#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:56:56 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179605 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/69/4506951.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_4506951
loop_
_publ_author_name
'Mali, Sachitanand M.'
'Schneider, Tobias F.'
'Bandyopadhyay, Anupam'
'Jadhav, Sandip V.'
'Werz, Daniel B.'
'Gopi, Hosahudya N.'
_publ_section_title
;
 Thiazole--Carbonyl Interactions: A Case Study Using Phenylalanine
 Thiazole Cyclic Tripeptides
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5643
_journal_paper_doi               10.1021/cg301147s
_journal_volume                  12
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C39 H36 N6 O6 S3,( C7 H8)'
_chemical_formula_sum            'C46 H44 N6 O6 S3'
_chemical_formula_weight         873.05
_chemical_melting_point          154
_chemical_name_common            'Cyclic peptide'
_chemical_name_systematic        'Tyrosine tricyclic Thz peptide'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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            4
_cell_length_a                   10.477(3)
_cell_length_b                   18.005(5)
_cell_length_c                   22.648(6)
_cell_measurement_temperature    100(2)
_cell_volume                     4272(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_pressure         101.325
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            24079
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.14
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Graphite monochromator'
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'square block'
_exptl_crystal_F_000             1832
_exptl_crystal_recrystallization_method Toluene
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         10310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.110
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                9498
_reflns_number_total             10310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301147s_si_002.cif
_cod_data_source_block           hng_tyr_thz_tricp_tolu
_cod_database_code               4506951
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
S1 S 0.58278(3) 0.18191(2) 0.062558(17) 0.03074(9) Uani 1 1 d .
S2 S -0.07840(4) -0.08825(2) 0.15373(2) 0.03858(11) Uani 1 1 d .
S3 S 0.34950(4) 0.11138(2) 0.415180(19) 0.03704(10) Uani 1 1 d .
O1 O 0.54635(12) 0.28497(7) -0.18185(6) 0.0437(3) Uani 1 1 d .
O2 O 0.63491(11) 0.23693(7) 0.25603(5) 0.0383(3) Uani 1 1 d .
O3 O 0.42857(17) 0.31056(11) 0.58958(6) 0.0673(5) Uani 1 1 d .
O4 O 0.00572(15) -0.01339(8) 0.35094(6) 0.0525(4) Uani 1 1 d .
O5 O -0.65964(11) -0.07119(8) 0.18005(7) 0.0470(3) Uani 1 1 d .
O6 O 0.22915(15) -0.01486(8) 0.02480(6) 0.0522(4) Uani 1 1 d .
N1 N 0.24715(11) 0.08078(7) 0.08757(5) 0.0254(2) Uani 1 1 d .
H1 H 0.2250 0.0986 0.1213 0.030 Uiso 1 1 calc R
N2 N 0.42155(11) 0.16721(7) 0.14577(5) 0.0236(2) Uani 1 1 d .
N3 N 0.42796(12) 0.20252(8) 0.26192(6) 0.0299(3) Uani 1 1 d .
H3 H 0.3610 0.1900 0.2423 0.036 Uiso 1 1 calc R
N4 N 0.23389(11) 0.12802(7) 0.31752(5) 0.0251(2) Uani 1 1 d .
N5 N 0.01506(12) 0.06262(8) 0.27279(6) 0.0297(3) Uani 1 1 d .
H5 H 0.0490 0.1018 0.2578 0.036 Uiso 1 1 calc R
N6 N 0.06284(11) 0.02568(7) 0.15792(6) 0.0247(2) Uani 1 1 d .
C1 C 0.33617(13) 0.12155(8) 0.05151(6) 0.0245(3) Uani 1 1 d .
H1A H 0.3776 0.0865 0.0245 0.029 Uiso 1 1 calc R
C2 C 0.26714(14) 0.18064(9) 0.01438(7) 0.0284(3) Uani 1 1 d .
H2A H 0.1876 0.1599 -0.0001 0.034 Uiso 1 1 calc R
H2B H 0.2463 0.2225 0.0395 0.034 Uiso 1 1 calc R
C3 C 0.34375(13) 0.20787(8) -0.03708(6) 0.0249(3) Uani 1 1 d .
C4 C 0.36727(14) 0.16165(8) -0.08410(7) 0.0292(3) Uani 1 1 d .
H4 H 0.3368 0.1132 -0.0828 0.035 Uiso 1 1 calc R
C5 C 0.43465(15) 0.18469(9) -0.13327(7) 0.0307(3) Uani 1 1 d .
H5A H 0.4492 0.1522 -0.1645 0.037 Uiso 1 1 calc R
C6 C 0.47983(14) 0.25632(9) -0.13531(7) 0.0296(3) Uani 1 1 d .
C7 C 0.45784(13) 0.30352(9) -0.08865(7) 0.0300(3) Uani 1 1 d .
H7 H 0.4881 0.3521 -0.0900 0.036 Uiso 1 1 calc R
C8 C 0.39109(13) 0.27920(9) -0.03981(7) 0.0280(3) Uani 1 1 d .
H8 H 0.3779 0.3114 -0.0083 0.034 Uiso 1 1 calc R
C9 C 0.5647(2) 0.23745(13) -0.23109(10) 0.0621(6) Uani 1 1 d .
H9A H 0.6152 0.1955 -0.2194 0.093 Uiso 1 1 calc R
H9B H 0.6079 0.2641 -0.2619 0.093 Uiso 1 1 calc R
H9C H 0.4833 0.2206 -0.2453 0.093 Uiso 1 1 calc R
C10 C 0.43665(12) 0.15514(8) 0.09007(7) 0.0232(3) Uani 1 1 d .
C11 C 0.62689(14) 0.21006(9) 0.13093(7) 0.0286(3) Uani 1 1 d .
H11 H 0.7056 0.2306 0.1406 0.034 Uiso 1 1 calc R
C12 C 0.53022(13) 0.19815(8) 0.16922(7) 0.0249(3) Uani 1 1 d .
C13 C 0.53740(13) 0.21462(8) 0.23303(7) 0.0274(3) Uani 1 1 d .
C14 C 0.41987(14) 0.20994(9) 0.32518(6) 0.0274(3) Uani 1 1 d .
H14 H 0.5047 0.2013 0.3421 0.033 Uiso 1 1 calc R
C15 C 0.37554(16) 0.28819(9) 0.34276(7) 0.0330(3) Uani 1 1 d .
H15A H 0.4284 0.3247 0.3230 0.040 Uiso 1 1 calc R
H15B H 0.2882 0.2954 0.3298 0.040 Uiso 1 1 calc R
C16 C 0.38307(16) 0.29998(9) 0.40809(7) 0.0319(3) Uani 1 1 d .
C17 C 0.49784(16) 0.31771(10) 0.43458(8) 0.0377(4) Uani 1 1 d .
H17 H 0.5688 0.3270 0.4110 0.045 Uiso 1 1 calc R
C18 C 0.50959(18) 0.32191(11) 0.49480(9) 0.0441(4) Uani 1 1 d .
H18 H 0.5877 0.3343 0.5117 0.053 Uiso 1 1 calc R
C19 C 0.4055(2) 0.30779(11) 0.53015(8) 0.0455(4) Uani 1 1 d .
C20 C 0.28863(18) 0.29278(11) 0.50511(8) 0.0438(4) Uani 1 1 d .
H20 H 0.2172 0.2854 0.5288 0.053 Uiso 1 1 calc R
C21 C 0.27860(16) 0.28881(10) 0.44419(8) 0.0366(4) Uani 1 1 d .
H21 H 0.1998 0.2784 0.4272 0.044 Uiso 1 1 calc R
C22 C 0.3235(3) 0.2969(2) 0.62750(10) 0.0839(9) Uani 1 1 d .
H22A H 0.2627 0.3365 0.6237 0.126 Uiso 1 1 calc R
H22B H 0.3528 0.2943 0.6676 0.126 Uiso 1 1 calc R
H22C H 0.2839 0.2508 0.6169 0.126 Uiso 1 1 calc R
C23 C 0.33170(14) 0.15159(8) 0.34729(7) 0.0256(3) Uani 1 1 d .
C24 C 0.21806(17) 0.05965(9) 0.40257(8) 0.0358(4) Uani 1 1 d .
H24 H 0.1842 0.0251 0.4288 0.043 Uiso 1 1 calc R
C25 C 0.16937(14) 0.07558(8) 0.34926(7) 0.0271(3) Uani 1 1 d .
C26 C 0.05578(14) 0.03780(9) 0.32486(7) 0.0298(3) Uani 1 1 d .
C27 C -0.08548(14) 0.02471(9) 0.24102(7) 0.0277(3) Uani 1 1 d .
H27 H -0.1176 -0.0161 0.2655 0.033 Uiso 1 1 calc R
C28 C -0.19658(15) 0.07781(10) 0.22722(9) 0.0382(4) Uani 1 1 d .
H28A H -0.2089 0.1110 0.2605 0.046 Uiso 1 1 calc R
H28B H -0.1743 0.1078 0.1932 0.046 Uiso 1 1 calc R
C29 C -0.31973(14) 0.03770(9) 0.21488(8) 0.0337(3) Uani 1 1 d .
C30 C -0.39741(17) 0.01655(12) 0.26074(9) 0.0447(4) Uani 1 1 d .
H30 H -0.3724 0.0273 0.2992 0.054 Uiso 1 1 calc R
C31 C -0.51194(17) -0.02026(12) 0.25152(9) 0.0450(4) Uani 1 1 d .
H31 H -0.5628 -0.0343 0.2833 0.054 Uiso 1 1 calc R
C32 C -0.54868(14) -0.03562(9) 0.19481(9) 0.0354(4) Uani 1 1 d .
C33 C -0.47274(16) -0.01496(9) 0.14801(9) 0.0362(4) Uani 1 1 d .
H33 H -0.4981 -0.0255 0.1095 0.043 Uiso 1 1 calc R
C34 C -0.35946(16) 0.02120(9) 0.15826(8) 0.0346(3) Uani 1 1 d .
H34 H -0.3085 0.0348 0.1264 0.041 Uiso 1 1 calc R
C35 C -0.73810(17) -0.09476(12) 0.22720(11) 0.0524(5) Uani 1 1 d .
H35A H -0.6921 -0.1295 0.2513 0.079 Uiso 1 1 calc R
H35B H -0.8133 -0.1182 0.2117 0.079 Uiso 1 1 calc R
H35C H -0.7622 -0.0526 0.2506 0.079 Uiso 1 1 calc R
C36 C -0.02855(13) -0.00717(8) 0.18601(7) 0.0262(3) Uani 1 1 d .
C37 C 0.03227(17) -0.07643(10) 0.09990(8) 0.0374(4) Uani 1 1 d .
H37 H 0.0457 -0.1089 0.0686 0.045 Uiso 1 1 calc R
C38 C 0.09756(15) -0.01355(8) 0.10914(7) 0.0277(3) Uani 1 1 d .
C39 C 0.19857(14) 0.01639(9) 0.07001(7) 0.0299(3) Uani 1 1 d .
C40 C 0.2672(2) 0.45565(11) 0.04921(10) 0.0490(5) Uani 1 1 d .
C41 C 0.2457(2) 0.40218(13) 0.09033(12) 0.0604(6) Uani 1 1 d .
H41 H 0.1624 0.3899 0.1006 0.073 Uiso 1 1 calc R
C42 C 0.3467(3) 0.36580(16) 0.11713(13) 0.0795(8) Uani 1 1 d .
H42 H 0.3311 0.3290 0.1450 0.095 Uiso 1 1 calc R
C43 C 0.4685(3) 0.38398(19) 0.10262(16) 0.0837(10) Uani 1 1 d .
H43 H 0.5366 0.3595 0.1203 0.100 Uiso 1 1 calc R
C44 C 0.4897(2) 0.43634(18) 0.06347(19) 0.0872(11) Uani 1 1 d .
H44 H 0.5733 0.4492 0.0543 0.105 Uiso 1 1 calc R
C45 C 0.3924(3) 0.47189(13) 0.03625(13) 0.0686(7) Uani 1 1 d .
H45 H 0.4105 0.5081 0.0082 0.082 Uiso 1 1 calc R
C46 C 0.1587(3) 0.49543(16) 0.02047(14) 0.0808(9) Uani 1 1 d .
H46A H 0.1071 0.4605 -0.0008 0.121 Uiso 1 1 calc R
H46B H 0.1914 0.5320 -0.0064 0.121 Uiso 1 1 calc R
H46C H 0.1078 0.5194 0.0501 0.121 Uiso 1 1 calc R
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
C11 S1 C10 89.75(7)
C37 S2 C36 89.51(8)
C24 S3 C23 89.57(8)
C6 O1 C9 116.63(14)
C19 O3 C22 116.91(19)
C32 O5 C35 116.74(16)
C39 N1 C1 121.56(13)
C10 N2 C12 110.16(12)
C13 N3 C14 121.42(13)
C23 N4 C25 110.09(13)
C26 N5 C27 121.03(13)
C36 N6 C38 111.09(13)
N1 C1 C10 109.31(12)
N1 C1 C2 110.99(11)
C10 C1 C2 111.76(12)
C3 C2 C1 113.59(12)
C4 C3 C8 117.72(14)
C4 C3 C2 120.07(13)
C8 C3 C2 122.20(14)
C3 C4 C5 122.29(14)
C6 C5 C4 118.99(15)
O1 C6 C5 123.81(15)
O1 C6 C7 116.45(14)
C5 C6 C7 119.74(14)
C6 C7 C8 120.30(14)
C3 C8 C7 120.94(15)
N2 C10 C1 123.57(12)
N2 C10 S1 114.57(11)
C1 C10 S1 121.86(11)
C12 C11 S1 109.57(11)
C11 C12 N2 115.95(13)
C11 C12 C13 123.93(13)
N2 C12 C13 120.11(12)
O2 C13 N3 124.39(15)
O2 C13 C12 121.91(14)
N3 C13 C12 113.71(13)
N3 C14 C23 107.82(12)
N3 C14 C15 111.13(13)
C23 C14 C15 111.92(13)
C16 C15 C14 111.74(13)
C21 C16 C17 117.81(15)
C21 C16 C15 121.52(15)
C17 C16 C15 120.53(15)
C18 C17 C16 121.53(17)
C17 C18 C19 119.81(18)
O3 C19 C20 124.72(19)
O3 C19 C18 115.18(19)
C20 C19 C18 120.09(17)
C19 C20 C21 119.21(17)
C16 C21 C20 121.46(17)
N4 C23 C14 123.16(13)
N4 C23 S3 114.51(11)
C14 C23 S3 122.32(11)
C25 C24 S3 110.17(12)
C24 C25 N4 115.67(14)
C24 C25 C26 122.98(14)
N4 C25 C26 121.32(13)
O4 C26 N5 123.19(15)
O4 C26 C25 121.02(15)
N5 C26 C25 115.77(13)
N5 C27 C36 107.76(12)
N5 C27 C28 111.02(13)
C36 C27 C28 111.77(14)
C29 C28 C27 112.84(14)
C30 C29 C34 117.66(16)
C30 C29 C28 120.05(17)
C34 C29 C28 122.30(16)
C29 C30 C31 122.11(19)
C32 C31 C30 118.76(18)
O5 C32 C31 124.23(17)
O5 C32 C33 115.42(17)
C31 C32 C33 120.35(16)
C34 C33 C32 119.82(17)
C33 C34 C29 121.31(17)
N6 C36 C27 121.98(14)
N6 C36 S2 113.92(12)
C27 C36 S2 124.09(11)
C38 C37 S2 110.06(13)
C37 C38 N6 115.41(14)
C37 C38 C39 125.37(15)
N6 C38 C39 119.18(13)
O6 C39 N1 123.89(14)
O6 C39 C38 121.70(14)
N1 C39 C38 114.35(13)
C41 C40 C45 117.1(2)
C41 C40 C46 120.8(2)
C45 C40 C46 122.1(2)
C40 C41 C42 120.6(2)
C43 C42 C41 119.9(3)
C44 C43 C42 119.7(3)
C43 C44 C45 121.3(3)
C44 C45 C40 121.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C11 1.6936(17)
S1 C10 1.7217(14)
S2 C37 1.6958(18)
S2 C36 1.7140(16)
S3 C24 1.6868(18)
S3 C23 1.7096(16)
O1 C6 1.3648(19)
O1 C9 1.419(3)
O2 C13 1.2151(18)
O3 C19 1.368(2)
O3 C22 1.417(3)
O4 C26 1.214(2)
O5 C32 1.369(2)
O5 C35 1.413(3)
O6 C39 1.211(2)
N1 C39 1.327(2)
N1 C1 1.4407(17)
N2 C10 1.2899(19)
N2 C12 1.3742(18)
N3 C13 1.3379(19)
N3 C14 1.4415(19)
N4 C23 1.2980(19)
N4 C25 1.3657(19)
N5 C26 1.331(2)
N5 C27 1.4468(19)
N6 C36 1.2927(19)
N6 C38 1.361(2)
C1 C10 1.496(2)
C1 C2 1.537(2)
C2 C3 1.498(2)
C3 C4 1.374(2)
C3 C8 1.378(2)
C4 C5 1.382(2)
C5 C6 1.375(2)
C6 C7 1.376(2)
C7 C8 1.380(2)
C11 C12 1.351(2)
C12 C13 1.477(2)
C14 C23 1.486(2)
C14 C15 1.536(2)
C15 C16 1.497(2)
C16 C21 1.381(2)
C16 C17 1.381(2)
C17 C18 1.371(3)
C18 C19 1.377(3)
C19 C20 1.376(3)
C20 C21 1.386(3)
C24 C25 1.342(2)
C25 C26 1.478(2)
C27 C36 1.496(2)
C27 C28 1.538(2)
C28 C29 1.505(2)
C29 C30 1.373(3)
C29 C34 1.380(3)
C30 C31 1.387(3)
C31 C32 1.369(3)
C32 C33 1.377(3)
C33 C34 1.373(2)
C37 C38 1.339(2)
C38 C39 1.482(2)
C40 C41 1.358(3)
C40 C45 1.375(3)
C40 C46 1.493(3)
C41 C42 1.385(4)
C42 C43 1.357(5)
C43 C44 1.313(5)
C44 C45 1.352(5)
