#------------------------------------------------------------------------------
#$Date: 2016-02-20 04:06:23 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202567.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_2202567
loop_
_publ_author_name
'Richard S. Glass'
'Donald R.Deardorff'
'Nhu Y. T. Stessman'
'Carducci, Michael D.'
_publ_section_title
(1α,6α,7α,7aβ)-2,3,5,6,7,7a-Hexahydro-1,6-epoxy-1H-pyrrolizin-7-ol
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1270
_journal_page_last               o1271
_journal_paper_doi               10.1107/S1600536803016970
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C7 H11 N O2'
_chemical_formula_moiety         'C7 H11 N O2'
_chemical_formula_sum            'C7 H11 N O2'
_chemical_formula_weight         141.17
_chemical_name_systematic
;
(1α,6α,7α,7aβ)-2,3,5,6,7,7a-Hexahydro-1,6-epoxy-1H-pyrrolizin-7-ol
;
_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                   9.9294(16)
_cell_length_b                   7.2910(12)
_cell_length_c                   9.1653(15)
_cell_measurement_reflns_used    2854
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      3.47
_cell_volume                     663.52(19)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6311
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         3.47
_diffrn_standards_decay_%        -0.34
_diffrn_standards_interval_time  529.3
_diffrn_standards_number         62
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.8931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         880
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0382P)²+0.1884P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0809
_reflns_number_gt                795
_reflns_number_total             880
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6216.cif
_cod_data_source_block           2
_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               2202567
_cod_database_fobs_code          2202567
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_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
_atom_site_type_symbol
O1 0.01469(17) 0.1313(2) 0.26377(19) 0.0351(4) Uani d . 1 . . O
H1A -0.049(3) 0.128(4) 0.309(4) 0.053 Uiso d . 1 . . H
C1 0.12400(19) 0.1983(3) 0.3451(2) 0.0266(4) Uani d . 1 . . C
H1B 0.2028 0.1133 0.3384 0.032 Uiso calc R 1 . . H
O2 0.00274(14) 0.40236(19) 0.48968(17) 0.0278(3) Uani d . 1 . . O
C2 0.09750(19) 0.2541(3) 0.5037(2) 0.0267(4) Uani d . 1 . . C
H2A 0.0667 0.1516 0.5680 0.032 Uiso calc R 1 . . H
C3 0.2343(2) 0.3352(3) 0.5451(2) 0.0289(4) Uani d . 1 . . C
H3A 0.2260 0.4200 0.6289 0.035 Uiso calc R 1 . . H
H3B 0.2997 0.2375 0.5697 0.035 Uiso calc R 1 . . H
N4 0.27594(16) 0.4365(2) 0.40824(19) 0.0249(3) Uani d . 1 . . N
C5 0.2674(2) 0.6374(3) 0.4267(3) 0.0307(5) Uani d . 1 . . C
H5A 0.3190 0.7005 0.3492 0.037 Uiso calc R 1 . . H
H5B 0.3045 0.6741 0.5226 0.037 Uiso calc R 1 . . H
C6 0.1160(2) 0.6882(3) 0.4167(3) 0.0332(5) Uani d . 1 . . C
H6A 0.0805 0.7261 0.5131 0.040 Uiso calc R 1 . . H
H6B 0.1012 0.7887 0.3459 0.040 Uiso calc R 1 . . H
C7 0.0495(2) 0.5109(3) 0.3650(2) 0.0267(4) Uani d . 1 . . C
H7A -0.0232 0.5332 0.2916 0.032 Uiso calc R 1 . . H
C8 0.16481(19) 0.3943(3) 0.3040(2) 0.0239(4) Uani d . 1 . . C
H8A 0.1863 0.4144 0.1986 0.029 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0353(8) 0.0405(8) 0.0295(8) -0.0126(7) 0.0049(6) -0.0091(8)
C1 0.0276(9) 0.0246(9) 0.0275(10) -0.0004(7) 0.0039(8) -0.0022(8)
O2 0.0236(6) 0.0310(6) 0.0287(7) 0.0001(6) 0.0054(6) -0.0015(6)
C2 0.0278(9) 0.0273(9) 0.0250(9) 0.0010(8) 0.0048(8) 0.0021(8)
C3 0.0270(10) 0.0357(11) 0.0239(10) 0.0001(8) 0.0001(8) 0.0038(9)
N4 0.0217(7) 0.0285(8) 0.0244(8) -0.0003(7) 0.0005(7) 0.0015(7)
C5 0.0312(10) 0.0286(10) 0.0323(11) -0.0071(8) 0.0004(9) -0.0025(9)
C6 0.0354(11) 0.0237(9) 0.0405(12) 0.0015(8) 0.0044(10) -0.0014(9)
C7 0.0238(9) 0.0268(9) 0.0295(10) 0.0032(8) -0.0009(8) 0.0012(8)
C8 0.0249(8) 0.0249(9) 0.0219(9) -0.0002(7) 0.0005(8) -0.0007(7)
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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 112(3)
O1 C1 C8 113.47(18)
O1 C1 C2 117.58(17)
C8 C1 C2 91.80(15)
O1 C1 H1B 110.9
C8 C1 H1B 110.9
C2 C1 H1B 110.9
C2 O2 C7 105.57(15)
O2 C2 C3 108.19(16)
O2 C2 C1 103.13(16)
C3 C2 C1 100.69(16)
O2 C2 H2A 114.5
C3 C2 H2A 114.5
C1 C2 H2A 114.5
N4 C3 C2 103.06(16)
N4 C3 H3A 111.2
C2 C3 H3A 111.2
N4 C3 H3B 111.2
C2 C3 H3B 111.2
H3A C3 H3B 109.1
C5 N4 C8 103.63(15)
C5 N4 C3 111.93(17)
C8 N4 C3 103.17(14)
N4 C5 C6 106.62(16)
N4 C5 H5A 110.4
C6 C5 H5A 110.4
N4 C5 H5B 110.4
C6 C5 H5B 110.4
H5A C5 H5B 108.6
C7 C6 C5 103.61(16)
C7 C6 H6A 111.0
C5 C6 H6A 111.0
C7 C6 H6B 111.0
C5 C6 H6B 111.0
H6A C6 H6B 109.0
O2 C7 C6 110.63(18)
O2 C7 C8 102.79(16)
C6 C7 C8 105.06(16)
O2 C7 H7A 112.6
C6 C7 H7A 112.6
C8 C7 H7A 112.6
N4 C8 C1 103.34(15)
N4 C8 C7 101.79(15)
C1 C8 C7 103.31(16)
N4 C8 H8A 115.5
C1 C8 H8A 115.5
C7 C8 H8A 115.5
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 C1 . 1.404(2) ?
O1 H1A . 0.76(3) ?
C1 C8 . 1.532(3) ?
C1 C2 . 1.532(3) ?
C1 H1B . 1.0000 ?
O2 C2 . 1.439(2) ?
O2 C7 . 1.465(3) ?
C2 C3 . 1.529(3) ?
C2 H2A . 1.0000 ?
C3 N4 . 1.513(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
N4 C5 . 1.477(3) ?
N4 C8 . 1.492(2) ?
C5 C6 . 1.551(3) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.527(3) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.532(3) ?
C7 H7A . 1.0000 ?
C8 H8A . 1.0000 ?
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
O1 H1A N4 3_455 0.76(3) 2.01(3) 2.760(2) 167(3)
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
C7 O2 C2 C3 65.4(2)
C7 O2 C2 C1 -40.65(19)
O1 C1 C2 O2 -62.7(2)
C8 C1 C2 O2 55.11(17)
O1 C1 C2 C3 -174.39(18)
C8 C1 C2 C3 -56.62(16)
O2 C2 C3 N4 -68.9(2)
C1 C2 C3 N4 38.83(18)
C2 C3 N4 C5 107.82(18)
C2 C3 N4 C8 -2.98(19)
C8 N4 C5 C6 33.9(2)
C3 N4 C5 C6 -76.6(2)
N4 C5 C6 C7 -9.9(2)
C2 O2 C7 C6 -104.85(18)
C2 O2 C7 C8 6.88(19)
C5 C6 C7 O2 93.1(2)
C5 C6 C7 C8 -17.2(2)
C5 N4 C8 C1 -151.00(16)
C3 N4 C8 C1 -34.16(19)
C5 N4 C8 C7 -44.06(19)
C3 N4 C8 C7 72.77(17)
O1 C1 C8 N4 177.33(16)
C2 C1 C8 N4 56.09(16)
O1 C1 C8 C7 71.5(2)
C2 C1 C8 C7 -49.69(17)
O2 C7 C8 N4 -77.98(16)
C6 C7 C8 N4 37.8(2)
O2 C7 C8 C1 28.98(19)
C6 C7 C8 C1 144.78(18)
