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#$Date: 2022-05-17 11:14:06 +0300 (Tue, 17 May 2022) $
#$Revision: 275480 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105277.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_8105277
loop_
_publ_author_name
'Al-Qawasmeh, Raed A.'
'Al-Soud, Yaseen A.'
'Alhelal, Kafa A. S.'
'Khanfar, Monther A.'
_publ_section_title
;
 Crystal structure of
 3-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-ylthio)-propanoic acid,
 C15H17N3O4S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              751
_journal_page_last               753
_journal_paper_doi               10.1515/ncrs-2020-0003
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C15 H17 N3 O4 S'
_chemical_formula_sum            'C15 H17 N3 O4 S'
_chemical_formula_weight         335.38
_chemical_melting_point          440
_chemical_name_systematic
;
3-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-ylthio)-propanoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 79.704(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7938(5)
_cell_length_b                   10.3071(4)
_cell_length_c                   18.0413(7)
_cell_measurement_reflns_used    3481
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0610
_cell_measurement_theta_min      4.0630
_cell_volume                     1608.91(13)
_computing_cell_refinement       'CrysAlisPro, Ver. 1.171.38.46 [1]'
_computing_data_collection       'CrysAlisPro, Ver. 1.171.38.46 [1]'
_computing_data_reduction        'CrysAlisPro, Ver. 1.171.38.46 [1]'
_computing_molecular_graphics    'Olex2 [2]'
_computing_publication_material  'Olex2 [2]'
_computing_structure_refinement  'Olex2 [2], ShelXL [4]'
_computing_structure_solution    'Olex2 [2], ShelXT [3]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -15.00  54.00   1.00   20.00    --  -16.36  19.00 -93.00   69
  2  ω    -66.00   0.00   1.00   20.00    --  -16.36 -19.00  99.00   66
  3  ω     23.00  79.00   1.00   20.00    --   16.98-142.00  76.00   56
  4  ω    -20.00   7.00   1.00   20.00    --  -16.36 -99.00-120.00   27
  5  ω    -17.00  41.00   1.00   20.00    --  -16.36  57.00 120.00   58
  6  ω    -88.00 -59.00   1.00   20.00    --  -16.36 178.00-180.00   29
  7  ω     -5.00  70.00   1.00   20.00    --   16.98  77.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0790304000
_diffrn_orient_matrix_UB_12      -0.0176538000
_diffrn_orient_matrix_UB_13      -0.0052952000
_diffrn_orient_matrix_UB_21      -0.0027845000
_diffrn_orient_matrix_UB_22      0.0018590000
_diffrn_orient_matrix_UB_23      0.0395544000
_diffrn_orient_matrix_UB_31      -0.0211593000
_diffrn_orient_matrix_UB_32      -0.0665287000
_diffrn_orient_matrix_UB_33      0.0025323000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13496
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.438
_diffrn_reflns_theta_min         3.029
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 [1]
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0610P)²+0.9860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2949
_reflns_number_total             3872
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0003_suppl.cif
_cod_data_source_block           exp_2513
_cod_database_code               8105277
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C16(H16a,H16b), C13(H13a,H13b), C6(H6a,H6b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C8(H8), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.3431(2) 0.5935(2) 0.12722(11) 0.0415(5) Uani 1 1 d . . . . .
C4 C 0.5704(2) 0.57847(18) 0.14962(10) 0.0347(4) Uani 1 1 d . . . . .
C5 C 0.4858(2) 0.49883(17) 0.20211(10) 0.0346(4) Uani 1 1 d . . . . .
C6 C 0.1992(3) 0.4443(3) 0.22675(14) 0.0572(6) Uani 1 1 d . . . . .
H6A H 0.2280 0.3607 0.2446 0.069 Uiso 1 1 calc R . . . .
H6B H 0.1286 0.4289 0.1920 0.069 Uiso 1 1 calc R . . . .
C7 C 0.1166(3) 0.5209(2) 0.29258(12) 0.0436(5) Uani 1 1 d . . . . .
C8 C 0.0151(3) 0.4556(3) 0.34764(14) 0.0591(7) Uani 1 1 d . . . . .
H8 H -0.0016 0.3671 0.3430 0.071 Uiso 1 1 calc R . . . .
C9 C -0.0615(3) 0.5232(4) 0.40970(17) 0.0784(9) Uani 1 1 d . . . . .
H9 H -0.1304 0.4795 0.4464 0.094 Uiso 1 1 calc R . . . .
C10 C -0.0372(3) 0.6529(4) 0.41781(17) 0.0754(9) Uani 1 1 d . . . . .
H10 H -0.0886 0.6969 0.4599 0.090 Uiso 1 1 calc R . . . .
C11 C 0.0630(3) 0.7177(3) 0.36372(16) 0.0633(7) Uani 1 1 d . . . . .
H11 H 0.0803 0.8059 0.3692 0.076 Uiso 1 1 calc R . . . .
C12 C 0.1386(3) 0.6525(2) 0.30091(13) 0.0535(6) Uani 1 1 d . . . . .
H12 H 0.2049 0.6976 0.2638 0.064 Uiso 1 1 calc R . . . .
C13 C 0.2072(3) 0.6336(3) 0.09344(15) 0.0556(6) Uani 1 1 d . . . . .
H13A H 0.1136 0.6226 0.1305 0.067 Uiso 1 1 calc R . . . .
H13B H 0.2167 0.7249 0.0803 0.067 Uiso 1 1 calc R . . . .
C14 C 0.1942(4) 0.5568(4) 0.02478(17) 0.0802(9) Uani 1 1 d . . . . .
H14A H 0.2882 0.5647 -0.0113 0.120 Uiso 1 1 calc GR . . . .
H14B H 0.1093 0.5890 0.0032 0.120 Uiso 1 1 calc GR . . . .
H14C H 0.1766 0.4672 0.0382 0.120 Uiso 1 1 calc GR . . . .
C15 C 0.4653(3) 0.4775(2) 0.35832(10) 0.0454(5) Uani 1 1 d . . . . .
H15A H 0.3552 0.4926 0.3626 0.055 Uiso 1 1 calc R . . . .
H15B H 0.4801 0.4213 0.3996 0.055 Uiso 1 1 calc R . . . .
C16 C 0.5440(3) 0.6050(2) 0.36621(11) 0.0457(5) Uani 1 1 d . . . . .
H16A H 0.5199 0.6653 0.3287 0.055 Uiso 1 1 calc R . . . .
H16B H 0.6550 0.5922 0.3572 0.055 Uiso 1 1 calc R . . . .
C17 C 0.4931(3) 0.6619(2) 0.44351(11) 0.0396(4) Uani 1 1 d . . . . .
N1 N 0.3383(2) 0.50834(17) 0.18600(9) 0.0410(4) Uani 1 1 d . . . . .
N3 N 0.4842(2) 0.63536(17) 0.10350(9) 0.0393(4) Uani 1 1 d . . . . .
N4 N 0.7315(2) 0.61092(19) 0.14151(11) 0.0493(5) Uani 1 1 d . . . . .
O1 O 0.7821(2) 0.6940(2) 0.09657(12) 0.0772(6) Uani 1 1 d . . . . .
O2 O 0.8101(3) 0.5537(3) 0.18006(15) 0.1054(9) Uani 1 1 d . . . . .
O3 O 0.3872(2) 0.62118(17) 0.48889(9) 0.0614(5) Uani 1 1 d . . . . .
O4 O 0.5777(2) 0.76200(18) 0.45648(9) 0.0647(5) Uani 1 1 d . . . . .
H4 H 0.5482 0.7882 0.4996 0.097 Uiso 1 1 calc GR . . . .
S1 S 0.53533(9) 0.39477(5) 0.26997(3) 0.0542(2) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 S1 C15 103.87(9) . .
C17 O4 H4 109.5 . .
C2 N3 C4 104.94(17) . .
C5 N1 C6 126.35(19) . .
C2 N1 C5 107.93(16) . .
C2 N1 C6 125.7(2) . .
O1 N4 C4 118.1(2) . .
O1 N4 O2 123.3(2) . .
O2 N4 C4 118.6(2) . .
N3 C4 N4 119.07(18) . .
N3 C4 C5 112.97(18) . .
C5 C4 N4 127.88(19) . .
N1 C5 S1 123.64(15) . .
C4 C5 S1 133.06(17) . .
C4 C5 N1 103.09(16) . .
O4 C17 C16 112.71(18) . .
O3 C17 O4 123.11(19) . .
O3 C17 C16 124.2(2) . .
N3 C2 N1 111.04(18) . .
N3 C2 C13 123.74(19) . .
N1 C2 C13 125.2(2) . .
S1 C15 H15A 108.8 . .
S1 C15 H15B 108.8 . .
H15A C15 H15B 107.7 . .
C16 C15 S1 113.85(15) . .
C16 C15 H15A 108.8 . .
C16 C15 H15B 108.8 . .
C12 C7 C6 123.04(19) . .
C12 C7 C8 118.9(2) . .
C8 C7 C6 118.1(2) . .
C17 C16 H16A 109.4 . .
C17 C16 H16B 109.4 . .
C15 C16 C17 111.26(18) . .
C15 C16 H16A 109.4 . .
C15 C16 H16B 109.4 . .
H16A C16 H16B 108.0 . .
C7 C12 H12 119.6 . .
C11 C12 C7 120.7(2) . .
C11 C12 H12 119.6 . .
C12 C11 H11 119.9 . .
C10 C11 C12 120.1(3) . .
C10 C11 H11 119.9 . .
C2 C13 H13A 109.2 . .
C2 C13 H13B 109.2 . .
H13A C13 H13B 107.9 . .
C14 C13 C2 112.2(2) . .
C14 C13 H13A 109.2 . .
C14 C13 H13B 109.2 . .
N1 C6 C7 113.70(18) . .
N1 C6 H6A 108.8 . .
N1 C6 H6B 108.8 . .
C7 C6 H6A 108.8 . .
C7 C6 H6B 108.8 . .
H6A C6 H6B 107.7 . .
C7 C8 H8 120.2 . .
C7 C8 C9 119.5(3) . .
C9 C8 H8 120.2 . .
C11 C10 H10 120.2 . .
C9 C10 C11 119.7(3) . .
C9 C10 H10 120.2 . .
C8 C9 H9 119.5 . .
C10 C9 C8 121.0(3) . .
C10 C9 H9 119.5 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C5 1.7407(19) .
S1 C15 1.816(2) .
O4 H4 0.8200 .
O4 C17 1.317(3) .
O3 C17 1.200(3) .
N3 C4 1.355(3) .
N3 C2 1.311(3) .
N1 C5 1.382(3) .
N1 C2 1.372(3) .
N1 C6 1.467(3) .
N4 O1 1.208(3) .
N4 C4 1.438(3) .
N4 O2 1.217(3) .
C4 C5 1.368(3) .
C17 C16 1.505(3) .
C2 C13 1.493(3) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 C16 1.503(3) .
C7 C12 1.381(3) .
C7 C6 1.501(3) .
C7 C8 1.385(3) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C12 H12 0.9300 .
C12 C11 1.381(3) .
C11 H11 0.9300 .
C11 C10 1.367(4) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C14 1.492(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C8 H8 0.9300 .
C8 C9 1.387(4) .
C10 H10 0.9300 .
C10 C9 1.365(5) .
C9 H9 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
