#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/08/7150897.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_7150897
loop_
_publ_author_name
'Nieto, Natalia'
'Munslow, Ian J.'
'Barr, Jonathan'
'Benet-Buchholz, J.'
'Vidal-Ferran, Anton'
_publ_contact_author
;
    Dr. Benet-Buchholz, Jordi
    The Institute of Chemical Research of Catalonia (ICIQ)    
    X-ray Diffraction Unit
    Avgda. Paīsos Catalans 16
    E-43007 Tarragona, Spain
;
_publ_section_title
;
 Dioxirane mediated asymmetric epoxidations: stereochemical studies via
 isotopic labeling
;
_journal_issue                   13
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2276
_journal_page_last               2281
_journal_paper_doi               10.1039/b801922c
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_sum            'C14 H22 O9'
_chemical_formula_weight         334.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 97.914(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8203(8)
_cell_length_b                   5.5939(7)
_cell_length_c                   20.585(3)
_cell_measurement_reflns_used    2152
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.54
_cell_measurement_theta_min      3.00
_cell_volume                     777.88(18)
_computing_cell_refinement       'Bruker-Nonius Apex v1.0-22 2002'
_computing_data_collection       'Bruker-Nonius Apex v1.0-22 2002'
_computing_data_reduction        'SAINT+ Version 7.06A Bruker-Nonius, 2004'
_computing_molecular_graphics    'Shelxtl Version 6.12 (Sheldrick, 2001)'
_computing_publication_material  'Shelxtl Version 6.12 (Sheldrick, 2001)'
_computing_structure_refinement  'Shelxtl Version 6.12 (Sheldrick, 2001)'
_computing_structure_solution    'Shelxtl Version 6.12 (Sheldrick, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.839
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13917
_diffrn_reflns_theta_full        39.71
_diffrn_reflns_theta_max         39.71
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           90
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.959513
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2.1 2003 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       neddle
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4265
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0500
_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)+(0.0589P)²+0.0708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                2978
_reflns_number_total             4265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b801922c.txt
_cod_data_source_block           nn152a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_cell_volume        777.89(17)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7150897
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 -0.5889(3) -0.5931(3) -0.31956(9) 0.0118(3) Uani 1 1 d . . .
O1 O -0.3829(2) -0.6357(2) -0.31602(7) 0.0140(3) Uani 1 1 d . . .
C2 C -0.6453(3) -0.5447(3) -0.24991(9) 0.0116(3) Uani 1 1 d . . .
O2 O -0.8004(3) -0.4744(3) -0.41355(7) 0.0179(3) Uani 1 1 d . . .
C3 C -0.5688(3) -0.7534(3) -0.20530(9) 0.0108(3) Uani 1 1 d . . .
H3 H -0.6450 -0.9006 -0.2204 0.013 Uiso 1 1 calc R . .
O3 O -0.7030(2) -0.7881(2) -0.34707(7) 0.0142(3) Uani 1 1 d . . .
C4 C -0.3485(3) -0.8029(3) -0.20514(9) 0.0130(3) Uani 1 1 d . . .
H4 H -0.3093 -0.9512 -0.1794 0.016 Uiso 1 1 calc R . .
O4 O -0.5578(2) -0.3249(2) -0.23076(7) 0.0141(3) Uani 1 1 d . . .
H4A H -0.5709 -0.2977 -0.1915 0.021 Uiso 1 1 calc R . .
C5 C -0.3099(3) -0.8335(3) -0.27548(9) 0.0146(4) Uani 1 1 d . . .
H5A H -0.1657 -0.8500 -0.2762 0.018 Uiso 1 1 calc R . .
H5B H -0.3745 -0.9823 -0.2936 0.018 Uiso 1 1 calc R . .
O5 O -0.8507(2) -0.5449(3) -0.24816(8) 0.0160(3) Uani 1 1 d . . .
C6 C -0.6348(3) -0.3900(3) -0.36959(10) 0.0163(4) Uani 1 1 d . . .
H6A H -0.6683 -0.2409 -0.3477 0.020 Uiso 1 1 calc R . .
H6B H -0.5203 -0.3592 -0.3932 0.020 Uiso 1 1 calc R . .
O6 O -0.6069(2) -0.6955(2) -0.13942(7) 0.0137(3) Uani 1 1 d . . .
C7 C -0.7884(3) -0.7290(3) -0.41321(9) 0.0159(4) Uani 1 1 d . . .
O7 O -0.6082(3) -1.0885(3) -0.11503(7) 0.0202(3) Uani 1 1 d . . .
C8 C -0.6548(4) -0.8165(4) -0.46189(10) 0.0218(4) Uani 1 1 d . . .
H8A H -0.5205 -0.7547 -0.4492 0.033 Uiso 1 1 calc R . .
H8B H -0.7062 -0.7594 -0.5060 0.033 Uiso 1 1 calc R . .
H8C H -0.6517 -0.9916 -0.4618 0.033 Uiso 1 1 calc R . .
O8 O -0.2328(2) -0.6024(3) -0.17726(7) 0.0143(3) Uani 1 1 d . . .
C9 C -0.9934(4) -0.8308(4) -0.42533(11) 0.0223(4) Uani 1 1 d . . .
H9A H -1.0534 -0.7928 -0.4702 0.033 Uiso 1 1 calc R . .
H9B H -1.0737 -0.7616 -0.3941 0.033 Uiso 1 1 calc R . .
H9C H -0.9871 -1.0047 -0.4197 0.033 Uiso 1 1 calc R . .
O9 O -0.1700(3) -0.7815(3) -0.07805(8) 0.0223(3) Uani 1 1 d . . .
C10 C -0.9628(3) -0.3393(4) -0.27547(12) 0.0209(4) Uani 1 1 d . . .
H10A H -0.9860 -0.3525 -0.3234 0.031 Uiso 1 1 calc R . .
H10B H -0.8881 -0.1929 -0.2630 0.031 Uiso 1 1 calc R . .
H10C H -1.0901 -0.3335 -0.2585 0.031 Uiso 1 1 calc R . .
C11 C -0.6206(3) -0.8818(3) -0.09878(9) 0.0138(3) Uani 1 1 d . . .
C12 C -0.6501(4) -0.8043(4) -0.03134(10) 0.0197(4) Uani 1 1 d . . .
H12A H -0.5213 -0.7901 -0.0039 0.030 Uiso 1 1 calc R . .
H12B H -0.7311 -0.9229 -0.0122 0.030 Uiso 1 1 calc R . .
H12C H -0.7174 -0.6491 -0.0337 0.030 Uiso 1 1 calc R . .
C13 C -0.1529(3) -0.6123(4) -0.11373(10) 0.0155(4) Uani 1 1 d . . .
C14 C -0.0429(3) -0.3854(4) -0.09447(11) 0.0194(4) Uani 1 1 d . . .
H14A H 0.0116 -0.3924 -0.0479 0.029 Uiso 1 1 calc R . .
H14B H -0.1336 -0.2493 -0.1021 0.029 Uiso 1 1 calc R . .
H14C H 0.0652 -0.3662 -0.1209 0.029 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 0.0016 '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
_geom_angle_publ_flag
O3 C1 O1 112.25(14) . . ?
O3 C1 C6 104.60(16) . . ?
O1 C1 C6 105.54(15) . . ?
O3 C1 C2 108.10(14) . . ?
O1 C1 C2 110.53(16) . . ?
C6 C1 C2 115.77(15) . . ?
C1 O1 C5 114.96(14) . . ?
O4 C2 O5 112.41(15) . . ?
O4 C2 C3 113.81(17) . . ?
O5 C2 C3 104.04(14) . . ?
O4 C2 C1 105.19(14) . . ?
O5 C2 C1 113.36(17) . . ?
C3 C2 C1 108.18(14) . . ?
C7 O2 C6 106.70(16) . . ?
O6 C3 C4 109.93(16) . . ?
O6 C3 C2 107.43(13) . . ?
C4 C3 C2 113.17(14) . . ?
C1 O3 C7 109.24(14) . . ?
O8 C4 C5 108.07(15) . . ?
O8 C4 C3 110.10(14) . . ?
C5 C4 C3 108.55(17) . . ?
O1 C5 C4 112.13(15) . . ?
C2 O5 C10 117.59(15) . . ?
O2 C6 C1 104.54(16) . . ?
C11 O6 C3 116.35(14) . . ?
O2 C7 O3 104.42(16) . . ?
O2 C7 C9 109.10(19) . . ?
O3 C7 C9 108.40(16) . . ?
O2 C7 C8 110.87(17) . . ?
O3 C7 C8 110.26(18) . . ?
C9 C7 C8 113.37(18) . . ?
C13 O8 C4 118.66(15) . . ?
O7 C11 O6 123.64(17) . . ?
O7 C11 C12 123.88(18) . . ?
O6 C11 C12 112.48(16) . . ?
O9 C13 O8 124.1(2) . . ?
O9 C13 C14 125.9(2) . . ?
O8 C13 C14 110.03(17) . . ?
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 O3 1.413(2) . ?
C1 O1 1.417(2) . ?
C1 C6 1.536(3) . ?
C1 C2 1.558(2) . ?
O1 C5 1.434(2) . ?
C2 O4 1.400(2) . ?
C2 O5 1.406(2) . ?
C2 C3 1.532(3) . ?
O2 C7 1.426(2) . ?
O2 C6 1.427(3) . ?
C3 O6 1.452(2) . ?
C3 C4 1.527(3) . ?
O3 C7 1.444(2) . ?
C4 O8 1.444(2) . ?
C4 C5 1.517(2) . ?
O5 C10 1.451(3) . ?
O6 C11 1.348(2) . ?
C7 C9 1.498(3) . ?
C7 C8 1.525(3) . ?
O7 C11 1.210(2) . ?
O8 C13 1.347(2) . ?
O9 C13 1.213(3) . ?
C11 C12 1.494(3) . ?
C13 C14 1.500(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 O1 C5 -61.95(19) . . . . ?
C6 C1 O1 C5 -175.30(15) . . . . ?
C2 C1 O1 C5 58.83(19) . . . . ?
O3 C1 C2 O4 -168.90(15) . . . . ?
O1 C1 C2 O4 67.89(18) . . . . ?
C6 C1 C2 O4 -52.0(2) . . . . ?
O3 C1 C2 O5 -45.7(2) . . . . ?
O1 C1 C2 O5 -168.91(14) . . . . ?
C6 C1 C2 O5 71.2(2) . . . . ?
O3 C1 C2 C3 69.1(2) . . . . ?
O1 C1 C2 C3 -54.08(19) . . . . ?
C6 C1 C2 C3 -173.97(17) . . . . ?
O4 C2 C3 O6 58.51(19) . . . . ?
O5 C2 C3 O6 -64.16(18) . . . . ?
C1 C2 C3 O6 175.02(15) . . . . ?
O4 C2 C3 C4 -63.02(19) . . . . ?
O5 C2 C3 C4 174.31(15) . . . . ?
C1 C2 C3 C4 53.5(2) . . . . ?
O1 C1 O3 C7 -105.29(17) . . . . ?
C6 C1 O3 C7 8.64(19) . . . . ?
C2 C1 O3 C7 132.54(16) . . . . ?
O6 C3 C4 O8 -55.24(17) . . . . ?
C2 C3 C4 O8 64.88(19) . . . . ?
O6 C3 C4 C5 -173.35(15) . . . . ?
C2 C3 C4 C5 -53.23(19) . . . . ?
C1 O1 C5 C4 -59.2(2) . . . . ?
O8 C4 C5 O1 -66.0(2) . . . . ?
C3 C4 C5 O1 53.4(2) . . . . ?
O4 C2 O5 C10 44.7(2) . . . . ?
C3 C2 O5 C10 168.30(16) . . . . ?
C1 C2 O5 C10 -74.4(2) . . . . ?
C7 O2 C6 C1 -27.8(2) . . . . ?
O3 C1 C6 O2 11.64(19) . . . . ?
O1 C1 C6 O2 130.23(16) . . . . ?
C2 C1 C6 O2 -107.20(18) . . . . ?
C4 C3 O6 C11 -80.41(19) . . . . ?
C2 C3 O6 C11 156.05(17) . . . . ?
C6 O2 C7 O3 33.3(2) . . . . ?
C6 O2 C7 C9 149.05(15) . . . . ?
C6 O2 C7 C8 -85.4(2) . . . . ?
C1 O3 C7 O2 -25.8(2) . . . . ?
C1 O3 C7 C9 -142.05(16) . . . . ?
C1 O3 C7 C8 93.31(19) . . . . ?
C5 C4 O8 C13 -143.83(17) . . . . ?
C3 C4 O8 C13 97.76(19) . . . . ?
C3 O6 C11 O7 -2.0(3) . . . . ?
C3 O6 C11 C12 177.24(18) . . . . ?
C4 O8 C13 O9 0.8(3) . . . . ?
C4 O8 C13 C14 -178.87(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653422
