#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/42/7204234.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_7204234
loop_
_publ_author_name
'Aggarwal, Varinder K.'
'Charmant, Jonathan P. H.'
'Ciampi, Cinzia'
'Hornby, Jonathan M.'
'O'Brien, Christopher J.'
'Hynd, George'
'Parsons, Richard'
_publ_section_title
;
 Additions of stabilised and semi-stabilised sulfur ylides to tosyl
 protected imines: are they under kinetic or thermodynamic control?
;
_journal_issue                   23
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3159
_journal_paper_doi               10.1039/b107275g
_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            b107275g.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               7204234
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
_atom_site_disorder_assembly
_atom_site_disorder_group
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9373235
