#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228451.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_2228451
loop_
_publ_author_name
'Yuan, Jing'
'Cai, Zhi-Qiang'
'Huang, Chang-Jiang'
'Xu, Wei-Ren'
_publ_section_title
;
 (2R,4R)-1-(tert-Butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylic
 acid
;
_journal_coeditor_code           KP2285
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3258
_journal_paper_doi               10.1107/S1600536810047707
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H19 N O5'
_chemical_formula_moiety         'C11 H19 N O5'
_chemical_formula_sum            'C11 H19 N O5'
_chemical_formula_weight         245.27
_chemical_name_systematic
;
(2R,4R)-1-(tert-Butoxycarbonyl)-4-methoxypyrrolidine-2-
carboxylic acid
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 90.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.4299(13)
_cell_length_b                   9.784(2)
_cell_length_c                   10.279(2)
_cell_measurement_reflns_used    1953
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      3.2
_cell_volume                     646.7(2)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7923
_diffrn_reflns_theta_full        27.74
_diffrn_reflns_theta_max         27.74
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.162
_refine_ls_abs_structure_details 'None, Friedel Pairs merged'
_refine_ls_extinction_coef       0.55(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1601
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0370
_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)+(0.0494P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                1059
_reflns_number_total             1601
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            kp2285.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     P2yb
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2228451
_cod_database_fobs_code          2228451
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.9616(2) 0.74085(17) 0.56702(14) 0.0482(4) Uani d . 1 . .
O O2 1.2349(3) 0.63017(18) 0.30520(17) 0.0550(5) Uani d . 1 . .
O O3 1.1022(3) 0.83878(17) 0.27707(17) 0.0505(5) Uani d . 1 . .
H H3 1.253(5) 0.861(4) 0.262(3) 0.093(11) Uiso d . 1 . .
O O4 0.4931(2) 0.92660(17) 0.24970(16) 0.0472(5) Uani d . 1 . .
O O5 0.6949(2) 0.80182(16) 0.10995(13) 0.0462(5) Uani d . 1 . .
N N1 0.7106(2) 0.7625(2) 0.32240(16) 0.0387(4) Uani d . 1 . .
C C1 1.0873(3) 0.7059(2) 0.2972(2) 0.0383(5) Uani d . 1 . .
C C2 0.8634(3) 0.6534(2) 0.3036(2) 0.0375(5) Uani d . 1 . .
H H2 0.8304 0.6019 0.2244 0.045 Uiso calc R 1 . .
C C3 0.8259(4) 0.5636(2) 0.4235(2) 0.0490(6) Uani d . 1 . .
H H3A 0.7087 0.5027 0.4103 0.059 Uiso calc R 1 . .
H H3B 0.9482 0.5099 0.4448 0.059 Uiso calc R 1 . .
C C4 0.7804(4) 0.6680(2) 0.5283(2) 0.0461(6) Uani d . 1 . .
H H4 0.7092 0.6269 0.6028 0.055 Uiso calc R 1 . .
C C5 0.6428(3) 0.7725(3) 0.45841(19) 0.0454(6) Uani d . 1 . .
H H5A 0.4968 0.7493 0.4670 0.054 Uiso calc R 1 . .
H H5B 0.6654 0.8638 0.4924 0.054 Uiso calc R 1 . .
C C6 1.1031(4) 0.6610(3) 0.6413(2) 0.0632(8) Uani d . 1 . .
H H6A 1.0289 0.6135 0.7084 0.095 Uiso calc R 1 . .
H H6B 1.2057 0.7197 0.6801 0.095 Uiso calc R 1 . .
H H6C 1.1706 0.5960 0.5856 0.095 Uiso calc R 1 . .
C C7 0.6240(3) 0.8376(2) 0.2284(2) 0.0381(5) Uani d . 1 . .
C C8 0.6706(4) 0.8926(2) -0.0042(2) 0.0463(6) Uani d . 1 . .
C C9 0.7760(5) 1.0273(3) 0.0251(3) 0.0712(9) Uani d . 1 . .
H H9A 0.7098 1.0697 0.0983 0.107 Uiso calc R 1 . .
H H9B 0.7650 1.0863 -0.0493 0.107 Uiso calc R 1 . .
H H9C 0.9200 1.0115 0.0447 0.107 Uiso calc R 1 . .
C C10 0.7858(5) 0.8146(4) -0.1077(2) 0.0734(9) Uani d . 1 . .
H H10A 0.9256 0.7975 -0.0791 0.110 Uiso calc R 1 . .
H H10B 0.7884 0.8672 -0.1865 0.110 Uiso calc R 1 . .
H H10C 0.7167 0.7291 -0.1235 0.110 Uiso calc R 1 . .
C C11 0.4450(5) 0.9100(4) -0.0410(3) 0.0750(9) Uani d . 1 . .
H H11A 0.3765 0.8229 -0.0382 0.113 Uiso calc R 1 . .
H H11B 0.4356 0.9469 -0.1274 0.113 Uiso calc R 1 . .
H H11C 0.3794 0.9714 0.0191 0.113 Uiso calc R 1 . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O1 C4 . . 113.5(2) ?
C1 O3 H3 . . 108(2) ?
C7 O5 C8 . . 121.67(18) ?
C7 N1 C2 . . 125.79(17) ?
C7 N1 C5 . . 121.89(19) ?
C2 N1 C5 . . 112.03(17) ?
O2 C1 O3 . . 123.9(2) ?
O2 C1 C2 . . 122.1(2) ?
O3 C1 C2 . . 113.93(19) ?
N1 C2 C1 . . 113.13(18) ?
N1 C2 C3 . . 101.81(17) ?
C1 C2 C3 . . 112.11(17) ?
N1 C2 H2 . . 109.8 ?
C1 C2 H2 . . 109.8 ?
C3 C2 H2 . . 109.8 ?
C4 C3 C2 . . 102.49(18) ?
C4 C3 H3A . . 111.3 ?
C2 C3 H3A . . 111.3 ?
C4 C3 H3B . . 111.3 ?
C2 C3 H3B . . 111.3 ?
H3A C3 H3B . . 109.2 ?
O1 C4 C3 . . 112.24(19) ?
O1 C4 C5 . . 105.62(19) ?
C3 C4 C5 . . 103.28(17) ?
O1 C4 H4 . . 111.7 ?
C3 C4 H4 . . 111.7 ?
C5 C4 H4 . . 111.7 ?
N1 C5 C4 . . 103.27(19) ?
N1 C5 H5A . . 111.1 ?
C4 C5 H5A . . 111.1 ?
N1 C5 H5B . . 111.1 ?
C4 C5 H5B . . 111.1 ?
H5A C5 H5B . . 109.1 ?
O1 C6 H6A . . 109.5 ?
O1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
O1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O4 C7 N1 . . 123.01(19) ?
O4 C7 O5 . . 125.3(2) ?
N1 C7 O5 . . 111.70(19) ?
O5 C8 C10 . . 101.8(2) ?
O5 C8 C11 . . 111.5(2) ?
C10 C8 C11 . . 110.7(2) ?
O5 C8 C9 . . 108.62(19) ?
C10 C8 C9 . . 111.2(2) ?
C11 C8 C9 . . 112.5(2) ?
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 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.421(3) ?
O1 C4 . 1.422(3) ?
O2 C1 . 1.206(3) ?
O3 C1 . 1.320(3) ?
O3 H3 . 1.00(3) ?
O4 C7 . 1.231(3) ?
O5 C7 . 1.347(3) ?
O5 C8 . 1.480(3) ?
N1 C7 . 1.335(3) ?
N1 C2 . 1.464(3) ?
N1 C5 . 1.469(3) ?
C1 C2 . 1.530(3) ?
C2 C3 . 1.533(3) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.513(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.530(3) ?
C4 H4 . 0.9800 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C8 C10 . 1.506(3) ?
C8 C11 . 1.508(4) ?
C8 C9 . 1.512(4) ?
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 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O4 1_655 1.00(3) 1.68(4) 2.672(2) 169(4)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C2 C1 . . . . 85.8(2) ?
C5 N1 C2 C1 . . . . -100.3(2) ?
C7 N1 C2 C3 . . . . -153.7(2) ?
C5 N1 C2 C3 . . . . 20.2(2) ?
O2 C1 C2 N1 . . . . 166.64(19) ?
O3 C1 C2 N1 . . . . -16.0(2) ?
O2 C1 C2 C3 . . . . 52.2(3) ?
O3 C1 C2 C3 . . . . -130.4(2) ?
N1 C2 C3 C4 . . . . -37.2(2) ?
C1 C2 C3 C4 . . . . 84.0(2) ?
C6 O1 C4 C3 . . . . -71.9(2) ?
C6 O1 C4 C5 . . . . 176.29(19) ?
C2 C3 C4 O1 . . . . -72.3(2) ?
C2 C3 C4 C5 . . . . 40.9(2) ?
C7 N1 C5 C4 . . . . 179.02(19) ?
C2 N1 C5 C4 . . . . 4.8(2) ?
O1 C4 C5 N1 . . . . 89.6(2) ?
C3 C4 C5 N1 . . . . -28.4(2) ?
C2 N1 C7 O4 . . . . 178.7(2) ?
C5 N1 C7 O4 . . . . 5.3(3) ?
C2 N1 C7 O5 . . . . -0.3(3) ?
C5 N1 C7 O5 . . . . -173.6(2) ?
C8 O5 C7 O4 . . . . 18.7(3) ?
C8 O5 C7 N1 . . . . -162.41(18) ?
C7 O5 C8 C10 . . . . 175.9(2) ?
C7 O5 C8 C11 . . . . -65.9(3) ?
C7 O5 C8 C9 . . . . 58.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9634063
