#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:13:45 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180294 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150894.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_7150894
loop_
_publ_author_name
'Raffaelli, Barbara'
'Pohjoispää, Monika'
'Hase, Tapio'
'Cardin, Christine J.'
'Gan, Yu'
'Wähälä, Kristiina'
_publ_section_title
;
 Stereochemistry and rearrangement reactions of hydroxylignanolactones
;
_journal_issue                   14
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2619
_journal_page_last               2627
_journal_paper_doi               10.1039/b801593g
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H20 N2 O12'
_chemical_formula_weight         564.45
_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                 112.234(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.1713(3)
_cell_length_b                   7.04220(10)
_cell_length_c                   14.1832(3)
_cell_measurement_reflns_used    13566
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      60.9750
_cell_measurement_theta_min      3.3617
_cell_volume                     1217.74(5)
_computing_cell_refinement       'Crysalis Red, Oxford Diffraction Ltd'
_computing_data_collection       'Crysalis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'Crysalis Red, Oxford Diffraction Ltd'
_computing_molecular_graphics    'ORTEP-III (Johnson, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 16.2086
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method
'high and low resolution path 3982 frames, counting time 2 and 20 s.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu k\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17995
_diffrn_reflns_theta_full        61.05
_diffrn_reflns_theta_max         61.05
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    1.057
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Oxford Diffraction Ltd. Empirical absorption correction using
spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         3252
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          2.214
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1045P)²+0.8194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                3154
_reflns_number_total             3252
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b801593g.txt
_cod_data_source_block           br605
_cod_original_cell_volume        1217.74(4)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7150894
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
O12 O 0.26504(9) 0.5231(2) 0.14812(9) 0.0232(3) Uani 1 1 d . . .
O7 O 0.17694(10) 0.8020(2) 0.13347(9) 0.0284(3) Uani 1 1 d . . .
O3 O 0.41966(11) 0.2236(2) -0.16454(10) 0.0325(3) Uani 1 1 d . . .
O2 O 0.41560(12) -0.1980(2) 0.29556(10) 0.0383(4) Uani 1 1 d . . .
O5 O -0.03022(10) -0.0944(2) -0.08592(9) 0.0266(3) Uani 1 1 d . . .
O6 O -0.01004(11) -0.3291(2) -0.19132(10) 0.0308(3) Uani 1 1 d . . .
O11 O 0.01278(14) 0.9424(3) 0.38094(11) 0.0474(4) Uani 1 1 d . . .
C2" C 0.14028(14) 0.7276(3) 0.31215(13) 0.0237(4) Uani 1 1 d . . .
H2" H 0.1159 0.8435 0.2802 0.028 Uiso 1 1 calc R . .
C9 C 0.40313(14) 0.2814(3) -0.09241(14) 0.0238(4) Uani 1 1 d . . .
N2 N 0.05572(14) 0.8065(3) 0.43360(12) 0.0335(4) Uani 1 1 d . . .
O9 O 0.29356(14) 0.0911(3) 0.42034(12) 0.0435(4) Uani 1 1 d . . .
O4 O 0.46986(10) 0.2350(2) 0.00437(10) 0.0296(3) Uani 1 1 d . . .
O1 O 0.55133(11) -0.0771(2) 0.43885(10) 0.0358(4) Uani 1 1 d . . .
C6" C 0.23586(14) 0.4304(3) 0.32431(13) 0.0251(4) Uani 1 1 d . . .
H6" H 0.2759 0.3472 0.3009 0.030 Uiso 1 1 calc R . .
C4" C 0.15335(16) 0.5050(3) 0.44691(14) 0.0294(5) Uani 1 1 d . . .
H4" H 0.1374 0.4721 0.5033 0.035 Uiso 1 1 calc R . .
C3" C 0.11951(15) 0.6757(3) 0.39686(13) 0.0253(4) Uani 1 1 d . . .
N1 N 0.24844(14) 0.2016(3) 0.45866(13) 0.0348(4) Uani 1 1 d . . .
C4 C 0.05337(15) -0.1740(3) -0.19284(13) 0.0248(4) Uani 1 1 d . . .
C3 C 0.04173(14) -0.0332(3) -0.13001(13) 0.0225(4) Uani 1 1 d . . .
C2 C 0.08813(15) 0.1415(3) -0.12380(13) 0.0240(4) Uani 1 1 d . . .
H2 H 0.0772 0.2361 -0.0829 0.029 Uiso 1 1 calc R . .
C8' C 0.31555(14) 0.3858(3) 0.01732(13) 0.0217(4) Uani 1 1 d . . .
H8' H 0.2709 0.2768 0.0208 0.026 Uiso 1 1 calc R . .
C3' C 0.45114(15) -0.0285(3) 0.27208(14) 0.0256(4) Uani 1 1 d . . .
C5" C 0.21204(15) 0.3856(3) 0.40891(15) 0.0272(4) Uani 1 1 d . . .
C7 C 0.20252(16) 0.3682(3) -0.18025(14) 0.0259(4) Uani 1 1 d . . .
H7A H 0.1495 0.4629 -0.1790 0.031 Uiso 1 1 calc R . .
H7B H 0.2139 0.3847 -0.2434 0.031 Uiso 1 1 calc R . .
O8 O 0.23315(15) 0.1677(3) 0.53702(13) 0.0527(5) Uani 1 1 d . . .
C1" C 0.19874(14) 0.6020(3) 0.27533(13) 0.0224(4) Uani 1 1 d . . .
C9' C 0.27488(16) 0.5629(3) 0.05169(14) 0.0262(4) Uani 1 1 d . . .
H9'1 H 0.3260 0.6664 0.0596 0.031 Uiso 1 1 calc R . .
H9'2 H 0.2042 0.5997 0.0014 0.031 Uiso 1 1 calc R . .
C1' C 0.46728(14) 0.2341(3) 0.17498(14) 0.0242(4) Uani 1 1 d . . .
C6' C 0.55001(17) 0.3063(4) 0.26147(15) 0.0330(5) Uani 1 1 d . . .
H6' H 0.5836 0.4202 0.2569 0.040 Uiso 1 1 calc R . .
O10 O 0.04825(18) 0.7709(3) 0.51451(14) 0.0648(6) Uani 1 1 d . . .
C5 C 0.11558(16) -0.1468(3) -0.25076(15) 0.0288(5) Uani 1 1 d . . .
H5 H 0.1237 -0.2415 -0.2930 0.035 Uiso 1 1 calc R . .
C8 C 0.31115(14) 0.4082(3) -0.09159(13) 0.0229(4) Uani 1 1 d . . .
H8 H 0.3320 0.5393 -0.0989 0.027 Uiso 1 1 calc R . .
C1 C 0.15337(15) 0.1743(3) -0.18147(13) 0.0244(4) Uani 1 1 d . . .
C7" C 0.21250(14) 0.6569(3) 0.17927(13) 0.0214(4) Uani 1 1 d . . .
C7' C 0.43728(15) 0.3429(3) 0.07791(14) 0.0248(4) Uani 1 1 d . . .
H7' H 0.4776 0.4633 0.0926 0.030 Uiso 1 1 calc R . .
C036 C -0.04864(17) -0.2905(3) -0.11162(15) 0.0285(4) Uani 1 1 d . . .
H03A H -0.1262 -0.3193 -0.1343 0.034 Uiso 1 1 calc R . .
H03B H -0.0096 -0.3683 -0.0526 0.034 Uiso 1 1 calc R . .
C6 C 0.16588(15) 0.0302(3) -0.24292(14) 0.0275(4) Uani 1 1 d . . .
H6 H 0.2094 0.0524 -0.2803 0.033 Uiso 1 1 calc R . .
C2' C 0.41601(15) 0.0627(3) 0.18032(14) 0.0273(4) Uani 1 1 d . . .
H2' H 0.3601 0.0129 0.1235 0.033 Uiso 1 1 calc R . .
C4' C 0.53334(15) 0.0450(3) 0.35751(14) 0.0295(4) Uani 1 1 d . . .
C5' C 0.58399(18) 0.2114(4) 0.35545(16) 0.0382(5) Uani 1 1 d . . .
H5' H 0.6386 0.2604 0.4134 0.046 Uiso 1 1 calc R . .
C041 C 0.4816(2) -0.2357(4) 0.39874(17) 0.0460(6) Uani 1 1 d . . .
H04A H 0.5252 -0.3489 0.4035 0.055 Uiso 1 1 calc R . .
H04B H 0.4356 -0.2568 0.4374 0.055 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 0.0181 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7" O12 C9' 114.65(15) . . ?
C3' O2 C041 106.39(17) . . ?
C3 O5 C036 105.37(14) . . ?
C4 O6 C036 105.07(15) . . ?
C3" C2" C1" 118.52(19) . . ?
C3" C2" H2" 120.7 . . ?
C1" C2" H2" 120.7 . . ?
O3 C9 O4 121.65(17) . . ?
O3 C9 C8 127.96(17) . . ?
O4 C9 C8 110.39(15) . . ?
O11 N2 O10 123.98(18) . . ?
O11 N2 C3" 118.16(15) . . ?
O10 N2 C3" 117.86(19) . . ?
C9 O4 C7' 109.83(14) . . ?
C4' O1 C041 105.85(15) . . ?
C5" C6" C1" 118.64(19) . . ?
C5" C6" H6" 120.7 . . ?
C1" C6" H6" 120.7 . . ?
C3" C4" C5" 116.64(17) . . ?
C3" C4" H4" 121.7 . . ?
C5" C4" H4" 121.7 . . ?
C2" C3" C4" 123.11(19) . . ?
C2" C3" N2 118.17(19) . . ?
C4" C3" N2 118.70(16) . . ?
O9 N1 O8 123.6(2) . . ?
O9 N1 C5" 118.25(16) . . ?
O8 N1 C5" 118.19(19) . . ?
C5 C4 O6 128.37(19) . . ?
C5 C4 C3 121.5(2) . . ?
O6 C4 C3 110.05(15) . . ?
C2 C3 C4 122.30(16) . . ?
C2 C3 O5 128.19(17) . . ?
C4 C3 O5 109.24(17) . . ?
C3 C2 C1 117.85(18) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C9' C8' C8 110.98(16) . . ?
C9' C8' C7' 113.88(16) . . ?
C8 C8' C7' 102.58(13) . . ?
C9' C8' H8' 109.7 . . ?
C8 C8' H8' 109.7 . . ?
C7' C8' H8' 109.7 . . ?
C2' C3' O2 128.22(18) . . ?
C2' C3' C4' 121.9(2) . . ?
O2 C3' C4' 109.83(17) . . ?
C4" C5" C6" 122.8(2) . . ?
C4" C5" N1 118.63(17) . . ?
C6" C5" N1 118.53(19) . . ?
C1 C7 C8 116.05(17) . . ?
C1 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C1 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C6" C1" C2" 120.25(17) . . ?
C6" C1" C7" 122.79(17) . . ?
C2" C1" C7" 116.86(18) . . ?
O12 C9' C8' 108.33(16) . . ?
O12 C9' H9'1 110.0 . . ?
C8' C9' H9'1 110.0 . . ?
O12 C9' H9'2 110.0 . . ?
C8' C9' H9'2 110.0 . . ?
H9'1 C9' H9'2 108.4 . . ?
C6' C1' C2' 120.02(18) . . ?
C6' C1' C7' 118.08(18) . . ?
C2' C1' C7' 121.89(17) . . ?
C1' C6' C5' 121.6(2) . . ?
C1' C6' H6' 119.2 . . ?
C5' C6' H6' 119.2 . . ?
C4 C5 C6 116.69(19) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
C9 C8 C7 112.85(16) . . ?
C9 C8 C8' 102.87(15) . . ?
C7 C8 C8' 118.44(14) . . ?
C9 C8 H8 107.4 . . ?
C7 C8 H8 107.4 . . ?
C8' C8 H8 107.4 . . ?
C6 C1 C2 119.2(2) . . ?
C6 C1 C7 121.12(16) . . ?
C2 C1 C7 119.62(18) . . ?
O7 C7" O12 124.21(16) . . ?
O7 C7" C1" 123.70(17) . . ?
O12 C7" C1" 112.04(16) . . ?
O4 C7' C1' 109.91(16) . . ?
O4 C7' C8' 103.09(14) . . ?
C1' C7' C8' 118.25(15) . . ?
O4 C7' H7' 108.4 . . ?
C1' C7' H7' 108.4 . . ?
C8' C7' H7' 108.4 . . ?
O5 C036 O6 108.03(15) . . ?
O5 C036 H03A 110.1 . . ?
O6 C036 H03A 110.1 . . ?
O5 C036 H03B 110.1 . . ?
O6 C036 H03B 110.1 . . ?
H03A C036 H03B 108.4 . . ?
C1 C6 C5 122.51(17) . . ?
C1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C3' C2' C1' 117.46(17) . . ?
C3' C2' H2' 121.3 . . ?
C1' C2' H2' 121.3 . . ?
C5' C4' C3' 122.21(19) . . ?
C5' C4' O1 128.64(18) . . ?
C3' C4' O1 109.14(19) . . ?
C4' C5' C6' 116.7(2) . . ?
C4' C5' H5' 121.6 . . ?
C6' C5' H5' 121.6 . . ?
O2 C041 O1 108.51(19) . . ?
O2 C041 H04A 110.0 . . ?
O1 C041 H04A 110.0 . . ?
O2 C041 H04B 110.0 . . ?
O1 C041 H04B 110.0 . . ?
H04A C041 H04B 108.4 . . ?
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
O12 C7" 1.339(2) . ?
O12 C9' 1.449(2) . ?
O7 C7" 1.206(2) . ?
O3 C9 1.195(2) . ?
O2 C3' 1.368(3) . ?
O2 C041 1.416(3) . ?
O5 C3 1.387(2) . ?
O5 C036 1.425(3) . ?
O6 C4 1.380(3) . ?
O6 C036 1.430(2) . ?
O11 N2 1.214(3) . ?
C2" C3" 1.379(3) . ?
C2" C1" 1.397(3) . ?
C2" H2" 0.9300 . ?
C9 O4 1.360(2) . ?
C9 C8 1.509(3) . ?
N2 O10 1.215(2) . ?
N2 C3" 1.469(3) . ?
O9 N1 1.224(3) . ?
O4 C7' 1.479(2) . ?
O1 C4' 1.385(2) . ?
O1 C041 1.421(3) . ?
C6" C5" 1.387(3) . ?
C6" C1" 1.387(3) . ?
C6" H6" 0.9300 . ?
C4" C3" 1.382(3) . ?
C4" C5" 1.382(3) . ?
C4" H4" 0.9300 . ?
N1 O8 1.226(2) . ?
N1 C5" 1.467(3) . ?
C4 C5 1.376(3) . ?
C4 C3 1.380(3) . ?
C3 C2 1.362(3) . ?
C2 C1 1.412(3) . ?
C2 H2 0.9300 . ?
C8' C9' 1.509(3) . ?
C8' C8 1.532(2) . ?
C8' C7' 1.535(3) . ?
C8' H8' 0.9800 . ?
C3' C2' 1.366(3) . ?
C3' C4' 1.384(3) . ?
C7 C1 1.508(3) . ?
C7 C8 1.532(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1" C7" 1.492(3) . ?
C9' H9'1 0.9700 . ?
C9' H9'2 0.9700 . ?
C1' C6' 1.393(3) . ?
C1' C2' 1.399(3) . ?
C1' C7' 1.492(3) . ?
C6' C5' 1.404(3) . ?
C6' H6' 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C8 H8 0.9800 . ?
C1 C6 1.388(3) . ?
C7' H7' 0.9800 . ?
C036 H03A 0.9700 . ?
C036 H03B 0.9700 . ?
C6 H6 0.9300 . ?
C2' H2' 0.9300 . ?
C4' C5' 1.354(3) . ?
C5' H5' 0.9300 . ?
C041 H04A 0.9700 . ?
C041 H04B 0.9700 . ?
