#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/94/2229431.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_2229431
loop_
_publ_author_name
'Gayathri, P.'
'Thiruvalluvar, A.'
'Rajeswari, K.'
'Pandiarajan, K.'
'Butcher, R. J.'
_publ_section_title
;
 1-Benzyl-3,5-bis[(E)-3-thienylmethylidene]piperidin-4-one
;
_journal_coeditor_code           JJ2073
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o571
_journal_paper_doi               10.1107/S1600536811003758
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H19 N O S2'
_chemical_formula_moiety         'C22 H19 N O S2'
_chemical_formula_structural     'C22 H19 N O S2'
_chemical_formula_sum            'C22 H19 N O S2'
_chemical_formula_weight         377.52
_chemical_melting_point          429
_chemical_name_common            piperidin-4-one
_chemical_name_systematic
;
1-Benzyl-3,5-bis[(E)-3-thienylmethylidene]piperidin-4-one
;
_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
_cell_angle_alpha                112.657(6)
_cell_angle_beta                 95.845(5)
_cell_angle_gamma                98.512(5)
_cell_formula_units_Z            2
_cell_length_a                   6.1809(3)
_cell_length_b                   12.7391(9)
_cell_length_c                   12.9251(7)
_cell_measurement_reflns_used    3996
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.0032
_cell_measurement_theta_min      6.3810
_cell_volume                     914.65(11)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6091
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.17
_diffrn_reflns_theta_min         6.39
_exptl_absorpt_coefficient_mu    2.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0635P)²+0.4312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                3114
_reflns_number_total             3615
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jj2073.cif
_cod_data_source_block           I
_cod_database_code               2229431
_cod_database_fobs_code          2229431
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1A 0.18315(9) 1.03620(4) 0.61944(5) 0.0240(2) Uani d PD 0.7990(10) A 1
S S2A 0.73267(10) 0.08626(5) 0.16709(6) 0.0279(2) Uani d PD 0.7990(10) A 1
O O1 0.8340(2) 0.63874(10) 0.50798(10) 0.0306(3) Uani d . 1.000 . .
N N1 0.3176(2) 0.57437(11) 0.26094(11) 0.0217(4) Uani d . 1.000 . .
C C1 0.3584(3) 0.46955(14) 0.27383(14) 0.0246(4) Uani d . 1.000 . .
C C2 0.5717(3) 0.49305(13) 0.35403(13) 0.0214(4) Uani d . 1.000 A .
C C3 0.6540(3) 0.61272(14) 0.44395(13) 0.0220(4) Uani d . 1.000 . .
C C4 0.5080(3) 0.69853(13) 0.45572(13) 0.0201(4) Uani d . 1.000 A .
C C5 0.2948(3) 0.66158(13) 0.37148(13) 0.0212(4) Uani d . 1.000 . .
C C6 0.5750(3) 0.80356(12) 0.54314(13) 0.0210(4) Uani d D 1.000 . .
C C7A 0.4685(3) 0.90348(14) 0.5796(3) 0.0183(5) Uani d PD 0.7990(10) A 1
C C8A 0.2461(4) 0.90208(14) 0.5516(3) 0.0207(6) Uani d PD 0.7990(10) A 1
C C9A 0.4535(3) 1.0966(3) 0.6871(4) 0.0329(4) Uani d PD 0.7990(10) A 1
C C10A 0.5831(4) 1.0177(2) 0.6602(3) 0.0234(6) Uani d PD 0.7990(10) A 1
C C11 0.6925(3) 0.41222(11) 0.34934(12) 0.0223(4) Uani d D 1.000 . .
C C12A 0.6495(7) 0.28977(15) 0.2719(3) 0.0228(5) Uani d PD 0.7990(10) A 1
C C13A 0.8188(6) 0.22914(15) 0.2613(3) 0.0238(7) Uani d PD 0.7990(10) A 1
C C14A 0.4666(3) 0.1060(3) 0.1415(4) 0.0310(5) Uani d PD 0.7990(10) A 1
C C15A 0.4455(6) 0.2152(2) 0.2014(4) 0.0263(6) Uani d PD 0.7990(10) A 1
C C16 0.1124(3) 0.54282(14) 0.17762(14) 0.0250(4) Uani d . 1.000 . .
C C17 0.0842(3) 0.63387(14) 0.13266(13) 0.0231(4) Uani d . 1.000 . .
C C18 0.2395(3) 0.66337(15) 0.07197(14) 0.0276(5) Uani d . 1.000 . .
C C19 0.2113(3) 0.74264(16) 0.02500(15) 0.0310(5) Uani d . 1.000 . .
C C20 0.0256(3) 0.79278(16) 0.03671(15) 0.0320(5) Uani d . 1.000 . .
C C21 -0.1304(3) 0.76399(16) 0.09586(15) 0.0325(5) Uani d . 1.000 . .
C C22 -0.1007(3) 0.68515(15) 0.14398(14) 0.0278(5) Uani d . 1.000 . .
C C8B 0.5804(14) 1.0004(7) 0.6512(15) 0.0207(6) Uani d PD 0.2010(10) A 2
C C9B 0.1915(10) 1.0076(7) 0.6059(10) 0.0240(2) Uani d PD 0.2010(10) A 2
S S1B 0.4253(4) 1.1062(3) 0.6913(4) 0.0329(4) Uani d PD 0.2010(10) A 2
S S2B 0.4472(4) 0.0861(3) 0.1254(4) 0.0310(5) Uani d PD 0.2010(10) A 2
C C13B 0.438(2) 0.2290(5) 0.2021(17) 0.0238(7) Uani d PD 0.2010(10) A 2
C C14B 0.7253(7) 0.1115(10) 0.1784(12) 0.0279(2) Uani d PD 0.2010(10) A 2
C C7B 0.4467(8) 0.8937(4) 0.5864(15) 0.0183(5) Uani d PD 0.2010(10) A 2
C C12B 0.640(3) 0.2900(3) 0.2707(10) 0.0228(5) Uani d PD 0.2010(10) A 2
C C10B 0.221(2) 0.9007(8) 0.5623(14) 0.0234(6) Uani d PD 0.2010(10) A 2
C C15B 0.800(3) 0.2159(10) 0.2558(16) 0.0263(6) Uani d PD 0.2010(10) A 2
H H1B 0.36535 0.40961 0.19840 0.0296 Uiso calc R 1.000 . .
H H5A 0.25596 0.73017 0.36152 0.0255 Uiso calc R 1.000 . .
H H5B 0.17305 0.62863 0.40123 0.0255 Uiso calc R 1.000 . .
H H1A 0.23312 0.43872 0.30305 0.0296 Uiso calc R 1.000 . .
H H16A 0.11277 0.46894 0.11292 0.0300 Uiso calc R 1.000 . .
H H16B -0.01661 0.52956 0.21384 0.0300 Uiso calc R 1.000 . .
H H18 0.36607 0.62866 0.06278 0.0331 Uiso calc R 1.000 . .
H H19 0.31915 0.76265 -0.01525 0.0372 Uiso calc R 1.000 . .
H H20 0.00581 0.84676 0.00415 0.0383 Uiso calc R 1.000 . .
H H21 -0.25789 0.79798 0.10372 0.0390 Uiso calc R 1.000 . .
H H22 -0.20800 0.66618 0.18501 0.0333 Uiso calc R 1.000 . .
H H6 0.713(3) 0.8169(16) 0.5895(17) 0.026(5) Uiso d . 1.000 . .
H H8A 0.14054 0.83497 0.50085 0.0249 Uiso calc PR 0.7990(10) A 1
H H9A 0.50486 1.17598 0.73726 0.0395 Uiso calc PR 0.7990(10) A 1
H H10A 0.73660 1.03548 0.69141 0.0281 Uiso calc PR 0.7990(10) A 1
H H11 0.823(3) 0.4373(16) 0.4015(17) 0.026(5) Uiso d . 1.000 . .
H H13A 0.96646 0.26254 0.30162 0.0286 Uiso calc PR 0.7990(10) A 1
H H14A 0.34781 0.04620 0.09052 0.0372 Uiso calc PR 0.7990(10) A 1
H H15A 0.30930 0.24073 0.19759 0.0316 Uiso calc PR 0.7990(10) A 1
H H8B 0.73734 1.01388 0.67126 0.0249 Uiso calc PR 0.2010(10) A 2
H H9B 0.05409 1.02885 0.59182 0.0288 Uiso calc PR 0.2010(10) A 2
H H10B 0.10440 0.83526 0.51955 0.0281 Uiso calc PR 0.2010(10) A 2
H H13B 0.31035 0.26169 0.19782 0.0286 Uiso calc PR 0.2010(10) A 2
H H14B 0.81485 0.05504 0.15365 0.0335 Uiso calc PR 0.2010(10) A 2
H H15B 0.94614 0.24115 0.29862 0.0316 Uiso calc PR 0.2010(10) A 2
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'
S S 0.3331 0.5567 ' 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8A S1A C9A . . . 92.00(17) no
C8B S1B C9B . . . 90.4(6) no
C13A S2A C14A . . . 91.2(2) no
C13B S2B C14B . . . 91.2(7) no
C1 N1 C5 . . . 109.61(13) no
C5 N1 C16 . . . 110.43(13) no
C1 N1 C16 . . . 108.34(14) no
N1 C1 C2 . . . 111.86(15) no
C1 C2 C3 . . . 118.18(16) no
C1 C2 C11 . . . 123.85(15) no
C3 C2 C11 . . . 117.97(15) no
O1 C3 C2 . . . 121.03(17) no
C2 C3 C4 . . . 117.50(15) no
O1 C3 C4 . . . 121.44(16) no
C5 C4 C6 . . . 124.57(17) no
C3 C4 C6 . . . 117.12(16) no
C3 C4 C5 . . . 118.29(14) no
N1 C5 C4 . . . 110.75(14) no
C4 C6 C7A . . . 130.47(19) no
C4 C6 C7B . . . 127.9(5) no
C6 C7A C8A . . . 126.3(2) no
C8A C7A C10A . . . 110.5(2) no
C6 C7A C10A . . . 123.0(2) no
C6 C7B C10B . . . 134.6(12) no
C6 C7B C8B . . . 112.0(6) no
C8B C7B C10B . . . 112.4(9) no
S1A C8A C7A . . . 111.9(2) no
S1B C8B C7B . . . 110.7(7) no
S1A C9A C10A . . . 111.6(3) no
S1B C9B C10B . . . 113.6(8) no
C7A C10A C9A . . . 114.0(3) no
C7B C10B C9B . . . 112.2(11) no
C2 C11 C12A . . . 129.3(2) no
C2 C11 C12B . . . 127.0(7) no
C11 C12A C13A . . . 119.8(3) no
C11 C12A C15A . . . 129.5(3) no
C13A C12A C15A . . . 110.7(3) no
C13B C12B C15B . . . 110.8(11) no
C11 C12B C13B . . . 126.5(13) no
C11 C12B C15B . . . 122.8(14) no
S2A C13A C12A . . . 112.4(3) no
S2B C13B C12B . . . 111.1(9) no
S2A C14A C15A . . . 112.4(3) no
S2B C14B C15B . . . 112.9(10) no
C12A C15A C14A . . . 113.3(3) no
C12B C15B C14B . . . 113.7(14) no
N1 C16 C17 . . . 113.51(15) no
C18 C17 C22 . . . 118.42(17) no
C16 C17 C18 . . . 119.81(17) no
C16 C17 C22 . . . 121.66(16) no
C17 C18 C19 . . . 120.85(17) no
C18 C19 C20 . . . 120.05(18) no
C19 C20 C21 . . . 119.84(19) no
C20 C21 C22 . . . 120.03(18) no
C17 C22 C21 . . . 120.80(17) no
N1 C1 H1A . . . 109.00 no
N1 C1 H1B . . . 109.00 no
C2 C1 H1A . . . 109.00 no
C2 C1 H1B . . . 109.00 no
H1A C1 H1B . . . 108.00 no
N1 C5 H5A . . . 109.00 no
N1 C5 H5B . . . 109.00 no
C4 C5 H5A . . . 109.00 no
C4 C5 H5B . . . 109.00 no
H5A C5 H5B . . . 108.00 no
C4 C6 H6 . . . 116.8(13) no
C7A C6 H6 . . . 112.8(13) no
C7B C6 H6 . . . 114.6(14) no
S1A C8A H8A . . . 124.00 no
C7A C8A H8A . . . 124.00 no
C7B C8B H8B . . . 125.00 no
S1B C8B H8B . . . 125.00 no
C10A C9A H9A . . . 124.00 no
S1A C9A H9A . . . 124.00 no
C10B C9B H9B . . . 123.00 no
S1B C9B H9B . . . 123.00 no
C9A C10A H10A . . . 123.00 no
C7A C10A H10A . . . 123.00 no
C9B C10B H10B . . . 124.00 no
C7B C10B H10B . . . 124.00 no
C12A C11 H11 . . . 114.6(13) no
C2 C11 H11 . . . 116.2(13) no
C12B C11 H11 . . . 116.8(15) no
C12A C13A H13A . . . 124.00 no
S2A C13A H13A . . . 124.00 no
S2B C13B H13B . . . 124.00 no
C12B C13B H13B . . . 125.00 no
S2A C14A H14A . . . 124.00 no
C15A C14A H14A . . . 124.00 no
S2B C14B H14B . . . 124.00 no
C15B C14B H14B . . . 124.00 no
C12A C15A H15A . . . 123.00 no
C14A C15A H15A . . . 123.00 no
C12B C15B H15B . . . 123.00 no
C14B C15B H15B . . . 123.00 no
H16A C16 H16B . . . 108.00 no
N1 C16 H16B . . . 109.00 no
C17 C16 H16A . . . 109.00 no
N1 C16 H16A . . . 109.00 no
C17 C16 H16B . . . 109.00 no
C17 C18 H18 . . . 120.00 no
C19 C18 H18 . . . 120.00 no
C18 C19 H19 . . . 120.00 no
C20 C19 H19 . . . 120.00 no
C19 C20 H20 . . . 120.00 no
C21 C20 H20 . . . 120.00 no
C20 C21 H21 . . . 120.00 no
C22 C21 H21 . . . 120.00 no
C21 C22 H22 . . . 120.00 no
C17 C22 H22 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1A C8A . . 1.718(3) no
S1A C9A . . 1.718(3) no
S1B C9B . . 1.719(10) no
S1B C8B . . 1.718(12) no
S2A C13A . . 1.718(3) no
S2A C14A . . 1.718(2) no
S2B C13B . . 1.718(15) no
S2B C14B . . 1.719(8) no
O1 C3 . . 1.235(2) no
N1 C5 . . 1.470(2) no
N1 C16 . . 1.472(2) no
N1 C1 . . 1.462(2) no
C1 C2 . . 1.506(3) no
C2 C3 . . 1.490(2) no
C2 C11 . . 1.345(2) no
C3 C4 . . 1.491(3) no
C4 C6 . . 1.347(2) no
C4 C5 . . 1.508(2) no
C6 C7A . . 1.458(3) no
C6 C7B . . 1.458(9) no
C7A C8A . . 1.381(3) no
C7A C10A . . 1.443(4) no
C7B C8B . . 1.372(18) no
C7B C10B . . 1.422(14) no
C9A C10A . . 1.341(4) no
C9B C10B . . 1.307(17) no
C11 C12A . . 1.458(3) no
C11 C12B . . 1.458(9) no
C12A C15A . . 1.438(6) no
C12A C13A . . 1.377(5) no
C12B C13B . . 1.38(2) no
C12B C15B . . 1.44(2) no
C14A C15A . . 1.340(6) no
C14B C15B . . 1.30(2) no
C16 C17 . . 1.507(3) no
C17 C18 . . 1.397(3) no
C17 C22 . . 1.391(3) no
C18 C19 . . 1.386(3) no
C19 C20 . . 1.388(3) no
C20 C21 . . 1.382(3) no
C21 C22 . . 1.394(3) no
C1 H1A . . 0.9900 no
C1 H1B . . 0.9900 no
C5 H5A . . 0.9900 no
C5 H5B . . 0.9900 no
C6 H6 . . 0.943(19) no
C8A H8A . . 0.9500 no
C8B H8B . . 0.9500 no
C9A H9A . . 0.9500 no
C9B H9B . . 0.9500 no
C10A H10A . . 0.9500 no
C10B H10B . . 0.9500 no
C11 H11 . . 0.92(2) no
C13A H13A . . 0.9500 no
C13B H13B . . 0.9500 no
C14A H14A . . 0.9500 no
C14B H14B . . 0.9500 no
C15A H15A . . 0.9500 no
C15B H15B . . 0.9500 no
C16 H16A . . 0.9900 no
C16 H16B . . 0.9900 no
C18 H18 . . 0.9500 no
C19 H19 . . 0.9500 no
C20 H20 . . 0.9500 no
C21 H21 . . 0.9500 no
C22 H22 . . 0.9500 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1A C8A 3.648(3) . 2_576 no
S1A S1A 3.3576(9) . 2_576 no
S1A S2A 3.6853(9) . 2_666 no
S1A C21 3.6606(19) . 2_576 no
S1B C21 3.469(4) . 2_576 no
S1B C6 3.631(5) . 2_676 no
S1B C18 3.502(5) . 2_676 no
S1B C5 3.609(5) . 2_676 no
S1B C4 3.670(5) . 2_676 no
S2A C9A 3.651(4) . 2_666 no
S2A S1A 3.6853(9) . 2_666 no
S2A C10A 3.598(3) . 2_666 no
S2A C8A 3.569(3) . 2_666 no
S2A C7A 3.582(3) . 2_666 no
S2B C14B 3.692(15) . 2_655 no
S2B C8B 3.475(16) . 2_666 no
S2B S2B 3.335(6) . 2_655 no
S2B C7B 3.618(17) . 2_666 no
S1A H10A 3.0000 . 1_455 no
S1B H21 2.8300 . 2_576 no
S1B H5A 2.9700 . 2_676 no
S2A H20 3.1600 . 2_665 no
S2A H14A 3.0400 . 2_655 no
S2B H19 3.0900 . 2_665 no
O1 C15B 3.296(19) . 2_766 no
O1 C13A 3.177(4) . 2_766 no
O1 H10B 2.7400 . 1_655 no
O1 H11 2.79(2) . 2_766 no
O1 H13A 2.3900 . 2_766 no
O1 H6 2.38(2) . . no
O1 H11 2.39(2) . . no
O1 H5B 2.6200 . 1_655 no
O1 H15B 2.4900 . 2_766 no
N1 H18 2.9300 . . no
C1 C15A 3.154(4) . . no
C1 C13B 2.974(12) . . no
C4 C11 3.568(2) . 2_666 no
C4 S1B 3.670(5) . 2_676 no
C5 C10B 3.228(15) . . no
C5 S1B 3.609(5) . 2_676 no
C5 C8A 3.133(3) . . no
C6 C15A 3.415(5) . 2_666 no
C6 C12B 3.372(12) . 2_666 no
C6 S1B 3.631(5) . 2_676 no
C6 C13B 3.481(18) . 2_666 no
C6 C12A 3.381(4) . 2_666 no
C7A C13A 3.573(4) . 2_666 no
C7A C9A 3.529(6) . 2_676 no
C7A S2A 3.582(3) . 2_666 no
C7B S2B 3.618(17) . 2_666 no
C7B C15B 3.26(2) . 2_666 no
C7B C14B 3.34(2) . 2_666 no
C7B C12B 3.512(14) . 2_666 no
C8A S2A 3.569(3) . 2_666 no
C8A C5 3.133(3) . . no
C8A C13A 3.452(4) . 2_666 no
C8A C10A 3.475(4) . 2_676 no
C8A S1A 3.648(3) . 2_576 no
C8B S2B 3.475(16) . 2_666 no
C8B C14B 3.595(18) . 2_666 no
C9A C18 3.520(5) . 2_676 no
C9A S2A 3.651(4) . 2_666 no
C9A C7A 3.529(6) . 2_676 no
C9B C9B 3.357(14) . 2_576 no
C10A C14A 3.504(6) . 2_666 no
C10A C8A 3.475(4) . 2_676 no
C10A S2A 3.598(3) . 2_666 no
C10B C15B 3.23(2) . 2_666 no
C10B C14B 3.40(2) . 2_666 no
C10B C5 3.228(15) . . no
C11 C4 3.568(2) . 2_666 no
C12A C6 3.381(4) . 2_666 no
C12B C6 3.372(12) . 2_666 no
C12B C7B 3.512(14) . 2_666 no
C13A C8A 3.452(4) . 2_666 no
C13A O1 3.177(4) . 2_766 no
C13A C7A 3.573(4) . 2_666 no
C13B C6 3.481(18) . 2_666 no
C13B C1 2.974(12) . . no
C14A C10A 3.504(6) . 2_666 no
C14B C7B 3.34(2) . 2_666 no
C14B C10B 3.40(2) . 2_666 no
C14B C8B 3.595(18) . 2_666 no
C14B S2B 3.692(15) . 2_655 no
C15A C6 3.415(5) . 2_666 no
C15A C1 3.154(4) . . no
C15B C10B 3.23(2) . 2_666 no
C15B O1 3.296(19) . 2_766 no
C15B C7B 3.26(2) . 2_666 no
C16 C18 3.520(2) . 2_565 no
C18 C16 3.520(2) . 2_565 no
C18 S1B 3.502(5) . 2_676 no
C18 C9A 3.520(5) . 2_676 no
C21 S1B 3.469(4) . 2_576 no
C21 S1A 3.6606(19) . 2_576 no
C1 H13B 2.4000 . . no
C1 H15A 2.6500 . . no
C2 H13B 2.9500 . . no
C4 H8A 3.0300 . . no
C5 H10B 2.8100 . . no
C5 H8A 2.5900 . . no
C7A H5A 2.8500 . . no
C7B H5A 2.8400 . . no
C8A H5A 2.6000 . . no
C9A H5A 2.9400 . 2_676 no
C9A H21 2.9900 . 2_576 no
C9B H9B 2.6700 . 2_576 no
C9B H8B 3.0200 . 1_455 no
C10B H9B 2.9700 . 2_576 no
C10B H5A 2.7200 . . no
C12A H1B 2.8100 . . no
C12B H1B 2.7600 . . no
C13B H19 3.0000 . 2_665 no
C13B H1B 2.4300 . . no
C13B H1A 3.0200 . . no
C14A H19 3.0200 . 2_665 no
C15A H1B 2.6100 . . no
C15A H19 3.0200 . 2_665 no
C17 H5A 2.7500 . . no
C17 H16A 2.9700 . 2_565 no
C17 H9A 3.0500 . 2_676 no
C18 H16A 2.8400 . 2_565 no
C18 H9A 2.6700 . 2_676 no
C19 H16A 2.9000 . 2_565 no
C19 H9A 3.0800 . 2_676 no
C20 H16A 3.0700 . 2_565 no
H1A H13A 2.5700 . 1_455 no
H1A H16B 2.5000 . . no
H1A C13B 3.0200 . . no
H1A H5B 2.3700 . . no
H1A H15A 2.5000 . . no
H1A H13B 2.2900 . . no
H1B C15A 2.6100 . . no
H1B H15A 2.1200 . . no
H1B C13B 2.4300 . . no
H1B H13B 1.8600 . . no
H1B C12A 2.8100 . . no
H1B C12B 2.7600 . . no
H1B H16A 2.2100 . . no
H5A C10B 2.7200 . . no
H5A C7B 2.8400 . . no
H5A C7A 2.8500 . . no
H5A C8A 2.6000 . . no
H5A C17 2.7500 . . no
H5A H8A 2.0600 . . no
H5A C9A 2.9400 . 2_676 no
H5A S1B 2.9700 . 2_676 no
H5A H10B 2.3400 . . no
H5A H9A 2.5100 . 2_676 no
H5B H1A 2.3700 . . no
H5B H8A 2.4900 . . no
H5B O1 2.6200 . 1_455 no
H5B H16B 2.3400 . . no
H6 O1 2.38(2) . . no
H6 H10A 2.5500 . . no
H6 H8B 2.2900 . . no
H8A H5B 2.4900 . . no
H8A H5A 2.0600 . . no
H8A C4 3.0300 . . no
H8A C5 2.5900 . . no
H8B C9B 3.0200 . 1_655 no
H8B H6 2.2900 . . no
H8B H9B 2.3200 . 1_655 no
H9A C17 3.0500 . 2_676 no
H9A H5A 2.5100 . 2_676 no
H9A C19 3.0800 . 2_676 no
H9A C18 2.6700 . 2_676 no
H9B H9B 2.1900 . 2_576 no
H9B H8B 2.3200 . 1_455 no
H9B C10B 2.9700 . 2_576 no
H9B C9B 2.6700 . 2_576 no
H10A H6 2.5500 . . no
H10A S1A 3.0000 . 1_655 no
H10B H5A 2.3400 . . no
H10B C5 2.8100 . . no
H10B O1 2.7400 . 1_455 no
H11 O1 2.79(2) . 2_766 no
H11 O1 2.39(2) . . no
H11 H13A 2.4500 . . no
H13A O1 2.3900 . 2_766 no
H13A H1A 2.5700 . 1_655 no
H13A H11 2.4500 . . no
H13B H1B 1.8600 . . no
H13B C2 2.9500 . . no
H13B H1A 2.2900 . . no
H13B C1 2.4000 . . no
H14A S2A 3.0400 . 2_655 no
H15A C1 2.6500 . . no
H15A H1B 2.1200 . . no
H15A H1A 2.5000 . . no
H15B O1 2.4900 . 2_766 no
H16A C17 2.9700 . 2_565 no
H16A H1B 2.2100 . . no
H16A C20 3.0700 . 2_565 no
H16A C18 2.8400 . 2_565 no
H16A C19 2.9000 . 2_565 no
H16B H22 2.3600 . . no
H16B H1A 2.5000 . . no
H16B H5B 2.3400 . . no
H18 N1 2.9300 . . no
H19 S2B 3.0900 . 2_665 no
H19 C14A 3.0200 . 2_665 no
H19 C15A 3.0200 . 2_665 no
H19 C13B 3.0000 . 2_665 no
H20 S2A 3.1600 . 2_665 no
H21 S1B 2.8300 . 2_576 no
H21 C9A 2.9900 . 2_576 no
H22 H16B 2.3600 . . no
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
C13A H13A O1 2_766 0.95 2.39 3.177(4) 140 yes
C16 H16A Cg6 2_565 0.99 2.68 3.6017(19) 156 yes
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
C9A S1A C8A C7A . . . . -0.2(3) no
C8A S1A C9A C10A . . . . -0.9(3) no
C14A S2A C13A C12A . . . . -0.4(3) no
C13A S2A C14A C15A . . . . 0.0(4) no
C5 N1 C1 C2 . . . . -62.00(18) no
C16 N1 C1 C2 . . . . 177.45(13) no
C16 N1 C5 C4 . . . . -177.33(14) no
C1 N1 C16 C17 . . . . -164.29(14) no
C5 N1 C16 C17 . . . . 75.66(18) no
C1 N1 C5 C4 . . . . 63.39(18) no
N1 C1 C2 C11 . . . . -153.36(16) no
N1 C1 C2 C3 . . . . 26.7(2) no
C11 C2 C3 C4 . . . . -174.12(16) no
C3 C2 C11 C12A . . . . 179.2(2) no
C11 C2 C3 O1 . . . . 4.2(3) no
C1 C2 C11 C12A . . . . -0.8(3) no
C1 C2 C3 C4 . . . . 5.8(2) no
C1 C2 C3 O1 . . . . -175.89(16) no
O1 C3 C4 C5 . . . . 177.70(16) no
O1 C3 C4 C6 . . . . -3.6(3) no
C2 C3 C4 C5 . . . . -4.0(2) no
C2 C3 C4 C6 . . . . 174.63(16) no
C3 C4 C5 N1 . . . . -29.9(2) no
C3 C4 C6 C7A . . . . -177.8(2) no
C5 C4 C6 C7A . . . . 0.7(3) no
C6 C4 C5 N1 . . . . 151.56(17) no
C4 C6 C7A C8A . . . . 19.5(4) no
C4 C6 C7A C10A . . . . -166.4(3) no
C10A C7A C8A S1A . . . . 1.2(3) no
C6 C7A C8A S1A . . . . 175.9(2) no
C6 C7A C10A C9A . . . . -176.8(3) no
C8A C7A C10A C9A . . . . -1.9(4) no
S1A C9A C10A C7A . . . . 1.7(4) no
C2 C11 C12A C15A . . . . -18.5(5) no
C2 C11 C12A C13A . . . . 163.1(2) no
C15A C12A C13A S2A . . . . 0.7(4) no
C11 C12A C13A S2A . . . . 179.4(2) no
C11 C12A C15A C14A . . . . -179.2(3) no
C13A C12A C15A C14A . . . . -0.7(5) no
S2A C14A C15A C12A . . . . 0.4(5) no
N1 C16 C17 C18 . . . . 62.1(2) no
N1 C16 C17 C22 . . . . -121.80(17) no
C16 C17 C18 C19 . . . . 176.81(16) no
C22 C17 C18 C19 . . . . 0.6(3) no
C16 C17 C22 C21 . . . . -176.10(16) no
C18 C17 C22 C21 . . . . 0.1(3) no
C17 C18 C19 C20 . . . . -0.8(3) no
C18 C19 C20 C21 . . . . 0.4(3) no
C19 C20 C21 C22 . . . . 0.3(3) no
C20 C21 C22 C17 . . . . -0.5(3) no
