl2 C30 1.800(5) .
Br1 C3 1.918(5) .
Br2 C8 1.907(5) .
Br3 C13 1.917(4) .
Br4 C18 1.914(4) .
Br5 C23 1.915(4) .
Br6 C28 1.903(4) .
N1 C41 1.382(6) .
N1 C40 1.383(6) .
N1 C1A 1.450(6) .
N2 C37 1.386(5) .
N2 C36 1.394(5) .
N2 C1B 1.442(5) .
N3 C33 1.384(5) .
N3 C32 1.396(6) .
N3 C1C 1.466(6) .
C1 C2 1.495(7) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C42 1.390(7) .
C2 C3 1.405(6) .
C3 C4 1.354(7) .
C4 C5 1.389(6) .
C4 H4 0.9500 .
C5 C41 1.408(6) .
C5 C6 1.443(6) .
C6 C7 1.391(6) .
C6 C40 1.397(6) .
C7 C8 1.368(6) .
C7 H7 0.9500 .
C8 C9 1.412(6) .
C9 C39 1.385(6) .
C9 C10 1.478(7) .
C10 C11 1.323(6) .
C10 H10 0.9500 .
C11 C12 1.488(6) .
C11 H11 0.9500 .
C12 C13 1.381(6) .
C12 C38 1.405(6) .
C13 C14 1.376(6) .
C14 C15 1.392(6) .
C14 H14 0.9500 .
C15 C37 1.407(6) .
C15 C16 1.460(6) .
C16 C17 1.391(6) .
C16 C36 1.396(6) .
C17 C18 1.360(6) .
C17 H17 0.9500 .
C18 C19 1.411(6) .
C19 C35 1.386(6) .
C19 C20 1.481(6) .
C20 C21 1.332(6) .
C20 H20 0.9500 .
C21 C22 1.468(6) .
C21 H21 0.9500 .
C22 C34 1.385(6) .
C22 C23 1.401(6) .
C23 C24 1.372(6) .
C24 C25 1.383(6) .
C24 H24 0.9500 .
C25 C33 1.407(6) .
C25 C26 1.433(6) .
C26 C32 1.398(6) .
C26 C27 1.406(6) .
C27 C28 1.383(6) .
C27 H27 0.9500 .
C28 C29 1.393(6) .
C29 C31 1.394(6) .
C29 C30 1.498(6) .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C31 C32 1.383(6) .
C31 H31 0.9500 .
C33 C34 1.403(6) .
C34 H34 0.9500 .
C35 C36 1.383(6) .
C35 H35 0.9500 .
C37 C38 1.386(6) .
C38 H38 0.9500 .
C39 C40 1.390(6) .
C39 H39 0.9500 .
C41 C42 1.377(6) .
C42 H42 0.9500 .
C1A C2A 1.505(7) .
C1A H1A1 0.9900 .
C1A H1A2 0.9900 .
C2A C3A 1.525(7) .
C2A H2A1 0.9900 .
C2A H2A2 0.9900 .
C3A C4A 1.479(8) .
C3A H3A1 0.9900 .
C3A H3A2 0.9900 .
C4A H4A1 0.9800 .
C4A H4A2 0.9800 .
C4A H4A3 0.9800 .
C1B C2B 1.511(6) .
C1B H1B1 0.9900 .
C1B H1B2 0.9900 .
C2B C3B 1.519(6) .
C2B H2B1 0.9900 .
C2B H2B2 0.9900 .
C3B C4B 1.497(7) .
C3B H3B1 0.9900 .
C3B H3B2 0.9900 .
C4B H4B1 0.9800 .
C4B H4B2 0.9800 .
C4B H4B3 0.9800 .
C1C C2C 1.501(7) .
C1C H1C1 0.9900 .
C1C H1C2 0.9900 .
C2C C3C 1.431(8) .
C2C H2C1 0.9900 .
C2C H2C2 0.9900 .
C3C C4C 1.549(8) .
C3C H3C1 0.9900 .
C3C H3C2 0.9900 .
C4C H4C1 0.9800 .
C4C H4C2 0.9800 .
C4C H4C3 0.9800 .
C3D C4D 1.43(4) .
C3D H3D1 0.9900 .
C3D H3D2 0.9900 .
C4D H4D1 0.9800 .
C4D H4D2 0.9800 .
C4D H4D3 0.9800 .
C01 C02 1.318(16) .
C01 C04 1.35(2) .
C01 C03 1.393(18) .
C01 H01 0.9170 .
C02 C03 1.397(17) 2_665
C02 H02 0.9500 .
C03 C02 1.397(17) 2_665
C03 H03 0.9500 .
C04 H01 0.5139 .
C04 H04A 0.9800 .
C04 H04B 0.9800 .
C04 H04C 0.9800 .
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
C1 H1B Br4 0.99 3.00 3.674(5) 126.3 2_666
C7 H7 Br6 0.95 3.07 3.862(5) 141.8 2_556
C17 H17 Br5 0.95 3.08 3.678(5) 122.8 2_565
C30 H30B Br1 0.99 3.08 3.859(5) 136.5 .
C31 H31 Br1 0.95 3.10 3.967(5) 151.8 .
C42 H42 Br6 0.95 3.10 3.863(5) 139.0 1_655
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_4
Cl1 C1 C2 C42 91.6(5) .
Cl1 C1 C2 C3 -85.7(5) .
C42 C2 C3 C4 1.7(7) .
C1 C2 C3 C4 179.0(5) .
C42 C2 C3 Br1 -179.5(3) .
C1 C2 C3 Br1 -2.2(6) .
C2 C3 C4 C5 -1.8(7) .
Br1 C3 C4 C5 179.4(3) .
C3 C4 C5 C41 0.9(6) .
C3 C4 C5 C6 -177.6(5) .
C4 C5 C6 C7 -0.8(9) .
C41 C5 C6 C7 -179.4(5) .
C4 C5 C6 C40 178.1(5) .
C41 C5 C6 C40 -0.5(5) .
C40 C6 C7 C8 -0.8(7) .
C5 C6 C7 C8 178.0(5) .
C6 C7 C8 C9 -1.2(7) .
C6 C7 C8 Br2 -176.7(3) .
C7 C8 C9 C39 1.9(7) .
Br2 C8 C9 C39 177.5(3) .
C7 C8 C9 C10 -175.4(4) .
Br2 C8 C9 C10 0.2(6) .
C39 C9 C10 C11 -67.6(6) .
C8 C9 C10 C11 109.7(6) .
C9 C10 C11 C12 -8.8(8) .
C10 C11 C12 C13 123.0(5) .
C10 C11 C12 C38 -58.5(6) .
C38 C12 C13 C14 -0.4(7) .
C11 C12 C13 C14 178.2(4) .
C38 C12 C13 Br3 177.6(3) .
C11 C12 C13 Br3 -3.9(6) .
C12 C13 C14 C15 0.2(7) .
Br3 C13 C14 C15 -177.8(3) .
C13 C14 C15 C37 0.1(6) .
C13 C14 C15 C16 178.8(5) .
C14 C15 C16 C17 2.3(9) .
C37 C15 C16 C17 -178.9(5) .
C14 C15 C16 C36 -179.2(5) .
C37 C15 C16 C36 -0.4(5) .
C36 C16 C17 C18 0.1(6) .
C15 C16 C17 C18 178.4(5) .
C16 C17 C18 C19 0.0(7) .
C16 C17 C18 Br4 -178.5(3) .
C17 C18 C19 C35 -0.7(7) .
Br4 C18 C19 C35 177.8(3) .
C17 C18 C19 C20 -178.1(4) .
Br4 C18 C19 C20 0.4(6) .
C35 C19 C20 C21 27.6(7) .
C18 C19 C20 C21 -155.1(5) .
C19 C20 C21 C22 6.4(8) .
C20 C21 C22 C34 57.5(7) .
C20 C21 C22 C23 -121.4(6) .
C34 C22 C23 C24 -2.0(7) .
C21 C22 C23 C24 176.9(4) .
C34 C22 C23 Br5 -179.7(3) .
C21 C22 C23 Br5 -0.9(6) .
C22 C23 C24 C25 1.0(7) .
Br5 C23 C24 C25 178.8(3) .
C23 C24 C25 C33 1.3(7) .
C23 C24 C25 C26 -179.4(5) .
C24 C25 C26 C32 -179.2(5) .
C33 C25 C26 C32 0.1(5) .
C24 C25 C26 C27 2.0(9) .
C33 C25 C26 C27 -178.7(5) .
C32 C26 C27 C28 0.6(6) .
C25 C26 C27 C28 179.2(5) .
C26 C27 C28 C29 0.3(7) .
C26 C27 C28 Br6 -178.4(3) .
C27 C28 C29 C31 -0.8(7) .
Br6 C28 C29 C31 177.8(3) .
C27 C28 C29 C30 -179.9(4) .
Br6 C28 C29 C30 -1.2(6) .
C28 C29 C30 Cl2 84.3(5) .
C31 C29 C30 Cl2 -94.7(5) .
C28 C29 C31 C32 0.4(7) .
C30 C29 C31 C32 179.5(4) .
C29 C31 C32 N3 179.7(4) .
C29 C31 C32 C26 0.5(7) .
C33 N3 C32 C31 179.5(5) .
C1C N3 C32 C31 0.2(7) .
C33 N3 C32 C26 -1.3(5) .
C1C N3 C32 C26 179.5(4) .
C27 C26 C32 C31 -1.0(7) .
C25 C26 C32 C31 -180.0(4) .
C27 C26 C32 N3 179.7(4) .
C25 C26 C32 N3 0.7(5) .
C32 N3 C33 C34 -177.3(4) .
C1C N3 C33 C34 1.9(8) .
C32 N3 C33 C25 1.3(5) .
C1C N3 C33 C25 -179.4(4) .
C24 C25 C33 N3 178.6(4) .
C26 C25 C33 N3 -0.9(5) .
C24 C25 C33 C34 -2.7(6) .
C26 C25 C33 C34 177.9(4) .
C23 C22 C34 C33 0.7(6) .
C21 C22 C34 C33 -178.2(4) .
N3 C33 C34 C22 -179.9(4) .
C25 C33 C34 C22 1.6(6) .
C18 C19 C35 C36 1.3(6) .
C20 C19 C35 C36 178.6(4) .
C19 C35 C36 N2 -178.0(4) .
C19 C35 C36 C16 -1.3(6) .
C37 N2 C36 C35 178.9(4) .
C1B N2 C36 C35 -6.7(7) .
C37 N2 C36 C16 1.9(5) .
C1B N2 C36 C16 176.3(4) .
C17 C16 C36 C35 0.6(6) .
C15 C16 C36 C35 -178.2(4) .
C17 C16 C36 N2 177.9(4) .
C15 C16 C36 N2 -0.9(5) .
C36 N2 C37 C38 178.8(4) .
C1B N2 C37 C38 4.3(7) .
C36 N2 C37 C15 -2.1(5) .
C1B N2 C37 C15 -176.7(4) .
C14 C15 C37 C38 -0.3(6) .
C16 C15 C37 C38 -179.3(4) .
C14 C15 C37 N2 -179.5(4) .
C16 C15 C37 N2 1.5(5) .
N2 C37 C38 C12 179.1(4) .
C15 C37 C38 C12 0.1(6) .
C13 C12 C38 C37 0.2(6) .
C11 C12 C38 C37 -178.4(4) .
C8 C9 C39 C40 -0.6(6) .
C10 C9 C39 C40 176.9(4) .
C41 N1 C40 C39 176.4(4) .
C1A N1 C40 C39 -7.1(7) .
C41 N1 C40 C6 -2.1(5) .
C1A N1 C40 C6 174.4(4) .
C9 C39 C40 N1 -179.7(4) .
C9 C39 C40 C6 -1.4(7) .
C7 C6 C40 N1 -179.3(4) .
C5 C6 C40 N1 1.6(5) .
C7 C6 C40 C39 2.1(7) .
C5 C6 C40 C39 -177.0(4) .
C40 N1 C41 C42 -177.9(5) .
C1A N1 C41 C42 5.7(8) .
C40 N1 C41 C5 1.7(5) .
C1A N1 C41 C5 -174.7(4) .
C4 C5 C41 C42 0.0(7) .
C6 C5 C41 C42 178.9(4) .
C4 C5 C41 N1 -179.6(4) .
C6 C5 C41 N1 -0.7(5) .
N1 C41 C42 C2 179.5(5) .
C5 C41 C42 C2 0.0(7) .
C3 C2 C42 C41 -0.8(7) .
C1 C2 C42 C41 -178.2(4) .
C41 N1 C1A C2A -101.5(6) .
C40 N1 C1A C2A 82.7(6) .
N1 C1A C2A C3A -178.4(5) .
C1A C2A C3A C4A 171.5(6) .
C37 N2 C1B C2B 75.8(5) .
C36 N2 C1B C2B -97.7(5) .
N2 C1B C2B C3B 178.4(4) .
C1B C2B C3B C4B 173.5(4) .
C33 N3 C1C C2C -96.2(6) .
C32 N3 C1C C2C 83.0(6) .
N3 C1C C2C C3C 73.0(6) .
C1C C2C C3C C4C -176.7(5) .
C04 C01 C02 C03 174.8(13) 2_665
C03 C01 C02 C03 2.0(18) 2_665
C02 C01 C03 C02 -1.9(16) 2_665
C04 C01 C03 C02 -176.6(10) 2_665
