#Supplementary Material (ESI) for Chemical Communications
#This journal is (c) The Royal Society of Chemistry 2011

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dr Roberto Paolesse'
_publ_contact_author_email       roberto.paolesse@uniroma2.it

_publ_section_title              
;
Functionalization of the corrole ring:
the role of isocorrole intermediates
;
loop_
_publ_author_name
L.Tortora
S.Nardis
F.Fronczek
K.Smith
R.Paolesse

# Attachment '- 804886.cif'

data_2-Br-5-OH-17-NO2-ttisocorrH2
_database_code_depnum_ccdc_archive 'CCDC 804886'
#TrackingRef '- 804886.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'0.89(C40 H30 Br1 N5 O3), 0.11(C40 H29 Br2 N5 O3)'
_chemical_formula_sum            'C40 H29.89 Br1.11 N5 O3'
_chemical_formula_weight         717.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1 '
_symmetry_space_group_name_H-M   'P -1 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.086(2)
_cell_length_b                   13.041(3)
_cell_length_c                   13.928(3)
_cell_angle_alpha                72.718(15)
_cell_angle_beta                 70.046(15)
_cell_angle_gamma                86.335(18)
_cell_volume                     1642.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    6460
_cell_measurement_theta_min      4.6
_cell_measurement_theta_max      65.7

_exptl_crystal_description       fragment
_exptl_crystal_colour            'dark blue'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             735
_exptl_absorpt_coefficient_mu    2.251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  0.896
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa Apex-II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27580
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1689
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.5
_diffrn_reflns_theta_max         66.4
_reflns_number_total             27581
_reflns_number_gt                18061
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker Apex2'
_computing_cell_refinement       'Bruker Apex2'
_computing_data_reduction        'Bruker Apex2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The crystal was a
non-merohedral twin, by 180.0 degree rotation about the 1 0 1 reciprocal
lattice direction, twin law
[0.403 -0.259 0.597]
[0.000 -1.000 0.000]
[1.403 -0.259 -0.403].
Refinement vs. HKLF5 data yielded BASF parameter 0.420(2).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0907P)^2^+4.1978P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         27581
_refine_ls_number_parameters     458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.139
_refine_ls_R_factor_gt           0.082
_refine_ls_wR_factor_ref         0.242
_refine_ls_wR_factor_gt          0.209
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.26921(4) 0.28409(4) 0.88746(3) 0.02580(15) Uani 1 1 d . . .
O1 O 0.6046(3) 0.8593(2) 0.7650(2) 0.0251(6) Uani 1 1 d . . .
H10H H 0.5616 0.8541 0.8297 0.038 Uiso 1 1 calc R . .
O2 O 0.3314(3) 0.6124(2) 1.0708(2) 0.0266(6) Uani 1 1 d . . .
O3 O 0.4782(3) 0.7496(2) 0.9810(2) 0.0278(6) Uani 1 1 d . . .
N1 N 0.5815(3) 0.6032(3) 0.7429(3) 0.0217(7) Uani 1 1 d . . .
H1N H 0.6419 0.6130 0.6778 0.026 Uiso 1 1 calc R . .
N2 N 0.7945(3) 0.7154(3) 0.5827(2) 0.0209(7) Uani 1 1 d . . .
N3 N 0.7992(3) 0.5551(3) 0.4675(2) 0.0225(7) Uani 1 1 d . . .
H3N H 0.7516 0.5639 0.5303 0.027 Uiso 1 1 calc R . .
N4 N 0.5816(3) 0.4698(3) 0.6376(2) 0.0222(7) Uani 1 1 d . A .
N5 N 0.4235(3) 0.6641(3) 0.9879(2) 0.0233(8) Uani 1 1 d . . .
C1 C 0.4812(4) 0.5196(3) 0.7950(3) 0.0207(8) Uani 1 1 d . A .
C2 C 0.4083(4) 0.5297(3) 0.8941(3) 0.0194(8) Uani 1 1 d . . .
H2 H 0.3334 0.4836 0.9486 0.023 Uiso 1 1 calc R . .
C3 C 0.4677(4) 0.6233(4) 0.8989(3) 0.0221(9) Uani 1 1 d . . .
C4 C 0.5760(4) 0.6675(3) 0.8030(3) 0.0207(8) Uani 1 1 d . . .
C5 C 0.6794(4) 0.7638(3) 0.7564(3) 0.0212(9) Uani 1 1 d . . .
C6 C 0.7661(4) 0.7872(3) 0.6367(3) 0.0201(8) Uani 1 1 d . . .
C7 C 0.8348(4) 0.8902(3) 0.5735(3) 0.0226(9) Uani 1 1 d . . .
H7 H 0.8283 0.9532 0.5955 0.027 Uiso 1 1 calc R . .
C8 C 0.9106(4) 0.8794(3) 0.4762(3) 0.0227(9) Uani 1 1 d . . .
H8 H 0.9690 0.9334 0.4167 0.027 Uiso 1 1 calc R . .
C9 C 0.8855(4) 0.7699(3) 0.4804(3) 0.0209(8) Uani 1 1 d . . .
C10 C 0.9374(4) 0.7290(3) 0.3938(3) 0.0223(9) Uani 1 1 d . . .
C11 C 0.9005(4) 0.6256(3) 0.3895(3) 0.0252(9) Uani 1 1 d . . .
C12 C 0.9521(5) 0.5824(4) 0.3035(3) 0.0321(10) Uani 1 1 d . . .
H12 H 1.0251 0.6138 0.2378 0.038 Uiso 1 1 calc R . .
C13 C 0.8799(4) 0.4882(4) 0.3301(3) 0.0345(11) Uani 1 1 d . . .
H13 H 0.8929 0.4425 0.2860 0.041 Uiso 1 1 calc R . .
C14 C 0.7804(4) 0.4692(3) 0.4364(3) 0.0235(9) Uani 1 1 d . . .
C15 C 0.6761(4) 0.3827(3) 0.4988(3) 0.0211(8) Uani 1 1 d . . .
C16 C 0.5787(4) 0.3854(3) 0.5956(3) 0.0201(8) Uani 1 1 d . A .
C17 C 0.4710(4) 0.3050(3) 0.6745(3) 0.0244(9) Uani 1 1 d . . .
H17 H 0.4463 0.2391 0.6675 0.029 Uiso 0.892(2) 1 calc PR A 1
Br2 Br 0.4429(4) 0.1757(3) 0.6855(3) 0.0295(16) Uani 0.108(2) 1 d P A 2
C18 C 0.4130(4) 0.3433(3) 0.7602(3) 0.0224(9) Uani 1 1 d . A .
C19 C 0.4874(4) 0.4460(3) 0.7329(3) 0.0201(8) Uani 1 1 d . . .
C20 C 0.7922(4) 0.7474(3) 0.8110(3) 0.0182(8) Uani 1 1 d . . .
C21 C 0.8482(4) 0.6479(3) 0.8394(3) 0.0242(9) Uani 1 1 d . . .
H21 H 0.8127 0.5873 0.8298 0.029 Uiso 1 1 calc R . .
C22 C 0.9565(4) 0.6365(3) 0.8819(3) 0.0173(8) Uani 1 1 d . . .
H22 H 0.9959 0.5682 0.8995 0.021 Uiso 1 1 calc R . .
C23 C 1.0077(4) 0.7226(4) 0.8990(3) 0.0233(9) Uani 1 1 d . . .
C24 C 0.9489(4) 0.8230(3) 0.8720(3) 0.0229(9) Uani 1 1 d . . .
H24 H 0.9831 0.8832 0.8830 0.028 Uiso 1 1 calc R . .
C25 C 0.8410(4) 0.8348(3) 0.8294(3) 0.0198(8) Uani 1 1 d . . .
H25 H 0.8004 0.9027 0.8126 0.024 Uiso 1 1 calc R . .
C26 C 1.1258(4) 0.7091(4) 0.9443(4) 0.0358(11) Uani 1 1 d . . .
H26A H 1.1483 0.6332 0.9633 0.054 Uiso 1 1 calc R . .
H26B H 1.0964 0.7337 1.0082 0.054 Uiso 1 1 calc R . .
H26C H 1.2094 0.7518 0.8908 0.054 Uiso 1 1 calc R . .
C27 C 1.0359(4) 0.7973(3) 0.2923(3) 0.0251(9) Uani 1 1 d . . .
C28 C 1.1774(5) 0.8176(4) 0.2778(3) 0.0356(11) Uani 1 1 d . . .
H28 H 1.2107 0.7907 0.3363 0.043 Uiso 1 1 calc R . .
C29 C 1.2684(5) 0.8757(4) 0.1803(4) 0.0436(12) Uani 1 1 d . . .
H29 H 1.3640 0.8877 0.1724 0.052 Uiso 1 1 calc R . .
C30 C 1.2232(6) 0.9172(4) 0.0930(4) 0.0458(13) Uani 1 1 d . . .
C31 C 1.0840(6) 0.8983(4) 0.1079(4) 0.0444(13) Uani 1 1 d . . .
H31 H 1.0505 0.9269 0.0497 0.053 Uiso 1 1 calc R . .
C32 C 0.9924(5) 0.8394(4) 0.2039(3) 0.0329(10) Uani 1 1 d . . .
H32 H 0.8974 0.8270 0.2106 0.039 Uiso 1 1 calc R . .
C33 C 1.3260(7) 0.9803(4) -0.0148(4) 0.073(2) Uani 1 1 d . . .
H33A H 1.2845 0.9869 -0.0705 0.110 Uiso 1 1 calc R . .
H33B H 1.4143 0.9424 -0.0308 0.110 Uiso 1 1 calc R . .
H33C H 1.3453 1.0520 -0.0125 0.110 Uiso 1 1 calc R . .
C34 C 0.6782(4) 0.2916(3) 0.4554(3) 0.0196(8) Uani 1 1 d . . .
C35 C 0.8023(4) 0.2392(3) 0.4221(3) 0.0217(8) Uani 1 1 d . . .
H35 H 0.8869 0.2619 0.4269 0.026 Uiso 1 1 calc R . .
C36 C 0.8029(4) 0.1544(3) 0.3820(3) 0.0244(9) Uani 1 1 d . . .
H36 H 0.8887 0.1197 0.3592 0.029 Uiso 1 1 calc R . .
C37 C 0.6815(4) 0.1181(3) 0.3739(3) 0.0244(9) Uani 1 1 d . . .
C38 C 0.5577(4) 0.1706(4) 0.4081(3) 0.0287(10) Uani 1 1 d . . .
H38 H 0.4734 0.1473 0.4035 0.034 Uiso 1 1 calc R . .
C39 C 0.5543(4) 0.2562(4) 0.4486(3) 0.0263(9) Uani 1 1 d . . .
H39 H 0.4684 0.2907 0.4717 0.032 Uiso 1 1 calc R . .
C40 C 0.6830(4) 0.0262(4) 0.3291(3) 0.0298(10) Uani 1 1 d . . .
H40A H 0.7694 0.0320 0.2675 0.045 Uiso 1 1 calc R . .
H40B H 0.6006 0.0287 0.3064 0.045 Uiso 1 1 calc R . .
H40C H 0.6798 -0.0420 0.3841 0.045 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0247(2) 0.0274(3) 0.0204(2) -0.00675(17) -0.00063(15) -0.00555(17)
O1 0.0238(14) 0.0261(17) 0.0303(15) -0.0134(13) -0.0116(12) 0.0070(13)
O2 0.0256(15) 0.0339(18) 0.0199(14) -0.0117(13) -0.0048(12) 0.0064(13)
O3 0.0286(15) 0.0295(18) 0.0317(16) -0.0181(13) -0.0108(12) 0.0036(14)
N1 0.0201(16) 0.022(2) 0.0240(17) -0.0080(15) -0.0082(13) 0.0021(15)
N2 0.0225(16) 0.0242(19) 0.0167(16) -0.0078(14) -0.0067(13) 0.0054(14)
N3 0.0237(17) 0.023(2) 0.0185(16) -0.0096(15) -0.0015(14) -0.0017(15)
N4 0.0260(17) 0.0201(19) 0.0233(17) -0.0117(15) -0.0080(14) 0.0062(15)
N5 0.0175(16) 0.031(2) 0.0239(18) -0.0114(16) -0.0085(15) 0.0055(16)
C1 0.0185(19) 0.022(2) 0.023(2) -0.0054(18) -0.0096(16) 0.0007(17)
C2 0.0181(19) 0.019(2) 0.0223(19) -0.0077(17) -0.0077(15) 0.0050(17)
C3 0.0198(19) 0.030(2) 0.021(2) -0.0141(18) -0.0077(16) 0.0088(18)
C4 0.0195(19) 0.025(2) 0.024(2) -0.0156(18) -0.0098(16) 0.0109(17)
C5 0.0195(19) 0.020(2) 0.028(2) -0.0145(18) -0.0084(16) 0.0116(17)
C6 0.0180(19) 0.020(2) 0.027(2) -0.0106(18) -0.0102(16) 0.0000(17)
C7 0.022(2) 0.016(2) 0.034(2) -0.0094(18) -0.0129(17) 0.0004(17)
C8 0.023(2) 0.021(2) 0.024(2) -0.0050(18) -0.0094(16) -0.0040(17)
C9 0.022(2) 0.018(2) 0.0203(19) -0.0011(17) -0.0065(16) -0.0032(17)
C10 0.021(2) 0.021(2) 0.021(2) -0.0035(18) -0.0050(16) -0.0019(17)
C11 0.026(2) 0.022(2) 0.021(2) -0.0041(18) -0.0005(17) -0.0039(18)
C12 0.037(2) 0.030(3) 0.021(2) -0.008(2) 0.0019(18) 0.002(2)
C13 0.035(2) 0.042(3) 0.027(2) -0.026(2) 0.0016(18) 0.007(2)
C14 0.023(2) 0.020(2) 0.029(2) -0.0114(18) -0.0065(17) 0.0037(18)
C15 0.025(2) 0.015(2) 0.0194(19) -0.0012(17) -0.0066(16) 0.0050(17)
C16 0.021(2) 0.015(2) 0.0231(19) -0.0077(17) -0.0043(16) -0.0003(17)
C17 0.023(2) 0.026(2) 0.022(2) -0.0082(18) -0.0040(16) -0.0002(18)
Br2 0.035(3) 0.029(3) 0.022(2) -0.0135(18) 0.0006(16) -0.0098(18)
C18 0.025(2) 0.023(2) 0.022(2) -0.0105(18) -0.0081(16) 0.0035(18)
C19 0.0220(19) 0.018(2) 0.0174(18) -0.0004(16) -0.0057(15) -0.0054(17)
C20 0.0150(18) 0.025(2) 0.0158(18) -0.0099(17) -0.0037(14) 0.0026(17)
C21 0.020(2) 0.028(2) 0.026(2) -0.0126(18) -0.0055(16) 0.0022(18)
C22 0.0155(18) 0.018(2) 0.0160(17) -0.0050(16) -0.0035(14) 0.0060(16)
C23 0.0145(19) 0.034(3) 0.0199(19) -0.0116(19) -0.0009(15) 0.0027(18)
C24 0.023(2) 0.026(2) 0.0183(18) -0.0079(17) -0.0026(16) -0.0033(18)
C25 0.0226(19) 0.016(2) 0.0228(19) -0.0100(17) -0.0075(16) 0.0038(17)
C26 0.027(2) 0.045(3) 0.052(3) -0.030(3) -0.020(2) 0.007(2)
C27 0.033(2) 0.022(2) 0.018(2) -0.0086(18) -0.0040(17) 0.0043(19)
C28 0.031(2) 0.032(3) 0.029(2) 0.004(2) -0.0021(19) 0.006(2)
C29 0.033(3) 0.034(3) 0.041(3) -0.001(2) 0.006(2) 0.000(2)
C30 0.071(4) 0.018(3) 0.025(2) -0.003(2) 0.010(2) 0.003(2)
C31 0.089(4) 0.020(3) 0.026(2) -0.009(2) -0.020(3) 0.003(3)
C32 0.052(3) 0.022(2) 0.029(2) -0.0085(19) -0.017(2) 0.001(2)
C33 0.124(6) 0.021(3) 0.031(3) -0.002(2) 0.023(3) 0.001(3)
C34 0.0194(19) 0.023(2) 0.0167(18) -0.0116(17) -0.0015(15) 0.0028(17)
C35 0.0199(19) 0.020(2) 0.0190(19) 0.0010(17) -0.0040(15) -0.0003(17)
C36 0.027(2) 0.017(2) 0.025(2) -0.0075(18) -0.0048(17) 0.0082(17)
C37 0.035(2) 0.022(2) 0.0189(19) -0.0089(18) -0.0113(17) 0.0073(19)
C38 0.032(2) 0.034(3) 0.027(2) -0.014(2) -0.0155(18) 0.006(2)
C39 0.025(2) 0.031(3) 0.031(2) -0.017(2) -0.0145(18) 0.0096(19)
C40 0.034(2) 0.028(3) 0.032(2) -0.017(2) -0.0114(19) 0.008(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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

Br1 C18 1.849(4) . ?
O1 C5 1.429(5) . ?
O1 H10H 0.8400 . ?
O2 N5 1.239(4) . ?
O3 N5 1.240(5) . ?
N1 C4 1.336(5) . ?
N1 C1 1.381(5) . ?
N1 H1N 0.8800 . ?
N2 C6 1.327(5) . ?
N2 C9 1.402(5) . ?
N3 C11 1.356(5) . ?
N3 C14 1.360(5) . ?
N3 H3N 0.8800 . ?
N4 C19 1.301(5) . ?
N4 C16 1.396(5) . ?
N5 C3 1.415(5) . ?
C1 C2 1.366(5) . ?
C1 C19 1.458(5) . ?
C2 C3 1.423(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(6) . ?
C4 C5 1.518(6) . ?
C5 C6 1.540(5) . ?
C5 C20 1.544(5) . ?
C6 C7 1.436(6) . ?
C7 C8 1.354(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.447(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(5) . ?
C10 C11 1.445(6) . ?
C10 C27 1.478(6) . ?
C11 C12 1.400(6) . ?
C12 C13 1.355(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.435(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.442(6) . ?
C15 C16 1.381(5) . ?
C15 C34 1.480(5) . ?
C16 C17 1.461(6) . ?
C17 C18 1.363(5) . ?
C17 Br2 1.680(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.460(6) . ?
C20 C21 1.383(6) . ?
C20 C25 1.391(5) . ?
C21 C22 1.391(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.402(6) . ?
C23 C26 1.506(5) . ?
C24 C25 1.388(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.395(6) . ?
C27 C28 1.403(6) . ?
C28 C29 1.374(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.391(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.375(8) . ?
C30 C33 1.523(7) . ?
C31 C32 1.367(7) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.391(5) . ?
C34 C39 1.401(6) . ?
C35 C36 1.378(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.391(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.390(6) . ?
C37 C40 1.504(6) . ?
C38 C39 1.387(6) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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 O1 H10H 109.5 . . ?
C4 N1 C1 112.1(3) . . ?
C4 N1 H1N 124.0 . . ?
C1 N1 H1N 124.0 . . ?
C6 N2 C9 105.3(3) . . ?
C11 N3 C14 111.4(3) . . ?
C11 N3 H3N 124.3 . . ?
C14 N3 H3N 124.3 . . ?
C19 N4 C16 107.4(3) . . ?
O2 N5 O3 122.1(3) . . ?
O2 N5 C3 118.6(3) . . ?
O3 N5 C3 119.3(3) . . ?
C2 C1 N1 107.6(3) . . ?
C2 C1 C19 138.9(4) . . ?
N1 C1 C19 113.4(3) . . ?
C1 C2 C3 105.7(3) . . ?
C1 C2 H2 127.1 . . ?
C3 C2 H2 127.1 . . ?
C4 C3 N5 125.7(4) . . ?
C4 C3 C2 109.3(3) . . ?
N5 C3 C2 125.0(4) . . ?
N1 C4 C3 105.3(4) . . ?
N1 C4 C5 118.4(3) . . ?
C3 C4 C5 136.3(3) . . ?
O1 C5 C4 109.9(3) . . ?
O1 C5 C6 104.9(3) . . ?
C4 C5 C6 115.3(3) . . ?
O1 C5 C20 111.5(3) . . ?
C4 C5 C20 111.1(3) . . ?
C6 C5 C20 103.9(3) . . ?
N2 C6 C7 112.6(3) . . ?
N2 C6 C5 125.3(4) . . ?
C7 C6 C5 121.9(3) . . ?
C8 C7 C6 106.1(3) . . ?
C8 C7 H7 126.9 . . ?
C6 C7 H7 126.9 . . ?
C7 C8 C9 106.8(4) . . ?
C7 C8 H8 126.6 . . ?
C9 C8 H8 126.6 . . ?
C10 C9 N2 126.3(4) . . ?
C10 C9 C8 124.4(4) . . ?
N2 C9 C8 109.2(3) . . ?
C9 C10 C11 126.7(4) . . ?
C9 C10 C27 118.9(4) . . ?
C11 C10 C27 114.4(3) . . ?
N3 C11 C12 107.0(4) . . ?
N3 C11 C10 125.2(3) . . ?
C12 C11 C10 127.7(4) . . ?
C13 C12 C11 108.2(4) . . ?
C13 C12 H12 125.9 . . ?
C11 C12 H12 125.9 . . ?
C12 C13 C14 108.4(4) . . ?
C12 C13 H13 125.8 . . ?
C14 C13 H13 125.8 . . ?
N3 C14 C13 105.0(4) . . ?
N3 C14 C15 125.2(3) . . ?
C13 C14 C15 129.7(4) . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 C34 121.7(3) . . ?
C14 C15 C34 117.7(3) . . ?
C15 C16 N4 121.0(3) . . ?
C15 C16 C17 130.1(4) . . ?
N4 C16 C17 108.6(3) . . ?
C18 C17 C16 106.2(4) . . ?
C18 C17 Br2 120.5(3) . . ?
C16 C17 Br2 131.3(3) . . ?
C18 C17 H17 126.9 . . ?
C16 C17 H17 126.9 . . ?
C17 C18 C19 106.1(3) . . ?
C17 C18 Br1 129.6(3) . . ?
C19 C18 Br1 124.3(3) . . ?
N4 C19 C1 116.4(3) . . ?
N4 C19 C18 111.7(3) . . ?
C1 C19 C18 131.7(3) . . ?
C21 C20 C25 119.5(3) . . ?
C21 C20 C5 121.0(3) . . ?
C25 C20 C5 119.4(3) . . ?
C20 C21 C22 120.1(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 121.1(4) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 118.7(3) . . ?
C22 C23 C26 120.4(4) . . ?
C24 C23 C26 120.8(4) . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C20 120.2(4) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 117.0(4) . . ?
C32 C27 C10 120.4(4) . . ?
C28 C27 C10 122.5(4) . . ?
C29 C28 C27 121.0(4) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 121.2(5) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C31 C30 C29 117.6(4) . . ?
C31 C30 C33 121.9(5) . . ?
C29 C30 C33 120.5(5) . . ?
C32 C31 C30 122.0(4) . . ?
C32 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
C31 C32 C27 121.2(4) . . ?
C31 C32 H32 119.4 . . ?
C27 C32 H32 119.4 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C39 119.1(4) . . ?
C35 C34 C15 120.6(3) . . ?
C39 C34 C15 120.3(3) . . ?
C36 C35 C34 120.1(4) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 122.0(4) . . ?
C35 C36 H36 119.0 . . ?
C37 C36 H36 119.0 . . ?
C38 C37 C36 117.5(4) . . ?
C38 C37 C40 120.7(4) . . ?
C36 C37 C40 121.8(4) . . ?
C39 C38 C37 121.7(4) . . ?
C39 C38 H38 119.2 . . ?
C37 C38 H38 119.2 . . ?
C38 C39 C34 119.7(4) . . ?
C38 C39 H39 120.2 . . ?
C34 C39 H39 120.2 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

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
C4 N1 C1 C2 -0.7(4) . . . . ?
C4 N1 C1 C19 -178.2(3) . . . . ?
N1 C1 C2 C3 0.6(4) . . . . ?
C19 C1 C2 C3 177.1(5) . . . . ?
O2 N5 C3 C4 -175.5(3) . . . . ?
O3 N5 C3 C4 4.1(6) . . . . ?
O2 N5 C3 C2 4.2(5) . . . . ?
O3 N5 C3 C2 -176.2(3) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 N5 179.9(3) . . . . ?
C1 N1 C4 C3 0.4(4) . . . . ?
C1 N1 C4 C5 -179.6(3) . . . . ?
N5 C3 C4 N1 179.7(3) . . . . ?
C2 C3 C4 N1 0.0(4) . . . . ?
N5 C3 C4 C5 -0.3(7) . . . . ?
C2 C3 C4 C5 -179.9(4) . . . . ?
N1 C4 C5 O1 127.2(3) . . . . ?
C3 C4 C5 O1 -52.9(6) . . . . ?
N1 C4 C5 C6 9.0(5) . . . . ?
C3 C4 C5 C6 -171.1(4) . . . . ?
N1 C4 C5 C20 -109.0(4) . . . . ?
C3 C4 C5 C20 71.0(5) . . . . ?
C9 N2 C6 C7 0.5(4) . . . . ?
C9 N2 C6 C5 -174.9(3) . . . . ?
O1 C5 C6 N2 -145.2(3) . . . . ?
C4 C5 C6 N2 -24.2(5) . . . . ?
C20 C5 C6 N2 97.7(4) . . . . ?
O1 C5 C6 C7 39.8(4) . . . . ?
C4 C5 C6 C7 160.8(3) . . . . ?
C20 C5 C6 C7 -77.4(4) . . . . ?
N2 C6 C7 C8 -0.9(4) . . . . ?
C5 C6 C7 C8 174.6(3) . . . . ?
C6 C7 C8 C9 0.9(4) . . . . ?
C6 N2 C9 C10 -176.1(4) . . . . ?
C6 N2 C9 C8 0.1(4) . . . . ?
C7 C8 C9 C10 175.6(4) . . . . ?
C7 C8 C9 N2 -0.7(4) . . . . ?
N2 C9 C10 C11 4.7(6) . . . . ?
C8 C9 C10 C11 -171.0(4) . . . . ?
N2 C9 C10 C27 -178.4(3) . . . . ?
C8 C9 C10 C27 6.0(6) . . . . ?
C14 N3 C11 C12 -1.0(5) . . . . ?
C14 N3 C11 C10 174.6(4) . . . . ?
C9 C10 C11 N3 5.9(7) . . . . ?
C27 C10 C11 N3 -171.2(4) . . . . ?
C9 C10 C11 C12 -179.5(4) . . . . ?
C27 C10 C11 C12 3.4(6) . . . . ?
N3 C11 C12 C13 1.0(5) . . . . ?
C10 C11 C12 C13 -174.4(4) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C11 N3 C14 C13 0.6(4) . . . . ?
C11 N3 C14 C15 -176.8(4) . . . . ?
C12 C13 C14 N3 0.1(5) . . . . ?
C12 C13 C14 C15 177.4(4) . . . . ?
N3 C14 C15 C16 4.3(6) . . . . ?
C13 C14 C15 C16 -172.4(4) . . . . ?
N3 C14 C15 C34 -175.5(3) . . . . ?
C13 C14 C15 C34 7.8(6) . . . . ?
C14 C15 C16 N4 -2.4(6) . . . . ?
C34 C15 C16 N4 177.4(3) . . . . ?
C14 C15 C16 C17 -175.6(4) . . . . ?
C34 C15 C16 C17 4.2(6) . . . . ?
C19 N4 C16 C15 -174.1(4) . . . . ?
C19 N4 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C18 174.1(4) . . . . ?
N4 C16 C17 C18 0.2(4) . . . . ?
C15 C16 C17 Br2 10.7(7) . . . . ?
N4 C16 C17 Br2 -163.1(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
Br2 C17 C18 C19 164.8(3) . . . . ?
C16 C17 C18 Br1 179.0(3) . . . . ?
Br2 C17 C18 Br1 -15.5(6) . . . . ?
C16 N4 C19 C1 174.9(3) . . . . ?
C16 N4 C19 C18 -0.9(4) . . . . ?
C2 C1 C19 N4 -178.2(4) . . . . ?
N1 C1 C19 N4 -1.8(5) . . . . ?
C2 C1 C19 C18 -3.4(8) . . . . ?
N1 C1 C19 C18 172.9(4) . . . . ?
C17 C18 C19 N4 1.1(5) . . . . ?
Br1 C18 C19 N4 -178.6(3) . . . . ?
C17 C18 C19 C1 -173.9(4) . . . . ?
Br1 C18 C19 C1 6.4(6) . . . . ?
O1 C5 C20 C21 161.4(3) . . . . ?
C4 C5 C20 C21 38.4(4) . . . . ?
C6 C5 C20 C21 -86.2(4) . . . . ?
O1 C5 C20 C25 -20.4(5) . . . . ?
C4 C5 C20 C25 -143.3(3) . . . . ?
C6 C5 C20 C25 92.0(4) . . . . ?
C25 C20 C21 C22 -2.6(5) . . . . ?
C5 C20 C21 C22 175.7(3) . . . . ?
C20 C21 C22 C23 1.5(5) . . . . ?
C21 C22 C23 C24 -0.4(5) . . . . ?
C21 C22 C23 C26 -179.5(4) . . . . ?
C22 C23 C24 C25 0.2(5) . . . . ?
C26 C23 C24 C25 179.4(4) . . . . ?
C23 C24 C25 C20 -1.3(5) . . . . ?
C21 C20 C25 C24 2.4(5) . . . . ?
C5 C20 C25 C24 -175.8(3) . . . . ?
C9 C10 C27 C32 -109.2(4) . . . . ?
C11 C10 C27 C32 68.1(5) . . . . ?
C9 C10 C27 C28 74.6(5) . . . . ?
C11 C10 C27 C28 -108.1(5) . . . . ?
C32 C27 C28 C29 -0.5(7) . . . . ?
C10 C27 C28 C29 175.7(4) . . . . ?
C27 C28 C29 C30 0.6(7) . . . . ?
C28 C29 C30 C31 0.1(7) . . . . ?
C28 C29 C30 C33 -179.2(5) . . . . ?
C29 C30 C31 C32 -1.0(7) . . . . ?
C33 C30 C31 C32 178.3(4) . . . . ?
C30 C31 C32 C27 1.2(7) . . . . ?
C28 C27 C32 C31 -0.3(6) . . . . ?
C10 C27 C32 C31 -176.7(4) . . . . ?
C16 C15 C34 C35 -128.2(4) . . . . ?
C14 C15 C34 C35 51.6(5) . . . . ?
C16 C15 C34 C39 51.0(5) . . . . ?
C14 C15 C34 C39 -129.2(4) . . . . ?
C39 C34 C35 C36 0.6(6) . . . . ?
C15 C34 C35 C36 179.9(4) . . . . ?
C34 C35 C36 C37 -0.3(6) . . . . ?
C35 C36 C37 C38 -0.1(6) . . . . ?
C35 C36 C37 C40 179.3(4) . . . . ?
C36 C37 C38 C39 0.1(6) . . . . ?
C40 C37 C38 C39 -179.3(4) . . . . ?
C37 C38 C39 C34 0.2(6) . . . . ?
C35 C34 C39 C38 -0.6(6) . . . . ?
C15 C34 C39 C38 -179.8(4) . . . . ?

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
O1 H10H O3 0.84 2.06 2.790(4) 145.2 .
N1 H1N N2 0.88 1.93 2.632(5) 135.5 .
N3 H3N N2 0.88 2.41 2.979(4) 122.7 .
N3 H3N N4 0.88 2.03 2.620(5) 123.7 .

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        66.4
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         1.49
_refine_diff_density_min         -1.47
_refine_diff_density_rms         0.159
# END OF CIF