#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:19:53 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180500 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/69/7216909.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_7216909
loop_
_publ_author_name
'Kyne, Graham M.'
'Light, Mark E.'
'Hursthouse, Mike B.'
'Mendoza, Javier de'
'Kilburn, Jeremy D.'
_publ_section_title
;
 Enantioselective amino acid recognition using acyclic thiourea receptors
;
_journal_issue                   11
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1258
_journal_paper_doi               10.1039/b102298a
_journal_year                    2001
_chemical_formula_sum            'C23 H32 N6 O2 S'
_chemical_formula_weight         456.61
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.975(2)
_cell_angle_beta                 79.123(2)
_cell_angle_gamma                65.1932(12)
_cell_formula_units_Z            2
_cell_length_a                   9.4566(3)
_cell_length_b                   10.7149(4)
_cell_length_c                   13.2326(4)
_cell_measurement_reflns_used    4737
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.10
_cell_volume                     1190.56(7)
_computing_cell_refinement       'DENZO & SCALEPACK'
_computing_data_collection       'COLLECT and DENZO'
_computing_data_reduction        DENZO
_computing_molecular_graphics    CAMERON
_computing_publication_material  WINGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius kappac CCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18090
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0228P)²+0.8702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                3975
_reflns_number_total             4737
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b102298a.txt
_cod_data_source_block           s92
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multiscan'
changed to 'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0228P)^2^+0.8702P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0228P)^2^+0.8702P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7216909
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_calc_flag
S1 S 0.72083(6) 0.10694(5) 0.40123(4) 0.03051(15) Uani 1 d
O2 O 1.35620(15) 0.50588(13) 0.33828(10) 0.0266(3) Uani 1 d
N5 N 1.02594(17) 0.42400(15) 0.34957(11) 0.0222(3) Uani 1 d
O1 O 0.15813(17) 0.60678(15) 0.96759(11) 0.0385(4) Uani 1 d
N6 N 1.15029(19) 0.58644(16) 0.25466(12) 0.0261(3) Uani 1 d
N4 N 0.69807(18) 0.35471(16) 0.46105(12) 0.0248(3) Uani 1 d
N2 N 0.38835(17) 0.34157(15) 0.76433(11) 0.0226(3) Uani 1 d
N1 N 0.37059(18) 0.57952(16) 0.84151(12) 0.0253(3) Uani 1 d
N3 N 0.57049(18) 0.26331(16) 0.57841(12) 0.0261(3) Uani 1 d
C6 C 0.2790(2) 0.40159(19) 0.85211(13) 0.0238(4) Uani 1 d
C7 C 0.1834(2) 0.3430(2) 0.90267(15) 0.0289(4) Uani 1 d
C18 C 1.1666(2) 0.40938(17) 0.36880(13) 0.0220(4) Uani 1 d
C14 C 0.9656(2) 0.33872(18) 0.39153(13) 0.0229(4) Uani 1 d
C19 C 1.2321(2) 0.50563(17) 0.31896(13) 0.0222(4) Uani 1 d
C11 C 0.5246(2) 0.15931(19) 0.62401(14) 0.0251(4) Uani 1 d
C5 C 0.2638(2) 0.53935(19) 0.89282(14) 0.0254(4) Uani 1 d
C10 C 0.4032(2) 0.22151(18) 0.72386(13) 0.0231(4) Uani 1 d
C17 C 1.2513(2) 0.31223(19) 0.42915(15) 0.0275(4) Uani 1 d
C12 C 0.6614(2) 0.24731(18) 0.48385(13) 0.0218(4) Uani 1 d
C16 C 1.1882(2) 0.2230(2) 0.47141(16) 0.0309(4) Uani 1 d
C13 C 0.8067(2) 0.3591(2) 0.36956(14) 0.0267(4) Uani 1 d
C20 C 1.1903(2) 0.69156(19) 0.20328(15) 0.0262(4) Uani 1 d
C15 C 1.0452(2) 0.23597(19) 0.45225(15) 0.0273(4) Uani 1 d
C8 C 0.2016(2) 0.2170(2) 0.86103(15) 0.0313(4) Uani 1 d
C21 C 1.1152(2) 0.8280(2) 0.26959(15) 0.0281(4) Uani 1 d
C9 C 0.3120(2) 0.1550(2) 0.77079(15) 0.0281(4) Uani 1 d
C22 C 1.1520(3) 0.9403(2) 0.21636(17) 0.0326(4) Uani 1 d
C3 C 0.4824(2) 0.6994(2) 0.94101(16) 0.0294(4) Uani 1 d
C4 C 0.3748(2) 0.70987(19) 0.86643(15) 0.0279(4) Uani 1 d
C23 C 1.0669(3) 0.9924(2) 0.12762(19) 0.0410(5) Uani 1 d
C2 C 0.5057(3) 0.8314(2) 0.95156(17) 0.0347(5) Uani 1 d
C1 C 0.6228(4) 0.8424(3) 0.8612(2) 0.0551(7) Uani 1 d
H20A H 1.157(2) 0.697(2) 0.1367(16) 0.028(5) Uiso 1 d
H15 H 0.999(2) 0.177(2) 0.4793(15) 0.027(5) Uiso 1 d
H13B H 0.823(2) 0.283(2) 0.3183(15) 0.024(5) Uiso 1 d
H17 H 1.346(3) 0.307(2) 0.4398(16) 0.031(5) Uiso 1 d
H11B H 0.478(2) 0.126(2) 0.5763(16) 0.027(5) Uiso 1 d
H13A H 0.759(2) 0.446(2) 0.3396(16) 0.029(5) Uiso 1 d
H20B H 1.309(3) 0.653(2) 0.1902(16) 0.031(5) Uiso 1 d
H11A H 0.619(3) 0.078(2) 0.6397(16) 0.033(6) Uiso 1 d
H4A H 0.264(3) 0.779(2) 0.8969(16) 0.034(6) Uiso 1 d
H21B H 1.001(3) 0.857(2) 0.2887(16) 0.033(6) Uiso 1 d
H4B H 0.412(3) 0.739(2) 0.7986(17) 0.035(6) Uiso 1 d
H3B H 0.588(3) 0.620(2) 0.9140(18) 0.042(6) Uiso 1 d
H21A H 1.157(2) 0.812(2) 0.3359(17) 0.033(6) Uiso 1 d
H22A H 1.270(3) 0.904(2) 0.1897(17) 0.039(6) Uiso 1 d
H1N H 0.437(2) 0.525(2) 0.7894(17) 0.027(5) Uiso 1 d
H8 H 0.137(3) 0.170(2) 0.8951(17) 0.039(6) Uiso 1 d
H9 H 0.329(3) 0.067(2) 0.7350(17) 0.038(6) Uiso 1 d
H2B H 0.542(3) 0.832(3) 1.017(2) 0.048(7) Uiso 1 d
H23C H 0.949(3) 1.028(3) 0.153(2) 0.059(8) Uiso 1 d
H7 H 0.107(3) 0.390(2) 0.9654(17) 0.031(5) Uiso 1 d
H2A H 0.406(3) 0.909(2) 0.9589(17) 0.036(6) Uiso 1 d
H16 H 1.247(3) 0.151(2) 0.5159(18) 0.045(6) Uiso 1 d
H23A H 1.089(3) 1.072(3) 0.0970(19) 0.051(7) Uiso 1 d
H6N H 1.065(3) 0.578(2) 0.2495(17) 0.038(6) Uiso 1 d
H23B H 1.100(3) 0.918(3) 0.071(2) 0.050(7) Uiso 1 d
H1C H 0.731(4) 0.768(3) 0.854(2) 0.067(9) Uiso 1 d
H1B H 0.640(3) 0.921(3) 0.870(2) 0.059(8) Uiso 1 d
H22B H 1.123(3) 1.020(3) 0.266(2) 0.057(7) Uiso 1 d
H3A H 0.435(3) 0.676(2) 1.0084(19) 0.042(6) Uiso 1 d
H1A H 0.592(3) 0.833(3) 0.795(2) 0.062(8) Uiso 1 d
HN4 H 0.672(2) 0.416(2) 0.5110(17) 0.028(5) Uiso 1 d
HN3 H 0.553(3) 0.333(2) 0.6196(18) 0.038(6) Uiso 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 N5 C18 117.67(15)
C19 N6 C20 123.56(16)
C12 N4 C13 125.59(16)
C10 N2 C6 118.65(15)
C5 N1 C4 123.72(16)
C12 N3 C11 124.64(16)
N2 C6 C7 122.72(17)
N2 C6 C5 116.47(15)
C7 C6 C5 120.80(16)
C6 C7 C8 118.22(17)
N5 C18 C17 123.95(16)
N5 C18 C19 116.20(15)
C17 C18 C19 119.85(16)
N5 C14 C15 121.96(16)
N5 C14 C13 116.33(16)
C15 C14 C13 121.72(16)
O2 C19 N6 123.91(16)
O2 C19 C18 120.52(16)
N6 C19 C18 115.57(15)
N3 C11 C10 109.40(15)
O1 C5 N1 124.41(17)
O1 C5 C6 120.76(16)
N1 C5 C6 114.83(15)
N2 C10 C9 122.08(16)
N2 C10 C11 116.95(15)
C9 C10 C11 120.97(16)
C18 C17 C16 117.86(17)
N3 C12 N4 113.92(16)
N3 C12 S1 122.57(13)
N4 C12 S1 123.50(14)
C15 C16 C17 119.00(18)
N4 C13 C14 112.33(15)
N6 C20 C21 112.00(15)
C16 C15 C14 119.55(17)
C9 C8 C7 119.67(17)
C20 C21 C22 112.90(16)
C8 C9 C10 118.64(18)
C23 C22 C21 113.45(17)
C4 C3 C2 111.88(17)
N1 C4 C3 113.38(16)
C1 C2 C3 112.69(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C12 1.6833(18)
O2 C19 1.248(2)
N5 C14 1.337(2)
N5 C18 1.346(2)
O1 C5 1.233(2)
N6 C19 1.326(2)
N6 C20 1.461(2)
N4 C12 1.353(2)
N4 C13 1.447(2)
N2 C10 1.335(2)
N2 C6 1.349(2)
N1 C5 1.331(2)
N1 C4 1.454(2)
N3 C12 1.343(2)
N3 C11 1.449(2)
C6 C7 1.381(3)
C6 C5 1.511(3)
C7 C8 1.388(3)
C18 C17 1.380(3)
C18 C19 1.505(2)
C14 C15 1.399(3)
C14 C13 1.510(3)
C11 C10 1.515(2)
C10 C9 1.396(2)
C17 C16 1.391(3)
C16 C15 1.373(3)
C20 C21 1.518(3)
C8 C9 1.380(3)
C21 C22 1.525(3)
C22 C23 1.522(3)
C3 C4 1.518(3)
C3 C2 1.529(3)
C2 C1 1.510(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 H1N N2 0.86(2) 2.23(2) 2.674(2) 111.5(16) .
N1 H1N O2 0.86(2) 2.24(2) 2.978(2) 144.3(18) 2_766
N6 H6N N5 0.86(2) 2.23(2) 2.674(2) 112.4(18) .
N4 HN4 O2 0.85(2) 2.09(2) 2.897(2) 157.5(19) 2_766
N3 HN3 N2 0.86(2) 2.20(2) 2.629(2) 110.4(18) .
N3 HN3 O2 0.86(2) 2.34(2) 3.089(2) 145.9(19) 2_766
