#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/44/7154473.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_7154473
loop_
_publ_author_name
'Shibuya, M.'
'Sudoh, T.'
'Kawamura, T.'
'Yamamoto, Y.'
_publ_section_title
;
 A lactone-fused cyclohexadiene as a versatile platform for diversified
 synthesis of 5,6,5-tricyclic scaffolds.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5862
_journal_page_last               5866
_journal_paper_doi               10.1039/c5ob00729a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C11 H12 O5'
_chemical_formula_weight         224.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-15 deposited with the CCDC.
2015-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.899(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.939(3)
_cell_length_b                   6.3984(13)
_cell_length_c                   11.757(3)
_cell_measurement_reflns_used    1797
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      3.16
_cell_volume                     969.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6980
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.707908
_exptl_absorpt_correction_type   'empirical (SADABS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0476
_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)+(0.0780P)²+0.1882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                1969
_reflns_number_total             2402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00729a2.cif
_cod_data_source_block           su61
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154473--7154475.cif.
;
_cod_original_cell_volume        969.8(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7154473
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.27536(12) -0.1896(2) 0.21152(13) 0.0170(3) Uani 1 1 d .
H1A H 0.2414 -0.3088 0.1696 0.020 Uiso 1 1 calc R
H1B H 0.3279 -0.2457 0.2698 0.020 Uiso 1 1 calc R
C2 C 0.32827(11) -0.0464(2) 0.12759(12) 0.0135(3) Uani 1 1 d .
C3 C 0.44487(11) -0.0147(3) 0.15053(13) 0.0176(3) Uani 1 1 d .
H3A H 0.4654 -0.0140 0.2336 0.021 Uiso 1 1 calc R
H3B H 0.4833 -0.1273 0.1146 0.021 Uiso 1 1 calc R
C4 C 0.37389(11) 0.3123(2) 0.09590(14) 0.0161(3) Uani 1 1 d .
H4A H 0.3505 0.3481 0.0159 0.019 Uiso 1 1 calc R
H4B H 0.3873 0.4434 0.1394 0.019 Uiso 1 1 calc R
C5 C 0.29299(11) 0.1818(2) 0.14879(12) 0.0133(3) Uani 1 1 d .
C6 C 0.17846(11) 0.1938(2) 0.12093(12) 0.0133(3) Uani 1 1 d .
C7 C 0.10316(11) 0.3134(2) 0.04300(14) 0.0163(3) Uani 1 1 d .
H7A H 0.1083 0.4652 0.0586 0.020 Uiso 1 1 calc R
H7B H 0.1149 0.2878 -0.0379 0.020 Uiso 1 1 calc R
C8 C 0.01622(11) 0.0851(2) 0.15525(13) 0.0170(3) Uani 1 1 d .
C9 C 0.12792(11) 0.0609(2) 0.18316(13) 0.0145(3) Uani 1 1 d .
C10 C 0.19465(11) -0.0621(2) 0.26924(13) 0.0160(3) Uani 1 1 d .
H10 H 0.1514 -0.1545 0.3148 0.019 Uiso 1 1 calc R
C11 C 0.29999(12) -0.1095(2) 0.00347(13) 0.0169(3) Uani 1 1 d .
H11A H 0.3285 -0.0072 -0.0474 0.025 Uiso 1 1 calc R
H11B H 0.2243 -0.1141 -0.0115 0.025 Uiso 1 1 calc R
H11C H 0.3289 -0.2479 -0.0103 0.025 Uiso 1 1 calc R
O1 O 0.46570(8) 0.18532(18) 0.10054(10) 0.0190(3) Uani 1 1 d .
O2 O 0.00327(7) 0.23157(18) 0.06961(9) 0.0169(3) Uani 1 1 d .
O3 O -0.05705(8) 0.00298(19) 0.19321(10) 0.0231(3) Uani 1 1 d .
O4 O 0.24995(8) 0.09115(19) 0.34167(9) 0.0192(3) Uani 1 1 d .
O5 O 0.31213(8) 0.22842(18) 0.27037(9) 0.0166(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0170(7) 0.0154(7) 0.0187(8) 0.0038(6) 0.0019(6) 0.0036(6)
C2 0.0133(6) 0.0147(7) 0.0124(7) -0.0008(6) 0.0013(5) 0.0031(6)
C3 0.0133(7) 0.0206(8) 0.0187(7) 0.0003(6) 0.0011(5) 0.0026(6)
C4 0.0117(6) 0.0175(8) 0.0191(7) -0.0001(6) 0.0009(5) -0.0011(6)
C5 0.0130(6) 0.0162(7) 0.0107(7) -0.0005(5) 0.0006(5) 0.0015(5)
C6 0.0123(7) 0.0138(7) 0.0138(7) -0.0022(5) 0.0005(5) 0.0011(5)
C7 0.0103(6) 0.0179(8) 0.0206(8) 0.0042(6) 0.0002(5) 0.0002(6)
C8 0.0162(7) 0.0184(8) 0.0165(7) -0.0005(6) 0.0019(6) 0.0012(6)
C9 0.0132(7) 0.0165(7) 0.0141(7) -0.0015(6) 0.0023(5) 0.0011(6)
C10 0.0153(7) 0.0187(7) 0.0141(7) 0.0018(6) 0.0017(5) 0.0003(6)
C11 0.0190(7) 0.0178(7) 0.0139(7) -0.0045(6) 0.0016(5) 0.0016(6)
O1 0.0116(5) 0.0207(6) 0.0251(6) 0.0010(5) 0.0039(4) 0.0014(4)
O2 0.0097(5) 0.0204(6) 0.0204(6) 0.0036(4) 0.0002(4) 0.0008(4)
O3 0.0133(5) 0.0274(7) 0.0290(6) 0.0044(5) 0.0049(4) -0.0026(5)
O4 0.0194(5) 0.0274(6) 0.0110(5) -0.0008(4) 0.0034(4) -0.0021(5)
O5 0.0163(5) 0.0223(6) 0.0113(5) -0.0036(4) 0.0019(4) -0.0036(4)
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'
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
C10 C1 C2 108.84(12)
C3 C2 C11 110.92(12)
C3 C2 C1 116.80(12)
C11 C2 C1 111.65(12)
C3 C2 C5 98.44(12)
C11 C2 C5 110.58(12)
C1 C2 C5 107.55(11)
O1 C3 C2 105.20(12)
O1 C4 C5 105.71(12)
O5 C5 C6 106.65(11)
O5 C5 C4 102.93(11)
C6 C5 C4 126.16(12)
O5 C5 C2 108.72(11)
C6 C5 C2 108.23(12)
C4 C5 C2 103.25(11)
C9 C6 C7 109.88(13)
C9 C6 C5 111.84(13)
C7 C6 C5 138.27(13)
O2 C7 C6 103.27(12)
O3 C8 O2 121.25(13)
O3 C8 C9 131.75(15)
O2 C8 C9 107.00(12)
C6 C9 C8 109.39(14)
C6 C9 C10 115.22(13)
C8 C9 C10 135.16(13)
O4 C10 C9 105.60(13)
O4 C10 C1 107.50(12)
C9 C10 C1 110.91(12)
C4 O1 C3 109.55(11)
C8 O2 C7 110.37(11)
C10 O4 O5 109.32(10)
C5 O5 O4 111.97(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C10 1.529(2)
C1 C2 1.549(2)
C2 C3 1.523(2)
C2 C11 1.528(2)
C2 C5 1.556(2)
C3 O1 1.4435(19)
C4 O1 1.4364(18)
C4 C5 1.514(2)
C5 O5 1.4605(17)
C5 C6 1.492(2)
C6 C9 1.330(2)
C6 C7 1.490(2)
C7 O2 1.4531(17)
C8 O3 1.2025(18)
C8 O2 1.3754(19)
C8 C9 1.463(2)
C9 C10 1.497(2)
C10 O4 1.4473(19)
O4 O5 1.4955(15)
