#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/35/1503520.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_1503520
loop_
_publ_author_name
'Davies, Stephen G.'
'Lee, James A.'
'Roberts, Paul M.'
'Thomson, James E.'
'Yin, Jingda'
_publ_section_title
;
 Parallel kinetic resolution of acyclic γ-amino-α,β-unsaturated esters:
 application to the asymmetric synthesis of 4-aminopyrrolidin-2-ones.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              218
_journal_page_last               221
_journal_paper_doi               10.1021/ol203011u
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C8 H16 N2 O2'
_chemical_formula_sum            'C8 H16 N2 O2'
_chemical_formula_weight         172.23
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.5392(6)
_cell_length_b                   6.7124(4)
_cell_length_c                   20.4694(10)
_cell_measurement_reflns_used    1911
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      3
_cell_volume                     1860.27(17)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4781
_diffrn_reflns_theta_full        75.120
_diffrn_reflns_theta_max         76.200
_diffrn_reflns_theta_min         4.320
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1802
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0608
_refine_ls_shift/su_max          0.0002210
_refine_ls_shift/su_mean         0.0000209
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 5.80P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1994
_refine_ls_wR_factor_gt          0.1944
_refine_ls_wR_factor_ref         0.1994
_reflns_limit_h_max              16
_reflns_limit_h_min              0
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                1574
_reflns_number_total             1911
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.15
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0708
_oxford_refine_ls_scale          8.3(6)
_oxford_reflns_number_all        1911
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol203011u_si_002.cif
_cod_data_source_block           70
_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.

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               1503520
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE O   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE N   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE N   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
O1 O 0.61707(17) 0.4463(4) 0.77299(11) 0.0271 1.0000 Uani .
C2 C 0.6050(2) 0.6565(5) 0.77587(15) 0.0239 1.0000 Uani .
C3 C 0.6372(2) 0.7544(5) 0.71262(15) 0.0203 1.0000 Uani .
N4 N 0.74254(19) 0.7261(4) 0.69939(13) 0.0220 1.0000 Uani .
C5 C 0.7642(2) 0.6695(5) 0.63828(15) 0.0225 1.0000 Uani .
O6 O 0.84874(17) 0.6471(4) 0.61641(12) 0.0294 1.0000 Uani .
C7 C 0.6697(2) 0.6434(5) 0.60024(15) 0.0240 1.0000 Uani .
C8 C 0.5861(2) 0.6717(5) 0.65060(15) 0.0207 1.0000 Uani .
N9 N 0.50688(19) 0.8079(4) 0.63062(12) 0.0217 1.0000 Uani .
C10 C 0.4501(2) 0.7433(6) 0.57245(16) 0.0280 1.0000 Uani .
C11 C 0.3843(3) 0.9157(7) 0.55191(19) 0.0437 1.0000 Uani .
C12 C 0.3909(3) 0.5575(8) 0.5877(2) 0.0472 1.0000 Uani .
H21 H 0.6435 0.7103 0.8132 0.0291 1.0000 Uiso R
H22 H 0.5343 0.6866 0.7831 0.0294 1.0000 Uiso R
H31 H 0.6207 0.9009 0.7167 0.0245 1.0000 Uiso R
H71 H 0.6652 0.7469 0.5661 0.0305 1.0000 Uiso R
H72 H 0.6663 0.5108 0.5795 0.0308 1.0000 Uiso R
H81 H 0.5561 0.5407 0.6623 0.0265 1.0000 Uiso R
H101 H 0.4956 0.7150 0.5349 0.0327 1.0000 Uiso R
H111 H 0.3529 0.8795 0.5111 0.0668 1.0000 Uiso R
H112 H 0.3358 0.9365 0.5853 0.0669 1.0000 Uiso R
H113 H 0.4239 1.0341 0.5452 0.0671 1.0000 Uiso R
H121 H 0.3516 0.5285 0.5493 0.0744 1.0000 Uiso R
H122 H 0.3502 0.5819 0.6254 0.0738 1.0000 Uiso R
H123 H 0.4357 0.4479 0.5962 0.0742 1.0000 Uiso R
H91 H 0.5344 0.9237 0.6212 0.0278 1.0000 Uiso R
H41 H 0.7860 0.7776 0.7240 0.0274 1.0000 Uiso R
H11 H 0.5833 0.3919 0.8024 0.0423 1.0000 Uiso R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0302(12) 0.0230(12) 0.0281(12) 0.0038(10) 0.0100(10) 0.0023(10)
C2 0.0252(15) 0.0240(16) 0.0227(15) -0.0009(13) 0.0031(12) 0.0007(14)
C3 0.0172(14) 0.0212(15) 0.0225(15) -0.0009(12) -0.0001(11) -0.0022(12)
N4 0.0169(12) 0.0236(13) 0.0253(12) -0.0009(11) -0.0005(10) -0.0021(11)
C5 0.0229(15) 0.0193(15) 0.0253(15) 0.0033(12) 0.0005(12) 0.0009(13)
O6 0.0231(11) 0.0308(13) 0.0345(13) 0.0043(11) 0.0069(10) 0.0064(10)
C7 0.0247(15) 0.0254(17) 0.0218(15) -0.0013(13) -0.0001(12) 0.0045(14)
C8 0.0206(14) 0.0202(15) 0.0212(15) 0.0008(12) 0.0000(12) -0.0009(12)
N9 0.0180(12) 0.0241(13) 0.0231(13) 0.0003(11) -0.0014(10) -0.0014(11)
C10 0.0219(15) 0.042(2) 0.0202(15) -0.0015(14) -0.0014(12) -0.0042(15)
C11 0.035(2) 0.065(3) 0.0306(19) -0.0025(19) -0.0089(16) 0.016(2)
C12 0.044(2) 0.060(3) 0.038(2) -0.003(2) -0.0076(18) -0.025(2)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 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_publ_flag
C2 O1 H11 109.8 no
O1 C2 C3 111.2(3) yes
O1 C2 H21 109.4 no
C3 C2 H21 110.4 no
O1 C2 H22 108.7 no
C3 C2 H22 108.5 no
H21 C2 H22 108.6 no
C2 C3 N4 112.4(3) yes
C2 C3 C8 114.6(3) yes
N4 C3 C8 103.7(2) yes
C2 C3 H31 106.7 no
N4 C3 H31 110.9 no
C8 C3 H31 108.5 no
C3 N4 C5 115.0(3) yes
C3 N4 H41 120.9 no
C5 N4 H41 121.2 no
N4 C5 O6 125.1(3) yes
N4 C5 C7 109.2(3) yes
O6 C5 C7 125.7(3) yes
C5 C7 C8 105.3(2) yes
C5 C7 H71 109.6 no
C8 C7 H71 110.0 no
C5 C7 H72 111.4 no
C8 C7 H72 111.3 no
H71 C7 H72 109.1 no
C7 C8 C3 105.3(2) yes
C7 C8 N9 115.3(3) yes
C3 C8 N9 109.4(3) yes
C7 C8 H81 110.5 no
C3 C8 H81 107.6 no
N9 C8 H81 108.6 no
C8 N9 C10 114.9(3) yes
C8 N9 H91 107.5 no
C10 N9 H91 107.5 no
N9 C10 C11 107.7(3) yes
N9 C10 C12 110.5(3) yes
C11 C10 C12 112.0(3) yes
N9 C10 H101 110.6 no
C11 C10 H101 107.0 no
C12 C10 H101 109.0 no
C10 C11 H111 107.7 no
C10 C11 H112 108.4 no
H111 C11 H112 110.7 no
C10 C11 H113 109.8 no
H111 C11 H113 109.1 no
H112 C11 H113 111.1 no
C10 C12 H121 106.9 no
C10 C12 H122 109.1 no
H121 C12 H122 111.7 no
C10 C12 H123 109.4 no
H121 C12 H123 109.7 no
H122 C12 H123 110.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.422(4) yes
O1 H11 0.839 no
C2 C3 1.516(4) yes
C2 H21 0.992 no
C2 H22 0.989 no
C3 N4 1.464(4) yes
C3 C8 1.549(4) yes
C3 H31 1.012 no
N4 C5 1.340(4) yes
N4 H41 0.848 no
C5 O6 1.238(4) yes
C5 C7 1.508(4) yes
C7 C8 1.543(4) yes
C7 H71 0.988 no
C7 H72 0.987 no
C8 N9 1.467(4) yes
C8 H81 0.998 no
N9 C10 1.483(4) yes
N9 H91 0.884 no
C10 C11 1.520(5) yes
C10 C12 1.515(6) yes
C10 H101 1.004 no
C11 H111 0.967 no
C11 H112 0.958 no
C11 H113 0.969 no
C12 H121 0.968 no
C12 H122 0.964 no
C12 H123 0.969 no
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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 H72 O6 3_645 137.41(9) 0.987 2.563 3.357(5) yes
N9 H91 O6 3_655 156.95(9) 0.884 2.182 3.015(5) yes
N4 H41 O1 3_655 169.26(10) 0.848 2.002 2.840(5) yes
O1 H11 N9 6_646 170.35(11) 0.839 1.921 2.752(5) yes
