#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/93/2229367.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229367
loop_
_publ_author_name
'Bortoluzzi, Adailton J.'
'Policarpi, Everton B.'
'Mora, Cristiano'
'Oliveira, Kely N.'
'Nunes, Ricardo J.'
_publ_section_title
;
 4-[(1,3-Dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)methyl]-N'-[(E)-4-nitrobenzylidene]benzenesulfonohydrazide
 dimethyl sulfoxide monosolvate
;
_journal_coeditor_code           FF2001
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o627
_journal_page_last               o628
_journal_paper_doi               10.1107/S1600536811004697
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C26 H18 N4 O6 S, C2 H6 O S'
_chemical_formula_moiety         'C26 H18 N4 O6 S, C2 H6 O S'
_chemical_formula_sum            'C28 H24 N4 O7 S2'
_chemical_formula_weight         592.63
_chemical_name_systematic
;
4-[(1,3-Dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)methyl]-
N'-[(E)-4-nitrobenzylidene]benzenesulfonohydrazide
dimethyl sulfoxide monosolvate
;
_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                107.268(7)
_cell_angle_beta                 101.789(7)
_cell_angle_gamma                96.319(8)
_cell_formula_units_Z            2
_cell_length_a                   9.1520(10)
_cell_length_b                   11.9710(10)
_cell_length_c                   13.9100(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.41
_cell_measurement_theta_min      8.53
_cell_volume                     1400.6(2)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1996)'
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5055
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.425
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0792P)²+0.6130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1626
_reflns_number_gt                3075
_reflns_number_total             4737
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ff2001.cif
_cod_data_source_block           I
_cod_database_code               2229367
_cod_database_fobs_code          2229367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.34031(11) 0.73620(8) 0.53120(6) 0.0597(3) Uani d . 1 . .
N N1 0.8354(3) 1.1992(2) 0.8805(2) 0.0571(7) Uani d . 1 . .
N N2 0.4477(3) 0.6426(2) 0.55446(19) 0.0540(7) Uani d . 1 . .
H H2N 0.5170 0.6398 0.5273 0.058(12) Uiso d R 1 . .
N N3 0.4776(3) 0.6399(2) 0.65605(19) 0.0501(6) Uani d . 1 . .
O O1 0.6771(4) 1.2526(3) 0.9840(2) 0.1026(11) Uani d . 1 . .
O O2 0.9903(3) 1.1379(3) 0.7756(2) 0.0987(10) Uani d . 1 . .
O O3 0.3260(3) 0.7192(2) 0.42331(18) 0.0797(8) Uani d . 1 . .
O O4 0.2088(3) 0.7188(2) 0.5685(2) 0.0766(8) Uani d . 1 . .
C C2 0.7994(4) 1.2237(3) 0.9760(3) 0.0626(9) Uani d . 1 . .
C C3 0.9105(4) 1.2127(3) 1.0630(2) 0.0547(8) Uani d . 1 . .
C C4 0.8859(5) 1.2441(4) 1.1612(3) 0.0767(11) Uani d . 1 . .
H H4 0.7994 1.2747 1.1724 0.092 Uiso calc R 1 . .
C C5 0.9881(6) 1.2309(4) 1.2432(3) 0.0864(13) Uani d . 1 . .
H H5 0.9706 1.2547 1.3092 0.104 Uiso calc R 1 . .
C C6 1.1117(6) 1.1846(4) 1.2296(3) 0.0803(13) Uani d . 1 . .
H H6 1.1779 1.1753 1.2858 0.096 Uiso calc R 1 . .
C C7 1.1429(4) 1.1495(3) 1.1304(3) 0.0645(10) Uani d . 1 . .
C C8 1.2697(5) 1.1010(4) 1.1103(5) 0.0918(15) Uani d . 1 . .
H H8 1.3383 1.0895 1.1643 0.110 Uiso calc R 1 . .
C C9 1.2953(5) 1.0705(4) 1.0149(6) 0.1053(19) Uani d . 1 . .
H H9 1.3799 1.0370 1.0038 0.126 Uiso calc R 1 . .
C C10 1.1970(5) 1.0884(4) 0.9325(4) 0.0845(13) Uani d . 1 . .
H H10 1.2170 1.0683 0.8672 0.101 Uiso calc R 1 . .
C C11 1.0701(4) 1.1359(3) 0.9479(3) 0.0547(8) Uani d . 1 . .
C C12 1.0410(4) 1.1663(3) 1.0464(3) 0.0492(8) Uani d . 1 . .
C C13 0.9662(4) 1.1572(3) 0.8612(3) 0.0636(10) Uani d . 1 . .
C C14 0.7269(5) 1.2149(3) 0.7930(3) 0.0737(11) Uani d . 1 . .
H H14A 0.7827 1.2462 0.7515 0.088 Uiso calc R 1 . .
H H14B 0.6660 1.2723 0.8202 0.088 Uiso calc R 1 . .
C C15 0.6233(4) 1.0984(3) 0.7248(3) 0.0602(9) Uani d . 1 . .
C C16 0.6623(5) 1.0275(3) 0.6388(3) 0.0680(10) Uani d . 1 . .
H H16 0.7496 1.0539 0.6214 0.082 Uiso calc R 1 . .
C C17 0.5738(4) 0.9184(3) 0.5784(3) 0.0636(9) Uani d . 1 . .
H H17 0.6009 0.8715 0.5208 0.076 Uiso calc R 1 . .
C C18 0.4443(4) 0.8797(3) 0.6049(2) 0.0535(8) Uani d . 1 . .
C C19 0.4011(4) 0.9501(4) 0.6880(3) 0.0714(10) Uani d . 1 . .
H H19 0.3127 0.9246 0.7045 0.086 Uiso calc R 1 . .
C C20 0.4909(5) 1.0596(4) 0.7469(3) 0.0765(11) Uani d . 1 . .
H H20 0.4611 1.1079 0.8027 0.092 Uiso calc R 1 . .
C C21 0.5844(4) 0.5873(3) 0.6806(2) 0.0500(8) Uani d . 1 . .
H H21 0.6372 0.5541 0.6320 0.060 Uiso calc R 1 . .
C C22 0.6255(4) 0.5781(3) 0.7849(2) 0.0475(7) Uani d . 1 . .
C C23 0.7517(4) 0.5304(3) 0.8140(3) 0.0580(9) Uani d . 1 . .
H H23 0.8057 0.4994 0.7655 0.070 Uiso calc R 1 . .
C C24 0.7984(4) 0.5285(3) 0.9143(3) 0.0613(9) Uani d . 1 . .
H H24 0.8839 0.4973 0.9341 0.074 Uiso calc R 1 . .
C C25 0.7162(4) 0.5734(3) 0.9838(2) 0.0550(8) Uani d . 1 . .
C C26 0.5894(4) 0.6196(3) 0.9578(3) 0.0638(9) Uani d . 1 . .
H H26 0.5356 0.6495 1.0067 0.077 Uiso calc R 1 . .
C C27 0.5431(4) 0.6209(3) 0.8576(3) 0.0615(9) Uani d . 1 . .
H H27 0.4561 0.6507 0.8382 0.074 Uiso calc R 1 . .
N N4 0.7691(4) 0.5767(3) 1.0923(3) 0.0733(9) Uani d . 1 . .
O O5 0.6974(4) 0.6209(4) 1.1535(2) 0.1111(12) Uani d . 1 . .
O O6 0.8819(4) 0.5387(4) 1.1166(2) 0.1188(13) Uani d . 1 . .
S S2 0.74498(12) 0.64956(10) 0.39415(8) 0.0747(3) Uani d . 1 . .
O O1S 0.7208(3) 0.6673(3) 0.5003(2) 0.0830(8) Uani d . 1 . .
C C1S 0.8748(5) 0.5522(4) 0.3777(3) 0.0833(12) Uani d . 1 . .
H H1S1 0.8257 0.4734 0.3689 0.125 Uiso calc R 1 . .
H H1S2 0.9591 0.5784 0.4379 0.125 Uiso calc R 1 . .
H H1S3 0.9105 0.5515 0.3173 0.125 Uiso calc R 1 . .
C C2S 0.8693(6) 0.7814(4) 0.4070(4) 0.1081(17) Uani d . 1 . .
H H2S1 0.8157 0.8468 0.4170 0.162 Uiso calc R 1 . .
H H2S2 0.9049 0.7705 0.3451 0.162 Uiso calc R 1 . .
H H2S3 0.9542 0.7979 0.4657 0.162 Uiso calc R 1 . .
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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 S1 O3 . . 120.25(16) ?
O4 S1 N2 . . 108.61(16) ?
O3 S1 N2 . . 103.64(16) ?
O4 S1 C18 . . 107.94(17) ?
O3 S1 C18 . . 109.03(15) ?
N2 S1 C18 . . 106.58(15) ?
C2 N1 C13 . . 123.8(3) ?
C2 N1 C14 . . 118.4(3) ?
C13 N1 C14 . . 117.7(3) ?
N3 N2 S1 . . 115.3(2) ?
N3 N2 H2N . . 117.1 ?
S1 N2 H2N . . 114.1 ?
C21 N3 N2 . . 115.5(3) ?
O1 C2 N1 . . 119.3(3) ?
O1 C2 C3 . . 122.8(3) ?
N1 C2 C3 . . 117.9(3) ?
C4 C3 C12 . . 119.4(3) ?
C4 C3 C2 . . 120.4(3) ?
C12 C3 C2 . . 120.1(3) ?
C3 C4 C5 . . 120.8(4) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C6 C5 C4 . . 121.3(4) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C7 . . 120.7(4) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C8 C7 C6 . . 124.0(4) ?
C8 C7 C12 . . 117.6(4) ?
C6 C7 C12 . . 118.3(4) ?
C9 C8 C7 . . 121.7(5) ?
C9 C8 H8 . . 119.1 ?
C7 C8 H8 . . 119.1 ?
C8 C9 C10 . . 120.9(4) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
C11 C10 C9 . . 119.9(5) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C10 C11 C12 . . 119.8(4) ?
C10 C11 C13 . . 120.2(4) ?
C12 C11 C13 . . 119.9(3) ?
C11 C12 C3 . . 120.5(3) ?
C11 C12 C7 . . 120.1(3) ?
C3 C12 C7 . . 119.4(3) ?
O2 C13 N1 . . 120.1(4) ?
O2 C13 C11 . . 122.6(4) ?
N1 C13 C11 . . 117.3(3) ?
N1 C14 C15 . . 111.5(3) ?
N1 C14 H14A . . 109.3 ?
C15 C14 H14A . . 109.3 ?
N1 C14 H14B . . 109.3 ?
C15 C14 H14B . . 109.3 ?
H14A C14 H14B . . 108.0 ?
C20 C15 C16 . . 118.5(3) ?
C20 C15 C14 . . 121.5(4) ?
C16 C15 C14 . . 120.0(4) ?
C17 C16 C15 . . 121.1(4) ?
C17 C16 H16 . . 119.5 ?
C15 C16 H16 . . 119.5 ?
C16 C17 C18 . . 119.1(4) ?
C16 C17 H17 . . 120.4 ?
C18 C17 H17 . . 120.4 ?
C19 C18 C17 . . 120.7(3) ?
C19 C18 S1 . . 121.3(3) ?
C17 C18 S1 . . 118.0(3) ?
C18 C19 C20 . . 119.2(4) ?
C18 C19 H19 . . 120.4 ?
C20 C19 H19 . . 120.4 ?
C15 C20 C19 . . 121.4(4) ?
C15 C20 H20 . . 119.3 ?
C19 C20 H20 . . 119.3 ?
N3 C21 C22 . . 120.5(3) ?
N3 C21 H21 . . 119.7 ?
C22 C21 H21 . . 119.7 ?
C23 C22 C27 . . 118.9(3) ?
C23 C22 C21 . . 119.9(3) ?
C27 C22 C21 . . 121.1(3) ?
C24 C23 C22 . . 120.7(3) ?
C24 C23 H23 . . 119.6 ?
C22 C23 H23 . . 119.6 ?
C25 C24 C23 . . 118.5(3) ?
C25 C24 H24 . . 120.7 ?
C23 C24 H24 . . 120.7 ?
C24 C25 C26 . . 122.6(3) ?
C24 C25 N4 . . 118.9(3) ?
C26 C25 N4 . . 118.5(3) ?
C25 C26 C27 . . 118.6(3) ?
C25 C26 H26 . . 120.7 ?
C27 C26 H26 . . 120.7 ?
C26 C27 C22 . . 120.6(3) ?
C26 C27 H27 . . 119.7 ?
C22 C27 H27 . . 119.7 ?
O6 N4 O5 . . 123.1(4) ?
O6 N4 C25 . . 119.1(4) ?
O5 N4 C25 . . 117.7(4) ?
O1S S2 C1S . . 106.61(19) ?
O1S S2 C2S . . 104.8(2) ?
C1S S2 C2S . . 97.5(2) ?
S2 C1S H1S1 . . 109.5 ?
S2 C1S H1S2 . . 109.5 ?
H1S1 C1S H1S2 . . 109.5 ?
S2 C1S H1S3 . . 109.5 ?
H1S1 C1S H1S3 . . 109.5 ?
H1S2 C1S H1S3 . . 109.5 ?
S2 C2S H2S1 . . 109.5 ?
S2 C2S H2S2 . . 109.5 ?
H2S1 C2S H2S2 . . 109.5 ?
S2 C2S H2S3 . . 109.5 ?
H2S1 C2S H2S3 . . 109.5 ?
H2S2 C2S H2S3 . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O4 . 1.423(3) ?
S1 O3 . 1.429(2) ?
S1 N2 . 1.630(3) ?
S1 C18 . 1.762(3) ?
N1 C2 . 1.388(4) ?
N1 C13 . 1.394(5) ?
N1 C14 . 1.478(4) ?
N2 N3 . 1.394(3) ?
N2 H2N . 0.8006 ?
N3 C21 . 1.263(4) ?
O1 C2 . 1.224(4) ?
O2 C13 . 1.214(4) ?
C2 C3 . 1.461(5) ?
C3 C4 . 1.377(5) ?
C3 C12 . 1.404(5) ?
C4 C5 . 1.380(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.336(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.415(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.395(6) ?
C7 C12 . 1.418(5) ?
C8 C9 . 1.344(7) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.391(7) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.375(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.399(5) ?
C11 C13 . 1.481(5) ?
C14 C15 . 1.517(5) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C20 . 1.375(5) ?
C15 C16 . 1.384(5) ?
C16 C17 . 1.381(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.383(5) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.373(5) ?
C19 C20 . 1.383(5) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 C22 . 1.462(4) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.383(4) ?
C22 C27 . 1.394(4) ?
C23 C24 . 1.381(5) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.367(5) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.369(5) ?
C25 N4 . 1.474(4) ?
C26 C27 . 1.377(5) ?
C26 H26 . 0.9300 ?
C27 H27 . 0.9300 ?
N4 O6 . 1.200(4) ?
N4 O5 . 1.213(4) ?
S2 O1S . 1.494(3) ?
S2 C1S . 1.755(4) ?
S2 C2S . 1.781(5) ?
C1S H1S1 . 0.9600 ?
C1S H1S2 . 0.9600 ?
C1S H1S3 . 0.9600 ?
C2S H2S1 . 0.9600 ?
C2S H2S2 . 0.9600 ?
C2S H2S3 . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2N O1S . 0.80 1.99 2.764(4) 163 y
C8 H8 Cg 2_777 0.93 2.903 3.799(6) 162 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O4 S1 N2 N3 . . . . -49.9(3) ?
O3 S1 N2 N3 . . . . -178.9(2) ?
C18 S1 N2 N3 . . . . 66.1(3) ?
S1 N2 N3 C21 . . . . -165.8(2) ?
C13 N1 C2 O1 . . . . -175.1(3) ?
C14 N1 C2 O1 . . . . 2.9(5) ?
C13 N1 C2 C3 . . . . 4.6(5) ?
C14 N1 C2 C3 . . . . -177.4(3) ?
O1 C2 C3 C4 . . . . -5.1(6) ?
N1 C2 C3 C4 . . . . 175.2(3) ?
O1 C2 C3 C12 . . . . 172.8(4) ?
N1 C2 C3 C12 . . . . -6.8(5) ?
C12 C3 C4 C5 . . . . 0.2(6) ?
C2 C3 C4 C5 . . . . 178.1(4) ?
C3 C4 C5 C6 . . . . -1.7(7) ?
C4 C5 C6 C7 . . . . 1.1(7) ?
C5 C6 C7 C8 . . . . 179.7(4) ?
C5 C6 C7 C12 . . . . 0.8(5) ?
C6 C7 C8 C9 . . . . -179.1(4) ?
C12 C7 C8 C9 . . . . -0.2(6) ?
C7 C8 C9 C10 . . . . 1.2(7) ?
C8 C9 C10 C11 . . . . -1.2(7) ?
C9 C10 C11 C12 . . . . 0.2(5) ?
C9 C10 C11 C13 . . . . 179.0(4) ?
C10 C11 C12 C3 . . . . -178.8(3) ?
C13 C11 C12 C3 . . . . 2.5(4) ?
C10 C11 C12 C7 . . . . 0.7(5) ?
C13 C11 C12 C7 . . . . -178.0(3) ?
C4 C3 C12 C11 . . . . -178.7(3) ?
C2 C3 C12 C11 . . . . 3.3(5) ?
C4 C3 C12 C7 . . . . 1.8(5) ?
C2 C3 C12 C7 . . . . -176.2(3) ?
C8 C7 C12 C11 . . . . -0.7(5) ?
C6 C7 C12 C11 . . . . 178.2(3) ?
C8 C7 C12 C3 . . . . 178.8(3) ?
C6 C7 C12 C3 . . . . -2.3(5) ?
C2 N1 C13 O2 . . . . -179.9(3) ?
C14 N1 C13 O2 . . . . 2.1(5) ?
C2 N1 C13 C11 . . . . 1.1(5) ?
C14 N1 C13 C11 . . . . -176.9(3) ?
C10 C11 C13 O2 . . . . -2.5(5) ?
C12 C11 C13 O2 . . . . 176.2(3) ?
C10 C11 C13 N1 . . . . 176.5(3) ?
C12 C11 C13 N1 . . . . -4.8(4) ?
C2 N1 C14 C15 . . . . -96.1(4) ?
C13 N1 C14 C15 . . . . 82.0(4) ?
N1 C14 C15 C20 . . . . 86.5(5) ?
N1 C14 C15 C16 . . . . -92.5(4) ?
C20 C15 C16 C17 . . . . -2.3(5) ?
C14 C15 C16 C17 . . . . 176.8(3) ?
C15 C16 C17 C18 . . . . -0.1(5) ?
C16 C17 C18 C19 . . . . 2.1(5) ?
C16 C17 C18 S1 . . . . -176.1(3) ?
O4 S1 C18 C19 . . . . 5.1(3) ?
O3 S1 C18 C19 . . . . 137.3(3) ?
N2 S1 C18 C19 . . . . -111.5(3) ?
O4 S1 C18 C17 . . . . -176.8(3) ?
O3 S1 C18 C17 . . . . -44.6(3) ?
N2 S1 C18 C17 . . . . 66.7(3) ?
C17 C18 C19 C20 . . . . -1.6(5) ?
S1 C18 C19 C20 . . . . 176.6(3) ?
C16 C15 C20 C19 . . . . 2.8(6) ?
C14 C15 C20 C19 . . . . -176.2(3) ?
C18 C19 C20 C15 . . . . -0.9(6) ?
N2 N3 C21 C22 . . . . -179.6(2) ?
N3 C21 C22 C23 . . . . -173.8(3) ?
N3 C21 C22 C27 . . . . 3.6(5) ?
C27 C22 C23 C24 . . . . -2.0(5) ?
C21 C22 C23 C24 . . . . 175.5(3) ?
C22 C23 C24 C25 . . . . 0.7(5) ?
C23 C24 C25 C26 . . . . 0.3(5) ?
C23 C24 C25 N4 . . . . -177.2(3) ?
C24 C25 C26 C27 . . . . -0.1(5) ?
N4 C25 C26 C27 . . . . 177.5(3) ?
C25 C26 C27 C22 . . . . -1.2(5) ?
C23 C22 C27 C26 . . . . 2.2(5) ?
C21 C22 C27 C26 . . . . -175.3(3) ?
C24 C25 N4 O6 . . . . -0.8(5) ?
C26 C25 N4 O6 . . . . -178.5(4) ?
C24 C25 N4 O5 . . . . 177.4(4) ?
C26 C25 N4 O5 . . . . -0.3(5) ?
