#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/91/1519117.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_1519117
loop_
_publ_author_name
'Ward, Robert S.'
'Harman, Mary'
'Hursthouse, Michael B.'
_publ_section_title
;
 C21H22O6
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              1022
_journal_year                    1992
_chemical_formula_sum            'C21 H22 O6'
_chemical_formula_weight         370.39
_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
_cell_angle_alpha                81.84(3)
_cell_angle_beta                 84.41(3)
_cell_angle_gamma                78.71(1)
_cell_formula_units_Z            2
_cell_length_a                   8.270(5)
_cell_length_b                   8.870(4)
_cell_length_c                   13.050(9)
_cell_measurement_temperature    293(2)
_cell_volume                     926.9(10)
_computing_cell_refinement       REFINE
_computing_data_collection       'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_data_reduction        'ABSURD (Karaulov, 1992)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.2479
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4396
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            unk
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unk
_exptl_crystal_F_000             392
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.446
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.446
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                1145
_reflns_number_total             3801
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-1022.cif
_cod_data_source_block           s80
_cod_depositor_comments
;
Citation :
Ward, Robert S. and Harman, Mary and Hursthouse, Michael B. (1992) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/1022)

http://ecrystals.chem.soton.ac.uk/1022/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519117
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
O1 O 0.0696(3) 0.6730(3) 0.36517(18) 0.0619(6) Uani 1 1 d . . .
H1 H 0.0615 0.7628 0.3374 0.093 Uiso 1 1 calc R . .
O2 O -0.1086(3) 0.8255(2) 0.20975(18) 0.0612(6) Uani 1 1 d . . .
O3 O -0.4528(3) 0.2493(3) -0.04282(15) 0.0577(6) Uani 1 1 d . . .
O4 O -0.1863(3) 0.0407(3) 0.60982(18) 0.0689(7) Uani 1 1 d . . .
O5 O -0.7222(3) 0.1986(3) 0.06317(17) 0.0668(7) Uani 1 1 d . . .
O6 O -0.4600(3) 0.1179(2) 0.61944(15) 0.0556(6) Uani 1 1 d . . .
C1 C -0.0370(3) 0.6013(3) 0.3240(2) 0.0412(6) Uani 1 1 d . . .
C2 C -0.0538(3) 0.4531(3) 0.3668(2) 0.0396(6) Uani 1 1 d . . .
C3 C -0.1651(3) 0.3751(3) 0.33098(19) 0.0363(6) Uani 1 1 d . . .
C4 C -0.2607(3) 0.4509(3) 0.24910(19) 0.0358(6) Uani 1 1 d . . .
C5 C -0.2405(4) 0.6015(3) 0.2052(2) 0.0403(6) Uani 1 1 d . . .
C6 C -0.1318(4) 0.6765(3) 0.2430(2) 0.0421(6) Uani 1 1 d . . .
C7 C -0.2406(6) 0.9291(4) 0.1621(3) 0.0580(9) Uani 1 1 d . . .
C8 C -0.1836(4) 0.2179(3) 0.3890(2) 0.0409(6) Uani 1 1 d . . .
C9 C -0.3208(4) 0.2371(3) 0.4764(2) 0.0388(6) Uani 1 1 d . . .
C10 C -0.4955(4) 0.2391(3) 0.4491(2) 0.0405(6) Uani 1 1 d . . .
C11 C -0.5703(4) 0.3786(3) 0.3744(2) 0.0416(6) Uani 1 1 d . . .
C12 C -0.5289(3) 0.3500(3) 0.26194(19) 0.0375(6) Uani 1 1 d . . .
C13 C -0.3850(3) 0.3798(3) 0.20590(19) 0.0367(6) Uani 1 1 d . . .
C14 C -0.3067(4) 0.1201(3) 0.5727(2) 0.0468(7) Uani 1 1 d . . .
C15 C -0.5830(4) 0.2208(4) 0.5566(2) 0.0510(7) Uani 1 1 d . . .
C16 C -0.6435(4) 0.2882(3) 0.2159(2) 0.0429(6) Uani 1 1 d . . .
C17 C -0.6152(4) 0.2569(3) 0.1138(2) 0.0467(7) Uani 1 1 d . . .
C18 C -0.4702(4) 0.2868(3) 0.05610(19) 0.0414(6) Uani 1 1 d . . .
C19 C -0.3588(4) 0.3489(3) 0.1010(2) 0.0403(6) Uani 1 1 d . . .
C20 C -0.8753(5) 0.1785(7) 0.1176(3) 0.1090(19) Uani 1 1 d . . .
H20A H -0.8550 0.1113 0.1813 0.164 Uiso 1 1 calc R . .
H20B H -0.9373 0.1332 0.0757 0.164 Uiso 1 1 calc R . .
H20C H -0.9371 0.2773 0.1327 0.164 Uiso 1 1 calc R . .
C21 C -0.3072(5) 0.2739(5) -0.1045(2) 0.0722(11) Uani 1 1 d . . .
H21A H -0.3005 0.3818 -0.1120 0.108 Uiso 1 1 calc R . .
H21B H -0.3102 0.2428 -0.1717 0.108 Uiso 1 1 calc R . .
H21C H -0.2123 0.2138 -0.0716 0.108 Uiso 1 1 calc R . .
H2 H 0.012(4) 0.402(3) 0.427(2) 0.048(8) Uiso 1 1 d . . .
H5 H -0.311(3) 0.656(3) 0.1493(19) 0.032(6) Uiso 1 1 d . . .
H71 H -0.352(5) 0.937(4) 0.202(3) 0.086(13) Uiso 1 1 d . . .
H72 H -0.256(5) 0.906(5) 0.096(3) 0.092(13) Uiso 1 1 d . . .
H73 H -0.209(5) 1.033(5) 0.150(3) 0.085(12) Uiso 1 1 d . . .
H81 H -0.081(4) 0.172(3) 0.418(2) 0.041(7) Uiso 1 1 d . . .
H82 H -0.211(4) 0.148(3) 0.342(2) 0.045(8) Uiso 1 1 d . . .
H9 H -0.316(4) 0.338(3) 0.5008(19) 0.041(7) Uiso 1 1 d . . .
H10 H -0.493(4) 0.146(3) 0.413(2) 0.048(8) Uiso 1 1 d . . .
H111 H -0.528(4) 0.476(3) 0.3855(19) 0.039(7) Uiso 1 1 d . . .
H112 H -0.680(4) 0.394(3) 0.390(2) 0.049(8) Uiso 1 1 d . . .
H151 H -0.617(4) 0.321(4) 0.589(2) 0.055(9) Uiso 1 1 d . . .
H152 H -0.682(4) 0.175(4) 0.560(2) 0.057(9) Uiso 1 1 d . . .
H16 H -0.741(4) 0.260(4) 0.257(2) 0.055(9) Uiso 1 1 d . . .
H19 H -0.252(4) 0.376(3) 0.063(2) 0.047(8) 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'
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
C1 O1 H1 109.5 . .
C6 O2 C7 117.2(3) . .
C18 O3 C21 117.8(2) . .
C17 O5 C20 117.1(2) . .
C14 O6 C15 109.8(2) . .
O1 C1 C2 118.8(3) . .
O1 C1 C6 121.5(3) . .
C2 C1 C6 119.7(2) . .
C1 C2 C3 121.8(3) . .
C1 C2 H2 119.0(16) . .
C3 C2 H2 119.2(16) . .
C2 C3 C4 118.5(2) . .
C2 C3 C8 117.4(2) . .
C4 C3 C8 124.0(2) . .
C3 C4 C5 119.1(2) . .
C3 C4 C13 123.0(2) . .
C5 C4 C13 117.9(2) . .
C6 C5 C4 121.2(3) . .
C6 C5 H5 119.9(14) . .
C4 C5 H5 118.8(15) . .
O2 C6 C5 126.0(3) . .
O2 C6 C1 114.2(2) . .
C5 C6 C1 119.7(2) . .
O2 C7 H71 116(2) . .
O2 C7 H72 113(3) . .
H71 C7 H72 106(3) . .
O2 C7 H73 107(2) . .
H71 C7 H73 109(3) . .
H72 C7 H73 106(3) . .
C3 C8 C9 110.1(2) . .
C3 C8 H81 107.9(16) . .
C9 C8 H81 109.8(16) . .
C3 C8 H82 111.9(15) . .
C9 C8 H82 108.5(17) . .
H81 C8 H82 109(2) . .
C14 C9 C10 101.7(2) . .
C14 C9 C8 118.2(2) . .
C10 C9 C8 117.1(2) . .
C14 C9 H9 104.9(15) . .
C10 C9 H9 109.3(17) . .
C8 C9 H9 104.8(16) . .
C15 C10 C9 100.7(2) . .
C15 C10 C11 116.2(2) . .
C9 C10 C11 115.6(2) . .
C15 C10 H10 110.9(16) . .
C9 C10 H10 107.5(18) . .
C11 C10 H10 105.8(16) . .
C12 C11 C10 111.5(2) . .
C12 C11 H111 108.7(14) . .
C10 C11 H111 110.6(15) . .
C12 C11 H112 110.7(18) . .
C10 C11 H112 106.6(19) . .
H111 C11 H112 109(2) . .
C13 C12 C16 120.2(2) . .
C13 C12 C11 123.1(2) . .
C16 C12 C11 116.7(3) . .
C12 C13 C19 118.4(2) . .
C12 C13 C4 122.9(2) . .
C19 C13 C4 118.6(2) . .
O4 C14 O6 121.3(3) . .
O4 C14 C9 130.1(3) . .
O6 C14 C9 108.6(3) . .
O6 C15 C10 104.1(2) . .
O6 C15 H151 107.6(17) . .
C10 C15 H151 114.6(17) . .
O6 C15 H152 109.3(19) . .
C10 C15 H152 114.6(18) . .
H151 C15 H152 106(3) . .
C17 C16 C12 120.7(3) . .
C17 C16 H16 118.8(18) . .
C12 C16 H16 120.4(18) . .
O5 C17 C16 124.1(3) . .
O5 C17 C18 116.3(2) . .
C16 C17 C18 119.7(3) . .
O3 C18 C19 125.4(3) . .
O3 C18 C17 115.1(3) . .
C19 C18 C17 119.6(2) . .
C18 C19 C13 121.4(3) . .
C18 C19 H19 123.8(16) . .
C13 C19 H19 114.8(16) . .
O5 C20 H20A 109.5 . .
O5 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
O5 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
O3 C21 H21A 109.5 . .
O3 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
O3 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.370(3) .
O1 H1 0.8200 .
O2 C6 1.375(3) .
O2 C7 1.414(4) .
O3 C18 1.366(3) .
O3 C21 1.417(4) .
O4 C14 1.202(4) .
O5 C17 1.370(3) .
O5 C20 1.421(4) .
O6 C14 1.355(4) .
O6 C15 1.459(4) .
C1 C2 1.382(4) .
C1 C6 1.391(4) .
C2 C3 1.404(4) .
C2 H2 1.00(3) .
C3 C4 1.405(3) .
C3 C8 1.517(4) .
C4 C5 1.412(4) .
C4 C13 1.497(4) .
C5 C6 1.381(4) .
C5 H5 0.99(3) .
C7 H71 1.01(4) .
C7 H72 0.94(4) .
C7 H73 0.99(4) .
C8 C9 1.531(4) .
C8 H81 0.95(3) .
C8 H82 1.00(3) .
C9 C14 1.511(4) .
C9 C10 1.518(4) .
C9 H9 1.00(3) .
C10 C15 1.517(4) .
C10 C11 1.530(4) .
C10 H10 1.00(3) .
C11 C12 1.519(4) .
C11 H111 1.03(3) .
C11 H112 0.90(3) .
C12 C13 1.386(4) .
C12 C16 1.402(4) .
C13 C19 1.422(4) .
C15 H151 1.02(3) .
C15 H152 0.98(3) .
C16 C17 1.389(4) .
C16 H16 0.98(3) .
C17 C18 1.402(4) .
C18 C19 1.375(4) .
C19 H19 1.03(3) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
