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#$Date: 2016-03-26 15:33:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180305 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/19/7151992.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_7151992
loop_
_publ_author_name
'Mali, Sachitanand M.'
'Bandyopadhyay, Anupam'
'Jadhav, Sandip V.'
'Kumar, Mothukuri Ganesh'
'Gopi, Hosahudya N.'
_publ_section_title
;
 Synthesis of α, β-unsaturated γ-amino esters with unprecedented
 high (E)-stereoselectivity and their conformational analysis in
 peptides.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6566
_journal_page_last               6574
_journal_paper_doi               10.1039/c1ob05732d
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C13 H24 N O4'
_chemical_formula_sum            'C13 H24 N O4'
_chemical_formula_weight         258.33
_chemical_name_common            Boc-dgAib-OEt
_chemical_name_systematic
'(E)-ethyl 4-(tert-butoxycarbonylamino)-4-methylpent-2-enoate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_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                 90.923(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.669(2)
_cell_length_b                   9.092(2)
_cell_length_c                   15.882(4)
_cell_measurement_reflns_used    1853
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.06
_cell_measurement_theta_min      2.58
_cell_volume                     1540.4(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_pressure         101.325
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0563
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16600
_diffrn_reflns_theta_full        30.28
_diffrn_reflns_theta_max         30.28
_diffrn_reflns_theta_min         2.58
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Graphite monochromator'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             564
_exptl_crystal_recrystallization_method MeOH
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         4448
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1649
_refine_ls_R_factor_gt           0.0651
_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)+(0.1201P)²+0.0056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2427
_reflns_number_gt                1713
_reflns_number_total             4448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05732d.txt
_cod_data_source_block           mo_anu_aibdg_1_0m
_cod_original_cell_volume        1540.3(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7151992
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
O1 O -0.2593(2) 0.6560(3) 0.95965(13) 0.1027(7) Uani 1 1 d .
O2 O -0.2944(2) 0.5430(3) 0.83821(14) 0.1103(8) Uani 1 1 d .
O3 O 0.14799(18) 0.74120(19) 0.83030(11) 0.0784(6) Uani 1 1 d .
O4 O 0.26227(16) 0.69316(18) 0.94912(11) 0.0729(6) Uani 1 1 d .
N1 N 0.17749(18) 0.5081(2) 0.87952(12) 0.0619(6) Uani 1 1 d .
H1 H 0.2191 0.4569 0.9159 0.074 Uiso 1 1 calc R
C1 C 0.1466(3) 0.9118(4) 0.9930(2) 0.0972(10) Uani 1 1 d .
H1A H 0.1568 1.0098 1.0144 0.146 Uiso 1 1 calc R
H1B H 0.1046 0.8525 1.0339 0.146 Uiso 1 1 calc R
H1C H 0.0977 0.9144 0.9418 0.146 Uiso 1 1 calc R
C2 C 0.2739(2) 0.8464(3) 0.97565(17) 0.0717(7) Uani 1 1 d .
C3 C 0.3423(3) 0.9355(4) 0.9106(2) 0.1027(11) Uani 1 1 d .
H3A H 0.4248 0.8958 0.9035 0.154 Uiso 1 1 calc R
H3B H 0.3486 1.0358 0.9291 0.154 Uiso 1 1 calc R
H3C H 0.2970 0.9315 0.8580 0.154 Uiso 1 1 calc R
C4 C 0.3499(4) 0.8353(4) 1.0572(2) 0.1100(12) Uani 1 1 d .
H4A H 0.4295 0.7906 1.0462 0.165 Uiso 1 1 calc R
H4B H 0.3052 0.7764 1.0969 0.165 Uiso 1 1 calc R
H4C H 0.3630 0.9320 1.0800 0.165 Uiso 1 1 calc R
C5 C 0.1915(2) 0.6553(3) 0.88119(15) 0.0597(6) Uani 1 1 d .
C6 C 0.0956(2) 0.4293(2) 0.81939(14) 0.0594(6) Uani 1 1 d .
C7 C 0.1358(3) 0.4554(3) 0.72846(16) 0.0796(8) Uani 1 1 d .
H7A H 0.2212 0.4247 0.7222 0.119 Uiso 1 1 calc R
H7B H 0.1286 0.5582 0.7153 0.119 Uiso 1 1 calc R
H7C H 0.0827 0.3998 0.6909 0.119 Uiso 1 1 calc R
C8 C 0.1098(3) 0.2660(3) 0.83960(19) 0.0812(8) Uani 1 1 d .
H8A H 0.0917 0.2495 0.8979 0.122 Uiso 1 1 calc R
H8B H 0.1941 0.2354 0.8286 0.122 Uiso 1 1 calc R
H8C H 0.0525 0.2102 0.8050 0.122 Uiso 1 1 calc R
C9 C -0.0406(2) 0.4709(3) 0.82933(16) 0.0629(6) Uani 1 1 d .
H9 H -0.0961 0.4380 0.7876 0.075 Uiso 1 1 calc R
C10 C -0.0894(2) 0.5489(3) 0.89081(15) 0.0661(7) Uani 1 1 d .
H10 H -0.0340 0.5825 0.9323 0.079 Uiso 1 1 calc R
C11 C -0.2198(3) 0.5875(3) 0.90035(18) 0.0750(8) Uani 1 1 d .
C12 C -0.4292(4) 0.5756(8) 0.8491(3) 0.186(3) Uani 1 1 d D
H12A H -0.4690 0.4926 0.8763 0.223 Uiso 1 1 calc R
H12B H -0.4377 0.6605 0.8856 0.223 Uiso 1 1 calc R
C13 C -0.4862(5) 0.6018(12) 0.7775(4) 0.271(5) Uani 1 1 d D
H13A H -0.4329 0.6598 0.7425 0.407 Uiso 1 1 calc R
H13B H -0.5626 0.6544 0.7874 0.407 Uiso 1 1 calc R
H13C H -0.5051 0.5104 0.7498 0.407 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 O2 C12 115.2(3)
C5 O4 C2 121.14(19)
C5 N1 C6 124.15(19)
O4 C2 C3 110.7(2)
O4 C2 C1 110.8(2)
C3 C2 C1 111.1(3)
O4 C2 C4 103.0(2)
C3 C2 C4 111.2(3)
C1 C2 C4 109.8(3)
O3 C5 N1 125.9(2)
O3 C5 O4 124.9(2)
N1 C5 O4 109.21(19)
N1 C6 C9 111.86(19)
N1 C6 C8 106.3(2)
C9 C6 C8 108.3(2)
N1 C6 C7 111.4(2)
C9 C6 C7 110.1(2)
C8 C6 C7 108.7(2)
C10 C9 C6 127.0(2)
C9 C10 C11 126.8(2)
O1 C11 O2 121.7(3)
O1 C11 C10 123.7(3)
O2 C11 C10 114.6(2)
C13 C12 O2 112.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.211(3)
O2 C11 1.321(3)
O2 C12 1.482(5)
O3 C5 1.211(3)
O4 C5 1.351(3)
O4 C2 1.460(3)
N1 C5 1.347(3)
N1 C6 1.470(3)
C1 C2 1.512(4)
C2 C3 1.510(4)
C2 C4 1.520(4)
C6 C9 1.513(3)
C6 C8 1.527(3)
C6 C7 1.531(4)
C9 C10 1.320(3)
C10 C11 1.445(4)
C12 C13 1.303(6)
