#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/79/2207926.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_2207926
loop_
_publ_author_name
'Ricardo R. Contreras'
'Bernardo Fontal'
'Isolda Romero'
'Reinaldo Atencio'
'Alexander Briceño'
_publ_section_title
;
 Intramolecular hydrogen bonding in dibenzyl
 2,2'-(propane-1,3-diyldiimino)bis(cyclopent-1-ene-1-carbodithioate)
;
_journal_coeditor_code           WN6402
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o205
_journal_page_last               o208
_journal_paper_doi               10.1107/S1600536805040353
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C29 H34 N2 S4'
_chemical_formula_moiety         'C29 H34 N2 S4'
_chemical_formula_sum            'C29 H34 N2 S4'
_chemical_formula_weight         538.82
_chemical_name_systematic
;
dibenzyl
2,2'-(propane-1,3-diyldiimino)bis(cyclopent-1-ene-1-carbodithioate)
;
_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                90.62(3)
_cell_angle_beta                 94.24(3)
_cell_angle_gamma                101.25(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8860(3)
_cell_length_b                   12.427(3)
_cell_length_c                   14.752(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      37.16
_cell_measurement_theta_min      32.36
_cell_volume                     1413.6(5)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation, 1999)
;
_computing_molecular_graphics
;
SHELXLTL-NT and DIAMOND (Brandenburg, 1998)
;
_computing_publication_material  'SHELXLTL-NT and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXLTL-NT
_computing_structure_solution    'SHELXLTL-NT (Bruker, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC-7S'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5320
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.9206
_exptl_absorpt_correction_T_min  0.8607
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0418P)²+0.4751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                3374
_reflns_number_total             4986
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6402.cif
_cod_data_source_block           I
_cod_database_code               2207926
_cod_database_fobs_code          2207926
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
S1 0.21448(10) 0.30419(6) 0.96602(5) 0.0608(2) Uani d . 1 S
S2 0.08771(9) 0.32118(7) 1.15285(5) 0.0586(2) Uani d . 1 S
S3 0.06427(10) 0.75861(6) 0.62016(5) 0.0618(2) Uani d . 1 S
S4 -0.29686(10) 0.69583(6) 0.52618(5) 0.0595(2) Uani d . 1 S
N1 0.3263(3) 0.54046(19) 0.91476(14) 0.0506(5) Uani d . 1 N
H1 0.3145 0.4711 0.9047 0.061 Uiso d R 1 H
N2 0.1485(3) 0.53990(18) 0.67601(14) 0.0508(5) Uani d . 1 N
H2 0.1780 0.6138 0.6756 0.061 Uiso d R 1 H
C1 0.1804(3) 0.3821(2) 1.05541(16) 0.0488(6) Uani d . 1 C
C2 0.2153(3) 0.4956(2) 1.06151(16) 0.0476(6) Uani d . 1 C
C3 0.2833(3) 0.5686(2) 0.99481(17) 0.0479(6) Uani d . 1 C
C4 0.2983(4) 0.6850(2) 1.02507(19) 0.0587(7) Uani d . 1 C
H4A 0.2073 0.7170 0.9948 0.070 Uiso calc R 1 H
H4B 0.4100 0.7284 1.0128 0.070 Uiso calc R 1 H
C5 0.2791(4) 0.6781(3) 1.1272(2) 0.0711(9) Uani d . 1 C
H5A 0.3918 0.6885 1.1608 0.085 Uiso calc R 1 H
H5B 0.2181 0.7335 1.1475 0.085 Uiso calc R 1 H
C6 0.1755(4) 0.5638(2) 1.14068(18) 0.0570(7) Uani d . 1 C
H6A 0.0524 0.5642 1.1391 0.068 Uiso calc R 1 H
H6B 0.2117 0.5352 1.1983 0.068 Uiso calc R 1 H
C7 0.0752(4) 0.1756(2) 1.1360(2) 0.0701(9) Uani d . 1 C
H7A -0.0152 0.1365 1.1713 0.084 Uiso calc R 1 H
H7B 0.0412 0.1566 1.0724 0.084 Uiso calc R 1 H
C8 0.2416(4) 0.1368(2) 1.1621(2) 0.0654(8) Uani d . 1 C
C9 0.3256(4) 0.1627(3) 1.2468(2) 0.0704(9) Uani d . 1 C
H9 0.2789 0.2048 1.2872 0.085 Uiso calc R 1 H
C10 0.4773(5) 0.1281(3) 1.2740(3) 0.0932(12) Uani d . 1 C
H10 0.5316 0.1459 1.3318 0.112 Uiso calc R 1 H
C11 0.5451(6) 0.0678(4) 1.2146(4) 0.1239(18) Uani d . 1 C
H11 0.6485 0.0456 1.2317 0.149 Uiso calc R 1 H
C12 0.4656(8) 0.0385(4) 1.1300(4) 0.139(2) Uani d . 1 C
H12 0.5128 -0.0045 1.0907 0.166 Uiso calc R 1 H
C13 0.3115(6) 0.0743(3) 1.1033(3) 0.1067(13) Uani d . 1 C
H13 0.2569 0.0556 1.0457 0.128 Uiso calc R 1 H
C14 0.3896(3) 0.6170(2) 0.84486(17) 0.0545(7) Uani d . 1 C
H14A 0.4937 0.6672 0.8690 0.065 Uiso calc R 1 H
H14B 0.3026 0.6598 0.8271 0.065 Uiso calc R 1 H
C15 0.4294(3) 0.5550(2) 0.76260(18) 0.0562(7) Uani d . 1 C
H15A 0.4796 0.6078 0.7193 0.067 Uiso calc R 1 H
H15B 0.5161 0.5125 0.7816 0.067 Uiso calc R 1 H
C16 0.2756(3) 0.4787(2) 0.71502(18) 0.0549(7) Uani d . 1 C
H16A 0.3145 0.4375 0.6671 0.066 Uiso calc R 1 H
H16B 0.2216 0.4269 0.7581 0.066 Uiso calc R 1 H
C17 -0.0070(3) 0.4951(2) 0.63891(16) 0.0459(6) Uani d . 1 C
C18 -0.1306(3) 0.5495(2) 0.59732(16) 0.0472(6) Uani d . 1 C
C19 -0.2887(3) 0.4653(2) 0.56291(18) 0.0542(7) Uani d . 1 C
H19A -0.2991 0.4608 0.4970 0.065 Uiso calc R 1 H
H19B -0.3934 0.4841 0.5837 0.065 Uiso calc R 1 H
C20 -0.2591(4) 0.3572(2) 0.6024(2) 0.0724(9) Uani d . 1 C
H20A -0.3304 0.3378 0.6528 0.087 Uiso calc R 1 H
H20B -0.2888 0.2988 0.5564 0.087 Uiso calc R 1 H
C21 -0.0692(4) 0.3734(2) 0.63445(19) 0.0556(7) Uani d . 1 C
H21A -0.0543 0.3422 0.6938 0.067 Uiso calc R 1 H
H21B -0.0063 0.3392 0.5920 0.067 Uiso calc R 1 H
C22 -0.1094(3) 0.6619(2) 0.58455(16) 0.0481(6) Uani d . 1 C
C23 -0.2355(4) 0.8398(2) 0.4999(2) 0.0678(8) Uani d . 1 C
H23A -0.3360 0.8737 0.5019 0.081 Uiso calc R 1 H
H23B -0.1483 0.8759 0.5460 0.081 Uiso calc R 1 H
C24 -0.1655(4) 0.8569(2) 0.4084(2) 0.0624(8) Uani d . 1 C
C25 0.0087(5) 0.8942(2) 0.4006(3) 0.0809(10) Uani d . 1 C
H25 0.0842 0.9105 0.4526 0.097 Uiso calc R 1 H
C26 0.0722(6) 0.9075(3) 0.3144(3) 0.0981(13) Uani d . 1 C
H26 0.1897 0.9337 0.3088 0.118 Uiso calc R 1 H
C27 -0.0406(7) 0.8815(3) 0.2375(3) 0.0972(13) Uani d . 1 C
H27 0.0015 0.8893 0.1802 0.117 Uiso calc R 1 H
C28 -0.2103(6) 0.8452(3) 0.2452(3) 0.0928(11) Uani d . 1 C
H28 -0.2855 0.8284 0.1932 0.111 Uiso calc R 1 H
C29 -0.2743(5) 0.8325(3) 0.3298(2) 0.0790(9) Uani d . 1 C
H29 -0.3923 0.8071 0.3340 0.095 Uiso calc R 1 H
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'
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
_geom_angle_publ_flag
C1 S2 C7 105.12(14) y
C22 S4 C23 105.38(14) y
C3 N1 C14 125.1(2) y
C3 N1 H1 115.1 n
C14 N1 H1 119.8 n
C17 N2 C16 124.8(2) y
C17 N2 H2 116.6 n
C16 N2 H2 118.5 n
C2 C1 S1 126.2(2) y
C2 C1 S2 112.62(19) y
S1 C1 S2 121.15(17) y
C1 C2 C3 126.9(2) y
C1 C2 C6 125.2(2) y
C3 C2 C6 107.8(2) y
N1 C3 C2 125.8(3) y
N1 C3 C4 122.8(2) y
C2 C3 C4 111.4(2) y
C3 C4 C5 103.9(2) n
C3 C4 H4A 111.0 n
C5 C4 H4A 111.0 n
C3 C4 H4B 111.0 n
C5 C4 H4B 111.0 n
H4A C4 H4B 109.0 n
C6 C5 C4 105.2(2) y
C6 C5 H5A 110.7 n
C4 C5 H5A 110.7 n
C6 C5 H5B 110.7 n
C4 C5 H5B 110.7 n
H5A C5 H5B 108.8 n
C5 C6 C2 104.4(2) y
C5 C6 H6A 110.9 n
C2 C6 H6A 110.9 n
C5 C6 H6B 110.9 n
C2 C6 H6B 110.9 n
H6A C6 H6B 108.9 n
C8 C7 S2 114.6(2) y
C8 C7 H7A 108.6 n
S2 C7 H7A 108.6 n
C8 C7 H7B 108.6 n
S2 C7 H7B 108.6 n
H7A C7 H7B 107.6 n
C13 C8 C9 118.4(4) n
C13 C8 C7 121.5(4) n
C9 C8 C7 120.1(3) n
C8 C9 C10 122.1(3) n
C8 C9 H9 119.0 n
C10 C9 H9 119.0 n
C11 C10 C9 118.5(4) n
C11 C10 H10 120.7 n
C9 C10 H10 120.7 n
C10 C11 C12 121.8(5) n
C10 C11 H11 119.1 n
C12 C11 H11 119.1 n
C11 C12 C13 119.1(5) n
C11 C12 H12 120.4 n
C13 C12 H12 120.4 n
C8 C13 C12 120.1(4) n
C8 C13 H13 120.0 n
C12 C13 H13 120.0 n
N1 C14 C15 110.2(2) y
N1 C14 H14A 109.6 n
C15 C14 H14A 109.6 n
N1 C14 H14B 109.6 n
C15 C14 H14B 109.6 n
H14A C14 H14B 108.1 n
C16 C15 C14 115.0(2) y
C16 C15 H15A 108.5 n
C14 C15 H15A 108.5 n
C16 C15 H15B 108.5 n
C14 C15 H15B 108.5 n
H15A C15 H15B 107.5 n
N2 C16 C15 111.0(2) y
N2 C16 H16A 109.4 n
C15 C16 H16A 109.4 n
N2 C16 H16B 109.4 n
C15 C16 H16B 109.4 n
H16A C16 H16B 108.0 n
N2 C17 C18 127.1(2) y
N2 C17 C21 121.4(2) y
C18 C17 C21 111.4(2) y
C22 C18 C17 126.0(2) y
C22 C18 C19 124.9(2) y
C17 C18 C19 108.9(2) y
C18 C19 C20 105.1(2) n
C18 C19 H19A 110.7 n
C20 C19 H19A 110.7 n
C18 C19 H19B 110.7 n
C20 C19 H19B 110.7 n
H19A C19 H19B 108.8 n
C21 C20 C19 107.0(2) n
C21 C20 H20A 110.3 n
C19 C20 H20A 110.3 n
C21 C20 H20B 110.3 n
C19 C20 H20B 110.3 n
H20A C20 H20B 108.6 n
C17 C21 C20 104.8(2) n
C17 C21 H21A 110.8 n
C20 C21 H21A 110.8 n
C17 C21 H21B 110.8 n
C20 C21 H21B 110.8 n
H21A C21 H21B 108.9 n
C18 C22 S3 126.8(2) y
C18 C22 S4 111.27(19) y
S3 C22 S4 121.87(16) y
C24 C23 S4 112.7(2) y
C24 C23 H23A 109.0 n
S4 C23 H23A 109.0 n
C24 C23 H23B 109.0 n
S4 C23 H23B 109.0 n
H23A C23 H23B 107.8 n
C25 C24 C29 118.6(3) n
C25 C24 C23 120.8(3) n
C29 C24 C23 120.6(3) n
C24 C25 C26 119.9(4) n
C24 C25 H25 120.0 n
C26 C25 H25 120.0 n
C27 C26 C25 119.7(4) n
C27 C26 H26 120.1 n
C25 C26 H26 120.1 n
C28 C27 C26 120.3(4) n
C28 C27 H27 119.9 n
C26 C27 H27 119.9 n
C27 C28 C29 120.5(4) n
C27 C28 H28 119.8 n
C29 C28 H28 119.8 n
C28 C29 C24 121.1(4) n
C28 C29 H29 119.5 n
C24 C29 H29 119.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.695(3) y
S2 C1 1.771(3) y
S2 C7 1.805(3) y
S3 C22 1.683(3) y
S4 C22 1.780(3) y
S4 C23 1.814(3) y
N1 C3 1.315(3) y
N1 C14 1.459(3) y
N1 H1 0.8583 n
N2 C17 1.320(3) y
N2 C16 1.461(3) y
N2 H2 0.9019 n
C1 C2 1.385(4) y
C2 C3 1.409(4) y
C2 C6 1.522(4) n
C3 C4 1.489(4) y
C4 C5 1.527(4) n
C4 H4A 0.9700 n
C4 H4B 0.9700 n
C5 C6 1.517(4) n
C5 H5A 0.9700 n
C5 H5B 0.9700 n
C6 H6A 0.9700 n
C6 H6B 0.9700 n
C7 C8 1.510(4) n
C7 H7A 0.9700 n
C7 H7B 0.9700 n
C8 C13 1.372(5) n
C8 C9 1.375(4) n
C9 C10 1.382(5) n
C9 H9 0.9300 n
C10 C11 1.351(6) n
C10 H10 0.9300 n
C11 C12 1.367(7) n
C11 H11 0.9300 n
C12 C13 1.404(6) n
C12 H12 0.9300 n
C13 H13 0.9300 n
C14 C15 1.515(4) n
C14 H14A 0.9700 n
C14 H14B 0.9700 n
C15 C16 1.508(4) n
C15 H15A 0.9700 n
C15 H15B 0.9700 n
C16 H16A 0.9700 n
C16 H16B 0.9700 n
C17 C18 1.400(4) y
C17 C21 1.495(4) n
C18 C22 1.390(4) y
C18 C19 1.515(4) n
C19 C20 1.523(4) n
C19 H19A 0.9700 n
C19 H19B 0.9700 n
C20 C21 1.511(4) n
C20 H20A 0.9700 n
C20 H20B 0.9700 n
C21 H21A 0.9700 n
C21 H21B 0.9700 n
C23 C24 1.497(4) n
C23 H23A 0.9700 n
C23 H23B 0.9700 n
C24 C25 1.375(4) n
C24 C29 1.385(4) n
C25 C26 1.402(5) n
C25 H25 0.9300 n
C26 C27 1.383(6) n
C26 H26 0.9300 n
C27 C28 1.341(5) n
C27 H27 0.9300 n
C28 C29 1.379(5) n
C28 H28 0.9300 n
C29 H29 0.9300 n
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
N1 H1 S1 1_555 0.86 2.29 3.018(3) 142 y
N2 H2 S3 1_555 0.90 2.29 3.030(2) 138 y
C7 H7B S1 1_555 0.97 2.66 3.140(3) 111 y
C23 H23B S3 1_555 0.97 2.62 3.179(3) 117 y
C14 H14A Cg3 2_667 0.97 2.99 3.64(5) 125 y
C21 H21A Cg4 2_566 0.97 3.13 3.58(4) 110 y
C21 H21B Cg4 2_566 0.97 3.13 3.58(4) 110 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126640
