#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/42/2204225.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_2204225
loop_
_publ_author_name
'Liu, Sheng-Gui'
'You, Xiao-Zeng'
'Li, Yi-Zhi'
'Zuo, Jing-Lin'
_publ_section_title
;
 N,N'-Bis[2-(methylsulfanyl)phenyl]pyridine-2,6-dicarboxamide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1527
_journal_page_last               o1529
_journal_paper_doi               10.1107/S1600536804018409
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C21 H19 N3 O2 S2'
_chemical_formula_moiety         'C21 H19 N3 O2 S2'
_chemical_formula_sum            'C21 H19 N3 O2 S2'
_chemical_formula_weight         409.51
_chemical_name_systematic
;
N,N'-Bis[2-(methylsulfanyl)phenyl]pyridine-2,6-dicarboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.87(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8370(18)
_cell_length_b                   15.488(3)
_cell_length_c                   15.155(3)
_cell_measurement_reflns_used    3904
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      2.55
_cell_measurement_theta_min      1.32
_cell_volume                     1995.2(7)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Bruker, 2000)'
_computing_data_reduction        'SHELXTL (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       2θ/ω
_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  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3742
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        0.01
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XPREP; Bruker, 2000)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.373
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.04P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                2135
_reflns_number_total             3499
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6122.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2204225
_cod_database_fobs_code          2204225
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 1.05337(9) 0.21342(4) 0.61157(5) 0.0641(3) Uani d . 1 S
S2 0.59847(10) 0.18067(5) 0.57724(5) 0.0718(3) Uani d . 1 S
C19 0.4391(3) 0.17435(17) 0.47455(19) 0.0583(8) Uani d . 1 C
N1 0.9838(3) 0.38965(13) 0.65753(14) 0.0538(6) Uani d . 1 N
H1 0.9106 0.3565 0.6262 0.065 Uiso calc R 1 H
N2 0.7382(3) 0.43443(13) 0.51209(15) 0.0495(6) Uani d . 1 N
N3 0.5225(3) 0.31273(14) 0.43400(15) 0.0565(6) Uani d . 1 N
H3 0.6012 0.3080 0.4819 0.068 Uiso calc R 1 H
O1 1.0619(2) 0.52912(11) 0.67501(12) 0.0578(5) Uani d . 1 O
O2 0.4087(2) 0.40713(12) 0.32000(13) 0.0618(5) Uani d . 1 O
C1 1.1470(3) 0.26533(17) 0.71643(18) 0.0538(7) Uani d . 1 C
C2 1.2614(3) 0.22392(18) 0.78626(19) 0.0620(8) Uani d . 1 C
H2 1.2886 0.1667 0.7800 0.074 Uiso calc R 1 H
C3 1.3326(4) 0.27010(19) 0.8645(2) 0.0664(9) Uani d . 1 C
H3A 1.4101 0.2439 0.9109 0.080 Uiso calc R 1 H
C4 1.2907(4) 0.35470(18) 0.8752(2) 0.0675(9) Uani d . 1 C
H4 1.3400 0.3847 0.9285 0.081 Uiso calc R 1 H
C5 1.1776(3) 0.39443(18) 0.80796(19) 0.0604(8) Uani d . 1 C
H5 1.1498 0.4513 0.8158 0.073 Uiso calc R 1 H
C6 1.1024(3) 0.34983(17) 0.72664(18) 0.0527(7) Uani d . 1 C
C7 0.9721(3) 0.47365(17) 0.63493(19) 0.0539(7) Uani d . 1 C
C8 0.8374(3) 0.49672(17) 0.55350(19) 0.0530(7) Uani d . 1 C
C9 0.8258(3) 0.58194(18) 0.52240(19) 0.0584(8) Uani d . 1 C
H9 0.8960 0.6239 0.5532 0.070 Uiso calc R 1 H
C10 0.7096(3) 0.60193(18) 0.4461(2) 0.0606(8) Uani d . 1 C
H10 0.7001 0.6580 0.4234 0.073 Uiso calc R 1 H
C11 0.6054(3) 0.53906(17) 0.4022(2) 0.0585(8) Uani d . 1 C
H11 0.5242 0.5522 0.3504 0.070 Uiso calc R 1 H
C12 0.6248(3) 0.45622(17) 0.4370(2) 0.0549(7) Uani d . 1 C
C13 0.5079(3) 0.38950(18) 0.39029(19) 0.0546(7) Uani d . 1 C
C14 0.4253(3) 0.23941(18) 0.41121(19) 0.0569(8) Uani d . 1 C
C15 0.3206(3) 0.23240(18) 0.3253(2) 0.0660(9) Uani d . 1 C
H15 0.3133 0.2763 0.2824 0.079 Uiso calc R 1 H
C16 0.2254(4) 0.15906(18) 0.3029(2) 0.0722(9) Uani d . 1 C
H16 0.1540 0.1533 0.2454 0.087 Uiso calc R 1 H
C17 0.2404(4) 0.09599(19) 0.3681(2) 0.0715(9) Uani d . 1 C
H17 0.1771 0.0472 0.3540 0.086 Uiso calc R 1 H
C18 0.3454(3) 0.10195(18) 0.4536(2) 0.0652(8) Uani d . 1 C
H18 0.3530 0.0580 0.4965 0.078 Uiso calc R 1 H
C20 1.0713(3) 0.10119(17) 0.6377(2) 0.0727(9) Uani d . 1 C
H20A 1.1774 0.0829 0.6437 0.109 Uiso calc R 1 H
H20B 1.0008 0.0692 0.5893 0.109 Uiso calc R 1 H
H20C 1.0453 0.0909 0.6943 0.109 Uiso calc R 1 H
C21 0.5491(4) 0.11973(18) 0.65366(19) 0.0720(9) Uani d . 1 C
H21A 0.4469 0.1364 0.6583 0.108 Uiso calc R 1 H
H21B 0.6247 0.1268 0.7122 0.108 Uiso calc R 1 H
H21C 0.5467 0.0604 0.6352 0.108 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'
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
_geom_angle_publ_flag
C1 S1 C20 104.59(13) y
C21 S2 C19 106.47(14) y
C14 C19 C18 120.2(3) ?
C14 C19 S2 117.7(2) ?
C18 C19 S2 121.6(2) ?
C7 N1 C6 127.2(2) ?
C7 N1 H1 116.4 ?
C6 N1 H1 116.4 ?
C12 N2 C8 117.3(2) ?
C13 N3 C14 128.3(2) ?
C13 N3 H3 115.9 ?
C14 N3 H3 115.9 ?
C6 C1 C2 121.0(2) ?
C6 C1 S1 116.8(2) ?
C2 C1 S1 122.2(2) ?
C3 C2 C1 118.4(3) ?
C3 C2 H2 120.8 ?
C1 C2 H2 120.8 ?
C2 C3 C4 121.2(3) ?
C2 C3 H3A 119.4 ?
C4 C3 H3A 119.4 ?
C5 C4 C3 120.4(3) ?
C5 C4 H4 119.8 ?
C3 C4 H4 119.8 ?
C4 C5 C6 120.4(3) ?
C4 C5 H5 119.8 ?
C6 C5 H5 119.8 ?
C1 C6 N1 120.5(2) ?
C1 C6 C5 118.6(2) ?
N1 C6 C5 120.9(2) ?
O1 C7 N1 124.4(3) ?
O1 C7 C8 120.3(2) ?
N1 C7 C8 115.3(2) ?
N2 C8 C9 123.0(3) ?
N2 C8 C7 118.9(2) ?
C9 C8 C7 118.0(3) ?
C10 C9 C8 118.2(3) ?
C10 C9 H9 120.9 ?
C8 C9 H9 120.9 ?
C9 C10 C11 120.0(3) ?
C9 C10 H10 120.0 ?
C11 C10 H10 120.0 ?
C10 C11 C12 118.4(3) ?
C10 C11 H11 120.8 ?
C12 C11 H11 120.8 ?
N2 C12 C11 123.0(3) ?
N2 C12 C13 119.2(2) ?
C11 C12 C13 117.7(3) ?
O2 C13 N3 125.4(3) ?
O2 C13 C12 120.0(3) ?
N3 C13 C12 114.6(2) ?
C19 C14 C15 120.7(3) ?
C19 C14 N3 119.2(2) ?
C15 C14 N3 120.1(3) ?
C14 C15 C16 119.8(3) ?
C14 C15 H15 120.1 ?
C16 C15 H15 120.1 ?
C17 C16 C15 118.1(3) ?
C17 C16 H16 121.0 ?
C15 C16 H16 121.0 ?
C16 C17 C18 122.6(3) ?
C16 C17 H17 118.7 ?
C18 C17 H17 118.7 ?
C17 C18 C19 118.7(3) ?
C17 C18 H18 120.7 ?
C19 C18 H18 120.7 ?
S1 C20 H20A 109.5 ?
S1 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
S1 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
S2 C21 H21A 109.5 ?
S2 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
S2 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.771(3) y
S1 C20 1.780(3) y
S2 C21 1.643(3) y
S2 C19 1.793(3) y
C19 C14 1.374(4) ?
C19 C18 1.378(3) ?
N1 C7 1.342(3) y
N1 C6 1.405(3) ?
N1 H1 0.8600 ?
N2 C12 1.338(3) ?
N2 C8 1.339(3) ?
N3 C13 1.350(3) y
N3 C14 1.409(3) ?
N3 H3 0.8600 ?
O1 C7 1.213(3) ?
O2 C13 1.211(3) ?
C1 C6 1.388(3) ?
C1 C2 1.403(4) ?
C2 C3 1.380(4) ?
C2 H2 0.9300 ?
C3 C4 1.383(4) ?
C3 H3A 0.9300 ?
C4 C5 1.363(4) ?
C4 H4 0.9300 ?
C5 C6 1.411(3) ?
C5 H5 0.9300 ?
C7 C8 1.505(4) ?
C8 C9 1.396(4) ?
C9 C10 1.356(4) ?
C9 H9 0.9300 ?
C10 C11 1.380(4) ?
C10 H10 0.9300 ?
C11 C12 1.380(3) ?
C11 H11 0.9300 ?
C12 C13 1.495(4) ?
C14 C15 1.380(3) ?
C15 C16 1.399(3) ?
C15 H15 0.9300 ?
C16 C17 1.370(4) ?
C16 H16 0.9300 ?
C17 C18 1.375(4) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 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
N1 H1 S1 . 0.86 2.59 2.924(2) 104 yes
N1 H1 N2 . 0.86 2.31 2.726(3) 110 yes
N3 H3 S2 . 0.86 2.45 2.924(2) 115 yes
N3 H3 N2 . 0.86 2.28 2.712(3) 111 yes
C2 H2 O1 2_746 0.93 2.50 3.374(3) 156 yes
C5 H5 O1 . 0.93 2.39 2.886(3) 113 ?
C15 H15 O2 . 0.93 2.21 2.823(3) 123 ?
C20 H20C O2 4_666 0.96 2.52 3.448(3) 163 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130494
