#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:29:13 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180301 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/15/7151596.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_7151596
loop_
_publ_author_name
'Kodato, Shinichi'
'Linders, Joannes T. M.'
'Gu, Xiao-Hui'
'Yamada, Koichiro'
'Flippen-Anderson, Judith L'
'Deschamps, Jeffrey R.'
'Jacobson, Arthur E.'
'Rice, Kenner C.'
_publ_section_title
;
 Synthesis of
 rac-(1R,4aR,9aR)-2-methyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-6-ol.
 An unusual double rearrangement leading to the ortho- and para-f
 oxide-bridged phenylmorphan isomers.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              330
_journal_page_last               336
_journal_paper_doi               10.1039/b312633c
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C15 H20 N O2, Br'
_chemical_formula_sum            'C15 H20 Br N O2'
_chemical_formula_weight         326.23
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.14(2)
_cell_angle_beta                 97.91(2)
_cell_angle_gamma                103.65(2)
_cell_formula_units_Z            4
_cell_length_a                   10.841(2)
_cell_length_b                   11.998(3)
_cell_length_c                   12.157(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_volume                     1465.5(6)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_publication_material  'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_structure_refinement  'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0835
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5233
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.803
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'Bruker XPREP v5.1 (Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0754
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²+9.1372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.2017
_reflns_number_gt                2908
_reflns_number_total             4895
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b312633c.txt
_cod_data_source_block           rice44
_cod_database_code               7151596
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.38571(11) 0.49481(9) 0.26180(9) 0.0551(4) Uani 1 1 d . . .
C1 C 0.3751(10) 0.1962(8) 0.1260(8) 0.045(2) Uani 1 1 d . . .
H1A H 0.4301 0.1983 0.1979 0.054 Uiso 1 1 calc R . .
N2 N 0.4582(7) 0.2636(7) 0.0570(6) 0.0395(19) Uani 1 1 d . . .
C2A C 0.5567(10) 0.2021(9) 0.0197(9) 0.054(3) Uani 1 1 d . . .
H2AA H 0.6067 0.2454 -0.0242 0.080 Uiso 1 1 calc R . .
H2AB H 0.5134 0.1227 -0.0270 0.080 Uiso 1 1 calc R . .
H2AC H 0.6131 0.1990 0.0864 0.080 Uiso 1 1 calc R . .
C3 C 0.3887(10) 0.2917(9) -0.0451(8) 0.048(3) Uani 1 1 d . . .
H3A H 0.3604 0.2204 -0.1093 0.057 Uiso 1 1 calc R . .
H3B H 0.4495 0.3516 -0.0676 0.057 Uiso 1 1 calc R . .
C4 C 0.2710(10) 0.3368(9) -0.0236(8) 0.047(3) Uani 1 1 d . . .
H4A H 0.2178 0.3303 -0.0970 0.056 Uiso 1 1 calc R . .
H4B H 0.3003 0.4202 0.0191 0.056 Uiso 1 1 calc R . .
C4A C 0.1890(9) 0.2658(8) 0.0444(7) 0.037(2) Uani 1 1 d . . .
C4B C 0.0933(9) 0.3175(8) 0.1041(7) 0.036(2) Uani 1 1 d . . .
C5 C -0.0014(9) 0.3675(8) 0.0693(8) 0.042(2) Uani 1 1 d . . .
H5A H -0.0097 0.3833 -0.0024 0.050 Uiso 1 1 calc R . .
C6 C -0.0852(9) 0.3944(8) 0.1422(8) 0.039(2) Uani 1 1 d . . .
O6 O -0.1760(7) 0.4472(7) 0.1037(7) 0.067(2) Uani 1 1 d . . .
H6 H -0.2202 0.4596 0.1523 0.080 Uiso 1 1 calc R . .
C7 C -0.0748(10) 0.3686(10) 0.2477(9) 0.057(3) Uani 1 1 d . . .
H7A H -0.1333 0.3840 0.2944 0.069 Uiso 1 1 calc R . .
C8 C 0.0231(11) 0.3194(10) 0.2851(9) 0.059(3) Uani 1 1 d . . .
H8A H 0.0320 0.3036 0.3568 0.071 Uiso 1 1 calc R . .
C9 C 0.1048(10) 0.2957(8) 0.2128(8) 0.045(2) Uani 1 1 d . . .
O9 O 0.2067(7) 0.2448(6) 0.2352(5) 0.0518(19) Uani 1 1 d . . .
C9A C 0.2850(9) 0.2735(8) 0.1534(7) 0.038(2) Uani 1 1 d . . .
H9AA H 0.3380 0.3563 0.1845 0.045 Uiso 1 1 calc R . .
C10 C 0.1164(11) 0.1362(9) -0.0219(9) 0.057(3) Uani 1 1 d . . .
H10A H 0.0539 0.1051 0.0213 0.069 Uiso 1 1 calc R . .
H10B H 0.0684 0.1360 -0.0954 0.069 Uiso 1 1 calc R . .
C11 C 0.2024(10) 0.0517(9) -0.0445(10) 0.056(3) Uani 1 1 d . . .
H11A H 0.1486 -0.0301 -0.0698 0.067 Uiso 1 1 calc R . .
H11B H 0.2473 0.0672 -0.1055 0.067 Uiso 1 1 calc R . .
C12 C 0.3012(11) 0.0686(9) 0.0644(10) 0.058(3) Uani 1 1 d . . .
H12A H 0.2564 0.0339 0.1176 0.070 Uiso 1 1 calc R . .
H12B H 0.3630 0.0247 0.0440 0.070 Uiso 1 1 calc R . .
Br2 Br -0.39869(11) 0.06184(10) 0.26788(8) 0.0535(4) Uani 1 1 d . . .
C1' C 0.4102(12) -0.1763(10) 0.4083(9) 0.059(3) Uani 1 1 d . . .
H1'A H 0.4847 -0.1053 0.4318 0.070 Uiso 1 1 calc R . .
N2' N 0.4102(9) -0.2477(8) 0.4990(7) 0.051(2) Uani 1 1 d . . .
C2A' C 0.5269(12) -0.2905(11) 0.5151(10) 0.076(4) Uani 1 1 d . . .
H2AD H 0.5216 -0.3349 0.5716 0.113 Uiso 1 1 calc R . .
H2AE H 0.6027 -0.2236 0.5410 0.113 Uiso 1 1 calc R . .
H2AF H 0.5321 -0.3408 0.4432 0.113 Uiso 1 1 calc R . .
C3' C 0.2894(12) -0.3496(11) 0.4785(10) 0.067(3) Uani 1 1 d . . .
H3'A H 0.2917 -0.3805 0.5456 0.080 Uiso 1 1 calc R . .
H3'B H 0.2914 -0.4128 0.4134 0.080 Uiso 1 1 calc R . .
C4' C 0.1589(13) -0.3180(11) 0.4544(10) 0.072(4) Uani 1 1 d . . .
H4'A H 0.0886 -0.3909 0.4242 0.087 Uiso 1 1 calc R . .
H4'B H 0.1431 -0.2740 0.5260 0.087 Uiso 1 1 calc R . .
C4A' C 0.1610(11) -0.2451(9) 0.3698(9) 0.052(3) Uani 1 1 d . . .
C4B' C 0.0672(11) -0.1711(10) 0.3641(8) 0.053(3) Uani 1 1 d . . .
C5' C -0.0717(12) -0.2026(10) 0.3598(9) 0.068(3) Uani 1 1 d . . .
H5'A H -0.1132 -0.2727 0.2959 0.082 Uiso 1 1 calc R . .
H5'B H -0.0879 -0.2230 0.4303 0.082 Uiso 1 1 calc R . .
C6' C -0.1293(11) -0.1095(11) 0.3465(9) 0.059(3) Uani 1 1 d . . .
O6' O -0.2599(8) -0.1358(8) 0.3465(8) 0.084(3) Uani 1 1 d . . .
H6' H -0.2990 -0.1291 0.2867 0.101 Uiso 1 1 calc R . .
C7' C -0.0632(11) -0.0031(11) 0.3353(9) 0.061(3) Uani 1 1 d . . .
H7'A H -0.1067 0.0532 0.3254 0.073 Uiso 1 1 calc R . .
C8' C 0.0708(13) 0.0226(11) 0.3385(10) 0.069(3) Uani 1 1 d . . .
H8'A H 0.1186 0.0955 0.3325 0.083 Uiso 1 1 calc R . .
C9' C 0.1266(11) -0.0661(10) 0.3509(9) 0.057(3) Uani 1 1 d . . .
O9' O 0.2635(7) -0.0521(6) 0.3577(6) 0.060(2) Uani 1 1 d . . .
C9A' C 0.2842(11) -0.1410(9) 0.4137(9) 0.055(3) Uani 1 1 d . . .
H9AB H 0.2864 -0.1076 0.4956 0.066 Uiso 1 1 calc R . .
C10' C 0.1636(13) -0.3110(11) 0.2440(9) 0.069(3) Uani 1 1 d . . .
H10C H 0.0953 -0.3246 0.1828 0.083 Uiso 1 1 calc R . .
C11' C 0.2827(13) -0.3513(10) 0.2272(9) 0.066(3) Uani 1 1 d . . .
H11C H 0.2831 -0.4172 0.2607 0.079 Uiso 1 1 calc R . .
H11D H 0.2802 -0.3793 0.1453 0.079 Uiso 1 1 calc R . .
C12' C 0.4052(13) -0.2521(11) 0.2821(10) 0.070(3) Uani 1 1 d . . .
H12C H 0.4170 -0.1985 0.2330 0.084 Uiso 1 1 calc R . .
H12D H 0.4779 -0.2863 0.2843 0.084 Uiso 1 1 calc R . .
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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C1 C9A 111.9(9) . . ?
C12 C1 N2 115.8(8) . . ?
C9A C1 N2 101.4(7) . . ?
C12 C1 H1A 109.1 . . ?
C9A C1 H1A 109.1 . . ?
N2 C1 H1A 109.1 . . ?
C2A N2 C3 109.2(7) . . ?
C2A N2 C1 111.0(7) . . ?
C3 N2 C1 117.5(7) . . ?
N2 C2A H2AA 109.5 . . ?
N2 C2A H2AB 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
N2 C2A H2AC 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N2 C3 C4 114.5(7) . . ?
N2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
N2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C4A 111.8(7) . . ?
C3 C4 H4A 109.3 . . ?
C4A C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C4A C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C4B C4A C9A 97.6(7) . . ?
C4B C4A C10 106.5(8) . . ?
C9A C4A C10 112.0(7) . . ?
C4B C4A C4 119.5(7) . . ?
C9A C4A C4 104.8(8) . . ?
C10 C4A C4 115.0(8) . . ?
C5 C4B C9 119.2(8) . . ?
C5 C4B C4A 133.5(8) . . ?
C9 C4B C4A 107.0(7) . . ?
C4B C5 C6 119.4(8) . . ?
C4B C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
O6 C6 C7 122.9(9) . . ?
O6 C6 C5 116.7(8) . . ?
C7 C6 C5 120.4(8) . . ?
C6 O6 H6 109.5 . . ?
C6 C7 C8 120.6(9) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C9 C8 C7 117.7(9) . . ?
C9 C8 H8A 121.2 . . ?
C7 C8 H8A 121.2 . . ?
C8 C9 C4B 122.6(9) . . ?
C8 C9 O9 125.4(9) . . ?
C4B C9 O9 112.0(8) . . ?
C9 O9 C9A 102.8(6) . . ?
O9 C9A C1 115.4(7) . . ?
O9 C9A C4A 105.7(7) . . ?
C1 C9A C4A 111.4(7) . . ?
O9 C9A H9AA 108.0 . . ?
C1 C9A H9AA 108.0 . . ?
C4A C9A H9AA 108.0 . . ?
C11 C10 C4A 115.3(9) . . ?
C11 C10 H10A 108.5 . . ?
C4A C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C4A C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 110.7(8) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C1 C12 C11 115.3(8) . . ?
C1 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C1 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C9A' C1' N2' 101.1(8) . . ?
C9A' C1' C12' 110.0(9) . . ?
N2' C1' C12' 113.8(8) . . ?
C9A' C1' H1'A 110.5 . . ?
N2' C1' H1'A 110.5 . . ?
C12' C1' H1'A 110.5 . . ?
C2A' N2' C3' 110.1(9) . . ?
C2A' N2' C1' 112.9(8) . . ?
C3' N2' C1' 114.4(8) . . ?
N2' C2A' H2AD 109.5 . . ?
N2' C2A' H2AE 109.5 . . ?
H2AD C2A' H2AE 109.5 . . ?
N2' C2A' H2AF 109.5 . . ?
H2AD C2A' H2AF 109.5 . . ?
H2AE C2A' H2AF 109.5 . . ?
N2' C3' C4' 115.5(9) . . ?
N2' C3' H3'A 108.4 . . ?
C4' C3' H3'A 108.4 . . ?
N2' C3' H3'B 108.4 . . ?
C4' C3' H3'B 108.4 . . ?
H3'A C3' H3'B 107.5 . . ?
C4A' C4' C3' 111.1(10) . . ?
C4A' C4' H4'A 109.4 . . ?
C3' C4' H4'A 109.4 . . ?
C4A' C4' H4'B 109.4 . . ?
C3' C4' H4'B 109.4 . . ?
H4'A C4' H4'B 108.0 . . ?
C4' C4A' C4B' 119.6(9) . . ?
C4' C4A' C9A' 107.0(9) . . ?
C4B' C4A' C9A' 96.6(8) . . ?
C4' C4A' C10' 115.6(9) . . ?
C4B' C4A' C10' 108.3(8) . . ?
C9A' C4A' C10' 107.4(9) . . ?
C9' C4B' C5' 119.8(10) . . ?
C9' C4B' C4A' 109.8(10) . . ?
C5' C4B' C4A' 130.1(10) . . ?
C6' C5' C4B' 113.5(11) . . ?
C6' C5' H5'A 108.9 . . ?
C4B' C5' H5'A 108.9 . . ?
C6' C5' H5'B 108.9 . . ?
C4B' C5' H5'B 108.9 . . ?
H5'A C5' H5'B 107.7 . . ?
C7' C6' O6' 121.5(10) . . ?
C7' C6' C5' 124.0(12) . . ?
O6' C6' C5' 114.5(11) . . ?
C6' O6' H6' 109.5 . . ?
C6' C7' C8' 120.4(12) . . ?
C6' C7' H7'A 119.8 . . ?
C8' C7' H7'A 119.8 . . ?
C9' C8' C7' 116.0(12) . . ?
C9' C8' H8'A 122.0 . . ?
C7' C8' H8'A 122.0 . . ?
C4B' C9' C8' 126.3(12) . . ?
C4B' C9' O9' 111.3(10) . . ?
C8' C9' O9' 122.4(11) . . ?
C9A' O9' C9' 101.9(8) . . ?
O9' C9A' C1' 117.3(8) . . ?
O9' C9A' C4A' 106.0(8) . . ?
C1' C9A' C4A' 114.6(9) . . ?
O9' C9A' H9AB 106.0 . . ?
C1' C9A' H9AB 106.0 . . ?
C4A' C9A' H9AB 106.0 . . ?
C11' C10' C4A' 116.3(9) . . ?
C11' C10' H10C 121.8 . . ?
C4A' C10' H10C 121.8 . . ?
C12' C11' C10' 111.7(9) . . ?
C12' C11' H11C 109.3 . . ?
C10' C11' H11C 109.3 . . ?
C12' C11' H11D 109.3 . . ?
C10' C11' H11D 109.3 . . ?
H11C C11' H11D 107.9 . . ?
C11' C12' C1' 115.8(10) . . ?
C11' C12' H12C 108.3 . . ?
C1' C12' H12C 108.3 . . ?
C11' C12' H12D 108.3 . . ?
C1' C12' H12D 108.3 . . ?
H12C C12' H12D 107.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C12 1.510(14) . ?
C1 C9A 1.518(11) . ?
C1 N2 1.530(11) . ?
C1 H1A 0.9800 . ?
N2 C2A 1.497(11) . ?
N2 C3 1.509(11) . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C3 C4 1.529(12) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C4A 1.538(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4A C4B 1.515(12) . ?
C4A C9A 1.539(12) . ?
C4A C10 1.537(13) . ?
C4B C5 1.371(12) . ?
C4B C9 1.399(12) . ?
C5 C6 1.395(12) . ?
C5 H5A 0.9300 . ?
C6 O6 1.376(10) . ?
C6 C7 1.382(13) . ?
O6 H6 0.8200 . ?
C7 C8 1.402(14) . ?
C7 H7A 0.9300 . ?
C8 C9 1.363(13) . ?
C8 H8A 0.9300 . ?
C9 O9 1.406(11) . ?
O9 C9A 1.442(10) . ?
C9A H9AA 0.9800 . ?
C10 C11 1.538(13) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.526(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C1' C9A' 1.528(14) . ?
C1' N2' 1.543(12) . ?
C1' C12' 1.582(14) . ?
C1' H1'A 0.9800 . ?
N2' C2A' 1.479(12) . ?
N2' C3' 1.513(15) . ?
C2A' H2AD 0.9600 . ?
C2A' H2AE 0.9600 . ?
C2A' H2AF 0.9600 . ?
C3' C4' 1.555(16) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C4' C4A' 1.493(14) . ?
C4' H4'A 0.9700 . ?
C4' H4'B 0.9700 . ?
C4A' C4B' 1.504(14) . ?
C4A' C9A' 1.531(15) . ?
C4A' C10' 1.562(14) . ?
C4B' C9' 1.329(15) . ?
C4B' C5' 1.454(15) . ?
C5' C6' 1.430(15) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C6' C7' 1.355(15) . ?
C6' O6' 1.376(13) . ?
O6' H6' 0.8200 . ?
C7' C8' 1.404(16) . ?
C7' H7'A 0.9300 . ?
C8' C9' 1.369(15) . ?
C8' H8'A 0.9300 . ?
C9' O9' 1.442(13) . ?
O9' C9A' 1.433(11) . ?
C9A' H9AB 0.9800 . ?
C10' C11' 1.505(16) . ?
C10' H10C 0.9300 . ?
C11' C12' 1.508(16) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 N2 C2A -58.7(11) . . . . ?
C9A C1 N2 C2A -180.0(8) . . . . ?
C12 C1 N2 C3 68.1(10) . . . . ?
C9A C1 N2 C3 -53.2(10) . . . . ?
C2A N2 C3 C4 170.8(9) . . . . ?
C1 N2 C3 C4 43.2(11) . . . . ?
N2 C3 C4 C4A -42.2(12) . . . . ?
C3 C4 C4A C4B 162.2(8) . . . . ?
C3 C4 C4A C9A 54.4(10) . . . . ?
C3 C4 C4A C10 -69.1(11) . . . . ?
C9A C4A C4B C5 160.7(11) . . . . ?
C10 C4A C4B C5 -83.5(13) . . . . ?
C4 C4A C4B C5 49.0(15) . . . . ?
C9A C4A C4B C9 -25.6(9) . . . . ?
C10 C4A C4B C9 90.2(9) . . . . ?
C4 C4A C4B C9 -137.3(9) . . . . ?
C9 C4B C5 C6 -0.8(14) . . . . ?
C4A C4B C5 C6 172.3(9) . . . . ?
C4B C5 C6 O6 178.4(9) . . . . ?
C4B C5 C6 C7 -1.4(15) . . . . ?
O6 C6 C7 C8 -177.2(10) . . . . ?
C5 C6 C7 C8 2.5(16) . . . . ?
C6 C7 C8 C9 -1.5(17) . . . . ?
C7 C8 C9 C4B -0.7(17) . . . . ?
C7 C8 C9 O9 -178.9(10) . . . . ?
C5 C4B C9 C8 1.8(15) . . . . ?
C4A C4B C9 C8 -173.0(10) . . . . ?
C5 C4B C9 O9 -179.8(9) . . . . ?
C4A C4B C9 O9 5.5(11) . . . . ?
C8 C9 O9 C9A -162.5(10) . . . . ?
C4B C9 O9 C9A 19.1(10) . . . . ?
C9 O9 C9A C1 -159.4(8) . . . . ?
C9 O9 C9A C4A -35.8(9) . . . . ?
C12 C1 C9A O9 65.8(11) . . . . ?
N2 C1 C9A O9 -170.2(7) . . . . ?
C12 C1 C9A C4A -54.7(10) . . . . ?
N2 C1 C9A C4A 69.4(9) . . . . ?
C4B C4A C9A O9 37.6(8) . . . . ?
C10 C4A C9A O9 -73.7(9) . . . . ?
C4 C4A C9A O9 160.9(7) . . . . ?
C4B C4A C9A C1 163.6(7) . . . . ?
C10 C4A C9A C1 52.3(10) . . . . ?
C4 C4A C9A C1 -73.1(9) . . . . ?
C4B C4A C10 C11 -154.6(9) . . . . ?
C9A C4A C10 C11 -49.0(12) . . . . ?
C4 C4A C10 C11 70.5(12) . . . . ?
C4A C10 C11 C12 45.8(13) . . . . ?
C9A C1 C12 C11 54.1(11) . . . . ?
N2 C1 C12 C11 -61.4(11) . . . . ?
C10 C11 C12 C1 -48.4(12) . . . . ?
C9A' C1' N2' C2A' -178.0(9) . . . . ?
C12' C1' N2' C2A' 64.1(13) . . . . ?
C9A' C1' N2' C3' 55.1(10) . . . . ?
C12' C1' N2' C3' -62.8(12) . . . . ?
C2A' N2' C3' C4' -177.3(9) . . . . ?
C1' N2' C3' C4' -48.9(11) . . . . ?
N2' C3' C4' C4A' 45.4(13) . . . . ?
C3' C4' C4A' C4B' -159.4(10) . . . . ?
C3' C4' C4A' C9A' -51.2(12) . . . . ?
C3' C4' C4A' C10' 68.4(13) . . . . ?
C4' C4A' C4B' C9' 139.1(11) . . . . ?
C9A' C4A' C4B' C9' 25.3(10) . . . . ?
C10' C4A' C4B' C9' -85.5(11) . . . . ?
C4' C4A' C4B' C5' -47.4(16) . . . . ?
C9A' C4A' C4B' C5' -161.2(10) . . . . ?
C10' C4A' C4B' C5' 88.0(13) . . . . ?
C9' C4B' C5' C6' -2.8(14) . . . . ?
C4A' C4B' C5' C6' -175.8(10) . . . . ?
C4B' C5' C6' C7' 2.0(16) . . . . ?
C4B' C5' C6' O6' -177.7(9) . . . . ?
O6' C6' C7' C8' 178.4(10) . . . . ?
C5' C6' C7' C8' -1.3(17) . . . . ?
C6' C7' C8' C9' 1.3(16) . . . . ?
C5' C4B' C9' C8' 3.4(17) . . . . ?
C4A' C4B' C9' C8' 177.6(10) . . . . ?
C5' C4B' C9' O9' -179.9(9) . . . . ?
C4A' C4B' C9' O9' -5.6(12) . . . . ?
C7' C8' C9' C4B' -2.5(17) . . . . ?
C7' C8' C9' O9' -178.9(9) . . . . ?
C4B' C9' O9' C9A' -18.6(11) . . . . ?
C8' C9' O9' C9A' 158.3(10) . . . . ?
C9' O9' C9A' C1' 164.3(9) . . . . ?
C9' O9' C9A' C4A' 34.9(9) . . . . ?
N2' C1' C9A' O9' 167.4(9) . . . . ?
C12' C1' C9A' O9' -72.0(12) . . . . ?
N2' C1' C9A' C4A' -67.3(10) . . . . ?
C12' C1' C9A' C4A' 53.3(11) . . . . ?
C4' C4A' C9A' O9' -160.3(8) . . . . ?
C4B' C4A' C9A' O9' -36.6(9) . . . . ?
C10' C4A' C9A' O9' 75.0(9) . . . . ?
C4' C4A' C9A' C1' 68.7(10) . . . . ?
C4B' C4A' C9A' C1' -167.6(8) . . . . ?
C10' C4A' C9A' C1' -56.0(11) . . . . ?
C4' C4A' C10' C11' -65.0(15) . . . . ?
C4B' C4A' C10' C11' 157.7(10) . . . . ?
C9A' C4A' C10' C11' 54.3(12) . . . . ?
C4A' C10' C11' C12' -50.0(14) . . . . ?
C10' C11' C12' C1' 45.4(13) . . . . ?
C9A' C1' C12' C11' -47.1(13) . . . . ?
N2' C1' C12' C11' 65.5(13) . . . . ?
