#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/22/1512287.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_1512287
loop_
_publ_author_name
'Baran, Arif'
'Aydin, Gokay'
'Savran, Tahir'
'Sahin, Ertan'
'Balci, Metin'
_publ_section_title
;
 Trisequential photooxygenation reaction: application to the synthesis of
 carbasugars.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4350
_journal_page_last               4353
_journal_paper_doi               10.1021/ol401823m
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C8 H16 O7, H2 O'
_chemical_formula_sum            'C8 H18 O8'
_chemical_formula_weight         242.22
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-08-06T13:27:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.0160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7832(2)
_cell_length_b                   7.8499(2)
_cell_length_c                   17.0819(5)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.21
_cell_volume                     1020.79(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0092
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20117
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.035(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.033
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0493P)²+0.4202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                1996
_reflns_number_total             2086
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol401823m_si_003.cif
_cod_data_source_block           arif_sakarya_0m_6agustos2_a
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1512287
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O4 O 0.80396(12) 0.64030(11) 0.20043(5) 0.0258(2) Uani 1 1 d U
H4 H 0.7875 0.5515 0.2231 0.039 Uiso 1 1 calc R
O5 O 0.84794(13) 0.73831(11) 0.00006(5) 0.0281(2) Uani 1 1 d U
H5 H 0.8872 0.8227 -0.0184 0.042 Uiso 1 1 calc R
O3 O 0.95087(12) 1.05757(10) 0.07703(5) 0.0263(2) Uani 1 1 d U
H3A H 0.8869 1.1243 0.0944 0.039 Uiso 1 1 calc R
O2 O 1.26992(11) 0.95675(11) 0.17007(6) 0.0271(2) Uani 1 1 d U
H2 H 1.3684 0.9364 0.1624 0.041 Uiso 1 1 calc R
O1 O 1.34160(11) 0.60205(11) 0.18429(6) 0.0309(2) Uani 1 1 d U
H1 H 1.4066 0.644 0.2235 0.046 Uiso 1 1 calc R
O7 O 0.74367(12) 0.30871(11) 0.12220(6) 0.0308(2) Uani 1 1 d U
H7 H 0.6537 0.2852 0.1378 0.046 Uiso 1 1 calc R
O6 O 0.60398(12) 0.90810(13) 0.14501(6) 0.0347(3) Uani 1 1 d U
H6 H 0.6407 0.8377 0.18 0.052 Uiso 1 1 calc R
C3 C 0.96399(14) 0.90291(13) 0.12144(6) 0.0180(2) Uani 1 1 d U
H3 H 0.9424 0.9268 0.1749 0.022 Uiso 1 1 calc R
C5 C 0.84687(14) 0.60141(14) 0.12453(6) 0.0184(2) Uani 1 1 d U
C2 C 1.14911(14) 0.83250(14) 0.12977(7) 0.0194(2) Uani 1 1 d U
H2A H 1.1729 0.8105 0.0765 0.023 Uiso 1 1 calc R
C4 C 0.82553(14) 0.77414(14) 0.07890(6) 0.0187(2) Uani 1 1 d U
C6 C 1.03633(14) 0.53607(14) 0.13681(7) 0.0208(3) Uani 1 1 d U
H6A H 1.0482 0.4335 0.1692 0.025 Uiso 1 1 calc R
H6B H 1.0623 0.507 0.0853 0.025 Uiso 1 1 calc R
C1 C 1.16693(14) 0.66807(14) 0.17754(7) 0.0209(3) Uani 1 1 d U
H1A H 1.146 0.6913 0.2312 0.025 Uiso 1 1 calc R
C7 C 0.72067(16) 0.46699(15) 0.08009(8) 0.0262(3) Uani 1 1 d U
H7A H 0.6005 0.5057 0.0751 0.031 Uiso 1 1 calc R
H7B H 0.7424 0.4512 0.0267 0.031 Uiso 1 1 calc R
C8 C 0.64171(16) 0.85204(16) 0.07096(8) 0.0273(3) Uani 1 1 d U
H8A H 0.6308 0.9481 0.0345 0.033 Uiso 1 1 calc R
H8B H 0.5548 0.7679 0.0475 0.033 Uiso 1 1 calc R
O8 O 1.44382(12) 0.27300(12) 0.18072(6) 0.0330(2) Uani 1 1 d .
H8C H 1.3599 0.2034 0.1612 0.070(7) Uiso 1 1 d .
H8D H 1.3979 0.3767 0.1831 0.072(7) Uiso 1 1 d .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C5 O4 H4 109.5
C4 O5 H5 109.5
C3 O3 H3A 109.5
C2 O2 H2 109.5
C1 O1 H1 109.5
C7 O7 H7 109.5
C8 O6 H6 109.5
O3 C3 C2 108.72(9)
O3 C3 C4 109.99(9)
C2 C3 C4 111.14(9)
O3 C3 H3 109
C2 C3 H3 109
C4 C3 H3 109
O4 C5 C7 110.37(9)
O4 C5 C6 110.18(9)
C7 C5 C6 109.67(9)
O4 C5 C4 104.26(8)
C7 C5 C4 111.21(9)
C6 C5 C4 111.06(9)
O2 C2 C1 110.14(9)
O2 C2 C3 108.21(9)
C1 C2 C3 109.74(9)
O2 C2 H2A 109.6
C1 C2 H2A 109.6
C3 C2 H2A 109.6
O5 C4 C8 106.91(9)
O5 C4 C3 111.34(9)
C8 C4 C3 109.09(9)
O5 C4 C5 106.31(9)
C8 C4 C5 113.06(9)
C3 C4 C5 110.09(9)
C1 C6 C5 111.59(9)
C1 C6 H6A 109.3
C5 C6 H6A 109.3
C1 C6 H6B 109.3
C5 C6 H6B 109.3
H6A C6 H6B 108
O1 C1 C6 108.85(9)
O1 C1 C2 109.20(9)
C6 C1 C2 110.92(9)
O1 C1 H1A 109.3
C6 C1 H1A 109.3
C2 C1 H1A 109.3
O7 C7 C5 110.47(10)
O7 C7 H7A 109.6
C5 C7 H7A 109.6
O7 C7 H7B 109.6
C5 C7 H7B 109.6
H7A C7 H7B 108.1
O6 C8 C4 113.86(10)
O6 C8 H8A 108.8
C4 C8 H8A 108.8
O6 C8 H8B 108.8
C4 C8 H8B 108.8
H8A C8 H8B 107.7
H8C O8 H8D 108.45(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C5 1.4373(13)
O4 H4 0.82
O5 C4 1.4218(13)
O5 H5 0.82
O3 C3 1.4239(13)
O3 H3A 0.82
O2 C2 1.4283(13)
O2 H2 0.82
O1 C1 1.4370(13)
O1 H1 0.82
O7 C7 1.4281(15)
O7 H7 0.82
O6 C8 1.4265(16)
O6 H6 0.82
C3 C2 1.5219(14)
C3 C4 1.5443(15)
C3 H3 0.98
C5 C7 1.5311(16)
C5 C6 1.5339(15)
C5 C4 1.5555(15)
C2 C1 1.5179(16)
C2 H2A 0.98
C4 C8 1.5357(16)
C6 C1 1.5155(15)
C6 H6A 0.97
C6 H6B 0.97
C1 H1A 0.98
C7 H7A 0.97
C7 H7B 0.97
C8 H8A 0.97
C8 H8B 0.97
O8 H8C 0.8634(9)
O8 H8D 0.8933(9)
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
O3 C3 C2 O2 59.34(11)
C4 C3 C2 O2 -179.46(9)
O3 C3 C2 C1 179.54(9)
C4 C3 C2 C1 -59.26(12)
O3 C3 C4 O5 58.99(11)
C2 C3 C4 O5 -61.46(12)
O3 C3 C4 C8 -58.76(11)
C2 C3 C4 C8 -179.22(9)
O3 C3 C4 C5 176.63(8)
C2 C3 C4 C5 56.18(12)
O4 C5 C4 O5 -173.79(8)
C7 C5 C4 O5 -54.85(11)
C6 C5 C4 O5 67.58(11)
O4 C5 C4 C8 -56.79(12)
C7 C5 C4 C8 62.14(12)
C6 C5 C4 C8 -175.43(9)
O4 C5 C4 C3 65.49(10)
C7 C5 C4 C3 -175.57(9)
C6 C5 C4 C3 -53.14(12)
O4 C5 C6 C1 -60.73(12)
C7 C5 C6 C1 177.59(9)
C4 C5 C6 C1 54.27(12)
C5 C6 C1 O1 -177.65(9)
C5 C6 C1 C2 -57.48(12)
O2 C2 C1 O1 -61.54(11)
C3 C2 C1 O1 179.43(9)
O2 C2 C1 C6 178.49(8)
C3 C2 C1 C6 59.46(12)
O4 C5 C7 O7 -65.59(12)
C6 C5 C7 O7 55.98(13)
C4 C5 C7 O7 179.21(9)
O5 C4 C8 O6 -175.24(10)
C3 C4 C8 O6 -54.73(13)
C5 C4 C8 O6 68.12(13)
