#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/16/7151600.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_7151600
loop_
_publ_author_name
'Urones, Julio G.'
'Garrido, Narciso M.'
'Díez, David'
'El Hammoumi, Mohamed M.'
'Dominguez, Sara H.'
'Antonio Casaseca, J.'
'Davies, Stephen G.'
'Smith, Andrew D.'
_publ_section_title
;
 Asymmetric synthesis of the stereoisomers of
 2-amino-5-carboxymethyl-cyclopentane-1-carboxylate.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              364
_journal_page_last               372
_journal_paper_doi               10.1039/b313386a
_journal_volume                  2
_journal_year                    2004
_chemical_formula_sum            'C25 H31 N O4'
_chemical_formula_weight         409.51
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.0640(10)
_cell_length_b                   13.9610(10)
_cell_length_c                   9.1430(10)
_cell_measurement_temperature    293(2)
_cell_volume                     2305.8(3)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       CRYSOM
_computing_data_reduction        XRAY80
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Seifert XRD 3003 SC'
_diffrn_measurement_method       2theta-omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0091
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2087
_diffrn_reflns_theta_max         65.35
_diffrn_reflns_theta_min         4.00
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             880
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.7
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.20(42)
_refine_ls_extinction_coef       0.0467(25)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.047
_refine_ls_goodness_of_fit_obs   1.041
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         2087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_restrained_S_obs      1.041
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_obs          0.0457
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w=1/[\s^2^(Fo^2^)+(0.0937P)^2^+0.2319P] where
P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_wR_factor_all         0.1272
_refine_ls_wR_factor_obs         0.1210
_reflns_number_observed          1934
_reflns_number_total             2087
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b313386a.txt
_cod_data_source_block           testr
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7151600
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.08740(11) 0.40194(15) 0.4502(3) 0.0475(5) Uani 1 d . .
O1 O 0.19002(14) 0.5239(2) 0.7849(3) 0.0921(9) Uani 1 d . .
O2 O 0.0837(2) 0.5975(2) 0.7393(2) 0.0786(7) Uani 1 d . .
O3 O 0.22667(13) 0.8338(2) 0.4010(4) 0.0877(9) Uani 1 d . .
O4 O 0.34217(11) 0.7802(2) 0.4213(3) 0.0751(7) Uani 1 d . .
C1 C 0.08420(14) 0.5065(2) 0.4560(3) 0.0489(6) Uani 1 d . .
H1 H 0.04073(14) 0.5238(2) 0.5145(3) 0.059 Uiso 1 calc R .
C2 C 0.15274(14) 0.5466(2) 0.5354(3) 0.0482(6) Uani 1 d . .
H2 H 0.19447(14) 0.5040(2) 0.5141(3) 0.058 Uiso 1 calc R .
C3 C 0.16914(14) 0.6440(2) 0.4634(4) 0.0532(7) Uani 1 d . .
H3 H 0.13580(14) 0.6929(2) 0.5030(4) 0.064 Uiso 1 calc R .
C4 C 0.1495(2) 0.6240(2) 0.3034(4) 0.0685(9) Uani 1 d . .
H4A H 0.1407(2) 0.6832(2) 0.2508(4) 0.082 Uiso 1 calc R .
H4B H 0.1890(2) 0.5891(2) 0.2552(4) 0.082 Uiso 1 calc R .
C5 C 0.0798(2) 0.5642(2) 0.3107(4) 0.0707(9) Uani 1 d . .
H5A H 0.0771(2) 0.5211(2) 0.2277(4) 0.085 Uiso 1 calc R .
H5B H 0.0364(2) 0.6050(2) 0.3102(4) 0.085 Uiso 1 calc R .
C6 C 0.1454(2) 0.5534(2) 0.6987(4) 0.0565(7) Uani 1 d . .
C7 C 0.0711(3) 0.6102(3) 0.8942(4) 0.108(2) Uani 1 d . .
H7A H 0.0228(8) 0.6370(24) 0.9095(5) 0.161 Uiso 1 calc R .
H7B H 0.1078(12) 0.6526(21) 0.9336(9) 0.161 Uiso 1 calc R .
H7C H 0.0743(21) 0.5492(5) 0.9425(7) 0.161 Uiso 1 calc R .
C8 C 0.2491(2) 0.6741(2) 0.4871(4) 0.0624(8) Uani 1 d . .
H8A H 0.2595(2) 0.6722(2) 0.5911(4) 0.075 Uiso 1 calc R .
H8B H 0.2811(2) 0.6275(2) 0.4401(4) 0.075 Uiso 1 calc R .
C9 C 0.2685(2) 0.7713(2) 0.4310(4) 0.0593(8) Uani 1 d . .
C10 C 0.3697(2) 0.8728(3) 0.3774(6) 0.0955(13) Uani 1 d . .
H10A H 0.4225(3) 0.8698(7) 0.3665(39) 0.143 Uiso 1 calc R .
H10B H 0.3573(18) 0.9194(6) 0.4506(21) 0.143 Uiso 1 calc R .
H10C H 0.3477(16) 0.8907(12) 0.2859(22) 0.143 Uiso 1 calc R .
C11 C 0.01535(15) 0.3533(2) 0.4626(3) 0.0540(7) Uani 1 d . .
H11 H 0.02549(15) 0.2848(2) 0.4496(3) 0.065 Uiso 1 calc R .
C12 C -0.0394(2) 0.3804(4) 0.3421(4) 0.0870(13) Uani 1 d . .
H12A H -0.0538(14) 0.4462(8) 0.3536(21) 0.131 Uiso 1 calc R .
H12B H -0.0824(8) 0.3402(16) 0.3487(23) 0.131 Uiso 1 calc R .
H12C H -0.0164(6) 0.3718(22) 0.2483(4) 0.131 Uiso 1 calc R .
C13 C -0.01477(14) 0.3640(2) 0.6168(3) 0.0467(6) Uani 1 d . .
C14 C 0.03122(15) 0.3507(2) 0.7344(3) 0.0585(8) Uani 1 d . .
H14 H 0.08106(15) 0.3379(2) 0.7181(3) 0.070 Uiso 1 calc R .
C15 C 0.0056(2) 0.3559(3) 0.8756(4) 0.0695(9) Uani 1 d . .
H15 H 0.0382(2) 0.3469(3) 0.9531(4) 0.083 Uiso 1 calc R .
C16 C -0.0683(2) 0.3744(3) 0.9032(4) 0.0715(9) Uani 1 d . .
H16 H -0.0859(2) 0.3782(3) 0.9987(4) 0.086 Uiso 1 calc R .
C17 C -0.1148(2) 0.3869(3) 0.7874(4) 0.0738(10) Uani 1 d . .
H17 H -0.1646(2) 0.3995(3) 0.8042(4) 0.089 Uiso 1 calc R .
C18 C -0.0889(2) 0.3813(2) 0.6455(4) 0.0633(8) Uani 1 d . .
H18 H -0.1218(2) 0.3893(2) 0.5681(4) 0.076 Uiso 1 calc R .
C19 C 0.1351(2) 0.3625(2) 0.3364(3) 0.0600(8) Uani 1 d . .
H19A H 0.1776(2) 0.4040(2) 0.3232(3) 0.072 Uiso 1 calc R .
H19B H 0.1081(2) 0.3603(2) 0.2447(3) 0.072 Uiso 1 calc R .
C20 C 0.1610(2) 0.2635(2) 0.3751(4) 0.0573(7) Uani 1 d . .
C21 C 0.2066(2) 0.2489(3) 0.4957(4) 0.0719(9) Uani 1 d . .
H21 H 0.2210(2) 0.3012(3) 0.5518(4) 0.086 Uiso 1 calc R .
C22 C 0.2306(2) 0.1596(3) 0.5334(6) 0.0891(11) Uani 1 d . .
H22 H 0.2612(2) 0.1519(3) 0.6144(6) 0.107 Uiso 1 calc R .
C23 C 0.2103(3) 0.0823(3) 0.4540(8) 0.104(2) Uani 1 d . .
H23 H 0.2265(3) 0.0217(3) 0.4811(8) 0.125 Uiso 1 calc R .
C24 C 0.1666(3) 0.0927(3) 0.3359(7) 0.105(2) Uani 1 d . .
H24 H 0.1529(3) 0.0395(3) 0.2811(7) 0.126 Uiso 1 calc R .
C25 C 0.1417(2) 0.1839(3) 0.2958(5) 0.0845(11) Uani 1 d . .
H25 H 0.1116(2) 0.1907(3) 0.2140(5) 0.101 Uiso 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'
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'
H H 0.0000 0.0000 '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
C19 N1 C1 115.2(2) . . ?
C19 N1 C11 113.7(2) . . ?
C1 N1 C11 115.0(2) . . ?
C6 O2 C7 117.6(3) . . ?
C9 O4 C10 116.4(3) . . ?
N1 C1 C2 110.4(2) . . ?
N1 C1 C5 119.2(3) . . ?
C2 C1 C5 104.7(2) . . ?
N1 C1 H1 107.30(14) . . ?
C2 C1 H1 107.3(2) . . ?
C5 C1 H1 107.3(2) . . ?
C6 C2 C3 112.7(2) . . ?
C6 C2 C1 114.8(2) . . ?
C3 C2 C1 105.9(2) . . ?
C6 C2 H2 107.7(2) . . ?
C3 C2 H2 107.68(14) . . ?
C1 C2 H2 107.68(14) . . ?
C8 C3 C4 114.0(3) . . ?
C8 C3 C2 111.5(2) . . ?
C4 C3 C2 101.7(2) . . ?
C8 C3 H3 109.8(2) . . ?
C4 C3 H3 109.8(2) . . ?
C2 C3 H3 109.79(14) . . ?
C5 C4 C3 104.6(3) . . ?
C5 C4 H4A 110.8(2) . . ?
C3 C4 H4A 110.8(2) . . ?
C5 C4 H4B 110.8(2) . . ?
C3 C4 H4B 110.8(2) . . ?
H4A C4 H4B 108.9 . . ?
C4 C5 C1 106.3(3) . . ?
C4 C5 H5A 110.5(2) . . ?
C1 C5 H5A 110.5(2) . . ?
C4 C5 H5B 110.5(2) . . ?
C1 C5 H5B 110.5(2) . . ?
H5A C5 H5B 108.7 . . ?
O1 C6 O2 122.7(3) . . ?
O1 C6 C2 124.9(3) . . ?
O2 C6 C2 112.5(2) . . ?
O2 C7 H7A 109.5(3) . . ?
O2 C7 H7B 109.5(3) . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5(2) . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C3 115.2(3) . . ?
C9 C8 H8A 108.5(2) . . ?
C3 C8 H8A 108.5(2) . . ?
C9 C8 H8B 108.5(2) . . ?
C3 C8 H8B 108.5(2) . . ?
H8A C8 H8B 107.5 . . ?
O3 C9 O4 123.3(3) . . ?
O3 C9 C8 126.8(3) . . ?
O4 C9 C8 110.0(3) . . ?
O4 C10 H10A 109.5(2) . . ?
O4 C10 H10B 109.5(2) . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5(2) . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C13 110.0(2) . . ?
N1 C11 C12 113.7(3) . . ?
C13 C11 C12 114.4(3) . . ?
N1 C11 H11 106.0(2) . . ?
C13 C11 H11 106.0(2) . . ?
C12 C11 H11 106.0(2) . . ?
C11 C12 H12A 109.5(2) . . ?
C11 C12 H12B 109.5(2) . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5(2) . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 117.4(3) . . ?
C14 C13 C11 119.8(2) . . ?
C18 C13 C11 122.6(3) . . ?
C13 C14 C15 121.7(3) . . ?
C13 C14 H14 119.1(2) . . ?
C15 C14 H14 119.1(2) . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.8(2) . . ?
C16 C15 H15 119.8(2) . . ?
C17 C16 C15 118.5(3) . . ?
C17 C16 H16 120.8(2) . . ?
C15 C16 H16 120.8(2) . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17 119.5(2) . . ?
C18 C17 H17 119.5(2) . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H18 119.5(2) . . ?
C13 C18 H18 119.5(2) . . ?
N1 C19 C20 111.3(2) . . ?
N1 C19 H19A 109.37(15) . . ?
C20 C19 H19A 109.4(2) . . ?
N1 C19 H19B 109.4(2) . . ?
C20 C19 H19B 109.4(2) . . ?
H19A C19 H19B 108.0 . . ?
C25 C20 C21 116.8(3) . . ?
C25 C20 C19 122.8(3) . . ?
C21 C20 C19 120.4(3) . . ?
C22 C21 C20 121.5(4) . . ?
C22 C21 H21 119.2(3) . . ?
C20 C21 H21 119.2(2) . . ?
C23 C22 C21 120.4(5) . . ?
C23 C22 H22 119.8(3) . . ?
C21 C22 H22 119.8(3) . . ?
C24 C23 C22 120.3(4) . . ?
C24 C23 H23 119.8(3) . . ?
C22 C23 H23 119.8(3) . . ?
C23 C24 C25 119.8(4) . . ?
C23 C24 H24 120.1(3) . . ?
C25 C24 H24 120.1(3) . . ?
C20 C25 C24 121.1(4) . . ?
C20 C25 H25 119.4(2) . . ?
C24 C25 H25 119.4(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
N1 C19 1.458(4) . ?
N1 C1 1.462(3) . ?
N1 C11 1.473(3) . ?
O1 C6 1.201(4) . ?
O2 C6 1.325(4) . ?
O2 C7 1.446(5) . ?
O3 C9 1.187(4) . ?
O4 C9 1.339(4) . ?
O4 C10 1.441(4) . ?
C1 C2 1.541(4) . ?
C1 C5 1.556(4) . ?
C1 H1 0.98 . ?
C2 C6 1.502(5) . ?
C2 C3 1.539(4) . ?
C2 H2 0.98 . ?
C3 C8 1.520(4) . ?
C3 C4 1.531(5) . ?
C3 H3 0.98 . ?
C4 C5 1.512(5) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C8 C9 1.492(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?
C11 C13 1.519(4) . ?
C11 C12 1.528(4) . ?
C11 H11 0.98 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 C14 1.371(4) . ?
C13 C18 1.387(4) . ?
C14 C15 1.373(5) . ?
C14 H14 0.93 . ?
C15 C16 1.384(5) . ?
C15 H15 0.93 . ?
C16 C17 1.362(5) . ?
C16 H16 0.93 . ?
C17 C18 1.381(5) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 C20 1.502(4) . ?
C19 H19A 0.97 . ?
C19 H19B 0.97 . ?
C20 C25 1.372(4) . ?
C20 C21 1.391(5) . ?
C21 C22 1.365(5) . ?
C21 H21 0.93 . ?
C22 C23 1.352(7) . ?
C22 H22 0.93 . ?
C23 C24 1.345(8) . ?
C23 H23 0.93 . ?
C24 C25 1.399(6) . ?
C24 H24 0.93 . ?
C25 H25 0.93 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9146806
