#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/79/1517946.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_1517946
loop_
_publ_author_name
'Matviitsuk, Anastassia'
'Berndt, Falko'
'Mahrwald, Rainer'
_publ_section_title
;
 Four into one: organocatalyzed stereoselective conjugate addition of
 unprotected and unactivated carbohydrates.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5474
_journal_page_last               5477
_journal_paper_doi               10.1021/ol5027443
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H16 O6'
_chemical_formula_sum            'C14 H16 O6'
_chemical_formula_weight         280.27
_chemical_name_systematic
;
 ?
;
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8338(3)
_cell_length_b                   7.2865(3)
_cell_length_c                   28.1501(16)
_cell_measurement_reflns_used    10768
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.70
_cell_measurement_theta_min      3.15
_cell_volume                     1401.72(12)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            19428
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.153
_diffrn_reflns_theta_min         3.148
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.3(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0214P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0545
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2289
_reflns_number_total             2784
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5027443_si_002.cif
_cod_data_source_block           anm234
_cod_depositor_comments
'Adding full bibliography for 1517946--1517947.cif.'
_cod_database_code               1517946
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.2960(2) 0.7000(2) 0.89716(5) 0.0228(4) Uani 1 1 d . .
O2 O 0.0174(2) 0.5977(2) 0.86222(5) 0.0201(4) Uani 1 1 d . .
O3 O -0.2520(2) 1.1993(2) 0.86557(6) 0.0253(4) Uani 1 1 d . .
O4 O -0.0348(3) 0.3357(2) 0.93558(6) 0.0239(4) Uani 1 1 d . .
H4 H -0.092(4) 0.293(4) 0.9121(10) 0.047(10) Uiso 1 1 d . .
O5 O 0.3164(3) 0.2293(2) 0.97865(6) 0.0227(4) Uani 1 1 d . .
H5 H 0.371(4) 0.224(4) 1.0037(10) 0.045(10) Uiso 1 1 d . .
O6 O 0.5599(3) 0.5559(2) 1.00336(6) 0.0242(4) Uani 1 1 d . .
H6 H 0.627(4) 0.461(4) 1.0094(9) 0.037(9) Uiso 1 1 d . .
C1 C 0.1165(3) 0.6114(3) 0.90687(8) 0.0194(5) Uani 1 1 d . .
H1 H 0.0389 0.6814 0.9299 0.023 Uiso 1 1 calc R U
C2 C -0.0813(3) 0.7448(3) 0.84493(8) 0.0193(5) Uani 1 1 d . .
C3 C -0.0974(3) 0.9089(3) 0.86643(8) 0.0212(5) Uani 1 1 d . .
H3 H -0.0227 0.9337 0.8933 0.025 Uiso 1 1 calc R U
C4 C -0.2281(4) 1.0456(3) 0.84847(8) 0.0231(6) Uani 1 1 d . .
H4A H -0.3011 1.0159 0.8217 0.028 Uiso 1 1 calc R U
C5 C -0.1675(3) 0.6983(3) 0.79778(8) 0.0183(5) Uani 1 1 d . .
C6 C -0.2891(4) 0.5463(3) 0.79224(8) 0.0222(6) Uani 1 1 d . .
H6A H -0.3237 0.4760 0.8185 0.027 Uiso 1 1 calc R U
C7 C -0.3585(4) 0.5001(3) 0.74750(8) 0.0251(6) Uani 1 1 d . .
H7 H -0.4406 0.3993 0.7438 0.030 Uiso 1 1 calc R U
C8 C -0.3057(4) 0.6036(3) 0.70836(8) 0.0245(6) Uani 1 1 d . .
H8 H -0.3509 0.5711 0.6783 0.029 Uiso 1 1 calc R U
C9 C -0.1862(4) 0.7550(3) 0.71368(8) 0.0258(6) Uani 1 1 d . .
H9 H -0.1518 0.8248 0.6873 0.031 Uiso 1 1 calc R U
C10 C -0.1178(3) 0.8029(3) 0.75817(8) 0.0223(6) Uani 1 1 d . .
H10 H -0.0381 0.9054 0.7617 0.027 Uiso 1 1 calc R U
C11 C 0.1479(4) 0.4159(3) 0.92355(8) 0.0183(5) Uani 1 1 d . .
H11 H 0.2109 0.3442 0.8984 0.022 Uiso 1 1 calc R U
C12 C 0.2751(3) 0.4162(3) 0.96744(7) 0.0184(5) Uani 1 1 d . .
H12 H 0.2018 0.4713 0.9938 0.022 Uiso 1 1 calc R U
C13 C 0.4608(4) 0.5258(3) 0.95939(8) 0.0197(5) Uani 1 1 d . .
H13 H 0.5469 0.4605 0.9373 0.024 Uiso 1 1 calc R U
C14 C 0.4123(4) 0.7149(3) 0.93986(8) 0.0225(6) Uani 1 1 d . .
H14A H 0.3408 0.7843 0.9636 0.027 Uiso 1 1 calc R U
H14B H 0.5326 0.7803 0.9329 0.027 Uiso 1 1 calc R U
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
C1 O1 C14 110.56(16)
C2 O2 C1 119.69(18)
C11 O4 H4 113(2)
C12 O5 H5 109(2)
C13 O6 H6 107.8(18)
O1 C1 O2 105.84(17)
O1 C1 C11 111.49(19)
O2 C1 C11 105.86(17)
O1 C1 H1 111.1
O2 C1 H1 111.1
C11 C1 H1 111.1
C3 C2 O2 125.6(2)
C3 C2 C5 124.8(2)
O2 C2 C5 109.7(2)
C2 C3 C4 120.8(2)
C2 C3 H3 119.6
C4 C3 H3 119.6
O3 C4 C3 125.4(2)
O3 C4 H4A 117.3
C3 C4 H4A 117.3
C10 C5 C6 119.4(2)
C10 C5 C2 119.5(2)
C6 C5 C2 121.1(2)
C7 C6 C5 119.9(2)
C7 C6 H6A 120.0
C5 C6 H6A 120.0
C8 C7 C6 120.1(2)
C8 C7 H7 120.0
C6 C7 H7 120.0
C9 C8 C7 120.2(2)
C9 C8 H8 119.9
C7 C8 H8 119.9
C8 C9 C10 120.0(2)
C8 C9 H9 120.0
C10 C9 H9 120.0
C9 C10 C5 120.3(2)
C9 C10 H10 119.8
C5 C10 H10 119.8
O4 C11 C12 108.15(18)
O4 C11 C1 109.7(2)
C12 C11 C1 109.47(18)
O4 C11 H11 109.8
C12 C11 H11 109.8
C1 C11 H11 109.8
O5 C12 C11 107.06(18)
O5 C12 C13 111.72(19)
C11 C12 C13 111.12(18)
O5 C12 H12 109.0
C11 C12 H12 109.0
C13 C12 H12 109.0
O6 C13 C12 110.37(18)
O6 C13 C14 106.14(18)
C12 C13 C14 110.4(2)
O6 C13 H13 110.0
C12 C13 H13 110.0
C14 C13 H13 110.0
O1 C14 C13 110.65(18)
O1 C14 H14A 109.5
C13 C14 H14A 109.5
O1 C14 H14B 109.5
C13 C14 H14B 109.5
H14A C14 H14B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.413(3)
O1 C14 1.445(3)
O2 C2 1.356(3)
O2 C1 1.431(3)
O3 C4 1.230(3)
O4 C11 1.419(3)
O4 H4 0.83(3)
O5 C12 1.426(3)
O5 H5 0.80(3)
O6 C13 1.428(3)
O6 H6 0.85(3)
C1 C11 1.516(3)
C1 H1 0.9800
C2 C3 1.344(3)
C2 C5 1.491(3)
C3 C4 1.431(3)
C3 H3 0.9300
C4 H4A 0.9300
C5 C10 1.393(3)
C5 C6 1.393(3)
C6 C7 1.387(3)
C6 H6A 0.9300
C7 C8 1.383(3)
C7 H7 0.9300
C8 C9 1.381(3)
C8 H8 0.9300
C9 C10 1.382(3)
C9 H9 0.9300
C10 H10 0.9300
C11 C12 1.510(3)
C11 H11 0.9800
C12 C13 1.517(3)
C12 H12 0.9800
C13 C14 1.520(3)
C13 H13 0.9800
C14 H14A 0.9700
C14 H14B 0.9700
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
C14 O1 C1 O2 -177.80(17)
C14 O1 C1 C11 -63.2(2)
C2 O2 C1 O1 -80.8(2)
C2 O2 C1 C11 160.72(18)
C1 O2 C2 C3 -0.4(3)
C1 O2 C2 C5 178.66(19)
O2 C2 C3 C4 -170.8(2)
C5 C2 C3 C4 10.2(4)
C2 C3 C4 O3 -179.7(2)
C3 C2 C5 C10 57.2(3)
O2 C2 C5 C10 -121.8(2)
C3 C2 C5 C6 -126.1(3)
O2 C2 C5 C6 54.9(3)
C10 C5 C6 C7 0.3(4)
C2 C5 C6 C7 -176.4(2)
C5 C6 C7 C8 0.6(4)
C6 C7 C8 C9 -1.0(4)
C7 C8 C9 C10 0.5(4)
C8 C9 C10 C5 0.5(4)
C6 C5 C10 C9 -0.9(4)
C2 C5 C10 C9 175.9(2)
O1 C1 C11 O4 176.55(17)
O2 C1 C11 O4 -68.8(2)
O1 C1 C11 C12 58.0(2)
O2 C1 C11 C12 172.68(18)
O4 C11 C12 O5 66.4(2)
C1 C11 C12 O5 -174.13(19)
O4 C11 C12 C13 -171.32(18)
C1 C11 C12 C13 -51.9(2)
O5 C12 C13 O6 -72.1(2)
C11 C12 C13 O6 168.43(18)
O5 C12 C13 C14 170.89(17)
C11 C12 C13 C14 51.4(2)
C1 O1 C14 C13 61.5(2)
O6 C13 C14 O1 -174.96(18)
C12 C13 C14 O1 -55.3(3)
