#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/88/2008822.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_2008822
loop_
_publ_author_name
'Stájer, Géza'
'Virág, Miklós'
'Sillanpää, Reijo'
_publ_section_title
;Two isomers of
 1,4a,5,7,8,9,9a,10,11,12a-decahydro-1,4-methanocyclopenta[b]pyrrolo[1,6a-a][3,1]benzoxazin-11-one
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1342
_journal_page_last               1344
_journal_paper_doi               10.1107/S0108270199005600
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C15 H19 N O2'
_chemical_formula_weight         245.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.28(2)
_cell_angle_beta                 109.745(16)
_cell_angle_gamma                100.48(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7236(18)
_cell_length_b                   9.748(3)
_cell_length_c                   8.1340(19)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      18.2
_cell_measurement_theta_min      15.8
_cell_volume                     624.2(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1995)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1997)'
_computing_molecular_graphics    'Ortep-3  (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et. al. 1993)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Rigaku AFC5S'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2363
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        -0.58
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0330P)²+0.2245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                1558
_reflns_number_total             2202
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            os1062.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.2245P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.2245P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2008822
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 -0.0122(2) -0.2154(2) -0.7155(2) 0.0648(5) Uani d . 1 . . O
O6 -0.22356(17) -0.44469(14) -0.38677(19) 0.0427(4) Uani d . 1 . . O
N12 -0.0798(2) -0.26023(17) -0.4766(2) 0.0337(4) Uani d . 1 . . N
C1 0.2283(3) -0.1483(2) -0.2589(3) 0.0420(5) Uani d . 1 . . C
H1 0.2700 -0.0826 -0.3235 0.050 Uiso calc R 1 . . H
C2 0.1796(3) -0.0806(2) -0.1120(3) 0.0460(6) Uani d . 1 . . C
H2 0.1516 0.0069 -0.1012 0.055 Uiso calc R 1 . . H
C3 0.1838(3) -0.1676(2) -0.0009(3) 0.0471(6) Uani d . 1 . . C
H3 0.1597 -0.1522 0.1023 0.057 Uiso calc R 1 . . H
C4A 0.0851(2) -0.3839(2) -0.2466(3) 0.0377(5) Uani d . 1 . . C
H4a 0.1153 -0.4699 -0.2911 0.045 Uiso calc R 1 . . H
C4 0.2347(3) -0.2969(2) -0.0721(3) 0.0448(5) Uani d . 1 . . C
H4 0.2813 -0.3523 0.0155 0.054 Uiso calc R 1 . . H
C5 -0.0821(3) -0.4309(2) -0.2241(3) 0.0438(5) Uani d . 1 . . C
H5A -0.0885 -0.5220 -0.1888 0.053 Uiso calc R 1 . . H
H5B -0.0872 -0.3613 -0.1292 0.053 Uiso calc R 1 . . H
C6A -0.2286(2) -0.3105(2) -0.4347(3) 0.0348(5) Uani d . 1 . . C
C7 -0.2532(3) -0.2014(2) -0.2949(3) 0.0419(5) Uani d . 1 . . C
H7A -0.3040 -0.2495 -0.2227 0.050 Uiso calc R 1 . . H
H7B -0.1466 -0.1363 -0.2166 0.050 Uiso calc R 1 . . H
C8 -0.3692(3) -0.1221(2) -0.4053(3) 0.0493(6) Uani d . 1 . . C
H8A -0.3075 -0.0490 -0.4445 0.059 Uiso calc R 1 . . H
H8B -0.4271 -0.0779 -0.3378 0.059 Uiso calc R 1 . . H
C9A -0.3799(3) -0.3291(2) -0.6118(3) 0.0428(5) Uani d . 1 . . C
H9A -0.4412 -0.4299 -0.6584 0.051 Uiso calc R 1 . . H
C9 -0.4917(3) -0.2395(3) -0.5634(3) 0.0515(6) Uani d . 1 . . C
H9B -0.5486 -0.1996 -0.6628 0.062 Uiso calc R 1 . . H
H9C -0.5751 -0.2965 -0.5300 0.062 Uiso calc R 1 . . H
C10 -0.3036(3) -0.2758(3) -0.7410(3) 0.0554(6) Uani d . 1 . . C
H10A -0.3417 -0.3481 -0.8511 0.067 Uiso calc R 1 . . H
H10B -0.3363 -0.1896 -0.7699 0.067 Uiso calc R 1 . . H
C11 -0.1166(3) -0.2454(2) -0.6484(3) 0.0435(5) Uani d . 1 . . C
C12A 0.0860(2) -0.2818(2) -0.3775(3) 0.0352(5) Uani d . 1 . . C
H12A 0.1249 -0.3266 -0.4667 0.042 Uiso calc R 1 . . H
C13 0.3551(3) -0.2256(3) -0.1533(3) 0.0512(6) Uani d . 1 . . C
H13A 0.3837 -0.2939 -0.2300 0.061 Uiso calc R 1 . . H
H13B 0.4562 -0.1602 -0.0640 0.061 Uiso calc R 1 . . H
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 -1 1
1 -2 1
1 -3 1
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
C6A O6 C5 111.35(15) y
C11 N12 C6A 113.81(17) y
C11 N12 C12A 118.75(17) y
C6A N12 C12A 122.71(15) y
C2 C1 C13 100.10(18) y
C2 C1 C12A 108.97(17) y
C13 C1 C12A 98.45(17) y
C3 C2 C1 107.9(2) y
C2 C3 C4 107.5(2) y
C5 C4A C12A 115.36(16) ?
C5 C4A C4 115.07(17) ?
C12A C4A C4 101.88(16) ?
C3 C4 C13 99.95(18) ?
C3 C4 C4A 107.48(17) ?
C13 C4 C4A 100.18(17) ?
O6 C5 C4A 111.91(16) y
O6 C6A N12 108.74(15) y
O6 C6A C7 112.87(16) y
N12 C6A C7 114.22(16) y
O6 C6A C9A 110.22(16) y
N12 C6A C9A 104.71(16) y
C7 C6A C9A 105.69(16) ?
C8 C7 C6A 104.37(17) ?
C7 C8 C9 103.08(18) ?
C10 C9A C9 114.21(19) ?
C10 C9A C6A 105.30(17) ?
C9 C9A C6A 105.47(17) ?
C8 C9 C9A 103.73(18) ?
C11 C10 C9A 106.70(18) ?
O1 C11 N12 124.6(2) y
O1 C11 C10 126.3(2) y
N12 C11 C10 109.03(19) y
N12 C12A C1 118.04(17) y
N12 C12A C4A 114.41(16) y
C1 C12A C4A 103.31(16) ?
C4 C13 C1 93.39(16) ?
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 C11 . 1.224(3) y
O6 C6A . 1.421(2) y
O6 C5 . 1.441(2) y
N12 C11 . 1.360(3) y
N12 C6A . 1.468(2) y
N12 C12A . 1.469(2) y
C1 C2 . 1.503(3) ?
C1 C13 . 1.542(3) ?
C1 C12A . 1.551(3) ?
C2 C3 . 1.321(3) y
C3 C4 . 1.513(3) ?
C4A C5 . 1.527(3) ?
C4A C12A . 1.559(3) ?
C4A C4 . 1.561(3) ?
C4 C13 . 1.535(3) ?
C6A C7 . 1.540(3) ?
C6A C9A . 1.551(3) ?
C7 C8 . 1.517(3) ?
C8 C9 . 1.520(3) ?
C9A C10 . 1.524(3) ?
C9A C9 . 1.529(3) ?
C10 C11 . 1.498(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
_geom_torsion_publ_flag
C13 C1 C2 C3 -33.3(2) ?
C12A C1 C2 C3 69.3(2) ?
C1 C2 C3 C4 -0.3(2) ?
C2 C3 C4 C13 34.0(2) ?
C2 C3 C4 C4A -70.1(2) ?
C5 C4A C4 C3 -57.0(2) ?
C12A C4A C4 C3 68.5(2) ?
C5 C4A C4 C13 -160.94(18) ?
C12A C4A C4 C13 -35.4(2) ?
C6A O6 C5 C4A -64.5(2) y
C12A C4A C5 O6 33.2(2) y
C4 C4A C5 O6 151.46(17) ?
C5 O6 C6A N12 64.7(2) y
C5 O6 C6A C7 -63.1(2) ?
C5 O6 C6A C9A 178.97(16) ?
C11 N12 C6A O6 117.91(18) ?
C12A N12 C6A O6 -37.4(2) y
C11 N12 C6A C7 -115.03(19) ?
C12A N12 C6A C7 89.7(2) ?
C11 N12 C6A C9A 0.1(2) ?
C12A N12 C6A C9A -155.17(17) ?
O6 C6A C7 C8 -141.75(17) ?
N12 C6A C7 C8 93.4(2) ?
C9A C6A C7 C8 -21.2(2) ?
C6A C7 C8 C9 38.9(2) ?
O6 C6A C9A C10 -120.93(18) ?
N12 C6A C9A C10 -4.1(2) ?
C7 C6A C9A C10 116.82(18) ?
O6 C6A C9A C9 117.95(19) ?
N12 C6A C9A C9 -125.26(18) ?
C7 C6A C9A C9 -4.3(2) ?
C7 C8 C9 C9A -41.7(2) ?
C10 C9A C9 C8 -87.0(2) ?
C6A C9A C9 C8 28.1(2) ?
C9 C9A C10 C11 121.7(2) ?
C6A C9A C10 C11 6.5(2) ?
C6A N12 C11 O1 -174.2(2) ?
C12A N12 C11 O1 -17.8(3) ?
C6A N12 C11 C10 4.1(2) ?
C12A N12 C11 C10 160.46(18) ?
C9A C10 C11 O1 171.6(2) ?
C9A C10 C11 N12 -6.6(2) ?
C11 N12 C12A C1 93.7(2) ?
C6A N12 C12A C1 -112.2(2) ?
C11 N12 C12A C4A -144.42(18) ?
C6A N12 C12A C4A 9.7(3) y
C2 C1 C12A N12 63.4(2) ?
C13 C1 C12A N12 167.19(16) ?
C2 C1 C12A C4A -64.0(2) ?
C13 C1 C12A C4A 39.81(19) ?
C5 C4A C12A N12 -7.1(2) y
C4 C4A C12A N12 -132.51(17) ?
C5 C4A C12A C1 122.49(19) ?
C4 C4A C12A C1 -2.9(2) ?
C3 C4 C13 C1 -50.38(19) ?
C4A C4 C13 C1 59.58(19) ?
C2 C1 C13 C4 50.33(19) ?
C12A C1 C13 C4 -60.79(18) ?
