#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/15/7151597.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_7151597
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         'C17 H25 Cl N O2, H2 O, Cl'
_chemical_formula_sum            'C17 H27 Cl2 N O3'
_chemical_formula_weight         364.30
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 92.720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5210(10)
_cell_length_b                   8.1870(10)
_cell_length_c                   17.336(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_volume                     924.5(2)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            1989
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  0.787
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'Bruker XPREP v5.1 (Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.19(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0310
_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)+(0.0551P)²+0.1304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                1674
_reflns_number_total             1767
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b312633c.txt
_cod_data_source_block           rice45
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7151597
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
Cl1 Cl 0.18602(10) 0.47958(10) 0.82480(4) 0.0443(2) Uani 1 1 d . . .
N1 N -0.0053(4) 0.3014(3) 0.61525(14) 0.0402(6) Uani 1 1 d . . .
H1 H -0.1024 0.3757 0.5997 0.044 Uiso 1 1 calc R . .
C2 C -0.0941(5) 0.1320(5) 0.60359(18) 0.0515(8) Uani 1 1 d . . .
H2A H 0.0147 0.0516 0.6009 0.057 Uiso 1 1 calc R . .
H2B H -0.1791 0.1269 0.5562 0.057 Uiso 1 1 calc R . .
C3 C -0.2220(5) 0.1002(4) 0.67323(18) 0.0455(7) Uani 1 1 d . . .
H3A H -0.1898 -0.0062 0.6952 0.050 Uiso 1 1 calc R . .
H3B H -0.3672 0.1034 0.6583 0.050 Uiso 1 1 calc R . .
C4 C -0.1669(4) 0.2386(4) 0.73358(15) 0.0343(6) Uani 1 1 d . . .
C5 C -0.3405(4) 0.3659(4) 0.72792(17) 0.0386(6) Uani 1 1 d . . .
H5A H -0.3829 0.3799 0.6739 0.042 Uiso 1 1 calc R . .
H5B H -0.4572 0.3231 0.7541 0.042 Uiso 1 1 calc R . .
C6 C -0.2857(5) 0.5336(4) 0.76201(19) 0.0436(7) Uani 1 1 d . . .
H6A H -0.4027 0.6062 0.7552 0.048 Uiso 1 1 calc R . .
H6B H -0.2527 0.5229 0.8169 0.048 Uiso 1 1 calc R . .
C7 C -0.1031(5) 0.6057(4) 0.72241(18) 0.0436(7) Uani 1 1 d . . .
H7A H -0.1421 0.6280 0.6688 0.048 Uiso 1 1 calc R . .
H7B H -0.0647 0.7084 0.7469 0.048 Uiso 1 1 calc R . .
C8 C 0.0794(4) 0.4916(4) 0.72635(14) 0.0368(6) Uani 1 1 d . . .
H8 H 0.1846 0.5351 0.6934 0.040 Uiso 1 1 calc R . .
C9 C 0.0309(4) 0.3157(4) 0.70172(15) 0.0334(6) Uani 1 1 d . . .
H9 H 0.1483 0.2467 0.7175 0.037 Uiso 1 1 calc R . .
C10 C -0.1292(4) 0.1654(4) 0.81492(16) 0.0348(6) Uani 1 1 d . . .
C11 C 0.0258(4) 0.0506(4) 0.83081(17) 0.0401(7) Uani 1 1 d . . .
C12 C 0.0547(4) -0.0171(5) 0.90357(17) 0.0491(7) Uani 1 1 d . . .
H12 H 0.1585 -0.0935 0.9129 0.054 Uiso 1 1 calc R . .
C13 C -0.0691(5) 0.0277(5) 0.96280(18) 0.0490(8) Uani 1 1 d . . .
H13 H -0.0468 -0.0164 1.0119 0.054 Uiso 1 1 calc R . .
C14 C -0.2257(4) 0.1383(4) 0.94820(16) 0.0388(6) Uani 1 1 d . . .
C15 C -0.2553(4) 0.2059(3) 0.87485(16) 0.0361(6) Uani 1 1 d . . .
H15 H -0.3617 0.2800 0.8656 0.040 Uiso 1 1 calc R . .
O16 O 0.1433(3) 0.0055(3) 0.77007(12) 0.0528(6) Uani 1 1 d . . .
C17 C 0.3280(5) -0.0817(5) 0.7864(2) 0.0541(8) Uani 1 1 d . . .
H17A H 0.3930 -0.1046 0.7390 0.065 Uiso 1 1 calc R . .
H17B H 0.2978 -0.1824 0.8118 0.065 Uiso 1 1 calc R . .
H17C H 0.4184 -0.0171 0.8194 0.065 Uiso 1 1 calc R . .
O18 O -0.3449(3) 0.1730(3) 1.00942(12) 0.0514(6) Uani 1 1 d . . .
C19 C -0.5232(6) 0.2701(6) 0.9956(3) 0.0626(10) Uani 1 1 d . . .
H19A H -0.5913 0.2846 1.0430 0.075 Uiso 1 1 calc R . .
H19B H -0.6142 0.2166 0.9585 0.075 Uiso 1 1 calc R . .
H19C H -0.4845 0.3747 0.9759 0.075 Uiso 1 1 calc R . .
C20 C 0.1808(5) 0.3281(5) 0.56980(19) 0.0569(9) Uani 1 1 d . . .
H20A H 0.1447 0.3170 0.5157 0.068 Uiso 1 1 calc R . .
H20B H 0.2835 0.2487 0.5847 0.068 Uiso 1 1 calc R . .
H20C H 0.2337 0.4359 0.5798 0.068 Uiso 1 1 calc R . .
Cl2 Cl -0.40917(17) 0.24306(15) 0.40932(6) 0.0747(3) Uani 1 1 d . . .
O1S O -0.2790(4) 0.4905(5) 0.53447(16) 0.0677(7) Uani 1 1 d . . .
H1S H -0.374(7) 0.559(6) 0.551(3) 0.081 Uiso 1 1 d . . .
H2S H -0.339(7) 0.431(7) 0.498(3) 0.081 Uiso 1 1 d . . .
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'
Cl Cl 0.1484 0.1585 '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
C20 N1 C9 114.8(2) . . ?
C20 N1 C2 112.3(3) . . ?
C9 N1 C2 104.1(2) . . ?
C20 N1 H1 108.5 . . ?
C9 N1 H1 108.5 . . ?
C2 N1 H1 108.5 . . ?
N1 C2 C3 105.7(3) . . ?
N1 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
N1 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C2 C3 C4 106.8(3) . . ?
C2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C5 C4 C10 114.0(2) . . ?
C5 C4 C9 108.8(2) . . ?
C10 C4 C9 112.5(2) . . ?
C5 C4 C3 107.5(2) . . ?
C10 C4 C3 110.5(2) . . ?
C9 C4 C3 102.9(2) . . ?
C6 C5 C4 115.2(2) . . ?
C6 C5 H5A 108.5 . . ?
C4 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C7 C6 C5 110.3(3) . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 111.8(3) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 114.6(2) . . ?
C7 C8 Cl1 110.0(2) . . ?
C9 C8 Cl1 106.0(2) . . ?
C7 C8 H8 108.7 . . ?
C9 C8 H8 108.7 . . ?
Cl1 C8 H8 108.7 . . ?
N1 C9 C8 111.7(2) . . ?
N1 C9 C4 103.1(2) . . ?
C8 C9 C4 116.4(2) . . ?
N1 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
C4 C9 H9 108.4 . . ?
C15 C10 C11 117.3(2) . . ?
C15 C10 C4 121.0(2) . . ?
C11 C10 C4 121.6(2) . . ?
O16 C11 C12 122.1(3) . . ?
O16 C11 C10 116.8(2) . . ?
C12 C11 C10 121.0(3) . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
O18 C14 C13 115.8(3) . . ?
O18 C14 C15 124.3(3) . . ?
C13 C14 C15 119.9(3) . . ?
C14 C15 C10 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C11 O16 C17 118.6(2) . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 O18 C19 118.3(3) . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H1S O1S H2S 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
Cl1 C8 1.815(3) . ?
N1 C20 1.494(4) . ?
N1 C9 1.511(4) . ?
N1 C2 1.513(4) . ?
N1 H1 0.9100 . ?
C2 C3 1.522(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.572(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.538(4) . ?
C4 C10 1.541(4) . ?
C4 C9 1.560(4) . ?
C5 C6 1.530(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.522(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.512(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.531(4) . ?
C8 H8 0.9800 . ?
C9 H9 0.9800 . ?
C10 C15 1.395(4) . ?
C10 C11 1.398(4) . ?
C11 O16 1.382(3) . ?
C11 C12 1.383(4) . ?
C12 C13 1.385(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?
C14 O18 1.375(3) . ?
C14 C15 1.392(4) . ?
C15 H15 0.9300 . ?
O16 C17 1.417(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O18 C19 1.419(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O1S H1S 0.90(5) . ?
O1S H2S 0.88(5) . ?
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
C20 N1 C2 C3 158.7(3) . . . . ?
C9 N1 C2 C3 33.9(3) . . . . ?
N1 C2 C3 C4 -11.9(3) . . . . ?
C2 C3 C4 C5 101.1(3) . . . . ?
C2 C3 C4 C10 -133.9(3) . . . . ?
C2 C3 C4 C9 -13.6(3) . . . . ?
C10 C4 C5 C6 75.9(3) . . . . ?
C9 C4 C5 C6 -50.5(3) . . . . ?
C3 C4 C5 C6 -161.3(2) . . . . ?
C4 C5 C6 C7 58.3(3) . . . . ?
C5 C6 C7 C8 -55.2(3) . . . . ?
C6 C7 C8 C9 49.4(3) . . . . ?
C6 C7 C8 Cl1 -70.0(3) . . . . ?
C20 N1 C9 C8 68.6(3) . . . . ?
C2 N1 C9 C8 -168.3(2) . . . . ?
C20 N1 C9 C4 -165.6(3) . . . . ?
C2 N1 C9 C4 -42.5(3) . . . . ?
C7 C8 C9 N1 73.7(3) . . . . ?
Cl1 C8 C9 N1 -164.76(17) . . . . ?
C7 C8 C9 C4 -44.4(3) . . . . ?
Cl1 C8 C9 C4 77.1(2) . . . . ?
C5 C4 C9 N1 -79.8(3) . . . . ?
C10 C4 C9 N1 152.9(2) . . . . ?
C3 C4 C9 N1 34.1(3) . . . . ?
C5 C4 C9 C8 42.9(3) . . . . ?
C10 C4 C9 C8 -84.4(3) . . . . ?
C3 C4 C9 C8 156.8(2) . . . . ?
C5 C4 C10 C15 4.4(4) . . . . ?
C9 C4 C10 C15 128.8(3) . . . . ?
C3 C4 C10 C15 -116.9(3) . . . . ?
C5 C4 C10 C11 -178.6(3) . . . . ?
C9 C4 C10 C11 -54.1(4) . . . . ?
C3 C4 C10 C11 60.2(3) . . . . ?
C15 C10 C11 O16 177.0(3) . . . . ?
C4 C10 C11 O16 -0.2(4) . . . . ?
C15 C10 C11 C12 -1.2(5) . . . . ?
C4 C10 C11 C12 -178.4(3) . . . . ?
O16 C11 C12 C13 -178.4(3) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C11 C12 C13 C14 1.5(5) . . . . ?
C12 C13 C14 O18 178.3(3) . . . . ?
C12 C13 C14 C15 -1.2(5) . . . . ?
O18 C14 C15 C10 -179.8(3) . . . . ?
C13 C14 C15 C10 -0.3(4) . . . . ?
C11 C10 C15 C14 1.5(4) . . . . ?
C4 C10 C15 C14 178.7(3) . . . . ?
C12 C11 O16 C17 -15.3(5) . . . . ?
C10 C11 O16 C17 166.5(3) . . . . ?
C13 C14 O18 C19 -172.4(3) . . . . ?
C15 C14 O18 C19 7.1(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21188991
