#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:12:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180381 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/50/7205003.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_7205003
loop_
_publ_author_name
'Al-Busafi, Saleh'
'Doncaster, Jeremy R.'
'Drew, Michael G. B.'
'Regan, Andrew C.'
'Whitehead, Roger C.'
_publ_section_title
;
 Exploitation of chemical predisposition in synthesis: an approach to the
 manzamenones
;
_journal_issue                   4
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              476
_journal_paper_doi               10.1039/b110829h
_journal_year                    2002
_chemical_formula_sum            'C18 H22 O7'
_chemical_formula_weight         350.36
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 101.400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.628(13)
_cell_length_b                   11.417(12)
_cell_length_c                   14.112(15)
_cell_measurement_reflns_used    3401
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.52
_cell_volume                     1837(3)
_computing_cell_refinement       XDS
_computing_data_collection       'XDS (Kabsch, 1991)'
_computing_data_reduction        XDS
_computing_molecular_graphics    PLATON(Spek,1994)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Marresearch Image Plate'
_diffrn_measurement_method
'95 frames at 2^o intervals, counting time 2 min.'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1071
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            '3401 B'
_diffrn_reflns_theta_max         26.10
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       misshapen
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.1905
_refine_ls_R_factor_gt           0.0897
_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)+(0.1463P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2198
_refine_ls_wR_factor_ref         0.2623
_reflns_number_gt                1208
_reflns_number_total             3401
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b110829h.txt
_cod_data_source_block           29b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1463P)^2^+0.0000P] 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^)+(0.1463P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               7205003
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0663(4) 0.8837(5) 0.3728(3) 0.0635(13) Uani 1 d . . .
C2 C 0.9951(4) 0.9804(4) 0.3172(3) 0.0667(14) Uani 1 d . . .
C3 C 0.8918(5) 0.9372(6) 0.2702(4) 0.0858(17) Uani 1 d . . .
C4 C 0.8823(4) 0.8120(5) 0.2940(4) 0.0755(15) Uani 1 d . . .
H4 H 0.8122 0.8027 0.3221 0.091 Uiso 1 calc R . .
C5 C 0.8659(4) 0.7361(4) 0.2032(3) 0.0594(12) Uani 1 d . . .
H5 H 0.7869 0.7476 0.1645 0.071 Uiso 1 calc R . .
C6 C 0.8837(4) 0.6004(5) 0.2354(4) 0.0702(14) Uani 1 d . . .
C7 C 0.9674(4) 0.5739(5) 0.3092(3) 0.0740(15) Uani 1 d . . .
H7 H 0.9757 0.4961 0.3291 0.089 Uiso 1 calc R . .
C8 C 1.0503(4) 0.6628(4) 0.3630(3) 0.0590(12) Uani 1 d . . .
H8 H 1.1099 0.6779 0.3242 0.071 Uiso 1 calc R . .
C9 C 0.9888(4) 0.7778(5) 0.3716(3) 0.0713(15) Uani 1 d . . .
H9 H 0.9627 0.7765 0.4335 0.086 Uiso 1 calc R . .
O11 O 1.1705(3) 0.8966(3) 0.4167(3) 0.0915(12) Uani 1 d . . .
C21 C 1.0380(5) 1.1076(5) 0.3111(4) 0.0767(15) Uani 1 d . . .
O23 O 1.1072(3) 1.1433(3) 0.3900(2) 0.0803(11) Uani 1 d . . .
O22 O 1.0147(5) 1.1646(4) 0.2379(3) 0.1271(17) Uani 1 d . . .
C24 C 1.1491(5) 1.2607(4) 0.3881(4) 0.0813(16) Uani 1 d . . .
H24A H 1.0845 1.3142 0.3829 0.098 Uiso 1 calc R . .
H24B H 1.1862 1.2705 0.3337 0.098 Uiso 1 calc R . .
H24C H 1.2048 1.2763 0.4467 0.098 Uiso 1 calc R . .
C31 C 0.7914(7) 1.0044(7) 0.2102(7) 0.145(3) Uani 1 d . . .
H31A H 0.7183 0.9700 0.2198 0.174 Uiso 1 calc R . .
H31B H 0.7939 1.0843 0.2339 0.174 Uiso 1 calc R . .
C32 C 0.7908(11) 1.0070(8) 0.1187(9) 0.200(5) Uani 1 d . . .
H32A H 0.7131 1.0249 0.0840 0.240 Uiso 1 calc R . .
H32B H 0.8144 0.9320 0.0984 0.240 Uiso 1 calc R . .
H32C H 0.8443 1.0660 0.1056 0.240 Uiso 1 calc R . .
C51 C 0.9580(4) 0.7546(4) 0.1393(3) 0.0583(12) Uani 1 d . . .
O52 O 1.0572(3) 0.7814(4) 0.1698(2) 0.0931(13) Uani 1 d . . .
O53 O 0.9134(3) 0.7399(4) 0.0478(2) 0.1040(15) Uani 1 d . . .
C54 C 0.9991(7) 0.7508(8) -0.0151(4) 0.153(4) Uani 1 d . . .
H54A H 0.9608 0.7377 -0.0810 0.183 Uiso 1 calc R . .
H54B H 1.0601 0.6938 0.0033 0.183 Uiso 1 calc R . .
H54C H 1.0325 0.8280 -0.0088 0.183 Uiso 1 calc R . .
C61 C 0.7982(5) 0.5143(5) 0.1772(5) 0.0935(18) Uani 1 d . . .
H61A H 0.7199 0.5332 0.1867 0.112 Uiso 1 calc R . .
H61B H 0.7990 0.5258 0.1092 0.112 Uiso 1 calc R . .
C62 C 0.8197(7) 0.3939(7) 0.1995(5) 0.135(3) Uani 1 d . . .
H62A H 0.7548 0.3480 0.1665 0.162 Uiso 1 calc R . .
H62B H 0.8289 0.3825 0.2680 0.162 Uiso 1 calc R . .
H62C H 0.8901 0.3699 0.1790 0.162 Uiso 1 calc R . .
C81 C 1.1132(5) 0.6183(5) 0.4583(4) 0.0728(14) Uani 1 d . . .
O82 O 1.0883(4) 0.6409(4) 0.5362(3) 0.0969(13) Uani 1 d . . .
O83 O 1.1972(4) 0.5473(4) 0.4478(3) 0.0953(12) Uani 1 d . . .
H83 H 1.2339 0.5276 0.5012 0.114 Uiso 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 C1 C2 123.3(5) . . ?
O11 C1 C9 128.1(5) . . ?
C2 C1 C9 108.5(4) . . ?
C3 C2 C1 109.5(5) . . ?
C3 C2 C21 125.8(5) . . ?
C1 C2 C21 124.7(5) . . ?
C2 C3 C4 110.0(5) . . ?
C2 C3 C31 127.3(6) . . ?
C4 C3 C31 122.3(6) . . ?
C3 C4 C5 111.2(4) . . ?
C3 C4 C9 108.8(5) . . ?
C5 C4 C9 113.9(4) . . ?
C4 C5 C51 115.2(4) . . ?
C4 C5 C6 108.7(4) . . ?
C51 C5 C6 103.3(3) . . ?
C7 C6 C61 125.7(5) . . ?
C7 C6 C5 118.6(4) . . ?
C61 C6 C5 115.7(4) . . ?
C6 C7 C8 123.2(5) . . ?
C81 C8 C7 112.2(4) . . ?
C81 C8 C9 112.4(4) . . ?
C7 C8 C9 111.2(4) . . ?
C1 C9 C8 114.0(4) . . ?
C1 C9 C4 101.6(4) . . ?
C8 C9 C4 119.5(4) . . ?
O22 C21 O23 124.0(6) . . ?
O22 C21 C2 122.4(5) . . ?
O23 C21 C2 113.5(4) . . ?
C21 O23 C24 115.7(4) . . ?
C32 C31 C3 115.1(10) . . ?
O52 C51 O53 124.0(4) . . ?
O52 C51 C5 124.0(4) . . ?
O53 C51 C5 112.0(4) . . ?
C51 O53 C54 113.9(4) . . ?
C62 C61 C6 116.0(5) . . ?
O82 C81 O83 123.5(5) . . ?
O82 C81 C8 125.5(6) . . ?
O83 C81 C8 110.9(5) . . ?
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 O11 1.257(6) . ?
C1 C2 1.505(7) . ?
C1 C9 1.505(7) . ?
C2 C3 1.346(7) . ?
C2 C21 1.543(8) . ?
C3 C4 1.478(8) . ?
C3 C31 1.509(8) . ?
C4 C5 1.527(7) . ?
C4 C9 1.532(6) . ?
C5 C51 1.544(6) . ?
C5 C6 1.617(7) . ?
C6 C7 1.313(7) . ?
C6 C61 1.519(7) . ?
C7 C8 1.499(6) . ?
C8 C81 1.487(7) . ?
C8 C9 1.511(7) . ?
C21 O22 1.205(6) . ?
C21 O23 1.304(6) . ?
O23 C24 1.428(6) . ?
C31 C32 1.290(12) . ?
C51 O52 1.189(5) . ?
C51 O53 1.304(5) . ?
O53 C54 1.465(7) . ?
C61 C62 1.422(9) . ?
C81 O82 1.218(6) . ?
C81 O83 1.301(6) . ?
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
O11 C1 C2 C3 173.8(5) . . . . ?
C9 C1 C2 C3 -10.4(5) . . . . ?
O11 C1 C2 C21 -3.1(7) . . . . ?
C9 C1 C2 C21 172.7(4) . . . . ?
C1 C2 C3 C4 3.0(6) . . . . ?
C21 C2 C3 C4 179.8(4) . . . . ?
C1 C2 C3 C31 176.6(6) . . . . ?
C21 C2 C3 C31 -6.6(9) . . . . ?
C2 C3 C4 C5 -120.8(5) . . . . ?
C31 C3 C4 C5 65.2(7) . . . . ?
C2 C3 C4 C9 5.4(6) . . . . ?
C31 C3 C4 C9 -168.6(6) . . . . ?
C3 C4 C5 C51 52.9(6) . . . . ?
C9 C4 C5 C51 -70.5(5) . . . . ?
C3 C4 C5 C6 168.1(4) . . . . ?
C9 C4 C5 C6 44.8(5) . . . . ?
C4 C5 C6 C7 -40.0(5) . . . . ?
C51 C5 C6 C7 82.8(5) . . . . ?
C4 C5 C6 C61 138.8(4) . . . . ?
C51 C5 C6 C61 -98.4(5) . . . . ?
C61 C6 C7 C8 179.2(4) . . . . ?
C5 C6 C7 C8 -2.2(7) . . . . ?
C6 C7 C8 C81 163.8(5) . . . . ?
C6 C7 C8 C9 36.9(6) . . . . ?
O11 C1 C9 C8 -41.9(7) . . . . ?
C2 C1 C9 C8 142.5(4) . . . . ?
O11 C1 C9 C4 -171.8(5) . . . . ?
C2 C1 C9 C4 12.6(5) . . . . ?
C81 C8 C9 C1 84.7(5) . . . . ?
C7 C8 C9 C1 -148.4(4) . . . . ?
C81 C8 C9 C4 -154.9(4) . . . . ?
C7 C8 C9 C4 -28.1(6) . . . . ?
C3 C4 C9 C1 -11.0(5) . . . . ?
C5 C4 C9 C1 113.6(5) . . . . ?
C3 C4 C9 C8 -137.4(5) . . . . ?
C5 C4 C9 C8 -12.8(6) . . . . ?
C3 C2 C21 O22 -34.6(8) . . . . ?
C1 C2 C21 O22 141.8(6) . . . . ?
C3 C2 C21 O23 149.7(5) . . . . ?
C1 C2 C21 O23 -34.0(6) . . . . ?
O22 C21 O23 C24 4.5(8) . . . . ?
C2 C21 O23 C24 -179.9(4) . . . . ?
C2 C3 C31 C32 94.4(10) . . . . ?
C4 C3 C31 C32 -92.7(10) . . . . ?
C4 C5 C51 O52 31.4(7) . . . . ?
C6 C5 C51 O52 -86.9(6) . . . . ?
C4 C5 C51 O53 -147.0(4) . . . . ?
C6 C5 C51 O53 94.7(4) . . . . ?
O52 C51 O53 C54 4.5(8) . . . . ?
C5 C51 O53 C54 -177.1(5) . . . . ?
C7 C6 C61 C62 -6.8(9) . . . . ?
C5 C6 C61 C62 174.6(5) . . . . ?
C7 C8 C81 O82 -100.5(6) . . . . ?
C9 C8 C81 O82 25.8(7) . . . . ?
C7 C8 C81 O83 77.1(5) . . . . ?
C9 C8 C81 O83 -156.6(4) . . . . ?
