#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/42/2204257.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_2204257
loop_
_publ_author_name
'Brito, Ivań'
'Vargas, Danitza'
'Leoń, Yasna'
'Caŕdenas, Alejandro'
'Loṕez-Rodriǵuez, Matiás'
'Wittke, Oscar'
_publ_section_title
;
 N,N-Dibenzyltriphenylmethanesulfenamide
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1668
_journal_page_last               o1670
_journal_paper_doi               10.1107/S1600536804021427
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C33 H29 N S'
_chemical_formula_moiety         'C33 H29 N S'
_chemical_formula_sum            'C33 H29 N S'
_chemical_formula_weight         471.63
_chemical_melting_point          409
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                106.822(13)
_cell_angle_beta                 99.037(13)
_cell_angle_gamma                100.245(19)
_cell_formula_units_Z            2
_cell_length_a                   10.009(2)
_cell_length_b                   10.519(3)
_cell_length_c                   13.3110(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.41
_cell_measurement_theta_min      11.97
_cell_volume                     1287.3(5)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius 1994)'
_computing_data_reduction        'XCDA4 (Harms, 1996)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5442
_diffrn_reflns_theta_full        73.91
_diffrn_reflns_theta_max         73.91
_diffrn_reflns_theta_min         5.16
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 120
_diffrn_standards_interval_time  1
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.263
_exptl_absorpt_correction_T_max  0.8274
_exptl_absorpt_correction_T_min  0.7160
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0525P)²+0.217P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                3437
_reflns_number_total             5207
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ac6116.cif
_cod_data_source_block           I
_cod_database_code               2204257
_cod_database_fobs_code          2204257
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 0.05767(5) 0.42981(5) 0.25809(4) 0.05087(16) Uani d . 1 S
N1 -0.00227(17) 0.26189(17) 0.18844(13) 0.0496(4) Uani d . 1 N
C1 0.22993(19) 0.44546(18) 0.34880(15) 0.0399(4) Uani d . 1 C
C2 0.26318(19) 0.59537(19) 0.42044(15) 0.0410(4) Uani d . 1 C
C3 0.3031(2) 0.6345(2) 0.53182(16) 0.0447(5) Uani d . 1 C
H3 0.3048 0.5679 0.5649 0.042(5) Uiso calc R 1 H
C4 0.3404(2) 0.7709(2) 0.59438(17) 0.0507(5) Uani d . 1 C
H4 0.3676 0.7952 0.6688 0.060(6) Uiso calc R 1 H
C5 0.3375(2) 0.8709(2) 0.54715(19) 0.0567(6) Uani d . 1 C
H5 0.3624 0.9626 0.5893 0.053(6) Uiso calc R 1 H
C6 0.2975(2) 0.8343(2) 0.43707(19) 0.0590(6) Uani d . 1 C
H6 0.2948 0.9015 0.4048 0.066(7) Uiso calc R 1 H
C7 0.2613(2) 0.6987(2) 0.37440(18) 0.0505(5) Uani d . 1 C
H7 0.2351 0.6756 0.3 0.047(6) Uiso calc R 1 H
C8 0.33973(19) 0.41776(19) 0.28167(15) 0.0412(4) Uani d . 1 C
C9 0.3234(2) 0.2907(2) 0.20559(17) 0.0533(5) Uani d . 1 C
H9 0.2442 0.2225 0.1947 0.048(6) Uiso calc R 1 H
C10 0.4215(2) 0.2631(3) 0.14585(19) 0.0626(6) Uani d . 1 C
H10 0.4075 0.1774 0.0948 0.071(7) Uiso calc R 1 H
C11 0.5398(3) 0.3616(3) 0.16129(19) 0.0653(7) Uani d . 1 C
H11 0.6054 0.3435 0.1202 0.068(7) Uiso calc R 1 H
C12 0.5605(2) 0.4869(3) 0.2378(2) 0.0624(6) Uani d . 1 C
H12 0.6413 0.5535 0.2497 0.074(7) Uiso calc R 1 H
C13 0.4614(2) 0.5148(2) 0.29760(17) 0.0500(5) Uani d . 1 C
H13 0.4768 0.6002 0.3494 0.052(6) Uiso calc R 1 H
C14 0.21018(19) 0.34865(18) 0.41448(15) 0.0404(4) Uani d . 1 C
C15 0.0974(2) 0.3378(2) 0.46367(17) 0.0501(5) Uani d . 1 C
H15 0.0313 0.3876 0.454 0.056(6) Uiso calc R 1 H
C16 0.0820(3) 0.2544(2) 0.52653(19) 0.0609(6) Uani d . 1 C
H16 0.0055 0.2481 0.558 0.077(8) Uiso calc R 1 H
C17 0.1793(3) 0.1808(2) 0.54282(19) 0.0610(6) Uani d . 1 C
H17 0.1678 0.123 0.5837 0.064(7) Uiso calc R 1 H
C18 0.2934(2) 0.1936(2) 0.49816(18) 0.0533(5) Uani d . 1 C
H18 0.361 0.1465 0.5108 0.065(7) Uiso calc R 1 H
C19 0.3086(2) 0.27632(18) 0.43426(16) 0.0440(5) Uani d . 1 C
H19 0.3863 0.2833 0.4042 0.037(5) Uiso calc R 1 H
C20 -0.0075(2) 0.2198(2) 0.07144(17) 0.0540(5) Uani d . 1 C
H20A -0.0026 0.1248 0.0473 0.065(7) Uiso calc R 1 H
H20B 0.0746 0.2734 0.0598 0.056(6) Uiso calc R 1 H
C21 -0.1225(2) 0.1886(2) 0.21632(18) 0.0538(5) Uani d . 1 C
H21A -0.2073 0.1945 0.1731 0.055(6) Uiso calc R 1 H
H21B -0.1218 0.2331 0.2913 0.062(6) Uiso calc R 1 H
C22 -0.1348(2) 0.2351(2) 0.00215(17) 0.0537(5) Uani d . 1 C
C23 -0.1528(3) 0.3613(3) 0.0002(2) 0.0681(6) Uani d . 1 C
H23 -0.0867 0.4396 0.0444 0.080(9) Uiso calc R 1 H
C24 -0.2672(3) 0.3737(4) -0.0661(2) 0.0866(9) Uani d . 1 C
H24 -0.2776 0.4597 -0.0665 0.092(9) Uiso calc R 1 H
C25 -0.3650(3) 0.2594(5) -0.1312(3) 0.0960(10) Uani d . 1 C
H25 -0.4423 0.2674 -0.1757 0.107(10) Uiso calc R 1 H
C26 -0.3490(3) 0.1334(4) -0.1307(3) 0.0977(10) Uani d . 1 C
H26 -0.4152 0.0554 -0.1752 0.117(11) Uiso calc R 1 H
C27 -0.2346(3) 0.1220(3) -0.0643(2) 0.0759(7) Uani d . 1 C
H27 -0.2248 0.0356 -0.0645 0.081(9) Uiso calc R 1 H
C28 -0.1243(2) 0.0395(2) 0.19885(17) 0.0510(5) Uani d . 1 C
C29 -0.2440(3) -0.0607(3) 0.1463(2) 0.0682(7) Uani d . 1 C
H29 -0.3233 -0.0362 0.119 0.077(8) Uiso calc R 1 H
C30 -0.2490(3) -0.1966(3) 0.1333(2) 0.0807(8) Uani d . 1 C
H30 -0.3308 -0.2626 0.0971 0.087(8) Uiso calc R 1 H
C31 -0.1335(3) -0.2345(3) 0.1737(2) 0.0753(7) Uani d . 1 C
H31 -0.1365 -0.3258 0.1659 0.094(9) Uiso calc R 1 H
C32 -0.0142(3) -0.1363(3) 0.2256(2) 0.0724(7) Uani d . 1 C
H32 0.0651 -0.1613 0.2523 0.097(10) Uiso calc R 1 H
C33 -0.0096(2) -0.0006(3) 0.2390(2) 0.0632(6) Uani d . 1 C
H33 0.0723 0.065 0.2759 0.069(7) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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
_geom_angle_publ_flag
N1 S1 C1 105.61(8) y
C21 N1 C20 113.52(16) y
C21 N1 S1 116.97(14) y
C20 N1 S1 116.77(14) y
C14 C1 C2 111.42(15) y
C14 C1 C8 112.01(14) y
C2 C1 C8 111.58(15) y
C14 C1 S1 109.78(12) y
C2 C1 S1 101.39(12) y
C8 C1 S1 110.15(12) y
C3 C2 C7 117.50(18) ?
C3 C2 C1 122.12(16) ?
C7 C2 C1 120.29(17) ?
C4 C3 C2 121.07(19) ?
C4 C3 H3 119.5 ?
C2 C3 H3 119.5 ?
C5 C4 C3 120.3(2) ?
C5 C4 H4 119.8 ?
C3 C4 H4 119.8 ?
C4 C5 C6 119.5(2) ?
C4 C5 H5 120.2 ?
C6 C5 H5 120.2 ?
C5 C6 C7 120.4(2) ?
C5 C6 H6 119.8 ?
C7 C6 H6 119.8 ?
C6 C7 C2 121.2(2) ?
C6 C7 H7 119.4 ?
C2 C7 H7 119.4 ?
C13 C8 C9 117.18(18) ?
C13 C8 C1 122.07(17) ?
C9 C8 C1 120.67(17) ?
C10 C9 C8 121.6(2) ?
C10 C9 H9 119.2 ?
C8 C9 H9 119.2 ?
C11 C10 C9 120.3(2) ?
C11 C10 H10 119.9 ?
C9 C10 H10 119.9 ?
C12 C11 C10 119.4(2) ?
C12 C11 H11 120.3 ?
C10 C11 H11 120.3 ?
C11 C12 C13 120.2(2) ?
C11 C12 H12 119.9 ?
C13 C12 H12 119.9 ?
C12 C13 C8 121.2(2) ?
C12 C13 H13 119.4 ?
C8 C13 H13 119.4 ?
C19 C14 C15 117.32(18) ?
C19 C14 C1 121.44(17) ?
C15 C14 C1 121.07(16) ?
C16 C15 C14 121.3(2) ?
C16 C15 H15 119.4 ?
C14 C15 H15 119.4 ?
C17 C16 C15 120.3(2) ?
C17 C16 H16 119.8 ?
C15 C16 H16 119.8 ?
C18 C17 C16 119.3(2) ?
C18 C17 H17 120.4 ?
C16 C17 H17 120.4 ?
C17 C18 C19 120.5(2) ?
C17 C18 H18 119.7 ?
C19 C18 H18 119.7 ?
C14 C19 C18 121.19(19) ?
C14 C19 H19 119.4 ?
C18 C19 H19 119.4 ?
N1 C20 C22 115.60(17) ?
N1 C20 H20A 108.4 ?
C22 C20 H20A 108.4 ?
N1 C20 H20B 108.4 ?
C22 C20 H20B 108.4 ?
H20A C20 H20B 107.4 ?
N1 C21 C28 113.32(17) ?
N1 C21 H21A 108.9 ?
C28 C21 H21A 108.9 ?
N1 C21 H21B 108.9 ?
C28 C21 H21B 108.9 ?
H21A C21 H21B 107.7 ?
C27 C22 C23 117.6(2) ?
C27 C22 C20 120.6(2) ?
C23 C22 C20 121.7(2) ?
C22 C23 C24 121.2(3) ?
C22 C23 H23 119.4 ?
C24 C23 H23 119.4 ?
C25 C24 C23 119.9(3) ?
C25 C24 H24 120 ?
C23 C24 H24 120 ?
C26 C25 C24 119.8(3) ?
C26 C25 H25 120.1 ?
C24 C25 H25 120.1 ?
C25 C26 C27 119.9(3) ?
C25 C26 H26 120 ?
C27 C26 H26 120 ?
C22 C27 C26 121.5(3) ?
C22 C27 H27 119.2 ?
C26 C27 H27 119.2 ?
C33 C28 C29 117.5(2) ?
C33 C28 C21 121.66(19) ?
C29 C28 C21 120.7(2) ?
C28 C29 C30 121.5(2) ?
C28 C29 H29 119.2 ?
C30 C29 H29 119.2 ?
C31 C30 C29 120.1(2) ?
C31 C30 H30 120 ?
C29 C30 H30 120 ?
C32 C31 C30 119.0(3) ?
C32 C31 H31 120.5 ?
C30 C31 H31 120.5 ?
C31 C32 C33 120.8(3) ?
C31 C32 H32 119.6 ?
C33 C32 H32 119.6 ?
C28 C33 C32 121.0(2) ?
C28 C33 H33 119.5 ?
C32 C33 H33 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 N1 1.6852(18) y
S1 C1 1.8941(19) y
N1 C21 1.469(3) y
N1 C20 1.480(3) y
C1 C14 1.529(3) y
C1 C2 1.533(3) y
C1 C8 1.537(3) y
C2 C3 1.389(3) ?
C2 C7 1.396(3) ?
C3 C4 1.383(3) ?
C3 H3 0.93 ?
C4 C5 1.374(3) ?
C4 H4 0.93 ?
C5 C6 1.375(3) ?
C5 H5 0.93 ?
C6 C7 1.376(3) ?
C6 H6 0.93 ?
C7 H7 0.93 ?
C8 C13 1.386(3) ?
C8 C9 1.388(3) ?
C9 C10 1.376(3) ?
C9 H9 0.93 ?
C10 C11 1.372(3) ?
C10 H10 0.93 ?
C11 C12 1.370(3) ?
C11 H11 0.93 ?
C12 C13 1.385(3) ?
C12 H12 0.93 ?
C13 H13 0.93 ?
C14 C19 1.385(3) ?
C14 C15 1.395(3) ?
C15 C16 1.382(3) ?
C15 H15 0.93 ?
C16 C17 1.377(3) ?
C16 H16 0.93 ?
C17 C18 1.371(3) ?
C17 H17 0.93 ?
C18 C19 1.388(3) ?
C18 H18 0.93 ?
C19 H19 0.93 ?
C20 C22 1.513(3) y
C20 H20A 0.97 ?
C20 H20B 0.97 ?
C21 C28 1.514(3) y
C21 H21A 0.97 ?
C21 H21B 0.97 ?
C22 C27 1.374(3) ?
C22 C23 1.378(3) ?
C23 C24 1.382(4) ?
C23 H23 0.93 ?
C24 C25 1.366(5) ?
C24 H24 0.93 ?
C25 C26 1.365(5) ?
C25 H25 0.93 ?
C26 C27 1.378(4) ?
C26 H26 0.93 ?
C27 H27 0.93 ?
C28 C33 1.375(3) ?
C28 C29 1.377(3) ?
C29 C30 1.380(4) ?
C29 H29 0.93 ?
C30 C31 1.370(4) ?
C30 H30 0.93 ?
C31 C32 1.363(4) ?
C31 H31 0.93 ?
C32 C33 1.379(3) ?
C32 H32 0.93 ?
C33 H33 0.93 ?
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
C9 H9 N1 0.93 2.57 3.185(3) 124
C15 H15 S1 0.93 2.81 3.148(3) 103
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
C1 S1 N1 C21 108.64(16)
C1 S1 N1 C20 -112.05(15)
N1 S1 C1 C14 -53.23(14)
N1 S1 C1 C2 -171.16(11)
N1 S1 C1 C8 70.57(14)
C14 C1 C2 C3 14.5(2)
C8 C1 C2 C3 -111.50(19)
S1 C1 C2 C3 131.27(16)
C14 C1 C2 C7 -168.95(17)
C8 C1 C2 C7 65.0(2)
S1 C1 C2 C7 -52.2(2)
C7 C2 C3 C4 -0.4(3)
C1 C2 C3 C4 176.18(17)
C2 C3 C4 C5 0.6(3)
C3 C4 C5 C6 -0.2(3)
C4 C5 C6 C7 -0.4(3)
C5 C6 C7 C2 0.5(3)
C3 C2 C7 C6 -0.1(3)
C1 C2 C7 C6 -176.76(18)
C14 C1 C8 C13 -117.65(19)
C2 C1 C8 C13 8.1(2)
S1 C1 C8 C13 119.86(17)
C14 C1 C8 C9 59.1(2)
C2 C1 C8 C9 -175.17(17)
S1 C1 C8 C9 -63.4(2)
C13 C8 C9 C10 -2.1(3)
C1 C8 C9 C10 -178.99(19)
C8 C9 C10 C11 0.7(3)
C9 C10 C11 C12 1.0(4)
C10 C11 C12 C13 -1.3(3)
C11 C12 C13 C8 -0.1(3)
C9 C8 C13 C12 1.8(3)
C1 C8 C13 C12 178.64(18)
C2 C1 C14 C19 -107.92(19)
C8 C1 C14 C19 17.9(2)
S1 C1 C14 C19 140.57(16)
C2 C1 C14 C15 67.1(2)
C8 C1 C14 C15 -167.08(17)
S1 C1 C14 C15 -44.4(2)
C19 C14 C15 C16 -2.2(3)
C1 C14 C15 C16 -177.47(19)
C14 C15 C16 C17 0.6(3)
C15 C16 C17 C18 1.6(4)
C16 C17 C18 C19 -2.1(3)
C15 C14 C19 C18 1.7(3)
C1 C14 C19 C18 176.91(18)
C17 C18 C19 C14 0.5(3)
C21 N1 C20 C22 57.5(2)
S1 N1 C20 C22 -83.2(2)
C20 N1 C21 C28 69.8(2)
S1 N1 C21 C28 -149.62(15)
N1 C20 C22 C27 -109.1(2)
N1 C20 C22 C23 73.2(3)
C27 C22 C23 C24 0.0(4)
C20 C22 C23 C24 177.8(2)
C22 C23 C24 C25 0.1(4)
C23 C24 C25 C26 -0.3(4)
C24 C25 C26 C27 0.3(5)
C23 C22 C27 C26 0.0(4)
C20 C22 C27 C26 -177.8(2)
C25 C26 C27 C22 -0.1(5)
N1 C21 C28 C33 50.1(3)
N1 C21 C28 C29 -133.1(2)
C33 C28 C29 C30 -0.6(4)
C21 C28 C29 C30 -177.5(2)
C28 C29 C30 C31 0.5(4)
C29 C30 C31 C32 -0.6(4)
C30 C31 C32 C33 1.0(4)
C29 C28 C33 C32 1.0(4)
C21 C28 C33 C32 177.8(2)
C31 C32 C33 C28 -1.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130476
