#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/39/2233957.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_2233957
loop_
_publ_author_name
'Oliveira, F. L.'
'Freire, K. R. L.'
'Aparicio, R.'
'Coelho, F.'
_publ_section_title
;
 (1S,2S,6R,7aR)-2-Benzyl-1,6-dihydroxyhexahydropyrrolizin-3-one
;
_journal_coeditor_code           PV2494
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o587
_journal_paper_doi               10.1107/S1600536812002334
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H17 N O3'
_chemical_formula_moiety         'C14 H17 N O3'
_chemical_formula_sum            'C14 H17 N O3'
_chemical_formula_weight         247.29
_chemical_name_systematic
;
(1S,2S,6R,7aR)-2-Benzyl-1,6-
dihydroxyhexahydropyrrolizin-3-one
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6241(3)
_cell_length_b                   13.6873(6)
_cell_length_c                   13.9726(6)
_cell_measurement_reflns_used    2295
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.53
_cell_measurement_theta_min      4.52
_cell_volume                     1266.84(10)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO'
_diffrn_measurement_method       'Bruker APEX CCD area-detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0106
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26923
_diffrn_reflns_theta_full        69.53
_diffrn_reflns_theta_max         69.53
_diffrn_reflns_theta_min         4.52
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.163
_refine_ls_abs_structure_details
;
Flack (1983) and
Hooft et al. (2008) [Hooft parameter = 0.00(2), (943 Bijvoet
pairs)]'
;
_refine_ls_abs_structure_Flack   0.00(16)
_refine_ls_extinction_coef       0.0086(8)
_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   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0261
_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)+(0.0491P)²+0.1808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                2290
_reflns_number_total             2295
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2494.cif
_cod_data_source_block           I
_cod_database_code               2233957
_cod_database_fobs_code          2233957
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
_atom_site_symmetry_multiplicity
O O1 0.38278(15) 0.66691(6) 0.06882(7) 0.0253(2) Uani d . 1 1
O O2 -0.07013(13) 0.91601(7) 0.27608(7) 0.0264(2) Uani d . 1 1
O O3 0.61142(13) 1.03167(6) 0.28357(7) 0.0238(2) Uani d . 1 1
N N1 0.21491(16) 0.88149(7) 0.19167(7) 0.0204(3) Uani d . 1 1
C C1 0.3664(2) 0.76715(9) 0.09195(9) 0.0217(3) Uani d . 1 1
H H1 0.3789 0.8046 0.0308 0.026 Uiso calc R 1 1
C C2 0.52450(19) 0.80862(9) 0.16169(9) 0.0216(3) Uani d . 1 1
H H2A 0.5399 0.7667 0.2189 0.026 Uiso calc R 1 1
H H2B 0.6575 0.8168 0.1304 0.026 Uiso calc R 1 1
C C3 0.42952(18) 0.90724(9) 0.18696(9) 0.0193(3) Uani d . 1 1
H H3 0.4529 0.9549 0.1338 0.023 Uiso calc R 1 1
C C4 0.46008(18) 0.95809(9) 0.28423(9) 0.0192(3) Uani d . 1 1
H H4 0.4913 0.9084 0.3346 0.023 Uiso calc R 1 1
C C5 0.25242(19) 1.00357(9) 0.30318(9) 0.0200(3) Uani d . 1 1
H H5 0.2442 1.0650 0.2646 0.024 Uiso calc R 1 1
C C6 0.20002(19) 1.03016(9) 0.40713(9) 0.0235(3) Uani d . 1 1
H H6A 0.2759 1.0898 0.4249 0.028 Uiso calc R 1 1
H H6B 0.0544 1.0461 0.4105 0.028 Uiso calc R 1 1
C C7 0.2453(2) 0.95143(9) 0.48012(9) 0.0256(3) Uani d . 1 1
C C8 0.1026(3) 0.87967(10) 0.50128(10) 0.0335(3) Uani d . 1 1
H H8 -0.0244 0.8801 0.4697 0.040 Uiso calc R 1 1
C C9 0.1451(3) 0.80737(11) 0.56844(10) 0.0428(4) Uani d . 1 1
H H9 0.0466 0.7591 0.5826 0.051 Uiso calc R 1 1
C C10 0.3288(3) 0.80545(11) 0.61435(10) 0.0421(4) Uani d . 1 1
H H10 0.3573 0.7556 0.6597 0.050 Uiso calc R 1 1
C C11 0.10960(19) 0.92968(8) 0.25733(9) 0.0210(3) Uani d . 1 1
C C12 0.4306(2) 0.94914(10) 0.52735(9) 0.0288(3) Uani d . 1 1
H H12 0.5291 0.9976 0.5137 0.035 Uiso calc R 1 1
C C13 0.4730(3) 0.87670(11) 0.59435(10) 0.0372(4) Uani d . 1 1
H H13 0.5996 0.8759 0.6263 0.045 Uiso calc R 1 1
C C14 0.1616(2) 0.79469(9) 0.13686(9) 0.0235(3) Uani d . 1 1
H H14A 0.0595 0.8096 0.0872 0.028 Uiso calc R 1 1
H H14B 0.1101 0.7420 0.1788 0.028 Uiso calc R 1 1
H H3A 0.737(4) 1.0009(16) 0.2841(14) 0.050(5) Uiso d . 1 1
H H1A 0.379(3) 0.6326(15) 0.1204(16) 0.043(5) Uiso d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1A 109.6(14)
C4 O3 H3A 107.9(14)
C11 N1 C14 129.85(11)
C11 N1 C3 114.90(10)
C14 N1 C3 114.06(10)
O1 C1 C2 116.78(11)
O1 C1 C14 113.45(11)
C2 C1 C14 104.54(10)
O1 C1 H1 107.2
C2 C1 H1 107.2
C14 C1 H1 107.2
C3 C2 C1 101.05(10)
C3 C2 H2A 111.6
C1 C2 H2A 111.6
C3 C2 H2B 111.6
C1 C2 H2B 111.6
H2A C2 H2B 109.4
N1 C3 C2 101.36(10)
N1 C3 C4 101.33(9)
C2 C3 C4 123.23(10)
N1 C3 H3 109.9
C2 C3 H3 109.9
C4 C3 H3 109.9
O3 C4 C5 110.27(9)
O3 C4 C3 114.03(10)
C5 C4 C3 102.59(10)
O3 C4 H4 109.9
C5 C4 H4 109.9
C3 C4 H4 109.9
C11 C5 C4 102.40(9)
C11 C5 C6 114.43(10)
C4 C5 C6 117.51(10)
C11 C5 H5 107.3
C4 C5 H5 107.3
C6 C5 H5 107.3
C7 C6 C5 115.04(10)
C7 C6 H6A 108.5
C5 C6 H6A 108.5
C7 C6 H6B 108.5
C5 C6 H6B 108.5
H6A C6 H6B 107.5
C12 C7 C8 118.72(13)
C12 C7 C6 120.64(12)
C8 C7 C6 120.64(14)
C9 C8 C7 120.42(16)
C9 C8 H8 119.8
C7 C8 H8 119.8
C10 C9 C8 120.42(15)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C13 119.97(15)
C9 C10 H10 120.0
C13 C10 H10 120.0
O2 C11 N1 125.35(12)
O2 C11 C5 127.58(11)
N1 C11 C5 107.07(11)
C13 C12 C7 120.81(14)
C13 C12 H12 119.6
C7 C12 H12 119.6
C12 C13 C10 119.65(16)
C12 C13 H13 120.2
C10 C13 H13 120.2
N1 C14 C1 101.53(10)
N1 C14 H14A 111.5
C1 C14 H14A 111.5
N1 C14 H14B 111.5
C1 C14 H14B 111.5
H14A C14 H14B 109.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4138(15)
O1 H1A 0.86(2)
O2 C11 1.2333(16)
O3 C4 1.4210(14)
O3 H3A 0.93(2)
N1 C11 1.3279(17)
N1 C14 1.4571(16)
N1 C3 1.4661(16)
C1 C2 1.5390(18)
C1 C14 1.5417(18)
C1 H1 1.0000
C2 C3 1.5306(16)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5403(16)
C3 H3 1.0000
C4 C5 1.5328(17)
C4 H4 1.0000
C5 C11 1.5258(17)
C5 C6 1.5371(16)
C5 H5 1.0000
C6 C7 1.5138(18)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C12 1.394(2)
C7 C8 1.395(2)
C8 C9 1.392(2)
C8 H8 0.9500
C9 C10 1.376(3)
C9 H9 0.9500
C10 C13 1.393(3)
C10 H10 0.9500
C12 C13 1.392(2)
C12 H12 0.9500
C13 H13 0.9500
C14 H14A 0.9900
C14 H14B 0.9900
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 H3A O2 1_655 0.93(2) 1.73(2) 2.6395(12) 164(2)
O1 H1A O3 3_645 0.86(2) 1.93(2) 2.7716(13) 167(19)
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
C(11) N(1) C(3) C(2) 145.23(10)
C(11) N(1) C(3) C(4) 17.61(13)
C(14) N(1) C(3) C(2) -23.51(13)
C(14) N(1) C(3) C(4) -151.12(10)
C(3) N(1) C(11) O(2) -176.49(12)
C(3) N(1) C(11) C(5) 3.73(13)
C(14) N(1) C(11) O(2) -9.9(2)
C(14) N(1) C(11) C(5) 170.29(11)
C(3) N(1) C(14) C(1) -1.76(13)
C(11) N(1) C(14) C(1) -168.41(12)
O(1) C(1) C(2) C(3) -167.02(10)
C(14) C(1) C(2) C(3) -40.78(12)
O(1) C(1) C(14) N(1) 154.80(10)
C(2) C(1) C(14) N(1) 26.51(12)
C(1) C(2) C(3) N(1) 38.05(11)
C(1) C(2) C(3) C(4) 149.83(11)
N(1) C(3) C(4) O(3) -149.89(9)
N(1) C(3) C(4) C(5) -30.67(11)
C(2) C(3) C(4) O(3) 98.31(13)
C(2) C(3) C(4) C(5) -142.47(11)
O(3) C(4) C(5) C(6) -78.74(13)
O(3) C(4) C(5) C(11) 154.95(10)
C(3) C(4) C(5) C(6) 159.44(10)
C(3) C(4) C(5) C(11) 33.13(12)
C(4) C(5) C(6) C(7) -47.18(15)
C(11) C(5) C(6) C(7) 72.99(14)
C(4) C(5) C(11) O(2) 156.61(12)
C(4) C(5) C(11) N(1) -23.61(12)
C(6) C(5) C(11) O(2) 28.33(18)
C(6) C(5) C(11) N(1) -151.89(10)
C(5) C(6) C(7) C(8) -87.85(15)
C(5) C(6) C(7) C(12) 92.02(14)
C(6) C(7) C(8) C(9) 179.96(13)
C(12) C(7) C(8) C(9) 0.1(2)
C(6) C(7) C(12) C(13) -179.84(12)
C(8) C(7) C(12) C(13) 0.0(2)
C(7) C(8) C(9) C(10) -0.4(2)
C(8) C(9) C(10) C(13) 0.6(2)
C(9) C(10) C(13) C(12) -0.5(2)
C(7) C(12) C(13) C(10) 0.2(2)
H(1A) O(1) C(1) C(2) 56.8(14)
H(1A) O(1) C(1) C(14) -64.9(14)
H(1A) O(1) C(1) H(1) 177
H(3A) O(3) C(4) C(3) -76.3(13)
H(3A) O(3) C(4) C(5) 168.9(13)
H(3A) O(3) C(4) H(4) 48
C(11) N(1) C(3) H(3) -99
C(14) N(1) C(3) H(3) 93
C(3) N(1) C(14) H(14A) -121
C(3) N(1) C(14) H(14B) 117
C(11) N(1) C(14) H(14A) 73
C(11) N(1) C(14) H(14B) -50
O(1) C(1) C(2) H(2A) -48
O(1) C(1) C(2) H(2B) 74
C(14) C(1) C(2) H(2A) 78
C(14) C(1) C(2) H(2B) -159
H(1) C(1) C(2) C(3) 73
H(1) C(1) C(2) H(2A) -169
H(1) C(1) C(2) H(2B) -46
O(1) C(1) C(14) H(14A) -86
O(1) C(1) C(14) H(14B) 36
C(2) C(1) C(14) H(14A) 145
C(2) C(1) C(14) H(14B) -92
H(1) C(1) C(14) N(1) -87
H(1) C(1) C(14) H(14A) 32
H(1) C(1) C(14) H(14B) 154
C(1) C(2) C(3) H(3) -78
H(2A) C(2) C(3) N(1) -81
H(2A) C(2) C(3) C(4) 31
H(2A) C(2) C(3) H(3) 163
H(2B) C(2) C(3) N(1) 157
H(2B) C(2) C(3) C(4) -91
H(2B) C(2) C(3) H(3) 41
N(1) C(3) C(4) H(4) 86
C(2) C(3) C(4) H(4) -26
H(3) C(3) C(4) O(3) -34
H(3) C(3) C(4) C(5) 86
H(3) C(3) C(4) H(4) -158
O(3) C(4) C(5) H(5) 42
C(3) C(4) C(5) H(5) -80
H(4) C(4) C(5) C(6) 43
H(4) C(4) C(5) C(11) -84
H(4) C(4) C(5) H(5) 163
C(4) C(5) C(6) H(6A) 75
C(4) C(5) C(6) H(6B) -169
C(11) C(5) C(6) H(6A) -165
C(11) C(5) C(6) H(6B) -49
H(5) C(5) C(6) C(7) -168
H(5) C(5) C(6) H(6A) -46
H(5) C(5) C(6) H(6B) 70
H(5) C(5) C(11) O(2) -91
H(5) C(5) C(11) N(1) 89
H(6A) C(6) C(7) C(8) 150
H(6A) C(6) C(7) C(12) -30
H(6B) C(6) C(7) C(8) 34
H(6B) C(6) C(7) C(12) -146
C(6) C(7) C(8) H(8) 0
C(12) C(7) C(8) H(8) -180
C(6) C(7) C(12) H(12) 0
C(8) C(7) C(12) H(12) -180
C(7) C(8) C(9) H(9) 180
H(8) C(8) C(9) C(10) 180
H(8) C(8) C(9) H(9) 0
C(8) C(9) C(10) H(10) -179
H(9) C(9) C(10) C(13) -179
H(9) C(9) C(10) H(10) 1
C(9) C(10) C(13) H(13) 179
H(10) C(10) C(13) C(12) 180
H(10) C(10) C(13) H(13) 0
C(7) C(12) C(13) H(13) -180
H(12) C(12) C(13) C(10) -180
H(12) C(12) C(13) H(13) 0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657537
