#------------------------------------------------------------------------------
#$Date: 2021-03-06 08:20:24 +0200 (Sat, 06 Mar 2021) $
#$Revision: 262792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243768.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_2243768
loop_
_publ_author_name
'Harish Chinthal, Chayanna'
'Yathirajan, Hemmige S.'
'Manju, Nagaraja'
'Kalluraya, Balakrishna'
'Foro, Sabine'
'Glidewell, Christopher'
_publ_section_title
;
 Reduced 3,4'-bipyrazoles carrying thiophene and thiazole substituents:
 structures of two intermediates and two products
;
_journal_coeditor_code           DX2035
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              335
_journal_page_last               340
_journal_paper_doi               10.1107/S2056989021002310
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C25 H23 N5 O S2'
_chemical_formula_moiety         'C25 H23 N5 O S2'
_chemical_formula_sum            'C25 H23 N5 O S2'
_chemical_formula_weight         473.60
_chemical_name_systematic
3'-Methyl-5'-(2-methylphenoxy)-1'-phenyl-5-(thiophen-2-yl)-3,4-dihydro-1'H,2H-3,4'-bipyrazole-2-carbothioamide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90.588(7)
_cell_angle_beta                 106.162(8)
_cell_angle_gamma                101.441(7)
_cell_formula_units_Z            2
_cell_length_a                   8.6269(7)
_cell_length_b                   9.8418(9)
_cell_length_c                   14.9000(10)
_cell_measurement_reflns_used    5098
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.941
_cell_measurement_theta_min      2.854
_cell_volume                     1188.05(18)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur
with Sapphire CCD detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0849
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8241
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.550
_diffrn_reflns_theta_min         2.854
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4898
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0380P)²+0.0763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                2524
_reflns_number_total             4898
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dx2035sup1.cif
_cod_data_source_block           Ia
_cod_original_cell_volume        1188.05(17)
_cod_database_code               2243768
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 -0.0795(2) 0.6663(2) 0.30851(14) 0.0406(6) Uani d 1 . .
N N2 -0.2192(2) 0.6179(2) 0.23518(15) 0.0451(6) Uani d 1 . .
C C3 -0.1670(3) 0.6245(3) 0.15926(18) 0.0421(7) Uani d 1 . .
C C4 0.0047(3) 0.6737(3) 0.18050(17) 0.0384(7) Uani d 1 . .
C C5 0.0541(3) 0.6994(3) 0.27513(17) 0.0384(7) Uani d 1 . .
C C11 -0.0885(3) 0.6605(3) 0.40219(18) 0.0445(7) Uani d 1 . .
C C12 0.0024(3) 0.7654(4) 0.4690(2) 0.0625(9) Uani d 1 . .
H H12 0.0687 0.8426 0.4532 0.075 Uiso calc 1 . .
C C13 -0.0067(4) 0.7541(5) 0.5603(2) 0.0816(12) Uani d 1 . .
H H13 0.0563 0.8232 0.6063 0.098 Uiso calc 1 . .
C C14 -0.1073(5) 0.6421(5) 0.5835(2) 0.0838(12) Uani d 1 . .
H H14 -0.1123 0.6354 0.6448 0.101 Uiso calc 1 . .
C C15 -0.2004(4) 0.5399(4) 0.5157(3) 0.0757(11) Uani d 1 . .
H H15 -0.2704 0.4648 0.5310 0.091 Uiso calc 1 . .
C C16 -0.1904(3) 0.5484(3) 0.4250(2) 0.0565(8) Uani d 1 . .
H H16 -0.2524 0.4784 0.3793 0.068 Uiso calc 1 . .
C C31 -0.2869(3) 0.5831(3) 0.06491(18) 0.0615(9) Uani d 1 . .
H H31A -0.2770 0.6581 0.0249 0.092 Uiso calc 1 . .
H H31B -0.3970 0.5616 0.0707 0.092 Uiso calc 1 . .
H H31C -0.2637 0.5027 0.0384 0.092 Uiso calc 1 . .
N N41 0.4015(2) 0.7247(3) 0.16104(14) 0.0415(6) Uani d 1 . .
N N42 0.2565(2) 0.6253(2) 0.14876(14) 0.0393(6) Uani d 1 . .
C C43 0.1056(3) 0.6826(3) 0.11269(17) 0.0412(7) Uani d 1 . .
H H43 0.0379 0.6306 0.0538 0.049 Uiso calc 1 . .
C C44 0.1805(3) 0.8295(3) 0.09133(18) 0.0496(8) Uani d 1 . .
H H44A 0.1515 0.8403 0.0244 0.060 Uiso calc 1 . .
H H44B 0.1441 0.8997 0.1218 0.060 Uiso calc 1 . .
C C45 0.3626(3) 0.8383(3) 0.13106(18) 0.0418(7) Uani d 1 . .
S S421 0.09307(9) 0.36681(8) 0.14413(5) 0.0559(3) Uani d 1 . .
C C422 0.2638(3) 0.4938(3) 0.16724(17) 0.0408(7) Uani d 1 . .
N N423 0.4148(3) 0.4679(3) 0.20351(18) 0.0538(7) Uani d 1 . .
H H42A 0.506(3) 0.539(3) 0.2180(18) 0.065 Uiso d 1 . .
H H42B 0.426(3) 0.380(3) 0.2139(19) 0.065 Uiso d 1 . .
S S451 0.69257(13) 0.96287(15) 0.18083(12) 0.0769(5) Uani d 0.866(3) A 1
C C452 0.4879(3) 0.9623(3) 0.13580(19) 0.0515(8) Uani d 0.866(3) A 1
C C453 0.4652(18) 1.0876(10) 0.1098(14) 0.0769(15) Uani d 0.866(3) A 1
H H453 0.3615 1.1067 0.0830 0.092 Uiso calc 0.866(3) A 1
C C454 0.6146(9) 1.1897(8) 0.1270(14) 0.104(2) Uani d 0.866(3) A 1
H H454 0.6204 1.2821 0.1127 0.125 Uiso calc 0.866(3) A 1
C C455 0.7456(8) 1.1343(6) 0.1666(8) 0.099(2) Uani d 0.866(3) A 1
H H455 0.8539 1.1848 0.1844 0.119 Uiso calc 0.866(3) A 1
S S551 0.456(3) 1.1213(19) 0.104(3) 0.0769(15) Uani d 0.134(3) A 2
C C552 0.4879(3) 0.9623(3) 0.13580(19) 0.0515(8) Uani d 0.134(3) A 2
C C553 0.6476(19) 0.960(4) 0.159(4) 0.0769(5) Uani d 0.134(3) A 2
H H553 0.6877 0.8792 0.1740 0.092 Uiso calc 0.134(3) A 2
C C554 0.751(3) 1.092(4) 0.158(6) 0.099(2) Uani d 0.134(3) A 2
H H554 0.8660 1.1083 0.1735 0.119 Uiso calc 0.134(3) A 2
C C555 0.661(4) 1.189(4) 0.133(10) 0.104(2) Uani d 0.134(3) A 2
H H555 0.7062 1.2828 0.1317 0.125 Uiso calc 0.134(3) A 2
O O51 0.20838(18) 0.73742(19) 0.33641(11) 0.0434(5) Uani d 1 . .
C C51 0.2920(3) 0.8764(3) 0.34104(17) 0.0432(7) Uani d 1 . .
C C52 0.4615(3) 0.8993(4) 0.37778(18) 0.0535(8) Uani d 1 . .
C C53 0.5473(5) 1.0365(5) 0.3857(2) 0.0833(13) Uani d 1 . .
H H53 0.6615 1.0564 0.4102 0.100 Uiso calc 1 . .
C C54 0.4682(7) 1.1423(5) 0.3583(3) 0.1011(15) Uani d 1 . .
H H54 0.5291 1.2330 0.3649 0.121 Uiso calc 1 . .
C C55 0.3006(6) 1.1174(4) 0.3213(3) 0.0882(12) Uani d 1 . .
H H55 0.2478 1.1901 0.3018 0.106 Uiso calc 1 . .
C C56 0.2104(4) 0.9822(4) 0.3131(2) 0.0626(9) Uani d 1 . .
H H56 0.0961 0.9634 0.2889 0.075 Uiso calc 1 . .
C C57 0.5475(4) 0.7841(4) 0.4051(2) 0.0804(11) Uani d 1 . .
H H57A 0.6602 0.8211 0.4398 0.121 Uiso calc 1 . .
H H57B 0.5441 0.7310 0.3500 0.121 Uiso calc 1 . .
H H57C 0.4940 0.7253 0.4435 0.121 Uiso calc 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
C5 N1 N2 . . 109.56(19) ?
C5 N1 C11 . . 130.2(2) ?
N2 N1 C11 . . 119.8(2) ?
C3 N2 N1 . . 105.00(18) ?
N2 C3 C4 . . 112.4(2) ?
N2 C3 C31 . . 120.2(2) ?
C4 C3 C31 . . 127.4(2) ?
C5 C4 C3 . . 103.8(2) ?
C5 C4 C43 . . 129.7(2) ?
C3 C4 C43 . . 126.3(2) ?
C4 C5 N1 . . 109.2(2) ?
C4 C5 O51 . . 130.8(2) ?
N1 C5 O51 . . 119.7(2) ?
C12 C11 C16 . . 120.5(3) ?
C12 C11 N1 . . 120.6(3) ?
C16 C11 N1 . . 118.8(3) ?
C11 C12 C13 . . 118.8(3) ?
C11 C12 H12 . . 120.6 ?
C13 C12 H12 . . 120.6 ?
C14 C13 C12 . . 120.8(3) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C15 C14 C13 . . 119.8(3) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C14 C15 C16 . . 120.1(3) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C11 C16 C15 . . 119.9(3) ?
C11 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C3 C31 H31A . . 109.5 ?
C3 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C3 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C45 N41 N42 . . 108.1(2) ?
C422 N42 N41 . . 119.9(2) ?
C422 N42 C43 . . 127.2(2) ?
N41 N42 C43 . . 112.9(2) ?
N42 C43 C4 . . 112.3(2) ?
N42 C43 C44 . . 101.01(19) ?
C4 C43 C44 . . 116.4(2) ?
N42 C43 H43 . . 108.9 ?
C4 C43 H43 . . 108.9 ?
C44 C43 H43 . . 108.9 ?
C45 C44 C43 . . 102.9(2) ?
C45 C44 H44A . . 111.2 ?
C43 C44 H44A . . 111.2 ?
C45 C44 H44B . . 111.2 ?
C43 C44 H44B . . 111.2 ?
H44A C44 H44B . . 109.1 ?
N41 C45 C452 . . 121.1(3) ?
N41 C45 C44 . . 114.4(2) ?
C452 C45 C44 . . 124.5(3) ?
N42 C422 N423 . . 116.4(2) ?
N42 C422 S421 . . 121.8(2) ?
N423 C422 S421 . . 121.7(2) ?
C422 N423 H42A . . 120.3(18) ?
C422 N423 H42B . . 119.2(18) ?
H42A N423 H42B . . 121(3) ?
C455 S451 C452 . . 91.8(3) ?
C453 C452 C45 . . 127.5(7) ?
C453 C452 S451 . . 111.0(6) ?
C45 C452 S451 . . 121.5(3) ?
C452 C453 C454 . . 113.8(8) ?
C452 C453 H453 . . 123.1 ?
C454 C453 H453 . . 123.1 ?
C455 C454 C453 . . 110.7(6) ?
C455 C454 H454 . . 124.7 ?
C453 C454 H454 . . 124.7 ?
C454 C455 S451 . . 112.7(5) ?
C454 C455 H455 . . 123.6 ?
S451 C455 H455 . . 123.6 ?
C554 C553 H553 . . 123.2 ?
C555 C554 C553 . . 110.8(13) ?
C555 C554 H554 . . 124.6 ?
C553 C554 H554 . . 124.6 ?
C554 C555 S551 . . 112.2(12) ?
C554 C555 H555 . . 123.9 ?
S551 C555 H555 . . 123.9 ?
C5 O51 C51 . . 117.9(2) ?
C56 C51 C52 . . 122.6(3) ?
C56 C51 O51 . . 122.3(2) ?
C52 C51 O51 . . 115.1(3) ?
C51 C52 C53 . . 116.4(3) ?
C51 C52 C57 . . 121.8(3) ?
C53 C52 C57 . . 121.7(3) ?
C54 C53 C52 . . 121.7(4) ?
C54 C53 H53 . . 119.2 ?
C52 C53 H53 . . 119.2 ?
C53 C54 C55 . . 121.0(4) ?
C53 C54 H54 . . 119.5 ?
C55 C54 H54 . . 119.5 ?
C54 C55 C56 . . 119.2(4) ?
C54 C55 H55 . . 120.4 ?
C56 C55 H55 . . 120.4 ?
C51 C56 C55 . . 119.2(3) ?
C51 C56 H56 . . 120.4 ?
C55 C56 H56 . . 120.4 ?
C52 C57 H57A . . 109.5 ?
C52 C57 H57B . . 109.5 ?
H57A C57 H57B . . 109.5 ?
C52 C57 H57C . . 109.5 ?
H57A C57 H57C . . 109.5 ?
H57B C57 H57C . . 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
N1 C5 . 1.362(3) ?
N1 N2 . 1.379(2) ?
N1 C11 . 1.421(3) ?
N2 C3 . 1.326(3) ?
C3 C4 . 1.407(3) ?
C3 C31 . 1.491(3) ?
C4 C5 . 1.360(3) ?
C4 C43 . 1.499(3) ?
C5 O51 . 1.366(3) ?
C11 C12 . 1.376(4) ?
C11 C16 . 1.376(4) ?
C12 C13 . 1.389(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.372(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.372(5) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.382(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C31 H31A . 0.9600 ?
C31 H31B . 0.9600 ?
C31 H31C . 0.9600 ?
N41 C45 . 1.280(3) ?
N41 N42 . 1.392(3) ?
N42 C422 . 1.336(3) ?
N42 C43 . 1.487(3) ?
C43 C44 . 1.537(3) ?
C43 H43 . 0.9800 ?
C44 C45 . 1.501(3) ?
C44 H44A . 0.9700 ?
C44 H44B . 0.9700 ?
C45 C452 . 1.447(4) ?
S421 C422 . 1.682(3) ?
C422 N423 . 1.341(3) ?
N423 H42A . 0.91(3) ?
N423 H42B . 0.90(3) ?
S451 C455 . 1.690(6) ?
S451 C452 . 1.704(3) ?
C452 C453 . 1.331(8) ?
C453 C454 . 1.426(13) ?
C453 H453 . 0.9300 ?
C454 C455 . 1.343(7) ?
C454 H454 . 0.9300 ?
C455 H455 . 0.9300 ?
S551 C555 . 1.690(12) ?
C553 C554 . 1.428(16) ?
C553 H553 . 0.9300 ?
C554 C555 . 1.344(12) ?
C554 H554 . 0.9300 ?
C555 H555 . 0.9300 ?
O51 C51 . 1.406(3) ?
C51 C56 . 1.374(4) ?
C51 C52 . 1.382(4) ?
C52 C53 . 1.392(5) ?
C52 C57 . 1.475(4) ?
C53 C54 . 1.361(5) ?
C53 H53 . 0.9300 ?
C54 C55 . 1.366(5) ?
C54 H54 . 0.9300 ?
C55 C56 . 1.387(4) ?
C55 H55 . 0.9300 ?
C56 H56 . 0.9300 ?
C57 H57A . 0.9600 ?
C57 H57B . 0.9600 ?
C57 H57C . 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
N423 H42A N2 1_655 0.92(3) 2.28(3) 3.111(3) 150(2) no
N423 H42A N41 . 0.92(3) 2.27(3) 2.628(4) 103(2) no
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
C5 N1 N2 C3 . . . . -0.7(3) ?
C11 N1 N2 C3 . . . . -173.9(2) ?
N1 N2 C3 C4 . . . . 1.1(3) ?
N1 N2 C3 C31 . . . . -178.5(2) ?
N2 C3 C4 C5 . . . . -1.1(3) ?
C31 C3 C4 C5 . . . . 178.5(3) ?
N2 C3 C4 C43 . . . . 174.5(3) ?
C31 C3 C4 C43 . . . . -5.8(5) ?
C3 C4 C5 N1 . . . . 0.6(3) ?
C43 C4 C5 N1 . . . . -174.8(3) ?
C3 C4 C5 O51 . . . . 173.7(3) ?
C43 C4 C5 O51 . . . . -1.7(5) ?
N2 N1 C5 C4 . . . . 0.0(3) ?
C11 N1 C5 C4 . . . . 172.3(3) ?
N2 N1 C5 O51 . . . . -174.0(2) ?
C11 N1 C5 O51 . . . . -1.7(4) ?
C5 N1 C11 C12 . . . . 45.3(4) ?
N2 N1 C11 C12 . . . . -143.1(3) ?
C5 N1 C11 C16 . . . . -135.0(3) ?
N2 N1 C11 C16 . . . . 36.6(4) ?
C16 C11 C12 C13 . . . . 2.0(5) ?
N1 C11 C12 C13 . . . . -178.3(3) ?
C11 C12 C13 C14 . . . . -1.6(5) ?
C12 C13 C14 C15 . . . . -0.1(6) ?
C13 C14 C15 C16 . . . . 1.3(5) ?
C12 C11 C16 C15 . . . . -0.8(4) ?
N1 C11 C16 C15 . . . . 179.5(3) ?
C14 C15 C16 C11 . . . . -0.9(5) ?
C45 N41 N42 C422 . . . . 174.3(2) ?
C45 N41 N42 C43 . . . . -4.4(3) ?
C422 N42 C43 C4 . . . . 64.4(3) ?
N41 N42 C43 C4 . . . . -117.0(2) ?
C422 N42 C43 C44 . . . . -170.8(2) ?
N41 N42 C43 C44 . . . . 7.7(3) ?
C5 C4 C43 N42 . . . . 41.7(4) ?
C3 C4 C43 N42 . . . . -132.8(3) ?
C5 C4 C43 C44 . . . . -74.0(4) ?
C3 C4 C43 C44 . . . . 111.5(3) ?
N42 C43 C44 C45 . . . . -7.5(2) ?
C4 C43 C44 C45 . . . . 114.3(2) ?
N42 N41 C45 C452 . . . . 179.1(2) ?
N42 N41 C45 C44 . . . . -1.3(3) ?
C43 C44 C45 N41 . . . . 6.1(3) ?
C43 C44 C45 C452 . . . . -174.4(2) ?
N41 N42 C422 N423 . . . . 4.6(3) ?
C43 N42 C422 N423 . . . . -177.0(2) ?
N41 N42 C422 S421 . . . . -174.18(16) ?
C43 N42 C422 S421 . . . . 4.2(3) ?
N41 C45 C452 C453 . . . . -178.0(11) ?
C44 C45 C452 C453 . . . . 2.5(12) ?
N41 C45 C452 S451 . . . . 0.3(4) ?
C44 C45 C452 S451 . . . . -179.2(2) ?
C455 S451 C452 C453 . . . . 1.4(10) ?
C455 S451 C452 C45 . . . . -177.2(4) ?
C45 C452 C453 C454 . . . . 177.6(11) ?
S451 C452 C453 C454 . . . . -0.9(18) ?
C452 C453 C454 C455 . . . . 0(2) ?
C453 C454 C455 S451 . . . . 1.4(18) ?
C452 S451 C455 C454 . . . . -1.6(11) ?
C553 C554 C555 S551 . . . . -4(13) ?
C4 C5 O51 C51 . . . . 76.6(4) ?
N1 C5 O51 C51 . . . . -110.9(3) ?
C5 O51 C51 C56 . . . . 22.5(3) ?
C5 O51 C51 C52 . . . . -158.9(2) ?
C56 C51 C52 C53 . . . . 0.2(4) ?
O51 C51 C52 C53 . . . . -178.3(2) ?
C56 C51 C52 C57 . . . . -178.4(3) ?
O51 C51 C52 C57 . . . . 3.1(4) ?
C51 C52 C53 C54 . . . . -0.2(5) ?
C57 C52 C53 C54 . . . . 178.4(3) ?
C52 C53 C54 C55 . . . . -0.5(6) ?
C53 C54 C55 C56 . . . . 1.1(6) ?
C52 C51 C56 C55 . . . . 0.4(4) ?
O51 C51 C56 C55 . . . . 178.8(2) ?
C54 C55 C56 C51 . . . . -1.0(5) ?

_cod_database_fobs_code 2243768
