#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:54:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180322 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/36/7153640.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_7153640
loop_
_publ_author_name
'Haynes, Cally J. E.'
'Busschaert, Nathalie'
'Kirby, Isabelle L.'
'Herniman, Julie'
'Light, Mark E.'
'Wells, Neil J.'
'Marques, Igor'
'Félix, Vítor'
'Gale, Philip A.'
_publ_section_title
;
 Acylthioureas as anion transporters: the effect of intramolecular
 hydrogen bonding.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              62
_journal_page_last               72
_journal_paper_doi               10.1039/c3ob41522h
_journal_volume                  12
_journal_year                    2014
_chemical_compound_source        'Cally-Jo Elizabeth Haynes'
_chemical_formula_moiety         'C14 H20 N2 O2'
_chemical_formula_sum            'C14 H20 N2 O2'
_chemical_formula_weight         248.32
_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                 101.193(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.166(3)
_cell_length_b                   34.07(2)
_cell_length_c                   7.566(5)
_cell_measurement_reflns_used    3816
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.3
_cell_measurement_theta_min      2.4
_cell_volume                     1306.3(14)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics
;
Images generated using CrystalMaker: a crystal and molecular 
structures program for Mac and Windows. CrystalMaker Software Ltd, 
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.905
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4606
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lath
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                1589
_reflns_number_total             2078
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ob41522h.txt
_cod_data_source_block           2012sot0005
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7153640
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
O1 O 0.7762(2) 0.21454(4) 0.4437(2) 0.0203(4) Uani 1 1 d .
O2 O 1.4293(2) 0.14138(4) 0.5316(2) 0.0245(4) Uani 1 1 d .
N1 N 1.2159(3) 0.19982(5) 0.4918(3) 0.0181(4) Uani 1 1 d .
H1 H 1.3726 0.2106 0.5007 0.022 Uiso 1 1 calc R
N2 N 0.9817(3) 0.14053(4) 0.4854(3) 0.0181(4) Uani 1 1 d .
H2 H 0.8353 0.1540 0.4516 0.022 Uiso 1 1 calc R
C1 C 0.8892(4) 0.29465(5) 0.3916(3) 0.0186(5) Uani 1 1 d .
H1A H 0.7238 0.2853 0.3284 0.022 Uiso 1 1 calc R
C2 C 0.9389(4) 0.33457(6) 0.3978(3) 0.0222(5) Uani 1 1 d .
H2A H 0.8104 0.3524 0.3373 0.027 Uiso 1 1 calc R
C3 C 1.1791(4) 0.34828(6) 0.4935(3) 0.0224(5) Uani 1 1 d .
H3 H 1.2145 0.3757 0.4989 0.027 Uiso 1 1 calc R
C4 C 1.3663(4) 0.32238(6) 0.5805(3) 0.0222(6) Uani 1 1 d .
H4 H 1.5287 0.3320 0.6472 0.027 Uiso 1 1 calc R
C5 C 1.3190(4) 0.28232(6) 0.5715(3) 0.0194(5) Uani 1 1 d .
H5 H 1.4502 0.2646 0.6296 0.023 Uiso 1 1 calc R
C6 C 1.0775(4) 0.26797(5) 0.4764(3) 0.0169(5) Uani 1 1 d .
C7 C 1.0089(4) 0.22544(6) 0.4683(3) 0.0169(5) Uani 1 1 d .
C8 C 1.2147(4) 0.15834(6) 0.5040(3) 0.0181(5) Uani 1 1 d .
C9 C 0.9693(4) 0.09851(5) 0.5213(3) 0.0198(5) Uani 1 1 d .
H9A H 0.7982 0.0926 0.5559 0.024 Uiso 1 1 calc R
H9B H 1.1109 0.0918 0.6250 0.024 Uiso 1 1 calc R
C10 C 0.9983(4) 0.07276(6) 0.3623(3) 0.0215(6) Uani 1 1 d .
H10A H 1.0054 0.0450 0.4011 0.026 Uiso 1 1 calc R
H10B H 1.1683 0.0790 0.3267 0.026 Uiso 1 1 calc R
C11 C 0.7767(4) 0.07743(6) 0.1979(3) 0.0227(6) Uani 1 1 d .
H11A H 0.6058 0.0724 0.2344 0.027 Uiso 1 1 calc R
H11B H 0.7753 0.1049 0.1548 0.027 Uiso 1 1 calc R
C12 C 0.8020(4) 0.05004(6) 0.0435(3) 0.0230(6) Uani 1 1 d .
H12A H 0.8087 0.0227 0.0880 0.028 Uiso 1 1 calc R
H12B H 0.9714 0.0555 0.0056 0.028 Uiso 1 1 calc R
C13 C 0.5795(4) 0.05339(6) -0.1208(3) 0.0250(6) Uani 1 1 d .
H13A H 0.4090 0.0492 -0.0824 0.030 Uiso 1 1 calc R
H13B H 0.5786 0.0803 -0.1698 0.030 Uiso 1 1 calc R
C14 C 0.6021(4) 0.02426(6) -0.2697(4) 0.0291(6) Uani 1 1 d .
H14A H 0.7695 0.0284 -0.3096 0.044 Uiso 1 1 calc R
H14B H 0.4551 0.0282 -0.3715 0.044 Uiso 1 1 calc R
H14C H 0.5961 -0.0026 -0.2238 0.044 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0134(7) 0.0228(8) 0.0247(12) 0.0006(6) 0.0036(7) -0.0014(6)
O2 0.0153(7) 0.0213(8) 0.0376(13) 0.0012(7) 0.0067(7) 0.0032(6)
N1 0.0119(8) 0.0178(9) 0.0254(14) 0.0000(7) 0.0054(8) -0.0006(7)
N2 0.0129(8) 0.0176(9) 0.0237(14) 0.0016(7) 0.0033(8) 0.0021(7)
C1 0.0159(10) 0.0234(12) 0.0173(16) -0.0008(9) 0.0051(10) -0.0005(9)
C2 0.0236(11) 0.0220(12) 0.0223(17) 0.0041(9) 0.0080(10) 0.0052(9)
C3 0.0269(11) 0.0177(11) 0.0256(17) -0.0013(9) 0.0128(11) -0.0008(9)
C4 0.0180(10) 0.0251(13) 0.0249(18) -0.0027(9) 0.0077(10) -0.0043(9)
C5 0.0165(10) 0.0216(12) 0.0206(17) -0.0012(9) 0.0047(10) 0.0021(9)
C6 0.0168(10) 0.0179(11) 0.0179(15) 0.0001(9) 0.0078(10) 0.0010(9)
C7 0.0179(10) 0.0230(12) 0.0103(15) 0.0000(8) 0.0039(9) 0.0014(9)
C8 0.0173(10) 0.0219(12) 0.0161(16) -0.0025(9) 0.0054(10) 0.0021(9)
C9 0.0175(10) 0.0183(11) 0.0242(16) 0.0032(9) 0.0053(10) 0.0000(9)
C10 0.0172(10) 0.0177(11) 0.0304(18) -0.0020(9) 0.0068(10) 0.0002(9)
C11 0.0192(10) 0.0181(12) 0.0318(19) -0.0002(9) 0.0079(11) 0.0014(9)
C12 0.0195(10) 0.0199(12) 0.0310(19) -0.0020(9) 0.0083(11) -0.0009(9)
C13 0.0230(11) 0.0230(12) 0.0295(19) -0.0006(10) 0.0063(11) 0.0004(9)
C14 0.0338(12) 0.0265(13) 0.0281(19) -0.0009(10) 0.0083(12) 0.0000(10)
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C8 129.32(16)
C8 N2 C9 119.92(16)
C2 C1 C6 121.16(19)
C1 C2 C3 119.28(19)
C4 C3 C2 120.40(19)
C3 C4 C5 120.4(2)
C4 C5 C6 120.00(19)
C1 C6 C5 118.74(18)
C1 C6 C7 118.46(18)
C5 C6 C7 122.76(18)
O1 C7 N1 122.77(18)
O1 C7 C6 120.95(16)
N1 C7 C6 116.28(16)
O2 C8 N2 124.74(19)
O2 C8 N1 117.66(17)
N2 C8 N1 117.60(17)
N2 C9 C10 113.81(18)
C9 C10 C11 114.29(16)
C12 C11 C10 113.55(16)
C11 C12 C13 114.63(17)
C14 C13 C12 113.61(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.237(2)
O2 C8 1.232(2)
N1 C7 1.365(2)
N1 C8 1.416(3)
N2 C8 1.331(2)
N2 C9 1.461(2)
C1 C2 1.383(3)
C1 C6 1.393(3)
C2 C3 1.391(3)
C3 C4 1.378(3)
C4 C5 1.386(3)
C5 C6 1.402(3)
C6 C7 1.490(3)
C9 C10 1.520(3)
C10 C11 1.526(3)
C11 C12 1.520(3)
C12 C13 1.524(3)
C13 C14 1.523(3)
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 O1 0.88 2.21 3.029(3) 153.8 1_655
N2 H2 O1 0.88 2.08 2.730(2) 129.7 .
N2 H2 O2 0.88 2.33 2.941(3) 126.4 1_455
