#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:57:15 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180324 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/38/7153858.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_7153858
loop_
_publ_author_name
'Huynh, Thi Ngoc Tram'
'Retailleau, Pascal'
'Denhez, Clément'
'Nguyen, Kim Phi Phung'
'Guillaume, Dom'
_publ_section_title
;
 Regioselective synthesis of 3,4,5-trisubstituted 2-aminofurans.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5098
_journal_page_last               5101
_journal_paper_doi               10.1039/c4ob01037j
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 N2 O6 S'
_chemical_formula_sum            'C21 H20 N2 O6 S'
_chemical_formula_weight         428.45
_chemical_name_systematic
; 
 methyl 2-(tert-butylamino)-5-(4-nitrophenyl)-4-
(thiophene-2-carbonyl)furan-3-carboxylate 
;
_space_group_IT_number           144
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   10.104(2)
_cell_length_b                   10.104(2)
_cell_length_c                   17.905(4)
_cell_measurement_reflns_used    1904
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      0.407
_cell_volume                     1583.0(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9134
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         2.59
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; 1832 Bijvoet pairs'
_refine_ls_abs_structure_Flack   0.07(9)
_refine_ls_extinction_coef       0.053(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0636P)²+0.3696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                3303
_reflns_number_total             3746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01037j2.cif
_cod_data_source_block           ntn157f2
_cod_depositor_comments
'Adding full bibliography for 7153857--7153858.cif.'
_cod_database_code               7153858
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
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 0.03397(10) 0.60531(10) 0.87793(4) 0.0672(3) Uani 1 1 d .
O1 O 0.3573(2) 0.2631(2) 0.75194(10) 0.0510(4) Uani 1 1 d .
O2 O 0.6816(2) 0.6619(3) 0.85634(13) 0.0663(6) Uani 1 1 d .
O3 O 0.4772(2) 0.6666(2) 0.90434(11) 0.0629(5) Uani 1 1 d .
C2 C 0.4799(3) 0.3881(3) 0.77858(15) 0.0480(6) Uani 1 1 d .
C3 C 0.4352(3) 0.4685(3) 0.82531(15) 0.0480(6) Uani 1 1 d .
C4 C 0.2708(3) 0.3823(3) 0.82618(14) 0.0461(6) Uani 1 1 d .
C5 C 0.2266(3) 0.2580(3) 0.78171(15) 0.0468(6) Uani 1 1 d .
C6 C 0.5439(3) 0.6056(3) 0.86239(14) 0.0512(6) Uani 1 1 d .
C7 C 0.5793(5) 0.8083(4) 0.9411(2) 0.0874(12) Uani 1 1 d .
H7A H 0.6276 0.7888 0.9824 0.131 Uiso 1 1 calc R
H7B H 0.5226 0.8549 0.9589 0.131 Uiso 1 1 calc R
H7C H 0.6559 0.8758 0.9064 0.131 Uiso 1 1 calc R
N1 N 0.6183(3) 0.4163(3) 0.75765(15) 0.0611(6) Uani 1 1 d D
H1N H 0.697(3) 0.490(3) 0.7814(18) 0.073 Uiso 1 1 d D
C8 C 0.6521(3) 0.3242(4) 0.70440(17) 0.0619(8) Uani 1 1 d .
C9 C 0.8235(4) 0.4074(6) 0.6958(3) 0.1112(18) Uani 1 1 d .
H9A H 0.8586 0.5104 0.6799 0.167 Uiso 1 1 calc R
H9B H 0.8514 0.3562 0.6593 0.167 Uiso 1 1 calc R
H9C H 0.8697 0.4086 0.7429 0.167 Uiso 1 1 calc R
C10 C 0.5935(5) 0.1644(5) 0.7366(2) 0.0877(11) Uani 1 1 d .
H10A H 0.6369 0.1725 0.7853 0.132 Uiso 1 1 calc R
H10B H 0.6226 0.1074 0.7043 0.132 Uiso 1 1 calc R
H10C H 0.4841 0.1129 0.7406 0.132 Uiso 1 1 calc R
C11 C 0.5801(5) 0.3172(4) 0.6284(2) 0.0752(9) Uani 1 1 d .
H11A H 0.4710 0.2542 0.6319 0.113 Uiso 1 1 calc R
H11B H 0.6183 0.2746 0.5921 0.113 Uiso 1 1 calc R
H11C H 0.6056 0.4185 0.6133 0.113 Uiso 1 1 calc R
C1' C 0.0847(3) 0.1315(3) 0.75342(14) 0.0464(6) Uani 1 1 d .
C2' C 0.0907(3) 0.0467(3) 0.69303(16) 0.0538(6) Uani 1 1 d .
H2' H 0.1847 0.0717 0.6723 0.065 Uiso 1 1 calc R
C3' C -0.0413(3) -0.0737(3) 0.66388(17) 0.0579(7) Uani 1 1 d .
H3' H -0.0370 -0.1298 0.6237 0.069 Uiso 1 1 calc R
C4' C -0.1787(3) -0.1087(3) 0.69540(17) 0.0558(7) Uani 1 1 d .
C5' C -0.1890(3) -0.0293(4) 0.7544(2) 0.0633(8) Uani 1 1 d .
H5' H -0.2838 -0.0559 0.7747 0.076 Uiso 1 1 calc R
C6' C -0.0568(3) 0.0917(4) 0.78413(17) 0.0600(7) Uani 1 1 d .
H6' H -0.0629 0.1460 0.8246 0.072 Uiso 1 1 calc R
N1' N -0.3198(3) -0.2368(3) 0.66486(19) 0.0749(8) Uani 1 1 d .
O1' O -0.4413(3) -0.2664(4) 0.69425(18) 0.1034(10) Uani 1 1 d .
O2' O -0.3093(3) -0.3046(3) 0.6111(2) 0.1017(9) Uani 1 1 d .
C1" C 0.1661(3) 0.4255(3) 0.86556(14) 0.0476(6) Uani 1 1 d .
O1" O 0.0890(3) 0.3501(3) 0.91834(12) 0.0717(6) Uani 1 1 d .
C2" C 0.1547(3) 0.5538(3) 0.83632(14) 0.0480(6) Uani 1 1 d .
C3" C 0.2265(3) 0.6447(3) 0.77386(15) 0.0510(6) Uani 1 1 d .
H3" H 0.2954 0.6347 0.7434 0.061 Uiso 1 1 calc R
C4" C 0.1795(4) 0.7543(4) 0.76341(19) 0.0676(8) Uani 1 1 d .
H4" H 0.2153 0.8257 0.7249 0.081 Uiso 1 1 calc R
C5" C 0.0781(4) 0.7445(4) 0.8148(2) 0.0727(9) Uani 1 1 d .
H5" H 0.0365 0.8083 0.8154 0.087 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
C5" S1 C2" 91.73(15)
C2 O1 C5 108.00(19)
C6 O3 C7 115.9(3)
N1 C2 O1 118.5(2)
N1 C2 C3 131.1(3)
O1 C2 C3 110.4(2)
C2 C3 C6 121.9(2)
C2 C3 C4 105.5(2)
C6 C3 C4 132.6(3)
C5 C4 C3 107.4(2)
C5 C4 C1" 126.0(2)
C3 C4 C1" 126.5(2)
C4 C5 O1 108.7(2)
C4 C5 C1' 137.7(2)
O1 C5 C1' 113.4(2)
O2 C6 O3 123.5(3)
O2 C6 C3 123.8(3)
O3 C6 C3 112.6(2)
O3 C7 H7A 109.5
O3 C7 H7B 109.5
H7A C7 H7B 109.5
O3 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C2 N1 C8 126.2(2)
C2 N1 H1N 117(2)
C8 N1 H1N 117(2)
N1 C8 C9 106.0(3)
N1 C8 C10 109.3(3)
C9 C8 C10 111.0(4)
N1 C8 C11 110.3(3)
C9 C8 C11 108.8(3)
C10 C8 C11 111.3(3)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C8 C11 H11A 109.5
C8 C11 H11B 109.5
H11A C11 H11B 109.5
C8 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C6' C1' C2' 118.8(3)
C6' C1' C5 122.4(3)
C2' C1' C5 118.8(2)
C3' C2' C1' 120.9(3)
C3' C2' H2' 119.6
C1' C2' H2' 119.6
C4' C3' C2' 118.6(3)
C4' C3' H3' 120.7
C2' C3' H3' 120.7
C5' C4' C3' 122.2(3)
C5' C4' N1' 118.8(3)
C3' C4' N1' 119.0(3)
C4' C5' C6' 119.5(3)
C4' C5' H5' 120.2
C6' C5' H5' 120.2
C5' C6' C1' 120.0(3)
C5' C6' H6' 120.0
C1' C6' H6' 120.0
O2' N1' O1' 124.1(3)
O2' N1' C4' 118.1(3)
O1' N1' C4' 117.8(3)
O1" C1" C2" 121.7(2)
O1" C1" C4 120.2(2)
C2" C1" C4 118.0(2)
C3" C2" C1" 128.9(2)
C3" C2" S1 111.2(2)
C1" C2" S1 119.89(19)
C2" C3" C4" 110.7(3)
C2" C3" H3" 124.7
C4" C3" H3" 124.7
C5" C4" C3" 113.1(3)
C5" C4" H4" 123.5
C3" C4" H4" 123.5
C4" C5" S1 113.3(3)
C4" C5" H5" 123.3
S1 C5" H5" 123.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5" 1.681(4)
S1 C2" 1.717(3)
O1 C2 1.339(3)
O1 C5 1.402(3)
O2 C6 1.217(3)
O3 C6 1.346(3)
O3 C7 1.439(4)
C2 N1 1.333(4)
C2 C3 1.390(4)
C3 C6 1.430(4)
C3 C4 1.439(4)
C4 C5 1.359(4)
C4 C1" 1.507(4)
C5 C1' 1.454(4)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
N1 C8 1.487(4)
N1 H1N 0.879(19)
C8 C9 1.508(5)
C8 C10 1.528(5)
C8 C11 1.528(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C1' C6' 1.390(4)
C1' C2' 1.400(4)
C2' C3' 1.381(4)
C2' H2' 0.9300
C3' C4' 1.371(4)
C3' H3' 0.9300
C4' C5' 1.362(5)
C4' N1' 1.470(4)
C5' C6' 1.388(5)
C5' H5' 0.9300
C6' H6' 0.9300
N1' O2' 1.217(4)
N1' O1' 1.228(4)
C1" O1" 1.219(3)
C1" C2" 1.455(4)
C2" C3" 1.398(4)
C3" C4" 1.418(4)
C3" H3" 0.9300
C4" C5" 1.344(5)
C4" H4" 0.9300
C5" H5" 0.9300
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
C5 O1 C2 N1 179.9(2)
C5 O1 C2 C3 -0.4(3)
N1 C2 C3 C6 -1.4(5)
O1 C2 C3 C6 178.9(2)
N1 C2 C3 C4 179.7(3)
O1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 0.3(3)
C6 C3 C4 C5 -178.3(3)
C2 C3 C4 C1" -176.6(2)
C6 C3 C4 C1" 4.8(5)
C3 C4 C5 O1 -0.6(3)
C1" C4 C5 O1 176.4(2)
C3 C4 C5 C1' -175.0(3)
C1" C4 C5 C1' 1.9(5)
C2 O1 C5 C4 0.6(3)
C2 O1 C5 C1' 176.6(2)
C7 O3 C6 O2 1.9(4)
C7 O3 C6 C3 -177.6(3)
C2 C3 C6 O2 -0.1(4)
C4 C3 C6 O2 178.3(3)
C2 C3 C6 O3 179.3(2)
C4 C3 C6 O3 -2.2(4)
O1 C2 N1 C8 2.3(4)
C3 C2 N1 C8 -177.4(3)
C2 N1 C8 C9 176.7(4)
C2 N1 C8 C10 -63.6(4)
C2 N1 C8 C11 59.1(4)
C4 C5 C1' C6' -16.1(5)
O1 C5 C1' C6' 169.7(2)
C4 C5 C1' C2' 163.9(3)
O1 C5 C1' C2' -10.3(3)
C6' C1' C2' C3' 0.6(4)
C5 C1' C2' C3' -179.5(3)
C1' C2' C3' C4' -0.1(4)
C2' C3' C4' C5' -0.3(4)
C2' C3' C4' N1' -179.9(3)
C3' C4' C5' C6' 0.2(5)
N1' C4' C5' C6' 179.8(3)
C4' C5' C6' C1' 0.3(5)
C2' C1' C6' C5' -0.7(4)
C5 C1' C6' C5' 179.3(3)
C5' C4' N1' O2' 178.5(3)
C3' C4' N1' O2' -1.9(4)
C5' C4' N1' O1' 0.0(4)
C3' C4' N1' O1' 179.6(3)
C5 C4 C1" O1" 70.7(4)
C3 C4 C1" O1" -112.9(3)
C5 C4 C1" C2" -106.2(3)
C3 C4 C1" C2" 70.1(3)
O1" C1" C2" C3" -175.3(3)
C4 C1" C2" C3" 1.5(4)
O1" C1" C2" S1 1.7(4)
C4 C1" C2" S1 178.62(19)
C5" S1 C2" C3" -0.4(2)
C5" S1 C2" C1" -178.0(2)
C1" C2" C3" C4" 177.8(3)
S1 C2" C3" C4" 0.5(3)
C2" C3" C4" C5" -0.4(4)
C3" C4" C5" S1 0.1(4)
C2" S1 C5" C4" 0.2(3)
