#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:00:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178455 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/76/4027614.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_4027614
loop_
_publ_author_name
'Jennifer R. Mazzone'
'Charles K. Zercher'
_publ_contact_author_address
;Department of Chemistry
23 Academic Way
University of New Hampshire
Durham, NH 03824
;
_publ_contact_author_email       chuck.zercher@unh.edu
_publ_contact_author_name        'Charles K. Zercher'
_publ_section_title
;
 Syntheses of Papyracillic Acids: Application of the Tandem Chain
 Extension-Acylation Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9171
_journal_page_last               9178
_journal_paper_doi               10.1021/jo3017617
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C13 H18 O7'
_chemical_formula_sum            'C13 H18 O7'
_chemical_formula_weight         286.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1652(6)
_cell_length_b                   12.6259(9)
_cell_length_c                   14.2540(11)
_cell_measurement_reflns_used    4418
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      23.2452
_cell_measurement_theta_min      2.8580
_cell_volume                     1469.49(19)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'GIS (Bruker, 2011)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'APEX2 (Bruker, 2011)'
_computing_publication_material  'APEX2 (Bruker, 2011)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART X2S benchtop diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9693
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.87
_diffrn_source                   'XOS X-beam microfocus source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.154
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0326
_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)+(0.0543P)²+0.0559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                2296
_reflns_number_total             2587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3017617_si_002_4.cif
_cod_data_source_block           Ketal_16b
_cod_database_code               4027614
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.9060(4) 0.0901(2) 0.68677(14) 0.0811(7) Uani d . 1
H H1A 1.0188 0.0694 0.6918 0.122 Uiso calc R 1
H H1B 0.8386 0.0394 0.7188 0.122 Uiso calc R 1
H H1C 0.8914 0.1587 0.7147 0.122 Uiso calc R 1
C C2 0.9430(2) 0.15870(14) 0.53456(13) 0.0476(4) Uani d . 1
C C3 0.88521(18) 0.15228(11) 0.43467(11) 0.0400(3) Uani d . 1
H H3 0.7708 0.1755 0.4323 0.048 Uiso calc R 1
C C4 0.89559(18) 0.04053(11) 0.39309(10) 0.0378(3) Uani d . 1
C C5 0.76413(18) -0.03731(11) 0.42023(10) 0.0373(3) Uani d . 1
C C6 0.8286(2) -0.12372(13) 0.45748(12) 0.0456(4) Uani d . 1
H H6 0.7718 -0.1838 0.4766 0.055 Uiso calc R 1
C C7 1.0035(2) -0.10760(13) 0.46305(13) 0.0463(4) Uani d . 1
C C8 0.4840(2) -0.07674(18) 0.43798(17) 0.0709(6) Uani d . 1
H H8A 0.4918 -0.1437 0.4064 0.106 Uiso calc R 1
H H8B 0.3786 -0.0459 0.426 0.106 Uiso calc R 1
H H8C 0.4975 -0.0872 0.5042 0.106 Uiso calc R 1
C C9 1.2079(3) 0.1154(2) 0.2209(2) 0.0924(8) Uani d . 1
H H9A 1.265 0.1555 0.2679 0.139 Uiso calc R 1
H H9B 1.2728 0.1124 0.1648 0.139 Uiso calc R 1
H H9C 1.1887 0.0449 0.2436 0.139 Uiso calc R 1
C C10 0.9348(2) 0.16431(15) 0.27079(13) 0.0570(5) Uani d . 1
C C11 0.9828(2) 0.21705(13) 0.36392(14) 0.0520(5) Uani d . 1
H H11 1.0995 0.2037 0.3749 0.062 Uiso calc R 1
C C12 0.7833(3) 0.2074(2) 0.22407(16) 0.0801(7) Uani d . 1
H H12A 0.8018 0.2796 0.2059 0.12 Uiso calc R 1
H H12B 0.693 0.2041 0.2671 0.12 Uiso calc R 1
H H12C 0.7587 0.1658 0.1695 0.12 Uiso calc R 1
C C13 0.9541(3) 0.33642(15) 0.36885(19) 0.0788(7) Uani d . 1
H H13A 0.8385 0.3505 0.3682 0.118 Uiso calc R 1
H H13B 1.0046 0.37 0.3158 0.118 Uiso calc R 1
H H13C 1.001 0.3638 0.4256 0.118 Uiso calc R 1
O O1 0.85981(16) 0.09442(11) 0.58917(8) 0.0608(4) Uani d . 1
O O2 1.0485(2) 0.21414(15) 0.56247(13) 0.1072(7) Uani d . 1
O O3 0.61127(13) -0.00630(9) 0.40365(8) 0.0494(3) Uani d . 1
O O4 1.10972(18) -0.16262(11) 0.49528(10) 0.0690(4) Uani d . 1
O O5 1.04298(12) -0.01155(8) 0.42419(8) 0.0456(3) Uani d . 1
O O6 0.90013(16) 0.05465(9) 0.29615(7) 0.0513(3) Uani d . 1
O O7 1.0557(2) 0.16498(13) 0.20090(11) 0.0851(5) Uani d . 1
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
O1 C1 H1A 109.5
O1 C1 H1B 109.5
H1A C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O2 C2 O1 123.00(18)
O2 C2 C3 125.55(17)
O1 C2 C3 111.45(14)
C2 C3 C11 115.72(14)
C2 C3 C4 113.51(12)
C11 C3 C4 102.08(13)
C2 C3 H3 108.4
C11 C3 H3 108.4
C4 C3 H3 108.4
O6 C4 O5 109.95(12)
O6 C4 C5 110.93(12)
O5 C4 C5 102.62(11)
O6 C4 C3 105.49(11)
O5 C4 C3 110.31(12)
C5 C4 C3 117.52(12)
C6 C5 O3 133.47(15)
C6 C5 C4 110.96(13)
O3 C5 C4 115.56(12)
C5 C6 C7 107.42(15)
C5 C6 H6 126.3
C7 C6 H6 126.3
O4 C7 O5 119.70(16)
O4 C7 C6 130.75(17)
O5 C7 C6 109.56(14)
O3 C8 H8A 109.5
O3 C8 H8B 109.5
H8A C8 H8B 109.5
O3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O7 C9 H9A 109.5
O7 C9 H9B 109.5
H9A C9 H9B 109.5
O7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O7 C10 O6 108.56(15)
O7 C10 C12 105.18(16)
O6 C10 C12 107.03(18)
O7 C10 C11 115.55(17)
O6 C10 C11 104.29(13)
C12 C10 C11 115.81(18)
C3 C11 C13 114.76(16)
C3 C11 C10 101.87(14)
C13 C11 C10 115.36(17)
C3 C11 H11 108.1
C13 C11 H11 108.1
C10 C11 H11 108.1
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C2 O1 C1 117.34(15)
C5 O3 C8 115.56(14)
C7 O5 C4 109.34(11)
C4 O6 C10 111.86(13)
C10 O7 C9 118.07(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.443(2)
C1 H1A 0.96
C1 H1B 0.96
C1 H1C 0.96
C2 O2 1.179(2)
C2 O1 1.314(2)
C2 C3 1.502(2)
C3 C11 1.524(2)
C3 C4 1.533(2)
C3 H3 0.98
C4 O6 1.3937(18)
C4 O5 1.4413(18)
C4 C5 1.506(2)
C5 C6 1.323(2)
C5 O3 1.3293(18)
C6 C7 1.445(2)
C6 H6 0.93
C7 O4 1.202(2)
C7 O5 1.372(2)
C8 O3 1.453(2)
C8 H8A 0.96
C8 H8B 0.96
C8 H8C 0.96
C9 O7 1.420(3)
C9 H9A 0.96
C9 H9B 0.96
C9 H9C 0.96
C10 O7 1.403(2)
C10 O6 1.459(2)
C10 C12 1.506(3)
C10 C11 1.536(3)
C11 C13 1.527(3)
C11 H11 0.98
C12 H12A 0.96
C12 H12B 0.96
C12 H12C 0.96
C13 H13A 0.96
C13 H13B 0.96
C13 H13C 0.96
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
O2 C2 C3 C11 5.3(3)
O1 C2 C3 C11 -175.20(15)
O2 C2 C3 C4 122.9(2)
O1 C2 C3 C4 -57.63(19)
C2 C3 C4 O6 -157.75(13)
C11 C3 C4 O6 -32.50(15)
C2 C3 C4 O5 -39.06(16)
C11 C3 C4 O5 86.19(14)
C2 C3 C4 C5 78.03(17)
C11 C3 C4 C5 -156.72(13)
O6 C4 C5 C6 114.76(15)
O5 C4 C5 C6 -2.63(17)
C3 C4 C5 C6 -123.80(15)
O6 C4 C5 O3 -65.98(16)
O5 C4 C5 O3 176.64(12)
C3 C4 C5 O3 55.47(18)
O3 C5 C6 C7 -175.76(17)
C4 C5 C6 C7 3.33(19)
C5 C6 C7 O4 176.61(19)
C5 C6 C7 O5 -2.8(2)
C2 C3 C11 C13 -73.6(2)
C4 C3 C11 C13 162.58(16)
C2 C3 C11 C10 160.98(14)
C4 C3 C11 C10 37.21(15)
O7 C10 C11 C3 -148.52(15)
O6 C10 C11 C3 -29.45(17)
C12 C10 C11 C3 87.87(18)
O7 C10 C11 C13 86.5(2)
O6 C10 C11 C13 -154.43(16)
C12 C10 C11 C13 -37.1(2)
O2 C2 O1 C1 -2.3(3)
C3 C2 O1 C1 178.15(18)
C6 C5 O3 C8 4.8(3)
C4 C5 O3 C8 -174.31(15)
O4 C7 O5 C4 -178.39(16)
C6 C7 O5 C4 1.12(19)
O6 C4 O5 C7 -117.30(13)
C5 C4 O5 C7 0.78(16)
C3 C4 O5 C7 126.77(13)
O5 C4 O6 C10 -104.62(14)
C5 C4 O6 C10 142.57(14)
C3 C4 O6 C10 14.31(17)
O7 C10 O6 C4 133.45(15)
C12 C10 O6 C4 -113.49(17)
C11 C10 O6 C4 9.74(19)
O6 C10 O7 C9 -57.6(3)
C12 C10 O7 C9 -171.9(2)
C11 C10 O7 C9 59.1(3)
