#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:47:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180096 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/42/7054271.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7054271
loop_
_publ_author_name
'Palmer, Joshua H.'
'Parkin, Gerard'
_publ_section_title
;
 Synthesis and Structural Characterization of 1-Arylimidazole-2-thiones
 and N,N'-Aryldiethoxyethylthioureas with Electronically Diverse
 Substituents: A Manifold of Hydrogen Bonding Networks.
;
_journal_issue                   9
_journal_name_full
'New journal of chemistry = Nouveau journal de chimie'
_journal_page_first              4071
_journal_page_last               4082
_journal_paper_doi               10.1039/C4NJ00521J
_journal_volume                  38
_journal_year                    2014
_chemical_formula_sum            'C14 H21 N3 O5 S'
_chemical_formula_weight         343.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.009(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.241(4)
_cell_length_b                   15.160(4)
_cell_length_c                   8.398(2)
_cell_measurement_reflns_used    2336
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.69
_cell_volume                     1654.7(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.1117
_diffrn_reflns_av_sigmaI/netI    0.1482
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8040
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1648
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0834
_reflns_number_gt                1820
_reflns_number_total             4104
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4nj00521j2.cif
_cod_data_source_block           tdaomeno2ph
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7054264--7054271.cif.

 Adding full bibliography for 7054264--7054403.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7054271
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S S 0.81190(6) 0.12435(5) 0.09685(9) 0.0305(2) Uani 1 1 d .
N1 N 0.7634(2) 0.19677(17) -0.1964(3) 0.0299(6) Uani 1 1 d .
H1 H 0.764(2) 0.2411(18) -0.258(3) 0.049(11) Uiso 1 1 d .
N2 N 0.8863(2) 0.27008(16) -0.0227(3) 0.0279(6) Uani 1 1 d .
H2 H 0.877(2) 0.3057(17) -0.092(3) 0.025(9) Uiso 1 1 d .
N3 N 0.92879(19) 0.44339(16) 0.1200(3) 0.0332(6) Uani 1 1 d .
O1 O 0.92252(16) 0.50180(13) 0.2185(3) 0.0450(6) Uani 1 1 d .
O2 O 0.88568(16) 0.44665(13) -0.0230(3) 0.0438(6) Uani 1 1 d .
O4 O 0.50075(15) 0.12340(13) -0.3277(2) 0.0355(5) Uani 1 1 d .
O5 O 0.57160(14) 0.26204(12) -0.3396(2) 0.0296(5) Uani 1 1 d .
O3 O 1.22319(14) 0.31689(12) 0.4799(2) 0.0329(5) Uani 1 1 d .
C1 C 0.9690(2) 0.28363(18) 0.1083(3) 0.0242(7) Uani 1 1 d .
C2 C 1.0327(2) 0.21467(18) 0.1739(3) 0.0284(7) Uani 1 1 d .
H2B H 1.0187 0.1569 0.1317 0.034 Uiso 1 1 calc R
C3 C 1.1149(2) 0.22757(18) 0.2971(3) 0.0289(7) Uani 1 1 d .
H3B H 1.1562 0.1788 0.3405 0.035 Uiso 1 1 calc R
C4 C 1.1386(2) 0.3114(2) 0.3595(3) 0.0282(7) Uani 1 1 d .
C5 C 1.0762(2) 0.38168(19) 0.3006(3) 0.0280(7) Uani 1 1 d .
H5A H 1.0899 0.4392 0.3444 0.034 Uiso 1 1 calc R
C6 C 0.9931(2) 0.36619(18) 0.1758(3) 0.0245(7) Uani 1 1 d .
C7 C 1.2477(2) 0.40117(17) 0.5525(3) 0.0382(8) Uani 1 1 d .
H7A H 1.3055 0.3953 0.6440 0.057 Uiso 1 1 calc R
H7B H 1.1877 0.4245 0.5915 0.057 Uiso 1 1 calc R
H7C H 1.2665 0.4417 0.4721 0.057 Uiso 1 1 calc R
C8 C 0.6784(2) 0.13724(18) -0.2518(3) 0.0294(7) Uani 1 1 d .
H8A H 0.6849 0.0849 -0.1800 0.035 Uiso 1 1 calc R
H8B H 0.6811 0.1169 -0.3629 0.035 Uiso 1 1 calc R
C9 C 0.5761(2) 0.18214(18) -0.2517(3) 0.0291(7) Uani 1 1 d .
H9A H 0.5674 0.1938 -0.1379 0.035 Uiso 1 1 calc R
C10 C 0.5518(2) 0.33843(18) -0.2508(4) 0.0373(8) Uani 1 1 d .
H10A H 0.6127 0.3523 -0.1662 0.045 Uiso 1 1 calc R
H10B H 0.4926 0.3275 -0.1971 0.045 Uiso 1 1 calc R
C11 C 0.5287(2) 0.41377(18) -0.3664(3) 0.0386(8) Uani 1 1 d .
H11A H 0.5101 0.4657 -0.3088 0.058 Uiso 1 1 calc R
H11B H 0.4712 0.3980 -0.4537 0.058 Uiso 1 1 calc R
H11C H 0.5895 0.4271 -0.4127 0.058 Uiso 1 1 calc R
C12 C 0.3980(2) 0.1540(2) -0.3337(4) 0.0473(9) Uani 1 1 d .
H12A H 0.3868 0.2096 -0.3963 0.057 Uiso 1 1 calc R
H12B H 0.3866 0.1656 -0.2225 0.057 Uiso 1 1 calc R
C13 C 0.3245(3) 0.0848(2) -0.4130(4) 0.0709(12) Uani 1 1 d .
H13A H 0.2539 0.1070 -0.4254 0.106 Uiso 1 1 calc R
H13B H 0.3320 0.0316 -0.3455 0.106 Uiso 1 1 calc R
H13C H 0.3394 0.0707 -0.5199 0.106 Uiso 1 1 calc R
C14 C 0.8209(2) 0.19976(18) -0.0470(3) 0.0253(7) Uani 1 1 d .
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
C14 N1 C8 126.2(3)
C14 N2 C1 127.3(3)
O1 N3 O2 123.5(3)
O1 N3 C6 118.0(2)
O2 N3 C6 118.5(2)
C9 O4 C12 113.7(2)
C9 O5 C10 114.6(2)
C4 O3 C7 117.4(2)
C6 C1 C2 116.3(3)
C6 C1 N2 122.3(3)
C2 C1 N2 121.4(3)
C3 C2 C1 121.9(3)
C2 C3 C4 120.5(3)
O3 C4 C5 124.8(3)
O3 C4 C3 115.6(3)
C5 C4 C3 119.7(3)
C4 C5 C6 118.3(3)
C1 C6 C5 123.3(3)
C1 C6 N3 121.0(2)
C5 C6 N3 115.7(3)
N1 C8 C9 111.1(2)
O4 C9 O5 110.6(2)
O4 C9 C8 105.9(2)
O5 C9 C8 109.5(2)
O5 C10 C11 108.4(2)
O4 C12 C13 108.8(3)
N1 C14 N2 113.4(3)
N1 C14 S 123.0(2)
N2 C14 S 123.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C14 1.684(3)
N1 C14 1.339(3)
N1 C8 1.448(3)
N2 C14 1.364(3)
N2 C1 1.412(3)
N3 O1 1.226(3)
N3 O2 1.228(3)
N3 C6 1.470(3)
O4 C9 1.397(3)
O4 C12 1.429(3)
O5 C9 1.414(3)
O5 C10 1.428(3)
O3 C4 1.360(3)
O3 C7 1.426(3)
C1 C6 1.386(4)
C1 C2 1.389(3)
C2 C3 1.365(3)
C3 C4 1.387(4)
C4 C5 1.381(4)
C5 C6 1.387(3)
C8 C9 1.516(4)
C10 C11 1.492(4)
C12 C13 1.497(4)
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
_geom_hbond_site_symmetry_A
N1 H1 S 0.85(3) 2.52(3) 3.348(3) 166(3) 4_565
N2 H2 S 0.78(2) 2.80(2) 3.541(3) 158(2) 4_565
