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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/66/7106613.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_7106613
loop_
_publ_author_name
'Marco Wenzel'
'Mark E. Light'
'Anthony P. Davis'
'Philip A. Gale'
_publ_section_title
;
 Thiourea isosteres as anion receptors and transmembrane transporters
;
_journal_name_full               Chem.Commun.
_journal_page_first              7641
_journal_paper_doi               10.1039/c1cc12439k
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C14 H20 N4'
_chemical_formula_sum            'C14 H20 N4'
_chemical_formula_weight         244.34
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.2071(2)
_cell_length_b                   11.2105(3)
_cell_length_c                   24.2602(6)
_cell_measurement_reflns_used    3561
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     2776.01(11)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on \\k-goniostat'
_diffrn_measurement_method       '\\f & \\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27023
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0099(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²\\l³/sin(2\\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0546
_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/[\\s²(Fo²)+(0.0549P)²+1.7032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1379
_reflns_number_gt                2806
_reflns_number_total             3585
_reflns_threshold_expression     >2\\s(I)
_cod_data_source_file            c1cc12439k.txt
_cod_data_source_block           2010mw0001
_cod_database_code               7106613
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6250(3) 0.6891(3) -0.02772(12) 0.0215(6) Uani 1 1 d . . .
C2 C 0.5003(3) 0.6563(3) -0.04543(13) 0.0251(7) Uani 1 1 d . . .
H2 H 0.4621 0.5867 -0.0321 0.030 Uiso 1 1 calc R . .
C3 C 0.4327(3) 0.7268(3) -0.08278(13) 0.0278(7) Uani 1 1 d . . .
H3 H 0.3488 0.7053 -0.0940 0.033 Uiso 1 1 calc R . .
C4 C 0.4901(3) 0.8295(3) -0.10343(13) 0.0289(7) Uani 1 1 d . . .
H4 H 0.4456 0.8761 -0.1290 0.035 Uiso 1 1 calc R . .
C5 C 0.6137(3) 0.8624(3) -0.08597(13) 0.0270(7) Uani 1 1 d . . .
H5 H 0.6517 0.9318 -0.0996 0.032 Uiso 1 1 calc R . .
C6 C 0.6815(3) 0.7930(3) -0.04826(13) 0.0258(7) Uani 1 1 d . . .
H6 H 0.7646 0.8158 -0.0367 0.031 Uiso 1 1 calc R . .
C7 C 0.6560(3) 0.5785(3) 0.05912(12) 0.0215(6) Uani 1 1 d . . .
C8 C 0.8146(3) 0.4363(3) 0.06534(12) 0.0219(6) Uani 1 1 d . . .
C9 C 0.4941(3) 0.5979(3) 0.13465(13) 0.0305(7) Uani 1 1 d . . .
H9A H 0.5335 0.5237 0.1468 0.037 Uiso 1 1 calc R . .
H9B H 0.4008 0.5841 0.1304 0.037 Uiso 1 1 calc R . .
C10 C 0.5142(4) 0.6902(4) 0.17825(16) 0.0481(10) Uani 1 1 d . . .
H10A H 0.4776 0.7650 0.1653 0.058 Uiso 1 1 calc R . .
H10B H 0.4655 0.6667 0.2108 0.058 Uiso 1 1 calc R . .
C11 C 0.6502(4) 0.7101(4) 0.19392(18) 0.0528(11) Uani 1 1 d . . .
H11A H 0.6999 0.7301 0.1611 0.063 Uiso 1 1 calc R . .
H11B H 0.6856 0.6364 0.2086 0.063 Uiso 1 1 calc R . .
C12 C 0.6702(4) 0.8106(4) 0.23738(17) 0.0490(10) Uani 1 1 d . . .
H12A H 0.6365 0.8850 0.2227 0.059 Uiso 1 1 calc R . .
H12B H 0.6201 0.7915 0.2702 0.059 Uiso 1 1 calc R . .
C13 C 0.8099(4) 0.8271(4) 0.25285(16) 0.0465(10) Uani 1 1 d . . .
H13A H 0.8589 0.8483 0.2200 0.056 Uiso 1 1 calc R . .
H13B H 0.8438 0.7516 0.2661 0.056 Uiso 1 1 calc R . .
C14 C 0.8342(4) 0.9212(4) 0.29633(17) 0.0456(10) Uani 1 1 d . . .
H14A H 0.9263 0.9260 0.3039 0.068 Uiso 1 1 calc R . .
H14B H 0.7882 0.9002 0.3295 0.068 Uiso 1 1 calc R . .
H14C H 0.8034 0.9970 0.2833 0.068 Uiso 1 1 calc R . .
C15 C 0.2326(3) 0.3198(3) 0.03230(12) 0.0224(7) Uani 1 1 d . . .
C16 C 0.3525(3) 0.3587(3) 0.05259(13) 0.0249(7) Uani 1 1 d . . .
H16 H 0.3855 0.4326 0.0420 0.030 Uiso 1 1 calc R . .
C17 C 0.4230(3) 0.2872(3) 0.08875(14) 0.0301(7) Uani 1 1 d . . .
H17 H 0.5043 0.3124 0.1016 0.036 Uiso 1 1 calc R . .
C18 C 0.3727(3) 0.1788(3) 0.10574(13) 0.0319(8) Uani 1 1 d . . .
H18 H 0.4196 0.1315 0.1303 0.038 Uiso 1 1 calc R . .
C19 C 0.2524(4) 0.1409(3) 0.08603(14) 0.0335(8) Uani 1 1 d . . .
H19 H 0.2184 0.0681 0.0976 0.040 Uiso 1 1 calc R . .
C20 C 0.1822(3) 0.2106(3) 0.04924(14) 0.0273(7) Uani 1 1 d . . .
H20 H 0.1018 0.1845 0.0359 0.033 Uiso 1 1 calc R . .
C21 C 0.2051(3) 0.4305(3) -0.05437(12) 0.0212(6) Uani 1 1 d . . .
C22 C 0.0375(3) 0.5633(3) -0.06521(12) 0.0224(6) Uani 1 1 d . . .
C23 C 0.3791(3) 0.4208(3) -0.12522(12) 0.0251(7) Uani 1 1 d . . .
H23A H 0.4683 0.4467 -0.1185 0.030 Uiso 1 1 calc R . .
H23B H 0.3312 0.4877 -0.1406 0.030 Uiso 1 1 calc R . .
C24 C 0.3804(3) 0.3191(3) -0.16685(13) 0.0259(7) Uani 1 1 d . . .
H24A H 0.4286 0.2524 -0.1514 0.031 Uiso 1 1 calc R . .
H24B H 0.4261 0.3451 -0.1998 0.031 Uiso 1 1 calc R . .
C25 C 0.2426(3) 0.2770(3) -0.18279(14) 0.0318(8) Uani 1 1 d . . .
H25A H 0.1948 0.2564 -0.1496 0.038 Uiso 1 1 calc R . .
H25B H 0.1966 0.3421 -0.2006 0.038 Uiso 1 1 calc R . .
C26 C 0.2444(4) 0.1692(3) -0.22148(13) 0.0319(8) Uani 1 1 d . . .
H26A H 0.2896 0.1041 -0.2033 0.038 Uiso 1 1 calc R . .
H26B H 0.1549 0.1439 -0.2280 0.038 Uiso 1 1 calc R . .
C27 C 0.3098(3) 0.1921(3) -0.27661(13) 0.0314(8) Uani 1 1 d . . .
H27A H 0.2681 0.2601 -0.2940 0.038 Uiso 1 1 calc R . .
H27B H 0.4010 0.2125 -0.2704 0.038 Uiso 1 1 calc R . .
C28 C 0.3030(4) 0.0865(3) -0.31524(16) 0.0437(10) Uani 1 1 d . . .
H28A H 0.3464 0.1059 -0.3492 0.066 Uiso 1 1 calc R . .
H28B H 0.2130 0.0674 -0.3226 0.066 Uiso 1 1 calc R . .
H28C H 0.3454 0.0191 -0.2985 0.066 Uiso 1 1 calc R . .
N1 N 0.6965(2) 0.6145(2) 0.00877(10) 0.0223(5) Uani 1 1 d . . .
H1 H 0.7720 0.5900 -0.0021 0.027 Uiso 1 1 calc R . .
N2 N 0.5491(2) 0.6296(2) 0.08099(10) 0.0239(6) Uani 1 1 d . . .
H7 H 0.5105 0.6845 0.0623 0.029 Uiso 1 1 calc R . .
N3 N 0.7165(2) 0.4936(2) 0.08830(10) 0.0245(6) Uani 1 1 d . . .
N4 N 0.9024(3) 0.3779(2) 0.05000(11) 0.0270(6) Uani 1 1 d . . .
N5 N 0.1597(2) 0.3918(2) -0.00503(10) 0.0230(6) Uani 1 1 d . . .
H15 H 0.0816 0.4121 0.0044 0.028 Uiso 1 1 calc R . .
N6 N 0.3187(2) 0.3858(2) -0.07281(10) 0.0227(6) Uani 1 1 d . . .
H21 H 0.3583 0.3338 -0.0528 0.027 Uiso 1 1 calc R . .
N7 N 0.1426(3) 0.5109(2) -0.08504(10) 0.0243(6) Uani 1 1 d . . .
N8 N -0.0553(3) 0.6162(2) -0.05204(11) 0.0277(6) 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 0.0000 '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 0.0000 '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
_geom_angle_publ_flag
C6 C1 C2 119.3(3) . . ?
C6 C1 N1 120.2(3) . . ?
C2 C1 N1 120.4(3) . . ?
C3 C2 C1 120.4(3) . . ?
C4 C3 C2 120.0(3) . . ?
C5 C4 C3 119.9(3) . . ?
C4 C5 C6 120.5(3) . . ?
C5 C6 C1 120.0(3) . . ?
N3 C7 N2 118.0(3) . . ?
N3 C7 N1 123.3(3) . . ?
N2 C7 N1 118.6(3) . . ?
N4 C8 N3 172.7(3) . . ?
N2 C9 C10 114.1(3) . . ?
C11 C10 C9 114.9(4) . . ?
C10 C11 C12 114.4(4) . . ?
C13 C12 C11 112.8(4) . . ?
C12 C13 C14 114.9(4) . . ?
C16 C15 C20 119.8(3) . . ?
C16 C15 N5 120.5(3) . . ?
C20 C15 N5 119.6(3) . . ?
C17 C16 C15 119.9(3) . . ?
C18 C17 C16 120.2(3) . . ?
C17 C18 C19 119.7(3) . . ?
C18 C19 C20 120.5(3) . . ?
C19 C20 C15 119.7(3) . . ?
N7 C21 N6 118.7(3) . . ?
N7 C21 N5 123.1(3) . . ?
N6 C21 N5 118.1(3) . . ?
N8 C22 N7 173.6(3) . . ?
N6 C23 C24 112.2(3) . . ?
C23 C24 C25 112.9(3) . . ?
C26 C25 C24 112.8(3) . . ?
C27 C26 C25 114.3(3) . . ?
C28 C27 C26 113.2(3) . . ?
C7 N1 C1 125.6(3) . . ?
C7 N2 C9 124.1(3) . . ?
C8 N3 C7 118.4(3) . . ?
C21 N5 C15 124.4(3) . . ?
C21 N6 C23 123.6(3) . . ?
C22 N7 C21 119.3(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.392(4) . ?
C1 C2 1.393(4) . ?
C1 N1 1.420(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.385(5) . ?
C4 C5 1.381(5) . ?
C5 C6 1.386(4) . ?
C7 N3 1.337(4) . ?
C7 N2 1.342(4) . ?
C7 N1 1.351(4) . ?
C8 N4 1.171(4) . ?
C8 N3 1.314(4) . ?
C9 N2 1.462(4) . ?
C9 C10 1.494(5) . ?
C10 C11 1.457(6) . ?
C11 C12 1.557(6) . ?
C12 C13 1.486(6) . ?
C13 C14 1.512(5) . ?
C15 C16 1.389(4) . ?
C15 C20 1.390(4) . ?
C15 N5 1.423(4) . ?
C16 C17 1.389(4) . ?
C17 C18 1.382(5) . ?
C18 C19 1.385(5) . ?
C19 C20 1.385(5) . ?
C21 N7 1.332(4) . ?
C21 N6 1.339(4) . ?
C21 N5 1.355(4) . ?
C22 N8 1.162(4) . ?
C22 N7 1.315(4) . ?
C23 N6 1.467(4) . ?
C23 C24 1.523(4) . ?
C24 C25 1.533(4) . ?
C25 C26 1.531(4) . ?
C26 C27 1.517(5) . ?
C27 C28 1.512(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350425
