#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/87/2208710.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2208710
loop_
_publ_author_name
'Chen, Shuang-Wei'
'Xu, Cai-Hong'
'Zheng, Guo-Rong'
'Jin, Xu-Fu'
_publ_section_title
;
 tert-Butyl
 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
;
_journal_coeditor_code           SJ2002
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1233
_journal_page_last               o1234
_journal_paper_doi               10.1107/S1600536806006039
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H21 N O3'
_chemical_formula_moiety         'C12 H21 N O3'
_chemical_formula_sum            'C12 H21 N O3'
_chemical_formula_weight         227.30
_chemical_name_systematic
;
tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1420(14)
_cell_length_b                   10.4997(12)
_cell_length_c                   10.7201(13)
_cell_measurement_reflns_used    2732
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.596
_cell_measurement_theta_min      5.331
_cell_volume                     1254.1(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.96
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7189
_diffrn_reflns_theta_full        28.3
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.301
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         1576
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0605P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                1353
_reflns_number_total             1576
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2002.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2208710
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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
O O1 0.71259(16) 0.45682(14) 0.1555(2) 0.0592(5) Uani d . 1
O O2 0.68745(15) 0.91877(15) -0.10261(15) 0.0519(4) Uani d . 1
O O3 0.59242(13) 0.96654(12) 0.07911(17) 0.0459(3) Uani d . 1
N N1 0.59626(17) 0.76753(15) 0.01393(16) 0.0430(4) Uani d . 1
C C1 0.55902(18) 0.71592(19) 0.1351(2) 0.0449(5) Uani d . 1
C C2 0.6717(2) 0.6797(2) 0.2068(2) 0.0482(5) Uani d . 1
C C3 0.7514(2) 0.5854(2) 0.1366(2) 0.0476(5) Uani d . 1
C C4 0.7552(2) 0.6115(2) -0.0032(2) 0.0518(5) Uani d . 1
H H4A 0.8156 0.6760 -0.0195 0.062 Uiso calc R 1
H H4B 0.7795 0.5343 -0.0460 0.062 Uiso calc R 1
C C5 0.6364(2) 0.65604(19) -0.0568(2) 0.0478(5) Uani d . 1
C C6 0.5320(3) 0.5641(3) -0.0327(3) 0.0643(7) Uani d . 1
C C7 0.4836(2) 0.6005(2) 0.0948(3) 0.0602(7) Uani d . 1
C C8 0.63150(16) 0.88712(18) -0.01075(18) 0.0371(4) Uani d . 1
C C9 0.60952(17) 1.10572(17) 0.0698(2) 0.0422(4) Uani d . 1
C C10 0.5475(3) 1.1536(2) 0.1866(3) 0.0627(7) Uani d . 1
H H10A 0.5843 1.1158 0.2587 0.094 Uiso calc R 1
H H10B 0.4642 1.1306 0.1839 0.094 Uiso calc R 1
H H10C 0.5548 1.2445 0.1912 0.094 Uiso calc R 1
C C11 0.7417(2) 1.1370(2) 0.0725(3) 0.0656(7) Uani d . 1
H H11A 0.7799 1.1016 0.0001 0.098 Uiso calc R 1
H H11B 0.7772 1.1015 0.1463 0.098 Uiso calc R 1
H H11C 0.7520 1.2278 0.0727 0.098 Uiso calc R 1
C C12 0.5476(3) 1.1548(2) -0.0461(3) 0.0679(7) Uani d . 1
H H12A 0.4639 1.1333 -0.0428 0.102 Uiso calc R 1
H H12B 0.5832 1.1165 -0.1185 0.102 Uiso calc R 1
H H12C 0.5563 1.2456 -0.0506 0.102 Uiso calc R 1
H H1 0.5111(19) 0.777(2) 0.181(2) 0.042(5) Uiso d . 1
H H2A 0.718(2) 0.750(3) 0.221(3) 0.058(7) Uiso d . 1
H H2B 0.656(2) 0.646(2) 0.286(3) 0.049(6) Uiso d . 1
H H5 0.645(2) 0.683(2) -0.144(3) 0.046(6) Uiso d . 1
H H6A 0.557(3) 0.481(4) -0.041(4) 0.085(10) Uiso d . 1
H H6B 0.469(3) 0.580(3) -0.090(4) 0.082(9) Uiso d . 1
H H7A 0.491(2) 0.533(2) 0.158(3) 0.047(6) Uiso d . 1
H H7B 0.396(3) 0.623(3) 0.092(3) 0.077(9) Uiso d . 1
H H3 0.828(2) 0.594(2) 0.165(3) 0.051(6) Uiso d . 1
H H1A 0.734(3) 0.441(3) 0.230(4) 0.080(10) Uiso d . 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
C3 O1 H1A 104(2)
C8 O3 C9 121.53(16)
C8 N1 C5 123.79(19)
C8 N1 C1 127.07(17)
C5 N1 C1 104.46(17)
N1 C1 C2 107.83(17)
N1 C1 C7 101.34(19)
C2 C1 C7 113.36(18)
N1 C1 H1 111.0(14)
C2 C1 H1 111.5(14)
C7 C1 H1 111.3(13)
C1 C2 C3 113.2(2)
C1 C2 H2A 110.6(16)
C3 C2 H2A 105.7(16)
C1 C2 H2B 113.7(14)
C3 C2 H2B 107.9(15)
H2A C2 H2B 105(2)
O1 C3 C4 108.5(2)
O1 C3 C2 111.4(2)
C4 C3 C2 112.52(19)
O1 C3 H3 108.9(16)
C4 C3 H3 107.0(17)
C2 C3 H3 108.3(16)
C5 C4 C3 113.9(2)
C5 C4 H4A 108.8
C3 C4 H4A 108.8
C5 C4 H4B 108.8
C3 C4 H4B 108.8
H4A C4 H4B 107.7
N1 C5 C4 108.45(18)
N1 C5 C6 100.6(2)
C4 C5 C6 113.8(2)
N1 C5 H5 106.8(14)
C4 C5 H5 111.5(14)
C6 C5 H5 114.7(14)
C7 C6 C5 105.3(2)
C7 C6 H6A 116(2)
C5 C6 H6A 110(2)
C7 C6 H6B 106(2)
C5 C6 H6B 110(2)
H6A C6 H6B 109(3)
C6 C7 C1 104.9(2)
C6 C7 H7A 114.2(14)
C1 C7 H7A 108.9(14)
C6 C7 H7B 112(2)
C1 C7 H7B 110.5(17)
H7A C7 H7B 106(2)
O2 C8 N1 124.56(19)
O2 C8 O3 125.30(17)
N1 C8 O3 110.10(17)
O3 C9 C11 109.88(17)
O3 C9 C12 109.47(18)
C11 C9 C12 112.7(2)
O3 C9 C10 102.33(17)
C11 C9 C10 110.9(2)
C12 C9 C10 110.98(18)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.432(3)
O1 H1A 0.85(4)
O2 C8 1.212(2)
O3 C8 1.347(3)
O3 C9 1.477(2)
N1 C8 1.342(3)
N1 C5 1.465(3)
N1 C1 1.468(3)
C1 C2 1.520(3)
C1 C7 1.537(3)
C1 H1 0.97(2)
C2 C3 1.529(3)
C2 H2A 0.91(3)
C2 H2B 0.94(3)
C3 C4 1.524(3)
C3 H3 0.91(2)
C4 C5 1.517(4)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.534(4)
C5 H5 0.98(3)
C6 C7 1.517(4)
C6 H6A 0.92(4)
C6 H6B 0.95(4)
C7 H7A 0.98(3)
C7 H7B 1.01(3)
C9 C11 1.509(3)
C9 C12 1.513(4)
C9 C10 1.515(4)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
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
C8 N1 C1 C2 -83.0(2)
C5 N1 C1 C2 73.2(2)
C8 N1 C1 C7 157.71(19)
C5 N1 C1 C7 -46.1(2)
N1 C1 C2 C3 -56.6(2)
C7 C1 C2 C3 54.7(3)
C1 C2 C3 O1 -84.2(2)
C1 C2 C3 C4 37.9(3)
O1 C3 C4 C5 86.8(2)
C2 C3 C4 C5 -36.9(3)
C8 N1 C5 C4 85.0(2)
C1 N1 C5 C4 -72.1(2)
C8 N1 C5 C6 -155.3(2)
C1 N1 C5 C6 47.6(2)
C3 C4 C5 N1 54.7(3)
C3 C4 C5 C6 -56.3(3)
N1 C5 C6 C7 -29.7(2)
C4 C5 C6 C7 86.1(2)
C5 C6 C7 C1 2.6(3)
N1 C1 C7 C6 25.5(2)
C2 C1 C7 C6 -89.8(2)
C5 N1 C8 O2 9.9(3)
C1 N1 C8 O2 161.8(2)
C5 N1 C8 O3 -172.07(18)
C1 N1 C8 O3 -20.2(3)
C9 O3 C8 O2 3.4(3)
C9 O3 C8 N1 -174.66(17)
C8 O3 C9 C11 -64.5(3)
C8 O3 C9 C12 59.8(2)
C8 O3 C9 C10 177.61(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13583572
