#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:45:47 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180314 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/28/7152850.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_7152850
loop_
_publ_author_name
'Shankar, Sreejith P.'
'Jagodzinska, Monika'
'Malpezzi, Luciana'
'Lazzari, Paolo'
'Manca, Ilaria'
'Greig, Iain R.'
'Sani, Monica'
'Zanda, Matteo'
_publ_section_title
;
 Synthesis and structure-activity relationship studies of novel tubulysin
 U analogues - effect on cytotoxicity of structural variations in the
 tubuvaline fragment.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2273
_journal_page_last               2287
_journal_paper_doi               10.1039/c3ob27111k
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C17 H28 N2 O5 S'
_chemical_formula_sum            'C17 H28 N2 O5 S'
_chemical_formula_weight         372.47
_chemical_name_systematic
;
Ethyl 2-(3-(tert-butoxycarbonylamino)-4-methylpentanoyl)
thiazole-4-carboxylate
;
_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                90.000(5)
_cell_angle_beta                 98.510(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   12.756(5)
_cell_length_b                   15.696(5)
_cell_length_c                   10.018(5)
_cell_measurement_reflns_used    66
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.15
_cell_measurement_theta_min      5.73
_cell_volume                     1983.7(14)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Siemens P4 diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_av_sigmaI/netI    0.0971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6420
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_reflns_theta_min         3.50
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.690
_exptl_absorpt_correction_T_max  0.9054
_exptl_absorpt_correction_T_min  0.2966
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XSCANS, Siemens 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0016(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   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0611P)²+0.3346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1584
_reflns_number_gt                2392
_reflns_number_total             3233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob27111k.txt
_cod_data_source_block           ms992
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'psi scan' changed to
'psi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7152850
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.70862(7) 0.09334(6) 0.78561(8) 0.0517(3) Uani 1 1 d . . .
O1 O 0.8424(2) 0.21530(18) 0.9204(2) 0.0489(6) Uani 1 1 d . . .
H1O H 0.826(4) 0.270(4) 0.942(4) 0.059 Uiso 0.80(8) 1 d P A 1
H1O' H 0.788(18) 0.219(13) 0.952(19) 0.059 Uiso 0.20(8) 1 d P A 2
O2 O 0.5947(2) 0.01626(19) 0.3525(3) 0.0783(8) Uani 1 1 d . . .
O3 O 0.73827(19) 0.08769(15) 0.3129(2) 0.0604(7) Uani 1 1 d . . .
O4 O 1.20704(17) 0.26307(17) 1.0719(2) 0.0590(7) Uani 1 1 d . . .
O5 O 1.31928(16) 0.21980(15) 0.92922(18) 0.0498(6) Uani 1 1 d . . .
N1 N 0.77294(18) 0.14980(14) 0.5724(2) 0.0382(6) Uani 1 1 d . . .
N2 N 1.15480(18) 0.25308(17) 0.8459(2) 0.0416(6) Uani 1 1 d . . .
H2N H 1.181(3) 0.244(2) 0.768(3) 0.053(9) Uiso 1 1 d . . .
C1 C 1.0449(2) 0.27866(19) 0.8485(3) 0.0395(7) Uani 1 1 d . . .
H1 H 1.029(2) 0.2742(17) 0.942(3) 0.038(7) Uiso 1 1 d . . .
C2 C 0.9720(2) 0.21367(18) 0.7671(3) 0.0385(6) Uani 1 1 d . . .
H2B H 0.9792 0.2189 0.6724 0.046 Uiso 1 1 calc R . .
H2C H 0.9944 0.1567 0.7961 0.046 Uiso 1 1 calc R . .
C3 C 0.8557(2) 0.22504(18) 0.7827(3) 0.0387(6) Uani 1 1 d . . .
H3 H 0.827(2) 0.2845(18) 0.749(3) 0.037(7) Uiso 1 1 d . . .
C4 C 0.7850(2) 0.15997(17) 0.7036(3) 0.0362(6) Uani 1 1 d . . .
C5 C 1.0249(3) 0.3715(2) 0.8084(3) 0.0489(8) Uani 1 1 d . . .
H5 H 0.954(3) 0.3845(19) 0.815(3) 0.046(8) Uiso 1 1 d . . .
C6 C 1.0412(4) 0.3910(2) 0.6646(4) 0.0735(11) Uani 1 1 d . . .
H6A H 0.9983 0.3534 0.6037 0.110 Uiso 1 1 calc R . .
H6B H 1.1145 0.3831 0.6558 0.110 Uiso 1 1 calc R . .
H6C H 1.0212 0.4490 0.6433 0.110 Uiso 1 1 calc R . .
C7 C 1.0912(3) 0.4311(3) 0.9071(4) 0.0764(12) Uani 1 1 d . . .
H7A H 1.0794 0.4183 0.9974 0.115 Uiso 1 1 calc R . .
H7B H 1.0711 0.4890 0.8858 0.115 Uiso 1 1 calc R . .
H7C H 1.1649 0.4236 0.9002 0.115 Uiso 1 1 calc R . .
C8 C 0.6564(2) 0.0507(2) 0.6355(3) 0.0496(8) Uani 1 1 d . . .
H8 H 0.6052 0.0080 0.6247 0.059 Uiso 1 1 calc R . .
C9 C 0.6987(2) 0.08656(18) 0.5331(3) 0.0392(6) Uani 1 1 d . . .
C10 C 0.6704(2) 0.0602(2) 0.3914(3) 0.0484(8) Uani 1 1 d . . .
C11 C 0.7279(3) 0.0528(3) 0.1761(3) 0.0737(12) Uani 1 1 d . . .
H11A H 0.7540 0.0938 0.1165 0.088 Uiso 1 1 calc R . .
H11B H 0.6538 0.0419 0.1429 0.088 Uiso 1 1 calc R . .
C12 C 0.7885(4) -0.0269(3) 0.1757(4) 0.0903(14) Uani 1 1 d . . .
H12A H 0.7810 -0.0493 0.0856 0.135 Uiso 1 1 calc R . .
H12B H 0.7621 -0.0677 0.2340 0.135 Uiso 1 1 calc R . .
H12C H 0.8620 -0.0159 0.2074 0.135 Uiso 1 1 calc R . .
C13 C 1.2254(2) 0.24692(19) 0.9588(3) 0.0390(6) Uani 1 1 d . . .
C14 C 1.4121(3) 0.2156(3) 1.0359(3) 0.0566(9) Uani 1 1 d . . .
C15 C 1.4981(3) 0.1862(4) 0.9575(4) 0.1027(18) Uani 1 1 d . . .
H15A H 1.4820 0.1299 0.9231 0.154 Uiso 1 1 calc R . .
H15B H 1.5649 0.1856 1.0159 0.154 Uiso 1 1 calc R . .
H15C H 1.5021 0.2245 0.8837 0.154 Uiso 1 1 calc R . .
C16 C 1.3943(3) 0.1522(3) 1.1437(4) 0.0790(12) Uani 1 1 d . . .
H16A H 1.3801 0.0971 1.1035 0.119 Uiso 1 1 calc R . .
H16B H 1.3349 0.1699 1.1856 0.119 Uiso 1 1 calc R . .
H16C H 1.4565 0.1493 1.2104 0.119 Uiso 1 1 calc R . .
C17 C 1.4366(3) 0.3035(3) 1.0917(4) 0.0877(15) Uani 1 1 d . . .
H17A H 1.3813 0.3215 1.1408 0.132 Uiso 1 1 calc R . .
H17B H 1.4411 0.3424 1.0188 0.132 Uiso 1 1 calc R . .
H17C H 1.5029 0.3026 1.1511 0.132 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C8 S C4 89.56(14)
C10 O3 C11 117.2(3)
C13 O5 C14 120.0(2)
C4 N1 C9 110.2(2)
C13 N2 C1 122.1(2)
N2 C1 C5 112.4(3)
N2 C1 C2 108.4(2)
C5 C1 C2 115.6(2)
C3 C2 C1 113.0(2)
O1 C3 C4 106.8(2)
O1 C3 C2 110.1(2)
C4 C3 C2 112.5(2)
N1 C4 C3 125.6(3)
N1 C4 S 114.5(2)
C3 C4 S 119.9(2)
C6 C5 C1 113.8(3)
C6 C5 C7 110.5(3)
C1 C5 C7 111.2(3)
C9 C8 S 111.1(2)
C8 C9 N1 114.5(3)
C8 C9 C10 123.2(3)
N1 C9 C10 122.3(3)
O2 C10 O3 123.9(3)
O2 C10 C9 122.9(3)
O3 C10 C9 113.1(3)
O3 C11 C12 110.2(3)
O4 C13 N2 124.9(3)
O4 C13 O5 124.8(3)
N2 C13 O5 110.2(2)
O5 C14 C17 109.2(3)
O5 C14 C16 111.0(3)
C17 C14 C16 112.6(3)
O5 C14 C15 101.7(3)
C17 C14 C15 110.2(4)
C16 C14 C15 111.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C8 1.691(3)
S C4 1.719(3)
O1 C3 1.423(3)
O2 C10 1.204(4)
O3 C10 1.324(4)
O3 C11 1.464(4)
O4 C13 1.218(3)
O5 C13 1.345(3)
O5 C14 1.474(3)
N1 C4 1.310(3)
N1 C9 1.388(3)
N2 C13 1.341(3)
N2 C1 1.462(4)
C1 C5 1.522(4)
C1 C2 1.532(4)
C2 C3 1.525(4)
C3 C4 1.508(4)
C5 C6 1.517(5)
C5 C7 1.524(4)
C8 C9 1.351(4)
C9 C10 1.471(4)
C11 C12 1.471(5)
C14 C17 1.503(6)
C14 C16 1.510(5)
C14 C15 1.514(5)
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
O1 H1O N1 0.91(6) 2.01(5) 2.826(3) 149(4) 4_566
N2 H2N O4 0.90(4) 2.05(4) 2.930(3) 166(3) 4_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C13 N2 C1 C5 101.4(3)
C13 N2 C1 C2 -129.6(3)
N2 C1 C2 C3 170.1(2)
C5 C1 C2 C3 -62.7(3)
C1 C2 C3 O1 -60.2(3)
C1 C2 C3 C4 -179.2(2)
C9 N1 C4 C3 -177.6(2)
C9 N1 C4 S 0.6(3)
O1 C3 C4 N1 178.4(3)
C2 C3 C4 N1 -60.7(4)
O1 C3 C4 S 0.3(3)
C2 C3 C4 S 121.3(2)
C8 S C4 N1 -0.9(2)
C8 S C4 C3 177.4(2)
N2 C1 C5 C6 63.2(4)
C2 C1 C5 C6 -62.0(4)
N2 C1 C5 C7 -62.4(3)
C2 C1 C5 C7 172.4(3)
C4 S C8 C9 0.9(3)
S C8 C9 N1 -0.8(4)
S C8 C9 C10 178.2(2)
C4 N1 C9 C8 0.1(4)
C4 N1 C9 C10 -178.8(3)
C11 O3 C10 O2 -8.6(5)
C11 O3 C10 C9 169.6(3)
C8 C9 C10 O2 13.8(5)
N1 C9 C10 O2 -167.3(3)
C8 C9 C10 O3 -164.3(3)
N1 C9 C10 O3 14.5(4)
C10 O3 C11 C12 -87.0(4)
C1 N2 C13 O4 -1.5(5)
C1 N2 C13 O5 178.1(3)
C14 O5 C13 O4 -6.0(5)
C14 O5 C13 N2 174.4(3)
C13 O5 C14 C17 -61.2(4)
C13 O5 C14 C16 63.5(4)
C13 O5 C14 C15 -177.7(3)
