#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/43/7204315.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_7204315
loop_
_publ_author_name
'Diana Bričkutė'
'Frank A. Sløk'
'Christian Rømming'
'Algirdas Šačkus'
_publ_section_title
;
 Facile synthesis of 2-substituted ethyl
 2-(2-amino-5-ethoxycarbonylthiazol-4-yl)ethanoates
;
_journal_issue                   5
_journal_name_full               'J. Chem. Soc., Perkin Trans. 1'
_journal_page_first              652
_journal_page_last               656
_journal_paper_doi               10.1039/b110022j
_journal_year                    2002
_chemical_formula_sum            'C14 H15 N3 O4 S'
_chemical_formula_weight         321.35
_chemical_melting_point          139.0(10)
_chemical_name_systematic
; 
ethyl 2-[5-ethoxycarbonyl-2-(1-pyrrolo)thiazol-4-yl]-2-iminoethanoate 
;
_space_group_IT_number           14
_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                 103.416(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7843(11)
_cell_length_b                   15.848(2)
_cell_length_c                   13.0532(18)
_cell_measurement_temperature    293(2)
_cell_volume                     1566.4(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26718
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         6.85
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.062
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                2744
_reflns_number_total             3821
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b110022j.txt
_cod_data_source_block           11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '138-140' was changed to '139.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7204315
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
S1 S 0.24363(6) 0.51600(3) -0.03466(3) 0.04816(14) Uani 1 1 d . . .
O1 O 0.1745(2) 0.34750(9) 0.17469(10) 0.0704(4) Uani 1 1 d . . .
O2 O 0.11470(17) 0.34557(8) -0.00330(9) 0.0571(3) Uani 1 1 d . . .
O3 O 0.2761(2) 0.47664(12) 0.43362(11) 0.0797(5) Uani 1 1 d . . .
O4 O 0.10698(18) 0.53524(10) 0.28863(10) 0.0671(4) Uani 1 1 d . . .
N1 N 0.40209(18) 0.58956(9) 0.13894(10) 0.0458(3) Uani 1 1 d . . .
N2 N 0.39857(18) 0.67125(9) -0.01315(10) 0.0476(3) Uani 1 1 d . . .
N3 N 0.5417(2) 0.46033(14) 0.32016(14) 0.0719(5) Uani 1 1 d . . .
H3 H 0.552(3) 0.4532(15) 0.388(2) 0.074(7) Uiso 1 1 d . . .
C1 C 0.2566(2) 0.46336(11) 0.08373(12) 0.0462(4) Uani 1 1 d . . .
C2 C 0.3447(2) 0.51201(11) 0.16501(12) 0.0446(3) Uani 1 1 d . . .
C3 C 0.3577(2) 0.59897(10) 0.03654(12) 0.0434(3) Uani 1 1 d . . .
C4 C 0.3623(3) 0.68611(14) -0.12078(15) 0.0615(5) Uani 1 1 d . . .
H4 H 0.309(3) 0.6440(16) -0.1643(19) 0.079(7) Uiso 1 1 d . . .
C5 C 0.4171(3) 0.76495(14) -0.13620(17) 0.0669(5) Uani 1 1 d . . .
H5 H 0.413(3) 0.7920(16) -0.204(2) 0.091(7) Uiso 1 1 d . . .
C6 C 0.4919(3) 0.80042(14) -0.03633(17) 0.0647(5) Uani 1 1 d . . .
H6 H 0.544(3) 0.8537(16) -0.0227(17) 0.076(7) Uiso 1 1 d . . .
C7 C 0.4798(3) 0.74267(12) 0.03816(16) 0.0586(5) Uani 1 1 d . . .
H7 H 0.520(3) 0.7431(14) 0.1149(19) 0.073(6) Uiso 1 1 d . . .
C8 C 0.1792(2) 0.37974(11) 0.09160(13) 0.0508(4) Uani 1 1 d . . .
C9 C 0.0380(3) 0.26131(13) -0.00270(18) 0.0633(5) Uani 1 1 d . . .
H9A H -0.057(3) 0.2642(15) 0.0371(19) 0.077(7) Uiso 1 1 d . . .
H9B H 0.134(3) 0.2223(15) 0.0316(19) 0.079(7) Uiso 1 1 d . . .
C10 C -0.0336(5) 0.2351(2) -0.1139(2) 0.0886(8) Uani 1 1 d . . .
H10A H -0.115(5) 0.281(2) -0.153(3) 0.129(12) Uiso 1 1 d . . .
H10B H 0.070(4) 0.2249(19) -0.146(2) 0.108(10) Uiso 1 1 d . . .
H10C H -0.087(4) 0.180(2) -0.118(2) 0.108(9) Uiso 1 1 d . . .
C11 C 0.3891(2) 0.48708(11) 0.27900(12) 0.0494(4) Uani 1 1 d . . .
C12 C 0.2508(2) 0.49794(12) 0.34326(13) 0.0542(4) Uani 1 1 d . . .
C13 C -0.0370(4) 0.5503(3) 0.3443(3) 0.0907(9) Uani 1 1 d . . .
H13A H -0.074(4) 0.494(2) 0.338(2) 0.105(11) Uiso 1 1 d . . .
H13B H 0.021(5) 0.578(2) 0.411(3) 0.140(13) Uiso 1 1 d . . .
C14 C -0.1551(4) 0.6147(2) 0.2857(2) 0.0816(7) Uani 1 1 d . . .
H14A H -0.076(5) 0.667(3) 0.301(3) 0.142(12) Uiso 1 1 d . . .
H14B H -0.261(5) 0.623(2) 0.323(3) 0.124(10) Uiso 1 1 d . . .
H14C H -0.204(5) 0.600(2) 0.209(3) 0.137(12) Uiso 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 0.0016 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C1 88.31(8) . . ?
C8 O2 C9 115.49(14) . . ?
C12 O4 C13 116.65(16) . . ?
C3 N1 C2 109.27(13) . . ?
C4 N2 C3 126.71(15) . . ?
C4 N2 C7 108.22(15) . . ?
C3 N2 C7 125.05(14) . . ?
C11 N3 H3 109.0(15) . . ?
C2 C1 C8 126.67(15) . . ?
C2 C1 S1 109.62(13) . . ?
C8 C1 S1 123.70(12) . . ?
C1 C2 N1 116.53(14) . . ?
C1 C2 C11 125.61(15) . . ?
N1 C2 C11 117.83(14) . . ?
N1 C3 N2 122.40(14) . . ?
N1 C3 S1 116.26(12) . . ?
N2 C3 S1 121.34(11) . . ?
C5 C4 N2 108.10(18) . . ?
C5 C4 H4 134.3(15) . . ?
N2 C4 H4 117.6(15) . . ?
C4 C5 C6 107.88(18) . . ?
C4 C5 H5 126.4(15) . . ?
C6 C5 H5 125.6(15) . . ?
C7 C6 C5 108.10(19) . . ?
C7 C6 H6 124.9(14) . . ?
C5 C6 H6 127.0(14) . . ?
C6 C7 N2 107.70(18) . . ?
C6 C7 H7 132.2(14) . . ?
N2 C7 H7 120.1(14) . . ?
O1 C8 O2 125.24(17) . . ?
O1 C8 C1 122.90(16) . . ?
O2 C8 C1 111.86(14) . . ?
O2 C9 C10 108.10(19) . . ?
O2 C9 H9A 108.2(14) . . ?
C10 C9 H9A 111.5(14) . . ?
O2 C9 H9B 107.9(14) . . ?
C10 C9 H9B 109.8(14) . . ?
H9A C9 H9B 111(2) . . ?
C9 C10 H10A 109.6(19) . . ?
C9 C10 H10B 107.3(17) . . ?
H10A C10 H10B 112(3) . . ?
C9 C10 H10C 111.4(18) . . ?
H10A C10 H10C 114(3) . . ?
H10B C10 H10C 102(2) . . ?
N3 C11 C2 119.29(16) . . ?
N3 C11 C12 121.46(16) . . ?
C2 C11 C12 119.21(14) . . ?
O3 C12 O4 125.68(17) . . ?
O3 C12 C11 122.37(16) . . ?
O4 C12 C11 111.92(14) . . ?
C14 C13 O4 108.0(2) . . ?
C14 C13 H13A 119(2) . . ?
O4 C13 H13A 93(2) . . ?
C14 C13 H13B 105(2) . . ?
O4 C13 H13B 105(2) . . ?
H13A C13 H13B 125(3) . . ?
C13 C14 H14A 101(2) . . ?
C13 C14 H14B 108.2(18) . . ?
H14A C14 H14B 108(3) . . ?
C13 C14 H14C 113(2) . . ?
H14A C14 H14C 117(3) . . ?
H14B C14 H14C 109(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
S1 C3 1.7314(16) . ?
S1 C1 1.7385(16) . ?
O1 C8 1.207(2) . ?
O2 C8 1.338(2) . ?
O2 C9 1.464(2) . ?
O3 C12 1.198(2) . ?
O4 C12 1.319(2) . ?
O4 C13 1.489(3) . ?
N1 C3 1.309(2) . ?
N1 C2 1.377(2) . ?
N2 C4 1.387(2) . ?
N2 C3 1.389(2) . ?
N2 C7 1.390(2) . ?
N3 C11 1.258(2) . ?
N3 H3 0.88(2) . ?
C1 C2 1.361(2) . ?
C1 C8 1.469(3) . ?
C2 C11 1.500(2) . ?
C4 C5 1.350(3) . ?
C4 H4 0.91(2) . ?
C5 C6 1.415(3) . ?
C5 H5 0.98(3) . ?
C6 C7 1.354(3) . ?
C6 H6 0.94(3) . ?
C7 H7 0.98(2) . ?
C9 C10 1.488(3) . ?
C9 H9A 1.00(2) . ?
C9 H9B 0.99(3) . ?
C10 H10A 1.02(4) . ?
C10 H10B 1.01(3) . ?
C10 H10C 0.97(3) . ?
C11 C12 1.520(2) . ?
C13 C14 1.464(4) . ?
C13 H13A 0.94(3) . ?
C13 H13B 0.99(4) . ?
C14 H14A 1.03(4) . ?
C14 H14B 1.06(4) . ?
C14 H14C 1.02(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21142828
