#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:18:41 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180499 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/68/7216878.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_7216878
loop_
_publ_author_name
'Yamada, Takeshi'
'Iritani, Masashi'
'Doi, Mitsunobu'
'Minoura, Katsuhiko'
'Ito, Tadayoshi'
'Numata, Atsushi'
_publ_section_title
;
 Absolute stereostructures of cell-adhesion inhibitors, macrosphelides C,
 Eâ€“G and I, produced by a Periconia species separated
 from an Aplysia sea hare
;
_journal_issue                   22
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3046
_journal_paper_doi               10.1039/b104337b
_journal_year                    2001
_chemical_formula_sum            'C16 H22 O7'
_chemical_formula_weight         326.34
_chemical_name_common            mpc
_chemical_name_systematic
; 
Macrosphelide C
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.514(2)
_cell_length_b                   28.460(2)
_cell_length_c                   5.860(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      21.07
_cell_measurement_theta_min      18.89
_cell_volume                     1753.5(7)
_computing_cell_refinement       'MSC/AFC Diffractmeter Control Software'
_computing_data_collection       'MSC/AFC Diffractmeter Control Software'
_computing_data_reduction        'MSC/AFC Diffractmeter Control Software'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson 1996)'
_computing_publication_material  'PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      288(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku AFC5R'
_diffrn_measurement_method       2θ-ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku RU200'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2864
_diffrn_reflns_theta_full        67.63
_diffrn_reflns_theta_max         67.63
_diffrn_reflns_theta_min         3.11
_diffrn_standards_decay_%        1.6
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   \y-scan
_exptl_absorpt_process_details   'North, Phillips & Mathews (1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       0.0075(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0437
_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)+(0.0441P)²+0.6740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                2185
_reflns_number_total             2473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b104337b.txt
_cod_data_source_block           mpc
_cod_original_cell_volume        1753.4(7)
_cod_original_sg_symbol_H-M      'P21 21 21'
_cod_database_code               7216878
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6396(3) 0.06086(10) 0.2130(5) 0.0579(7) Uani 1 1 d .
O1 O 0.6759(2) 0.04823(10) 0.0286(4) 0.0867(8) Uani 1 1 d .
C2 C 0.7213(3) 0.06531(12) 0.4230(6) 0.0689(8) Uani 1 1 d .
H2A H 0.6893 0.0910 0.5154 0.083 Uiso 1 1 calc R
H2B H 0.7136 0.0367 0.5120 0.083 Uiso 1 1 calc R
C3 C 0.8589(3) 0.07385(12) 0.3742(6) 0.0707(9) Uani 1 1 d .
H3 H 0.8916 0.0496 0.2707 0.085 Uiso 1 1 calc R
O4 O 0.86158(18) 0.11965(8) 0.2625(4) 0.0742(6) Uani 1 1 d .
C5 C 0.9612(3) 0.12974(16) 0.1327(6) 0.0823(11) Uani 1 1 d .
O5 O 1.0529(2) 0.10485(14) 0.1130(5) 0.1155(11) Uani 1 1 d .
C7 C 0.8445(3) 0.20053(13) 0.0158(6) 0.0771(10) Uani 1 1 d .
H7 H 0.7781 0.1901 0.1073 0.093 Uiso 1 1 calc R
C8 C 0.8223(4) 0.24498(14) -0.1189(7) 0.0877(11) Uani 1 1 d .
H8A H 0.9036 0.2578 -0.1660 0.105 Uiso 1 1 calc R
H8B H 0.7810 0.2680 -0.0217 0.105 Uiso 1 1 calc R
C9 C 0.7409(3) 0.23659(12) -0.3275(6) 0.0710(9) Uani 1 1 d .
H9 H 0.7888 0.2176 -0.4374 0.085 Uiso 1 1 calc R
O10 O 0.63285(19) 0.20971(7) -0.2454(3) 0.0627(5) Uani 1 1 d .
C11 C 0.5677(3) 0.18504(10) -0.3997(5) 0.0564(7) Uani 1 1 d .
O11 O 0.5860(2) 0.18825(9) -0.6026(4) 0.0819(7) Uani 1 1 d .
C12 C 0.4720(3) 0.15393(10) -0.2985(5) 0.0563(7) Uani 1 1 d .
H12 H 0.4105 0.1415 -0.3953 0.068 Uiso 1 1 calc R
C13 C 0.4662(2) 0.14223(10) -0.0826(5) 0.0521(6) Uani 1 1 d .
H13 H 0.5274 0.1545 0.0154 0.063 Uiso 1 1 calc R
C14 C 0.3674(2) 0.11044(11) 0.0160(5) 0.0582(7) Uani 1 1 d .
H14 H 0.3284 0.1261 0.1475 0.070 Uiso 1 1 calc R
O14 O 0.27180(18) 0.10168(11) -0.1490(4) 0.0830(7) Uani 1 1 d .
H14A H 0.2019 0.1019 -0.0871 0.125 Uiso 1 1 calc R
C15 C 0.4212(2) 0.06325(10) 0.0939(5) 0.0590(7) Uani 1 1 d .
H15 H 0.4559 0.0459 -0.0365 0.071 Uiso 1 1 calc R
O16 O 0.52021(17) 0.07225(7) 0.2606(4) 0.0597(5) Uani 1 1 d .
C17 C 0.3222(3) 0.03377(12) 0.2170(8) 0.0870(11) Uani 1 1 d .
H17A H 0.3594 0.0045 0.2631 0.130 Uiso 1 1 calc R
H17B H 0.2519 0.0278 0.1164 0.130 Uiso 1 1 calc R
H17C H 0.2925 0.0504 0.3493 0.130 Uiso 1 1 calc R
C18 C 0.6972(5) 0.28140(13) -0.4423(7) 0.0972(13) Uani 1 1 d .
H18A H 0.6467 0.2738 -0.5736 0.146 Uiso 1 1 calc R
H18B H 0.7699 0.2994 -0.4889 0.146 Uiso 1 1 calc R
H18C H 0.6472 0.2995 -0.3371 0.146 Uiso 1 1 calc R
C19 C 0.9382(4) 0.07557(16) 0.5878(7) 0.1025(14) Uani 1 1 d .
H19A H 1.0255 0.0809 0.5480 0.154 Uiso 1 1 calc R
H19B H 0.9308 0.0463 0.6678 0.154 Uiso 1 1 calc R
H19C H 0.9087 0.1006 0.6838 0.154 Uiso 1 1 calc R
C6 C 0.9490(3) 0.17529(18) 0.0157(7) 0.0934(13) Uani 1 1 d .
H6 H 1.0193 0.1868 -0.0627 0.112 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'
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
O1 C1 O16 124.3(3)
O1 C1 C2 125.3(3)
O16 C1 C2 110.4(3)
C3 C2 C1 114.2(3)
O4 C3 C2 104.5(2)
O4 C3 C19 109.5(3)
C2 C3 C19 112.5(3)
C5 O4 C3 117.8(3)
O5 C5 O4 124.1(4)
O5 C5 C6 123.0(4)
O4 C5 C6 112.9(3)
C6 C7 C8 126.0(3)
C7 C8 C9 112.2(3)
O10 C9 C8 105.0(2)
O10 C9 C18 110.7(3)
C8 C9 C18 113.5(3)
C11 O10 C9 117.0(2)
O11 C11 O10 123.1(3)
O11 C11 C12 123.6(3)
O10 C11 C12 113.3(2)
C13 C12 C11 125.2(3)
C12 C13 C14 124.1(3)
O14 C14 C13 109.6(2)
O14 C14 C15 108.2(2)
C13 C14 C15 113.0(2)
O16 C15 C17 105.6(3)
O16 C15 C14 108.2(2)
C17 C15 C14 111.9(2)
C1 O16 C15 119.6(2)
C7 C6 C5 123.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.201(4)
C1 O16 1.326(3)
C1 C2 1.506(4)
C2 C3 1.494(4)
C3 O4 1.459(4)
C3 C19 1.504(5)
O4 C5 1.326(4)
C5 O5 1.202(5)
C5 C6 1.472(6)
C7 C6 1.313(5)
C7 C8 1.509(5)
C8 C9 1.511(5)
C9 O10 1.452(4)
C9 C18 1.513(5)
O10 C11 1.334(3)
C11 O11 1.208(3)
C11 C12 1.466(4)
C12 C13 1.309(4)
C13 C14 1.494(4)
C14 O14 1.417(3)
C14 C15 1.527(4)
C15 O16 1.450(3)
C15 C17 1.520(4)
