#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/26/4022681.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_4022681
loop_
_publ_author_name
'Marie-Christine Matos'
'Paul V. Murphy'
_publ_section_title
;
 Synthesis of Macrolide-Saccharide Hybrids by Ring-Closing Metathesis
 of Precursors Derived from Glycitols and Benzoic Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1803
_journal_page_last               1806
_journal_paper_doi               10.1021/jo062159l
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_formula_sum            'C16 H22 O7'
_chemical_formula_weight         326.34
_chemical_name_systematic
; 
 ? 
;
_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                   5.7090(6)
_cell_length_b                   7.6470(7)
_cell_length_c                   34.415(3)
_cell_measurement_reflns_used    6733
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.11
_cell_measurement_theta_min      2.37
_cell_volume                     1502.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            14798
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.7959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0617P)²+0.3778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                2221
_reflns_number_total             2330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062159lsi20061017_024346.cif
_cod_data_source_block           mur34
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022681
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
O1 O -0.1330(2) 0.63264(16) 0.86496(3) 0.0148(3) Uani 1 1 d .
C1 C 0.0148(3) 0.7697(2) 0.85011(5) 0.0146(3) Uani 1 1 d .
H1A H 0.1716 0.7613 0.8623 0.018 Uiso 1 1 calc R
H1B H -0.0530 0.8847 0.8570 0.018 Uiso 1 1 calc R
C2 C 0.0389(3) 0.7563(2) 0.80660(5) 0.0133(3) Uani 1 1 d .
H2 H 0.1650 0.8402 0.7989 0.016 Uiso 1 1 calc R
O2 O -0.1699(2) 0.81024(17) 0.78662(4) 0.0169(3) Uani 1 1 d .
H2A H -0.2799 0.7417 0.7922 0.025 Uiso 1 1 calc R
C3 C 0.1122(3) 0.5767(2) 0.79120(5) 0.0120(3) Uani 1 1 d .
H3 H -0.0292 0.4997 0.7901 0.014 Uiso 1 1 calc R
O3 O 0.1917(2) 0.60755(16) 0.75264(3) 0.0157(3) Uani 1 1 d .
H3A H 0.1949 0.5127 0.7404 0.024 Uiso 1 1 calc R
C4 C 0.2970(3) 0.4891(2) 0.81657(5) 0.0121(3) Uani 1 1 d .
H4 H 0.2376 0.4869 0.8439 0.014 Uiso 1 1 calc R
O4 O 0.5033(2) 0.59332(18) 0.81565(4) 0.0192(3) Uani 1 1 d .
H4A H 0.5738 0.5848 0.8370 0.029 Uiso 1 1 calc R
C5 C 0.3511(3) 0.3004(2) 0.80429(5) 0.0145(3) Uani 1 1 d .
H5 H 0.4197 0.2999 0.7776 0.017 Uiso 1 1 calc R
O5 O 0.1426(3) 0.19934(18) 0.80470(4) 0.0188(3) Uani 1 1 d .
H5A H 0.0774 0.2052 0.7829 0.028 Uiso 1 1 calc R
C6 C 0.5194(3) 0.2139(3) 0.83228(5) 0.0174(4) Uani 1 1 d .
H6A H 0.5538 0.0929 0.8238 0.021 Uiso 1 1 calc R
H6B H 0.6684 0.2800 0.8334 0.021 Uiso 1 1 calc R
O6 O 0.4067(2) 0.21260(17) 0.87056(3) 0.0162(3) Uani 1 1 d .
C7 C 0.4224(3) 0.0647(2) 0.89092(5) 0.0148(3) Uani 1 1 d .
O7 O 0.5428(3) -0.0567(2) 0.88156(4) 0.0274(3) Uani 1 1 d .
C8 C 0.2780(3) 0.0615(2) 0.92742(5) 0.0138(3) Uani 1 1 d .
C9 C 0.3525(3) -0.0651(2) 0.95432(5) 0.0166(3) Uani 1 1 d .
H9 H 0.4873 -0.1334 0.9487 0.020 Uiso 1 1 calc R
C10 C 0.2334(4) -0.0923(2) 0.98879(5) 0.0187(4) Uani 1 1 d .
H10 H 0.2856 -0.1783 1.0067 0.022 Uiso 1 1 calc R
C11 C 0.0362(4) 0.0080(2) 0.99685(5) 0.0189(4) Uani 1 1 d .
H11 H -0.0464 -0.0083 1.0205 0.023 Uiso 1 1 calc R
C12 C -0.0396(3) 0.1317(2) 0.97035(5) 0.0186(4) Uani 1 1 d .
H12 H -0.1757 0.1983 0.9761 0.022 Uiso 1 1 calc R
C13 C 0.0782(3) 0.1619(2) 0.93519(5) 0.0142(3) Uani 1 1 d .
C14 C -0.0280(3) 0.2994(2) 0.90903(5) 0.0147(3) Uani 1 1 d .
H14A H -0.2008 0.2890 0.9098 0.018 Uiso 1 1 calc R
H14B H 0.0233 0.2783 0.8820 0.018 Uiso 1 1 calc R
C15 C 0.0427(3) 0.4860(2) 0.92115(5) 0.0151(3) Uani 1 1 d .
H15A H 0.0507 0.4923 0.9499 0.018 Uiso 1 1 calc R
H15B H 0.2007 0.5120 0.9108 0.018 Uiso 1 1 calc R
C16 C -0.1287(3) 0.6233(2) 0.90645(5) 0.0160(3) Uani 1 1 d .
H16A H -0.2877 0.5952 0.9161 0.019 Uiso 1 1 calc R
H16B H -0.0840 0.7390 0.9171 0.019 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 0.0033 0.0000 '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 0.0000 '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
C16 O1 C1 112.37(14)
O1 C1 C2 110.92(14)
O1 C1 H1A 109.5
C2 C1 H1A 109.5
O1 C1 H1B 109.5
C2 C1 H1B 109.5
H1A C1 H1B 108.0
O2 C2 C1 112.36(15)
O2 C2 C3 108.59(14)
C1 C2 C3 115.43(14)
O2 C2 H2 106.6
C1 C2 H2 106.6
C3 C2 H2 106.6
C2 O2 H2A 109.5
O3 C3 C4 112.71(14)
O3 C3 C2 105.17(13)
C4 C3 C2 112.67(14)
O3 C3 H3 108.7
C4 C3 H3 108.7
C2 C3 H3 108.7
C3 O3 H3A 109.5
O4 C4 C3 108.29(13)
O4 C4 C5 110.73(14)
C3 C4 C5 113.25(14)
O4 C4 H4 108.1
C3 C4 H4 108.1
C5 C4 H4 108.1
C4 O4 H4A 109.5
O5 C5 C6 106.75(14)
O5 C5 C4 109.89(14)
C6 C5 C4 111.31(14)
O5 C5 H5 109.6
C6 C5 H5 109.6
C4 C5 H5 109.6
C5 O5 H5A 109.5
O6 C6 C5 107.25(14)
O6 C6 H6A 110.3
C5 C6 H6A 110.3
O6 C6 H6B 110.3
C5 C6 H6B 110.3
H6A C6 H6B 108.5
C7 O6 C6 116.64(14)
O7 C7 O6 123.64(16)
O7 C7 C8 121.75(16)
O6 C7 C8 114.61(15)
C13 C8 C9 119.88(16)
C13 C8 C7 126.67(15)
C9 C8 C7 113.33(16)
C10 C9 C8 121.31(17)
C10 C9 H9 119.3
C8 C9 H9 119.3
C9 C10 C11 119.12(17)
C9 C10 H10 120.4
C11 C10 H10 120.4
C12 C11 C10 119.92(17)
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 C13 122.08(18)
C11 C12 H12 119.0
C13 C12 H12 119.0
C8 C13 C12 117.68(16)
C8 C13 C14 126.47(16)
C12 C13 C14 115.84(16)
C13 C14 C15 112.19(14)
C13 C14 H14A 109.2
C15 C14 H14A 109.2
C13 C14 H14B 109.2
C15 C14 H14B 109.2
H14A C14 H14B 107.9
C16 C15 C14 112.38(15)
C16 C15 H15A 109.1
C14 C15 H15A 109.1
C16 C15 H15B 109.1
C14 C15 H15B 109.1
H15A C15 H15B 107.9
O1 C16 C15 112.18(14)
O1 C16 H16A 109.2
C15 C16 H16A 109.2
O1 C16 H16B 109.2
C15 C16 H16B 109.2
H16A C16 H16B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C16 1.430(2)
O1 C1 1.439(2)
C1 C2 1.507(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 O2 1.436(2)
C2 C3 1.530(2)
C2 H2 1.0000
O2 H2A 0.8400
C3 O3 1.422(2)
C3 C4 1.525(2)
C3 H3 1.0000
O3 H3A 0.8400
C4 O4 1.423(2)
C4 C5 1.535(2)
C4 H4 1.0000
O4 H4A 0.8400
C5 O5 1.419(2)
C5 C6 1.513(2)
C5 H5 1.0000
O5 H5A 0.8400
C6 O6 1.466(2)
C6 H6A 0.9900
C6 H6B 0.9900
O6 C7 1.333(2)
C7 O7 1.199(2)
C7 C8 1.503(2)
C8 C13 1.401(3)
C8 C9 1.405(2)
C9 C10 1.383(3)
C9 H9 0.9500
C10 C11 1.390(3)
C10 H10 0.9500
C11 C12 1.383(3)
C11 H11 0.9500
C12 C13 1.403(3)
C12 H12 0.9500
C13 C14 1.511(2)
C14 C15 1.540(2)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.522(2)
C15 H15A 0.9900
C15 H15B 0.9900
C16 H16A 0.9900
C16 H16B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O3 0.84 2.10 2.8337(18) 145.6 3_546
O4 H4A O1 0.84 1.97 2.6982(18) 145.2 1_655
O3 H3A O2 0.84 1.81 2.6478(18) 174.2 3_546
O2 H2A O4 0.84 1.86 2.6889(18) 167.1 1_455
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
C16 O1 C1 C2 170.25(14)
O1 C1 C2 O2 73.62(17)
O1 C1 C2 C3 -51.6(2)
O2 C2 C3 O3 70.03(16)
C1 C2 C3 O3 -162.78(15)
O2 C2 C3 C4 -166.83(14)
C1 C2 C3 C4 -39.6(2)
O3 C3 C4 O4 55.25(18)
C2 C3 C4 O4 -63.58(18)
O3 C3 C4 C5 -67.97(18)
C2 C3 C4 C5 173.20(14)
O4 C4 C5 O5 -178.92(12)
C3 C4 C5 O5 -57.06(17)
O4 C4 C5 C6 63.04(18)
C3 C4 C5 C6 -175.10(15)
O5 C5 C6 O6 -59.36(18)
C4 C5 C6 O6 60.56(19)
C5 C6 O6 C7 136.12(16)
C6 O6 C7 O7 8.5(3)
C6 O6 C7 C8 -172.25(15)
O7 C7 C8 C13 -157.07(19)
O6 C7 C8 C13 23.6(3)
O7 C7 C8 C9 19.0(3)
O6 C7 C8 C9 -160.28(16)
C13 C8 C9 C10 -0.6(3)
C7 C8 C9 C10 -176.96(17)
C8 C9 C10 C11 0.0(3)
C9 C10 C11 C12 0.6(3)
C10 C11 C12 C13 -0.7(3)
C9 C8 C13 C12 0.5(3)
C7 C8 C13 C12 176.36(17)
C9 C8 C13 C14 -178.37(17)
C7 C8 C13 C14 -2.5(3)
C11 C12 C13 C8 0.2(3)
C11 C12 C13 C14 179.13(18)
C8 C13 C14 C15 -99.4(2)
C12 C13 C14 C15 81.7(2)
C13 C14 C15 C16 -157.74(15)
C1 O1 C16 C15 -96.70(17)
C14 C15 C16 O1 -64.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17268741
